Bis(2,2'-bipyridine)(2-hy-droxy-2,2-diphenyl-acetato)-copper(II) nitrate dihydrate.

In the title complex, [Cu(C(14)H(11)O(3))(C(10)H(8)N(2))(2)]NO(3)·2H(2)O, the Cu(II) atom is coordinated by four N atoms from two 2,2'-bipyridine ligands and two O atoms from one benzilate ligand in a distorted octa-hedral geometry. A supra-molecular network is formed via inter-molecular O-H⋯O and C-H⋯O hydrogen-bonding inter-actions. π-π stacking inter-actions between neighboring pyridine rings are also present, the centroid-centroid distance being 3.808 (2) Å.

Related literature

For related structures, see: Carballo et al. (2005 ▶); Herrmann et al. (1994 ▶); Qiu et al. (2007 ▶).

Experimental

Crystal data

[Cu(C14H11O3)(C10H8N2)2]NO3·2H2O

M = 701.18

Monoclinic,

a = 10.612 (2) Å

b = 25.758 (6) Å

c = 12.322 (3) Å

β = 108.220 (3)°

V = 3199.3 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 296 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.848, T max = 0.872

16165 measured reflections

5750 independent reflections

3659 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.138

S = 1.00

5750 reflections

434 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035555/pv2323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035555/pv2323Isup2.hkl

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

[Cu(C14H11O3)(C10H8N2)2]NO3·2H2O	F(000) = 1452
Mr = 701.18	Dx = 1.456 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2592 reflections
a = 10.612 (2) Å	θ = 2.2–22.7°
b = 25.758 (6) Å	µ = 0.74 mm−1
c = 12.322 (3) Å	T = 296 K
β = 108.220 (3)°	Block, blue
V = 3199.3 (13) Å3	0.23 × 0.21 × 0.19 mm
Z = 4

Bruker APEXII area-detector diffractometer	5750 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→9
Tmin = 0.848, Tmax = 0.872	k = −30→30
16165 measured reflections	l = −14→13

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.053P)2 + 2.8562P] where P = (Fo2 + 2Fc2)/3
5750 reflections	(Δ/σ)max < 0.001
434 parameters	Δρmax = 0.56 e Å−3
6 restraints	Δρmin = −0.51 e Å−3

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.

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 > 2sigma(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
Cu1	0.41218 (5)	0.128914 (18)	0.88185 (4)	0.03907 (17)
O1	0.6773 (3)	0.12292 (11)	1.0021 (2)	0.0493 (7)
O2	0.5624 (3)	0.15418 (10)	0.8330 (2)	0.0416 (7)
O3	0.9044 (3)	0.15772 (12)	0.9953 (2)	0.0487 (7)
H3	0.8800	0.1396	1.0397	0.073*
O4	0.9802 (5)	0.43639 (17)	0.8832 (4)	0.1032 (14)
O5	1.1068 (4)	0.38476 (16)	0.8257 (4)	0.0910 (13)
O6	0.9367 (4)	0.42004 (17)	0.7058 (4)	0.0890 (12)
O1W	0.1694 (5)	0.02577 (18)	0.5874 (4)	0.1147 (15)
H2W	0.1658	0.0353	0.5204	0.172*
H1W	0.1207	−0.0011	0.5773	0.172*
O2W	0.6493 (5)	0.92807 (19)	0.5360 (4)	0.1224 (16)
H4W	0.6297	0.9527	0.4877	0.184*
H3W	0.7332	0.9259	0.5527	0.184*
N1	0.4082 (3)	0.19785 (13)	0.9567 (3)	0.0407 (8)
N2	0.2541 (3)	0.16914 (13)	0.7536 (3)	0.0422 (8)
N3	0.3174 (3)	0.08879 (13)	0.9731 (3)	0.0432 (8)
N4	0.4228 (3)	0.05833 (12)	0.8213 (3)	0.0414 (8)
N5	1.0072 (5)	0.41464 (17)	0.8048 (4)	0.0656 (11)
C1	0.4840 (4)	0.20910 (18)	1.0623 (4)	0.0509 (11)
H1	0.5372	0.1831	1.1055	0.061*
C2	0.4873 (5)	0.2571 (2)	1.1103 (4)	0.0637 (14)
H2	0.5397	0.2634	1.1851	0.076*
C3	0.4119 (5)	0.2954 (2)	1.0458 (5)	0.0705 (16)
H3A	0.4146	0.3287	1.0753	0.085*
C4	0.3318 (5)	0.28473 (18)	0.9368 (5)	0.0644 (14)
H4	0.2789	0.3107	0.8928	0.077*
C5	0.3301 (4)	0.23523 (16)	0.8930 (4)	0.0442 (10)
C6	0.2447 (4)	0.21925 (16)	0.7790 (3)	0.0415 (10)
C7	0.1595 (5)	0.25249 (19)	0.7035 (4)	0.0591 (13)
H7	0.1552	0.2873	0.7221	0.071*
C8	0.0810 (5)	0.2338 (2)	0.6007 (4)	0.0714 (15)
H8	0.0226	0.2557	0.5488	0.086*
C9	0.0892 (5)	0.1829 (2)	0.5753 (4)	0.0701 (15)
H9	0.0365	0.1695	0.5059	0.084*
C10	0.1764 (5)	0.15173 (18)	0.6536 (4)	0.0547 (12)
H10	0.1814	0.1168	0.6360	0.066*
C11	0.2639 (5)	0.10780 (19)	1.0494 (4)	0.0549 (12)
H11	0.2707	0.1433	1.0639	0.066*
C12	0.1999 (5)	0.0782 (2)	1.1073 (4)	0.0670 (14)
H12	0.1633	0.0928	1.1596	0.080*
C13	0.1914 (6)	0.0260 (2)	1.0854 (5)	0.0752 (16)
H13	0.1497	0.0044	1.1242	0.090*
C14	0.2437 (5)	0.0054 (2)	1.0070 (4)	0.0623 (13)
H14	0.2363	−0.0300	0.9911	0.075*
C15	0.3082 (4)	0.03765 (16)	0.9512 (4)	0.0434 (10)
C16	0.3693 (4)	0.02037 (16)	0.8674 (3)	0.0417 (10)
C17	0.3744 (5)	−0.03074 (17)	0.8344 (4)	0.0560 (12)
H17	0.3370	−0.0569	0.8664	0.067*
C18	0.4351 (5)	−0.04255 (18)	0.7543 (4)	0.0639 (14)
H18	0.4390	−0.0768	0.7316	0.077*
C19	0.4897 (5)	−0.00371 (18)	0.7080 (4)	0.0626 (13)
H19	0.5320	−0.0109	0.6541	0.075*
C20	0.4803 (5)	0.04618 (17)	0.7434 (4)	0.0518 (12)
H20	0.5161	0.0728	0.7112	0.062*
C21	0.6700 (4)	0.14445 (14)	0.9122 (4)	0.0387 (10)
C22	0.8000 (4)	0.16241 (15)	0.8909 (3)	0.0376 (9)
C23	0.7908 (4)	0.21966 (15)	0.8583 (3)	0.0393 (10)
C24	0.7320 (5)	0.25356 (16)	0.9140 (4)	0.0506 (11)
H24	0.6962	0.2409	0.9687	0.061*
C25	0.7252 (5)	0.30584 (18)	0.8902 (5)	0.0645 (14)
H25	0.6849	0.3282	0.9286	0.077*
C26	0.7776 (5)	0.32494 (18)	0.8103 (4)	0.0606 (13)
H26	0.7723	0.3602	0.7932	0.073*
C27	0.8376 (5)	0.29183 (19)	0.7558 (4)	0.0610 (13)
H27	0.8742	0.3048	0.7020	0.073*
C28	0.8451 (4)	0.23917 (17)	0.7792 (4)	0.0511 (11)
H28	0.8868	0.2171	0.7415	0.061*
C29	0.8237 (4)	0.12686 (15)	0.7997 (3)	0.0392 (9)
C30	0.7340 (5)	0.12378 (17)	0.6913 (4)	0.0546 (12)
H30	0.6588	0.1447	0.6715	0.066*
C31	0.7548 (6)	0.0900 (2)	0.6122 (4)	0.0709 (15)
H31	0.6929	0.0877	0.5397	0.085*
C32	0.8672 (7)	0.0595 (2)	0.6401 (6)	0.0791 (17)
H32	0.8820	0.0370	0.5864	0.095*
C33	0.9555 (6)	0.0627 (2)	0.7457 (6)	0.0794 (17)
H33	1.0314	0.0422	0.7646	0.095*
C34	0.9351 (5)	0.09591 (18)	0.8255 (4)	0.0592 (13)
H34	0.9971	0.0975	0.8980	0.071*

	U11	U22	U33	U12	U13	U23
Cu1	0.0364 (3)	0.0342 (3)	0.0450 (3)	−0.0020 (2)	0.0105 (2)	0.0002 (2)
O1	0.0513 (19)	0.0515 (18)	0.0466 (18)	0.0013 (15)	0.0173 (15)	0.0154 (14)
O2	0.0374 (17)	0.0392 (16)	0.0461 (17)	−0.0033 (13)	0.0101 (14)	0.0019 (13)
O3	0.0391 (17)	0.056 (2)	0.0426 (17)	−0.0052 (14)	0.0012 (14)	0.0060 (14)
O4	0.122 (4)	0.099 (3)	0.101 (3)	−0.014 (3)	0.052 (3)	−0.037 (3)
O5	0.083 (3)	0.087 (3)	0.106 (3)	0.021 (2)	0.035 (3)	0.023 (2)
O6	0.072 (3)	0.113 (3)	0.075 (3)	−0.002 (2)	0.013 (2)	0.013 (2)
O1W	0.105 (4)	0.113 (4)	0.120 (4)	−0.008 (3)	0.025 (3)	−0.028 (3)
O2W	0.091 (3)	0.142 (4)	0.126 (4)	0.007 (3)	0.022 (3)	0.002 (3)
N1	0.0338 (19)	0.045 (2)	0.043 (2)	−0.0035 (16)	0.0108 (17)	−0.0041 (16)
N2	0.036 (2)	0.040 (2)	0.046 (2)	0.0015 (16)	0.0063 (17)	−0.0025 (16)
N3	0.037 (2)	0.043 (2)	0.049 (2)	0.0013 (16)	0.0127 (17)	0.0030 (16)
N4	0.040 (2)	0.040 (2)	0.043 (2)	−0.0030 (16)	0.0110 (17)	0.0023 (16)
N5	0.069 (3)	0.060 (3)	0.072 (3)	−0.016 (2)	0.028 (3)	0.000 (2)
C1	0.042 (3)	0.057 (3)	0.051 (3)	−0.003 (2)	0.010 (2)	−0.008 (2)
C2	0.050 (3)	0.075 (4)	0.066 (3)	−0.008 (3)	0.017 (3)	−0.027 (3)
C3	0.061 (3)	0.058 (3)	0.091 (4)	−0.004 (3)	0.021 (3)	−0.039 (3)
C4	0.058 (3)	0.047 (3)	0.084 (4)	0.008 (2)	0.016 (3)	−0.007 (3)
C5	0.035 (2)	0.042 (2)	0.055 (3)	0.001 (2)	0.014 (2)	−0.006 (2)
C6	0.034 (2)	0.046 (3)	0.044 (3)	0.0041 (19)	0.011 (2)	0.000 (2)
C7	0.051 (3)	0.056 (3)	0.065 (3)	0.016 (2)	0.011 (3)	0.012 (2)
C8	0.054 (3)	0.087 (4)	0.060 (4)	0.023 (3)	−0.002 (3)	0.014 (3)
C9	0.053 (3)	0.090 (4)	0.051 (3)	0.006 (3)	−0.007 (3)	−0.005 (3)
C10	0.050 (3)	0.051 (3)	0.054 (3)	0.001 (2)	0.003 (2)	−0.006 (2)
C11	0.050 (3)	0.059 (3)	0.061 (3)	0.000 (2)	0.026 (3)	0.000 (2)
C12	0.061 (3)	0.081 (4)	0.069 (3)	−0.001 (3)	0.034 (3)	0.005 (3)
C13	0.083 (4)	0.078 (4)	0.076 (4)	−0.013 (3)	0.041 (3)	0.018 (3)
C14	0.067 (3)	0.056 (3)	0.066 (3)	−0.006 (3)	0.023 (3)	0.011 (2)
C15	0.035 (2)	0.043 (3)	0.046 (3)	−0.0045 (19)	0.003 (2)	0.009 (2)
C16	0.036 (2)	0.040 (2)	0.043 (3)	−0.0039 (18)	0.003 (2)	0.0070 (19)
C17	0.064 (3)	0.037 (3)	0.065 (3)	−0.009 (2)	0.018 (3)	0.004 (2)
C18	0.075 (4)	0.040 (3)	0.072 (4)	−0.001 (3)	0.018 (3)	−0.007 (2)
C19	0.071 (4)	0.049 (3)	0.073 (3)	0.000 (3)	0.030 (3)	−0.010 (2)
C20	0.054 (3)	0.049 (3)	0.054 (3)	−0.009 (2)	0.018 (2)	−0.003 (2)
C21	0.041 (3)	0.030 (2)	0.044 (3)	0.0003 (18)	0.012 (2)	−0.0027 (18)
C22	0.033 (2)	0.041 (2)	0.037 (2)	−0.0013 (18)	0.0094 (19)	0.0019 (18)
C23	0.035 (2)	0.035 (2)	0.044 (2)	−0.0055 (18)	0.008 (2)	−0.0010 (18)
C24	0.060 (3)	0.040 (3)	0.057 (3)	−0.007 (2)	0.025 (2)	−0.003 (2)
C25	0.070 (4)	0.045 (3)	0.080 (4)	−0.001 (3)	0.025 (3)	−0.008 (3)
C26	0.055 (3)	0.041 (3)	0.075 (4)	−0.006 (2)	0.006 (3)	0.007 (3)
C27	0.061 (3)	0.053 (3)	0.067 (3)	−0.013 (3)	0.018 (3)	0.017 (3)
C28	0.051 (3)	0.050 (3)	0.056 (3)	−0.005 (2)	0.022 (2)	0.003 (2)
C29	0.039 (2)	0.036 (2)	0.047 (2)	−0.0025 (19)	0.019 (2)	0.0019 (19)
C30	0.067 (3)	0.050 (3)	0.047 (3)	0.003 (2)	0.018 (2)	−0.003 (2)
C31	0.095 (5)	0.065 (3)	0.054 (3)	−0.010 (3)	0.025 (3)	−0.009 (3)
C32	0.107 (5)	0.058 (3)	0.091 (5)	0.005 (3)	0.058 (4)	−0.012 (3)
C33	0.073 (4)	0.074 (4)	0.099 (5)	0.016 (3)	0.040 (4)	−0.001 (3)
C34	0.048 (3)	0.063 (3)	0.069 (3)	0.010 (2)	0.022 (3)	0.002 (3)

Cu1—O2	1.982 (3)	C11—H11	0.9300
Cu1—N4	1.982 (3)	C12—C13	1.369 (7)
Cu1—N1	2.007 (3)	C12—H12	0.9300
Cu1—N3	2.013 (3)	C13—C14	1.362 (7)
Cu1—N2	2.174 (3)	C13—H13	0.9300
O1—C21	1.220 (5)	C14—C15	1.388 (6)
O2—C21	1.274 (5)	C14—H14	0.9300
O3—C22	1.417 (4)	C15—C16	1.450 (6)
O3—H3	0.8200	C16—C17	1.384 (6)
O4—N5	1.225 (5)	C17—C18	1.370 (6)
O5—N5	1.267 (5)	C17—H17	0.9300
O6—N5	1.223 (5)	C18—C19	1.367 (7)
O1W—H2W	0.8499	C18—H18	0.9300
O1W—H1W	0.8501	C19—C20	1.371 (6)
O2W—H4W	0.8499	C19—H19	0.9300
O2W—H3W	0.8499	C20—H20	0.9300
N1—C1	1.330 (5)	C21—C22	1.553 (6)
N1—C5	1.350 (5)	C22—C23	1.523 (5)
N2—C10	1.328 (5)	C22—C29	1.530 (5)
N2—C6	1.339 (5)	C23—C28	1.374 (6)
N3—C11	1.334 (5)	C23—C24	1.375 (6)
N3—C15	1.342 (5)	C24—C25	1.375 (6)
N4—C20	1.326 (5)	C24—H24	0.9300
N4—C16	1.343 (5)	C25—C26	1.365 (7)
C1—C2	1.366 (6)	C25—H25	0.9300
C1—H1	0.9300	C26—C27	1.360 (7)
C2—C3	1.359 (7)	C26—H26	0.9300
C2—H2	0.9300	C27—C28	1.384 (6)
C3—C4	1.374 (7)	C27—H27	0.9300
C3—H3A	0.9300	C28—H28	0.9300
C4—C5	1.383 (6)	C29—C34	1.378 (6)
C4—H4	0.9300	C29—C30	1.379 (6)
C5—C6	1.473 (6)	C30—C31	1.375 (6)
C6—C7	1.375 (6)	C30—H30	0.9300
C7—C8	1.368 (7)	C31—C32	1.379 (8)
C7—H7	0.9300	C31—H31	0.9300
C8—C9	1.356 (7)	C32—C33	1.347 (8)
C8—H8	0.9300	C32—H32	0.9300
C9—C10	1.369 (6)	C33—C34	1.371 (7)
C9—H9	0.9300	C33—H33	0.9300
C10—H10	0.9300	C34—H34	0.9300
C11—C12	1.362 (6)
O2—Cu1—N4	92.34 (13)	C12—C13—H13	119.8
O2—Cu1—N1	89.06 (12)	C13—C14—C15	119.5 (5)
N4—Cu1—N1	175.10 (14)	C13—C14—H14	120.3
O2—Cu1—N3	158.18 (12)	C15—C14—H14	120.3
N4—Cu1—N3	80.61 (14)	N3—C15—C14	120.2 (4)
N1—Cu1—N3	96.40 (14)	N3—C15—C16	115.1 (4)
O2—Cu1—N2	97.69 (12)	C14—C15—C16	124.7 (4)
N4—Cu1—N2	106.57 (13)	N4—C16—C17	120.5 (4)
N1—Cu1—N2	77.87 (13)	N4—C16—C15	114.9 (4)
N3—Cu1—N2	104.11 (13)	C17—C16—C15	124.7 (4)
C21—O2—Cu1	108.4 (3)	C18—C17—C16	119.6 (4)
C22—O3—H3	109.5	C18—C17—H17	120.2
H2W—O1W—H1W	104.6	C16—C17—H17	120.2
H4W—O2W—H3W	103.2	C19—C18—C17	119.6 (4)
C1—N1—C5	119.1 (4)	C19—C18—H18	120.2
C1—N1—Cu1	123.3 (3)	C17—C18—H18	120.2
C5—N1—Cu1	117.5 (3)	C18—C19—C20	118.1 (5)
C10—N2—C6	118.1 (4)	C18—C19—H19	120.9
C10—N2—Cu1	128.9 (3)	C20—C19—H19	120.9
C6—N2—Cu1	112.8 (3)	N4—C20—C19	123.2 (4)
C11—N3—C15	118.8 (4)	N4—C20—H20	118.4
C11—N3—Cu1	127.0 (3)	C19—C20—H20	118.4
C15—N3—Cu1	114.1 (3)	O1—C21—O2	125.0 (4)
C20—N4—C16	119.1 (4)	O1—C21—C22	118.8 (4)
C20—N4—Cu1	125.6 (3)	O2—C21—C22	116.3 (3)
C16—N4—Cu1	115.3 (3)	O3—C22—C23	106.8 (3)
O6—N5—O4	120.8 (5)	O3—C22—C29	110.7 (3)
O6—N5—O5	118.8 (5)	C23—C22—C29	113.4 (3)
O4—N5—O5	120.3 (5)	O3—C22—C21	107.8 (3)
N1—C1—C2	123.2 (5)	C23—C22—C21	110.2 (3)
N1—C1—H1	118.4	C29—C22—C21	107.7 (3)
C2—C1—H1	118.4	C28—C23—C24	118.6 (4)
C3—C2—C1	118.2 (5)	C28—C23—C22	122.3 (4)
C3—C2—H2	120.9	C24—C23—C22	119.0 (4)
C1—C2—H2	120.9	C23—C24—C25	121.2 (4)
C2—C3—C4	119.8 (5)	C23—C24—H24	119.4
C2—C3—H3A	120.1	C25—C24—H24	119.4
C4—C3—H3A	120.1	C26—C25—C24	120.0 (5)
C3—C4—C5	119.6 (5)	C26—C25—H25	120.0
C3—C4—H4	120.2	C24—C25—H25	120.0
C5—C4—H4	120.2	C27—C26—C25	119.3 (5)
N1—C5—C4	120.0 (4)	C27—C26—H26	120.4
N1—C5—C6	116.0 (4)	C25—C26—H26	120.4
C4—C5—C6	124.0 (4)	C26—C27—C28	121.2 (5)
N2—C6—C7	121.6 (4)	C26—C27—H27	119.4
N2—C6—C5	115.0 (3)	C28—C27—H27	119.4
C7—C6—C5	123.4 (4)	C23—C28—C27	119.8 (4)
C8—C7—C6	119.2 (5)	C23—C28—H28	120.1
C8—C7—H7	120.4	C27—C28—H28	120.1
C6—C7—H7	120.4	C34—C29—C30	118.2 (4)
C9—C8—C7	119.3 (5)	C34—C29—C22	120.2 (4)
C9—C8—H8	120.3	C30—C29—C22	121.6 (4)
C7—C8—H8	120.3	C31—C30—C29	120.5 (5)
C8—C9—C10	118.8 (5)	C31—C30—H30	119.7
C8—C9—H9	120.6	C29—C30—H30	119.7
C10—C9—H9	120.6	C30—C31—C32	120.1 (5)
N2—C10—C9	122.9 (4)	C30—C31—H31	119.9
N2—C10—H10	118.6	C32—C31—H31	119.9
C9—C10—H10	118.6	C33—C32—C31	119.5 (5)
N3—C11—C12	123.7 (5)	C33—C32—H32	120.3
N3—C11—H11	118.2	C31—C32—H32	120.3
C12—C11—H11	118.2	C32—C33—C34	120.9 (5)
C11—C12—C13	117.4 (5)	C32—C33—H33	119.6
C11—C12—H12	121.3	C34—C33—H33	119.6
C13—C12—H12	121.3	C33—C34—C29	120.8 (5)
C14—C13—C12	120.4 (5)	C33—C34—H34	119.6
C14—C13—H13	119.8	C29—C34—H34	119.6

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H3W···O5i	0.85	2.16	2.844 (6)	138
O1W—H1W···O4ii	0.85	2.07	2.884 (7)	159
O2W—H3W···O1Wiii	0.85	2.59	3.041 (7)	114
O1W—H2W···O2Wiii	0.85	2.46	3.041 (7)	126
O1W—H2W···O4iv	0.85	2.28	2.856 (6)	125
O3—H3···O6v	0.82	2.48	3.210 (5)	149
O3—H3···O1	0.82	2.10	2.597 (4)	119
C20—H20···O2	0.93	2.53	3.019 (5)	113
C30—H30···O2	0.93	2.52	2.994 (5)	112
C34—H34···O3	0.93	2.35	2.728 (6)	104
C10—H10···O1W	0.93	2.41	3.341 (7)	174
C8—H8···O3iv	0.93	2.54	3.389 (6)	152
C4—H4···O5vi	0.93	2.59	3.488 (6)	162
C12—H12···O5vii	0.93	2.38	3.285 (7)	165
C14—H14···O1viii	0.93	2.56	3.420 (6)	155
C17—H17···O1viii	0.93	2.39	3.270 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H3W⋯O5i	0.85	2.16	2.844 (6)	138
O1W—H1W⋯O4ii	0.85	2.07	2.884 (7)	159
O2W—H3W⋯O1Wiii	0.85	2.59	3.041 (7)	114
O1W—H2W⋯O2Wiii	0.85	2.46	3.041 (7)	126
O1W—H2W⋯O4iv	0.85	2.28	2.856 (6)	125
O3—H3⋯O6v	0.82	2.48	3.210 (5)	149
O3—H3⋯O1	0.82	2.10	2.597 (4)	119
C10—H10⋯O1W	0.93	2.41	3.341 (7)	174
C8—H8⋯O3iv	0.93	2.54	3.389 (6)	152
C4—H4⋯O5vi	0.93	2.59	3.488 (6)	162
C12—H12⋯O5vii	0.93	2.38	3.285 (7)	165
C14—H14⋯O1viii	0.93	2.56	3.420 (6)	155
C17—H17⋯O1viii	0.93	2.39	3.270 (5)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .