N′-(4-Hydr­oxy-3-methoxy­benzyl­idene)isonicotinohydrazide monohydrate

Shi, X.-F.; He, L.; Ma, G.-Z.; Yuan, C.-C.

doi:10.1107/S1600536807004874

N′-(4-Hydroxy-3-methoxybenzylidene)isonicotinohydrazide monohydrate

X.-F. Shi, L. He, G.-Z. Ma and C.-C. Yuan

The asymmetric unit of the title compound, C₁₄H₁₃N₃O₃·H₂O, contains one molecule of N′-(4-hydroxy-3-methoxybenzylidene)isonicotinohydrazide and one solvent water molecule. The crystal packing is stabilized by O—H

N and O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004874/bt2252sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004874/bt2252Isup2.hkl Contains datablock I

CCDC reference: 641506

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.002 Å
R factor = 0.039
wR factor = 0.109
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.32

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

N'-(4-Hydroxy-3-methoxybenzylidene)isonicotinohydazide monohydrate top

Crystal data top

C₁₄H₁₅N₃O₄	D_x = 1.393 Mg m⁻³
M_r = 289.29	Melting point = 492–495 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
a = 13.343 (3) Å	Cell parameters from 2280 reflections
b = 6.5277 (13) Å	θ = 2.6–26.3°
c = 16.005 (3) Å	µ = 0.10 mm⁻¹
β = 98.420 (4)°	T = 294 K
V = 1379.0 (5) Å³	Block, colorless
Z = 4	0.26 × 0.20 × 0.18 mm
F(000) = 608

Data collection top

Bruker SMART diffractometer	2826 independent reflections
Radiation source: fine-focus sealed tube	1847 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→14
T_min = 0.973, T_max = 0.982	k = −8→8
7600 measured reflections	l = −14→20

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0492P)² + 0.2925P] where P = (F_o² + 2F_c²)/3
2826 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.16 e Å⁻³
3 restraints	Δρ_min = −0.16 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.43809 (10)	0.77106 (19)	0.40493 (10)	0.0623 (4)
O2	1.06930 (9)	0.8686 (2)	0.31664 (9)	0.0535 (4)
H2	1.0776 (18)	0.990 (3)	0.3396 (14)	0.080*
O3	0.94522 (9)	1.08280 (18)	0.40071 (8)	0.0459 (3)
N1	0.18203 (11)	0.2035 (2)	0.37348 (10)	0.0491 (4)
N2	0.53408 (10)	0.5008 (2)	0.38051 (10)	0.0412 (4)
H2A	0.5433 (15)	0.373 (3)	0.3804 (12)	0.049*
N3	0.61921 (10)	0.6221 (2)	0.37714 (9)	0.0406 (4)
C1	0.26915 (14)	0.1321 (3)	0.35493 (14)	0.0544 (5)
H1	0.2709	−0.0021	0.3357	0.065*
C2	0.35733 (14)	0.2450 (3)	0.36242 (14)	0.0505 (5)
H2B	0.4166	0.1863	0.3494	0.061*
C3	0.35696 (12)	0.4446 (2)	0.38914 (11)	0.0359 (4)
C4	0.26716 (14)	0.5203 (3)	0.40934 (14)	0.0551 (6)
H4	0.2632	0.6542	0.4284	0.066*
C5	0.18303 (14)	0.3945 (3)	0.40092 (15)	0.0587 (6)
H5	0.1233	0.4477	0.4155	0.070*
C6	0.44677 (13)	0.5868 (3)	0.39315 (11)	0.0389 (4)
C7	0.69124 (12)	0.5283 (3)	0.34852 (11)	0.0388 (4)
H7	0.6811	0.3929	0.3314	0.047*
C8	0.78864 (12)	0.6241 (3)	0.34154 (11)	0.0360 (4)
C9	0.81646 (12)	0.8153 (2)	0.37732 (11)	0.0359 (4)
H9	0.7723	0.8862	0.4067	0.043*
C10	0.90944 (12)	0.8982 (2)	0.36891 (10)	0.0347 (4)
C11	0.97676 (12)	0.7914 (3)	0.32485 (11)	0.0374 (4)
C12	0.94930 (13)	0.6032 (3)	0.29006 (11)	0.0418 (4)
H12	0.9936	0.5316	0.2610	0.050*
C13	0.85576 (12)	0.5206 (3)	0.29833 (11)	0.0404 (4)
H13	0.8377	0.3935	0.2745	0.048*
C14	0.89027 (14)	1.1798 (3)	0.45948 (12)	0.0492 (5)
H14A	0.8234	1.2134	0.4320	0.074*
H14B	0.9248	1.3028	0.4802	0.074*
H14C	0.8855	1.0887	0.5058	0.074*
O4	0.60654 (11)	0.0880 (2)	0.43262 (10)	0.0579 (4)
H4A	0.595 (2)	0.106 (4)	0.4841 (13)	0.087*
H4B	0.5877 (19)	−0.032 (3)	0.4252 (16)	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0456 (8)	0.0329 (7)	0.1120 (12)	−0.0063 (6)	0.0238 (8)	−0.0136 (7)
O2	0.0326 (7)	0.0622 (9)	0.0692 (9)	−0.0186 (6)	0.0196 (6)	−0.0190 (7)
O3	0.0352 (7)	0.0382 (7)	0.0657 (8)	−0.0091 (5)	0.0121 (6)	−0.0118 (6)
N1	0.0289 (8)	0.0486 (10)	0.0709 (11)	−0.0095 (7)	0.0115 (7)	−0.0017 (8)
N2	0.0262 (8)	0.0295 (7)	0.0690 (11)	−0.0083 (7)	0.0106 (7)	−0.0023 (8)
N3	0.0269 (8)	0.0352 (8)	0.0594 (10)	−0.0098 (6)	0.0058 (7)	0.0005 (7)
C1	0.0359 (11)	0.0411 (11)	0.0895 (16)	−0.0096 (8)	0.0200 (10)	−0.0108 (11)
C2	0.0308 (10)	0.0391 (10)	0.0857 (15)	−0.0048 (8)	0.0223 (9)	−0.0112 (10)
C3	0.0279 (9)	0.0350 (9)	0.0459 (10)	−0.0037 (7)	0.0087 (7)	−0.0006 (8)
C4	0.0354 (10)	0.0420 (11)	0.0909 (16)	−0.0017 (9)	0.0189 (10)	−0.0136 (10)
C5	0.0301 (10)	0.0559 (13)	0.0935 (16)	0.0001 (9)	0.0211 (10)	−0.0100 (12)
C6	0.0334 (10)	0.0320 (9)	0.0520 (11)	−0.0054 (7)	0.0089 (8)	−0.0027 (8)
C7	0.0284 (9)	0.0348 (9)	0.0516 (11)	−0.0063 (7)	0.0002 (8)	0.0022 (8)
C8	0.0254 (8)	0.0367 (9)	0.0450 (10)	−0.0042 (7)	0.0022 (7)	0.0059 (8)
C9	0.0248 (9)	0.0377 (9)	0.0447 (10)	0.0003 (7)	0.0039 (7)	0.0011 (8)
C10	0.0272 (9)	0.0333 (9)	0.0422 (9)	−0.0039 (7)	0.0002 (7)	0.0006 (8)
C11	0.0240 (8)	0.0461 (10)	0.0423 (10)	−0.0075 (7)	0.0054 (7)	−0.0006 (8)
C12	0.0323 (9)	0.0470 (10)	0.0470 (10)	−0.0039 (8)	0.0084 (8)	−0.0078 (9)
C13	0.0343 (9)	0.0361 (9)	0.0496 (11)	−0.0059 (8)	0.0024 (8)	−0.0034 (8)
C14	0.0466 (11)	0.0418 (11)	0.0590 (12)	0.0000 (9)	0.0071 (9)	−0.0112 (9)
O4	0.0562 (9)	0.0379 (7)	0.0805 (10)	−0.0085 (7)	0.0135 (8)	−0.0065 (8)

Geometric parameters (Å, º) top

O1—C6	1.225 (2)	C4—H4	0.9300
O2—C11	1.358 (2)	C5—H5	0.9300
O2—H2	0.876 (16)	C7—C8	1.461 (2)
O3—C10	1.3668 (19)	C7—H7	0.9300
O3—C14	1.423 (2)	C8—C13	1.385 (2)
N1—C5	1.321 (2)	C8—C9	1.400 (2)
N1—C1	1.326 (2)	C9—C10	1.378 (2)
N2—C6	1.335 (2)	C9—H9	0.9300
N2—N3	1.3923 (18)	C10—C11	1.405 (2)
N2—H2A	0.841 (19)	C11—C12	1.376 (2)
N3—C7	1.280 (2)	C12—C13	1.384 (2)
C1—C2	1.379 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.371 (2)	C14—H14A	0.9600
C2—H2B	0.9300	C14—H14B	0.9600
C3—C4	1.377 (2)	C14—H14C	0.9600
C3—C6	1.510 (2)	O4—H4A	0.87 (2)
C4—C5	1.381 (3)	O4—H4B	0.83 (2)

C11—O2—H2	110.9 (15)	C8—C7—H7	118.5
C10—O3—C14	116.92 (13)	C13—C8—C9	119.14 (15)
C5—N1—C1	116.08 (15)	C13—C8—C7	118.49 (15)
C6—N2—N3	120.10 (14)	C9—C8—C7	122.37 (16)
C6—N2—H2A	123.2 (14)	C10—C9—C8	119.90 (16)
N3—N2—H2A	116.3 (14)	C10—C9—H9	120.0
C7—N3—N2	113.67 (14)	C8—C9—H9	120.0
N1—C1—C2	123.89 (18)	O3—C10—C9	125.47 (15)
N1—C1—H1	118.1	O3—C10—C11	114.20 (14)
C2—C1—H1	118.1	C9—C10—C11	120.33 (15)
C3—C2—C1	119.55 (17)	O2—C11—C12	118.95 (16)
C3—C2—H2B	120.2	O2—C11—C10	121.45 (15)
C1—C2—H2B	120.2	C12—C11—C10	119.59 (15)
C2—C3—C4	117.17 (15)	C11—C12—C13	119.97 (17)
C2—C3—C6	123.94 (15)	C11—C12—H12	120.0
C4—C3—C6	118.81 (15)	C13—C12—H12	120.0
C3—C4—C5	119.12 (18)	C12—C13—C8	121.06 (16)
C3—C4—H4	120.4	C12—C13—H13	119.5
C5—C4—H4	120.4	C8—C13—H13	119.5
N1—C5—C4	124.17 (18)	O3—C14—H14A	109.5
N1—C5—H5	117.9	O3—C14—H14B	109.5
C4—C5—H5	117.9	H14A—C14—H14B	109.5
O1—C6—N2	122.71 (15)	O3—C14—H14C	109.5
O1—C6—C3	121.18 (15)	H14A—C14—H14C	109.5
N2—C6—C3	116.08 (15)	H14B—C14—H14C	109.5
N3—C7—C8	123.09 (16)	H4A—O4—H4B	100 (2)
N3—C7—H7	118.5

C6—N2—N3—C7	−166.97 (16)	N3—C7—C8—C9	9.9 (3)
C5—N1—C1—C2	−0.3 (3)	C13—C8—C9—C10	0.3 (2)
N1—C1—C2—C3	−1.1 (3)	C7—C8—C9—C10	179.87 (15)
C1—C2—C3—C4	1.6 (3)	C14—O3—C10—C9	11.8 (2)
C1—C2—C3—C6	−175.09 (19)	C14—O3—C10—C11	−168.05 (15)
C2—C3—C4—C5	−0.7 (3)	C8—C9—C10—O3	179.92 (15)
C6—C3—C4—C5	176.14 (19)	C8—C9—C10—C11	−0.3 (2)
C1—N1—C5—C4	1.3 (3)	O3—C10—C11—O2	0.7 (2)
C3—C4—C5—N1	−0.8 (3)	C9—C10—C11—O2	−179.13 (16)
N3—N2—C6—O1	−2.4 (3)	O3—C10—C11—C12	179.84 (15)
N3—N2—C6—C3	175.49 (15)	C9—C10—C11—C12	0.0 (2)
C2—C3—C6—O1	168.7 (2)	O2—C11—C12—C13	179.38 (16)
C4—C3—C6—O1	−8.0 (3)	C10—C11—C12—C13	0.2 (3)
C2—C3—C6—N2	−9.3 (3)	C11—C12—C13—C8	−0.2 (3)
C4—C3—C6—N2	174.06 (18)	C9—C8—C13—C12	−0.1 (3)
N2—N3—C7—C8	−178.33 (15)	C7—C8—C13—C12	−179.67 (16)
N3—C7—C8—C13	−170.50 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N3ⁱ	0.83 (2)	2.44 (2)	3.179 (2)	149 (2)
O4—H4B···O1ⁱ	0.83 (2)	2.36 (2)	3.0391 (19)	140 (2)
O4—H4A···O1ⁱⁱ	0.87 (2)	2.05 (2)	2.901 (2)	165 (2)
N2—H2A···O4	0.841 (19)	2.16 (2)	2.942 (2)	154.1 (18)
O2—H2···O3	0.88 (2)	2.22 (2)	2.6757 (18)	112 (2)
O2—H2···N1ⁱⁱⁱ	0.88 (2)	1.99 (2)	2.733 (2)	142 (2)

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

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N′-(4-Hydr­oxy-3-methoxy­benzyl­idene)isonicotinohydrazide monohydrate

Supporting information

Key indicators

checkCIF/PLATON results

N′-(4-Hydroxy-3-methoxybenzylidene)isonicotinohydrazide monohydrate