5-(Benzo­[1,3]­dioxol-5-yl)-7-(4-chloro­phenyl)-3-methyl-1-phenyl-1,6,7,8-tetra­hydro­pyrazolo­[3,4-b][1,4]­diazepine

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).

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](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

---

Computing details

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

Crystal data

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) Å^3	Plate, yellow
Z = 8	0.25 × 0.20 × 0.02 mm
F(000) = 1904

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0779P)^2 + 0.4063P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C153—H15A···O252^i	0.99	2.48	3.327 (3)	144
C16—H16A···N12^ii	0.99	2.54	3.429 (3)	150
C172—H172···N24	0.95	2.56	3.426 (3)	152
C275—H275···O251^iii	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.