Diaqua-bis-(4-formyl-benzoato-κO(1))bis-(nicotinamide-κN(1))zinc.

In the title complex, [Zn(C(8)H(5)O(3))(2)(C(6)H(6)N(2)O)(2)(H(2)O)(2)], the Zn(II) cation is located on an inversion center and is coordinated by two 4-formyl-benzoate (FB) anions, two nicotinamide (NA) ligands and two water mol-ecules. The four O atoms in the equatorial plane around the Zn(II) cation form a slightly distorted square-planar arrangement, while the slightly distorted octa-hedral coordination is completed by the two N atoms of the NA ligands in the axial positions. The dihedral angle between the carboxyl-ate group and the adjacent benzene ring is 24.13 (8)°, while the pyridine ring and the benzene ring are oriented at a dihedral angle of 88.52 (4)°. The coordinating water mol-ecule links with the carboxyl-ate group via an O-H⋯O hydrogen bond. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds, and a weak C-H⋯π inter-action link the mol-ecules into a two-dimensional network parallel to (010). These networks are linked via C-H⋯O and π-π inter-actions between inversion-related benzene rings [centroid-centroid distance = 3.8483 (7) Å], forming a three-dimensional supra-molecular structure.

Related literature

For literature on niacin, see: Krishnamachari (1974 ▶). For information on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Aydın et al. (2012 ▶); Hökelek et al. (2009 ▶); Necefoğlu et al. (2011 ▶); Sertçelik et al. (2012a ▶,b ▶,c ▶,d ▶); Sertçelik et al. (2009a ▶,b ▶,c ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Zn(C8H5O3)2(C6H6N2O)2(H2O)2]

M = 643.92

Triclinic,

a = 7.7861 (2) Å

b = 9.7877 (3) Å

c = 9.9087 (3) Å

α = 77.851 (3)°

β = 71.462 (2)°

γ = 86.720 (3)°

V = 699.87 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.94 mm−1

T = 100 K

0.44 × 0.37 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.682, T max = 0.831

12257 measured reflections

3475 independent reflections

3413 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.060

S = 1.06

3475 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203320X/su2483sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203320X/su2483Isup2.hkl

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

[Zn(C8H5O3)2(C6H6N2O)2(H2O)2]	Z = 1
Mr = 643.92	F(000) = 332
Triclinic, P1	Dx = 1.528 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7861 (2) Å	Cell parameters from 9923 reflections
b = 9.7877 (3) Å	θ = 2.7–28.5°
c = 9.9087 (3) Å	µ = 0.94 mm−1
α = 77.851 (3)°	T = 100 K
β = 71.462 (2)°	Block, colourless
γ = 86.720 (3)°	0.44 × 0.37 × 0.20 mm
V = 699.87 (4) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	3475 independent reflections
Radiation source: fine-focus sealed tube	3413 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.682, Tmax = 0.831	k = −13→13
12257 measured reflections	l = −11→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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0274P)2 + 0.3774P] where P = (Fo2 + 2Fc2)/3
3475 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.31 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
Zn1	0.0000	0.0000	0.0000	0.01128 (6)
O1	0.12362 (11)	0.18202 (9)	0.00926 (9)	0.01501 (16)
O2	−0.11031 (11)	0.27782 (9)	0.15725 (9)	0.01613 (17)
O3	0.49521 (14)	0.66936 (13)	0.32150 (15)	0.0404 (3)
O4	−0.43332 (12)	0.00146 (9)	−0.33495 (9)	0.01797 (17)
O5	0.26589 (11)	−0.08294 (9)	−0.07850 (10)	0.01534 (16)
H51	0.345 (3)	−0.042 (2)	−0.144 (2)	0.033 (5)*
H52	0.238 (3)	−0.151 (2)	−0.110 (2)	0.038 (5)*
N1	−0.00282 (13)	0.09203 (10)	−0.21362 (11)	0.01310 (18)
N2	−0.32692 (15)	0.13245 (12)	−0.56057 (11)	0.0178 (2)
H21	−0.245 (2)	0.1865 (18)	−0.6267 (19)	0.025 (4)*
H22	−0.411 (2)	0.1018 (19)	−0.584 (2)	0.027 (4)*
C1	0.05609 (15)	0.26503 (11)	0.09352 (12)	0.0128 (2)
C2	0.18554 (15)	0.35243 (11)	0.12616 (12)	0.0128 (2)
C3	0.36219 (15)	0.30780 (12)	0.11172 (13)	0.0151 (2)
H3	0.4044	0.2294	0.0723	0.018*
C4	0.47558 (16)	0.38054 (12)	0.15623 (14)	0.0169 (2)
H4	0.5932	0.3501	0.1479	0.020*
C5	0.41325 (16)	0.49869 (12)	0.21317 (14)	0.0170 (2)
C6	0.23814 (16)	0.54657 (13)	0.22349 (15)	0.0194 (2)
H6	0.1980	0.6273	0.2590	0.023*
C7	0.12464 (15)	0.47344 (12)	0.18077 (14)	0.0168 (2)
H7	0.0075	0.5046	0.1883	0.020*
C8	0.53693 (18)	0.57168 (15)	0.26194 (17)	0.0257 (3)
H8	0.665 (2)	0.5325 (17)	0.2463 (18)	0.021 (4)*
C9	−0.14410 (15)	0.06794 (11)	−0.25551 (12)	0.0132 (2)
H9	−0.2391	0.0122	−0.1889	0.016*
C10	−0.15524 (15)	0.12221 (11)	−0.39338 (12)	0.0131 (2)
C11	−0.01372 (16)	0.20686 (13)	−0.49174 (13)	0.0178 (2)
H11	−0.0168	0.2454	−0.5851	0.021*
C12	0.13251 (16)	0.23309 (13)	−0.44870 (13)	0.0192 (2)
H12	0.2284	0.2897	−0.5127	0.023*
C13	0.13337 (15)	0.17388 (12)	−0.30955 (13)	0.0156 (2)
H13	0.2316	0.1913	−0.2812	0.019*
C14	−0.31742 (15)	0.08240 (12)	−0.42808 (12)	0.0140 (2)

	U11	U22	U33	U12	U13	U23
Zn1	0.01063 (9)	0.01353 (9)	0.01123 (9)	−0.00014 (6)	−0.00480 (6)	−0.00367 (6)
O1	0.0147 (4)	0.0165 (4)	0.0146 (4)	−0.0020 (3)	−0.0042 (3)	−0.0051 (3)
O2	0.0119 (4)	0.0183 (4)	0.0189 (4)	−0.0008 (3)	−0.0044 (3)	−0.0056 (3)
O3	0.0237 (5)	0.0457 (7)	0.0640 (8)	−0.0008 (5)	−0.0123 (5)	−0.0392 (6)
O4	0.0172 (4)	0.0235 (4)	0.0141 (4)	−0.0062 (3)	−0.0064 (3)	−0.0016 (3)
O5	0.0122 (4)	0.0179 (4)	0.0160 (4)	−0.0007 (3)	−0.0034 (3)	−0.0050 (3)
N1	0.0130 (4)	0.0147 (4)	0.0129 (4)	−0.0003 (3)	−0.0053 (3)	−0.0036 (3)
N2	0.0183 (5)	0.0233 (5)	0.0135 (5)	−0.0057 (4)	−0.0080 (4)	−0.0014 (4)
C1	0.0140 (5)	0.0127 (5)	0.0120 (5)	−0.0013 (4)	−0.0060 (4)	0.0002 (4)
C2	0.0128 (5)	0.0131 (5)	0.0125 (5)	−0.0018 (4)	−0.0042 (4)	−0.0018 (4)
C3	0.0141 (5)	0.0136 (5)	0.0184 (5)	0.0005 (4)	−0.0052 (4)	−0.0050 (4)
C4	0.0125 (5)	0.0170 (5)	0.0227 (6)	0.0010 (4)	−0.0068 (4)	−0.0054 (4)
C5	0.0141 (5)	0.0176 (5)	0.0207 (6)	−0.0026 (4)	−0.0053 (4)	−0.0066 (4)
C6	0.0159 (5)	0.0164 (5)	0.0274 (6)	0.0003 (4)	−0.0050 (5)	−0.0108 (5)
C7	0.0124 (5)	0.0162 (5)	0.0227 (6)	0.0011 (4)	−0.0055 (4)	−0.0062 (4)
C8	0.0166 (6)	0.0289 (7)	0.0367 (8)	−0.0025 (5)	−0.0086 (5)	−0.0162 (6)
C9	0.0127 (5)	0.0141 (5)	0.0138 (5)	−0.0011 (4)	−0.0048 (4)	−0.0033 (4)
C10	0.0135 (5)	0.0144 (5)	0.0128 (5)	−0.0001 (4)	−0.0052 (4)	−0.0041 (4)
C11	0.0190 (5)	0.0219 (5)	0.0118 (5)	−0.0034 (4)	−0.0052 (4)	−0.0005 (4)
C12	0.0154 (5)	0.0230 (6)	0.0170 (6)	−0.0064 (4)	−0.0032 (4)	−0.0007 (5)
C13	0.0129 (5)	0.0175 (5)	0.0175 (5)	−0.0015 (4)	−0.0055 (4)	−0.0043 (4)
C14	0.0145 (5)	0.0158 (5)	0.0140 (5)	0.0001 (4)	−0.0061 (4)	−0.0053 (4)

Zn1—O1	2.1047 (8)	C3—H3	0.9300
Zn1—O1i	2.1047 (8)	C4—C3	1.3902 (16)
Zn1—O5	2.1446 (8)	C4—C5	1.3883 (16)
Zn1—O5i	2.1446 (8)	C4—H4	0.9300
Zn1—N1	2.1253 (10)	C5—C6	1.3955 (17)
Zn1—N1i	2.1253 (10)	C5—C8	1.4803 (17)
O1—C1	1.2614 (14)	C6—H6	0.9300
O2—C1	1.2600 (14)	C7—C6	1.3822 (16)
O3—C8	1.2032 (17)	C7—H7	0.9300
O4—C14	1.2402 (14)	C8—H8	1.022 (17)
O5—H51	0.79 (2)	C9—C10	1.3859 (16)
O5—H52	0.86 (2)	C9—H9	0.9300
N1—C9	1.3413 (14)	C10—C11	1.3900 (16)
N1—C13	1.3437 (14)	C10—C14	1.5011 (15)
N2—C14	1.3250 (16)	C11—C12	1.3901 (17)
N2—H21	0.861 (18)	C11—H11	0.9300
N2—H22	0.847 (19)	C12—H12	0.9300
C1—C2	1.5082 (15)	C13—C12	1.3806 (17)
C2—C3	1.3912 (15)	C13—H13	0.9300
C2—C7	1.4009 (15)
O1—Zn1—O1i	180.00 (2)	C3—C4—H4	120.0
O1—Zn1—O5	88.01 (3)	C5—C4—C3	119.98 (11)
O1i—Zn1—O5	91.99 (3)	C5—C4—H4	120.0
O1—Zn1—O5i	91.99 (3)	C4—C5—C6	120.33 (11)
O1i—Zn1—O5i	88.01 (3)	C4—C5—C8	118.35 (11)
O1—Zn1—N1	89.84 (3)	C6—C5—C8	121.32 (11)
O1i—Zn1—N1	90.16 (3)	C5—C6—H6	120.1
O1—Zn1—N1i	90.16 (3)	C7—C6—C5	119.71 (11)
O1i—Zn1—N1i	89.84 (3)	C7—C6—H6	120.1
O5i—Zn1—O5	180.00 (5)	C2—C7—H7	119.9
N1—Zn1—O5	92.47 (3)	C6—C7—C2	120.18 (11)
N1i—Zn1—O5	87.53 (3)	C6—C7—H7	119.9
N1—Zn1—O5i	87.53 (3)	O3—C8—C5	124.61 (12)
N1i—Zn1—O5i	92.47 (3)	O3—C8—H8	119.0 (9)
N1i—Zn1—N1	180.00 (6)	C5—C8—H8	116.4 (9)
C1—O1—Zn1	126.47 (7)	N1—C9—C10	123.12 (10)
Zn1—O5—H51	123.5 (14)	N1—C9—H9	118.4
Zn1—O5—H52	98.4 (13)	C10—C9—H9	118.4
H52—O5—H51	105.2 (18)	C9—C10—C11	118.07 (10)
C9—N1—Zn1	119.49 (8)	C9—C10—C14	117.71 (10)
C9—N1—C13	118.35 (10)	C11—C10—C14	124.20 (10)
C13—N1—Zn1	122.16 (8)	C10—C11—C12	119.12 (11)
C14—N2—H21	123.1 (12)	C10—C11—H11	120.4
C14—N2—H22	117.9 (12)	C12—C11—H11	120.4
H22—N2—H21	118.6 (17)	C11—C12—H12	120.5
O1—C1—C2	117.40 (10)	C13—C12—C11	119.04 (11)
O2—C1—O1	125.67 (10)	C13—C12—H12	120.5
O2—C1—C2	116.89 (10)	N1—C13—C12	122.30 (11)
C3—C2—C1	119.98 (10)	N1—C13—H13	118.8
C3—C2—C7	119.82 (10)	C12—C13—H13	118.8
C7—C2—C1	120.05 (10)	O4—C14—N2	122.62 (11)
C2—C3—H3	120.0	O4—C14—C10	119.55 (10)
C4—C3—C2	119.93 (10)	N2—C14—C10	117.79 (10)
C4—C3—H3	120.0
O5—Zn1—O1—C1	−152.50 (9)	C1—C2—C3—C4	−173.27 (11)
O5i—Zn1—O1—C1	27.50 (9)	C7—C2—C3—C4	2.26 (17)
N1—Zn1—O1—C1	115.03 (9)	C1—C2—C7—C6	173.98 (11)
N1i—Zn1—O1—C1	−64.97 (9)	C3—C2—C7—C6	−1.55 (18)
O1—Zn1—N1—C9	−143.10 (8)	C5—C4—C3—C2	−0.88 (18)
O1i—Zn1—N1—C9	36.90 (8)	C3—C4—C5—C6	−1.22 (19)
O1—Zn1—N1—C13	37.17 (9)	C3—C4—C5—C8	178.85 (12)
O1i—Zn1—N1—C13	−142.83 (9)	C4—C5—C6—C7	1.9 (2)
O5—Zn1—N1—C9	128.89 (8)	C8—C5—C6—C7	−178.14 (12)
O5i—Zn1—N1—C9	−51.11 (8)	C4—C5—C8—O3	−174.99 (15)
O5—Zn1—N1—C13	−50.84 (9)	C6—C5—C8—O3	5.1 (2)
O5i—Zn1—N1—C13	129.16 (9)	C2—C7—C6—C5	−0.54 (19)
Zn1—O1—C1—O2	−21.18 (16)	N1—C9—C10—C11	−0.77 (17)
Zn1—O1—C1—C2	156.07 (7)	N1—C9—C10—C14	177.58 (10)
Zn1—N1—C9—C10	−179.02 (8)	C9—C10—C11—C12	0.27 (17)
C13—N1—C9—C10	0.72 (17)	C14—C10—C11—C12	−177.96 (11)
Zn1—N1—C13—C12	179.57 (9)	C9—C10—C14—O4	−1.27 (16)
C9—N1—C13—C12	−0.16 (17)	C9—C10—C14—N2	−178.98 (10)
O1—C1—C2—C3	−23.65 (15)	C11—C10—C14—O4	176.97 (11)
O1—C1—C2—C7	160.83 (11)	C11—C10—C14—N2	−0.74 (17)
O2—C1—C2—C3	153.83 (11)	C10—C11—C12—C13	0.23 (19)
O2—C1—C2—C7	−21.68 (16)	N1—C13—C12—C11	−0.30 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O2ii	0.862 (17)	2.087 (17)	2.8789 (13)	152.4 (16)
N2—H22···O4iii	0.849 (17)	2.058 (18)	2.8904 (15)	166.4 (18)
O5—H51···O4iv	0.79 (2)	2.10 (2)	2.8597 (13)	161 (2)
O5—H52···O2i	0.86 (2)	1.85 (2)	2.6845 (13)	163 (2)
C4—H4···O2iv	0.93	2.40	3.3245 (16)	173
C13—H13···O3v	0.93	2.47	3.3083 (17)	150
C6—H6···Cg2vi	0.93	2.72	3.6361 (14)	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O2i	0.862 (17)	2.087 (17)	2.8789 (13)	152.4 (16)
N2—H22⋯O4ii	0.849 (17)	2.058 (18)	2.8904 (15)	166.4 (18)
O5—H51⋯O4iii	0.79 (2)	2.10 (2)	2.8597 (13)	161 (2)
O5—H52⋯O2iv	0.86 (2)	1.85 (2)	2.6845 (13)	163 (2)
C4—H4⋯O2iii	0.93	2.40	3.3245 (16)	173
C13—H13⋯O3v	0.93	2.47	3.3083 (17)	150
C6—H6⋯Cg2vi	0.93	2.72	3.6361 (14)	167

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