Pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dithione.

The seven-membered fused-ring in the title compound, C(12)H(12)N(2)S(2), adopts a boat conformation (with the two phenyl-ene C atoms representing the stern and the methine C atom the prow). This methine C atom and the tertiary N atom also belong to a five-membered ring, which has an envelope conformation. In the crystal structure, mol-ecules are linked about a center of inversion by pairs of N-H⋯S hydrogen bonds.

Related literature

For background to pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dione, see: Antonow et al. (2007 ▶); Kamal et al. (2007 ▶). For a related structure, Neidle et al. (1991 ▶).

Experimental

Crystal data

C12H12N2S2

M = 248.36

Monoclinic,

a = 13.9831 (5) Å

b = 10.0134 (3) Å

c = 8.2670 (3) Å

β = 97.089 (1)°

V = 1148.68 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 200 K

0.12 × 0.10 × 0.07 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.950, T max = 0.970

14013 measured reflections

3017 independent reflections

2117 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.01

3017 reflections

193 parameters

12 restraints

All H-atom parameters refined

Δρmax = 0.39 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021410/xu2774sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021410/xu2774Isup2.hkl

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

C12H12N2S2	F(000) = 520
Mr = 248.36	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2753 reflections
a = 13.9831 (5) Å	θ = 2.5–26.5°
b = 10.0134 (3) Å	µ = 0.44 mm−1
c = 8.2670 (3) Å	T = 200 K
β = 97.089 (1)°	Prism, colorless
V = 1148.68 (7) Å3	0.12 × 0.10 × 0.07 mm
Z = 4

Bruker X8 APEXII diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	2117 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 28.9°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.950, Tmax = 0.970	k = −12→13
14013 measured reflections	l = −11→11

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.047P)2 + 0.5062P] where P = (Fo2 + 2Fc2)/3
3017 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.39 e Å−3
12 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.60817 (4)	0.35830 (6)	0.60020 (8)	0.02972 (16)
S2	0.92223 (4)	0.75918 (6)	0.51650 (7)	0.02991 (16)
N1	0.62240 (12)	0.61932 (18)	0.5884 (2)	0.0221 (4)
N2	0.82707 (11)	0.57256 (17)	0.6540 (2)	0.0196 (4)
C1	0.65476 (14)	0.7511 (2)	0.6273 (2)	0.0205 (4)
C2	0.58339 (16)	0.8462 (2)	0.6410 (3)	0.0277 (5)
C3	0.60718 (17)	0.9769 (2)	0.6798 (3)	0.0318 (5)
C4	0.70347 (18)	1.0143 (2)	0.7079 (3)	0.0307 (5)
C5	0.77396 (16)	0.9220 (2)	0.6894 (3)	0.0251 (5)
C6	0.75250 (14)	0.7891 (2)	0.6467 (2)	0.0191 (4)
C7	0.83258 (14)	0.7001 (2)	0.6109 (2)	0.0194 (4)
C8	0.90083 (16)	0.4717 (2)	0.6291 (3)	0.0274 (5)
C9	0.86119 (16)	0.3432 (2)	0.6929 (3)	0.0284 (5)
C10	0.80322 (16)	0.3926 (2)	0.8260 (3)	0.0251 (5)
C11	0.75591 (14)	0.5204 (2)	0.7555 (2)	0.0190 (4)
C12	0.66077 (14)	0.5040 (2)	0.6465 (2)	0.0205 (4)
H1	0.5667 (10)	0.611 (2)	0.534 (2)	0.027 (6)*
H2	0.5176 (8)	0.822 (2)	0.628 (3)	0.034 (7)*
H3	0.5592 (13)	1.0406 (19)	0.694 (3)	0.030 (6)*
H4	0.7233 (16)	1.1027 (13)	0.736 (3)	0.032 (7)*
H5	0.8403 (8)	0.948 (2)	0.708 (3)	0.021 (6)*
H81	0.9608 (11)	0.498 (2)	0.697 (2)	0.030 (6)*
H82	0.9116 (16)	0.471 (2)	0.5138 (14)	0.034 (7)*
H91	0.8196 (14)	0.296 (2)	0.606 (2)	0.029 (6)*
H92	0.9130 (13)	0.281 (2)	0.736 (3)	0.037 (7)*
H11	0.7457 (14)	0.5865 (16)	0.8397 (19)	0.017 (5)*
H101	0.8467 (13)	0.421 (2)	0.9245 (19)	0.029 (6)*
H102	0.7565 (13)	0.3271 (18)	0.859 (2)	0.025 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0233 (3)	0.0180 (3)	0.0459 (3)	−0.0022 (2)	−0.0034 (2)	0.0011 (3)
S2	0.0248 (3)	0.0352 (4)	0.0300 (3)	−0.0034 (2)	0.0043 (2)	0.0035 (2)
N1	0.0172 (9)	0.0175 (10)	0.0299 (9)	−0.0008 (7)	−0.0039 (7)	−0.0007 (7)
N2	0.0172 (8)	0.0202 (10)	0.0211 (8)	0.0010 (7)	0.0012 (7)	−0.0007 (7)
C1	0.0238 (10)	0.0169 (11)	0.0202 (9)	0.0007 (8)	0.0004 (8)	−0.0004 (8)
C2	0.0244 (11)	0.0242 (12)	0.0344 (12)	0.0036 (9)	0.0037 (9)	−0.0019 (10)
C3	0.0360 (13)	0.0219 (13)	0.0382 (13)	0.0085 (10)	0.0074 (10)	−0.0027 (10)
C4	0.0455 (14)	0.0177 (12)	0.0289 (11)	−0.0002 (10)	0.0041 (10)	−0.0019 (9)
C5	0.0300 (12)	0.0222 (12)	0.0220 (10)	−0.0046 (9)	−0.0008 (9)	0.0023 (9)
C6	0.0232 (10)	0.0180 (11)	0.0157 (9)	0.0001 (8)	0.0013 (8)	0.0009 (8)
C7	0.0191 (10)	0.0229 (11)	0.0150 (9)	−0.0025 (8)	−0.0027 (7)	−0.0005 (8)
C8	0.0224 (11)	0.0276 (13)	0.0317 (12)	0.0081 (10)	0.0015 (9)	−0.0012 (10)
C9	0.0259 (11)	0.0223 (12)	0.0351 (12)	0.0073 (9)	−0.0042 (10)	−0.0028 (10)
C10	0.0296 (12)	0.0187 (11)	0.0254 (10)	0.0021 (9)	−0.0035 (9)	0.0012 (9)
C11	0.0221 (10)	0.0162 (10)	0.0184 (9)	0.0004 (8)	0.0016 (8)	0.0000 (8)
C12	0.0203 (10)	0.0197 (11)	0.0224 (10)	0.0019 (8)	0.0065 (8)	−0.0010 (8)

S1—C12	1.657 (2)	C4—H4	0.947 (10)
S2—C7	1.665 (2)	C5—C6	1.400 (3)
N1—C12	1.337 (3)	C5—H5	0.956 (9)
N1—C1	1.419 (3)	C6—C7	1.489 (3)
N1—H1	0.855 (10)	C8—C9	1.520 (3)
N2—C7	1.330 (3)	C8—H81	0.984 (10)
N2—C11	1.474 (2)	C8—H82	0.984 (9)
N2—C8	1.476 (3)	C9—C10	1.527 (3)
C1—C2	1.394 (3)	C9—H91	0.986 (10)
C1—C6	1.409 (3)	C9—H92	0.986 (10)
C2—C3	1.379 (3)	C10—C11	1.523 (3)
C2—H2	0.944 (10)	C10—H101	0.996 (10)
C3—C4	1.389 (3)	C10—H102	0.986 (9)
C3—H3	0.942 (10)	C11—C12	1.521 (3)
C4—C5	1.374 (3)	C11—H11	0.984 (9)
C12—N1—C1	128.23 (17)	N2—C8—C9	103.87 (17)
C12—N1—H1	113.8 (16)	N2—C8—H81	107.5 (14)
C1—N1—H1	117.1 (16)	C9—C8—H81	110.5 (14)
C7—N2—C11	123.94 (16)	N2—C8—H82	109.3 (14)
C7—N2—C8	123.70 (17)	C9—C8—H82	116.0 (15)
C11—N2—C8	111.65 (16)	H81—C8—H82	109.2 (19)
C2—C1—C6	120.0 (2)	C8—C9—C10	102.99 (18)
C2—C1—N1	116.23 (18)	C8—C9—H91	110.8 (14)
C6—C1—N1	123.69 (18)	C10—C9—H91	111.3 (13)
C3—C2—C1	120.8 (2)	C8—C9—H92	112.0 (14)
C3—C2—H2	118.2 (16)	C10—C9—H92	112.0 (14)
C1—C2—H2	120.9 (16)	H91—C9—H92	108 (2)
C2—C3—C4	119.7 (2)	C11—C10—C9	103.89 (17)
C2—C3—H3	121.1 (15)	C11—C10—H101	105.2 (14)
C4—C3—H3	119.1 (15)	C9—C10—H101	111.0 (13)
C5—C4—C3	119.6 (2)	C11—C10—H102	113.1 (13)
C5—C4—H4	117.6 (15)	C9—C10—H102	114.2 (13)
C3—C4—H4	122.8 (15)	H101—C10—H102	109.0 (18)
C4—C5—C6	122.2 (2)	N2—C11—C12	107.68 (15)
C4—C5—H5	119.9 (14)	N2—C11—C10	102.94 (16)
C6—C5—H5	117.9 (14)	C12—C11—C10	116.32 (17)
C5—C6—C1	117.39 (19)	N2—C11—H11	109.3 (12)
C5—C6—C7	118.44 (18)	C12—C11—H11	107.4 (12)
C1—C6—C7	123.96 (19)	C10—C11—H11	112.9 (12)
N2—C7—C6	116.84 (17)	N1—C12—C11	113.76 (17)
N2—C7—S2	122.59 (16)	N1—C12—S1	122.01 (15)
C6—C7—S2	120.55 (16)	C11—C12—S1	124.22 (15)
C12—N1—C1—C2	−140.9 (2)	C5—C6—C7—S2	−36.1 (2)
C12—N1—C1—C6	41.2 (3)	C1—C6—C7—S2	138.49 (17)
C6—C1—C2—C3	−2.6 (3)	C7—N2—C8—C9	−178.51 (18)
N1—C1—C2—C3	179.4 (2)	C11—N2—C8—C9	10.8 (2)
C1—C2—C3—C4	−0.9 (3)	N2—C8—C9—C10	−30.2 (2)
C2—C3—C4—C5	3.0 (3)	C8—C9—C10—C11	38.8 (2)
C3—C4—C5—C6	−1.6 (3)	C7—N2—C11—C12	79.1 (2)
C4—C5—C6—C1	−1.8 (3)	C8—N2—C11—C12	−110.28 (18)
C4—C5—C6—C7	173.16 (19)	C7—N2—C11—C10	−157.51 (18)
C2—C1—C6—C5	3.8 (3)	C8—N2—C11—C10	13.1 (2)
N1—C1—C6—C5	−178.33 (18)	C9—C10—C11—N2	−31.7 (2)
C2—C1—C6—C7	−170.78 (19)	C9—C10—C11—C12	85.7 (2)
N1—C1—C6—C7	7.0 (3)	C1—N1—C12—C11	−6.1 (3)
C11—N2—C7—C6	−9.7 (3)	C1—N1—C12—S1	174.50 (16)
C8—N2—C7—C6	−179.26 (17)	N2—C11—C12—N1	−65.3 (2)
C11—N2—C7—S2	171.99 (14)	C10—C11—C12—N1	179.85 (18)
C8—N2—C7—S2	2.5 (3)	N2—C11—C12—S1	114.07 (17)
C5—C6—C7—N2	145.61 (19)	C10—C11—C12—S1	−0.8 (3)
C1—C6—C7—N2	−39.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.86 (1)	2.58 (1)	3.411 (2)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86 (1)	2.58 (1)	3.411 (2)	166 (2)

Symmetry code: (i) .