Aqua­(2,2′-bi­pyridine-κ2N,N′)bis(5-chloro­salicylato-κO)zinc(II)

Wen, D.; Ta, H.; Zhong, C.; Xie, T.; Wu, L.

doi:10.1107/S1600536807042316

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Aqua(2,2′-bipyridine-κ²N,N′)bis(5-chlorosalicylato-κO)zinc(II)

D. Wen, H. Ta, C. Zhong, T. Xie and L. Wu

In the title complex, [Zn(C₇H₄ClO₃)₂(C₁₀H₈N₂)(H₂O)], the Zn^II atom is coordinated by two 5-chlorosalicylate ligands, one 2,2′-bipyridine ligand and one water molecule, displaying a distorted trigonal–bipyramidal geometry. The crystal structure is stabilized by intra- and intermolecular O—H

O and intermolecular C—H

Cl hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042316/hy2079sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042316/hy2079Isup2.hkl Contains datablock I

CCDC reference: 663543

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.031
wR factor = 0.094
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       1.98
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Metal salicylate complexes are of current interest owing to their intriguing structural features and biological applications (Brownless et al., 1999; Lemoine, Bendada & Viossat, 2004; Lemoine, Viossat et al., 2004; Wang et al., 2004; Wen et al., 2007a,b). We report here the structure of a zinc(II) complex with 5-chlorosalicylate ligand (Melnik et al., 2001).

The title complex was synthesized under hydrothermal conditions. The Zn^II atom is coordinated in a distorted trigonal bipyramidal geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from a 2,2'-bipyridine ligand and one water O atom (Fig. 1 and Table 1). The water molecule, hydroxyl groups and the uncoordinated carboxylate oxygen atoms form intra- and intermolecular O—H···O hydrogen bonds while the 2,2'-bipyridine ligand forms an intermolecular C—H···Cl hydrogen bond with the Cl atom of a 5-chlorosalicylate ligand (Table 2), generating an extended chain architecture along the a axis (Fig. 2). The crystal structure is stabilized by the O—H···O and C—H···Cl hydrogen bonds.

Related literature top

For related literature, see: Brownless et al. (1999); Lemoine, Bendada & Viossat (2004); Lemoine, Viossat et al. (2004); Melnik et al. (2001); Wang et al. (2004); Wen et al. (2007a,b).

Experimental top

A mixture of Zn(NO₃)₂.6H₂O (0.030 g, 0.1 mmol), 2,2'-bipyridine (0.016 g, 0.1 mmol), 5-chlorosalicylic acid (0.035 g, 0.2 mmol) and distilled water (10 ml) was put into a 20 ml Teflon-lined autoclave and then heated at 413 K for 48 h. Yellow block-like crystals of the title compound suitable for X-ray analysis were collected from the reaction mixture.

Structure description top

For related literature, see: Brownless et al. (1999); Lemoine, Bendada & Viossat (2004); Lemoine, Viossat et al. (2004); Melnik et al. (2001); Wang et al. (2004); Wen et al. (2007a,b).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of the title compoud. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the extended hydrogen-bonding (dashed lines) chain along the a axis.

Aquabis(5-chlorosalicylato-κO)(2,2'-bipyridine-κ²N,N')zinc(II) top

Crystal data top

[Zn(C₇H₄ClO₃)₂(C₁₀H₈N₂)(H₂O)]	Z = 2
M_r = 582.67	F(000) = 592
Triclinic, P1	D_x = 1.639 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.114 (5) Å	Cell parameters from 4865 reflections
b = 11.141 (6) Å	θ = 3.1–26.5°
c = 11.553 (6) Å	µ = 1.32 mm⁻¹
α = 112.72 (2)°	T = 293 K
β = 93.208 (19)°	Block, yellow
γ = 97.93 (2)°	0.52 × 0.50 × 0.47 mm
V = 1180.8 (11) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4865 independent reflections
Radiation source: rotation anode	4269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 26.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.511, T_max = 0.541	k = −13→13
10689 measured reflections	l = −14→14

Refinement top

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0575P)² + 0.1147P] where P = (F_o² + 2F_c²)/3
4865 reflections	(Δ/σ)_max = 0.001
337 parameters	Δρ_max = 0.28 e Å⁻³
4 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Zn(C₇H₄ClO₃)₂(C₁₀H₈N₂)(H₂O)]	γ = 97.93 (2)°
M_r = 582.67	V = 1180.8 (11) Å³
Triclinic, P1	Z = 2
a = 10.114 (5) Å	Mo Kα radiation
b = 11.141 (6) Å	µ = 1.32 mm⁻¹
c = 11.553 (6) Å	T = 293 K
α = 112.72 (2)°	0.52 × 0.50 × 0.47 mm
β = 93.208 (19)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4865 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4269 reflections with I > 2σ(I)
T_min = 0.511, T_max = 0.541	R_int = 0.023
10689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	4 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.28 e Å⁻³
4865 reflections	Δρ_min = −0.63 e Å⁻³
337 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.93725 (2)	0.88977 (2)	0.26799 (2)	0.03437 (9)
N1	1.07977 (17)	0.94611 (18)	0.15880 (17)	0.0397 (4)
N2	0.92448 (17)	1.08927 (17)	0.31238 (16)	0.0377 (4)
O1	0.84114 (15)	0.89774 (15)	0.42384 (14)	0.0427 (3)
O2	0.86926 (16)	0.70100 (16)	0.41829 (16)	0.0491 (4)
O3	0.7135 (2)	0.58124 (18)	0.51632 (19)	0.0605 (5)
H3B	0.781 (2)	0.599 (3)	0.486 (3)	0.073*
O4	0.78536 (14)	0.77602 (14)	0.13849 (13)	0.0398 (3)
O5	0.92178 (15)	0.63737 (17)	0.04523 (16)	0.0528 (4)
O6	0.83933 (18)	0.4330 (2)	−0.14905 (18)	0.0645 (5)
H6B	0.889 (3)	0.489 (3)	−0.088 (2)	0.077*
O7	1.06808 (15)	0.78652 (16)	0.31565 (14)	0.0431 (3)
H7B	1.019 (2)	0.749 (2)	0.351 (2)	0.052*
H7A	1.098 (2)	0.7280 (19)	0.2633 (18)	0.052*
C1	0.70639 (19)	0.8041 (2)	0.53918 (18)	0.0356 (4)
C2	0.6614 (2)	0.6930 (2)	0.5648 (2)	0.0424 (5)
C3	0.5595 (3)	0.6961 (3)	0.6410 (2)	0.0548 (6)
H3A	0.5278	0.6216	0.6560	0.066*
C4	0.5055 (3)	0.8082 (3)	0.6941 (2)	0.0558 (6)
H4A	0.4387	0.8105	0.7466	0.067*
C5	0.5500 (2)	0.9180 (2)	0.6698 (2)	0.0466 (5)
C6	0.6491 (2)	0.9165 (2)	0.59318 (19)	0.0404 (4)
H6A	0.6782	0.9910	0.5773	0.049*
C7	0.81292 (19)	0.8010 (2)	0.45482 (18)	0.0360 (4)
C8	0.6974 (2)	0.58857 (19)	−0.04858 (18)	0.0341 (4)
C9	0.7182 (2)	0.4718 (2)	−0.1443 (2)	0.0428 (5)
C10	0.6134 (3)	0.3919 (2)	−0.2364 (2)	0.0532 (6)
H10A	0.6279	0.3143	−0.3000	0.064*
C11	0.4887 (2)	0.4273 (2)	−0.2335 (2)	0.0496 (5)
H11A	0.4180	0.3732	−0.2942	0.060*
C12	0.4687 (2)	0.5434 (2)	−0.1404 (2)	0.0398 (5)
C13	0.5701 (2)	0.6234 (2)	−0.04767 (18)	0.0355 (4)
H13A	0.5541	0.7005	0.0156	0.043*
C14	0.8089 (2)	0.6724 (2)	0.05218 (19)	0.0364 (4)
C15	1.1575 (2)	0.8696 (2)	0.0834 (2)	0.0483 (5)
H15A	1.1523	0.7833	0.0771	0.058*
C16	1.2435 (3)	0.9120 (3)	0.0157 (2)	0.0550 (6)
H16A	1.2951	0.8554	−0.0364	0.066*
C17	1.2532 (3)	1.0403 (3)	0.0252 (3)	0.0587 (6)
H17A	1.3111	1.0720	−0.0203	0.070*
C18	1.1753 (3)	1.1200 (3)	0.1037 (2)	0.0540 (6)
H18A	1.1808	1.2072	0.1126	0.065*
C19	1.0892 (2)	1.0712 (2)	0.16902 (19)	0.0376 (4)
C20	1.0020 (2)	1.1516 (2)	0.25444 (19)	0.0386 (4)
C21	0.9986 (3)	1.2815 (2)	0.2744 (2)	0.0517 (6)
H21A	1.0529	1.3231	0.2336	0.062*
C22	0.9138 (3)	1.3490 (2)	0.3554 (3)	0.0565 (6)
H22A	0.9101	1.4364	0.3695	0.068*
C23	0.8360 (3)	1.2871 (3)	0.4143 (2)	0.0553 (6)
H23A	0.7785	1.3315	0.4693	0.066*
C24	0.8430 (2)	1.1564 (2)	0.3917 (2)	0.0471 (5)
H24A	0.7898	1.1142	0.4326	0.057*
Cl1	0.47871 (7)	1.05894 (8)	0.73805 (8)	0.0718 (2)
Cl2	0.31025 (6)	0.58675 (7)	−0.14145 (7)	0.06070 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03880 (14)	0.02641 (14)	0.03341 (14)	0.00365 (9)	0.00601 (9)	0.00750 (10)
N1	0.0443 (9)	0.0303 (9)	0.0408 (9)	0.0028 (7)	0.0071 (8)	0.0112 (8)
N2	0.0434 (9)	0.0299 (9)	0.0340 (8)	0.0064 (7)	−0.0002 (7)	0.0073 (7)
O1	0.0515 (8)	0.0353 (8)	0.0426 (8)	0.0099 (7)	0.0167 (7)	0.0146 (7)
O2	0.0550 (9)	0.0390 (9)	0.0560 (9)	0.0161 (7)	0.0201 (8)	0.0174 (8)
O3	0.0731 (11)	0.0379 (9)	0.0780 (13)	0.0130 (9)	0.0271 (10)	0.0275 (9)
O4	0.0433 (7)	0.0306 (8)	0.0355 (7)	0.0023 (6)	0.0017 (6)	0.0041 (6)
O5	0.0399 (8)	0.0440 (9)	0.0578 (10)	0.0066 (7)	0.0012 (7)	0.0034 (8)
O6	0.0549 (10)	0.0540 (12)	0.0600 (11)	0.0229 (9)	0.0037 (8)	−0.0077 (9)
O7	0.0492 (8)	0.0423 (9)	0.0363 (8)	0.0156 (7)	0.0107 (6)	0.0106 (7)
C1	0.0369 (9)	0.0338 (11)	0.0293 (9)	0.0018 (8)	0.0026 (8)	0.0069 (8)
C2	0.0481 (11)	0.0356 (12)	0.0407 (11)	0.0017 (9)	0.0040 (9)	0.0142 (10)
C3	0.0602 (14)	0.0522 (15)	0.0551 (14)	−0.0001 (12)	0.0142 (12)	0.0269 (13)
C4	0.0524 (13)	0.0661 (17)	0.0497 (13)	0.0079 (12)	0.0203 (11)	0.0227 (13)
C5	0.0452 (11)	0.0474 (13)	0.0413 (11)	0.0094 (10)	0.0110 (9)	0.0101 (10)
C6	0.0444 (10)	0.0355 (11)	0.0377 (10)	0.0043 (9)	0.0054 (9)	0.0114 (9)
C7	0.0387 (9)	0.0312 (10)	0.0306 (9)	0.0034 (8)	0.0010 (8)	0.0054 (8)
C8	0.0419 (10)	0.0263 (10)	0.0310 (9)	0.0020 (8)	0.0050 (8)	0.0093 (8)
C9	0.0495 (11)	0.0350 (11)	0.0381 (11)	0.0103 (9)	0.0053 (9)	0.0073 (9)
C10	0.0682 (15)	0.0366 (12)	0.0392 (12)	0.0078 (11)	0.0000 (11)	−0.0004 (10)
C11	0.0575 (13)	0.0400 (13)	0.0406 (11)	−0.0027 (10)	−0.0085 (10)	0.0101 (10)
C12	0.0426 (10)	0.0389 (12)	0.0409 (11)	0.0030 (9)	0.0002 (9)	0.0212 (10)
C13	0.0468 (10)	0.0267 (10)	0.0335 (9)	0.0056 (8)	0.0059 (8)	0.0125 (8)
C14	0.0409 (10)	0.0293 (10)	0.0365 (10)	0.0013 (8)	0.0037 (8)	0.0123 (9)
C15	0.0535 (12)	0.0359 (12)	0.0534 (13)	0.0081 (10)	0.0164 (11)	0.0142 (11)
C16	0.0569 (13)	0.0534 (16)	0.0537 (14)	0.0105 (12)	0.0177 (11)	0.0183 (12)
C17	0.0669 (15)	0.0567 (16)	0.0599 (15)	0.0043 (13)	0.0217 (13)	0.0313 (14)
C18	0.0712 (16)	0.0422 (13)	0.0548 (14)	0.0070 (12)	0.0135 (12)	0.0260 (12)
C19	0.0429 (10)	0.0323 (10)	0.0335 (10)	0.0011 (8)	−0.0015 (8)	0.0114 (9)
C20	0.0451 (10)	0.0309 (10)	0.0351 (10)	0.0042 (8)	−0.0050 (8)	0.0100 (9)
C21	0.0657 (14)	0.0351 (12)	0.0545 (13)	0.0076 (10)	0.0021 (12)	0.0193 (11)
C22	0.0676 (15)	0.0347 (12)	0.0640 (16)	0.0169 (11)	−0.0013 (13)	0.0146 (12)
C23	0.0587 (13)	0.0440 (14)	0.0558 (14)	0.0225 (11)	0.0017 (12)	0.0080 (12)
C24	0.0494 (12)	0.0400 (13)	0.0459 (12)	0.0118 (10)	0.0050 (10)	0.0095 (10)
Cl1	0.0735 (4)	0.0640 (4)	0.0754 (5)	0.0299 (4)	0.0333 (4)	0.0159 (4)
Cl2	0.0481 (3)	0.0614 (4)	0.0732 (4)	0.0105 (3)	−0.0080 (3)	0.0291 (3)

Geometric parameters (Å, º) top

Zn1—O4	1.9863 (17)	C6—H6A	0.9300
Zn1—O7	2.0507 (17)	C8—C13	1.394 (3)
Zn1—O1	2.0715 (17)	C8—C9	1.396 (3)
Zn1—N2	2.104 (2)	C8—C14	1.490 (3)
Zn1—N1	2.1514 (19)	C9—C10	1.389 (3)
N1—C15	1.339 (3)	C10—C11	1.371 (4)
N1—C19	1.342 (3)	C10—H10A	0.9300
N2—C24	1.342 (3)	C11—C12	1.376 (3)
N2—C20	1.346 (3)	C11—H11A	0.9300
O1—C7	1.263 (3)	C12—C13	1.371 (3)
O2—C7	1.258 (2)	C12—Cl2	1.736 (2)
O3—C2	1.348 (3)	C13—H13A	0.9300
O3—H3B	0.82 (3)	C15—C16	1.356 (3)
O4—C14	1.264 (3)	C15—H15A	0.9300
O5—C14	1.254 (2)	C16—C17	1.380 (4)
O6—C9	1.351 (3)	C16—H16A	0.9300
O6—H6B	0.82 (3)	C17—C18	1.372 (4)
O7—H7B	0.826 (10)	C17—H17A	0.9300
O7—H7A	0.810 (10)	C18—C19	1.372 (3)
C1—C6	1.389 (3)	C18—H18A	0.9300
C1—C2	1.403 (3)	C19—C20	1.479 (3)
C1—C7	1.488 (3)	C20—C21	1.380 (3)
C2—C3	1.389 (3)	C21—C22	1.379 (4)
C3—C4	1.367 (4)	C21—H21A	0.9300
C3—H3A	0.9300	C22—C23	1.352 (4)
C4—C5	1.380 (4)	C22—H22A	0.9300
C4—H4A	0.9300	C23—C24	1.389 (3)
C5—C6	1.372 (3)	C23—H23A	0.9300
C5—Cl1	1.740 (2)	C24—H24A	0.9300

O4—Zn1—O7	113.87 (7)	O6—C9—C8	121.2 (2)
O4—Zn1—O1	96.40 (7)	C10—C9—C8	120.3 (2)
O7—Zn1—O1	88.52 (7)	C11—C10—C9	120.0 (2)
O4—Zn1—N2	109.12 (7)	C11—C10—H10A	120.0
O7—Zn1—N2	136.91 (7)	C9—C10—H10A	120.0
O1—Zn1—N2	89.69 (7)	C10—C11—C12	119.7 (2)
O4—Zn1—N1	103.25 (8)	C10—C11—H11A	120.2
O7—Zn1—N1	90.52 (7)	C12—C11—H11A	120.2
O1—Zn1—N1	158.89 (7)	C13—C12—C11	121.4 (2)
N2—Zn1—N1	76.73 (7)	C13—C12—Cl2	120.20 (17)
C15—N1—C19	118.18 (19)	C11—C12—Cl2	118.42 (17)
C15—N1—Zn1	126.70 (15)	C12—C13—C8	119.75 (19)
C19—N1—Zn1	115.13 (14)	C12—C13—H13A	120.1
C24—N2—C20	118.58 (19)	C8—C13—H13A	120.1
C24—N2—Zn1	124.50 (16)	O5—C14—O4	123.54 (19)
C20—N2—Zn1	116.90 (14)	O5—C14—C8	118.04 (18)
C7—O1—Zn1	124.19 (13)	O4—C14—C8	118.40 (17)
C2—O3—H3B	106 (2)	N1—C15—C16	123.1 (2)
C14—O4—Zn1	117.68 (13)	N1—C15—H15A	118.4
C9—O6—H6B	106 (2)	C16—C15—H15A	118.4
Zn1—O7—H7B	100.3 (17)	C15—C16—C17	119.0 (2)
Zn1—O7—H7A	122.6 (18)	C15—C16—H16A	120.5
H7B—O7—H7A	105 (3)	C17—C16—H16A	120.5
C6—C1—C2	118.89 (19)	C18—C17—C16	118.3 (2)
C6—C1—C7	120.63 (19)	C18—C17—H17A	120.9
C2—C1—C7	120.48 (19)	C16—C17—H17A	120.9
O3—C2—C3	118.2 (2)	C19—C18—C17	120.1 (2)
O3—C2—C1	121.9 (2)	C19—C18—H18A	120.0
C3—C2—C1	119.9 (2)	C17—C18—H18A	120.0
C4—C3—C2	120.2 (2)	N1—C19—C18	121.3 (2)
C4—C3—H3A	119.9	N1—C19—C20	115.92 (18)
C2—C3—H3A	119.9	C18—C19—C20	122.8 (2)
C3—C4—C5	120.1 (2)	N2—C20—C21	121.5 (2)
C3—C4—H4A	119.9	N2—C20—C19	115.30 (18)
C5—C4—H4A	119.9	C21—C20—C19	123.2 (2)
C6—C5—C4	120.6 (2)	C22—C21—C20	119.3 (2)
C6—C5—Cl1	120.34 (19)	C22—C21—H21A	120.4
C4—C5—Cl1	119.05 (18)	C20—C21—H21A	120.4
C5—C6—C1	120.3 (2)	C23—C22—C21	119.5 (2)
C5—C6—H6A	119.9	C23—C22—H22A	120.2
C1—C6—H6A	119.9	C21—C22—H22A	120.2
O2—C7—O1	123.97 (19)	C22—C23—C24	119.2 (2)
O2—C7—C1	117.45 (19)	C22—C23—H23A	120.4
O1—C7—C1	118.57 (18)	C24—C23—H23A	120.4
C13—C8—C9	118.82 (19)	N2—C24—C23	121.9 (2)
C13—C8—C14	120.88 (18)	N2—C24—H24A	119.1
C9—C8—C14	120.28 (18)	C23—C24—H24A	119.1
O6—C9—C10	118.4 (2)

O4—Zn1—N1—C15	−74.08 (19)	C14—C8—C9—O6	−0.9 (3)
O7—Zn1—N1—C15	40.62 (19)	C13—C8—C9—C10	−0.3 (3)
O1—Zn1—N1—C15	127.8 (2)	C14—C8—C9—C10	178.3 (2)
N2—Zn1—N1—C15	179.06 (19)	O6—C9—C10—C11	179.2 (2)
O4—Zn1—N1—C19	105.74 (15)	C8—C9—C10—C11	−0.1 (4)
O7—Zn1—N1—C19	−139.56 (15)	C9—C10—C11—C12	1.1 (4)
O1—Zn1—N1—C19	−52.3 (2)	C10—C11—C12—C13	−1.8 (4)
N2—Zn1—N1—C19	−1.13 (14)	C10—C11—C12—Cl2	178.80 (19)
O4—Zn1—N2—C24	80.39 (18)	C11—C12—C13—C8	1.4 (3)
O7—Zn1—N2—C24	−103.76 (18)	Cl2—C12—C13—C8	−179.18 (15)
O1—Zn1—N2—C24	−16.27 (17)	C9—C8—C13—C12	−0.4 (3)
N1—Zn1—N2—C24	−179.96 (18)	C14—C8—C13—C12	−178.97 (18)
O4—Zn1—N2—C20	−98.18 (15)	Zn1—O4—C14—O5	0.9 (3)
O7—Zn1—N2—C20	77.67 (17)	Zn1—O4—C14—C8	−177.68 (13)
O1—Zn1—N2—C20	165.16 (14)	C13—C8—C14—O5	−178.77 (19)
N1—Zn1—N2—C20	1.47 (14)	C9—C8—C14—O5	2.7 (3)
O4—Zn1—O1—C7	69.96 (17)	C13—C8—C14—O4	−0.1 (3)
O7—Zn1—O1—C7	−43.90 (17)	C9—C8—C14—O4	−178.68 (19)
N2—Zn1—O1—C7	179.16 (16)	C19—N1—C15—C16	−1.0 (3)
N1—Zn1—O1—C7	−131.49 (19)	Zn1—N1—C15—C16	178.78 (19)
O7—Zn1—O4—C14	−35.97 (16)	N1—C15—C16—C17	0.7 (4)
O1—Zn1—O4—C14	−127.18 (15)	C15—C16—C17—C18	0.2 (4)
N2—Zn1—O4—C14	140.92 (14)	C16—C17—C18—C19	−0.8 (4)
N1—Zn1—O4—C14	60.59 (16)	C15—N1—C19—C18	0.4 (3)
C6—C1—C2—O3	−179.4 (2)	Zn1—N1—C19—C18	−179.41 (17)
C7—C1—C2—O3	1.0 (3)	C15—N1—C19—C20	−179.48 (18)
C6—C1—C2—C3	1.3 (3)	Zn1—N1—C19—C20	0.7 (2)
C7—C1—C2—C3	−178.3 (2)	C17—C18—C19—N1	0.5 (4)
O3—C2—C3—C4	178.8 (2)	C17—C18—C19—C20	−179.6 (2)
C1—C2—C3—C4	−1.9 (4)	C24—N2—C20—C21	−0.4 (3)
C2—C3—C4—C5	1.5 (4)	Zn1—N2—C20—C21	178.29 (16)
C3—C4—C5—C6	−0.4 (4)	C24—N2—C20—C19	179.77 (18)
C3—C4—C5—Cl1	179.7 (2)	Zn1—N2—C20—C19	−1.6 (2)
C4—C5—C6—C1	−0.2 (3)	N1—C19—C20—N2	0.6 (3)
Cl1—C5—C6—C1	179.72 (16)	C18—C19—C20—N2	−179.3 (2)
C2—C1—C6—C5	−0.2 (3)	N1—C19—C20—C21	−179.3 (2)
C7—C1—C6—C5	179.32 (19)	C18—C19—C20—C21	0.8 (3)
Zn1—O1—C7—O2	20.1 (3)	N2—C20—C21—C22	−0.1 (3)
Zn1—O1—C7—C1	−159.64 (13)	C19—C20—C21—C22	179.8 (2)
C6—C1—C7—O2	173.64 (19)	C20—C21—C22—C23	0.3 (4)
C2—C1—C7—O2	−6.8 (3)	C21—C22—C23—C24	−0.1 (4)
C6—C1—C7—O1	−6.6 (3)	C20—N2—C24—C23	0.6 (3)
C2—C1—C7—O1	172.97 (19)	Zn1—N2—C24—C23	−177.97 (17)
C13—C8—C9—O6	−179.5 (2)	C22—C23—C24—N2	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O2	0.82 (1)	1.85 (1)	2.640 (2)	160 (2)
O7—H7A···O6ⁱ	0.82 (1)	1.98 (1)	2.786 (3)	171 (2)
O3—H3B···O2	0.82 (3)	1.78 (2)	2.516 (3)	148 (3)
O6—H6B···O5	0.82 (3)	1.74 (2)	2.498 (3)	152 (2)
C16—H16A···Cl2ⁱⁱ	0.93	2.79	3.552 (3)	140

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₄ClO₃)₂(C₁₀H₈N₂)(H₂O)]
M_r	582.67
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.114 (5), 11.141 (6), 11.553 (6)
α, β, γ (°)	112.72 (2), 93.208 (19), 97.93 (2)
V (Å³)	1180.8 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.52 × 0.50 × 0.47

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.511, 0.541
No. of measured, independent and observed [I > 2σ(I)] reflections	10689, 4865, 4269
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.094, 1.11
No. of reflections	4865
No. of parameters	337
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.63

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Selected geometric parameters (Å, º) top

Zn1—O4	1.9863 (17)	Zn1—N2	2.104 (2)
Zn1—O7	2.0507 (17)	Zn1—N1	2.1514 (19)
Zn1—O1	2.0715 (17)

O4—Zn1—O7	113.87 (7)	O1—Zn1—N2	89.69 (7)
O4—Zn1—O1	96.40 (7)	O4—Zn1—N1	103.25 (8)
O7—Zn1—O1	88.52 (7)	O7—Zn1—N1	90.52 (7)
O4—Zn1—N2	109.12 (7)	O1—Zn1—N1	158.89 (7)
O7—Zn1—N2	136.91 (7)	N2—Zn1—N1	76.73 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O2	0.82 (1)	1.85 (1)	2.640 (2)	160 (2)
O7—H7A···O6ⁱ	0.82 (1)	1.98 (1)	2.786 (3)	171 (2)
O3—H3B···O2	0.82 (3)	1.78 (2)	2.516 (3)	148 (3)
O6—H6B···O5	0.82 (3)	1.74 (2)	2.498 (3)	152 (2)
C16—H16A···Cl2ⁱⁱ	0.93	2.792	3.552 (3)	140

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

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