5,7-Di­bromo-4′-(4-bromo­benzoyl)-1′-methyl-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-3′′-1H-indole-2,2′′(3H,3′′H)-dione methanol solvate

The pyrrolidine ring of the title compound, C₂₆H₁₈Br₃N₃O₃·CH₄O, adopts an envelope conformation. The molecular structure is stabilized by C—H...O interactions and the packing is stabilized by N—H...O and O—H...N intermolecular interactions, which also include the methanol solvent molecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.055
• wR factor = 0.185
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C H4 O

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

5,7-Dibromo-4'-(4-bromobenzoyl)-1'-methyl-1H-indole-3-spiro-2'-pyrrolidine- 3'-spiro-3''-1H-indole-2,2''(3H,3''H)-dione methanol solvate

Crystal data

C26H18Br3N3O3·CH4O	F(000) = 2736
Mr = 692.21	Dx = 1.685 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 46.242 (4) Å	Cell parameters from 2677 reflections
b = 7.7993 (6) Å	θ = 2.7–21.5°
c = 15.3204 (12) Å	µ = 4.47 mm^−1
β = 98.958 (2)°	T = 293 K
V = 5458.0 (7) Å^3	Block, colourless
Z = 8	0.23 × 0.20 × 0.18 mm

Data collection

CCD Area Detector diffractometer	6293 independent reflections
Radiation source: fine-focus sealed tube	3493 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 28.0°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −60→51
Tmin = 0.381, Tmax = 0.447	k = −10→9
16092 measured reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.1114P)^2 + 0.9332P] where P = (Fo^2 + 2Fc^2)/3
6293 reflections	(Δ/σ)max < 0.001
337 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −0.61 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
Br1	0.237895 (16)	0.54185 (9)	0.27369 (5)	0.0903 (3)
Br2	0.225197 (14)	−0.05019 (8)	0.47586 (4)	0.0720 (2)
Br3	−0.022985 (16)	0.70637 (10)	0.13258 (5)	0.0956 (3)
N1	0.16351 (9)	−0.0606 (4)	0.3395 (2)	0.0469 (9)
H1	0.1657	−0.1376	0.3801	0.056*
C2	0.14063 (10)	−0.0555 (5)	0.2723 (3)	0.0408 (10)
O3	0.12123 (7)	−0.1608 (3)	0.2581 (2)	0.0490 (8)
C4	0.14446 (10)	0.1050 (5)	0.2142 (3)	0.0392 (10)
C5	0.17273 (10)	0.1783 (5)	0.2623 (3)	0.0420 (10)
C6	0.18930 (11)	0.3165 (6)	0.2427 (3)	0.0491 (11)
H6	0.1831	0.3855	0.1938	0.059*
C7	0.21537 (12)	0.3493 (6)	0.2977 (3)	0.0546 (13)
C8	0.22564 (11)	0.2478 (6)	0.3679 (3)	0.0533 (12)
H8	0.2433	0.2737	0.4035	0.064*
C9	0.20966 (10)	0.1061 (6)	0.3858 (3)	0.0471 (11)
C10	0.18298 (10)	0.0739 (5)	0.3345 (3)	0.0420 (10)
C11	0.11613 (9)	0.2217 (5)	0.2051 (2)	0.0366 (9)
C12	0.09840 (10)	0.1686 (6)	0.1129 (3)	0.0444 (11)
H12	0.0993	0.2655	0.0727	0.053*
C13	0.11589 (12)	0.0231 (6)	0.0805 (3)	0.0563 (13)
H13A	0.1094	−0.0872	0.0994	0.068*
H13B	0.1142	0.0240	0.0166	0.068*
N14	0.14617 (9)	0.0599 (4)	0.1222 (2)	0.0473 (9)
C15	0.16646 (14)	−0.0822 (6)	0.1124 (4)	0.0661 (15)
H15A	0.1856	−0.0548	0.1435	0.099*
H15B	0.1675	−0.0990	0.0509	0.099*
H15C	0.1595	−0.1852	0.1364	0.099*
C16	0.12555 (10)	0.4111 (5)	0.2024 (3)	0.0424 (10)
O17	0.13491 (8)	0.4789 (4)	0.1405 (2)	0.0593 (9)
N18	0.12130 (9)	0.4842 (4)	0.2782 (2)	0.0497 (10)
H18	0.1274	0.5852	0.2945	0.060*
C19	0.10593 (10)	0.3777 (6)	0.3279 (3)	0.0436 (10)
C20	0.09582 (13)	0.4140 (7)	0.4066 (3)	0.0603 (14)
H20	0.1000	0.5180	0.4355	0.072*
C21	0.07939 (12)	0.2904 (7)	0.4401 (3)	0.0613 (14)
H21	0.0724	0.3113	0.4929	0.074*
C22	0.07302 (11)	0.1376 (7)	0.3976 (3)	0.0525 (12)
H22	0.0614	0.0578	0.4211	0.063*
C23	0.08371 (10)	0.1004 (5)	0.3199 (3)	0.0426 (10)
H23	0.0794	−0.0038	0.2913	0.051*
C24	0.10082 (9)	0.2202 (5)	0.2860 (2)	0.0365 (9)
C25	0.06637 (11)	0.1303 (7)	0.1138 (3)	0.0506 (12)
O26	0.05776 (9)	−0.0167 (5)	0.1057 (3)	0.0729 (11)
C27	0.04596 (11)	0.2728 (6)	0.1215 (3)	0.0521 (12)
C28	0.01687 (13)	0.2358 (8)	0.1309 (4)	0.0731 (16)
H28	0.0112	0.1220	0.1348	0.088*
C29	−0.00322 (14)	0.3629 (9)	0.1345 (4)	0.0849 (19)
H29	−0.0225	0.3365	0.1402	0.102*
C30	0.00552 (13)	0.5308 (8)	0.1295 (4)	0.0664 (15)
C31	0.03333 (13)	0.5728 (7)	0.1237 (3)	0.0638 (14)
H31	0.0389	0.6872	0.1224	0.077*
C32	0.05340 (12)	0.4440 (7)	0.1197 (3)	0.0586 (13)
H32	0.0726	0.4733	0.1155	0.070*
O33	0.15880 (9)	−0.3009 (5)	0.4744 (2)	0.0700 (11)
H33	0.1553	−0.2718	0.5231	0.105*
C34	0.17499 (18)	−0.4559 (8)	0.4823 (5)	0.091 (2)
H34A	0.1923	−0.4418	0.5253	0.136*
H34B	0.1805	−0.4849	0.4262	0.136*
H34C	0.1632	−0.5461	0.5008	0.136*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0841 (5)	0.0870 (5)	0.0984 (5)	−0.0488 (4)	0.0097 (4)	0.0154 (4)
Br2	0.0680 (4)	0.0726 (4)	0.0705 (4)	−0.0001 (3)	−0.0050 (3)	0.0123 (3)
Br3	0.0747 (5)	0.1062 (6)	0.1032 (5)	0.0222 (4)	0.0054 (4)	0.0139 (4)
N1	0.056 (2)	0.035 (2)	0.050 (2)	−0.0026 (17)	0.0107 (19)	0.0045 (16)
C2	0.055 (3)	0.026 (2)	0.045 (2)	0.004 (2)	0.018 (2)	−0.0037 (17)
O3	0.058 (2)	0.0215 (14)	0.068 (2)	−0.0081 (14)	0.0139 (16)	−0.0021 (13)
C4	0.051 (3)	0.027 (2)	0.042 (2)	−0.0069 (18)	0.014 (2)	−0.0039 (17)
C5	0.052 (3)	0.032 (2)	0.044 (2)	−0.0026 (19)	0.017 (2)	−0.0065 (18)
C6	0.055 (3)	0.042 (3)	0.053 (3)	−0.012 (2)	0.016 (2)	−0.001 (2)
C7	0.064 (3)	0.043 (3)	0.061 (3)	−0.020 (2)	0.023 (3)	−0.010 (2)
C8	0.048 (3)	0.055 (3)	0.057 (3)	−0.007 (2)	0.008 (2)	−0.012 (2)
C9	0.053 (3)	0.042 (2)	0.047 (2)	0.002 (2)	0.009 (2)	−0.005 (2)
C10	0.053 (3)	0.030 (2)	0.046 (2)	0.0018 (19)	0.019 (2)	−0.0059 (18)
C11	0.048 (3)	0.025 (2)	0.037 (2)	−0.0080 (17)	0.0052 (18)	−0.0005 (16)
C12	0.058 (3)	0.039 (2)	0.036 (2)	−0.010 (2)	0.007 (2)	−0.0010 (18)
C13	0.075 (4)	0.052 (3)	0.041 (2)	−0.015 (3)	0.008 (2)	−0.011 (2)
N14	0.059 (3)	0.041 (2)	0.045 (2)	−0.0077 (18)	0.0173 (18)	−0.0109 (16)
C15	0.090 (4)	0.046 (3)	0.069 (3)	0.001 (3)	0.032 (3)	−0.015 (2)
C16	0.048 (3)	0.030 (2)	0.048 (2)	−0.0086 (19)	0.002 (2)	0.0115 (18)
O17	0.070 (2)	0.0431 (18)	0.066 (2)	−0.0148 (17)	0.0161 (18)	0.0142 (16)
N18	0.066 (3)	0.0246 (18)	0.057 (2)	−0.0048 (18)	0.006 (2)	−0.0107 (16)
C19	0.047 (3)	0.035 (2)	0.048 (2)	0.002 (2)	0.003 (2)	−0.0013 (19)
C20	0.072 (4)	0.056 (3)	0.055 (3)	0.012 (3)	0.015 (3)	−0.018 (2)
C21	0.068 (4)	0.075 (4)	0.046 (3)	0.012 (3)	0.023 (3)	0.000 (3)
C22	0.048 (3)	0.062 (3)	0.050 (3)	0.009 (2)	0.015 (2)	0.013 (2)
C23	0.049 (3)	0.034 (2)	0.044 (2)	0.003 (2)	0.005 (2)	0.0010 (18)
C24	0.043 (2)	0.031 (2)	0.034 (2)	−0.0002 (18)	0.0009 (18)	0.0017 (16)
C25	0.062 (3)	0.057 (3)	0.031 (2)	−0.018 (3)	0.003 (2)	0.001 (2)
O26	0.080 (3)	0.054 (2)	0.085 (3)	−0.026 (2)	0.014 (2)	−0.0138 (19)
C27	0.054 (3)	0.056 (3)	0.043 (2)	−0.012 (2)	−0.002 (2)	0.005 (2)
C28	0.058 (4)	0.058 (3)	0.100 (4)	−0.019 (3)	0.003 (3)	0.006 (3)
C29	0.045 (4)	0.095 (5)	0.112 (5)	−0.020 (3)	0.001 (3)	0.016 (4)
C30	0.053 (3)	0.080 (4)	0.063 (3)	0.000 (3)	0.001 (3)	0.013 (3)
C31	0.065 (4)	0.058 (3)	0.068 (3)	−0.002 (3)	0.008 (3)	0.016 (3)
C32	0.053 (3)	0.062 (3)	0.061 (3)	−0.010 (3)	0.010 (2)	0.012 (2)
O33	0.095 (3)	0.062 (2)	0.058 (2)	0.008 (2)	0.028 (2)	0.0152 (18)
C34	0.112 (6)	0.077 (5)	0.087 (4)	0.019 (4)	0.030 (4)	0.012 (3)

Geometric parameters (Å, º)

Br1—C7	1.896 (5)	C16—O17	1.222 (5)
Br2—C9	1.897 (5)	C16—N18	1.337 (6)
Br3—C30	1.906 (6)	N18—C19	1.393 (6)
N1—C2	1.357 (6)	N18—H18	0.8600
N1—C10	1.392 (5)	C19—C20	1.389 (6)
N1—H1	0.8600	C19—C24	1.389 (6)
C2—O3	1.211 (5)	C20—C21	1.375 (8)
C2—C4	1.561 (6)	C20—H20	0.9300
C4—N14	1.467 (5)	C21—C22	1.368 (7)
C4—C5	1.510 (6)	C21—H21	0.9300
C4—C11	1.584 (6)	C22—C23	1.389 (6)
C5—C6	1.382 (6)	C22—H22	0.9300
C5—C10	1.396 (6)	C23—C24	1.378 (6)
C6—C7	1.383 (7)	C23—H23	0.9300
C6—H6	0.9300	C25—O26	1.213 (6)
C7—C8	1.360 (7)	C25—C27	1.475 (7)
C8—C9	1.381 (6)	C27—C32	1.381 (7)
C8—H8	0.9300	C27—C28	1.405 (7)
C9—C10	1.378 (6)	C28—C29	1.365 (9)
C11—C24	1.519 (6)	C28—H28	0.9300
C11—C16	1.543 (5)	C29—C30	1.376 (9)
C11—C12	1.575 (6)	C29—H29	0.9300
C12—C25	1.513 (7)	C30—C31	1.343 (8)
C12—C13	1.521 (7)	C31—C32	1.376 (7)
C12—H12	0.9800	C31—H31	0.9300
C13—N14	1.474 (6)	C32—H32	0.9300
C13—H13A	0.9700	O33—C34	1.417 (7)
C13—H13B	0.9700	O33—H33	0.8200
N14—C15	1.474 (6)	C34—H34A	0.9600
C15—H15A	0.9600	C34—H34B	0.9600
C15—H15B	0.9600	C34—H34C	0.9600
C15—H15C	0.9600
C2—N1—C10	111.8 (4)	H15A—C15—H15C	109.5
C2—N1—H1	124.1	H15B—C15—H15C	109.5
C10—N1—H1	124.1	O17—C16—N18	127.5 (4)
O3—C2—N1	125.8 (4)	O17—C16—C11	124.8 (4)
O3—C2—C4	126.0 (4)	N18—C16—C11	107.7 (3)
N1—C2—C4	108.1 (4)	C16—N18—C19	112.1 (3)
N14—C4—C5	112.8 (3)	C16—N18—H18	123.9
N14—C4—C2	112.5 (3)	C19—N18—H18	123.9
C5—C4—C2	101.1 (3)	C20—C19—C24	121.7 (4)
N14—C4—C11	102.8 (3)	C20—C19—N18	128.4 (4)
C5—C4—C11	117.8 (3)	C24—C19—N18	109.8 (4)
C2—C4—C11	110.2 (3)	C21—C20—C19	117.5 (5)
C6—C5—C10	119.8 (4)	C21—C20—H20	121.3
C6—C5—C4	131.0 (4)	C19—C20—H20	121.3
C10—C5—C4	109.1 (4)	C22—C21—C20	121.6 (4)
C5—C6—C7	118.1 (4)	C22—C21—H21	119.2
C5—C6—H6	120.9	C20—C21—H21	119.2
C7—C6—H6	120.9	C21—C22—C23	120.7 (5)
C8—C7—C6	122.6 (4)	C21—C22—H22	119.6
C8—C7—Br1	118.6 (4)	C23—C22—H22	119.6
C6—C7—Br1	118.8 (4)	C24—C23—C22	118.9 (4)
C7—C8—C9	119.4 (5)	C24—C23—H23	120.5
C7—C8—H8	120.3	C22—C23—H23	120.5
C9—C8—H8	120.3	C23—C24—C19	119.5 (4)
C10—C9—C8	119.5 (4)	C23—C24—C11	132.9 (4)
C10—C9—Br2	120.1 (3)	C19—C24—C11	107.6 (3)
C8—C9—Br2	120.3 (4)	O26—C25—C27	121.1 (5)
C9—C10—N1	129.4 (4)	O26—C25—C12	119.5 (5)
C9—C10—C5	120.6 (4)	C27—C25—C12	119.4 (4)
N1—C10—C5	109.9 (4)	C32—C27—C28	116.5 (5)
C24—C11—C16	101.5 (3)	C32—C27—C25	124.2 (5)
C24—C11—C12	119.1 (4)	C28—C27—C25	119.2 (5)
C16—C11—C12	109.7 (3)	C29—C28—C27	121.6 (5)
C24—C11—C4	114.1 (3)	C29—C28—H28	119.2
C16—C11—C4	108.6 (3)	C27—C28—H28	119.2
C12—C11—C4	103.6 (3)	C28—C29—C30	118.7 (6)
C25—C12—C13	115.3 (4)	C28—C29—H29	120.6
C25—C12—C11	114.7 (3)	C30—C29—H29	120.6
C13—C12—C11	105.1 (4)	C31—C30—C29	121.9 (6)
C25—C12—H12	107.1	C31—C30—Br3	119.9 (5)
C13—C12—H12	107.1	C29—C30—Br3	118.2 (5)
C11—C12—H12	107.1	C30—C31—C32	119.0 (5)
N14—C13—C12	103.4 (3)	C30—C31—H31	120.5
N14—C13—H13A	111.1	C32—C31—H31	120.5
C12—C13—H13A	111.1	C31—C32—C27	122.2 (5)
N14—C13—H13B	111.1	C31—C32—H32	118.9
C12—C13—H13B	111.1	C27—C32—H32	118.9
H13A—C13—H13B	109.1	C34—O33—H33	109.5
C4—N14—C13	105.9 (3)	O33—C34—H34A	109.5
C4—N14—C15	114.1 (4)	O33—C34—H34B	109.5
C13—N14—C15	112.7 (4)	H34A—C34—H34B	109.5
N14—C15—H15A	109.5	O33—C34—H34C	109.5
N14—C15—H15B	109.5	H34A—C34—H34C	109.5
H15A—C15—H15B	109.5	H34B—C34—H34C	109.5
N14—C15—H15C	109.5
C10—N1—C2—O3	176.3 (4)	C11—C4—N14—C13	−41.4 (4)
C10—N1—C2—C4	−1.1 (5)	C5—C4—N14—C15	66.1 (5)
O3—C2—C4—N14	−56.6 (6)	C2—C4—N14—C15	−47.5 (5)
N1—C2—C4—N14	120.8 (4)	C11—C4—N14—C15	−165.9 (4)
O3—C2—C4—C5	−177.2 (4)	C12—C13—N14—C4	44.6 (4)
N1—C2—C4—C5	0.2 (4)	C12—C13—N14—C15	170.0 (4)
O3—C2—C4—C11	57.5 (5)	C24—C11—C16—O17	−168.5 (4)
N1—C2—C4—C11	−125.1 (4)	C12—C11—C16—O17	−41.7 (6)
N14—C4—C5—C6	55.7 (6)	C4—C11—C16—O17	70.9 (5)
C2—C4—C5—C6	176.1 (4)	C24—C11—C16—N18	10.9 (4)
C11—C4—C5—C6	−63.8 (6)	C12—C11—C16—N18	137.8 (4)
N14—C4—C5—C10	−119.8 (4)	C4—C11—C16—N18	−109.6 (4)
C2—C4—C5—C10	0.7 (4)	O17—C16—N18—C19	170.1 (5)
C11—C4—C5—C10	120.7 (4)	C11—C16—N18—C19	−9.3 (5)
C10—C5—C6—C7	−1.9 (6)	C16—N18—C19—C20	−175.1 (5)
C4—C5—C6—C7	−177.0 (4)	C16—N18—C19—C24	3.4 (5)
C5—C6—C7—C8	2.3 (7)	C24—C19—C20—C21	−2.6 (7)
C5—C6—C7—Br1	−178.3 (3)	N18—C19—C20—C21	175.7 (5)
C6—C7—C8—C9	0.0 (7)	C19—C20—C21—C22	−0.3 (8)
Br1—C7—C8—C9	−179.4 (3)	C20—C21—C22—C23	1.7 (8)
C7—C8—C9—C10	−2.7 (7)	C21—C22—C23—C24	−0.2 (7)
C7—C8—C9—Br2	173.8 (4)	C22—C23—C24—C19	−2.7 (6)
C8—C9—C10—N1	179.0 (4)	C22—C23—C24—C11	179.1 (4)
Br2—C9—C10—N1	2.5 (6)	C20—C19—C24—C23	4.2 (7)
C8—C9—C10—C5	3.1 (6)	N18—C19—C24—C23	−174.4 (4)
Br2—C9—C10—C5	−173.4 (3)	C20—C19—C24—C11	−177.2 (4)
C2—N1—C10—C9	−174.7 (4)	N18—C19—C24—C11	4.2 (5)
C2—N1—C10—C5	1.5 (5)	C16—C11—C24—C23	169.5 (4)
C6—C5—C10—C9	−0.8 (6)	C12—C11—C24—C23	49.0 (6)
C4—C5—C10—C9	175.3 (4)	C4—C11—C24—C23	−73.9 (6)
C6—C5—C10—N1	−177.4 (4)	C16—C11—C24—C19	−8.9 (4)
C4—C5—C10—N1	−1.3 (5)	C12—C11—C24—C19	−129.3 (4)
N14—C4—C11—C24	153.0 (3)	C4—C11—C24—C19	107.7 (4)
C5—C4—C11—C24	−82.3 (4)	C13—C12—C25—O26	13.7 (6)
C2—C4—C11—C24	32.8 (4)	C11—C12—C25—O26	−108.5 (5)
N14—C4—C11—C16	−94.6 (4)	C13—C12—C25—C27	−164.3 (4)
C5—C4—C11—C16	30.1 (5)	C11—C12—C25—C27	73.4 (5)
C2—C4—C11—C16	145.2 (3)	O26—C25—C27—C32	−171.4 (5)
N14—C4—C11—C12	21.9 (4)	C12—C25—C27—C32	6.6 (7)
C5—C4—C11—C12	146.6 (3)	O26—C25—C27—C28	8.1 (7)
C2—C4—C11—C12	−98.2 (4)	C12—C25—C27—C28	−173.9 (4)
C24—C11—C12—C25	3.5 (5)	C32—C27—C28—C29	2.5 (8)
C16—C11—C12—C25	−112.7 (4)	C25—C27—C28—C29	−177.1 (5)
C4—C11—C12—C25	131.5 (4)	C27—C28—C29—C30	−0.6 (10)
C24—C11—C12—C13	−124.1 (4)	C28—C29—C30—C31	−1.8 (9)
C16—C11—C12—C13	119.7 (4)	C28—C29—C30—Br3	178.9 (5)
C4—C11—C12—C13	3.9 (4)	C29—C30—C31—C32	2.2 (9)
C25—C12—C13—N14	−155.6 (4)	Br3—C30—C31—C32	−178.6 (4)
C11—C12—C13—N14	−28.3 (4)	C30—C31—C32—C27	−0.1 (8)
C5—C4—N14—C13	−169.3 (4)	C28—C27—C32—C31	−2.1 (8)
C2—C4—N14—C13	77.1 (4)	C25—C27—C32—C31	177.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N18—H18···O3^i	0.86	2.07	2.786 (4)	141
O33—H33···N14^ii	0.82	2.33	3.069 (5)	151
C31—H31···O26^i	0.93	2.50	3.420 (7)	173
N1—H1···O33	0.86	1.99	2.823 (5)	164
C6—H6···O17	0.93	2.37	3.025 (6)	128
C12—H12···O17	0.98	2.46	2.943 (5)	110
C13—H13A···O3	0.97	2.47	3.051 (6)	118
C23—H23···O3	0.93	2.41	2.927 (5)	115

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