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The asymmetric unit of the title compound, C13H9Cl2N3O2·H2O, consists of a Schiff base mol­ecule and a solvent water mol­ecule. The Schiff base mol­ecule is approximately planar and displays a trans configuration with respect to the C=N double bond. The crystal structure is stabilized by inter­molecular N—H...O, O—H...O, C—H...N, and C—H...O hydrogen bonds, forming a network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035811/sj2118sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035811/sj2118Isup2.hkl
Contains datablock I

CCDC reference: 624989

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.079
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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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 26.48 From the CIF: _reflns_number_total 2831 Count of symmetry unique reflns 1498 Completeness (_total/calc) 188.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1333 Fraction of Friedel pairs measured 0.890 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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 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, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

2'-[1-(3,5-Dichloro-2-hydroxyphenyl)methylidene]isonicotinohydrazide monohydrate top
Crystal data top
C13H9Cl2N3O2·H2OF(000) = 336
Mr = 328.15Dx = 1.558 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2023 reflections
a = 3.887 (1) Åθ = 2.2–25.3°
b = 13.638 (2) ŵ = 0.48 mm1
c = 13.231 (2) ÅT = 298 K
β = 94.546 (2)°Plate, yellow
V = 699.2 (2) Å30.27 × 0.20 × 0.08 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
2831 independent reflections
Radiation source: fine-focus sealed tube2544 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 26.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 44
Tmin = 0.882, Tmax = 0.963k = 1716
5674 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0386P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2831 reflectionsΔρmax = 0.20 e Å3
200 parametersΔρmin = 0.18 e Å3
5 restraintsAbsolute structure: Flack (1983), 1334 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (6)
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
xyzUiso*/Ueq
Cl10.07913 (18)0.44139 (5)0.06095 (4)0.0566 (2)
Cl20.04126 (17)0.81937 (5)0.16325 (5)0.05529 (19)
O10.3599 (5)0.76380 (13)0.34784 (13)0.0508 (5)
H10.45670.74460.40150.076*
O20.8904 (6)0.77859 (14)0.60033 (14)0.0630 (6)
O30.9592 (6)0.91318 (14)0.44046 (15)0.0672 (6)
N10.7014 (5)0.64091 (17)0.46519 (14)0.0433 (5)
N20.8925 (5)0.61886 (16)0.55450 (15)0.0428 (5)
N31.5082 (5)0.62932 (18)0.90787 (15)0.0468 (5)
C10.4171 (6)0.59183 (18)0.30808 (17)0.0374 (5)
C20.2997 (6)0.68703 (18)0.28483 (16)0.0359 (5)
C30.1100 (6)0.70221 (18)0.19224 (17)0.0384 (5)
C40.0416 (6)0.62775 (19)0.12375 (17)0.0375 (5)
H40.08440.63950.06220.045*
C50.1637 (6)0.53534 (18)0.14820 (17)0.0390 (5)
C60.3469 (6)0.51603 (18)0.23913 (17)0.0400 (6)
H60.42350.45280.25450.048*
C70.6201 (6)0.57092 (19)0.40369 (17)0.0419 (6)
H70.68930.50710.41950.050*
C80.9743 (6)0.69402 (19)0.61934 (17)0.0418 (6)
C91.1685 (6)0.66692 (17)0.71766 (17)0.0358 (5)
C101.2112 (7)0.73894 (19)0.79069 (19)0.0453 (6)
H101.12650.80180.77760.054*
C111.3806 (7)0.7167 (2)0.88319 (18)0.0497 (6)
H111.40690.76640.93140.060*
C121.4706 (6)0.5606 (2)0.83668 (19)0.0464 (6)
H121.56330.49900.85170.056*
C131.3026 (6)0.57472 (18)0.74182 (17)0.0424 (6)
H131.27990.52360.69520.051*
H20.952 (8)0.5566 (10)0.568 (2)0.080*
H3B0.920 (8)0.880 (2)0.4918 (16)0.080*
H3A1.112 (7)0.885 (2)0.409 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0775 (5)0.0463 (4)0.0436 (3)0.0087 (3)0.0111 (3)0.0093 (3)
Cl20.0675 (4)0.0409 (3)0.0550 (4)0.0058 (3)0.0099 (3)0.0109 (3)
O10.0670 (12)0.0444 (10)0.0381 (10)0.0030 (9)0.0138 (8)0.0062 (8)
O20.0927 (15)0.0499 (12)0.0430 (10)0.0145 (10)0.0145 (10)0.0074 (9)
O30.1035 (19)0.0423 (13)0.0547 (12)0.0009 (10)0.0000 (11)0.0047 (9)
N10.0451 (12)0.0558 (13)0.0277 (10)0.0017 (10)0.0057 (9)0.0035 (9)
N20.0505 (12)0.0491 (13)0.0268 (10)0.0035 (10)0.0095 (9)0.0031 (10)
N30.0496 (12)0.0544 (13)0.0342 (11)0.0029 (10)0.0105 (9)0.0030 (10)
C10.0384 (12)0.0472 (15)0.0264 (11)0.0003 (11)0.0007 (9)0.0040 (10)
C20.0372 (12)0.0403 (13)0.0294 (12)0.0037 (10)0.0031 (9)0.0016 (10)
C30.0404 (13)0.0355 (13)0.0386 (13)0.0003 (10)0.0016 (10)0.0086 (10)
C40.0394 (12)0.0460 (13)0.0254 (11)0.0070 (10)0.0078 (9)0.0048 (10)
C50.0401 (13)0.0436 (14)0.0325 (12)0.0086 (11)0.0014 (10)0.0020 (10)
C60.0432 (13)0.0405 (14)0.0354 (13)0.0008 (10)0.0032 (10)0.0007 (10)
C70.0473 (14)0.0471 (15)0.0301 (12)0.0022 (12)0.0037 (10)0.0050 (11)
C80.0473 (14)0.0439 (14)0.0335 (13)0.0023 (12)0.0007 (10)0.0066 (11)
C90.0374 (12)0.0415 (14)0.0277 (11)0.0037 (10)0.0035 (9)0.0046 (9)
C100.0548 (16)0.0375 (14)0.0423 (14)0.0002 (12)0.0040 (11)0.0001 (11)
C110.0632 (16)0.0492 (16)0.0346 (14)0.0036 (13)0.0100 (12)0.0067 (12)
C120.0496 (15)0.0441 (15)0.0438 (14)0.0027 (12)0.0079 (12)0.0062 (12)
C130.0533 (14)0.0384 (13)0.0338 (13)0.0011 (11)0.0070 (11)0.0028 (11)
Geometric parameters (Å, º) top
Cl1—C51.738 (2)C2—C31.394 (3)
Cl2—C31.735 (2)C3—C41.373 (3)
O1—C21.347 (3)C4—C51.376 (4)
O1—H10.8200C4—H40.9300
O2—C81.219 (3)C5—C61.374 (3)
O3—H3B0.842 (10)C6—H60.9300
O3—H3A0.84 (3)C7—H70.9300
N1—C71.278 (3)C8—C91.498 (3)
N1—N21.378 (3)C9—C101.379 (3)
N2—C81.358 (3)C9—C131.389 (3)
N2—H20.894 (10)C10—C111.377 (3)
N3—C111.322 (3)C10—H100.9300
N3—C121.329 (3)C11—H110.9300
C1—C61.391 (3)C12—C131.381 (3)
C1—C21.402 (3)C12—H120.9300
C1—C71.465 (3)C13—H130.9300
C2—O1—H1109.5C5—C6—H6120.2
H3B—O3—H3A110 (2)C1—C6—H6120.2
C7—N1—N2118.2 (2)N1—C7—C1119.6 (2)
C8—N2—N1117.4 (2)N1—C7—H7120.2
C8—N2—H2123 (2)C1—C7—H7120.2
N1—N2—H2119 (2)O2—C8—N2122.6 (2)
C11—N3—C12116.3 (2)O2—C8—C9121.4 (2)
C6—C1—C2120.0 (2)N2—C8—C9116.0 (2)
C6—C1—C7119.1 (2)C10—C9—C13117.5 (2)
C2—C1—C7120.9 (2)C10—C9—C8117.2 (2)
O1—C2—C3118.8 (2)C13—C9—C8125.3 (2)
O1—C2—C1123.10 (19)C11—C10—C9119.3 (2)
C3—C2—C1118.1 (2)C11—C10—H10120.4
C4—C3—C2122.1 (2)C9—C10—H10120.4
C4—C3—Cl2119.39 (17)N3—C11—C10124.2 (2)
C2—C3—Cl2118.51 (19)N3—C11—H11117.9
C3—C4—C5118.5 (2)C10—C11—H11117.9
C3—C4—H4120.8N3—C12—C13124.3 (3)
C5—C4—H4120.8N3—C12—H12117.8
C6—C5—C4121.8 (2)C13—C12—H12117.8
C6—C5—Cl1119.86 (19)C12—C13—C9118.5 (2)
C4—C5—Cl1118.38 (18)C12—C13—H13120.8
C5—C6—C1119.5 (2)C9—C13—H13120.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.580 (3)145
N2—H2···O3i0.89 (2)1.99 (2)2.863 (3)165
O3—H3A···O1ii0.84 (3)2.11 (3)2.895 (3)155
O3—H3B···O20.84 (2)2.00 (2)2.829 (3)167 (3)
C4—H4···N3iii0.932.493.394 (3)165
C7—H7···O3i0.932.563.320 (3)140
C13—H13···O3i0.932.473.364 (3)162
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x+1, y, z; (iii) x2, y, z1.
 

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