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Acta Cryst. (2009). E65, m239-m240    [ doi:10.1107/S1600536809003055 ]

Diaquabis(1,10-phenanthroline-[kappa]2N,N')zinc(II) 2-hydroxy-5-sulfonatobenzoate tetrahydrate

K.-L. Zhang, B. Yang and S. W. Ng

Abstract top

The water-coordinated metal centre in the title salt, [Zn(C12H8N2)2(H2O)2]C7H4O6S·4H2O, is chelated by the two bidentate N-heterocycles, leading to an overall distorted octahedral environment. The cation, dianion and solvent water molecules interact by O-H...O hydrogen bonds to form a layer motif. The SO3 group is disordered over two positions with respect to the O atoms in a 0.76 (1):0.24 (1) ratio. One of the solvent water molecules is also disordered over two positions in a 0.56 (4):0.44 (4) ratio.

Related literature top

For the isostructural manganese(II), nickel(II) and cobalt(II) analogues, see: Fan et al. (2005); Chen et al. (2005); Zhu & Fan (2005).

Experimental top

1,10-Phenanthroline monohydrate (0.10 g, 0.5 mmol) was dissolved in methanol (10 ml). To this solution was added zinc nitrate hexahydrate (0.15 g, 0.5 mmol) dissolved in water (10 ml). The solution was then mixed with an aqueous solution of 5-sulfosalicylic acid (0.11 g, 0.5 mmol) and sodium hydroxide (0.04 g, 1 mmol). Crystals separated after several days. These were collected and washed with methanol; yield: 50%. CH&N elemental analysis: Calc. for C31H32N4O12SZn: C 49.63, H 4.27, N 7.47%. Found: C 49.71, H 4.31, N, 7.41%.

Refinement top

The –SO3 group is disordered over two positions with respect to the O atoms. The S—O distances were restrained to 0.01 Å of each other, as were the O···O distances. The anisotropic temperature factors were restrained to be nearly isotropic. The disordered refined to a 0.76 (1):0.24 ratio. One of the lattice water molecules is also disordered over two positions in a 0.56 (4):0.44 ratio. The temperature factors of the two components were restrained to be equal to each other. The anisotropic temperature factors were also restrained to be nearly isotropic.

The carbon-bound H atoms were placed in calculated positions and were allowed to ride on the parent atoms. The oxygen-bound ones were located in a difference Fourier map, and were refined with distance restraints O—H = 0.85 (1) and H···H = 1.39 (1) Å. Their temperature factors were tied by a factor of 1.5.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of [Zn(OH2)2(C12H8N2)2][C7H4O6S].4H2O; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radii. The disorder is not shown.
Diaquabis(1,10-phenanthroline-κ2N,N')zinc(II) 2-hydroxy-5-sulfonatobenzoate tetrahydrate top
Crystal data top
[Zn(C12H8N2)2(H2O)2]C7H4O6S·4H2OZ = 2
Mr = 750.04F(000) = 776
Triclinic, P1Dx = 1.514 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.075 (1) ÅCell parameters from 2300 reflections
b = 12.263 (1) Åθ = 2.5–22.9°
c = 13.927 (1) ŵ = 0.88 mm−1
α = 96.937 (2)°T = 293 K
β = 101.495 (2)°Block, colourless
γ = 98.856 (2)°0.38 × 0.30 × 0.22 mm
V = 1645.5 (2) Å3
Data collection top
Bruker APEXII area-detector
diffractometer		7315 independent reflections
Radiation source: fine-focus sealed tube4849 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→12
Tmin = 0.36, Tmax = 0.82k = −14→15
10806 measured reflectionsl = −18→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 0.93 w = 1/[σ2(Fo2) + (0.0512P)2]
where P = (Fo2 + 2Fc2)/3
7315 reflections(Δ/σ)max = 0.001
513 parametersΔρmax = 0.28 e Å−3
106 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[Zn(C12H8N2)2(H2O)2]C7H4O6S·4H2Oγ = 98.856 (2)°
Mr = 750.04V = 1645.5 (2) Å3
Triclinic, P1Z = 2
a = 10.075 (1) ÅMo Kα radiation
b = 12.263 (1) ŵ = 0.88 mm−1
c = 13.927 (1) ÅT = 293 K
α = 96.937 (2)°0.38 × 0.30 × 0.22 mm
β = 101.495 (2)°
Data collection top
Bruker APEXII area-detector
diffractometer		7315 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4849 reflections with I > 2σ(I)
Tmin = 0.36, Tmax = 0.82Rint = 0.020
10806 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095Δρmax = 0.28 e Å−3
S = 0.93Δρmin = −0.35 e Å−3
7315 reflectionsAbsolute structure: ?
513 parametersFlack parameter: ?
106 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.50705 (3)0.73388 (2)0.26312 (2)0.03952 (10)
S11.09039 (9)0.91846 (6)0.82131 (5)0.0656 (2)
N10.40757 (18)0.83635 (15)0.35340 (14)0.0376 (4)
N20.5761 (2)0.69351 (16)0.40972 (14)0.0417 (5)
N30.5781 (2)0.59926 (17)0.18305 (14)0.0439 (5)
N40.32841 (19)0.59452 (15)0.22700 (14)0.0402 (5)
O10.9002 (2)0.85085 (16)0.42946 (13)0.0634 (5)
O20.9822 (2)0.70605 (17)0.36560 (14)0.0701 (6)
O31.1172 (3)0.59708 (19)0.47739 (18)0.0844 (7)
H31.064 (4)0.613 (4)0.428 (2)0.127*
O40.9776 (4)0.9750 (3)0.7937 (2)0.0854 (15)0.757 (7)
O51.0879 (5)0.8618 (3)0.9044 (3)0.0724 (11)0.757 (7)
O61.2238 (5)0.9995 (3)0.8373 (3)0.1028 (16)0.757 (7)
O4'0.9391 (7)0.8922 (10)0.8218 (8)0.104 (5)0.243 (7)
O5'1.1646 (14)0.8780 (11)0.9059 (9)0.101 (5)0.243 (7)
O6'1.1326 (10)1.0279 (5)0.8124 (7)0.054 (3)0.243 (7)
O1W0.69078 (17)0.84787 (16)0.28148 (14)0.0517 (4)
H110.757 (2)0.841 (2)0.3255 (15)0.078*
H120.713 (3)0.8936 (19)0.2443 (16)0.078*
O2W0.42757 (19)0.79208 (16)0.13328 (14)0.0555 (5)
H210.3404 (11)0.779 (2)0.114 (2)0.083*
H220.459 (2)0.8582 (13)0.127 (2)0.083*
O3W0.1536 (2)0.73101 (18)0.05280 (15)0.0658 (5)
H310.103 (3)0.742 (3)0.0938 (18)0.099*
H320.134 (3)0.770 (2)0.0068 (16)0.099*
O4W0.2383 (3)1.0300 (3)0.0895 (2)0.1163 (9)
H410.182 (4)1.052 (4)0.123 (3)0.174*
H420.190 (4)0.990 (4)0.035 (2)0.174*
O5W−0.0022 (2)0.78419 (18)0.18724 (16)0.0698 (6)
H51−0.008 (4)0.8523 (12)0.190 (2)0.105*
H52−0.010 (4)0.763 (2)0.2422 (14)0.105*
O6W0.5032 (7)1.0198 (5)0.1338 (4)0.0941 (15)0.54 (6)
O6W'0.4960 (7)0.9808 (5)0.0703 (5)0.0941 (15)0.46
H610.5655 (17)1.030 (3)0.1029 (18)0.141*
H620.429 (2)1.038 (4)0.105 (3)0.141*
C10.4359 (2)0.82539 (18)0.45066 (17)0.0364 (5)
C20.5265 (2)0.74973 (19)0.48134 (17)0.0387 (5)
C30.6591 (3)0.6232 (2)0.4370 (2)0.0579 (7)
H3A0.69320.58420.38870.069*
C40.6975 (3)0.6053 (3)0.5344 (3)0.0764 (9)
H40.75560.55500.55050.092*
C50.6491 (3)0.6622 (3)0.6058 (2)0.0751 (9)
H50.67470.65120.67130.090*
C60.5605 (3)0.7376 (2)0.58146 (19)0.0545 (7)
C70.5041 (3)0.8011 (3)0.6521 (2)0.0681 (8)
H70.52750.79390.71880.082*
C80.4186 (3)0.8704 (2)0.6232 (2)0.0589 (8)
H80.38320.91010.67030.071*
C90.3807 (2)0.88451 (19)0.52230 (19)0.0443 (6)
C100.2908 (3)0.9557 (2)0.4877 (2)0.0531 (7)
H100.25120.99600.53170.064*
C110.2621 (3)0.9652 (2)0.3902 (2)0.0542 (7)
H11A0.20221.01160.36690.065*
C120.3231 (2)0.90484 (19)0.3246 (2)0.0461 (6)
H12A0.30350.91320.25810.055*
C130.4829 (3)0.50289 (19)0.15053 (16)0.0411 (6)
C140.3499 (2)0.50073 (19)0.17326 (16)0.0407 (5)
C150.2076 (3)0.5927 (2)0.25028 (19)0.0496 (6)
H150.19270.65620.28730.060*
C160.1008 (3)0.4998 (2)0.2220 (2)0.0602 (7)
H160.01750.50200.24070.072*
C170.1194 (3)0.4070 (2)0.1673 (2)0.0624 (8)
H170.04840.34530.14720.075*
C180.2475 (3)0.4041 (2)0.14070 (18)0.0516 (7)
C190.2778 (4)0.3086 (2)0.0854 (2)0.0712 (9)
H190.21020.24480.06330.085*
C200.4028 (4)0.3099 (2)0.0649 (2)0.0696 (9)
H200.42060.24630.02990.084*
C210.5102 (3)0.4076 (2)0.09595 (18)0.0533 (7)
C220.6413 (3)0.4162 (3)0.0741 (2)0.0641 (8)
H22A0.66410.35550.03820.077*
C230.7349 (3)0.5124 (3)0.1051 (2)0.0644 (8)
H230.82140.51800.09010.077*
C240.7002 (3)0.6032 (2)0.15969 (19)0.0551 (7)
H240.76520.66870.18050.066*
C250.9671 (3)0.7750 (2)0.4384 (2)0.0512 (6)
C261.0362 (2)0.7593 (2)0.54018 (19)0.0449 (6)
C271.0324 (2)0.8337 (2)0.62312 (18)0.0442 (6)
H270.98820.89420.61450.053*
C281.0928 (3)0.8198 (2)0.71780 (19)0.0484 (6)
C291.1577 (3)0.7286 (3)0.7311 (2)0.0644 (8)
H291.19690.71770.79470.077*
C301.1638 (3)0.6547 (3)0.6508 (3)0.0714 (9)
H301.20750.59410.66030.086*
C311.1054 (3)0.6693 (2)0.5552 (2)0.0573 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04032 (17)0.04133 (17)0.03760 (16)0.01290 (12)0.00851 (12)0.00213 (11)
S10.0877 (6)0.0620 (5)0.0438 (4)0.0094 (4)0.0046 (4)0.0170 (4)
N10.0359 (11)0.0355 (10)0.0403 (11)0.0103 (8)0.0060 (9)0.0005 (9)
N20.0415 (11)0.0416 (11)0.0453 (12)0.0148 (9)0.0107 (9)0.0085 (9)
N30.0423 (12)0.0524 (12)0.0394 (11)0.0176 (10)0.0097 (9)0.0041 (9)
N40.0406 (11)0.0406 (11)0.0409 (11)0.0097 (9)0.0107 (9)0.0062 (9)
O10.0622 (12)0.0758 (13)0.0498 (11)0.0292 (11)−0.0026 (9)0.0050 (10)
O20.0863 (15)0.0732 (13)0.0538 (12)0.0241 (11)0.0205 (11)0.0014 (10)
O30.116 (2)0.0723 (14)0.0890 (18)0.0524 (14)0.0495 (16)0.0187 (13)
O40.123 (3)0.084 (3)0.0535 (18)0.055 (2)0.0025 (17)0.0085 (16)
O50.106 (3)0.068 (2)0.0442 (17)0.009 (2)0.0146 (19)0.0256 (15)
O60.113 (3)0.083 (2)0.088 (2)−0.029 (2)−0.010 (2)0.0347 (19)
O4'0.100 (7)0.099 (8)0.115 (8)−0.011 (5)0.075 (6)−0.024 (6)
O5'0.139 (10)0.096 (8)0.065 (7)0.025 (7)0.007 (7)0.026 (5)
O6'0.066 (6)0.046 (4)0.064 (5)0.021 (4)0.025 (4)0.025 (4)
O1W0.0425 (10)0.0623 (12)0.0495 (11)0.0061 (9)0.0048 (8)0.0192 (9)
O2W0.0574 (11)0.0635 (12)0.0460 (11)0.0180 (10)0.0058 (10)0.0111 (10)
O3W0.0660 (13)0.0783 (14)0.0580 (13)0.0261 (11)0.0105 (10)0.0185 (11)
O4W0.145 (3)0.096 (2)0.099 (2)0.0271 (19)0.0184 (19)−0.0103 (16)
O5W0.0734 (14)0.0677 (13)0.0767 (15)0.0189 (12)0.0283 (12)0.0169 (11)
O6W0.115 (3)0.091 (3)0.078 (3)0.013 (2)0.024 (3)0.023 (3)
O6W'0.115 (3)0.091 (3)0.078 (3)0.013 (2)0.024 (3)0.023 (3)
C10.0338 (12)0.0333 (12)0.0398 (13)0.0011 (10)0.0098 (10)0.0001 (10)
C20.0371 (13)0.0393 (13)0.0390 (13)0.0047 (10)0.0080 (10)0.0070 (10)
C30.0621 (18)0.0594 (17)0.0632 (19)0.0307 (15)0.0179 (15)0.0210 (14)
C40.084 (2)0.083 (2)0.080 (2)0.0452 (19)0.0197 (19)0.0421 (19)
C50.087 (2)0.094 (2)0.0559 (19)0.032 (2)0.0137 (17)0.0404 (18)
C60.0597 (17)0.0634 (17)0.0434 (15)0.0095 (14)0.0134 (13)0.0190 (13)
C70.084 (2)0.084 (2)0.0392 (16)0.0082 (18)0.0221 (15)0.0144 (15)
C80.0627 (19)0.0658 (18)0.0488 (17)0.0029 (15)0.0277 (15)−0.0032 (14)
C90.0404 (14)0.0418 (13)0.0487 (15)0.0005 (11)0.0170 (12)−0.0036 (11)
C100.0445 (15)0.0436 (14)0.072 (2)0.0066 (12)0.0261 (14)−0.0097 (13)
C110.0415 (15)0.0450 (15)0.076 (2)0.0176 (12)0.0113 (14)0.0008 (14)
C120.0420 (14)0.0425 (14)0.0535 (16)0.0158 (11)0.0050 (12)0.0060 (12)
C130.0552 (15)0.0397 (13)0.0308 (12)0.0174 (12)0.0069 (11)0.0088 (10)
C140.0516 (15)0.0383 (13)0.0314 (12)0.0094 (11)0.0043 (11)0.0095 (10)
C150.0439 (15)0.0537 (16)0.0527 (16)0.0095 (12)0.0134 (12)0.0091 (12)
C160.0488 (17)0.0710 (19)0.0586 (18)0.0008 (14)0.0124 (14)0.0139 (15)
C170.0621 (19)0.0613 (18)0.0537 (18)−0.0128 (15)0.0043 (14)0.0145 (15)
C180.0693 (19)0.0425 (14)0.0380 (14)0.0025 (13)0.0045 (13)0.0095 (11)
C190.106 (3)0.0404 (16)0.059 (2)0.0000 (16)0.0144 (19)0.0007 (14)
C200.114 (3)0.0418 (16)0.0536 (18)0.0264 (17)0.0167 (19)−0.0018 (13)
C210.083 (2)0.0474 (15)0.0351 (14)0.0336 (15)0.0106 (13)0.0069 (12)
C220.092 (2)0.073 (2)0.0411 (16)0.0530 (19)0.0180 (16)0.0075 (14)
C230.0593 (18)0.101 (2)0.0461 (17)0.0459 (18)0.0169 (14)0.0138 (16)
C240.0457 (15)0.0748 (19)0.0482 (16)0.0234 (14)0.0118 (13)0.0053 (14)
C250.0460 (15)0.0575 (16)0.0501 (16)0.0075 (13)0.0133 (13)0.0064 (13)
C260.0374 (13)0.0493 (14)0.0539 (16)0.0117 (11)0.0170 (12)0.0151 (12)
C270.0372 (13)0.0491 (14)0.0500 (15)0.0132 (11)0.0106 (11)0.0139 (12)
C280.0452 (15)0.0537 (15)0.0515 (16)0.0091 (12)0.0146 (12)0.0216 (13)
C290.0629 (19)0.078 (2)0.066 (2)0.0272 (16)0.0183 (15)0.0413 (17)
C300.082 (2)0.071 (2)0.088 (2)0.0460 (18)0.0382 (19)0.0433 (19)
C310.0589 (17)0.0553 (16)0.070 (2)0.0202 (14)0.0297 (15)0.0212 (15)
Geometric parameters (Å, °) top
Zn1—O2W2.0810 (18)C4—C51.358 (4)
Zn1—O1W2.0914 (17)C4—H40.9300
Zn1—N12.1615 (17)C5—C61.406 (4)
Zn1—N22.164 (2)C5—H50.9300
Zn1—N32.1720 (18)C6—C71.438 (4)
Zn1—N42.2130 (19)C7—C81.341 (4)
S1—O6'1.372 (5)C7—H70.9300
S1—O51.422 (3)C8—C91.420 (4)
S1—O41.433 (3)C8—H80.9300
S1—O5'1.448 (6)C9—C101.409 (4)
S1—O61.503 (3)C10—C111.354 (4)
S1—O4'1.511 (6)C10—H100.9300
S1—C281.773 (3)C11—C121.400 (3)
N1—C121.325 (3)C11—H11A0.9300
N1—C11.355 (3)C12—H12A0.9300
N2—C31.327 (3)C13—C211.410 (3)
N2—C21.363 (3)C13—C141.434 (3)
N3—C241.330 (3)C14—C181.407 (3)
N3—C131.367 (3)C15—C161.398 (4)
N4—C151.318 (3)C15—H150.9300
N4—C141.365 (3)C16—C171.351 (4)
O1—C251.234 (3)C16—H160.9300
O2—C251.288 (3)C17—C181.417 (4)
O3—C311.351 (3)C17—H170.9300
O3—H30.853 (11)C18—C191.430 (4)
O1W—H110.832 (10)C19—C201.344 (4)
O1W—H120.843 (10)C19—H190.9300
O2W—H210.849 (10)C20—C211.443 (4)
O2W—H220.845 (10)C20—H200.9300
O3W—H310.849 (10)C21—C221.405 (4)
O3W—H320.853 (10)C22—C231.356 (4)
O4W—H410.859 (11)C22—H22A0.9300
O4W—H420.858 (11)C23—C241.400 (4)
O5W—H510.844 (10)C23—H230.9300
O5W—H520.851 (10)C24—H240.9300
O6W—O6W'0.937 (6)C25—C261.498 (4)
O6W—H610.831 (11)C26—C271.394 (3)
O6W—H620.843 (8)C26—C311.408 (3)
O6W'—H610.857 (11)C27—C281.380 (3)
O6W'—H621.17 (3)C27—H270.9300
C1—C91.415 (3)C28—C291.393 (4)
C1—C21.441 (3)C29—C301.369 (4)
C2—C61.400 (3)C29—H290.9300
C3—C41.388 (4)C30—C311.388 (4)
C3—H3A0.9300C30—H300.9300
O2W—Zn1—O1W89.83 (7)C2—C6—C5116.4 (2)
O2W—Zn1—N193.87 (7)C2—C6—C7119.3 (3)
O1W—Zn1—N197.42 (7)C5—C6—C7124.3 (3)
O2W—Zn1—N2171.00 (7)C8—C7—C6121.0 (3)
O1W—Zn1—N290.11 (7)C8—C7—H7119.5
N1—Zn1—N277.21 (7)C6—C7—H7119.5
O2W—Zn1—N392.55 (7)C7—C8—C9121.5 (2)
O1W—Zn1—N394.26 (8)C7—C8—H8119.2
N1—Zn1—N3166.67 (7)C9—C8—H8119.2
N2—Zn1—N396.43 (7)C10—C9—C1116.7 (2)
O2W—Zn1—N489.26 (7)C10—C9—C8124.0 (2)
O1W—Zn1—N4170.12 (7)C1—C9—C8119.4 (2)
N1—Zn1—N492.46 (7)C11—C10—C9119.9 (2)
N2—Zn1—N492.32 (7)C11—C10—H10120.0
N3—Zn1—N475.96 (7)C9—C10—H10120.0
O6'—S1—O5133.1 (4)C10—C11—C12119.6 (2)
O6'—S1—O467.2 (4)C10—C11—H11A120.2
O5—S1—O4115.8 (2)C12—C11—H11A120.2
O6'—S1—O5'116.8 (5)N1—C12—C11122.8 (2)
O5—S1—O5'30.8 (5)N1—C12—H12A118.6
O4—S1—O5'140.9 (7)C11—C12—H12A118.6
O6'—S1—O642.2 (3)N3—C13—C21122.9 (2)
O5—S1—O6110.5 (2)N3—C13—C14117.6 (2)
O4—S1—O6109.3 (2)C21—C13—C14119.5 (2)
O5'—S1—O682.5 (5)N4—C14—C18122.4 (2)
O6'—S1—O4'112.4 (5)N4—C14—C13117.5 (2)
O5—S1—O4'76.4 (5)C18—C14—C13120.0 (2)
O4—S1—O4'46.8 (5)N4—C15—C16123.2 (2)
O5'—S1—O4'107.2 (5)N4—C15—H15118.4
O6—S1—O4'151.4 (4)C16—C15—H15118.4
O6'—S1—C28114.8 (3)C17—C16—C15119.5 (3)
O5—S1—C28108.38 (19)C17—C16—H16120.2
O4—S1—C28108.01 (15)C15—C16—H16120.2
O5'—S1—C28104.5 (6)C16—C17—C18119.7 (3)
O6—S1—C28104.2 (2)C16—C17—H17120.2
O4'—S1—C2899.3 (4)C18—C17—H17120.2
C12—N1—C1118.06 (19)C14—C18—C17117.0 (2)
C12—N1—Zn1128.06 (16)C14—C18—C19119.4 (3)
C1—N1—Zn1113.88 (14)C17—C18—C19123.6 (3)
C3—N2—C2117.8 (2)C20—C19—C18120.8 (3)
C3—N2—Zn1128.40 (17)C20—C19—H19119.6
C2—N2—Zn1113.79 (15)C18—C19—H19119.6
C24—N3—C13118.0 (2)C19—C20—C21121.7 (3)
C24—N3—Zn1126.88 (18)C19—C20—H20119.2
C13—N3—Zn1115.07 (15)C21—C20—H20119.2
C15—N4—C14118.1 (2)C22—C21—C13116.6 (3)
C15—N4—Zn1128.09 (16)C22—C21—C20124.7 (2)
C14—N4—Zn1113.80 (15)C13—C21—C20118.6 (3)
C31—O3—H3104 (3)C23—C22—C21120.4 (2)
Zn1—O1W—H11117.2 (17)C23—C22—H22A119.8
Zn1—O1W—H12129.0 (17)C21—C22—H22A119.8
H11—O1W—H12112.9 (17)C22—C23—C24119.5 (3)
Zn1—O2W—H21116 (2)C22—C23—H23120.3
Zn1—O2W—H22118 (2)C24—C23—H23120.3
H21—O2W—H22109.6 (16)N3—C24—C23122.6 (3)
H31—O3W—H32108.2 (16)N3—C24—H24118.7
H41—O4W—H42107.2 (18)C23—C24—H24118.7
H51—O5W—H52109.5 (17)O1—C25—O2124.6 (3)
O6W'—O6W—H6157.6 (9)O1—C25—C26119.1 (2)
O6W'—O6W—H6282 (3)O2—C25—C26116.2 (2)
H61—O6W—H62113.0 (18)C27—C26—C31118.1 (2)
O6W—O6W'—H6154.9 (9)C27—C26—C25120.4 (2)
O6W—O6W'—H6245.5 (13)C31—C26—C25121.5 (2)
H61—O6W'—H6286 (2)C28—C27—C26121.5 (2)
N1—C1—C9123.0 (2)C28—C27—H27119.2
N1—C1—C2117.85 (19)C26—C27—H27119.2
C9—C1—C2119.2 (2)C27—C28—C29119.3 (3)
N2—C2—C6123.1 (2)C27—C28—S1120.31 (19)
N2—C2—C1117.3 (2)C29—C28—S1120.4 (2)
C6—C2—C1119.6 (2)C30—C29—C28120.3 (3)
N2—C3—C4123.0 (3)C30—C29—H29119.9
N2—C3—H3A118.5C28—C29—H29119.9
C4—C3—H3A118.5C29—C30—C31120.7 (3)
C5—C4—C3119.0 (3)C29—C30—H30119.6
C5—C4—H4120.5C31—C30—H30119.6
C3—C4—H4120.5O3—C31—C30119.2 (3)
C4—C5—C6120.6 (3)O3—C31—C26120.8 (3)
C4—C5—H5119.7C30—C31—C26120.0 (3)
C6—C5—H5119.7
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11···O10.83 (1)1.81 (1)2.632 (2)170 (3)
O1W—H12···O6i0.84 (1)1.95 (1)2.793 (4)177 (2)
O1W—H12···O6'i0.84 (1)2.04 (2)2.787 (7)147 (2)
O2W—H21···O3W0.85 (1)1.87 (1)2.714 (3)170 (3)
O2W—H22···O6W0.85 (1)1.95 (1)2.778 (6)166 (3)
O2W—H22···O6W'0.85 (1)1.80 (2)2.615 (6)160 (3)
O3W—H31···O5W0.85 (1)1.91 (1)2.754 (3)173 (3)
O3W—H32···O5ii0.85 (1)1.95 (1)2.805 (4)178 (3)
O3W—H32···O5'ii0.85 (1)2.08 (2)2.892 (10)159 (3)
O4W—H41···O4iii0.86 (1)2.17 (3)2.962 (5)153 (5)
O4W—H41···O4'iii0.86 (1)1.74 (2)2.598 (8)173 (5)
O4W—H42···O5ii0.86 (1)2.22 (1)3.065 (5)169 (5)
O4W—H42···O5'ii0.86 (1)2.08 (2)2.869 (15)153 (4)
O5W—H51···O4iii0.84 (1)2.07 (1)2.900 (4)168 (4)
O5W—H51···O6'iii0.84 (1)2.07 (2)2.823 (8)148 (3)
O5W—H52···O2iv0.85 (1)1.94 (1)2.792 (3)175 (3)
O6W—H61···O6i0.83 (1)2.22 (3)2.751 (8)122 (3)
O6W—H62···O4W0.84 (1)1.88 (2)2.642 (7)150 (4)
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x−1, y, z−1; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11···O10.83 (1)1.81 (1)2.632 (2)170 (3)
O1W—H12···O6i0.84 (1)1.95 (1)2.793 (4)177 (2)
O1W—H12···O6'i0.84 (1)2.04 (2)2.787 (7)147 (2)
O2W—H21···O3W0.85 (1)1.87 (1)2.714 (3)170 (3)
O2W—H22···O6W0.85 (1)1.95 (1)2.778 (6)166 (3)
O2W—H22···O6W'0.85 (1)1.80 (2)2.615 (6)160 (3)
O3W—H31···O5W0.85 (1)1.91 (1)2.754 (3)173 (3)
O3W—H32···O5ii0.85 (1)1.95 (1)2.805 (4)178 (3)
O3W—H32···O5'ii0.85 (1)2.08 (2)2.892 (10)159 (3)
O4W—H41···O4iii0.86 (1)2.17 (3)2.962 (5)153 (5)
O4W—H41···O4'iii0.86 (1)1.74 (2)2.598 (8)173 (5)
O4W—H42···O5ii0.86 (1)2.22 (1)3.065 (5)169 (5)
O4W—H42···O5'ii0.86 (1)2.08 (2)2.869 (15)153 (4)
O5W—H51···O4iii0.84 (1)2.07 (1)2.900 (4)168 (4)
O5W—H51···O6'iii0.84 (1)2.07 (2)2.823 (8)148 (3)
O5W—H52···O2iv0.85 (1)1.94 (1)2.792 (3)175 (3)
O6W—H61···O6i0.83 (1)2.22 (3)2.751 (8)122 (3)
O6W—H62···O4W0.84 (1)1.88 (2)2.642 (7)150 (4)
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x−1, y, z−1; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z.
Acknowledgements top

The authors thank the Fujian Institute for Research on the Structure of Matter for the diffraction measurements. We thank the Foundation of Jiangsu Provincial Key Programme of Physical Chemistry in Yangzhou University and the University of Malaya for supporting this study.

references
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