Diethyl 5-bromo-4,7-dimethoxy­indan-2,2-dicarboxyl­ate

The title compound, C₁₇H₂₁BrO₆, was prepared by nucleophilic alkyl­ation of 1-bromo-3,4-bis(bromomethyl)-2,5-di­methoxy­benzene. It crystallizes with two independent mol­ecules in the asymmetric unit. The bond lengths and angles are generally within the normal ranges. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds and weak C—H...π(arene) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 122 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.081
• Data-to-parameter ratio = 31.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.87 Ratio

Author Response: The large range in the Ueq(max)/Ueq(min) value is reasonable for this tructure because it is the peripheral carbon atoms which have the large values.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.21 Ratio

Author Response: The large range in the Ueq(max)/Ueq(min) value is reasonable for this tructure because it is the peripheral carbon atoms which have the large values.

PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.00 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C13A
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         40

Alert level G
ABSTY01_ALERT_1_G  Extra text has been found in the _exptl_absorpt_correction_type
            field, which should be only a single keyword. A literature
            citation should be included in the _exptl_absorpt_process_details
            field.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

The title compound, (I), was prepared for use as a building block in the syntheses of single-walled carbon nanotube (SWNT) interacting compounds. It crystallizes in the triclinic space group P1 with two independent molecules in the asymmetric unit (Fig. 1). The corresponding bond lengths and angles of the two molecules agree with each other, but the molecules differ in the orientations of the ester groups. In both molecules, one of the methoxy groups is coplanar with the benzene ring, while the other is almost perpendicular to the benzene ring (see torsions angles in Table 1) and the five-membered rings of the indan ring system adopt envelope conformations. The crystal packing of (I) is stabilized mainly by weak intermolecular C—H···O hydrogen bonds and weak C—H···π(arene) interactions (Table 2 and Fig. 2).

S2. Experimental

1-Bromo-3,4-bis(bromomethyl)-2,5-dimethoxybenzene (50 g, 0.12 mol), prepared as described by Hammershøj et al. (2005), was dissolved in dried tetrahydrofuran (800 ml) and NaH (80% suspension in oil, 14 g) was added. The reaction mixture was stirred under an N₂ atmosphere for 10 min at room temperature. Diethylmalonate (20 g, 0.2 mol) was dissolved in dried tetrahydrofuran (200 ml) and added over a 50 min period under an N₂ atmosphere. After 2 h, brine (800 ml) was added and the mixture was extracted with diethyl ether (3 × 200 ml). The combined organic extracts were dried with MgSO₄ and evaporated to dryness in vacuo yielding a pale green oil. Purification by crystallization in methanol yielded compound (I) as a white powder (30.2 g, 60%; m.p. 359–361 K); ¹H NMR (300 MHz, CDCl₃): δ 6.6 (1H, s), 4.15 (4H, s, J 7.14 Hz), 3.72 (3H, s), 3.7 (3H, s), 3.5 (2H, s), 3.4 (2H, s), 1.2 (6H, t); ¹³C NMR (100 MHz, CDCl₃): δ 170.2, 151.1, 145.9, 134.0, 128.1, 113.6, 112.8, 60.8, 59.4, 54.7, 37.4, 36.6, 12.9; m/e: 402 (71), 328 (100), 253 (94), 69(59.5) and 32 (87.5%); analysis calculated for C₁₇H₂₁BrO₆: C 50.89, H 5.28%; found: C 51.03, H 5.27%. [Omit ¹³C NMR from publication due to lack of assignments?]

S3. Refinement

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.95–0.99 Å and U_iso(H) = 1.2–1.5U_eq(C).

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of (I). C—H···O hydrogen bonds and C—H···π(arene) interactions are shown as brown lines.

Diethyl 5-bromo-4,7-dimethoxyindan-2,2-dicarboxylate

Crystal data

C17H21BrO6	Z = 4
Mr = 401.24	F(000) = 824
Triclinic, P1	Dx = 1.481 Mg m^−3
Hall symbol: -P 1	Melting point = 86–88 K
a = 11.1440 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1630 (7) Å	Cell parameters from 45017 reflections
c = 15.7690 (14) Å	θ = 1.4–33.0°
α = 75.782 (5)°	µ = 2.31 mm^−1
β = 77.534 (7)°	T = 122 K
γ = 73.395 (5)°	Prism, white
V = 1799.7 (2) Å^3	0.59 × 0.34 × 0.19 mm

Data collection

Nonius KappaCCD area-detector diffractometer	13426 independent reflections
Radiation source: fine-focus sealed tube	11251 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω and ϕ scans	θmax = 33.0°, θmin = 1.4°
Absorption correction: gaussian integration (Coppens, 1970)	h = −17→17
Tmin = 0.427, Tmax = 0.768	k = −17→16
72293 measured reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0247P)^2 + 1.4569P] where P = (Fo^2 + 2Fc^2)/3
13426 reflections	(Δ/σ)max = 0.002
433 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.65 e Å^−3

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
Br1B	0.369897 (13)	0.418763 (14)	−0.024836 (10)	0.01906 (4)
Br1A	0.619151 (16)	0.150871 (17)	0.464061 (13)	0.02890 (5)
O4B	−0.36276 (9)	0.92325 (10)	−0.06419 (7)	0.01613 (19)
O3A	−0.02489 (10)	0.71534 (11)	0.33896 (7)	0.0192 (2)
O3B	−0.22685 (10)	0.81749 (10)	−0.16557 (7)	0.01681 (19)
O1A	0.42439 (11)	0.30944 (11)	0.34134 (7)	0.0202 (2)
O5B	−0.18508 (12)	1.05739 (11)	0.01939 (7)	0.0214 (2)
O6B	−0.17127 (10)	1.09389 (9)	−0.12922 (6)	0.01437 (18)
O1B	0.24196 (10)	0.65731 (10)	−0.15150 (7)	0.01521 (18)
O2A	0.33824 (10)	0.49569 (10)	0.65124 (7)	0.0172 (2)
C8B	−0.14590 (12)	0.88055 (12)	−0.05577 (8)	0.0112 (2)
O2B	−0.07670 (10)	0.56274 (10)	0.16846 (6)	0.01503 (18)
C1A	0.36762 (13)	0.44428 (13)	0.57708 (9)	0.0127 (2)
C7A	0.17528 (14)	0.61475 (14)	0.51764 (9)	0.0162 (2)
H7AA	0.1958	0.6863	0.5335	0.019*
H7AB	0.1044	0.5895	0.5617	0.019*
C12B	−0.24713 (12)	0.86930 (12)	−0.10343 (9)	0.0119 (2)
C2A	0.46651 (13)	0.33836 (13)	0.56252 (9)	0.0150 (2)
H2A	0.5214	0.2968	0.6051	0.018*
C6B	−0.02936 (12)	0.68863 (12)	0.02915 (8)	0.0110 (2)
C1B	0.00871 (12)	0.58008 (12)	0.09288 (8)	0.0112 (2)
O6A	0.11175 (10)	0.87541 (10)	0.39525 (7)	0.01708 (19)
O5A	0.28954 (10)	0.76599 (11)	0.32194 (7)	0.0197 (2)
C5B	0.04917 (12)	0.71517 (12)	−0.05050 (8)	0.0106 (2)
C8A	0.14155 (13)	0.65201 (13)	0.42213 (9)	0.0131 (2)
C13B	−0.47135 (14)	0.92250 (15)	−0.10169 (10)	0.0194 (3)
H13BA	−0.5437	0.9132	−0.0537	0.023*
H13BB	−0.4495	0.8491	−0.1317	0.023*
C4B	0.16913 (12)	0.63488 (12)	−0.06958 (8)	0.0117 (2)
C2B	0.12871 (13)	0.49928 (13)	0.07637 (9)	0.0130 (2)
H2B	0.1572	0.4257	0.1192	0.016*
C5A	0.30858 (13)	0.45844 (13)	0.43537 (9)	0.0129 (2)
C9B	−0.00974 (12)	0.83843 (13)	−0.10749 (9)	0.0129 (2)
H9BA	−0.0132	0.8253	−0.1667	0.015*
H9BB	0.0388	0.9030	−0.1148	0.015*
C7B	−0.15124 (13)	0.79013 (13)	0.03702 (9)	0.0137 (2)
H7BA	−0.1558	0.8363	0.0842	0.016*
H7BB	−0.2254	0.7528	0.0501	0.016*
C12A	−0.00118 (13)	0.68641 (13)	0.42253 (9)	0.0153 (2)
C3B	0.20644 (12)	0.52853 (13)	−0.00446 (9)	0.0127 (2)
C4A	0.40568 (13)	0.35182 (13)	0.41946 (9)	0.0147 (2)
O4A	−0.08100 (11)	0.68666 (13)	0.48731 (8)	0.0273 (3)
C3A	0.48342 (13)	0.29438 (13)	0.48379 (10)	0.0160 (2)
C15B	−0.17139 (12)	1.01968 (13)	−0.04831 (9)	0.0126 (2)
C6A	0.28934 (12)	0.50391 (13)	0.51267 (8)	0.0123 (2)
C9A	0.21017 (14)	0.53489 (14)	0.37772 (9)	0.0157 (2)
H9AA	0.1501	0.4848	0.3771	0.019*
H9AB	0.2504	0.5622	0.3162	0.019*
C16B	−0.18867 (14)	1.23033 (13)	−0.13404 (10)	0.0156 (2)
H16BA	−0.1487	1.2687	−0.1929	0.019*
H16BB	−0.1465	1.2424	−0.0886	0.019*
C15A	0.19117 (13)	0.76898 (13)	0.37282 (9)	0.0140 (2)
C16A	0.14748 (16)	0.99388 (14)	0.35006 (11)	0.0213 (3)
H16AA	0.1609	1.0007	0.2851	0.026*
H16AB	0.2272	0.9958	0.3672	0.026*
C10A	0.41040 (15)	0.43277 (16)	0.72134 (10)	0.0210 (3)
H10AA	0.3804	0.4792	0.7702	0.025*
H10AB	0.5002	0.4304	0.6995	0.025*
H10AC	0.4001	0.3455	0.7424	0.025*
C10B	−0.04076 (15)	0.45055 (14)	0.23398 (9)	0.0185 (3)
H10BA	−0.1089	0.4489	0.2850	0.022*
H10BB	0.0370	0.4513	0.2531	0.022*
H10BC	−0.0258	0.3747	0.2086	0.022*
C11B	0.33152 (16)	0.73108 (16)	−0.15717 (11)	0.0241 (3)
H11BA	0.3792	0.7424	−0.2174	0.029*
H11BB	0.3903	0.6863	−0.1149	0.029*
H11BC	0.2860	0.8147	−0.1431	0.029*
C17B	−0.32748 (15)	1.29643 (15)	−0.11915 (11)	0.0210 (3)
H17BA	−0.3371	1.3875	−0.1226	0.025*
H17BB	−0.3668	1.2592	−0.0605	0.025*
H17BC	−0.3689	1.2856	−0.1647	0.025*
C13A	−0.15783 (15)	0.76139 (17)	0.32701 (12)	0.0238 (3)
H13AA	−0.2109	0.7190	0.3776	0.029*
H13AB	−0.1688	0.7403	0.2722	0.029*
C11A	0.35392 (19)	0.2173 (2)	0.34724 (13)	0.0322 (4)
H11AA	0.3707	0.1901	0.2903	0.039*
H11AB	0.2631	0.2557	0.3617	0.039*
H11AC	0.3799	0.1432	0.3937	0.039*
C17A	0.0414 (2)	1.10264 (16)	0.37687 (13)	0.0305 (4)
H17AA	0.0629	1.1836	0.3474	0.037*
H17AB	0.0292	1.0951	0.4412	0.037*
H17AC	−0.0369	1.1000	0.3594	0.037*
C14B	−0.50813 (18)	1.0445 (2)	−0.16707 (14)	0.0340 (4)
H14BA	−0.5808	1.0430	−0.1921	0.041*
H14BB	−0.4365	1.0531	−0.2147	0.041*
H14BC	−0.5310	1.1168	−0.1370	0.041*
C14A	−0.1991 (3)	0.9023 (2)	0.3211 (2)	0.0600 (8)
H14AA	−0.2883	0.9328	0.3130	0.072*
H14AB	−0.1469	0.9440	0.2707	0.072*
H14AC	−0.1891	0.9227	0.3758	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1B	0.01267 (6)	0.01661 (7)	0.02272 (7)	0.00240 (5)	−0.00023 (5)	−0.00366 (5)
Br1A	0.02201 (8)	0.02654 (9)	0.03630 (9)	0.00841 (6)	−0.00793 (7)	−0.01680 (7)
O4B	0.0109 (4)	0.0202 (5)	0.0180 (5)	−0.0007 (4)	−0.0031 (3)	−0.0079 (4)
O3A	0.0146 (5)	0.0253 (5)	0.0161 (5)	−0.0021 (4)	−0.0042 (4)	−0.0030 (4)
O3B	0.0196 (5)	0.0174 (5)	0.0150 (4)	−0.0044 (4)	−0.0026 (4)	−0.0063 (4)
O1A	0.0216 (5)	0.0236 (5)	0.0171 (5)	−0.0049 (4)	0.0010 (4)	−0.0117 (4)
O5B	0.0325 (6)	0.0178 (5)	0.0152 (5)	−0.0048 (4)	−0.0046 (4)	−0.0063 (4)
O6B	0.0190 (5)	0.0103 (4)	0.0129 (4)	−0.0018 (3)	−0.0033 (3)	−0.0023 (3)
O1B	0.0137 (4)	0.0181 (5)	0.0129 (4)	−0.0048 (4)	0.0030 (3)	−0.0050 (4)
O2A	0.0175 (5)	0.0206 (5)	0.0111 (4)	0.0012 (4)	−0.0034 (4)	−0.0045 (4)
C8B	0.0108 (5)	0.0112 (5)	0.0107 (5)	−0.0011 (4)	−0.0019 (4)	−0.0020 (4)
O2B	0.0146 (4)	0.0151 (4)	0.0108 (4)	−0.0012 (4)	0.0012 (3)	0.0001 (3)
C1A	0.0128 (5)	0.0139 (6)	0.0108 (5)	−0.0037 (4)	−0.0003 (4)	−0.0021 (4)
C7A	0.0191 (6)	0.0161 (6)	0.0102 (5)	0.0012 (5)	−0.0020 (5)	−0.0035 (5)
C12B	0.0125 (5)	0.0092 (5)	0.0129 (5)	−0.0021 (4)	−0.0025 (4)	−0.0002 (4)
C2A	0.0119 (5)	0.0158 (6)	0.0165 (6)	−0.0016 (5)	−0.0022 (4)	−0.0035 (5)
C6B	0.0097 (5)	0.0115 (5)	0.0117 (5)	−0.0019 (4)	−0.0014 (4)	−0.0033 (4)
C1B	0.0115 (5)	0.0114 (5)	0.0109 (5)	−0.0029 (4)	−0.0008 (4)	−0.0032 (4)
O6A	0.0183 (5)	0.0132 (4)	0.0172 (5)	−0.0047 (4)	0.0021 (4)	−0.0016 (4)
O5A	0.0138 (4)	0.0237 (5)	0.0189 (5)	−0.0046 (4)	0.0013 (4)	−0.0025 (4)
C5B	0.0104 (5)	0.0106 (5)	0.0111 (5)	−0.0026 (4)	−0.0012 (4)	−0.0029 (4)
C8A	0.0131 (5)	0.0134 (6)	0.0112 (5)	−0.0019 (4)	−0.0010 (4)	−0.0018 (4)
C13B	0.0128 (6)	0.0233 (7)	0.0240 (7)	−0.0049 (5)	−0.0053 (5)	−0.0052 (6)
C4B	0.0110 (5)	0.0121 (5)	0.0118 (5)	−0.0026 (4)	0.0001 (4)	−0.0035 (4)
C2B	0.0129 (5)	0.0113 (5)	0.0137 (5)	−0.0018 (4)	−0.0021 (4)	−0.0021 (4)
C5A	0.0138 (5)	0.0130 (6)	0.0113 (5)	−0.0039 (4)	−0.0003 (4)	−0.0019 (4)
C9B	0.0116 (5)	0.0125 (5)	0.0113 (5)	−0.0008 (4)	0.0003 (4)	−0.0007 (4)
C7B	0.0116 (5)	0.0143 (6)	0.0112 (5)	0.0002 (4)	0.0004 (4)	−0.0011 (4)
C12A	0.0154 (6)	0.0139 (6)	0.0162 (6)	−0.0049 (5)	−0.0018 (5)	−0.0015 (5)
C3B	0.0096 (5)	0.0111 (5)	0.0161 (6)	−0.0004 (4)	−0.0011 (4)	−0.0038 (4)
C4A	0.0138 (6)	0.0162 (6)	0.0145 (6)	−0.0039 (5)	0.0006 (4)	−0.0061 (5)
O4A	0.0180 (5)	0.0414 (7)	0.0196 (5)	−0.0100 (5)	0.0031 (4)	−0.0027 (5)
C3A	0.0120 (5)	0.0144 (6)	0.0207 (6)	−0.0008 (5)	−0.0009 (5)	−0.0064 (5)
C15B	0.0104 (5)	0.0132 (6)	0.0137 (5)	−0.0015 (4)	−0.0022 (4)	−0.0031 (4)
C6A	0.0127 (5)	0.0118 (5)	0.0109 (5)	−0.0027 (4)	−0.0005 (4)	−0.0012 (4)
C9A	0.0188 (6)	0.0160 (6)	0.0118 (5)	−0.0020 (5)	−0.0030 (5)	−0.0041 (5)
C16B	0.0175 (6)	0.0109 (5)	0.0185 (6)	−0.0039 (5)	−0.0034 (5)	−0.0021 (5)
C15A	0.0131 (5)	0.0162 (6)	0.0121 (5)	−0.0025 (5)	−0.0040 (4)	−0.0016 (4)
C16A	0.0249 (7)	0.0148 (6)	0.0226 (7)	−0.0089 (5)	−0.0005 (6)	0.0015 (5)
C10A	0.0225 (7)	0.0256 (7)	0.0137 (6)	−0.0006 (6)	−0.0067 (5)	−0.0044 (5)
C10B	0.0207 (6)	0.0192 (7)	0.0115 (6)	−0.0031 (5)	−0.0014 (5)	0.0015 (5)
C11B	0.0230 (7)	0.0251 (8)	0.0245 (7)	−0.0134 (6)	0.0095 (6)	−0.0084 (6)
C17B	0.0193 (7)	0.0161 (6)	0.0240 (7)	0.0008 (5)	−0.0023 (5)	−0.0044 (5)
C13A	0.0162 (6)	0.0285 (8)	0.0291 (8)	−0.0032 (6)	−0.0096 (6)	−0.0074 (6)
C11A	0.0347 (9)	0.0370 (10)	0.0347 (9)	−0.0137 (8)	−0.0025 (7)	−0.0219 (8)
C17A	0.0404 (10)	0.0156 (7)	0.0302 (8)	−0.0058 (7)	0.0028 (7)	−0.0035 (6)
C14B	0.0254 (8)	0.0381 (10)	0.0362 (10)	−0.0069 (7)	−0.0162 (7)	0.0058 (8)
C14A	0.0493 (14)	0.0354 (12)	0.101 (2)	0.0145 (10)	−0.0494 (15)	−0.0210 (13)

Geometric parameters (Å, º)

Br1B—C3B	1.8941 (13)	C2B—C3B	1.4008 (18)
Br1A—C3A	1.8994 (14)	C2B—H2B	0.95
O4B—C12B	1.3421 (16)	C5A—C6A	1.3850 (18)
O4B—C13B	1.4599 (17)	C5A—C4A	1.3943 (19)
O3A—C12A	1.3428 (17)	C5A—C9A	1.5072 (19)
O3A—C13A	1.4602 (18)	C9B—H9BA	0.99
O3B—C12B	1.2057 (16)	C9B—H9BB	0.99
O1A—C4A	1.3798 (17)	C7B—H7BA	0.99
O1A—C11A	1.438 (2)	C7B—H7BB	0.99
O5B—C15B	1.2058 (17)	C12A—O4A	1.2011 (18)
O6B—C15B	1.3397 (16)	C4A—C3A	1.390 (2)
O6B—C16B	1.4642 (17)	C9A—H9AA	0.99
O1B—C4B	1.3764 (16)	C9A—H9AB	0.99
O1B—C11B	1.4413 (18)	C16B—C17B	1.506 (2)
O2A—C1A	1.3642 (16)	C16B—H16BA	0.99
O2A—C10A	1.4287 (18)	C16B—H16BB	0.99
C8B—C15B	1.5263 (19)	C16A—C17A	1.505 (2)
C8B—C12B	1.5320 (18)	C16A—H16AA	0.99
C8B—C7B	1.5603 (18)	C16A—H16AB	0.99
C8B—C9B	1.5604 (18)	C10A—H10AA	0.98
O2B—C1B	1.3660 (16)	C10A—H10AB	0.98
O2B—C10B	1.4327 (17)	C10A—H10AC	0.98
C1A—C2A	1.3945 (19)	C10B—H10BA	0.98
C1A—C6A	1.3980 (19)	C10B—H10BB	0.98
C7A—C6A	1.5028 (19)	C10B—H10BC	0.98
C7A—C8A	1.5588 (19)	C11B—H11BA	0.98
C7A—H7AA	0.99	C11B—H11BB	0.98
C7A—H7AB	0.99	C11B—H11BC	0.98
C2A—C3A	1.401 (2)	C17B—H17BA	0.98
C2A—H2A	0.95	C17B—H17BB	0.98
C6B—C5B	1.3864 (17)	C17B—H17BC	0.98
C6B—C1B	1.3965 (18)	C13A—C14A	1.493 (3)
C6B—C7B	1.5036 (18)	C13A—H13AA	0.99
C1B—C2B	1.3947 (18)	C13A—H13AB	0.99
O6A—C15A	1.3380 (17)	C11A—H11AA	0.98
O6A—C16A	1.4597 (18)	C11A—H11AB	0.98
O5A—C15A	1.2080 (17)	C11A—H11AC	0.98
C5B—C4B	1.3982 (17)	C17A—H17AA	0.98
C5B—C9B	1.5043 (18)	C17A—H17AB	0.98
C8A—C12A	1.5249 (19)	C17A—H17AC	0.98
C8A—C15A	1.5308 (19)	C14B—H14BA	0.98
C8A—C9A	1.5594 (19)	C14B—H14BB	0.98
C13B—C14B	1.503 (2)	C14B—H14BC	0.98
C13B—H13BA	0.99	C14A—H14AA	0.98
C13B—H13BB	0.99	C14A—H14AB	0.98
C4B—C3B	1.3929 (18)	C14A—H14AC	0.98
C12B—O4B—C13B	117.25 (11)	C2A—C3A—Br1A	118.44 (11)
C12A—O3A—C13A	116.70 (12)	O5B—C15B—O6B	124.80 (13)
C4A—O1A—C11A	112.74 (12)	O5B—C15B—C8B	125.58 (12)
C15B—O6B—C16B	116.45 (11)	O6B—C15B—C8B	109.57 (11)
C4B—O1B—C11B	114.84 (11)	C5A—C6A—C1A	120.77 (12)
C1A—O2A—C10A	117.59 (11)	C5A—C6A—C7A	111.95 (12)
C15B—C8B—C12B	108.10 (10)	C1A—C6A—C7A	127.22 (12)
C15B—C8B—C7B	111.82 (11)	C5A—C9A—C8A	103.80 (11)
C12B—C8B—C7B	109.14 (11)	C5A—C9A—H9AA	111.0
C15B—C8B—C9B	109.16 (11)	C8A—C9A—H9AA	111.0
C12B—C8B—C9B	111.55 (10)	C5A—C9A—H9AB	111.0
C7B—C8B—C9B	107.10 (10)	C8A—C9A—H9AB	111.0
C1B—O2B—C10B	116.92 (11)	H9AA—C9A—H9AB	109.0
O2A—C1A—C2A	125.11 (12)	O6B—C16B—C17B	110.76 (12)
O2A—C1A—C6A	115.66 (12)	O6B—C16B—H16BA	109.5
C2A—C1A—C6A	119.22 (12)	C17B—C16B—H16BA	109.5
C6A—C7A—C8A	103.52 (10)	O6B—C16B—H16BB	109.5
C6A—C7A—H7AA	111.1	C17B—C16B—H16BB	109.5
C8A—C7A—H7AA	111.1	H16BA—C16B—H16BB	108.1
C6A—C7A—H7AB	111.1	O5A—C15A—O6A	124.40 (13)
C8A—C7A—H7AB	111.1	O5A—C15A—C8A	124.96 (13)
H7AA—C7A—H7AB	109.0	O6A—C15A—C8A	110.63 (11)
O3B—C12B—O4B	124.82 (12)	O6A—C16A—C17A	107.70 (13)
O3B—C12B—C8B	125.46 (12)	O6A—C16A—H16AA	110.2
O4B—C12B—C8B	109.70 (11)	C17A—C16A—H16AA	110.2
C1A—C2A—C3A	118.70 (13)	O6A—C16A—H16AB	110.2
C1A—C2A—H2A	120.6	C17A—C16A—H16AB	110.2
C3A—C2A—H2A	120.6	H16AA—C16A—H16AB	108.5
C5B—C6B—C1B	120.93 (12)	O2A—C10A—H10AA	109.5
C5B—C6B—C7B	112.25 (11)	O2A—C10A—H10AB	109.5
C1B—C6B—C7B	126.78 (11)	H10AA—C10A—H10AB	109.5
O2B—C1B—C2B	124.94 (12)	O2A—C10A—H10AC	109.5
O2B—C1B—C6B	115.95 (11)	H10AA—C10A—H10AC	109.5
C2B—C1B—C6B	119.10 (12)	H10AB—C10A—H10AC	109.5
C15A—O6A—C16A	115.50 (11)	O2B—C10B—H10BA	109.5
C6B—C5B—C4B	121.29 (12)	O2B—C10B—H10BB	109.5
C6B—C5B—C9B	111.63 (11)	H10BA—C10B—H10BB	109.5
C4B—C5B—C9B	127.05 (11)	O2B—C10B—H10BC	109.5
C12A—C8A—C15A	107.95 (11)	H10BA—C10B—H10BC	109.5
C12A—C8A—C7A	112.07 (11)	H10BB—C10B—H10BC	109.5
C15A—C8A—C7A	108.39 (11)	O1B—C11B—H11BA	109.5
C12A—C8A—C9A	111.49 (11)	O1B—C11B—H11BB	109.5
C15A—C8A—C9A	110.80 (11)	H11BA—C11B—H11BB	109.5
C7A—C8A—C9A	106.12 (11)	O1B—C11B—H11BC	109.5
O4B—C13B—C14B	110.00 (13)	H11BA—C11B—H11BC	109.5
O4B—C13B—H13BA	109.7	H11BB—C11B—H11BC	109.5
C14B—C13B—H13BA	109.7	C16B—C17B—H17BA	109.5
O4B—C13B—H13BB	109.7	C16B—C17B—H17BB	109.5
C14B—C13B—H13BB	109.7	H17BA—C17B—H17BB	109.5
H13BA—C13B—H13BB	108.2	C16B—C17B—H17BC	109.5
O1B—C4B—C3B	122.43 (12)	H17BA—C17B—H17BC	109.5
O1B—C4B—C5B	120.52 (12)	H17BB—C17B—H17BC	109.5
C3B—C4B—C5B	116.92 (12)	O3A—C13A—C14A	109.77 (15)
C1B—C2B—C3B	118.83 (12)	O3A—C13A—H13AA	109.7
C1B—C2B—H2B	120.6	C14A—C13A—H13AA	109.7
C3B—C2B—H2B	120.6	O3A—C13A—H13AB	109.7
C6A—C5A—C4A	121.30 (12)	C14A—C13A—H13AB	109.7
C6A—C5A—C9A	111.22 (12)	H13AA—C13A—H13AB	108.2
C4A—C5A—C9A	127.43 (12)	O1A—C11A—H11AA	109.5
C5B—C9B—C8B	104.20 (10)	O1A—C11A—H11AB	109.5
C5B—C9B—H9BA	110.9	H11AA—C11A—H11AB	109.5
C8B—C9B—H9BA	110.9	O1A—C11A—H11AC	109.5
C5B—C9B—H9BB	110.9	H11AA—C11A—H11AC	109.5
C8B—C9B—H9BB	110.9	H11AB—C11A—H11AC	109.5
H9BA—C9B—H9BB	108.9	C16A—C17A—H17AA	109.5
C6B—C7B—C8B	103.88 (10)	C16A—C17A—H17AB	109.5
C6B—C7B—H7BA	111.0	H17AA—C17A—H17AB	109.5
C8B—C7B—H7BA	111.0	C16A—C17A—H17AC	109.5
C6B—C7B—H7BB	111.0	H17AA—C17A—H17AC	109.5
C8B—C7B—H7BB	111.0	H17AB—C17A—H17AC	109.5
H7BA—C7B—H7BB	109.0	C13B—C14B—H14BA	109.5
O4A—C12A—O3A	124.68 (14)	C13B—C14B—H14BB	109.5
O4A—C12A—C8A	125.66 (13)	H14BA—C14B—H14BB	109.5
O3A—C12A—C8A	109.65 (11)	C13B—C14B—H14BC	109.5
C4B—C3B—C2B	122.90 (12)	H14BA—C14B—H14BC	109.5
C4B—C3B—Br1B	118.98 (10)	H14BB—C14B—H14BC	109.5
C2B—C3B—Br1B	118.12 (10)	C13A—C14A—H14AA	109.5
O1A—C4A—C3A	122.46 (13)	C13A—C14A—H14AB	109.5
O1A—C4A—C5A	120.31 (13)	H14AA—C14A—H14AB	109.5
C3A—C4A—C5A	117.20 (12)	C13A—C14A—H14AC	109.5
C4A—C3A—C2A	122.79 (13)	H14AA—C14A—H14AC	109.5
C4A—C3A—Br1A	118.77 (10)	H14AB—C14A—H14AC	109.5
C10A—O2A—C1A—C2A	−3.1 (2)	O1B—C4B—C3B—C2B	−174.67 (12)
C10A—O2A—C1A—C6A	175.94 (13)	C5B—C4B—C3B—C2B	1.2 (2)
C13B—O4B—C12B—O3B	−2.1 (2)	O1B—C4B—C3B—Br1B	5.94 (18)
C13B—O4B—C12B—C8B	179.38 (11)	C5B—C4B—C3B—Br1B	−178.14 (10)
C15B—C8B—C12B—O3B	130.40 (14)	C1B—C2B—C3B—C4B	−0.2 (2)
C7B—C8B—C12B—O3B	−107.76 (15)	C1B—C2B—C3B—Br1B	179.16 (10)
C9B—C8B—C12B—O3B	10.38 (18)	C11A—O1A—C4A—C3A	91.78 (18)
C15B—C8B—C12B—O4B	−51.13 (14)	C11A—O1A—C4A—C5A	−90.35 (17)
C7B—C8B—C12B—O4B	70.71 (13)	C6A—C5A—C4A—O1A	−178.95 (13)
C9B—C8B—C12B—O4B	−171.15 (11)	C9A—C5A—C4A—O1A	3.8 (2)
O2A—C1A—C2A—C3A	178.48 (13)	C6A—C5A—C4A—C3A	−1.0 (2)
C6A—C1A—C2A—C3A	−0.6 (2)	C9A—C5A—C4A—C3A	−178.18 (13)
C10B—O2B—C1B—C2B	−2.13 (19)	O1A—C4A—C3A—C2A	178.74 (13)
C10B—O2B—C1B—C6B	178.69 (12)	C5A—C4A—C3A—C2A	0.8 (2)
C5B—C6B—C1B—O2B	−179.36 (12)	O1A—C4A—C3A—Br1A	−0.82 (19)
C7B—C6B—C1B—O2B	2.87 (19)	C5A—C4A—C3A—Br1A	−178.76 (10)
C5B—C6B—C1B—C2B	1.41 (19)	C1A—C2A—C3A—C4A	0.0 (2)
C7B—C6B—C1B—C2B	−176.36 (13)	C1A—C2A—C3A—Br1A	179.52 (10)
C1B—C6B—C5B—C4B	−0.36 (19)	C16B—O6B—C15B—O5B	0.3 (2)
C7B—C6B—C5B—C4B	177.70 (12)	C16B—O6B—C15B—C8B	−177.28 (11)
C1B—C6B—C5B—C9B	−178.33 (12)	C12B—C8B—C15B—O5B	125.31 (15)
C7B—C6B—C5B—C9B	−0.27 (16)	C7B—C8B—C15B—O5B	5.15 (19)
C6A—C7A—C8A—C12A	139.70 (12)	C9B—C8B—C15B—O5B	−113.18 (15)
C6A—C7A—C8A—C15A	−101.27 (12)	C12B—C8B—C15B—O6B	−57.16 (13)
C6A—C7A—C8A—C9A	17.78 (14)	C7B—C8B—C15B—O6B	−177.32 (10)
C12B—O4B—C13B—C14B	−93.70 (16)	C9B—C8B—C15B—O6B	64.35 (13)
C11B—O1B—C4B—C3B	−89.85 (16)	C4A—C5A—C6A—C1A	0.4 (2)
C11B—O1B—C4B—C5B	94.38 (15)	C9A—C5A—C6A—C1A	178.00 (12)
C6B—C5B—C4B—O1B	175.06 (12)	C4A—C5A—C6A—C7A	−176.81 (13)
C9B—C5B—C4B—O1B	−7.3 (2)	C9A—C5A—C6A—C7A	0.83 (16)
C6B—C5B—C4B—C3B	−0.94 (19)	O2A—C1A—C6A—C5A	−178.72 (12)
C9B—C5B—C4B—C3B	176.70 (13)	C2A—C1A—C6A—C5A	0.4 (2)
O2B—C1B—C2B—C3B	179.74 (12)	O2A—C1A—C6A—C7A	−2.0 (2)
C6B—C1B—C2B—C3B	−1.11 (19)	C2A—C1A—C6A—C7A	177.13 (13)
C6B—C5B—C9B—C8B	−5.74 (14)	C8A—C7A—C6A—C5A	−11.90 (15)
C4B—C5B—C9B—C8B	176.43 (12)	C8A—C7A—C6A—C1A	171.15 (13)
C15B—C8B—C9B—C5B	130.49 (11)	C6A—C5A—C9A—C8A	10.63 (15)
C12B—C8B—C9B—C5B	−110.12 (12)	C4A—C5A—C9A—C8A	−171.92 (13)
C7B—C8B—C9B—C5B	9.24 (14)	C12A—C8A—C9A—C5A	−139.68 (11)
C5B—C6B—C7B—C8B	6.14 (15)	C15A—C8A—C9A—C5A	100.07 (12)
C1B—C6B—C7B—C8B	−175.93 (12)	C7A—C8A—C9A—C5A	−17.39 (14)
C15B—C8B—C7B—C6B	−128.90 (11)	C15B—O6B—C16B—C17B	−85.52 (15)
C12B—C8B—C7B—C6B	111.55 (12)	C16A—O6A—C15A—O5A	3.2 (2)
C9B—C8B—C7B—C6B	−9.35 (14)	C16A—O6A—C15A—C8A	−178.16 (12)
C13A—O3A—C12A—O4A	5.9 (2)	C12A—C8A—C15A—O5A	−139.96 (14)
C13A—O3A—C12A—C8A	−174.81 (12)	C7A—C8A—C15A—O5A	98.44 (16)
C15A—C8A—C12A—O4A	−118.83 (16)	C9A—C8A—C15A—O5A	−17.62 (19)
C7A—C8A—C12A—O4A	0.5 (2)	C12A—C8A—C15A—O6A	41.38 (14)
C9A—C8A—C12A—O4A	119.25 (16)	C7A—C8A—C15A—O6A	−80.21 (13)
C15A—C8A—C12A—O3A	61.86 (14)	C9A—C8A—C15A—O6A	163.72 (11)
C7A—C8A—C12A—O3A	−178.85 (11)	C15A—O6A—C16A—C17A	174.49 (13)
C9A—C8A—C12A—O3A	−60.06 (15)	C12A—O3A—C13A—C14A	86.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AB···O4A	0.99	2.44	2.850 (2)	104
C2A—H2A···O5A^i	0.95	2.46	3.369 (2)	160
C2B—H2B···O3B^ii	0.95	2.56	3.419 (2)	150
C13B—H13BB···O3B	0.99	2.36	2.717 (2)	100
C9B—H9BA···O3B	0.99	2.40	2.852 (2)	107
C7B—H7BA···O5B	0.99	2.38	2.849 (2)	108
C9A—H9AB···O5A	0.99	2.46	2.840 (2)	102
C16A—H16AA···O3B^iii	0.99	2.57	3.260 (2)	127
C10A—H10AA···O1B^iv	0.98	2.55	3.462 (2)	155
C10B—H10BA···O2A^v	0.98	2.49	3.381 (2)	150
C11B—H11BC···O5B^iii	0.98	2.57	3.427 (2)	146
C17B—H17BC···O5A^iii	0.98	2.59	3.352 (2)	134
C13A—H13AA···Cg1^v	0.99	2.82	3.799 (2)	171
C16B—H16BB···Cg2^iii	0.99	2.57	3.459 (2)	150

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z; (iv) x, y, z+1; (v) −x, −y+1, −z+1.