2′-(5-Bromo-1H-indol-3-ylmethyl­ene)benzene­sulfonohydrazine

The mol­ecules of the title compound, C₁₅H₁₂BrN₃O₂S, are linked by N_amino–H...O_sulfon­yl and N_indol­yl–H...N_imino hydrogen bonds into a layer motif. The dihedral angle between the aromatic ring mean planes in the molecule is 76.44 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.027
• wR factor = 0.082
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            Faint
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.80

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.798
            Tmax scaled      0.306 Tmin scaled      0.263

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 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
   1 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

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S1. Comment

The crystal structure of 2'-(1H-indol-3-ylmethylene)benzenesulfonohydrazine consists of molecules that are linked by N_amino–H···O_sulfonoy and N_indolyl–H···N_imino hydrogen bonds into layers (Ali, Yusnita, Wan Jefrey & Ng, 2007; Ali, Yusnita & Ng, 2007. The presence of the bromine substituent in the 5-position of the indolyl portion leads to a similar layer structure for the title compound (I).

Related literature

For related structures, see: Ali, Yusnita, Wan Jefrey & Ng (2007); Ali, Yusnita & Ng (2007).

S2. Experimental

Benzenesulfohydrazine (0.3 g, 2 mmol) and 5-bromoindole-3-carbaldehyde (0.3 g, 2 mmol) were dissolved in ethanol (50 ml). The reactants were heated under reflux for 1 h. The solvent was removed to give the Schiff base, which was purified by recrystallzation from ethanol to yield faint yellow blocks of (I).

S3. Refinement

The carbon-bound H atoms were placed at calculated positions (C–H = 0.95–0.98 Å), and they were included in the refinement in the riding model approximation with U(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). The N-bound H atoms were located in a difference Fourier map, and were refined with a distance restraint [N–H = 0.88 (1) Å]; their U_iso values were freely refined.

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: SHELXL97.

Figures

Fig. 1. View of the molecular structure of (I). Displacement ellipsoids are drawn at the 70% probability level and H atoms are shown as spheres of arbitrary radius.

2'-(5-Bromo-1H-indol-3-ylmethylene)benzenesulfonohydrazine

Crystal data

C15H12BrN3O2S	F(000) = 1520
Mr = 378.25	Dx = 1.714 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9228 reflections
a = 33.1196 (4) Å	θ = 2.4–33.5°
b = 8.9260 (1) Å	µ = 2.96 mm^−1
c = 9.9158 (1) Å	T = 173 K
V = 2931.36 (6) Å^3	Block, faint yellow
Z = 8	0.50 × 0.40 × 0.40 mm

Data collection

Bruker APEXII CCD diffractometer	3375 independent reflections
Radiation source: medium-focus sealed tube	3270 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −43→43
Tmin = 0.330, Tmax = 0.384	k = −11→11
59138 measured reflections	l = −12→12

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)] = 0.027	Hydrogen site location: difmap and geom
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 4.5513P] where P = (Fo^2 + 2Fc^2)/3
3375 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.41 e Å^−3
2 restraints	Δρmin = −0.39 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	0.517836 (6)	0.70758 (2)	0.45443 (2)	0.02107 (9)
S1	0.702481 (14)	0.49278 (5)	0.24367 (5)	0.01426 (11)
O1	0.70538 (5)	0.58662 (18)	0.12640 (15)	0.0204 (3)
O2	0.72824 (5)	0.36427 (18)	0.25464 (16)	0.0226 (3)
N1	0.71431 (5)	0.59551 (19)	0.37560 (17)	0.0140 (3)
H1N	0.7194 (9)	0.536 (3)	0.443 (2)	0.031 (8)*
N2	0.68493 (5)	0.70889 (18)	0.40448 (18)	0.0132 (3)
N3	0.64834 (5)	1.0919 (2)	0.68965 (18)	0.0180 (4)
H3N	0.6499 (9)	1.164 (2)	0.749 (2)	0.026 (7)*
C1	0.65175 (6)	0.4387 (2)	0.2608 (2)	0.0151 (4)
C2	0.62208 (7)	0.5210 (2)	0.1940 (2)	0.0189 (4)
H2	0.6293	0.6011	0.1357	0.023*
C3	0.58184 (7)	0.4838 (3)	0.2140 (2)	0.0252 (5)
H3	0.5612	0.5398	0.1705	0.030*
C4	0.57173 (7)	0.3650 (3)	0.2974 (2)	0.0283 (5)
H4	0.5441	0.3404	0.3113	0.034*
C5	0.60142 (8)	0.2821 (3)	0.3604 (2)	0.0276 (5)
H5	0.5941	0.1996	0.4157	0.033*
C6	0.64192 (7)	0.3184 (3)	0.3435 (2)	0.0217 (4)
H6	0.6624	0.2622	0.3875	0.026*
C7	0.69757 (6)	0.8008 (2)	0.4945 (2)	0.0136 (4)
H7	0.7251	0.7987	0.5215	0.016*
C8	0.67028 (6)	0.9073 (2)	0.55495 (19)	0.0144 (4)
C9	0.68164 (6)	1.0224 (2)	0.6400 (2)	0.0168 (4)
H9A	0.7087	1.0489	0.6606	0.020*
C10	0.61404 (6)	1.0226 (2)	0.6410 (2)	0.0149 (4)
C11	0.57348 (6)	1.0512 (2)	0.6664 (2)	0.0179 (4)
H11	0.5655	1.1323	0.7223	0.021*
C12	0.54506 (6)	0.9581 (2)	0.6078 (2)	0.0173 (4)
H12	0.5171	0.9745	0.6233	0.021*
C13	0.55780 (6)	0.8393 (2)	0.5253 (2)	0.0152 (4)
C14	0.59775 (6)	0.8105 (2)	0.4965 (2)	0.0135 (4)
H14	0.6054	0.7299	0.4394	0.016*
C15	0.62673 (6)	0.9053 (2)	0.55482 (19)	0.0132 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01373 (12)	0.02226 (13)	0.02720 (14)	−0.00269 (7)	−0.00048 (8)	−0.00370 (8)
S1	0.0148 (2)	0.0144 (2)	0.0136 (2)	−0.00029 (17)	0.00231 (17)	−0.00240 (17)
O1	0.0248 (8)	0.0238 (8)	0.0126 (7)	−0.0057 (6)	0.0030 (6)	−0.0004 (6)
O2	0.0194 (8)	0.0200 (8)	0.0284 (8)	0.0047 (6)	0.0012 (6)	−0.0081 (6)
N1	0.0145 (8)	0.0136 (8)	0.0137 (8)	0.0023 (6)	−0.0012 (6)	−0.0020 (6)
N2	0.0128 (8)	0.0124 (8)	0.0143 (8)	0.0025 (6)	0.0011 (6)	0.0003 (6)
N3	0.0209 (9)	0.0140 (8)	0.0191 (8)	0.0015 (7)	−0.0034 (7)	−0.0061 (7)
C1	0.0155 (9)	0.0150 (9)	0.0147 (9)	−0.0024 (7)	0.0023 (7)	−0.0037 (7)
C2	0.0200 (10)	0.0159 (10)	0.0207 (10)	−0.0011 (8)	−0.0017 (8)	−0.0029 (8)
C3	0.0174 (10)	0.0268 (12)	0.0315 (12)	0.0020 (9)	−0.0022 (9)	−0.0099 (9)
C4	0.0224 (11)	0.0362 (13)	0.0264 (11)	−0.0104 (10)	0.0065 (9)	−0.0130 (10)
C5	0.0340 (13)	0.0326 (13)	0.0163 (10)	−0.0158 (10)	0.0048 (9)	0.0002 (9)
C6	0.0264 (11)	0.0214 (10)	0.0171 (10)	−0.0039 (9)	−0.0013 (8)	0.0009 (8)
C7	0.0129 (9)	0.0135 (9)	0.0145 (9)	−0.0003 (7)	−0.0004 (7)	0.0016 (7)
C8	0.0166 (9)	0.0125 (9)	0.0141 (9)	−0.0005 (7)	−0.0023 (7)	0.0000 (7)
C9	0.0186 (9)	0.0143 (9)	0.0175 (9)	0.0001 (7)	−0.0026 (8)	−0.0018 (7)
C10	0.0184 (9)	0.0126 (9)	0.0137 (9)	0.0029 (7)	−0.0028 (7)	−0.0006 (7)
C11	0.0226 (10)	0.0172 (9)	0.0138 (9)	0.0067 (8)	−0.0003 (8)	−0.0024 (8)
C12	0.0144 (9)	0.0207 (10)	0.0169 (9)	0.0043 (8)	0.0005 (8)	0.0007 (8)
C13	0.0156 (9)	0.0169 (9)	0.0132 (9)	−0.0008 (8)	−0.0020 (7)	0.0010 (7)
C14	0.0148 (9)	0.0124 (8)	0.0132 (9)	0.0009 (7)	0.0005 (7)	−0.0006 (7)
C15	0.0161 (9)	0.0118 (8)	0.0118 (8)	0.0015 (7)	0.0000 (7)	0.0016 (7)

Geometric parameters (Å, º)

Br1—C13	1.905 (2)	C4—H4	0.9500
S1—O2	1.4337 (16)	C5—C6	1.390 (3)
S1—O1	1.4363 (15)	C5—H5	0.9500
S1—N1	1.6448 (17)	C6—H6	0.9500
S1—C1	1.756 (2)	C7—C8	1.442 (3)
N1—N2	1.433 (2)	C7—H7	0.9500
N1—H1N	0.872 (10)	C8—C9	1.381 (3)
N2—C7	1.282 (3)	C8—C15	1.442 (3)
N3—C9	1.358 (3)	C9—H9A	0.9500
N3—C10	1.381 (3)	C10—C11	1.390 (3)
N3—H3N	0.876 (10)	C10—C15	1.416 (3)
C1—C6	1.390 (3)	C11—C12	1.383 (3)
C1—C2	1.394 (3)	C11—H11	0.9500
C2—C3	1.388 (3)	C12—C13	1.405 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.386 (4)	C13—C14	1.378 (3)
C3—H3	0.9500	C14—C15	1.404 (3)
C4—C5	1.380 (4)	C14—H14	0.9500
O2—S1—O1	119.23 (10)	C5—C6—H6	120.8
O2—S1—N1	104.12 (9)	C1—C6—H6	120.8
O1—S1—N1	107.63 (9)	N2—C7—C8	120.41 (19)
O2—S1—C1	110.00 (10)	N2—C7—H7	119.8
O1—S1—C1	107.60 (10)	C8—C7—H7	119.8
N1—S1—C1	107.71 (9)	C9—C8—C15	106.38 (18)
N2—N1—S1	113.01 (13)	C9—C8—C7	124.99 (19)
N2—N1—H1N	114 (2)	C15—C8—C7	128.18 (18)
S1—N1—H1N	108 (2)	N3—C9—C8	109.91 (18)
C7—N2—N1	111.66 (16)	N3—C9—H9A	125.0
C9—N3—C10	109.67 (17)	C8—C9—H9A	125.0
C9—N3—H3N	122.2 (19)	N3—C10—C11	130.53 (19)
C10—N3—H3N	127.9 (19)	N3—C10—C15	107.34 (17)
C6—C1—C2	121.5 (2)	C11—C10—C15	122.12 (19)
C6—C1—S1	119.57 (17)	C12—C11—C10	118.13 (19)
C2—C1—S1	118.92 (16)	C12—C11—H11	120.9
C3—C2—C1	118.9 (2)	C10—C11—H11	120.9
C3—C2—H2	120.6	C11—C12—C13	119.59 (18)
C1—C2—H2	120.6	C11—C12—H12	120.2
C2—C3—C4	120.0 (2)	C13—C12—H12	120.2
C2—C3—H3	120.0	C14—C13—C12	123.36 (19)
C4—C3—H3	120.0	C14—C13—Br1	118.43 (15)
C5—C4—C3	120.5 (2)	C12—C13—Br1	118.18 (15)
C5—C4—H4	119.7	C13—C14—C15	117.34 (18)
C3—C4—H4	119.7	C13—C14—H14	121.3
C4—C5—C6	120.5 (2)	C15—C14—H14	121.3
C4—C5—H5	119.7	C14—C15—C10	119.42 (18)
C6—C5—H5	119.7	C14—C15—C8	133.76 (18)
C5—C6—C1	118.5 (2)	C10—C15—C8	106.69 (17)
O2—S1—N1—N2	−164.15 (13)	C15—C8—C9—N3	−1.0 (2)
O1—S1—N1—N2	68.38 (15)	C7—C8—C9—N3	−173.81 (19)
C1—S1—N1—N2	−47.37 (16)	C9—N3—C10—C11	178.1 (2)
S1—N1—N2—C7	−170.42 (14)	C9—N3—C10—C15	−1.0 (2)
O2—S1—C1—C6	32.1 (2)	N3—C10—C11—C12	−177.0 (2)
O1—S1—C1—C6	163.45 (17)	C15—C10—C11—C12	1.9 (3)
N1—S1—C1—C6	−80.77 (18)	C10—C11—C12—C13	−0.1 (3)
O2—S1—C1—C2	−149.89 (16)	C11—C12—C13—C14	−1.2 (3)
O1—S1—C1—C2	−18.54 (19)	C11—C12—C13—Br1	176.74 (16)
N1—S1—C1—C2	97.24 (17)	C12—C13—C14—C15	0.7 (3)
C6—C1—C2—C3	1.8 (3)	Br1—C13—C14—C15	−177.22 (14)
S1—C1—C2—C3	−176.16 (16)	C13—C14—C15—C10	1.1 (3)
C1—C2—C3—C4	−1.1 (3)	C13—C14—C15—C8	176.2 (2)
C2—C3—C4—C5	−0.5 (3)	N3—C10—C15—C14	176.72 (17)
C3—C4—C5—C6	1.4 (4)	C11—C10—C15—C14	−2.4 (3)
C4—C5—C6—C1	−0.7 (3)	N3—C10—C15—C8	0.3 (2)
C2—C1—C6—C5	−0.9 (3)	C11—C10—C15—C8	−178.80 (19)
S1—C1—C6—C5	177.05 (17)	C9—C8—C15—C14	−175.2 (2)
N1—N2—C7—C8	−169.22 (17)	C7—C8—C15—C14	−2.7 (4)
N2—C7—C8—C9	−171.7 (2)	C9—C8—C15—C10	0.4 (2)
N2—C7—C8—C15	17.1 (3)	C7—C8—C15—C10	172.88 (19)
C10—N3—C9—C8	1.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1^i	0.87 (1)	2.17 (2)	2.986 (2)	155 (3)
N3—H3n···N2^ii	0.88 (1)	2.24 (2)	3.028 (2)	150 (3)

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+2, z+1/2.