A twofold inter­penetrating three-dimensional zinc–organic framework built from naphthalene-1,4-di­carboxyl­ate and 4,4′-bi­pyridine ligands

A novel three-dimensional Zn^II complex, poly[[(μ₂-4,4′-bi­pyridine)(μ₄-naphthalene-1,4-di­carboxyl­ato)(μ₂-naphthalene-1,4-di­carboxyl­ato)dizinc(II)] di­methyl­formamide monosolvate monohydrate], {[Zn₂(C₁₂H₆O₄)₂(C₁₀H₈N₂)]·2C₃H₇NO·H₂O)}_n, has been prepared by the solvothermal assembly of Zn(NO₃)·6H₂O, naphthalene-1,4-di­carb­oxy­lic acid and 4,4′-bi­pyridine. The two crystallographically independent Zn atoms adopt the same four-coordinated tetra­hedral geometry (ZnO₃N) by bonding to three O atoms from three different naphthalene-1,4-di­carboxyl­ate (1,4-ndc) ligands and one N atom from a 4,4′-bi­pyridine (bpy) ligand. The supra­molecular secondary building unit (SBU) is a distorted paddle-wheel-like {Zn₂(COO)₂N₂O₂} unit and these units are linked by 1,4-ndc ligands within the layer to form a two-dimensional net parallel to the ab plane, which is further connected by bpy ligands to form the three-dimensional framework. The single net leaves voids that are filled by mutual inter­penetration of an independent equivalent framework in a twofold inter­penetrating architecture. The title compound is stable up to 673 K. Excitation and luminescence data observed at room temperature show that it emits bright-blue fluorescence.

Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Poly[[(µ₂-4,4'-bipyridine)(µ₄-naphthalene-1,4-dicarboxylato)(µ₂-naphthalene-1,4-dicarboxylato)dizinc(II)] dimethylformamide monosolvate monohydrate]

Crystal data

[Zn2(C12H6O4)2(C10H8N2)]·C3H7NO·H2O	Z = 2
Mr = 806.37	F(000) = 824
Triclinic, P1	Dx = 1.576 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.239 (2) Å	Cell parameters from 2895 reflections
b = 12.191 (2) Å	θ = 2.4–27.9°
c = 13.910 (3) Å	µ = 1.48 mm^−1
α = 94.60 (3)°	T = 293 K
β = 93.75 (3)°	Block, colourless
γ = 99.87 (3)°	0.30 × 0.25 × 0.21 mm
V = 1699.5 (6) Å^3

Data collection

Rigaku/MSC Mercury CCD area-detector diffractometer	6120 independent reflections
Radiation source: fine-focus sealed tube	4067 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω scans	θmax = 25.2°, θmin = 3.1°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −12→12
Tmin = 0.661, Tmax = 0.745	k = −14→14
13552 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 2.P] where P = (Fo^2 + 2Fc^2)/3
6120 reflections	(Δ/σ)max = 0.001
477 parameters	Δρmax = 0.79 e Å^−3
3 restraints	Δρmin = −0.97 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.

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.

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

	x	y	z	Uiso*/Ueq
Zn1	0.27797 (5)	−0.01907 (5)	0.77177 (4)	0.04007 (18)
Zn2	0.23890 (5)	0.80378 (5)	0.53952 (4)	0.04046 (18)
O1	0.3246 (4)	0.1214 (3)	0.7161 (3)	0.0716 (12)
O2	0.1766 (4)	0.1518 (4)	0.8159 (3)	0.0741 (12)
O3	0.3945 (5)	0.6463 (4)	0.5476 (3)	0.0756 (12)
O4	0.2073 (4)	0.6723 (3)	0.6071 (3)	0.0638 (10)
O5	0.4087 (3)	0.9020 (3)	0.5839 (2)	0.0442 (8)
O6	0.4305 (3)	0.9066 (3)	0.7441 (2)	0.0492 (9)
O7	1.0766 (3)	0.8666 (3)	0.5628 (2)	0.0507 (9)
O8	1.1046 (3)	0.8958 (3)	0.7231 (2)	0.0538 (9)
O9	0.2308 (6)	0.5872 (5)	0.1504 (4)	0.1129 (19)
N1	0.2349 (4)	0.8087 (3)	0.3960 (3)	0.0415 (9)
N2	0.2778 (4)	0.9507 (4)	−0.0854 (3)	0.0462 (10)
N3	0.2006 (6)	0.5212 (5)	0.2972 (5)	0.0840 (17)
C1	0.2931 (5)	0.5111 (4)	0.6470 (4)	0.0491 (12)
C2	0.3285 (6)	0.4216 (5)	0.5961 (4)	0.0575 (14)
H2	0.3617	0.4298	0.5360	0.069*
C3	0.3149 (5)	0.3176 (5)	0.6340 (4)	0.0577 (14)
H3	0.3390	0.2577	0.5979	0.069*
C4	0.2672 (5)	0.3010 (4)	0.7226 (4)	0.0476 (12)
C5	0.1911 (6)	0.3867 (5)	0.8744 (4)	0.0637 (16)
H5	0.1807	0.3183	0.9008	0.076*
C6	0.1650 (7)	0.4782 (6)	0.9269 (5)	0.0781 (19)
H6	0.1366	0.4711	0.9886	0.094*
C7	0.1797 (7)	0.5826 (6)	0.8904 (4)	0.0765 (19)
H7	0.1622	0.6443	0.9279	0.092*
C8	0.2202 (6)	0.5938 (5)	0.7988 (4)	0.0625 (15)
H8	0.2296	0.6634	0.7745	0.075*
C9	0.2480 (5)	0.5002 (4)	0.7407 (4)	0.0495 (12)
C10	0.2343 (5)	0.3942 (4)	0.7792 (4)	0.0485 (12)
C11	0.2556 (5)	0.1869 (5)	0.7554 (4)	0.0548 (14)
C12	0.3035 (6)	0.6181 (5)	0.5974 (4)	0.0550 (14)
C13	0.6132 (4)	0.8711 (4)	0.6570 (3)	0.0379 (10)
C14	0.6790 (4)	0.9049 (4)	0.5793 (3)	0.0410 (11)
H14	0.6336	0.9316	0.5287	0.049*
C15	0.8146 (4)	0.8999 (4)	0.5749 (3)	0.0418 (11)
H15	0.8570	0.9213	0.5205	0.050*
C16	0.8849 (4)	0.8640 (4)	0.6493 (3)	0.0388 (11)
C17	0.8825 (5)	0.7709 (5)	0.8035 (4)	0.0544 (14)
H17	0.9730	0.7697	0.8026	0.065*
C18	0.8149 (6)	0.7251 (5)	0.8759 (4)	0.0653 (17)
H18	0.8597	0.6950	0.9248	0.078*
C19	0.6781 (6)	0.7235 (5)	0.8766 (4)	0.0658 (17)
H19	0.6321	0.6909	0.9255	0.079*
C20	0.6120 (5)	0.7688 (5)	0.8069 (4)	0.0533 (14)
H20	0.5207	0.7657	0.8083	0.064*
C21	0.6788 (4)	0.8210 (4)	0.7316 (3)	0.0390 (11)
C22	0.8180 (4)	0.8200 (4)	0.7296 (3)	0.0409 (11)
C23	0.4733 (4)	0.8940 (4)	0.6621 (3)	0.0398 (11)
C24	1.0329 (4)	0.8751 (4)	0.6451 (4)	0.0414 (11)
C25	0.3484 (5)	0.8117 (4)	0.3520 (3)	0.0449 (12)
H25	0.4233	0.7976	0.3871	0.054*
C26	0.3586 (5)	0.8346 (4)	0.2576 (3)	0.0455 (12)
H26	0.4387	0.8345	0.2296	0.055*
C27	0.2496 (5)	0.8579 (4)	0.2039 (3)	0.0436 (12)
C28	0.1317 (5)	0.8511 (5)	0.2484 (4)	0.0527 (14)
H28	0.0551	0.8632	0.2143	0.063*
C29	0.1280 (5)	0.8266 (5)	0.3428 (3)	0.0490 (13)
H29	0.0478	0.8223	0.3712	0.059*
C30	0.2592 (5)	0.8891 (4)	0.1039 (3)	0.0457 (12)
C31	0.3497 (6)	0.8527 (6)	0.0447 (4)	0.0673 (17)
H31	0.4064	0.8068	0.0674	0.081*
C32	0.3554 (6)	0.8846 (6)	−0.0478 (4)	0.0657 (17)
H32	0.4167	0.8588	−0.0863	0.079*
C33	0.1944 (6)	0.9885 (6)	−0.0272 (4)	0.0688 (18)
H33	0.1424	1.0378	−0.0501	0.083*
C34	0.1812 (6)	0.9579 (6)	0.0658 (4)	0.0712 (19)
H34	0.1188	0.9845	0.1028	0.085*
C35	0.1615 (8)	0.5598 (7)	0.2156 (6)	0.089 (2)
H35	0.0725	0.5666	0.2072	0.107*
C36	0.3378 (7)	0.5079 (7)	0.3178 (6)	0.104 (3)
H36A	0.3901	0.5362	0.2674	0.156*
H36B	0.3415	0.4301	0.3209	0.156*
H36C	0.3725	0.5487	0.3786	0.156*
C37	0.1080 (8)	0.4880 (8)	0.3692 (6)	0.114 (3)
H37A	0.0224	0.5049	0.3498	0.172*
H37B	0.1404	0.5282	0.4307	0.172*
H37C	0.1001	0.4092	0.3744	0.172*
O1W	0.4748 (8)	0.6107 (10)	0.0698 (9)	0.198 (4)
H2W	0.526 (11)	0.567 (11)	0.081 (13)	0.297*
H1W	0.404 (9)	0.599 (13)	0.096 (12)	0.297*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0394 (3)	0.0495 (4)	0.0333 (3)	0.0127 (2)	0.0016 (2)	0.0073 (2)
Zn2	0.0405 (3)	0.0526 (4)	0.0312 (3)	0.0145 (2)	0.0012 (2)	0.0099 (3)
O1	0.063 (2)	0.052 (3)	0.107 (3)	0.0212 (19)	0.016 (2)	0.022 (2)
O2	0.077 (3)	0.068 (3)	0.082 (3)	0.015 (2)	0.009 (2)	0.031 (2)
O3	0.100 (3)	0.063 (3)	0.070 (3)	0.018 (2)	0.028 (3)	0.020 (2)
O4	0.069 (2)	0.060 (3)	0.068 (3)	0.019 (2)	0.003 (2)	0.024 (2)
O5	0.0377 (17)	0.059 (2)	0.0380 (19)	0.0153 (15)	−0.0049 (15)	0.0127 (16)
O6	0.0441 (19)	0.075 (3)	0.0349 (19)	0.0232 (17)	0.0088 (15)	0.0138 (17)
O7	0.0430 (18)	0.078 (3)	0.0390 (19)	0.0211 (17)	0.0125 (16)	0.0213 (18)
O8	0.0410 (18)	0.078 (3)	0.041 (2)	0.0066 (17)	−0.0033 (16)	0.0111 (18)
O9	0.148 (5)	0.112 (5)	0.075 (4)	0.019 (4)	0.002 (4)	0.000 (3)
N1	0.045 (2)	0.048 (3)	0.031 (2)	0.0124 (18)	−0.0018 (18)	0.0028 (18)
N2	0.051 (2)	0.060 (3)	0.032 (2)	0.023 (2)	0.0013 (18)	0.0040 (19)
N3	0.084 (4)	0.084 (4)	0.076 (4)	0.010 (3)	−0.011 (3)	−0.013 (3)
C1	0.063 (3)	0.047 (3)	0.039 (3)	0.013 (2)	−0.003 (2)	0.011 (2)
C2	0.072 (4)	0.054 (4)	0.050 (3)	0.018 (3)	0.008 (3)	0.011 (3)
C3	0.065 (3)	0.051 (4)	0.060 (4)	0.019 (3)	0.003 (3)	0.007 (3)
C4	0.046 (3)	0.047 (3)	0.053 (3)	0.014 (2)	−0.003 (2)	0.013 (3)
C5	0.085 (4)	0.063 (4)	0.048 (3)	0.021 (3)	−0.001 (3)	0.021 (3)
C6	0.119 (6)	0.073 (5)	0.046 (4)	0.027 (4)	0.006 (4)	0.007 (3)
C7	0.116 (5)	0.067 (5)	0.051 (4)	0.028 (4)	0.009 (4)	0.004 (3)
C8	0.083 (4)	0.055 (4)	0.051 (3)	0.021 (3)	−0.001 (3)	0.004 (3)
C9	0.054 (3)	0.049 (3)	0.046 (3)	0.013 (2)	−0.009 (2)	0.009 (2)
C10	0.054 (3)	0.047 (3)	0.044 (3)	0.012 (2)	−0.008 (2)	0.009 (2)
C11	0.045 (3)	0.052 (4)	0.068 (4)	0.012 (2)	−0.010 (3)	0.013 (3)
C12	0.067 (4)	0.053 (4)	0.047 (3)	0.013 (3)	−0.001 (3)	0.010 (3)
C13	0.034 (2)	0.045 (3)	0.036 (3)	0.0117 (19)	0.000 (2)	0.007 (2)
C14	0.040 (3)	0.053 (3)	0.032 (2)	0.014 (2)	−0.001 (2)	0.011 (2)
C15	0.044 (3)	0.051 (3)	0.033 (3)	0.012 (2)	0.004 (2)	0.012 (2)
C16	0.037 (2)	0.046 (3)	0.036 (3)	0.014 (2)	0.002 (2)	0.010 (2)
C17	0.047 (3)	0.071 (4)	0.053 (3)	0.023 (3)	0.005 (3)	0.024 (3)
C18	0.067 (4)	0.087 (5)	0.054 (3)	0.032 (3)	0.003 (3)	0.041 (3)
C19	0.065 (4)	0.088 (5)	0.056 (4)	0.027 (3)	0.017 (3)	0.038 (3)
C20	0.051 (3)	0.065 (4)	0.052 (3)	0.020 (3)	0.014 (3)	0.028 (3)
C21	0.041 (3)	0.046 (3)	0.035 (2)	0.016 (2)	0.005 (2)	0.014 (2)
C22	0.044 (3)	0.052 (3)	0.032 (2)	0.018 (2)	0.002 (2)	0.015 (2)
C23	0.037 (2)	0.040 (3)	0.044 (3)	0.010 (2)	0.001 (2)	0.015 (2)
C24	0.040 (3)	0.047 (3)	0.041 (3)	0.013 (2)	0.002 (2)	0.017 (2)
C25	0.040 (3)	0.059 (3)	0.040 (3)	0.018 (2)	−0.001 (2)	0.008 (2)
C26	0.044 (3)	0.065 (4)	0.030 (3)	0.014 (2)	0.008 (2)	0.007 (2)
C27	0.044 (3)	0.057 (3)	0.030 (2)	0.010 (2)	−0.002 (2)	0.007 (2)
C28	0.041 (3)	0.081 (4)	0.038 (3)	0.019 (3)	−0.002 (2)	0.008 (3)
C29	0.040 (3)	0.074 (4)	0.034 (3)	0.013 (2)	0.000 (2)	0.011 (3)
C30	0.052 (3)	0.056 (3)	0.032 (3)	0.016 (2)	0.000 (2)	0.009 (2)
C31	0.082 (4)	0.092 (5)	0.044 (3)	0.049 (4)	0.012 (3)	0.023 (3)
C32	0.079 (4)	0.098 (5)	0.037 (3)	0.048 (4)	0.019 (3)	0.021 (3)
C33	0.077 (4)	0.103 (5)	0.044 (3)	0.055 (4)	0.010 (3)	0.023 (3)
C34	0.072 (4)	0.118 (6)	0.041 (3)	0.050 (4)	0.022 (3)	0.026 (3)
C35	0.103 (6)	0.085 (6)	0.073 (5)	0.015 (4)	−0.021 (5)	−0.010 (4)
C36	0.091 (5)	0.119 (7)	0.102 (6)	0.035 (5)	−0.010 (5)	−0.008 (5)
C37	0.108 (6)	0.137 (8)	0.088 (6)	0.000 (5)	−0.002 (5)	0.003 (5)
O1W	0.111 (6)	0.265 (11)	0.239 (10)	0.042 (6)	0.015 (6)	0.129 (9)

Geometric parameters (Å, º)

Zn1—O1	1.934 (4)	C9—C10	1.427 (7)
Zn1—O8^i	1.945 (3)	C13—C14	1.366 (6)
Zn1—O6^ii	1.979 (3)	C13—C21	1.431 (6)
Zn1—N2^iii	2.050 (4)	C13—C23	1.511 (6)
Zn2—O4	1.913 (4)	C14—C15	1.405 (6)
Zn2—O5	1.966 (3)	C14—H14	0.9300
Zn2—O7^iv	1.980 (3)	C15—C16	1.366 (6)
Zn2—N1	2.000 (4)	C15—H15	0.9300
O1—C11	1.269 (6)	C16—C22	1.439 (6)
O2—C11	1.255 (6)	C16—C24	1.504 (6)
O3—C12	1.216 (6)	C17—C18	1.360 (7)
O4—C12	1.285 (6)	C17—C22	1.414 (6)
O5—C23	1.255 (5)	C17—H17	0.9300
O6—C23	1.256 (5)	C18—C19	1.398 (7)
O6—Zn1^v	1.979 (3)	C18—H18	0.9300
O7—C24	1.258 (5)	C19—C20	1.354 (7)
O7—Zn2^vi	1.980 (3)	C19—H19	0.9300
O8—C24	1.253 (6)	C20—C21	1.422 (6)
O8—Zn1^vii	1.945 (3)	C20—H20	0.9300
O9—C35	1.220 (9)	C21—C22	1.429 (6)
N1—C29	1.340 (6)	C25—C26	1.371 (6)
N1—C25	1.346 (6)	C25—H25	0.9300
N2—C33	1.326 (6)	C26—C27	1.385 (6)
N2—C32	1.337 (6)	C26—H26	0.9300
N2—Zn1^viii	2.050 (4)	C27—C28	1.385 (6)
N3—C35	1.328 (9)	C27—C30	1.476 (6)
N3—C36	1.454 (8)	C28—C29	1.371 (7)
N3—C37	1.456 (9)	C28—H28	0.9300
C1—C2	1.367 (7)	C29—H29	0.9300
C1—C9	1.420 (7)	C30—C34	1.367 (7)
C1—C12	1.514 (7)	C30—C31	1.384 (7)
C2—C3	1.401 (7)	C31—C32	1.376 (7)
C2—H2	0.9300	C31—H31	0.9300
C3—C4	1.372 (7)	C32—H32	0.9300
C3—H3	0.9300	C33—C34	1.384 (7)
C4—C10	1.430 (7)	C33—H33	0.9300
C4—C11	1.486 (7)	C34—H34	0.9300
C5—C6	1.359 (8)	C35—H35	0.9300
C5—C10	1.427 (7)	C36—H36A	0.9600
C5—H5	0.9300	C36—H36B	0.9600
C6—C7	1.396 (9)	C36—H36C	0.9600
C6—H6	0.9300	C37—H37A	0.9600
C7—C8	1.376 (8)	C37—H37B	0.9600
C7—H7	0.9300	C37—H37C	0.9600
C8—C9	1.425 (8)	O1W—H2W	0.822 (10)
C8—H8	0.9300	O1W—H1W	0.825 (10)
O1—Zn1—O8^i	114.07 (17)	C15—C16—C24	117.7 (4)
O1—Zn1—O6^ii	102.14 (15)	C22—C16—C24	122.1 (4)
O8^i—Zn1—O6^ii	114.99 (16)	C18—C17—C22	121.4 (5)
O1—Zn1—N2^iii	129.03 (19)	C18—C17—H17	119.3
O8^i—Zn1—N2^iii	100.04 (16)	C22—C17—H17	119.3
O6^ii—Zn1—N2^iii	95.75 (14)	C17—C18—C19	119.9 (5)
O4—Zn2—O5	112.88 (16)	C17—C18—H18	120.0
O4—Zn2—O7^iv	100.76 (15)	C19—C18—H18	120.0
O5—Zn2—O7^iv	115.86 (15)	C20—C19—C18	120.8 (5)
O4—Zn2—N1	126.33 (17)	C20—C19—H19	119.6
O5—Zn2—N1	102.10 (15)	C18—C19—H19	119.6
O7^iv—Zn2—N1	98.80 (15)	C19—C20—C21	121.5 (5)
C11—O1—Zn1	105.9 (4)	C19—C20—H20	119.2
C12—O4—Zn2	109.5 (3)	C21—C20—H20	119.2
C23—O5—Zn2	123.1 (3)	C20—C21—C22	117.6 (4)
C23—O6—Zn1^v	124.6 (3)	C20—C21—C13	123.4 (4)
C24—O7—Zn2^vi	122.6 (3)	C22—C21—C13	118.9 (4)
C24—O8—Zn1^vii	138.7 (3)	C17—C22—C21	118.8 (4)
C29—N1—C25	117.1 (4)	C17—C22—C16	122.8 (4)
C29—N1—Zn2	122.6 (3)	C21—C22—C16	118.3 (4)
C25—N1—Zn2	119.5 (3)	O5—C23—O6	124.3 (4)
C33—N2—C32	116.3 (4)	O5—C23—C13	117.6 (4)
C33—N2—Zn1^viii	122.2 (4)	O6—C23—C13	118.1 (4)
C32—N2—Zn1^viii	121.3 (3)	O8—C24—O7	124.4 (4)
C35—N3—C36	121.2 (7)	O8—C24—C16	118.0 (4)
C35—N3—C37	121.7 (7)	O7—C24—C16	117.6 (4)
C36—N3—C37	117.0 (7)	N1—C25—C26	122.9 (4)
C2—C1—C9	120.0 (5)	N1—C25—H25	118.6
C2—C1—C12	116.5 (5)	C26—C25—H25	118.6
C9—C1—C12	123.6 (5)	C25—C26—C27	119.9 (4)
C1—C2—C3	120.4 (5)	C25—C26—H26	120.0
C1—C2—H2	119.8	C27—C26—H26	120.0
C3—C2—H2	119.8	C26—C27—C28	117.0 (4)
C4—C3—C2	122.2 (5)	C26—C27—C30	121.3 (4)
C4—C3—H3	118.9	C28—C27—C30	121.7 (4)
C2—C3—H3	118.9	C29—C28—C27	120.0 (5)
C3—C4—C10	118.7 (5)	C29—C28—H28	120.0
C3—C4—C11	117.7 (5)	C27—C28—H28	120.0
C10—C4—C11	123.5 (5)	N1—C29—C28	122.9 (4)
C6—C5—C10	120.9 (6)	N1—C29—H29	118.5
C6—C5—H5	119.6	C28—C29—H29	118.5
C10—C5—H5	119.6	C34—C30—C31	116.5 (5)
C5—C6—C7	121.6 (6)	C34—C30—C27	121.5 (4)
C5—C6—H6	119.2	C31—C30—C27	121.9 (5)
C7—C6—H6	119.2	C32—C31—C30	119.7 (5)
C8—C7—C6	119.7 (6)	C32—C31—H31	120.1
C8—C7—H7	120.2	C30—C31—H31	120.1
C6—C7—H7	120.2	N2—C32—C31	123.7 (5)
C7—C8—C9	120.8 (6)	N2—C32—H32	118.2
C7—C8—H8	119.6	C31—C32—H32	118.2
C9—C8—H8	119.6	N2—C33—C34	123.1 (5)
C1—C9—C8	121.4 (5)	N2—C33—H33	118.4
C1—C9—C10	119.5 (5)	C34—C33—H33	118.4
C8—C9—C10	119.0 (5)	C30—C34—C33	120.6 (5)
C9—C10—C5	118.0 (5)	C30—C34—H34	119.7
C9—C10—C4	119.1 (5)	C33—C34—H34	119.7
C5—C10—C4	122.8 (5)	O9—C35—N3	126.5 (8)
O2—C11—O1	119.4 (5)	O9—C35—H35	116.8
O2—C11—C4	123.0 (5)	N3—C35—H35	116.8
O1—C11—C4	117.6 (5)	N3—C36—H36A	109.5
O3—C12—O4	122.9 (5)	N3—C36—H36B	109.5
O3—C12—C1	121.0 (5)	H36A—C36—H36B	109.5
O4—C12—C1	115.9 (5)	N3—C36—H36C	109.5
C14—C13—C21	120.2 (4)	H36A—C36—H36C	109.5
C14—C13—C23	117.1 (4)	H36B—C36—H36C	109.5
C21—C13—C23	122.7 (4)	N3—C37—H37A	109.5
C13—C14—C15	120.8 (4)	N3—C37—H37B	109.5
C13—C14—H14	119.6	H37A—C37—H37B	109.5
C15—C14—H14	119.6	N3—C37—H37C	109.5
C16—C15—C14	120.9 (4)	H37A—C37—H37C	109.5
C16—C15—H15	119.6	H37B—C37—H37C	109.5
C14—C15—H15	119.6	H2W—O1W—H1W	115 (2)
C15—C16—C22	120.2 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O9	0.83 (1)	1.96 (2)	2.784 (10)	173 (14)