4,6-Di-tert-butyl-2,3-di-hydroxy-benzalde-hyde.

The title compound, C15H22O3, crystallizes with two independent mol-ecules in the asymmetric unit. In each mol-ecule, one hy-droxy group (at position 2) is involved in an intra-molecular O-H⋯O hydrogen bond, and another one (at position 3) exhibits bifurcated hydrogen-bonding being involved in intra- and inter-molecular O-H⋯O inter-actions. In the crystal, O-H⋯O hydrogen bonds link alternating independent mol-ecules into chains running along [010].

Related literature

For the crystal structure of 2,3-di­hydroxy­benzaldehyde, see: Ng (2005 ▶). For applications of Shiff base ligands based on 2,3-di­hydroxy­benzaldehyde, see: Albrecht et al. (2004 ▶); Furutachi et al. (2010 ▶); Belmonte et al. (2012 ▶).

Experimental

Crystal data

C15H22O3

M = 250.33

Triclinic,

a = 9.3113 (9) Å

b = 10.6511 (10) Å

c = 15.3962 (15) Å

α = 95.242 (2)°

β = 103.085 (2)°

γ = 95.492 (2)°

V = 1470.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.70 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.948, T max = 0.988

8903 measured reflections

5740 independent reflections

4411 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.06

5740 reflections

361 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025488/cv5427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025488/cv5427Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025488/cv5427Isup3.cml

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

C15H22O3	Z = 4
Mr = 250.33	F(000) = 544
Triclinic, P1	Dx = 1.131 Mg m−3
Hall symbol: -P 1	Melting point: 115 K
a = 9.3113 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6511 (10) Å	Cell parameters from 900 reflections
c = 15.3962 (15) Å	θ = 2–30°
α = 95.242 (2)°	µ = 0.08 mm−1
β = 103.085 (2)°	T = 100 K
γ = 95.492 (2)°	Prism, yellow
V = 1470.4 (2) Å3	0.70 × 0.16 × 0.16 mm

Bruker SMART APEX CCD area-detector diffractometer	5740 independent reflections
Radiation source: fine-focus sealed tube	4411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −11→11
Tmin = 0.948, Tmax = 0.988	k = −11→13
8903 measured reflections	l = −18→18

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.0779P)2 + 0.0742P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.25 e Å−3
5740 reflections	Δρmin = −0.21 e Å−3
361 parameters

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.

	x	y	z	Uiso*/Ueq
O1A	0.13058 (9)	−0.38259 (6)	0.24551 (5)	0.0316 (2)
H1A	0.1319 (16)	−0.3993 (13)	0.1884 (10)	0.054 (4)*
O2A	0.14084 (8)	−0.22900 (6)	0.12158 (5)	0.02752 (18)
H2A	0.1392 (16)	−0.1505 (13)	0.0745 (10)	0.057 (4)*
O3A	0.15955 (9)	−0.01066 (7)	0.07434 (5)	0.02887 (19)
C1A	0.15563 (11)	−0.25515 (9)	0.27164 (7)	0.0226 (2)
C2A	0.16112 (11)	−0.17213 (9)	0.20646 (7)	0.0216 (2)
C3A	0.18605 (10)	−0.03905 (9)	0.22842 (7)	0.0214 (2)
C4A	0.21238 (11)	0.01227 (9)	0.32024 (7)	0.0223 (2)
C5A	0.20502 (11)	−0.07376 (9)	0.38215 (7)	0.0229 (2)
H5AA	0.2218	−0.0407	0.4435	0.027*
C6A	0.17450 (11)	−0.20648 (9)	0.36057 (7)	0.0232 (2)
C7A	0.18009 (12)	0.03568 (9)	0.15347 (7)	0.0253 (2)
H7A	0.1889 (13)	0.1306 (11)	0.1631 (8)	0.031 (3)*
C8A	0.24859 (12)	0.15602 (9)	0.35317 (7)	0.0261 (3)
C9A	0.28235 (14)	0.18201 (10)	0.45588 (8)	0.0352 (3)
H9AA	0.1952	0.1507	0.4768	0.053*
H9AB	0.3066	0.2736	0.4741	0.053*
H9AC	0.3668	0.1383	0.4823	0.053*
C10A	0.11678 (13)	0.22788 (10)	0.31648 (8)	0.0337 (3)
H10A	0.0299	0.1942	0.3368	0.051*
H10B	0.0940	0.2169	0.2507	0.051*
H10C	0.1423	0.3184	0.3385	0.051*
C11A	0.38925 (13)	0.21161 (10)	0.32590 (8)	0.0331 (3)
H11A	0.3704	0.2048	0.2603	0.050*
H11B	0.4719	0.1641	0.3493	0.050*
H11C	0.4146	0.3011	0.3508	0.050*
C12A	0.15986 (13)	−0.29441 (10)	0.43265 (7)	0.0295 (3)
C13A	0.17984 (15)	−0.22047 (11)	0.52559 (8)	0.0369 (3)
H13A	0.1043	−0.1620	0.5233	0.055*
H13B	0.2789	−0.1721	0.5437	0.055*
H13C	0.1691	−0.2801	0.5692	0.055*
C14A	0.00288 (14)	−0.36849 (11)	0.40655 (8)	0.0382 (3)
H14A	−0.0111	−0.4201	0.3485	0.057*
H14B	−0.0713	−0.3086	0.4020	0.057*
H14C	−0.0088	−0.4240	0.4525	0.057*
C15A	0.27806 (14)	−0.38673 (11)	0.43956 (8)	0.0387 (3)
H15A	0.2660	−0.4369	0.3812	0.058*
H15B	0.2664	−0.4437	0.4846	0.058*
H15C	0.3772	−0.3385	0.4573	0.058*
O1B	0.19869 (9)	0.08055 (6)	−0.08108 (5)	0.02929 (19)
H1B	0.1807 (18)	0.0734 (14)	−0.0277 (11)	0.067 (5)*
O2B	0.14124 (8)	0.25992 (6)	0.03230 (5)	0.02881 (18)
H2B	0.1334 (19)	0.3373 (15)	0.0690 (11)	0.075 (5)*
O3B	0.14462 (10)	0.48947 (7)	0.08636 (5)	0.0382 (2)
C1B	0.22899 (11)	0.20423 (9)	−0.09443 (7)	0.0229 (2)
C2B	0.19582 (11)	0.30029 (9)	−0.03624 (7)	0.0227 (2)
C3B	0.22243 (11)	0.42972 (9)	−0.04678 (7)	0.0242 (2)
C4B	0.28051 (11)	0.46447 (9)	−0.12054 (7)	0.0241 (2)
C5B	0.31494 (11)	0.36661 (9)	−0.17478 (7)	0.0247 (2)
H5BA	0.3557	0.3885	−0.2234	0.030*
C6B	0.29418 (11)	0.23659 (9)	−0.16335 (7)	0.0230 (2)
C7B	0.19374 (14)	0.51970 (10)	0.02154 (8)	0.0338 (3)
H7B	0.2122 (16)	0.6105 (13)	0.0160 (10)	0.055 (4)*
C8B	0.30439 (12)	0.60314 (10)	−0.14183 (8)	0.0302 (3)
C9B	0.43000 (15)	0.68113 (11)	−0.06932 (10)	0.0469 (4)
H9BA	0.4426	0.7687	−0.0837	0.070*
H9BB	0.5226	0.6436	−0.0671	0.070*
H9BC	0.4049	0.6809	−0.0108	0.070*
C10B	0.16044 (14)	0.66445 (11)	−0.15304 (9)	0.0418 (3)
H10D	0.1763	0.7494	−0.1714	0.063*
H10E	0.1305	0.6712	−0.0959	0.063*
H10F	0.0821	0.6121	−0.1991	0.063*
C11B	0.34989 (16)	0.60891 (11)	−0.23132 (9)	0.0459 (4)
H11D	0.3606	0.6974	−0.2441	0.069*
H11E	0.2734	0.5587	−0.2796	0.069*
H11F	0.4447	0.5743	−0.2274	0.069*
C12B	0.34396 (12)	0.13435 (10)	−0.22352 (7)	0.0279 (3)
C13B	0.42121 (14)	0.19175 (11)	−0.29129 (8)	0.0379 (3)
H13D	0.3519	0.2374	−0.3309	0.057*
H13E	0.4530	0.1237	−0.3272	0.057*
H13F	0.5081	0.2508	−0.2591	0.057*
C14B	0.20742 (14)	0.04340 (11)	−0.27618 (8)	0.0378 (3)
H14D	0.1382	0.0911	−0.3141	0.057*
H14E	0.1581	0.0036	−0.2340	0.057*
H14F	0.2390	−0.0225	−0.3140	0.057*
C15B	0.45488 (13)	0.06066 (11)	−0.16510 (8)	0.0358 (3)
H15D	0.5414	0.1194	−0.1319	0.054*
H15E	0.4869	−0.0042	−0.2035	0.054*
H15F	0.4072	0.0198	−0.1226	0.054*

	U11	U22	U33	U12	U13	U23
O1A	0.0487 (5)	0.0195 (3)	0.0268 (4)	−0.0008 (3)	0.0121 (4)	0.0013 (3)
O2A	0.0381 (4)	0.0244 (3)	0.0206 (4)	0.0004 (3)	0.0105 (3)	0.0001 (3)
O3A	0.0371 (4)	0.0276 (3)	0.0233 (4)	0.0024 (3)	0.0099 (3)	0.0047 (3)
C1A	0.0237 (5)	0.0197 (4)	0.0254 (5)	0.0007 (4)	0.0085 (4)	0.0027 (4)
C2A	0.0216 (5)	0.0247 (5)	0.0187 (5)	0.0008 (4)	0.0069 (4)	0.0005 (4)
C3A	0.0190 (5)	0.0214 (4)	0.0257 (5)	0.0020 (4)	0.0087 (4)	0.0043 (4)
C4A	0.0184 (5)	0.0233 (5)	0.0257 (5)	0.0028 (4)	0.0065 (4)	0.0019 (4)
C5A	0.0233 (5)	0.0252 (5)	0.0205 (5)	0.0017 (4)	0.0072 (4)	0.0006 (4)
C6A	0.0209 (5)	0.0254 (5)	0.0240 (5)	0.0018 (4)	0.0063 (4)	0.0043 (4)
C7A	0.0260 (5)	0.0254 (5)	0.0259 (5)	0.0023 (4)	0.0090 (4)	0.0037 (4)
C8A	0.0289 (5)	0.0225 (5)	0.0268 (5)	−0.0012 (4)	0.0099 (4)	−0.0006 (4)
C9A	0.0444 (7)	0.0274 (5)	0.0314 (6)	−0.0031 (5)	0.0101 (5)	−0.0043 (4)
C10A	0.0368 (6)	0.0237 (5)	0.0414 (7)	0.0052 (4)	0.0120 (5)	0.0000 (4)
C11A	0.0320 (6)	0.0298 (5)	0.0362 (6)	−0.0049 (4)	0.0105 (5)	0.0007 (4)
C12A	0.0351 (6)	0.0289 (5)	0.0250 (6)	0.0017 (4)	0.0075 (5)	0.0077 (4)
C13A	0.0491 (7)	0.0382 (6)	0.0252 (6)	0.0048 (5)	0.0107 (5)	0.0093 (5)
C14A	0.0422 (7)	0.0395 (6)	0.0353 (6)	−0.0043 (5)	0.0141 (5)	0.0136 (5)
C15A	0.0484 (7)	0.0333 (6)	0.0345 (6)	0.0091 (5)	0.0054 (6)	0.0118 (5)
O1B	0.0419 (4)	0.0208 (3)	0.0293 (4)	0.0014 (3)	0.0179 (3)	0.0031 (3)
O2B	0.0417 (4)	0.0246 (3)	0.0253 (4)	0.0046 (3)	0.0177 (3)	0.0045 (3)
O3B	0.0614 (5)	0.0276 (4)	0.0314 (4)	0.0090 (3)	0.0219 (4)	0.0026 (3)
C1B	0.0244 (5)	0.0206 (4)	0.0237 (5)	0.0012 (4)	0.0058 (4)	0.0041 (4)
C2B	0.0243 (5)	0.0258 (5)	0.0190 (5)	0.0016 (4)	0.0071 (4)	0.0051 (4)
C3B	0.0247 (5)	0.0235 (5)	0.0245 (5)	0.0042 (4)	0.0045 (4)	0.0054 (4)
C4B	0.0201 (5)	0.0261 (5)	0.0254 (5)	0.0001 (4)	0.0036 (4)	0.0072 (4)
C5B	0.0208 (5)	0.0309 (5)	0.0235 (5)	0.0007 (4)	0.0067 (4)	0.0078 (4)
C6B	0.0195 (5)	0.0286 (5)	0.0202 (5)	0.0014 (4)	0.0046 (4)	0.0012 (4)
C7B	0.0471 (7)	0.0253 (5)	0.0318 (6)	0.0068 (5)	0.0135 (5)	0.0054 (4)
C8B	0.0290 (5)	0.0257 (5)	0.0361 (6)	−0.0009 (4)	0.0069 (5)	0.0114 (4)
C9B	0.0423 (7)	0.0293 (6)	0.0591 (9)	−0.0062 (5)	−0.0059 (7)	0.0095 (6)
C10B	0.0364 (6)	0.0305 (5)	0.0613 (8)	0.0034 (5)	0.0112 (6)	0.0217 (5)
C11B	0.0562 (8)	0.0345 (6)	0.0534 (8)	−0.0021 (5)	0.0235 (6)	0.0196 (5)
C12B	0.0287 (5)	0.0322 (5)	0.0250 (5)	0.0032 (4)	0.0122 (4)	−0.0003 (4)
C13B	0.0427 (6)	0.0439 (6)	0.0335 (6)	0.0085 (5)	0.0210 (5)	0.0043 (5)
C14B	0.0378 (6)	0.0408 (6)	0.0322 (6)	−0.0012 (5)	0.0112 (5)	−0.0107 (5)
C15B	0.0373 (6)	0.0364 (6)	0.0377 (6)	0.0109 (5)	0.0159 (5)	0.0013 (5)

O1A—C1A	1.3623 (11)	O1B—C1B	1.3645 (12)
O1A—H1A	0.885 (15)	O1B—H1B	0.883 (17)
O2A—C2A	1.3535 (12)	O2B—C2B	1.3567 (13)
O2A—H2A	1.154 (14)	O2B—H2B	0.974 (17)
O3A—C7A	1.2373 (13)	O3B—C7B	1.2436 (15)
C1A—C6A	1.3849 (15)	C1B—C6B	1.3899 (15)
C1A—C2A	1.4030 (14)	C1B—C2B	1.4011 (15)
C2A—C3A	1.4112 (13)	C2B—C3B	1.4078 (14)
C3A—C4A	1.4260 (14)	C3B—C4B	1.4269 (15)
C3A—C7A	1.4545 (15)	C3B—C7B	1.4450 (16)
C4A—C5A	1.3893 (14)	C4B—C5B	1.3830 (15)
C4A—C8A	1.5483 (13)	C4B—C8B	1.5482 (14)
C5A—C6A	1.4086 (13)	C5B—C6B	1.4124 (14)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C12A	1.5366 (15)	C6B—C12B	1.5380 (15)
C7A—H7A	1.001 (11)	C7B—H7B	0.981 (14)
C8A—C9A	1.5345 (16)	C8B—C10B	1.5284 (17)
C8A—C10A	1.5349 (16)	C8B—C11B	1.5350 (19)
C8A—C11A	1.5454 (16)	C8B—C9B	1.5355 (16)
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C11A—H11A	0.9800	C11B—H11D	0.9800
C11A—H11B	0.9800	C11B—H11E	0.9800
C11A—H11C	0.9800	C11B—H11F	0.9800
C12A—C13A	1.5323 (16)	C12B—C13B	1.5335 (17)
C12A—C15A	1.5372 (17)	C12B—C15B	1.5347 (16)
C12A—C14A	1.5414 (16)	C12B—C14B	1.5382 (15)
C13A—H13A	0.9800	C13B—H13D	0.9800
C13A—H13B	0.9800	C13B—H13E	0.9800
C13A—H13C	0.9800	C13B—H13F	0.9800
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15B	0.9800	C15B—H15E	0.9800
C15A—H15C	0.9800	C15B—H15F	0.9800
C1A—O1A—H1A	110.9 (9)	C1B—O1B—H1B	112.1 (10)
C2A—O2A—H2A	107.9 (7)	C2B—O2B—H2B	105.0 (10)
O1A—C1A—C6A	121.43 (9)	O1B—C1B—C6B	121.39 (9)
O1A—C1A—C2A	118.85 (9)	O1B—C1B—C2B	119.02 (10)
C6A—C1A—C2A	119.71 (9)	C6B—C1B—C2B	119.58 (9)
O2A—C2A—C1A	115.16 (8)	O2B—C2B—C1B	115.32 (9)
O2A—C2A—C3A	122.78 (9)	O2B—C2B—C3B	122.63 (9)
C1A—C2A—C3A	122.06 (9)	C1B—C2B—C3B	122.02 (10)
C2A—C3A—C4A	118.86 (9)	C2B—C3B—C4B	119.22 (9)
C2A—C3A—C7A	116.16 (9)	C2B—C3B—C7B	116.57 (10)
C4A—C3A—C7A	124.98 (9)	C4B—C3B—C7B	124.17 (9)
C5A—C4A—C3A	116.85 (9)	C5B—C4B—C3B	116.59 (9)
C5A—C4A—C8A	119.49 (9)	C5B—C4B—C8B	119.99 (10)
C3A—C4A—C8A	123.65 (9)	C3B—C4B—C8B	123.41 (9)
C4A—C5A—C6A	124.74 (9)	C4B—C5B—C6B	124.97 (10)
C4A—C5A—H5AA	117.6	C4B—C5B—H5BA	117.5
C6A—C5A—H5AA	117.6	C6B—C5B—H5BA	117.5
C1A—C6A—C5A	117.68 (9)	C1B—C6B—C5B	117.45 (9)
C1A—C6A—C12A	120.97 (9)	C1B—C6B—C12B	120.95 (9)
C5A—C6A—C12A	121.34 (9)	C5B—C6B—C12B	121.59 (10)
O3A—C7A—C3A	124.01 (9)	O3B—C7B—C3B	124.19 (10)
O3A—C7A—H7A	115.1 (7)	O3B—C7B—H7B	117.6 (9)
C3A—C7A—H7A	120.8 (7)	C3B—C7B—H7B	118.2 (9)
C9A—C8A—C10A	106.64 (9)	C10B—C8B—C11B	105.50 (10)
C9A—C8A—C11A	106.03 (9)	C10B—C8B—C9B	111.32 (10)
C10A—C8A—C11A	110.55 (9)	C11B—C8B—C9B	106.67 (10)
C9A—C8A—C4A	111.89 (9)	C10B—C8B—C4B	111.07 (9)
C10A—C8A—C4A	111.07 (8)	C11B—C8B—C4B	111.32 (9)
C11A—C8A—C4A	110.48 (9)	C9B—C8B—C4B	110.77 (9)
C8A—C9A—H9AA	109.5	C8B—C9B—H9BA	109.5
C8A—C9A—H9AB	109.5	C8B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
C8A—C9A—H9AC	109.5	C8B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
C8A—C10A—H10A	109.5	C8B—C10B—H10D	109.5
C8A—C10A—H10B	109.5	C8B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C8A—C10A—H10C	109.5	C8B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C8A—C11A—H11A	109.5	C8B—C11B—H11D	109.5
C8A—C11A—H11B	109.5	C8B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C8A—C11A—H11C	109.5	C8B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C13A—C12A—C6A	112.27 (9)	C13B—C12B—C15B	107.54 (10)
C13A—C12A—C15A	107.87 (9)	C13B—C12B—C6B	112.18 (9)
C6A—C12A—C15A	110.06 (10)	C15B—C12B—C6B	109.49 (9)
C13A—C12A—C14A	107.79 (10)	C13B—C12B—C14B	108.16 (9)
C6A—C12A—C14A	108.50 (9)	C15B—C12B—C14B	110.12 (9)
C15A—C12A—C14A	110.33 (9)	C6B—C12B—C14B	109.32 (9)
C12A—C13A—H13A	109.5	C12B—C13B—H13D	109.5
C12A—C13A—H13B	109.5	C12B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C12A—C13A—H13C	109.5	C12B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C12A—C14A—H14A	109.5	C12B—C14B—H14D	109.5
C12A—C14A—H14B	109.5	C12B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C12A—C14A—H14C	109.5	C12B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C12A—C15A—H15A	109.5	C12B—C15B—H15D	109.5
C12A—C15A—H15B	109.5	C12B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C12A—C15A—H15C	109.5	C12B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
O1A—C1A—C2A—O2A	−0.23 (14)	O1B—C1B—C2B—O2B	2.92 (13)
C6A—C1A—C2A—O2A	−179.75 (9)	C6B—C1B—C2B—O2B	−175.97 (8)
O1A—C1A—C2A—C3A	179.77 (9)	O1B—C1B—C2B—C3B	−179.19 (9)
C6A—C1A—C2A—C3A	0.25 (16)	C6B—C1B—C2B—C3B	1.93 (15)
O2A—C2A—C3A—C4A	−177.43 (9)	O2B—C2B—C3B—C4B	179.78 (9)
C1A—C2A—C3A—C4A	2.57 (15)	C1B—C2B—C3B—C4B	2.04 (15)
O2A—C2A—C3A—C7A	3.57 (14)	O2B—C2B—C3B—C7B	2.22 (14)
C1A—C2A—C3A—C7A	−176.43 (9)	C1B—C2B—C3B—C7B	−175.52 (10)
C2A—C3A—C4A—C5A	−2.79 (14)	C2B—C3B—C4B—C5B	−3.52 (14)
C7A—C3A—C4A—C5A	176.12 (10)	C7B—C3B—C4B—C5B	173.84 (10)
C2A—C3A—C4A—C8A	176.94 (9)	C2B—C3B—C4B—C8B	175.97 (9)
C7A—C3A—C4A—C8A	−4.15 (16)	C7B—C3B—C4B—C8B	−6.67 (16)
C3A—C4A—C5A—C6A	0.36 (15)	C3B—C4B—C5B—C6B	1.28 (15)
C8A—C4A—C5A—C6A	−179.38 (9)	C8B—C4B—C5B—C6B	−178.23 (9)
O1A—C1A—C6A—C5A	177.85 (9)	O1B—C1B—C6B—C5B	177.04 (9)
C2A—C1A—C6A—C5A	−2.65 (15)	C2B—C1B—C6B—C5B	−4.10 (14)
O1A—C1A—C6A—C12A	−3.19 (15)	O1B—C1B—C6B—C12B	−4.00 (14)
C2A—C1A—C6A—C12A	176.32 (9)	C2B—C1B—C6B—C12B	174.86 (9)
C4A—C5A—C6A—C1A	2.40 (16)	C4B—C5B—C6B—C1B	2.58 (15)
C4A—C5A—C6A—C12A	−176.56 (10)	C4B—C5B—C6B—C12B	−176.38 (9)
C2A—C3A—C7A—O3A	−2.33 (16)	C2B—C3B—C7B—O3B	−1.77 (17)
C4A—C3A—C7A—O3A	178.74 (10)	C4B—C3B—C7B—O3B	−179.20 (10)
C5A—C4A—C8A—C9A	3.81 (14)	C5B—C4B—C8B—C10B	123.69 (11)
C3A—C4A—C8A—C9A	−175.91 (10)	C3B—C4B—C8B—C10B	−55.79 (13)
C5A—C4A—C8A—C10A	−115.24 (11)	C5B—C4B—C8B—C11B	6.45 (14)
C3A—C4A—C8A—C10A	65.03 (13)	C3B—C4B—C8B—C11B	−173.02 (10)
C5A—C4A—C8A—C11A	121.69 (11)	C5B—C4B—C8B—C9B	−112.06 (12)
C3A—C4A—C8A—C11A	−58.03 (13)	C3B—C4B—C8B—C9B	68.47 (14)
C1A—C6A—C12A—C13A	−178.10 (10)	C1B—C6B—C12B—C13B	−176.58 (9)
C5A—C6A—C12A—C13A	0.83 (15)	C5B—C6B—C12B—C13B	2.35 (13)
C1A—C6A—C12A—C15A	61.73 (12)	C1B—C6B—C12B—C15B	−57.26 (12)
C5A—C6A—C12A—C15A	−119.34 (11)	C5B—C6B—C12B—C15B	121.66 (10)
C1A—C6A—C12A—C14A	−59.08 (14)	C1B—C6B—C12B—C14B	63.45 (12)
C5A—C6A—C12A—C14A	119.85 (11)	C5B—C6B—C12B—C14B	−117.63 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2A	0.885 (15)	2.169 (15)	2.6360 (10)	112.4 (11)
O2A—H2A···O3A	1.154 (14)	1.484 (14)	2.5013 (10)	142.7 (12)
O1B—H1B···O2B	0.883 (17)	2.212 (16)	2.6443 (10)	109.7 (12)
O2B—H2B···O3B	0.974 (17)	1.608 (16)	2.5046 (10)	150.9 (16)
O1B—H1B···O3A	0.883 (17)	1.916 (17)	2.7485 (11)	156.4 (15)
O1A—H1A···O3Bi	0.885 (15)	1.912 (15)	2.7289 (11)	152.9 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O2A	0.885 (15)	2.169 (15)	2.6360 (10)	112.4 (11)
O2A—H2A⋯O3A	1.154 (14)	1.484 (14)	2.5013 (10)	142.7 (12)
O1B—H1B⋯O2B	0.883 (17)	2.212 (16)	2.6443 (10)	109.7 (12)
O2B—H2B⋯O3B	0.974 (17)	1.608 (16)	2.5046 (10)	150.9 (16)
O1B—H1B⋯O3A	0.883 (17)	1.916 (17)	2.7485 (11)	156.4 (15)
O1A—H1A⋯O3B i	0.885 (15)	1.912 (15)	2.7289 (11)	152.9 (13)

Symmetry code: (i) .