Di­spiro­[cyclo­propane-1,1′(2′H)-cyclo­buta­[b]­naphthalene-2′,1′′-cyclo­propane]-3′,8′-dione

The title compound, C₁₆H₁₂O₂, contains two independent mol­ecules in the asymmetric unit. In both mol­ecules, the benzo­quinone system is essentially planar and the cyclo­butene ring is coplanar with it; the cyclo­propyl planes are orthogonal to the cyclo­butene ring. The crystal packing is stabilized by C—H...O interactions as well as van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C3B    -   C4B      =       9.74 su

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C10B   in Main Residue .          ?
PLAT333_ALERT_2_C Large Av Benzene C-C Dist. C1A    -   C12A     =       1.45 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range    C1B    -   C12B     =       0.17 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.28
           From the CIF: _reflns_number_total               3147
           Count of symmetry unique reflns         3168
           Completeness (_total/calc)             99.34%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Dispiro[cyclopropane-1,1'(2'H)-cyclobuta[b]naphthalene-2',1''-cyclopropane] -3',8'-dione

Crystal data

C16H12O2	F(000) = 496
Mr = 236.26	Dx = 1.309 Mg m^−3
Monoclinic, P21	Melting point: 377-376 K K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.7281 (5) Å	Cell parameters from 4723 reflections
b = 8.2720 (4) Å	θ = 2.4–28.2°
c = 16.9772 (9) Å	µ = 0.09 mm^−1
β = 102.0473 (9)°	T = 293 K
V = 1198.74 (11) Å^3	Block, yellow
Z = 4	0.70 × 0.34 × 0.24 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3147 independent reflections
Radiation source: fine-focus sealed tube	2797 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→10
Tmin = 0.943, Tmax = 0.980	l = −22→18
7540 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 0.1341P] where P = (Fo^2 + 2Fc^2)/3
3147 reflections	(Δ/σ)max = 0.001
324 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.17 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
O1A	0.4316 (2)	0.9273 (2)	0.04930 (8)	0.0556 (4)
O2A	0.69988 (19)	0.9227 (3)	0.36950 (8)	0.0618 (5)
C1A	0.6100 (2)	1.0530 (3)	0.15811 (11)	0.0422 (4)
C2A	0.6529 (3)	1.1716 (3)	0.10926 (14)	0.0524 (5)
H2A	0.6093	1.1715	0.0544	0.063*
C3A	0.7598 (3)	1.2900 (3)	0.14117 (17)	0.0637 (6)
H3A	0.7891	1.3678	0.1076	0.076*
C4A	0.8234 (3)	1.2930 (3)	0.22332 (18)	0.0661 (7)
H4A	0.8937	1.3740	0.2447	0.079*
C5A	0.7828 (3)	1.1761 (3)	0.27331 (14)	0.0543 (6)
H5A	0.8264	1.1785	0.3282	0.065*
C6A	0.6770 (2)	1.0544 (3)	0.24214 (12)	0.0438 (4)
C7A	0.6422 (2)	0.9249 (3)	0.29724 (11)	0.0447 (5)
C8A	0.5375 (2)	0.7986 (3)	0.25666 (11)	0.0424 (4)
C9A	0.4657 (2)	0.6423 (3)	0.27142 (11)	0.0437 (4)
C10A	0.3963 (2)	0.6374 (3)	0.18020 (11)	0.0408 (4)
C11A	0.4740 (2)	0.7969 (3)	0.17626 (11)	0.0401 (4)
C12A	0.4971 (2)	0.9243 (3)	0.12045 (11)	0.0412 (4)
C13A	0.2399 (2)	0.5771 (3)	0.13621 (13)	0.0500 (5)
H13A	0.1830	0.6422	0.0922	0.060*
H13B	0.1748	0.5208	0.1672	0.060*
C14A	0.3866 (3)	0.4948 (3)	0.12468 (13)	0.0485 (5)
H14A	0.4183	0.5104	0.0737	0.058*
H14B	0.4101	0.3889	0.1487	0.058*
C15A	0.3892 (3)	0.5975 (4)	0.33999 (14)	0.0591 (6)
H15A	0.2888	0.5428	0.3271	0.071*
H15B	0.4024	0.6706	0.3856	0.071*
C16A	0.5312 (3)	0.5067 (3)	0.32665 (13)	0.0572 (6)
H16A	0.6296	0.5250	0.3643	0.069*
H16B	0.5160	0.3973	0.3059	0.069*
O1B	−0.0766 (2)	0.6523 (2)	0.31542 (10)	0.0602 (4)
O2B	0.2452 (3)	1.1503 (3)	0.21864 (12)	0.0793 (6)
C1B	−0.0311 (2)	0.8134 (3)	0.20593 (11)	0.0450 (5)
C2B	−0.1380 (3)	0.7243 (3)	0.14923 (14)	0.0567 (6)
H2B	−0.1970	0.6431	0.1665	0.068*
C3B	−0.1562 (3)	0.7562 (4)	0.06804 (16)	0.0723 (9)
H3B	−0.2275	0.6975	0.0304	0.087*
C4B	−0.0672 (4)	0.8763 (5)	0.04343 (13)	0.0824 (11)
H4B	−0.0773	0.8957	−0.0114	0.099*
C5B	0.0371 (4)	0.9691 (4)	0.09813 (14)	0.0702 (8)
H5B	0.0944	1.0508	0.0801	0.084*
C6B	0.0555 (3)	0.9387 (3)	0.18075 (12)	0.0503 (5)
C7B	0.1677 (3)	1.0429 (3)	0.23977 (14)	0.0519 (5)
C8B	0.1719 (2)	1.0013 (2)	0.32377 (12)	0.0422 (4)
C9B	0.2512 (2)	1.0433 (3)	0.40827 (12)	0.0423 (4)
C10B	0.1562 (2)	0.9059 (3)	0.43496 (10)	0.0380 (4)
C11B	0.0899 (2)	0.8799 (2)	0.34740 (10)	0.0371 (4)
C12B	−0.0131 (2)	0.7701 (3)	0.29325 (11)	0.0404 (4)
C13B	0.2040 (3)	0.7829 (3)	0.50079 (12)	0.0492 (5)
H13C	0.3036	0.7984	0.5379	0.059*
H13D	0.1754	0.6710	0.4885	0.059*
C14B	0.0744 (2)	0.9009 (3)	0.50456 (12)	0.0496 (5)
H14C	−0.0320	0.8599	0.4945	0.060*
H14D	0.0961	0.9873	0.5440	0.060*
C15B	0.4208 (3)	1.0856 (4)	0.43899 (16)	0.0627 (7)
H15C	0.4760	1.0317	0.4874	0.075*
H15D	0.4840	1.1083	0.3996	0.075*
C16B	0.2955 (3)	1.2051 (3)	0.44722 (17)	0.0599 (6)
H16C	0.2832	1.2998	0.4127	0.072*
H16D	0.2753	1.2231	0.5006	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0726 (10)	0.0553 (9)	0.0327 (6)	−0.0043 (8)	−0.0031 (6)	0.0021 (7)
O2A	0.0669 (10)	0.0743 (12)	0.0363 (7)	0.0117 (9)	−0.0070 (6)	−0.0110 (8)
C1A	0.0455 (9)	0.0392 (10)	0.0403 (9)	0.0103 (8)	0.0050 (7)	−0.0076 (8)
C2A	0.0645 (13)	0.0424 (12)	0.0498 (11)	0.0052 (10)	0.0105 (10)	−0.0072 (10)
C3A	0.0760 (16)	0.0433 (12)	0.0742 (16)	−0.0045 (12)	0.0212 (13)	−0.0089 (12)
C4A	0.0626 (14)	0.0467 (13)	0.0867 (19)	−0.0043 (11)	0.0098 (13)	−0.0242 (14)
C5A	0.0501 (11)	0.0527 (13)	0.0558 (12)	0.0085 (11)	0.0009 (9)	−0.0224 (11)
C6A	0.0418 (9)	0.0445 (11)	0.0435 (10)	0.0108 (9)	0.0049 (8)	−0.0134 (9)
C7A	0.0415 (9)	0.0551 (12)	0.0346 (8)	0.0152 (9)	0.0013 (7)	−0.0090 (9)
C8A	0.0423 (9)	0.0503 (11)	0.0328 (8)	0.0122 (9)	0.0040 (7)	−0.0014 (8)
C9A	0.0441 (10)	0.0524 (11)	0.0339 (8)	0.0142 (9)	0.0061 (7)	0.0044 (9)
C10A	0.0416 (9)	0.0445 (10)	0.0346 (9)	0.0088 (8)	0.0040 (7)	0.0023 (8)
C11A	0.0418 (9)	0.0434 (10)	0.0327 (8)	0.0078 (8)	0.0021 (7)	−0.0016 (8)
C12A	0.0476 (10)	0.0403 (10)	0.0340 (8)	0.0079 (9)	0.0049 (7)	−0.0024 (8)
C13A	0.0448 (10)	0.0493 (12)	0.0510 (11)	0.0056 (9)	−0.0013 (8)	−0.0030 (10)
C14A	0.0570 (12)	0.0430 (11)	0.0445 (10)	0.0078 (9)	0.0082 (9)	−0.0002 (9)
C15A	0.0616 (13)	0.0730 (17)	0.0458 (11)	0.0186 (12)	0.0186 (10)	0.0134 (11)
C16A	0.0653 (14)	0.0605 (14)	0.0449 (11)	0.0215 (12)	0.0093 (10)	0.0144 (11)
O1B	0.0685 (10)	0.0578 (10)	0.0544 (9)	−0.0237 (9)	0.0130 (7)	−0.0143 (8)
O2B	0.1065 (15)	0.0608 (12)	0.0802 (13)	−0.0141 (12)	0.0411 (11)	0.0120 (11)
C1B	0.0454 (10)	0.0484 (11)	0.0378 (9)	0.0180 (9)	0.0012 (8)	−0.0079 (8)
C2B	0.0513 (12)	0.0619 (14)	0.0497 (11)	0.0230 (11)	−0.0056 (9)	−0.0187 (11)
C3B	0.0782 (17)	0.082 (2)	0.0456 (12)	0.0396 (17)	−0.0130 (11)	−0.0165 (13)
C4B	0.115 (2)	0.092 (2)	0.0315 (10)	0.061 (2)	−0.0038 (12)	−0.0004 (13)
C5B	0.102 (2)	0.0625 (16)	0.0483 (13)	0.0354 (16)	0.0208 (13)	0.0129 (12)
C6B	0.0631 (12)	0.0484 (12)	0.0384 (9)	0.0229 (10)	0.0083 (9)	0.0024 (9)
C7B	0.0625 (13)	0.0450 (12)	0.0520 (12)	0.0087 (10)	0.0208 (10)	0.0080 (10)
C8B	0.0442 (10)	0.0372 (10)	0.0452 (10)	0.0020 (8)	0.0091 (8)	−0.0021 (8)
C9B	0.0366 (9)	0.0421 (10)	0.0480 (10)	−0.0031 (8)	0.0077 (7)	−0.0073 (9)
C10B	0.0348 (8)	0.0404 (10)	0.0364 (8)	0.0008 (8)	0.0021 (6)	−0.0040 (8)
C11B	0.0344 (8)	0.0386 (10)	0.0363 (8)	0.0022 (7)	0.0029 (7)	−0.0018 (7)
C12B	0.0355 (8)	0.0436 (11)	0.0406 (9)	0.0038 (8)	0.0045 (7)	−0.0087 (8)
C13B	0.0578 (12)	0.0477 (12)	0.0386 (10)	0.0028 (10)	0.0017 (8)	0.0002 (9)
C14B	0.0469 (10)	0.0599 (13)	0.0425 (9)	−0.0029 (10)	0.0103 (8)	−0.0067 (10)
C15B	0.0405 (10)	0.0726 (17)	0.0767 (16)	−0.0158 (11)	0.0158 (10)	−0.0321 (14)
C16B	0.0628 (14)	0.0474 (13)	0.0736 (15)	−0.0132 (11)	0.0236 (12)	−0.0192 (12)

Geometric parameters (Å, º)

O1A—C12A	1.224 (2)	O1B—C12B	1.219 (3)
O2A—C7A	1.225 (2)	O2B—C7B	1.215 (3)
C1A—C2A	1.385 (3)	C1B—C6B	1.401 (3)
C1A—C6A	1.424 (3)	C1B—C2B	1.402 (3)
C1A—C12A	1.500 (3)	C1B—C12B	1.501 (3)
C2A—C3A	1.383 (3)	C2B—C3B	1.380 (4)
C2A—H2A	0.93	C2B—H2B	0.93
C3A—C4A	1.390 (4)	C3B—C4B	1.379 (5)
C3A—H3A	0.93	C3B—H3B	0.93
C4A—C5A	1.381 (4)	C4B—C5B	1.388 (5)
C4A—H4A	0.93	C4B—H4B	0.93
C5A—C6A	1.394 (3)	C5B—C6B	1.401 (3)
C5A—H5A	0.93	C5B—H5B	0.93
C6A—C7A	1.494 (3)	C6B—C7B	1.516 (4)
C7A—C8A	1.463 (3)	C7B—C8B	1.460 (3)
C8A—C11A	1.362 (2)	C8B—C11B	1.343 (3)
C8A—C9A	1.480 (3)	C8B—C9B	1.498 (3)
C9A—C16A	1.497 (3)	C9B—C15B	1.505 (3)
C9A—C15A	1.504 (3)	C9B—C16B	1.508 (3)
C9A—C10A	1.541 (3)	C9B—C10B	1.531 (3)
C10A—C11A	1.491 (3)	C10B—C11B	1.494 (2)
C10A—C13A	1.498 (3)	C10B—C14B	1.503 (3)
C10A—C14A	1.501 (3)	C10B—C13B	1.504 (3)
C11A—C12A	1.459 (3)	C11B—C12B	1.460 (3)
C13A—C14A	1.499 (3)	C13B—C14B	1.506 (3)
C13A—H13A	0.97	C13B—H13C	0.9700
C13A—H13B	0.97	C13B—H13D	0.97
C14A—H14A	0.97	C14B—H14C	0.97
C14A—H14B	0.97	C14B—H14D	0.97
C15A—C16A	1.506 (3)	C15B—C16B	1.503 (4)
C15A—H15A	0.97	C15B—H15C	0.97
C15A—H15B	0.97	C15B—H15D	0.97
C16A—H16A	0.97	C16B—H16C	0.97
C16A—H16B	0.97	C16B—H16D	0.97
C2A—C1A—C6A	119.2 (2)	C6B—C1B—C2B	120.2 (2)
C2A—C1A—C12A	118.87 (18)	C6B—C1B—C12B	121.71 (18)
C6A—C1A—C12A	121.88 (19)	C2B—C1B—C12B	118.1 (2)
C3A—C2A—C1A	120.8 (2)	C3B—C2B—C1B	120.5 (3)
C3A—C2A—H2A	119.6	C3B—C2B—H2B	119.8
C1A—C2A—H2A	119.6	C1B—C2B—H2B	119.8
C2A—C3A—C4A	120.1 (3)	C4B—C3B—C2B	119.1 (3)
C2A—C3A—H3A	120.0	C4B—C3B—H3B	120.5
C4A—C3A—H3A	120.0	C2B—C3B—H3B	120.5
C5A—C4A—C3A	120.3 (2)	C3B—C4B—C5B	121.9 (2)
C5A—C4A—H4A	119.8	C3B—C4B—H4B	119.1
C3A—C4A—H4A	119.8	C5B—C4B—H4B	119.1
C4A—C5A—C6A	120.5 (2)	C4B—C5B—C6B	119.5 (3)
C4A—C5A—H5A	119.8	C4B—C5B—H5B	120.2
C6A—C5A—H5A	119.8	C6B—C5B—H5B	120.2
C5A—C6A—C1A	119.1 (2)	C5B—C6B—C1B	118.8 (2)
C5A—C6A—C7A	119.02 (19)	C5B—C6B—C7B	118.9 (2)
C1A—C6A—C7A	121.79 (19)	C1B—C6B—C7B	122.30 (17)
O2A—C7A—C8A	123.1 (2)	O2B—C7B—C8B	124.0 (2)
O2A—C7A—C6A	122.9 (2)	O2B—C7B—C6B	122.9 (2)
C8A—C7A—C6A	113.95 (16)	C8B—C7B—C6B	113.1 (2)
C11A—C8A—C7A	124.2 (2)	C11B—C8B—C7B	124.19 (19)
C11A—C8A—C9A	93.61 (17)	C11B—C8B—C9B	93.20 (16)
C7A—C8A—C9A	142.10 (18)	C7B—C8B—C9B	142.5 (2)
C8A—C9A—C16A	129.82 (19)	C8B—C9B—C15B	127.62 (18)
C8A—C9A—C15A	128.2 (2)	C8B—C9B—C16B	130.6 (2)
C16A—C9A—C15A	60.24 (15)	C15B—C9B—C16B	59.85 (16)
C8A—C9A—C10A	86.81 (15)	C8B—C9B—C10B	86.61 (14)
C16A—C9A—C10A	128.9 (2)	C15B—C9B—C10B	128.7 (2)
C15A—C9A—C10A	128.81 (19)	C16B—C9B—C10B	129.42 (18)
C11A—C10A—C13A	130.37 (18)	C11B—C10B—C14B	129.01 (16)
C11A—C10A—C14A	129.32 (17)	C11B—C10B—C13B	129.18 (18)
C13A—C10A—C14A	59.96 (15)	C14B—C10B—C13B	60.08 (15)
C11A—C10A—C9A	86.26 (16)	C11B—C10B—C9B	86.20 (14)
C13A—C10A—C9A	129.47 (18)	C14B—C10B—C9B	128.94 (18)
C14A—C10A—C9A	127.62 (18)	C13B—C10B—C9B	129.68 (16)
C8A—C11A—C12A	124.1 (2)	C8B—C11B—C12B	124.99 (17)
C8A—C11A—C10A	93.29 (17)	C8B—C11B—C10B	93.99 (16)
C12A—C11A—C10A	142.55 (17)	C12B—C11B—C10B	140.88 (18)
O1A—C12A—C11A	123.8 (2)	O1B—C12B—C11B	124.22 (18)
O1A—C12A—C1A	122.39 (19)	O1B—C12B—C1B	122.32 (19)
C11A—C12A—C1A	113.79 (16)	C11B—C12B—C1B	113.44 (18)
C10A—C13A—C14A	60.13 (14)	C10B—C13B—C14B	59.93 (14)
C10A—C13A—H13A	117.8	C10B—C13B—H13C	117.8
C14A—C13A—H13A	117.8	C14B—C13B—H13C	117.8
C10A—C13A—H13B	117.8	C10B—C13B—H13D	117.8
C14A—C13A—H13B	117.8	C14B—C13B—H13D	117.8
H13A—C13A—H13B	114.9	H13C—C13B—H13D	114.9
C13A—C14A—C10A	59.91 (14)	C10B—C14B—C13B	59.99 (13)
C13A—C14A—H14A	117.8	C10B—C14B—H14C	117.8
C10A—C14A—H14A	117.8	C13B—C14B—H14C	117.8
C13A—C14A—H14B	117.8	C10B—C14B—H14D	117.8
C10A—C14A—H14B	117.8	C13B—C14B—H14D	117.8
H14A—C14A—H14B	114.9	H14C—C14B—H14D	114.9
C9A—C15A—C16A	59.66 (14)	C16B—C15B—C9B	60.18 (15)
C9A—C15A—H15A	117.8	C16B—C15B—H15C	117.8
C16A—C15A—H15A	117.8	C9B—C15B—H15C	117.8
C9A—C15A—H15B	117.8	C16B—C15B—H15D	117.8
C16A—C15A—H15B	117.8	C9B—C15B—H15D	117.8
H15A—C15A—H15B	114.9	H15C—C15B—H15D	114.9
C9A—C16A—C15A	60.10 (14)	C15B—C16B—C9B	59.97 (15)
C9A—C16A—H16A	117.8	C15B—C16B—H16C	117.8
C15A—C16A—H16A	117.8	C9B—C16B—H16C	117.8
C9A—C16A—H16B	117.8	C15B—C16B—H16D	117.8
C15A—C16A—H16B	117.8	C9B—C16B—H16D	117.8
H16A—C16A—H16B	114.9	H16C—C16B—H16D	114.9
C6A—C1A—C2A—C3A	0.2 (3)	C6B—C1B—C2B—C3B	1.7 (3)
C12A—C1A—C2A—C3A	−178.2 (2)	C12B—C1B—C2B—C3B	−178.31 (19)
C1A—C2A—C3A—C4A	−1.2 (4)	C1B—C2B—C3B—C4B	0.3 (3)
C2A—C3A—C4A—C5A	1.3 (4)	C2B—C3B—C4B—C5B	−1.8 (4)
C3A—C4A—C5A—C6A	−0.4 (4)	C3B—C4B—C5B—C6B	1.2 (4)
C4A—C5A—C6A—C1A	−0.6 (3)	C4B—C5B—C6B—C1B	0.8 (3)
C4A—C5A—C6A—C7A	176.8 (2)	C4B—C5B—C6B—C7B	−179.0 (2)
C2A—C1A—C6A—C5A	0.7 (3)	C2B—C1B—C6B—C5B	−2.2 (3)
C12A—C1A—C6A—C5A	179.10 (18)	C12B—C1B—C6B—C5B	177.8 (2)
C2A—C1A—C6A—C7A	−176.64 (18)	C2B—C1B—C6B—C7B	177.5 (2)
C12A—C1A—C6A—C7A	1.7 (3)	C12B—C1B—C6B—C7B	−2.5 (3)
C5A—C6A—C7A—O2A	1.8 (3)	C5B—C6B—C7B—O2B	−1.4 (3)
C1A—C6A—C7A—O2A	179.17 (19)	C1B—C6B—C7B—O2B	178.8 (2)
C5A—C6A—C7A—C8A	−176.25 (18)	C5B—C6B—C7B—C8B	178.3 (2)
C1A—C6A—C7A—C8A	1.1 (3)	C1B—C6B—C7B—C8B	−1.5 (3)
O2A—C7A—C8A—C11A	−178.86 (19)	O2B—C7B—C8B—C11B	−178.0 (2)
C6A—C7A—C8A—C11A	−0.8 (3)	C6B—C7B—C8B—C11B	2.2 (3)
O2A—C7A—C8A—C9A	−2.2 (4)	O2B—C7B—C8B—C9B	−2.9 (4)
C6A—C7A—C8A—C9A	175.8 (2)	C6B—C7B—C8B—C9B	177.3 (2)
C11A—C8A—C9A—C16A	141.8 (2)	C11B—C8B—C9B—C15B	137.6 (2)
C7A—C8A—C9A—C16A	−35.4 (4)	C7B—C8B—C9B—C15B	−38.3 (4)
C11A—C8A—C9A—C15A	−137.8 (2)	C11B—C8B—C9B—C16B	−142.5 (2)
C7A—C8A—C9A—C15A	45.0 (4)	C7B—C8B—C9B—C16B	41.6 (4)
C11A—C8A—C9A—C10A	1.20 (15)	C11B—C8B—C9B—C10B	−0.55 (15)
C7A—C8A—C9A—C10A	−176.0 (3)	C7B—C8B—C9B—C10B	−176.5 (3)
C8A—C9A—C10A—C11A	−1.09 (13)	C8B—C9B—C10B—C11B	0.50 (13)
C16A—C9A—C10A—C11A	−142.3 (2)	C15B—C9B—C10B—C11B	−136.9 (2)
C15A—C9A—C10A—C11A	137.5 (2)	C16B—C9B—C10B—C11B	143.2 (2)
C8A—C9A—C10A—C13A	−143.0 (2)	C8B—C9B—C10B—C14B	−138.7 (2)
C16A—C9A—C10A—C13A	75.8 (3)	C15B—C9B—C10B—C14B	83.9 (3)
C15A—C9A—C10A—C13A	−4.5 (4)	C16B—C9B—C10B—C14B	3.9 (3)
C8A—C9A—C10A—C14A	137.6 (2)	C8B—C9B—C10B—C13B	140.6 (2)
C16A—C9A—C10A—C14A	−3.6 (3)	C15B—C9B—C10B—C13B	3.2 (3)
C15A—C9A—C10A—C14A	−83.8 (3)	C16B—C9B—C10B—C13B	−76.7 (3)
C7A—C8A—C11A—C12A	−2.5 (3)	C7B—C8B—C11B—C12B	1.1 (3)
C9A—C8A—C11A—C12A	179.54 (18)	C9B—C8B—C11B—C12B	−175.90 (18)
C7A—C8A—C11A—C10A	176.69 (18)	C7B—C8B—C11B—C10B	177.6 (2)
C9A—C8A—C11A—C10A	−1.24 (15)	C9B—C8B—C11B—C10B	0.57 (15)
C13A—C10A—C11A—C8A	142.5 (2)	C14B—C10B—C11B—C8B	138.6 (2)
C14A—C10A—C11A—C8A	−136.3 (2)	C13B—C10B—C11B—C8B	−141.0 (2)
C9A—C10A—C11A—C8A	1.19 (14)	C9B—C10B—C11B—C8B	−0.56 (15)
C13A—C10A—C11A—C12A	−38.6 (4)	C14B—C10B—C11B—C12B	−46.0 (4)
C14A—C10A—C11A—C12A	42.6 (4)	C13B—C10B—C11B—C12B	34.4 (4)
C9A—C10A—C11A—C12A	−179.9 (3)	C9B—C10B—C11B—C12B	174.9 (2)
C8A—C11A—C12A—O1A	−175.0 (2)	C8B—C11B—C12B—O1B	173.6 (2)
C10A—C11A—C12A—O1A	6.2 (4)	C10B—C11B—C12B—O1B	−0.8 (4)
C8A—C11A—C12A—C1A	5.1 (3)	C8B—C11B—C12B—C1B	−4.9 (3)
C10A—C11A—C12A—C1A	−173.6 (2)	C10B—C11B—C12B—C1B	−179.3 (2)
C2A—C1A—C12A—O1A	−6.1 (3)	C6B—C1B—C12B—O1B	−173.1 (2)
C6A—C1A—C12A—O1A	175.48 (19)	C2B—C1B—C12B—O1B	6.9 (3)
C2A—C1A—C12A—C11A	173.75 (18)	C6B—C1B—C12B—C11B	5.4 (3)
C6A—C1A—C12A—C11A	−4.6 (3)	C2B—C1B—C12B—C11B	−174.57 (17)
C11A—C10A—C13A—C14A	118.0 (2)	C11B—C10B—C13B—C14B	−117.9 (2)
C9A—C10A—C13A—C14A	−115.9 (3)	C9B—C10B—C13B—C14B	117.7 (2)
C11A—C10A—C14A—C13A	−119.6 (2)	C11B—C10B—C14B—C13B	118.2 (2)
C9A—C10A—C14A—C13A	118.8 (2)	C9B—C10B—C14B—C13B	−118.8 (2)
C8A—C9A—C15A—C16A	−119.3 (2)	C8B—C9B—C15B—C16B	120.2 (3)
C10A—C9A—C15A—C16A	118.0 (3)	C10B—C9B—C15B—C16B	−118.4 (2)
C8A—C9A—C16A—C15A	116.8 (3)	C8B—C9B—C16B—C15B	−115.6 (3)
C10A—C9A—C16A—C15A	−117.8 (3)	C10B—C9B—C16B—C15B	117.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4A···O1B^i	0.93	2.58	3.387 (3)	145
C15B—H15D···O2A	0.97	2.56	3.216 (3)	125

Symmetry code: (i) x+1, y+1, z.