N,N′-Bis(2-chloro­phen­yl)-4-(4-chloro­phen­yl)-2,6-dimeth­yl-1,4-dihydro­pyridine-3,5-dicarboxamide

In the title compound, C₂₇H₂₂Cl₃N₃O₂, the dihydro­pyridine ring has a boat conformation. The mol­ecules are linked by N—H...O, N—H...Cl, C—H...N and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.181
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.82

Author Response: ...We have collected data on kappa IP diffractometer and processed using Denzo; and as we know that the DENZO image processing package is known to have problems with certain strong reflections. They are often excluded from the data set leading to a lower value for the above parameter.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT411_ALERT_2_C Short Inter H...H Contact  H26    ..  H26     ..       2.14 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H4     ..  H21     ..       1.91 Ang.

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.88
           From the CIF: _reflns_number_total               4452
           From the CIF: _diffrn_reflns_limit_ max hkl   24.   11.   29.
           From the CIF: _diffrn_reflns_limit_ min hkl  -23.  -10.  -29.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   27.   14.   29.
           Calculated minimum hkl  -27.  -14.  -29.

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N,N'-Bis(2-chlorophenyl)-4-(4-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine- 3,5-dicarboxamide

Crystal data

C27H22Cl3N3O2	F(000) = 2176
Mr = 526.83	Dx = 1.440 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8244 reflections
a = 20.566 (2) Å	θ = 2.2–27.9°
b = 10.698 (1) Å	µ = 0.41 mm^−1
c = 22.789 (2) Å	T = 295 K
β = 104.300 (2)°	Block, pale yellow
V = 4858.6 (6) Å^3	0.25 × 0.2 × 0.2 mm
Z = 8

Data collection

MacScience DIPLabo 32001 diffractometer	3458 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 27.9°, θmin = 2.2°
Detector resolution: 10.0 pixels mm^-1	h = −23→24
ω scans	k = −10→11
8244 measured reflections	l = −29→29
4452 independent reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.181	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0987P)^2 + 5.2071P] where P = (Fo^2 + 2Fc^2)/3
4452 reflections	(Δ/σ)max = 0.001
318 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl18	0.09102 (6)	0.59825 (9)	−0.00269 (5)	0.0810 (4)
Cl28	0.41371 (6)	1.26469 (11)	−0.00586 (4)	0.0846 (4)
Cl33	0.04486 (5)	1.44280 (9)	−0.16350 (5)	0.0743 (4)
O10	0.23572 (14)	0.9927 (2)	0.00425 (9)	0.0709 (9)
O20	0.33356 (12)	1.1223 (2)	−0.22633 (9)	0.0632 (9)
N1	0.21442 (14)	0.8233 (2)	−0.18927 (10)	0.0524 (9)
N11	0.16902 (15)	0.8247 (2)	−0.01223 (11)	0.0550 (10)
N21	0.36877 (15)	1.1488 (3)	−0.12580 (11)	0.0622 (10)
C2	0.19948 (15)	0.8127 (3)	−0.13359 (12)	0.0435 (10)
C3	0.21686 (15)	0.9062 (2)	−0.09306 (11)	0.0401 (9)
C4	0.24833 (14)	1.0261 (2)	−0.10979 (11)	0.0396 (9)
C5	0.27892 (15)	1.0058 (3)	−0.16375 (11)	0.0425 (9)
C6	0.25785 (17)	0.9107 (3)	−0.20244 (12)	0.0491 (10)
C7	0.2789 (2)	0.8814 (3)	−0.25950 (15)	0.0678 (13)
C8	0.16615 (19)	0.6912 (3)	−0.12704 (14)	0.0587 (13)
C9	0.20840 (15)	0.9112 (3)	−0.03013 (11)	0.0422 (9)
C12	0.14778 (16)	0.8193 (3)	0.04172 (13)	0.0508 (10)
C13	0.1610 (2)	0.9116 (4)	0.08624 (14)	0.0632 (13)
C14	0.1362 (2)	0.9002 (5)	0.13694 (17)	0.0823 (18)
C15	0.0981 (2)	0.7991 (5)	0.14445 (18)	0.0874 (18)
C16	0.0845 (2)	0.7072 (4)	0.10163 (18)	0.0753 (17)
C17	0.10930 (18)	0.7173 (3)	0.05090 (15)	0.0599 (11)
C19	0.32807 (16)	1.0958 (3)	−0.17539 (12)	0.0453 (10)
C22	0.41969 (17)	1.2387 (3)	−0.12260 (15)	0.0578 (11)
C23	0.4476 (2)	1.2680 (5)	−0.17038 (18)	0.0837 (16)
C24	0.4981 (2)	1.3571 (5)	−0.1624 (2)	0.0977 (19)
C25	0.5221 (2)	1.4148 (4)	−0.1085 (2)	0.0876 (19)
C26	0.4971 (2)	1.3843 (4)	−0.0602 (2)	0.0761 (16)
C27	0.44584 (18)	1.2982 (3)	−0.06770 (16)	0.0601 (12)
C29	0.19763 (14)	1.1314 (2)	−0.12286 (11)	0.0386 (9)
C30	0.13900 (16)	1.1194 (3)	−0.16827 (12)	0.0475 (10)
C31	0.09226 (16)	1.2138 (3)	−0.18055 (14)	0.0522 (11)
C32	0.10354 (16)	1.3226 (3)	−0.14752 (13)	0.0493 (10)
C34	0.16127 (17)	1.3383 (3)	−0.10235 (13)	0.0511 (10)
C35	0.20752 (16)	1.2425 (3)	−0.09022 (12)	0.0464 (10)
H1	0.19540	0.77210	−0.21740	0.0630*
H4	0.28450	1.05080	−0.07500	0.0480*
H7A	0.24920	0.92240	−0.29310	0.1020*
H7B	0.27700	0.79270	−0.26610	0.1020*
H7C	0.32390	0.91030	−0.25570	0.1020*
H8A	0.19080	0.64920	−0.09120	0.0880*
H8B	0.16510	0.63970	−0.16180	0.0880*
H8C	0.12110	0.70650	−0.12390	0.0880*
H11	0.15520	0.76490	−0.03740	0.0660*
H13	0.18650	0.98100	0.08170	0.0760*
H14	0.14540	0.96200	0.16650	0.0990*
H15	0.08140	0.79310	0.17880	0.1050*
H16	0.05870	0.63840	0.10660	0.0900*
H21	0.36280	1.12430	−0.09160	0.0740*
H23	0.43270	1.22810	−0.20750	0.1000*
H24	0.51580	1.37780	−0.19500	0.1170*
H25	0.55560	1.47500	−0.10440	0.1050*
H26	0.51440	1.42130	−0.02270	0.0910*
H30	0.13120	1.04600	−0.19080	0.0570*
H31	0.05320	1.20410	−0.21110	0.0630*
H34	0.16900	1.41240	−0.08040	0.0610*
H35	0.24630	1.25240	−0.05940	0.0560*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl18	0.0925 (9)	0.0607 (6)	0.1038 (8)	−0.0138 (5)	0.0506 (6)	0.0022 (4)
Cl28	0.0837 (9)	0.1103 (8)	0.0659 (6)	−0.0267 (6)	0.0303 (5)	−0.0191 (5)
Cl33	0.0617 (7)	0.0631 (6)	0.1028 (7)	0.0124 (4)	0.0292 (5)	0.0148 (4)
O10	0.091 (2)	0.0860 (17)	0.0404 (11)	−0.0415 (14)	0.0254 (11)	−0.0146 (10)
O20	0.0744 (18)	0.0755 (15)	0.0434 (12)	−0.0065 (12)	0.0215 (11)	0.0152 (10)
N1	0.068 (2)	0.0539 (15)	0.0395 (12)	−0.0093 (12)	0.0211 (11)	−0.0101 (10)
N11	0.069 (2)	0.0587 (16)	0.0442 (13)	−0.0158 (13)	0.0273 (12)	−0.0057 (11)
N21	0.063 (2)	0.0812 (19)	0.0451 (14)	−0.0243 (15)	0.0187 (12)	0.0070 (12)
C2	0.048 (2)	0.0457 (16)	0.0385 (14)	−0.0001 (12)	0.0137 (12)	−0.0001 (11)
C3	0.0408 (19)	0.0455 (15)	0.0352 (13)	−0.0011 (11)	0.0117 (11)	0.0025 (10)
C4	0.0415 (19)	0.0463 (15)	0.0327 (12)	−0.0054 (11)	0.0122 (11)	0.0005 (10)
C5	0.0424 (19)	0.0523 (16)	0.0354 (13)	0.0038 (12)	0.0145 (11)	0.0052 (11)
C6	0.060 (2)	0.0529 (17)	0.0395 (15)	0.0059 (13)	0.0218 (13)	0.0009 (11)
C7	0.092 (3)	0.071 (2)	0.0525 (18)	0.0033 (19)	0.0407 (19)	−0.0063 (15)
C8	0.080 (3)	0.0479 (18)	0.0516 (17)	−0.0121 (15)	0.0230 (16)	−0.0077 (13)
C9	0.0437 (19)	0.0491 (16)	0.0348 (13)	−0.0022 (12)	0.0117 (11)	0.0022 (10)
C12	0.049 (2)	0.0645 (19)	0.0433 (15)	0.0045 (14)	0.0197 (13)	0.0099 (12)
C13	0.063 (3)	0.086 (2)	0.0454 (17)	0.0008 (18)	0.0224 (15)	−0.0006 (15)
C14	0.081 (3)	0.120 (4)	0.053 (2)	−0.001 (3)	0.0299 (19)	−0.007 (2)
C15	0.084 (3)	0.131 (4)	0.060 (2)	0.012 (3)	0.042 (2)	0.020 (2)
C16	0.067 (3)	0.092 (3)	0.079 (3)	0.007 (2)	0.041 (2)	0.031 (2)
C17	0.057 (2)	0.067 (2)	0.0627 (19)	0.0080 (16)	0.0282 (16)	0.0185 (15)
C19	0.044 (2)	0.0527 (17)	0.0433 (15)	0.0087 (13)	0.0184 (13)	0.0105 (11)
C22	0.045 (2)	0.071 (2)	0.0603 (19)	−0.0077 (16)	0.0184 (15)	0.0108 (15)
C23	0.068 (3)	0.122 (3)	0.066 (2)	−0.027 (3)	0.0260 (19)	0.013 (2)
C24	0.066 (3)	0.138 (4)	0.094 (3)	−0.031 (3)	0.029 (2)	0.036 (3)
C25	0.060 (3)	0.089 (3)	0.112 (4)	−0.018 (2)	0.018 (2)	0.019 (2)
C26	0.058 (3)	0.071 (2)	0.099 (3)	−0.0094 (18)	0.019 (2)	−0.006 (2)
C27	0.051 (2)	0.064 (2)	0.068 (2)	−0.0037 (16)	0.0200 (16)	0.0014 (15)
C29	0.0429 (18)	0.0453 (15)	0.0312 (12)	−0.0050 (12)	0.0158 (11)	0.0014 (10)
C30	0.047 (2)	0.0508 (17)	0.0445 (15)	−0.0079 (13)	0.0107 (13)	−0.0075 (11)
C31	0.040 (2)	0.0628 (19)	0.0524 (17)	−0.0042 (14)	0.0090 (13)	0.0002 (13)
C32	0.050 (2)	0.0497 (17)	0.0544 (17)	0.0007 (13)	0.0247 (14)	0.0072 (12)
C34	0.063 (2)	0.0438 (16)	0.0504 (16)	−0.0021 (14)	0.0212 (14)	−0.0048 (12)
C35	0.052 (2)	0.0500 (17)	0.0375 (14)	−0.0063 (13)	0.0115 (12)	−0.0060 (11)

Geometric parameters (Å, º)

Cl18—C17	1.740 (3)	C22—C23	1.386 (5)
Cl28—C27	1.735 (4)	C23—C24	1.388 (7)
Cl33—C32	1.739 (3)	C24—C25	1.354 (6)
O10—C9	1.213 (4)	C25—C26	1.365 (6)
O20—C19	1.227 (3)	C26—C27	1.378 (6)
N1—C2	1.382 (4)	C29—C35	1.390 (4)
N1—C6	1.376 (4)	C29—C30	1.387 (4)
N11—C9	1.357 (4)	C30—C31	1.375 (5)
N11—C12	1.404 (4)	C31—C32	1.374 (4)
N21—C19	1.353 (4)	C32—C34	1.376 (4)
N21—C22	1.410 (5)	C34—C35	1.379 (5)
N1—H1	0.8603	C4—H4	0.9800
N11—H11	0.8594	C7—H7A	0.9596
N21—H21	0.8594	C7—H7B	0.9600
C2—C8	1.494 (5)	C7—H7C	0.9592
C2—C3	1.348 (4)	C8—H8A	0.9599
C3—C4	1.527 (3)	C8—H8B	0.9608
C3—C9	1.488 (4)	C8—H8C	0.9608
C4—C5	1.529 (4)	C13—H13	0.9294
C4—C29	1.514 (4)	C14—H14	0.9294
C5—C19	1.467 (5)	C15—H15	0.9315
C5—C6	1.346 (4)	C16—H16	0.9305
C6—C7	1.502 (5)	C23—H23	0.9293
C12—C13	1.394 (5)	C24—H24	0.9312
C12—C17	1.394 (5)	C25—H25	0.9308
C13—C14	1.379 (5)	C26—H26	0.9292
C14—C15	1.371 (7)	C30—H30	0.9302
C15—C16	1.365 (6)	C31—H31	0.9298
C16—C17	1.378 (5)	C34—H34	0.9298
C22—C27	1.388 (5)	C35—H35	0.9295
Cl18···N11	2.943 (3)	C19···H7B^iv	3.0759
Cl28···C34^i	3.399 (3)	C19···H23	2.8190
Cl28···N21	2.935 (3)	C24···H8C^ix	2.9442
Cl33···C8^ii	3.599 (4)	C25···H8C^ix	3.0963
Cl18···H11	2.4621	C26···H26^x	2.8585
Cl28···H21	2.4818	C30···H25^vii	2.9462
Cl33···H16^iii	2.8873	C32···H7C^iv	3.0979
O10···C13	2.833 (5)	H1···H7B	2.2398
O10···C29	3.176 (3)	H1···H8B	2.0952
O10···C35	3.391 (4)	H1···O20^vi	2.0470
O10···C34^i	3.227 (4)	H1···C19^vi	3.0293
O20···C23	2.842 (5)	H4···O10	2.3557
O20···N1^iv	2.891 (3)	H4···N21	2.5366
O20···C7	2.838 (4)	H4···H21	1.9119
O10···H13	2.2446	H4···H35	2.3522
O10···H34^i	2.4904	H7A···H14^xi	2.4420
O10···H4	2.3557	H7B···H1	2.2398
O10···H8A^v	2.6524	H7B···O20^vi	2.8860
O20···H7C	2.3591	H7B···C19^vi	3.0759
O20···H23	2.2782	H7C···O20	2.3591
O20···H1^iv	2.0470	H7C···C19	2.6865
O20···H7B^iv	2.8860	H7C···C32^vi	3.0979
O20···H8B^iv	2.5631	H8A···N11	2.7134
N1···O20^vi	2.891 (3)	H8A···H11	2.0037
N11···C8	2.969 (4)	H8A···H34^viii	2.5949
N11···Cl18	2.943 (3)	H8A···O10^v	2.6524
N11···C25^vii	3.405 (5)	H8A···C9^v	3.0869
N21···Cl28	2.935 (3)	H8A···C13^v	3.0912
N1···H30	2.9287	H8B···H1	2.0952
N11···H8C	2.7942	H8B···O20^vi	2.5631
N11···H8A	2.7134	H8C···N11	2.7942
N21···H4	2.5366	H8C···H11	2.0212
C2···C30	3.529 (5)	H8C···C24^vii	2.9442
C6···C30	3.536 (5)	H8C···C25^vii	3.0963
C7···O20	2.838 (4)	H11···Cl18	2.4621
C8···Cl33^viii	3.599 (4)	H11···C2	2.6234
C8···N11	2.969 (4)	H11···C8	2.2523
C12···C26^vii	3.453 (5)	H11···H8A	2.0037
C13···O10	2.833 (5)	H11···H8C	2.0212
C17···C26^vii	3.470 (6)	H13···O10	2.2446
C23···O20	2.842 (5)	H13···C9	2.7968
C25···N11^ix	3.405 (5)	H14···H7A^xii	2.4420
C26···C17^ix	3.470 (6)	H16···Cl33^iii	2.8873
C26···C12^ix	3.453 (5)	H21···Cl28	2.4818
C29···O10	3.176 (3)	H21···C4	2.5171
C30···C2	3.529 (5)	H21···H4	1.9119
C30···C6	3.536 (5)	H23···O20	2.2782
C34···O10^i	3.227 (4)	H23···C19	2.8190
C34···Cl28^i	3.399 (3)	H24···H24^xiii	2.4293
C35···O10	3.391 (4)	H25···C30^ix	2.9462
C2···H11	2.6234	H26···C26^x	2.8585
C2···H30	2.9994	H26···H26^x	2.1353
C3···H30	2.8919	H26···C12^ix	2.9801
C4···H21	2.5171	H30···N1	2.9287
C5···H30	2.9781	H30···C2	2.9994
C6···H30	3.0481	H30···C3	2.8919
C8···H11	2.2523	H30···C5	2.9781
C9···H13	2.7968	H30···C6	3.0481
C9···H8A^v	3.0869	H31···H31^xiv	2.4526
C12···H26^vii	2.9801	H34···H8A^ii	2.5949
C13···H8A^v	3.0912	H34···O10^i	2.4904
C19···H7C	2.6865	H35···H4	2.3522
C19···H1^iv	3.0293
C2—N1—C6	124.0 (2)	C30—C29—C35	117.6 (3)
C9—N11—C12	129.0 (2)	C4—C29—C35	121.9 (2)
C19—N21—C22	128.8 (3)	C4—C29—C30	120.5 (2)
C6—N1—H1	118.04	C29—C30—C31	121.3 (3)
C2—N1—H1	117.95	C30—C31—C32	119.7 (3)
C12—N11—H11	115.51	Cl33—C32—C31	119.8 (2)
C9—N11—H11	115.50	Cl33—C32—C34	119.5 (2)
C19—N21—H21	115.60	C31—C32—C34	120.7 (3)
C22—N21—H21	115.57	C32—C34—C35	119.0 (3)
N1—C2—C3	119.1 (3)	C29—C35—C34	121.7 (3)
N1—C2—C8	112.0 (2)	C3—C4—H4	107.96
C3—C2—C8	128.9 (3)	C5—C4—H4	107.94
C2—C3—C9	127.8 (3)	C29—C4—H4	107.87
C2—C3—C4	120.6 (2)	C6—C7—H7A	109.44
C4—C3—C9	111.6 (2)	C6—C7—H7B	109.43
C3—C4—C5	111.4 (2)	C6—C7—H7C	109.43
C3—C4—C29	111.1 (2)	H7A—C7—H7B	109.48
C5—C4—C29	110.3 (2)	H7A—C7—H7C	109.54
C6—C5—C19	120.2 (3)	H7B—C7—H7C	109.50
C4—C5—C19	119.4 (2)	C2—C8—H8A	109.47
C4—C5—C6	120.3 (3)	C2—C8—H8B	109.51
N1—C6—C5	119.5 (3)	C2—C8—H8C	109.51
N1—C6—C7	112.9 (3)	H8A—C8—H8B	109.43
C5—C6—C7	127.6 (3)	H8A—C8—H8C	109.43
O10—C9—N11	120.8 (2)	H8B—C8—H8C	109.48
O10—C9—C3	120.2 (3)	C12—C13—H13	119.93
N11—C9—C3	119.1 (2)	C14—C13—H13	119.98
N11—C12—C17	118.3 (3)	C13—C14—H14	119.55
N11—C12—C13	124.2 (3)	C15—C14—H14	119.41
C13—C12—C17	117.5 (3)	C14—C15—H15	120.00
C12—C13—C14	120.1 (4)	C16—C15—H15	119.89
C13—C14—C15	121.0 (4)	C15—C16—H16	120.34
C14—C15—C16	120.1 (4)	C17—C16—H16	120.29
C15—C16—C17	119.4 (4)	C22—C23—H23	120.24
C12—C17—C16	121.9 (3)	C24—C23—H23	120.16
Cl18—C17—C12	120.0 (3)	C23—C24—H24	119.08
Cl18—C17—C16	118.1 (3)	C25—C24—H24	119.24
O20—C19—N21	120.7 (3)	C24—C25—H25	120.09
O20—C19—C5	123.5 (3)	C26—C25—H25	120.10
N21—C19—C5	115.8 (2)	C25—C26—H26	120.34
N21—C22—C23	124.0 (3)	C27—C26—H26	120.40
N21—C22—C27	118.5 (3)	C29—C30—H30	119.30
C23—C22—C27	117.4 (3)	C31—C30—H30	119.42
C22—C23—C24	119.6 (4)	C30—C31—H31	120.12
C23—C24—C25	121.7 (4)	C32—C31—H31	120.16
C24—C25—C26	119.8 (4)	C32—C34—H34	120.51
C25—C26—C27	119.3 (4)	C35—C34—H34	120.53
Cl28—C27—C22	119.8 (3)	C29—C35—H35	119.12
C22—C27—C26	122.2 (4)	C34—C35—H35	119.17
Cl28—C27—C26	118.1 (3)
C6—N1—C2—C3	13.8 (5)	C4—C5—C6—N1	−7.6 (4)
C6—N1—C2—C8	−164.8 (3)	C6—C5—C19—N21	−150.5 (3)
C2—N1—C6—C7	165.0 (3)	C19—C5—C6—N1	176.6 (3)
C2—N1—C6—C5	−12.0 (5)	C4—C5—C19—N21	33.7 (4)
C9—N11—C12—C13	4.6 (5)	N11—C12—C13—C14	177.9 (4)
C9—N11—C12—C17	−177.4 (3)	N11—C12—C17—Cl18	2.1 (4)
C12—N11—C9—C3	−172.0 (3)	N11—C12—C17—C16	−177.7 (3)
C12—N11—C9—O10	7.0 (5)	C13—C12—C17—Cl18	−179.8 (3)
C19—N21—C22—C27	167.2 (3)	C17—C12—C13—C14	−0.1 (5)
C22—N21—C19—C5	−179.1 (3)	C13—C12—C17—C16	0.5 (5)
C19—N21—C22—C23	−15.7 (6)	C12—C13—C14—C15	−0.3 (6)
C22—N21—C19—O20	1.6 (6)	C13—C14—C15—C16	0.5 (7)
N1—C2—C3—C9	−177.0 (3)	C14—C15—C16—C17	−0.1 (6)
C8—C2—C3—C9	1.4 (5)	C15—C16—C17—Cl18	179.9 (3)
N1—C2—C3—C4	4.1 (4)	C15—C16—C17—C12	−0.3 (6)
C8—C2—C3—C4	−177.5 (3)	N21—C22—C27—C26	177.9 (3)
C2—C3—C9—N11	−12.5 (5)	N21—C22—C23—C24	−179.3 (4)
C4—C3—C9—O10	−12.5 (4)	C23—C22—C27—Cl28	−179.4 (3)
C9—C3—C4—C5	160.4 (2)	N21—C22—C27—Cl28	−2.1 (5)
C2—C3—C4—C29	103.0 (3)	C27—C22—C23—C24	−2.1 (6)
C2—C3—C9—O10	168.5 (3)	C23—C22—C27—C26	0.6 (6)
C9—C3—C4—C29	−76.1 (3)	C22—C23—C24—C25	1.4 (7)
C4—C3—C9—N11	166.5 (3)	C23—C24—C25—C26	0.9 (7)
C2—C3—C4—C5	−20.5 (4)	C24—C25—C26—C27	−2.4 (6)
C3—C4—C5—C6	22.3 (4)	C25—C26—C27—C22	1.6 (6)
C3—C4—C5—C19	−161.9 (3)	C25—C26—C27—Cl28	−178.3 (3)
C3—C4—C29—C35	121.1 (3)	C35—C29—C30—C31	−0.1 (4)
C29—C4—C5—C19	74.2 (3)	C30—C29—C35—C34	−0.4 (4)
C29—C4—C5—C6	−101.7 (3)	C4—C29—C30—C31	179.7 (3)
C5—C4—C29—C35	−114.7 (3)	C4—C29—C35—C34	179.9 (3)
C3—C4—C29—C30	−58.6 (3)	C29—C30—C31—C32	0.2 (5)
C5—C4—C29—C30	65.5 (3)	C30—C31—C32—Cl33	179.3 (2)
C19—C5—C6—C7	0.1 (5)	C30—C31—C32—C34	0.2 (5)
C4—C5—C19—O20	−147.0 (3)	Cl33—C32—C34—C35	−179.8 (2)
C6—C5—C19—O20	28.8 (5)	C31—C32—C34—C35	−0.7 (5)
C4—C5—C6—C7	175.9 (3)	C32—C34—C35—C29	0.7 (5)

Symmetry codes: (i) −x+1/2, −y+5/2, −z; (ii) x, y+1, z; (iii) −x, −y+2, −z; (iv) −x+1/2, y+1/2, −z−1/2; (v) −x+1/2, −y+3/2, −z; (vi) −x+1/2, y−1/2, −z−1/2; (vii) x−1/2, y−1/2, z; (viii) x, y−1, z; (ix) x+1/2, y+1/2, z; (x) −x+1, −y+3, −z; (xi) x, −y+2, z−1/2; (xii) x, −y+2, z+1/2; (xiii) −x+1, y, −z−1/2; (xiv) −x, y, −z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O20^vi	0.86	2.05	2.891 (3)	167
N11—H11···Cl18	0.86	2.46	2.943 (3)	116
N21—H21···Cl28	0.86	2.48	2.935 (3)	114
C4—H4···N21	0.98	2.54	2.905 (4)	102
C7—H7C···O20	0.96	2.36	2.838 (4)	110
C8—H8B···O20^vi	0.96	2.56	3.423 (4)	149
C13—H13···O10	0.93	2.24	2.833 (5)	121
C23—H23···O20	0.93	2.28	2.842 (5)	119
C34—H34···O10^i	0.93	2.49	3.227 (4)	136

Symmetry codes: (i) −x+1/2, −y+5/2, −z; (vi) −x+1/2, y−1/2, −z−1/2.