(E)-N'-[3-(4-Chloro-benzo-yloxy)benzyl-idene]pyridine-4-carbohydrazide acetic acid monosolvate monohydrate.

In the Schiff base mol-ecule of the title compound, C(20)H(14)ClN(3)O(3)·CH(3)COOH·H(2)O, the central benzene ring makes dihedral angles of 36.26 (7) and 27.59 (8)°, respectively, with the terminal chloro-phenyl 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 = 457.86

Triclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.03

3936 reflections

298 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

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.

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

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

C20H14ClN3O3·C2H4O2·H2O	Z = 2
Mr = 457.86	F(000) = 476
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0473P)2 + 0.2041P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3936 reflections	Δρmax = 0.15 e Å−3
298 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .