(E)-4-Chloro-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)benzohydrazide mono­hydrate

In the title compound, C₁₅H₁₃ClN₂O₃·H₂O, the mol­ecule adopts a trans configuration with respect to the C=N double bond. The dihedral angle between the two rings is 15.03 (3)°. The structure is stabilized by intra­molecular O—H...N and intermolecular N—H...O and O—H...O hydrogen bonds, forming an intricate three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.095
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.63 mm
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O4      ..       2.64 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2522
           Count of symmetry unique reflns         1519
           Completeness (_total/calc)            166.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1003
           Fraction of Friedel pairs measured     0.660
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

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

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S1. Comment

Recently, we have reported some organotin(IV) complexes with Schiff base of o-vanillin-2-thiophenoylhydrazone (Yin & Chen, 2006). As an extension of our work on the structural characterization of Schiff base compounds, the title compound, (I), is reported here (Scheme).

The molecule adopts a trans conformation with respect to the C8=N2 double bond length of 1.282 (4) Å (Fig. 1). The C1—N1 bond [1.350 (4) Å] and N1—N2 bond [1.380 (3) Å] are intermediate between a double bond and a single bond because of conjugation effects in the molecule. The two benzene rings make a dihedral angle of 15.0 (2) Å.

The occurrence of N—H···O and O—H···O hydrogen bonds (Table 1) results in the formation of an intricated three dimensionnal network (Fig. 2).

Related literature

For related compounds see: Yin & Chen (2006).

S2. Experimental

Compound (I) was synthesized by the reaction of 4-chlorobenzohydrazide (5 mmol) with 2-hydroxy-3-methoxybenzaldehyde (5 mmol). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

S3. Refinement

All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) and N—H = 0.86 Å with U_iso(H) = 1.2U_eq(C or N). H atoms of water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O—H= 0.85 (1)Å and H···H= 1.39 (2) Å) with U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997a); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. Molecular structure of (I), with atom-labelling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. H bonds are shown as dashed lines.
	Fig. 2. Partial packing view showing the inticated N—H···O and O—H···O hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) 1 - x, 1/2 + y, 3/2 - z; (ii) x - 1, y, z].

(E)-4-chloro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate

Crystal data

C15H13ClN2O3·H2O	F(000) = 672
Mr = 322.74	Dx = 1.488 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1656 reflections
a = 4.8651 (16) Å	θ = 3.1–21.9°
b = 12.9403 (17) Å	µ = 0.29 mm^−1
c = 22.884 (3) Å	T = 298 K
V = 1440.7 (5) Å^3	Block, colourless
Z = 4	0.63 × 0.13 × 0.10 mm

Data collection

CCD area-detector diffractometer	2522 independent reflections
Radiation source: fine-focus sealed tube	1689 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.841, Tmax = 0.972	k = −15→11
7353 measured reflections	l = −27→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0396P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2522 reflections	Δρmax = 0.20 e Å^−3
208 parameters	Δρmin = −0.21 e Å^−3
3 restraints	Absolute structure: Flack (1983), 1003 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.44005 (19)	0.94535 (6)	0.99650 (3)	0.0487 (3)
N1	0.5212 (6)	0.89997 (19)	0.78551 (10)	0.0398 (8)
H1	0.4895	0.9640	0.7930	0.048*
N2	0.7123 (6)	0.8731 (2)	0.74363 (11)	0.0393 (7)
O1	0.4210 (6)	0.73389 (17)	0.80590 (10)	0.0599 (8)
O2	1.0116 (6)	0.75187 (16)	0.67217 (9)	0.0472 (6)
H2	0.9081	0.7627	0.6998	0.071*
O3	1.3785 (5)	0.73687 (17)	0.59184 (10)	0.0511 (7)
O4	0.5138 (6)	0.62346 (17)	0.70642 (9)	0.0569 (8)
H16	0.522 (9)	0.662 (2)	0.7362 (9)	0.085*
H17	0.404 (7)	0.646 (3)	0.6806 (11)	0.085*
C1	0.3841 (8)	0.8254 (3)	0.81471 (14)	0.0408 (9)
C2	0.1830 (7)	0.8619 (2)	0.85941 (13)	0.0334 (8)
C3	0.0707 (8)	0.7873 (2)	0.89629 (13)	0.0445 (9)
H3	0.1256	0.7188	0.8923	0.053*
C4	−0.1173 (8)	0.8124 (3)	0.93798 (14)	0.0439 (10)
H4	−0.1894	0.7616	0.9623	0.053*
C5	−0.1999 (7)	0.9138 (3)	0.94387 (12)	0.0358 (9)
C6	−0.0920 (8)	0.9884 (2)	0.90805 (13)	0.0380 (9)
H6	−0.1482	1.0567	0.9121	0.046*
C7	0.0972 (7)	0.9631 (2)	0.86649 (13)	0.0389 (9)
H7	0.1695	1.0145	0.8426	0.047*
C8	0.8421 (8)	0.9500 (3)	0.72158 (13)	0.0411 (9)
H8	0.8010	1.0163	0.7346	0.049*
C9	1.0492 (7)	0.9369 (2)	0.67743 (12)	0.0350 (8)
C10	1.1250 (7)	0.8417 (2)	0.65468 (12)	0.0341 (9)
C11	1.3243 (7)	0.8360 (3)	0.61088 (13)	0.0379 (9)
C12	1.4518 (8)	0.9226 (3)	0.59104 (14)	0.0441 (9)
H12	1.5860	0.9177	0.5622	0.053*
C13	1.3812 (9)	1.0186 (3)	0.61392 (15)	0.0531 (11)
H13	1.4685	1.0780	0.6006	0.064*
C14	1.1836 (8)	1.0251 (3)	0.65588 (15)	0.0481 (10)
H14	1.1363	1.0897	0.6707	0.058*
C15	1.6082 (8)	0.7249 (3)	0.55397 (15)	0.0567 (11)
H15A	1.7717	0.7478	0.5736	0.085*
H15B	1.5805	0.7654	0.5193	0.085*
H15C	1.6273	0.6534	0.5435	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0443 (5)	0.0541 (6)	0.0476 (5)	−0.0028 (5)	0.0090 (5)	−0.0020 (4)
N1	0.042 (2)	0.0359 (17)	0.0417 (15)	0.0058 (15)	0.0079 (15)	−0.0073 (13)
N2	0.0376 (19)	0.0410 (19)	0.0393 (16)	0.0035 (16)	0.0042 (15)	−0.0046 (14)
O1	0.087 (2)	0.0306 (14)	0.0618 (15)	0.0113 (15)	0.0204 (17)	0.0000 (12)
O2	0.0457 (17)	0.0405 (14)	0.0555 (15)	−0.0067 (13)	0.0194 (13)	0.0013 (11)
O3	0.0486 (18)	0.0449 (15)	0.0597 (15)	−0.0042 (13)	0.0200 (14)	−0.0067 (12)
O4	0.074 (2)	0.0400 (15)	0.0571 (16)	0.0051 (16)	0.0115 (16)	−0.0022 (12)
C1	0.048 (2)	0.037 (2)	0.0376 (19)	0.0046 (19)	−0.004 (2)	0.0051 (17)
C2	0.033 (2)	0.034 (2)	0.0331 (17)	0.0000 (17)	−0.0048 (17)	−0.0034 (15)
C3	0.055 (3)	0.0281 (19)	0.051 (2)	0.001 (2)	−0.001 (2)	0.0007 (16)
C4	0.048 (3)	0.036 (2)	0.048 (2)	0.0012 (19)	0.013 (2)	0.0072 (16)
C5	0.032 (2)	0.042 (2)	0.0329 (18)	−0.0028 (18)	−0.0028 (17)	0.0009 (16)
C6	0.036 (2)	0.0316 (19)	0.0466 (19)	0.0033 (18)	0.001 (2)	−0.0030 (17)
C7	0.046 (2)	0.033 (2)	0.0378 (18)	−0.0042 (19)	0.0059 (19)	0.0051 (15)
C8	0.037 (2)	0.043 (2)	0.0434 (19)	0.005 (2)	−0.0043 (18)	−0.0045 (17)
C9	0.0310 (19)	0.038 (2)	0.0362 (17)	0.0080 (19)	−0.0043 (18)	0.0007 (16)
C10	0.032 (2)	0.035 (2)	0.0347 (19)	−0.0038 (18)	−0.0011 (17)	0.0034 (15)
C11	0.038 (2)	0.041 (2)	0.0351 (18)	−0.0034 (19)	−0.0005 (18)	−0.0002 (16)
C12	0.038 (2)	0.052 (2)	0.0419 (18)	−0.004 (2)	0.0014 (19)	0.0037 (18)
C13	0.052 (3)	0.042 (2)	0.065 (2)	−0.009 (2)	0.006 (2)	0.0122 (19)
C14	0.047 (3)	0.039 (2)	0.059 (2)	0.0032 (19)	−0.006 (2)	−0.0006 (17)
C15	0.043 (3)	0.069 (3)	0.058 (2)	0.003 (2)	0.015 (2)	−0.016 (2)

Geometric parameters (Å, º)

Cl1—C5	1.727 (3)	C5—C6	1.371 (4)
N1—C1	1.350 (4)	C6—C7	1.363 (4)
N1—N2	1.380 (3)	C6—H6	0.9300
N1—H1	0.8600	C7—H7	0.9300
N2—C8	1.282 (4)	C8—C9	1.437 (5)
O1—C1	1.215 (4)	C8—H8	0.9300
O2—C10	1.348 (3)	C9—C10	1.387 (4)
O2—H2	0.8200	C9—C14	1.405 (5)
O3—C11	1.380 (4)	C10—C11	1.397 (4)
O3—C15	1.422 (4)	C11—C12	1.359 (4)
O4—H16	0.84 (3)	C12—C13	1.391 (5)
O4—H17	0.85 (3)	C12—H12	0.9300
C1—C2	1.492 (4)	C13—C14	1.361 (5)
C2—C7	1.384 (4)	C13—H13	0.9300
C2—C3	1.394 (4)	C14—H14	0.9300
C3—C4	1.361 (5)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.379 (5)	C15—H15C	0.9600
C4—H4	0.9300
C1—N1—N2	119.8 (3)	N2—C8—C9	122.1 (3)
C1—N1—H1	120.1	N2—C8—H8	119.0
N2—N1—H1	120.1	C9—C8—H8	119.0
C8—N2—N1	114.2 (3)	C10—C9—C14	117.8 (3)
C10—O2—H2	109.5	C10—C9—C8	123.7 (3)
C11—O3—C15	116.3 (3)	C14—C9—C8	118.5 (3)
H16—O4—H17	113 (2)	O2—C10—C9	123.1 (3)
O1—C1—N1	122.8 (3)	O2—C10—C11	116.8 (3)
O1—C1—C2	121.3 (3)	C9—C10—C11	120.1 (3)
N1—C1—C2	115.9 (3)	C12—C11—O3	125.0 (3)
C7—C2—C3	117.8 (3)	C12—C11—C10	120.8 (3)
C7—C2—C1	125.3 (3)	O3—C11—C10	114.1 (3)
C3—C2—C1	116.9 (3)	C11—C12—C13	119.9 (3)
C4—C3—C2	121.5 (3)	C11—C12—H12	120.1
C4—C3—H3	119.2	C13—C12—H12	120.1
C2—C3—H3	119.2	C14—C13—C12	119.7 (4)
C3—C4—C5	119.4 (3)	C14—C13—H13	120.2
C3—C4—H4	120.3	C12—C13—H13	120.2
C5—C4—H4	120.3	C13—C14—C9	121.7 (3)
C6—C5—C4	120.0 (3)	C13—C14—H14	119.1
C6—C5—Cl1	120.6 (3)	C9—C14—H14	119.1
C4—C5—Cl1	119.4 (3)	O3—C15—H15A	109.5
C7—C6—C5	120.4 (3)	O3—C15—H15B	109.5
C7—C6—H6	119.8	H15A—C15—H15B	109.5
C5—C6—H6	119.8	O3—C15—H15C	109.5
C6—C7—C2	120.8 (3)	H15A—C15—H15C	109.5
C6—C7—H7	119.6	H15B—C15—H15C	109.5
C2—C7—H7	119.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^i	0.86	2.06	2.903 (3)	165
O2—H2···N2	0.82	1.99	2.694 (3)	144
O2—H2···O4	0.82	2.64	3.040 (4)	112
O4—H16···O1	0.84 (3)	1.91 (2)	2.725 (3)	161 (4)
O4—H17···O2^ii	0.85 (3)	2.36 (3)	3.057 (4)	140 (3)
O4—H17···O3^ii	0.85 (3)	2.35 (3)	3.076 (3)	144 (4)

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