2′-[1-(2-Hydroxy­phen­yl)ethyl­idene]benzene­sulfonohydrazide

Ali, H.M.; Laila, M.; Wan Jefrey, B.; Ng, S.W.

doi:10.1107/S160053680700952X

2′-[1-(2-Hydroxyphenyl)ethylidene]benzenesulfonohydrazide

H. M. Ali, M. Laila, B. Wan Jefrey and S. W. Ng

The molecules of the title compound, C₁₄H₁₄N₂O₃S are, linked by an N—H

O_sulfonyl hydrogen bond into a chain.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700952X/hb2307sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680700952X/hb2307Isup2.hkl Contains datablock I

CCDC reference: 643003

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.031
wR factor = 0.106
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.772     0.916
            Tmin(prime) and Tmax expected:      0.883     0.914
            RR(prime) =      0.872
            Please check that your absorption correction is appropriate.
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            Faint
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87

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

   1 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
   2 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

Computing details top

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'-[1-(2-Hydroxyphenyl)ethylidene]benzenesulfonohydrazide top

Crystal data top

C₁₄H₁₄N₂O₃S	F(000) = 608
M_r = 290.33	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5143 reflections
a = 5.1821 (1) Å	θ = 3–34.2°
b = 13.3799 (2) Å	µ = 0.24 mm⁻¹
c = 19.9277 (4) Å	T = 173 K
β = 91.973 (1)°	Block, faint yellow
V = 1380.89 (4) Å³	0.50 × 0.40 × 0.37 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3171 independent reflections
Radiation source: medium-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.772, T_max = 0.916	k = −16→17
13444 measured reflections	l = −25→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0578P)² + 0.6609P] where P = (F_o² + 2F_c²)/3
3171 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.40 e Å⁻³
2 restraints	Δρ_min = −0.47 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.71144 (6)	0.35885 (2)	0.511686 (16)	0.01513 (12)
O1	0.44963 (19)	0.35013 (8)	0.48699 (5)	0.0225 (2)
O2	0.7934 (2)	0.44171 (7)	0.55251 (5)	0.0233 (2)
O3	0.5576 (2)	0.14049 (7)	0.36472 (5)	0.0226 (2)
H3o	0.622 (4)	0.1872 (13)	0.3890 (10)	0.047 (6)*
N1	0.8930 (2)	0.36583 (8)	0.44564 (6)	0.0163 (2)
H1n	1.048 (2)	0.3805 (14)	0.4558 (9)	0.029 (5)*
N2	0.8496 (2)	0.28740 (8)	0.40066 (5)	0.0155 (2)
C1	0.7853 (2)	0.24698 (10)	0.55488 (6)	0.0169 (3)
C2	0.9955 (3)	0.24478 (12)	0.60037 (7)	0.0245 (3)
H2	1.1017	0.3020	0.6071	0.029*
C3	1.0464 (3)	0.15684 (14)	0.63570 (9)	0.0335 (4)
H3	1.1887	0.1538	0.6670	0.040*
C4	0.6835 (3)	0.07667 (12)	0.57976 (9)	0.0335 (4)
H4	0.5789	0.0190	0.5728	0.040*
C5	0.8912 (3)	0.07396 (13)	0.62558 (9)	0.0358 (4)
H5	0.9270	0.0145	0.6502	0.043*
C6	0.6287 (3)	0.16378 (11)	0.54400 (8)	0.0241 (3)
H6	0.4865	0.1664	0.5127	0.029*
C7	1.1955 (3)	0.35527 (10)	0.33186 (7)	0.0188 (3)
H7A	1.1729	0.4166	0.3578	0.028*
H7B	1.1863	0.3710	0.2838	0.028*
H7C	1.3642	0.3258	0.3436	0.028*
C8	0.9857 (2)	0.28223 (9)	0.34768 (6)	0.0150 (3)
C9	0.9196 (2)	0.19960 (9)	0.30089 (6)	0.0160 (3)
C10	1.0673 (3)	0.18340 (11)	0.24416 (7)	0.0209 (3)
H10	1.2099	0.2260	0.2365	0.025*
C11	1.0113 (3)	0.10712 (11)	0.19898 (7)	0.0243 (3)
H11	1.1154	0.0974	0.1612	0.029*
C12	0.8017 (3)	0.04493 (11)	0.20932 (7)	0.0244 (3)
H12	0.7610	−0.0070	0.1782	0.029*
C13	0.6520 (3)	0.05825 (10)	0.26478 (7)	0.0222 (3)
H13	0.5087	0.0156	0.2715	0.027*
C14	0.7104 (3)	0.13409 (10)	0.31100 (7)	0.0173 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01641 (19)	0.01291 (18)	0.01627 (18)	0.00021 (10)	0.00357 (12)	0.00030 (10)
O1	0.0156 (5)	0.0253 (5)	0.0270 (5)	0.0033 (4)	0.0027 (4)	0.0057 (4)
O2	0.0348 (6)	0.0156 (5)	0.0198 (5)	−0.0034 (4)	0.0077 (4)	−0.0039 (4)
O3	0.0239 (5)	0.0200 (5)	0.0245 (5)	−0.0073 (4)	0.0074 (4)	−0.0053 (4)
N1	0.0172 (6)	0.0157 (5)	0.0162 (5)	−0.0044 (4)	0.0029 (4)	−0.0026 (4)
N2	0.0167 (5)	0.0138 (5)	0.0160 (5)	−0.0011 (4)	0.0006 (4)	−0.0018 (4)
C1	0.0180 (6)	0.0157 (6)	0.0173 (6)	0.0022 (5)	0.0042 (5)	0.0022 (5)
C2	0.0202 (7)	0.0279 (7)	0.0254 (7)	0.0015 (5)	0.0001 (5)	0.0022 (6)
C3	0.0262 (8)	0.0430 (10)	0.0311 (8)	0.0111 (7)	−0.0010 (6)	0.0112 (7)
C4	0.0404 (9)	0.0190 (7)	0.0415 (9)	−0.0023 (6)	0.0063 (7)	0.0080 (6)
C5	0.0381 (9)	0.0298 (8)	0.0401 (9)	0.0127 (7)	0.0093 (7)	0.0173 (7)
C6	0.0260 (7)	0.0197 (7)	0.0266 (7)	−0.0032 (6)	0.0008 (6)	0.0033 (6)
C7	0.0197 (6)	0.0174 (6)	0.0194 (6)	−0.0028 (5)	0.0040 (5)	0.0018 (5)
C8	0.0152 (6)	0.0137 (6)	0.0161 (6)	0.0008 (4)	−0.0003 (4)	0.0019 (5)
C9	0.0171 (6)	0.0151 (6)	0.0158 (6)	0.0022 (5)	−0.0003 (5)	0.0003 (5)
C10	0.0221 (7)	0.0215 (7)	0.0194 (6)	0.0008 (5)	0.0031 (5)	−0.0005 (5)
C11	0.0290 (7)	0.0261 (7)	0.0180 (6)	0.0042 (6)	0.0033 (5)	−0.0038 (6)
C12	0.0290 (7)	0.0215 (7)	0.0226 (7)	0.0036 (6)	−0.0043 (6)	−0.0074 (5)
C13	0.0227 (7)	0.0183 (6)	0.0254 (7)	−0.0009 (5)	−0.0024 (5)	−0.0039 (5)
C14	0.0178 (6)	0.0156 (6)	0.0183 (6)	0.0019 (5)	0.0004 (5)	−0.0003 (5)

Geometric parameters (Å, º) top

S1—O2	1.4310 (10)	C5—H5	0.9500
S1—O1	1.4320 (10)	C6—H6	0.9500
S1—N1	1.6465 (12)	C7—C8	1.5035 (18)
S1—C1	1.7622 (13)	C7—H7A	0.9800
O3—C14	1.3562 (17)	C7—H7B	0.9800
O3—H3o	0.85 (1)	C7—H7C	0.9800
N1—N2	1.3934 (15)	C8—C9	1.4788 (17)
N1—H1n	0.84 (1)	C9—C10	1.4035 (18)
N2—C8	1.2917 (17)	C9—C14	1.4138 (19)
C1—C6	1.3904 (19)	C10—C11	1.385 (2)
C1—C2	1.3931 (19)	C10—H10	0.9500
C2—C3	1.392 (2)	C11—C12	1.389 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C5	1.380 (3)	C12—C13	1.383 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.388 (3)	C13—C14	1.3966 (18)
C4—C6	1.390 (2)	C13—H13	0.9500
C4—H4	0.9500

O2—S1—O1	121.18 (6)	C1—C6—H6	120.5
O2—S1—N1	104.11 (6)	C8—C7—H7A	109.5
O1—S1—N1	106.89 (6)	C8—C7—H7B	109.5
O2—S1—C1	108.98 (6)	H7A—C7—H7B	109.5
O1—S1—C1	106.62 (6)	C8—C7—H7C	109.5
N1—S1—C1	108.55 (6)	H7A—C7—H7C	109.5
C14—O3—H3o	105.5 (16)	H7B—C7—H7C	109.5
N2—N1—S1	112.80 (8)	N2—C8—C9	115.74 (11)
N2—N1—H1n	117.4 (13)	N2—C8—C7	123.77 (12)
S1—N1—H1n	112.7 (13)	C9—C8—C7	120.48 (11)
C8—N2—N1	119.05 (11)	C10—C9—C14	117.45 (12)
C6—C1—C2	121.58 (13)	C10—C9—C8	120.15 (12)
C6—C1—S1	119.21 (11)	C14—C9—C8	122.39 (12)
C2—C1—S1	119.19 (11)	C11—C10—C9	121.98 (13)
C3—C2—C1	118.51 (14)	C11—C10—H10	119.0
C3—C2—H2	120.7	C9—C10—H10	119.0
C1—C2—H2	120.7	C10—C11—C12	119.48 (13)
C5—C3—C2	120.40 (15)	C10—C11—H11	120.3
C5—C3—H3	119.8	C12—C11—H11	120.3
C2—C3—H3	119.8	C13—C12—C11	120.27 (13)
C5—C4—C6	119.95 (15)	C13—C12—H12	119.9
C5—C4—H4	120.0	C11—C12—H12	119.9
C6—C4—H4	120.0	C12—C13—C14	120.38 (13)
C3—C5—C4	120.65 (15)	C12—C13—H13	119.8
C3—C5—H5	119.7	C14—C13—H13	119.8
C4—C5—H5	119.7	O3—C14—C13	116.56 (12)
C4—C6—C1	118.91 (14)	O3—C14—C9	123.02 (12)
C4—C6—H6	120.5	C13—C14—C9	120.42 (13)

O2—S1—N1—N2	177.17 (9)	N1—N2—C8—C9	−177.23 (10)
O1—S1—N1—N2	−53.46 (10)	N1—N2—C8—C7	1.42 (18)
C1—S1—N1—N2	61.19 (10)	N2—C8—C9—C10	−175.71 (12)
S1—N1—N2—C8	−177.79 (9)	C7—C8—C9—C10	5.59 (18)
O2—S1—C1—C6	149.42 (11)	N2—C8—C9—C14	3.90 (18)
O1—S1—C1—C6	17.04 (13)	C7—C8—C9—C14	−174.80 (12)
N1—S1—C1—C6	−97.79 (12)	C14—C9—C10—C11	0.6 (2)
O2—S1—C1—C2	−28.97 (13)	C8—C9—C10—C11	−179.75 (12)
O1—S1—C1—C2	−161.35 (11)	C9—C10—C11—C12	0.6 (2)
N1—S1—C1—C2	83.81 (12)	C10—C11—C12—C13	−0.8 (2)
C6—C1—C2—C3	−0.4 (2)	C11—C12—C13—C14	−0.2 (2)
S1—C1—C2—C3	177.94 (11)	C12—C13—C14—O3	−178.52 (12)
C1—C2—C3—C5	0.0 (2)	C12—C13—C14—C9	1.4 (2)
C2—C3—C5—C4	0.5 (3)	C10—C9—C14—O3	178.33 (12)
C6—C4—C5—C3	−0.6 (3)	C8—C9—C14—O3	−1.3 (2)
C5—C4—C6—C1	0.2 (2)	C10—C9—C14—C13	−1.62 (19)
C2—C1—C6—C4	0.3 (2)	C8—C9—C14—C13	178.76 (12)
S1—C1—C6—C4	−178.08 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N2	0.85 (1)	1.80 (1)	2.568 (1)	150 (2)
N1—H1n···O1ⁱ	0.84 (1)	2.19 (1)	2.980 (2)	156 (2)

Symmetry code: (i) x+1, y, z.

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2′-[1-(2-Hydroxy­phen­yl)ethyl­idene]benzene­sulfonohydrazide

Supporting information

Key indicators

checkCIF/PLATON results

2′-[1-(2-Hydroxyphenyl)ethylidene]benzenesulfonohydrazide