(E)-N′-[3-(4-Chloro­benzo­yloxy)benzyl­idene]pyridine-4-carbohydrazide acetic acid monosolvate monohydrate

Diao, C.-H.; Fan, Z.

doi:10.1107/S1600536812017369

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1517

doi:10.1107/S1600536812017369

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(E)-N′-[3-(4-Chlorobenzoyloxy)benzylidene]pyridine-4-carbohydrazide acetic acid monosolvate monohydrate

Chun-Hua Diao ^a and Zhi Fan ^a ^*

^aCollege of Sciences, Tianjin University of Science and Technology, Tianjin 300457, People's Republic of China
^*Correspondence e-mail: zhifan@tust.edu.cn

(Received 10 April 2012; accepted 19 April 2012; online 25 April 2012)

In the Schiff base molecule of the title compound, C₂₀H₁₄ClN₃O₃·CH₃COOH·H₂O, the central benzene ring makes dihedral angles of 36.26 (7) and 27.59 (8)°, respectively, with the terminal chlorophenyl and pyridine rings. In the crystal, the three components are linked by O—H⋯O, N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds into a double-tape structure along the a axis.

Related literature

For general background to the use of Schiff base derivatives in the development of protein and enzyme mimics, see: Santos et al. (2001 ). For closely related crystal structures, see: Diao et al. (2007 ); Peralta et al. (2007 ); de Souza et al. (2007 ); Wardell et al. (2005 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₄ClN₃O₃·C₂H₄O₂·H₂O
M_r = 457.86
Triclinic, $[P \overline 1]$
a = 6.6666 (15) Å
b = 7.5437 (17) Å
c = 24.781 (6) Å
α = 81.526 (4)°
β = 82.969 (4)°
γ = 66.632 (4)°
V = 1128.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 294 K
0.18 × 0.16 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.979
5755 measured reflections
3936 independent reflections
2501 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.119
S = 1.03
3936 reflections
298 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O3	0.86 (3)	2.00 (3)	2.843 (2)	166 (2)
O6—H6B⋯O4ⁱ	0.86 (2)	1.98 (2)	2.812 (3)	165 (3)
O5—H5A⋯N3ⁱⁱ	0.82	1.85	2.646 (3)	164
N2—H2⋯O6ⁱⁱⁱ	0.86	2.04	2.879 (2)	164
C14—H14⋯O6ⁱⁱⁱ	0.93	2.59	3.367 (4)	141
C17—H17⋯O6ⁱⁱⁱ	0.93	2.50	3.331 (3)	149
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y, z-1; (iii) x+1, y, z.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); 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.

Supporting information

Crystal structure: contains datablock global. DOI: 10.1107/S1600536812017369/is5118sup1.cif

checkCIF report

Comment top

Many Schiff base derivatives have been synthesized and found to exhibit important pharmacological properties, such as antibacterial, antitumor and antitoxic activities (Santos et al., 2001). Among the large number of the compounds, isonicotinohydrazide forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them have been reported (Wardell et al., 2005; Peralta et al., 2007; de Souza et al., 2007).

In order to obtain more detailed information on the structural conformation of the molecule that may be of value in structure-activity analysis, we report here the synthesis and structure of the title compound, (I), as part of our study of isonicotinoylhydrazones (Diao et al., 2007).

In (I) (Fig. 1), the central benzene ring (C8–C14/O2) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0255 Å. This plane makes dihedral angles of 27.59 (8) and 36.26 (7)° with the pyridine ring (C16–C20/N3) and the terminal benzene ring (C1–C6),respectively. The dihedral angle between the pyridine ring and the benzene ring is 26.03 (7)°. All bond lengths are within normal ranges (Allen et al., 1987).

The acetic acid molecule and the water molecule are effectively tethered to the Schiff base component by a combination of independent hydrogen bonds, two O—H···O, one N—H···O, one O—H···N and one C—H···O types (Fig. 2 and Table 2).

Related literature top

For general background to the use of Schiff base derivatives in the development of protein and enzyme mimics, see: Santos et al. (2001). For closely related crystal structures, see: Diao et al. (2007); Peralta et al. (2007); de Souza et al. (2007); Wardell et al. (2005). For reference bond-length data, see: Allen et al. (1987).

Experimental top

An anhydrous ethanol solution (50 ml) of 3-formylphenyl 4-chlorobenzoate (2.61 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of isonicotinohydrazide (1.37 g, 10 mmol) and the mixture stirred at 350 K for 5 h under N₂, giving a white precipitate. The product was isolated, recrystallized from ethanol, and then dried in a vacuum to give pure compound (I) in 72% yield. Colorless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a solution of ethanol and acetic acid (80:20 v/v).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
	Fig. 2. A packing diagram for the title compound with the hydrogen bonds drawn as dashed lines. H atoms not involved in the hydrogen bonds have been omitted.

(E)-N'-[3-(4-Chlorobenzoyloxy)benzylidene]pyridine-4- carbohydrazide acetic acid monosolvate monohydrate top

Crystal data top

C₂₀H₁₄ClN₃O₃·C₂H₄O₂·H₂O	Z = 2
M_r = 457.86	F(000) = 476
Triclinic, P1	D_x = 1.347 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6666 (15) Å	Cell parameters from 1984 reflections
b = 7.5437 (17) Å	θ = 2.5–25.2°
c = 24.781 (6) Å	µ = 0.21 mm⁻¹
α = 81.526 (4)°	T = 294 K
β = 82.969 (4)°	Block, colorless
γ = 66.632 (4)°	0.18 × 0.16 × 0.10 mm
V = 1128.7 (5) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3936 independent reflections
Radiation source: fine-focus sealed tube	2501 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.928, T_max = 0.979	k = −8→8
5755 measured reflections	l = −27→29

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0473P)² + 0.2041P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3936 reflections	Δρ_max = 0.15 e Å⁻³
298 parameters	Δρ_min = −0.17 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (17)

Crystal data top

C₂₀H₁₄ClN₃O₃·C₂H₄O₂·H₂O	γ = 66.632 (4)°
M_r = 457.86	V = 1128.7 (5) Å³
Triclinic, P1	Z = 2
a = 6.6666 (15) Å	Mo Kα radiation
b = 7.5437 (17) Å	µ = 0.21 mm⁻¹
c = 24.781 (6) Å	T = 294 K
α = 81.526 (4)°	0.18 × 0.16 × 0.10 mm
β = 82.969 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3936 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2501 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.979	R_int = 0.019
5755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	3 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.15 e Å⁻³
3936 reflections	Δρ_min = −0.17 e Å⁻³
298 parameters

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 > 2σ(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
Cl1	1.33537 (13)	0.76087 (12)	0.41389 (3)	0.0905 (3)
O1	0.5002 (3)	0.8179 (3)	0.59922 (8)	0.0951 (7)
O2	0.7889 (3)	0.6503 (3)	0.64925 (7)	0.0686 (5)
O3	0.3270 (2)	0.7186 (2)	0.98573 (7)	0.0608 (5)
N1	0.5560 (3)	0.6798 (3)	0.88899 (8)	0.0524 (5)
N2	0.6335 (3)	0.7116 (3)	0.93397 (7)	0.0534 (5)
H2	0.7581	0.7221	0.9319	0.064*
N3	0.7533 (4)	0.8006 (3)	1.12485 (8)	0.0626 (6)
C1	0.7913 (5)	0.7979 (5)	0.50434 (12)	0.0820 (9)
H1	0.6443	0.8341	0.4987	0.098*
C2	0.9364 (5)	0.8039 (4)	0.46046 (11)	0.0809 (9)
H2A	0.8882	0.8445	0.4254	0.097*
C3	1.1507 (4)	0.7501 (4)	0.46886 (10)	0.0628 (7)
C4	1.2231 (5)	0.6916 (5)	0.52037 (11)	0.0822 (9)
H4	1.3702	0.6559	0.5258	0.099*
C5	1.0767 (4)	0.6859 (4)	0.56408 (11)	0.0742 (8)
H5	1.1258	0.6454	0.5991	0.089*
C6	0.8596 (4)	0.7392 (3)	0.55674 (10)	0.0563 (6)
C7	0.6938 (4)	0.7422 (4)	0.60230 (11)	0.0643 (7)
C8	0.6574 (4)	0.6336 (4)	0.69716 (10)	0.0573 (6)
C9	0.4946 (4)	0.5648 (4)	0.69816 (11)	0.0669 (7)
H9	0.4609	0.5348	0.6662	0.080*
C10	0.3821 (4)	0.5412 (4)	0.74740 (11)	0.0659 (7)
H10	0.2705	0.4958	0.7486	0.079*
C11	0.4328 (4)	0.5838 (3)	0.79477 (10)	0.0580 (6)
H11	0.3540	0.5691	0.8276	0.070*
C12	0.6014 (4)	0.6488 (3)	0.79379 (9)	0.0511 (6)
C13	0.7122 (4)	0.6747 (4)	0.74412 (10)	0.0573 (6)
H13	0.8239	0.7201	0.7426	0.069*
C14	0.6656 (4)	0.6871 (4)	0.84357 (10)	0.0581 (6)
H14	0.7887	0.7173	0.8421	0.070*
C15	0.5077 (4)	0.7258 (3)	0.98161 (9)	0.0474 (6)
C16	0.6030 (3)	0.7529 (3)	1.03005 (9)	0.0450 (5)
C17	0.8176 (4)	0.7278 (4)	1.03257 (10)	0.0626 (7)
H17	0.9165	0.6951	1.0022	0.075*
C18	0.8846 (4)	0.7516 (4)	1.08031 (11)	0.0713 (8)
H18	1.0309	0.7321	1.0814	0.086*
C19	0.5476 (4)	0.8251 (4)	1.12229 (10)	0.0636 (7)
H19	0.4521	0.8590	1.1532	0.076*
C20	0.4667 (4)	0.8032 (4)	1.07641 (10)	0.0594 (7)
H20	0.3199	0.8225	1.0767	0.071*
O4	1.0439 (3)	0.9861 (3)	0.19590 (9)	0.0936 (7)
O5	0.8367 (4)	0.8213 (3)	0.22488 (7)	0.0878 (6)
H5A	0.8297	0.8234	0.1920	0.132*
C21	0.9595 (5)	0.9109 (4)	0.23256 (11)	0.0660 (7)
C22	0.9809 (6)	0.9134 (5)	0.29172 (12)	0.1010 (11)
H22A	1.1128	0.9314	0.2958	0.151*
H22B	0.9867	0.7924	0.3116	0.151*
H22C	0.8570	1.0181	0.3058	0.151*
O6	0.0290 (3)	0.7824 (3)	0.90528 (8)	0.0777 (6)
H6A	0.134 (4)	0.765 (4)	0.9249 (10)	0.117*
H6B	0.018 (5)	0.864 (4)	0.8768 (8)	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0937 (6)	0.1030 (6)	0.0582 (5)	−0.0225 (5)	0.0095 (4)	−0.0146 (4)
O1	0.0563 (12)	0.1292 (18)	0.0847 (15)	−0.0278 (12)	−0.0173 (10)	0.0215 (12)
O2	0.0556 (10)	0.0987 (13)	0.0469 (10)	−0.0248 (10)	−0.0071 (8)	−0.0053 (9)
O3	0.0446 (9)	0.0839 (12)	0.0618 (11)	−0.0325 (9)	−0.0085 (8)	−0.0052 (9)
N1	0.0542 (12)	0.0602 (12)	0.0502 (12)	−0.0289 (10)	−0.0117 (10)	−0.0023 (9)
N2	0.0512 (11)	0.0751 (13)	0.0467 (12)	−0.0376 (10)	−0.0089 (9)	−0.0021 (9)
N3	0.0690 (14)	0.0746 (14)	0.0544 (13)	−0.0382 (12)	−0.0109 (11)	−0.0031 (10)
C1	0.0660 (18)	0.117 (3)	0.0624 (19)	−0.0361 (17)	−0.0226 (15)	0.0082 (16)
C2	0.083 (2)	0.104 (2)	0.0537 (18)	−0.0337 (18)	−0.0217 (16)	0.0064 (15)
C3	0.0722 (17)	0.0602 (15)	0.0519 (15)	−0.0195 (14)	−0.0023 (13)	−0.0129 (12)
C4	0.0588 (17)	0.123 (3)	0.0561 (18)	−0.0247 (17)	−0.0066 (14)	−0.0115 (16)
C5	0.0655 (17)	0.107 (2)	0.0449 (15)	−0.0256 (16)	−0.0122 (13)	−0.0066 (14)
C6	0.0581 (15)	0.0588 (15)	0.0527 (15)	−0.0211 (12)	−0.0122 (12)	−0.0056 (11)
C7	0.0613 (17)	0.0715 (17)	0.0618 (17)	−0.0257 (14)	−0.0178 (14)	−0.0013 (13)
C8	0.0514 (14)	0.0650 (16)	0.0524 (15)	−0.0184 (13)	−0.0058 (12)	−0.0071 (12)
C9	0.0721 (17)	0.0750 (18)	0.0613 (17)	−0.0312 (15)	−0.0091 (14)	−0.0189 (13)
C10	0.0687 (17)	0.0780 (18)	0.0680 (18)	−0.0430 (15)	−0.0068 (14)	−0.0153 (14)
C11	0.0581 (15)	0.0636 (16)	0.0588 (16)	−0.0295 (13)	−0.0036 (12)	−0.0091 (12)
C12	0.0498 (13)	0.0557 (14)	0.0495 (14)	−0.0215 (11)	−0.0086 (11)	−0.0039 (11)
C13	0.0500 (14)	0.0720 (17)	0.0562 (16)	−0.0297 (13)	−0.0100 (12)	−0.0034 (12)
C14	0.0566 (15)	0.0740 (17)	0.0550 (16)	−0.0373 (13)	−0.0093 (12)	−0.0025 (12)
C15	0.0464 (13)	0.0474 (13)	0.0507 (14)	−0.0217 (11)	−0.0097 (11)	0.0034 (10)
C16	0.0433 (12)	0.0474 (13)	0.0475 (13)	−0.0231 (10)	−0.0060 (10)	0.0033 (10)
C17	0.0501 (14)	0.0955 (19)	0.0517 (15)	−0.0379 (14)	−0.0007 (11)	−0.0106 (13)
C18	0.0582 (16)	0.108 (2)	0.0625 (18)	−0.0458 (16)	−0.0087 (14)	−0.0108 (16)
C19	0.0685 (17)	0.0755 (18)	0.0487 (15)	−0.0307 (15)	0.0001 (12)	−0.0076 (12)
C20	0.0481 (14)	0.0770 (17)	0.0574 (16)	−0.0305 (13)	−0.0008 (12)	−0.0045 (13)
O4	0.0878 (14)	0.1262 (18)	0.0788 (14)	−0.0620 (14)	−0.0170 (11)	0.0218 (12)
O5	0.1197 (17)	0.1169 (16)	0.0548 (12)	−0.0778 (15)	−0.0107 (12)	0.0026 (12)
C21	0.0703 (18)	0.0653 (17)	0.0599 (17)	−0.0235 (15)	−0.0166 (14)	0.0033 (13)
C22	0.146 (3)	0.096 (2)	0.068 (2)	−0.049 (2)	−0.040 (2)	0.0006 (17)
O6	0.0587 (11)	0.1268 (17)	0.0607 (12)	−0.0549 (12)	−0.0152 (9)	0.0147 (11)

Geometric parameters (Å, º) top

Cl1—C3	1.736 (3)	C10—C11	1.375 (3)
O1—C7	1.194 (3)	C10—H10	0.9300
O2—C7	1.353 (3)	C11—C12	1.389 (3)
O2—C8	1.408 (3)	C11—H11	0.9300
O3—C15	1.218 (2)	C12—C13	1.385 (3)
N1—C14	1.271 (3)	C12—C14	1.456 (3)
N1—N2	1.373 (2)	C13—H13	0.9300
N2—C15	1.353 (3)	C14—H14	0.9300
N2—H2	0.8600	C15—C16	1.499 (3)
N3—C19	1.317 (3)	C16—C20	1.374 (3)
N3—C18	1.322 (3)	C16—C17	1.375 (3)
C1—C2	1.372 (4)	C17—C18	1.374 (3)
C1—C6	1.380 (3)	C17—H17	0.9300
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.356 (4)	C19—C20	1.373 (3)
C2—H2A	0.9300	C19—H19	0.9300
C3—C4	1.368 (3)	C20—H20	0.9300
C4—C5	1.374 (4)	O4—C21	1.200 (3)
C4—H4	0.9300	O5—C21	1.295 (3)
C5—C6	1.368 (3)	O5—H5A	0.8200
C5—H5	0.9300	C21—C22	1.494 (4)
C6—C7	1.476 (4)	C22—H22A	0.9600
C8—C9	1.372 (3)	C22—H22B	0.9600
C8—C13	1.373 (3)	C22—H22C	0.9600
C9—C10	1.379 (3)	O6—H6A	0.854 (10)
C9—H9	0.9300	O6—H6B	0.852 (10)

C7—O2—C8	119.8 (2)	C13—C12—C11	118.7 (2)
C14—N1—N2	116.74 (19)	C13—C12—C14	119.7 (2)
C15—N2—N1	117.92 (19)	C11—C12—C14	121.6 (2)
C15—N2—H2	121.0	C8—C13—C12	120.2 (2)
N1—N2—H2	121.0	C8—C13—H13	119.9
C19—N3—C18	116.7 (2)	C12—C13—H13	119.9
C2—C1—C6	121.2 (3)	N1—C14—C12	121.0 (2)
C2—C1—H1	119.4	N1—C14—H14	119.5
C6—C1—H1	119.4	C12—C14—H14	119.5
C3—C2—C1	119.2 (3)	O3—C15—N2	123.0 (2)
C3—C2—H2A	120.4	O3—C15—C16	121.0 (2)
C1—C2—H2A	120.4	N2—C15—C16	116.0 (2)
C2—C3—C4	120.9 (3)	C20—C16—C17	116.8 (2)
C2—C3—Cl1	119.7 (2)	C20—C16—C15	117.7 (2)
C4—C3—Cl1	119.4 (2)	C17—C16—C15	125.5 (2)
C3—C4—C5	119.5 (3)	C18—C17—C16	119.4 (2)
C3—C4—H4	120.2	C18—C17—H17	120.3
C5—C4—H4	120.2	C16—C17—H17	120.3
C6—C5—C4	120.8 (2)	N3—C18—C17	123.8 (2)
C6—C5—H5	119.6	N3—C18—H18	118.1
C4—C5—H5	119.6	C17—C18—H18	118.1
C5—C6—C1	118.4 (3)	N3—C19—C20	123.4 (2)
C5—C6—C7	123.2 (2)	N3—C19—H19	118.3
C1—C6—C7	118.4 (2)	C20—C19—H19	118.3
O1—C7—O2	123.4 (3)	C19—C20—C16	119.9 (2)
O1—C7—C6	125.3 (2)	C19—C20—H20	120.0
O2—C7—C6	111.3 (2)	C16—C20—H20	120.0
C9—C8—C13	121.3 (2)	C21—O5—H5A	109.5
C9—C8—O2	122.2 (2)	O4—C21—O5	123.3 (3)
C13—C8—O2	116.3 (2)	O4—C21—C22	123.9 (3)
C8—C9—C10	118.7 (2)	O5—C21—C22	112.8 (3)
C8—C9—H9	120.6	C21—C22—H22A	109.5
C10—C9—H9	120.6	C21—C22—H22B	109.5
C11—C10—C9	120.8 (2)	H22A—C22—H22B	109.5
C11—C10—H10	119.6	C21—C22—H22C	109.5
C9—C10—H10	119.6	H22A—C22—H22C	109.5
C10—C11—C12	120.3 (2)	H22B—C22—H22C	109.5
C10—C11—H11	119.9	H6A—O6—H6B	115.3 (17)
C12—C11—H11	119.9

C14—N1—N2—C15	172.9 (2)	C10—C11—C12—C13	1.8 (3)
C6—C1—C2—C3	0.4 (5)	C10—C11—C12—C14	−177.3 (2)
C1—C2—C3—C4	−0.5 (5)	C9—C8—C13—C12	−0.6 (4)
C1—C2—C3—Cl1	−178.9 (2)	O2—C8—C13—C12	−175.4 (2)
C2—C3—C4—C5	0.5 (5)	C11—C12—C13—C8	−1.0 (3)
Cl1—C3—C4—C5	178.9 (2)	C14—C12—C13—C8	178.0 (2)
C3—C4—C5—C6	−0.4 (5)	N2—N1—C14—C12	177.86 (19)
C4—C5—C6—C1	0.3 (4)	C13—C12—C14—N1	174.2 (2)
C4—C5—C6—C7	−177.9 (3)	C11—C12—C14—N1	−6.7 (4)
C2—C1—C6—C5	−0.3 (5)	N1—N2—C15—O3	−2.7 (3)
C2—C1—C6—C7	178.1 (3)	N1—N2—C15—C16	177.73 (18)
C8—O2—C7—O1	2.7 (4)	O3—C15—C16—C20	−11.2 (3)
C8—O2—C7—C6	−178.4 (2)	N2—C15—C16—C20	168.4 (2)
C5—C6—C7—O1	166.5 (3)	O3—C15—C16—C17	167.4 (2)
C1—C6—C7—O1	−11.8 (4)	N2—C15—C16—C17	−13.0 (3)
C5—C6—C7—O2	−12.4 (4)	C20—C16—C17—C18	0.7 (4)
C1—C6—C7—O2	169.4 (2)	C15—C16—C17—C18	−178.0 (2)
C7—O2—C8—C9	50.5 (3)	C19—N3—C18—C17	0.7 (4)
C7—O2—C8—C13	−134.6 (2)	C16—C17—C18—N3	−1.0 (4)
C13—C8—C9—C10	1.4 (4)	C18—N3—C19—C20	−0.3 (4)
O2—C8—C9—C10	176.0 (2)	N3—C19—C20—C16	0.1 (4)
C8—C9—C10—C11	−0.6 (4)	C17—C16—C20—C19	−0.3 (3)
C9—C10—C11—C12	−1.0 (4)	C15—C16—C20—C19	178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3	0.86 (3)	2.00 (3)	2.843 (2)	166 (2)
O6—H6B···O4ⁱ	0.86 (2)	1.98 (2)	2.812 (3)	165 (3)
O5—H5A···N3ⁱⁱ	0.82	1.85	2.646 (3)	164
N2—H2···O6ⁱⁱⁱ	0.86	2.04	2.879 (2)	164
C14—H14···O6ⁱⁱⁱ	0.93	2.59	3.367 (4)	141
C17—H17···O6ⁱⁱⁱ	0.93	2.50	3.331 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄ClN₃O₃·C₂H₄O₂·H₂O
M_r	457.86
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	6.6666 (15), 7.5437 (17), 24.781 (6)
α, β, γ (°)	81.526 (4), 82.969 (4), 66.632 (4)
V (Å³)	1128.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.18 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	5755, 3936, 2501
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.119, 1.03
No. of reflections	3936
No. of parameters	298
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3	0.86 (3)	2.00 (3)	2.843 (2)	166 (2)
O6—H6B···O4ⁱ	0.86 (2)	1.98 (2)	2.812 (3)	165 (3)
O5—H5A···N3ⁱⁱ	0.82	1.85	2.646 (3)	164
N2—H2···O6ⁱⁱⁱ	0.86	2.04	2.879 (2)	164
C14—H14···O6ⁱⁱⁱ	0.93	2.59	3.367 (4)	141
C17—H17···O6ⁱⁱⁱ	0.93	2.50	3.331 (3)	149

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diao, C.-H., Fan, Z. & Chen, X. (2007). Acta Cryst. C63, o717–o719. Web of Science CSD CrossRef IUCr Journals Google Scholar
Peralta, M. A., Souza, M. N. V. de, Wardell, S. M. S. V., Wardell, J. L., Low, J. N. & Glidewell, C. (2007). Acta Cryst. C63, o68–o72. Web of Science CSD CrossRef IUCr Journals Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Souza, M. V. N. de, Wardell, S. M. S. V., Wardell, J. L., Low, J. N. & Glidewell, C. (2007). Acta Cryst. C63, o166–o168. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wardell, S. M. S. V., Souza, M. V. N. de, Wardell, J. L., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o683–o689. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page o1517

doi:10.1107/S1600536812017369

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-[3-(4-Chloro­benzo­yl­oxy)benzyl­­idene]pyridine-4-carbohydrazide acetic acid monosolvate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-[3-(4-Chlorobenzoyloxy)benzylidene]pyridine-4-carbohydrazide acetic acid monosolvate monohydrate