10-(2-Bromo-4,5-dimethoxy­benz­yl)-7-chloro-5-cyclo­propyl-9-methyl-5,10-dihydro-4,5,6,10-tetra­azadibenzo[a,d]cyclo­hepten-11-one

In the crystal structure of the title compound, C₂₄H₂₂BrClN₄O₃, there are C—H...O and C—H...Br intermolecular hydrogen bonds, and also C—H...O, C—H...Br and C—H...N intramolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.155
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97

Author Response: ...We have collected data on kappa IP diffractometer and processed using Denzo; and 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.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H14    ..  H29B    ..       2.13 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

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

10-(2-Bromo-4,5-dimethoxy-benzyl) -7-chloro-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo [a,d]cyclohepten-11-one

Crystal data

C24H22BrClN4O3	F(000) = 1080
Mr = 529.82	Dx = 1.495 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7627 reflections
a = 9.0680 (9) Å	θ = 2.4–25.0°
b = 16.7840 (9) Å	µ = 1.89 mm^−1
c = 16.1960 (16) Å	T = 295 K
β = 107.260 (2)°	Block, pale yellow
V = 2354.0 (4) Å^3	0.30 × 0.25 × 0.25 mm
Z = 4

Data collection

MacScience DIPLabo 32001 diffractometer	2933 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
Detector resolution: 10.0 pixels mm^-1	h = −10→10
ω scans	k = −19→19
7627 measured reflections	l = −19→19
4048 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0944P)^2 + 0.2553P] where P = (Fo^2 + 2Fc^2)/3
4048 reflections	(Δ/σ)max < 0.001
301 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.68 e Å^−3

Special details

Experimental. Melting points were determined using SELACO-650 hot-stage melting-point apparatus and are uncorrected. Infrared (IR) spectra were recorded using a Jasco FTIR-4100 series. Nuclear magnetic resonance (¹H NMR) spectra were recorded on Shimadzu AMX 400-Bruker, 400 MHz s pectrometer using CDCl₃ as solvent and TMS as an internal standard. Elemental analyses (CHNS) were performed on a Vario EL III Elementar. Silica gel column chromatography was performed using Merck 7734 silica gel (60–120 mesh) and Merck-made TLC plates. Melting point: 461–463 K. IR (KBr, cm^-1) ν: 1222, 1640, 2926, 3000, 3073 ¹H NMR (CDCl₃, 400 MHz) δ: 8.45 (1H, m), 8.06 (1H, m), 7.02 (1H, s), 7.08 (1H, m), 6.95 (1H, m), 7.0 (1H, s), 4.25 (1H, d), 5.85 (1H, d), 2.32 (5H, s), 1.65 (3H, s), 3.80 (3H, s), 3.84 (3H, s). Elemental analysis data in (%) for C₂₄H₂₂BrClN₄O₃; Calculated: C 54.41, H 4.19, N 10.57. Found: C 54.43, H 4.17, N 10.54.

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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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
Br29	0.4986 (5)	0.59422 (3)	0.25969 (3)	0.0653 (2)
Cl1	0.32343 (16)	0.42506 (8)	−0.04134 (8)	0.0751 (5)
O18	−0.0942 (4)	0.50473 (19)	0.3195 (2)	0.0680 (12)
O30	0.6757 (4)	0.35892 (18)	0.4785 (2)	0.0710 (12)
O32	0.4100 (4)	0.33985 (18)	0.5024 (2)	0.0712 (12)
N3	0.2026 (4)	0.39674 (18)	0.0827 (2)	0.0464 (11)
N5	0.0908 (4)	0.35607 (16)	0.1890 (2)	0.0429 (10)
N7	−0.1413 (4)	0.28578 (19)	0.1416 (2)	0.0597 (14)
N13	0.0640 (4)	0.51688 (17)	0.23551 (19)	0.0423 (10)
C2	0.2354 (5)	0.4551 (3)	0.0358 (3)	0.0528 (16)
C4	0.1380 (4)	0.4182 (2)	0.1435 (2)	0.0426 (12)
C6	−0.0690 (5)	0.3527 (2)	0.1766 (2)	0.0455 (12)
C8	−0.2938 (6)	0.2832 (3)	0.1273 (3)	0.0687 (17)
C9	−0.3788 (6)	0.3443 (3)	0.1452 (3)	0.0640 (17)
C10	−0.3020 (5)	0.4116 (2)	0.1843 (3)	0.0548 (17)
C11	−0.1448 (5)	0.4175 (2)	0.2006 (3)	0.0456 (12)
C12	−0.0573 (5)	0.4835 (2)	0.2555 (3)	0.0472 (12)
C14	0.1086 (4)	0.4973 (2)	0.1605 (2)	0.0405 (12)
C15	0.1360 (5)	0.5565 (2)	0.1063 (2)	0.0480 (14)
C16	0.2010 (5)	0.5339 (2)	0.0426 (3)	0.0543 (14)
C17	0.0957 (6)	0.6434 (2)	0.1145 (3)	0.0651 (16)
C19	0.1711 (5)	0.2815 (2)	0.1934 (3)	0.0535 (16)
C20	0.2053 (6)	0.2374 (3)	0.2763 (3)	0.078 (2)
C21	0.3295 (6)	0.2800 (3)	0.2511 (3)	0.0711 (18)
C22	0.1787 (5)	0.5617 (2)	0.3045 (3)	0.0500 (14)
C23	0.3164 (5)	0.5098 (2)	0.3490 (2)	0.0467 (12)
C24	0.2998 (5)	0.4502 (2)	0.4058 (3)	0.0524 (14)
C25	0.4187 (5)	0.4000 (2)	0.4476 (3)	0.0546 (14)
C26	0.5637 (5)	0.4096 (2)	0.4337 (3)	0.0511 (14)
C27	0.5831 (5)	0.4673 (2)	0.3779 (3)	0.0509 (12)
C28	0.4587 (5)	0.5161 (2)	0.3360 (3)	0.0483 (14)
C31	0.8231 (6)	0.3641 (3)	0.4658 (4)	0.085 (2)
C33	0.2655 (6)	0.3249 (3)	0.5151 (4)	0.081 (2)
H10	0.2209	0.5715	0.0051	0.0650*
H13A	0.3702	0.3286	0.2819	0.0850*
H13B	0.4046	0.2481	0.2339	0.0850*
H14	0.1489	0.2499	0.1403	0.0640*
H15A	0.2044	0.1797	0.2741	0.0930*
H15B	0.1700	0.2603	0.3221	0.0930*
H18	−0.3566	0.4531	0.1996	0.0660*
H19	−0.4857	0.3406	0.1313	0.0770*
H20	−0.3455	0.2368	0.1038	0.0820*
H22A	0.1301	0.5804	0.3468	0.0600*
H22B	0.2136	0.6078	0.2795	0.0600*
H24	0.2046	0.4441	0.4158	0.0630*
H27	0.6784	0.4739	0.3681	0.0610*
H29A	0.2348	0.3703	0.5421	0.1210*
H29B	0.2731	0.2791	0.5517	0.1210*
H29C	0.1902	0.3151	0.4603	0.1210*
H30A	0.8146	0.3522	0.4066	0.1280*
H30B	0.8916	0.3266	0.5029	0.1280*
H30C	0.8630	0.4171	0.4793	0.1280*
H33A	0.1884	0.6730	0.1408	0.0980*
H33B	0.0276	0.6474	0.1498	0.0980*
H33C	0.0456	0.6648	0.0582	0.0980*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br29	0.0683 (4)	0.0623 (3)	0.0702 (4)	−0.0057 (2)	0.0282 (3)	0.0174 (2)
Cl1	0.0850 (9)	0.1010 (9)	0.0526 (7)	0.0071 (6)	0.0408 (7)	0.0055 (6)
O18	0.066 (2)	0.087 (2)	0.062 (2)	−0.0144 (16)	0.0357 (18)	−0.0233 (16)
O30	0.060 (2)	0.082 (2)	0.072 (2)	0.0123 (15)	0.0210 (17)	0.0291 (17)
O32	0.068 (2)	0.083 (2)	0.068 (2)	−0.0006 (16)	0.0285 (18)	0.0299 (16)
N3	0.049 (2)	0.0530 (18)	0.0397 (18)	0.0028 (14)	0.0172 (15)	0.0018 (14)
N5	0.053 (2)	0.0377 (16)	0.0440 (18)	0.0039 (13)	0.0235 (16)	0.0029 (12)
N7	0.062 (3)	0.0508 (19)	0.067 (2)	−0.0112 (16)	0.020 (2)	−0.0088 (16)
N13	0.0436 (19)	0.0464 (17)	0.0386 (18)	0.0002 (13)	0.0147 (15)	−0.0034 (13)
C2	0.056 (3)	0.070 (3)	0.036 (2)	0.000 (2)	0.019 (2)	0.0006 (18)
C4	0.043 (2)	0.050 (2)	0.035 (2)	0.0023 (15)	0.0121 (17)	0.0016 (15)
C6	0.048 (2)	0.052 (2)	0.038 (2)	0.0005 (16)	0.0151 (18)	0.0052 (16)
C8	0.064 (3)	0.067 (3)	0.073 (3)	−0.018 (2)	0.017 (3)	−0.009 (2)
C9	0.048 (3)	0.078 (3)	0.065 (3)	−0.013 (2)	0.015 (2)	0.002 (2)
C10	0.050 (3)	0.065 (3)	0.052 (3)	0.0030 (19)	0.019 (2)	0.0024 (19)
C11	0.047 (2)	0.051 (2)	0.043 (2)	−0.0016 (16)	0.0200 (18)	0.0012 (16)
C12	0.045 (2)	0.055 (2)	0.043 (2)	0.0048 (17)	0.0152 (19)	−0.0010 (17)
C14	0.039 (2)	0.047 (2)	0.035 (2)	0.0023 (15)	0.0104 (17)	0.0019 (15)
C15	0.052 (3)	0.049 (2)	0.041 (2)	−0.0014 (17)	0.0105 (19)	0.0073 (17)
C16	0.062 (3)	0.062 (2)	0.039 (2)	−0.003 (2)	0.015 (2)	0.0123 (18)
C17	0.080 (3)	0.048 (2)	0.065 (3)	0.006 (2)	0.018 (3)	0.0133 (19)
C19	0.064 (3)	0.043 (2)	0.061 (3)	0.0074 (18)	0.030 (2)	0.0010 (18)
C20	0.100 (4)	0.060 (3)	0.087 (4)	0.024 (3)	0.049 (3)	0.024 (2)
C21	0.067 (3)	0.054 (2)	0.095 (4)	0.019 (2)	0.028 (3)	0.010 (2)
C22	0.055 (3)	0.050 (2)	0.048 (2)	−0.0005 (18)	0.020 (2)	−0.0044 (18)
C23	0.050 (2)	0.050 (2)	0.041 (2)	−0.0047 (17)	0.0151 (19)	−0.0067 (16)
C24	0.045 (2)	0.068 (3)	0.047 (2)	−0.0066 (19)	0.018 (2)	0.0010 (19)
C25	0.060 (3)	0.061 (2)	0.045 (2)	−0.002 (2)	0.019 (2)	0.0114 (19)
C26	0.052 (3)	0.057 (2)	0.044 (2)	0.0002 (18)	0.0136 (19)	0.0065 (18)
C27	0.045 (2)	0.063 (2)	0.047 (2)	−0.0029 (18)	0.017 (2)	0.0014 (19)
C28	0.054 (3)	0.048 (2)	0.044 (2)	−0.0062 (17)	0.0160 (19)	−0.0011 (16)
C31	0.064 (4)	0.103 (4)	0.096 (4)	0.020 (3)	0.034 (3)	0.024 (3)
C33	0.076 (4)	0.101 (4)	0.072 (3)	−0.014 (3)	0.031 (3)	0.028 (3)

Geometric parameters (Å, º)

Br29—C28	1.909 (4)	C22—C23	1.518 (6)
Cl1—C2	1.745 (5)	C23—C24	1.397 (5)
O18—C12	1.233 (6)	C23—C28	1.372 (7)
O30—C26	1.358 (5)	C24—C25	1.378 (6)
O30—C31	1.414 (7)	C25—C26	1.408 (7)
O32—C25	1.362 (5)	C26—C27	1.371 (6)
O32—C33	1.408 (7)	C27—C28	1.396 (6)
N3—C2	1.326 (6)	C8—H20	0.9302
N3—C4	1.336 (5)	C9—H19	0.9299
N5—C4	1.415 (5)	C10—H18	0.9298
N5—C6	1.404 (6)	C16—H10	0.9299
N5—C19	1.439 (5)	C17—H33A	0.9604
N7—C6	1.339 (5)	C17—H33B	0.9603
N7—C8	1.333 (7)	C17—H33C	0.9597
N13—C12	1.356 (6)	C19—H14	0.9791
N13—C14	1.428 (5)	C20—H15A	0.9690
N13—C22	1.485 (5)	C20—H15B	0.9702
C2—C16	1.371 (6)	C21—H13A	0.9701
C4—C14	1.397 (5)	C21—H13B	0.9699
C6—C11	1.402 (5)	C22—H22A	0.9702
C8—C9	1.365 (7)	C22—H22B	0.9689
C9—C10	1.378 (6)	C24—H24	0.9300
C10—C11	1.374 (7)	C27—H27	0.9304
C11—C12	1.493 (6)	C31—H30A	0.9598
C14—C15	1.396 (5)	C31—H30B	0.9600
C15—C16	1.384 (6)	C31—H30C	0.9608
C15—C17	1.519 (5)	C33—H29A	0.9600
C19—C20	1.483 (6)	C33—H29B	0.9606
C19—C21	1.463 (7)	C33—H29C	0.9599
C20—C21	1.490 (8)
Br29···C15	3.541 (4)	C27···H30C	2.7158
Br29···C21^i	3.514 (5)	C31···H27	2.5278
Br29···H22B	2.7067	C31···H22A^viii	3.0815
Br29···H33A	3.1866	C33···H24	2.5233
Br29···H18^ii	3.0066	C33···H14^x	2.8422
Br29···H13B^i	2.7199	H10···H33C	2.5554
Br29···H15A^i	3.2382	H13A···C4	2.9864
Cl1···C10^iii	3.556 (4)	H13A···C24	3.0594
O18···C27^iv	3.390 (6)	H13A···C25	2.8515
O30···O32	2.571 (5)	H13A···C26	2.9003
O30···C8^v	3.343 (6)	H13B···Br29^vii	2.7199
O32···O30	2.571 (5)	H14···N3	2.7297
O18···H27^iv	2.4703	H14···N7	2.7057
O18···H22A	2.3263	H14···C33^ix	2.8422
O18···H24	2.8813	H14···H29B^ix	2.1269
O18···H18	2.7279	H15A···Br29^vii	3.2382
O30···H20^v	2.6397	H15B···H29C	2.3762
O32···H20^v	2.6659	H18···Br29^iv	3.0066
N3···C21	3.277 (6)	H18···O18	2.7279
N5···N13	2.832 (4)	H19···N3^iv	2.8594
N7···C20	3.351 (6)	H19···C21^iv	3.0882
N13···N5	2.832 (4)	H20···O30^vi	2.6397
N3···H33C^iii	2.8796	H20···O32^vi	2.6659
N3···H19^ii	2.8594	H22A···O18	2.3263
N3···H14	2.7297	H22A···H24	2.5477
N7···H14	2.7057	H22A···C31^viii	3.0815
N13···H33B	2.5618	H22B···Br29	2.7067
C2···C15^iii	3.475 (6)	H22B···C15	2.8167
C4···C23	3.587 (5)	H22B···C17	2.6355
C8···O30^vi	3.343 (6)	H22B···H33A	2.4477
C10···Cl1^iii	3.556 (4)	H22B···H33B	2.3657
C12···C24	3.471 (7)	H24···O18	2.8813
C14···C28	3.592 (6)	H24···C12	3.0264
C15···Br29	3.541 (4)	H24···C33	2.5233
C15···C2^iii	3.475 (6)	H24···H22A	2.5477
C17···C22	3.247 (6)	H24···H29A	2.3369
C20···N7	3.351 (6)	H24···H29C	2.2979
C21···N3	3.277 (6)	H27···O18^ii	2.4703
C21···Br29^vii	3.514 (5)	H27···C31	2.5278
C22···C17	3.247 (6)	H27···H30A	2.3726
C23···C4	3.587 (5)	H27···H30C	2.2728
C24···C12	3.471 (7)	H29A···C24	2.7912
C24···C26^viii	3.452 (6)	H29A···H24	2.3369
C26···C24^viii	3.452 (6)	H29B···C19^x	2.9011
C27···O18^ii	3.390 (6)	H29B···H14^x	2.1269
C28···C14	3.592 (6)	H29C···C24	2.7256
C4···H13A	2.9864	H29C···H15B	2.3762
C12···H24	3.0264	H29C···H24	2.2979
C15···H22B	2.8167	H30A···C27	2.7885
C17···H22B	2.6355	H30A···H27	2.3726
C19···H29B^ix	2.9011	H30C···C27	2.7158
C21···H19^ii	3.0882	H30C···H27	2.2728
C22···H33B	2.8613	H33A···Br29	3.1866
C24···H29C	2.7256	H33A···H22B	2.4477
C24···H29A	2.7912	H33B···N13	2.5618
C24···H13A	3.0594	H33B···C22	2.8613
C25···H13A	2.8515	H33B···H22B	2.3657
C26···H13A	2.9003	H33C···H10	2.5554
C27···H30A	2.7885	H33C···N3^iii	2.8796
C26—O30—C31	118.2 (4)	Br29—C28—C23	121.3 (3)
C25—O32—C33	117.6 (4)	Br29—C28—C27	115.9 (3)
C2—N3—C4	116.4 (3)	C23—C28—C27	122.8 (4)
C4—N5—C6	114.5 (3)	N7—C8—H20	117.98
C4—N5—C19	116.1 (3)	C9—C8—H20	117.92
C6—N5—C19	117.2 (3)	C8—C9—H19	120.82
C6—N7—C8	116.9 (4)	C10—C9—H19	120.94
C12—N13—C14	124.2 (3)	C9—C10—H18	119.99
C12—N13—C22	117.8 (3)	C11—C10—H18	119.93
C14—N13—C22	116.4 (3)	C2—C16—H10	120.63
Cl1—C2—N3	115.1 (4)	C15—C16—H10	120.59
Cl1—C2—C16	120.0 (4)	C15—C17—H33A	109.50
N3—C2—C16	124.9 (4)	C15—C17—H33B	109.45
N3—C4—N5	116.9 (3)	C15—C17—H33C	109.55
N3—C4—C14	123.5 (3)	H33A—C17—H33B	109.43
N5—C4—C14	119.5 (3)	H33A—C17—H33C	109.46
N5—C6—N7	116.7 (3)	H33B—C17—H33C	109.43
N5—C6—C11	120.0 (3)	N5—C19—H14	117.29
N7—C6—C11	123.3 (4)	C20—C19—H14	117.26
N7—C8—C9	124.1 (5)	C21—C19—H14	117.31
C8—C9—C10	118.2 (5)	C19—C20—H15A	117.92
C9—C10—C11	120.1 (4)	C19—C20—H15B	117.82
C6—C11—C10	117.2 (4)	C21—C20—H15A	117.93
C6—C11—C12	121.5 (4)	C21—C20—H15B	117.85
C10—C11—C12	120.4 (4)	H15A—C20—H15B	115.02
O18—C12—N13	121.5 (4)	C19—C21—H13A	117.75
O18—C12—C11	119.1 (4)	C19—C21—H13B	117.77
N13—C12—C11	119.3 (4)	C20—C21—H13A	117.77
N13—C14—C4	120.3 (3)	C20—C21—H13B	117.78
N13—C14—C15	121.3 (3)	H13A—C21—H13B	114.80
C4—C14—C15	118.2 (3)	N13—C22—H22A	109.37
C14—C15—C16	117.9 (3)	N13—C22—H22B	109.43
C14—C15—C17	122.4 (4)	C23—C22—H22A	109.42
C16—C15—C17	119.7 (3)	C23—C22—H22B	109.39
C2—C16—C15	118.8 (4)	H22A—C22—H22B	108.05
N5—C19—C20	116.5 (4)	C23—C24—H24	118.71
N5—C19—C21	115.7 (4)	C25—C24—H24	118.60
C20—C19—C21	60.7 (3)	C26—C27—H27	120.26
C19—C20—C21	59.0 (3)	C28—C27—H27	120.30
C19—C21—C20	60.3 (3)	O30—C31—H30A	109.47
N13—C22—C23	111.1 (3)	O30—C31—H30B	109.43
C22—C23—C24	119.3 (4)	O30—C31—H30C	109.40
C22—C23—C28	124.2 (3)	H30A—C31—H30B	109.52
C24—C23—C28	116.5 (4)	H30A—C31—H30C	109.46
C23—C24—C25	122.7 (4)	H30B—C31—H30C	109.55
O32—C25—C24	125.8 (4)	O32—C33—H29A	109.47
O32—C25—C26	115.3 (4)	O32—C33—H29B	109.47
C24—C25—C26	118.9 (4)	O32—C33—H29C	109.45
O30—C26—C25	115.4 (4)	H29A—C33—H29B	109.36
O30—C26—C27	124.9 (4)	H29A—C33—H29C	109.53
C25—C26—C27	119.7 (4)	H29B—C33—H29C	109.54
C26—C27—C28	119.4 (4)
C31—O30—C26—C25	178.4 (4)	N7—C6—C11—C12	167.2 (4)
C31—O30—C26—C27	−1.6 (6)	N7—C6—C11—C10	−2.0 (6)
C33—O32—C25—C26	−176.8 (4)	N5—C6—C11—C12	−12.8 (6)
C33—O32—C25—C24	2.9 (6)	N5—C6—C11—C10	178.0 (4)
C4—N3—C2—C16	−3.4 (7)	N7—C8—C9—C10	−3.2 (7)
C4—N3—C2—Cl1	178.7 (3)	C8—C9—C10—C11	3.0 (7)
C2—N3—C4—N5	174.9 (4)	C9—C10—C11—C12	−169.9 (4)
C2—N3—C4—C14	−1.8 (6)	C9—C10—C11—C6	−0.6 (6)
C19—N5—C4—N3	25.5 (5)	C10—C11—C12—N13	−143.5 (4)
C19—N5—C6—N7	−21.8 (5)	C10—C11—C12—O18	38.7 (6)
C6—N5—C4—N3	−116.0 (4)	C6—C11—C12—O18	−130.2 (4)
C19—N5—C6—C11	158.2 (4)	C6—C11—C12—N13	47.6 (6)
C4—N5—C19—C21	73.0 (5)	C4—C14—C15—C17	174.9 (4)
C4—N5—C6—C11	−60.8 (4)	C4—C14—C15—C16	−4.5 (6)
C19—N5—C4—C14	−157.7 (3)	N13—C14—C15—C17	−10.2 (6)
C4—N5—C6—N7	119.3 (3)	N13—C14—C15—C16	170.4 (4)
C6—N5—C4—C14	60.8 (4)	C14—C15—C16—C2	−0.1 (6)
C6—N5—C19—C21	−146.5 (4)	C17—C15—C16—C2	−179.5 (4)
C6—N5—C19—C20	−78.0 (5)	N5—C19—C21—C20	107.3 (5)
C4—N5—C19—C20	141.5 (4)	N5—C19—C20—C21	−106.0 (4)
C8—N7—C6—C11	2.0 (5)	N13—C22—C23—C24	−73.4 (5)
C6—N7—C8—C9	0.7 (6)	N13—C22—C23—C28	105.2 (4)
C8—N7—C6—N5	−178.1 (3)	C24—C23—C28—C27	−1.3 (6)
C12—N13—C22—C23	96.5 (4)	C24—C23—C28—Br29	179.6 (3)
C22—N13—C12—C11	−160.1 (3)	C28—C23—C24—C25	0.3 (6)
C14—N13—C12—C11	4.9 (6)	C22—C23—C28—Br29	1.0 (5)
C14—N13—C22—C23	−69.8 (4)	C22—C23—C24—C25	179.0 (4)
C12—N13—C14—C4	−54.6 (5)	C22—C23—C28—C27	−179.9 (4)
C22—N13—C14—C4	110.7 (4)	C23—C24—C25—C26	0.9 (6)
C22—N13—C12—O18	17.7 (6)	C23—C24—C25—O32	−178.7 (4)
C12—N13—C14—C15	130.6 (4)	C24—C25—C26—O30	178.7 (4)
C14—N13—C12—O18	−177.3 (4)	O32—C25—C26—O30	−1.6 (5)
C22—N13—C14—C15	−64.1 (5)	C24—C25—C26—C27	−1.3 (6)
Cl1—C2—C16—C15	−177.8 (3)	O32—C25—C26—C27	178.4 (4)
N3—C2—C16—C15	4.3 (7)	C25—C26—C27—C28	0.4 (6)
N5—C4—C14—N13	14.1 (5)	O30—C26—C27—C28	−179.6 (4)
N5—C4—C14—C15	−170.9 (3)	C26—C27—C28—Br29	−179.9 (3)
N3—C4—C14—C15	5.7 (6)	C26—C27—C28—C23	0.9 (6)
N3—C4—C14—N13	−169.3 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H13B···Br29^vii	0.97	2.72	3.514 (5)	139
C22—H22A···O18	0.97	2.33	2.730 (6)	104
C22—H22B···Br29	0.97	2.71	3.239 (5)	115
C27—H27···O18^ii	0.93	2.47	3.390 (6)	170
C17—H33B···N13	0.96	2.56	2.961 (5)	105

Symmetry codes: (ii) x+1, y, z; (vii) −x+1, y−1/2, −z+1/2.