16-[(E)-4-Bromo-benzyl-idene]-13-(4-bromo-phen-yl)-2-hy-droxy-11-methyl-1,11-diaza-penta-cyclo-[12.3.1.0.0.0]octa-deca-3(8),4,6-triene-9,15-dione.

In the title pyrrolidine compound, C(30)H(24)Br(2)N(2)O(3), the two fused pyrrolidine rings adopt envelope and twisted conformations, whereas the piperidine ring adopts an envelope conformation. The essentially planar 2,3-dihydro-indanone unit [maximum deviation = -0.0163 (19) Å] is inclined at inter-planar angles of 14.29 (9) and 61.07 (9)° to the two benzene rings. In the crystal, adjacent mol-ecules are linked into dimers by inter-molecular O-H⋯N and C-H⋯O hydrogen bonds. Short inter-molecular Br⋯Br inter-actions [3.5140 (6) Å] further inter-connect these dimers into double dimeric columns along the b axis.

Related literature

For general background to and applications of the title pyrrolidine compound, see: Huryn et al. (1991 ▶); Suzuki et al. (1994 ▶); Waldmann (1995 ▶). For the preparation, see: Kumar et al. (2010 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For closely related pyrrolidine structures, see: Kumar et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C30H24Br2N2O3

M = 620.33

Monoclinic,

a = 13.3490 (18) Å

b = 9.1243 (12) Å

c = 22.541 (3) Å

β = 113.191 (6)°

V = 2523.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 3.25 mm−1

T = 100 K

0.39 × 0.38 × 0.18 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.362, T max = 0.600

25337 measured reflections

7357 independent reflections

5709 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.02

7357 reflections

339 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.27 e Å−3

Δρmin = −0.94 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051585/sj5073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051585/sj5073Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H24Br2N2O3	F(000) = 1248
Mr = 620.33	Dx = 1.633 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7088 reflections
a = 13.3490 (18) Å	θ = 2.7–29.9°
b = 9.1243 (12) Å	µ = 3.25 mm−1
c = 22.541 (3) Å	T = 100 K
β = 113.191 (6)°	Block, yellow
V = 2523.7 (6) Å3	0.39 × 0.38 × 0.18 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	7357 independent reflections
Radiation source: fine-focus sealed tube	5709 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.362, Tmax = 0.600	k = −12→12
25337 measured reflections	l = −31→31

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.067P)2 + 0.5579P] where P = (Fo2 + 2Fc2)/3
7357 reflections	(Δ/σ)max = 0.001
339 parameters	Δρmax = 1.27 e Å−3
0 restraints	Δρmin = −0.94 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Br1	0.75505 (2)	−0.12072 (3)	0.698221 (14)	0.03673 (9)
Br2	0.04211 (2)	1.10857 (3)	0.764653 (13)	0.04012 (10)
O1	0.42011 (12)	0.74248 (18)	0.64632 (8)	0.0298 (4)
O2	0.33814 (13)	0.67728 (18)	0.48068 (8)	0.0279 (3)
O3	0.07211 (11)	0.37326 (16)	0.49214 (7)	0.0203 (3)
N1	0.19684 (13)	0.41022 (19)	0.59993 (8)	0.0185 (3)
N2	0.10821 (13)	0.66492 (19)	0.47739 (8)	0.0188 (3)
C1	0.65306 (19)	0.3089 (3)	0.65943 (12)	0.0309 (5)
H1A	0.6778	0.3929	0.6461	0.037*
C2	0.7103 (2)	0.1791 (3)	0.66670 (14)	0.0369 (6)
H2A	0.7731	0.1759	0.6584	0.044*
C3	0.67343 (19)	0.0541 (3)	0.68643 (11)	0.0278 (5)
C4	0.58098 (17)	0.0572 (3)	0.70013 (10)	0.0258 (4)
H4A	0.5567	−0.0275	0.7132	0.031*
C5	0.52520 (16)	0.1883 (3)	0.69400 (10)	0.0245 (4)
H5A	0.4648	0.1918	0.7048	0.029*
C6	0.55817 (16)	0.3155 (2)	0.67190 (10)	0.0223 (4)
C7	0.50039 (16)	0.4559 (2)	0.65988 (10)	0.0212 (4)
H7A	0.5431	0.5379	0.6620	0.025*
C8	0.39434 (15)	0.4838 (2)	0.64618 (9)	0.0197 (4)
C9	0.35805 (16)	0.6388 (2)	0.62815 (10)	0.0206 (4)
C10	0.23733 (15)	0.6582 (2)	0.58527 (9)	0.0178 (4)
C11	0.17469 (16)	0.5606 (2)	0.61558 (10)	0.0193 (4)
H11A	0.2017	0.5751	0.6619	0.023*
H11B	0.0972	0.5818	0.5967	0.023*
C12	0.30882 (16)	0.3701 (2)	0.64265 (10)	0.0201 (4)
H12A	0.3273	0.2782	0.6278	0.024*
H12B	0.3114	0.3541	0.6858	0.024*
C13	0.23320 (18)	0.9689 (3)	0.66853 (11)	0.0285 (5)
H13A	0.3058	0.9774	0.6741	0.034*
C14	0.1991 (2)	1.0335 (3)	0.71292 (12)	0.0321 (5)
H14A	0.2480	1.0853	0.7478	0.038*
C15	0.09096 (19)	1.0199 (3)	0.70461 (11)	0.0274 (4)
C16	0.01713 (19)	0.9433 (2)	0.65255 (11)	0.0273 (4)
H16A	−0.0553	0.9346	0.6474	0.033*
C17	0.05257 (18)	0.8798 (2)	0.60831 (11)	0.0247 (4)
H17A	0.0033	0.8288	0.5732	0.030*
C18	0.16138 (18)	0.8914 (2)	0.61564 (11)	0.0220 (4)
C19	0.20385 (16)	0.8202 (2)	0.56940 (10)	0.0202 (4)
H19A	0.2696	0.8740	0.5731	0.024*
C20	0.12693 (17)	0.8198 (2)	0.49721 (10)	0.0221 (4)
H20A	0.0586	0.8675	0.4910	0.027*
H20B	0.1602	0.8713	0.4720	0.027*
C21	0.20367 (15)	0.5807 (2)	0.51872 (9)	0.0175 (4)
C22	0.29550 (16)	0.5715 (2)	0.49399 (10)	0.0207 (4)
C23	0.32090 (16)	0.4148 (2)	0.49005 (10)	0.0214 (4)
C24	0.39758 (18)	0.3521 (3)	0.46964 (12)	0.0276 (5)
H24A	0.4416	0.4107	0.4561	0.033*
C25	0.40643 (19)	0.2012 (3)	0.47010 (13)	0.0330 (5)
H25A	0.4578	0.1577	0.4574	0.040*
C26	0.3394 (2)	0.1134 (3)	0.48941 (13)	0.0328 (5)
H26A	0.3456	0.0120	0.4887	0.039*
C27	0.26277 (18)	0.1761 (2)	0.50979 (11)	0.0263 (4)
H27A	0.2180	0.1174	0.5227	0.032*
C28	0.25500 (16)	0.3277 (2)	0.51039 (10)	0.0203 (4)
C29	0.17847 (15)	0.4177 (2)	0.53055 (9)	0.0172 (4)
C30	0.07438 (18)	0.6445 (3)	0.40754 (10)	0.0245 (4)
H30A	0.0698	0.5417	0.3978	0.037*
H30B	0.1268	0.6894	0.3939	0.037*
H30C	0.0044	0.6891	0.3852	0.037*
H1O3	0.032 (2)	0.380 (3)	0.5121 (14)	0.024 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.04380 (16)	0.02974 (15)	0.04459 (16)	0.01490 (10)	0.02593 (13)	0.01142 (10)
Br2	0.05369 (18)	0.03787 (16)	0.03862 (15)	−0.01126 (11)	0.02871 (13)	−0.01324 (11)
O1	0.0211 (7)	0.0207 (8)	0.0386 (9)	−0.0050 (6)	0.0022 (7)	−0.0016 (7)
O2	0.0250 (7)	0.0239 (8)	0.0379 (9)	−0.0036 (6)	0.0156 (7)	0.0014 (7)
O3	0.0131 (6)	0.0238 (8)	0.0214 (7)	−0.0039 (5)	0.0041 (6)	−0.0033 (5)
N1	0.0160 (7)	0.0167 (8)	0.0204 (8)	0.0008 (6)	0.0047 (6)	0.0014 (6)
N2	0.0178 (7)	0.0175 (8)	0.0186 (7)	0.0017 (6)	0.0046 (6)	0.0019 (6)
C1	0.0300 (11)	0.0273 (12)	0.0418 (13)	0.0038 (9)	0.0212 (10)	0.0098 (10)
C2	0.0363 (13)	0.0328 (13)	0.0538 (16)	0.0098 (11)	0.0307 (12)	0.0144 (12)
C3	0.0311 (11)	0.0256 (11)	0.0295 (11)	0.0080 (9)	0.0151 (9)	0.0043 (9)
C4	0.0231 (10)	0.0265 (11)	0.0246 (10)	0.0002 (8)	0.0061 (8)	0.0073 (8)
C5	0.0168 (9)	0.0305 (12)	0.0233 (10)	0.0025 (8)	0.0049 (8)	0.0062 (8)
C6	0.0178 (9)	0.0269 (11)	0.0200 (9)	0.0003 (8)	0.0049 (7)	0.0018 (8)
C7	0.0173 (8)	0.0210 (10)	0.0208 (9)	−0.0015 (7)	0.0027 (7)	0.0011 (7)
C8	0.0156 (8)	0.0217 (10)	0.0171 (8)	0.0003 (7)	0.0014 (7)	0.0019 (7)
C9	0.0168 (8)	0.0205 (10)	0.0217 (9)	−0.0009 (7)	0.0044 (7)	−0.0007 (7)
C10	0.0145 (8)	0.0155 (9)	0.0201 (8)	0.0000 (7)	0.0034 (7)	−0.0001 (7)
C11	0.0189 (9)	0.0169 (9)	0.0201 (9)	−0.0003 (7)	0.0057 (7)	−0.0003 (7)
C12	0.0162 (8)	0.0187 (10)	0.0216 (9)	0.0002 (7)	0.0031 (7)	0.0025 (7)
C13	0.0224 (10)	0.0241 (11)	0.0333 (11)	−0.0013 (8)	0.0048 (9)	−0.0068 (9)
C14	0.0321 (11)	0.0281 (12)	0.0311 (11)	−0.0023 (10)	0.0072 (10)	−0.0085 (10)
C15	0.0344 (11)	0.0207 (10)	0.0276 (10)	0.0015 (9)	0.0127 (9)	−0.0006 (8)
C16	0.0286 (10)	0.0215 (11)	0.0329 (11)	−0.0021 (9)	0.0134 (9)	−0.0023 (9)
C17	0.0229 (10)	0.0208 (10)	0.0268 (10)	−0.0020 (8)	0.0058 (8)	−0.0044 (8)
C18	0.0224 (9)	0.0157 (9)	0.0247 (10)	0.0012 (7)	0.0058 (8)	−0.0001 (7)
C19	0.0199 (9)	0.0151 (9)	0.0225 (9)	0.0006 (7)	0.0051 (7)	−0.0002 (7)
C20	0.0243 (10)	0.0166 (9)	0.0220 (9)	0.0015 (8)	0.0053 (8)	0.0020 (7)
C21	0.0144 (8)	0.0167 (9)	0.0197 (9)	0.0005 (7)	0.0050 (7)	0.0002 (7)
C22	0.0166 (8)	0.0229 (10)	0.0219 (9)	−0.0009 (7)	0.0067 (7)	−0.0005 (8)
C23	0.0161 (8)	0.0226 (10)	0.0237 (9)	−0.0015 (7)	0.0061 (8)	−0.0032 (8)
C24	0.0203 (10)	0.0299 (12)	0.0340 (11)	−0.0005 (9)	0.0121 (9)	−0.0052 (9)
C25	0.0241 (10)	0.0334 (13)	0.0419 (13)	0.0034 (9)	0.0137 (10)	−0.0103 (11)
C26	0.0307 (11)	0.0217 (11)	0.0452 (14)	0.0045 (9)	0.0139 (11)	−0.0057 (10)
C27	0.0218 (9)	0.0207 (10)	0.0340 (11)	0.0002 (8)	0.0084 (9)	−0.0026 (9)
C28	0.0164 (8)	0.0192 (10)	0.0228 (9)	0.0010 (7)	0.0051 (7)	−0.0029 (8)
C29	0.0137 (8)	0.0158 (9)	0.0197 (9)	−0.0013 (7)	0.0039 (7)	−0.0008 (7)
C30	0.0222 (9)	0.0282 (11)	0.0204 (9)	−0.0018 (8)	0.0056 (8)	0.0012 (8)

Br1—C3	1.891 (2)	C12—H12B	0.9700
Br2—C15	1.899 (2)	C13—C14	1.384 (3)
O1—C9	1.217 (3)	C13—C18	1.393 (3)
O2—C22	1.217 (3)	C13—H13A	0.9300
O3—C29	1.400 (2)	C14—C15	1.386 (3)
O3—H1O3	0.82 (3)	C14—H14A	0.9300
N1—C12	1.470 (2)	C15—C16	1.388 (3)
N1—C11	1.476 (3)	C16—C17	1.387 (3)
N1—C29	1.486 (3)	C16—H16A	0.9300
N2—C21	1.466 (2)	C17—C18	1.400 (3)
N2—C30	1.469 (3)	C17—H17A	0.9300
N2—C20	1.473 (3)	C18—C19	1.515 (3)
C1—C2	1.384 (3)	C19—C20	1.545 (3)
C1—C6	1.403 (3)	C19—H19A	0.9800
C1—H1A	0.9300	C20—H20A	0.9700
C2—C3	1.382 (3)	C20—H20B	0.9700
C2—H2A	0.9300	C21—C22	1.536 (3)
C3—C4	1.385 (3)	C21—C29	1.571 (3)
C4—C5	1.387 (3)	C22—C23	1.480 (3)
C4—H4A	0.9300	C23—C28	1.391 (3)
C5—C6	1.400 (3)	C23—C24	1.399 (3)
C5—H5A	0.9300	C24—C25	1.382 (4)
C6—C7	1.465 (3)	C24—H24A	0.9300
C7—C8	1.349 (3)	C25—C26	1.392 (4)
C7—H7A	0.9300	C25—H25A	0.9300
C8—C9	1.498 (3)	C26—C27	1.398 (3)
C8—C12	1.522 (3)	C26—H26A	0.9300
C9—C10	1.528 (3)	C27—C28	1.387 (3)
C10—C19	1.545 (3)	C27—H27A	0.9300
C10—C11	1.552 (3)	C28—C29	1.513 (3)
C10—C21	1.556 (3)	C30—H30A	0.9600
C11—H11A	0.9700	C30—H30B	0.9600
C11—H11B	0.9700	C30—H30C	0.9600
C12—H12A	0.9700
C29—O3—H1O3	110.9 (19)	C17—C16—C15	119.2 (2)
C12—N1—C11	108.83 (16)	C17—C16—H16A	120.4
C12—N1—C29	113.86 (16)	C15—C16—H16A	120.4
C11—N1—C29	104.09 (15)	C16—C17—C18	121.0 (2)
C21—N2—C30	116.00 (16)	C16—C17—H17A	119.5
C21—N2—C20	108.01 (15)	C18—C17—H17A	119.5
C30—N2—C20	112.97 (16)	C13—C18—C17	118.1 (2)
C2—C1—C6	120.9 (2)	C13—C18—C19	119.26 (19)
C2—C1—H1A	119.6	C17—C18—C19	122.58 (19)
C6—C1—H1A	119.6	C18—C19—C20	116.89 (17)
C3—C2—C1	119.6 (2)	C18—C19—C10	113.80 (17)
C3—C2—H2A	120.2	C20—C19—C10	104.67 (16)
C1—C2—H2A	120.2	C18—C19—H19A	107.0
C2—C3—C4	121.1 (2)	C20—C19—H19A	107.0
C2—C3—Br1	118.87 (17)	C10—C19—H19A	107.0
C4—C3—Br1	120.01 (18)	N2—C20—C19	106.54 (16)
C3—C4—C5	119.0 (2)	N2—C20—H20A	110.4
C3—C4—H4A	120.5	C19—C20—H20A	110.4
C5—C4—H4A	120.5	N2—C20—H20B	110.4
C4—C5—C6	121.2 (2)	C19—C20—H20B	110.4
C4—C5—H5A	119.4	H20A—C20—H20B	108.6
C6—C5—H5A	119.4	N2—C21—C22	114.61 (16)
C5—C6—C1	118.1 (2)	N2—C21—C10	102.89 (15)
C5—C6—C7	125.05 (19)	C22—C21—C10	113.96 (16)
C1—C6—C7	116.9 (2)	N2—C21—C29	114.45 (15)
C8—C7—C6	129.5 (2)	C22—C21—C29	105.35 (16)
C8—C7—H7A	115.3	C10—C21—C29	105.46 (15)
C6—C7—H7A	115.3	O2—C22—C23	127.68 (19)
C7—C8—C9	115.98 (18)	O2—C22—C21	124.3 (2)
C7—C8—C12	125.56 (19)	C23—C22—C21	108.00 (17)
C9—C8—C12	118.28 (17)	C28—C23—C24	121.0 (2)
O1—C9—C8	122.53 (18)	C28—C23—C22	110.04 (18)
O1—C9—C10	122.10 (19)	C24—C23—C22	129.0 (2)
C8—C9—C10	115.37 (17)	C25—C24—C23	118.4 (2)
C9—C10—C19	113.19 (16)	C25—C24—H24A	120.8
C9—C10—C11	105.79 (16)	C23—C24—H24A	120.8
C19—C10—C11	119.58 (16)	C24—C25—C26	120.8 (2)
C9—C10—C21	112.92 (16)	C24—C25—H25A	119.6
C19—C10—C21	105.32 (16)	C26—C25—H25A	119.6
C11—C10—C21	99.37 (15)	C25—C26—C27	120.7 (2)
N1—C11—C10	103.57 (15)	C25—C26—H26A	119.6
N1—C11—H11A	111.0	C27—C26—H26A	119.6
C10—C11—H11A	111.0	C28—C27—C26	118.6 (2)
N1—C11—H11B	111.0	C28—C27—H27A	120.7
C10—C11—H11B	111.0	C26—C27—H27A	120.7
H11A—C11—H11B	109.0	C27—C28—C23	120.47 (19)
N1—C12—C8	114.38 (16)	C27—C28—C29	127.28 (19)
N1—C12—H12A	108.7	C23—C28—C29	112.24 (18)
C8—C12—H12A	108.7	O3—C29—N1	110.15 (16)
N1—C12—H12B	108.7	O3—C29—C28	107.30 (16)
C8—C12—H12B	108.7	N1—C29—C28	116.11 (16)
H12A—C12—H12B	107.6	O3—C29—C21	113.68 (16)
C14—C13—C18	121.6 (2)	N1—C29—C21	105.32 (15)
C14—C13—H13A	119.2	C28—C29—C21	104.35 (16)
C18—C13—H13A	119.2	N2—C30—H30A	109.5
C13—C14—C15	119.1 (2)	N2—C30—H30B	109.5
C13—C14—H14A	120.5	H30A—C30—H30B	109.5
C15—C14—H14A	120.5	N2—C30—H30C	109.5
C14—C15—C16	121.0 (2)	H30A—C30—H30C	109.5
C14—C15—Br2	119.81 (18)	H30B—C30—H30C	109.5
C16—C15—Br2	119.24 (17)
C6—C1—C2—C3	0.1 (4)	C30—N2—C21—C22	40.0 (2)
C1—C2—C3—C4	−1.1 (4)	C20—N2—C21—C22	−88.0 (2)
C1—C2—C3—Br1	−178.4 (2)	C30—N2—C21—C10	164.25 (16)
C2—C3—C4—C5	−0.2 (4)	C20—N2—C21—C10	36.29 (19)
Br1—C3—C4—C5	177.03 (17)	C30—N2—C21—C29	−81.9 (2)
C3—C4—C5—C6	2.5 (3)	C20—N2—C21—C29	150.15 (17)
C4—C5—C6—C1	−3.5 (3)	C9—C10—C21—N2	−154.75 (16)
C4—C5—C6—C7	175.8 (2)	C19—C10—C21—N2	−30.76 (19)
C2—C1—C6—C5	2.1 (4)	C11—C10—C21—N2	93.58 (16)
C2—C1—C6—C7	−177.2 (2)	C9—C10—C21—C22	−30.1 (2)
C5—C6—C7—C8	−24.2 (4)	C19—C10—C21—C22	93.93 (19)
C1—C6—C7—C8	155.0 (2)	C11—C10—C21—C22	−141.74 (17)
C6—C7—C8—C9	−172.5 (2)	C9—C10—C21—C29	84.99 (19)
C6—C7—C8—C12	2.6 (4)	C19—C10—C21—C29	−151.01 (15)
C7—C8—C9—O1	−26.2 (3)	C11—C10—C21—C29	−26.68 (17)
C12—C8—C9—O1	158.3 (2)	N2—C21—C22—O2	54.7 (3)
C7—C8—C9—C10	153.83 (18)	C10—C21—C22—O2	−63.4 (3)
C12—C8—C9—C10	−21.6 (3)	C29—C21—C22—O2	−178.56 (19)
O1—C9—C10—C19	−1.2 (3)	N2—C21—C22—C23	−125.52 (18)
C8—C9—C10—C19	178.73 (17)	C10—C21—C22—C23	116.32 (19)
O1—C9—C10—C11	−134.0 (2)	C29—C21—C22—C23	1.2 (2)
C8—C9—C10—C11	45.9 (2)	O2—C22—C23—C28	179.2 (2)
O1—C9—C10—C21	118.4 (2)	C21—C22—C23—C28	−0.6 (2)
C8—C9—C10—C21	−61.7 (2)	O2—C22—C23—C24	−0.9 (4)
C12—N1—C11—C10	75.54 (18)	C21—C22—C23—C24	179.3 (2)
C29—N1—C11—C10	−46.21 (18)	C28—C23—C24—C25	0.0 (3)
C9—C10—C11—N1	−72.53 (18)	C22—C23—C24—C25	−179.9 (2)
C19—C10—C11—N1	158.33 (16)	C23—C24—C25—C26	1.0 (4)
C21—C10—C11—N1	44.65 (17)	C24—C25—C26—C27	−1.1 (4)
C11—N1—C12—C8	−49.2 (2)	C25—C26—C27—C28	0.0 (4)
C29—N1—C12—C8	66.4 (2)	C26—C27—C28—C23	1.1 (3)
C7—C8—C12—N1	−153.2 (2)	C26—C27—C28—C29	−179.9 (2)
C9—C8—C12—N1	21.8 (3)	C24—C23—C28—C27	−1.1 (3)
C18—C13—C14—C15	0.4 (4)	C22—C23—C28—C27	178.8 (2)
C13—C14—C15—C16	−0.3 (4)	C24—C23—C28—C29	179.77 (19)
C13—C14—C15—Br2	−179.64 (18)	C22—C23—C28—C29	−0.3 (2)
C14—C15—C16—C17	−0.1 (4)	C12—N1—C29—O3	146.41 (17)
Br2—C15—C16—C17	179.31 (17)	C11—N1—C29—O3	−95.24 (18)
C15—C16—C17—C18	0.3 (3)	C12—N1—C29—C28	24.2 (2)
C14—C13—C18—C17	−0.1 (3)	C11—N1—C29—C28	142.58 (17)
C14—C13—C18—C19	−178.7 (2)	C12—N1—C29—C21	−90.63 (18)
C16—C17—C18—C13	−0.2 (3)	C11—N1—C29—C21	27.72 (18)
C16—C17—C18—C19	178.3 (2)	C27—C28—C29—O3	−57.1 (3)
C13—C18—C19—C20	−144.0 (2)	C23—C28—C29—O3	121.97 (18)
C17—C18—C19—C20	37.5 (3)	C27—C28—C29—N1	66.6 (3)
C13—C18—C19—C10	93.7 (2)	C23—C28—C29—N1	−114.36 (19)
C17—C18—C19—C10	−84.8 (2)	C27—C28—C29—C21	−178.0 (2)
C9—C10—C19—C18	−92.9 (2)	C23—C28—C29—C21	1.0 (2)
C11—C10—C19—C18	32.8 (2)	N2—C21—C29—O3	8.9 (2)
C21—C10—C19—C18	143.27 (17)	C22—C21—C29—O3	−117.90 (17)
C9—C10—C19—C20	138.31 (18)	C10—C21—C29—O3	121.25 (17)
C11—C10—C19—C20	−96.0 (2)	N2—C21—C29—N1	−111.75 (17)
C21—C10—C19—C20	14.5 (2)	C22—C21—C29—N1	121.43 (16)
C21—N2—C20—C19	−27.7 (2)	C10—C21—C29—N1	0.58 (18)
C30—N2—C20—C19	−157.37 (17)	N2—C21—C29—C28	125.49 (17)
C18—C19—C20—N2	−119.92 (19)	C22—C21—C29—C28	−1.32 (19)
C10—C19—C20—N2	7.0 (2)	C10—C21—C29—C28	−122.17 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2i	0.83 (3)	2.02 (3)	2.773 (2)	151 (3)
C11—H11B···O3i	0.97	2.39	3.288 (3)	153
C17—H17A···O3i	0.93	2.33	3.203 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N2i	0.83 (3)	2.02 (3)	2.773 (2)	151 (3)
C11—H11B⋯O3i	0.97	2.39	3.288 (3)	153
C17—H17A⋯O3i	0.93	2.33	3.203 (3)	157

Symmetry code: (i) .