Poly[bis-(dimethyl-ammonium) [bis-(dimethyl-amine-κN)tris-(μ(2)-terephthalato-κO:O)dizinc(II)] N,N-dimethyl-formamide disolvate hexa-hydrate].

The title compound, {(C(2)H(8)N)(2)[Zn(2)(C(8)H(4)O(4))(3)(C(2)H(7)N)(2)]·2C(3)H(7)NO·6H(2)O}(n), consists of two-dimensional non-inter-penetrated sheets with 6(3) topology, which are stacked together in an …ABAB… packing mode along the c axis. The distance between adjacent A and B sheets is ca 7.3 Å. In the structure, the Zn(II) center is coordinated by three O atoms from three terephthalate groups and one N atom from one dimethyl-amine ligand, adopting a distorted tetra-hedral geometry. All solvent water mol-ecules are disordered. In the structure, N-H⋯O and O-H⋯O hydrogen bonds are observed.

Related literature

For background to metal-organic frameworks, see: Kitagawa et al. (2004 ▶); Rowsell et al. (2004 ▶); Tranchemontagne et al. (2008 ▶); Wang et al. (2008 ▶); Hawxwell et al. (2006 ▶). For related structures, see: Wang et al. (2007 ▶); Go et al.(2007 ▶); Dai et al. (2004 ▶); Guo et al. (2009 ▶); He et al. (2005 ▶); Zhu et al. (2007 ▶); Clausen et al. (2005 ▶); Dybtsev et al. (2004 ▶); Robin & Fromm (2006 ▶); Rowsell & Yaghi (2004 ▶); Suh et al. (2008 ▶); Wu et al. (2005 ▶).

Experimental

Crystal data

(C2H8N)2[Zn2(C8H4O4)3(C2H7N)2]·2C3H7NO·6H2O

M = 1059.72

Orthorhombic,

a = 18.421 (6) Å

b = 30.906 (11) Å

c = 11.346 (4) Å

V = 6459 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 291 K

0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.81, T max = 0.85

49068 measured reflections

6463 independent reflections

3985 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.106

S = 1.04

6463 reflections

358 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030177/at2837sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030177/at2837Isup2.hkl

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

(C2H8N)2[Zn2(C8H4O4)3(C2H7N)2]·2C3H7NO·6H2O	F(000) = 2232
Mr = 1059.72	Dx = 1.090 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 6858 reflections
a = 18.421 (6) Å	θ = 2.2–23.6°
b = 30.906 (11) Å	µ = 0.80 mm−1
c = 11.346 (4) Å	T = 291 K
V = 6459 (4) Å3	Block, colourless
Z = 4	0.28 × 0.22 × 0.20 mm

Bruker SMART APEX CCD diffractometer	6463 independent reflections
Radiation source: sealed tube	3985 reflections with I > 2σ(I)
graphite	Rint = 0.090
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −22→22
Tmin = 0.81, Tmax = 0.85	k = −35→38
49068 measured reflections	l = −13→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0437P)2] where P = (Fo2 + 2Fc2)/3
6463 reflections	(Δ/σ)max < 0.001
358 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.44 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	Occ. (<1)
Zn1	0.748174 (18)	0.574369 (10)	0.82017 (3)	0.03184 (10)
O1	0.65833 (10)	0.56316 (7)	0.90871 (16)	0.0365 (5)
O2	0.66892 (11)	0.49777 (6)	0.82720 (15)	0.0346 (4)
O3	0.84206 (11)	0.54729 (7)	0.85243 (16)	0.0379 (5)
O4	0.80801 (10)	0.52970 (7)	1.03599 (16)	0.0396 (5)
O5	0.75628 (10)	0.63783 (6)	0.79740 (15)	0.0330 (4)
O6	0.78004 (10)	0.63646 (6)	0.98921 (16)	0.0346 (4)
N1	0.73121 (13)	0.55959 (8)	0.6450 (2)	0.0358 (6)
H1A	0.7200	0.5310	0.6400	0.043*
C1	0.63617 (15)	0.52421 (10)	0.8892 (2)	0.0358 (7)
C2	0.56500 (15)	0.51227 (9)	0.9466 (2)	0.0343 (6)
C3	0.52584 (15)	0.54188 (9)	1.0140 (2)	0.0349 (6)
H3	0.5431	0.5699	1.0241	0.042*
C4	0.53859 (14)	0.47065 (9)	0.9343 (2)	0.0338 (6)
H4	0.5648	0.4507	0.8902	0.041*
C5	0.85371 (15)	0.53206 (9)	0.9570 (2)	0.0303 (6)
C6	0.92994 (15)	0.51533 (9)	0.9779 (2)	0.0348 (6)
C7	0.97830 (16)	0.50915 (9)	0.8842 (2)	0.0347 (6)
H7	0.9637	0.5152	0.8076	0.042*
C8	0.95059 (16)	0.50634 (9)	1.0942 (2)	0.0375 (7)
H8	0.9182	0.5105	1.1561	0.045*
C9	0.76932 (16)	0.65657 (10)	0.8979 (3)	0.0390 (7)
C10	0.76968 (16)	0.70493 (10)	0.8943 (3)	0.0388 (7)
C11	0.77888 (16)	0.72718 (9)	0.9980 (2)	0.0368 (7)
H11	0.7851	0.7121	1.0683	0.044*
C12	0.75900 (15)	0.72744 (10)	0.7922 (3)	0.0399 (7)
H12	0.7517	0.7125	0.7220	0.048*
C13	0.79857 (15)	0.56728 (10)	0.5745 (2)	0.0361 (7)
H13A	0.7985	0.5488	0.5065	0.054*
H13B	0.8404	0.5610	0.6220	0.054*
H13C	0.8001	0.5970	0.5497	0.054*
C14	0.66929 (16)	0.58483 (10)	0.5948 (3)	0.0384 (7)
H14A	0.6832	0.6146	0.5867	0.058*
H14B	0.6282	0.5828	0.6466	0.058*
H14C	0.6566	0.5733	0.5190	0.058*
N2	0.71822 (14)	0.58391 (7)	0.1646 (2)	0.0354 (6)
H2A	0.7433	0.5721	0.1039	0.043*
H2B	0.6898	0.6051	0.1400	0.043*
C15	0.76977 (15)	0.60535 (9)	0.2428 (3)	0.0367 (7)
H15A	0.7630	0.5950	0.3219	0.055*
H15B	0.7618	0.6360	0.2405	0.055*
H15C	0.8184	0.5991	0.2175	0.055*
C16	0.67670 (15)	0.54833 (9)	0.2260 (3)	0.0368 (7)
H16A	0.7052	0.5371	0.2899	0.055*
H16B	0.6666	0.5255	0.1709	0.055*
H16C	0.6319	0.5597	0.2561	0.055*
N3	0.99518 (13)	0.65769 (8)	0.7182 (2)	0.0429 (6)
O7	0.94026 (11)	0.70680 (7)	0.62427 (17)	0.0433 (5)
C17	1.07238 (16)	0.66164 (10)	0.6734 (3)	0.0437 (7)
H17A	1.0783	0.6889	0.6338	0.066*
H17B	1.0823	0.6385	0.6194	0.066*
H17C	1.1055	0.6601	0.7387	0.066*
C18	0.97423 (16)	0.61309 (10)	0.7612 (3)	0.0399 (7)
H18A	0.9970	0.6076	0.8359	0.060*
H18B	0.9899	0.5918	0.7051	0.060*
H18C	0.9225	0.6115	0.7700	0.060*
C19	0.94719 (16)	0.69498 (10)	0.7315 (3)	0.0422 (8)
H19	0.9272	0.7069	0.7995	0.051*
O8	0.9438 (3)	0.67157 (17)	−0.0031 (4)	0.0440 (13)	0.40
H8X	0.9746	0.6689	−0.0584	0.053*	0.40
H8Y	0.9637	0.6652	0.0622	0.053*	0.40
O9	0.8541 (3)	0.71662 (18)	0.2652 (5)	0.0474 (13)	0.40
H9X	0.8835	0.7354	0.2384	0.057*	0.40
H9Y	0.8109	0.7258	0.2577	0.057*	0.40
O10	0.8853 (4)	0.6581 (2)	0.4696 (6)	0.0503 (18)	0.30
H10X	0.9200	0.6760	0.4780	0.060*	0.30
H10Y	0.8986	0.6333	0.4938	0.060*	0.30
O11	0.9212 (4)	0.6362 (2)	0.3470 (6)	0.0475 (18)	0.30
H11X	0.9660	0.6296	0.3475	0.057*	0.30
H11Y	0.9033	0.6426	0.2802	0.057*	0.30
O12	0.5802 (4)	0.6679 (2)	0.4913 (6)	0.0494 (18)	0.30
H12X	0.5468	0.6616	0.4425	0.059*	0.30
H12Y	0.5761	0.6937	0.5166	0.059*	0.30
O13	0.6421 (4)	0.7102 (2)	0.3095 (6)	0.0480 (18)	0.30
H13E	0.6165	0.7006	0.2528	0.072*	0.30
H13F	0.6247	0.7342	0.3331	0.072*	0.30
O14	0.5498 (4)	0.7708 (2)	0.2396 (6)	0.0467 (17)	0.30
H14E	0.5208	0.7614	0.1873	0.056*	0.30
H14F	0.5316	0.7931	0.2722	0.056*	0.30
O15	0.5532 (4)	0.6179 (2)	0.2001 (6)	0.0437 (17)	0.30
H15X	0.5213	0.6289	0.2452	0.052*	0.30
H15Y	0.5933	0.6311	0.2089	0.052*	0.30
O16	0.7248 (3)	0.67473 (17)	0.5303 (5)	0.0454 (13)	0.40
H16X	0.6995	0.6740	0.4677	0.055*	0.40
H16Y	0.7597	0.6925	0.5220	0.055*	0.40

	U11	U22	U33	U12	U13	U23
Zn1	0.03285 (19)	0.02973 (17)	0.03293 (17)	0.00038 (15)	−0.00052 (13)	−0.00070 (13)
O1	0.0329 (11)	0.0421 (12)	0.0345 (10)	−0.0038 (9)	−0.0018 (8)	0.0003 (9)
O2	0.0368 (11)	0.0372 (11)	0.0297 (9)	−0.0015 (9)	−0.0077 (8)	0.0008 (8)
O3	0.0346 (11)	0.0463 (12)	0.0327 (10)	0.0112 (10)	−0.0048 (8)	−0.0049 (9)
O4	0.0354 (12)	0.0464 (13)	0.0370 (10)	0.0076 (9)	−0.0040 (9)	−0.0066 (9)
O5	0.0330 (11)	0.0335 (10)	0.0326 (10)	−0.0033 (9)	−0.0025 (8)	−0.0010 (8)
O6	0.0371 (11)	0.0300 (10)	0.0367 (10)	−0.0031 (9)	−0.0023 (8)	−0.0054 (8)
N1	0.0339 (14)	0.0394 (14)	0.0340 (12)	0.0024 (10)	−0.0009 (9)	0.0002 (11)
C1	0.0351 (17)	0.0433 (18)	0.0291 (14)	−0.0044 (13)	0.0054 (12)	−0.0048 (13)
C2	0.0320 (16)	0.0354 (16)	0.0356 (14)	−0.0002 (13)	0.0018 (12)	0.0039 (12)
C3	0.0307 (16)	0.0355 (16)	0.0386 (14)	0.0028 (13)	−0.0045 (12)	−0.0043 (12)
C4	0.0273 (16)	0.0383 (16)	0.0357 (14)	−0.0078 (12)	−0.0012 (11)	−0.0057 (12)
C5	0.0290 (16)	0.0275 (14)	0.0342 (15)	−0.0017 (11)	−0.0044 (12)	−0.0034 (12)
C6	0.0333 (16)	0.0373 (16)	0.0339 (14)	−0.0013 (13)	0.0062 (12)	0.0002 (12)
C7	0.0338 (16)	0.0372 (16)	0.0330 (14)	0.0048 (13)	0.0015 (12)	−0.0067 (12)
C8	0.0285 (15)	0.0458 (18)	0.0381 (14)	0.0021 (13)	−0.0027 (12)	−0.0015 (13)
C9	0.0422 (18)	0.0308 (16)	0.0440 (16)	0.0016 (13)	0.0018 (13)	−0.0051 (14)
C10	0.0435 (18)	0.0312 (15)	0.0418 (15)	0.0020 (13)	−0.0039 (13)	0.0024 (13)
C11	0.0390 (16)	0.0367 (15)	0.0347 (15)	0.0005 (13)	0.0066 (12)	0.0017 (12)
C12	0.0430 (18)	0.0376 (16)	0.0393 (16)	0.0082 (14)	0.0040 (13)	0.0076 (12)
C13	0.0384 (17)	0.0369 (17)	0.0331 (14)	−0.0002 (13)	−0.0042 (12)	−0.0084 (12)
C14	0.0385 (17)	0.0413 (18)	0.0356 (15)	0.0044 (13)	0.0035 (13)	−0.0107 (12)
N2	0.0398 (14)	0.0327 (14)	0.0337 (12)	−0.0028 (11)	0.0066 (10)	0.0004 (10)
C15	0.0370 (17)	0.0334 (15)	0.0397 (15)	−0.0177 (13)	0.0012 (12)	−0.0102 (12)
C16	0.0316 (16)	0.0323 (16)	0.0465 (16)	−0.0011 (12)	0.0123 (13)	0.0159 (12)
N3	0.0420 (16)	0.0411 (15)	0.0455 (14)	0.0119 (12)	0.0147 (12)	0.0146 (11)
O7	0.0435 (13)	0.0435 (12)	0.0428 (11)	0.0153 (10)	0.0121 (9)	0.0114 (9)
C17	0.0383 (18)	0.0393 (18)	0.0534 (18)	−0.0045 (14)	−0.0091 (14)	−0.0137 (15)
C18	0.0336 (16)	0.0411 (17)	0.0451 (16)	−0.0150 (13)	−0.0167 (13)	0.0163 (14)
C19	0.0383 (18)	0.0489 (19)	0.0393 (16)	0.0136 (15)	0.0184 (13)	0.0106 (14)
O8	0.053 (3)	0.046 (3)	0.033 (2)	0.006 (3)	0.016 (2)	0.013 (2)
O9	0.036 (3)	0.059 (4)	0.047 (3)	−0.001 (3)	−0.004 (2)	−0.004 (3)
O10	0.050 (5)	0.050 (5)	0.050 (4)	−0.001 (4)	−0.019 (4)	0.007 (3)
O11	0.048 (4)	0.054 (5)	0.040 (4)	0.017 (4)	−0.014 (3)	−0.011 (3)
O12	0.050 (5)	0.054 (5)	0.044 (4)	−0.002 (4)	−0.002 (3)	−0.003 (3)
O13	0.054 (5)	0.039 (4)	0.051 (4)	−0.002 (3)	−0.003 (3)	−0.011 (3)
O14	0.041 (4)	0.055 (4)	0.044 (4)	−0.001 (3)	0.005 (3)	0.017 (3)
O15	0.038 (4)	0.042 (4)	0.051 (4)	0.020 (3)	0.006 (3)	0.017 (3)
O16	0.047 (3)	0.047 (3)	0.042 (3)	0.022 (3)	0.003 (2)	0.010 (2)

Zn1—O3	1.956 (2)	N2—C16	1.509 (3)
Zn1—O1	1.967 (2)	N2—H2A	0.9063
Zn1—O5	1.984 (2)	N2—H2B	0.8851
Zn1—N1	2.063 (2)	C15—H15A	0.9600
O1—C1	1.290 (4)	C15—H15B	0.9600
O2—C1	1.236 (3)	C15—H15C	0.9600
O3—C5	1.295 (3)	C16—H16A	0.9600
O4—C5	1.231 (3)	C16—H16B	0.9600
O5—C9	1.301 (3)	C16—H16C	0.9600
O6—C9	1.224 (3)	N3—C19	1.460 (4)
N1—C14	1.494 (4)	N3—C18	1.512 (4)
N1—C13	1.495 (4)	N3—C17	1.515 (4)
N1—H1A	0.9100	O7—C19	1.277 (3)
C1—C2	1.510 (4)	C17—H17A	0.9600
C2—C4	1.382 (4)	C17—H17B	0.9600
C2—C3	1.394 (4)	C17—H17C	0.9600
C3—C4i	1.379 (4)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C3i	1.379 (4)	C18—H18C	0.9600
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.515 (4)	O8—H8X	0.8500
C6—C7	1.400 (4)	O8—H8Y	0.8501
C6—C8	1.402 (4)	O9—H9X	0.8500
C7—C8ii	1.416 (4)	O9—H9Y	0.8499
C7—H7	0.9300	O10—O11	1.682 (9)
C8—C7ii	1.416 (4)	O10—H10X	0.8500
C8—H8	0.9300	O10—H10Y	0.8501
C9—C10	1.495 (4)	O11—H11X	0.8501
C10—C12	1.366 (4)	O11—H11Y	0.8501
C10—C11	1.373 (4)	O12—H12X	0.8500
C11—C11iii	1.411 (6)	O12—H12Y	0.8499
C11—H11	0.9300	O13—H13E	0.8499
C12—C12iii	1.394 (6)	O13—H13F	0.8501
C12—H12	0.9300	O14—O14iii	1.287 (14)
C13—H13A	0.9600	O14—H14E	0.8501
C13—H13B	0.9600	O14—H14F	0.8501
C13—H13C	0.9600	O15—H15X	0.8499
C14—H14A	0.9600	O15—H15Y	0.8500
C14—H14B	0.9600	O16—H16X	0.8500
C14—H14C	0.9600	O16—H16Y	0.8499
N2—C15	1.459 (3)
O3—Zn1—O1	124.97 (9)	N1—C14—H14A	109.5
O3—Zn1—O5	112.39 (8)	N1—C14—H14B	109.5
O1—Zn1—O5	107.69 (8)	H14A—C14—H14B	109.5
O3—Zn1—N1	102.68 (9)	N1—C14—H14C	109.5
O1—Zn1—N1	109.00 (9)	H14A—C14—H14C	109.5
O5—Zn1—N1	96.02 (9)	H14B—C14—H14C	109.5
C1—O1—Zn1	110.06 (17)	C15—N2—C16	112.4 (2)
C5—O3—Zn1	118.27 (18)	C15—N2—H2A	108.3
C9—O5—Zn1	109.86 (18)	C16—N2—H2A	108.4
C14—N1—C13	110.3 (2)	C15—N2—H2B	104.0
C14—N1—Zn1	111.51 (17)	C16—N2—H2B	112.7
C13—N1—Zn1	110.75 (17)	H2A—N2—H2B	111.0
C14—N1—H1A	108.1	N2—C15—H15A	109.5
C13—N1—H1A	108.1	N2—C15—H15B	109.5
Zn1—N1—H1A	108.1	H15A—C15—H15B	109.5
O2—C1—O1	124.1 (3)	N2—C15—H15C	109.5
O2—C1—C2	120.5 (3)	H15A—C15—H15C	109.5
O1—C1—C2	115.4 (2)	H15B—C15—H15C	109.5
C4—C2—C3	119.0 (3)	N2—C16—H16A	109.5
C4—C2—C1	119.3 (3)	N2—C16—H16B	109.5
C3—C2—C1	121.7 (3)	H16A—C16—H16B	109.5
C4i—C3—C2	119.6 (3)	N2—C16—H16C	109.5
C4i—C3—H3	120.2	H16A—C16—H16C	109.5
C2—C3—H3	120.2	H16B—C16—H16C	109.5
C3i—C4—C2	121.4 (3)	C19—N3—C18	122.1 (2)
C3i—C4—H4	119.3	C19—N3—C17	122.6 (2)
C2—C4—H4	119.3	C18—N3—C17	114.9 (2)
O4—C5—O3	125.1 (3)	N3—C17—H17A	109.5
O4—C5—C6	120.0 (2)	N3—C17—H17B	109.5
O3—C5—C6	114.9 (2)	H17A—C17—H17B	109.5
C7—C6—C8	121.0 (3)	N3—C17—H17C	109.5
C7—C6—C5	121.2 (2)	H17A—C17—H17C	109.5
C8—C6—C5	117.8 (2)	H17B—C17—H17C	109.5
C6—C7—C8ii	120.3 (3)	N3—C18—H18A	109.5
C6—C7—H7	119.9	N3—C18—H18B	109.5
C8ii—C7—H7	119.9	H18A—C18—H18B	109.5
C6—C8—C7ii	118.7 (3)	N3—C18—H18C	109.5
C6—C8—H8	120.6	H18A—C18—H18C	109.5
C7ii—C8—H8	120.6	H18B—C18—H18C	109.5
O6—C9—O5	123.1 (3)	O7—C19—N3	100.8 (2)
O6—C9—C10	122.0 (3)	O7—C19—H19	129.6
O5—C9—C10	115.0 (3)	N3—C19—H19	129.6
C12—C10—C11	119.3 (3)	H8X—O8—H8Y	109.5
C12—C10—C9	122.1 (3)	H9X—O9—H9Y	109.5
C11—C10—C9	118.6 (3)	O11—O10—H10X	93.4
C10—C11—C11iii	120.06 (17)	O11—O10—H10Y	78.0
C10—C11—H11	120.0	H10X—O10—H10Y	109.5
C11iii—C11—H11	120.0	O10—O11—H11X	118.2
C10—C12—C12iii	120.63 (19)	O10—O11—H11Y	119.4
C10—C12—H12	119.7	H11X—O11—H11Y	116.1
C12iii—C12—H12	119.7	H12X—O12—H12Y	111.8
N1—C13—H13A	109.5	H13E—O13—H13F	109.5
N1—C13—H13B	109.5	O14iii—O14—H14E	70.0
H13A—C13—H13B	109.5	O14iii—O14—H14F	144.0
N1—C13—H13C	109.5	H14E—O14—H14F	109.5
H13A—C13—H13C	109.5	H15X—O15—H15Y	109.8
H13B—C13—H13C	109.5	H16X—O16—H16Y	109.8
O3—Zn1—O1—C1	−68.3 (2)	C1—C2—C4—C3i	179.4 (2)
O5—Zn1—O1—C1	156.34 (17)	Zn1—O3—C5—O4	6.8 (4)
N1—Zn1—O1—C1	53.3 (2)	Zn1—O3—C5—C6	−174.73 (17)
O1—Zn1—O3—C5	−23.0 (2)	O4—C5—C6—C7	166.5 (3)
O5—Zn1—O3—C5	110.6 (2)	O3—C5—C6—C7	−12.1 (4)
N1—Zn1—O3—C5	−147.4 (2)	O4—C5—C6—C8	−13.7 (4)
O3—Zn1—O5—C9	−72.17 (19)	O3—C5—C6—C8	167.7 (2)
O1—Zn1—O5—C9	69.27 (19)	C8—C6—C7—C8ii	−0.1 (5)
N1—Zn1—O5—C9	−178.56 (18)	C5—C6—C7—C8ii	179.7 (3)
O3—Zn1—N1—C14	−168.38 (18)	C7—C6—C8—C7ii	0.1 (5)
O1—Zn1—N1—C14	57.3 (2)	C5—C6—C8—C7ii	−179.7 (3)
O5—Zn1—N1—C14	−53.78 (19)	Zn1—O5—C9—O6	5.0 (4)
O3—Zn1—N1—C13	−45.2 (2)	Zn1—O5—C9—C10	−174.5 (2)
O1—Zn1—N1—C13	−179.48 (17)	O6—C9—C10—C12	178.8 (3)
O5—Zn1—N1—C13	69.45 (19)	O5—C9—C10—C12	−1.7 (4)
Zn1—O1—C1—O2	2.5 (3)	O6—C9—C10—C11	−3.2 (5)
Zn1—O1—C1—C2	−176.58 (18)	O5—C9—C10—C11	176.3 (3)
O2—C1—C2—C4	3.4 (4)	C12—C10—C11—C11iii	−1.4 (3)
O1—C1—C2—C4	−177.5 (2)	C9—C10—C11—C11iii	−179.46 (18)
O2—C1—C2—C3	−178.0 (3)	C11—C10—C12—C12iii	1.4 (4)
O1—C1—C2—C3	1.1 (4)	C9—C10—C12—C12iii	179.40 (19)
C4—C2—C3—C4i	−0.8 (4)	C18—N3—C19—O7	−122.2 (3)
C1—C2—C3—C4i	−179.4 (2)	C17—N3—C19—O7	65.0 (3)
C3—C2—C4—C3i	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4iv	0.91	2.27	3.109 (3)	152
N1—H1A···O2	0.91	2.54	3.040 (3)	115
N2—H2A···O4v	0.91	1.93	2.770 (3)	153
N2—H2B···O15	0.89	2.64	3.241 (7)	127
O8—H8X···O12vi	0.85	2.09	2.519 (9)	111
O8—H8X···N3v	0.85	2.59	3.329 (5)	147
O9—H9X···O9iii	0.85	1.61	2.063 (11)	110
O10—H10X···O7	0.85	1.95	2.524 (7)	124
O11—H11Y···O9	0.85	2.47	2.927 (9)	115
O11—H11X···O15vi	0.85	1.73	2.552 (10)	161
O12—H12X···O8vii	0.85	2.04	2.519 (9)	115
O13—H13F···O13iii	0.85	1.77	2.460 (14)	137
O13—H13F···O14	0.85	2.08	2.650 (10)	124
O15—H15X···O11vii	0.85	2.13	2.552 (10)	110
O16—H16X···O12	0.85	2.22	2.709 (9)	116
O16—H16X···O13	0.85	2.37	3.131 (9)	150
O16—H16Y···O10	0.85	2.62	3.079 (9)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.91	2.27	3.109 (3)	152
N1—H1A⋯O2	0.91	2.54	3.040 (3)	115
N2—H2A⋯O4ii	0.91	1.93	2.770 (3)	153
N2—H2B⋯O15	0.89	2.64	3.241 (7)	127
O8—H8X⋯O12iii	0.85	2.09	2.519 (9)	111
O8—H8X⋯N3ii	0.85	2.59	3.329 (5)	147
O9—H9X⋯O9iv	0.85	1.61	2.063 (11)	110
O10—H10X⋯O7	0.85	1.95	2.524 (7)	124
O11—H11Y⋯O9	0.85	2.47	2.927 (9)	115
O11—H11X⋯O15iii	0.85	1.73	2.552 (10)	161
O12—H12X⋯O8v	0.85	2.04	2.519 (9)	115
O13—H13F⋯O13iv	0.85	1.77	2.460 (14)	137
O13—H13F⋯O14	0.85	2.08	2.650 (10)	124
O15—H15X⋯O11v	0.85	2.13	2.552 (10)	110
O16—H16X⋯O12	0.85	2.22	2.709 (9)	116
O16—H16X⋯O13	0.85	2.37	3.131 (9)	150
O16—H16Y⋯O10	0.85	2.62	3.079 (9)	116

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