5-[(E)-2-Bromo-benzyl-idene]-8-(2-bromo-phen-yl)-2-hy-droxy-10-methyl-3,10-di-aza-hexa-cyclo-[10.7.1.1.0.0.0]henicosa-1(20),12,14,16,18-pentaen-6-one.

In the title compound, C(33)H(26)Br(2)N(2)O(2), the piperidine group adopts an envelope conformation while the two pyrrolidine groups adopt half-chair and envelope conformations. The dihydro-acenaphthyl-ene group is almost planar, with a maximum deviation of 0.105 (1) Å. The dihedral angle between the two bromo-phenyl rings is 60.19 (8)°. An intra-molecular O-H⋯N inter-action is observed, generating an S(5) ring motif. The crystal structure is stabilized by inter-molecular C-H⋯O inter-actions. Short Br⋯Br [3.461 (1) Å] and Br⋯C [3.322 (2) Å] inter-molecular contacts are observed, as well as π-π inter-actions [centroid-centroid distance = 3.793 (1) Å].

Related literature

For biological studies of five-membered heterocycles, pyrrolidines and piperidines, see: Shi et al. (2009 ▶); Nair & Suja (2007 ▶); Nájera & Sansano (2005 ▶); Coldham & Hufton (2005 ▶); Daly et al. (1986 ▶); El-Subbagh et al. (2000 ▶); Dimmock et al. (2001 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For the graph-set description of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For a closely related crystal structure, see: Kumar et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C33H26Br2N2O2

M = 642.38

Triclinic,

a = 8.3334 (14) Å

b = 12.4213 (19) Å

c = 12.8062 (19) Å

α = 80.623 (4)°

β = 79.787 (4)°

γ = 88.213 (4)°

V = 1287.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.19 mm−1

T = 100 K

0.52 × 0.41 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.288, T max = 0.584

27238 measured reflections

9152 independent reflections

8233 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.105

S = 1.18

9152 reflections

357 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.99 e Å−3

Δρmin = −1.17 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/S1600536810033295/wn2405sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033295/wn2405Isup2.hkl

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

C33H26Br2N2O2	Z = 2
Mr = 642.38	F(000) = 648
Triclinic, P1	Dx = 1.657 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3334 (14) Å	Cell parameters from 9995 reflections
b = 12.4213 (19) Å	θ = 3.3–35.1°
c = 12.8062 (19) Å	µ = 3.19 mm−1
α = 80.623 (4)°	T = 100 K
β = 79.787 (4)°	Block, yellow
γ = 88.213 (4)°	0.52 × 0.41 × 0.19 mm
V = 1287.2 (3) Å3

Bruker APEXII DUO CCD area-detector diffractometer	9152 independent reflections
Radiation source: fine-focus sealed tube	8233 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 32.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.288, Tmax = 0.584	k = −18→18
27238 measured reflections	l = −19→19

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.2037P] where P = (Fo2 + 2Fc2)/3
9152 reflections	(Δ/σ)max = 0.004
357 parameters	Δρmax = 0.99 e Å−3
0 restraints	Δρmin = −1.17 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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	0.856585 (19)	1.068250 (12)	0.386199 (13)	0.01626 (5)
Br2	1.025391 (18)	0.886819 (12)	−0.064263 (12)	0.01437 (5)
O1	0.65922 (15)	0.94414 (9)	0.09019 (9)	0.0152 (2)
O2	0.55092 (14)	0.49704 (9)	0.16200 (10)	0.0131 (2)
N1	0.70944 (16)	0.61925 (10)	0.22074 (10)	0.0111 (2)
N2	0.45256 (16)	0.66041 (10)	0.02417 (10)	0.0109 (2)
C1	0.5433 (2)	0.80453 (13)	0.49862 (13)	0.0169 (3)
H1A	0.4852	0.7568	0.4705	0.020*
C2	0.5306 (2)	0.79520 (14)	0.60979 (14)	0.0193 (3)
H2A	0.4666	0.7406	0.6551	0.023*
C3	0.6137 (2)	0.86754 (14)	0.65250 (13)	0.0193 (3)
H3A	0.6054	0.8614	0.7266	0.023*
C4	0.7092 (2)	0.94912 (13)	0.58513 (13)	0.0173 (3)
H4A	0.7636	0.9985	0.6138	0.021*
C5	0.72276 (19)	0.95632 (12)	0.47468 (12)	0.0131 (2)
C6	0.64227 (19)	0.88461 (12)	0.42811 (12)	0.0132 (2)
C7	0.65161 (19)	0.89702 (12)	0.31078 (12)	0.0139 (3)
H7A	0.6384	0.9672	0.2749	0.017*
C8	0.67730 (18)	0.81722 (12)	0.25027 (12)	0.0124 (2)
C9	0.67026 (18)	0.84990 (12)	0.13230 (12)	0.0117 (2)
C10	0.66598 (17)	0.75367 (11)	0.07288 (11)	0.0104 (2)
C11	0.78932 (18)	0.66652 (12)	0.11188 (12)	0.0122 (2)
H11A	0.8086	0.6113	0.0655	0.015*
H11B	0.8924	0.6998	0.1134	0.015*
C12	0.71804 (19)	0.69952 (12)	0.29215 (12)	0.0135 (2)
H12A	0.8275	0.6978	0.3084	0.016*
H12B	0.6443	0.6764	0.3592	0.016*
C13	0.49859 (17)	0.69498 (11)	0.11969 (11)	0.0101 (2)
C14	0.54394 (17)	0.59505 (11)	0.20430 (11)	0.0106 (2)
C15	0.41293 (18)	0.59321 (12)	0.30260 (12)	0.0115 (2)
C16	0.3780 (2)	0.52059 (13)	0.39629 (13)	0.0161 (3)
H16A	0.4395	0.4573	0.4076	0.019*
C17	0.2453 (2)	0.54430 (14)	0.47598 (13)	0.0189 (3)
H17A	0.2209	0.4953	0.5397	0.023*
C18	0.1516 (2)	0.63738 (14)	0.46208 (13)	0.0182 (3)
H18A	0.0664	0.6506	0.5161	0.022*
C19	0.18568 (19)	0.71303 (12)	0.36501 (12)	0.0137 (2)
C20	0.10036 (19)	0.81138 (13)	0.33826 (13)	0.0153 (3)
H20A	0.0130	0.8321	0.3869	0.018*
C21	0.14739 (19)	0.87631 (12)	0.23970 (13)	0.0148 (3)
H21A	0.0902	0.9406	0.2237	0.018*
C22	0.27944 (18)	0.84897 (12)	0.16176 (12)	0.0128 (2)
H22A	0.3084	0.8945	0.0962	0.015*
C23	0.36326 (17)	0.75363 (11)	0.18568 (11)	0.0106 (2)
C24	0.31619 (18)	0.68768 (12)	0.28712 (12)	0.0113 (2)
C25	0.50120 (18)	0.75089 (12)	−0.06406 (12)	0.0128 (2)
H25A	0.4250	0.8112	−0.0589	0.015*
H25B	0.5053	0.7274	−0.1331	0.015*
C26	0.67185 (18)	0.78475 (12)	−0.05064 (11)	0.0112 (2)
H26A	0.6810	0.8643	−0.0699	0.013*
C27	0.81308 (18)	0.73321 (12)	−0.11802 (11)	0.0117 (2)
C28	0.97428 (18)	0.76858 (12)	−0.12970 (12)	0.0120 (2)
C29	1.10552 (19)	0.72043 (13)	−0.18784 (12)	0.0149 (3)
H29A	1.2106	0.7463	−0.1930	0.018*
C30	1.0790 (2)	0.63323 (13)	−0.23832 (13)	0.0173 (3)
H30A	1.1661	0.5992	−0.2762	0.021*
C31	0.9204 (2)	0.59773 (13)	−0.23128 (13)	0.0170 (3)
H31A	0.9011	0.5409	−0.2666	0.020*
C32	0.7901 (2)	0.64644 (13)	−0.17176 (12)	0.0150 (3)
H32A	0.6851	0.6208	−0.1675	0.018*
C33	0.28025 (18)	0.63124 (12)	0.03566 (12)	0.0132 (2)
H33A	0.2641	0.6003	−0.0257	0.020*
H33B	0.2139	0.6954	0.0405	0.020*
H33C	0.2501	0.5789	0.0997	0.020*
H1O2	0.547 (4)	0.516 (2)	0.104 (2)	0.028 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.01810 (8)	0.01305 (8)	0.01711 (8)	−0.00218 (5)	−0.00054 (6)	−0.00328 (6)
Br2	0.01454 (8)	0.01177 (8)	0.01788 (8)	−0.00154 (5)	−0.00447 (5)	−0.00345 (5)
O1	0.0200 (5)	0.0107 (4)	0.0152 (5)	−0.0001 (4)	−0.0042 (4)	−0.0015 (4)
O2	0.0173 (5)	0.0089 (4)	0.0143 (5)	0.0019 (4)	−0.0043 (4)	−0.0039 (4)
N1	0.0120 (5)	0.0103 (5)	0.0112 (5)	0.0008 (4)	−0.0027 (4)	−0.0017 (4)
N2	0.0113 (5)	0.0117 (5)	0.0100 (5)	−0.0005 (4)	−0.0021 (4)	−0.0017 (4)
C1	0.0182 (7)	0.0154 (6)	0.0167 (7)	−0.0008 (5)	−0.0006 (5)	−0.0035 (5)
C2	0.0225 (7)	0.0163 (7)	0.0164 (7)	−0.0009 (6)	0.0025 (6)	−0.0006 (5)
C3	0.0255 (8)	0.0194 (7)	0.0124 (6)	0.0030 (6)	−0.0032 (6)	−0.0016 (5)
C4	0.0206 (7)	0.0176 (7)	0.0148 (6)	0.0013 (5)	−0.0045 (5)	−0.0048 (5)
C5	0.0141 (6)	0.0113 (6)	0.0137 (6)	0.0014 (5)	−0.0021 (5)	−0.0024 (5)
C6	0.0149 (6)	0.0122 (6)	0.0126 (6)	0.0016 (5)	−0.0020 (5)	−0.0031 (5)
C7	0.0155 (6)	0.0122 (6)	0.0143 (6)	0.0001 (5)	−0.0031 (5)	−0.0027 (5)
C8	0.0138 (6)	0.0114 (6)	0.0125 (6)	−0.0003 (5)	−0.0035 (5)	−0.0021 (5)
C9	0.0107 (6)	0.0115 (6)	0.0135 (6)	−0.0013 (4)	−0.0026 (5)	−0.0031 (5)
C10	0.0110 (5)	0.0094 (5)	0.0107 (6)	0.0002 (4)	−0.0019 (4)	−0.0016 (4)
C11	0.0111 (6)	0.0120 (6)	0.0131 (6)	0.0015 (5)	−0.0028 (5)	−0.0008 (5)
C12	0.0167 (6)	0.0115 (6)	0.0135 (6)	−0.0003 (5)	−0.0058 (5)	−0.0026 (5)
C13	0.0112 (5)	0.0083 (5)	0.0105 (5)	0.0008 (4)	−0.0014 (4)	−0.0011 (4)
C14	0.0118 (6)	0.0081 (5)	0.0124 (6)	0.0010 (4)	−0.0029 (4)	−0.0024 (4)
C15	0.0122 (6)	0.0103 (5)	0.0118 (6)	0.0002 (4)	−0.0018 (5)	−0.0011 (4)
C16	0.0190 (7)	0.0131 (6)	0.0151 (6)	0.0017 (5)	−0.0027 (5)	0.0004 (5)
C17	0.0198 (7)	0.0188 (7)	0.0146 (7)	0.0006 (6)	0.0007 (5)	0.0031 (5)
C18	0.0180 (7)	0.0197 (7)	0.0142 (6)	0.0014 (6)	0.0019 (5)	−0.0002 (5)
C19	0.0133 (6)	0.0135 (6)	0.0141 (6)	0.0007 (5)	−0.0009 (5)	−0.0031 (5)
C20	0.0139 (6)	0.0151 (6)	0.0175 (7)	0.0030 (5)	−0.0019 (5)	−0.0059 (5)
C21	0.0145 (6)	0.0130 (6)	0.0178 (7)	0.0042 (5)	−0.0039 (5)	−0.0045 (5)
C22	0.0142 (6)	0.0108 (6)	0.0137 (6)	0.0017 (5)	−0.0037 (5)	−0.0015 (5)
C23	0.0109 (5)	0.0095 (5)	0.0116 (6)	0.0008 (4)	−0.0022 (4)	−0.0024 (4)
C24	0.0115 (6)	0.0105 (5)	0.0121 (6)	0.0005 (4)	−0.0025 (5)	−0.0017 (5)
C25	0.0126 (6)	0.0140 (6)	0.0112 (6)	−0.0001 (5)	−0.0024 (5)	−0.0002 (5)
C26	0.0119 (6)	0.0109 (5)	0.0104 (6)	0.0003 (4)	−0.0017 (4)	−0.0012 (4)
C27	0.0132 (6)	0.0110 (6)	0.0104 (6)	−0.0011 (5)	−0.0011 (5)	−0.0010 (4)
C28	0.0136 (6)	0.0104 (6)	0.0117 (6)	0.0001 (5)	−0.0022 (5)	−0.0013 (5)
C29	0.0132 (6)	0.0157 (6)	0.0147 (6)	0.0007 (5)	−0.0006 (5)	−0.0014 (5)
C30	0.0191 (7)	0.0164 (7)	0.0158 (7)	0.0023 (5)	0.0000 (5)	−0.0041 (5)
C31	0.0211 (7)	0.0141 (6)	0.0159 (6)	−0.0006 (5)	−0.0009 (5)	−0.0053 (5)
C32	0.0160 (6)	0.0143 (6)	0.0147 (6)	−0.0029 (5)	−0.0004 (5)	−0.0046 (5)
C33	0.0113 (6)	0.0137 (6)	0.0149 (6)	−0.0007 (5)	−0.0022 (5)	−0.0037 (5)

Br1—C5	1.8963 (15)	C14—C15	1.511 (2)
Br2—C28	1.8993 (15)	C15—C16	1.370 (2)
O1—C9	1.2144 (18)	C15—C24	1.410 (2)
O2—C14	1.4065 (17)	C16—C17	1.424 (2)
O2—H1O2	0.75 (3)	C16—H16A	0.9300
N1—C11	1.4697 (19)	C17—C18	1.380 (2)
N1—C12	1.4698 (19)	C17—H17A	0.9300
N1—C14	1.4785 (19)	C18—C19	1.421 (2)
N2—C33	1.4680 (19)	C18—H18A	0.9300
N2—C25	1.4684 (19)	C19—C24	1.405 (2)
N2—C13	1.4750 (19)	C19—C20	1.418 (2)
C1—C2	1.395 (2)	C20—C21	1.382 (2)
C1—C6	1.407 (2)	C20—H20A	0.9300
C1—H1A	0.9300	C21—C22	1.421 (2)
C2—C3	1.385 (3)	C21—H21A	0.9300
C2—H2A	0.9300	C22—C23	1.3749 (19)
C3—C4	1.388 (2)	C22—H22A	0.9300
C3—H3A	0.9300	C23—C24	1.416 (2)
C4—C5	1.387 (2)	C25—C26	1.542 (2)
C4—H4A	0.9300	C25—H25A	0.9700
C5—C6	1.397 (2)	C25—H25B	0.9700
C6—C7	1.474 (2)	C26—C27	1.521 (2)
C7—C8	1.344 (2)	C26—H26A	0.9800
C7—H7A	0.9300	C27—C28	1.402 (2)
C8—C9	1.510 (2)	C27—C32	1.405 (2)
C8—C12	1.523 (2)	C28—C29	1.387 (2)
C9—C10	1.522 (2)	C29—C30	1.391 (2)
C10—C11	1.554 (2)	C29—H29A	0.9300
C10—C26	1.558 (2)	C30—C31	1.389 (2)
C10—C13	1.569 (2)	C30—H30A	0.9300
C11—H11A	0.9700	C31—C32	1.394 (2)
C11—H11B	0.9700	C31—H31A	0.9300
C12—H12A	0.9700	C32—H32A	0.9300
C12—H12B	0.9700	C33—H33A	0.9600
C13—C23	1.526 (2)	C33—H33B	0.9600
C13—C14	1.592 (2)	C33—H33C	0.9600
C14—O2—H1O2	103 (2)	C16—C15—C14	132.30 (13)
C11—N1—C12	108.02 (12)	C24—C15—C14	108.17 (12)
C11—N1—C14	102.44 (11)	C15—C16—C17	118.42 (14)
C12—N1—C14	115.63 (11)	C15—C16—H16A	120.8
C33—N2—C25	112.31 (12)	C17—C16—H16A	120.8
C33—N2—C13	114.95 (12)	C18—C17—C16	122.38 (15)
C25—N2—C13	105.24 (11)	C18—C17—H17A	118.8
C2—C1—C6	121.38 (16)	C16—C17—H17A	118.8
C2—C1—H1A	119.3	C17—C18—C19	119.82 (14)
C6—C1—H1A	119.3	C17—C18—H18A	120.1
C3—C2—C1	119.73 (16)	C19—C18—H18A	120.1
C3—C2—H2A	120.1	C24—C19—C20	116.51 (14)
C1—C2—H2A	120.1	C24—C19—C18	116.89 (14)
C2—C3—C4	120.28 (15)	C20—C19—C18	126.60 (14)
C2—C3—H3A	119.9	C21—C20—C19	119.84 (14)
C4—C3—H3A	119.9	C21—C20—H20A	120.1
C5—C4—C3	119.32 (15)	C19—C20—H20A	120.1
C5—C4—H4A	120.3	C20—C21—C22	122.79 (14)
C3—C4—H4A	120.3	C20—C21—H21A	118.6
C4—C5—C6	122.33 (14)	C22—C21—H21A	118.6
C4—C5—Br1	117.66 (12)	C23—C22—C21	118.38 (14)
C6—C5—Br1	120.00 (11)	C23—C22—H22A	120.8
C5—C6—C1	116.92 (14)	C21—C22—H22A	120.8
C5—C6—C7	121.47 (14)	C22—C23—C24	118.82 (13)
C1—C6—C7	121.48 (14)	C22—C23—C13	132.51 (13)
C8—C7—C6	126.64 (14)	C24—C23—C13	108.52 (12)
C8—C7—H7A	116.7	C19—C24—C15	122.94 (13)
C6—C7—H7A	116.7	C19—C24—C23	123.65 (13)
C7—C8—C9	116.44 (13)	C15—C24—C23	113.41 (13)
C7—C8—C12	124.44 (14)	N2—C25—C26	105.15 (11)
C9—C8—C12	119.08 (12)	N2—C25—H25A	110.7
O1—C9—C8	122.98 (13)	C26—C25—H25A	110.7
O1—C9—C10	123.03 (13)	N2—C25—H25B	110.7
C8—C9—C10	113.85 (12)	C26—C25—H25B	110.7
C9—C10—C11	108.11 (12)	H25A—C25—H25B	108.8
C9—C10—C26	114.98 (11)	C27—C26—C25	114.83 (12)
C11—C10—C26	117.57 (11)	C27—C26—C10	113.94 (12)
C9—C10—C13	106.44 (11)	C25—C26—C10	102.43 (11)
C11—C10—C13	101.86 (11)	C27—C26—H26A	108.4
C26—C10—C13	106.49 (11)	C25—C26—H26A	108.4
N1—C11—C10	104.01 (11)	C10—C26—H26A	108.4
N1—C11—H11A	111.0	C28—C27—C32	115.83 (13)
C10—C11—H11A	111.0	C28—C27—C26	122.18 (13)
N1—C11—H11B	111.0	C32—C27—C26	121.98 (13)
C10—C11—H11B	111.0	C29—C28—C27	123.13 (14)
H11A—C11—H11B	109.0	C29—C28—Br2	115.84 (11)
N1—C12—C8	116.67 (12)	C27—C28—Br2	121.03 (11)
N1—C12—H12A	108.1	C28—C29—C30	119.60 (15)
C8—C12—H12A	108.1	C28—C29—H29A	120.2
N1—C12—H12B	108.1	C30—C29—H29A	120.2
C8—C12—H12B	108.1	C31—C30—C29	119.04 (15)
H12A—C12—H12B	107.3	C31—C30—H30A	120.5
N2—C13—C23	114.26 (12)	C29—C30—H30A	120.5
N2—C13—C10	102.66 (11)	C30—C31—C32	120.60 (15)
C23—C13—C10	119.66 (11)	C30—C31—H31A	119.7
N2—C13—C14	112.84 (11)	C32—C31—H31A	119.7
C23—C13—C14	103.45 (11)	C31—C32—C27	121.75 (15)
C10—C13—C14	103.78 (11)	C31—C32—H32A	119.1
O2—C14—N1	108.22 (11)	C27—C32—H32A	119.1
O2—C14—C15	112.29 (12)	N2—C33—H33A	109.5
N1—C14—C15	114.63 (12)	N2—C33—H33B	109.5
O2—C14—C13	110.91 (11)	H33A—C33—H33B	109.5
N1—C14—C13	105.17 (11)	N2—C33—H33C	109.5
C15—C14—C13	105.37 (11)	H33A—C33—H33C	109.5
C16—C15—C24	119.53 (14)	H33B—C33—H33C	109.5
C6—C1—C2—C3	1.5 (3)	C10—C13—C14—C15	135.81 (11)
C1—C2—C3—C4	0.0 (3)	O2—C14—C15—C16	51.9 (2)
C2—C3—C4—C5	−1.0 (3)	N1—C14—C15—C16	−72.2 (2)
C3—C4—C5—C6	0.5 (2)	C13—C14—C15—C16	172.71 (16)
C3—C4—C5—Br1	−179.35 (13)	O2—C14—C15—C24	−128.68 (13)
C4—C5—C6—C1	1.0 (2)	N1—C14—C15—C24	107.29 (14)
Br1—C5—C6—C1	−179.16 (11)	C13—C14—C15—C24	−7.84 (15)
C4—C5—C6—C7	176.88 (15)	C24—C15—C16—C17	−0.9 (2)
Br1—C5—C6—C7	−3.2 (2)	C14—C15—C16—C17	178.52 (16)
C2—C1—C6—C5	−2.0 (2)	C15—C16—C17—C18	−0.1 (3)
C2—C1—C6—C7	−177.90 (15)	C16—C17—C18—C19	0.5 (3)
C5—C6—C7—C8	135.05 (17)	C17—C18—C19—C24	0.0 (2)
C1—C6—C7—C8	−49.2 (2)	C17—C18—C19—C20	179.44 (16)
C6—C7—C8—C9	175.99 (14)	C24—C19—C20—C21	0.0 (2)
C6—C7—C8—C12	−6.2 (3)	C18—C19—C20—C21	−179.40 (16)
C7—C8—C9—O1	7.5 (2)	C19—C20—C21—C22	0.2 (2)
C12—C8—C9—O1	−170.38 (14)	C20—C21—C22—C23	0.2 (2)
C7—C8—C9—C10	−168.33 (13)	C21—C22—C23—C24	−0.9 (2)
C12—C8—C9—C10	13.77 (19)	C21—C22—C23—C13	174.12 (15)
O1—C9—C10—C11	142.12 (15)	N2—C13—C23—C22	−61.5 (2)
C8—C9—C10—C11	−42.03 (16)	C10—C13—C23—C22	60.7 (2)
O1—C9—C10—C26	8.5 (2)	C14—C13—C23—C22	175.42 (15)
C8—C9—C10—C26	−175.62 (12)	N2—C13—C23—C24	113.85 (13)
O1—C9—C10—C13	−109.10 (16)	C10—C13—C23—C24	−123.91 (13)
C8—C9—C10—C13	66.74 (15)	C14—C13—C23—C24	−9.21 (15)
C12—N1—C11—C10	−73.52 (14)	C20—C19—C24—C15	179.51 (14)
C14—N1—C11—C10	49.00 (13)	C18—C19—C24—C15	−1.0 (2)
C9—C10—C11—N1	73.21 (14)	C20—C19—C24—C23	−0.8 (2)
C26—C10—C11—N1	−154.57 (12)	C18—C19—C24—C23	178.75 (15)
C13—C10—C11—N1	−38.68 (13)	C16—C15—C24—C19	1.5 (2)
C11—N1—C12—C8	44.67 (17)	C14—C15—C24—C19	−178.07 (14)
C14—N1—C12—C8	−69.37 (17)	C16—C15—C24—C23	−178.31 (14)
C7—C8—C12—N1	168.00 (15)	C14—C15—C24—C23	2.16 (17)
C9—C8—C12—N1	−14.3 (2)	C22—C23—C24—C19	1.2 (2)
C33—N2—C13—C23	−31.95 (17)	C13—C23—C24—C19	−174.92 (14)
C25—N2—C13—C23	92.16 (14)	C22—C23—C24—C15	−179.05 (14)
C33—N2—C13—C10	−163.06 (11)	C13—C23—C24—C15	4.84 (17)
C25—N2—C13—C10	−38.96 (13)	C33—N2—C25—C26	169.39 (11)
C33—N2—C13—C14	85.87 (14)	C13—N2—C25—C26	43.64 (14)
C25—N2—C13—C14	−150.02 (12)	N2—C25—C26—C27	95.36 (14)
C9—C10—C13—N2	143.27 (11)	N2—C25—C26—C10	−28.69 (13)
C11—C10—C13—N2	−103.58 (12)	C9—C10—C26—C27	122.63 (13)
C26—C10—C13—N2	20.15 (13)	C11—C10—C26—C27	−6.42 (18)
C9—C10—C13—C23	15.49 (17)	C13—C10—C26—C27	−119.76 (13)
C11—C10—C13—C23	128.64 (13)	C9—C10—C26—C25	−112.74 (13)
C26—C10—C13—C23	−107.63 (14)	C11—C10—C26—C25	118.21 (13)
C9—C10—C13—C14	−99.04 (12)	C13—C10—C26—C25	4.87 (13)
C11—C10—C13—C14	14.11 (13)	C25—C26—C27—C28	168.94 (13)
C26—C10—C13—C14	137.84 (11)	C10—C26—C27—C28	−73.35 (17)
C11—N1—C14—O2	79.77 (13)	C25—C26—C27—C32	−11.6 (2)
C12—N1—C14—O2	−163.02 (12)	C10—C26—C27—C32	106.11 (16)
C11—N1—C14—C15	−154.06 (12)	C32—C27—C28—C29	−1.7 (2)
C12—N1—C14—C15	−36.85 (17)	C26—C27—C28—C29	177.82 (14)
C11—N1—C14—C13	−38.81 (13)	C32—C27—C28—Br2	178.85 (11)
C12—N1—C14—C13	78.40 (14)	C26—C27—C28—Br2	−1.7 (2)
N2—C13—C14—O2	7.93 (16)	C27—C28—C29—C30	0.5 (2)
C23—C13—C14—O2	131.93 (12)	Br2—C28—C29—C30	179.96 (12)
C10—C13—C14—O2	−102.44 (13)	C28—C29—C30—C31	1.4 (2)
N2—C13—C14—N1	124.69 (12)	C29—C30—C31—C32	−2.0 (3)
C23—C13—C14—N1	−111.31 (12)	C30—C31—C32—C27	0.7 (3)
C10—C13—C14—N1	14.32 (13)	C28—C27—C32—C31	1.1 (2)
N2—C13—C14—C15	−113.81 (13)	C26—C27—C32—C31	−178.41 (15)
C23—C13—C14—C15	10.19 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.75 (3)	2.12 (3)	2.6735 (18)	132 (3)
C32—H32A···O2i	0.93	2.47	3.374 (2)	163
C33—H33A···O2i	0.96	2.55	3.292 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.75 (3)	2.12 (3)	2.6735 (18)	132 (3)
C32—H32A⋯O2i	0.93	2.47	3.374 (2)	163
C33—H33A⋯O2i	0.96	2.55	3.292 (2)	134

Symmetry code: (i) .