(E)-2-[(2,4,6-Tri-meth-oxy-benzyl-idene)amino]-phenol.

There are two independent mol-ecules in the asymmetric unit of the title compound, C16H17NO4, with similar conformations but some differences in their bond angles. Each mol-ecule adopts a trans configuration with respect to the methyl-idene C=N bond and is twisted with a dihedral angle between the two substituted benzene rings of 80.52 (7)° in one mol-ecule and 83.53 (7)° in the other. All meth-oxy groups are approximately coplanar with the attached benzene rings, with Cmeth-yl-O-C-C torsion angles ranging from -6.7 (2) to 5.07 (19)°. In the crystal, independent mol-ecules are linked together by O-H⋯N and O-H⋯O hydrogen bonds and a π-π inter-action [centroid-centroid distance of 3.6030 (9) Å], forming a dimer. The dimers are further linked by weak C-H⋯O inter-actions and another π-π inter-action [centroid-centroid distance of 3.9452 (9) Å] into layers lying parallel to the ab plane.

Related literature

For organic bond-length data, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to and application of aza-stilbene, see: Cheng et al. (2010 ▶); da Silva et al. (2011 ▶); Fujita et al. (2012 ▶); Lu et al. (2012 ▶); Tamizh et al. (2012 ▶). For related structures, see: Kaewmanee et al. (2013 ▶); Sun et al. (2011 ▶).

Experimental

Crystal data

C16H17NO4

M = 287.31

Triclinic,

a = 7.3819 (6) Å

b = 11.7036 (9) Å

c = 16.4373 (13) Å

α = 89.469 (2)°

β = 85.616 (2)°

γ = 80.456 (2)°

V = 1396.34 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.49 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.985

29313 measured reflections

8129 independent reflections

5872 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.148

S = 1.02

8129 reflections

393 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032996/is5324sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032996/is5324Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032996/is5324Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H17NO4	Z = 4
Mr = 287.31	F(000) = 608
Triclinic, P1	Dx = 1.367 Mg m−3
Hall symbol: -P 1	Melting point = 450–452 K
a = 7.3819 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7036 (9) Å	Cell parameters from 8129 reflections
c = 16.4373 (13) Å	θ = 2.5–30.0°
α = 89.469 (2)°	µ = 0.10 mm−1
β = 85.616 (2)°	T = 100 K
γ = 80.456 (2)°	Block, colourless
V = 1396.34 (19) Å3	0.49 × 0.16 × 0.16 mm

Bruker SMART APEX2 CCD area-detector diffractometer	8129 independent reflections
Radiation source: fine-focus sealed tube	5872 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.33 pixels mm-1	θmax = 30.0°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −16→16
Tmin = 0.954, Tmax = 0.985	l = −23→23
29313 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0788P)2 + 0.2397P] where P = (Fo2 + 2Fc2)/3
8129 reflections	(Δ/σ)max = 0.001
393 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.21415 (16)	0.83067 (9)	0.10628 (6)	0.0249 (2)
O2A	0.19684 (16)	0.59610 (10)	0.34830 (7)	0.0292 (3)
O3A	0.27544 (15)	0.98999 (9)	0.36114 (6)	0.0221 (2)
O4A	0.58266 (14)	1.21472 (9)	0.13823 (6)	0.0210 (2)
H1O4	0.597 (3)	1.164 (2)	0.1779 (13)	0.043 (6)*
N1A	0.29206 (16)	1.11109 (10)	0.21219 (7)	0.0180 (2)
C1A	0.23748 (19)	0.91116 (12)	0.23397 (8)	0.0174 (3)
C2A	0.21676 (19)	0.81294 (12)	0.18822 (8)	0.0187 (3)
C3A	0.2025 (2)	0.70672 (12)	0.22379 (9)	0.0205 (3)
H3AA	0.1881	0.6424	0.1915	0.025*
C4A	0.20979 (19)	0.69651 (13)	0.30743 (9)	0.0206 (3)
C5A	0.2352 (2)	0.78998 (13)	0.35564 (9)	0.0206 (3)
H5AA	0.2417	0.7813	0.4129	0.025*
C6A	0.25065 (19)	0.89475 (12)	0.31884 (8)	0.0181 (3)
C7A	0.23176 (19)	1.01974 (12)	0.19062 (8)	0.0184 (3)
H7AA	0.1768	1.0241	0.1400	0.022*
C8A	0.2556 (2)	1.20881 (12)	0.16002 (8)	0.0175 (3)
C9A	0.40463 (19)	1.25893 (12)	0.12645 (8)	0.0179 (3)
C10A	0.3708 (2)	1.35666 (13)	0.07741 (8)	0.0212 (3)
H10A	0.4711	1.3905	0.0541	0.025*
C11A	0.1919 (2)	1.40519 (13)	0.06215 (9)	0.0227 (3)
H11A	0.1706	1.4718	0.0286	0.027*
C12A	0.0448 (2)	1.35683 (13)	0.09567 (9)	0.0231 (3)
H12A	−0.0776	1.3907	0.0857	0.028*
C13A	0.0767 (2)	1.25830 (13)	0.14406 (9)	0.0216 (3)
H13A	−0.0244	1.2245	0.1664	0.026*
C14A	0.2055 (2)	0.73234 (14)	0.05636 (9)	0.0283 (4)
H14A	0.2138	0.7546	−0.0013	0.042*
H14B	0.0886	0.7047	0.0698	0.042*
H14C	0.3082	0.6705	0.0664	0.042*
C15A	0.1543 (2)	0.50165 (14)	0.30235 (12)	0.0311 (4)
H15A	0.1412	0.4364	0.3389	0.047*
H15B	0.2539	0.4776	0.2600	0.047*
H15C	0.0387	0.5264	0.2767	0.047*
C16A	0.2807 (3)	0.97923 (15)	0.44755 (9)	0.0296 (4)
H16A	0.2969	1.0533	0.4708	0.044*
H16B	0.3838	0.9192	0.4602	0.044*
H16C	0.1650	0.9578	0.4710	0.044*
O1B	0.72943 (15)	0.80124 (9)	0.39270 (6)	0.0223 (2)
O2B	0.67530 (15)	0.56611 (9)	0.15954 (6)	0.0231 (2)
O3B	0.73981 (16)	0.96203 (9)	0.13077 (6)	0.0249 (2)
O4B	0.38451 (14)	1.24458 (9)	0.33850 (6)	0.0221 (2)
H2O4	0.389 (3)	1.186 (2)	0.3050 (14)	0.053 (7)*
N1B	0.69329 (16)	1.09095 (10)	0.27678 (7)	0.0186 (2)
C1B	0.73499 (19)	0.88062 (12)	0.26160 (8)	0.0178 (3)
C6B	0.72703 (19)	0.86652 (13)	0.17664 (8)	0.0187 (3)
C5B	0.7097 (2)	0.76005 (13)	0.14376 (8)	0.0202 (3)
H5BA	0.7063	0.7512	0.0865	0.024*
C4B	0.69737 (19)	0.66679 (12)	0.19584 (8)	0.0182 (3)
C3B	0.70674 (19)	0.67617 (12)	0.27957 (8)	0.0183 (3)
H3BA	0.7005	0.6115	0.3144	0.022*
C2B	0.72559 (19)	0.78316 (13)	0.31088 (8)	0.0176 (3)
C7B	0.74811 (19)	0.98811 (12)	0.30235 (8)	0.0182 (3)
H7BA	0.8028	0.9816	0.3530	0.022*
C8B	0.71474 (19)	1.18242 (12)	0.32963 (8)	0.0175 (3)
C9B	0.5554 (2)	1.26007 (12)	0.35589 (8)	0.0178 (3)
C10B	0.5708 (2)	1.35514 (13)	0.40419 (8)	0.0206 (3)
H10B	0.4644	1.4100	0.4201	0.025*
C11B	0.7414 (2)	1.36955 (13)	0.42898 (9)	0.0246 (3)
H11B	0.7507	1.4335	0.4627	0.030*
C12B	0.8977 (2)	1.29117 (14)	0.40481 (9)	0.0252 (3)
H12B	1.0138	1.3007	0.4226	0.030*
C13B	0.8846 (2)	1.19849 (14)	0.35456 (9)	0.0219 (3)
H13B	0.9924	1.1457	0.3371	0.026*
C14B	0.7287 (2)	0.70361 (14)	0.44500 (9)	0.0257 (3)
H14D	0.7280	0.7283	0.5018	0.039*
H14E	0.8390	0.6461	0.4311	0.039*
H14F	0.6185	0.6692	0.4380	0.039*
C15B	0.6564 (2)	0.47040 (13)	0.21263 (9)	0.0249 (3)
H15D	0.6355	0.4043	0.1805	0.037*
H15E	0.5516	0.4926	0.2528	0.037*
H15F	0.7691	0.4488	0.2409	0.037*
C16B	0.7402 (3)	0.95075 (15)	0.04466 (9)	0.0343 (4)
H16D	0.7459	1.0261	0.0190	0.051*
H16E	0.6274	0.9236	0.0312	0.051*
H16F	0.8477	0.8947	0.0245	0.051*

	U11	U22	U33	U12	U13	U23
O1A	0.0414 (6)	0.0140 (5)	0.0205 (5)	−0.0081 (5)	−0.0030 (4)	−0.0023 (4)
O2A	0.0367 (6)	0.0142 (5)	0.0373 (6)	−0.0064 (5)	−0.0023 (5)	0.0087 (5)
O3A	0.0320 (6)	0.0150 (5)	0.0194 (5)	−0.0032 (4)	−0.0044 (4)	−0.0008 (4)
O4A	0.0235 (5)	0.0143 (5)	0.0247 (5)	−0.0016 (4)	−0.0030 (4)	0.0060 (4)
N1A	0.0231 (6)	0.0106 (6)	0.0204 (5)	−0.0027 (5)	−0.0029 (4)	0.0024 (4)
C1A	0.0199 (6)	0.0114 (6)	0.0209 (6)	−0.0033 (5)	−0.0005 (5)	0.0003 (5)
C2A	0.0215 (7)	0.0139 (7)	0.0206 (6)	−0.0032 (5)	−0.0008 (5)	−0.0006 (5)
C3A	0.0216 (7)	0.0107 (7)	0.0291 (7)	−0.0023 (5)	−0.0009 (5)	0.0000 (5)
C4A	0.0183 (6)	0.0122 (7)	0.0306 (7)	−0.0015 (5)	0.0004 (5)	0.0058 (5)
C5A	0.0219 (7)	0.0172 (7)	0.0217 (6)	−0.0004 (6)	−0.0011 (5)	0.0044 (5)
C6A	0.0177 (6)	0.0134 (7)	0.0225 (6)	−0.0007 (5)	−0.0010 (5)	−0.0006 (5)
C7A	0.0229 (7)	0.0135 (7)	0.0187 (6)	−0.0026 (5)	−0.0013 (5)	−0.0005 (5)
C8A	0.0265 (7)	0.0102 (6)	0.0159 (6)	−0.0028 (5)	−0.0032 (5)	0.0002 (5)
C9A	0.0245 (7)	0.0102 (6)	0.0186 (6)	−0.0006 (5)	−0.0033 (5)	−0.0010 (5)
C10A	0.0307 (7)	0.0126 (7)	0.0204 (6)	−0.0044 (6)	−0.0022 (5)	0.0024 (5)
C11A	0.0354 (8)	0.0124 (7)	0.0197 (6)	−0.0002 (6)	−0.0058 (6)	0.0028 (5)
C12A	0.0281 (7)	0.0180 (7)	0.0217 (7)	0.0029 (6)	−0.0065 (5)	0.0003 (5)
C13A	0.0252 (7)	0.0178 (7)	0.0214 (6)	−0.0023 (6)	−0.0030 (5)	−0.0003 (5)
C14A	0.0417 (9)	0.0196 (8)	0.0251 (7)	−0.0108 (7)	0.0011 (6)	−0.0073 (6)
C15A	0.0290 (8)	0.0124 (7)	0.0527 (10)	−0.0054 (6)	−0.0043 (7)	0.0068 (7)
C16A	0.0450 (9)	0.0232 (8)	0.0199 (7)	−0.0011 (7)	−0.0070 (6)	−0.0005 (6)
O1B	0.0351 (6)	0.0147 (5)	0.0166 (5)	−0.0032 (4)	−0.0006 (4)	0.0012 (4)
O2B	0.0333 (6)	0.0137 (5)	0.0229 (5)	−0.0053 (4)	−0.0017 (4)	−0.0016 (4)
O3B	0.0439 (6)	0.0113 (5)	0.0179 (5)	−0.0004 (5)	−0.0014 (4)	0.0026 (4)
O4B	0.0219 (5)	0.0165 (5)	0.0274 (5)	−0.0010 (4)	−0.0028 (4)	−0.0063 (4)
N1B	0.0225 (6)	0.0125 (6)	0.0197 (5)	0.0002 (5)	−0.0013 (4)	−0.0018 (4)
C1B	0.0196 (6)	0.0121 (7)	0.0204 (6)	0.0005 (5)	−0.0006 (5)	0.0005 (5)
C6B	0.0211 (6)	0.0139 (7)	0.0195 (6)	0.0010 (5)	−0.0004 (5)	0.0011 (5)
C5B	0.0253 (7)	0.0155 (7)	0.0182 (6)	0.0012 (6)	−0.0014 (5)	−0.0007 (5)
C4B	0.0187 (6)	0.0132 (7)	0.0219 (6)	−0.0006 (5)	−0.0002 (5)	−0.0016 (5)
C3B	0.0204 (6)	0.0123 (6)	0.0214 (6)	−0.0012 (5)	0.0008 (5)	0.0013 (5)
C2B	0.0183 (6)	0.0158 (7)	0.0174 (6)	0.0007 (5)	0.0003 (5)	−0.0003 (5)
C7B	0.0217 (6)	0.0143 (7)	0.0181 (6)	−0.0011 (5)	−0.0010 (5)	0.0000 (5)
C8B	0.0242 (7)	0.0118 (6)	0.0162 (6)	−0.0017 (5)	−0.0020 (5)	0.0014 (5)
C9B	0.0241 (7)	0.0121 (6)	0.0170 (6)	−0.0026 (5)	−0.0019 (5)	0.0015 (5)
C10B	0.0304 (7)	0.0128 (7)	0.0181 (6)	−0.0033 (6)	0.0007 (5)	0.0004 (5)
C11B	0.0374 (8)	0.0169 (7)	0.0218 (7)	−0.0106 (6)	−0.0037 (6)	−0.0002 (5)
C12B	0.0300 (8)	0.0232 (8)	0.0250 (7)	−0.0103 (7)	−0.0070 (6)	0.0045 (6)
C13B	0.0237 (7)	0.0182 (7)	0.0236 (7)	−0.0034 (6)	−0.0020 (5)	0.0037 (5)
C14B	0.0392 (9)	0.0195 (8)	0.0185 (7)	−0.0050 (7)	−0.0030 (6)	0.0042 (6)
C15B	0.0310 (8)	0.0165 (7)	0.0288 (7)	−0.0086 (6)	−0.0019 (6)	0.0007 (6)
C16B	0.0635 (12)	0.0194 (8)	0.0185 (7)	−0.0026 (8)	−0.0030 (7)	0.0031 (6)

O1A—C2A	1.3620 (17)	O1B—C2B	1.3665 (16)
O1A—C14A	1.4324 (16)	O1B—C14B	1.4240 (18)
O2A—C4A	1.3616 (18)	O2B—C4B	1.3647 (16)
O2A—C15A	1.4345 (19)	O2B—C15B	1.4321 (18)
O3A—C6A	1.3641 (16)	O3B—C6B	1.3547 (17)
O3A—C16A	1.4276 (17)	O3B—C16B	1.4225 (17)
O4A—C9A	1.3579 (17)	O4B—C9B	1.3555 (17)
O4A—H1O4	0.88 (2)	O4B—H2O4	0.87 (2)
N1A—C7A	1.2868 (17)	N1B—C7B	1.2823 (19)
N1A—C8A	1.4251 (18)	N1B—C8B	1.4213 (17)
C1A—C6A	1.4149 (19)	C1B—C2B	1.401 (2)
C1A—C2A	1.4149 (18)	C1B—C6B	1.4145 (19)
C1A—C7A	1.447 (2)	C1B—C7B	1.4514 (19)
C2A—C3A	1.385 (2)	C6B—C5B	1.3918 (19)
C3A—C4A	1.383 (2)	C5B—C4B	1.392 (2)
C3A—H3AA	0.9500	C5B—H5BA	0.9500
C4A—C5A	1.402 (2)	C4B—C3B	1.3894 (19)
C5A—C6A	1.380 (2)	C3B—C2B	1.3903 (19)
C5A—H5AA	0.9500	C3B—H3BA	0.9500
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C13A	1.395 (2)	C8B—C13B	1.390 (2)
C8A—C9A	1.405 (2)	C8B—C9B	1.4040 (19)
C9A—C10A	1.393 (2)	C9B—C10B	1.3977 (18)
C10A—C11A	1.388 (2)	C10B—C11B	1.389 (2)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.382 (2)	C11B—C12B	1.385 (2)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.393 (2)	C12B—C13B	1.390 (2)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
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
C16A—H16A	0.9800	C16B—H16D	0.9800
C16A—H16B	0.9800	C16B—H16E	0.9800
C16A—H16C	0.9800	C16B—H16F	0.9800
C2A—O1A—C14A	117.14 (12)	C2B—O1B—C14B	117.47 (11)
C4A—O2A—C15A	117.14 (12)	C4B—O2B—C15B	116.49 (11)
C6A—O3A—C16A	117.32 (12)	C6B—O3B—C16B	117.65 (12)
C9A—O4A—H1O4	114.6 (14)	C9B—O4B—H2O4	111.6 (15)
C7A—N1A—C8A	115.68 (12)	C7B—N1B—C8B	115.77 (12)
C6A—C1A—C2A	116.46 (13)	C2B—C1B—C6B	117.29 (13)
C6A—C1A—C7A	126.30 (12)	C2B—C1B—C7B	117.12 (12)
C2A—C1A—C7A	117.12 (12)	C6B—C1B—C7B	125.57 (13)
O1A—C2A—C3A	122.60 (12)	O3B—C6B—C5B	123.26 (12)
O1A—C2A—C1A	114.70 (12)	O3B—C6B—C1B	115.65 (12)
C3A—C2A—C1A	122.69 (13)	C5B—C6B—C1B	121.09 (14)
C4A—C3A—C2A	118.44 (13)	C4B—C5B—C6B	119.10 (13)
C4A—C3A—H3AA	120.8	C4B—C5B—H5BA	120.4
C2A—C3A—H3AA	120.8	C6B—C5B—H5BA	120.4
O2A—C4A—C3A	123.05 (13)	O2B—C4B—C3B	122.34 (13)
O2A—C4A—C5A	115.53 (13)	O2B—C4B—C5B	115.84 (12)
C3A—C4A—C5A	121.40 (13)	C3B—C4B—C5B	121.83 (13)
C6A—C5A—C4A	119.17 (13)	C4B—C3B—C2B	117.98 (13)
C6A—C5A—H5AA	120.4	C4B—C3B—H3BA	121.0
C4A—C5A—H5AA	120.4	C2B—C3B—H3BA	121.0
O3A—C6A—C5A	122.97 (12)	O1B—C2B—C3B	121.90 (13)
O3A—C6A—C1A	115.27 (12)	O1B—C2B—C1B	115.37 (12)
C5A—C6A—C1A	121.75 (12)	C3B—C2B—C1B	122.69 (12)
N1A—C7A—C1A	127.95 (13)	N1B—C7B—C1B	126.50 (13)
N1A—C7A—H7AA	116.0	N1B—C7B—H7BA	116.7
C1A—C7A—H7AA	116.0	C1B—C7B—H7BA	116.7
C13A—C8A—C9A	119.40 (13)	C13B—C8B—C9B	119.66 (13)
C13A—C8A—N1A	121.91 (13)	C13B—C8B—N1B	123.03 (13)
C9A—C8A—N1A	118.64 (13)	C9B—C8B—N1B	117.30 (12)
O4A—C9A—C10A	117.89 (13)	O4B—C9B—C10B	118.09 (12)
O4A—C9A—C8A	122.80 (13)	O4B—C9B—C8B	122.48 (12)
C10A—C9A—C8A	119.30 (13)	C10B—C9B—C8B	119.40 (13)
C11A—C10A—C9A	120.70 (14)	C11B—C10B—C9B	120.17 (14)
C11A—C10A—H10A	119.6	C11B—C10B—H10B	119.9
C9A—C10A—H10A	119.6	C9B—C10B—H10B	119.9
C12A—C11A—C10A	120.20 (14)	C12B—C11B—C10B	120.32 (13)
C12A—C11A—H11A	119.9	C12B—C11B—H11B	119.8
C10A—C11A—H11A	119.9	C10B—C11B—H11B	119.8
C11A—C12A—C13A	119.72 (14)	C11B—C12B—C13B	119.90 (14)
C11A—C12A—H12A	120.1	C11B—C12B—H12B	120.1
C13A—C12A—H12A	120.1	C13B—C12B—H12B	120.1
C12A—C13A—C8A	120.66 (14)	C12B—C13B—C8B	120.49 (14)
C12A—C13A—H13A	119.7	C12B—C13B—H13B	119.8
C8A—C13A—H13A	119.7	C8B—C13B—H13B	119.8
O1A—C14A—H14A	109.5	O1B—C14B—H14D	109.5
O1A—C14A—H14B	109.5	O1B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
O1A—C14A—H14C	109.5	O1B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
O2A—C15A—H15A	109.5	O2B—C15B—H15D	109.5
O2A—C15A—H15B	109.5	O2B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O2A—C15A—H15C	109.5	O2B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
O3A—C16A—H16A	109.5	O3B—C16B—H16D	109.5
O3A—C16A—H16B	109.5	O3B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O3A—C16A—H16C	109.5	O3B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C14A—O1A—C2A—C3A	−3.2 (2)	C16B—O3B—C6B—C5B	−1.7 (2)
C14A—O1A—C2A—C1A	176.06 (13)	C16B—O3B—C6B—C1B	177.43 (14)
C6A—C1A—C2A—O1A	−176.76 (12)	C2B—C1B—C6B—O3B	−178.87 (12)
C7A—C1A—C2A—O1A	6.93 (18)	C7B—C1B—C6B—O3B	2.5 (2)
C6A—C1A—C2A—C3A	2.5 (2)	C2B—C1B—C6B—C5B	0.3 (2)
C7A—C1A—C2A—C3A	−173.82 (13)	C7B—C1B—C6B—C5B	−178.30 (13)
O1A—C2A—C3A—C4A	178.87 (13)	O3B—C6B—C5B—C4B	−179.96 (13)
C1A—C2A—C3A—C4A	−0.3 (2)	C1B—C6B—C5B—C4B	0.9 (2)
C15A—O2A—C4A—C3A	−6.7 (2)	C15B—O2B—C4B—C3B	1.86 (19)
C15A—O2A—C4A—C5A	174.54 (13)	C15B—O2B—C4B—C5B	−178.03 (12)
C2A—C3A—C4A—O2A	179.90 (13)	C6B—C5B—C4B—O2B	178.19 (12)
C2A—C3A—C4A—C5A	−1.5 (2)	C6B—C5B—C4B—C3B	−1.7 (2)
O2A—C4A—C5A—C6A	179.65 (12)	O2B—C4B—C3B—C2B	−178.70 (12)
C3A—C4A—C5A—C6A	0.9 (2)	C5B—C4B—C3B—C2B	1.2 (2)
C16A—O3A—C6A—C5A	−1.5 (2)	C14B—O1B—C2B—C3B	5.07 (19)
C16A—O3A—C6A—C1A	177.08 (13)	C14B—O1B—C2B—C1B	−177.21 (12)
C4A—C5A—C6A—O3A	179.96 (13)	C4B—C3B—C2B—O1B	177.67 (13)
C4A—C5A—C6A—C1A	1.4 (2)	C4B—C3B—C2B—C1B	0.1 (2)
C2A—C1A—C6A—O3A	178.33 (12)	C6B—C1B—C2B—O1B	−178.54 (12)
C7A—C1A—C6A—O3A	−5.7 (2)	C7B—C1B—C2B—O1B	0.18 (18)
C2A—C1A—C6A—C5A	−3.0 (2)	C6B—C1B—C2B—C3B	−0.8 (2)
C7A—C1A—C6A—C5A	172.89 (14)	C7B—C1B—C2B—C3B	177.88 (13)
C8A—N1A—C7A—C1A	−175.58 (13)	C8B—N1B—C7B—C1B	177.48 (13)
C6A—C1A—C7A—N1A	23.4 (2)	C2B—C1B—C7B—N1B	−152.97 (14)
C2A—C1A—C7A—N1A	−160.71 (14)	C6B—C1B—C7B—N1B	25.6 (2)
C7A—N1A—C8A—C13A	58.87 (17)	C7B—N1B—C8B—C13B	59.30 (19)
C7A—N1A—C8A—C9A	−123.60 (14)	C7B—N1B—C8B—C9B	−121.81 (14)
C13A—C8A—C9A—O4A	−178.98 (12)	C13B—C8B—C9B—O4B	−175.24 (13)
N1A—C8A—C9A—O4A	3.44 (19)	N1B—C8B—C9B—O4B	5.8 (2)
C13A—C8A—C9A—C10A	−0.43 (19)	C13B—C8B—C9B—C10B	2.5 (2)
N1A—C8A—C9A—C10A	−178.01 (12)	N1B—C8B—C9B—C10B	−176.43 (12)
O4A—C9A—C10A—C11A	179.19 (12)	O4B—C9B—C10B—C11B	174.92 (13)
C8A—C9A—C10A—C11A	0.6 (2)	C8B—C9B—C10B—C11B	−2.9 (2)
C9A—C10A—C11A—C12A	0.0 (2)	C9B—C10B—C11B—C12B	1.2 (2)
C10A—C11A—C12A—C13A	−0.8 (2)	C10B—C11B—C12B—C13B	0.9 (2)
C11A—C12A—C13A—C8A	0.9 (2)	C11B—C12B—C13B—C8B	−1.3 (2)
C9A—C8A—C13A—C12A	−0.3 (2)	C9B—C8B—C13B—C12B	−0.4 (2)
N1A—C8A—C13A—C12A	177.19 (12)	N1B—C8B—C13B—C12B	178.47 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H1O4···O3B	0.88 (2)	2.53 (2)	2.9924 (15)	114.0 (17)
O4A—H1O4···N1B	0.88 (2)	1.96 (2)	2.7897 (15)	158 (2)
O4B—H2O4···N1A	0.88 (2)	2.00 (2)	2.8013 (16)	151 (2)
O4B—H2O4···N1B	0.88 (2)	2.35 (2)	2.7891 (16)	111.1 (18)
C13B—H13B···O3Ai	0.95	2.59	3.4639 (19)	154
C15B—H15D···O4Aii	0.98	2.43	3.3847 (18)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4A—H1O4⋯O3B	0.88 (2)	2.53 (2)	2.9924 (15)	114.0 (17)
O4A—H1O4⋯N1B	0.88 (2)	1.96 (2)	2.7897 (15)	158 (2)
O4B—H2O4⋯N1A	0.88 (2)	2.00 (2)	2.8013 (16)	151 (2)
O4B—H2O4⋯N1B	0.88 (2)	2.35 (2)	2.7891 (16)	111.1 (18)
C13B—H13B⋯O3A i	0.95	2.59	3.4639 (19)	154
C15B—H15D⋯O4A ii	0.98	2.43	3.3847 (18)	164

Symmetry codes: (i) ; (ii) .