Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800019620/ob6017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800019620/ob6017Isup2.hkl |
CCDC reference: 155888
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.109
- Data-to-parameter ratio = 11.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from an ethanol solution.
All H atoms were included in the refinement at calculated positions as riding models, with C—H set to 0.95 Å, except for the indole NH group, which was located on difference syntheses and for which both positional and displacement parameters were refined. The unit cell for (I) was initially determined as orthorhombic C [a = 21.5564 (8), b = 32.161 (1), c = 6.8627 (4) Å], but it was not possible to obtain a solution in this setting. The structure was eventually solved as primitive monoclinic in P21/n. However, the refinement was poor, R1 was around 26% and the ellipsoids were unreasonable. It was noted that a and c were approximately equal in length and the structure was refined as a pseudo-merohedral twin (twin law: 001, 010, 100). This resulted in a final R1 value of 4.4%, sensible ellipsoids and a twin component of 0.46 (1).
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The mlecular configuration and atom-numbering scheme for (I), showing 30% probability ellipsoids. |
C32H22N6 | Dx = 1.370 Mg m−3 |
Mr = 490.56 | Melting point: 484-487 K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 19.3539 (8) Å | Cell parameters from 8137 reflections |
b = 6.8609 (3) Å | θ = 2.9–30.5° |
c = 19.3579 (8) Å | µ = 0.08 mm−1 |
β = 112.325 (2)° | T = 150 K |
V = 2377.77 (17) Å3 | Prism, colourless |
Z = 4 | 0.28 × 0.12 × 0.04 mm |
F(000) = 1024 |
Enraf Nonius KappaCCD area detector diffractometer | 4179 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 3199 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 9.091 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ϕ and ω scans | h = −22→22 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −8→8 |
Tmin = 0.977, Tmax = 0.997 | l = −23→21 |
11617 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max = 0.001 |
4179 reflections | Δρmax = 0.22 e Å−3 |
353 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0087 (13) |
C32H22N6 | V = 2377.77 (17) Å3 |
Mr = 490.56 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 19.3539 (8) Å | µ = 0.08 mm−1 |
b = 6.8609 (3) Å | T = 150 K |
c = 19.3579 (8) Å | 0.28 × 0.12 × 0.04 mm |
β = 112.325 (2)° |
Enraf Nonius KappaCCD area detector diffractometer | 4179 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 3199 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.997 | Rint = 0.062 |
11617 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | Δρmax = 0.22 e Å−3 |
4179 reflections | Δρmin = −0.21 e Å−3 |
353 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 1.4708 (0.0272) x - 6.6299 (0.0025) y + 4.9610 (0.0258) z = 3.5277 (0.0290) * 0.0035 (0.0016) N1A * 0.0001 (0.0017) C2A * -0.0035 (0.0017) C3A * 0.0055 (0.0016) C4A * -0.0056 (0.0016) C13A Rms deviation of fitted atoms = 0.0041 - 1.7517 (0.0186) x - 5.4799 (0.0046) y + 11.3177 (0.0171) z = 11.1609 (0.0200) Angle to previous plane (with approximate e.s.d.) = 22.34 (0.12) * -0.0027 (0.0018) N14A * 0.0092 (0.0018) C15A * -0.0064 (0.0018) C16A * -0.0023 (0.0018) C17A * 0.0085 (0.0019) C18A * -0.0063 (0.0019) C19A Rms deviation of fitted atoms = 0.0064 7.2754 (0.0241) x + 6.3302 (0.0036) y - 1.2228 (0.0263) z = 1.1150 (0.0161) Angle to previous plane (with approximate e.s.d.) = 43.97 (0.09) * 0.0083 (0.0015) N1B * -0.0061 (0.0016) C2B * 0.0017 (0.0016) C3B * 0.0033 (0.0015) C4B * -0.0072 (0.0016) C13B Rms deviation of fitted atoms = 0.0058 11.0024 (0.0188) x + 5.5454 (0.0049) y - 1.4334 (0.0198) z = 1.4377 (0.0162) Angle to previous plane (with approximate e.s.d.) = 13.43 (0.14) * -0.0007 (0.0018) N14B * 0.0056 (0.0020) C15B * -0.0041 (0.0020) C16B * -0.0018 (0.0018) C17B * 0.0065 (0.0019) C18B * -0.0054 (0.0020) C19B Rms deviation of fitted atoms = 0.0045 |
x | y | z | Uiso*/Ueq | ||
N1A | 0.15848 (12) | 0.2457 (4) | 1.08718 (12) | 0.0274 (5) | |
H1A | 0.1606 (16) | 0.211 (5) | 1.0421 (17) | 0.046 (9)* | |
C2A | 0.21773 (15) | 0.2826 (4) | 1.15331 (14) | 0.0296 (6) | |
C3A | 0.18996 (15) | 0.3292 (4) | 1.20662 (15) | 0.0326 (7) | |
H3A | 0.2185 | 0.3618 | 1.2572 | 0.039* | |
C4A | 0.11103 (15) | 0.3200 (4) | 1.17275 (14) | 0.0307 (7) | |
C5A | 0.05249 (16) | 0.3459 (4) | 1.19924 (16) | 0.0368 (7) | |
H5A | 0.0637 | 0.3785 | 1.2500 | 0.044* | |
C6A | −0.01954 (17) | 0.3237 (4) | 1.15132 (17) | 0.0395 (7) | |
H6A | −0.0584 | 0.3337 | 1.1698 | 0.047* | |
C7A | −0.03836 (16) | 0.2855 (4) | 1.07322 (16) | 0.0328 (7) | |
C8A | −0.11228 (16) | 0.2788 (4) | 1.02123 (17) | 0.0391 (8) | |
H8A | −0.1527 | 0.2936 | 1.0372 | 0.047* | |
C9A | −0.12561 (16) | 0.2508 (5) | 0.94751 (18) | 0.0422 (8) | |
H9A | −0.1753 | 0.2470 | 0.9114 | 0.051* | |
C10A | −0.06551 (16) | 0.2281 (4) | 0.92620 (17) | 0.0385 (7) | |
H10A | −0.0760 | 0.2090 | 0.8746 | 0.046* | |
N11A | 0.00560 (13) | 0.2309 (3) | 0.97225 (12) | 0.0329 (6) | |
C12A | 0.01843 (15) | 0.2601 (4) | 1.04585 (15) | 0.0295 (7) | |
C13A | 0.09330 (15) | 0.2696 (4) | 1.09789 (14) | 0.0273 (6) | |
N14A | 0.44505 (12) | 0.2436 (4) | 1.17273 (12) | 0.0325 (6) | |
C15A | 0.42470 (15) | 0.3467 (4) | 1.22055 (14) | 0.0333 (7) | |
H15A | 0.4627 | 0.4125 | 1.2601 | 0.040* | |
C16A | 0.35186 (14) | 0.3638 (4) | 1.21620 (14) | 0.0317 (6) | |
H16A | 0.3407 | 0.4420 | 1.2511 | 0.038* | |
C17A | 0.29513 (14) | 0.2652 (4) | 1.16004 (13) | 0.0268 (6) | |
C18A | 0.31586 (14) | 0.1556 (4) | 1.11112 (14) | 0.0290 (6) | |
H18A | 0.2793 | 0.0840 | 1.0723 | 0.035* | |
C19A | 0.38967 (14) | 0.1501 (4) | 1.11860 (14) | 0.0319 (7) | |
H19A | 0.4020 | 0.0760 | 1.0834 | 0.038* | |
N1B | 0.08954 (13) | 0.2008 (3) | 0.65358 (12) | 0.0275 (5) | |
H1B | 0.0473 (18) | 0.231 (5) | 0.6572 (17) | 0.054 (10)* | |
C2B | 0.15420 (14) | 0.1351 (4) | 0.71018 (14) | 0.0266 (6) | |
C3B | 0.20314 (14) | 0.0741 (4) | 0.67907 (14) | 0.0304 (6) | |
H3B | 0.2518 | 0.0238 | 0.7054 | 0.037* | |
C4B | 0.16844 (14) | 0.0991 (4) | 0.60068 (14) | 0.0293 (6) | |
C5B | 0.18996 (16) | 0.0619 (4) | 0.53947 (15) | 0.0339 (7) | |
H5B | 0.2380 | 0.0102 | 0.5477 | 0.041* | |
C6B | 0.14134 (16) | 0.1008 (4) | 0.46924 (16) | 0.0376 (7) | |
H6B | 0.1561 | 0.0767 | 0.4285 | 0.045* | |
C7B | 0.06835 (16) | 0.1771 (4) | 0.45472 (15) | 0.0319 (7) | |
C8B | 0.01579 (18) | 0.2151 (4) | 0.38216 (16) | 0.0389 (8) | |
H8B | 0.0285 | 0.1933 | 0.3400 | 0.047* | |
C9B | −0.05314 (17) | 0.2831 (4) | 0.37279 (16) | 0.0384 (8) | |
H9B | −0.0889 | 0.3100 | 0.3242 | 0.046* | |
C10B | −0.07059 (16) | 0.3125 (4) | 0.43517 (15) | 0.0359 (7) | |
H10B | −0.1194 | 0.3580 | 0.4274 | 0.043* | |
N11B | −0.02409 (12) | 0.2817 (3) | 0.50478 (11) | 0.0301 (6) | |
C12B | 0.04491 (15) | 0.2142 (4) | 0.51387 (15) | 0.0283 (6) | |
C13B | 0.09753 (15) | 0.1763 (4) | 0.58688 (14) | 0.0273 (6) | |
N14B | 0.17849 (12) | 0.1479 (3) | 0.93954 (12) | 0.0334 (6) | |
C15B | 0.22530 (15) | 0.0499 (4) | 0.91572 (14) | 0.0353 (7) | |
H15B | 0.2655 | −0.0182 | 0.9520 | 0.042* | |
C16B | 0.21956 (15) | 0.0408 (4) | 0.84310 (14) | 0.0341 (6) | |
H16B | 0.2544 | −0.0332 | 0.8303 | 0.041* | |
C17B | 0.16212 (14) | 0.1410 (4) | 0.78820 (14) | 0.0277 (6) | |
C18B | 0.11361 (16) | 0.2448 (4) | 0.81175 (14) | 0.0309 (7) | |
H18B | 0.0739 | 0.3171 | 0.7767 | 0.037* | |
C19B | 0.12297 (14) | 0.2434 (4) | 0.88622 (14) | 0.0313 (7) | |
H19B | 0.0882 | 0.3138 | 0.9005 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0270 (14) | 0.0283 (13) | 0.0270 (13) | 0.0002 (10) | 0.0106 (10) | −0.0021 (10) |
C2A | 0.0329 (16) | 0.0288 (16) | 0.0244 (14) | −0.0009 (12) | 0.0078 (12) | 0.0031 (11) |
C3A | 0.0380 (16) | 0.0334 (17) | 0.0259 (14) | 0.0034 (13) | 0.0116 (12) | 0.0010 (12) |
C4A | 0.0398 (17) | 0.0237 (16) | 0.0331 (15) | 0.0026 (12) | 0.0189 (13) | 0.0034 (12) |
C5A | 0.0466 (17) | 0.0343 (17) | 0.0368 (16) | 0.0054 (14) | 0.0241 (14) | 0.0044 (13) |
C6A | 0.0438 (18) | 0.0364 (18) | 0.0502 (18) | 0.0082 (14) | 0.0313 (15) | 0.0037 (15) |
C7A | 0.0362 (16) | 0.0236 (15) | 0.0452 (17) | 0.0015 (12) | 0.0229 (14) | 0.0035 (13) |
C8A | 0.0340 (18) | 0.0303 (17) | 0.059 (2) | −0.0013 (12) | 0.0238 (16) | 0.0022 (14) |
C9A | 0.0269 (18) | 0.0366 (18) | 0.058 (2) | 0.0002 (13) | 0.0102 (15) | 0.0006 (16) |
C10A | 0.0390 (19) | 0.0321 (17) | 0.0396 (16) | −0.0009 (14) | 0.0097 (14) | 0.0001 (14) |
N11A | 0.0347 (14) | 0.0298 (14) | 0.0321 (13) | −0.0023 (11) | 0.0101 (11) | −0.0007 (11) |
C12A | 0.0326 (17) | 0.0215 (14) | 0.0362 (16) | −0.0004 (12) | 0.0151 (13) | 0.0007 (12) |
C13A | 0.0311 (16) | 0.0234 (15) | 0.0294 (15) | 0.0017 (12) | 0.0138 (12) | 0.0035 (12) |
N14A | 0.0324 (14) | 0.0340 (14) | 0.0280 (12) | 0.0000 (11) | 0.0080 (10) | 0.0037 (11) |
C15A | 0.0342 (15) | 0.0339 (17) | 0.0271 (14) | −0.0020 (12) | 0.0063 (12) | 0.0006 (12) |
C16A | 0.0344 (15) | 0.0334 (16) | 0.0238 (13) | 0.0027 (13) | 0.0073 (11) | −0.0013 (12) |
C17A | 0.0284 (16) | 0.0279 (15) | 0.0210 (13) | 0.0048 (11) | 0.0060 (12) | 0.0053 (11) |
C18A | 0.0288 (15) | 0.0327 (16) | 0.0229 (13) | 0.0006 (12) | 0.0069 (11) | −0.0002 (12) |
C19A | 0.0328 (16) | 0.0318 (17) | 0.0277 (14) | 0.0020 (13) | 0.0078 (12) | 0.0021 (12) |
N1B | 0.0265 (14) | 0.0289 (13) | 0.0274 (13) | 0.0002 (10) | 0.0104 (11) | −0.0030 (10) |
C2B | 0.0275 (14) | 0.0256 (14) | 0.0266 (13) | −0.0026 (12) | 0.0102 (11) | −0.0011 (12) |
C3B | 0.0280 (14) | 0.0259 (15) | 0.0340 (14) | −0.0016 (11) | 0.0078 (12) | −0.0029 (12) |
C4B | 0.0310 (14) | 0.0233 (15) | 0.0353 (15) | −0.0044 (11) | 0.0145 (11) | −0.0051 (12) |
C5B | 0.0374 (15) | 0.0284 (16) | 0.0408 (16) | −0.0031 (13) | 0.0205 (13) | −0.0059 (13) |
C6B | 0.0527 (18) | 0.0301 (16) | 0.0396 (16) | −0.0096 (15) | 0.0283 (15) | −0.0109 (14) |
C7B | 0.0449 (18) | 0.0229 (15) | 0.0324 (15) | −0.0088 (13) | 0.0196 (13) | −0.0047 (12) |
C8B | 0.058 (2) | 0.0286 (17) | 0.0328 (16) | −0.0145 (15) | 0.0209 (15) | −0.0050 (13) |
C9B | 0.052 (2) | 0.0271 (16) | 0.0300 (16) | −0.0106 (14) | 0.0086 (14) | −0.0018 (12) |
C10B | 0.0393 (17) | 0.0293 (17) | 0.0333 (16) | −0.0069 (12) | 0.0072 (13) | −0.0019 (12) |
N11B | 0.0361 (14) | 0.0235 (13) | 0.0282 (12) | −0.0043 (10) | 0.0094 (10) | 0.0004 (9) |
C12B | 0.0372 (16) | 0.0167 (14) | 0.0327 (15) | −0.0053 (11) | 0.0150 (12) | −0.0004 (11) |
C13B | 0.0334 (15) | 0.0237 (15) | 0.0288 (14) | −0.0050 (12) | 0.0163 (12) | −0.0039 (11) |
N14B | 0.0330 (13) | 0.0363 (14) | 0.0276 (12) | −0.0008 (11) | 0.0078 (11) | 0.0007 (11) |
C15B | 0.0344 (15) | 0.0349 (17) | 0.0314 (15) | 0.0064 (13) | 0.0068 (12) | 0.0035 (13) |
C16B | 0.0371 (15) | 0.0313 (16) | 0.0325 (15) | 0.0063 (13) | 0.0118 (12) | −0.0003 (13) |
C17B | 0.0270 (14) | 0.0236 (15) | 0.0305 (14) | −0.0046 (12) | 0.0088 (12) | −0.0013 (12) |
C18B | 0.0285 (15) | 0.0322 (16) | 0.0276 (14) | 0.0028 (12) | 0.0057 (12) | 0.0012 (12) |
C19B | 0.0261 (15) | 0.0345 (16) | 0.0316 (15) | 0.0023 (12) | 0.0090 (13) | −0.0027 (13) |
N1A—C2A | 1.379 (3) | N1B—C13B | 1.368 (3) |
N1A—C13A | 1.364 (3) | N1B—C2B | 1.388 (3) |
N1A—H1A | 0.92 (3) | N1B—H1B | 0.87 (3) |
C2A—C3A | 1.370 (4) | C2B—C3B | 1.367 (4) |
C2A—C17A | 1.458 (4) | C2B—C17B | 1.459 (4) |
C3A—C4A | 1.417 (4) | C3B—C4B | 1.417 (4) |
C3A—H3A | 0.95 | C3B—H3B | 0.95 |
C4A—C13A | 1.400 (4) | C4B—C13B | 1.399 (4) |
C4A—C5A | 1.421 (3) | C4B—C5B | 1.420 (3) |
C5A—C6A | 1.358 (4) | C5B—C6B | 1.354 (4) |
C5A—H5A | 0.95 | C5B—H5B | 0.95 |
C6A—C7A | 1.438 (4) | C6B—C7B | 1.431 (4) |
C6A—H6A | 0.95 | C6B—H6B | 0.95 |
C7A—C12A | 1.401 (4) | C7B—C12B | 1.406 (4) |
C7A—C8A | 1.403 (4) | C7B—C8B | 1.411 (4) |
C8A—C9A | 1.364 (4) | C8B—C9B | 1.359 (4) |
C8A—H8A | 0.95 | C8B—H8B | 0.95 |
C9A—C10A | 1.382 (4) | C9B—C10B | 1.387 (4) |
C9A—H9A | 0.95 | C9B—H9B | 0.95 |
C10A—N11A | 1.326 (3) | C10B—N11B | 1.323 (3) |
C10A—H10A | 0.95 | C10B—H10B | 0.95 |
N11A—C12A | 1.365 (3) | N11B—C12B | 1.360 (4) |
C12A—C13A | 1.418 (4) | C12B—C13B | 1.417 (4) |
N14A—C15A | 1.338 (4) | N14B—C19B | 1.344 (3) |
N14A—C19A | 1.343 (3) | N14B—C15B | 1.343 (3) |
C15A—C16A | 1.385 (4) | C15B—C16B | 1.369 (4) |
C15A—H15A | 0.95 | C15B—H15B | 0.95 |
C16A—C17A | 1.392 (4) | C16B—C17B | 1.393 (4) |
C16A—H16A | 0.95 | C16B—H16B | 0.95 |
C17A—C18A | 1.383 (4) | C17B—C18B | 1.386 (4) |
C18A—C19A | 1.381 (4) | C18B—C19B | 1.383 (4) |
C18A—H18A | 0.95 | C18B—H18B | 0.95 |
C19A—H19A | 0.95 | C19B—H19B | 0.95 |
C2A—N1A—C13A | 109.1 (2) | C13B—N1B—C2B | 108.3 (2) |
C2A—N1A—H1A | 127.4 (18) | C13B—N1B—H1B | 123 (2) |
C13A—N1A—H1A | 123.5 (18) | C2B—N1B—H1B | 127 (2) |
C3A—C2A—N1A | 108.4 (2) | C3B—C2B—N1B | 108.6 (2) |
C3A—C2A—C17A | 129.4 (2) | C3B—C2B—C17B | 130.3 (2) |
N1A—C2A—C17A | 122.1 (2) | N1B—C2B—C17B | 121.1 (2) |
C2A—C3A—C4A | 107.7 (2) | C2B—C3B—C4B | 108.0 (2) |
C2A—C3A—H3A | 126.2 | C2B—C3B—H3B | 126.0 |
C4A—C3A—H3A | 126.2 | C4B—C3B—H3B | 126.0 |
C13A—C4A—C3A | 106.7 (2) | C13B—C4B—C5B | 119.1 (2) |
C13A—C4A—C5A | 119.3 (3) | C13B—C4B—C3B | 106.4 (2) |
C3A—C4A—C5A | 134.0 (3) | C5B—C4B—C3B | 134.6 (2) |
C6A—C5A—C4A | 119.5 (3) | C6B—C5B—C4B | 119.3 (3) |
C6A—C5A—H5A | 120.3 | C6B—C5B—H5B | 120.3 |
C4A—C5A—H5A | 120.3 | C4B—C5B—H5B | 120.3 |
C5A—C6A—C7A | 121.5 (3) | C5B—C6B—C7B | 121.8 (3) |
C5A—C6A—H6A | 119.2 | C5B—C6B—H6B | 119.1 |
C7A—C6A—H6A | 119.2 | C7B—C6B—H6B | 119.1 |
C12A—C7A—C8A | 117.2 (3) | C12B—C7B—C8B | 116.3 (3) |
C12A—C7A—C6A | 119.9 (3) | C12B—C7B—C6B | 120.4 (2) |
C8A—C7A—C6A | 122.8 (3) | C8B—C7B—C6B | 123.2 (3) |
C9A—C8A—C7A | 119.4 (3) | C9B—C8B—C7B | 119.8 (3) |
C9A—C8A—H8A | 120.3 | C9B—C8B—H8B | 120.1 |
C7A—C8A—H8A | 120.3 | C7B—C8B—H8B | 120.1 |
C8A—C9A—C10A | 118.8 (3) | C8B—C9B—C10B | 119.0 (3) |
C8A—C9A—H9A | 120.6 | C8B—C9B—H9B | 120.5 |
C10A—C9A—H9A | 120.6 | C10B—C9B—H9B | 120.5 |
N11A—C10A—C9A | 125.0 (3) | N11B—C10B—C9B | 124.6 (3) |
N11A—C10A—H10A | 117.5 | N11B—C10B—H10B | 117.7 |
C9A—C10A—H10A | 117.5 | C9B—C10B—H10B | 117.7 |
C10A—N11A—C12A | 115.8 (3) | C10B—N11B—C12B | 116.2 (2) |
N11A—C12A—C7A | 123.7 (3) | N11B—C12B—C7B | 124.1 (2) |
N11A—C12A—C13A | 118.7 (2) | N11B—C12B—C13B | 119.3 (2) |
C7A—C12A—C13A | 117.5 (2) | C7B—C12B—C13B | 116.5 (3) |
N1A—C13A—C4A | 108.1 (2) | N1B—C13B—C4B | 108.7 (2) |
N1A—C13A—C12A | 129.9 (2) | N1B—C13B—C12B | 128.5 (2) |
C4A—C13A—C12A | 122.0 (2) | C4B—C13B—C12B | 122.8 (2) |
C15A—N14A—C19A | 115.8 (2) | C19B—N14B—C15B | 115.3 (2) |
N14A—C15A—C16A | 124.3 (2) | N14B—C15B—C16B | 125.0 (3) |
N14A—C15A—H15A | 117.9 | N14B—C15B—H15B | 117.5 |
C16A—C15A—H15A | 117.9 | C16B—C15B—H15B | 117.5 |
C15A—C16A—C17A | 119.3 (3) | C15B—C16B—C17B | 119.4 (3) |
C15A—C16A—H16A | 120.4 | C15B—C16B—H16B | 120.3 |
C17A—C16A—H16A | 120.4 | C17B—C16B—H16B | 120.3 |
C18A—C17A—C16A | 116.8 (2) | C18B—C17B—C16B | 116.5 (2) |
C18A—C17A—C2A | 122.6 (2) | C18B—C17B—C2B | 122.4 (2) |
C16A—C17A—C2A | 120.6 (2) | C16B—C17B—C2B | 121.0 (2) |
C19A—C18A—C17A | 120.0 (2) | C19B—C18B—C17B | 120.1 (3) |
C19A—C18A—H18A | 120.0 | C19B—C18B—H18B | 119.9 |
C17A—C18A—H18A | 120.0 | C17B—C18B—H18B | 119.9 |
N14A—C19A—C18A | 123.8 (3) | N14B—C19B—C18B | 123.6 (3) |
N14A—C19A—H19A | 118.1 | N14B—C19B—H19B | 118.2 |
C18A—C19A—H19A | 118.1 | C18B—C19B—H19B | 118.2 |
C13A—N1A—C2A—C3A | 0.3 (3) | C13B—N1B—C2B—C3B | 1.4 (3) |
C13A—N1A—C2A—C17A | 178.8 (2) | C13B—N1B—C2B—C17B | −179.5 (2) |
N1A—C2A—C3A—C4A | 0.3 (3) | N1B—C2B—C3B—C4B | −0.8 (3) |
C17A—C2A—C3A—C4A | −177.9 (3) | C17B—C2B—C3B—C4B | −179.8 (3) |
C2A—C3A—C4A—C13A | −0.9 (3) | C2B—C3B—C4B—C13B | −0.1 (3) |
C2A—C3A—C4A—C5A | 177.5 (3) | C2B—C3B—C4B—C5B | −179.4 (3) |
C13A—C4A—C5A—C6A | −0.8 (4) | C13B—C4B—C5B—C6B | −0.4 (4) |
C3A—C4A—C5A—C6A | −179.0 (3) | C3B—C4B—C5B—C6B | 178.8 (3) |
C4A—C5A—C6A—C7A | −3.6 (4) | C4B—C5B—C6B—C7B | −0.5 (4) |
C5A—C6A—C7A—C12A | 3.4 (4) | C5B—C6B—C7B—C12B | 0.0 (4) |
C5A—C6A—C7A—C8A | −174.3 (3) | C5B—C6B—C7B—C8B | −178.5 (3) |
C12A—C7A—C8A—C9A | −0.8 (4) | C12B—C7B—C8B—C9B | −0.2 (4) |
C6A—C7A—C8A—C9A | 176.9 (3) | C6B—C7B—C8B—C9B | 178.3 (3) |
C7A—C8A—C9A—C10A | 0.6 (4) | C7B—C8B—C9B—C10B | −0.4 (4) |
C8A—C9A—C10A—N11A | 0.1 (5) | C8B—C9B—C10B—N11B | 1.0 (4) |
C9A—C10A—N11A—C12A | −0.5 (4) | C9B—C10B—N11B—C12B | −0.8 (4) |
C10A—N11A—C12A—C7A | 0.2 (4) | C10B—N11B—C12B—C7B | 0.1 (4) |
C10A—N11A—C12A—C13A | −178.5 (2) | C10B—N11B—C12B—C13B | −179.5 (2) |
C8A—C7A—C12A—N11A | 0.5 (4) | C8B—C7B—C12B—N11B | 0.4 (4) |
C6A—C7A—C12A—N11A | −177.4 (3) | C6B—C7B—C12B—N11B | −178.2 (2) |
C8A—C7A—C12A—C13A | 179.1 (2) | C8B—C7B—C12B—C13B | −180.0 (2) |
C6A—C7A—C12A—C13A | 1.3 (4) | C6B—C7B—C12B—C13B | 1.4 (4) |
C2A—N1A—C13A—C4A | −0.9 (3) | C2B—N1B—C13B—C4B | −1.5 (3) |
C2A—N1A—C13A—C12A | 175.5 (3) | C2B—N1B—C13B—C12B | 176.9 (3) |
C3A—C4A—C13A—N1A | 1.1 (3) | C5B—C4B—C13B—N1B | −179.6 (2) |
C5A—C4A—C13A—N1A | −177.6 (2) | C3B—C4B—C13B—N1B | 1.0 (3) |
C3A—C4A—C13A—C12A | −175.7 (3) | C5B—C4B—C13B—C12B | 1.9 (4) |
C5A—C4A—C13A—C12A | 5.6 (4) | C3B—C4B—C13B—C12B | −177.5 (2) |
N11A—C12A—C13A—N1A | −3.1 (5) | N11B—C12B—C13B—N1B | −1.0 (4) |
C7A—C12A—C13A—N1A | 178.2 (3) | C7B—C12B—C13B—N1B | 179.4 (2) |
N11A—C12A—C13A—C4A | 172.9 (3) | N11B—C12B—C13B—C4B | 177.3 (2) |
C7A—C12A—C13A—C4A | −5.8 (4) | C7B—C12B—C13B—C4B | −2.3 (4) |
C19A—N14A—C15A—C16A | −1.2 (4) | C19B—N14B—C15B—C16B | −0.6 (4) |
N14A—C15A—C16A—C17A | 1.6 (4) | N14B—C15B—C16B—C17B | 0.9 (5) |
C15A—C16A—C17A—C18A | −0.4 (4) | C15B—C16B—C17B—C18B | −0.2 (4) |
C15A—C16A—C17A—C2A | −179.1 (2) | C15B—C16B—C17B—C2B | 179.9 (2) |
C3A—C2A—C17A—C18A | 157.1 (3) | C3B—C2B—C17B—C18B | 166.0 (3) |
N1A—C2A—C17A—C18A | −21.0 (4) | N1B—C2B—C17B—C18B | −13.0 (4) |
C3A—C2A—C17A—C16A | −24.3 (4) | C3B—C2B—C17B—C16B | −14.1 (4) |
N1A—C2A—C17A—C16A | 157.6 (3) | N1B—C2B—C17B—C16B | 167.0 (2) |
C16A—C17A—C18A—C19A | −1.0 (4) | C16B—C17B—C18B—C19B | −0.8 (4) |
C2A—C17A—C18A—C19A | 177.7 (2) | C2B—C17B—C18B—C19B | 179.1 (3) |
C15A—N14A—C19A—C18A | −0.3 (4) | C15B—N14B—C19B—C18B | −0.5 (4) |
C17A—C18A—C19A—N14A | 1.5 (4) | C17B—C18B—C19B—N14B | 1.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···N14B | 0.92 (3) | 2.18 (3) | 3.100 (3) | 173 (3) |
N1B—H1B···N14Ai | 0.87 (3) | 2.12 (3) | 2.982 (3) | 171 (3) |
C18A—H18A···N14B | 0.95 | 2.61 | 3.376 (3) | 138 |
C18B—H18B···N14Ai | 0.95 | 2.57 | 3.350 (3) | 139 |
C19B—H19B···N11A | 0.95 | 2.55 | 3.289 (4) | 135 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C32H22N6 |
Mr | 490.56 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 19.3539 (8), 6.8609 (3), 19.3579 (8) |
β (°) | 112.325 (2) |
V (Å3) | 2377.77 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.12 × 0.04 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.977, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11617, 4179, 3199 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.109, 0.89 |
No. of reflections | 4179 |
No. of parameters | 353 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.21 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···N14B | 0.92 (3) | 2.18 (3) | 3.100 (3) | 173 (3) |
N1B—H1B···N14Ai | 0.87 (3) | 2.12 (3) | 2.982 (3) | 171 (3) |
C18A—H18A···N14B | 0.95 | 2.61 | 3.376 (3) | 138.3 |
C18B—H18B···N14Ai | 0.95 | 2.57 | 3.350 (3) | 139.0 |
C19B—H19B···N11A | 0.95 | 2.55 | 3.289 (4) | 134.8 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
NO COMMENT