N′-[(1E)-4-Hy­droxy-3-meth­oxy­benzylidene]isonicotinohydrazide monohydrate

In the title hydrate, C₁₄H₁₃N₃O₃·H₂O, the dihedral angle between the pyridine and benzene rings is 2.52 (9)°. Intra­molecular O—H...O hydrogen bonds occur. In the crystal, O—H...O, O—H...N, N—H...O and C—H...O hydrogen bonds link the components into a three-dimensional network. π–π inter­actions are also observed.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.114
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5856
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   8.9602
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5856
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.971 Note
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.96 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H8C    ..  H12     ..       2.07 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.586         68 Report

Alert level G
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          56 %
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b).

N'-[(1E)-4-Hydroxy-3-methoxybenzylidene]isonicotinohydrazide monohydrate

Crystal data

C14H13N3O3·H2O	Dx = 1.401 Mg m^−3
Mr = 289.29	Melting point: 298 K
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 8.3687 (7) Å	Cell parameters from 2249 reflections
b = 13.0913 (10) Å	θ = 4.9–64.5°
c = 12.6778 (11) Å	µ = 0.88 mm^−1
β = 99.086 (5)°	T = 296 K
V = 1371.5 (2) Å^3	Prism, colourless
Z = 4	0.24 × 0.20 × 0.12 mm
F(000) = 576

Data collection

Bruker SMART CCD area-detector diffractometer	2249 independent reflections
Radiation source: fine-focus sealed tube	1805 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω and φ scans	θmax = 64.5°, θmin = 4.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −7→9
Tmin = 0.770, Tmax = 1.000	k = −14→15
7361 measured reflections	l = −14→12

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.2398P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.114	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.25 e Å^−3
2249 reflections	Δρmin = −0.25 e Å^−3
251 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0065 (7)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.01283 (15)	0.81847 (9)	0.90314 (11)	0.0528 (4)
O2	−0.04008 (15)	0.61830 (10)	0.93903 (12)	0.0539 (4)
O3	0.81796 (17)	0.55219 (9)	0.64551 (13)	0.0627 (4)
O4	0.7956 (2)	0.43537 (13)	0.83061 (19)	0.0730 (5)
N5	1.22351 (17)	0.77082 (12)	0.50647 (12)	0.0476 (4)
N6	0.72171 (17)	0.70837 (12)	0.67777 (13)	0.0439 (4)
N7	0.59405 (17)	0.66654 (11)	0.72119 (12)	0.0469 (4)
C8	0.0359 (3)	0.92178 (15)	0.8789 (2)	0.0645 (7)
C9	0.12124 (18)	0.74987 (12)	0.87380 (13)	0.0378 (4)
C10	0.25461 (19)	0.77494 (14)	0.82747 (14)	0.0404 (4)
C11	0.35901 (19)	0.69995 (13)	0.80039 (14)	0.0413 (4)
C12	0.3261 (2)	0.59800 (14)	0.82145 (16)	0.0478 (5)
C13	0.1922 (2)	0.57302 (13)	0.86640 (16)	0.0468 (5)
C14	0.0886 (2)	0.64756 (13)	0.89347 (14)	0.0400 (4)
C15	0.4981 (2)	0.73119 (15)	0.75230 (15)	0.0452 (5)
C16	0.8276 (2)	0.64568 (13)	0.64171 (14)	0.0411 (4)
C17	0.96296 (18)	0.69426 (12)	0.59529 (13)	0.0361 (4)
C18	0.9779 (2)	0.79793 (13)	0.57671 (15)	0.0423 (4)
C19	1.1081 (2)	0.83129 (14)	0.53230 (15)	0.0446 (5)
C20	1.2073 (2)	0.67153 (15)	0.52461 (19)	0.0570 (6)
C21	1.0808 (2)	0.63071 (14)	0.56764 (17)	0.0499 (5)
H2	−0.106 (3)	0.678 (2)	0.955 (2)	0.107 (9)*
H6	0.731 (3)	0.7757 (18)	0.6774 (16)	0.058 (6)*
H10	0.283 (2)	0.8450 (16)	0.8173 (16)	0.058 (6)*
H13	0.168 (2)	0.5017 (16)	0.8816 (16)	0.064 (6)*
H18	0.900 (2)	0.8477 (15)	0.5953 (15)	0.055 (5)*
H12	0.402 (3)	0.5455 (15)	0.8037 (16)	0.063 (6)*
H19	1.118 (2)	0.9016 (16)	0.5182 (16)	0.058 (6)*
H15	0.519 (2)	0.8058 (17)	0.7452 (15)	0.057 (6)*
H21	1.075 (3)	0.5576 (17)	0.5790 (17)	0.068 (6)*
H20	1.289 (3)	0.6279 (17)	0.5081 (17)	0.070 (7)*
H8A	−0.051 (3)	0.9615 (18)	0.8970 (19)	0.080 (7)*
H8B	0.143 (3)	0.9463 (18)	0.918 (2)	0.089 (8)*
H8C	0.031 (3)	0.930 (2)	0.792 (2)	0.102 (9)*
H4B	0.785 (4)	0.475 (2)	0.770 (2)	0.103 (10)*
H4A	0.841 (4)	0.472 (3)	0.867 (3)	0.132 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0479 (7)	0.0351 (7)	0.0847 (10)	0.0084 (5)	0.0386 (7)	0.0072 (6)
O2	0.0455 (8)	0.0385 (7)	0.0868 (11)	0.0000 (5)	0.0386 (7)	0.0034 (6)
O3	0.0569 (8)	0.0407 (7)	0.1011 (12)	−0.0071 (6)	0.0452 (8)	−0.0036 (7)
O4	0.0819 (12)	0.0538 (9)	0.0861 (13)	−0.0240 (8)	0.0218 (10)	0.0032 (9)
N5	0.0380 (8)	0.0474 (8)	0.0618 (10)	−0.0014 (6)	0.0216 (7)	0.0035 (7)
N6	0.0354 (8)	0.0421 (9)	0.0599 (10)	−0.0036 (6)	0.0250 (7)	−0.0039 (7)
N7	0.0346 (8)	0.0539 (9)	0.0576 (10)	−0.0046 (7)	0.0237 (7)	−0.0048 (7)
C8	0.0622 (14)	0.0354 (10)	0.105 (2)	0.0109 (9)	0.0420 (14)	0.0106 (11)
C9	0.0327 (8)	0.0353 (9)	0.0485 (10)	0.0047 (7)	0.0156 (7)	0.0002 (7)
C10	0.0348 (9)	0.0390 (9)	0.0504 (11)	0.0001 (7)	0.0160 (7)	0.0013 (8)
C11	0.0335 (9)	0.0479 (10)	0.0457 (10)	0.0003 (7)	0.0161 (7)	−0.0029 (8)
C12	0.0411 (10)	0.0431 (10)	0.0642 (12)	0.0057 (8)	0.0240 (9)	−0.0066 (9)
C13	0.0429 (10)	0.0358 (9)	0.0667 (13)	0.0015 (7)	0.0235 (9)	−0.0030 (9)
C14	0.0351 (9)	0.0388 (9)	0.0498 (10)	−0.0018 (7)	0.0183 (7)	0.0005 (7)
C15	0.0377 (10)	0.0501 (11)	0.0516 (11)	0.0004 (8)	0.0185 (8)	−0.0023 (8)
C16	0.0327 (9)	0.0404 (9)	0.0535 (11)	−0.0031 (7)	0.0170 (7)	−0.0030 (8)
C17	0.0283 (8)	0.0389 (8)	0.0429 (10)	−0.0011 (6)	0.0116 (7)	−0.0035 (7)
C18	0.0356 (9)	0.0384 (9)	0.0557 (11)	0.0010 (7)	0.0155 (8)	−0.0042 (8)
C19	0.0394 (10)	0.0378 (10)	0.0596 (12)	−0.0038 (7)	0.0170 (8)	0.0012 (8)
C20	0.0459 (11)	0.0466 (11)	0.0870 (16)	0.0072 (9)	0.0371 (10)	0.0075 (10)
C21	0.0434 (10)	0.0378 (10)	0.0744 (14)	0.0033 (8)	0.0280 (9)	0.0049 (9)

Geometric parameters (Å, º)

O1—C9	1.3691 (19)	C10—C11	1.393 (2)
O1—C8	1.407 (2)	C10—H10	0.96 (2)
O2—C14	1.355 (2)	C11—C12	1.397 (3)
O2—H2	0.99 (3)	C11—C15	1.455 (2)
O3—C16	1.228 (2)	C12—C13	1.374 (3)
O4—H4B	0.92 (3)	C12—H12	0.99 (2)
O4—H4A	0.73 (3)	C13—C14	1.384 (2)
N5—C19	1.329 (2)	C13—H13	0.98 (2)
N5—C20	1.331 (2)	C15—H15	1.00 (2)
N6—C16	1.340 (2)	C16—C17	1.498 (2)
N6—N7	1.389 (2)	C17—C21	1.377 (2)
N6—H6	0.88 (2)	C17—C18	1.386 (2)
N7—C15	1.272 (2)	C18—C19	1.375 (3)
C8—H8A	0.95 (3)	C18—H18	0.97 (2)
C8—H8B	1.01 (3)	C19—H19	0.94 (2)
C8—H8C	1.10 (3)	C20—C21	1.373 (3)
C9—C10	1.380 (2)	C20—H20	0.94 (2)
C9—C14	1.397 (2)	C21—H21	0.97 (2)
C9—O1—C8	116.83 (14)	C12—C13—H13	120.9 (12)
C14—O2—H2	111.8 (16)	C14—C13—H13	117.9 (13)
H4B—O4—H4A	97 (3)	O2—C14—C13	118.52 (15)
C19—N5—C20	116.19 (16)	O2—C14—C9	122.53 (15)
C16—N6—N7	119.02 (15)	C13—C14—C9	118.95 (16)
C16—N6—H6	123.2 (15)	N7—C15—C11	121.94 (18)
N7—N6—H6	117.8 (15)	N7—C15—H15	119.6 (12)
C15—N7—N6	115.06 (15)	C11—C15—H15	118.4 (12)
O1—C8—H8A	109.6 (15)	O3—C16—N6	123.10 (16)
O1—C8—H8B	109.9 (14)	O3—C16—C17	119.78 (15)
H8A—C8—H8B	111 (2)	N6—C16—C17	117.12 (15)
O1—C8—H8C	109.3 (14)	C21—C17—C18	117.44 (16)
H8A—C8—H8C	106 (2)	C21—C17—C16	117.37 (15)
H8B—C8—H8C	111 (2)	C18—C17—C16	125.18 (15)
O1—C9—C10	125.07 (15)	C19—C18—C17	118.63 (16)
O1—C9—C14	115.08 (14)	C19—C18—H18	119.2 (12)
C10—C9—C14	119.85 (15)	C17—C18—H18	122.1 (12)
C9—C10—C11	121.21 (16)	N5—C19—C18	124.45 (17)
C9—C10—H10	120.9 (13)	N5—C19—H19	116.3 (13)
C11—C10—H10	117.7 (13)	C18—C19—H19	119.3 (13)
C10—C11—C12	118.41 (16)	N5—C20—C21	123.69 (18)
C10—C11—C15	118.65 (16)	N5—C20—H20	117.2 (14)
C12—C11—C15	122.94 (16)	C21—C20—H20	119.1 (14)
C13—C12—C11	120.34 (16)	C20—C21—C17	119.60 (17)
C13—C12—H12	121.8 (12)	C20—C21—H21	120.1 (14)
C11—C12—H12	117.8 (12)	C17—C21—H21	120.3 (14)
C12—C13—C14	121.23 (17)
C16—N6—N7—C15	−179.18 (16)	C10—C11—C15—N7	−176.74 (17)
C8—O1—C9—C10	3.4 (3)	C12—C11—C15—N7	3.8 (3)
C8—O1—C9—C14	−176.32 (19)	N7—N6—C16—O3	−0.3 (3)
O1—C9—C10—C11	179.83 (16)	N7—N6—C16—C17	179.83 (14)
C14—C9—C10—C11	−0.5 (3)	O3—C16—C17—C21	−6.0 (3)
C9—C10—C11—C12	−0.2 (3)	N6—C16—C17—C21	173.86 (17)
C9—C10—C11—C15	−179.66 (16)	O3—C16—C17—C18	173.15 (18)
C10—C11—C12—C13	0.9 (3)	N6—C16—C17—C18	−7.0 (3)
C15—C11—C12—C13	−179.58 (18)	C21—C17—C18—C19	−0.1 (3)
C11—C12—C13—C14	−1.1 (3)	C16—C17—C18—C19	−179.19 (17)
C12—C13—C14—O2	−179.03 (18)	C20—N5—C19—C18	0.9 (3)
C12—C13—C14—C9	0.4 (3)	C17—C18—C19—N5	−0.8 (3)
O1—C9—C14—O2	−0.5 (3)	C19—N5—C20—C21	−0.2 (3)
C10—C9—C14—O2	179.79 (17)	N5—C20—C21—C17	−0.6 (4)
O1—C9—C14—C13	−179.92 (16)	C18—C17—C21—C20	0.7 (3)
C10—C9—C14—C13	0.4 (3)	C16—C17—C21—C20	179.90 (19)
N6—N7—C15—C11	−179.50 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	1.00 (3)	2.24 (3)	2.7081 (18)	107.4 (18)
O2—H2···N5^i	1.00 (3)	1.79 (3)	2.699 (2)	150 (2)
O4—H4A···O2^ii	0.73 (4)	2.28 (4)	2.986 (2)	163 (4)
O4—H4B···O3	0.92 (3)	1.93 (3)	2.832 (3)	166 (3)
N6—H6···O4^iii	0.89 (2)	2.10 (2)	2.976 (2)	169 (2)
C8—H8A···O3^iv	0.95 (2)	2.51 (2)	3.390 (3)	154 (2)
C15—H15···O4^iii	1.00 (2)	2.58 (2)	3.436 (3)	143.1 (14)
C18—H18···O4^iii	0.977 (18)	2.316 (18)	3.272 (3)	165.9 (16)
C20—H20···O1^v	0.94 (2)	2.56 (2)	3.189 (2)	124.5 (17)

Symmetry codes: (i) x−3/2, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) x+3/2, −y+3/2, z−1/2.