2′-(5-Bromo-2-hydroxy­benzyl­idene)benzene­sulfonohydrazide

The two symmetry-independent mol­ecules of the title compound, C₁₃H₁₁ClN₂O₃S, are linked by N—H...O_s (s = sulfon­yl) and N—H...O_h (h = hydr­oxy) hydrogen bonds to furnish a chain that propagates along the a axis of the monoclinic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.111
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.568     0.688
            Tmin and Tmax expected:      0.470     0.667
            RR =      1.174
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.19
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .         20 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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'-(5-Bromo-2-hydroxybenzylidene)benzenesulfonohydrazide

Crystal data

C13H11BrN2O3S	F(000) = 1424
Mr = 355.21	Dx = 1.695 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8789 reflections
a = 11.6084 (2) Å	θ = 2.3–29.8°
b = 14.5141 (2) Å	µ = 3.11 mm^−1
c = 17.3216 (2) Å	T = 173 K
β = 107.416 (1)°	Block, yellow
V = 2784.65 (7) Å^3	0.25 × 0.21 × 0.13 mm
Z = 8

Data collection

Bruker APEXII diffractometer	6377 independent reflections
Radiation source: medium-focus sealed tube	5044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.568, Tmax = 0.688	k = −18→18
53670 measured reflections	l = −22→22

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) = 0.111	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0657P)^2] where P = (Fo^2 + 2Fc^2)/3
6377 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 1.26 e Å^−3
0 restraints	Δρmin = −1.22 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	0.56285 (3)	0.65277 (2)	0.814002 (18)	0.04416 (11)
Br2	0.20668 (3)	0.64910 (2)	−0.00042 (2)	0.04955 (12)
S1	0.17312 (6)	0.59244 (4)	0.28106 (4)	0.02619 (15)
S2	0.86013 (5)	0.61415 (4)	0.43572 (4)	0.02182 (13)
O1	0.52836 (17)	0.61489 (14)	0.46119 (11)	0.0341 (4)
H1O	0.4569	0.6061	0.4323	0.051*
O2	0.28572 (19)	0.56649 (12)	0.27068 (12)	0.0383 (5)
O3	0.06336 (19)	0.54602 (12)	0.23904 (12)	0.0406 (5)
O4	0.74262 (18)	0.61147 (16)	0.15618 (12)	0.0420 (5)
H4O	0.7598	0.6031	0.2063	0.063*
O5	0.94116 (15)	0.57559 (12)	0.39612 (11)	0.0294 (4)
O6	0.86399 (16)	0.58565 (11)	0.51537 (10)	0.0277 (4)
N1	0.29682 (19)	0.59772 (13)	0.43076 (13)	0.0261 (4)
N2	0.18622 (19)	0.57766 (14)	0.37665 (12)	0.0276 (5)
H2N	0.1256	0.5578	0.3928	0.033*
N3	0.69483 (19)	0.60071 (13)	0.29775 (12)	0.0243 (4)
N4	0.72265 (18)	0.58623 (13)	0.38068 (12)	0.0250 (4)
H4N	0.6695	0.5633	0.4026	0.030*
C1	0.5312 (2)	0.62262 (16)	0.54021 (16)	0.0267 (5)
C2	0.6427 (3)	0.63321 (18)	0.59825 (18)	0.0318 (6)
H2	0.7138	0.6341	0.5819	0.038*
C3	0.6519 (3)	0.64242 (16)	0.67872 (18)	0.0322 (6)
H3	0.7286	0.6500	0.7178	0.039*
C4	0.5477 (3)	0.64055 (16)	0.70223 (17)	0.0297 (6)
C5	0.4357 (2)	0.62875 (17)	0.64609 (16)	0.0293 (6)
H5	0.3654	0.6267	0.6634	0.035*
C6	0.4254 (2)	0.61980 (16)	0.56420 (16)	0.0255 (5)
C7	0.3064 (2)	0.60483 (16)	0.50610 (15)	0.0268 (5)
H7	0.2369	0.6004	0.5241	0.032*
C8	0.1519 (2)	0.71070 (16)	0.25983 (14)	0.0233 (5)
C9	0.0423 (3)	0.74171 (19)	0.20901 (16)	0.0368 (6)
H9	−0.0216	0.6998	0.1859	0.044*
C10	0.0284 (3)	0.8352 (2)	0.1928 (2)	0.0485 (8)
H10	−0.0459	0.8576	0.1579	0.058*
C11	0.1207 (3)	0.89599 (19)	0.22662 (18)	0.0380 (7)
H11	0.1098	0.9600	0.2151	0.046*
C12	0.2282 (3)	0.86437 (17)	0.27677 (19)	0.0365 (7)
H12	0.2915	0.9065	0.3004	0.044*
C13	0.2449 (2)	0.77090 (17)	0.29320 (17)	0.0327 (6)
H13	0.3199	0.7487	0.3272	0.039*
C14	0.6204 (2)	0.61589 (18)	0.12340 (16)	0.0291 (5)
C15	0.5746 (3)	0.6236 (2)	0.04012 (18)	0.0397 (7)
H15	0.6282	0.6227	0.0081	0.048*
C16	0.4518 (3)	0.63254 (19)	0.00296 (18)	0.0385 (7)
H16	0.4210	0.6382	−0.0542	0.046*
C17	0.3741 (2)	0.63311 (17)	0.05044 (17)	0.0316 (6)
C18	0.4175 (2)	0.62199 (18)	0.13270 (17)	0.0318 (6)
H18	0.3628	0.6201	0.1640	0.038*
C19	0.5413 (2)	0.61339 (16)	0.17095 (15)	0.0258 (5)
C20	0.5825 (2)	0.60264 (16)	0.25810 (15)	0.0268 (5)
H20	0.5245	0.5969	0.2866	0.032*
C21	0.8752 (2)	0.73471 (15)	0.43386 (14)	0.0226 (5)
C22	0.9108 (2)	0.77385 (17)	0.37144 (15)	0.0278 (5)
H22	0.9278	0.7363	0.3313	0.033*
C23	0.9211 (3)	0.86883 (18)	0.36902 (18)	0.0342 (6)
H23	0.9447	0.8970	0.3266	0.041*
C24	0.8972 (2)	0.92242 (19)	0.42767 (18)	0.0361 (6)
H24	0.9041	0.9875	0.4251	0.043*
C25	0.8633 (3)	0.88367 (18)	0.49029 (18)	0.0357 (6)
H25	0.8487	0.9216	0.5311	0.043*
C26	0.8508 (2)	0.78858 (17)	0.49321 (16)	0.0293 (5)
H26	0.8259	0.7609	0.5353	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03720 (19)	0.0647 (2)	0.02948 (17)	−0.00338 (13)	0.00838 (13)	−0.00174 (13)
Br2	0.02653 (18)	0.0681 (2)	0.0454 (2)	−0.00696 (13)	−0.00249 (14)	0.01995 (15)
S1	0.0311 (4)	0.0229 (3)	0.0279 (3)	−0.0025 (2)	0.0140 (3)	−0.0019 (2)
S2	0.0193 (3)	0.0242 (3)	0.0216 (3)	0.0012 (2)	0.0055 (2)	0.0004 (2)
O1	0.0241 (10)	0.0494 (11)	0.0308 (10)	0.0009 (9)	0.0113 (8)	0.0018 (9)
O2	0.0462 (13)	0.0308 (9)	0.0494 (12)	0.0089 (8)	0.0319 (10)	0.0056 (8)
O3	0.0501 (13)	0.0357 (10)	0.0358 (11)	−0.0185 (9)	0.0128 (10)	−0.0106 (8)
O4	0.0268 (11)	0.0701 (14)	0.0298 (11)	0.0016 (10)	0.0093 (9)	0.0052 (10)
O5	0.0219 (9)	0.0324 (9)	0.0352 (10)	0.0031 (7)	0.0104 (8)	−0.0044 (7)
O6	0.0299 (10)	0.0302 (9)	0.0217 (9)	0.0000 (7)	0.0056 (7)	0.0042 (7)
N1	0.0218 (11)	0.0245 (10)	0.0322 (12)	0.0010 (8)	0.0081 (9)	0.0064 (8)
N2	0.0228 (11)	0.0336 (11)	0.0284 (11)	−0.0026 (9)	0.0104 (9)	0.0067 (9)
N3	0.0242 (11)	0.0283 (10)	0.0195 (10)	−0.0021 (8)	0.0052 (8)	0.0001 (8)
N4	0.0218 (11)	0.0317 (10)	0.0212 (10)	−0.0054 (8)	0.0059 (8)	0.0017 (8)
C1	0.0270 (14)	0.0231 (11)	0.0325 (14)	0.0018 (10)	0.0127 (11)	0.0037 (10)
C2	0.0236 (13)	0.0340 (13)	0.0401 (16)	0.0013 (11)	0.0130 (12)	0.0052 (11)
C3	0.0255 (14)	0.0317 (13)	0.0358 (15)	0.0001 (10)	0.0039 (12)	0.0040 (11)
C4	0.0318 (15)	0.0272 (12)	0.0299 (14)	0.0015 (10)	0.0091 (12)	0.0029 (10)
C5	0.0256 (14)	0.0329 (13)	0.0321 (14)	0.0017 (10)	0.0126 (11)	0.0019 (11)
C6	0.0252 (13)	0.0200 (11)	0.0325 (14)	0.0020 (9)	0.0103 (11)	0.0052 (9)
C7	0.0262 (14)	0.0241 (12)	0.0329 (14)	0.0009 (10)	0.0130 (11)	0.0048 (10)
C8	0.0250 (13)	0.0270 (11)	0.0192 (11)	0.0015 (9)	0.0084 (10)	0.0002 (9)
C9	0.0333 (16)	0.0446 (16)	0.0264 (14)	−0.0018 (12)	−0.0003 (12)	0.0030 (11)
C10	0.0424 (19)	0.0530 (19)	0.0410 (18)	0.0149 (15)	−0.0012 (15)	0.0170 (14)
C11	0.0474 (19)	0.0297 (13)	0.0406 (16)	0.0118 (12)	0.0189 (14)	0.0124 (12)
C12	0.0406 (17)	0.0252 (12)	0.0421 (17)	−0.0030 (11)	0.0098 (14)	0.0033 (11)
C13	0.0269 (14)	0.0281 (13)	0.0378 (15)	0.0020 (10)	0.0017 (11)	0.0038 (11)
C14	0.0247 (14)	0.0323 (13)	0.0297 (14)	−0.0019 (10)	0.0070 (11)	0.0015 (11)
C15	0.0330 (17)	0.0581 (18)	0.0292 (15)	−0.0024 (14)	0.0111 (13)	0.0021 (13)
C16	0.0381 (17)	0.0491 (16)	0.0249 (14)	−0.0079 (13)	0.0039 (12)	0.0057 (12)
C17	0.0242 (14)	0.0329 (13)	0.0325 (15)	−0.0065 (10)	0.0007 (11)	0.0070 (11)
C18	0.0266 (14)	0.0374 (14)	0.0309 (14)	−0.0036 (11)	0.0078 (11)	0.0056 (11)
C19	0.0264 (13)	0.0253 (11)	0.0251 (13)	−0.0024 (10)	0.0068 (10)	0.0014 (9)
C20	0.0233 (13)	0.0307 (13)	0.0271 (13)	−0.0022 (10)	0.0085 (10)	0.0009 (10)
C21	0.0183 (12)	0.0242 (11)	0.0240 (12)	−0.0005 (9)	0.0042 (9)	0.0011 (9)
C22	0.0254 (13)	0.0323 (13)	0.0245 (13)	−0.0007 (10)	0.0057 (10)	0.0017 (10)
C23	0.0302 (15)	0.0352 (14)	0.0336 (15)	−0.0045 (11)	0.0039 (12)	0.0104 (11)
C24	0.0305 (15)	0.0277 (13)	0.0452 (17)	−0.0046 (11)	0.0039 (12)	0.0013 (12)
C25	0.0351 (16)	0.0292 (13)	0.0422 (16)	−0.0022 (11)	0.0108 (13)	−0.0088 (12)
C26	0.0288 (14)	0.0309 (13)	0.0299 (13)	0.0003 (10)	0.0111 (11)	0.0009 (10)

Geometric parameters (Å, º)

Br1—C4	1.899 (3)	C8—C9	1.387 (4)
Br2—C17	1.893 (3)	C9—C10	1.385 (4)
S1—O2	1.4225 (19)	C9—H9	0.9500
S1—O3	1.432 (2)	C10—C11	1.377 (5)
S1—N2	1.631 (2)	C10—H10	0.9500
S1—C8	1.757 (2)	C11—C12	1.369 (4)
S2—O6	1.4281 (17)	C11—H11	0.9500
S2—O5	1.4335 (17)	C12—C13	1.388 (3)
S2—N4	1.646 (2)	C12—H12	0.9500
S2—C21	1.760 (2)	C13—H13	0.9500
O1—C1	1.364 (3)	C14—C15	1.385 (4)
O1—H1O	0.8400	C14—C19	1.406 (3)
O4—C14	1.362 (3)	C15—C16	1.383 (4)
O4—H4O	0.8400	C15—H15	0.9500
N1—C7	1.280 (3)	C16—C17	1.391 (4)
N1—N2	1.375 (3)	C16—H16	0.9500
N2—H2N	0.8800	C17—C18	1.371 (4)
N3—C20	1.279 (3)	C18—C19	1.396 (4)
N3—N4	1.391 (3)	C18—H18	0.9500
N4—H4N	0.8800	C19—C20	1.449 (4)
C1—C2	1.389 (4)	C20—H20	0.9500
C1—C6	1.410 (3)	C21—C26	1.386 (3)
C2—C3	1.372 (4)	C21—C22	1.389 (3)
C2—H2	0.9500	C22—C23	1.385 (3)
C3—C4	1.387 (4)	C22—H22	0.9500
C3—H3	0.9500	C23—C24	1.372 (4)
C4—C5	1.381 (4)	C23—H23	0.9500
C5—C6	1.393 (4)	C24—C25	1.379 (4)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.461 (4)	C25—C26	1.390 (4)
C7—H7	0.9500	C25—H25	0.9500
C8—C13	1.375 (3)	C26—H26	0.9500
O2—S1—O3	121.49 (12)	C11—C10—H10	119.6
O2—S1—N2	106.47 (12)	C9—C10—H10	119.6
O3—S1—N2	104.62 (11)	C12—C11—C10	120.1 (3)
O2—S1—C8	108.00 (11)	C12—C11—H11	120.0
O3—S1—C8	107.77 (12)	C10—C11—H11	120.0
N2—S1—C8	107.79 (11)	C11—C12—C13	120.2 (3)
O6—S2—O5	120.92 (11)	C11—C12—H12	119.9
O6—S2—N4	103.47 (11)	C13—C12—H12	119.9
O5—S2—N4	106.74 (11)	C8—C13—C12	119.4 (3)
O6—S2—C21	109.34 (11)	C8—C13—H13	120.3
O5—S2—C21	107.24 (11)	C12—C13—H13	120.3
N4—S2—C21	108.58 (11)	O4—C14—C15	117.7 (2)
C1—O1—H1O	109.5	O4—C14—C19	122.4 (2)
C14—O4—H4O	109.5	C15—C14—C19	119.9 (3)
C7—N1—N2	119.4 (2)	C16—C15—C14	120.9 (3)
N1—N2—S1	116.65 (16)	C16—C15—H15	119.6
N1—N2—H2N	121.7	C14—C15—H15	119.6
S1—N2—H2N	121.7	C15—C16—C17	119.1 (3)
C20—N3—N4	116.2 (2)	C15—C16—H16	120.5
N3—N4—S2	116.50 (15)	C17—C16—H16	120.5
N3—N4—H4N	121.7	C18—C17—C16	120.8 (3)
S2—N4—H4N	121.7	C18—C17—Br2	120.3 (2)
O1—C1—C2	118.2 (2)	C16—C17—Br2	118.9 (2)
O1—C1—C6	122.1 (2)	C17—C18—C19	120.6 (2)
C2—C1—C6	119.7 (2)	C17—C18—H18	119.7
C3—C2—C1	121.2 (3)	C19—C18—H18	119.7
C3—C2—H2	119.4	C18—C19—C14	118.7 (2)
C1—C2—H2	119.4	C18—C19—C20	118.4 (2)
C2—C3—C4	119.1 (3)	C14—C19—C20	122.9 (2)
C2—C3—H3	120.4	N3—C20—C19	121.8 (2)
C4—C3—H3	120.4	N3—C20—H20	119.1
C5—C4—C3	121.0 (3)	C19—C20—H20	119.1
C5—C4—Br1	120.7 (2)	C26—C21—C22	121.4 (2)
C3—C4—Br1	118.3 (2)	C26—C21—S2	120.25 (18)
C4—C5—C6	120.3 (2)	C22—C21—S2	118.37 (18)
C4—C5—H5	119.9	C23—C22—C21	118.6 (2)
C6—C5—H5	119.9	C23—C22—H22	120.7
C5—C6—C1	118.7 (2)	C21—C22—H22	120.7
C5—C6—C7	119.4 (2)	C24—C23—C22	120.2 (2)
C1—C6—C7	121.9 (2)	C24—C23—H23	119.9
N1—C7—C6	119.4 (2)	C22—C23—H23	119.9
N1—C7—H7	120.3	C23—C24—C25	121.3 (3)
C6—C7—H7	120.3	C23—C24—H24	119.4
C13—C8—C9	121.1 (2)	C25—C24—H24	119.4
C13—C8—S1	119.30 (19)	C24—C25—C26	119.4 (2)
C9—C8—S1	119.6 (2)	C24—C25—H25	120.3
C10—C9—C8	118.4 (3)	C26—C25—H25	120.3
C10—C9—H9	120.8	C21—C26—C25	119.1 (2)
C8—C9—H9	120.8	C21—C26—H26	120.5
C11—C10—C9	120.9 (3)	C25—C26—H26	120.5
C7—N1—N2—S1	166.54 (18)	C10—C11—C12—C13	0.5 (5)
O2—S1—N2—N1	36.3 (2)	C9—C8—C13—C12	1.0 (4)
O3—S1—N2—N1	166.13 (17)	S1—C8—C13—C12	−179.8 (2)
C8—S1—N2—N1	−79.35 (19)	C11—C12—C13—C8	−1.2 (4)
C20—N3—N4—S2	−162.14 (17)	O4—C14—C15—C16	−177.1 (3)
O6—S2—N4—N3	−175.90 (16)	C19—C14—C15—C16	2.6 (4)
O5—S2—N4—N3	−47.31 (19)	C14—C15—C16—C17	−0.5 (4)
C21—S2—N4—N3	68.01 (19)	C15—C16—C17—C18	−2.1 (4)
O1—C1—C2—C3	179.3 (2)	C15—C16—C17—Br2	178.1 (2)
C6—C1—C2—C3	−1.0 (4)	C16—C17—C18—C19	2.5 (4)
C1—C2—C3—C4	0.4 (4)	Br2—C17—C18—C19	−177.74 (18)
C2—C3—C4—C5	0.6 (4)	C17—C18—C19—C14	−0.3 (4)
C2—C3—C4—Br1	179.67 (19)	C17—C18—C19—C20	179.4 (2)
C3—C4—C5—C6	−0.9 (4)	O4—C14—C19—C18	177.5 (2)
Br1—C4—C5—C6	−179.97 (17)	C15—C14—C19—C18	−2.2 (4)
C4—C5—C6—C1	0.3 (4)	O4—C14—C19—C20	−2.3 (4)
C4—C5—C6—C7	178.3 (2)	C15—C14—C19—C20	178.1 (2)
O1—C1—C6—C5	−179.6 (2)	N4—N3—C20—C19	−177.4 (2)
C2—C1—C6—C5	0.7 (3)	C18—C19—C20—N3	−175.1 (2)
O1—C1—C6—C7	2.4 (4)	C14—C19—C20—N3	4.6 (4)
C2—C1—C6—C7	−177.3 (2)	O6—S2—C21—C26	−20.1 (2)
N2—N1—C7—C6	175.8 (2)	O5—S2—C21—C26	−152.9 (2)
C5—C6—C7—N1	179.2 (2)	N4—S2—C21—C26	92.1 (2)
C1—C6—C7—N1	−2.9 (3)	O6—S2—C21—C22	160.42 (19)
O2—S1—C8—C13	−47.0 (2)	O5—S2—C21—C22	27.7 (2)
O3—S1—C8—C13	−179.9 (2)	N4—S2—C21—C22	−87.3 (2)
N2—S1—C8—C13	67.7 (2)	C26—C21—C22—C23	−0.4 (4)
O2—S1—C8—C9	132.2 (2)	S2—C21—C22—C23	179.0 (2)
O3—S1—C8—C9	−0.7 (2)	C21—C22—C23—C24	0.5 (4)
N2—S1—C8—C9	−113.1 (2)	C22—C23—C24—C25	0.4 (4)
C13—C8—C9—C10	−0.3 (4)	C23—C24—C25—C26	−1.3 (4)
S1—C8—C9—C10	−179.5 (2)	C22—C21—C26—C25	−0.5 (4)
C8—C9—C10—C11	−0.3 (5)	S2—C21—C26—C25	−179.9 (2)
C9—C10—C11—C12	0.2 (5)	C24—C25—C26—C21	1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84	1.86	2.592 (3)	146
O4—H4o···N3	0.84	1.95	2.676 (3)	144
N2—H2n···O5^i	0.88	2.17	2.963 (3)	149
N4—H4n···O1	0.88	2.30	3.015 (3)	139

Symmetry code: (i) x−1, y, z.