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The title compound, C26H21ClN4O2, crystallizes in space group P21/c with two molecules in the asymmetric unit. There are no significant differences between the bonds and angles of the two molecules; however, there are significant differences in the magnitudes of some of the equivlent torsion angles involving the chiral C7 atoms (located at the points of attachment of the 4-chlorophenyl substituents).
Supporting information
CCDC reference: 202985
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.150
- Data-to-parameter ratio = 16.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(18) - H(18) ?
PLAT_420 Alert C D-H Without Acceptor N(28) - H(28) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
5-(Benzo[1,3]dioxol-5-yl)-7-(4-chloro-phenyl)-3-methyl-1-phenyl-1,6,7,8-
tetrahydropyrazolo[3,4-
b][1,4]diazepine
top
Crystal data top
C26H21ClN4O2 | Dx = 1.412 Mg m−3 |
Mr = 456.92 | Melting point: 459 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3422 (2) Å | Cell parameters from 9748 reflections |
b = 15.6889 (3) Å | θ = 3.1–27.5° |
c = 24.1716 (5) Å | µ = 0.21 mm−1 |
β = 92.437 (1)° | T = 120 K |
V = 4297.37 (14) Å3 | Plate, yellow |
Z = 8 | 0.25 × 0.20 × 0.02 mm |
F(000) = 1904 | |
Data collection top
Nonius KappaCCD diffractometer | 9748 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 6221 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
φ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −12→14 |
Tmin = 0.949, Tmax = 0.996 | k = −20→20 |
34725 measured reflections | l = −30→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0779P)2 + 0.4063P] where P = (Fo2 + 2Fc2)/3 |
9748 reflections | (Δ/σ)max = 0.001 |
597 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
(Fox & Holmes, 1966) which effectively corrects for absorption effects. High
redundancy data were used in the scaling program hence the 'multi-scan' code
word was used. No transmission coefficients are available from the program
(only scale factors for each frame). The scale factors in the experimental
table are calculated from the 'size' command in the SHELXL97 input
file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 1.09193 (15) | 0.40707 (12) | 0.06170 (7) | 0.0236 (4) | |
C111 | 1.17045 (18) | 0.42800 (15) | 0.10730 (9) | 0.0251 (5) | |
C112 | 1.1356 (2) | 0.48035 (15) | 0.14992 (9) | 0.0291 (5) | |
C113 | 1.2151 (2) | 0.50005 (17) | 0.19340 (10) | 0.0340 (6) | |
C114 | 1.3293 (2) | 0.46907 (17) | 0.19426 (10) | 0.0354 (6) | |
C115 | 1.3643 (2) | 0.41844 (17) | 0.15118 (10) | 0.0372 (6) | |
C116 | 1.28551 (19) | 0.39670 (16) | 0.10779 (10) | 0.0308 (5) | |
N12 | 1.13995 (15) | 0.38786 (12) | 0.01142 (7) | 0.0250 (4) | |
C13 | 1.04855 (18) | 0.37627 (14) | −0.02329 (9) | 0.0227 (5) | |
C13A | 0.93916 (18) | 0.38694 (14) | 0.00263 (8) | 0.0218 (5) | |
C131 | 1.0662 (2) | 0.35610 (15) | −0.08284 (9) | 0.0274 (5) | |
N14 | 0.83130 (15) | 0.37476 (11) | −0.02612 (7) | 0.0219 (4) | |
C15 | 0.73154 (18) | 0.39607 (15) | −0.00677 (8) | 0.0253 (5) | |
C15A | 0.53750 (19) | 0.32726 (14) | −0.12668 (9) | 0.0244 (5) | |
C15B | 0.42986 (19) | 0.31534 (15) | −0.10247 (9) | 0.0261 (5) | |
C151 | 0.62384 (18) | 0.37361 (14) | −0.04065 (8) | 0.0228 (5) | |
C152 | 0.63470 (19) | 0.35729 (14) | −0.09785 (8) | 0.0248 (5) | |
C153 | 0.4162 (2) | 0.26118 (16) | −0.18697 (10) | 0.0336 (6) | |
C154 | 0.41503 (19) | 0.33392 (15) | −0.04764 (9) | 0.0289 (5) | |
C155 | 0.51431 (19) | 0.36235 (15) | −0.01736 (9) | 0.0278 (5) | |
O151 | 0.52513 (13) | 0.30750 (11) | −0.18258 (6) | 0.0310 (4) | |
O152 | 0.34664 (13) | 0.28840 (11) | −0.14209 (6) | 0.0326 (4) | |
C16 | 0.7214 (2) | 0.44288 (16) | 0.04783 (9) | 0.0322 (5) | |
Cl17 | 0.57007 (5) | 0.45444 (4) | 0.31807 (2) | 0.03402 (16) | |
C17 | 0.77730 (19) | 0.39453 (17) | 0.09631 (9) | 0.0304 (5) | |
C171 | 0.72199 (18) | 0.41184 (15) | 0.15106 (9) | 0.0265 (5) | |
C172 | 0.69761 (19) | 0.34343 (15) | 0.18525 (9) | 0.0285 (5) | |
C173 | 0.65209 (19) | 0.35679 (15) | 0.23664 (9) | 0.0278 (5) | |
C174 | 0.62906 (18) | 0.43828 (15) | 0.25345 (9) | 0.0248 (5) | |
C175 | 0.6498 (2) | 0.50792 (15) | 0.22038 (9) | 0.0291 (5) | |
C176 | 0.69678 (19) | 0.49423 (16) | 0.16895 (9) | 0.0302 (5) | |
C18A | 0.97106 (18) | 0.40492 (14) | 0.05782 (8) | 0.0225 (5) | |
N18 | 0.90327 (15) | 0.41701 (12) | 0.10345 (7) | 0.0250 (4) | |
N21 | 0.43325 (15) | 0.13167 (12) | 0.01575 (7) | 0.0238 (4) | |
C211 | 0.35466 (18) | 0.11406 (14) | −0.02983 (8) | 0.0235 (5) | |
C212 | 0.23971 (19) | 0.14703 (15) | −0.02969 (9) | 0.0291 (5) | |
C213 | 0.1604 (2) | 0.12844 (16) | −0.07317 (10) | 0.0325 (6) | |
C214 | 0.1942 (2) | 0.07858 (16) | −0.11720 (10) | 0.0340 (6) | |
C215 | 0.3076 (2) | 0.04605 (16) | −0.11698 (9) | 0.0302 (5) | |
C216 | 0.38757 (19) | 0.06211 (14) | −0.07323 (9) | 0.0259 (5) | |
N22 | 0.38614 (15) | 0.14693 (12) | 0.06711 (7) | 0.0249 (4) | |
C23 | 0.47793 (18) | 0.16079 (14) | 0.10080 (8) | 0.0235 (5) | |
C23A | 0.58691 (18) | 0.15466 (14) | 0.07371 (8) | 0.0213 (5) | |
C231 | 0.4625 (2) | 0.18013 (16) | 0.16071 (9) | 0.0290 (5) | |
N24 | 0.69467 (15) | 0.16667 (11) | 0.10187 (7) | 0.0223 (4) | |
C25 | 0.79488 (19) | 0.14937 (15) | 0.08181 (9) | 0.0261 (5) | |
C25A | 0.98779 (19) | 0.17747 (14) | 0.20884 (9) | 0.0248 (5) | |
C25B | 1.09384 (19) | 0.20358 (15) | 0.18758 (9) | 0.0300 (5) | |
C252 | 0.89078 (18) | 0.15975 (14) | 0.17592 (8) | 0.0235 (5) | |
C253 | 1.1172 (2) | 0.1976 (2) | 0.27971 (11) | 0.0491 (8) | |
C254 | 1.1070 (2) | 0.21115 (15) | 0.13153 (10) | 0.0305 (5) | |
C255 | 1.00837 (19) | 0.19254 (15) | 0.09724 (9) | 0.0281 (5) | |
O251 | 0.99978 (14) | 0.17208 (12) | 0.26581 (6) | 0.0353 (4) | |
O252 | 1.17703 (14) | 0.21381 (12) | 0.22996 (7) | 0.0406 (4) | |
C26 | 0.8103 (2) | 0.10713 (18) | 0.02590 (9) | 0.0351 (6) | |
C271 | 0.79974 (18) | 0.12315 (16) | −0.07712 (9) | 0.0273 (5) | |
C28A | 0.55397 (18) | 0.13709 (14) | 0.01858 (9) | 0.0226 (5) | |
C251 | 0.90051 (19) | 0.16702 (14) | 0.11786 (9) | 0.0246 (5) | |
Cl27 | 0.96273 (5) | 0.06001 (5) | −0.23882 (2) | 0.0460 (2) | |
C27 | 0.74625 (19) | 0.14791 (17) | −0.02304 (9) | 0.0321 (6) | |
C272 | 0.8191 (2) | 0.03907 (16) | −0.09182 (9) | 0.0332 (6) | |
C273 | 0.8690 (2) | 0.01905 (16) | −0.14164 (9) | 0.0328 (6) | |
C274 | 0.89811 (19) | 0.08438 (16) | −0.17631 (9) | 0.0284 (5) | |
C275 | 0.8786 (2) | 0.16800 (16) | −0.16310 (9) | 0.0309 (5) | |
C276 | 0.83089 (19) | 0.18685 (16) | −0.11294 (9) | 0.0294 (5) | |
N28 | 0.62102 (15) | 0.12519 (12) | −0.02697 (7) | 0.0251 (4) | |
H112 | 1.0577 | 0.5027 | 0.1494 | 0.035* | |
H113 | 1.1906 | 0.5351 | 0.2228 | 0.041* | |
H114 | 1.3831 | 0.4825 | 0.2242 | 0.042* | |
H115 | 1.4432 | 0.3982 | 0.1512 | 0.045* | |
H116 | 1.3099 | 0.3608 | 0.0788 | 0.037* | |
H13A | 1.0891 | 0.4080 | −0.1022 | 0.041* | |
H13B | 0.9924 | 0.3339 | −0.0999 | 0.041* | |
H13C | 1.1284 | 0.3132 | −0.0854 | 0.041* | |
H152 | 0.7069 | 0.3669 | −0.1154 | 0.030* | |
H15A | 0.3743 | 0.2733 | −0.2229 | 0.040* | |
H15B | 0.4313 | 0.1991 | −0.1845 | 0.040* | |
H154 | 0.3408 | 0.3277 | −0.0313 | 0.035* | |
H155 | 0.5074 | 0.3747 | 0.0209 | 0.033* | |
H16A | 0.7599 | 0.4993 | 0.0452 | 0.039* | |
H16B | 0.6369 | 0.4525 | 0.0546 | 0.039* | |
H17 | 0.7711 | 0.3321 | 0.0883 | 0.037* | |
H172 | 0.7124 | 0.2870 | 0.1732 | 0.034* | |
H173 | 0.6369 | 0.3099 | 0.2601 | 0.033* | |
H175 | 0.6323 | 0.5640 | 0.2325 | 0.035* | |
H176 | 0.7119 | 0.5415 | 0.1457 | 0.036* | |
H18 | 0.9428 | 0.3947 | 0.1357 | 0.030* | |
H212 | 0.2164 | 0.1819 | 0.0000 | 0.035* | |
H213 | 0.0822 | 0.1500 | −0.0729 | 0.039* | |
H214 | 0.1398 | 0.0669 | −0.1472 | 0.041* | |
H215 | 0.3310 | 0.0122 | −0.1472 | 0.036* | |
H216 | 0.4643 | 0.0378 | −0.0729 | 0.031* | |
H23A | 0.4778 | 0.2408 | 0.1676 | 0.044* | |
H23B | 0.5179 | 0.1458 | 0.1835 | 0.044* | |
H23C | 0.3815 | 0.1665 | 0.1703 | 0.044* | |
H252 | 0.8187 | 0.1430 | 0.1914 | 0.028* | |
H25A | 1.1585 | 0.1520 | 0.3012 | 0.059* | |
H25B | 1.1169 | 0.2497 | 0.3028 | 0.059* | |
H254 | 1.1797 | 0.2282 | 0.1169 | 0.037* | |
H255 | 1.0147 | 0.1974 | 0.0583 | 0.034* | |
H26A | 0.8956 | 0.1061 | 0.0187 | 0.042* | |
H26B | 0.7836 | 0.0472 | 0.0284 | 0.042* | |
H27 | 0.7525 | 0.2112 | −0.0188 | 0.039* | |
H272 | 0.7979 | −0.0054 | −0.0675 | 0.040* | |
H273 | 0.8827 | −0.0386 | −0.1515 | 0.039* | |
H275 | 0.8977 | 0.2123 | −0.1880 | 0.037* | |
H276 | 0.8193 | 0.2447 | −0.1030 | 0.035* | |
H28 | 0.5821 | 0.1399 | −0.0612 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0145 (9) | 0.0341 (11) | 0.0225 (9) | 0.0004 (8) | 0.0049 (7) | 0.0003 (8) |
C111 | 0.0174 (11) | 0.0328 (13) | 0.0251 (11) | −0.0044 (9) | 0.0001 (9) | 0.0056 (10) |
C112 | 0.0197 (11) | 0.0373 (13) | 0.0302 (12) | 0.0000 (10) | 0.0013 (9) | 0.0021 (11) |
C113 | 0.0283 (12) | 0.0474 (15) | 0.0262 (11) | −0.0063 (11) | 0.0010 (10) | −0.0009 (11) |
C114 | 0.0239 (12) | 0.0513 (16) | 0.0304 (12) | −0.0064 (11) | −0.0055 (10) | 0.0043 (12) |
C115 | 0.0191 (12) | 0.0489 (16) | 0.0433 (14) | 0.0013 (11) | −0.0012 (11) | 0.0058 (13) |
C116 | 0.0209 (12) | 0.0387 (14) | 0.0331 (12) | 0.0021 (10) | 0.0038 (10) | 0.0010 (11) |
N12 | 0.0193 (9) | 0.0315 (11) | 0.0246 (9) | 0.0007 (8) | 0.0062 (8) | −0.0007 (8) |
C13 | 0.0200 (11) | 0.0239 (11) | 0.0245 (11) | −0.0010 (9) | 0.0046 (9) | 0.0016 (9) |
C13A | 0.0175 (10) | 0.0246 (11) | 0.0236 (10) | −0.0006 (9) | 0.0036 (9) | 0.0004 (9) |
C131 | 0.0234 (11) | 0.0319 (13) | 0.0272 (11) | 0.0004 (10) | 0.0053 (9) | −0.0028 (10) |
N14 | 0.0173 (9) | 0.0259 (10) | 0.0226 (9) | −0.0014 (7) | 0.0023 (7) | 0.0004 (8) |
C15 | 0.0191 (11) | 0.0362 (13) | 0.0206 (10) | −0.0002 (9) | 0.0011 (9) | 0.0045 (10) |
C15A | 0.0223 (11) | 0.0289 (12) | 0.0220 (11) | 0.0029 (9) | 0.0022 (9) | 0.0014 (9) |
C15B | 0.0194 (11) | 0.0283 (12) | 0.0304 (12) | 0.0000 (9) | −0.0024 (9) | 0.0011 (10) |
C151 | 0.0183 (10) | 0.0277 (12) | 0.0225 (10) | 0.0005 (9) | 0.0027 (9) | 0.0028 (9) |
C152 | 0.0201 (11) | 0.0325 (13) | 0.0220 (10) | 0.0016 (9) | 0.0018 (9) | 0.0044 (10) |
C153 | 0.0259 (12) | 0.0386 (14) | 0.0359 (13) | 0.0007 (11) | −0.0035 (10) | −0.0080 (11) |
C154 | 0.0169 (11) | 0.0379 (13) | 0.0324 (12) | −0.0021 (10) | 0.0062 (9) | −0.0003 (11) |
C155 | 0.0226 (11) | 0.0375 (13) | 0.0237 (11) | 0.0003 (10) | 0.0046 (9) | 0.0012 (10) |
O151 | 0.0254 (8) | 0.0439 (10) | 0.0236 (8) | 0.0004 (7) | −0.0014 (7) | −0.0041 (7) |
O152 | 0.0200 (8) | 0.0421 (10) | 0.0353 (9) | 0.0001 (7) | −0.0041 (7) | −0.0072 (8) |
C16 | 0.0247 (12) | 0.0418 (14) | 0.0304 (12) | 0.0002 (11) | 0.0038 (10) | −0.0018 (11) |
Cl17 | 0.0322 (3) | 0.0485 (4) | 0.0220 (3) | 0.0003 (3) | 0.0084 (2) | −0.0026 (3) |
C17 | 0.0188 (11) | 0.0478 (15) | 0.0249 (11) | 0.0010 (10) | 0.0034 (9) | −0.0040 (11) |
C171 | 0.0144 (10) | 0.0413 (14) | 0.0241 (11) | 0.0007 (9) | 0.0023 (9) | −0.0050 (10) |
C172 | 0.0229 (11) | 0.0351 (13) | 0.0277 (11) | 0.0055 (10) | 0.0015 (10) | −0.0022 (10) |
C173 | 0.0248 (12) | 0.0347 (13) | 0.0237 (11) | 0.0010 (10) | −0.0001 (9) | 0.0024 (10) |
C174 | 0.0174 (11) | 0.0354 (13) | 0.0215 (10) | −0.0008 (9) | 0.0011 (9) | −0.0024 (10) |
C175 | 0.0291 (12) | 0.0306 (13) | 0.0279 (11) | 0.0011 (10) | 0.0049 (10) | −0.0027 (10) |
C176 | 0.0248 (12) | 0.0382 (14) | 0.0279 (12) | −0.0030 (10) | 0.0056 (10) | 0.0044 (10) |
C18A | 0.0156 (10) | 0.0271 (12) | 0.0250 (11) | 0.0007 (9) | 0.0035 (9) | 0.0026 (9) |
N18 | 0.0149 (9) | 0.0401 (11) | 0.0202 (9) | −0.0002 (8) | 0.0017 (7) | 0.0004 (8) |
N21 | 0.0163 (9) | 0.0356 (11) | 0.0197 (8) | −0.0010 (8) | 0.0034 (7) | −0.0001 (8) |
C211 | 0.0188 (11) | 0.0290 (12) | 0.0228 (10) | −0.0036 (9) | 0.0017 (9) | 0.0038 (9) |
C212 | 0.0223 (11) | 0.0345 (13) | 0.0305 (12) | −0.0005 (10) | 0.0029 (10) | 0.0002 (10) |
C213 | 0.0170 (11) | 0.0404 (14) | 0.0400 (13) | 0.0021 (10) | −0.0001 (10) | 0.0032 (12) |
C214 | 0.0251 (12) | 0.0451 (15) | 0.0311 (12) | −0.0065 (11) | −0.0057 (10) | 0.0047 (12) |
C215 | 0.0262 (12) | 0.0391 (14) | 0.0253 (11) | −0.0083 (10) | 0.0020 (10) | −0.0006 (10) |
C216 | 0.0186 (11) | 0.0305 (12) | 0.0287 (11) | −0.0022 (9) | 0.0035 (9) | 0.0026 (10) |
N22 | 0.0207 (9) | 0.0328 (11) | 0.0217 (9) | 0.0017 (8) | 0.0066 (8) | −0.0009 (8) |
C23 | 0.0205 (11) | 0.0272 (12) | 0.0230 (11) | 0.0004 (9) | 0.0043 (9) | −0.0001 (9) |
C23A | 0.0186 (10) | 0.0247 (11) | 0.0210 (10) | −0.0011 (9) | 0.0036 (9) | −0.0023 (9) |
C231 | 0.0246 (12) | 0.0382 (14) | 0.0247 (11) | −0.0004 (10) | 0.0056 (10) | −0.0038 (10) |
N24 | 0.0201 (9) | 0.0257 (10) | 0.0211 (9) | −0.0003 (8) | 0.0027 (7) | −0.0010 (8) |
C25 | 0.0212 (11) | 0.0356 (13) | 0.0216 (11) | 0.0008 (10) | 0.0028 (9) | 0.0009 (10) |
C25A | 0.0225 (11) | 0.0310 (12) | 0.0210 (11) | 0.0060 (9) | 0.0015 (9) | −0.0026 (9) |
C25B | 0.0215 (12) | 0.0363 (14) | 0.0317 (12) | 0.0015 (10) | −0.0059 (10) | −0.0076 (11) |
C252 | 0.0175 (10) | 0.0303 (12) | 0.0228 (11) | 0.0023 (9) | 0.0029 (9) | −0.0010 (9) |
C253 | 0.0242 (13) | 0.091 (2) | 0.0318 (13) | 0.0047 (14) | −0.0027 (11) | −0.0146 (15) |
C254 | 0.0221 (12) | 0.0343 (13) | 0.0352 (13) | −0.0029 (10) | 0.0033 (10) | 0.0067 (11) |
C255 | 0.0220 (11) | 0.0381 (14) | 0.0244 (11) | 0.0018 (10) | 0.0020 (9) | 0.0068 (10) |
O251 | 0.0252 (8) | 0.0596 (12) | 0.0206 (8) | 0.0051 (8) | −0.0027 (7) | −0.0058 (8) |
O252 | 0.0231 (9) | 0.0648 (13) | 0.0332 (9) | −0.0046 (8) | −0.0063 (7) | −0.0068 (9) |
C26 | 0.0246 (12) | 0.0531 (16) | 0.0278 (12) | 0.0040 (11) | 0.0023 (10) | −0.0037 (12) |
C271 | 0.0152 (11) | 0.0438 (14) | 0.0230 (11) | −0.0011 (10) | 0.0011 (9) | −0.0074 (11) |
C28A | 0.0179 (10) | 0.0263 (12) | 0.0240 (10) | 0.0012 (9) | 0.0038 (9) | 0.0013 (9) |
C251 | 0.0213 (11) | 0.0289 (12) | 0.0238 (11) | 0.0013 (9) | 0.0028 (9) | 0.0010 (10) |
Cl27 | 0.0305 (3) | 0.0875 (5) | 0.0203 (3) | 0.0129 (3) | 0.0050 (2) | −0.0050 (3) |
C27 | 0.0202 (11) | 0.0527 (16) | 0.0238 (11) | −0.0031 (11) | 0.0037 (9) | −0.0078 (11) |
C272 | 0.0343 (13) | 0.0422 (15) | 0.0233 (11) | −0.0059 (11) | 0.0020 (10) | 0.0035 (11) |
C273 | 0.0369 (14) | 0.0350 (14) | 0.0262 (12) | 0.0055 (11) | −0.0015 (10) | −0.0046 (10) |
C274 | 0.0181 (11) | 0.0484 (15) | 0.0188 (10) | 0.0048 (10) | 0.0024 (9) | −0.0022 (10) |
C275 | 0.0261 (12) | 0.0396 (14) | 0.0270 (12) | −0.0054 (10) | 0.0008 (10) | 0.0045 (11) |
C276 | 0.0236 (12) | 0.0338 (13) | 0.0306 (12) | 0.0018 (10) | 0.0004 (10) | −0.0036 (10) |
N28 | 0.0173 (9) | 0.0397 (11) | 0.0185 (8) | −0.0007 (8) | 0.0036 (7) | −0.0013 (8) |
Geometric parameters (Å, º) top
N11—C18A | 1.371 (3) | N21—C28A | 1.371 (3) |
N11—N12 | 1.386 (2) | N21—N22 | 1.393 (2) |
N11—C111 | 1.426 (3) | N21—C211 | 1.415 (3) |
C111—C112 | 1.388 (3) | C211—C216 | 1.392 (3) |
C111—C116 | 1.394 (3) | C211—C212 | 1.403 (3) |
C112—C113 | 1.390 (3) | C212—C213 | 1.385 (3) |
C112—H112 | 0.95 | C212—H212 | 0.95 |
C113—C114 | 1.383 (3) | C213—C214 | 1.387 (3) |
C113—H113 | 0.95 | C213—H213 | 0.95 |
C114—C115 | 1.381 (4) | C214—C215 | 1.384 (3) |
C114—H114 | 0.95 | C214—H214 | 0.95 |
C115—C116 | 1.391 (3) | C215—C216 | 1.387 (3) |
C115—H115 | 0.95 | C215—H215 | 0.95 |
C116—H116 | 0.95 | C216—H216 | 0.95 |
N12—C13 | 1.318 (3) | N22—C23 | 1.312 (3) |
C13—C13A | 1.423 (3) | C23—C23A | 1.427 (3) |
C13—C131 | 1.495 (3) | C23—C231 | 1.497 (3) |
C13A—N14 | 1.394 (3) | C23A—N24 | 1.386 (3) |
C13A—C18A | 1.396 (3) | C23A—C28A | 1.396 (3) |
C131—H13A | 0.98 | C231—H23A | 0.98 |
C131—H13B | 0.98 | C231—H23B | 0.98 |
C131—H13C | 0.98 | C231—H23C | 0.98 |
N14—C15 | 1.287 (3) | N24—C25 | 1.283 (3) |
C15—C151 | 1.484 (3) | C25—C251 | 1.477 (3) |
C15—C16 | 1.519 (3) | C25—C26 | 1.522 (3) |
C15A—C152 | 1.363 (3) | C25A—C252 | 1.359 (3) |
C15A—O151 | 1.388 (3) | C25A—O251 | 1.381 (3) |
C15A—C15B | 1.389 (3) | C25A—C25B | 1.390 (3) |
C15B—C154 | 1.374 (3) | C25B—O252 | 1.372 (3) |
C15B—O152 | 1.382 (3) | C25B—C254 | 1.374 (3) |
C151—C155 | 1.397 (3) | C252—C251 | 1.417 (3) |
C151—C152 | 1.417 (3) | C252—H252 | 0.95 |
C152—H152 | 0.95 | C253—O251 | 1.418 (3) |
C153—O152 | 1.433 (3) | C253—O252 | 1.428 (3) |
C153—O151 | 1.434 (3) | C253—H25A | 0.99 |
C153—H15A | 0.99 | C253—H25B | 0.99 |
C153—H15B | 0.99 | C254—C255 | 1.394 (3) |
C154—C155 | 1.390 (3) | C254—H254 | 0.95 |
C154—H154 | 0.95 | C255—C251 | 1.399 (3) |
C155—H155 | 0.95 | C255—H255 | 0.95 |
C16—C17 | 1.513 (3) | C26—C27 | 1.504 (3) |
C16—H16A | 0.99 | C26—H26A | 0.99 |
C16—H16B | 0.99 | C26—H26B | 0.99 |
Cl17—C174 | 1.744 (2) | C271—C276 | 1.378 (3) |
C17—N18 | 1.475 (3) | C271—C272 | 1.386 (3) |
C17—C171 | 1.513 (3) | C271—C27 | 1.515 (3) |
C17—H17 | 1.00 | C27—N28 | 1.464 (3) |
C171—C172 | 1.389 (3) | Cl27—C274 | 1.749 (2) |
C171—C176 | 1.397 (3) | C28A—N28 | 1.377 (3) |
C172—C173 | 1.381 (3) | C27—H27 | 1.00 |
C172—H172 | 0.95 | C272—C273 | 1.388 (3) |
C173—C174 | 1.370 (3) | C272—H272 | 0.95 |
C173—H173 | 0.95 | C273—C274 | 1.373 (3) |
C174—C175 | 1.380 (3) | C273—H273 | 0.95 |
C175—C176 | 1.390 (3) | C274—C275 | 1.370 (3) |
C175—H175 | 0.95 | C275—C276 | 1.381 (3) |
C176—H176 | 0.95 | C275—H275 | 0.95 |
C18A—N18 | 1.384 (3) | C276—H276 | 0.95 |
N18—H18 | 0.9499 | N28—H28 | 0.9498 |
| | | |
C18A—N11—N12 | 111.33 (17) | C28A—N21—N22 | 111.41 (17) |
C18A—N11—C111 | 130.45 (17) | C28A—N21—C211 | 130.25 (17) |
N12—N11—C111 | 118.18 (16) | N22—N21—C211 | 118.34 (16) |
C112—C111—C116 | 119.9 (2) | C216—C211—C212 | 119.8 (2) |
C112—C111—N11 | 121.47 (19) | C216—C211—N21 | 121.40 (19) |
C116—C111—N11 | 118.6 (2) | C212—C211—N21 | 118.76 (19) |
C111—C112—C113 | 119.8 (2) | C213—C212—C211 | 119.6 (2) |
C111—C112—H112 | 120.1 | C213—C212—H212 | 120.2 |
C113—C112—H112 | 120.1 | C211—C212—H212 | 120.2 |
C114—C113—C112 | 120.7 (2) | C212—C213—C214 | 120.6 (2) |
C114—C113—H113 | 119.7 | C212—C213—H213 | 119.7 |
C112—C113—H113 | 119.7 | C214—C213—H213 | 119.7 |
C115—C114—C113 | 119.3 (2) | C215—C214—C213 | 119.4 (2) |
C115—C114—H114 | 120.3 | C215—C214—H214 | 120.3 |
C113—C114—H114 | 120.3 | C213—C214—H214 | 120.3 |
C114—C115—C116 | 120.9 (2) | C214—C215—C216 | 120.9 (2) |
C114—C115—H115 | 119.6 | C214—C215—H215 | 119.5 |
C116—C115—H115 | 119.6 | C216—C215—H215 | 119.5 |
C115—C116—C111 | 119.4 (2) | C215—C216—C211 | 119.6 (2) |
C115—C116—H116 | 120.3 | C215—C216—H216 | 120.2 |
C111—C116—H116 | 120.3 | C211—C216—H216 | 120.2 |
C13—N12—N11 | 105.10 (16) | C23—N22—N21 | 104.91 (16) |
N12—C13—C13A | 112.35 (18) | N22—C23—C23A | 112.58 (18) |
N12—C13—C131 | 120.55 (18) | N22—C23—C231 | 120.75 (18) |
C13A—C13—C131 | 127.1 (2) | C23A—C23—C231 | 126.67 (19) |
N14—C13A—C18A | 133.66 (18) | N24—C23A—C28A | 133.63 (18) |
N14—C13A—C13 | 121.82 (18) | N24—C23A—C23 | 121.91 (18) |
C18A—C13A—C13 | 104.42 (18) | C28A—C23A—C23 | 104.45 (18) |
C13—C131—H13A | 109.5 | C23—C231—H23A | 109.5 |
C13—C131—H13B | 109.5 | C23—C231—H23B | 109.5 |
H13A—C131—H13B | 109.5 | H23A—C231—H23B | 109.5 |
C13—C131—H13C | 109.5 | C23—C231—H23C | 109.5 |
H13A—C131—H13C | 109.5 | H23A—C231—H23C | 109.5 |
H13B—C131—H13C | 109.5 | H23B—C231—H23C | 109.5 |
C15—N14—C13A | 123.34 (18) | C25—N24—C23A | 124.21 (18) |
N14—C15—C151 | 116.98 (18) | N24—C25—C251 | 116.52 (19) |
N14—C15—C16 | 122.81 (19) | N24—C25—C26 | 124.4 (2) |
C151—C15—C16 | 120.20 (18) | C251—C25—C26 | 118.98 (18) |
C152—C15A—O151 | 128.40 (19) | C252—C25A—O251 | 127.9 (2) |
C152—C15A—C15B | 122.5 (2) | C252—C25A—C25B | 122.4 (2) |
O151—C15A—C15B | 109.03 (19) | O251—C25A—C25B | 109.68 (19) |
C154—C15B—O152 | 128.69 (19) | O252—C25B—C254 | 128.7 (2) |
C154—C15B—C15A | 121.6 (2) | O252—C25B—C25A | 109.69 (19) |
O152—C15B—C15A | 109.63 (18) | C254—C25B—C25A | 121.5 (2) |
C155—C151—C152 | 119.1 (2) | C25A—C252—C251 | 117.91 (19) |
C155—C151—C15 | 122.21 (19) | C25A—C252—H252 | 121.0 |
C152—C151—C15 | 118.54 (18) | C251—C252—H252 | 121.0 |
C15A—C152—C151 | 117.35 (19) | O251—C253—O252 | 109.01 (19) |
C15A—C152—H152 | 121.3 | O251—C253—H25A | 109.9 |
C151—C152—H152 | 121.3 | O252—C253—H25A | 109.9 |
O152—C153—O151 | 107.06 (18) | O251—C253—H25B | 109.9 |
O152—C153—H15A | 110.3 | O252—C253—H25B | 109.9 |
O151—C153—H15A | 110.3 | H25A—C253—H25B | 108.3 |
O152—C153—H15B | 110.3 | C25B—C254—C255 | 116.7 (2) |
O151—C153—H15B | 110.3 | C25B—C254—H254 | 121.6 |
H15A—C153—H15B | 108.6 | C255—C254—H254 | 121.6 |
C15B—C154—C155 | 116.51 (19) | C254—C255—C251 | 122.7 (2) |
C15B—C154—H154 | 121.7 | C254—C255—H255 | 118.7 |
C155—C154—H154 | 121.7 | C251—C255—H255 | 118.7 |
C154—C155—C151 | 122.9 (2) | C25A—O251—C253 | 105.72 (18) |
C154—C155—H155 | 118.6 | C25B—O252—C253 | 105.76 (17) |
C151—C155—H155 | 118.6 | C27—C26—C25 | 116.3 (2) |
C15A—O151—C153 | 103.67 (16) | C27—C26—H26A | 108.2 |
C15B—O152—C153 | 103.54 (16) | C25—C26—H26A | 108.2 |
C17—C16—C15 | 112.7 (2) | C27—C26—H26B | 108.2 |
C17—C16—H16A | 109.1 | C25—C26—H26B | 108.2 |
C15—C16—H16A | 109.1 | H26A—C26—H26B | 107.4 |
C17—C16—H16B | 109.1 | C276—C271—C272 | 118.8 (2) |
C15—C16—H16B | 109.1 | C276—C271—C27 | 118.6 (2) |
H16A—C16—H16B | 107.8 | C272—C271—C27 | 122.6 (2) |
N18—C17—C16 | 110.07 (19) | N28—C27—C26 | 112.5 (2) |
N18—C17—C171 | 106.88 (17) | N21—C28A—N28 | 122.42 (19) |
C16—C17—C171 | 114.32 (19) | N21—C28A—C23A | 106.63 (17) |
N18—C17—H17 | 108.5 | N28—C28A—C23A | 130.95 (19) |
C16—C17—H17 | 108.5 | C255—C251—C252 | 118.8 (2) |
C171—C17—H17 | 108.5 | C255—C251—C25 | 122.89 (19) |
C172—C171—C176 | 118.83 (19) | C252—C251—C25 | 118.27 (18) |
C172—C171—C17 | 118.8 (2) | N28—C27—C271 | 107.74 (18) |
C176—C171—C17 | 122.3 (2) | C26—C27—C271 | 111.82 (19) |
C173—C172—C171 | 120.6 (2) | N28—C27—H27 | 108.2 |
C173—C172—H172 | 119.7 | C26—C27—H27 | 108.2 |
C171—C172—H172 | 119.7 | C271—C27—H27 | 108.2 |
C174—C173—C172 | 119.4 (2) | C271—C272—C273 | 120.8 (2) |
C174—C173—H173 | 120.3 | C271—C272—H272 | 119.6 |
C172—C173—H173 | 120.3 | C273—C272—H272 | 119.6 |
C173—C174—C175 | 121.9 (2) | C274—C273—C272 | 118.6 (2) |
C173—C174—Cl17 | 119.11 (17) | C274—C273—H273 | 120.7 |
C175—C174—Cl17 | 119.02 (17) | C272—C273—H273 | 120.7 |
C174—C175—C176 | 118.5 (2) | C275—C274—C273 | 121.8 (2) |
C174—C175—H175 | 120.8 | C275—C274—Cl27 | 119.21 (18) |
C176—C175—H175 | 120.8 | C273—C274—Cl27 | 118.99 (19) |
C175—C176—C171 | 120.8 (2) | C274—C275—C276 | 118.9 (2) |
C175—C176—H176 | 119.6 | C274—C275—H275 | 120.6 |
C171—C176—H176 | 119.6 | C276—C275—H275 | 120.6 |
N11—C18A—N18 | 122.00 (19) | C271—C276—C275 | 121.1 (2) |
N11—C18A—C13A | 106.76 (17) | C271—C276—H276 | 119.4 |
N18—C18A—C13A | 131.22 (19) | C275—C276—H276 | 119.4 |
C18A—N18—C17 | 116.24 (17) | C28A—N28—C27 | 118.84 (17) |
C18A—N18—H18 | 110.2 | C28A—N28—H28 | 114.3 |
C17—N18—H18 | 115.4 | C27—N28—H28 | 114.3 |
| | | |
C18A—N11—C111—C112 | −24.9 (3) | C28A—N21—C211—C216 | 30.4 (3) |
N12—N11—C111—C112 | 152.7 (2) | N22—N21—C211—C216 | −150.0 (2) |
C18A—N11—C111—C116 | 156.9 (2) | C28A—N21—C211—C212 | −152.4 (2) |
N12—N11—C111—C116 | −25.5 (3) | N22—N21—C211—C212 | 27.3 (3) |
C116—C111—C112—C113 | −1.2 (3) | C216—C211—C212—C213 | −0.8 (3) |
N11—C111—C112—C113 | −179.3 (2) | N21—C211—C212—C213 | −178.1 (2) |
C111—C112—C113—C114 | 1.0 (4) | C211—C212—C213—C214 | −0.9 (3) |
C112—C113—C114—C115 | 0.3 (4) | C212—C213—C214—C215 | 1.1 (4) |
C113—C114—C115—C116 | −1.5 (4) | C213—C214—C215—C216 | 0.5 (4) |
C114—C115—C116—C111 | 1.4 (4) | C214—C215—C216—C211 | −2.2 (3) |
C112—C111—C116—C115 | 0.0 (3) | C212—C211—C216—C215 | 2.4 (3) |
N11—C111—C116—C115 | 178.2 (2) | N21—C211—C216—C215 | 179.62 (19) |
C18A—N11—N12—C13 | 1.6 (2) | C28A—N21—N22—C23 | −0.5 (2) |
C111—N11—N12—C13 | −176.42 (19) | C211—N21—N22—C23 | 179.79 (19) |
N11—N12—C13—C13A | −0.2 (2) | N21—N22—C23—C23A | −0.5 (2) |
N11—N12—C13—C131 | 178.61 (19) | N21—N22—C23—C231 | 179.8 (2) |
N12—C13—C13A—N14 | −177.83 (19) | N22—C23—C23A—N24 | −179.68 (19) |
C131—C13—C13A—N14 | 3.4 (3) | C231—C23—C23A—N24 | 0.0 (3) |
N12—C13—C13A—C18A | −1.1 (2) | N22—C23—C23A—C28A | 1.2 (2) |
C131—C13—C13A—C18A | −179.9 (2) | C231—C23—C23A—C28A | −179.1 (2) |
C18A—C13A—N14—C15 | 15.3 (4) | C28A—C23A—N24—C25 | −12.3 (4) |
C13—C13A—N14—C15 | −169.1 (2) | C23—C23A—N24—C25 | 169.0 (2) |
C13A—N14—C15—C151 | −175.92 (19) | C23A—N24—C25—C251 | 179.57 (19) |
C13A—N14—C15—C16 | 4.7 (3) | C23A—N24—C25—C26 | −4.7 (4) |
C152—C15A—C15B—C154 | 0.5 (4) | C252—C25A—C25B—O252 | −177.8 (2) |
O151—C15A—C15B—C154 | −177.0 (2) | O251—C25A—C25B—O252 | 1.3 (3) |
C152—C15A—C15B—O152 | 177.1 (2) | C252—C25A—C25B—C254 | −1.4 (4) |
O151—C15A—C15B—O152 | −0.4 (3) | O251—C25A—C25B—C254 | 177.7 (2) |
N14—C15—C151—C155 | 154.9 (2) | O251—C25A—C252—C251 | −177.7 (2) |
C16—C15—C151—C155 | −25.7 (3) | C25B—C25A—C252—C251 | 1.2 (3) |
N14—C15—C151—C152 | −20.6 (3) | O252—C25B—C254—C255 | 176.5 (2) |
C16—C15—C151—C152 | 158.8 (2) | C25A—C25B—C254—C255 | 0.9 (4) |
O151—C15A—C152—C151 | 179.2 (2) | C25B—C254—C255—C251 | −0.2 (4) |
C15B—C15A—C152—C151 | 2.2 (3) | C252—C25A—O251—C253 | −179.8 (2) |
C155—C151—C152—C15A | −3.0 (3) | C25B—C25A—O251—C253 | 1.1 (3) |
C15—C151—C152—C15A | 172.6 (2) | O252—C253—O251—C25A | −3.1 (3) |
O152—C15B—C154—C155 | −178.1 (2) | C254—C25B—O252—C253 | −179.2 (3) |
C15A—C15B—C154—C155 | −2.2 (3) | C25A—C25B—O252—C253 | −3.1 (3) |
C15B—C154—C155—C151 | 1.2 (4) | O251—C253—O252—C25B | 3.9 (3) |
C152—C151—C155—C154 | 1.4 (3) | N24—C25—C26—C27 | 52.7 (3) |
C15—C151—C155—C154 | −174.1 (2) | C251—C25—C26—C27 | −131.7 (2) |
C152—C15A—O151—C153 | 167.1 (2) | C25—C26—C27—N28 | −79.3 (3) |
C15B—C15A—O151—C153 | −15.6 (2) | N22—N21—C28A—N28 | −179.48 (19) |
O152—C153—O151—C15A | 25.7 (2) | C211—N21—C28A—N28 | 0.2 (4) |
C154—C15B—O152—C153 | −167.5 (2) | N22—N21—C28A—C23A | 1.3 (2) |
C15A—C15B—O152—C153 | 16.2 (2) | C211—N21—C28A—C23A | −179.1 (2) |
O151—C153—O152—C15B | −25.9 (2) | N24—C23A—C28A—N21 | 179.6 (2) |
N14—C15—C16—C17 | −58.6 (3) | C23—C23A—C28A—N21 | −1.4 (2) |
C151—C15—C16—C17 | 122.0 (2) | N24—C23A—C28A—N28 | 0.4 (4) |
C15—C16—C17—N18 | 88.4 (2) | C23—C23A—C28A—N28 | 179.4 (2) |
C15—C16—C17—C171 | −151.3 (2) | C254—C255—C251—C252 | 0.0 (3) |
N18—C17—C171—C172 | −103.2 (2) | C254—C255—C251—C25 | 178.4 (2) |
C16—C17—C171—C172 | 134.7 (2) | C25A—C252—C251—C255 | −0.5 (3) |
N18—C17—C171—C176 | 75.5 (3) | C25A—C252—C251—C25 | −178.9 (2) |
C16—C17—C171—C176 | −46.6 (3) | N24—C25—C251—C255 | −147.5 (2) |
C176—C171—C172—C173 | −1.7 (3) | C26—C25—C251—C255 | 36.6 (3) |
C17—C171—C172—C173 | 177.1 (2) | N24—C25—C251—C252 | 30.9 (3) |
C171—C172—C173—C174 | 1.1 (3) | C26—C25—C251—C252 | −145.1 (2) |
C172—C173—C174—C175 | 0.2 (3) | C25—C26—C27—C271 | 159.3 (2) |
C172—C173—C174—Cl17 | 179.29 (17) | C276—C271—C27—N28 | 108.4 (2) |
C173—C174—C175—C176 | −0.8 (3) | C272—C271—C27—N28 | −71.9 (3) |
Cl17—C174—C175—C176 | −179.98 (17) | C276—C271—C27—C26 | −127.5 (2) |
C174—C175—C176—C171 | 0.3 (3) | C272—C271—C27—C26 | 52.2 (3) |
C172—C171—C176—C175 | 1.0 (3) | C276—C271—C272—C273 | 0.1 (3) |
C17—C171—C176—C175 | −177.7 (2) | C27—C271—C272—C273 | −179.6 (2) |
N12—N11—C18A—N18 | 176.13 (19) | C271—C272—C273—C274 | −0.4 (4) |
C111—N11—C18A—N18 | −6.2 (4) | C272—C273—C274—C275 | −0.4 (3) |
N12—N11—C18A—C13A | −2.3 (2) | C272—C273—C274—Cl27 | 179.22 (18) |
C111—N11—C18A—C13A | 175.4 (2) | C273—C274—C275—C276 | 1.5 (3) |
N14—C13A—C18A—N11 | 178.1 (2) | Cl27—C274—C275—C276 | −178.07 (17) |
C13—C13A—C18A—N11 | 2.0 (2) | C272—C271—C276—C275 | 1.1 (3) |
N14—C13A—C18A—N18 | −0.1 (4) | C27—C271—C276—C275 | −179.2 (2) |
C13—C13A—C18A—N18 | −176.2 (2) | C274—C275—C276—C271 | −1.9 (3) |
N11—C18A—N18—C17 | −166.9 (2) | N21—C28A—N28—C27 | 168.4 (2) |
C13A—C18A—N18—C17 | 11.1 (3) | C23A—C28A—N28—C27 | −12.5 (4) |
C16—C17—N18—C18A | −56.0 (3) | C26—C27—N28—C28A | 52.7 (3) |
C171—C17—N18—C18A | 179.35 (19) | C271—C27—N28—C28A | 176.37 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C153—H15A···O252i | 0.99 | 2.48 | 3.327 (3) | 144 |
C16—H16A···N12ii | 0.99 | 2.54 | 3.429 (3) | 150 |
C172—H172···N24 | 0.95 | 2.56 | 3.426 (3) | 152 |
C275—H275···O251iii | 0.95 | 2.45 | 3.367 (3) | 163 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z; (iii) x, −y+1/2, z−1/2. |
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