Small Molecule X-ray Facility

School Of Chemistry
Structure Report
Filename: TCD132 , Compound 1

Submitted by: Pierce Kavanagh, John Power

Reference: TLC3
Group: Kavanagh

Fig. 1. Asymmetric unit of TCD132. Displacement ellipsoids shown at 50%.

2/10/14

Brendan Twamley
Fig. 2. Packing diagram of TCD132 viewed down the a-axis. Hydrogen atoms omitted for clarity.
 Crystal Structure Report for TCD132, Compound 1

A specimen of C20H16N2O2, approximate dimensions 0.040 mm x 0.100 mm x 0.270 mm,

was used for the X-ray crystallographic analysis. The X-ray intensity data were measured at
100(2)K using an Oxford Cryosystems Cobra low temperature device using a MiTeGen
micromount. See Table 1 for collection parameters and exposure time. Bruker APEX
software was used to correct for Lorentz and polarization effects.

A total of 1865 frames were collected. The total exposure time was 18.13 hours. The frames
were integrated with the Bruker SAINT software package using a narrow-frame algorithm.
The integration of the data using a monoclinic unit cell yielded a total of 46288 reflections to
a maximum θ angle of 26.40° (0.80 Å resolution), of which 3353 were independent (average
redundancy 13.805, completeness = 99.8%, Rint =9.90%, Rsig = 4.77%) and 2299 (68.57%)
were greater than 2σ(F2). The final cell constants
of a = 9.0836(4) Å, b = 16.5254(7) Å, c =11.0183(5) Å, β = 98.8792(18)°, volume
= 1634.14(12) Å3, are based upon the refinement of the XYZ-centroids of 6373 reflections
above 20 σ(I) with 4.93° < 2θ < 52.67°. Data were corrected for absorption effects using the
multi-scan method (SADABS). The ratio of minimum to maximum apparent transmission
was 0.928. The calculated minimum and maximum transmission coefficients (based on
crystal size) are0.6914 and 0.7454.

The structure was solved and refined using the Bruker SHELXTL Software Package, using
the space group P 1 21/c 1, with Z = 4 for the formula unit, C20H16N2O2. The final anisotropic
full-matrix least-squares refinement on F2 with 219 variables converged at R1 = 4.75%, for
the observed data and wR2 = 11.44% for all data. The goodness-of-fit was 1.036. The largest
peak in the final difference electron density synthesis was 0.235 e-/Å3 and the largest hole
was -0.250 e-/Å3 with an RMS deviation of 0.048 e-/Å3. On the basis of the final model, the
calculated density was 1.286 g/cm3 and F(000), 664 e-.

References:
Bruker APEX v2012.12-0, Bruker AXS Inc., Madison, Wisconsin, USA.

SADABS (2014/3) Bruker AXS Inc., Madison, Wisconsin, USA; Sheldrick, G. M.

University of Göttingen, Germany.

SHELXL-2014, (2014), Bruker AXS Inc., Madison, Wisconsin, USA; Sheldrick, G. M.

University of Göttingen, Germany.

Acknowledgement:
Facility funded by PRTLI and ERDF.
Table 1: Data collection details for TCD132.
Axis dx/mm 2θ/° ω/° φ/° χ/° Width/° Frames Time/s Wavelength/Å Voltage/kV Current/mA Temperature/K
Omega 50.376 25.24 315.23 285.36 66.49 1.00 82 35.00 0.71073 50 30.0 100
Phi 50.376 24.13 278.95 265.00 23.00 1.00 214 35.00 0.71073 50 30.0 100
Omega 50.376 24.13 11.20 255.00 -54.74 1.00 133 35.00 0.71073 50 30.0 100
Omega 50.376 24.13 11.20 102.00 -54.74 1.00 133 35.00 0.71073 50 30.0 100
Omega 50.376 24.13 11.20 306.00 -54.74 1.00 133 35.00 0.71073 50 30.0 100
Omega 50.376 24.13 11.20 153.00 -54.74 1.00 133 35.00 0.71073 50 30.0 100
Omega 50.376 24.13 11.20 51.00 -54.74 1.00 133 35.00 0.71073 50 30.0 100
Phi 50.376 24.13 352.47 356.00 -23.00 1.00 184 35.00 0.71073 50 30.0 100
Phi 50.376 24.13 10.58 188.00 -57.06 1.00 184 35.00 0.71073 50 30.0 100
Omega 50.376 24.13 11.20 0.00 -54.74 1.00 133 35.00 0.71073 50 30.0 100
Omega 50.376 9.13 355.20 0.00 -54.74 1.00 135 35.00 0.71073 50 30.0 100
Omega 50.376 9.13 355.20 180.00 -54.74 1.00 135 35.00 0.71073 50 30.0 100
Omega 50.376 24.13 11.20 204.00 -54.74 1.00 133 35.00 0.71073 50 30.0 100
 Table 2. Crystal data and structure refinement for tcd132.
Identification code tcd132
Empirical formula C20H16N2O2
Formula weight 316.35
Temperature 100(2) K
Wavelength 0.71073 Å
Crystal system Monoclinic
Space group P21/c
Unit cell dimensions a = 9.0836(4) Å α= 90°.
b = 16.5254(7) Å β= 98.8792(18)°.
c = 11.0183(5) Å γ = 90°.
Volume 1634.14(12) Å3
Z 4
Density (calculated) 1.286 Mg/m3
Absorption coefficient 0.084 mm-1
F(000) 664
Crystal size 0.270 x 0.100 x 0.040 mm3
Theta range for data collection 2.240 to 26.401°.
Index ranges -11≤h≤11, -20≤k≤20, -13≤l≤13
Reflections collected 46288
Independent reflections 3353 [R(int) = 0.0990]
Completeness to theta = 25.242° 100.0 %
Absorption correction Semi-empirical from equivalents
Max. and min. transmission 0.7454 and 0.6914
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 3353 / 0 / 219
Goodness-of-fit on F2 1.036
Final R indices [I>2σ(I)] R1 = 0.0475, wR2 = 0.1018
R indices (all data) R1 = 0.0844, wR2 = 0.1144
Largest diff. peak and hole 0.235 and -0.250 e.Å-3
Table 3. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103)
for tcd132. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
________________________________________________________________________________
x y z U(eq)
________________________________________________________________________________
C(1) 2002(2) 5577(1) 7680(2) 18(1)
C(2) 1372(2) 6378(1) 7099(2) 18(1)
C(3) 459(2) 6364(1) 5965(2) 24(1)
C(4) -104(2) 7080(1) 5426(2) 29(1)
C(5) 222(2) 7809(1) 6025(2) 30(1)
C(6) 1112(2) 7825(1) 7158(2) 29(1)
C(7) 1692(2) 7115(1) 7695(2) 23(1)
C(8) 2452(2) 5696(1) 9012(2) 19(1)
N(9) 2737(2) 5814(1) 10047(1) 25(1)
C(10) 721(2) 4936(1) 7501(2) 19(1)
C(11) -592(2) 5110(1) 8125(2) 25(1)
O(12) 802(1) 4358(1) 6846(1) 25(1)
C(13) 3394(2) 5275(1) 7101(2) 18(1)
C(14) 4632(2) 5922(1) 7259(2) 18(1)
C(15) 5608(2) 5969(1) 8352(2) 21(1)
C(16) 6685(2) 6576(1) 8524(2) 25(1)
C(17) 6799(2) 7121(1) 7591(2) 29(1)
C(18) 5825(2) 7076(1) 6503(2) 29(1)
C(19) 4744(2) 6482(1) 6335(2) 24(1)
C(20) 2944(2) 5106(1) 5776(2) 20(1)
N(21) 2673(2) 4981(1) 4747(2) 29(1)
C(22) 4007(2) 4461(1) 7714(2) 20(1)
C(23) 5125(2) 4012(1) 7103(2) 27(1)
O(24) 3577(2) 4223(1) 8633(1) 26(1)
________________________________________________________________________________
Table 4. Bond lengths [Å] and angles [°] for tcd132.
_____________________________________________________
C(1)-C(8) 1.475(2) C(22)-O(24) 1.206(2)
C(1)-C(2) 1.541(2) C(22)-C(23) 1.499(3)
C(1)-C(10) 1.563(2) C(23)-H(23A) 0.9800
C(1)-C(13) 1.582(2) C(23)-H(23B) 0.9800
C(2)-C(3) 1.388(2) C(23)-H(23C) 0.9800
C(2)-C(7) 1.393(3)
C(3)-C(4) 1.386(3) C(8)-C(1)-C(2) 109.13(14)
C(3)-H(3A) 0.9500 C(8)-C(1)-C(10) 107.54(14)
C(4)-C(5) 1.383(3) C(2)-C(1)-C(10) 107.92(14)
C(4)-H(4A) 0.9500 C(8)-C(1)-C(13) 109.12(14)
C(5)-C(6) 1.379(3) C(2)-C(1)-C(13) 111.87(14)
C(5)-H(5A) 0.9500 C(10)-C(1)-C(13) 111.15(14)
C(6)-C(7) 1.381(3) C(3)-C(2)-C(7) 119.43(17)
C(6)-H(6A) 0.9500 C(3)-C(2)-C(1) 119.38(16)
C(7)-H(7A) 0.9500 C(7)-C(2)-C(1) 121.18(15)
C(8)-N(9) 1.146(2) C(4)-C(3)-C(2) 120.00(18)
C(10)-O(12) 1.207(2) C(4)-C(3)-H(3A) 120.0
C(10)-C(11) 1.494(3) C(2)-C(3)-H(3A) 120.0
C(11)-H(11A) 0.9800 C(5)-C(4)-C(3) 120.12(18)
C(11)-H(11B) 0.9800 C(5)-C(4)-H(4A) 119.9
C(11)-H(11C) 0.9800 C(3)-C(4)-H(4A) 119.9
C(13)-C(20) 1.480(2) C(6)-C(5)-C(4) 120.06(18)
C(13)-C(14) 1.542(2) C(6)-C(5)-H(5A) 120.0
C(13)-C(22) 1.569(2) C(4)-C(5)-H(5A) 120.0
C(14)-C(15) 1.383(2) C(5)-C(6)-C(7) 120.21(18)
C(14)-C(19) 1.392(2) C(5)-C(6)-H(6A) 119.9
C(15)-C(16) 1.394(3) C(7)-C(6)-H(6A) 119.9
C(15)-H(15A) 0.9500 C(6)-C(7)-C(2) 120.18(18)
C(16)-C(17) 1.383(3) C(6)-C(7)-H(7A) 119.9
C(16)-H(16A) 0.9500 C(2)-C(7)-H(7A) 119.9
C(17)-C(18) 1.378(3) N(9)-C(8)-C(1) 176.37(19)
C(17)-H(17A) 0.9500 O(12)-C(10)-C(11) 123.65(17)
C(18)-C(19) 1.381(3) O(12)-C(10)-C(1) 119.94(16)
C(18)-H(18A) 0.9500 C(11)-C(10)-C(1) 116.34(15)
C(19)-H(19A) 0.9500 C(10)-C(11)-H(11A) 109.5
C(20)-N(21) 1.142(2) C(10)-C(11)-H(11B) 109.5
H(11A)-C(11)-H(11B) 109.5 C(18)-C(17)-C(16) 120.03(18)
C(10)-C(11)-H(11C) 109.5 C(18)-C(17)-H(17A) 120.0
H(11A)-C(11)-H(11C) 109.5 C(16)-C(17)-H(17A) 120.0
H(11B)-C(11)-H(11C) 109.5 C(17)-C(18)-C(19) 120.19(19)
C(20)-C(13)-C(14) 109.10(14) C(17)-C(18)-H(18A) 119.9
C(20)-C(13)-C(22) 106.78(14) C(19)-C(18)-H(18A) 119.9
C(14)-C(13)-C(22) 109.99(14) C(18)-C(19)-C(14) 120.38(18)
C(20)-C(13)-C(1) 109.96(14) C(18)-C(19)-H(19A) 119.8
C(14)-C(13)-C(1) 110.47(14) C(14)-C(19)-H(19A) 119.8
C(22)-C(13)-C(1) 110.46(14) N(21)-C(20)-C(13) 176.48(19)
C(15)-C(14)-C(19) 119.36(17) O(24)-C(22)-C(23) 123.11(17)
C(15)-C(14)-C(13) 119.72(15) O(24)-C(22)-C(13) 120.11(16)
C(19)-C(14)-C(13) 120.87(16) C(23)-C(22)-C(13) 116.77(15)
C(14)-C(15)-C(16) 120.09(17) C(22)-C(23)-H(23A) 109.5
C(14)-C(15)-H(15A) 120.0 C(22)-C(23)-H(23B) 109.5
C(16)-C(15)-H(15A) 120.0 H(23A)-C(23)-H(23B) 109.5
C(17)-C(16)-C(15) 119.94(18) C(22)-C(23)-H(23C) 109.5
C(17)-C(16)-H(16A) 120.0 H(23A)-C(23)-H(23C) 109.5
C(15)-C(16)-H(16A) 120.0 H(23B)-C(23)-H(23C) 109.5
_____________________________________________________________
Table 5. Anisotropic displacement parameters (Å2x 103) for tcd132. The anisotropic
displacement factor exponent takes the form: -2π2[ h2 a*2U11 + ... + 2 h k a* b* U12 ]
______________________________________________________________________________
U11 U22 U33 U23 U13 U12
______________________________________________________________________________
C(1) 17(1) 19(1) 18(1) 0(1) 3(1) -1(1)
C(2) 16(1) 19(1) 20(1) 2(1) 5(1) 0(1)
C(3) 24(1) 23(1) 23(1) 1(1) 2(1) -2(1)
C(4) 27(1) 31(1) 26(1) 4(1) -2(1) 0(1)
C(5) 25(1) 24(1) 40(1) 10(1) 1(1) 2(1)
C(6) 26(1) 20(1) 39(1) -1(1) 2(1) 0(1)
C(7) 20(1) 24(1) 26(1) -2(1) 1(1) -1(1)
C(8) 16(1) 18(1) 23(1) 1(1) 4(1) 0(1)
N(9) 23(1) 29(1) 23(1) 0(1) 4(1) 1(1)
C(10) 20(1) 20(1) 17(1) 4(1) 0(1) -1(1)
C(11) 21(1) 28(1) 26(1) -1(1) 5(1) -4(1)
O(12) 27(1) 22(1) 27(1) -3(1) 6(1) -4(1)
C(13) 19(1) 19(1) 17(1) -2(1) 2(1) -1(1)
C(14) 16(1) 18(1) 22(1) -2(1) 5(1) 1(1)
C(15) 19(1) 20(1) 24(1) 1(1) 4(1) 3(1)
C(16) 19(1) 27(1) 29(1) -6(1) 0(1) 0(1)
C(17) 25(1) 26(1) 37(1) -7(1) 9(1) -7(1)
C(18) 34(1) 25(1) 29(1) 2(1) 9(1) -7(1)
C(19) 26(1) 27(1) 21(1) 0(1) 4(1) -2(1)
C(20) 17(1) 20(1) 23(1) 0(1) 4(1) -1(1)
N(21) 26(1) 37(1) 24(1) -1(1) 4(1) -5(1)
C(22) 20(1) 22(1) 18(1) -2(1) -2(1) -3(1)
C(23) 27(1) 25(1) 28(1) -1(1) 6(1) 4(1)
O(24) 31(1) 25(1) 23(1) 4(1) 6(1) 2(1)
______________________________________________________________________________
Table 6. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å2x 10 3)
for tcd132.
________________________________________________________________________________
x y z U(eq)
________________________________________________________________________________

H(3A) 220 5863 5559 28

H(4A) -714 7070 4644 35
H(5A) -168 8299 5656 36
H(6A) 1328 8326 7570 34
H(7A) 2310 7129 8473 28
H(11A) -818 4633 8591 37
H(11B) -1455 5242 7507 37
H(11C) -365 5569 8685 37
H(15A) 5544 5587 8986 25
H(16A) 7341 6616 9282 30
H(17A) 7549 7527 7700 35
H(18A) 5899 7455 5866 35
H(19A) 4072 6456 5584 29
H(23A) 5732 3666 7706 40
H(23B) 5770 4401 6766 40
H(23C) 4605 3678 6437 40
________________________________________________________________________________
Table 7. Torsion angles [°] for tcd132.
________________________________________________________________
C(8)-C(1)-C(2)-C(3) -159.67(16) C(10)-C(1)-C(13)-C(14) 178.72(14)
C(10)-C(1)-C(2)-C(3) -43.1(2) C(8)-C(1)-C(13)-C(22) 59.07(18)
C(13)-C(1)-C(2)-C(3) 79.5(2) C(2)-C(1)-C(13)-C(22) 179.92(14)
C(8)-C(1)-C(2)-C(7) 19.8(2) C(10)-C(1)-C(13)-C(22) -59.36(17)
C(10)-C(1)-C(2)-C(7) 136.42(16) C(20)-C(13)-C(14)-C(15) -155.90(16)
C(13)-C(1)-C(2)-C(7) -101.01(18) C(22)-C(13)-C(14)-C(15) -39.1(2)
C(7)-C(2)-C(3)-C(4) 1.1(3) C(1)-C(13)-C(14)-C(15) 83.11(19)
C(1)-C(2)-C(3)-C(4) -179.33(17) C(20)-C(13)-C(14)-C(19) 26.8(2)
C(2)-C(3)-C(4)-C(5) -1.1(3) C(22)-C(13)-C(14)-C(19) 143.63(16)
C(3)-C(4)-C(5)-C(6) 0.3(3) C(1)-C(13)-C(14)-C(19) -94.17(19)
C(4)-C(5)-C(6)-C(7) 0.5(3) C(19)-C(14)-C(15)-C(16) 0.4(3)
C(5)-C(6)-C(7)-C(2) -0.5(3) C(13)-C(14)-C(15)-C(16) -176.94(16)
C(3)-C(2)-C(7)-C(6) -0.4(3) C(14)-C(15)-C(16)-C(17) -1.4(3)
C(1)-C(2)-C(7)-C(6) -179.89(17) C(15)-C(16)-C(17)-C(18) 1.6(3)
C(8)-C(1)-C(10)-O(12) -128.69(17) C(16)-C(17)-C(18)-C(19) -0.7(3)
C(2)-C(1)-C(10)-O(12) 113.70(18) C(17)-C(18)-C(19)-C(14) -0.4(3)
C(13)-C(1)-C(10)-O(12) -9.3(2) C(15)-C(14)-C(19)-C(18) 0.5(3)
C(8)-C(1)-C(10)-C(11) 54.28(19) C(13)-C(14)-C(19)-C(18) 177.79(17)
C(2)-C(1)-C(10)-C(11) -63.33(19) C(20)-C(13)-C(22)-O(24) -131.26(17)
C(13)-C(1)-C(10)-C(11) 173.66(15) C(14)-C(13)-C(22)-O(24) 110.49(18)
C(8)-C(1)-C(13)-C(20) 176.68(15) C(1)-C(13)-C(22)-O(24) -11.7(2)
C(2)-C(1)-C(13)-C(20) -62.47(18) C(20)-C(13)-C(22)-C(23) 48.8(2)
C(10)-C(1)-C(13)-C(20) 58.25(18) C(14)-C(13)-C(22)-C(23) -69.49(19)
C(8)-C(1)-C(13)-C(14) -62.85(18) C(1)-C(13)-C(22)-C(23) 168.30(15)
C(2)-C(1)-C(13)-C(14) 58.00(18)
________________________________________________________________
Table 8. Hydrogen bonds for tcd132 [Å and °].
____________________________________________________________________________
D-H...A d(D-H) d(H...A) d(D...A) <(DHA)
____________________________________________________________________________
C(11)-H(11A)...N(9)#1 0.98 2.58 3.376(2) 139
C(11)-H(11B)...N(21)#2 0.98 2.58 3.429(3) 144
C(23)-H(23B)...N(21)#3 0.98 2.56 3.489(2) 159
____________________________________________________________________________
Symmetry transformations used to generate equivalent atoms:
#1 -x,-y+1,-z+2 #2 -x,-y+1,-z+1 #3 -x+1,-y+1,-z+1
 Small Molecule X-ray Facility
School Of Chemistry
Structure Report
Filename: TCD148 , Compound 2.

Submitted by: Pierce Kavanagh, John Power

Reference: PKJPCN
Group: Kavanagh

Fig. 1. Asymmetric unit of TCD148. Displacement ellipsoids shown at 50%. Hydrogen atoms
omitted for clarity.

28/10/14

Brendan Twamley
 Crystal Structure Report for TCD148, Compound 2.

A specimen of C18H12N2, approximate dimensions 0.080 mm x 0.110 mm x 0.200 mm, was

used for the X-ray crystallographic analysis. The X-ray intensity data were measured at
100(2)K using an Oxford Cryosystems Cobra low temperature device using a MiTeGen
micromount. See Table 1 for collection parameters and exposure time. Bruker APEX
software was used to correct for Lorentz and polarization effects.

A total of 4033 frames were collected. The total exposure time was 39.21 hours. The
integration of the data using an orthorhombic unit cell yielded a total of 81867 reflections to a
maximum θ angle of 26.54° (0.80 Å resolution), of which 5536 were independent (average
redundancy 14.788, completeness = 99.9%, Rint = 5.84%, Rsig = 2.71%) and 4817 (87.01%)
were greater than 2σ(F2).The final cell constants of a = 8.7061(3) Å, b = 11.6316(4) Å, c =
26.4065(9) Å, volume = 2674.08(16) Å3, are based upon the refinement of the XYZ-centroids
of reflections above 20 σ(I). Data were corrected for absorption effects using the numerical
method (SADABS). The calculated minimum and maximum transmission coefficients
(based on crystal size) are 0.9061 and 1.0000.

The structure was solved and refined using the Bruker SHELXTL Software Package, using
the space group P212121, with Z = 8 for the formula unit, C18H12N2.The final anisotropic full-
matrix least-squares refinement on F2 with 363 variables converged at R1 = 3.59%, for the
observed data and wR2 = 8.34% for all data. The goodness-of-fit was 1.048. The largest peak
in the final difference electron density synthesis was 0.170 e-/Å3 and the largest hole was -
0.188 e-/Å3 with an RMS deviation of 0.044 e-/Å3. On the basis of the final model, the
calculated density was 1.273 g/cm3 and F(000), 1072 e-.

Refinement Note: The racemate crystallized in a chiral space group. Flack parameter
refinement is inapplicable.

References:
Bruker APEX v2012.12-0, Bruker AXS Inc., Madison, Wisconsin, USA.

SADABS (2014/3) Bruker AXS Inc., Madison, Wisconsin, USA; Sheldrick, G. M.

University of Göttingen, Germany.

SHELXL-2014, (2014), Bruker AXS Inc., Madison, Wisconsin, USA; Sheldrick, G. M.

University of Göttingen, Germany.

Acknowledgement:
Facility funded by PRTLI and ERDF.
Table 1: Data collection details for TCD148.
Axis dx/mm 2θ/° ω/° φ/° χ/° Width/° Frames Time/s Wavelength/Å Voltage/kV Current/mA Temperature/K
Phi 50.000 22.63 277.45 360.00 23.00 0.50 720 35.00 0.71073 50 30.0 100
Omega 50.000 23.73 315.79 262.82 66.68 0.50 160 35.00 0.71073 50 30.0 100
Omega 50.000 22.63 9.70 204.00 -54.74 0.50 266 35.00 0.71073 50 30.0 100
Omega 50.000 23.73 285.93 307.17 61.39 0.50 221 35.00 0.71073 50 30.0 100
Omega 50.000 22.63 9.70 153.00 -54.74 0.50 266 35.00 0.71073 50 30.0 100
Phi 50.000 22.63 9.08 209.75 -57.06 0.50 393 35.00 0.71073 50 30.0 100
Omega 50.000 22.63 9.70 0.00 -54.74 0.50 266 35.00 0.71073 50 30.0 100
Omega 50.000 22.63 9.70 51.00 -54.74 0.50 266 35.00 0.71073 50 30.0 100
Omega 50.000 7.63 353.70 0.00 -54.74 0.50 270 35.00 0.71073 50 30.0 100
Omega 50.000 7.63 353.70 270.00 -54.74 0.50 270 35.00 0.71073 50 30.0 100
Phi 50.000 22.63 350.97 196.00 -23.00 0.50 400 35.00 0.71073 50 30.0 100
Omega 50.000 22.63 9.70 102.00 -54.74 0.50 266 35.00 0.71073 50 30.0 100
Omega 50.000 23.73 263.32 74.61 53.72 0.50 269 35.00 0.71073 50 30.0 100
 Table 2. Crystal data and structure refinement for tcd148.
Identification code tcd148
Empirical formula C18H12N2
Formula weight 256.30
Temperature 100(2) K
Wavelength 0.71073 Å
Crystal system Orthorhombic
Space group P212121
Unit cell dimensions a = 8.7061(3) Å α= 90°.
b = 11.6316(4) Å β= 90°.
c = 26.4065(9) Å γ = 90°.
Volume 2674.08(16) Å3
Z 8
Density (calculated) 1.273 Mg/m3
Absorption coefficient 0.076 mm-1
F(000) 1072
Crystal size 0.200 x 0.110 x 0.080 mm3
Theta range for data collection 1.542 to 26.535°.
Index ranges -10≤h≤10, -14≤k≤14, -33≤l≤33
Reflections collected 81867
Independent reflections 5536 [R(int) = 0.0584]
Completeness to theta = 25.242° 100.0 %
Absorption correction Numerical
Max. and min. transmission 1.0000 and 0.9061
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 5536 / 0 / 363
Goodness-of-fit on F2 1.048
Final R indices [I>2σ(I)] R1 = 0.0359, wR2 = 0.0785
R indices (all data) R1 = 0.0470, wR2 = 0.0834
Absolute structure parameter Inapplicable
Largest diff. peak and hole 0.170 and -0.188 e.Å-3
Table 3. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103)
for tcd148. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
________________________________________________________________________________
x y z U(eq)
________________________________________________________________________________
N(21) 4510(2) 9740(2) 2699(1) 26(1)
C(22) 3728(3) 9277(2) 2982(1) 20(1)
C(23) 2745(3) 8721(2) 3346(1) 18(1)
C(24) 1846(3) 9347(2) 3728(1) 18(1)
C(25) 1747(3) 10511(2) 3838(1) 20(1)
C(26) 865(3) 10842(2) 4254(1) 22(1)
C(27) 98(3) 10034(2) 4547(1) 22(1)
C(28) 195(3) 8860(2) 4433(1) 20(1)
C(29) 1079(2) 8539(2) 4024(1) 17(1)
C(30) 1457(3) 7326(2) 3829(1) 18(1)
C(31) 2584(3) 7578(2) 3393(1) 19(1)
C(32) 3359(3) 6642(2) 3107(1) 23(1)
C(33) 2302(3) 6701(2) 4232(1) 20(1)
N(34) 2950(2) 6227(2) 4548(1) 27(1)
C(35) 35(3) 6638(2) 3669(1) 18(1)
C(36) -745(3) 5955(2) 4018(1) 23(1)
C(37) -2091(3) 5392(2) 3880(1) 26(1)
C(38) -2643(3) 5485(2) 3390(1) 26(1)
C(39) -1864(3) 6152(2) 3041(1) 24(1)
C(40) -531(3) 6735(2) 3179(1) 21(1)
N(1) 9353(2) -534(2) 2685(1) 26(1)
C(2) 8668(3) -107(2) 3005(1) 20(1)
C(3) 7769(3) 409(2) 3402(1) 20(1)
C(4) 6839(3) -241(2) 3763(1) 19(1)
C(5) 6642(3) -1414(2) 3827(1) 22(1)
C(6) 5685(3) -1785(2) 4216(1) 22(1)
C(7) 4936(3) -1001(2) 4526(1) 23(1)
C(8) 5142(3) 179(2) 4467(1) 22(1)
C(9) 6107(3) 541(2) 4083(1) 19(1)
C(10) 6561(3) 1770(2) 3924(1) 18(1)
C(11) 7686(3) 1553(2) 3486(1) 20(1)
C(12) 8527(3) 2495(2) 3227(1) 26(1)
C(13) 7395(3) 2350(2) 4342(1) 22(1)
N(14) 8053(2) 2808(2) 4659(1) 29(1)
C(15) 5142(3) 2484(2) 3771(1) 20(1)
C(16) 4673(3) 2526(2) 3270(1) 22(1)
C(17) 3349(3) 3132(2) 3136(1) 26(1)
C(18) 2492(3) 3678(2) 3505(1) 28(1)
C(19) 2943(3) 3624(2) 4008(1) 28(1)
C(20) 4278(3) 3038(2) 4141(1) 23(1)
________________________________________________________________________________
Table 4. Bond lengths [Å] and angles [°] for tcd148.
_____________________________________________________
N(21)-C(22) 1.146(3) C(3)-C(11) 1.351(3)
C(22)-C(23) 1.440(3) C(3)-C(4) 1.462(3)
C(23)-C(31) 1.343(3) C(4)-C(5) 1.385(3)
C(23)-C(24) 1.468(3) C(4)-C(9) 1.397(3)
C(24)-C(25) 1.387(3) C(5)-C(6) 1.392(3)
C(24)-C(29) 1.394(3) C(5)-H(5A) 0.9500
C(25)-C(26) 1.395(3) C(6)-C(7) 1.389(3)
C(25)-H(25A) 0.9500 C(6)-H(6A) 0.9500
C(26)-C(27) 1.389(3) C(7)-C(8) 1.393(3)
C(26)-H(26A) 0.9500 C(7)-H(7A) 0.9500
C(27)-C(28) 1.401(3) C(8)-C(9) 1.381(3)
C(27)-H(27A) 0.9500 C(8)-H(8A) 0.9500
C(28)-C(29) 1.377(3) C(9)-C(10) 1.541(3)
C(28)-H(28A) 0.9500 C(10)-C(13) 1.482(3)
C(29)-C(30) 1.538(3) C(10)-C(11) 1.538(3)
C(30)-C(33) 1.484(3) C(10)-C(15) 1.542(3)
C(30)-C(35) 1.533(3) C(11)-C(12) 1.484(3)
C(30)-C(31) 1.542(3) C(12)-H(12A) 0.9800
C(31)-C(32) 1.486(3) C(12)-H(12B) 0.9800
C(32)-H(32A) 0.9800 C(12)-H(12C) 0.9800
C(32)-H(32B) 0.9800 C(13)-N(14) 1.147(3)
C(32)-H(32C) 0.9800 C(15)-C(16) 1.387(3)
C(33)-N(34) 1.146(3) C(15)-C(20) 1.392(3)
C(35)-C(40) 1.390(3) C(16)-C(17) 1.396(3)
C(35)-C(36) 1.393(3) C(16)-H(16A) 0.9500
C(36)-C(37) 1.391(3) C(17)-C(18) 1.381(4)
C(36)-H(36A) 0.9500 C(17)-H(17A) 0.9500
C(37)-C(38) 1.383(3) C(18)-C(19) 1.386(4)
C(37)-H(37A) 0.9500 C(18)-H(18A) 0.9500
C(38)-C(39) 1.384(3) C(19)-C(20) 1.393(3)
C(38)-H(38A) 0.9500 C(19)-H(19A) 0.9500
C(39)-C(40) 1.393(3) C(20)-H(20A) 0.9500
C(39)-H(39A) 0.9500
C(40)-H(40A) 0.9500 N(21)-C(22)-C(23) 178.5(2)
N(1)-C(2) 1.148(3) C(31)-C(23)-C(22) 124.6(2)
C(2)-C(3) 1.438(3) C(31)-C(23)-C(24) 111.90(19)
C(22)-C(23)-C(24) 123.49(19) C(37)-C(36)-C(35) 120.4(2)
C(25)-C(24)-C(29) 120.7(2) C(37)-C(36)-H(36A) 119.8
C(25)-C(24)-C(23) 131.4(2) C(35)-C(36)-H(36A) 119.8
C(29)-C(24)-C(23) 107.83(18) C(38)-C(37)-C(36) 120.1(2)
C(24)-C(25)-C(26) 117.9(2) C(38)-C(37)-H(37A) 120.0
C(24)-C(25)-H(25A) 121.0 C(36)-C(37)-H(37A) 120.0
C(26)-C(25)-H(25A) 121.0 C(37)-C(38)-C(39) 119.8(2)
C(27)-C(26)-C(25) 121.1(2) C(37)-C(38)-H(38A) 120.1
C(27)-C(26)-H(26A) 119.4 C(39)-C(38)-H(38A) 120.1
C(25)-C(26)-H(26A) 119.4 C(38)-C(39)-C(40) 120.4(2)
C(26)-C(27)-C(28) 120.7(2) C(38)-C(39)-H(39A) 119.8
C(26)-C(27)-H(27A) 119.7 C(40)-C(39)-H(39A) 119.8
C(28)-C(27)-H(27A) 119.7 C(35)-C(40)-C(39) 120.0(2)
C(29)-C(28)-C(27) 117.8(2) C(35)-C(40)-H(40A) 120.0
C(29)-C(28)-H(28A) 121.1 C(39)-C(40)-H(40A) 120.0
C(27)-C(28)-H(28A) 121.1 N(1)-C(2)-C(3) 178.3(2)
C(28)-C(29)-C(24) 121.7(2) C(11)-C(3)-C(2) 124.0(2)
C(28)-C(29)-C(30) 129.1(2) C(11)-C(3)-C(4) 111.84(19)
C(24)-C(29)-C(30) 109.17(18) C(2)-C(3)-C(4) 124.13(19)
C(33)-C(30)-C(35) 110.00(18) C(5)-C(4)-C(9) 120.8(2)
C(33)-C(30)-C(29) 108.40(17) C(5)-C(4)-C(3) 131.1(2)
C(35)-C(30)-C(29) 113.49(18) C(9)-C(4)-C(3) 108.16(18)
C(33)-C(30)-C(31) 108.29(18) C(4)-C(5)-C(6) 118.0(2)
C(35)-C(30)-C(31) 114.02(17) C(4)-C(5)-H(5A) 121.0
C(29)-C(30)-C(31) 102.22(17) C(6)-C(5)-H(5A) 121.0
C(23)-C(31)-C(32) 129.2(2) C(7)-C(6)-C(5) 120.8(2)
C(23)-C(31)-C(30) 108.83(19) C(7)-C(6)-H(6A) 119.6
C(32)-C(31)-C(30) 121.93(19) C(5)-C(6)-H(6A) 119.6
C(31)-C(32)-H(32A) 109.5 C(6)-C(7)-C(8) 121.4(2)
C(31)-C(32)-H(32B) 109.5 C(6)-C(7)-H(7A) 119.3
H(32A)-C(32)-H(32B) 109.5 C(8)-C(7)-H(7A) 119.3
C(31)-C(32)-H(32C) 109.5 C(9)-C(8)-C(7) 117.5(2)
H(32A)-C(32)-H(32C) 109.5 C(9)-C(8)-H(8A) 121.2
H(32B)-C(32)-H(32C) 109.5 C(7)-C(8)-H(8A) 121.2
N(34)-C(33)-C(30) 179.3(2) C(8)-C(9)-C(4) 121.5(2)
C(40)-C(35)-C(36) 119.3(2) C(8)-C(9)-C(10) 129.7(2)
C(40)-C(35)-C(30) 120.0(2) C(4)-C(9)-C(10) 108.79(18)
C(36)-C(35)-C(30) 120.62(19) C(13)-C(10)-C(11) 108.84(18)
C(13)-C(10)-C(9) 110.15(17) C(20)-C(15)-C(10) 119.82(19)
C(11)-C(10)-C(9) 102.47(17) C(15)-C(16)-C(17) 120.1(2)
C(13)-C(10)-C(15) 110.10(18) C(15)-C(16)-H(16A) 119.9
C(11)-C(10)-C(15) 113.60(17) C(17)-C(16)-H(16A) 119.9
C(9)-C(10)-C(15) 111.43(18) C(18)-C(17)-C(16) 120.1(2)
C(3)-C(11)-C(12) 128.7(2) C(18)-C(17)-H(17A) 120.0
C(3)-C(11)-C(10) 108.67(19) C(16)-C(17)-H(17A) 120.0
C(12)-C(11)-C(10) 122.62(19) C(17)-C(18)-C(19) 120.1(2)
C(11)-C(12)-H(12A) 109.5 C(17)-C(18)-H(18A) 120.0
C(11)-C(12)-H(12B) 109.5 C(19)-C(18)-H(18A) 120.0
H(12A)-C(12)-H(12B) 109.5 C(18)-C(19)-C(20) 120.1(2)
C(11)-C(12)-H(12C) 109.5 C(18)-C(19)-H(19A) 120.0
H(12A)-C(12)-H(12C) 109.5 C(20)-C(19)-H(19A) 120.0
H(12B)-C(12)-H(12C) 109.5 C(15)-C(20)-C(19) 120.0(2)
N(14)-C(13)-C(10) 178.9(2) C(15)-C(20)-H(20A) 120.0
C(16)-C(15)-C(20) 119.7(2) C(19)-C(20)-H(20A) 120.0
C(16)-C(15)-C(10) 120.42(19)
_____________________________________________________________
Table 5. Anisotropic displacement parameters (Å2x 103) for tcd148. The anisotropic
displacement factor exponent takes the form: -2π2[ h2 a*2U11 + ... + 2 h k a* b* U12 ]
______________________________________________________________________________
U11 U22 U33 U23 U13 U12
______________________________________________________________________________
N(21) 24(1) 28(1) 26(1) 4(1) 2(1) -2(1)
C(22) 18(1) 21(1) 22(1) 0(1) -3(1) 2(1)
C(23) 14(1) 22(1) 18(1) 0(1) -2(1) -1(1)
C(24) 13(1) 21(1) 19(1) 2(1) -3(1) -1(1)
C(25) 16(1) 19(1) 25(1) 3(1) -2(1) -3(1)
C(26) 19(1) 19(1) 28(1) -3(1) -2(1) -1(1)
C(27) 18(1) 25(1) 24(1) -4(1) 1(1) 2(1)
C(28) 20(1) 20(1) 20(1) 0(1) 1(1) -2(1)
C(29) 15(1) 17(1) 19(1) 0(1) -4(1) -2(1)
C(30) 17(1) 19(1) 18(1) 1(1) 0(1) 0(1)
C(31) 15(1) 24(1) 18(1) 2(1) -1(1) 0(1)
C(32) 22(1) 22(1) 25(1) 0(1) 3(1) 3(1)
C(33) 21(1) 17(1) 23(1) 0(1) 1(1) -2(1)
N(34) 27(1) 24(1) 31(1) 3(1) -6(1) -2(1)
C(35) 16(1) 16(1) 23(1) -4(1) 1(1) 2(1)
C(36) 25(1) 21(1) 24(1) 0(1) 0(1) 0(1)
C(37) 24(1) 19(1) 37(1) 1(1) 4(1) -3(1)
C(38) 20(1) 19(1) 41(1) -6(1) -4(1) 2(1)
C(39) 21(1) 22(1) 28(1) -5(1) -4(1) 6(1)
C(40) 22(1) 18(1) 24(1) -1(1) 1(1) 4(1)
N(1) 26(1) 27(1) 26(1) 0(1) 3(1) 2(1)
C(2) 17(1) 21(1) 24(1) 0(1) -2(1) -3(1)
C(3) 16(1) 24(1) 19(1) -2(1) -2(1) 0(1)
C(4) 16(1) 21(1) 19(1) -1(1) -4(1) 2(1)
C(5) 18(1) 21(1) 25(1) -3(1) -2(1) -1(1)
C(6) 19(1) 19(1) 28(1) 3(1) -5(1) -2(1)
C(7) 21(1) 27(1) 21(1) 4(1) -1(1) -2(1)
C(8) 21(1) 24(1) 20(1) -2(1) -1(1) 2(1)
C(9) 16(1) 19(1) 21(1) 0(1) -4(1) -1(1)
C(10) 19(1) 17(1) 19(1) -2(1) 0(1) 1(1)
C(11) 18(1) 23(1) 19(1) -2(1) -3(1) 0(1)
C(12) 25(1) 25(1) 28(1) -3(1) 4(1) -3(1)
C(13) 22(1) 20(1) 24(1) 0(1) 2(1) 4(1)
N(14) 31(1) 26(1) 30(1) -5(1) -5(1) 2(1)
C(15) 19(1) 15(1) 25(1) 1(1) 1(1) -3(1)
C(16) 20(1) 19(1) 27(1) 3(1) 2(1) -2(1)
C(17) 23(1) 24(1) 32(1) 8(1) -4(1) -3(1)
C(18) 18(1) 17(1) 49(2) 4(1) -2(1) 1(1)
C(19) 24(1) 18(1) 43(1) -4(1) 6(1) 2(1)
C(20) 24(1) 18(1) 28(1) -3(1) 1(1) 0(1)
______________________________________________________________________________
Table 6. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å2x 10 3)
for tcd148.
________________________________________________________________________________
x y z U(eq)
________________________________________________________________________________

H(25A) 2263 11066 3636 24

H(26A) 787 11634 4338 26
H(27A) -499 10280 4828 27
H(28A) -331 8304 4631 24
H(32A) 3867 6119 3345 35
H(32B) 4125 6974 2878 35
H(32C) 2595 6214 2910 35
H(36A) -356 5873 4352 28
H(37A) -2632 4943 4122 32
H(38A) -3555 5093 3295 32
H(39A) -2240 6212 2704 28
H(40A) -8 7199 2938 25
H(5A) 7145 -1948 3611 26
H(6A) 5542 -2586 4270 27
H(7A) 4269 -1275 4784 28
H(8A) 4638 714 4682 26
H(12A) 9092 2948 3479 39
H(12B) 7793 2991 3050 39
H(12C) 9251 2167 2982 39
H(16A) 5252 2141 3016 26
H(17A) 3038 3170 2792 31
H(18A) 1592 4091 3414 33
H(19A) 2341 3987 4262 34
H(20A) 4599 3016 4485 28
________________________________________________________________________________
Table 7. Torsion angles [°] for tcd148.
________________________________________________________________
C(31)-C(23)-C(24)-C(25) 175.6(2) C(31)-C(30)-C(35)-C(36) 153.8(2)
C(22)-C(23)-C(24)-C(25) -2.0(4) C(40)-C(35)-C(36)-C(37) -1.1(3)
C(31)-C(23)-C(24)-C(29) -0.4(3) C(30)-C(35)-C(36)-C(37) 175.8(2)
C(22)-C(23)-C(24)-C(29) -177.9(2) C(35)-C(36)-C(37)-C(38) 1.6(3)
C(29)-C(24)-C(25)-C(26) 0.3(3) C(36)-C(37)-C(38)-C(39) -0.8(3)
C(23)-C(24)-C(25)-C(26) -175.2(2) C(37)-C(38)-C(39)-C(40) -0.4(3)
C(24)-C(25)-C(26)-C(27) -0.6(3) C(36)-C(35)-C(40)-C(39) 0.0(3)
C(25)-C(26)-C(27)-C(28) 0.2(3) C(30)-C(35)-C(40)-C(39) -177.02(19)
C(26)-C(27)-C(28)-C(29) 0.4(3) C(38)-C(39)-C(40)-C(35) 0.8(3)
C(27)-C(28)-C(29)-C(24) -0.6(3) C(11)-C(3)-C(4)-C(5) -177.2(2)
C(27)-C(28)-C(29)-C(30) 176.6(2) C(2)-C(3)-C(4)-C(5) 2.7(4)
C(25)-C(24)-C(29)-C(28) 0.3(3) C(11)-C(3)-C(4)-C(9) 1.4(3)
C(23)-C(24)-C(29)-C(28) 176.76(19) C(2)-C(3)-C(4)-C(9) -178.7(2)
C(25)-C(24)-C(29)-C(30) -177.4(2) C(9)-C(4)-C(5)-C(6) 0.5(3)
C(23)-C(24)-C(29)-C(30) -1.0(2) C(3)-C(4)-C(5)-C(6) 178.9(2)
C(28)-C(29)-C(30)-C(33) -61.5(3) C(4)-C(5)-C(6)-C(7) 0.9(3)
C(24)-C(29)-C(30)-C(33) 116.0(2) C(5)-C(6)-C(7)-C(8) -1.5(3)
C(28)-C(29)-C(30)-C(35) 61.0(3) C(6)-C(7)-C(8)-C(9) 0.7(3)
C(24)-C(29)-C(30)-C(35) -121.5(2) C(7)-C(8)-C(9)-C(4) 0.7(3)
C(28)-C(29)-C(30)-C(31) -175.8(2) C(7)-C(8)-C(9)-C(10) 180.0(2)
C(24)-C(29)-C(30)-C(31) 1.7(2) C(5)-C(4)-C(9)-C(8) -1.3(3)
C(22)-C(23)-C(31)-C(32) 1.6(4) C(3)-C(4)-C(9)-C(8) 180.0(2)
C(24)-C(23)-C(31)-C(32) -175.9(2) C(5)-C(4)-C(9)-C(10) 179.3(2)
C(22)-C(23)-C(31)-C(30) 179.04(19) C(3)-C(4)-C(9)-C(10) 0.5(2)
C(24)-C(23)-C(31)-C(30) 1.5(3) C(8)-C(9)-C(10)-C(13) 63.0(3)
C(33)-C(30)-C(31)-C(23) -116.3(2) C(4)-C(9)-C(10)-C(13) -117.6(2)
C(35)-C(30)-C(31)-C(23) 120.9(2) C(8)-C(9)-C(10)-C(11) 178.7(2)
C(29)-C(30)-C(31)-C(23) -1.9(2) C(4)-C(9)-C(10)-C(11) -1.9(2)
C(33)-C(30)-C(31)-C(32) 61.4(3) C(8)-C(9)-C(10)-C(15) -59.5(3)
C(35)-C(30)-C(31)-C(32) -61.4(3) C(4)-C(9)-C(10)-C(15) 119.9(2)
C(29)-C(30)-C(31)-C(32) 175.7(2) C(2)-C(3)-C(11)-C(12) -4.2(4)
C(33)-C(30)-C(35)-C(40) -151.1(2) C(4)-C(3)-C(11)-C(12) 175.7(2)
C(29)-C(30)-C(35)-C(40) 87.3(2) C(2)-C(3)-C(11)-C(10) 177.46(19)
C(31)-C(30)-C(35)-C(40) -29.2(3) C(4)-C(3)-C(11)-C(10) -2.6(3)
C(33)-C(30)-C(35)-C(36) 32.0(3) C(13)-C(10)-C(11)-C(3) 119.4(2)
C(29)-C(30)-C(35)-C(36) -89.7(2) C(9)-C(10)-C(11)-C(3) 2.8(2)
C(15)-C(10)-C(11)-C(3) -117.6(2) C(9)-C(10)-C(15)-C(20) 84.1(2)
C(13)-C(10)-C(11)-C(12) -59.1(3) C(20)-C(15)-C(16)-C(17) 0.7(3)
C(9)-C(10)-C(11)-C(12) -175.7(2) C(10)-C(15)-C(16)-C(17) 177.20(19)
C(15)-C(10)-C(11)-C(12) 64.0(3) C(15)-C(16)-C(17)-C(18) -0.9(3)
C(13)-C(10)-C(15)-C(16) 145.2(2) C(16)-C(17)-C(18)-C(19) -0.1(3)
C(11)-C(10)-C(15)-C(16) 22.8(3) C(17)-C(18)-C(19)-C(20) 1.2(3)
C(9)-C(10)-C(15)-C(16) -92.3(2) C(16)-C(15)-C(20)-C(19) 0.4(3)
C(13)-C(10)-C(15)-C(20) -38.4(3) C(10)-C(15)-C(20)-C(19) -176.05(19)
C(11)-C(10)-C(15)-C(20) -160.7(2) C(18)-C(19)-C(20)-C(15) -1.4(3)
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