Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033168/dn2215sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033168/dn2215Isup2.hkl |
CCDC reference: 657802
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
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 Uiso(H) = 1.2Ueq(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 Uiso(H) = 1.5Ueq(O).
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).
For related compounds see: Yin & Chen (2006).
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).
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) Å3 | Block, colourless |
Z = 4 | 0.63 × 0.13 × 0.10 mm |
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 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) = 0.095 | w = 1/[σ2(Fo2) + (0.0396P)2] where P = (Fo2 + 2Fc2)/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) |
C15H13ClN2O3·H2O | V = 1440.7 (5) Å3 |
Mr = 322.74 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.8651 (16) Å | µ = 0.29 mm−1 |
b = 12.9403 (17) Å | T = 298 K |
c = 22.884 (3) Å | 0.63 × 0.13 × 0.10 mm |
CCD area-detector diffractometer | 2522 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1689 reflections with I > 2σ(I) |
Tmin = 0.841, Tmax = 0.972 | Rint = 0.065 |
7353 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | Δρmax = 0.20 e Å−3 |
S = 0.97 | Δρmin = −0.21 e Å−3 |
2522 reflections | Absolute structure: Flack (1983), 1003 Friedel pairs |
208 parameters | Absolute structure parameter: 0.08 (10) |
3 restraints |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 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···O2ii | 0.85 (3) | 2.36 (3) | 3.057 (4) | 140 (3) |
O4—H17···O3ii | 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. |
Experimental details
Crystal data | |
Chemical formula | C15H13ClN2O3·H2O |
Mr | 322.74 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 4.8651 (16), 12.9403 (17), 22.884 (3) |
V (Å3) | 1440.7 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.63 × 0.13 × 0.10 |
Data collection | |
Diffractometer | CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.841, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7353, 2522, 1689 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.095, 0.97 |
No. of reflections | 2522 |
No. of parameters | 208 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.21 |
Absolute structure | Flack (1983), 1003 Friedel pairs |
Absolute structure parameter | 0.08 (10) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); PLATON (Spek, 2003), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.86 | 2.06 | 2.903 (3) | 165.0 |
O2—H2···N2 | 0.82 | 1.99 | 2.694 (3) | 143.6 |
O2—H2···O4 | 0.82 | 2.64 | 3.040 (4) | 112.0 |
O4—H16···O1 | 0.84 (3) | 1.914 (18) | 2.725 (3) | 161 (4) |
O4—H17···O2ii | 0.85 (3) | 2.36 (3) | 3.057 (4) | 140 (3) |
O4—H17···O3ii | 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. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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).