11-[(E)-4-Bromo-benzyl-idene]-8-(4-bromo-phen-yl)-14-hy-droxy-3,13-diaza-hepta-cyclo-[13.7.1.1.0.0.0.0]tetra-cosa-1(22),15,17,19(23),20-pentaen-10-one.

In the title compound, C(35)H(28)Br(2)N(2)O(2), the piperidone ring adopts a chair conformation and the five-membered ring of the pyrrolidine ring adopts an envelope conformation. The naphthalene ring system makes dihedral angles of 37.12 (8) and 50.62 (9)° with the terminal bromo-substituted benzene rings. The dihedral angle between the two bromo-substituted benzene rings is 72.54 (10)°. In the crystal, adjacent mol-ecules are connected by a pair of inter-molecular C-H⋯O hydrogen bonds, forming an inversion dimer. An intra-molecular O-H⋯N hydrogen bond is also present.

Related literature

For details of cyclo­addition, see: Babu & Raghunathan (2007 ▶); Boruah et al. (2007 ▶); Dondas et al. (2004 ▶); Hong et al. (2007 ▶); Karthikeyan et al. (2007 ▶); Liddell (1998 ▶); Ramesh et al. (2007 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C35H28Br2N2O2

M = 668.41

Triclinic,

a = 8.4833 (10) Å

b = 11.8334 (13) Å

c = 14.8942 (17) Å

α = 79.868 (2)°

β = 80.705 (2)°

γ = 77.359 (2)°

V = 1424.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.88 mm−1

T = 100 K

0.44 × 0.17 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.364, T max = 0.657

14706 measured reflections

6459 independent reflections

5384 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.07

6459 reflections

374 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.48 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/S1600536810042091/is2614sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042091/is2614Isup2.hkl

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

C35H28Br2N2O2	Z = 2
Mr = 668.41	F(000) = 676
Triclinic, P1	Dx = 1.559 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4833 (10) Å	Cell parameters from 6649 reflections
b = 11.8334 (13) Å	θ = 2.4–28.4°
c = 14.8942 (17) Å	µ = 2.88 mm−1
α = 79.868 (2)°	T = 100 K
β = 80.705 (2)°	Block, colourless
γ = 77.359 (2)°	0.44 × 0.17 × 0.16 mm
V = 1424.4 (3) Å3

Bruker APEXII DUO CCD area-detector diffractometer	6459 independent reflections
Radiation source: fine-focus sealed tube	5384 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
Tmin = 0.364, Tmax = 0.657	k = −15→15
14706 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.030P)2 + 0.5557P] where P = (Fo2 + 2Fc2)/3
6459 reflections	(Δ/σ)max = 0.003
374 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.48 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.95912 (3)	0.70022 (2)	0.375928 (15)	0.03029 (7)
Br2	0.50038 (3)	0.80345 (2)	1.346623 (16)	0.03079 (8)
O1	0.36372 (17)	0.90896 (12)	0.88975 (10)	0.0203 (3)
O2	0.11709 (19)	0.50546 (13)	0.90383 (10)	0.0213 (3)
N1	0.3708 (2)	0.56045 (14)	0.88753 (11)	0.0159 (3)
N2	−0.02666 (19)	0.70855 (14)	0.94557 (11)	0.0157 (3)
C1	0.7446 (3)	0.66951 (19)	0.64742 (15)	0.0225 (4)
H1A	0.7501	0.6124	0.6990	0.027*
C2	0.8377 (3)	0.64507 (19)	0.56501 (15)	0.0254 (5)
H2A	0.9044	0.5720	0.5610	0.030*
C3	0.8299 (3)	0.7308 (2)	0.48903 (14)	0.0228 (4)
C4	0.7332 (3)	0.84159 (19)	0.49339 (14)	0.0225 (4)
H4A	0.7310	0.8990	0.4419	0.027*
C5	0.6406 (3)	0.86453 (18)	0.57587 (14)	0.0213 (4)
H5A	0.5758	0.9384	0.5794	0.026*
C6	0.6419 (2)	0.77957 (18)	0.65411 (13)	0.0182 (4)
C7	0.5367 (2)	0.81193 (17)	0.73743 (13)	0.0174 (4)
H7A	0.5086	0.8919	0.7400	0.021*
C8	0.4743 (2)	0.74428 (17)	0.81089 (13)	0.0157 (4)
C9	0.3618 (2)	0.80907 (17)	0.88225 (13)	0.0150 (4)
C10	0.2428 (2)	0.73992 (16)	0.94201 (13)	0.0136 (4)
C11	0.3388 (2)	0.61511 (16)	0.97163 (13)	0.0158 (4)
H11A	0.4399	0.6181	0.9929	0.019*
H11B	0.2746	0.5724	1.0203	0.019*
C12	0.4976 (2)	0.61138 (17)	0.82450 (13)	0.0168 (4)
H12A	0.5039	0.5869	0.7650	0.020*
H12B	0.6014	0.5787	0.8472	0.020*
C13	0.2392 (2)	0.70348 (18)	1.17155 (14)	0.0192 (4)
H13A	0.1953	0.6386	1.1697	0.023*
C14	0.3250 (3)	0.70395 (19)	1.24397 (14)	0.0217 (4)
H14A	0.3397	0.6396	1.2898	0.026*
C15	0.3874 (2)	0.80129 (18)	1.24641 (14)	0.0201 (4)
C16	0.3701 (3)	0.89758 (19)	1.17861 (14)	0.0228 (4)
H16A	0.4137	0.9624	1.1810	0.027*
C17	0.2856 (2)	0.89479 (18)	1.10674 (14)	0.0189 (4)
H17A	0.2737	0.9589	1.0605	0.023*
C18	0.2184 (2)	0.79958 (16)	1.10161 (13)	0.0151 (4)
C19	0.1330 (2)	0.80060 (16)	1.01924 (13)	0.0145 (4)
H19A	0.0937	0.8824	0.9940	0.017*
C20	−0.0118 (2)	0.73723 (17)	1.03739 (13)	0.0157 (4)
H20A	0.0135	0.6647	1.0802	0.019*
C21	−0.1792 (2)	0.80658 (19)	1.07021 (14)	0.0216 (4)
H21A	−0.1806	0.8900	1.0586	0.026*
H21B	−0.2099	0.7836	1.1354	0.026*
C22	−0.2933 (3)	0.7743 (2)	1.01281 (15)	0.0237 (4)
H22A	−0.3252	0.7005	1.0398	0.028*
H22B	−0.3904	0.8348	1.0072	0.028*
C23	−0.1894 (2)	0.76447 (19)	0.91974 (15)	0.0218 (4)
H23A	−0.2285	0.7163	0.8852	0.026*
H23B	−0.1884	0.8410	0.8836	0.026*
C24	0.1223 (2)	0.71519 (16)	0.88158 (13)	0.0137 (4)
C25	0.1053 (2)	0.78952 (17)	0.78823 (13)	0.0165 (4)
C26	0.0509 (3)	0.90806 (18)	0.76295 (15)	0.0220 (4)
H26A	0.0155	0.9579	0.8071	0.026*
C27	0.0505 (3)	0.9519 (2)	0.66793 (17)	0.0302 (5)
H27A	0.0114	1.0313	0.6507	0.036*
C28	0.1049 (3)	0.8824 (2)	0.60051 (16)	0.0333 (5)
H28A	0.1034	0.9152	0.5391	0.040*
C29	0.1642 (3)	0.7598 (2)	0.62403 (15)	0.0253 (5)
C30	0.2261 (3)	0.6766 (2)	0.56313 (15)	0.0330 (6)
H30A	0.2332	0.7008	0.5000	0.040*
C31	0.2762 (3)	0.5598 (2)	0.59660 (16)	0.0326 (6)
H31A	0.3143	0.5063	0.5554	0.039*
C32	0.2708 (3)	0.5194 (2)	0.69231 (15)	0.0257 (5)
H32A	0.3041	0.4404	0.7139	0.031*
C33	0.2154 (2)	0.59901 (18)	0.75230 (14)	0.0186 (4)
C34	0.1594 (2)	0.71801 (18)	0.71875 (14)	0.0187 (4)
C35	0.2080 (2)	0.58723 (16)	0.85513 (13)	0.0156 (4)
H1O2	0.035 (4)	0.538 (2)	0.9321 (19)	0.037 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.02851 (13)	0.03823 (14)	0.02268 (12)	−0.00510 (10)	0.00563 (9)	−0.01058 (9)
Br2	0.03305 (14)	0.03556 (14)	0.02841 (13)	−0.00501 (10)	−0.01459 (10)	−0.00954 (10)
O1	0.0203 (8)	0.0184 (7)	0.0235 (7)	−0.0077 (6)	0.0010 (6)	−0.0048 (6)
O2	0.0213 (8)	0.0153 (7)	0.0275 (8)	−0.0092 (6)	0.0025 (6)	−0.0015 (6)
N1	0.0155 (8)	0.0147 (8)	0.0164 (8)	−0.0019 (6)	−0.0024 (6)	−0.0002 (6)
N2	0.0117 (8)	0.0177 (8)	0.0184 (8)	−0.0053 (6)	−0.0026 (6)	−0.0006 (6)
C1	0.0177 (11)	0.0235 (11)	0.0230 (10)	−0.0020 (8)	0.0011 (8)	−0.0004 (8)
C2	0.0218 (11)	0.0233 (11)	0.0289 (11)	−0.0033 (9)	0.0038 (9)	−0.0057 (9)
C3	0.0185 (10)	0.0330 (12)	0.0182 (10)	−0.0077 (9)	0.0028 (8)	−0.0084 (9)
C4	0.0254 (11)	0.0249 (11)	0.0177 (10)	−0.0079 (9)	−0.0022 (8)	−0.0017 (8)
C5	0.0228 (11)	0.0196 (10)	0.0216 (10)	−0.0051 (8)	−0.0021 (8)	−0.0031 (8)
C6	0.0154 (10)	0.0223 (10)	0.0179 (10)	−0.0068 (8)	−0.0007 (8)	−0.0032 (8)
C7	0.0161 (10)	0.0180 (9)	0.0192 (10)	−0.0049 (8)	−0.0027 (8)	−0.0032 (8)
C8	0.0095 (9)	0.0199 (10)	0.0182 (9)	−0.0022 (7)	−0.0028 (7)	−0.0041 (8)
C9	0.0129 (9)	0.0165 (9)	0.0161 (9)	−0.0025 (7)	−0.0050 (7)	−0.0011 (7)
C10	0.0118 (9)	0.0146 (9)	0.0142 (9)	−0.0021 (7)	−0.0031 (7)	−0.0014 (7)
C11	0.0156 (10)	0.0142 (9)	0.0164 (9)	−0.0012 (7)	−0.0037 (7)	−0.0002 (7)
C12	0.0136 (10)	0.0169 (9)	0.0194 (9)	−0.0018 (7)	−0.0022 (7)	−0.0029 (8)
C13	0.0195 (10)	0.0199 (10)	0.0189 (10)	−0.0065 (8)	−0.0011 (8)	−0.0032 (8)
C14	0.0222 (11)	0.0246 (11)	0.0166 (10)	−0.0020 (9)	−0.0030 (8)	−0.0010 (8)
C15	0.0162 (10)	0.0259 (11)	0.0195 (10)	−0.0018 (8)	−0.0032 (8)	−0.0090 (8)
C16	0.0216 (11)	0.0246 (11)	0.0250 (11)	−0.0071 (9)	−0.0034 (9)	−0.0076 (9)
C17	0.0181 (10)	0.0183 (10)	0.0201 (10)	−0.0042 (8)	−0.0012 (8)	−0.0027 (8)
C18	0.0119 (9)	0.0157 (9)	0.0165 (9)	−0.0011 (7)	0.0001 (7)	−0.0030 (7)
C19	0.0127 (9)	0.0128 (9)	0.0171 (9)	−0.0022 (7)	−0.0013 (7)	−0.0007 (7)
C20	0.0139 (10)	0.0157 (9)	0.0171 (9)	−0.0039 (8)	−0.0018 (7)	−0.0004 (7)
C21	0.0129 (10)	0.0273 (11)	0.0222 (10)	−0.0020 (8)	0.0011 (8)	−0.0026 (8)
C22	0.0135 (10)	0.0265 (11)	0.0298 (11)	−0.0034 (8)	−0.0023 (8)	−0.0021 (9)
C23	0.0127 (10)	0.0257 (11)	0.0282 (11)	−0.0029 (8)	−0.0063 (8)	−0.0046 (9)
C24	0.0120 (9)	0.0121 (9)	0.0172 (9)	−0.0037 (7)	−0.0031 (7)	0.0001 (7)
C25	0.0121 (9)	0.0200 (10)	0.0172 (9)	−0.0055 (8)	−0.0044 (7)	0.0029 (8)
C26	0.0199 (11)	0.0185 (10)	0.0263 (11)	−0.0045 (8)	−0.0043 (8)	0.0026 (8)
C27	0.0277 (13)	0.0243 (11)	0.0343 (13)	−0.0051 (10)	−0.0081 (10)	0.0109 (10)
C28	0.0298 (13)	0.0455 (15)	0.0213 (11)	−0.0106 (11)	−0.0075 (10)	0.0115 (10)
C29	0.0211 (11)	0.0355 (12)	0.0210 (10)	−0.0105 (9)	−0.0066 (9)	0.0009 (9)
C30	0.0293 (13)	0.0566 (16)	0.0163 (10)	−0.0149 (12)	−0.0037 (9)	−0.0050 (10)
C31	0.0305 (13)	0.0462 (15)	0.0266 (12)	−0.0114 (11)	−0.0012 (10)	−0.0172 (11)
C32	0.0251 (12)	0.0286 (12)	0.0270 (11)	−0.0082 (9)	−0.0037 (9)	−0.0095 (9)
C33	0.0143 (10)	0.0240 (10)	0.0194 (10)	−0.0072 (8)	−0.0029 (8)	−0.0031 (8)
C34	0.0165 (10)	0.0231 (10)	0.0185 (10)	−0.0081 (8)	−0.0060 (8)	0.0002 (8)
C35	0.0148 (10)	0.0139 (9)	0.0182 (9)	−0.0044 (7)	−0.0013 (7)	−0.0012 (7)

Br1—C3	1.901 (2)	C15—C16	1.382 (3)
Br2—C15	1.9063 (19)	C16—C17	1.390 (3)
O1—C9	1.210 (2)	C16—H16A	0.9300
O2—C35	1.399 (2)	C17—C18	1.388 (3)
O2—H1O2	0.81 (3)	C17—H17A	0.9300
N1—C11	1.470 (2)	C18—C19	1.519 (3)
N1—C12	1.470 (3)	C19—C20	1.539 (3)
N1—C35	1.487 (2)	C19—H19A	0.9800
N2—C24	1.463 (2)	C20—C21	1.529 (3)
N2—C23	1.474 (2)	C20—H20A	0.9800
N2—C20	1.496 (2)	C21—C22	1.536 (3)
C1—C2	1.388 (3)	C21—H21A	0.9700
C1—C6	1.409 (3)	C21—H21B	0.9700
C1—H1A	0.9300	C22—C23	1.526 (3)
C2—C3	1.380 (3)	C22—H22A	0.9700
C2—H2A	0.9300	C22—H22B	0.9700
C3—C4	1.392 (3)	C23—H23A	0.9700
C4—C5	1.383 (3)	C23—H23B	0.9700
C4—H4A	0.9300	C24—C25	1.519 (3)
C5—C6	1.398 (3)	C24—C35	1.616 (3)
C5—H5A	0.9300	C25—C26	1.382 (3)
C6—C7	1.464 (3)	C25—C34	1.408 (3)
C7—C8	1.345 (3)	C26—C27	1.419 (3)
C7—H7A	0.9300	C26—H26A	0.9300
C8—C9	1.506 (3)	C27—C28	1.368 (4)
C8—C12	1.523 (3)	C27—H27A	0.9300
C9—C10	1.515 (3)	C28—C29	1.428 (3)
C10—C19	1.536 (2)	C28—H28A	0.9300
C10—C11	1.549 (3)	C29—C34	1.408 (3)
C10—C24	1.569 (2)	C29—C30	1.415 (3)
C11—H11A	0.9700	C30—C31	1.382 (4)
C11—H11B	0.9700	C30—H30A	0.9300
C12—H12A	0.9700	C31—C32	1.418 (3)
C12—H12B	0.9700	C31—H31A	0.9300
C13—C14	1.397 (3)	C32—C33	1.369 (3)
C13—C18	1.401 (3)	C32—H32A	0.9300
C13—H13A	0.9300	C33—C34	1.412 (3)
C14—C15	1.377 (3)	C33—C35	1.505 (3)
C14—H14A	0.9300
C35—O2—H1O2	110 (2)	C18—C19—C20	116.38 (16)
C11—N1—C12	108.25 (15)	C10—C19—C20	101.97 (14)
C11—N1—C35	102.77 (14)	C18—C19—H19A	108.0
C12—N1—C35	115.10 (15)	C10—C19—H19A	108.0
C24—N2—C23	122.19 (16)	C20—C19—H19A	108.0
C24—N2—C20	111.43 (14)	N2—C20—C21	105.40 (15)
C23—N2—C20	109.51 (15)	N2—C20—C19	104.64 (15)
C2—C1—C6	121.0 (2)	C21—C20—C19	117.58 (16)
C2—C1—H1A	119.5	N2—C20—H20A	109.6
C6—C1—H1A	119.5	C21—C20—H20A	109.6
C3—C2—C1	119.1 (2)	C19—C20—H20A	109.6
C3—C2—H2A	120.5	C20—C21—C22	103.60 (16)
C1—C2—H2A	120.5	C20—C21—H21A	111.0
C2—C3—C4	121.69 (19)	C22—C21—H21A	111.0
C2—C3—Br1	119.80 (16)	C20—C21—H21B	111.0
C4—C3—Br1	118.47 (16)	C22—C21—H21B	111.0
C5—C4—C3	118.6 (2)	H21A—C21—H21B	109.0
C5—C4—H4A	120.7	C23—C22—C21	103.12 (16)
C3—C4—H4A	120.7	C23—C22—H22A	111.1
C4—C5—C6	121.70 (19)	C21—C22—H22A	111.1
C4—C5—H5A	119.1	C23—C22—H22B	111.1
C6—C5—H5A	119.1	C21—C22—H22B	111.1
C5—C6—C1	117.91 (18)	H22A—C22—H22B	109.1
C5—C6—C7	117.39 (18)	N2—C23—C22	102.76 (16)
C1—C6—C7	124.70 (19)	N2—C23—H23A	111.2
C8—C7—C6	130.21 (19)	C22—C23—H23A	111.2
C8—C7—H7A	114.9	N2—C23—H23B	111.2
C6—C7—H7A	114.9	C22—C23—H23B	111.2
C7—C8—C9	115.48 (17)	H23A—C23—H23B	109.1
C7—C8—C12	126.23 (17)	N2—C24—C25	117.47 (15)
C9—C8—C12	118.14 (17)	N2—C24—C10	103.75 (14)
O1—C9—C8	122.78 (18)	C25—C24—C10	118.48 (16)
O1—C9—C10	122.87 (17)	N2—C24—C35	110.44 (15)
C8—C9—C10	114.33 (16)	C25—C24—C35	102.85 (15)
C9—C10—C19	115.73 (15)	C10—C24—C35	102.89 (14)
C9—C10—C11	107.62 (15)	C26—C25—C34	118.66 (18)
C19—C10—C11	115.94 (16)	C26—C25—C24	131.91 (18)
C9—C10—C24	109.71 (15)	C34—C25—C24	109.42 (17)
C19—C10—C24	104.93 (15)	C25—C26—C27	118.3 (2)
C11—C10—C24	101.86 (14)	C25—C26—H26A	120.8
N1—C11—C10	103.98 (14)	C27—C26—H26A	120.8
N1—C11—H11A	111.0	C28—C27—C26	122.9 (2)
C10—C11—H11A	111.0	C28—C27—H27A	118.6
N1—C11—H11B	111.0	C26—C27—H27A	118.6
C10—C11—H11B	111.0	C27—C28—C29	120.3 (2)
H11A—C11—H11B	109.0	C27—C28—H28A	119.8
N1—C12—C8	116.06 (16)	C29—C28—H28A	119.8
N1—C12—H12A	108.3	C34—C29—C30	116.9 (2)
C8—C12—H12A	108.3	C34—C29—C28	115.7 (2)
N1—C12—H12B	108.3	C30—C29—C28	127.4 (2)
C8—C12—H12B	108.3	C31—C30—C29	120.6 (2)
H12A—C12—H12B	107.4	C31—C30—H30A	119.7
C14—C13—C18	120.83 (19)	C29—C30—H30A	119.7
C14—C13—H13A	119.6	C30—C31—C32	121.6 (2)
C18—C13—H13A	119.6	C30—C31—H31A	119.2
C15—C14—C13	118.9 (2)	C32—C31—H31A	119.2
C15—C14—H14A	120.5	C33—C32—C31	118.6 (2)
C13—C14—H14A	120.5	C33—C32—H32A	120.7
C14—C15—C16	122.01 (18)	C31—C32—H32A	120.7
C14—C15—Br2	118.98 (16)	C32—C33—C34	120.08 (19)
C16—C15—Br2	119.01 (15)	C32—C33—C35	131.8 (2)
C15—C16—C17	118.09 (19)	C34—C33—C35	108.01 (16)
C15—C16—H16A	121.0	C29—C34—C25	124.07 (19)
C17—C16—H16A	121.0	C29—C34—C33	122.07 (19)
C18—C17—C16	122.2 (2)	C25—C34—C33	113.82 (17)
C18—C17—H17A	118.9	O2—C35—N1	108.74 (15)
C16—C17—H17A	118.9	O2—C35—C33	113.94 (15)
C17—C18—C13	117.91 (17)	N1—C35—C33	113.66 (16)
C17—C18—C19	119.40 (17)	O2—C35—C24	108.79 (15)
C13—C18—C19	122.62 (17)	N1—C35—C24	105.65 (14)
C18—C19—C10	113.92 (15)	C33—C35—C24	105.59 (15)
C6—C1—C2—C3	0.6 (3)	C23—N2—C24—C25	4.1 (2)
C1—C2—C3—C4	1.1 (3)	C20—N2—C24—C25	−128.02 (17)
C1—C2—C3—Br1	178.94 (16)	C23—N2—C24—C10	137.01 (17)
C2—C3—C4—C5	−1.3 (3)	C20—N2—C24—C10	4.87 (19)
Br1—C3—C4—C5	−179.23 (15)	C23—N2—C24—C35	−113.35 (18)
C3—C4—C5—C6	−0.1 (3)	C20—N2—C24—C35	114.51 (16)
C4—C5—C6—C1	1.7 (3)	C9—C10—C24—N2	−150.70 (15)
C4—C5—C6—C7	−178.66 (19)	C19—C10—C24—N2	−25.76 (18)
C2—C1—C6—C5	−2.0 (3)	C11—C10—C24—N2	95.48 (16)
C2—C1—C6—C7	178.4 (2)	C9—C10—C24—C25	−18.4 (2)
C5—C6—C7—C8	157.1 (2)	C19—C10—C24—C25	106.54 (18)
C1—C6—C7—C8	−23.3 (3)	C11—C10—C24—C25	−132.22 (17)
C6—C7—C8—C9	−176.58 (18)	C9—C10—C24—C35	94.16 (17)
C6—C7—C8—C12	−1.1 (3)	C19—C10—C24—C35	−140.89 (15)
C7—C8—C9—O1	−21.9 (3)	C11—C10—C24—C35	−19.66 (18)
C12—C8—C9—O1	162.27 (18)	N2—C24—C25—C26	63.1 (3)
C7—C8—C9—C10	156.46 (17)	C10—C24—C25—C26	−62.8 (3)
C12—C8—C9—C10	−19.4 (2)	C35—C24—C25—C26	−175.4 (2)
O1—C9—C10—C19	−5.1 (3)	N2—C24—C25—C34	−117.82 (18)
C8—C9—C10—C19	176.55 (15)	C10—C24—C25—C34	116.24 (18)
O1—C9—C10—C11	−136.63 (19)	C35—C24—C25—C34	3.7 (2)
C8—C9—C10—C11	45.05 (19)	C34—C25—C26—C27	0.7 (3)
O1—C9—C10—C24	113.3 (2)	C24—C25—C26—C27	179.7 (2)
C8—C9—C10—C24	−65.00 (19)	C25—C26—C27—C28	−1.6 (3)
C12—N1—C11—C10	73.46 (18)	C26—C27—C28—C29	0.7 (4)
C35—N1—C11—C10	−48.73 (18)	C27—C28—C29—C34	1.0 (3)
C9—C10—C11—N1	−72.90 (17)	C27—C28—C29—C30	−179.3 (2)
C19—C10—C11—N1	155.71 (15)	C34—C29—C30—C31	1.1 (3)
C24—C10—C11—N1	42.46 (18)	C28—C29—C30—C31	−178.6 (2)
C11—N1—C12—C8	−47.2 (2)	C29—C30—C31—C32	−1.3 (4)
C35—N1—C12—C8	67.1 (2)	C30—C31—C32—C33	−0.5 (3)
C7—C8—C12—N1	−155.72 (18)	C31—C32—C33—C34	2.4 (3)
C9—C8—C12—N1	19.6 (2)	C31—C32—C33—C35	−174.0 (2)
C18—C13—C14—C15	0.8 (3)	C30—C29—C34—C25	178.4 (2)
C13—C14—C15—C16	−1.1 (3)	C28—C29—C34—C25	−1.8 (3)
C13—C14—C15—Br2	178.65 (15)	C30—C29—C34—C33	0.8 (3)
C14—C15—C16—C17	0.5 (3)	C28—C29—C34—C33	−179.4 (2)
Br2—C15—C16—C17	−179.23 (15)	C26—C25—C34—C29	1.0 (3)
C15—C16—C17—C18	0.4 (3)	C24—C25—C34—C29	−178.22 (18)
C16—C17—C18—C13	−0.6 (3)	C26—C25—C34—C33	178.72 (18)
C16—C17—C18—C19	−177.76 (18)	C24—C25—C34—C33	−0.5 (2)
C14—C13—C18—C17	0.0 (3)	C32—C33—C34—C29	−2.6 (3)
C14—C13—C18—C19	177.05 (18)	C35—C33—C34—C29	174.52 (18)
C17—C18—C19—C10	94.5 (2)	C32—C33—C34—C25	179.59 (19)
C13—C18—C19—C10	−82.5 (2)	C35—C33—C34—C25	−3.3 (2)
C17—C18—C19—C20	−147.24 (18)	C11—N1—C35—O2	−81.90 (17)
C13—C18—C19—C20	35.7 (3)	C12—N1—C35—O2	160.66 (15)
C9—C10—C19—C18	−76.7 (2)	C11—N1—C35—C33	150.04 (16)
C11—C10—C19—C18	50.8 (2)	C12—N1—C35—C33	32.6 (2)
C24—C10—C19—C18	162.24 (15)	C11—N1—C35—C24	34.74 (18)
C9—C10—C19—C20	157.07 (15)	C12—N1—C35—C24	−82.70 (18)
C11—C10—C19—C20	−75.47 (19)	C32—C33—C35—O2	−58.7 (3)
C24—C10—C19—C20	36.01 (18)	C34—C33—C35—O2	124.68 (18)
C24—N2—C20—C21	142.38 (16)	C32—C33—C35—N1	66.7 (3)
C23—N2—C20—C21	4.1 (2)	C34—C33—C35—N1	−109.99 (18)
C24—N2—C20—C19	17.7 (2)	C32—C33—C35—C24	−178.0 (2)
C23—N2—C20—C19	−120.52 (17)	C34—C33—C35—C24	5.4 (2)
C18—C19—C20—N2	−157.36 (15)	N2—C24—C35—O2	−1.9 (2)
C10—C19—C20—N2	−32.76 (18)	C25—C24—C35—O2	−128.07 (16)
C18—C19—C20—C21	86.1 (2)	C10—C24—C35—O2	108.29 (16)
C10—C19—C20—C21	−149.26 (17)	N2—C24—C35—N1	−118.52 (16)
N2—C20—C21—C22	20.2 (2)	C25—C24—C35—N1	115.33 (16)
C19—C20—C21—C22	136.26 (18)	C10—C24—C35—N1	−8.31 (19)
C20—C21—C22—C23	−36.4 (2)	N2—C24—C35—C33	120.76 (16)
C24—N2—C23—C22	−159.72 (16)	C25—C24—C35—C33	−5.39 (19)
C20—N2—C23—C22	−26.8 (2)	C10—C24—C35—C33	−129.03 (16)
C21—C22—C23—N2	38.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.81 (3)	2.01 (2)	2.578 (2)	127 (3)
C20—H20A···O2i	0.98	2.46	3.130 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.81 (3)	2.01 (2)	2.578 (2)	127 (3)
C20—H20A⋯O2i	0.98	2.46	3.130 (3)	125

Symmetry code: (i) .