A sterically congested cis-stilbene and its phospho­nium salt precursor

Triphenyl(2,4,5-tri­meth­oxy­benz­yl)phospho­nium chloride is formed in solvent-free form by the reaction under anhydrous conditions between tri­phenyl­phosphane and 2,4,5-tri­meth­oxy­benzyl chloride, but when it is crystallized from a mixture of ethyl acetate and chloro­form in the presence of air it forms a stoichiometric monohydrate, C₂₈H₂₈O₃P⁺·Cl⁻·H₂O, (I). The reactions between the anhydrous phospho­nium salt and alk­oxy-substituted benzaldehydes, using Wittig reactions in the presence of potassium tert-butoxide, provide a series of multiply substituted stilbenes, most of which were assigned the Z configuration on the basis of their NMR spectra. However, no such deduction could be made for the symmetrically substituted (Z)-2,2′,4,4′,5,5′-hexa­meth­oxy­stilbene, C₂₀H₂₄O₆, (II). Compound (II) does in fact have the Z configuration and the mol­ecular geometry provides evidence for steric congestion around the central double bond; in particular, the central alkene fragment is nonplanar, with a C—C=C—C torsion angle of 7.8 (4)°. In hydrated salt (I), the chloride anions and water mol­ecules are linked by O—H...Cl hydrogen bonds to form C₂¹(4) chains; each cation is linked by C—H...O hydrogen bonds to two different chains, so forming a sheet structure. There are no direction-specific inter­molecular inter­actions in the structure of (II).

Computing details

For both compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis RED (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) Triphenyl(3,4,5-trimethoxybenzyl)phosphonium chloride monohydrate

Crystal data

C28H28O3P^+·Cl^−·H2O	F(000) = 1048
Mr = 496.94	Dx = 1.339 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 14.5660 (4) Å	Cell parameters from 4719 reflections
b = 15.8567 (3) Å	θ = 3.1–71.4°
c = 11.0472 (3) Å	µ = 2.25 mm^−1
β = 104.872 (3)°	T = 173 K
V = 2466.08 (11) Å^3	Block, pink
Z = 4	0.40 × 0.31 × 0.25 mm

Data collection

Agilent Eos Gemini diffractometer	4209 reflections with I > 2σ(I)
Radiation source: Enhance (Cu) X-ray source	Rint = 0.033
ω scans	θmax = 71.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −17→17
Tmin = 0.338, Tmax = 0.570	k = −19→12
9522 measured reflections	l = −11→13
4719 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0655P)^2 + 0.9657P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4719 reflections	Δρmax = 0.56 e Å^−3
310 parameters	Δρmin = −0.31 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.29050 (3)	0.38423 (3)	0.59848 (4)	0.01596 (12)
C7	0.19422 (12)	0.45803 (11)	0.59314 (16)	0.0195 (3)
H7A	0.1703	0.4499	0.6685	0.023*
H7B	0.2192	0.5162	0.5955	0.023*
C1	0.11271 (12)	0.44805 (11)	0.47800 (16)	0.0196 (3)
C2	0.03977 (12)	0.39217 (11)	0.47886 (16)	0.0202 (3)
C3	−0.03768 (12)	0.38402 (12)	0.37375 (17)	0.0227 (4)
H3	−0.0880	0.3462	0.3751	0.027*
C4	−0.04009 (13)	0.43175 (13)	0.26794 (17)	0.0247 (4)
C5	0.03427 (13)	0.48777 (12)	0.26544 (17)	0.0249 (4)
C6	0.10916 (12)	0.49630 (11)	0.37115 (17)	0.0220 (4)
H6	0.1586	0.5354	0.3710	0.026*
O2	0.04801 (9)	0.34810 (9)	0.58800 (12)	0.0250 (3)
C211	−0.01722 (15)	0.28096 (14)	0.5863 (2)	0.0335 (5)
H21A	−0.0143	0.2412	0.5194	0.050*
H21B	−0.0817	0.3038	0.5711	0.050*
H21C	−0.0005	0.2517	0.6671	0.050*
O4	−0.11330 (10)	0.43079 (11)	0.16142 (13)	0.0356 (3)
C411	−0.18810 (15)	0.37152 (15)	0.1551 (2)	0.0346 (5)
H41A	−0.2196	0.3836	0.2216	0.052*
H41B	−0.1618	0.3143	0.1660	0.052*
H41C	−0.2343	0.3759	0.0734	0.052*
O5	0.02547 (10)	0.53155 (10)	0.15638 (13)	0.0358 (4)
C511	0.10087 (17)	0.58634 (15)	0.1496 (2)	0.0374 (5)
H51A	0.1609	0.5550	0.1703	0.056*
H51B	0.1045	0.6328	0.2092	0.056*
H51C	0.0894	0.6092	0.0646	0.056*
C11	0.35395 (12)	0.41233 (11)	0.48458 (15)	0.0191 (3)
C12	0.35342 (12)	0.49557 (11)	0.44333 (17)	0.0215 (4)
H12	0.3180	0.5374	0.4732	0.026*
C13	0.40520 (13)	0.51680 (12)	0.35813 (18)	0.0252 (4)
H13	0.4032	0.5729	0.3272	0.030*
C14	0.45964 (13)	0.45657 (13)	0.31817 (17)	0.0263 (4)
H14	0.4950	0.4716	0.2601	0.032*
C15	0.46292 (13)	0.37421 (12)	0.36246 (18)	0.0261 (4)
H15	0.5020	0.3336	0.3368	0.031*
C16	0.40888 (12)	0.35148 (12)	0.44433 (17)	0.0219 (4)
H16	0.4093	0.2949	0.4727	0.026*
C21	0.36953 (12)	0.38576 (11)	0.75326 (16)	0.0189 (3)
C22	0.34202 (13)	0.42230 (13)	0.85333 (18)	0.0270 (4)
H22	0.2821	0.4494	0.8400	0.032*
C23	0.40302 (15)	0.41875 (15)	0.97277 (19)	0.0339 (5)
H23	0.3846	0.4434	1.0413	0.041*
C24	0.49029 (15)	0.37959 (14)	0.99246 (19)	0.0320 (4)
H24	0.5313	0.3770	1.0745	0.038*
C25	0.51838 (13)	0.34412 (13)	0.89312 (18)	0.0271 (4)
H25	0.5789	0.3180	0.9070	0.033*
C26	0.45825 (12)	0.34671 (11)	0.77333 (17)	0.0223 (4)
H26	0.4773	0.3221	0.7052	0.027*
C31	0.24490 (12)	0.27924 (10)	0.56497 (16)	0.0178 (3)
C32	0.19173 (12)	0.25865 (12)	0.44395 (16)	0.0211 (4)
H32	0.1837	0.2987	0.3782	0.025*
C33	0.15094 (13)	0.17956 (12)	0.42086 (17)	0.0253 (4)
H33	0.1149	0.1655	0.3388	0.030*
C34	0.16222 (14)	0.12040 (12)	0.5165 (2)	0.0283 (4)
H34	0.1334	0.0664	0.5002	0.034*
C35	0.21587 (14)	0.14078 (13)	0.63610 (18)	0.0273 (4)
H35	0.2243	0.1004	0.7015	0.033*
C36	0.25721 (12)	0.21989 (12)	0.66038 (16)	0.0224 (4)
H36	0.2939	0.2335	0.7423	0.027*
O1W	0.62816 (13)	0.26774 (13)	0.66686 (17)	0.0509 (5)
H111	0.6715	0.2749	0.6248	0.076*
H112	0.6670	0.2485	0.7474	0.076*
Cl1	0.72871 (3)	0.31459 (3)	0.43891 (5)	0.03452 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0146 (2)	0.0171 (2)	0.0155 (2)	−0.00040 (14)	0.00259 (15)	0.00018 (15)
C7	0.0173 (8)	0.0202 (8)	0.0206 (8)	0.0022 (6)	0.0042 (6)	−0.0004 (6)
C1	0.0170 (8)	0.0201 (8)	0.0213 (8)	0.0045 (6)	0.0039 (6)	−0.0004 (7)
C2	0.0191 (8)	0.0220 (8)	0.0195 (8)	0.0048 (6)	0.0048 (7)	0.0005 (6)
C3	0.0176 (8)	0.0250 (9)	0.0251 (9)	0.0004 (6)	0.0050 (7)	−0.0029 (7)
C4	0.0198 (8)	0.0316 (10)	0.0201 (8)	0.0049 (7)	0.0003 (7)	−0.0019 (7)
C5	0.0239 (9)	0.0294 (9)	0.0211 (9)	0.0063 (7)	0.0054 (7)	0.0042 (7)
C6	0.0186 (8)	0.0217 (9)	0.0256 (9)	0.0035 (6)	0.0055 (7)	0.0026 (7)
O2	0.0215 (6)	0.0289 (7)	0.0233 (6)	−0.0025 (5)	0.0034 (5)	0.0039 (5)
C211	0.0282 (10)	0.0370 (11)	0.0340 (11)	−0.0085 (8)	0.0057 (8)	0.0085 (9)
O4	0.0262 (7)	0.0525 (9)	0.0225 (7)	−0.0040 (6)	−0.0042 (5)	0.0047 (6)
C411	0.0251 (9)	0.0453 (12)	0.0288 (10)	−0.0018 (9)	−0.0015 (8)	−0.0072 (9)
O5	0.0313 (7)	0.0495 (9)	0.0243 (7)	0.0014 (6)	0.0026 (6)	0.0146 (6)
C511	0.0430 (12)	0.0365 (11)	0.0341 (11)	0.0039 (9)	0.0122 (9)	0.0121 (9)
C11	0.0163 (7)	0.0233 (9)	0.0170 (8)	−0.0021 (6)	0.0030 (6)	−0.0001 (6)
C12	0.0185 (8)	0.0218 (9)	0.0226 (8)	−0.0011 (6)	0.0021 (7)	−0.0004 (7)
C13	0.0234 (8)	0.0255 (9)	0.0246 (9)	−0.0054 (7)	0.0024 (7)	0.0045 (7)
C14	0.0231 (9)	0.0348 (10)	0.0219 (9)	−0.0094 (7)	0.0076 (7)	−0.0031 (7)
C15	0.0230 (9)	0.0299 (10)	0.0267 (9)	−0.0034 (7)	0.0088 (7)	−0.0080 (8)
C16	0.0217 (8)	0.0210 (8)	0.0222 (8)	−0.0022 (7)	0.0045 (7)	−0.0021 (7)
C21	0.0183 (8)	0.0197 (8)	0.0171 (8)	−0.0042 (6)	0.0016 (6)	0.0010 (6)
C22	0.0232 (9)	0.0333 (10)	0.0226 (9)	0.0008 (7)	0.0024 (7)	−0.0033 (8)
C23	0.0345 (10)	0.0452 (12)	0.0197 (9)	−0.0020 (9)	0.0029 (8)	−0.0080 (8)
C24	0.0302 (10)	0.0368 (11)	0.0228 (9)	−0.0046 (8)	−0.0045 (8)	0.0004 (8)
C25	0.0210 (8)	0.0279 (10)	0.0285 (9)	−0.0006 (7)	−0.0009 (7)	0.0045 (8)
C26	0.0206 (8)	0.0232 (9)	0.0218 (8)	−0.0023 (7)	0.0033 (7)	0.0014 (7)
C31	0.0168 (7)	0.0158 (8)	0.0209 (8)	−0.0010 (6)	0.0050 (6)	−0.0005 (6)
C32	0.0208 (8)	0.0235 (9)	0.0185 (8)	0.0028 (7)	0.0040 (6)	0.0007 (7)
C33	0.0239 (9)	0.0273 (9)	0.0215 (9)	−0.0007 (7)	0.0002 (7)	−0.0059 (7)
C34	0.0277 (9)	0.0224 (9)	0.0327 (10)	−0.0054 (7)	0.0039 (8)	−0.0026 (8)
C35	0.0305 (9)	0.0236 (9)	0.0264 (9)	−0.0035 (7)	0.0045 (7)	0.0042 (7)
C36	0.0227 (8)	0.0243 (9)	0.0182 (8)	−0.0013 (7)	0.0018 (6)	0.0009 (7)
O1W	0.0402 (9)	0.0675 (12)	0.0457 (10)	0.0153 (8)	0.0127 (8)	0.0077 (9)
Cl1	0.0279 (2)	0.0370 (3)	0.0400 (3)	−0.00231 (18)	0.0112 (2)	−0.0033 (2)

Geometric parameters (Å, º)

P1—C31	1.7954 (17)	C12—H12	0.9500
P1—C11	1.7981 (17)	C13—C14	1.384 (3)
P1—C21	1.7998 (17)	C13—H13	0.9500
P1—C7	1.8159 (17)	C14—C15	1.391 (3)
C7—C1	1.509 (2)	C14—H14	0.9500
C7—H7A	0.9900	C15—C16	1.390 (3)
C7—H7B	0.9900	C15—H15	0.9500
C1—C2	1.385 (3)	C16—H16	0.9500
C1—C6	1.396 (3)	C21—C22	1.395 (3)
C2—O2	1.372 (2)	C21—C26	1.398 (2)
C2—C3	1.402 (2)	C22—C23	1.390 (3)
C3—C4	1.385 (3)	C22—H22	0.9500
C3—H3	0.9500	C23—C24	1.381 (3)
C4—O4	1.370 (2)	C23—H23	0.9500
C4—C5	1.407 (3)	C24—C25	1.385 (3)
C5—O5	1.368 (2)	C24—H24	0.9500
C5—C6	1.385 (3)	C25—C26	1.387 (3)
C6—H6	0.9500	C25—H25	0.9500
O2—C211	1.424 (2)	C26—H26	0.9500
C211—H21A	0.9800	C31—C36	1.390 (2)
C211—H21B	0.9800	C31—C32	1.401 (2)
C211—H21C	0.9800	C32—C33	1.383 (3)
O4—C411	1.427 (3)	C32—H32	0.9500
C411—H41A	0.9800	C33—C34	1.391 (3)
C411—H41B	0.9800	C33—H33	0.9500
C411—H41C	0.9800	C34—C35	1.389 (3)
O5—C511	1.417 (3)	C34—H34	0.9500
C511—H51A	0.9800	C35—C36	1.388 (3)
C511—H51B	0.9800	C35—H35	0.9500
C511—H51C	0.9800	C36—H36	0.9500
C11—C12	1.396 (3)	O1W—H111	0.8817
C11—C16	1.397 (3)	O1W—H112	0.9726
C12—C13	1.390 (3)
C31—P1—C11	108.36 (8)	C16—C11—P1	119.39 (14)
C31—P1—C21	108.73 (8)	C13—C12—C11	119.44 (17)
C11—P1—C21	110.07 (8)	C13—C12—H12	120.3
C31—P1—C7	110.43 (8)	C11—C12—H12	120.3
C11—P1—C7	110.42 (8)	C14—C13—C12	120.25 (18)
C21—P1—C7	108.81 (8)	C14—C13—H13	119.9
C1—C7—P1	113.18 (12)	C12—C13—H13	119.9
C1—C7—H7A	108.9	C13—C14—C15	120.42 (17)
P1—C7—H7A	108.9	C13—C14—H14	119.8
C1—C7—H7B	108.9	C15—C14—H14	119.8
P1—C7—H7B	108.9	C16—C15—C14	119.88 (18)
H7A—C7—H7B	107.8	C16—C15—H15	120.1
C2—C1—C6	119.61 (16)	C14—C15—H15	120.1
C2—C1—C7	120.01 (16)	C15—C16—C11	119.61 (17)
C6—C1—C7	120.36 (16)	C15—C16—H16	120.2
C1—C2—O2	115.94 (15)	C11—C16—H16	120.2
C3—C2—O2	123.46 (16)	C22—C21—C26	120.00 (16)
C2—O2—C211	117.48 (14)	C22—C21—P1	120.98 (14)
C1—C2—C3	120.58 (16)	C26—C21—P1	118.97 (14)
C4—C3—C2	119.29 (17)	C23—C22—C21	119.46 (18)
C4—C3—H3	120.4	C23—C22—H22	120.3
C2—C3—H3	120.4	C21—C22—H22	120.3
C3—C4—O4	124.33 (17)	C24—C23—C22	120.40 (19)
C5—C4—O4	115.07 (17)	C24—C23—H23	119.8
C4—O4—C411	117.75 (16)	C22—C23—H23	119.8
C3—C4—C5	120.58 (16)	C23—C24—C25	120.33 (18)
C4—C5—O5	116.06 (16)	C23—C24—H24	119.8
C6—C5—O5	124.66 (18)	C25—C24—H24	119.8
C5—O5—C511	117.31 (16)	C24—C25—C26	120.07 (18)
C6—C5—C4	119.28 (17)	C24—C25—H25	120.0
C5—C6—C1	120.63 (17)	C26—C25—H25	120.0
C5—C6—H6	119.7	C25—C26—C21	119.72 (17)
C1—C6—H6	119.7	C25—C26—H26	120.1
O2—C211—H21A	109.5	C21—C26—H26	120.1
O2—C211—H21B	109.5	C36—C31—C32	119.87 (16)
H21A—C211—H21B	109.5	C36—C31—P1	120.17 (13)
O2—C211—H21C	109.5	C32—C31—P1	119.84 (13)
H21A—C211—H21C	109.5	C33—C32—C31	119.57 (16)
H21B—C211—H21C	109.5	C33—C32—H32	120.2
O4—C411—H41A	109.5	C31—C32—H32	120.2
O4—C411—H41B	109.5	C32—C33—C34	120.66 (17)
H41A—C411—H41B	109.5	C32—C33—H33	119.7
O4—C411—H41C	109.5	C34—C33—H33	119.7
H41A—C411—H41C	109.5	C35—C34—C33	119.57 (17)
H41B—C411—H41C	109.5	C35—C34—H34	120.2
O5—C511—H51A	109.5	C33—C34—H34	120.2
O5—C511—H51B	109.5	C36—C35—C34	120.29 (17)
H51A—C511—H51B	109.5	C36—C35—H35	119.9
O5—C511—H51C	109.5	C34—C35—H35	119.9
H51A—C511—H51C	109.5	C35—C36—C31	120.03 (16)
H51B—C511—H51C	109.5	C35—C36—H36	120.0
C12—C11—C16	120.33 (16)	C31—C36—H36	120.0
C12—C11—P1	120.14 (14)	H111—O1W—H112	101.3
C1—C7—P1—C11	71.96 (14)	C16—C11—C12—C13	2.4 (3)
C1—C7—P1—C21	−167.13 (12)	P1—C11—C12—C13	178.04 (13)
C1—C7—P1—C31	−47.87 (15)	C11—C12—C13—C14	−2.4 (3)
P1—C7—C1—C2	88.41 (17)	C12—C13—C14—C15	0.2 (3)
C3—C2—O2—C211	10.9 (3)	C13—C14—C15—C16	2.0 (3)
P1—C7—C1—C6	−93.06 (18)	C14—C15—C16—C11	−2.0 (3)
C6—C1—C2—O2	−179.09 (15)	C12—C11—C16—C15	−0.2 (3)
C7—C1—C2—O2	−0.6 (2)	P1—C11—C16—C15	−175.86 (13)
C6—C1—C2—C3	−0.3 (3)	C31—P1—C21—C22	−105.49 (16)
C7—C1—C2—C3	178.20 (16)	C11—P1—C21—C22	135.96 (15)
O2—C2—C3—C4	179.48 (16)	C31—P1—C21—C26	72.04 (15)
C1—C2—C3—C4	0.8 (3)	C11—P1—C21—C26	−46.51 (16)
C2—C3—C4—O4	−178.01 (18)	C7—P1—C21—C26	−167.64 (14)
C2—C3—C4—C5	0.1 (3)	C26—C21—C22—C23	−0.6 (3)
O4—C4—C5—O5	−2.1 (3)	P1—C21—C22—C23	176.88 (16)
C3—C4—C5—O5	179.59 (17)	C21—C22—C23—C24	0.1 (3)
O4—C4—C5—C6	176.78 (17)	C22—C23—C24—C25	0.6 (3)
C3—C4—C5—C6	−1.5 (3)	C23—C24—C25—C26	−0.9 (3)
O5—C5—C6—C1	−179.20 (17)	C24—C25—C26—C21	0.4 (3)
C4—C5—C6—C1	2.0 (3)	C22—C21—C26—C25	0.3 (3)
C2—C1—C6—C5	−1.1 (3)	P1—C21—C26—C25	−177.22 (14)
C7—C1—C6—C5	−179.63 (16)	C11—P1—C31—C36	132.16 (14)
C1—C2—O2—C211	−170.40 (17)	C21—P1—C31—C36	12.54 (16)
C7—P1—C11—C12	24.95 (16)	C7—P1—C31—C36	−106.77 (15)
C7—P1—C21—C22	14.84 (18)	C11—P1—C31—C32	−51.79 (15)
C7—P1—C31—C32	69.27 (15)	C21—P1—C31—C32	−171.41 (14)
C3—C4—O4—C411	−5.6 (3)	C36—C31—C32—C33	0.8 (3)
C5—C4—O4—C411	176.20 (17)	P1—C31—C32—C33	−175.30 (14)
C6—C5—O5—C511	3.3 (3)	C31—C32—C33—C34	0.0 (3)
C4—C5—O5—C511	−177.91 (18)	C32—C33—C34—C35	−0.7 (3)
C31—P1—C11—C12	146.02 (14)	C33—C34—C35—C36	0.6 (3)
C21—P1—C11—C12	−95.20 (15)	C34—C35—C36—C31	0.1 (3)
C31—P1—C11—C16	−38.31 (16)	C32—C31—C36—C35	−0.8 (3)
C21—P1—C11—C16	80.46 (15)	P1—C31—C36—C35	175.22 (14)
C7—P1—C11—C16	−159.38 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H111···Cl1	0.88	2.49	3.306 (2)	155
O1W—H112···Cl1^i	0.97	2.30	3.2592 (19)	167
C13—H13···O1W^ii	0.95	2.57	3.452 (3)	154
C26—H26···O1W	0.95	2.50	3.251 (3)	136
C12—H12···Cl1^ii	0.95	2.69	3.6033 (18)	161

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

(II) (Z)-2,2',4,4',5,5'-Hexamethoxystilbene

Crystal data

C20H24O6	F(000) = 768
Mr = 360.39	Dx = 1.311 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 17.0340 (7) Å	Cell parameters from 3466 reflections
b = 5.0747 (2) Å	θ = 4.1–71.2°
c = 22.6111 (10) Å	µ = 0.80 mm^−1
β = 110.917 (5)°	T = 173 K
V = 1825.75 (14) Å^3	Needle, colourless
Z = 4	0.49 × 0.06 × 0.04 mm

Data collection

Agilent Eos Gemini diffractometer	2814 reflections with I > 2σ(I)
Radiation source: Enhance (Cu) X-ray source	Rint = 0.031
ω scans	θmax = 71.2°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −15→20
Tmin = 0.713, Tmax = 0.969	k = −5→6
6599 measured reflections	l = −26→27
3453 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0869P)^2 + 0.1034P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3453 reflections	Δρmax = 0.27 e Å^−3
241 parameters	Δρmin = −0.25 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.38819 (10)	0.5381 (4)	0.43151 (8)	0.0290 (4)
H1	0.4463	0.5305	0.4566	0.035*
C11	0.36955 (10)	0.6376 (3)	0.36673 (8)	0.0238 (4)
C12	0.42253 (10)	0.8261 (4)	0.35547 (8)	0.0254 (4)
C13	0.40825 (10)	0.9177 (3)	0.29432 (8)	0.0258 (4)
H13	0.4440	1.0486	0.2875	0.031*
C14	0.34197 (11)	0.8180 (3)	0.24348 (8)	0.0235 (4)
C15	0.28932 (10)	0.6233 (3)	0.25352 (8)	0.0226 (3)
C16	0.30433 (10)	0.5350 (3)	0.31446 (8)	0.0229 (3)
H16	0.2694	0.4009	0.3211	0.027*
O12	0.48770 (9)	0.9093 (3)	0.40748 (7)	0.0395 (4)
C121	0.53989 (12)	1.1147 (4)	0.40051 (10)	0.0344 (4)
H12A	0.5660	1.0609	0.3702	0.052*
H12B	0.5837	1.1520	0.4416	0.052*
H12C	0.5061	1.2735	0.3849	0.052*
O14	0.32261 (9)	0.8951 (3)	0.18190 (6)	0.0325 (3)
C141	0.37063 (13)	1.1038 (4)	0.16999 (9)	0.0340 (4)
H14A	0.3501	1.1423	0.1245	0.051*
H14B	0.4299	1.0516	0.1840	0.051*
H14C	0.3650	1.2613	0.1932	0.051*
O15	0.22667 (8)	0.5331 (3)	0.20043 (6)	0.0321 (3)
C151	0.17237 (12)	0.3385 (4)	0.20989 (9)	0.0345 (4)
H15A	0.1304	0.2883	0.1690	0.052*
H15B	0.1440	0.4096	0.2373	0.052*
H15C	0.2053	0.1832	0.2300	0.052*
C2	0.33687 (11)	0.4565 (4)	0.46092 (8)	0.0266 (4)
H2	0.3648	0.3795	0.5013	0.032*
C21	0.24498 (10)	0.4653 (3)	0.44168 (7)	0.0211 (3)
C22	0.20550 (10)	0.2941 (3)	0.47111 (8)	0.0214 (3)
C23	0.11869 (10)	0.3011 (3)	0.45601 (8)	0.0244 (4)
H23	0.0929	0.1837	0.4763	0.029*
C24	0.06988 (10)	0.4784 (3)	0.41154 (8)	0.0247 (4)
C25	0.10805 (10)	0.6560 (3)	0.38227 (8)	0.0218 (3)
C26	0.19414 (10)	0.6489 (3)	0.39806 (8)	0.0215 (3)
H26	0.2198	0.7716	0.3789	0.026*
O22	0.25701 (7)	0.1233 (2)	0.51472 (6)	0.0279 (3)
C221	0.21943 (12)	−0.0434 (4)	0.54772 (9)	0.0304 (4)
H22A	0.1793	−0.1619	0.5176	0.046*
H22B	0.1900	0.0644	0.5692	0.046*
H22C	0.2631	−0.1476	0.5791	0.046*
O24	−0.01539 (8)	0.4969 (3)	0.39321 (7)	0.0377 (4)
C241	−0.05734 (12)	0.3007 (4)	0.41562 (11)	0.0387 (5)
H24A	−0.1182	0.3257	0.3960	0.058*
H24B	−0.0405	0.3152	0.4617	0.058*
H24C	−0.0422	0.1259	0.4046	0.058*
O25	0.05429 (8)	0.8244 (3)	0.33919 (6)	0.0300 (3)
C251	0.09023 (12)	0.9893 (4)	0.30469 (9)	0.0318 (4)
H25A	0.0458	1.0920	0.2735	0.048*
H25B	0.1188	0.8803	0.2828	0.048*
H25C	0.1309	1.1093	0.3340	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0158 (7)	0.0466 (10)	0.0230 (8)	−0.0009 (7)	0.0050 (7)	0.0050 (7)
C11	0.0180 (7)	0.0325 (9)	0.0227 (8)	0.0013 (6)	0.0093 (7)	0.0029 (7)
C12	0.0177 (8)	0.0340 (9)	0.0244 (8)	−0.0018 (6)	0.0074 (7)	−0.0006 (7)
C13	0.0234 (8)	0.0288 (8)	0.0276 (9)	−0.0041 (6)	0.0122 (7)	0.0013 (7)
C14	0.0268 (8)	0.0263 (8)	0.0212 (8)	−0.0003 (6)	0.0130 (7)	0.0006 (6)
C15	0.0199 (8)	0.0275 (8)	0.0203 (8)	−0.0018 (6)	0.0072 (7)	−0.0023 (6)
C16	0.0186 (7)	0.0285 (8)	0.0237 (8)	−0.0018 (6)	0.0102 (7)	0.0012 (6)
O12	0.0293 (7)	0.0557 (9)	0.0284 (7)	−0.0171 (6)	0.0039 (6)	0.0015 (6)
C121	0.0246 (9)	0.0380 (10)	0.0405 (10)	−0.0081 (7)	0.0114 (8)	−0.0100 (8)
O14	0.0399 (7)	0.0372 (7)	0.0217 (6)	−0.0097 (6)	0.0125 (6)	0.0028 (5)
C141	0.0438 (11)	0.0319 (9)	0.0326 (10)	−0.0052 (8)	0.0215 (9)	0.0033 (7)
O15	0.0322 (7)	0.0409 (7)	0.0217 (6)	−0.0135 (6)	0.0078 (5)	−0.0013 (5)
C151	0.0299 (9)	0.0385 (10)	0.0314 (10)	−0.0124 (8)	0.0063 (8)	−0.0004 (8)
C2	0.0229 (8)	0.0355 (9)	0.0199 (8)	−0.0012 (7)	0.0058 (7)	0.0044 (7)
C21	0.0218 (8)	0.0246 (8)	0.0185 (7)	−0.0029 (6)	0.0092 (6)	−0.0009 (6)
C22	0.0250 (8)	0.0212 (7)	0.0189 (8)	−0.0001 (6)	0.0087 (7)	0.0005 (6)
C23	0.0243 (8)	0.0249 (8)	0.0271 (8)	−0.0038 (6)	0.0130 (7)	0.0035 (6)
C24	0.0190 (8)	0.0278 (8)	0.0287 (9)	−0.0019 (6)	0.0103 (7)	0.0018 (7)
C25	0.0226 (8)	0.0211 (7)	0.0217 (8)	0.0004 (6)	0.0078 (7)	0.0019 (6)
C26	0.0239 (8)	0.0223 (7)	0.0216 (8)	−0.0027 (6)	0.0120 (7)	0.0010 (6)
O22	0.0237 (6)	0.0322 (6)	0.0275 (6)	−0.0010 (5)	0.0086 (5)	0.0100 (5)
C221	0.0320 (9)	0.0329 (9)	0.0269 (9)	−0.0031 (7)	0.0111 (8)	0.0097 (7)
O24	0.0196 (6)	0.0427 (8)	0.0524 (9)	0.0009 (5)	0.0149 (6)	0.0178 (6)
C241	0.0227 (8)	0.0478 (11)	0.0464 (12)	−0.0087 (8)	0.0135 (9)	0.0081 (9)
O25	0.0240 (6)	0.0303 (6)	0.0355 (7)	0.0030 (5)	0.0102 (6)	0.0120 (5)
C251	0.0324 (9)	0.0297 (9)	0.0322 (9)	0.0009 (7)	0.0103 (8)	0.0110 (7)

Geometric parameters (Å, º)

C1—C2	1.339 (2)	C2—C21	1.468 (2)
C1—C11	1.473 (2)	C2—H2	0.9500
C1—H1	0.9500	C21—C22	1.403 (2)
C11—C12	1.400 (2)	C21—C26	1.407 (2)
C11—C16	1.402 (2)	C22—O22	1.370 (2)
C12—O12	1.364 (2)	C22—C23	1.394 (2)
C12—C13	1.395 (2)	C23—C24	1.384 (2)
C13—C14	1.388 (3)	C23—H23	0.9500
C13—H13	0.9500	C24—O24	1.364 (2)
C14—O14	1.369 (2)	C24—C25	1.407 (2)
C14—C15	1.406 (2)	C25—O25	1.371 (2)
C15—O15	1.369 (2)	C25—C26	1.380 (2)
C15—C16	1.383 (2)	C26—H26	0.9500
C16—H16	0.9500	O22—C221	1.422 (2)
O12—C121	1.415 (2)	C221—H22A	0.9800
C121—H12A	0.9800	C221—H22B	0.9800
C121—H12B	0.9800	C221—H22C	0.9800
C121—H12C	0.9800	O24—C241	1.420 (2)
O14—C141	1.421 (2)	C241—H24A	0.9800
C141—H14A	0.9800	C241—H24B	0.9800
C141—H14B	0.9800	C241—H24C	0.9800
C141—H14C	0.9800	O25—C251	1.423 (2)
O15—C151	1.421 (2)	C251—H25A	0.9800
C151—H15A	0.9800	C251—H25B	0.9800
C151—H15B	0.9800	C251—H25C	0.9800
C151—H15C	0.9800
C2—C1—C11	130.75 (16)	C1—C2—C21	131.26 (16)
C2—C1—H1	114.6	C1—C2—H2	114.4
C11—C1—H1	114.6	C21—C2—H2	114.4
C12—C11—C16	117.97 (15)	C22—C21—C26	117.58 (14)
C12—C11—C1	119.42 (16)	C22—C21—C2	118.77 (15)
C16—C11—C1	122.40 (15)	C26—C21—C2	123.51 (15)
O12—C12—C11	115.72 (16)	O22—C22—C21	116.17 (14)
O12—C12—C13	123.46 (15)	O22—C22—C23	122.90 (14)
C13—C12—C11	120.82 (16)	C23—C22—C21	120.93 (15)
C14—C13—C12	120.12 (15)	C24—C23—C22	120.27 (15)
C14—C13—H13	119.9	C24—C23—H23	119.9
C12—C13—H13	119.9	C22—C23—H23	119.9
O14—C14—C13	124.60 (15)	O24—C24—C23	124.34 (15)
O14—C14—C15	115.41 (15)	O24—C24—C25	115.68 (15)
C13—C14—C15	119.99 (15)	C23—C24—C25	119.97 (15)
O15—C15—C14	115.84 (15)	O25—C25—C24	115.46 (14)
O15—C15—C16	125.03 (15)	O25—C25—C26	125.32 (14)
C16—C15—C14	119.13 (16)	C26—C25—C24	119.22 (15)
C15—C16—C11	121.91 (15)	C25—C26—C21	121.98 (14)
C15—C16—H16	119.0	C25—C26—H26	119.0
C11—C16—H16	119.0	C21—C26—H26	119.0
C12—O12—C121	118.83 (15)	C22—O22—C221	117.49 (13)
O12—C121—H12A	109.5	O22—C221—H22A	109.5
O12—C121—H12B	109.5	O22—C221—H22B	109.5
H12A—C121—H12B	109.5	H22A—C221—H22B	109.5
O12—C121—H12C	109.5	O22—C221—H22C	109.5
H12A—C121—H12C	109.5	H22A—C221—H22C	109.5
H12B—C121—H12C	109.5	H22B—C221—H22C	109.5
C14—O14—C141	117.38 (14)	C24—O24—C241	117.38 (15)
O14—C141—H14A	109.5	O24—C241—H24A	109.5
O14—C141—H14B	109.5	O24—C241—H24B	109.5
H14A—C141—H14B	109.5	H24A—C241—H24B	109.5
O14—C141—H14C	109.5	O24—C241—H24C	109.5
H14A—C141—H14C	109.5	H24A—C241—H24C	109.5
H14B—C141—H14C	109.5	H24B—C241—H24C	109.5
C15—O15—C151	116.48 (14)	C25—O25—C251	116.56 (13)
O15—C151—H15A	109.5	O25—C251—H25A	109.5
O15—C151—H15B	109.5	O25—C251—H25B	109.5
H15A—C151—H15B	109.5	H25A—C251—H25B	109.5
O15—C151—H15C	109.5	O25—C251—H25C	109.5
H15A—C151—H15C	109.5	H25A—C251—H25C	109.5
H15B—C151—H15C	109.5	H25B—C251—H25C	109.5
C2—C1—C11—C12	147.9 (2)	C1—C2—C21—C22	159.7 (2)
C2—C1—C11—C16	−37.5 (3)	C1—C2—C21—C26	−24.7 (3)
C16—C11—C12—O12	−176.60 (15)	C26—C21—C22—O22	−178.08 (14)
C1—C11—C12—O12	−1.8 (2)	C2—C21—C22—O22	−2.2 (2)
C16—C11—C12—C13	3.0 (2)	C26—C21—C22—C23	2.0 (2)
C1—C11—C12—C13	177.80 (16)	C2—C21—C22—C23	177.83 (15)
O12—C12—C13—C14	178.13 (16)	O22—C22—C23—C24	179.96 (16)
C11—C12—C13—C14	−1.4 (3)	C21—C22—C23—C24	−0.1 (3)
C12—C13—C14—O14	179.83 (16)	C22—C23—C24—O24	179.10 (17)
C12—C13—C14—C15	−0.3 (3)	C22—C23—C24—C25	−1.2 (3)
O14—C14—C15—O15	1.1 (2)	O24—C24—C25—O25	0.1 (2)
C13—C14—C15—O15	−178.75 (15)	C23—C24—C25—O25	−179.63 (15)
O14—C14—C15—C16	−179.75 (14)	O24—C24—C25—C26	−179.71 (16)
C13—C14—C15—C16	0.4 (2)	C23—C24—C25—C26	0.6 (3)
O15—C15—C16—C11	−179.67 (15)	O25—C25—C26—C21	−178.37 (15)
C14—C15—C16—C11	1.3 (2)	C24—C25—C26—C21	1.4 (2)
C12—C11—C16—C15	−2.9 (2)	C22—C21—C26—C25	−2.6 (2)
C1—C11—C16—C15	−177.59 (15)	C2—C21—C26—C25	−178.28 (16)
C13—C12—O12—C121	5.4 (3)	C23—C22—O22—C221	−3.2 (2)
C11—C12—O12—C121	−175.05 (16)	C21—C22—O22—C221	176.87 (15)
C13—C14—O14—C141	−4.2 (3)	C23—C24—O24—C241	−7.9 (3)
C15—C14—O14—C141	175.94 (15)	C25—C24—O24—C241	172.41 (17)
C16—C15—O15—C151	1.6 (2)	C26—C25—O25—C251	5.3 (2)
C14—C15—O15—C151	−179.30 (15)	C24—C25—O25—C251	−174.41 (15)
C11—C1—C2—C21	−7.8 (4)