2-Oxo-2H-chromen-4-yl 4-methyl-benzoate.

The asymmetric unit of the title compound, C17H12O4, consists of two independent mol-ecules. The chromen-2-one ring and the 4-methyl-benzoate side chain are inclined to one another at a dihedral angle of 64.79 (10)° in one mol-ecule and 88.3 (1)° in the other. In the crystal, mol-ecules form R 2 (2)(8) centrosymmetric dimers via C-H⋯O hydrogen bonds. These dimers are stacked by C-H⋯O hydrogen bonds, resulting in R 2 (2)(18) and R 3 (2)(16) ring motifs. π-π stacking inter-actions between two parallel chromen-2-one rings, with centroid-centroid distances of 3.743 (1) and 3.771 (1) Å, are also present.

Related literature

For related structures and background to coumarin derivatives, see: Abou et al. (2011 ▶, 2012a ▶,b ▶). For the biological activity of coumarin derivatives, see: Basanagouda et al. (2009 ▶); Vukovic et al. (2010 ▶); Emmanuel-Giota et al. (2001 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶). For π–π stacking inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

C17H12O4

M = 280.27

Triclinic,

a = 9.2790 (5) Å

b = 10.7696 (5) Å

c = 14.5758 (9) Å

α = 95.274 (2)°

β = 97.875 (2)°

γ = 104.788 (5)°

V = 1382.75 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.35 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

16045 measured reflections

6907 independent reflections

3981 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.193

S = 1.02

6907 reflections

381 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813015717/sj5325sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015717/sj5325Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015717/sj5325Isup3.cml

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

C17H12O4	Z = 4
Mr = 280.27	F(000) = 584
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Melting point: 393 K
a = 9.2790 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7696 (5) Å	Cell parameters from 16045 reflections
c = 14.5758 (9) Å	θ = 2.3–29.0°
α = 95.274 (2)°	µ = 0.10 mm−1
β = 97.875 (2)°	T = 298 K
γ = 104.788 (5)°	Prism, colourless
V = 1382.75 (13) Å3	0.35 × 0.20 × 0.20 mm

Nonius KappaCCD diffractometer	3981 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 29.0°, θmin = 2.3°
φ and ω scans	h = 0→12
16045 measured reflections	k = −14→13
6907 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.5338P] where P = (Fo2 + 2Fc2)/3
6907 reflections	(Δ/σ)max < 0.001
381 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 e Å−3
96 constraints

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O3A	0.11504 (16)	0.06541 (13)	0.19401 (10)	0.0531 (4)
O1A	0.01309 (17)	0.34133 (13)	0.03537 (10)	0.0563 (4)
O3B	0.59037 (18)	0.04620 (14)	0.18431 (10)	0.0586 (4)
O1B	0.48955 (17)	0.32568 (14)	0.02929 (10)	0.0571 (4)
C6A	0.1773 (2)	0.28926 (19)	0.16105 (14)	0.0465 (5)
C7A	0.0784 (2)	0.16012 (18)	0.14343 (14)	0.0470 (5)
O4A	0.0360 (2)	0.14818 (16)	0.31869 (12)	0.0733 (5)
O4B	0.4891 (2)	0.11458 (17)	0.30383 (12)	0.0769 (5)
C8A	−0.0434 (2)	0.1250 (2)	0.07677 (14)	0.0529 (5)
H8A	−0.1043	0.0402	0.0675	0.063*
O2B	0.28103 (19)	0.18531 (17)	−0.04626 (11)	0.0718 (5)
C11B	0.5954 (2)	−0.06380 (19)	0.31683 (14)	0.0475 (5)
C1A	0.1380 (2)	0.37749 (19)	0.10450 (14)	0.0486 (5)
O2A	−0.1896 (2)	0.19687 (17)	−0.04247 (11)	0.0747 (5)
C6B	0.6536 (2)	0.26919 (19)	0.15259 (14)	0.0485 (5)
C12A	0.1485 (2)	−0.1468 (2)	0.27689 (16)	0.0554 (5)
H12A	0.1548	−0.1467	0.2138	0.066*
C12B	0.6854 (2)	−0.1337 (2)	0.28147 (16)	0.0569 (5)
H12B	0.7191	−0.1180	0.2253	0.068*
C11A	0.1175 (2)	−0.04418 (19)	0.32675 (14)	0.0474 (5)
C8B	0.4294 (2)	0.1088 (2)	0.06938 (15)	0.0546 (5)
H8B	0.3672	0.0245	0.0597	0.065*
C5B	0.7849 (3)	0.3096 (2)	0.21943 (16)	0.0602 (6)
H5B	0.8122	0.2515	0.2572	0.072*
C10A	0.0850 (2)	0.0663 (2)	0.28306 (15)	0.0505 (5)
C7B	0.5523 (2)	0.14119 (19)	0.13453 (14)	0.0488 (5)
C10B	0.5508 (2)	0.0404 (2)	0.27117 (15)	0.0519 (5)
C9A	−0.0812 (3)	0.2178 (2)	0.01896 (15)	0.0550 (5)
C14B	0.6753 (3)	−0.2549 (2)	0.41256 (17)	0.0625 (6)
C5A	0.3081 (2)	0.3320 (2)	0.22844 (16)	0.0570 (5)
H5A	0.3369	0.2749	0.2666	0.068*
C2B	0.7047 (3)	0.4859 (2)	0.10754 (17)	0.0621 (6)
H2B	0.6776	0.5449	0.0706	0.075*
C14A	0.1632 (3)	−0.2525 (2)	0.41558 (18)	0.0642 (6)
C2A	0.2240 (3)	0.5053 (2)	0.11509 (17)	0.0607 (6)
H2A	0.1958	0.5634	0.0776	0.073*
C13A	0.1701 (3)	−0.2502 (2)	0.32218 (18)	0.0647 (6)
H13A	0.1897	−0.3198	0.2883	0.078*
C13B	0.7251 (3)	−0.2278 (2)	0.33042 (18)	0.0672 (6)
H13B	0.7873	−0.2738	0.3069	0.081*
C1B	0.6160 (2)	0.3591 (2)	0.09711 (15)	0.0504 (5)
C16A	0.1124 (3)	−0.0446 (2)	0.42087 (16)	0.0614 (6)
H16A	0.0937	0.0252	0.4550	0.074*
C16B	0.5426 (3)	−0.0917 (2)	0.39887 (16)	0.0645 (6)
H16B	0.4793	−0.0467	0.4222	0.077*
C9B	0.3917 (3)	0.2034 (2)	0.01344 (15)	0.0553 (5)
C15B	0.5834 (3)	−0.1862 (2)	0.44628 (18)	0.0704 (7)
H15B	0.5482	−0.2034	0.5018	0.084*
C15A	0.1347 (3)	−0.1482 (2)	0.46484 (17)	0.0669 (6)
H15A	0.1305	−0.1475	0.5283	0.080*
C3A	0.3513 (3)	0.5444 (2)	0.18176 (19)	0.0688 (7)
H3A	0.4100	0.6299	0.1894	0.083*
C3B	0.8335 (3)	0.5225 (2)	0.17352 (19)	0.0710 (7)
H3B	0.8947	0.6071	0.1809	0.085*
C4A	0.3943 (3)	0.4586 (2)	0.23823 (18)	0.0676 (6)
H4A	0.4816	0.4868	0.2828	0.081*
C4B	0.8738 (3)	0.4349 (3)	0.22938 (18)	0.0706 (7)
H4B	0.9615	0.4613	0.2738	0.085*
C17A	0.1883 (4)	−0.3653 (3)	0.4641 (2)	0.0970 (10)
H17A	0.2489	−0.4077	0.4311	0.145*
H17B	0.0925	−0.4256	0.4650	0.145*
H17C	0.2394	−0.3341	0.5270	0.145*
C17B	0.7220 (4)	−0.3568 (3)	0.4659 (2)	0.0941 (10)
H17D	0.7936	−0.3151	0.5209	0.141*
H17E	0.7674	−0.4073	0.4270	0.141*
H17F	0.6346	−0.4124	0.4837	0.141*

	U11	U22	U33	U12	U13	U23
O3A	0.0750 (9)	0.0470 (8)	0.0501 (8)	0.0318 (7)	0.0174 (7)	0.0181 (6)
O1A	0.0718 (10)	0.0490 (8)	0.0528 (9)	0.0237 (7)	0.0061 (7)	0.0169 (7)
O3B	0.0833 (10)	0.0533 (9)	0.0554 (9)	0.0381 (8)	0.0204 (8)	0.0221 (7)
O1B	0.0677 (9)	0.0519 (9)	0.0574 (9)	0.0229 (7)	0.0080 (7)	0.0205 (7)
C6A	0.0551 (11)	0.0456 (11)	0.0471 (11)	0.0241 (9)	0.0141 (9)	0.0115 (9)
C7A	0.0635 (12)	0.0413 (10)	0.0463 (11)	0.0256 (9)	0.0162 (9)	0.0140 (9)
O4A	0.1083 (13)	0.0706 (11)	0.0678 (11)	0.0547 (10)	0.0364 (10)	0.0261 (9)
O4B	0.1064 (14)	0.0820 (12)	0.0737 (11)	0.0626 (11)	0.0372 (10)	0.0318 (9)
C8A	0.0674 (13)	0.0441 (11)	0.0502 (12)	0.0188 (10)	0.0094 (10)	0.0115 (9)
O2B	0.0790 (11)	0.0765 (11)	0.0596 (10)	0.0251 (9)	−0.0017 (8)	0.0161 (8)
C11B	0.0487 (11)	0.0442 (11)	0.0519 (12)	0.0155 (8)	0.0060 (9)	0.0138 (9)
C1A	0.0587 (12)	0.0449 (11)	0.0498 (12)	0.0225 (9)	0.0149 (9)	0.0119 (9)
O2A	0.0893 (12)	0.0706 (11)	0.0604 (10)	0.0251 (9)	−0.0104 (9)	0.0129 (8)
C6B	0.0564 (12)	0.0506 (11)	0.0477 (12)	0.0250 (9)	0.0162 (9)	0.0125 (9)
C12A	0.0650 (13)	0.0490 (12)	0.0562 (13)	0.0203 (10)	0.0103 (10)	0.0140 (10)
C12B	0.0660 (13)	0.0522 (12)	0.0602 (14)	0.0251 (10)	0.0145 (10)	0.0158 (10)
C11A	0.0491 (11)	0.0452 (11)	0.0508 (12)	0.0149 (8)	0.0086 (9)	0.0148 (9)
C8B	0.0677 (13)	0.0468 (11)	0.0533 (13)	0.0199 (10)	0.0119 (10)	0.0123 (10)
C5B	0.0610 (13)	0.0673 (15)	0.0591 (14)	0.0270 (11)	0.0110 (10)	0.0140 (11)
C10A	0.0589 (12)	0.0484 (11)	0.0517 (12)	0.0217 (9)	0.0149 (9)	0.0152 (9)
C7B	0.0637 (13)	0.0470 (11)	0.0472 (11)	0.0276 (9)	0.0174 (9)	0.0162 (9)
C10B	0.0575 (12)	0.0504 (12)	0.0546 (13)	0.0233 (10)	0.0106 (9)	0.0143 (10)
C9A	0.0690 (14)	0.0524 (12)	0.0471 (12)	0.0231 (10)	0.0072 (10)	0.0090 (10)
C14B	0.0656 (14)	0.0467 (12)	0.0716 (16)	0.0135 (10)	−0.0054 (11)	0.0204 (11)
C5A	0.0583 (13)	0.0593 (13)	0.0599 (14)	0.0260 (10)	0.0098 (10)	0.0126 (11)
C2B	0.0731 (15)	0.0505 (13)	0.0728 (16)	0.0234 (11)	0.0255 (12)	0.0200 (11)
C14A	0.0637 (14)	0.0551 (13)	0.0766 (17)	0.0160 (10)	0.0061 (11)	0.0320 (12)
C2A	0.0721 (15)	0.0469 (12)	0.0719 (15)	0.0225 (11)	0.0234 (12)	0.0182 (11)
C13A	0.0791 (16)	0.0478 (12)	0.0753 (17)	0.0274 (11)	0.0139 (12)	0.0184 (11)
C13B	0.0781 (16)	0.0569 (14)	0.0772 (17)	0.0353 (12)	0.0106 (13)	0.0181 (12)
C1B	0.0556 (12)	0.0502 (12)	0.0532 (12)	0.0227 (9)	0.0155 (9)	0.0131 (9)
C16A	0.0754 (15)	0.0605 (14)	0.0558 (14)	0.0235 (11)	0.0196 (11)	0.0188 (11)
C16B	0.0726 (15)	0.0713 (15)	0.0614 (15)	0.0323 (12)	0.0185 (11)	0.0223 (12)
C9B	0.0672 (14)	0.0572 (13)	0.0475 (12)	0.0255 (11)	0.0108 (10)	0.0114 (10)
C15B	0.0786 (16)	0.0749 (16)	0.0636 (15)	0.0232 (13)	0.0127 (12)	0.0314 (13)
C15A	0.0760 (16)	0.0719 (16)	0.0582 (14)	0.0212 (12)	0.0132 (11)	0.0303 (12)
C3A	0.0692 (15)	0.0485 (13)	0.0898 (19)	0.0136 (11)	0.0226 (13)	0.0077 (12)
C3B	0.0689 (15)	0.0584 (14)	0.0841 (18)	0.0114 (12)	0.0204 (13)	0.0054 (13)
C4A	0.0573 (14)	0.0634 (15)	0.0784 (17)	0.0145 (11)	0.0062 (11)	0.0032 (12)
C4B	0.0609 (14)	0.0757 (17)	0.0711 (17)	0.0152 (12)	0.0066 (12)	0.0042 (13)
C17A	0.110 (2)	0.0798 (19)	0.114 (2)	0.0353 (17)	0.0117 (18)	0.0591 (18)
C17B	0.113 (2)	0.0727 (18)	0.100 (2)	0.0330 (16)	−0.0055 (18)	0.0416 (16)

O3A—C10A	1.364 (2)	C5B—C4B	1.374 (3)
O3A—C7A	1.395 (2)	C5B—H5B	0.9300
O1A—C9A	1.372 (3)	C14B—C13B	1.371 (3)
O1A—C1A	1.374 (3)	C14B—C15B	1.374 (3)
O3B—C10B	1.368 (2)	C14B—C17B	1.518 (3)
O3B—C7B	1.396 (2)	C5A—C4A	1.377 (3)
O1B—C1B	1.373 (3)	C5A—H5A	0.9300
O1B—C9B	1.374 (3)	C2B—C3B	1.373 (3)
C6A—C1A	1.397 (3)	C2B—C1B	1.384 (3)
C6A—C5A	1.398 (3)	C2B—H2B	0.9300
C6A—C7A	1.435 (3)	C14A—C13A	1.374 (3)
C7A—C8A	1.333 (3)	C14A—C15A	1.379 (3)
O4A—C10A	1.199 (2)	C14A—C17A	1.512 (3)
O4B—C10B	1.196 (2)	C2A—C3A	1.369 (3)
C8A—C9A	1.444 (3)	C2A—H2A	0.9300
C8A—H8A	0.9300	C13A—H13A	0.9300
O2B—C9B	1.213 (3)	C13B—H13B	0.9300
C11B—C12B	1.377 (3)	C16A—C15A	1.382 (3)
C11B—C16B	1.383 (3)	C16A—H16A	0.9300
C11B—C10B	1.474 (3)	C16B—C15B	1.382 (3)
C1A—C2A	1.387 (3)	C16B—H16B	0.9300
O2A—C9A	1.210 (3)	C15B—H15B	0.9300
C6B—C5B	1.396 (3)	C15A—H15A	0.9300
C6B—C1B	1.398 (3)	C3A—C4A	1.389 (3)
C6B—C7B	1.434 (3)	C3A—H3A	0.9300
C12A—C11A	1.379 (3)	C3B—C4B	1.389 (4)
C12A—C13A	1.389 (3)	C3B—H3B	0.9300
C12A—H12A	0.9300	C4A—H4A	0.9300
C12B—C13B	1.387 (3)	C4B—H4B	0.9300
C12B—H12B	0.9300	C17A—H17A	0.9600
C11A—C16A	1.380 (3)	C17A—H17B	0.9600
C11A—C10A	1.478 (3)	C17A—H17C	0.9600
C8B—C7B	1.328 (3)	C17B—H17D	0.9600
C8B—C9B	1.443 (3)	C17B—H17E	0.9600
C8B—H8B	0.9300	C17B—H17F	0.9600
C10A—O3A—C7A	117.12 (15)	C3B—C2B—H2B	120.7
C9A—O1A—C1A	122.10 (16)	C1B—C2B—H2B	120.7
C10B—O3B—C7B	116.80 (15)	C13A—C14A—C15A	118.3 (2)
C1B—O1B—C9B	122.14 (16)	C13A—C14A—C17A	121.2 (2)
C1A—C6A—C5A	118.44 (19)	C15A—C14A—C17A	120.4 (2)
C1A—C6A—C7A	116.09 (19)	C3A—C2A—C1A	118.7 (2)
C5A—C6A—C7A	125.46 (19)	C3A—C2A—H2A	120.6
C8A—C7A—O3A	118.30 (18)	C1A—C2A—H2A	120.6
C8A—C7A—C6A	122.48 (18)	C14A—C13A—C12A	121.8 (2)
O3A—C7A—C6A	119.12 (18)	C14A—C13A—H13A	119.1
C7A—C8A—C9A	120.4 (2)	C12A—C13A—H13A	119.1
C7A—C8A—H8A	119.8	C14B—C13B—C12B	121.8 (2)
C9A—C8A—H8A	119.8	C14B—C13B—H13B	119.1
C12B—C11B—C16B	119.31 (19)	C12B—C13B—H13B	119.1
C12B—C11B—C10B	123.22 (19)	O1B—C1B—C2B	116.85 (19)
C16B—C11B—C10B	117.47 (19)	O1B—C1B—C6B	121.46 (19)
O1A—C1A—C2A	116.91 (19)	C2B—C1B—C6B	121.7 (2)
O1A—C1A—C6A	121.55 (18)	C11A—C16A—C15A	120.5 (2)
C2A—C1A—C6A	121.5 (2)	C11A—C16A—H16A	119.8
C5B—C6B—C1B	118.4 (2)	C15A—C16A—H16A	119.8
C5B—C6B—C7B	125.57 (19)	C15B—C16B—C11B	120.3 (2)
C1B—C6B—C7B	116.06 (19)	C15B—C16B—H16B	119.9
C11A—C12A—C13A	119.2 (2)	C11B—C16B—H16B	119.9
C11A—C12A—H12A	120.4	O2B—C9B—O1B	116.8 (2)
C13A—C12A—H12A	120.4	O2B—C9B—C8B	126.1 (2)
C11B—C12B—C13B	119.3 (2)	O1B—C9B—C8B	117.19 (19)
C11B—C12B—H12B	120.3	C14B—C15B—C16B	120.9 (2)
C13B—C12B—H12B	120.3	C14B—C15B—H15B	119.5
C12A—C11A—C16A	119.53 (19)	C16B—C15B—H15B	119.5
C12A—C11A—C10A	122.71 (19)	C14A—C15A—C16A	120.6 (2)
C16A—C11A—C10A	117.74 (19)	C14A—C15A—H15A	119.7
C7B—C8B—C9B	120.5 (2)	C16A—C15A—H15A	119.7
C7B—C8B—H8B	119.7	C2A—C3A—C4A	121.1 (2)
C9B—C8B—H8B	119.7	C2A—C3A—H3A	119.5
C4B—C5B—C6B	120.1 (2)	C4A—C3A—H3A	119.5
C4B—C5B—H5B	120.0	C2B—C3B—C4B	120.9 (2)
C6B—C5B—H5B	120.0	C2B—C3B—H3B	119.6
O4A—C10A—O3A	122.06 (18)	C4B—C3B—H3B	119.5
O4A—C10A—C11A	125.86 (19)	C5A—C4A—C3A	120.2 (2)
O3A—C10A—C11A	112.07 (17)	C5A—C4A—H4A	119.9
C8B—C7B—O3B	119.35 (19)	C3A—C4A—H4A	119.9
C8B—C7B—C6B	122.58 (19)	C5B—C4B—C3B	120.4 (2)
O3B—C7B—C6B	117.97 (18)	C5B—C4B—H4B	119.8
O4B—C10B—O3B	121.76 (18)	C3B—C4B—H4B	119.8
O4B—C10B—C11B	126.1 (2)	C14A—C17A—H17A	109.5
O3B—C10B—C11B	112.09 (17)	C14A—C17A—H17B	109.5
O2A—C9A—O1A	116.75 (19)	H17A—C17A—H17B	109.5
O2A—C9A—C8A	125.9 (2)	C14A—C17A—H17C	109.5
O1A—C9A—C8A	117.37 (19)	H17A—C17A—H17C	109.5
C13B—C14B—C15B	118.3 (2)	H17B—C17A—H17C	109.5
C13B—C14B—C17B	121.1 (2)	C14B—C17B—H17D	109.5
C15B—C14B—C17B	120.6 (2)	C14B—C17B—H17E	109.5
C4A—C5A—C6A	120.0 (2)	H17D—C17B—H17E	109.5
C4A—C5A—H5A	120.0	C14B—C17B—H17F	109.5
C6A—C5A—H5A	120.0	H17D—C17B—H17F	109.5
C3B—C2B—C1B	118.6 (2)	H17E—C17B—H17F	109.5
C10A—O3A—C7A—C8A	−105.1 (2)	C1A—O1A—C9A—C8A	−0.8 (3)
C10A—O3A—C7A—C6A	78.5 (2)	C7A—C8A—C9A—O2A	−179.0 (2)
C1A—C6A—C7A—C8A	0.5 (3)	C7A—C8A—C9A—O1A	0.3 (3)
C5A—C6A—C7A—C8A	−178.7 (2)	C1A—C6A—C5A—C4A	0.4 (3)
C1A—C6A—C7A—O3A	176.72 (16)	C7A—C6A—C5A—C4A	179.6 (2)
C5A—C6A—C7A—O3A	−2.5 (3)	O1A—C1A—C2A—C3A	−178.52 (19)
O3A—C7A—C8A—C9A	−176.50 (17)	C6A—C1A—C2A—C3A	1.0 (3)
C6A—C7A—C8A—C9A	−0.2 (3)	C15A—C14A—C13A—C12A	−0.3 (4)
C9A—O1A—C1A—C2A	−179.40 (18)	C17A—C14A—C13A—C12A	−179.5 (2)
C9A—O1A—C1A—C6A	1.1 (3)	C11A—C12A—C13A—C14A	−0.8 (3)
C5A—C6A—C1A—O1A	178.39 (18)	C15B—C14B—C13B—C12B	0.1 (4)
C7A—C6A—C1A—O1A	−0.9 (3)	C17B—C14B—C13B—C12B	−179.0 (2)
C5A—C6A—C1A—C2A	−1.1 (3)	C11B—C12B—C13B—C14B	1.1 (4)
C7A—C6A—C1A—C2A	179.61 (18)	C9B—O1B—C1B—C2B	−178.96 (19)
C16B—C11B—C12B—C13B	−2.1 (3)	C9B—O1B—C1B—C6B	1.4 (3)
C10B—C11B—C12B—C13B	178.3 (2)	C3B—C2B—C1B—O1B	−178.88 (19)
C13A—C12A—C11A—C16A	1.6 (3)	C3B—C2B—C1B—C6B	0.8 (3)
C13A—C12A—C11A—C10A	−176.7 (2)	C5B—C6B—C1B—O1B	179.20 (18)
C1B—C6B—C5B—C4B	−0.1 (3)	C7B—C6B—C1B—O1B	−0.3 (3)
C7B—C6B—C5B—C4B	179.3 (2)	C5B—C6B—C1B—C2B	−0.5 (3)
C7A—O3A—C10A—O4A	−3.5 (3)	C7B—C6B—C1B—C2B	−179.91 (19)
C7A—O3A—C10A—C11A	175.57 (17)	C12A—C11A—C16A—C15A	−1.4 (3)
C12A—C11A—C10A—O4A	168.4 (2)	C10A—C11A—C16A—C15A	177.0 (2)
C16A—C11A—C10A—O4A	−9.9 (3)	C12B—C11B—C16B—C15B	1.9 (3)
C12A—C11A—C10A—O3A	−10.7 (3)	C10B—C11B—C16B—C15B	−178.4 (2)
C16A—C11A—C10A—O3A	171.03 (18)	C1B—O1B—C9B—O2B	177.83 (19)
C9B—C8B—C7B—O3B	−176.69 (18)	C1B—O1B—C9B—C8B	−1.9 (3)
C9B—C8B—C7B—C6B	−0.4 (3)	C7B—C8B—C9B—O2B	−178.3 (2)
C10B—O3B—C7B—C8B	−99.2 (2)	C7B—C8B—C9B—O1B	1.5 (3)
C10B—O3B—C7B—C6B	84.4 (2)	C13B—C14B—C15B—C16B	−0.2 (4)
C5B—C6B—C7B—C8B	−179.6 (2)	C17B—C14B—C15B—C16B	178.9 (2)
C1B—C6B—C7B—C8B	−0.2 (3)	C11B—C16B—C15B—C14B	−0.8 (4)
C5B—C6B—C7B—O3B	−3.3 (3)	C13A—C14A—C15A—C16A	0.6 (4)
C1B—C6B—C7B—O3B	176.12 (16)	C17A—C14A—C15A—C16A	179.7 (2)
C7B—O3B—C10B—O4B	−1.4 (3)	C11A—C16A—C15A—C14A	0.3 (4)
C7B—O3B—C10B—C11B	179.56 (17)	C1A—C2A—C3A—C4A	−0.2 (4)
C12B—C11B—C10B—O4B	−170.2 (2)	C1B—C2B—C3B—C4B	−0.6 (4)
C16B—C11B—C10B—O4B	10.1 (3)	C6A—C5A—C4A—C3A	0.4 (3)
C12B—C11B—C10B—O3B	8.8 (3)	C2A—C3A—C4A—C5A	−0.5 (4)
C16B—C11B—C10B—O3B	−170.85 (19)	C6B—C5B—C4B—C3B	0.3 (4)
C1A—O1A—C9A—O2A	178.64 (19)	C2B—C3B—C4B—C5B	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A···O4B	0.93	2.55	3.389 (3)	151
C8A—H8A···O2Bi	0.93	2.52	3.453 (3)	177
C8B—H8B···O2Ai	0.93	2.50	3.425 (3)	176
C12A—H12A···O2Ai	0.93	2.59	3.498 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5A—H5A⋯O4B	0.93	2.55	3.389 (3)	151
C8A—H8A⋯O2B i	0.93	2.52	3.453 (3)	177
C8B—H8B⋯O2A i	0.93	2.50	3.425 (3)	176
C12A—H12A⋯O2A i	0.93	2.59	3.498 (3)	167

Symmetry code: (i) .