Br...Br and van der Waals interactions along a homologous series: crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes

The crystalline structures of four homologues of the 1,2-dibromo-4,5-dialkoxybenzene series [Br₂C₆H₂(OC_nH_2n + 1)₂ for n = 2, 12, 14 and 18] have been solved by means of single-crystal crystallography. Comparison along the series, including the previously reported n = 10 and n = 16 derivatives, shows a clear metric trend (b and c essentially fixed along the series and a growing linearly with n), in spite of some subtle differences in space groups and/or packing modes. A uniform packing pattern for the aliphatic chains has been found for the n = 12 to 18 homologues, which slightly differs from that of the n = 10 derivative. The crystalline structures of all the higher homologues (n = 10–18) seem to arise from van der Waals interchain interactions and, to a lesser extent, type II Br...Br interactions. The dominant role of interchain interactions provides direct structural support for the usual interpretation of melting point trends like that found along this series. Atoms in Molecules (AIM) analysis allows a comparison of the relative magnitude of the interchain and Br...Br interactions, an analysis validated by the measured melting enthalpies.

Computing details

For all compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2014); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014/6, PLATON (Spek, 2003).

(N02)

Crystal data

C10H12Br2O2	F(000) = 632
Mr = 324.02	Dx = 1.828 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.663 (6) Å	Cell parameters from 1311 reflections
b = 7.943 (5) Å	θ = 4.3–26.7°
c = 8.924 (5) Å	µ = 6.86 mm^−1
β = 94.725 (5)°	T = 294 K
V = 1177.1 (11) Å^3	Plates, colourless
Z = 4	0.35 × 0.25 × 0.08 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	1455 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
ω scans, thick slices	θmax = 29.1°, θmin = 4.1°
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009)	h = −21→21
	k = −10→9
6449 measured reflections	l = −12→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.077	H-atom parameters constrained
wR(F^2) = 0.265	w = 1/[σ^2(Fo^2) + (0.1261P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2720 reflections	Δρmax = 0.85 e Å^−3
129 parameters	Δρmin = −1.05 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.61556 (7)	0.07692 (14)	0.53471 (10)	0.0709 (5)
Br2	0.52799 (8)	−0.12849 (17)	0.81051 (15)	0.0892 (6)
O1	0.8666 (4)	0.1329 (8)	0.9262 (6)	0.0644 (19)
O2	0.7979 (4)	−0.0170 (7)	1.1389 (5)	0.0548 (15)
C1	0.6695 (6)	0.0433 (10)	0.7249 (9)	0.050 (2)
C2	0.6317 (6)	−0.0364 (10)	0.8402 (10)	0.053 (2)
C3	0.6735 (6)	−0.0586 (10)	0.9808 (9)	0.055 (2)
H3	0.6490	−0.1127	1.0574	0.066*
C4	0.7518 (5)	0.0002 (10)	1.0059 (8)	0.0441 (19)
C5	0.7880 (7)	0.0821 (10)	0.8912 (8)	0.050 (2)
C6	0.7477 (6)	0.1033 (10)	0.7521 (9)	0.052 (2)
H6	0.7727	0.1576	0.6762	0.062*
C11	0.9136 (7)	0.1773 (12)	0.8052 (9)	0.059 (2)
H11A	0.8890	0.2707	0.7484	0.071*
H11B	0.9179	0.0825	0.7378	0.071*
C12	0.9945 (8)	0.2258 (15)	0.8746 (12)	0.087 (3)
H12A	1.0271	0.2647	0.7979	0.130*
H12B	1.0197	0.1299	0.9243	0.130*
H12C	0.9889	0.3140	0.9465	0.130*
C31	0.7604 (8)	−0.0978 (11)	1.2607 (9)	0.064 (3)
H31A	0.7468	−0.2134	1.2348	0.077*
H31B	0.7116	−0.0387	1.2812	0.077*
C32	0.8206 (8)	−0.0920 (13)	1.3958 (9)	0.078 (3)
H32A	0.8000	−0.1537	1.4769	0.116*
H32B	0.8298	0.0229	1.4259	0.116*
H32C	0.8703	−0.1415	1.3710	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0590 (8)	0.0921 (8)	0.0601 (6)	0.0093 (6)	−0.0041 (5)	0.0001 (4)
Br2	0.0601 (9)	0.1020 (10)	0.1030 (9)	−0.0268 (7)	−0.0073 (7)	0.0132 (6)
O1	0.052 (5)	0.088 (4)	0.053 (3)	−0.024 (4)	−0.001 (3)	0.009 (3)
O2	0.053 (4)	0.063 (3)	0.048 (3)	−0.007 (3)	0.007 (3)	0.006 (2)
C1	0.038 (6)	0.047 (4)	0.065 (5)	0.016 (4)	0.008 (4)	0.003 (4)
C2	0.039 (5)	0.039 (4)	0.081 (6)	−0.004 (4)	0.009 (5)	−0.002 (4)
C3	0.056 (7)	0.049 (4)	0.061 (5)	−0.017 (5)	0.015 (5)	0.009 (4)
C4	0.040 (5)	0.042 (4)	0.050 (4)	0.001 (4)	0.003 (4)	−0.001 (3)
C5	0.067 (7)	0.044 (4)	0.041 (4)	−0.008 (4)	0.022 (4)	0.002 (3)
C6	0.047 (6)	0.055 (5)	0.055 (5)	−0.001 (4)	0.014 (4)	−0.002 (4)
C11	0.062 (7)	0.063 (5)	0.054 (4)	−0.009 (5)	0.014 (5)	0.004 (4)
C12	0.067 (9)	0.087 (7)	0.107 (8)	0.008 (7)	0.013 (7)	0.013 (6)
C31	0.085 (9)	0.059 (5)	0.051 (4)	0.004 (5)	0.021 (5)	0.005 (4)
C32	0.099 (10)	0.091 (7)	0.043 (4)	−0.012 (7)	0.004 (5)	0.012 (4)

Geometric parameters (Å, º)

Br1—C1	1.873 (8)	C6—H6	0.9300
Br2—C2	1.875 (9)	C11—C12	1.486 (16)
O1—C5	1.381 (12)	C11—H11A	0.9700
O1—C11	1.430 (11)	C11—H11B	0.9700
O2—C4	1.367 (8)	C12—H12A	0.9600
O2—C31	1.447 (10)	C12—H12B	0.9600
C1—C6	1.390 (13)	C12—H12C	0.9600
C1—C2	1.401 (13)	C31—C32	1.503 (14)
C2—C3	1.395 (12)	C31—H31A	0.9700
C3—C4	1.386 (13)	C31—H31B	0.9700
C3—H3	0.9300	C32—H32A	0.9600
C4—C5	1.392 (11)	C32—H32B	0.9600
C5—C6	1.372 (12)	C32—H32C	0.9600
C5—O1—C11	118.0 (6)	C12—C11—H11A	110.4
C4—O2—C31	116.8 (7)	O1—C11—H11B	110.4
C6—C1—C2	119.9 (8)	C12—C11—H11B	110.4
C6—C1—Br1	118.8 (7)	H11A—C11—H11B	108.6
C2—C1—Br1	121.3 (7)	C11—C12—H12A	109.5
C3—C2—C1	119.7 (8)	C11—C12—H12B	109.5
C3—C2—Br2	117.7 (7)	H12A—C12—H12B	109.5
C1—C2—Br2	122.5 (7)	C11—C12—H12C	109.5
C4—C3—C2	119.8 (8)	H12A—C12—H12C	109.5
C4—C3—H3	120.1	H12B—C12—H12C	109.5
C2—C3—H3	120.1	O2—C31—C32	106.8 (9)
O2—C4—C3	124.1 (7)	O2—C31—H31A	110.4
O2—C4—C5	116.0 (8)	C32—C31—H31A	110.4
C3—C4—C5	119.9 (7)	O2—C31—H31B	110.4
C6—C5—O1	123.6 (8)	C32—C31—H31B	110.4
C6—C5—C4	120.8 (9)	H31A—C31—H31B	108.6
O1—C5—C4	115.5 (7)	C31—C32—H32A	109.5
C5—C6—C1	119.9 (9)	C31—C32—H32B	109.5
C5—C6—H6	120.1	H32A—C32—H32B	109.5
C1—C6—H6	120.1	C31—C32—H32C	109.5
O1—C11—C12	106.5 (7)	H32A—C32—H32C	109.5
O1—C11—H11A	110.4	H32B—C32—H32C	109.5

(N12)

Crystal data

C30H52Br2O2	F(000) = 1272
Mr = 604.53	Dx = 1.283 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.897 (6) Å	Cell parameters from 12520 reflections
b = 8.421 (4) Å	θ = 3.9–28.3°
c = 9.321 (5) Å	µ = 2.61 mm^−1
β = 91.622 (5)°	T = 294 K
V = 3130 (3) Å^3	Plates, colourless
Z = 4	0.28 × 0.18 × 0.10 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	7891 independent reflections
Radiation source: fine-focus sealed tube	4456 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.140
ω scans, thick slices	θmax = 29.3°, θmin = 3.9°
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009)	h = −54→54
Tmin = 0.48, Tmax = 0.82	k = −11→11
65286 measured reflections	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.093	H-atom parameters constrained
wR(F^2) = 0.230	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 27.2995P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
7891 reflections	Δρmax = 0.76 e Å^−3
309 parameters	Δρmin = −1.47 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.95217 (2)	0.44423 (11)	0.46744 (8)	0.0529 (3)
Br2	0.99375 (2)	0.64661 (12)	0.21468 (11)	0.0641 (3)
O1	0.86254 (13)	0.3303 (7)	0.0571 (5)	0.0486 (13)
O2	0.89218 (13)	0.5015 (6)	−0.1303 (5)	0.0444 (12)
C1	0.93564 (18)	0.4570 (8)	0.2763 (7)	0.0376 (15)
C2	0.95264 (16)	0.5426 (9)	0.1729 (8)	0.0382 (16)
C3	0.93934 (17)	0.5544 (8)	0.0351 (7)	0.0352 (15)
H3	0.9512	0.6082	−0.0344	0.042*
C4	0.90873 (17)	0.4874 (8)	−0.0007 (7)	0.0355 (15)
C5	0.89171 (17)	0.3973 (8)	0.1011 (8)	0.0363 (15)
C6	0.90599 (18)	0.3844 (8)	0.2392 (8)	0.0375 (16)
H6	0.8950	0.3249	0.3076	0.045*
C11	0.84029 (17)	0.2770 (9)	0.1642 (8)	0.0415 (17)
H11A	0.8352	0.3627	0.2296	0.050*
H11B	0.8503	0.1902	0.2189	0.050*
C12	0.80889 (18)	0.2223 (10)	0.0850 (8)	0.0442 (18)
H12A	0.8143	0.1319	0.0255	0.053*
H12B	0.8010	0.3069	0.0221	0.053*
C13	0.78072 (18)	0.1754 (10)	0.1842 (8)	0.0458 (18)
H13A	0.7883	0.0890	0.2458	0.055*
H13B	0.7754	0.2649	0.2449	0.055*
C14	0.74944 (19)	0.1240 (11)	0.1008 (9)	0.051 (2)
H14A	0.7549	0.0331	0.0420	0.061*
H14B	0.7426	0.2095	0.0367	0.061*
C15	0.71987 (19)	0.0801 (11)	0.1936 (9)	0.054 (2)
H15A	0.7264	−0.0069	0.2566	0.065*
H15B	0.7143	0.1702	0.2531	0.065*
C16	0.6890 (2)	0.0315 (12)	0.1044 (9)	0.060 (2)
H16A	0.6947	−0.0587	0.0451	0.072*
H16B	0.6827	0.1184	0.0408	0.072*
C17	0.6589 (2)	−0.0124 (13)	0.1943 (10)	0.063 (2)
H17A	0.6651	−0.0999	0.2573	0.076*
H17B	0.6532	0.0775	0.2539	0.076*
C18	0.6283 (2)	−0.0596 (13)	0.1041 (11)	0.068 (3)
H18A	0.6339	−0.1508	0.0460	0.082*
H18B	0.6225	0.0271	0.0395	0.082*
C19	0.5976 (2)	−0.1005 (14)	0.1928 (11)	0.074 (3)
H19A	0.6035	−0.1871	0.2573	0.089*
H19B	0.5921	−0.0093	0.2510	0.089*
C20	0.5671 (2)	−0.1472 (14)	0.1039 (11)	0.077 (3)
H20A	0.5726	−0.2389	0.0462	0.092*
H20B	0.5614	−0.0609	0.0388	0.092*
C21	0.5364 (3)	−0.1869 (19)	0.1917 (13)	0.104 (4)
H21A	0.5423	−0.2705	0.2593	0.125*
H21B	0.5302	−0.0939	0.2464	0.125*
C22	0.5066 (3)	−0.239 (2)	0.1014 (17)	0.140 (6)
H22A	0.4886	−0.2679	0.1626	0.210*
H22B	0.5126	−0.3293	0.0445	0.210*
H22C	0.4995	−0.1540	0.0393	0.210*
C31	0.90259 (18)	0.6290 (9)	−0.2237 (7)	0.0423 (17)
H31A	0.9225	0.5983	−0.2741	0.051*
H31B	0.9077	0.7237	−0.1680	0.051*
C32	0.87412 (18)	0.6605 (9)	−0.3288 (7)	0.0415 (17)
H32A	0.8689	0.5635	−0.3810	0.050*
H32B	0.8811	0.7394	−0.3977	0.050*
C33	0.84247 (18)	0.7193 (10)	−0.2561 (8)	0.0459 (18)
H33A	0.8345	0.6359	−0.1940	0.055*
H33B	0.8484	0.8097	−0.1961	0.055*
C34	0.81386 (19)	0.7680 (10)	−0.3598 (8)	0.0476 (18)
H34A	0.8214	0.8545	−0.4197	0.057*
H34B	0.8082	0.6790	−0.4220	0.057*
C35	0.78289 (19)	0.8198 (11)	−0.2821 (8)	0.050 (2)
H35A	0.7887	0.9099	−0.2216	0.060*
H35B	0.7760	0.7340	−0.2200	0.060*
C36	0.7531 (2)	0.8657 (11)	−0.3803 (9)	0.053 (2)
H36A	0.7597	0.9526	−0.4418	0.064*
H36B	0.7472	0.7762	−0.4413	0.064*
C37	0.7228 (2)	0.9151 (12)	−0.2977 (9)	0.057 (2)
H37A	0.7289	1.0049	−0.2371	0.069*
H37B	0.7166	0.8284	−0.2354	0.069*
C38	0.6921 (2)	0.9612 (12)	−0.3928 (10)	0.063 (2)
H38A	0.6982	1.0487	−0.4544	0.075*
H38B	0.6860	0.8718	−0.4538	0.075*
C39	0.6618 (2)	1.0090 (13)	−0.3088 (10)	0.064 (2)
H39A	0.6679	1.0984	−0.2478	0.076*
H39B	0.6558	0.9215	−0.2468	0.076*
C40	0.6312 (2)	1.0545 (13)	−0.4017 (11)	0.072 (3)
H40A	0.6371	1.1422	−0.4635	0.086*
H40B	0.6251	0.9652	−0.4628	0.086*
C41	0.6011 (3)	1.1018 (15)	−0.3169 (12)	0.085 (3)
H41A	0.5951	1.0141	−0.2553	0.102*
H41B	0.6072	1.1911	−0.2558	0.102*
C42	0.5709 (3)	1.1469 (17)	−0.4090 (15)	0.108 (4)
H42A	0.5530	1.1792	−0.3488	0.163*
H42B	0.5639	1.0572	−0.4657	0.163*
H42C	0.5767	1.2330	−0.4712	0.163*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0445 (5)	0.0743 (6)	0.0393 (4)	−0.0006 (4)	−0.0085 (3)	−0.0027 (4)
Br2	0.0376 (4)	0.0768 (6)	0.0771 (6)	−0.0205 (4)	−0.0107 (4)	0.0092 (5)
O1	0.042 (3)	0.062 (3)	0.042 (3)	−0.022 (3)	−0.002 (2)	0.006 (3)
O2	0.048 (3)	0.045 (3)	0.039 (3)	−0.012 (2)	−0.006 (2)	0.006 (2)
C1	0.038 (4)	0.036 (4)	0.038 (4)	0.009 (3)	−0.003 (3)	−0.006 (3)
C2	0.024 (3)	0.044 (4)	0.047 (4)	−0.002 (3)	0.001 (3)	0.005 (3)
C3	0.040 (4)	0.028 (3)	0.038 (4)	−0.007 (3)	0.005 (3)	0.004 (3)
C4	0.037 (4)	0.031 (3)	0.037 (4)	0.002 (3)	−0.004 (3)	−0.003 (3)
C5	0.027 (3)	0.033 (4)	0.048 (4)	−0.008 (3)	−0.003 (3)	0.002 (3)
C6	0.038 (4)	0.034 (4)	0.040 (4)	−0.004 (3)	−0.004 (3)	0.002 (3)
C11	0.037 (4)	0.045 (4)	0.043 (4)	−0.010 (3)	0.002 (3)	0.003 (3)
C12	0.036 (4)	0.053 (5)	0.044 (4)	−0.011 (3)	0.001 (3)	0.001 (4)
C13	0.035 (4)	0.053 (5)	0.049 (4)	−0.014 (3)	−0.001 (3)	0.002 (4)
C14	0.035 (4)	0.067 (5)	0.051 (5)	−0.008 (4)	0.001 (3)	−0.001 (4)
C15	0.038 (4)	0.075 (6)	0.049 (4)	−0.016 (4)	−0.003 (4)	0.002 (4)
C16	0.042 (5)	0.080 (7)	0.058 (5)	−0.016 (4)	−0.009 (4)	0.005 (5)
C17	0.044 (5)	0.080 (7)	0.065 (6)	−0.013 (5)	0.000 (4)	−0.003 (5)
C18	0.052 (5)	0.082 (7)	0.072 (6)	−0.015 (5)	0.002 (5)	−0.007 (5)
C19	0.054 (6)	0.097 (8)	0.072 (6)	−0.019 (5)	0.007 (5)	−0.008 (6)
C20	0.047 (5)	0.101 (8)	0.082 (7)	−0.013 (5)	−0.005 (5)	−0.005 (6)
C21	0.057 (7)	0.158 (13)	0.097 (9)	−0.022 (8)	0.014 (6)	−0.016 (9)
C22	0.068 (8)	0.197 (18)	0.156 (14)	−0.040 (10)	0.006 (9)	−0.033 (13)
C31	0.037 (4)	0.055 (5)	0.035 (4)	0.002 (3)	0.018 (3)	0.010 (3)
C32	0.044 (4)	0.046 (4)	0.035 (4)	−0.008 (3)	0.007 (3)	0.010 (3)
C33	0.042 (4)	0.052 (5)	0.044 (4)	0.004 (4)	0.008 (3)	0.004 (4)
C34	0.047 (4)	0.055 (5)	0.041 (4)	0.001 (4)	0.005 (3)	0.002 (4)
C35	0.042 (4)	0.061 (5)	0.048 (4)	0.003 (4)	0.004 (4)	0.004 (4)
C36	0.046 (5)	0.064 (5)	0.049 (5)	0.003 (4)	−0.002 (4)	0.003 (4)
C37	0.053 (5)	0.069 (6)	0.049 (5)	0.004 (4)	−0.002 (4)	0.000 (4)
C38	0.054 (5)	0.074 (6)	0.059 (5)	0.008 (5)	−0.006 (4)	0.001 (5)
C39	0.048 (5)	0.076 (6)	0.066 (6)	0.007 (5)	−0.001 (4)	−0.001 (5)
C40	0.056 (6)	0.084 (7)	0.074 (6)	0.011 (5)	−0.004 (5)	0.002 (6)
C41	0.066 (7)	0.101 (9)	0.088 (8)	0.018 (6)	0.002 (6)	0.004 (7)
C42	0.064 (7)	0.129 (12)	0.132 (11)	0.022 (8)	−0.013 (7)	−0.005 (9)

Geometric parameters (Å, º)

Br1—C1	1.886 (7)	C20—H20B	0.9700
Br2—C2	1.890 (7)	C21—C22	1.503 (16)
O1—C5	1.347 (8)	C21—H21A	0.9700
O1—C11	1.427 (8)	C21—H21B	0.9700
O2—C4	1.365 (8)	C22—H22A	0.9600
O2—C31	1.451 (8)	C22—H22B	0.9600
C1—C6	1.368 (10)	C22—H22C	0.9600
C1—C2	1.394 (10)	C31—C32	1.502 (10)
C2—C3	1.379 (9)	C31—H31A	0.9700
C3—C4	1.378 (9)	C31—H31B	0.9700
C3—H3	0.9300	C32—C33	1.532 (10)
C4—C5	1.404 (10)	C32—H32A	0.9700
C5—C6	1.397 (9)	C32—H32B	0.9700
C6—H6	0.9300	C33—C34	1.530 (10)
C11—C12	1.508 (9)	C33—H33A	0.9700
C11—H11A	0.9700	C33—H33B	0.9700
C11—H11B	0.9700	C34—C35	1.514 (10)
C12—C13	1.527 (10)	C34—H34A	0.9700
C12—H12A	0.9700	C34—H34B	0.9700
C12—H12B	0.9700	C35—C36	1.528 (11)
C13—C14	1.515 (10)	C35—H35A	0.9700
C13—H13A	0.9700	C35—H35B	0.9700
C13—H13B	0.9700	C36—C37	1.511 (11)
C14—C15	1.528 (10)	C36—H36A	0.9700
C14—H14A	0.9700	C36—H36B	0.9700
C14—H14B	0.9700	C37—C38	1.542 (11)
C15—C16	1.522 (10)	C37—H37A	0.9700
C15—H15A	0.9700	C37—H37B	0.9700
C15—H15B	0.9700	C38—C39	1.511 (12)
C16—C17	1.529 (12)	C38—H38A	0.9700
C16—H16A	0.9700	C38—H38B	0.9700
C16—H16B	0.9700	C39—C40	1.528 (12)
C17—C18	1.516 (12)	C39—H39A	0.9700
C17—H17A	0.9700	C39—H39B	0.9700
C17—H17B	0.9700	C40—C41	1.509 (14)
C18—C19	1.535 (12)	C40—H40A	0.9700
C18—H18A	0.9700	C40—H40B	0.9700
C18—H18B	0.9700	C41—C42	1.506 (14)
C19—C20	1.505 (12)	C41—H41A	0.9700
C19—H19A	0.9700	C41—H41B	0.9700
C19—H19B	0.9700	C42—H42A	0.9600
C20—C21	1.530 (14)	C42—H42B	0.9600
C20—H20A	0.9700	C42—H42C	0.9600
C5—O1—C11	117.9 (5)	C20—C21—H21A	108.9
C4—O2—C31	117.1 (5)	C22—C21—H21B	108.9
C6—C1—C2	119.4 (6)	C20—C21—H21B	108.9
C6—C1—Br1	119.4 (6)	H21A—C21—H21B	107.7
C2—C1—Br1	121.2 (5)	C21—C22—H22A	109.5
C3—C2—C1	119.9 (6)	C21—C22—H22B	109.5
C3—C2—Br2	117.8 (5)	H22A—C22—H22B	109.5
C1—C2—Br2	122.2 (5)	C21—C22—H22C	109.5
C4—C3—C2	120.7 (6)	H22A—C22—H22C	109.5
C4—C3—H3	119.6	H22B—C22—H22C	109.5
C2—C3—H3	119.6	O2—C31—C32	107.3 (6)
O2—C4—C3	125.6 (6)	O2—C31—H31A	110.2
O2—C4—C5	114.4 (6)	C32—C31—H31A	110.2
C3—C4—C5	120.0 (6)	O2—C31—H31B	110.2
O1—C5—C6	125.0 (6)	C32—C31—H31B	110.2
O1—C5—C4	116.8 (6)	H31A—C31—H31B	108.5
C6—C5—C4	118.2 (6)	C31—C32—C33	112.7 (6)
C1—C6—C5	121.7 (7)	C31—C32—H32A	109.0
C1—C6—H6	119.1	C33—C32—H32A	109.0
C5—C6—H6	119.1	C31—C32—H32B	109.0
O1—C11—C12	106.1 (6)	C33—C32—H32B	109.0
O1—C11—H11A	110.5	H32A—C32—H32B	107.8
C12—C11—H11A	110.5	C34—C33—C32	114.6 (6)
O1—C11—H11B	110.5	C34—C33—H33A	108.6
C12—C11—H11B	110.5	C32—C33—H33A	108.6
H11A—C11—H11B	108.7	C34—C33—H33B	108.6
C11—C12—C13	113.4 (6)	C32—C33—H33B	108.6
C11—C12—H12A	108.9	H33A—C33—H33B	107.6
C13—C12—H12A	108.9	C35—C34—C33	112.3 (6)
C11—C12—H12B	108.9	C35—C34—H34A	109.1
C13—C12—H12B	108.9	C33—C34—H34A	109.1
H12A—C12—H12B	107.7	C35—C34—H34B	109.1
C14—C13—C12	111.9 (6)	C33—C34—H34B	109.1
C14—C13—H13A	109.2	H34A—C34—H34B	107.9
C12—C13—H13A	109.2	C34—C35—C36	114.7 (7)
C14—C13—H13B	109.2	C34—C35—H35A	108.6
C12—C13—H13B	109.2	C36—C35—H35A	108.6
H13A—C13—H13B	107.9	C34—C35—H35B	108.6
C13—C14—C15	114.7 (7)	C36—C35—H35B	108.6
C13—C14—H14A	108.6	H35A—C35—H35B	107.6
C15—C14—H14A	108.6	C37—C36—C35	112.6 (7)
C13—C14—H14B	108.6	C37—C36—H36A	109.1
C15—C14—H14B	108.6	C35—C36—H36A	109.1
H14A—C14—H14B	107.6	C37—C36—H36B	109.1
C16—C15—C14	112.4 (7)	C35—C36—H36B	109.1
C16—C15—H15A	109.1	H36A—C36—H36B	107.8
C14—C15—H15A	109.1	C36—C37—C38	114.3 (7)
C16—C15—H15B	109.1	C36—C37—H37A	108.7
C14—C15—H15B	109.1	C38—C37—H37A	108.7
H15A—C15—H15B	107.8	C36—C37—H37B	108.7
C15—C16—C17	113.7 (7)	C38—C37—H37B	108.7
C15—C16—H16A	108.8	H37A—C37—H37B	107.6
C17—C16—H16A	108.8	C39—C38—C37	113.7 (7)
C15—C16—H16B	108.8	C39—C38—H38A	108.8
C17—C16—H16B	108.8	C37—C38—H38A	108.8
H16A—C16—H16B	107.7	C39—C38—H38B	108.8
C18—C17—C16	113.1 (8)	C37—C38—H38B	108.8
C18—C17—H17A	109.0	H38A—C38—H38B	107.7
C16—C17—H17A	109.0	C38—C39—C40	114.3 (8)
C18—C17—H17B	109.0	C38—C39—H39A	108.7
C16—C17—H17B	109.0	C40—C39—H39A	108.7
H17A—C17—H17B	107.8	C38—C39—H39B	108.7
C17—C18—C19	113.7 (8)	C40—C39—H39B	108.7
C17—C18—H18A	108.8	H39A—C39—H39B	107.6
C19—C18—H18A	108.8	C41—C40—C39	113.9 (8)
C17—C18—H18B	108.8	C41—C40—H40A	108.8
C19—C18—H18B	108.8	C39—C40—H40A	108.8
H18A—C18—H18B	107.7	C41—C40—H40B	108.8
C20—C19—C18	114.0 (8)	C39—C40—H40B	108.8
C20—C19—H19A	108.8	H40A—C40—H40B	107.7
C18—C19—H19A	108.8	C42—C41—C40	113.7 (10)
C20—C19—H19B	108.8	C42—C41—H41A	108.8
C18—C19—H19B	108.8	C40—C41—H41A	108.8
H19A—C19—H19B	107.6	C42—C41—H41B	108.8
C19—C20—C21	114.2 (9)	C40—C41—H41B	108.8
C19—C20—H20A	108.7	H41A—C41—H41B	107.7
C21—C20—H20A	108.7	C41—C42—H42A	109.5
C19—C20—H20B	108.7	C41—C42—H42B	109.5
C21—C20—H20B	108.7	H42A—C42—H42B	109.5
H20A—C20—H20B	107.6	C41—C42—H42C	109.5
C22—C21—C20	113.4 (11)	H42A—C42—H42C	109.5
C22—C21—H21A	108.9	H42B—C42—H42C	109.5

(N14)

Crystal data

C34H60Br2O2	F(000) = 1400
Mr = 660.64	Dx = 1.249 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 45.220 (7) Å	Cell parameters from 7679 reflections
b = 8.374 (4) Å	θ = 4.0–24.5°
c = 9.279 (4) Å	µ = 2.33 mm^−1
β = 91.809 (5)°	T = 294 K
V = 3512 (3) Å^3	Plates, colourless
Z = 4	0.60 × 0.34 × 0.12 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	9026 independent reflections
Radiation source: fine-focus sealed tube	4839 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.198
ω scans, thick slices	θmax = 29.3°, θmin = 3.7°
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009)	h = −60→59
	k = −11→11
74939 measured reflections	l = −12→12

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.107	w = 1/[σ^2(Fo^2) + (0.1331P)^2 + 15.6412P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.320	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 1.23 e Å^−3
9026 reflections	Δρmin = −1.26 e Å^−3
346 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0114 (13)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.04224 (2)	0.05553 (11)	−0.46682 (8)	0.0561 (3)
Br2	0.00586 (2)	−0.14667 (12)	−0.21278 (11)	0.0664 (4)
O1	0.12194 (14)	0.1671 (7)	−0.0568 (6)	0.0593 (15)
O2	0.09588 (12)	−0.0013 (6)	0.1334 (5)	0.0488 (12)
C1	0.05690 (17)	0.0413 (8)	−0.2735 (7)	0.0406 (15)
C2	0.04223 (16)	−0.0436 (7)	−0.1709 (8)	0.0406 (15)
C3	0.05422 (15)	−0.0549 (8)	−0.0312 (8)	0.0396 (15)
H3	0.0439	−0.1083	0.0395	0.048*
C4	0.08158 (17)	0.0136 (8)	0.0025 (7)	0.0413 (15)
C5	0.09576 (16)	0.1017 (8)	−0.1008 (7)	0.0409 (15)
C6	0.08380 (17)	0.1180 (8)	−0.2382 (8)	0.0428 (16)
H6	0.0934	0.1787	−0.3065	0.051*
C11	0.14181 (17)	0.2187 (10)	−0.1643 (9)	0.0524 (19)
H11A	0.1334	0.3075	−0.2186	0.063*
H11B	0.1457	0.1323	−0.2307	0.063*
C12	0.16972 (18)	0.2690 (11)	−0.0870 (9)	0.058 (2)
H12A	0.1765	0.1825	−0.0246	0.070*
H12B	0.1655	0.3599	−0.0262	0.070*
C13	0.19470 (19)	0.3140 (12)	−0.1868 (11)	0.063 (2)
H13A	0.1987	0.2245	−0.2496	0.076*
H13B	0.1884	0.4033	−0.2469	0.076*
C14	0.2225 (2)	0.3584 (14)	−0.1048 (11)	0.072 (3)
H14A	0.2281	0.2703	−0.0418	0.086*
H14B	0.2183	0.4495	−0.0441	0.086*
C15	0.2485 (2)	0.3990 (14)	−0.1951 (12)	0.076 (3)
H15A	0.2431	0.4877	−0.2579	0.092*
H15B	0.2528	0.3081	−0.2557	0.092*
C16	0.2765 (2)	0.4436 (15)	−0.1063 (13)	0.083 (3)
H16A	0.2721	0.5343	−0.0456	0.100*
H16B	0.2818	0.3549	−0.0435	0.100*
C17	0.3028 (2)	0.4848 (16)	−0.1959 (15)	0.093 (4)
H17A	0.2976	0.5751	−0.2572	0.112*
H17B	0.3069	0.3950	−0.2581	0.112*
C18	0.3305 (3)	0.5253 (17)	−0.1075 (16)	0.100 (4)
H18A	0.3263	0.6162	−0.0467	0.120*
H18B	0.3352	0.4358	−0.0445	0.120*
C19	0.3574 (3)	0.5636 (19)	−0.1930 (18)	0.111 (5)
H19A	0.3623	0.4705	−0.2496	0.134*
H19B	0.3524	0.6493	−0.2597	0.134*
C20	0.3843 (3)	0.612 (2)	−0.1038 (18)	0.111 (5)
H20A	0.3798	0.7086	−0.0510	0.133*
H20B	0.3889	0.5288	−0.0340	0.133*
C21	0.4110 (3)	0.641 (2)	−0.192 (2)	0.125 (5)
H21A	0.4066	0.7278	−0.2591	0.150*
H21B	0.4149	0.5465	−0.2480	0.150*
C22	0.4382 (3)	0.683 (2)	−0.103 (2)	0.133 (6)
H22A	0.4418	0.5993	−0.0331	0.160*
H22B	0.4344	0.7809	−0.0509	0.160*
C23	0.4656 (4)	0.706 (3)	−0.188 (3)	0.168 (8)
H23A	0.4690	0.6095	−0.2428	0.202*
H23B	0.4622	0.7921	−0.2562	0.202*
C24	0.4930 (5)	0.743 (4)	−0.101 (3)	0.248 (16)
H24A	0.5075	0.7885	−0.1616	0.371*
H24B	0.5007	0.6462	−0.0580	0.371*
H24C	0.4884	0.8172	−0.0258	0.371*
C31	0.08669 (17)	−0.1273 (9)	0.2289 (8)	0.0461 (17)
H31A	0.0817	−0.2227	0.1743	0.055*
H31B	0.0695	−0.0941	0.2811	0.055*
C32	0.11215 (18)	−0.1594 (9)	0.3314 (8)	0.0477 (17)
H32A	0.1062	−0.2396	0.4001	0.057*
H32B	0.1167	−0.0624	0.3848	0.057*
C33	0.14025 (18)	−0.2166 (10)	0.2598 (9)	0.0544 (19)
H33A	0.1353	−0.3087	0.2005	0.065*
H33B	0.1468	−0.1329	0.1961	0.065*
C34	0.16574 (19)	−0.2613 (11)	0.3605 (9)	0.058 (2)
H34A	0.1704	−0.1708	0.4224	0.070*
H34B	0.1596	−0.3484	0.4216	0.070*
C35	0.1933 (2)	−0.3106 (12)	0.2861 (11)	0.063 (2)
H35A	0.1989	−0.2242	0.2229	0.076*
H35B	0.1885	−0.4019	0.2255	0.076*
C36	0.2202 (2)	−0.3538 (12)	0.3802 (11)	0.070 (3)
H36A	0.2251	−0.2641	0.4427	0.084*
H36B	0.2152	−0.4434	0.4411	0.084*
C37	0.2467 (2)	−0.3963 (13)	0.2984 (12)	0.075 (3)
H37A	0.2515	−0.3067	0.2372	0.090*
H37B	0.2417	−0.4857	0.2358	0.090*
C38	0.2745 (2)	−0.4407 (15)	0.3902 (14)	0.085 (3)
H38A	0.2797	−0.3509	0.4520	0.102*
H38B	0.2697	−0.5299	0.4520	0.102*
C39	0.3004 (3)	−0.4840 (16)	0.3054 (17)	0.098 (4)
H39A	0.3047	−0.3965	0.2407	0.118*
H39B	0.2954	−0.5765	0.2467	0.118*
C40	0.3287 (3)	−0.5218 (19)	0.3976 (16)	0.104 (4)
H40A	0.3332	−0.4306	0.4589	0.125*
H40B	0.3246	−0.6115	0.4600	0.125*
C41	0.3555 (3)	−0.5606 (18)	0.3132 (18)	0.113 (5)
H41A	0.3602	−0.4683	0.2550	0.135*
H41B	0.3505	−0.6474	0.2476	0.135*
C42	0.3827 (3)	−0.607 (2)	0.4009 (19)	0.116 (5)
H42A	0.3874	−0.5211	0.4679	0.139*
H42B	0.3780	−0.7006	0.4574	0.139*
C43	0.4093 (3)	−0.642 (2)	0.317 (2)	0.133 (6)
H43A	0.4136	−0.5498	0.2581	0.159*
H43B	0.4049	−0.7307	0.2529	0.159*
C44	0.4364 (4)	−0.682 (3)	0.407 (2)	0.163 (8)
H44A	0.4531	−0.6896	0.3458	0.244*
H44B	0.4335	−0.7826	0.4543	0.244*
H44C	0.4399	−0.6002	0.4776	0.244*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0625 (6)	0.0683 (6)	0.0369 (4)	0.0007 (4)	−0.0088 (3)	−0.0034 (4)
Br2	0.0563 (6)	0.0707 (6)	0.0714 (6)	−0.0205 (4)	−0.0117 (4)	0.0098 (4)
O1	0.067 (4)	0.064 (3)	0.047 (3)	−0.020 (3)	−0.003 (3)	0.000 (3)
O2	0.066 (3)	0.040 (3)	0.040 (3)	−0.008 (2)	−0.010 (2)	0.007 (2)
C1	0.061 (4)	0.030 (3)	0.031 (3)	0.006 (3)	0.006 (3)	−0.001 (3)
C2	0.048 (4)	0.029 (3)	0.045 (4)	−0.004 (3)	−0.002 (3)	−0.001 (3)
C3	0.041 (4)	0.033 (3)	0.045 (4)	0.000 (3)	−0.001 (3)	0.003 (3)
C4	0.050 (4)	0.037 (3)	0.037 (3)	0.004 (3)	0.001 (3)	0.005 (3)
C5	0.047 (4)	0.040 (3)	0.035 (3)	−0.003 (3)	−0.006 (3)	0.005 (3)
C6	0.055 (4)	0.034 (3)	0.040 (4)	0.001 (3)	0.000 (3)	0.007 (3)
C11	0.047 (4)	0.047 (4)	0.063 (5)	−0.010 (3)	0.000 (4)	0.005 (4)
C12	0.052 (5)	0.067 (5)	0.056 (5)	−0.020 (4)	0.003 (4)	−0.001 (4)
C13	0.049 (5)	0.066 (5)	0.075 (6)	−0.014 (4)	0.004 (4)	0.004 (5)
C14	0.060 (6)	0.090 (7)	0.066 (6)	−0.011 (5)	−0.004 (5)	−0.004 (5)
C15	0.055 (6)	0.092 (7)	0.082 (7)	−0.013 (5)	−0.001 (5)	0.004 (6)
C16	0.054 (6)	0.102 (8)	0.092 (8)	−0.013 (5)	0.006 (5)	−0.004 (6)
C17	0.055 (6)	0.104 (9)	0.121 (10)	−0.011 (6)	0.002 (6)	−0.006 (8)
C18	0.068 (7)	0.107 (9)	0.126 (11)	−0.011 (7)	0.006 (7)	0.010 (8)
C19	0.071 (8)	0.117 (11)	0.147 (13)	−0.014 (7)	0.020 (8)	−0.002 (9)
C20	0.065 (7)	0.134 (12)	0.133 (12)	−0.017 (7)	0.009 (8)	−0.006 (10)
C21	0.092 (10)	0.139 (14)	0.144 (14)	−0.018 (9)	0.013 (10)	−0.004 (11)
C22	0.081 (10)	0.174 (17)	0.146 (14)	−0.020 (10)	0.008 (10)	0.014 (12)
C23	0.112 (14)	0.20 (2)	0.19 (2)	−0.012 (14)	0.024 (15)	0.002 (17)
C24	0.142 (19)	0.35 (4)	0.25 (3)	−0.09 (3)	0.06 (2)	−0.06 (3)
C31	0.053 (4)	0.047 (4)	0.038 (4)	−0.002 (3)	0.005 (3)	0.010 (3)
C32	0.062 (5)	0.042 (4)	0.040 (4)	0.002 (3)	0.005 (3)	0.005 (3)
C33	0.057 (5)	0.053 (4)	0.053 (4)	0.006 (4)	0.006 (4)	0.004 (4)
C34	0.061 (5)	0.061 (5)	0.054 (5)	0.004 (4)	−0.001 (4)	−0.003 (4)
C35	0.057 (5)	0.061 (5)	0.072 (6)	0.006 (4)	−0.002 (4)	−0.001 (4)
C36	0.062 (6)	0.072 (6)	0.074 (6)	0.012 (5)	−0.004 (5)	−0.001 (5)
C37	0.069 (6)	0.075 (6)	0.082 (7)	0.009 (5)	−0.005 (5)	0.004 (5)
C38	0.067 (7)	0.088 (8)	0.098 (8)	0.010 (6)	−0.001 (6)	−0.002 (6)
C39	0.063 (7)	0.088 (8)	0.142 (12)	0.012 (6)	−0.002 (7)	0.015 (8)
C40	0.074 (8)	0.122 (11)	0.115 (11)	0.009 (7)	−0.006 (7)	−0.020 (9)
C41	0.094 (10)	0.104 (10)	0.142 (13)	0.010 (8)	0.030 (9)	0.000 (9)
C42	0.079 (9)	0.126 (12)	0.141 (13)	0.015 (8)	−0.011 (9)	−0.009 (10)
C43	0.096 (11)	0.146 (15)	0.158 (16)	0.016 (10)	0.013 (11)	0.000 (12)
C44	0.095 (11)	0.19 (2)	0.20 (2)	0.029 (12)	−0.024 (12)	−0.045 (16)

Geometric parameters (Å, º)

Br1—C1	1.896 (7)	C22—H22B	0.9700
Br2—C2	1.887 (7)	C23—C24	1.49 (3)
O1—C5	1.355 (9)	C23—H23A	0.9700
O1—C11	1.431 (9)	C23—H23B	0.9700
O2—C4	1.363 (8)	C24—H24A	0.9600
O2—C31	1.448 (8)	C24—H24B	0.9600
C1—C2	1.375 (10)	C24—H24C	0.9600
C1—C6	1.405 (11)	C31—C32	1.494 (11)
C2—C3	1.392 (10)	C31—H31A	0.9700
C3—C4	1.391 (10)	C31—H31B	0.9700
C3—H3	0.9300	C32—C33	1.529 (11)
C4—C5	1.382 (10)	C32—H32A	0.9700
C5—C6	1.376 (10)	C32—H32B	0.9700
C6—H6	0.9300	C33—C34	1.508 (11)
C11—C12	1.492 (11)	C33—H33A	0.9700
C11—H11A	0.9700	C33—H33B	0.9700
C11—H11B	0.9700	C34—C35	1.503 (12)
C12—C13	1.530 (11)	C34—H34A	0.9700
C12—H12A	0.9700	C34—H34B	0.9700
C12—H12B	0.9700	C35—C36	1.517 (13)
C13—C14	1.496 (12)	C35—H35A	0.9700
C13—H13A	0.9700	C35—H35B	0.9700
C13—H13B	0.9700	C36—C37	1.481 (14)
C14—C15	1.502 (14)	C36—H36A	0.9700
C14—H14A	0.9700	C36—H36B	0.9700
C14—H14B	0.9700	C37—C38	1.542 (14)
C15—C16	1.536 (14)	C37—H37A	0.9700
C15—H15A	0.9700	C37—H37B	0.9700
C15—H15B	0.9700	C38—C39	1.478 (17)
C16—C17	1.511 (15)	C38—H38A	0.9700
C16—H16A	0.9700	C38—H38B	0.9700
C16—H16B	0.9700	C39—C40	1.548 (17)
C17—C18	1.515 (16)	C39—H39A	0.9700
C17—H17A	0.9700	C39—H39B	0.9700
C17—H17B	0.9700	C40—C41	1.499 (18)
C18—C19	1.507 (17)	C40—H40A	0.9700
C18—H18A	0.9700	C40—H40B	0.9700
C18—H18B	0.9700	C41—C42	1.504 (19)
C19—C20	1.506 (18)	C41—H41A	0.9700
C19—H19A	0.9700	C41—H41B	0.9700
C19—H19B	0.9700	C42—C43	1.48 (2)
C20—C21	1.498 (19)	C42—H42A	0.9700
C20—H20A	0.9700	C42—H42B	0.9700
C20—H20B	0.9700	C43—C44	1.50 (2)
C21—C22	1.50 (2)	C43—H43A	0.9700
C21—H21A	0.9700	C43—H43B	0.9700
C21—H21B	0.9700	C44—H44A	0.9600
C22—C23	1.50 (2)	C44—H44B	0.9600
C22—H22A	0.9700	C44—H44C	0.9600
C5—O1—C11	118.3 (6)	C22—C23—H23A	108.4
C4—O2—C31	118.4 (6)	C24—C23—H23B	108.4
C2—C1—C6	120.5 (6)	C22—C23—H23B	108.4
C2—C1—Br1	121.7 (6)	H23A—C23—H23B	107.5
C6—C1—Br1	117.8 (5)	C23—C24—H24A	109.5
C1—C2—C3	119.9 (7)	C23—C24—H24B	109.5
C1—C2—Br2	122.0 (6)	H24A—C24—H24B	109.5
C3—C2—Br2	118.1 (5)	C23—C24—H24C	109.5
C4—C3—C2	119.9 (7)	H24A—C24—H24C	109.5
C4—C3—H3	120.1	H24B—C24—H24C	109.5
C2—C3—H3	120.1	O2—C31—C32	106.9 (6)
O2—C4—C5	116.7 (6)	O2—C31—H31A	110.3
O2—C4—C3	123.8 (6)	C32—C31—H31A	110.3
C5—C4—C3	119.6 (6)	O2—C31—H31B	110.3
O1—C5—C6	123.6 (7)	C32—C31—H31B	110.3
O1—C5—C4	115.3 (6)	H31A—C31—H31B	108.6
C6—C5—C4	121.2 (7)	C31—C32—C33	114.5 (6)
C5—C6—C1	118.9 (7)	C31—C32—H32A	108.6
C5—C6—H6	120.6	C33—C32—H32A	108.6
C1—C6—H6	120.6	C31—C32—H32B	108.6
O1—C11—C12	106.9 (7)	C33—C32—H32B	108.6
O1—C11—H11A	110.3	H32A—C32—H32B	107.6
C12—C11—H11A	110.3	C34—C33—C32	116.0 (7)
O1—C11—H11B	110.3	C34—C33—H33A	108.3
C12—C11—H11B	110.3	C32—C33—H33A	108.3
H11A—C11—H11B	108.6	C34—C33—H33B	108.3
C11—C12—C13	114.1 (7)	C32—C33—H33B	108.3
C11—C12—H12A	108.7	H33A—C33—H33B	107.4
C13—C12—H12A	108.7	C35—C34—C33	114.4 (7)
C11—C12—H12B	108.7	C35—C34—H34A	108.7
C13—C12—H12B	108.7	C33—C34—H34A	108.7
H12A—C12—H12B	107.6	C35—C34—H34B	108.7
C14—C13—C12	112.2 (8)	C33—C34—H34B	108.7
C14—C13—H13A	109.2	H34A—C34—H34B	107.6
C12—C13—H13A	109.2	C34—C35—C36	117.6 (8)
C14—C13—H13B	109.2	C34—C35—H35A	107.9
C12—C13—H13B	109.2	C36—C35—H35A	107.9
H13A—C13—H13B	107.9	C34—C35—H35B	107.9
C13—C14—C15	115.5 (8)	C36—C35—H35B	107.9
C13—C14—H14A	108.4	H35A—C35—H35B	107.2
C15—C14—H14A	108.4	C37—C36—C35	114.1 (9)
C13—C14—H14B	108.4	C37—C36—H36A	108.7
C15—C14—H14B	108.4	C35—C36—H36A	108.7
H14A—C14—H14B	107.5	C37—C36—H36B	108.7
C14—C15—C16	113.7 (9)	C35—C36—H36B	108.7
C14—C15—H15A	108.8	H36A—C36—H36B	107.6
C16—C15—H15A	108.8	C36—C37—C38	115.6 (9)
C14—C15—H15B	108.8	C36—C37—H37A	108.4
C16—C15—H15B	108.8	C38—C37—H37A	108.4
H15A—C15—H15B	107.7	C36—C37—H37B	108.4
C17—C16—C15	114.2 (10)	C38—C37—H37B	108.4
C17—C16—H16A	108.7	H37A—C37—H37B	107.4
C15—C16—H16A	108.7	C39—C38—C37	114.3 (11)
C17—C16—H16B	108.7	C39—C38—H38A	108.7
C15—C16—H16B	108.7	C37—C38—H38A	108.7
H16A—C16—H16B	107.6	C39—C38—H38B	108.7
C16—C17—C18	113.9 (11)	C37—C38—H38B	108.7
C16—C17—H17A	108.8	H38A—C38—H38B	107.6
C18—C17—H17A	108.8	C38—C39—C40	114.3 (12)
C16—C17—H17B	108.8	C38—C39—H39A	108.7
C18—C17—H17B	108.8	C40—C39—H39A	108.7
H17A—C17—H17B	107.7	C38—C39—H39B	108.7
C19—C18—C17	115.5 (13)	C40—C39—H39B	108.7
C19—C18—H18A	108.4	H39A—C39—H39B	107.6
C17—C18—H18A	108.4	C41—C40—C39	115.0 (13)
C19—C18—H18B	108.4	C41—C40—H40A	108.5
C17—C18—H18B	108.4	C39—C40—H40A	108.5
H18A—C18—H18B	107.5	C41—C40—H40B	108.5
C20—C19—C18	114.9 (14)	C39—C40—H40B	108.5
C20—C19—H19A	108.6	H40A—C40—H40B	107.5
C18—C19—H19A	108.6	C40—C41—C42	115.7 (14)
C20—C19—H19B	108.6	C40—C41—H41A	108.4
C18—C19—H19B	108.6	C42—C41—H41A	108.4
H19A—C19—H19B	107.5	C40—C41—H41B	108.4
C21—C20—C19	113.3 (13)	C42—C41—H41B	108.4
C21—C20—H20A	108.9	H41A—C41—H41B	107.4
C19—C20—H20A	108.9	C43—C42—C41	115.6 (14)
C21—C20—H20B	108.9	C43—C42—H42A	108.4
C19—C20—H20B	108.9	C41—C42—H42A	108.4
H20A—C20—H20B	107.7	C43—C42—H42B	108.4
C20—C21—C22	113.5 (14)	C41—C42—H42B	108.4
C20—C21—H21A	108.9	H42A—C42—H42B	107.5
C22—C21—H21A	108.9	C42—C43—C44	114.7 (16)
C20—C21—H21B	108.9	C42—C43—H43A	108.6
C22—C21—H21B	108.9	C44—C43—H43A	108.6
H21A—C21—H21B	107.7	C42—C43—H43B	108.6
C21—C22—C23	115.0 (16)	C44—C43—H43B	108.6
C21—C22—H22A	108.5	H43A—C43—H43B	107.6
C23—C22—H22A	108.5	C43—C44—H44A	109.5
C21—C22—H22B	108.5	C43—C44—H44B	109.5
C23—C22—H22B	108.5	H44A—C44—H44B	109.5
H22A—C22—H22B	107.5	C43—C44—H44C	109.5
C24—C23—C22	115 (2)	H44A—C44—H44C	109.5
C24—C23—H23A	108.4	H44B—C44—H44C	109.5

(N18)

Crystal data

C42H76Br2O2	F(000) = 3312
Mr = 772.84	Dx = 1.232 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 110.750 (5) Å	Cell parameters from 13351 reflections
b = 8.2292 (3) Å	θ = 3.7–28.8°
c = 9.1539 (3) Å	µ = 1.98 mm^−1
β = 92.268 (2)°	T = 294 K
V = 8336.2 (5) Å^3	Playes, colourless
Z = 8	0.50 × 0.40 × 0.10 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	7623 independent reflections
Radiation source: fine-focus sealed tube	6136 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.153
ω scans, thick slices	θmax = 29.2°, θmin = 3.7°
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009)	h = −149→149
	k = −10→11
62353 measured reflections	l = −6→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.113	w = 1/[σ^2(Fo^2) + (0.0682P)^2 + 394.7825P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.292	(Δ/σ)max = 0.001
S = 1.13	Δρmax = 1.52 e Å^−3
7623 reflections	Δρmin = −1.69 e Å^−3
418 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
333 restraints	Extinction coefficient: 0.00129 (14)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.23285 (2)	0.30718 (11)	0.96884 (12)	0.0210 (3)
Br2	0.24751 (2)	0.10395 (12)	0.70806 (14)	0.0287 (4)
O1	0.19955 (5)	0.4169 (8)	0.5566 (8)	0.0219 (13)
O2	0.21017 (5)	0.2484 (7)	0.3618 (8)	0.0169 (11)
C1	0.22681 (7)	0.2944 (9)	0.7767 (11)	0.0119 (11)
C2	0.23242 (7)	0.2117 (9)	0.6701 (11)	0.0127 (11)
C3	0.22747 (7)	0.1935 (9)	0.5260 (11)	0.0122 (11)
H3AA	0.2316	0.1364	0.4555	0.015*
C4	0.21641 (7)	0.2632 (9)	0.4939 (11)	0.0112 (10)
C5	0.21039 (7)	0.3528 (10)	0.6013 (11)	0.0136 (11)
C6	0.21530 (7)	0.3675 (9)	0.7383 (11)	0.0104 (11)
H6AA	0.2112	0.4252	0.8083	0.013*
C11	0.19153 (7)	0.4687 (11)	0.6716 (11)	0.0197 (16)
H11A	0.1950	0.5581	0.7277	0.024*
H11B	0.1899	0.3796	0.7373	0.024*
C12	0.18023 (7)	0.5212 (12)	0.5881 (11)	0.0214 (17)
H12A	0.1775	0.4334	0.5241	0.026*
H12B	0.1821	0.6136	0.5272	0.026*
C13	0.16993 (7)	0.5680 (12)	0.6869 (12)	0.0207 (17)
H13A	0.1681	0.4763	0.7488	0.025*
H13B	0.1725	0.6572	0.7498	0.025*
C14	0.15860 (8)	0.6177 (13)	0.5998 (12)	0.0244 (19)
H14A	0.1605	0.7112	0.5403	0.029*
H14B	0.1563	0.5297	0.5341	0.029*
C15	0.14794 (8)	0.6597 (13)	0.6903 (12)	0.026 (2)
H15A	0.1502	0.7478	0.7563	0.031*
H15B	0.1460	0.5663	0.7493	0.031*
C16	0.13680 (8)	0.7099 (16)	0.5993 (13)	0.035 (2)
H16A	0.1346	0.6215	0.5336	0.042*
H16B	0.1389	0.8026	0.5398	0.042*
C17	0.12595 (8)	0.7537 (16)	0.6866 (13)	0.035 (2)
H17A	0.1280	0.8452	0.7495	0.042*
H17B	0.1240	0.6626	0.7488	0.042*
C18	0.11481 (9)	0.7971 (18)	0.5914 (15)	0.044 (3)
H18A	0.1168	0.8869	0.5280	0.052*
H18B	0.1127	0.7049	0.5296	0.052*
C19	0.10388 (10)	0.8442 (19)	0.6776 (15)	0.049 (3)
H19A	0.1060	0.9360	0.7398	0.059*
H19B	0.1018	0.7542	0.7405	0.059*
C20	0.09272 (10)	0.889 (2)	0.5820 (17)	0.058 (3)
H20A	0.0947	0.9788	0.5191	0.070*
H20B	0.0906	0.7970	0.5198	0.070*
C21	0.08193 (11)	0.935 (2)	0.6674 (18)	0.070 (4)
H21A	0.0841	1.0253	0.7312	0.083*
H21B	0.0798	0.8442	0.7286	0.083*
C22	0.07083 (13)	0.984 (3)	0.5725 (19)	0.083 (4)
H22A	0.0730	1.0759	0.5129	0.099*
H22B	0.0688	0.8943	0.5068	0.099*
C23	0.05979 (13)	1.027 (3)	0.654 (2)	0.090 (4)
H23A	0.0618	1.1173	0.7181	0.108*
H23B	0.0577	0.9351	0.7147	0.108*
C24	0.04869 (15)	1.072 (3)	0.558 (2)	0.107 (5)
H24A	0.0508	1.1631	0.4973	0.128*
H24B	0.0467	0.9809	0.4943	0.128*
C25	0.03767 (16)	1.115 (3)	0.640 (3)	0.118 (6)
H25A	0.0397	1.2061	0.7036	0.142*
H25B	0.0357	1.0239	0.7010	0.142*
C26	0.02666 (18)	1.159 (4)	0.547 (3)	0.126 (6)
H26A	0.0288	1.2490	0.4838	0.151*
H26B	0.0246	1.0676	0.4844	0.151*
C27	0.0158 (2)	1.206 (5)	0.625 (3)	0.178 (8)
H27A	0.0177	1.3012	0.6835	0.213*
H27B	0.0138	1.1186	0.6907	0.213*
C28	0.0047 (2)	1.243 (4)	0.528 (3)	0.149 (9)
H28A	−0.0008	1.3083	0.5815	0.223*
H28B	0.0008	1.1428	0.4997	0.223*
H28C	0.0071	1.3003	0.4428	0.223*
C31	0.21368 (7)	0.1196 (9)	0.2643 (11)	0.0150 (14)
H31A	0.2157	0.0222	0.3197	0.018*
H31B	0.2207	0.1522	0.2118	0.018*
C32	0.20319 (7)	0.0869 (10)	0.1579 (11)	0.0142 (14)
H32A	0.2056	0.0047	0.0887	0.017*
H32B	0.2013	0.1855	0.1035	0.017*
C33	0.19186 (7)	0.0299 (11)	0.2322 (11)	0.0153 (16)
H33A	0.1940	−0.0632	0.2931	0.018*
H33B	0.1892	0.1158	0.2961	0.018*
C34	0.18138 (7)	−0.0167 (12)	0.1296 (11)	0.0197 (17)
H34A	0.1838	−0.1059	0.0683	0.024*
H34B	0.1794	0.0748	0.0664	0.024*
C35	0.17015 (7)	−0.0668 (12)	0.2091 (11)	0.0196 (17)
H35A	0.1678	0.0222	0.2715	0.024*
H35B	0.1722	−0.1586	0.2718	0.024*
C36	0.15923 (8)	−0.1134 (13)	0.1097 (12)	0.0251 (19)
H36A	0.1572	−0.0227	0.0455	0.030*
H36B	0.1614	−0.2045	0.0489	0.030*
C37	0.14815 (8)	−0.1589 (14)	0.1935 (12)	0.027 (2)
H37A	0.1502	−0.2484	0.2586	0.032*
H37B	0.1460	−0.0672	0.2536	0.032*
C38	0.13723 (9)	−0.2073 (16)	0.0985 (14)	0.037 (2)
H38A	0.1394	−0.2991	0.0385	0.044*
H38B	0.1351	−0.1178	0.0335	0.044*
C39	0.12626 (8)	−0.2525 (16)	0.1837 (14)	0.035 (2)
H39A	0.1243	−0.1620	0.2464	0.042*
H39B	0.1283	−0.3444	0.2462	0.042*
C40	0.11506 (9)	−0.2959 (18)	0.0889 (15)	0.042 (3)
H40A	0.1130	−0.2041	0.0264	0.051*
H40B	0.1170	−0.3866	0.0263	0.051*
C41	0.10420 (10)	−0.3405 (19)	0.1761 (15)	0.047 (3)
H41A	0.1022	−0.2489	0.2374	0.056*
H41B	0.1064	−0.4308	0.2401	0.056*
C42	0.09300 (11)	−0.387 (2)	0.0825 (17)	0.058 (3)
H42A	0.0908	−0.2968	0.0190	0.070*
H42B	0.0950	−0.4783	0.0207	0.070*
C43	0.08221 (12)	−0.433 (3)	0.1683 (19)	0.075 (4)
H43A	0.0801	−0.3409	0.2285	0.090*
H43B	0.0845	−0.5217	0.2335	0.090*
C44	0.07108 (13)	−0.483 (3)	0.076 (2)	0.080 (4)
H44A	0.0689	−0.3956	0.0094	0.096*
H44B	0.0732	−0.5770	0.0178	0.096*
C45	0.06020 (13)	−0.525 (3)	0.161 (2)	0.087 (4)
H45A	0.0583	−0.4330	0.2222	0.105*
H45B	0.0623	−0.6154	0.2255	0.105*
C46	0.04897 (16)	−0.570 (3)	0.072 (2)	0.111 (5)
H46A	0.0468	−0.4788	0.0097	0.133*
H46B	0.0509	−0.6605	0.0094	0.133*
C47	0.03836 (17)	−0.615 (4)	0.156 (3)	0.120 (6)
H47A	0.0363	−0.5237	0.2176	0.145*
H47B	0.0406	−0.7049	0.2199	0.145*
C48	0.02720 (19)	−0.662 (4)	0.065 (3)	0.140 (8)
H48A	0.0204	−0.6679	0.1268	0.210*
H48B	0.0285	−0.7664	0.0211	0.210*
H48C	0.0257	−0.5825	−0.0098	0.210*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0259 (4)	0.0303 (5)	0.0065 (8)	0.0003 (3)	−0.0032 (4)	0.0026 (4)
Br2	0.0218 (4)	0.0347 (5)	0.0290 (10)	0.0129 (4)	−0.0064 (4)	−0.0080 (5)
O1	0.0233 (13)	0.033 (3)	0.010 (2)	0.0120 (16)	−0.0019 (11)	0.003 (2)
O2	0.026 (2)	0.016 (2)	0.0085 (16)	0.0046 (17)	−0.0037 (12)	−0.0001 (15)
C1	0.0171 (13)	0.013 (2)	0.0055 (9)	0.0048 (14)	−0.0003 (6)	0.0020 (7)
C2	0.0145 (9)	0.015 (2)	0.0085 (11)	0.0013 (13)	0.0003 (8)	−0.0018 (12)
C3	0.0188 (14)	0.009 (2)	0.0089 (11)	0.0005 (15)	−0.0012 (9)	−0.0008 (12)
C4	0.0182 (14)	0.010 (2)	0.0056 (16)	0.0003 (14)	0.0011 (8)	0.0028 (14)
C5	0.0200 (14)	0.016 (3)	0.0048 (16)	0.0051 (16)	−0.0011 (9)	0.0018 (14)
C6	0.0164 (13)	0.011 (2)	0.0041 (16)	0.0035 (13)	0.0005 (10)	0.0030 (15)
C11	0.0233 (18)	0.023 (4)	0.013 (3)	0.005 (2)	0.0009 (17)	0.001 (2)
C12	0.0230 (18)	0.030 (4)	0.011 (3)	0.007 (2)	0.002 (2)	0.002 (3)
C13	0.0220 (17)	0.028 (4)	0.012 (3)	0.004 (2)	0.002 (2)	0.000 (3)
C14	0.0239 (18)	0.037 (4)	0.012 (3)	0.008 (2)	0.001 (2)	−0.001 (3)
C15	0.0242 (18)	0.041 (5)	0.012 (3)	0.009 (2)	0.001 (2)	−0.001 (3)
C16	0.0270 (19)	0.059 (6)	0.019 (3)	0.012 (3)	−0.002 (2)	0.004 (3)
C17	0.0267 (19)	0.054 (6)	0.023 (4)	0.008 (3)	0.000 (2)	−0.001 (4)
C18	0.031 (2)	0.068 (7)	0.031 (4)	0.011 (3)	−0.005 (3)	0.000 (4)
C19	0.035 (2)	0.074 (7)	0.039 (4)	0.012 (3)	−0.001 (3)	−0.002 (4)
C20	0.040 (2)	0.084 (9)	0.051 (4)	0.012 (3)	−0.008 (3)	0.002 (4)
C21	0.046 (3)	0.097 (10)	0.065 (5)	0.015 (4)	0.001 (3)	0.000 (5)
C22	0.053 (3)	0.111 (11)	0.083 (5)	0.014 (4)	−0.009 (3)	0.008 (5)
C23	0.059 (3)	0.109 (12)	0.101 (5)	0.012 (4)	0.002 (3)	0.006 (6)
C24	0.066 (3)	0.141 (14)	0.113 (6)	0.018 (5)	−0.004 (4)	0.011 (6)
C25	0.075 (3)	0.144 (15)	0.137 (6)	0.018 (5)	0.010 (4)	0.010 (7)
C26	0.081 (3)	0.145 (15)	0.152 (7)	0.017 (5)	0.001 (4)	0.011 (7)
C27	0.098 (4)	0.27 (2)	0.168 (7)	0.054 (6)	0.009 (5)	0.008 (8)
C28	0.091 (5)	0.18 (2)	0.175 (10)	0.022 (8)	0.008 (7)	0.021 (12)
C31	0.0222 (16)	0.013 (2)	0.010 (2)	−0.0012 (16)	0.001 (2)	0.0006 (18)
C32	0.0186 (16)	0.021 (3)	0.004 (2)	−0.0035 (16)	0.0062 (18)	0.001 (2)
C33	0.0189 (16)	0.024 (4)	0.004 (3)	−0.0046 (19)	0.0060 (19)	0.001 (2)
C34	0.0208 (16)	0.032 (4)	0.007 (3)	−0.006 (2)	0.004 (2)	−0.001 (3)
C35	0.0207 (17)	0.030 (4)	0.008 (3)	−0.004 (2)	0.004 (2)	0.000 (3)
C36	0.0224 (17)	0.042 (5)	0.011 (3)	−0.007 (2)	0.003 (2)	−0.002 (3)
C37	0.0234 (18)	0.044 (5)	0.013 (3)	−0.007 (2)	0.004 (2)	−0.001 (3)
C38	0.0279 (19)	0.061 (6)	0.021 (4)	−0.011 (3)	0.000 (2)	−0.003 (3)
C39	0.027 (2)	0.051 (6)	0.025 (4)	−0.006 (3)	0.002 (2)	0.001 (4)
C40	0.031 (2)	0.065 (7)	0.031 (4)	−0.010 (3)	−0.002 (3)	0.001 (4)
C41	0.034 (2)	0.069 (7)	0.037 (4)	−0.010 (3)	0.002 (3)	0.003 (4)
C42	0.041 (2)	0.080 (8)	0.053 (4)	−0.011 (3)	−0.008 (3)	−0.001 (4)
C43	0.049 (3)	0.108 (10)	0.067 (5)	−0.018 (4)	0.001 (3)	0.001 (5)
C44	0.053 (3)	0.104 (11)	0.083 (5)	−0.013 (4)	−0.008 (3)	−0.005 (5)
C45	0.056 (3)	0.108 (11)	0.098 (5)	−0.008 (4)	0.000 (3)	0.004 (6)
C46	0.066 (3)	0.155 (14)	0.111 (6)	−0.022 (5)	−0.008 (4)	0.003 (6)
C47	0.073 (4)	0.157 (15)	0.131 (7)	−0.020 (5)	0.004 (4)	0.007 (7)
C48	0.082 (5)	0.20 (2)	0.142 (10)	−0.032 (8)	−0.003 (6)	0.007 (11)

Geometric parameters (Å, º)

Br1—C1	1.860 (10)	C26—H26B	0.9700
Br2—C2	1.911 (8)	C27—C28	1.51 (2)
O1—C5	1.360 (10)	C27—H27A	0.9700
O1—C11	1.467 (11)	C27—H27B	0.9700
O2—C4	1.374 (12)	C28—H28A	0.9600
O2—C31	1.448 (10)	C28—H28B	0.9600
C1—C2	1.360 (12)	C28—H28C	0.9600
C1—C6	1.441 (10)	C31—C32	1.510 (11)
C2—C3	1.416 (14)	C31—H31A	0.9700
C3—C4	1.374 (11)	C31—H31B	0.9700
C3—H3AA	0.9300	C32—C33	1.525 (10)
C4—C5	1.416 (12)	C32—H32A	0.9700
C5—C6	1.353 (14)	C32—H32B	0.9700
C6—H6AA	0.9300	C33—C34	1.513 (11)
C11—C12	1.504 (11)	C33—H33A	0.9700
C11—H11A	0.9700	C33—H33B	0.9700
C11—H11B	0.9700	C34—C35	1.523 (10)
C12—C13	1.533 (11)	C34—H34A	0.9700
C12—H12A	0.9700	C34—H34B	0.9700
C12—H12B	0.9700	C35—C36	1.533 (12)
C13—C14	1.515 (11)	C35—H35A	0.9700
C13—H13A	0.9700	C35—H35B	0.9700
C13—H13B	0.9700	C36—C37	1.520 (11)
C14—C15	1.509 (11)	C36—H36A	0.9700
C14—H14A	0.9700	C36—H36B	0.9700
C14—H14B	0.9700	C37—C38	1.515 (12)
C15—C16	1.518 (12)	C37—H37A	0.9700
C15—H15A	0.9700	C37—H37B	0.9700
C15—H15B	0.9700	C38—C39	1.516 (13)
C16—C17	1.513 (13)	C38—H38A	0.9700
C16—H16A	0.9700	C38—H38B	0.9700
C16—H16B	0.9700	C39—C40	1.527 (13)
C17—C18	1.525 (13)	C39—H39A	0.9700
C17—H17A	0.9700	C39—H39B	0.9700
C17—H17B	0.9700	C40—C41	1.515 (14)
C18—C19	1.521 (14)	C40—H40A	0.9700
C18—H18A	0.9700	C40—H40B	0.9700
C18—H18B	0.9700	C41—C42	1.529 (15)
C19—C20	1.530 (14)	C41—H41A	0.9700
C19—H19A	0.9700	C41—H41B	0.9700
C19—H19B	0.9700	C42—C43	1.503 (17)
C20—C21	1.503 (16)	C42—H42A	0.9700
C20—H20A	0.9700	C42—H42B	0.9700
C20—H20B	0.9700	C43—C44	1.524 (18)
C21—C22	1.529 (16)	C43—H43A	0.9700
C21—H21A	0.9700	C43—H43B	0.9700
C21—H21B	0.9700	C44—C45	1.499 (19)
C22—C23	1.498 (18)	C44—H44A	0.9700
C22—H22A	0.9700	C44—H44B	0.9700
C22—H22B	0.9700	C45—C46	1.50 (2)
C23—C24	1.525 (19)	C45—H45A	0.9700
C23—H23A	0.9700	C45—H45B	0.9700
C23—H23B	0.9700	C46—C47	1.47 (2)
C24—C25	1.50 (2)	C46—H46A	0.9700
C24—H24A	0.9700	C46—H46B	0.9700
C24—H24B	0.9700	C47—C48	1.51 (2)
C25—C26	1.50 (2)	C47—H47A	0.9700
C25—H25A	0.9700	C47—H47B	0.9700
C25—H25B	0.9700	C48—H48A	0.9600
C26—C27	1.47 (2)	C48—H48B	0.9600
C26—H26A	0.9700	C48—H48C	0.9600
C5—O1—C11	116.7 (7)	C28—C27—H27A	108.4
C4—O2—C31	118.0 (6)	C26—C27—H27B	108.4
C2—C1—C6	117.4 (9)	C28—C27—H27B	108.4
C2—C1—Br1	123.3 (6)	H27A—C27—H27B	107.5
C6—C1—Br1	119.2 (7)	C27—C28—H28A	109.5
C1—C2—C3	123.4 (8)	C27—C28—H28B	109.5
C1—C2—Br2	121.5 (7)	H28A—C28—H28B	109.5
C3—C2—Br2	115.1 (6)	C27—C28—H28C	109.5
C4—C3—C2	117.6 (8)	H28A—C28—H28C	109.5
C4—C3—H3AA	121.2	H28B—C28—H28C	109.5
C2—C3—H3AA	121.2	O2—C31—C32	108.1 (6)
O2—C4—C3	124.3 (8)	O2—C31—H31A	110.1
O2—C4—C5	115.0 (7)	C32—C31—H31A	110.1
C3—C4—C5	120.6 (9)	O2—C31—H31B	110.1
C6—C5—O1	124.2 (8)	C32—C31—H31B	110.1
C6—C5—C4	120.5 (8)	H31A—C31—H31B	108.4
O1—C5—C4	115.3 (8)	C31—C32—C33	113.1 (8)
C5—C6—C1	120.5 (8)	C31—C32—H32A	109.0
C5—C6—H6AA	119.7	C33—C32—H32A	109.0
C1—C6—H6AA	119.7	C31—C32—H32B	109.0
O1—C11—C12	103.5 (8)	C33—C32—H32B	109.0
O1—C11—H11A	111.1	H32A—C32—H32B	107.8
C12—C11—H11A	111.1	C34—C33—C32	115.2 (8)
O1—C11—H11B	111.1	C34—C33—H33A	108.5
C12—C11—H11B	111.1	C32—C33—H33A	108.5
H11A—C11—H11B	109.0	C34—C33—H33B	108.5
C11—C12—C13	113.3 (8)	C32—C33—H33B	108.5
C11—C12—H12A	108.9	H33A—C33—H33B	107.5
C13—C12—H12A	108.9	C33—C34—C35	113.1 (8)
C11—C12—H12B	108.9	C33—C34—H34A	108.9
C13—C12—H12B	108.9	C35—C34—H34A	108.9
H12A—C12—H12B	107.7	C33—C34—H34B	108.9
C14—C13—C12	112.2 (8)	C35—C34—H34B	108.9
C14—C13—H13A	109.2	H34A—C34—H34B	107.8
C12—C13—H13A	109.2	C34—C35—C36	115.1 (8)
C14—C13—H13B	109.2	C34—C35—H35A	108.5
C12—C13—H13B	109.2	C36—C35—H35A	108.5
H13A—C13—H13B	107.9	C34—C35—H35B	108.5
C15—C14—C13	115.0 (9)	C36—C35—H35B	108.5
C15—C14—H14A	108.5	H35A—C35—H35B	107.5
C13—C14—H14A	108.5	C37—C36—C35	113.3 (8)
C15—C14—H14B	108.5	C37—C36—H36A	108.9
C13—C14—H14B	108.5	C35—C36—H36A	108.9
H14A—C14—H14B	107.5	C37—C36—H36B	108.9
C14—C15—C16	113.4 (9)	C35—C36—H36B	108.9
C14—C15—H15A	108.9	H36A—C36—H36B	107.7
C16—C15—H15A	108.9	C38—C37—C36	114.7 (9)
C14—C15—H15B	108.9	C38—C37—H37A	108.6
C16—C15—H15B	108.9	C36—C37—H37A	108.6
H15A—C15—H15B	107.7	C38—C37—H37B	108.6
C15—C16—C17	114.9 (9)	C36—C37—H37B	108.6
C15—C16—H16A	108.6	H37A—C37—H37B	107.6
C17—C16—H16A	108.6	C37—C38—C39	114.0 (9)
C15—C16—H16B	108.6	C37—C38—H38A	108.7
C17—C16—H16B	108.6	C39—C38—H38A	108.7
H16A—C16—H16B	107.5	C37—C38—H38B	108.7
C16—C17—C18	113.3 (10)	C39—C38—H38B	108.7
C16—C17—H17A	108.9	H38A—C38—H38B	107.6
C18—C17—H17A	108.9	C38—C39—C40	114.5 (10)
C16—C17—H17B	108.9	C38—C39—H39A	108.6
C18—C17—H17B	108.9	C40—C39—H39A	108.6
H17A—C17—H17B	107.7	C38—C39—H39B	108.6
C19—C18—C17	113.9 (10)	C40—C39—H39B	108.6
C19—C18—H18A	108.8	H39A—C39—H39B	107.6
C17—C18—H18A	108.8	C41—C40—C39	113.6 (10)
C19—C18—H18B	108.8	C41—C40—H40A	108.8
C17—C18—H18B	108.8	C39—C40—H40A	108.8
H18A—C18—H18B	107.7	C41—C40—H40B	108.8
C18—C19—C20	113.9 (11)	C39—C40—H40B	108.8
C18—C19—H19A	108.8	H40A—C40—H40B	107.7
C20—C19—H19A	108.8	C40—C41—C42	114.2 (11)
C18—C19—H19B	108.8	C40—C41—H41A	108.7
C20—C19—H19B	108.8	C42—C41—H41A	108.7
H19A—C19—H19B	107.7	C40—C41—H41B	108.7
C21—C20—C19	113.9 (12)	C42—C41—H41B	108.7
C21—C20—H20A	108.8	H41A—C41—H41B	107.6
C19—C20—H20A	108.8	C43—C42—C41	114.4 (12)
C21—C20—H20B	108.8	C43—C42—H42A	108.6
C19—C20—H20B	108.8	C41—C42—H42A	108.6
H20A—C20—H20B	107.7	C43—C42—H42B	108.6
C20—C21—C22	114.1 (13)	C41—C42—H42B	108.6
C20—C21—H21A	108.7	H42A—C42—H42B	107.6
C22—C21—H21A	108.7	C42—C43—C44	114.9 (13)
C20—C21—H21B	108.7	C42—C43—H43A	108.5
C22—C21—H21B	108.7	C44—C43—H43A	108.5
H21A—C21—H21B	107.6	C42—C43—H43B	108.5
C23—C22—C21	115.7 (14)	C44—C43—H43B	108.5
C23—C22—H22A	108.4	H43A—C43—H43B	107.5
C21—C22—H22A	108.4	C45—C44—C43	115.2 (14)
C23—C22—H22B	108.4	C45—C44—H44A	108.5
C21—C22—H22B	108.4	C43—C44—H44A	108.5
H22A—C22—H22B	107.4	C45—C44—H44B	108.5
C22—C23—C24	115.4 (15)	C43—C44—H44B	108.5
C22—C23—H23A	108.4	H44A—C44—H44B	107.5
C24—C23—H23A	108.4	C44—C45—C46	116.1 (15)
C22—C23—H23B	108.4	C44—C45—H45A	108.3
C24—C23—H23B	108.4	C46—C45—H45A	108.3
H23A—C23—H23B	107.5	C44—C45—H45B	108.3
C25—C24—C23	115.4 (16)	C46—C45—H45B	108.3
C25—C24—H24A	108.4	H45A—C45—H45B	107.4
C23—C24—H24A	108.4	C47—C46—C45	116.1 (17)
C25—C24—H24B	108.4	C47—C46—H46A	108.3
C23—C24—H24B	108.4	C45—C46—H46A	108.3
H24A—C24—H24B	107.5	C47—C46—H46B	108.3
C24—C25—C26	115.9 (18)	C45—C46—H46B	108.3
C24—C25—H25A	108.3	H46A—C46—H46B	107.4
C26—C25—H25A	108.3	C46—C47—C48	115.4 (19)
C24—C25—H25B	108.3	C46—C47—H47A	108.4
C26—C25—H25B	108.3	C48—C47—H47A	108.4
H25A—C25—H25B	107.4	C46—C47—H47B	108.4
C27—C26—C25	117 (2)	C48—C47—H47B	108.4
C27—C26—H26A	108.1	H47A—C47—H47B	107.5
C25—C26—H26A	108.1	C47—C48—H48A	109.5
C27—C26—H26B	108.1	C47—C48—H48B	109.5
C25—C26—H26B	108.1	H48A—C48—H48B	109.5
H26A—C26—H26B	107.3	C47—C48—H48C	109.5
C26—C27—C28	115 (2)	H48A—C48—H48C	109.5
C26—C27—H27A	108.4	H48B—C48—H48C	109.5
C6—C1—C2—C3	−0.6 (12)	C16—C17—C18—C19	−179.0 (12)
Br1—C1—C2—C3	176.0 (6)	C17—C18—C19—C20	179.7 (13)
C6—C1—C2—Br2	−178.2 (6)	C18—C19—C20—C21	180.0 (14)
Br1—C1—C2—Br2	−1.6 (10)	C19—C20—C21—C22	178.7 (16)
C1—C2—C3—C4	−0.2 (12)	C20—C21—C22—C23	178.5 (18)
Br2—C2—C3—C4	177.6 (6)	C21—C22—C23—C24	−179 (2)
C31—O2—C4—C3	17.1 (11)	C22—C23—C24—C25	−180 (2)
C31—O2—C4—C5	−160.7 (7)	C23—C24—C25—C26	−180 (2)
C2—C3—C4—O2	−176.3 (7)	C24—C25—C26—C27	−179 (3)
C2—C3—C4—C5	1.4 (12)	C25—C26—C27—C28	−177 (3)
C11—O1—C5—C6	−15.6 (12)	C4—O2—C31—C32	159.2 (7)
C11—O1—C5—C4	162.9 (7)	O2—C31—C32—C33	−61.6 (9)
O2—C4—C5—C6	176.0 (7)	C31—C32—C33—C34	−175.6 (7)
C3—C4—C5—C6	−1.8 (12)	C32—C33—C34—C35	−177.9 (8)
O2—C4—C5—O1	−2.6 (11)	C33—C34—C35—C36	179.4 (8)
C3—C4—C5—O1	179.6 (7)	C34—C35—C36—C37	−178.7 (9)
O1—C5—C6—C1	179.5 (8)	C35—C36—C37—C38	−179.4 (10)
C4—C5—C6—C1	1.0 (12)	C36—C37—C38—C39	180.0 (10)
C2—C1—C6—C5	0.2 (12)	C37—C38—C39—C40	178.0 (11)
Br1—C1—C6—C5	−176.5 (6)	C38—C39—C40—C41	−180.0 (12)
C5—O1—C11—C12	−176.1 (7)	C39—C40—C41—C42	−178.9 (12)
O1—C11—C12—C13	175.1 (7)	C40—C41—C42—C43	179.6 (14)
C11—C12—C13—C14	−179.1 (8)	C41—C42—C43—C44	−178.7 (16)
C12—C13—C14—C15	177.9 (9)	C42—C43—C44—C45	−178.6 (18)
C13—C14—C15—C16	179.7 (9)	C43—C44—C45—C46	178 (2)
C14—C15—C16—C17	−179.7 (10)	C44—C45—C46—C47	179 (2)
C15—C16—C17—C18	−177.8 (11)	C45—C46—C47—C48	−179 (2)