5-Bromo-1H-indole-3-carbaldehyde thio-semicarbazone.

In the essentially planar title mol-ecule, C(10)H(9)BrN(4)S, the C=N double bond is in a trans configuration. In the crystal structure, the S atom acts as a hydrogen-bond acceptor for the aromatic NH, aliphatic NH and terminal NH(2) groups of three symmetry-related mol-ecules, forming a weak hydrogen-bonded layer structure.

Related literature

For a previous synthesis of the title compound, see: Dubey & Babu (2006 ▶). For related literature, see: Doyle et al. (1956 ▶); French & Blanz (1966 ▶); Fukukawa et al. (1966 ▶); Libermann et al. (1953 ▶); Usi (1968 ▶); Weller et al. (1954 ▶).

Experimental

Crystal data

C10H9BrN4S

M = 297.18

Triclinic,

a = 6.7731 (2) Å

b = 8.7551 (2) Å

c = 10.6539 (2) Å

α = 69.280 (1)°

β = 79.969 (1)°

γ = 72.886 (1)°

V = 563.00 (2) Å3

Z = 2

Mo Kα radiation

μ = 3.81 mm−1

T = 100 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.381, T max = 0.516 (expected range = 0.344–0.467)

6176 measured reflections

2563 independent reflections

2281 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.066

S = 1.06

2563 reflections

161 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801101X/lh2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801101X/lh2609Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H9BrN4S	Z = 2
Mr = 297.18	F000 = 296
Triclinic, P1	Dx = 1.753 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.7731 (2) Å	Cell parameters from 6604 reflections
b = 8.7551 (2) Å	θ = 4.0–28.3º
c = 10.6539 (2) Å	µ = 3.81 mm−1
α = 69.280 (1)º	T = 100 (2) K
β = 79.969 (1)º	Block, yellow
γ = 72.886 (1)º	0.30 × 0.20 × 0.20 mm
V = 563.00 (2) Å3

Bruker SMART APEX diffractometer	2563 independent reflections
Radiation source: fine-focus sealed tube	2281 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→8
Tmin = 0.381, Tmax = 0.516	k = −11→11
6176 measured reflections	l = −13→13

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)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2563 reflections	Δρmax = 0.36 e Å−3
161 parameters	Δρmin = −0.40 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Br1	0.51693 (4)	0.13022 (2)	0.31237 (2)	0.02102 (9)
S1	0.01187 (9)	0.22591 (6)	1.06142 (5)	0.01534 (12)
N1	0.2717 (3)	0.8577 (2)	0.27383 (17)	0.0153 (4)
N2	0.1383 (3)	0.4698 (2)	0.68281 (16)	0.0116 (3)
N3	0.0718 (3)	0.4342 (2)	0.81750 (16)	0.0118 (3)
N4	0.1492 (3)	0.1567 (2)	0.83268 (18)	0.0169 (4)
C1	0.1846 (3)	0.8475 (3)	0.4006 (2)	0.0151 (4)
H1	0.1266	0.9415	0.4320	0.018*
C2	0.3383 (3)	0.6981 (2)	0.2626 (2)	0.0122 (4)
C3	0.4355 (3)	0.6471 (3)	0.1529 (2)	0.0142 (4)
H3	0.4641	0.7265	0.0687	0.017*
C4	0.4889 (3)	0.4765 (3)	0.1711 (2)	0.0131 (4)
H4	0.5573	0.4359	0.0990	0.016*
C5	0.4422 (3)	0.3633 (2)	0.2960 (2)	0.0127 (4)
C6	0.3464 (3)	0.4108 (2)	0.40581 (19)	0.0118 (4)
H6	0.3184	0.3300	0.4893	0.014*
C7	0.2917 (3)	0.5832 (2)	0.38933 (19)	0.0109 (4)
C8	0.1921 (3)	0.6825 (2)	0.4770 (2)	0.0120 (4)
C9	0.1249 (3)	0.6266 (2)	0.6176 (2)	0.0127 (4)
H9	0.0693	0.7074	0.6633	0.015*
C10	0.0822 (3)	0.2737 (2)	0.8937 (2)	0.0123 (4)
H1N	0.254 (5)	0.953 (2)	0.207 (2)	0.028 (7)*
H3N	0.037 (4)	0.510 (2)	0.858 (2)	0.013 (6)*
H4N1	0.137 (4)	0.0533 (17)	0.876 (2)	0.023 (7)*
H4N2	0.173 (5)	0.190 (4)	0.7452 (11)	0.035 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.02971 (15)	0.01243 (12)	0.02039 (12)	−0.00512 (9)	0.00410 (9)	−0.00765 (8)
S1	0.0217 (3)	0.0111 (2)	0.0101 (2)	−0.0029 (2)	0.00152 (19)	−0.00200 (18)
N1	0.0190 (10)	0.0104 (8)	0.0119 (8)	−0.0022 (7)	0.0015 (7)	−0.0005 (6)
N2	0.0105 (8)	0.0144 (8)	0.0100 (8)	−0.0056 (6)	0.0021 (6)	−0.0034 (6)
N3	0.0154 (9)	0.0112 (8)	0.0091 (7)	−0.0032 (7)	0.0020 (6)	−0.0051 (6)
N4	0.0239 (10)	0.0117 (8)	0.0144 (8)	−0.0050 (7)	0.0044 (7)	−0.0056 (7)
C1	0.0176 (11)	0.0133 (9)	0.0127 (9)	−0.0021 (8)	0.0005 (8)	−0.0045 (8)
C2	0.0120 (10)	0.0108 (9)	0.0134 (9)	−0.0032 (7)	−0.0023 (8)	−0.0025 (7)
C3	0.0121 (10)	0.0167 (10)	0.0119 (9)	−0.0036 (8)	−0.0015 (8)	−0.0022 (7)
C4	0.0109 (10)	0.0174 (10)	0.0111 (9)	−0.0028 (8)	−0.0020 (7)	−0.0049 (7)
C5	0.0113 (10)	0.0106 (9)	0.0165 (9)	−0.0031 (7)	−0.0014 (8)	−0.0042 (7)
C6	0.0102 (10)	0.0124 (9)	0.0117 (9)	−0.0030 (7)	−0.0017 (7)	−0.0021 (7)
C7	0.0090 (10)	0.0132 (9)	0.0103 (9)	−0.0028 (7)	−0.0012 (7)	−0.0032 (7)
C8	0.0114 (10)	0.0116 (9)	0.0131 (9)	−0.0035 (8)	−0.0011 (7)	−0.0037 (7)
C9	0.0107 (10)	0.0137 (9)	0.0133 (9)	−0.0024 (8)	−0.0003 (8)	−0.0049 (7)
C10	0.0103 (10)	0.0129 (9)	0.0130 (9)	−0.0029 (7)	0.0001 (7)	−0.0038 (7)

Br1—C5	1.9032 (19)	C1—H1	0.9500
S1—C10	1.699 (2)	C2—C3	1.388 (3)
N1—C1	1.359 (3)	C2—C7	1.418 (3)
N1—C2	1.378 (3)	C3—C4	1.379 (3)
N1—H1N	0.878 (10)	C3—H3	0.9500
N2—C9	1.284 (3)	C4—C5	1.399 (3)
N2—N3	1.378 (2)	C4—H4	0.9500
N3—C10	1.339 (3)	C5—C6	1.372 (3)
N3—H3N	0.876 (10)	C6—C7	1.398 (3)
N4—C10	1.331 (3)	C6—H6	0.9500
N4—H4N1	0.880 (10)	C7—C8	1.447 (3)
N4—H4N2	0.873 (10)	C8—C9	1.437 (3)
C1—C8	1.376 (3)	C9—H9	0.9500
C1—N1—C2	109.25 (17)	C3—C4—H4	120.1
C1—N1—H1N	122.5 (19)	C5—C4—H4	120.1
C2—N1—H1N	126.2 (18)	C6—C5—C4	123.94 (18)
C9—N2—N3	115.12 (17)	C6—C5—Br1	118.76 (15)
C10—N3—N2	119.25 (16)	C4—C5—Br1	117.30 (15)
C10—N3—H3N	117.5 (16)	C5—C6—C7	117.04 (18)
N2—N3—H3N	122.8 (16)	C5—C6—H6	121.5
C10—N4—H4N1	119.9 (17)	C7—C6—H6	121.5
C10—N4—H4N2	118.1 (19)	C6—C7—C2	119.09 (17)
H4N1—N4—H4N2	120 (3)	C6—C7—C8	134.17 (18)
N1—C1—C8	110.69 (18)	C2—C7—C8	106.75 (17)
N1—C1—H1	124.7	C1—C8—C9	124.92 (18)
C8—C1—H1	124.7	C1—C8—C7	105.86 (17)
N1—C2—C3	129.70 (18)	C9—C8—C7	129.10 (18)
N1—C2—C7	107.45 (17)	N2—C9—C8	121.41 (18)
C3—C2—C7	122.85 (18)	N2—C9—H9	119.3
C4—C3—C2	117.27 (18)	C8—C9—H9	119.3
C4—C3—H3	121.4	N4—C10—N3	117.36 (18)
C2—C3—H3	121.4	N4—C10—S1	122.58 (16)
C3—C4—C5	119.81 (18)	N3—C10—S1	120.06 (15)
C9—N2—N3—C10	−179.30 (19)	C3—C2—C7—C6	0.3 (3)
C2—N1—C1—C8	0.5 (3)	N1—C2—C7—C8	0.4 (2)
C1—N1—C2—C3	180.0 (2)	C3—C2—C7—C8	179.9 (2)
C1—N1—C2—C7	−0.6 (2)	N1—C1—C8—C9	176.0 (2)
N1—C2—C3—C4	178.9 (2)	N1—C1—C8—C7	−0.2 (3)
C7—C2—C3—C4	−0.6 (3)	C6—C7—C8—C1	179.4 (2)
C2—C3—C4—C5	0.8 (3)	C2—C7—C8—C1	−0.2 (2)
C3—C4—C5—C6	−0.8 (3)	C6—C7—C8—C9	3.4 (4)
C3—C4—C5—Br1	179.01 (16)	C2—C7—C8—C9	−176.2 (2)
C4—C5—C6—C7	0.6 (3)	N3—N2—C9—C8	178.80 (19)
Br1—C5—C6—C7	−179.25 (15)	C1—C8—C9—N2	−179.4 (2)
C5—C6—C7—C2	−0.3 (3)	C7—C8—C9—N2	−4.0 (4)
C5—C6—C7—C8	−179.8 (2)	N2—N3—C10—N4	−2.8 (3)
N1—C2—C7—C6	−179.18 (18)	N2—N3—C10—S1	177.10 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S1i	0.88 (1)	2.60 (2)	3.390 (2)	150 (3)
N3—H3n···S1ii	0.88 (1)	2.65 (1)	3.508 (2)	167 (2)
N4—H4n1···S1iii	0.88 (1)	2.74 (1)	3.569 (2)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S1i	0.88 (1)	2.60 (2)	3.390 (2)	150 (3)
N3—H3n⋯S1ii	0.88 (1)	2.65 (1)	3.508 (2)	167 (2)
N4—H4n1⋯S1iii	0.88 (1)	2.74 (1)	3.569 (2)	158 (2)

Symmetry codes: (i) ; (ii) ; (iii) .