2′-[1-(4-Chloro-2-hydroxyphenyl)ethylidene]benzenesulfonohydrazide

Two mol­ecules of the title compound, C₁₄H₁₃ClN₂O₃S, are linked by two N—H...O_sulfon­yl hydrogen bonds about a center of inversion to furnish a hydrogen-bonded dimer.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.112
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT414_ALERT_2_B Short Intra D-H..H-X       H1N    ..  H7A     ..       1.85 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1     ..  C4      ..       2.91 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C2     ..  C2      ..       2.99 Ang.

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            Faint
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT411_ALERT_2_C Short Inter H...H Contact  H2     ..  H2      ..       2.10 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C3      ..       2.92 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C2     ..  C3      ..       3.12 Ang.

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

2'-(4-Chloro-2-hydroxyphenyl-1-ethylidene)benzenesulfonohydrazide

Crystal data

C14H13ClN2O3S	F(000) = 672
Mr = 324.77	Dx = 1.541 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 6589 reflections
a = 10.8711 (2) Å	θ = 2.6–32.3°
b = 5.7438 (1) Å	µ = 0.43 mm^−1
c = 22.4374 (4) Å	T = 173 K
β = 92.253 (1)°	Plate, faint yellow
V = 1399.94 (4) Å^3	0.45 × 0.14 × 0.06 mm
Z = 4

Data collection

Bruker APEXII diffractometer	3210 independent reflections
Radiation source: medium-focus sealed tube	2654 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.833, Tmax = 0.975	k = −7→7
20538 measured reflections	l = −29→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0611P)^2 + 0.7441P] where P = (Fo^2 + 2Fc^2)/3
3210 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.46 e Å^−3
2 restraints	Δρmin = −0.48 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S11	0.43700 (4)	0.39317 (8)	0.59182 (2)	0.01243 (13)
Cl1	−0.11349 (5)	1.53477 (9)	0.57969 (2)	0.02519 (16)
O1	0.14739 (14)	0.7311 (3)	0.68532 (7)	0.0212 (3)
O2	0.50840 (13)	0.2851 (2)	0.54648 (6)	0.0165 (3)
O3	0.36528 (13)	0.2497 (2)	0.62915 (6)	0.0174 (3)
N1	0.34439 (15)	0.5668 (3)	0.55328 (7)	0.0147 (3)
N2	0.26178 (15)	0.6920 (3)	0.58685 (7)	0.0142 (3)
C1	0.53514 (17)	0.5661 (3)	0.63788 (9)	0.0138 (4)
C2	0.57033 (19)	0.4825 (4)	0.69400 (9)	0.0179 (4)
H2	0.5387	0.3392	0.7079	0.022*
C3	0.65264 (19)	0.6119 (4)	0.72949 (10)	0.0222 (5)
H3	0.6785	0.5561	0.7678	0.027*
C4	0.6970 (2)	0.8225 (4)	0.70898 (10)	0.0238 (5)
H4	0.7524	0.9114	0.7336	0.029*
C5	0.6610 (2)	0.9038 (4)	0.65291 (10)	0.0232 (5)
H5	0.6920	1.0480	0.6392	0.028*
C6	0.57983 (18)	0.7758 (4)	0.61655 (10)	0.0183 (4)
H6	0.5553	0.8303	0.5779	0.022*
C7	0.2348 (2)	0.9688 (4)	0.50296 (9)	0.0197 (4)
H7A	0.2953	0.8694	0.4840	0.030*
H7B	0.2675	1.1272	0.5070	0.030*
H7C	0.1584	0.9715	0.4783	0.030*
C8	0.20904 (17)	0.8739 (3)	0.56357 (8)	0.0131 (4)
C9	0.11810 (17)	0.9921 (3)	0.60037 (9)	0.0135 (4)
C10	0.09194 (18)	0.9174 (3)	0.65861 (9)	0.0157 (4)
C11	0.00572 (19)	1.0363 (4)	0.69126 (9)	0.0190 (4)
H11	−0.0100	0.9862	0.7306	0.023*
C12	−0.05753 (18)	1.2256 (4)	0.66767 (9)	0.0182 (4)
H12	−0.1170	1.3043	0.6901	0.022*
C13	−0.03243 (18)	1.2986 (3)	0.61049 (9)	0.0165 (4)
C14	0.05416 (18)	1.1869 (3)	0.57741 (9)	0.0157 (4)
H14	0.0707	1.2424	0.5387	0.019*
H1O	0.190 (2)	0.673 (5)	0.6589 (10)	0.040 (8)*
H1N	0.377 (2)	0.626 (4)	0.5228 (8)	0.029 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S11	0.0138 (2)	0.0115 (2)	0.0120 (2)	0.00100 (16)	0.00102 (17)	0.00066 (17)
Cl1	0.0270 (3)	0.0204 (3)	0.0282 (3)	0.0106 (2)	0.0017 (2)	0.0009 (2)
O1	0.0242 (8)	0.0237 (8)	0.0162 (7)	0.0071 (6)	0.0048 (6)	0.0049 (6)
O2	0.0209 (7)	0.0144 (7)	0.0144 (7)	0.0044 (5)	0.0025 (6)	−0.0004 (5)
O3	0.0192 (7)	0.0167 (7)	0.0162 (7)	−0.0037 (6)	0.0013 (6)	0.0031 (6)
N1	0.0152 (8)	0.0163 (8)	0.0128 (8)	0.0044 (6)	0.0023 (6)	0.0028 (6)
N2	0.0129 (8)	0.0157 (8)	0.0142 (8)	0.0014 (6)	0.0020 (6)	−0.0017 (6)
C1	0.0116 (9)	0.0154 (9)	0.0145 (9)	0.0017 (7)	0.0017 (7)	−0.0029 (7)
C2	0.0182 (10)	0.0201 (10)	0.0157 (10)	0.0011 (8)	0.0030 (8)	0.0011 (8)
C3	0.0194 (10)	0.0315 (12)	0.0156 (10)	0.0041 (9)	−0.0009 (8)	−0.0044 (9)
C4	0.0176 (10)	0.0283 (11)	0.0254 (11)	−0.0010 (9)	0.0009 (8)	−0.0120 (9)
C5	0.0208 (10)	0.0177 (10)	0.0314 (12)	−0.0029 (8)	0.0047 (9)	−0.0032 (9)
C6	0.0170 (10)	0.0175 (10)	0.0205 (10)	0.0006 (8)	0.0019 (8)	0.0011 (8)
C7	0.0207 (10)	0.0209 (10)	0.0178 (10)	0.0052 (8)	0.0042 (8)	0.0040 (8)
C8	0.0114 (9)	0.0137 (9)	0.0139 (9)	−0.0020 (7)	−0.0008 (7)	0.0000 (7)
C9	0.0112 (9)	0.0152 (9)	0.0139 (9)	−0.0020 (7)	−0.0002 (7)	−0.0019 (7)
C10	0.0132 (9)	0.0173 (9)	0.0163 (10)	−0.0010 (7)	−0.0012 (7)	0.0001 (8)
C11	0.0186 (10)	0.0240 (10)	0.0145 (10)	−0.0005 (8)	0.0023 (8)	0.0009 (8)
C12	0.0140 (9)	0.0216 (10)	0.0192 (10)	0.0016 (8)	0.0013 (8)	−0.0060 (8)
C13	0.0150 (9)	0.0135 (9)	0.0208 (10)	0.0016 (7)	−0.0025 (8)	−0.0016 (8)
C14	0.0162 (9)	0.0158 (9)	0.0152 (9)	−0.0001 (7)	0.0011 (7)	−0.0001 (7)

Geometric parameters (Å, º)

S11—O3	1.4283 (14)	C5—C6	1.389 (3)
S11—O2	1.4439 (14)	C5—H5	0.9500
S11—N1	1.6394 (17)	C6—H6	0.9500
S11—C1	1.763 (2)	C7—C8	1.502 (3)
Cl1—C13	1.746 (2)	C7—H7A	0.9800
O1—C10	1.356 (2)	C7—H7B	0.9800
O1—H1O	0.840 (10)	C7—H7C	0.9800
N1—N2	1.394 (2)	C8—C9	1.478 (3)
N1—H1N	0.851 (10)	C9—C14	1.404 (3)
N2—C8	1.292 (2)	C9—C10	1.415 (3)
C1—C2	1.387 (3)	C10—C11	1.391 (3)
C1—C6	1.391 (3)	C11—C12	1.381 (3)
C2—C3	1.389 (3)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.387 (3)
C3—C4	1.388 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.380 (3)
C4—C5	1.384 (3)	C14—H14	0.9500
C4—H4	0.9500
O3—S11—O2	119.08 (9)	C1—C6—H6	120.7
O3—S11—N1	108.80 (9)	C8—C7—H7A	109.5
O2—S11—N1	103.06 (8)	C8—C7—H7B	109.5
O3—S11—C1	108.24 (9)	H7A—C7—H7B	109.5
O2—S11—C1	109.01 (9)	C8—C7—H7C	109.5
N1—S11—C1	108.15 (9)	H7A—C7—H7C	109.5
C10—O1—H1O	105 (2)	H7B—C7—H7C	109.5
N2—N1—S11	115.09 (13)	N2—C8—C9	116.21 (17)
N2—N1—H1N	121.6 (18)	N2—C8—C7	124.32 (18)
S11—N1—H1N	113.7 (18)	C9—C8—C7	119.47 (17)
C8—N2—N1	118.92 (16)	C14—C9—C10	117.77 (18)
C2—C1—C6	121.64 (19)	C14—C9—C8	119.56 (17)
C2—C1—S11	118.43 (15)	C10—C9—C8	122.67 (17)
C6—C1—S11	119.86 (16)	O1—C10—C11	116.85 (18)
C1—C2—C3	118.92 (19)	O1—C10—C9	123.06 (18)
C1—C2—H2	120.5	C11—C10—C9	120.09 (18)
C3—C2—H2	120.5	C12—C11—C10	121.36 (19)
C4—C3—C2	120.0 (2)	C12—C11—H11	119.3
C4—C3—H3	120.0	C10—C11—H11	119.3
C2—C3—H3	120.0	C11—C12—C13	118.65 (18)
C5—C4—C3	120.4 (2)	C11—C12—H12	120.7
C5—C4—H4	119.8	C13—C12—H12	120.7
C3—C4—H4	119.8	C14—C13—C12	121.36 (18)
C4—C5—C6	120.4 (2)	C14—C13—Cl1	119.53 (16)
C4—C5—H5	119.8	C12—C13—Cl1	119.11 (15)
C6—C5—H5	119.8	C13—C14—C9	120.75 (18)
C5—C6—C1	118.6 (2)	C13—C14—H14	119.6
C5—C6—H6	120.7	C9—C14—H14	119.6
O3—S11—N1—N2	51.48 (15)	N1—N2—C8—C7	−3.0 (3)
O2—S11—N1—N2	178.78 (13)	N2—C8—C9—C14	−178.07 (17)
C1—S11—N1—N2	−65.88 (15)	C7—C8—C9—C14	2.0 (3)
S11—N1—N2—C8	161.92 (14)	N2—C8—C9—C10	2.0 (3)
O3—S11—C1—C2	27.08 (18)	C7—C8—C9—C10	−177.92 (18)
O2—S11—C1—C2	−103.83 (17)	C14—C9—C10—O1	179.68 (18)
N1—S11—C1—C2	144.79 (16)	C8—C9—C10—O1	−0.4 (3)
O3—S11—C1—C6	−155.89 (15)	C14—C9—C10—C11	−0.2 (3)
O2—S11—C1—C6	73.20 (17)	C8—C9—C10—C11	179.72 (18)
N1—S11—C1—C6	−38.18 (18)	O1—C10—C11—C12	−178.78 (18)
C6—C1—C2—C3	−0.2 (3)	C9—C10—C11—C12	1.2 (3)
S11—C1—C2—C3	176.75 (15)	C10—C11—C12—C13	−0.9 (3)
C1—C2—C3—C4	0.9 (3)	C11—C12—C13—C14	−0.3 (3)
C2—C3—C4—C5	−0.8 (3)	C11—C12—C13—Cl1	178.99 (16)
C3—C4—C5—C6	0.2 (3)	C12—C13—C14—C9	1.2 (3)
C4—C5—C6—C1	0.5 (3)	Cl1—C13—C14—C9	−178.08 (15)
C2—C1—C6—C5	−0.4 (3)	C10—C9—C14—C13	−0.9 (3)
S11—C1—C6—C5	−177.36 (15)	C8—C9—C14—C13	179.11 (18)
N1—N2—C8—C9	177.17 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2	0.84 (1)	1.82 (2)	2.587 (2)	150 (3)
N1—H1n···O2^i	0.85 (1)	2.10 (1)	2.929 (2)	166 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.