Bis(4-formyl­benzoato-κO)bis­(1H-imid­azole-κN3)zinc(II)

Deng, Z.-P.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536807059296

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Bis(4-formylbenzoato-κO)bis(1H-imidazole-κN³)zinc(II)

Z.-P. Deng, S. Gao and S. W. Ng

The zinc centre in the title complex, [Zn(C₈H₅O₃)₂(C₃H₄N₂)₂], shows tetrahedral coordination. Adjacent molecules are linked by N—H

O hydrogen bonds into a layer structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059296/xu2375sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059296/xu2375Isup2.hkl Contains datablock I

CCDC reference: 672728

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.012 Å
R factor = 0.040
wR factor = 0.150
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H2<I>N<
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H4<I>N<

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               4493
           Count of symmetry unique reflns         2781
           Completeness (_total/calc)            161.56%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1712
           Fraction of Friedel pairs measured     0.616
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

As a part of our ongoing investigation on 4-formylbenzoate complexes (Deng et al., 2006a, 2006b, 2007), the title Zn^II complex has been prepared and its structure is reported here. The molecular structure is shown in Fig. 1. The Zn^II ion displays a tetrahedral coordination geometry (Table 1). Adjacent molecules are linked by N—H···O hydrogen bonds into a layer structure (Table 2 and Fig. 2).

Related literature top

For the diaqua complex, see Deng et al. (2006a), and for the aqua phenanthroline adduct, see Deng et al. (2006b). The monohydrated bis(benzimidazole) adduct is hydrogen bonded into a chain structure (see Deng et al., 2007).

Experimental top

Zinc sulfate heptahydrate (1.44 g, 5 mmol) was added to an aqueous solution (25 ml) of 4-formylbenzoic acid (1.5 g, 10 mmol) and imidazole (0.68 g, 10 mmol). The pH value of the mixture was about 6. The solution was allowed to evaporate at room temperature; colorless prismatic crystals separated from the filtered solution after several days. CH&N elemental analysis. Calc. for C₂₂H₁₈N₄O₆Zn: C 52.87, H 3.63, N 11.21%. Found: C 52.88, H 3.68, N 11.18%.

Computing details top

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

	Fig. 1. Thermal ellipsoid plot of the molecular structure. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. OLEX (Dolomanov et al., 2003) representation of the hydrogen-bonded layer structure.

Bis(4-formylbenzoato-κO)bis(1H-imidazole-κN³)zinc(II) top

Crystal data top

[Zn(C₈H₅O₃)₂(C₃H₄N₂)₂]	F(000) = 512
M_r = 499.77	D_x = 1.477 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8013 reflections
a = 11.9413 (9) Å	θ = 3.1–27.5°
b = 7.0455 (5) Å	µ = 1.14 mm⁻¹
c = 14.2092 (9) Å	T = 295 K
β = 109.904 (2)°	Prism, colorless
V = 1124.1 (1) Å³	0.36 × 0.25 × 0.21 mm
Z = 2

Data collection top

Rigaku RAXIS-RAPID IP diffractometer	4493 independent reflections
Radiation source: fine-focus sealed tube	2901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scan	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→15
T_min = 0.662, T_max = 0.796	k = −9→8
11106 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0471P)² + 1.7346P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.001
4493 reflections	Δρ_max = 1.17 e Å⁻³
299 parameters	Δρ_min = −1.12 e Å⁻³
1 restraint	Absolute structure: Flack (1983) parameter from 1716 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

[Zn(C₈H₅O₃)₂(C₃H₄N₂)₂]	V = 1124.1 (1) Å³
M_r = 499.77	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.9413 (9) Å	µ = 1.14 mm⁻¹
b = 7.0455 (5) Å	T = 295 K
c = 14.2092 (9) Å	0.36 × 0.25 × 0.21 mm
β = 109.904 (2)°

Data collection top

Rigaku RAXIS-RAPID IP diffractometer	4493 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2901 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.796	R_int = 0.042
11106 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.150	Δρ_max = 1.17 e Å⁻³
S = 1.13	Δρ_min = −1.12 e Å⁻³
4493 reflections	Absolute structure: Flack (1983) parameter from 1716 Friedel pairs
299 parameters	Absolute structure parameter: 0.01 (2)
1 restraint

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

	x	y	z	U_iso*/U_eq
Zn1	0.77235 (5)	0.49998 (13)	0.20968 (4)	0.0464 (2)
O1	0.8971 (4)	0.3416 (7)	0.1932 (4)	0.0585 (13)
O2	0.7697 (4)	0.1549 (8)	0.0823 (4)	0.0684 (15)
O3	1.3608 (7)	−0.2711 (12)	0.1953 (5)	0.111 (3)
O4	0.6612 (4)	0.3861 (8)	0.2687 (3)	0.0608 (13)
O5	0.7938 (4)	0.3692 (9)	0.4217 (4)	0.0719 (15)
O6	0.1902 (7)	0.3427 (14)	0.4523 (6)	0.126 (3)
N1	0.6505 (4)	0.5887 (8)	0.0812 (4)	0.0461 (12)
N2	0.4747 (5)	0.6479 (9)	−0.0238 (5)	0.0631 (17)
H2n	0.3998	0.6732	−0.0469	0.076*
N3	0.8663 (4)	0.7125 (8)	0.2943 (4)	0.0473 (13)
N4	1.0097 (5)	0.8557 (10)	0.4062 (4)	0.0622 (16)
H4n	1.0774	0.8759	0.4521	0.075*
C1	0.6901 (5)	0.3684 (10)	0.3637 (5)	0.0498 (16)
C2	0.5873 (6)	0.3511 (9)	0.4011 (4)	0.0462 (15)
C3	0.6076 (7)	0.3316 (11)	0.5034 (5)	0.0585 (18)
H3	0.6847	0.3235	0.5489	0.070*
C4	0.5090 (8)	0.3245 (11)	0.5363 (5)	0.064 (2)
H4	0.5215	0.3125	0.6043	0.077*
C5	0.3954 (7)	0.3348 (11)	0.4702 (6)	0.0616 (19)
C6	0.3780 (7)	0.3571 (12)	0.3701 (6)	0.064 (2)
H6	0.3008	0.3680	0.3249	0.077*
C7	0.4699 (6)	0.3635 (11)	0.3360 (5)	0.0535 (17)
H7	0.4550	0.3765	0.2677	0.064*
C8	0.2937 (10)	0.3301 (16)	0.5073 (8)	0.091 (3)
H8	0.3094	0.3168	0.5757	0.109*
C9	0.8711 (5)	0.1953 (10)	0.1381 (5)	0.0450 (14)
C10	0.9721 (6)	0.0645 (9)	0.1431 (5)	0.0459 (16)
C11	0.9491 (7)	−0.1102 (12)	0.0963 (6)	0.064 (2)
H11	0.8710	−0.1469	0.0618	0.077*
C12	1.0425 (8)	−0.2306 (12)	0.1007 (6)	0.074 (2)
H12	1.0270	−0.3478	0.0688	0.089*
C13	1.1581 (7)	−0.1771 (12)	0.1522 (6)	0.062 (2)
C14	1.1811 (6)	−0.0046 (18)	0.1993 (5)	0.073 (2)
H14	1.2593	0.0317	0.2336	0.087*
C15	1.0887 (5)	0.1152 (11)	0.1958 (6)	0.062 (2)
H15	1.1047	0.2310	0.2292	0.075*
C16	1.2565 (9)	−0.3093 (15)	0.1549 (7)	0.082 (3)
H16	1.2368	−0.4270	0.1241	0.098*
C17	0.6563 (6)	0.5897 (11)	−0.0136 (5)	0.0551 (17)
H17	0.7242	0.5678	−0.0300	0.066*
C18	0.5469 (7)	0.6276 (12)	−0.0788 (5)	0.064 (2)
H18	0.5252	0.6379	−0.1480	0.077*
C19	0.5387 (5)	0.6224 (10)	0.0710 (5)	0.0496 (16)
H19	0.5089	0.6274	0.1235	0.060*
C20	0.8343 (6)	0.8961 (11)	0.3001 (5)	0.0549 (17)
H20	0.7622	0.9505	0.2619	0.066*
C21	0.9231 (6)	0.9861 (16)	0.3696 (5)	0.0631 (17)
H21	0.9248	1.1126	0.3887	0.076*
C22	0.9740 (6)	0.6922 (12)	0.3605 (5)	0.0578 (18)
H22	1.0180	0.5803	0.3731	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0356 (3)	0.0558 (4)	0.0432 (3)	0.0037 (4)	0.0074 (2)	−0.0028 (5)
O1	0.041 (2)	0.057 (3)	0.070 (3)	0.004 (2)	0.009 (2)	−0.011 (3)
O2	0.035 (2)	0.080 (4)	0.074 (3)	0.004 (2)	−0.002 (2)	−0.016 (3)
O3	0.096 (5)	0.148 (7)	0.102 (5)	0.067 (5)	0.051 (4)	0.033 (5)
O4	0.054 (3)	0.076 (4)	0.044 (2)	−0.005 (2)	0.006 (2)	0.003 (2)
O5	0.049 (3)	0.101 (4)	0.055 (3)	0.007 (3)	0.005 (2)	0.016 (3)
O6	0.090 (5)	0.172 (8)	0.134 (6)	0.009 (6)	0.061 (5)	0.006 (6)
N1	0.032 (2)	0.061 (3)	0.043 (3)	0.005 (2)	0.010 (2)	−0.004 (2)
N2	0.034 (3)	0.072 (4)	0.072 (4)	0.007 (3)	0.003 (3)	0.008 (3)
N3	0.037 (3)	0.056 (4)	0.044 (3)	0.004 (2)	0.007 (2)	0.001 (3)
N4	0.058 (4)	0.071 (4)	0.048 (3)	−0.015 (3)	0.006 (3)	−0.015 (3)
C1	0.040 (3)	0.052 (4)	0.051 (4)	0.007 (3)	0.007 (3)	0.002 (3)
C2	0.055 (4)	0.042 (4)	0.042 (3)	0.005 (3)	0.018 (3)	−0.001 (3)
C3	0.062 (4)	0.061 (5)	0.053 (4)	0.010 (3)	0.019 (3)	0.003 (4)
C4	0.096 (6)	0.054 (5)	0.048 (4)	0.006 (4)	0.032 (4)	0.009 (3)
C5	0.061 (5)	0.057 (5)	0.074 (5)	0.007 (4)	0.031 (4)	0.004 (4)
C6	0.050 (4)	0.075 (5)	0.070 (5)	−0.006 (4)	0.025 (4)	−0.004 (4)
C7	0.049 (4)	0.062 (5)	0.047 (3)	0.003 (3)	0.013 (3)	−0.006 (3)
C8	0.099 (8)	0.095 (8)	0.099 (7)	0.014 (6)	0.060 (6)	0.003 (6)
C9	0.040 (3)	0.048 (4)	0.046 (3)	0.005 (3)	0.012 (3)	0.001 (3)
C10	0.040 (3)	0.046 (4)	0.054 (4)	0.008 (2)	0.019 (3)	0.003 (3)
C11	0.059 (5)	0.060 (5)	0.073 (5)	−0.003 (4)	0.023 (4)	−0.013 (4)
C12	0.096 (7)	0.055 (5)	0.077 (5)	0.016 (4)	0.037 (5)	−0.010 (4)
C13	0.067 (5)	0.069 (5)	0.058 (4)	0.019 (4)	0.032 (4)	0.008 (4)
C14	0.046 (3)	0.090 (6)	0.079 (4)	0.027 (6)	0.017 (3)	−0.012 (7)
C15	0.033 (3)	0.067 (5)	0.083 (5)	0.003 (3)	0.013 (3)	−0.021 (4)
C16	0.093 (7)	0.091 (7)	0.073 (5)	0.042 (6)	0.042 (5)	0.018 (5)
C17	0.053 (4)	0.066 (5)	0.043 (3)	0.002 (3)	0.012 (3)	0.003 (3)
C18	0.058 (4)	0.076 (6)	0.046 (4)	0.001 (4)	0.003 (3)	0.008 (4)
C19	0.031 (3)	0.062 (4)	0.049 (3)	0.004 (3)	0.005 (3)	−0.003 (3)
C20	0.049 (4)	0.065 (5)	0.051 (4)	0.011 (3)	0.017 (3)	0.003 (3)
C21	0.077 (4)	0.054 (4)	0.061 (4)	−0.004 (5)	0.027 (3)	−0.010 (5)
C22	0.045 (4)	0.064 (5)	0.052 (4)	−0.003 (3)	0.000 (3)	−0.010 (4)

Geometric parameters (Å, º) top

Zn1—O1	1.938 (5)	C5—C6	1.375 (10)
Zn1—O4	1.966 (5)	C5—C8	1.480 (12)
Zn1—N1	2.007 (5)	C6—C7	1.342 (9)
Zn1—N3	2.007 (6)	C6—H6	0.9300
O1—C9	1.267 (8)	C7—H7	0.9300
O2—C9	1.235 (7)	C8—H8	0.9300
O3—C16	1.212 (11)	C9—C10	1.500 (9)
O4—C1	1.281 (7)	C10—C11	1.382 (10)
O5—C1	1.232 (7)	C10—C15	1.384 (9)
O6—C8	1.220 (11)	C11—C12	1.385 (11)
N1—C19	1.315 (7)	C11—H11	0.9300
N1—C17	1.373 (8)	C12—C13	1.377 (12)
N2—C19	1.315 (8)	C12—H12	0.9300
N2—C18	1.354 (10)	C13—C14	1.369 (14)
N2—H2n	0.8600	C13—C16	1.489 (11)
N3—C22	1.318 (8)	C14—C15	1.377 (10)
N3—C20	1.360 (9)	C14—H14	0.9300
N4—C22	1.320 (10)	C15—H15	0.9300
N4—C21	1.348 (11)	C16—H16	0.9300
N4—H4n	0.8600	C17—C18	1.346 (10)
C1—C2	1.499 (9)	C17—H17	0.9300
C2—C7	1.395 (9)	C18—H18	0.9300
C2—C3	1.397 (9)	C19—H19	0.9300
C3—C4	1.408 (11)	C20—C21	1.337 (10)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.364 (11)	C21—H21	0.9300
C4—H4	0.9300	C22—H22	0.9300

O1—Zn1—O4	118.3 (2)	C5—C8—H8	118.5
O1—Zn1—N1	114.7 (2)	O2—C9—O1	124.4 (6)
O1—Zn1—N3	101.9 (2)	O2—C9—C10	119.1 (6)
O4—Zn1—N1	97.4 (2)	O1—C9—C10	116.5 (5)
O4—Zn1—N3	111.7 (2)	C11—C10—C15	119.3 (6)
N1—Zn1—N3	113.4 (2)	C11—C10—C9	120.0 (7)
C9—O1—Zn1	120.4 (4)	C15—C10—C9	120.7 (6)
C1—O4—Zn1	120.7 (4)	C10—C11—C12	119.9 (8)
C19—N1—C17	106.2 (5)	C10—C11—H11	120.1
C19—N1—Zn1	123.5 (4)	C12—C11—H11	120.1
C17—N1—Zn1	129.1 (4)	C13—C12—C11	120.2 (8)
C19—N2—C18	108.4 (5)	C13—C12—H12	119.9
C19—N2—H2n	125.8	C11—C12—H12	119.9
C18—N2—H2n	125.8	C14—C13—C12	120.1 (7)
C22—N3—C20	106.6 (6)	C14—C13—C16	121.1 (8)
C22—N3—Zn1	123.9 (5)	C12—C13—C16	118.8 (9)
C20—N3—Zn1	129.5 (4)	C13—C14—C15	120.1 (7)
C22—N4—C21	109.2 (6)	C13—C14—H14	120.0
C22—N4—H4n	125.4	C15—C14—H14	120.0
C21—N4—H4n	125.4	C14—C15—C10	120.5 (8)
O5—C1—O4	123.6 (6)	C14—C15—H15	119.8
O5—C1—C2	121.4 (6)	C10—C15—H15	119.8
O4—C1—C2	115.0 (5)	O3—C16—C13	123.3 (10)
C7—C2—C3	118.4 (6)	O3—C16—H16	118.4
C7—C2—C1	121.3 (6)	C13—C16—H16	118.4
C3—C2—C1	120.3 (6)	C18—C17—N1	108.4 (7)
C2—C3—C4	118.7 (7)	C18—C17—H17	125.8
C2—C3—H3	120.6	N1—C17—H17	125.8
C4—C3—H3	120.6	C17—C18—N2	106.4 (6)
C5—C4—C3	121.1 (7)	C17—C18—H18	126.8
C5—C4—H4	119.4	N2—C18—H18	126.8
C3—C4—H4	119.4	N1—C19—N2	110.6 (6)
C4—C5—C6	118.9 (7)	N1—C19—H19	124.7
C4—C5—C8	119.8 (8)	N2—C19—H19	124.7
C6—C5—C8	121.2 (8)	C21—C20—N3	109.1 (7)
C7—C6—C5	121.5 (7)	C21—C20—H20	125.4
C7—C6—H6	119.2	N3—C20—H20	125.4
C5—C6—H6	119.2	C20—C21—N4	105.9 (8)
C6—C7—C2	121.3 (7)	C20—C21—H21	127.1
C6—C7—H7	119.4	N4—C21—H21	127.1
C2—C7—H7	119.4	N3—C22—N4	109.2 (7)
O6—C8—C5	123.0 (10)	N3—C22—H22	125.4
O6—C8—H8	118.5	N4—C22—H22	125.4

O4—Zn1—O1—C9	61.0 (5)	C4—C5—C8—O6	178.4 (10)
N3—Zn1—O1—C9	−176.1 (5)	C6—C5—C8—O6	1.1 (15)
N1—Zn1—O1—C9	−53.2 (6)	Zn1—O1—C9—O2	9.4 (9)
O1—Zn1—O4—C1	81.4 (6)	Zn1—O1—C9—C10	−170.2 (4)
N3—Zn1—O4—C1	−36.4 (6)	O2—C9—C10—C11	−8.5 (10)
N1—Zn1—O4—C1	−155.2 (5)	O1—C9—C10—C11	171.1 (6)
O1—Zn1—N1—C19	149.5 (5)	O2—C9—C10—C15	172.6 (7)
O4—Zn1—N1—C19	23.6 (6)	O1—C9—C10—C15	−7.7 (10)
N3—Zn1—N1—C19	−94.0 (5)	C15—C10—C11—C12	−1.4 (11)
O1—Zn1—N1—C17	−16.0 (7)	C9—C10—C11—C12	179.8 (7)
O4—Zn1—N1—C17	−141.9 (6)	C10—C11—C12—C13	0.4 (13)
N3—Zn1—N1—C17	100.5 (6)	C11—C12—C13—C14	0.1 (13)
O1—Zn1—N3—C22	−31.2 (6)	C11—C12—C13—C16	−179.6 (8)
O4—Zn1—N3—C22	96.1 (6)	C12—C13—C14—C15	0.4 (13)
N1—Zn1—N3—C22	−155.0 (5)	C16—C13—C14—C15	−179.9 (8)
O1—Zn1—N3—C20	152.0 (6)	C13—C14—C15—C10	−1.4 (13)
O4—Zn1—N3—C20	−80.7 (6)	C11—C10—C15—C14	1.9 (12)
N1—Zn1—N3—C20	28.2 (6)	C9—C10—C15—C14	−179.3 (7)
Zn1—O4—C1—O5	−20.8 (10)	C14—C13—C16—O3	−2.4 (14)
Zn1—O4—C1—C2	157.8 (5)	C12—C13—C16—O3	177.2 (8)
O5—C1—C2—C7	175.5 (7)	C19—N1—C17—C18	1.1 (8)
O4—C1—C2—C7	−3.1 (10)	Zn1—N1—C17—C18	168.6 (5)
O5—C1—C2—C3	−1.3 (11)	N1—C17—C18—N2	−0.6 (9)
O4—C1—C2—C3	−179.8 (6)	C19—N2—C18—C17	−0.2 (9)
C7—C2—C3—C4	0.3 (11)	C17—N1—C19—N2	−1.2 (8)
C1—C2—C3—C4	177.1 (7)	Zn1—N1—C19—N2	−169.6 (5)
C2—C3—C4—C5	0.5 (11)	C18—N2—C19—N1	0.9 (9)
C3—C4—C5—C6	−1.6 (12)	C22—N3—C20—C21	0.3 (8)
C3—C4—C5—C8	−179.0 (8)	Zn1—N3—C20—C21	177.4 (5)
C4—C5—C6—C7	1.9 (13)	N3—C20—C21—N4	0.0 (8)
C8—C5—C6—C7	179.3 (9)	C22—N4—C21—C20	−0.2 (8)
C5—C6—C7—C2	−1.1 (13)	C20—N3—C22—N4	−0.4 (8)
C3—C2—C7—C6	0.0 (11)	Zn1—N3—C22—N4	−177.7 (5)
C1—C2—C7—C6	−176.8 (7)	C21—N4—C22—N3	0.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O2ⁱ	0.86	1.92	2.749 (7)	163
N4—H4n···O5ⁱⁱ	0.86	1.93	2.754 (7)	162

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₅O₃)₂(C₃H₄N₂)₂]
M_r	499.77
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	11.9413 (9), 7.0455 (5), 14.2092 (9)
β (°)	109.904 (2)
V (Å³)	1124.1 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.36 × 0.25 × 0.21

Data collection
Diffractometer	Rigaku RAXIS-RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.662, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	11106, 4493, 2901
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.150, 1.13
No. of reflections	4493
No. of parameters	299
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.17, −1.12
Absolute structure	Flack (1983) parameter from 1716 Friedel pairs
Absolute structure parameter	0.01 (2)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2007).

Selected geometric parameters (Å, º) top

Zn1—O1	1.938 (5)	Zn1—N1	2.007 (5)
Zn1—O4	1.966 (5)	Zn1—N3	2.007 (6)

O1—Zn1—O4	118.3 (2)	O4—Zn1—N1	97.4 (2)
O1—Zn1—N1	114.7 (2)	O4—Zn1—N3	111.7 (2)
O1—Zn1—N3	101.9 (2)	N1—Zn1—N3	113.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O2ⁱ	0.86	1.92	2.749 (7)	163
N4—H4n···O5ⁱⁱ	0.86	1.93	2.754 (7)	162

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

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