Methyl 4-isonicotinamido-benzoate monohydrate.

The title compound, C(14)H(12)N(2)O(3)·H(2)O, synthesized by the reaction of methyl 4-amino-benzoate with isonicotinoyl chloride hydro-chloride, is relatively planar, with the pyridine ring being inclined by 7.46 (7)° to the benzene ring. In the crystal, the methyl 4-isonicotinamido-benzoate mol-ecules are inter-linked by water mol-ecules via N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, leading to the formation of a double-chain ribbon-like structure.

Related literature

For the synthesis of methyl 4-amino­benzoate and isonicotinoyl chloride hydro­chloride, see: Margiotta et al. (2008 ▶). For the use of such ligands in coordination chemistry, see: Saeed et al. (2010 ▶); Kitagawa (2005 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12N2O3·H2O

M = 274.27

Triclinic,

a = 6.8836 (3) Å

b = 8.8810 (4) Å

c = 10.9658 (5) Å

α = 96.062 (1)°

β = 90.896 (1)°

γ = 95.854 (1)°

V = 662.91 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.48 × 0.37 × 0.27 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.973

7689 measured reflections

2318 independent reflections

1968 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.102

S = 1.06

2318 reflections

181 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024979/su2171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024979/su2171Isup2.hkl

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

C14H12N2O3·H2O	Z = 2
Mr = 274.27	F(000) = 288
Triclinic, P1	Dx = 1.374 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8836 (3) Å	Cell parameters from 4652 reflections
b = 8.8810 (4) Å	θ = 2.3–28.3°
c = 10.9658 (5) Å	µ = 0.10 mm−1
α = 96.062 (1)°	T = 296 K
β = 90.896 (1)°	Block, colourless
γ = 95.854 (1)°	0.48 × 0.37 × 0.27 mm
V = 662.91 (5) Å3

Bruker SMART 1K CCD area-detector diffractometer	2318 independent reflections
Radiation source: fine-focus sealed tube	1968 reflections with I > 2σ(I)
graphite	Rint = 0.015
Detector resolution: 8.192 pixels mm-1	θmax = 25.0°, θmin = 1.9°
thin–slice ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.952, Tmax = 0.973	l = −13→12
7689 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0526P)2 + 0.1234P] where P = (Fo2 + 2Fc2)/3
2318 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.14 e Å−3
3 restraints	Δρmin = −0.16 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 > 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
N1	0.02099 (15)	0.81758 (12)	0.39503 (10)	0.0431 (3)
H1A	−0.0956	0.7830	0.3698	0.052*
N2	−0.34705 (19)	0.52096 (14)	0.70330 (12)	0.0576 (3)
O3	0.61235 (16)	1.21607 (13)	0.08752 (10)	0.0623 (3)
O2	0.33143 (18)	1.24867 (15)	−0.00513 (11)	0.0772 (4)
O1	0.23987 (15)	0.81573 (15)	0.55168 (10)	0.0713 (4)
O1W	0.30526 (15)	1.33795 (13)	−0.24537 (9)	0.0662 (3)
H1WA	0.4223	1.3964	−0.2516	0.099*
H1WB	0.3142	1.3192	−0.1677	0.099*
C1	0.7154 (3)	1.3157 (2)	0.00895 (17)	0.0722 (5)
H1B	0.8527	1.3251	0.0290	0.108*
H1C	0.6685	1.4142	0.0207	0.108*
H1D	0.6937	1.2740	−0.0751	0.108*
C2	0.4195 (2)	1.19167 (16)	0.07065 (12)	0.0507 (4)
C3	0.3244 (2)	1.08944 (15)	0.15573 (11)	0.0440 (3)
C4	0.1229 (2)	1.05719 (15)	0.14751 (12)	0.0480 (3)
H4A	0.0521	1.0974	0.0881	0.058*
C5	0.0271 (2)	0.96663 (15)	0.22619 (12)	0.0462 (3)
H5A	−0.1079	0.9452	0.2192	0.055*
C6	0.13107 (19)	0.90658 (14)	0.31652 (11)	0.0397 (3)
C7	0.3329 (2)	0.93699 (16)	0.32434 (12)	0.0467 (3)
H7A	0.4041	0.8963	0.3833	0.056*
C8	0.4280 (2)	1.02781 (16)	0.24441 (13)	0.0479 (3)
H8A	0.5633	1.0479	0.2501	0.057*
C9	0.07765 (19)	0.78029 (15)	0.50566 (12)	0.0442 (3)
C10	−0.07614 (19)	0.69056 (14)	0.57202 (11)	0.0408 (3)
C11	−0.2737 (2)	0.69375 (16)	0.55336 (12)	0.0483 (3)
H11A	−0.3201	0.7522	0.4959	0.058*
C12	−0.4020 (2)	0.60887 (18)	0.62121 (14)	0.0573 (4)
H12A	−0.5351	0.6136	0.6086	0.069*
C13	−0.1559 (2)	0.51992 (17)	0.72155 (14)	0.0566 (4)
H13A	−0.1137	0.4597	0.7790	0.068*
C14	−0.0171 (2)	0.60287 (16)	0.66023 (13)	0.0515 (4)
H14A	0.1151	0.6002	0.6778	0.062*

	U11	U22	U33	U12	U13	U23
N1	0.0379 (6)	0.0495 (6)	0.0418 (6)	−0.0031 (5)	−0.0043 (4)	0.0129 (5)
N2	0.0608 (8)	0.0573 (7)	0.0527 (7)	−0.0070 (6)	0.0120 (6)	0.0074 (6)
O3	0.0606 (7)	0.0702 (7)	0.0580 (6)	−0.0041 (5)	0.0084 (5)	0.0254 (5)
O2	0.0824 (9)	0.0973 (9)	0.0553 (7)	−0.0071 (7)	−0.0077 (6)	0.0408 (6)
O1	0.0464 (6)	0.1138 (10)	0.0532 (6)	−0.0184 (6)	−0.0125 (5)	0.0349 (6)
O1W	0.0574 (6)	0.0887 (8)	0.0504 (6)	−0.0217 (6)	−0.0132 (5)	0.0287 (5)
C1	0.0783 (12)	0.0701 (11)	0.0688 (11)	−0.0096 (9)	0.0164 (9)	0.0245 (8)
C2	0.0648 (9)	0.0515 (8)	0.0351 (7)	−0.0004 (7)	0.0007 (6)	0.0076 (6)
C3	0.0542 (8)	0.0438 (7)	0.0331 (6)	0.0004 (6)	0.0002 (6)	0.0052 (5)
C4	0.0552 (8)	0.0509 (8)	0.0383 (7)	0.0027 (6)	−0.0103 (6)	0.0115 (6)
C5	0.0428 (7)	0.0516 (8)	0.0441 (7)	0.0010 (6)	−0.0069 (6)	0.0097 (6)
C6	0.0432 (7)	0.0388 (6)	0.0369 (6)	0.0018 (5)	−0.0015 (5)	0.0053 (5)
C7	0.0429 (7)	0.0545 (8)	0.0457 (7)	0.0061 (6)	−0.0028 (6)	0.0183 (6)
C8	0.0420 (7)	0.0565 (8)	0.0461 (7)	0.0018 (6)	0.0008 (6)	0.0134 (6)
C9	0.0410 (7)	0.0512 (7)	0.0401 (7)	0.0001 (6)	−0.0036 (5)	0.0090 (6)
C10	0.0428 (7)	0.0423 (7)	0.0365 (6)	0.0013 (5)	0.0017 (5)	0.0034 (5)
C11	0.0458 (8)	0.0580 (8)	0.0414 (7)	0.0048 (6)	−0.0005 (6)	0.0076 (6)
C12	0.0429 (8)	0.0741 (10)	0.0522 (8)	−0.0028 (7)	0.0048 (6)	0.0027 (7)
C13	0.0642 (10)	0.0536 (8)	0.0553 (9)	0.0076 (7)	0.0097 (7)	0.0193 (7)
C14	0.0473 (8)	0.0592 (8)	0.0513 (8)	0.0093 (6)	0.0046 (6)	0.0180 (7)

N1—C9	1.3528 (17)	C4—C5	1.3721 (19)
N1—C6	1.4078 (16)	C4—H4A	0.9300
N1—H1A	0.8600	C5—C6	1.3946 (17)
N2—C12	1.327 (2)	C5—H5A	0.9300
N2—C13	1.329 (2)	C6—C7	1.3879 (18)
O3—C2	1.3296 (18)	C7—C8	1.3807 (19)
O3—C1	1.4422 (17)	C7—H7A	0.9300
O2—C2	1.2043 (18)	C8—H8A	0.9300
O1—C9	1.2156 (16)	C9—C10	1.5032 (18)
O1W—H1WA	0.9207	C10—C11	1.3758 (19)
O1W—H1WB	0.8877	C10—C14	1.3853 (19)
C1—H1B	0.9600	C11—C12	1.380 (2)
C1—H1C	0.9600	C11—H11A	0.9300
C1—H1D	0.9600	C12—H12A	0.9300
C2—O2	1.2043 (18)	C13—C14	1.375 (2)
C2—C3	1.4833 (19)	C13—H13A	0.9300
C3—C4	1.387 (2)	C14—H14A	0.9300
C3—C8	1.3871 (19)
C9—N1—C6	127.41 (11)	C7—C6—C5	119.24 (12)
C9—N1—H1A	116.3	C7—C6—N1	124.08 (11)
C6—N1—H1A	116.3	C5—C6—N1	116.69 (11)
C12—N2—C13	116.54 (12)	C8—C7—C6	119.91 (12)
C2—O3—C1	116.54 (13)	C8—C7—H7A	120.0
O2—O2—C2	0(10)	C6—C7—H7A	120.0
H1WA—O1W—H1WB	100.2	C7—C8—C3	120.88 (13)
O3—C1—H1B	109.5	C7—C8—H8A	119.6
O3—C1—H1C	109.5	C3—C8—H8A	119.6
H1B—C1—H1C	109.5	O1—C9—N1	124.09 (12)
O3—C1—H1D	109.5	O1—C9—C10	120.49 (12)
H1B—C1—H1D	109.5	N1—C9—C10	115.42 (11)
H1C—C1—H1D	109.5	C11—C10—C14	117.50 (12)
O2—C2—O2	0.00 (10)	C11—C10—C9	123.90 (12)
O2—C2—O3	123.17 (13)	C14—C10—C9	118.56 (12)
O2—C2—O3	123.17 (13)	C10—C11—C12	118.98 (13)
O2—C2—C3	123.63 (14)	C10—C11—H11A	120.5
O2—C2—C3	123.63 (14)	C12—C11—H11A	120.5
O3—C2—C3	113.20 (12)	N2—C12—C11	123.99 (14)
C4—C3—C8	118.92 (12)	N2—C12—H12A	118.0
C4—C3—C2	118.31 (12)	C11—C12—H12A	118.0
C8—C3—C2	122.76 (13)	N2—C13—C14	123.67 (14)
C5—C4—C3	120.67 (12)	N2—C13—H13A	118.2
C5—C4—H4A	119.7	C14—C13—H13A	118.2
C3—C4—H4A	119.7	C13—C14—C10	119.26 (13)
C4—C5—C6	120.37 (12)	C13—C14—H14A	120.4
C4—C5—H5A	119.8	C10—C14—H14A	120.4
C6—C5—H5A	119.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1Wi	0.86	2.10	2.9014 (14)	155
O1W—H1WA···N2ii	0.92	1.94	2.8510 (16)	169
O1W—H1WB···O2	0.89	1.96	2.8385 (14)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1Wi	0.86	2.10	2.9014 (14)	155
O1W—H1WA⋯N2ii	0.92	1.94	2.8510 (16)	169
O1W—H1WB⋯O2	0.89	1.96	2.8385 (14)	172

Symmetry codes: (i) ; (ii) .