2,9b-trans-3,9b-cis-2,3-Bis(4-bromo­phenyl)-2,3,3a,4,5,9b,1',2',3',4'-deca­hydro-1H-benzo­[e]­indene-1-spiro-2'-naphthalene-1',9b-diol acetone solvate

The title compound, C₃₄H₃₀Br₂O₂.C₃H₆O, was synthesized by the dimerization of 2-(4-bromo­benzal)-1-tetralone, induced by a low-valent titanium reagent (TiCl₄/Zn). X-ray analysis reveals that the cyclo­hexane ring spiro-fused to the 5-membered ring adopts a boat conformation, while the other cyclo­hexane ring adopts a screw-boat conformation.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.045
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C5     -   C14     ..       7.16 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C6      ..       5.70 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C25    -   C26     ..       5.26 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C32
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        C36
PLAT731_ALERT_1_C Bond    Calc     0.81(3), Rep   0.810(10) ......       3.00 su-Rat
              O1   -H1O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.81(3), Rep   0.810(10) ......       3.00 su-Rat
              O1   -H1O     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.04(3), Rep   2.036(11) ......       2.73 su-Rat
              H1O  -O3      1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H6 O

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

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

---

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,9 b-cis-3,9 b-trans-2,3-Bis(4-bromophenyl)-2,3,3a,4,5,9 b,1',2',3',4'-decahydro- 1H-benzo[e]indene-1-spiro-2'-naphthalene-1',9 b-diol acetone solvate

Crystal data

C34H30Br2O2·C3H6O	Z = 2
Mr = 688.48	F(000) = 704
Triclinic, P1	Dx = 1.419 Mg m^−3
Hall symbol: -P 1	Melting point = 428–429 K
a = 11.427 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.042 (1) Å	Cell parameters from 27 reflections
c = 12.992 (2) Å	θ = 3.0–15.1°
α = 77.87 (1)°	µ = 2.55 mm^−1
β = 67.73 (1)°	T = 296 K
γ = 81.02 (1)°	Block, colorless
V = 1611.8 (4) Å^3	0.36 × 0.36 × 0.14 mm

Data collection

Siemens P4 diffractometer	2436 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 25.3°, θmin = 1.7°
ω scans	h = 0→13
Absorption correction: ψ scan (XSCANS; Siemens, 1994)	k = −14→14
Tmin = 0.446, Tmax = 0.700	l = −14→15
6445 measured reflections	3 standard reflections every 97 reflections
5836 independent reflections	intensity decay: 7.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.045	w = 1/[σ^2(Fo^2) + (0.01P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max = 0.001
5836 reflections	Δρmax = 0.36 e Å^−3
390 parameters	Δρmin = −0.30 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0067 (2)

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	0.46259 (3)	0.71697 (3)	0.38617 (4)	0.07577 (17)
Br2	0.61361 (4)	−0.02315 (4)	0.33515 (4)	0.0967 (2)
O1	1.2488 (2)	0.3894 (2)	0.0665 (2)	0.0493 (7)
O2	1.1133 (2)	0.5865 (2)	0.0305 (2)	0.0496 (7)
C1	0.9807 (3)	0.4336 (2)	0.2298 (2)	0.0324 (8)
H1	0.9927	0.4222	0.1539	0.039*
C2	0.9894 (2)	0.3141 (2)	0.2992 (2)	0.0335 (8)
H2	0.9795	0.3227	0.3755	0.040*
C3	1.1276 (3)	0.2693 (3)	0.2390 (2)	0.0391 (9)
H3	1.1284	0.2372	0.1753	0.047*
C4	1.2046 (3)	0.3764 (3)	0.1878 (3)	0.0374 (9)
C5	1.1038 (3)	0.4809 (2)	0.2206 (2)	0.0292 (8)
C6	1.1798 (3)	0.1737 (3)	0.3119 (3)	0.0573 (11)
H6A	1.2497	0.1297	0.2635	0.069*
H6B	1.1140	0.1231	0.3572	0.069*
C7	1.2260 (3)	0.2200 (3)	0.3896 (3)	0.0596 (11)
H7A	1.1557	0.2604	0.4413	0.072*
H7B	1.2601	0.1574	0.4335	0.072*
C8	1.3269 (3)	0.2992 (3)	0.3194 (3)	0.0471 (10)
C9	1.4324 (3)	0.2983 (3)	0.3491 (3)	0.0599 (11)
H9	1.4381	0.2501	0.4134	0.072*
C10	1.5283 (3)	0.3678 (3)	0.2846 (3)	0.0652 (13)
H10	1.5975	0.3673	0.3059	0.078*
C11	1.5210 (3)	0.4376 (3)	0.1886 (3)	0.0642 (12)
H11	1.5856	0.4844	0.1445	0.077*
C12	1.4177 (3)	0.4383 (3)	0.1576 (3)	0.0539 (10)
H12	1.4143	0.4851	0.0918	0.065*
C13	1.3187 (3)	0.3706 (3)	0.2228 (3)	0.0384 (9)
C14	1.0911 (2)	0.5099 (2)	0.3357 (2)	0.0390 (9)
H14A	1.0016	0.5219	0.3801	0.047*
H14B	1.1264	0.4446	0.3759	0.047*
C15	1.1562 (3)	0.6145 (3)	0.3275 (2)	0.0476 (9)
H15A	1.1426	0.6276	0.4025	0.057*
H15B	1.2468	0.6022	0.2876	0.057*
C16	1.1022 (3)	0.7165 (3)	0.2657 (3)	0.0433 (9)
C17	1.0635 (3)	0.8197 (3)	0.3030 (3)	0.0590 (11)
H17	1.0725	0.8292	0.3687	0.071*
C18	1.0117 (3)	0.9087 (3)	0.2443 (3)	0.0674 (12)
H18	0.9873	0.9788	0.2690	0.081*
C19	0.9963 (3)	0.8934 (3)	0.1489 (3)	0.0633 (12)
H19	0.9602	0.9532	0.1094	0.076*
C20	1.0337 (3)	0.7900 (3)	0.1102 (3)	0.0520 (10)
H20	1.0230	0.7809	0.0450	0.062*
C21	1.0869 (3)	0.7005 (3)	0.1684 (3)	0.0360 (9)
C22	1.1408 (3)	0.5887 (3)	0.1282 (3)	0.0403 (9)
H22	1.2333	0.5884	0.1031	0.048*
C23	0.8554 (3)	0.5052 (3)	0.2707 (3)	0.0327 (8)
C24	0.8161 (3)	0.5863 (3)	0.1954 (3)	0.0433 (10)
H24	0.8691	0.5979	0.1200	0.052*
C25	0.7010 (3)	0.6507 (3)	0.2280 (3)	0.0496 (10)
H25	0.6768	0.7048	0.1755	0.059*
C26	0.6234 (3)	0.6336 (3)	0.3389 (3)	0.0443 (10)
C27	0.6591 (3)	0.5551 (3)	0.4165 (3)	0.0461 (10)
H27	0.6058	0.5449	0.4919	0.055*
C28	0.7741 (3)	0.4909 (2)	0.3836 (3)	0.0445 (9)
H28	0.7977	0.4376	0.4369	0.053*
C29	0.8927 (3)	0.2359 (3)	0.3083 (3)	0.0358 (9)
C30	0.8677 (3)	0.2243 (3)	0.2160 (3)	0.0453 (10)
H30	0.9080	0.2681	0.1466	0.054*
C31	0.7833 (3)	0.1483 (3)	0.2237 (3)	0.0518 (10)
H31	0.7683	0.1410	0.1600	0.062*
C32	0.7221 (3)	0.0840 (3)	0.3267 (4)	0.0512 (11)
C33	0.7428 (3)	0.0961 (3)	0.4192 (3)	0.0605 (11)
H33	0.6999	0.0540	0.4888	0.073*
C34	0.8275 (3)	0.1707 (3)	0.4109 (3)	0.0498 (10)
H34	0.8414	0.1774	0.4754	0.060*
O3	1.4162 (3)	0.2020 (2)	−0.0190 (2)	0.1159 (12)
C35	1.5981 (4)	0.0979 (3)	−0.1286 (3)	0.1331 (18)
H35A	1.6391	0.0309	−0.0975	0.160*
H35B	1.6609	0.1414	−0.1888	0.160*
H35C	1.5405	0.0759	−0.1571	0.160*
C36	1.5252 (5)	0.1697 (4)	−0.0374 (4)	0.0829 (15)
C37	1.5946 (4)	0.1815 (4)	0.0315 (4)	0.167 (2)
H37A	1.5849	0.2596	0.0417	0.201*
H37B	1.6829	0.1590	−0.0050	0.201*
H37C	1.5622	0.1339	0.1036	0.201*
H1O	1.301 (2)	0.3380 (19)	0.043 (3)	0.090 (16)*
H2O	1.158 (2)	0.5284 (16)	0.014 (3)	0.063 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0418 (3)	0.0584 (3)	0.1137 (4)	0.0068 (2)	−0.0178 (2)	−0.0131 (3)
Br2	0.0859 (3)	0.0837 (4)	0.1250 (4)	−0.0443 (3)	−0.0257 (3)	−0.0229 (3)
O1	0.0498 (16)	0.0529 (18)	0.0386 (18)	0.0080 (14)	−0.0099 (14)	−0.0143 (15)
O2	0.0658 (17)	0.0452 (18)	0.0351 (17)	0.0052 (15)	−0.0189 (14)	−0.0067 (14)
C1	0.039 (2)	0.033 (2)	0.027 (2)	−0.0021 (17)	−0.0132 (18)	−0.0044 (18)
C2	0.036 (2)	0.035 (2)	0.034 (2)	−0.0010 (17)	−0.0180 (18)	−0.0070 (18)
C3	0.035 (2)	0.036 (2)	0.049 (2)	0.0028 (17)	−0.0183 (19)	−0.0115 (19)
C4	0.036 (2)	0.042 (2)	0.033 (2)	−0.0025 (18)	−0.0106 (19)	−0.0088 (19)
C5	0.034 (2)	0.030 (2)	0.025 (2)	−0.0018 (16)	−0.0128 (17)	−0.0052 (18)
C6	0.047 (2)	0.040 (3)	0.086 (3)	−0.0026 (19)	−0.025 (2)	−0.010 (2)
C7	0.061 (3)	0.044 (3)	0.072 (3)	0.001 (2)	−0.036 (2)	0.013 (2)
C8	0.043 (2)	0.040 (3)	0.061 (3)	0.0042 (19)	−0.024 (2)	−0.009 (2)
C9	0.056 (3)	0.063 (3)	0.071 (3)	0.014 (2)	−0.037 (3)	−0.019 (2)
C10	0.047 (3)	0.083 (4)	0.086 (4)	0.007 (2)	−0.040 (3)	−0.036 (3)
C11	0.038 (3)	0.061 (3)	0.095 (4)	−0.009 (2)	−0.018 (3)	−0.024 (3)
C12	0.037 (2)	0.056 (3)	0.064 (3)	−0.002 (2)	−0.013 (2)	−0.012 (2)
C13	0.034 (2)	0.037 (2)	0.046 (3)	0.0007 (18)	−0.013 (2)	−0.015 (2)
C14	0.038 (2)	0.038 (2)	0.041 (2)	−0.0012 (17)	−0.0169 (18)	−0.0022 (19)
C15	0.054 (2)	0.051 (3)	0.048 (2)	−0.008 (2)	−0.023 (2)	−0.018 (2)
C16	0.038 (2)	0.039 (3)	0.051 (3)	−0.0046 (19)	−0.013 (2)	−0.007 (2)
C17	0.067 (3)	0.048 (3)	0.065 (3)	0.005 (2)	−0.027 (2)	−0.017 (2)
C18	0.084 (3)	0.047 (3)	0.075 (3)	0.008 (2)	−0.030 (3)	−0.027 (3)
C19	0.084 (3)	0.037 (3)	0.060 (3)	0.015 (2)	−0.028 (3)	0.001 (2)
C20	0.062 (2)	0.046 (3)	0.042 (3)	−0.004 (2)	−0.014 (2)	−0.003 (2)
C21	0.039 (2)	0.032 (2)	0.031 (2)	−0.0065 (18)	−0.0070 (19)	−0.001 (2)
C22	0.042 (2)	0.045 (3)	0.036 (2)	−0.0012 (18)	−0.0165 (19)	−0.008 (2)
C23	0.034 (2)	0.025 (2)	0.044 (2)	−0.0034 (17)	−0.018 (2)	−0.0087 (19)
C24	0.041 (2)	0.046 (3)	0.039 (2)	−0.0092 (19)	−0.013 (2)	0.001 (2)
C25	0.043 (2)	0.038 (2)	0.070 (3)	0.003 (2)	−0.031 (2)	0.000 (2)
C26	0.032 (2)	0.041 (2)	0.059 (3)	−0.0009 (18)	−0.013 (2)	−0.013 (2)
C27	0.039 (2)	0.052 (3)	0.042 (3)	−0.0022 (19)	−0.010 (2)	−0.008 (2)
C28	0.040 (2)	0.050 (3)	0.042 (3)	−0.001 (2)	−0.014 (2)	−0.007 (2)
C29	0.035 (2)	0.033 (2)	0.036 (2)	0.0036 (17)	−0.009 (2)	−0.012 (2)
C30	0.047 (2)	0.042 (2)	0.046 (3)	−0.0083 (18)	−0.016 (2)	−0.005 (2)
C31	0.056 (2)	0.050 (3)	0.064 (3)	−0.002 (2)	−0.036 (2)	−0.014 (2)
C32	0.045 (2)	0.043 (3)	0.064 (3)	−0.0095 (19)	−0.013 (2)	−0.013 (2)
C33	0.064 (3)	0.052 (3)	0.057 (3)	−0.018 (2)	−0.005 (2)	−0.012 (2)
C34	0.060 (3)	0.046 (3)	0.041 (3)	−0.011 (2)	−0.013 (2)	−0.006 (2)
O3	0.099 (2)	0.123 (3)	0.141 (3)	0.056 (2)	−0.065 (2)	−0.061 (2)
C35	0.110 (4)	0.148 (5)	0.120 (4)	0.023 (3)	−0.030 (3)	−0.024 (4)
C36	0.092 (4)	0.065 (3)	0.094 (4)	0.022 (3)	−0.040 (4)	−0.028 (3)
C37	0.103 (4)	0.215 (6)	0.235 (7)	0.005 (4)	−0.076 (4)	−0.130 (5)

Geometric parameters (Å, º)

Br1—C26	1.895 (3)	C16—C17	1.377 (4)
Br2—C32	1.884 (3)	C16—C21	1.394 (4)
O1—C4	1.442 (3)	C17—C18	1.371 (4)
O1—H1O	0.810 (10)	C17—H17	0.9300
O2—C22	1.425 (3)	C18—C19	1.369 (4)
O2—H2O	0.815 (10)	C18—H18	0.9300
C1—C23	1.518 (3)	C19—C20	1.386 (4)
C1—C2	1.541 (3)	C19—H19	0.9300
C1—C5	1.553 (3)	C20—C21	1.380 (4)
C1—H1	0.9800	C20—H20	0.9300
C2—C29	1.516 (3)	C21—C22	1.503 (4)
C2—C3	1.540 (3)	C22—H22	0.9800
C2—H2	0.9800	C23—C24	1.381 (3)
C3—C6	1.528 (3)	C23—C28	1.398 (3)
C3—C4	1.558 (4)	C24—C25	1.382 (3)
C3—H3	0.9800	C24—H24	0.9300
C4—C13	1.524 (4)	C25—C26	1.368 (4)
C4—C5	1.579 (3)	C25—H25	0.9300
C5—C14	1.555 (3)	C26—C27	1.367 (4)
C5—C22	1.561 (3)	C27—C28	1.380 (3)
C6—C7	1.530 (3)	C27—H27	0.9300
C6—H6A	0.9700	C28—H28	0.9300
C6—H6B	0.9700	C29—C30	1.373 (3)
C7—C8	1.500 (4)	C29—C34	1.393 (3)
C7—H7A	0.9700	C30—C31	1.393 (4)
C7—H7B	0.9700	C30—H30	0.9300
C8—C13	1.390 (4)	C31—C32	1.380 (4)
C8—C9	1.397 (4)	C31—H31	0.9300
C9—C10	1.377 (4)	C32—C33	1.349 (4)
C9—H9	0.9300	C33—C34	1.381 (4)
C10—C11	1.372 (4)	C33—H33	0.9300
C10—H10	0.9300	C34—H34	0.9300
C11—C12	1.383 (4)	O3—C36	1.193 (4)
C11—H11	0.9300	C35—C36	1.518 (5)
C12—C13	1.390 (4)	C35—H35A	0.9600
C12—H12	0.9300	C35—H35B	0.9600
C14—C15	1.526 (3)	C35—H35C	0.9600
C14—H14A	0.9700	C36—C37	1.441 (5)
C14—H14B	0.9700	C37—H37A	0.9600
C15—C16	1.503 (4)	C37—H37B	0.9600
C15—H15A	0.9700	C37—H37C	0.9600
C15—H15B	0.9700
C4—O1—H1O	112 (2)	C17—C16—C15	123.5 (4)
C22—O2—H2O	96 (2)	C21—C16—C15	116.3 (3)
C23—C1—C2	116.3 (2)	C18—C17—C16	120.7 (4)
C23—C1—C5	118.8 (2)	C18—C17—H17	119.6
C2—C1—C5	101.4 (2)	C16—C17—H17	119.6
C23—C1—H1	106.5	C19—C18—C17	119.3 (4)
C2—C1—H1	106.5	C19—C18—H18	120.4
C5—C1—H1	106.5	C17—C18—H18	120.4
C29—C2—C3	113.4 (2)	C18—C19—C20	121.0 (4)
C29—C2—C1	115.3 (2)	C18—C19—H19	119.5
C3—C2—C1	102.4 (2)	C20—C19—H19	119.5
C29—C2—H2	108.5	C21—C20—C19	119.9 (3)
C3—C2—H2	108.5	C21—C20—H20	120.0
C1—C2—H2	108.5	C19—C20—H20	120.0
C6—C3—C2	114.0 (2)	C20—C21—C16	118.9 (3)
C6—C3—C4	116.0 (2)	C20—C21—C22	124.0 (4)
C2—C3—C4	106.0 (2)	C16—C21—C22	116.9 (3)
C6—C3—H3	106.7	O2—C22—C21	109.0 (3)
C2—C3—H3	106.7	O2—C22—C5	113.6 (3)
C4—C3—H3	106.7	C21—C22—C5	115.0 (3)
O1—C4—C13	108.5 (3)	O2—C22—H22	106.2
O1—C4—C3	108.6 (2)	C21—C22—H22	106.2
C13—C4—C3	113.9 (3)	C5—C22—H22	106.2
O1—C4—C5	105.8 (3)	C24—C23—C28	117.3 (3)
C13—C4—C5	114.6 (3)	C24—C23—C1	120.3 (3)
C3—C4—C5	105.1 (2)	C28—C23—C1	122.4 (3)
C1—C5—C14	110.7 (2)	C23—C24—C25	122.4 (3)
C1—C5—C22	113.5 (2)	C23—C24—H24	118.8
C14—C5—C22	108.9 (2)	C25—C24—H24	118.8
C1—C5—C4	101.3 (2)	C26—C25—C24	118.7 (3)
C14—C5—C4	111.6 (2)	C26—C25—H25	120.6
C22—C5—C4	110.8 (2)	C24—C25—H25	120.6
C3—C6—C7	111.9 (3)	C27—C26—C25	120.8 (3)
C3—C6—H6A	109.2	C27—C26—Br1	119.2 (3)
C7—C6—H6A	109.2	C25—C26—Br1	120.0 (3)
C3—C6—H6B	109.2	C26—C27—C28	120.2 (3)
C7—C6—H6B	109.2	C26—C27—H27	119.9
H6A—C6—H6B	107.9	C28—C27—H27	119.9
C8—C7—C6	109.1 (3)	C27—C28—C23	120.6 (3)
C8—C7—H7A	109.9	C27—C28—H28	119.7
C6—C7—H7A	109.9	C23—C28—H28	119.7
C8—C7—H7B	109.9	C30—C29—C34	117.1 (3)
C6—C7—H7B	109.9	C30—C29—C2	121.8 (3)
H7A—C7—H7B	108.3	C34—C29—C2	121.1 (3)
C13—C8—C9	119.5 (3)	C29—C30—C31	121.6 (3)
C13—C8—C7	120.8 (3)	C29—C30—H30	119.2
C9—C8—C7	119.7 (4)	C31—C30—H30	119.2
C10—C9—C8	121.0 (4)	C32—C31—C30	119.5 (3)
C10—C9—H9	119.5	C32—C31—H31	120.3
C8—C9—H9	119.5	C30—C31—H31	120.3
C11—C10—C9	119.5 (4)	C33—C32—C31	120.0 (3)
C11—C10—H10	120.2	C33—C32—Br2	120.8 (3)
C9—C10—H10	120.2	C31—C32—Br2	119.1 (3)
C10—C11—C12	120.0 (4)	C32—C33—C34	120.4 (3)
C10—C11—H11	120.0	C32—C33—H33	119.8
C12—C11—H11	120.0	C34—C33—H33	119.8
C11—C12—C13	121.3 (3)	C33—C34—C29	121.5 (3)
C11—C12—H12	119.3	C33—C34—H34	119.3
C13—C12—H12	119.3	C29—C34—H34	119.3
C12—C13—C8	118.5 (3)	C36—C35—H35A	109.5
C12—C13—C4	119.8 (3)	C36—C35—H35B	109.5
C8—C13—C4	121.7 (3)	H35A—C35—H35B	109.5
C15—C14—C5	114.9 (2)	C36—C35—H35C	109.5
C15—C14—H14A	108.5	H35A—C35—H35C	109.5
C5—C14—H14A	108.5	H35B—C35—H35C	109.5
C15—C14—H14B	108.5	O3—C36—C37	124.3 (5)
C5—C14—H14B	108.5	O3—C36—C35	121.5 (5)
H14A—C14—H14B	107.5	C37—C36—C35	113.8 (4)
C16—C15—C14	109.2 (2)	C36—C37—H37A	109.5
C16—C15—H15A	109.8	C36—C37—H37B	109.5
C14—C15—H15A	109.8	H37A—C37—H37B	109.5
C16—C15—H15B	109.8	C36—C37—H37C	109.5
C14—C15—H15B	109.8	H37A—C37—H37C	109.5
H15A—C15—H15B	108.3	H37B—C37—H37C	109.5
C17—C16—C21	120.2 (3)
C23—C1—C2—C29	59.0 (3)	C4—C5—C14—C15	103.7 (3)
C5—C1—C2—C29	−170.6 (2)	C5—C14—C15—C16	58.4 (3)
C23—C1—C2—C3	−177.3 (2)	C14—C15—C16—C17	132.5 (3)
C5—C1—C2—C3	−47.0 (3)	C14—C15—C16—C21	−44.6 (4)
C29—C2—C3—C6	−77.0 (3)	C21—C16—C17—C18	−1.3 (5)
C1—C2—C3—C6	158.1 (2)	C15—C16—C17—C18	−178.2 (3)
C29—C2—C3—C4	154.1 (3)	C16—C17—C18—C19	1.3 (5)
C1—C2—C3—C4	29.2 (3)	C17—C18—C19—C20	−0.9 (6)
C6—C3—C4—O1	118.7 (3)	C18—C19—C20—C21	0.3 (5)
C2—C3—C4—O1	−113.5 (3)	C19—C20—C21—C16	−0.2 (5)
C6—C3—C4—C13	−2.3 (4)	C19—C20—C21—C22	−174.4 (3)
C2—C3—C4—C13	125.5 (3)	C17—C16—C21—C20	0.7 (5)
C6—C3—C4—C5	−128.5 (3)	C15—C16—C21—C20	177.8 (3)
C2—C3—C4—C5	−0.7 (3)	C17—C16—C21—C22	175.3 (3)
C23—C1—C5—C14	56.2 (4)	C15—C16—C21—C22	−7.5 (4)
C2—C1—C5—C14	−72.6 (3)	C20—C21—C22—O2	−7.2 (4)
C23—C1—C5—C22	−66.5 (4)	C16—C21—C22—O2	178.4 (2)
C2—C1—C5—C22	164.7 (2)	C20—C21—C22—C5	−136.1 (3)
C23—C1—C5—C4	174.7 (3)	C16—C21—C22—C5	49.6 (4)
C2—C1—C5—C4	45.9 (3)	C1—C5—C22—O2	−35.9 (3)
O1—C4—C5—C1	87.1 (3)	C14—C5—C22—O2	−159.6 (2)
C13—C4—C5—C1	−153.5 (3)	C4—C5—C22—O2	77.3 (3)
C3—C4—C5—C1	−27.7 (3)	C1—C5—C22—C21	90.6 (3)
O1—C4—C5—C14	−155.1 (2)	C14—C5—C22—C21	−33.1 (4)
C13—C4—C5—C14	−35.7 (4)	C4—C5—C22—C21	−156.2 (3)
C3—C4—C5—C14	90.2 (3)	C2—C1—C23—C24	−151.8 (3)
O1—C4—C5—C22	−33.6 (3)	C5—C1—C23—C24	86.7 (4)
C13—C4—C5—C22	85.8 (3)	C2—C1—C23—C28	26.6 (4)
C3—C4—C5—C22	−148.4 (3)	C5—C1—C23—C28	−94.9 (3)
C2—C3—C6—C7	−81.9 (3)	C28—C23—C24—C25	−0.7 (5)
C4—C3—C6—C7	41.7 (4)	C1—C23—C24—C25	177.8 (3)
C3—C6—C7—C8	−58.3 (3)	C23—C24—C25—C26	0.1 (5)
C6—C7—C8—C13	36.9 (4)	C24—C25—C26—C27	0.7 (5)
C6—C7—C8—C9	−140.8 (3)	C24—C25—C26—Br1	−178.1 (2)
C13—C8—C9—C10	0.5 (5)	C25—C26—C27—C28	−0.7 (5)
C7—C8—C9—C10	178.2 (3)	Br1—C26—C27—C28	178.0 (2)
C8—C9—C10—C11	−1.1 (6)	C26—C27—C28—C23	0.0 (5)
C9—C10—C11—C12	0.3 (6)	C24—C23—C28—C27	0.7 (4)
C10—C11—C12—C13	1.0 (5)	C1—C23—C28—C27	−177.8 (3)
C11—C12—C13—C8	−1.6 (5)	C3—C2—C29—C30	−71.6 (4)
C11—C12—C13—C4	178.2 (3)	C1—C2—C29—C30	46.0 (4)
C9—C8—C13—C12	0.8 (5)	C3—C2—C29—C34	106.9 (3)
C7—C8—C13—C12	−176.9 (3)	C1—C2—C29—C34	−135.5 (3)
C9—C8—C13—C4	−178.9 (3)	C34—C29—C30—C31	−1.7 (4)
C7—C8—C13—C4	3.4 (5)	C2—C29—C30—C31	176.9 (3)
O1—C4—C13—C12	37.7 (4)	C29—C30—C31—C32	0.7 (5)
C3—C4—C13—C12	158.7 (3)	C30—C31—C32—C33	1.0 (5)
C5—C4—C13—C12	−80.2 (4)	C30—C31—C32—Br2	−177.4 (2)
O1—C4—C13—C8	−142.6 (3)	C31—C32—C33—C34	−1.6 (5)
C3—C4—C13—C8	−21.6 (4)	Br2—C32—C33—C34	176.7 (2)
C5—C4—C13—C8	99.5 (3)	C32—C33—C34—C29	0.6 (5)
C1—C5—C14—C15	−144.2 (2)	C30—C29—C34—C33	1.0 (5)
C22—C5—C14—C15	−18.9 (3)	C2—C29—C34—C33	−177.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.82 (1)	1.96 (2)	2.681 (3)	147 (3)
O1—H1O···O3	0.81 (1)	2.04 (1)	2.842 (3)	174 (3)