catena-Poly[[(4-formyl-benzoato-κO)(isonicotinamide-κN)zinc(II)]-μ-4-formyl-benzoato-κO:O].

In the title compound, [Zn(C(8)H(5)O(3))(2)(C(6)H(6)N(2)O)](n), the Zn(II) ion is tetrahedrally coordinated by two formyl-benzoate (FB) and one isonicotinamide (INA) ligands while symmetry-related FB ligands bridge adjacent Zn(II) ions, forming polymeric chains along the b axis. The carboxyl-ate groups in the two FB ions are twisted away from the attached benzene ring by 9.07 (2) and 26.2 (2)°. The two benzene rings of the FB ions are oriented at a dihedral angle of 81.30 (5)°. In the crystal, adjacent polymeric chains inter-act via N-H⋯O and C-H⋯O hydrogen bonds, π-π contacts between the formyl-benzoate rings [centroid-centroid distance = 3.7736 (8) Å] and weak C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For general background to niacin, see: Krishnamachari (1974 ▶). For the crystal structure of n class="Chemical">N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek & Necefoğlu (1996 ▶); Hökelek et al. (2009 ▶).

Experimental

Crystal data

[Zn(C8H5O3)2(C6n class="Species">H6N2O)]

M = 485.74

Monoclinic,

a = 13.3143 (2) Å

b = 6.7857 (1) Å

c = 21.3927 (3) Å

β = 91.458 (1)°

V = 1932.14 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.32 mm−1

T = 100 K

0.22 × 0.12 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.829, T max = 0.903

17841 measured reflections

4812 independent reflections

4086 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.080

S = 1.10

4812 reflections

297 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.39 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 datablocks I, global. DOI: 10.1107/S160053680904241X/ci2939sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904241X/ci2939Isup2.hkl

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

[Zn(C8H5O3)2(C6H6N2O)]	F(000) = 992
Mr = 485.74	Dx = 1.670 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9448 reflections
a = 13.3143 (2) Å	θ = 3.1–28.4°
b = 6.7857 (1) Å	µ = 1.32 mm−1
c = 21.3927 (3) Å	T = 100 K
β = 91.458 (1)°	Needle, colourless
V = 1932.14 (5) Å3	0.22 × 0.12 × 0.08 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	4812 independent reflections
Radiation source: fine-focus sealed tube	4086 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→14
Tmin = 0.829, Tmax = 0.903	k = −8→9
17841 measured reflections	l = −28→28

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.0092P] where P = (Fo2 + 2Fc2)/3
4812 reflections	(Δ/σ)max = 0.001
297 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.816160 (13)	0.51300 (2)	0.187880 (8)	0.01058 (7)
O1	0.95052 (8)	0.60767 (16)	0.20123 (5)	0.0149 (2)
O2	1.00643 (8)	0.55706 (16)	0.10502 (5)	0.0149 (2)
O3	0.77863 (8)	0.37932 (15)	0.26575 (5)	0.0134 (2)
O4	0.70741 (8)	0.67550 (14)	0.15404 (5)	0.0137 (2)
O5	0.83582 (11)	−0.07543 (19)	−0.07713 (6)	0.0312 (3)
O6	1.49773 (9)	0.61367 (17)	0.23858 (5)	0.0199 (3)
O7	1.10801 (11)	0.97953 (16)	0.45862 (6)	0.0236 (3)
N1	0.81632 (9)	0.29546 (17)	0.12295 (6)	0.0112 (3)
N2	0.91501 (11)	−0.28715 (18)	−0.01158 (6)	0.0182 (3)
H2A	0.9269	−0.3695	−0.0410	0.022*
H2B	0.9348	−0.3125	0.0262	0.022*
C1	1.02044 (11)	0.5821 (2)	0.16202 (7)	0.0110 (3)
C2	1.12564 (11)	0.5862 (2)	0.18971 (7)	0.0109 (3)
C3	1.14051 (12)	0.5879 (2)	0.25423 (7)	0.0126 (3)
H3	1.0857	0.5867	0.2803	0.015*
C4	1.23802 (12)	0.5913 (2)	0.27978 (7)	0.0131 (3)
H4	1.2487	0.5906	0.3229	0.016*
C5	1.31866 (11)	0.5957 (2)	0.24033 (7)	0.0122 (3)
C6	1.30379 (12)	0.5942 (2)	0.17551 (7)	0.0143 (3)
H6	1.3585	0.5979	0.1494	0.017*
C7	1.20746 (12)	0.5872 (2)	0.15043 (7)	0.0134 (3)
H7	1.1971	0.5832	0.1073	0.016*
C8	0.81930 (11)	0.3293 (2)	0.31722 (7)	0.0115 (3)
C9	0.89783 (12)	0.4527 (2)	0.34954 (7)	0.0114 (3)
C10	0.96360 (12)	0.3649 (2)	0.39317 (7)	0.0149 (3)
H10	0.9603	0.2299	0.4004	0.018*
C11	1.03354 (13)	0.4785 (2)	0.42548 (8)	0.0162 (3)
H11	1.0792	0.4188	0.4531	0.019*
C12	1.03609 (12)	0.6823 (2)	0.41700 (7)	0.0140 (3)
C13	0.97104 (12)	0.7698 (2)	0.37288 (7)	0.0138 (3)
H13	0.9730	0.9053	0.3666	0.017*
C14	0.90409 (12)	0.6556 (2)	0.33872 (7)	0.0122 (3)
H14	0.8627	0.7138	0.3083	0.015*
C15	0.86757 (11)	0.1289 (2)	0.13520 (7)	0.0125 (3)
H15	0.8924	0.1074	0.1757	0.015*
C16	0.88489 (13)	−0.0119 (2)	0.09003 (8)	0.0139 (3)
H16	0.9213	−0.1251	0.1000	0.017*
C17	0.84719 (12)	0.0179 (2)	0.02948 (8)	0.0126 (3)
C18	0.79165 (12)	0.1872 (2)	0.01756 (7)	0.0147 (3)
H18	0.7639	0.2097	−0.0221	0.018*
C19	0.77770 (12)	0.3220 (2)	0.06473 (7)	0.0136 (3)
H19	0.7404	0.4350	0.0561	0.016*
C20	0.86597 (12)	−0.1204 (2)	−0.02441 (7)	0.0157 (3)
C21	1.42128 (13)	0.6036 (2)	0.26818 (8)	0.0161 (3)
H21	1.4266 (13)	0.600 (3)	0.3157 (9)	0.028 (5)*
C22	1.10601 (13)	0.8010 (2)	0.45686 (8)	0.0188 (4)
H22	1.1561 (13)	0.714 (3)	0.4842 (9)	0.020 (5)*

	U11	U22	U33	U12	U13	U23
Zn1	0.01001 (11)	0.01290 (10)	0.00882 (11)	0.00080 (6)	−0.00023 (7)	−0.00111 (6)
O1	0.0092 (6)	0.0225 (6)	0.0129 (5)	−0.0007 (4)	0.0003 (4)	−0.0045 (4)
O2	0.0144 (6)	0.0195 (5)	0.0106 (5)	0.0021 (5)	−0.0019 (5)	−0.0020 (4)
O3	0.0120 (6)	0.0184 (5)	0.0098 (5)	−0.0013 (4)	−0.0021 (4)	0.0016 (4)
O4	0.0134 (6)	0.0141 (5)	0.0135 (5)	0.0030 (4)	−0.0013 (5)	−0.0022 (4)
O5	0.0524 (9)	0.0310 (7)	0.0097 (6)	0.0163 (7)	−0.0092 (6)	−0.0050 (5)
O6	0.0130 (6)	0.0295 (6)	0.0172 (6)	−0.0013 (5)	−0.0005 (5)	0.0005 (5)
O7	0.0279 (8)	0.0248 (6)	0.0181 (7)	−0.0107 (5)	0.0007 (6)	−0.0038 (5)
N1	0.0094 (7)	0.0145 (6)	0.0096 (6)	−0.0011 (5)	−0.0002 (5)	0.0003 (5)
N2	0.0256 (8)	0.0193 (6)	0.0094 (6)	0.0055 (6)	−0.0018 (6)	−0.0037 (5)
C1	0.0111 (8)	0.0103 (6)	0.0115 (7)	0.0008 (6)	−0.0008 (6)	−0.0005 (6)
C2	0.0111 (8)	0.0102 (6)	0.0113 (7)	0.0000 (6)	−0.0016 (6)	0.0001 (6)
C3	0.0128 (8)	0.0145 (7)	0.0106 (7)	0.0009 (6)	0.0017 (6)	0.0001 (6)
C4	0.0164 (8)	0.0143 (7)	0.0085 (7)	0.0000 (6)	−0.0008 (6)	−0.0002 (6)
C5	0.0121 (8)	0.0110 (7)	0.0135 (8)	0.0003 (6)	−0.0016 (6)	0.0002 (6)
C6	0.0113 (8)	0.0190 (7)	0.0127 (7)	−0.0008 (6)	0.0028 (6)	−0.0003 (6)
C7	0.0143 (8)	0.0183 (7)	0.0076 (7)	0.0006 (6)	−0.0008 (6)	0.0006 (6)
C8	0.0096 (8)	0.0138 (7)	0.0113 (7)	0.0029 (6)	0.0015 (6)	−0.0023 (6)
C9	0.0098 (8)	0.0154 (7)	0.0091 (7)	−0.0002 (6)	0.0015 (6)	−0.0020 (6)
C10	0.0173 (9)	0.0137 (7)	0.0137 (8)	0.0002 (6)	−0.0001 (7)	−0.0003 (6)
C11	0.0144 (9)	0.0206 (8)	0.0134 (8)	0.0021 (6)	−0.0043 (7)	−0.0003 (6)
C12	0.0113 (8)	0.0191 (7)	0.0117 (7)	−0.0021 (6)	−0.0004 (6)	−0.0029 (6)
C13	0.0149 (8)	0.0136 (7)	0.0129 (7)	−0.0015 (6)	0.0041 (6)	−0.0024 (6)
C14	0.0111 (8)	0.0164 (7)	0.0090 (7)	0.0020 (6)	0.0012 (6)	0.0004 (6)
C15	0.0116 (8)	0.0171 (7)	0.0087 (7)	0.0004 (6)	−0.0023 (6)	0.0008 (6)
C16	0.0157 (9)	0.0140 (7)	0.0120 (8)	0.0026 (6)	−0.0017 (7)	−0.0003 (5)
C17	0.0147 (8)	0.0143 (7)	0.0088 (8)	−0.0022 (6)	0.0006 (6)	−0.0003 (5)
C18	0.0169 (9)	0.0176 (7)	0.0094 (7)	−0.0006 (6)	−0.0029 (6)	0.0014 (6)
C19	0.0130 (8)	0.0150 (7)	0.0128 (7)	0.0019 (6)	−0.0011 (6)	0.0029 (6)
C20	0.0180 (9)	0.0185 (7)	0.0106 (7)	0.0001 (6)	−0.0013 (7)	−0.0024 (6)
C21	0.0173 (9)	0.0171 (7)	0.0139 (8)	0.0003 (6)	−0.0024 (7)	−0.0003 (6)
C22	0.0174 (9)	0.0260 (8)	0.0131 (8)	−0.0046 (7)	0.0007 (7)	−0.0018 (7)

Zn1—O1	1.9153 (11)	C7—C6	1.378 (2)
Zn1—O3	1.9723 (11)	C7—H7	0.93
Zn1—O4	1.9450 (10)	C8—O4ii	1.2669 (18)
Zn1—N1	2.0270 (12)	C8—C9	1.495 (2)
O1—C1	1.2807 (18)	C9—C10	1.397 (2)
O2—C1	1.2405 (18)	C9—C14	1.3990 (19)
O3—C8	1.2611 (17)	C10—H10	0.93
O4—C8i	1.2669 (18)	C11—C10	1.381 (2)
O5—C20	1.2261 (18)	C11—H11	0.93
O6—C21	1.214 (2)	C12—C11	1.395 (2)
O7—C22	1.2124 (19)	C12—C13	1.397 (2)
N1—C15	1.3427 (18)	C12—C22	1.484 (2)
N1—C19	1.3474 (18)	C13—C14	1.377 (2)
N2—C20	1.332 (2)	C13—H13	0.93
N2—H2A	0.86	C14—H14	0.93
N2—H2B	0.86	C15—H15	0.93
C2—C1	1.507 (2)	C16—C15	1.382 (2)
C2—C3	1.390 (2)	C16—C17	1.392 (2)
C2—C7	1.393 (2)	C16—H16	0.93
C3—C4	1.396 (2)	C18—C17	1.386 (2)
C3—H3	0.93	C18—H18	0.93
C4—H4	0.93	C19—C18	1.378 (2)
C5—C4	1.383 (2)	C19—H19	0.93
C5—C6	1.396 (2)	C20—C17	1.512 (2)
C5—C21	1.478 (2)	C21—H21	1.018 (19)
C6—H6	0.93	C22—H22	1.057 (17)
O1—Zn1—O3	106.50 (4)	C14—C9—C8	121.23 (13)
O1—Zn1—O4	123.30 (5)	C9—C10—H10	120.0
O1—Zn1—N1	109.22 (5)	C11—C10—C9	119.95 (14)
O3—Zn1—N1	104.39 (5)	C11—C10—H10	120.0
O4—Zn1—O3	111.89 (5)	C10—C11—C12	120.45 (15)
O4—Zn1—N1	99.88 (5)	C10—C11—H11	119.8
C1—O1—Zn1	123.27 (10)	C12—C11—H11	119.8
C8—O3—Zn1	138.48 (10)	C11—C12—C13	119.50 (14)
C8i—O4—Zn1	120.13 (10)	C11—C12—C22	118.70 (15)
C15—N1—Zn1	119.26 (10)	C13—C12—C22	121.77 (14)
C15—N1—C19	118.22 (13)	C12—C13—H13	120.0
C19—N1—Zn1	121.95 (10)	C14—C13—C12	120.09 (14)
C20—N2—H2A	120.0	C14—C13—H13	120.0
C20—N2—H2B	120.0	C9—C14—H14	119.8
H2A—N2—H2B	120.0	C13—C14—C9	120.42 (14)
O1—C1—C2	115.07 (13)	C13—C14—H14	119.8
O2—C1—O1	124.67 (14)	N1—C15—C16	122.57 (14)
O2—C1—C2	120.25 (14)	N1—C15—H15	118.7
C3—C2—C1	119.87 (14)	C16—C15—H15	118.7
C3—C2—C7	120.36 (14)	C15—C16—C17	119.19 (14)
C7—C2—C1	119.76 (13)	C15—C16—H16	120.4
C2—C3—C4	119.77 (14)	C17—C16—H16	120.4
C2—C3—H3	120.1	C16—C17—C20	123.82 (13)
C4—C3—H3	120.1	C18—C17—C16	118.00 (14)
C3—C4—H4	120.3	C18—C17—C20	118.16 (14)
C5—C4—C3	119.36 (14)	C17—C18—H18	120.1
C5—C4—H4	120.3	C19—C18—C17	119.77 (14)
C4—C5—C6	120.90 (14)	C19—C18—H18	120.1
C4—C5—C21	118.62 (14)	N1—C19—C18	122.20 (14)
C6—C5—C21	120.48 (14)	N1—C19—H19	118.9
C5—C6—H6	120.2	C18—C19—H19	118.9
C7—C6—C5	119.60 (14)	O5—C20—N2	123.26 (15)
C7—C6—H6	120.2	O5—C20—C17	119.35 (14)
C2—C7—H7	120.0	N2—C20—C17	117.39 (13)
C6—C7—C2	119.98 (14)	O6—C21—C5	124.78 (15)
C6—C7—H7	120.0	O6—C21—H21	119.0 (11)
O3—C8—O4ii	121.72 (14)	C5—C21—H21	116.3 (11)
O3—C8—C9	122.19 (13)	O7—C22—C12	124.98 (17)
O4ii—C8—C9	116.01 (13)	O7—C22—H22	121.9 (9)
C10—C9—C8	119.27 (13)	C12—C22—H22	113.1 (9)
C10—C9—C14	119.45 (14)
O3—Zn1—O1—C1	132.27 (11)	C21—C5—C4—C3	178.69 (13)
O4—Zn1—O1—C1	−96.44 (12)	C4—C5—C6—C7	−0.3 (2)
N1—Zn1—O1—C1	20.07 (13)	C21—C5—C6—C7	−179.85 (14)
O1—Zn1—O3—C8	−6.56 (15)	C4—C5—C21—O6	−177.81 (15)
O4—Zn1—O3—C8	−143.97 (14)	C6—C5—C21—O6	1.7 (2)
N1—Zn1—O3—C8	108.94 (15)	C2—C7—C6—C5	1.5 (2)
O1—Zn1—O4—C8i	−60.90 (13)	O3—C8—C9—C10	−158.23 (15)
O3—Zn1—O4—C8i	68.17 (12)	O3—C8—C9—C14	24.3 (2)
N1—Zn1—O4—C8i	178.16 (11)	O4ii—C8—C9—C10	24.8 (2)
O1—Zn1—N1—C15	62.86 (12)	O4ii—C8—C9—C14	−152.61 (15)
O1—Zn1—N1—C19	−108.32 (12)	C8—C9—C10—C11	−177.06 (15)
O3—Zn1—N1—C15	−50.72 (12)	C14—C9—C10—C11	0.4 (2)
O3—Zn1—N1—C19	138.10 (12)	C8—C9—C14—C13	174.28 (14)
O4—Zn1—N1—C15	−166.53 (11)	C10—C9—C14—C13	−3.2 (2)
O4—Zn1—N1—C19	22.29 (13)	C12—C11—C10—C9	2.9 (3)
Zn1—O1—C1—O2	25.4 (2)	C13—C12—C11—C10	−3.6 (3)
Zn1—O1—C1—C2	−155.21 (9)	C22—C12—C11—C10	174.41 (16)
Zn1—O3—C8—O4ii	−147.48 (12)	C11—C12—C13—C14	0.9 (2)
Zn1—O3—C8—C9	35.8 (2)	C22—C12—C13—C14	−177.08 (15)
Zn1—N1—C15—C16	−169.24 (12)	C11—C12—C22—O7	−171.97 (17)
C19—N1—C15—C16	2.3 (2)	C13—C12—C22—O7	6.0 (3)
Zn1—N1—C19—C18	169.38 (12)	C12—C13—C14—C9	2.5 (2)
C15—N1—C19—C18	−1.9 (2)	C17—C16—C15—N1	−0.7 (2)
C3—C2—C1—O1	9.2 (2)	C15—C16—C17—C18	−1.4 (2)
C3—C2—C1—O2	−171.42 (14)	C15—C16—C17—C20	176.70 (15)
C7—C2—C1—O1	−171.18 (13)	C19—C18—C17—C16	1.7 (2)
C7—C2—C1—O2	8.2 (2)	C19—C18—C17—C20	−176.45 (14)
C1—C2—C3—C4	179.87 (13)	N1—C19—C18—C17	−0.1 (2)
C7—C2—C3—C4	0.2 (2)	N2—C20—C17—C16	5.3 (2)
C1—C2—C7—C6	178.94 (14)	N2—C20—C17—C18	−176.65 (15)
C3—C2—C7—C6	−1.4 (2)	O5—C20—C17—C16	−174.85 (17)
C2—C3—C4—C5	0.9 (2)	O5—C20—C17—C18	3.2 (2)
C6—C5—C4—C3	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2iii	0.86	2.08	2.9242 (17)	165
N2—H2B···O2iv	0.86	2.11	2.9439 (17)	163
C4—H4···O5v	0.93	2.41	3.298 (2)	160
C6—H6···O7vi	0.93	2.50	3.223 (2)	135
C15—H15···O6vi	0.93	2.32	3.2049 (19)	159
C16—H16···O2iv	0.93	2.44	3.3541 (18)	169
C3—H3···Cg1	0.93	2.73	3.6332 (17)	163

Table 1

Selected bond lengths (Å)

Zn1—O1	1.9153 (11)
Zn1—O3	1.9723 (11)
Zn1—O4	1.9450 (10)
Zn1—N1	2.0270 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.08	2.9242 (17)	165
N2—H2B⋯O2ii	0.86	2.11	2.9439 (17)	163
C4—H4⋯O5iii	0.93	2.41	3.298 (2)	160
C6—H6⋯O7iv	0.93	2.50	3.223 (2)	135
C15—H15⋯O6iv	0.93	2.32	3.2049 (19)	159
C16—H16⋯O2ii	0.93	2.44	3.3541 (18)	169
C3—H3⋯Cg1	0.93	2.73	3.6332 (17)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C9–C14 ring.