Supramolecular cocrystals of O—H⋯O hydrogen-bonded 18-crown-6 with isophthalic acid derivatives: Hirshfeld surface analysis and third-order nonlinear optical properties

Balakrishnan, C.; Manonmani, M.; Rafi Ahamed, S.; Vinitha, G.; Meenakshisundaram, S.; Sockalingam, R.

doi:10.1107/S2052520620001821

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Supramolecular cocrystals of O—HO hydrogen-bonded 18-crown-6 with isophthalic acid derivatives: Hirshfeld surface analysis and third-order nonlinear optical properties

C. Balakrishnan, M. Manonmani, S. Rafi Ahamed, G. Vinitha, S. P. Meenakshisundaram and R. M. Sockalingam

Two cocrystals of 18-crown-6 with isophthalic acid derivatives, 5-hydroxyisophthalic acid and trimesic acid, have been successfully grown by the slow evaporation solution growth technique. Crystal structures of (18-crown-6)·6(5-hydroxyisophthalic acid)·10(H₂O) (I) and (18-crown-6)·2(trimesic acid)·2(H₂O) (II) elucidated by single crystal X-ray diffraction reveal that both cocrystals pack the centrosymmetric triclinic space group $P{\overline 1}$ . The molecules are associated by strong/weak hydrogen bonds, π

π and H

H stacking interactions. Powder X-ray diffraction analyses, experimental and simulated from single-crystal diffractogram data have been matched. The vibrational patterns in FT–IR spectra are used to identify the functional groups. The band gap energy is estimated by the application of the Kubelka–Munk algorithm. Hirshfeld surfaces derived from X-ray diffraction analysis reveal the type of molecular interactions and their relative contributions. The constructed supramolecular assembly of crown ether cocrystal is thoroughly described. Both cocrystals exhibit a significant third-order nonlinear optical response and it is observed that (I) possesses a significant first-order molecular hyperpolarizability whereas it is negligible for (II).

Keywords: supramolecular assembly; single-crystal X-ray diffraction; Hirshfeld surfaces; first-order molecular hyperpolarizability; Z-scan studies.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620001821/aw5031sup1.cif Contains datablocks I, II
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620001821/aw5031sup4.pdf Supporting Figures and Tables
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001821/aw5031Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001821/aw5031IIsup3.hkl Contains datablock II

CCDC references: 1840266; 1881994

Computing details top

For both structures, data collection: APEX3(Bruker, 2016); cell refinement: APEX3/SAINT (Bruker, 2016); data reduction: SAINT/XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT-2014/5 (Sheldrick, 2014); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2014).

(I) top

Crystal data top

C₁₂H₂₄O₆·6(C₈H₆O₅)·10(H₂O)	Z = 1
M_r = 1537.24	F(000) = 808
Triclinic, P1	D_x = 1.423 Mg m⁻³
a = 10.2989 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.3586 (3) Å	Cell parameters from 7200 reflections
c = 14.5679 (3) Å	θ = 3.1–25.2°
α = 115.521 (8)°	µ = 0.13 mm⁻¹
β = 103.490 (9)°	T = 296 K
γ = 100.116 (10)°	Block, colourless
V = 1794.39 (15) Å³	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker axs kappa apex3 CMOS Diffractometer	6303 independent reflections
Radiation source: fine-focus sealed tube	4548 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω and φ scan	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan SADABS (Bruker, 2016)	h = −12→12
T_min = 0.703, T_max = 0.745	k = −17→17
34311 measured reflections	l = −17→17

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0695P)² + 0.4321P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.130	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.33 e Å⁻³
6303 reflections	Δρ_min = −0.18 e Å⁻³
519 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
15 restraints	Extinction coefficient: 0.036 (3)

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.4179 (4)	1.0395 (3)	0.7783 (3)	0.0908 (10)
H1A	0.3337	1.0549	0.7910	0.109*
H1B	0.4106	1.0265	0.7059	0.109*
C2	0.3136 (3)	0.8508 (3)	0.7028 (2)	0.0800 (9)
H2A	0.3136	0.8381	0.6318	0.096*
H2B	0.2247	0.8610	0.7089	0.096*
C3	0.3310 (3)	0.7562 (2)	0.7160 (2)	0.0841 (10)
H3A	0.2610	0.6899	0.6556	0.101*
H3B	0.4234	0.7501	0.7162	0.101*
C4	0.3553 (3)	0.6945 (2)	0.8453 (3)	0.0829 (9)
H4A	0.4491	0.6945	0.8440	0.100*
H4B	0.2907	0.6218	0.7943	0.100*
C5	0.3530 (3)	0.7263 (2)	0.9571 (3)	0.0817 (9)
H5A	0.2612	0.7321	0.9594	0.098*
H5B	0.3692	0.6706	0.9750	0.098*
C6	0.4564 (4)	0.8651 (3)	1.1406 (3)	0.0866 (9)
H6A	0.4537	0.8067	1.1578	0.104*
H6B	0.3718	0.8851	1.1443	0.104*
C7	0.0825 (2)	0.12483 (15)	0.69289 (16)	0.0430 (5)
C8	0.1522 (2)	0.19584 (15)	0.80342 (15)	0.0400 (5)
H8	0.1620	0.1693	0.8518	0.048*
C9	0.2069 (2)	0.30615 (15)	0.84125 (14)	0.0360 (4)
C10	0.1922 (2)	0.34629 (15)	0.76942 (15)	0.0367 (4)
H10	0.2270	0.4205	0.7950	0.044*
C11	0.1249 (2)	0.27455 (15)	0.65874 (14)	0.0349 (4)
C12	0.0705 (2)	0.16409 (15)	0.62015 (15)	0.0403 (5)
H12	0.0262	0.1165	0.5461	0.048*
C13	0.1124 (2)	0.31725 (15)	0.58176 (15)	0.0377 (4)
C14	0.2843 (2)	0.38215 (16)	0.95902 (16)	0.0411 (5)
C15	0.0556 (2)	0.39603 (14)	0.19764 (15)	0.0356 (4)
H15	0.0214	0.3217	0.1718	0.043*
C16	0.0533 (2)	0.43469 (14)	0.12496 (15)	0.0361 (4)
C17	0.1018 (2)	0.54531 (15)	0.16345 (16)	0.0374 (4)
H17	0.0987	0.5718	0.1152	0.045*
C18	0.15510 (19)	0.61688 (14)	0.27484 (15)	0.0338 (4)
C19	0.1601 (2)	0.57863 (14)	0.34818 (15)	0.0352 (4)
H19	0.1973	0.6267	0.4225	0.042*
C20	0.1087 (2)	0.46770 (14)	0.30851 (15)	0.0346 (4)
C21	0.1084 (2)	0.42512 (15)	0.38493 (15)	0.0399 (5)
C22	0.2074 (2)	0.73567 (15)	0.31792 (16)	0.0380 (4)
C23	0.3733 (2)	1.16022 (14)	0.47208 (15)	0.0355 (4)
C24	0.3623 (2)	1.19893 (14)	0.39893 (15)	0.0377 (4)
H24	0.3297	1.1504	0.3248	0.045*
C25	0.4003 (2)	1.31022 (14)	0.43687 (15)	0.0376 (4)
C26	0.4538 (2)	1.38193 (15)	0.54759 (15)	0.0370 (4)
H26	0.4811	1.4565	0.5734	0.044*
C27	0.46670 (19)	1.34249 (14)	0.62022 (15)	0.0342 (4)
C28	0.4247 (2)	1.23141 (14)	0.58304 (15)	0.0359 (4)
H28	0.4309	1.2052	0.6317	0.043*
C29	0.3283 (2)	1.04096 (15)	0.42888 (16)	0.0421 (5)
C30	0.5270 (2)	1.41946 (15)	0.73910 (16)	0.0379 (4)
O1	0.42698 (18)	0.94519 (15)	0.78523 (13)	0.0662 (5)
O2	0.31536 (17)	0.76968 (12)	0.81577 (14)	0.0643 (5)
O3	0.45903 (18)	0.82823 (14)	1.03496 (16)	0.0654 (5)
O4	0.0263 (2)	0.01587 (11)	0.65036 (12)	0.0672 (5)
H4C	0.0264	0.0021	0.6995	0.101*
O5	0.30974 (18)	0.34277 (11)	1.02178 (11)	0.0557 (4)
H5C	0.3527	0.3923	1.0842	0.083*	0.5
O6	0.32201 (19)	0.48258 (11)	0.99059 (12)	0.0629 (5)
H6C	0.3636	0.5166	1.0564	0.094*	0.5
O7	0.16296 (17)	0.41784 (11)	0.61927 (11)	0.0531 (4)
H7A	0.1498	0.4315	0.5693	0.080*	0.5
O8	0.05249 (18)	0.24983 (12)	0.48100 (11)	0.0604 (5)
H8A	0.0672	0.2800	0.4460	0.091*	0.5
O9	0.00280 (17)	0.36782 (11)	0.01516 (11)	0.0519 (4)
H9C	−0.0018	0.3054	0.0014	0.078*
O10	0.05163 (17)	0.32501 (11)	0.34682 (11)	0.0545 (4)
H10A	0.0582	0.3116	0.3967	0.082*	0.5
O11	0.1640 (2)	0.49262 (11)	0.48586 (12)	0.0622 (5)
H11A	0.1495	0.4618	0.5202	0.093*	0.5
O12	0.25212 (17)	0.79844 (11)	0.41792 (12)	0.0525 (4)
H12A	0.2776	0.8615	0.4305	0.079*	0.5
O13	0.20216 (19)	0.76777 (11)	0.24754 (12)	0.0604 (5)
H13A	0.2301	0.8344	0.2788	0.091*	0.5
O14	0.28991 (19)	0.97848 (11)	0.32952 (12)	0.0600 (5)
H14A	0.2680	0.9153	0.3169	0.090*	0.5
O15	0.33341 (19)	1.00854 (11)	0.49908 (12)	0.0618 (5)
H15A	0.3101	0.9420	0.4680	0.093*	0.5
O16	0.54297 (17)	1.38102 (11)	0.80294 (11)	0.0533 (4)
H16A	0.5767	1.4310	0.8658	0.080*	0.5
O17	0.56176 (18)	1.52015 (11)	0.77044 (12)	0.0582 (4)
H17A	0.6029	1.5546	0.8363	0.087*	0.5
O18	0.38862 (17)	1.35306 (11)	0.36889 (11)	0.0522 (4)
H18C	0.3410	1.3049	0.3068	0.078*
O19	0.16804 (17)	0.89926 (13)	0.91178 (14)	0.0522 (4)
O20	0.60801 (16)	0.92715 (13)	0.94844 (14)	0.0560 (4)
O21	−0.0168 (2)	0.96437 (13)	0.80519 (14)	0.0588 (4)
O22	0.0132 (2)	0.83923 (12)	1.01794 (14)	0.0622 (5)
O23	0.2361 (2)	1.18932 (15)	0.15980 (13)	0.0613 (4)
H19A	0.247 (2)	0.9580 (17)	0.962 (2)	0.098 (10)*
H19B	0.198 (3)	0.8457 (17)	0.873 (2)	0.096 (10)*
H20A	0.547 (3)	0.933 (3)	0.898 (2)	0.114 (13)*
H20B	0.568 (3)	0.899 (3)	0.981 (2)	0.115 (13)*
H21A	−0.099 (2)	0.918 (3)	0.787 (3)	0.129 (15)*
H21B	0.052 (2)	0.948 (2)	0.842 (2)	0.095 (10)*
H22A	0.070 (3)	0.863 (2)	0.988 (2)	0.083 (9)*
H22B	0.025 (3)	0.897 (2)	1.0818 (18)	0.112 (12)*
H23A	0.174 (3)	1.200 (3)	0.114 (2)	0.110 (12)*
H23B	0.291 (3)	1.156 (2)	0.128 (2)	0.089 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.120 (3)	0.115 (3)	0.0670 (19)	0.053 (2)	0.0301 (19)	0.064 (2)
C2	0.0723 (19)	0.101 (2)	0.0352 (14)	0.0204 (16)	0.0097 (13)	0.0144 (14)
C3	0.0728 (19)	0.0755 (19)	0.0455 (15)	0.0100 (15)	0.0156 (13)	−0.0120 (14)
C4	0.0763 (19)	0.0358 (13)	0.106 (3)	0.0138 (13)	0.0203 (17)	0.0158 (15)
C5	0.0686 (18)	0.0503 (15)	0.132 (3)	0.0119 (13)	0.0257 (18)	0.0571 (18)
C6	0.107 (3)	0.093 (2)	0.090 (2)	0.030 (2)	0.042 (2)	0.066 (2)
C7	0.0628 (13)	0.0305 (10)	0.0295 (10)	0.0111 (9)	0.0128 (9)	0.0124 (8)
C8	0.0552 (12)	0.0369 (10)	0.0280 (10)	0.0148 (9)	0.0117 (9)	0.0174 (8)
C9	0.0415 (11)	0.0353 (10)	0.0266 (10)	0.0112 (8)	0.0093 (8)	0.0131 (8)
C10	0.0431 (11)	0.0308 (9)	0.0312 (10)	0.0086 (8)	0.0111 (8)	0.0133 (8)
C11	0.0396 (11)	0.0368 (10)	0.0280 (10)	0.0107 (8)	0.0119 (8)	0.0162 (8)
C12	0.0527 (12)	0.0352 (10)	0.0239 (9)	0.0090 (9)	0.0097 (9)	0.0107 (8)
C13	0.0453 (11)	0.0370 (11)	0.0282 (10)	0.0084 (9)	0.0117 (9)	0.0160 (8)
C14	0.0495 (12)	0.0365 (11)	0.0301 (10)	0.0101 (9)	0.0089 (9)	0.0140 (9)
C15	0.0432 (11)	0.0262 (9)	0.0333 (10)	0.0073 (8)	0.0085 (8)	0.0150 (8)
C16	0.0455 (11)	0.0309 (9)	0.0282 (10)	0.0099 (8)	0.0085 (8)	0.0144 (8)
C17	0.0485 (12)	0.0337 (10)	0.0354 (10)	0.0140 (8)	0.0136 (9)	0.0217 (9)
C18	0.0374 (10)	0.0289 (9)	0.0343 (10)	0.0100 (8)	0.0104 (8)	0.0162 (8)
C19	0.0422 (11)	0.0302 (9)	0.0277 (9)	0.0093 (8)	0.0095 (8)	0.0117 (8)
C20	0.0416 (11)	0.0304 (9)	0.0302 (10)	0.0087 (8)	0.0101 (8)	0.0158 (8)
C21	0.0528 (12)	0.0324 (10)	0.0308 (10)	0.0078 (9)	0.0122 (9)	0.0157 (9)
C22	0.0481 (12)	0.0295 (9)	0.0368 (11)	0.0119 (8)	0.0140 (9)	0.0172 (9)
C23	0.0406 (11)	0.0276 (9)	0.0320 (10)	0.0076 (8)	0.0092 (8)	0.0122 (8)
C24	0.0446 (11)	0.0294 (9)	0.0275 (10)	0.0053 (8)	0.0078 (8)	0.0090 (8)
C25	0.0443 (11)	0.0290 (9)	0.0334 (10)	0.0048 (8)	0.0091 (9)	0.0149 (8)
C26	0.0415 (11)	0.0260 (9)	0.0343 (10)	0.0044 (8)	0.0081 (8)	0.0121 (8)
C27	0.0343 (10)	0.0292 (9)	0.0299 (10)	0.0063 (8)	0.0068 (8)	0.0105 (8)
C28	0.0420 (11)	0.0310 (9)	0.0325 (10)	0.0086 (8)	0.0100 (8)	0.0163 (8)
C29	0.0559 (13)	0.0295 (10)	0.0343 (11)	0.0082 (9)	0.0126 (9)	0.0137 (9)
C30	0.0399 (11)	0.0308 (10)	0.0334 (10)	0.0067 (8)	0.0069 (8)	0.0125 (8)
O1	0.0630 (11)	0.0825 (12)	0.0442 (9)	0.0201 (9)	0.0120 (8)	0.0281 (9)
O2	0.0582 (10)	0.0447 (9)	0.0652 (11)	0.0167 (8)	0.0171 (8)	0.0083 (8)
O3	0.0668 (11)	0.0604 (10)	0.0814 (13)	0.0184 (9)	0.0313 (10)	0.0433 (10)
O4	0.1207 (15)	0.0292 (7)	0.0307 (8)	0.0041 (8)	0.0122 (9)	0.0115 (6)
O5	0.0810 (11)	0.0429 (8)	0.0286 (7)	0.0171 (8)	0.0018 (7)	0.0151 (7)
O6	0.0970 (13)	0.0354 (8)	0.0312 (8)	−0.0006 (8)	0.0034 (8)	0.0126 (6)
O7	0.0810 (11)	0.0392 (8)	0.0372 (8)	0.0104 (7)	0.0180 (8)	0.0218 (7)
O8	0.0885 (12)	0.0469 (9)	0.0286 (8)	−0.0012 (8)	0.0065 (8)	0.0195 (7)
O9	0.0850 (11)	0.0328 (7)	0.0285 (7)	0.0117 (7)	0.0102 (7)	0.0147 (6)
O10	0.0816 (11)	0.0349 (8)	0.0355 (8)	−0.0019 (7)	0.0096 (7)	0.0207 (6)
O11	0.1068 (13)	0.0368 (8)	0.0306 (8)	0.0068 (8)	0.0154 (8)	0.0164 (7)
O12	0.0763 (11)	0.0282 (7)	0.0400 (9)	0.0078 (7)	0.0109 (8)	0.0137 (7)
O13	0.1027 (13)	0.0319 (7)	0.0481 (9)	0.0135 (8)	0.0269 (9)	0.0234 (7)
O14	0.1048 (13)	0.0264 (7)	0.0358 (8)	0.0066 (8)	0.0225 (8)	0.0106 (6)
O15	0.1028 (13)	0.0315 (7)	0.0381 (9)	0.0071 (8)	0.0114 (8)	0.0181 (7)
O16	0.0719 (10)	0.0402 (8)	0.0307 (8)	0.0015 (7)	0.0054 (7)	0.0155 (7)
O17	0.0849 (12)	0.0304 (8)	0.0339 (8)	0.0119 (7)	−0.0004 (8)	0.0074 (6)
O18	0.0802 (11)	0.0315 (7)	0.0324 (8)	0.0036 (7)	0.0082 (7)	0.0162 (6)
O19	0.0533 (10)	0.0465 (9)	0.0562 (10)	0.0165 (8)	0.0227 (8)	0.0227 (8)
O20	0.0452 (9)	0.0573 (10)	0.0551 (10)	0.0106 (7)	0.0143 (8)	0.0227 (8)
O21	0.0638 (11)	0.0514 (10)	0.0533 (10)	0.0106 (9)	0.0099 (9)	0.0272 (8)
O22	0.0874 (13)	0.0405 (9)	0.0585 (11)	0.0129 (8)	0.0373 (10)	0.0209 (8)
O23	0.0675 (11)	0.0709 (11)	0.0384 (9)	0.0312 (9)	0.0143 (8)	0.0194 (8)

Geometric parameters (Å, º) top

C1—O1	1.418 (3)	C19—H19	0.9300
C1—C6ⁱ	1.490 (5)	C20—C21	1.483 (3)
C1—H1A	0.9700	C21—O10	1.258 (2)
C1—H1B	0.9700	C21—O11	1.270 (2)
C2—O1	1.425 (3)	C22—O12	1.248 (2)
C2—C3	1.486 (5)	C22—O13	1.287 (2)
C2—H2A	0.9700	C23—C28	1.387 (3)
C2—H2B	0.9700	C23—C24	1.391 (3)
C3—O2	1.434 (3)	C23—C29	1.483 (3)
C3—H3A	0.9700	C24—C25	1.389 (3)
C3—H3B	0.9700	C24—H24	0.9300
C4—O2	1.413 (3)	C25—O18	1.367 (2)
C4—C5	1.497 (5)	C25—C26	1.386 (3)
C4—H4A	0.9700	C26—C27	1.391 (3)
C4—H4B	0.9700	C26—H26	0.9300
C5—O3	1.433 (3)	C27—C28	1.389 (3)
C5—H5A	0.9700	C27—C30	1.488 (3)
C5—H5B	0.9700	C28—H28	0.9300
C6—O3	1.404 (4)	C29—O14	1.243 (2)
C6—C1ⁱ	1.490 (5)	C29—O15	1.288 (2)
C6—H6A	0.9700	C30—O16	1.265 (2)
C6—H6B	0.9700	C30—O17	1.265 (2)
C7—O4	1.359 (2)	O4—H4C	0.8200
C7—C12	1.391 (3)	O5—H5C	0.8200
C7—C8	1.392 (3)	O6—H6C	0.8200
C8—C9	1.385 (3)	O7—H7A	0.8200
C8—H8	0.9300	O8—H8A	0.8200
C9—C10	1.388 (3)	O9—H9C	0.8200
C9—C14	1.488 (3)	O10—H10A	0.8200
C10—C11	1.392 (3)	O11—H11A	0.8200
C10—H10	0.9300	O12—H12A	0.8200
C11—C12	1.385 (3)	O13—H13A	0.8200
C11—C13	1.484 (3)	O14—H14A	0.8200
C12—H12	0.9300	O15—H15A	0.8200
C13—O7	1.256 (2)	O16—H16A	0.8200
C13—O8	1.271 (2)	O17—H17A	0.8200
C14—O6	1.261 (2)	O18—H18C	0.8200
C14—O5	1.269 (2)	O19—H19A	0.923 (17)
C15—C20	1.387 (3)	O19—H19B	0.892 (17)
C15—C16	1.389 (3)	O20—H20A	0.895 (17)
C15—H15	0.9300	O20—H20B	0.871 (17)
C16—O9	1.365 (2)	O21—H21A	0.882 (18)
C16—C17	1.382 (3)	O21—H21B	0.910 (17)
C17—C18	1.393 (3)	O22—H22A	0.907 (17)
C17—H17	0.9300	O22—H22B	0.904 (17)
C18—C19	1.391 (3)	O23—H23A	0.888 (17)
C18—C22	1.480 (3)	O23—H23B	0.898 (17)
C19—C20	1.385 (2)

O1—C1—C6ⁱ	111.0 (2)	C16—C17—C18	119.70 (17)
O1—C1—H1A	109.4	C16—C17—H17	120.2
C6ⁱ—C1—H1A	109.4	C18—C17—H17	120.2
O1—C1—H1B	109.4	C19—C18—C17	120.92 (16)
C6ⁱ—C1—H1B	109.4	C19—C18—C22	118.43 (17)
H1A—C1—H1B	108.0	C17—C18—C22	120.64 (17)
O1—C2—C3	108.7 (2)	C20—C19—C18	118.81 (17)
O1—C2—H2A	110.0	C20—C19—H19	120.6
C3—C2—H2A	110.0	C18—C19—H19	120.6
O1—C2—H2B	110.0	C19—C20—C15	120.50 (17)
C3—C2—H2B	110.0	C19—C20—C21	119.86 (17)
H2A—C2—H2B	108.3	C15—C20—C21	119.64 (16)
O2—C3—C2	109.9 (2)	O10—C21—O11	123.55 (17)
O2—C3—H3A	109.7	O10—C21—C20	118.62 (17)
C2—C3—H3A	109.7	O11—C21—C20	117.82 (16)
O2—C3—H3B	109.7	O12—C22—O13	123.85 (17)
C2—C3—H3B	109.7	O12—C22—C18	119.58 (17)
H3A—C3—H3B	108.2	O13—C22—C18	116.56 (17)
O2—C4—C5	108.7 (2)	C28—C23—C24	120.84 (17)
O2—C4—H4A	109.9	C28—C23—C29	120.63 (17)
C5—C4—H4A	109.9	C24—C23—C29	118.53 (17)
O2—C4—H4B	109.9	C25—C24—C23	119.85 (17)
C5—C4—H4B	109.9	C25—C24—H24	120.1
H4A—C4—H4B	108.3	C23—C24—H24	120.1
O3—C5—C4	110.4 (2)	O18—C25—C26	117.80 (16)
O3—C5—H5A	109.6	O18—C25—C24	122.52 (17)
C4—C5—H5A	109.6	C26—C25—C24	119.68 (18)
O3—C5—H5B	109.6	C25—C26—C27	120.06 (16)
C4—C5—H5B	109.6	C25—C26—H26	120.0
H5A—C5—H5B	108.1	C27—C26—H26	120.0
O3—C6—C1ⁱ	111.3 (3)	C28—C27—C26	120.67 (17)
O3—C6—H6A	109.4	C28—C27—C30	119.27 (17)
C1ⁱ—C6—H6A	109.4	C26—C27—C30	120.06 (16)
O3—C6—H6B	109.4	C23—C28—C27	118.85 (18)
C1ⁱ—C6—H6B	109.4	C23—C28—H28	120.6
H6A—C6—H6B	108.0	C27—C28—H28	120.6
O4—C7—C12	116.91 (17)	O14—C29—O15	123.78 (17)
O4—C7—C8	122.96 (18)	O14—C29—C23	119.67 (17)
C12—C7—C8	120.12 (18)	O15—C29—C23	116.55 (17)
C9—C8—C7	119.91 (18)	O16—C30—O17	123.70 (18)
C9—C8—H8	120.0	O16—C30—C27	118.53 (16)
C7—C8—H8	120.0	O17—C30—C27	117.76 (17)
C8—C9—C10	120.30 (17)	C1—O1—C2	112.1 (2)
C8—C9—C14	120.16 (17)	C4—O2—C3	114.0 (2)
C10—C9—C14	119.52 (17)	C6—O3—C5	112.9 (2)
C9—C10—C11	119.49 (17)	C7—O4—H4C	109.5
C9—C10—H10	120.3	C14—O5—H5C	109.5
C11—C10—H10	120.3	C14—O6—H6C	109.5
C12—C11—C10	120.59 (17)	C13—O7—H7A	109.5
C12—C11—C13	119.97 (17)	C13—O8—H8A	109.5
C10—C11—C13	119.45 (17)	C16—O9—H9C	109.5
C11—C12—C7	119.57 (17)	C21—O10—H10A	109.5
C11—C12—H12	120.2	C21—O11—H11A	109.5
C7—C12—H12	120.2	C22—O12—H12A	109.5
O7—C13—O8	123.37 (17)	C22—O13—H13A	109.5
O7—C13—C11	118.45 (17)	C29—O14—H14A	109.5
O8—C13—C11	118.18 (17)	C29—O15—H15A	109.5
O6—C14—O5	123.70 (18)	C30—O16—H16A	109.5
O6—C14—C9	117.73 (17)	C30—O17—H17A	109.5
O5—C14—C9	118.56 (17)	C25—O18—H18C	109.5
C20—C15—C16	120.36 (16)	H19A—O19—H19B	107 (2)
C20—C15—H15	119.8	H20A—O20—H20B	113 (2)
C16—C15—H15	119.8	H21A—O21—H21B	109 (2)
O9—C16—C17	117.52 (16)	H22A—O22—H22B	107 (2)
O9—C16—C15	122.78 (16)	H23A—O23—H23B	111 (2)
C17—C16—C15	119.70 (17)

O1—C2—C3—O2	66.0 (3)	C19—C20—C21—O10	174.73 (19)
O2—C4—C5—O3	−66.0 (3)	C15—C20—C21—O10	−4.3 (3)
O4—C7—C8—C9	−180.0 (2)	C19—C20—C21—O11	−4.3 (3)
C12—C7—C8—C9	1.5 (3)	C15—C20—C21—O11	176.67 (19)
C7—C8—C9—C10	0.2 (3)	C19—C18—C22—O12	−1.2 (3)
C7—C8—C9—C14	−178.62 (19)	C17—C18—C22—O12	178.57 (18)
C8—C9—C10—C11	−1.5 (3)	C19—C18—C22—O13	179.39 (18)
C14—C9—C10—C11	177.30 (18)	C17—C18—C22—O13	−0.8 (3)
C9—C10—C11—C12	1.2 (3)	C28—C23—C24—C25	−1.4 (3)
C9—C10—C11—C13	−178.42 (17)	C29—C23—C24—C25	178.37 (18)
C10—C11—C12—C7	0.4 (3)	C23—C24—C25—O18	−178.37 (19)
C13—C11—C12—C7	−179.94 (19)	C23—C24—C25—C26	2.4 (3)
O4—C7—C12—C11	179.56 (19)	O18—C25—C26—C27	179.46 (18)
C8—C7—C12—C11	−1.8 (3)	C24—C25—C26—C27	−1.3 (3)
C12—C11—C13—O7	−179.95 (18)	C25—C26—C27—C28	−0.8 (3)
C10—C11—C13—O7	−0.3 (3)	C25—C26—C27—C30	178.70 (18)
C12—C11—C13—O8	−0.7 (3)	C24—C23—C28—C27	−0.7 (3)
C10—C11—C13—O8	178.91 (18)	C29—C23—C28—C27	179.52 (18)
C8—C9—C14—O6	−174.29 (19)	C26—C27—C28—C23	1.8 (3)
C10—C9—C14—O6	6.9 (3)	C30—C27—C28—C23	−177.73 (17)
C8—C9—C14—O5	6.2 (3)	C28—C23—C29—O14	−176.0 (2)
C10—C9—C14—O5	−172.59 (19)	C24—C23—C29—O14	4.2 (3)
C20—C15—C16—O9	179.74 (18)	C28—C23—C29—O15	3.2 (3)
C20—C15—C16—C17	−1.2 (3)	C24—C23—C29—O15	−176.59 (19)
O9—C16—C17—C18	−179.62 (17)	C28—C27—C30—O16	2.6 (3)
C15—C16—C17—C18	1.3 (3)	C26—C27—C30—O16	−176.99 (18)
C16—C17—C18—C19	−0.1 (3)	C28—C27—C30—O17	−178.68 (18)
C16—C17—C18—C22	−179.92 (18)	C26—C27—C30—O17	1.8 (3)
C17—C18—C19—C20	−1.1 (3)	C6ⁱ—C1—O1—C2	−175.3 (2)
C22—C18—C19—C20	178.70 (17)	C3—C2—O1—C1	−179.9 (2)
C18—C19—C20—C15	1.1 (3)	C5—C4—O2—C3	172.4 (2)
C18—C19—C20—C21	−177.92 (18)	C2—C3—O2—C4	−169.0 (2)
C16—C15—C20—C19	0.0 (3)	C1ⁱ—C6—O3—C5	170.2 (2)
C16—C15—C20—C21	179.07 (18)	C4—C5—O3—C6	176.6 (2)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O11	0.97	2.64	3.551 (3)	157
C12—H12···O4ⁱⁱ	0.93	2.52	3.419 (2)	164
C15—H15···O22ⁱⁱⁱ	0.93	2.62	3.280 (2)	129
C17—H17···O9^iv	0.93	2.50	3.383 (2)	158
C26—H26···O18^v	0.93	2.49	3.393 (2)	165
O4—H4C···O21^vi	0.82	1.95	2.760 (2)	168
O5—H5C···O17ⁱ	0.82	1.81	2.621 (2)	168
O6—H6C···O16ⁱ	0.82	1.81	2.614 (2)	167
O7—H7A···O11	0.82	1.80	2.595 (2)	164
O8—H8A···O10	0.82	1.81	2.6078 (19)	165
O9—H9C···O22ⁱⁱⁱ	0.82	1.95	2.766 (2)	175
O10—H10A···O8	0.82	1.80	2.6078 (19)	167
O11—H11A···O7	0.82	1.79	2.595 (2)	165
O12—H12A···O15	0.82	1.81	2.6033 (19)	162
O13—H13A···O14	0.82	1.80	2.6113 (19)	172
O14—H14A···O13	0.82	1.82	2.6113 (19)	163
O15—H15A···O12	0.82	1.79	2.6033 (19)	171
O16—H16A···O6ⁱ	0.82	1.81	2.614 (2)	164
O17—H17A···O5ⁱ	0.82	1.82	2.621 (2)	167
O18—H18C···O23	0.82	1.93	2.752 (2)	178
O19—H19A···O20ⁱ	0.92 (2)	1.74 (2)	2.664 (2)	176 (3)
O19—H19B···O2	0.89 (2)	1.87 (2)	2.731 (2)	162 (3)
O20—H20A···O1	0.90 (2)	1.91 (2)	2.798 (2)	175 (3)
O20—H20B···O3	0.87 (2)	1.90 (2)	2.764 (2)	172 (3)
O21—H21A···O23^vii	0.88 (2)	2.39 (3)	3.160 (3)	146 (3)
O21—H21B···O19	0.91 (2)	1.82 (2)	2.722 (2)	172 (3)
O22—H22A···O19	0.91 (2)	1.84 (2)	2.738 (2)	173 (3)
O22—H22B···O21^viii	0.90 (2)	1.99 (2)	2.872 (2)	164 (3)
O23—H23A···O22^vii	0.89 (2)	2.17 (2)	3.013 (3)	158 (3)
O23—H23B···O20^ix	0.90 (2)	1.88 (2)	2.778 (2)	174 (3)

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) −x+1, −y+3, −z+1; (vi) x, y−1, z; (vii) −x, −y+2, −z+1; (viii) −x, −y+2, −z+2; (ix) −x+1, −y+2, −z+1.

(II) top

Crystal data top

C₁₂H₂₄O₆·2(C₉H₆O₆)·2(H₂O)	Z = 1
M_r = 720.62	F(000) = 380
Triclinic, P1	D_x = 1.411 Mg m⁻³
a = 7.5073 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0208 (9) Å	Cell parameters from 9965 reflections
c = 14.7230 (16) Å	θ = 2.9–30.4°
α = 77.133 (4)°	µ = 0.12 mm⁻¹
β = 79.494 (4)°	T = 296 K
γ = 84.408 (4)°	Block, colourless
V = 848.29 (17) Å³	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker axs kappa apex3 CMOS Diffractometer	2965 independent reflections
Radiation source: fine-focus sealed tube	2384 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and φ scan	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan SADABS (Bruker, 2016)	h = −8→8
T_min = 0.714, T_max = 0.746	k = −9→9
24568 measured reflections	l = −17→17

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0658P)² + 0.4432P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2965 reflections	Δρ_max = 0.20 e Å⁻³
237 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3047 (5)	0.3435 (5)	1.1019 (3)	0.0932 (11)
H1A	0.3006	0.4440	1.1289	0.112*
H1B	0.2170	0.2661	1.1419	0.112*
C2	0.2601 (4)	0.3940 (4)	1.0054 (3)	0.0940 (12)
H2A	0.1562	0.4760	1.0050	0.113*
H2B	0.3619	0.4489	0.9626	0.113*
C3	0.1832 (5)	0.2927 (5)	0.8802 (3)	0.0973 (12)
H3A	0.2865	0.3462	0.8380	0.117*
H3B	0.0789	0.3740	0.8770	0.117*
C4	0.1468 (4)	0.1392 (6)	0.8508 (3)	0.1019 (13)
H4A	0.0566	0.0759	0.8982	0.122*
H4B	0.0996	0.1710	0.7918	0.122*
C5	0.2860 (6)	−0.1241 (5)	0.8200 (2)	0.0907 (11)
H5A	0.2387	−0.1076	0.7614	0.109*
H5B	0.1995	−0.1857	0.8705	0.109*
C6	0.4620 (6)	−0.2224 (4)	0.81275 (18)	0.0880 (12)
H6A	0.4504	−0.3274	0.7925	0.106*
H6B	0.5509	−0.1559	0.7661	0.106*
C7	0.6904 (2)	0.5953 (2)	0.52059 (13)	0.0310 (4)
C8	0.6803 (2)	0.4897 (2)	0.61002 (12)	0.0321 (4)
H8	0.6234	0.5313	0.6628	0.038*
C9	0.7548 (2)	0.3224 (2)	0.62084 (12)	0.0298 (4)
C10	0.8386 (2)	0.2612 (2)	0.54153 (12)	0.0316 (4)
H10	0.8883	0.1492	0.5483	0.038*
C11	0.8487 (2)	0.3663 (2)	0.45171 (12)	0.0313 (4)
C12	0.7749 (2)	0.5334 (2)	0.44136 (12)	0.0318 (4)
H12	0.7819	0.6040	0.3816	0.038*
C13	0.6096 (3)	0.7733 (2)	0.51109 (13)	0.0361 (4)
C14	0.7493 (2)	0.2070 (2)	0.71626 (12)	0.0332 (4)
C15	0.9387 (3)	0.3019 (2)	0.36618 (13)	0.0388 (5)
O1	0.4783 (3)	0.2627 (2)	1.09713 (12)	0.0662 (5)
O2	0.2201 (3)	0.2485 (2)	0.97351 (14)	0.0740 (6)
O3	0.3117 (3)	0.0342 (3)	0.83875 (12)	0.0718 (6)
O4	0.6319 (3)	0.86627 (18)	0.42674 (10)	0.0581 (5)
H4	0.5804	0.9611	0.4275	0.087*
O5	0.5244 (2)	0.82432 (18)	0.58067 (10)	0.0544 (4)
O6	0.6712 (2)	0.27946 (17)	0.78535 (9)	0.0492 (4)
H6	0.6781	0.2131	0.8359	0.074*
O7	0.8140 (2)	0.06026 (17)	0.72783 (9)	0.0454 (4)
O8	1.0098 (3)	0.1450 (2)	0.38775 (11)	0.0678 (6)
H8A	1.0526	0.1116	0.3391	0.102*
O9	0.9457 (3)	0.3822 (2)	0.28707 (10)	0.0683 (6)
O10	0.6836 (2)	0.1087 (2)	0.95193 (10)	0.0553 (4)
H10B	0.616 (3)	0.149 (3)	0.9945 (17)	0.074 (9)*
H10A	0.704 (5)	0.001 (2)	0.968 (2)	0.111 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.090 (2)	0.078 (2)	0.110 (3)	−0.0064 (17)	0.029 (2)	−0.054 (2)
C2	0.0652 (18)	0.0450 (15)	0.157 (4)	0.0136 (13)	0.002 (2)	−0.0140 (19)
C3	0.077 (2)	0.106 (3)	0.084 (2)	0.0282 (19)	−0.0168 (18)	0.021 (2)
C4	0.0588 (19)	0.167 (4)	0.072 (2)	−0.002 (2)	−0.0343 (16)	0.008 (2)
C5	0.117 (3)	0.121 (3)	0.0458 (16)	−0.061 (2)	−0.0213 (17)	−0.0114 (16)
C6	0.154 (3)	0.084 (2)	0.0335 (13)	−0.058 (2)	0.0104 (16)	−0.0270 (13)
C7	0.0330 (9)	0.0278 (9)	0.0319 (9)	0.0005 (7)	−0.0055 (7)	−0.0065 (7)
C8	0.0359 (9)	0.0316 (9)	0.0280 (9)	−0.0004 (7)	0.0000 (7)	−0.0099 (7)
C9	0.0330 (9)	0.0284 (9)	0.0272 (9)	−0.0011 (7)	−0.0015 (7)	−0.0071 (7)
C10	0.0381 (10)	0.0265 (9)	0.0290 (9)	0.0030 (7)	−0.0036 (7)	−0.0068 (7)
C11	0.0367 (10)	0.0301 (9)	0.0269 (9)	0.0008 (7)	−0.0040 (7)	−0.0076 (7)
C12	0.0373 (10)	0.0297 (9)	0.0265 (9)	−0.0004 (7)	−0.0048 (7)	−0.0033 (7)
C13	0.0433 (11)	0.0297 (9)	0.0339 (10)	0.0031 (8)	−0.0048 (8)	−0.0074 (8)
C14	0.0384 (10)	0.0317 (10)	0.0274 (9)	0.0004 (7)	−0.0002 (7)	−0.0074 (7)
C15	0.0498 (11)	0.0347 (10)	0.0299 (10)	0.0047 (8)	−0.0036 (8)	−0.0082 (8)
O1	0.0905 (13)	0.0588 (10)	0.0463 (10)	−0.0104 (9)	0.0143 (9)	−0.0234 (8)
O2	0.0697 (12)	0.0630 (12)	0.0757 (13)	0.0046 (9)	−0.0065 (10)	0.0061 (9)
O3	0.0747 (12)	0.0920 (14)	0.0521 (11)	−0.0256 (11)	−0.0226 (9)	−0.0035 (9)
O4	0.0895 (12)	0.0330 (8)	0.0391 (8)	0.0183 (8)	0.0021 (8)	−0.0007 (6)
O5	0.0818 (11)	0.0365 (8)	0.0372 (8)	0.0200 (7)	−0.0016 (7)	−0.0085 (6)
O6	0.0768 (11)	0.0363 (8)	0.0268 (7)	0.0115 (7)	0.0050 (7)	−0.0075 (6)
O7	0.0667 (10)	0.0333 (7)	0.0295 (7)	0.0114 (6)	0.0002 (6)	−0.0049 (6)
O8	0.1157 (15)	0.0441 (9)	0.0309 (8)	0.0339 (9)	0.0035 (8)	−0.0108 (7)
O9	0.1122 (15)	0.0538 (10)	0.0265 (8)	0.0251 (9)	0.0006 (8)	−0.0054 (7)
O10	0.0700 (11)	0.0572 (11)	0.0295 (8)	0.0073 (8)	0.0032 (7)	−0.0034 (7)

Geometric parameters (Å, º) top

C1—O1	1.395 (4)	C7—C13	1.482 (2)
C1—C2	1.479 (5)	C8—C9	1.389 (2)
C1—H1A	0.9700	C8—H8	0.9300
C1—H1B	0.9700	C9—C10	1.388 (2)
C2—O2	1.427 (4)	C9—C14	1.497 (2)
C2—H2A	0.9700	C10—C11	1.395 (3)
C2—H2B	0.9700	C10—H10	0.9300
C3—O2	1.412 (4)	C11—C12	1.386 (3)
C3—C4	1.457 (6)	C11—C15	1.490 (2)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—O5	1.234 (2)
C4—O3	1.434 (4)	C13—O4	1.289 (2)
C4—H4A	0.9700	C14—O7	1.216 (2)
C4—H4B	0.9700	C14—O6	1.303 (2)
C5—O3	1.396 (4)	C15—O9	1.194 (2)
C5—C6	1.471 (5)	C15—O8	1.312 (2)
C5—H5A	0.9700	O1—C6ⁱ	1.436 (4)
C5—H5B	0.9700	O4—H4	0.8200
C6—O1ⁱ	1.436 (4)	O6—H6	0.8200
C6—H6A	0.9700	O8—H8A	0.8200
C6—H6B	0.9700	O10—H10B	0.833 (17)
C7—C8	1.392 (3)	O10—H10A	0.848 (17)
C7—C12	1.392 (3)

O1—C1—C2	108.7 (2)	H6A—C6—H6B	108.2
O1—C1—H1A	110.0	C8—C7—C12	120.02 (16)
C2—C1—H1A	110.0	C8—C7—C13	119.20 (16)
O1—C1—H1B	110.0	C12—C7—C13	120.78 (16)
C2—C1—H1B	110.0	C9—C8—C7	120.33 (16)
H1A—C1—H1B	108.3	C9—C8—H8	119.8
O2—C2—C1	110.9 (3)	C7—C8—H8	119.8
O2—C2—H2A	109.5	C10—C9—C8	119.38 (16)
C1—C2—H2A	109.5	C10—C9—C14	119.08 (15)
O2—C2—H2B	109.5	C8—C9—C14	121.53 (15)
C1—C2—H2B	109.5	C9—C10—C11	120.53 (16)
H2A—C2—H2B	108.0	C9—C10—H10	119.7
O2—C3—C4	109.6 (3)	C11—C10—H10	119.7
O2—C3—H3A	109.8	C12—C11—C10	119.85 (16)
C4—C3—H3A	109.8	C12—C11—C15	119.23 (16)
O2—C3—H3B	109.8	C10—C11—C15	120.91 (16)
C4—C3—H3B	109.8	C11—C12—C7	119.88 (16)
H3A—C3—H3B	108.2	C11—C12—H12	120.1
O3—C4—C3	109.3 (3)	C7—C12—H12	120.1
O3—C4—H4A	109.8	O5—C13—O4	123.58 (17)
C3—C4—H4A	109.8	O5—C13—C7	120.62 (17)
O3—C4—H4B	109.8	O4—C13—C7	115.79 (16)
C3—C4—H4B	109.8	O7—C14—O6	123.47 (17)
H4A—C4—H4B	108.3	O7—C14—C9	122.94 (16)
O3—C5—C6	108.3 (2)	O6—C14—C9	113.58 (15)
O3—C5—H5A	110.0	O9—C15—O8	123.47 (18)
C6—C5—H5A	110.0	O9—C15—C11	124.48 (18)
O3—C5—H5B	110.0	O8—C15—C11	112.05 (16)
C6—C5—H5B	110.0	C1—O1—C6ⁱ	112.1 (3)
H5A—C5—H5B	108.4	C3—O2—C2	112.0 (3)
O1ⁱ—C6—C5	109.8 (2)	C5—O3—C4	113.2 (3)
O1ⁱ—C6—H6A	109.7	C13—O4—H4	109.5
C5—C6—H6A	109.7	C14—O6—H6	109.5
O1ⁱ—C6—H6B	109.7	C15—O8—H8A	109.5
C5—C6—H6B	109.7	H10B—O10—H10A	112 (2)

O1—C1—C2—O2	74.3 (3)	C12—C7—C13—O5	175.19 (18)
O2—C3—C4—O3	−70.1 (4)	C8—C7—C13—O4	176.72 (18)
O3—C5—C6—O1ⁱ	66.0 (3)	C12—C7—C13—O4	−3.5 (3)
C12—C7—C8—C9	0.2 (3)	C10—C9—C14—O7	−0.6 (3)
C13—C7—C8—C9	179.96 (17)	C8—C9—C14—O7	−179.74 (18)
C7—C8—C9—C10	−0.4 (3)	C10—C9—C14—O6	178.51 (17)
C7—C8—C9—C14	178.74 (16)	C8—C9—C14—O6	−0.6 (3)
C8—C9—C10—C11	0.2 (3)	C12—C11—C15—O9	−3.5 (3)
C14—C9—C10—C11	−178.92 (16)	C10—C11—C15—O9	176.8 (2)
C9—C10—C11—C12	0.1 (3)	C12—C11—C15—O8	176.67 (19)
C9—C10—C11—C15	179.86 (17)	C10—C11—C15—O8	−3.1 (3)
C10—C11—C12—C7	−0.3 (3)	C2—C1—O1—C6ⁱ	175.1 (2)
C15—C11—C12—C7	179.98 (17)	C4—C3—O2—C2	178.9 (3)
C8—C7—C12—C11	0.1 (3)	C1—C2—O2—C3	−177.9 (3)
C13—C7—C12—C11	−179.64 (17)	C6—C5—O3—C4	−177.9 (2)
C8—C7—C13—O5	−4.6 (3)	C3—C4—O3—C5	173.8 (3)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ⁱⁱ	0.97	2.61	3.441 (4)	144
C6—H6B···O7	0.97	2.66	3.519 (4)	149
O4—H4···O5ⁱⁱⁱ	0.82	1.81	2.628 (2)	175
O6—H6···O10	0.82	1.73	2.542 (2)	169
O8—H8A···O7^iv	0.82	1.96	2.7129 (19)	152
O10—H10B···O1	0.83 (2)	2.01 (2)	2.842 (2)	173 (3)
O10—H10A···O2ⁱ	0.85 (2)	2.07 (2)	2.902 (3)	169 (3)

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

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