Diaqua-bis-[4-(dimethyl-amino)-benzoato-κO]bis-(nicotinamide-κN)zinc(II) dihydrate.

In the centrosymmetric title structure, [Zn(C(9)H(10)NO(2))(2)(C(6)H(6)N(2)O)(2)(H(2)O)(2)]·2H(2)O, the Zn(II) cation, located on an inversion center, is coordinated by two 4-(methyl-amino)-benzoate anions, two nicotinamide ligands and two water mol-ecules in a slightly distorted octa-hedral geometry. The dihedral angle between the carboxyl-ate group and the attached benzene ring is 3.09 (9)°, while the pyridine and benzene rings are oriented at a dihedral angle of 77.10 (4)°. The uncoordinated water mol-ecule is linked to nicotinamide ligands by O-H⋯O hydrogen bonds. In the crystal, inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. A weak N-H⋯π inter-action also occurs.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1996 ▶, 2009a ▶,b ▶,c ▶); Hökelek & Necefoğlu (1998 ▶); Necefoğlu et al. (2010a ▶,b ▶).

Experimental

Crystal data

[Zn(C9H10NO2)2(C6H6N2O)2(H2O)2]·2H2O

M = 710.07

Triclinic,

a = 8.1810 (2) Å

b = 9.9877 (2) Å

c = 10.1982 (3) Å

α = 76.141 (2)°

β = 88.894 (3)°

γ = 78.200 (2)°

V = 791.55 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.84 mm−1

T = 100 K

0.40 × 0.24 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.783, T max = 0.856

14586 measured reflections

3975 independent reflections

3725 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 1.05

3975 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.21 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 publication routines (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046854/xu5088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046854/xu5088Isup2.hkl

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

[Zn(C9H10NO2)2(C6H6N2O)2(H2O)2]·2H2O	Z = 1
Mr = 710.07	F(000) = 372
Triclinic, P1	Dx = 1.490 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1810 (2) Å	Cell parameters from 7854 reflections
b = 9.9877 (2) Å	θ = 2.6–28.4°
c = 10.1982 (3) Å	µ = 0.84 mm−1
α = 76.141 (2)°	T = 100 K
β = 88.894 (3)°	Block, colorless
γ = 78.200 (2)°	0.40 × 0.24 × 0.18 mm
V = 791.55 (4) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	3975 independent reflections
Radiation source: fine-focus sealed tube	3725 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.783, Tmax = 0.856	k = −13→13
14586 measured reflections	l = −13→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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0322P)2 + 0.2491P] where P = (Fo2 + 2Fc2)/3
3975 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.21 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	0.02409 (7)
O1	0.14766 (12)	−0.13955 (9)	0.15299 (10)	0.0301 (2)
O2	0.01781 (15)	−0.12085 (10)	0.34423 (11)	0.0406 (3)
O3	0.22843 (14)	0.63006 (10)	−0.11818 (13)	0.0428 (3)
O4	0.16532 (13)	−0.08200 (11)	−0.14162 (11)	0.0305 (2)
H41	0.128 (3)	−0.035 (2)	−0.211 (2)	0.057 (6)*
H42	0.179 (3)	−0.165 (2)	−0.138 (2)	0.052 (6)*
O5	−0.1009 (2)	−0.13619 (14)	0.61334 (15)	0.0543 (3)
H51	−0.070 (3)	−0.136 (3)	0.533 (3)	0.083 (9)*
H52	−0.086 (3)	−0.063 (3)	0.628 (2)	0.069 (7)*
N1	0.15651 (14)	0.15584 (11)	−0.00723 (11)	0.0266 (2)
N2	0.00655 (17)	0.58552 (13)	−0.21424 (13)	0.0355 (3)
H21	−0.027 (2)	0.671 (2)	−0.2554 (18)	0.040 (5)*
H22	−0.047 (2)	0.529 (2)	−0.2306 (19)	0.041 (5)*
N3	0.45941 (17)	−0.75023 (13)	0.50923 (14)	0.0395 (3)
C1	0.11626 (17)	−0.18927 (13)	0.27526 (13)	0.0272 (3)
C2	0.20133 (16)	−0.33741 (13)	0.33617 (13)	0.0261 (3)
C3	0.31531 (17)	−0.41206 (14)	0.26313 (14)	0.0314 (3)
H3	0.3353	−0.3688	0.1746	0.038*
C4	0.39964 (18)	−0.54815 (15)	0.31784 (15)	0.0341 (3)
H4	0.4749	−0.5949	0.2659	0.041*
C5	0.37268 (17)	−0.61713 (13)	0.45193 (14)	0.0300 (3)
C6	0.2540 (2)	−0.54300 (15)	0.52383 (15)	0.0373 (3)
H6	0.2304	−0.5866	0.6114	0.045*
C7	0.1715 (2)	−0.40668 (15)	0.46724 (14)	0.0347 (3)
H7	0.0943	−0.3600	0.5178	0.042*
C8	0.5794 (3)	−0.82465 (18)	0.4327 (2)	0.0539 (5)
H8A	0.6301	−0.9151	0.4886	0.081*
H8B	0.6640	−0.7712	0.4028	0.081*
H8C	0.5241	−0.8373	0.3557	0.081*
C9	0.4290 (2)	−0.82016 (16)	0.64594 (18)	0.0481 (4)
H9A	0.5045	−0.9100	0.6712	0.072*
H9B	0.3160	−0.8336	0.6515	0.072*
H9C	0.4464	−0.7633	0.7061	0.072*
C10	0.10521 (16)	0.29304 (13)	−0.06636 (13)	0.0254 (2)
H10	−0.0026	0.3238	−0.1040	0.030*
C11	0.20513 (16)	0.39157 (13)	−0.07418 (13)	0.0255 (2)
C12	0.36499 (18)	0.34448 (15)	−0.01643 (16)	0.0333 (3)
H12	0.4347	0.4076	−0.0181	0.040*
C13	0.41990 (18)	0.20295 (16)	0.04360 (17)	0.0384 (3)
H13	0.5273	0.1692	0.0816	0.046*
C14	0.31197 (18)	0.11262 (14)	0.04593 (15)	0.0335 (3)
H14	0.3491	0.0174	0.0863	0.040*
C15	0.14646 (17)	0.54593 (13)	−0.13868 (14)	0.0290 (3)

	U11	U22	U33	U12	U13	U23
Zn1	0.02776 (11)	0.01681 (10)	0.02584 (11)	−0.00591 (7)	−0.00232 (8)	−0.00020 (7)
O1	0.0319 (5)	0.0245 (4)	0.0288 (5)	−0.0056 (4)	−0.0030 (4)	0.0035 (4)
O2	0.0583 (7)	0.0255 (5)	0.0311 (5)	0.0038 (4)	0.0011 (5)	−0.0040 (4)
O3	0.0468 (6)	0.0225 (5)	0.0621 (7)	−0.0132 (4)	0.0022 (5)	−0.0111 (5)
O4	0.0348 (5)	0.0206 (4)	0.0342 (6)	−0.0030 (4)	−0.0019 (4)	−0.0046 (4)
O5	0.0850 (10)	0.0309 (6)	0.0437 (8)	−0.0101 (6)	−0.0006 (7)	−0.0043 (5)
N1	0.0290 (5)	0.0203 (5)	0.0297 (6)	−0.0068 (4)	−0.0013 (4)	−0.0029 (4)
N2	0.0466 (7)	0.0213 (5)	0.0367 (7)	−0.0077 (5)	−0.0003 (5)	−0.0024 (5)
N3	0.0471 (7)	0.0252 (6)	0.0382 (7)	0.0033 (5)	−0.0064 (6)	−0.0005 (5)
C1	0.0325 (6)	0.0206 (5)	0.0275 (6)	−0.0065 (5)	−0.0063 (5)	−0.0023 (5)
C2	0.0303 (6)	0.0206 (5)	0.0255 (6)	−0.0049 (5)	−0.0032 (5)	−0.0017 (5)
C3	0.0349 (7)	0.0297 (6)	0.0254 (6)	−0.0046 (5)	0.0014 (5)	−0.0003 (5)
C4	0.0359 (7)	0.0300 (7)	0.0316 (7)	0.0012 (5)	0.0029 (5)	−0.0050 (5)
C5	0.0329 (7)	0.0224 (6)	0.0320 (7)	−0.0036 (5)	−0.0062 (5)	−0.0025 (5)
C6	0.0497 (9)	0.0280 (7)	0.0263 (7)	−0.0015 (6)	0.0031 (6)	0.0030 (5)
C7	0.0440 (8)	0.0270 (6)	0.0273 (7)	0.0007 (6)	0.0048 (6)	−0.0023 (5)
C8	0.0595 (11)	0.0315 (8)	0.0609 (11)	0.0102 (7)	−0.0030 (9)	−0.0085 (7)
C9	0.0647 (11)	0.0267 (7)	0.0436 (9)	−0.0036 (7)	−0.0102 (8)	0.0054 (6)
C10	0.0279 (6)	0.0217 (5)	0.0267 (6)	−0.0062 (5)	0.0004 (5)	−0.0050 (5)
C11	0.0320 (6)	0.0212 (5)	0.0254 (6)	−0.0085 (5)	0.0062 (5)	−0.0076 (5)
C12	0.0322 (7)	0.0300 (6)	0.0423 (8)	−0.0145 (5)	0.0037 (6)	−0.0110 (6)
C13	0.0299 (7)	0.0349 (7)	0.0494 (9)	−0.0081 (6)	−0.0076 (6)	−0.0067 (6)
C14	0.0325 (7)	0.0240 (6)	0.0409 (8)	−0.0053 (5)	−0.0053 (6)	−0.0016 (5)
C15	0.0373 (7)	0.0209 (6)	0.0304 (7)	−0.0086 (5)	0.0107 (5)	−0.0078 (5)

Zn1—O1	2.0442 (9)	C3—C4	1.3795 (19)
Zn1—O1i	2.0442 (9)	C3—H3	0.9300
Zn1—O4	2.1503 (11)	C4—H4	0.9300
Zn1—O4i	2.1503 (11)	C5—C4	1.411 (2)
Zn1—N1	2.1963 (10)	C5—C6	1.403 (2)
Zn1—N1i	2.1963 (10)	C6—H6	0.9300
O1—C1	1.2691 (16)	C7—C6	1.3802 (19)
O2—C1	1.2624 (17)	C7—H7	0.9300
O3—C15	1.2327 (17)	C8—H8A	0.9600
O4—H41	0.78 (2)	C8—H8B	0.9600
O4—H42	0.81 (2)	C8—H8C	0.9600
O5—H51	0.85 (3)	C9—H9A	0.9600
O5—H52	0.81 (3)	C9—H9B	0.9600
N1—C10	1.3402 (15)	C9—H9C	0.9600
N1—C14	1.3371 (17)	C10—C11	1.3900 (17)
N2—C15	1.3279 (19)	C10—H10	0.9300
N2—H21	0.845 (19)	C11—C12	1.3871 (19)
N2—H22	0.829 (19)	C12—C13	1.382 (2)
N3—C5	1.3675 (17)	C12—H12	0.9300
N3—C8	1.440 (2)	C13—H13	0.9300
N3—C9	1.444 (2)	C14—C13	1.3816 (19)
C1—C2	1.4881 (17)	C14—H14	0.9300
C2—C3	1.3911 (19)	C15—C11	1.5045 (17)
C2—C7	1.3923 (19)
O1i—Zn1—O1	180.00 (9)	C5—C4—H4	119.7
O1—Zn1—O4	88.47 (4)	N3—C5—C4	121.30 (13)
O1i—Zn1—O4	91.53 (4)	N3—C5—C6	121.57 (13)
O1—Zn1—O4i	91.53 (4)	C6—C5—C4	117.13 (12)
O1i—Zn1—O4i	88.47 (4)	C5—C6—H6	119.4
O1—Zn1—N1	90.96 (4)	C7—C6—C5	121.30 (13)
O1i—Zn1—N1	89.04 (4)	C7—C6—H6	119.4
O1—Zn1—N1i	89.04 (4)	C2—C7—H7	119.2
O1i—Zn1—N1i	90.96 (4)	C6—C7—C2	121.51 (14)
O4—Zn1—O4i	180.00 (8)	C6—C7—H7	119.2
O4—Zn1—N1	87.36 (4)	N3—C8—H8A	109.5
O4i—Zn1—N1	92.64 (4)	N3—C8—H8B	109.5
O4—Zn1—N1i	92.64 (4)	N3—C8—H8C	109.5
O4i—Zn1—N1i	87.36 (4)	H8A—C8—H8B	109.5
N1i—Zn1—N1	180.0	H8A—C8—H8C	109.5
C1—O1—Zn1	130.87 (9)	H8B—C8—H8C	109.5
Zn1—O4—H41	102.7 (16)	N3—C9—H9A	109.5
Zn1—O4—H42	117.8 (15)	N3—C9—H9B	109.5
H42—O4—H41	113 (2)	N3—C9—H9C	109.5
H52—O5—H51	106 (2)	H9A—C9—H9B	109.5
C10—N1—Zn1	122.97 (8)	H9A—C9—H9C	109.5
C14—N1—Zn1	119.13 (8)	H9B—C9—H9C	109.5
C14—N1—C10	117.87 (11)	N1—C10—C11	123.24 (12)
C15—N2—H21	120.5 (12)	N1—C10—H10	118.4
C15—N2—H22	123.3 (13)	C11—C10—H10	118.4
H21—N2—H22	115.9 (17)	C10—C11—C15	123.17 (12)
C5—N3—C8	120.47 (14)	C12—C11—C10	117.79 (11)
C5—N3—C9	120.68 (14)	C12—C11—C15	119.02 (11)
C8—N3—C9	118.82 (13)	C11—C12—H12	120.3
O1—C1—C2	116.26 (12)	C13—C12—C11	119.49 (12)
O2—C1—O1	123.66 (11)	C13—C12—H12	120.3
O2—C1—C2	120.08 (12)	C12—C13—H13	120.7
C3—C2—C1	120.65 (12)	C14—C13—C12	118.62 (13)
C3—C2—C7	117.35 (12)	C14—C13—H13	120.7
C7—C2—C1	122.00 (12)	N1—C14—C13	122.98 (12)
C2—C3—H3	118.9	N1—C14—H14	118.5
C4—C3—C2	122.10 (13)	C13—C14—H14	118.5
C4—C3—H3	118.9	O3—C15—N2	122.89 (13)
C3—C4—C5	120.56 (13)	O3—C15—C11	119.01 (13)
C3—C4—H4	119.7	N2—C15—C11	118.10 (12)
O4—Zn1—O1—C1	−158.28 (11)	O1—C1—C2—C7	−176.86 (13)
O4i—Zn1—O1—C1	21.72 (11)	O2—C1—C2—C3	−177.34 (13)
N1—Zn1—O1—C1	114.39 (11)	O2—C1—C2—C7	2.4 (2)
N1i—Zn1—O1—C1	−65.61 (11)	C1—C2—C3—C4	178.22 (13)
O1—Zn1—N1—C14	19.82 (11)	C7—C2—C3—C4	−1.5 (2)
O1i—Zn1—N1—C14	−160.18 (11)	C1—C2—C7—C6	−178.48 (14)
O1—Zn1—N1—C10	−162.18 (11)	C3—C2—C7—C6	1.3 (2)
O1i—Zn1—N1—C10	17.82 (11)	C2—C3—C4—C5	−0.1 (2)
O4—Zn1—N1—C10	109.39 (11)	N3—C5—C4—C3	−177.74 (14)
O4i—Zn1—N1—C10	−70.61 (11)	C6—C5—C4—C3	1.9 (2)
O4—Zn1—N1—C14	−68.60 (11)	N3—C5—C6—C7	177.47 (15)
O4i—Zn1—N1—C14	111.40 (11)	C4—C5—C6—C7	−2.2 (2)
Zn1—O1—C1—O2	−33.61 (19)	C2—C7—C6—C5	0.6 (2)
Zn1—O1—C1—C2	145.62 (9)	N1—C10—C11—C12	−0.6 (2)
Zn1—N1—C10—C11	−178.36 (9)	N1—C10—C11—C15	−179.02 (12)
C14—N1—C10—C11	−0.3 (2)	C10—C11—C12—C13	1.3 (2)
Zn1—N1—C14—C13	178.79 (12)	C15—C11—C12—C13	179.73 (14)
C10—N1—C14—C13	0.7 (2)	C11—C12—C13—C14	−1.0 (2)
C8—N3—C5—C4	−1.0 (2)	N1—C14—C13—C12	0.0 (3)
C8—N3—C5—C6	179.36 (15)	O3—C15—C11—C10	165.58 (13)
C9—N3—C5—C4	−179.22 (15)	O3—C15—C11—C12	−12.8 (2)
C9—N3—C5—C6	1.1 (2)	N2—C15—C11—C10	−13.6 (2)
O1—C1—C2—C3	3.40 (18)	N2—C15—C11—C12	168.04 (13)

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O5ii	0.85 (2)	2.05 (2)	2.8826 (19)	169.3 (2)
O4—H41···O2iii	0.78 (2)	2.00 (2)	2.7370 (16)	159 (2)
O4—H42···O3iv	0.81 (2)	1.96 (2)	2.7681 (15)	175.1 (2)
O5—H51···O2	0.85 (3)	2.02 (3)	2.8732 (19)	174 (3)
O5—H52···O2v	0.81 (3)	2.11 (3)	2.9150 (18)	173 (2)
C13—H13···O4vi	0.93	2.52	3.4422 (19)	170
N2—H22···Cg1iii	0.829 (19)	2.79 (2)	3.5200 (15)	147.9 (2)

Table 1

Selected bond lengths (Å)

Zn1—O1	2.0442 (9)
Zn1—O4	2.1503 (11)
Zn1—N1	2.1963 (10)

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O5i	0.85 (2)	2.05 (2)	2.8826 (19)	169.3 (2)
O4—H41⋯O2ii	0.78 (2)	2.00 (2)	2.7370 (16)	159 (2)
O4—H42⋯O3iii	0.81 (2)	1.96 (2)	2.7681 (15)	175.1 (2)
O5—H51⋯O2	0.85 (3)	2.02 (3)	2.8732 (19)	174 (3)
O5—H52⋯O2iv	0.81 (3)	2.11 (3)	2.9150 (18)	173 (2)
C13—H13⋯O4v	0.93	2.52	3.4422 (19)	170
N2—H22⋯Cg1ii	0.829 (19)	2.79 (2)	3.5200 (15)	147.9 (2)

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