4-(3-Methyl-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzene-sulfonamide.

In the title compound, C(18)H(17)N(3)O(2)S, the aromatic ring bearing the sulfamide unit is aligned at 61.65 (1)° with respect to the pyrrole ring; its amino group forms N-H⋯N and N-H⋯O hydrogen bonds to neighboring mol-ecules, generating sheets in the ac plane.

Related literature

For the crystal structure of a pyrrole synthesized using 2-acetyl­tetra­lone as a reactant, see: Portilla et al. (2007 ▶).

Experimental

Crystal data

C18H17N3O2S

M = 339.41

Monoclinic,

a = 4.8838 (1) Å

b = 27.3894 (4) Å

c = 12.2399 (2) Å

β = 94.738 (1)°

V = 1631.67 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.89 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.600, T max = 0.703

11808 measured reflections

3255 independent reflections

3166 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.184

S = 1.11

3255 reflections

226 parameters

14 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) global, I. DOI: 10.1107/S1600536811033186/bt5614sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033186/bt5614Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033186/bt5614Isup3.cml

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

C18H17N3O2S	F(000) = 712
Mr = 339.41	Dx = 1.382 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 7385 reflections
a = 4.8838 (1) Å	θ = 3.2–74.2°
b = 27.3894 (4) Å	µ = 1.89 mm−1
c = 12.2399 (2) Å	T = 100 K
β = 94.738 (1)°	Prism, orange brown
V = 1631.67 (5) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3255 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3166 reflections with I > 2σ(I)
Mirror	Rint = 0.018
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 3.2°
ω scans	h = −3→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −34→33
Tmin = 0.600, Tmax = 0.703	l = −14→15
11808 measured reflections

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0755P)2 + 3.2939P] where P = (Fo2 + 2Fc2)/3
3255 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.70 e Å−3
14 restraints	Δρmin = −0.65 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.89421 (18)	0.67458 (3)	0.78209 (7)	0.0424 (3)
O1	0.8478 (8)	0.63001 (10)	0.8387 (2)	0.0718 (11)
O2	1.1649 (6)	0.69481 (19)	0.7792 (3)	0.0936 (15)
N1	0.7213 (6)	0.71611 (10)	0.8343 (2)	0.0316 (6)
N2	0.4538 (6)	0.64587 (9)	0.3184 (2)	0.0325 (6)
N3	0.2861 (7)	0.68173 (10)	0.2717 (2)	0.0430 (8)
C1	0.4586 (7)	0.60588 (11)	0.2510 (2)	0.0286 (6)
C2	0.6045 (6)	0.55949 (10)	0.2675 (2)	0.0260 (6)
C3	0.8268 (6)	0.55121 (11)	0.3446 (2)	0.0287 (6)
H3	0.8945	0.5771	0.3909	0.034*
C4	0.9494 (7)	0.50567 (12)	0.3544 (2)	0.0338 (7)
H4	1.1012	0.5004	0.4068	0.041*
C5	0.8501 (7)	0.46774 (12)	0.2875 (3)	0.0348 (7)
H5	0.9295	0.4361	0.2957	0.042*
C6	0.6338 (7)	0.47599 (11)	0.2082 (2)	0.0305 (7)
H6	0.5698	0.4500	0.1616	0.037*
C7	0.5095 (6)	0.52151 (11)	0.1959 (2)	0.0260 (6)
C8	0.2724 (7)	0.53032 (12)	0.1096 (2)	0.0312 (7)
H8A	0.0975	0.5235	0.1423	0.037*
H8B	0.2875	0.5070	0.0486	0.037*
C9	0.2622 (8)	0.58217 (12)	0.0634 (2)	0.0373 (8)
H9A	0.4125	0.5870	0.0149	0.045*
H9B	0.0850	0.5878	0.0199	0.045*
C10	0.2932 (7)	0.61727 (12)	0.1578 (2)	0.0340 (7)
C11	0.1879 (8)	0.66404 (13)	0.1747 (3)	0.0407 (8)
C12	−0.0164 (11)	0.69262 (15)	0.1018 (4)	0.0586 (12)
H12A	−0.0683	0.7222	0.1399	0.088*
H12B	−0.1802	0.6726	0.0836	0.088*
H12C	0.0660	0.7016	0.0343	0.088*
C13	0.5657 (7)	0.65231 (11)	0.4290 (2)	0.0293 (7)
C14	0.7437 (8)	0.69042 (14)	0.4540 (3)	0.0435 (9)
H14	0.7941	0.7118	0.3979	0.052*
C15	0.8491 (8)	0.69741 (14)	0.5616 (3)	0.0462 (9)
H15	0.9728	0.7235	0.5798	0.055*
C16	0.7714 (7)	0.66571 (12)	0.6426 (3)	0.0316 (7)
C17	0.5945 (7)	0.62796 (12)	0.6171 (3)	0.0344 (7)
H17	0.5436	0.6065	0.6729	0.041*
C18	0.4900 (7)	0.62110 (12)	0.5098 (3)	0.0333 (7)
H18	0.3664	0.5950	0.4917	0.040*
H1	0.756 (10)	0.7464 (7)	0.815 (4)	0.061 (14)*
H2	0.547 (3)	0.7076 (14)	0.829 (3)	0.041 (11)*

	U11	U22	U33	U12	U13	U23
S1	0.0376 (5)	0.0539 (6)	0.0321 (5)	0.0161 (4)	−0.0181 (3)	−0.0213 (4)
O1	0.134 (3)	0.0376 (14)	0.0361 (14)	0.0337 (17)	−0.0418 (17)	−0.0086 (11)
O2	0.0354 (16)	0.172 (4)	0.072 (2)	0.001 (2)	−0.0045 (15)	−0.070 (3)
N1	0.0401 (16)	0.0257 (13)	0.0280 (13)	−0.0022 (11)	−0.0041 (11)	−0.0051 (10)
N2	0.0532 (17)	0.0240 (12)	0.0185 (12)	0.0055 (11)	−0.0070 (11)	0.0000 (9)
N3	0.069 (2)	0.0290 (14)	0.0290 (15)	0.0111 (14)	−0.0105 (14)	0.0018 (11)
C1	0.0418 (17)	0.0252 (14)	0.0182 (13)	−0.0001 (12)	−0.0021 (12)	0.0003 (11)
C2	0.0346 (16)	0.0257 (14)	0.0173 (13)	−0.0009 (12)	−0.0006 (11)	−0.0018 (11)
C3	0.0326 (16)	0.0316 (15)	0.0210 (14)	0.0013 (12)	−0.0039 (11)	−0.0035 (11)
C4	0.0394 (18)	0.0405 (17)	0.0208 (14)	0.0080 (14)	−0.0018 (12)	−0.0006 (12)
C5	0.0451 (19)	0.0299 (15)	0.0296 (16)	0.0081 (14)	0.0041 (14)	0.0006 (12)
C6	0.0451 (18)	0.0264 (14)	0.0203 (14)	−0.0047 (13)	0.0041 (12)	−0.0035 (11)
C7	0.0313 (15)	0.0293 (14)	0.0175 (13)	−0.0038 (12)	0.0024 (11)	−0.0023 (11)
C8	0.0371 (17)	0.0366 (16)	0.0189 (14)	−0.0040 (13)	−0.0039 (12)	−0.0048 (12)
C9	0.051 (2)	0.0397 (18)	0.0191 (14)	0.0002 (15)	−0.0066 (13)	−0.0019 (13)
C10	0.0474 (19)	0.0321 (16)	0.0211 (14)	−0.0003 (14)	−0.0058 (13)	0.0024 (12)
C11	0.059 (2)	0.0350 (17)	0.0256 (16)	0.0056 (16)	−0.0105 (15)	0.0034 (13)
C12	0.083 (3)	0.043 (2)	0.044 (2)	0.016 (2)	−0.026 (2)	0.0050 (17)
C13	0.0408 (17)	0.0245 (14)	0.0211 (14)	0.0039 (12)	−0.0056 (12)	−0.0041 (11)
C14	0.057 (2)	0.0407 (19)	0.0329 (18)	−0.0142 (17)	0.0063 (16)	−0.0043 (15)
C15	0.046 (2)	0.049 (2)	0.044 (2)	−0.0169 (17)	0.0021 (16)	−0.0193 (17)
C16	0.0301 (16)	0.0381 (16)	0.0248 (15)	0.0071 (13)	−0.0074 (12)	−0.0104 (12)
C17	0.0456 (19)	0.0330 (16)	0.0227 (15)	0.0008 (14)	−0.0085 (13)	−0.0001 (12)
C18	0.0418 (18)	0.0312 (15)	0.0247 (15)	−0.0050 (13)	−0.0098 (13)	−0.0008 (12)

S1—O1	1.431 (3)	C7—C8	1.521 (4)
S1—O2	1.437 (4)	C8—C9	1.528 (5)
S1—N1	1.582 (3)	C8—H8A	0.9900
S1—C16	1.778 (3)	C8—H8B	0.9900
N1—H1	0.882 (11)	C9—C10	1.502 (4)
N1—H2	0.880 (11)	C9—H9A	0.9900
N2—N3	1.373 (4)	C9—H9B	0.9900
N2—C1	1.372 (4)	C10—C11	1.402 (5)
N2—C13	1.428 (4)	C11—C12	1.503 (5)
N3—C11	1.334 (5)	C12—H12A	0.9800
C1—C10	1.377 (4)	C12—H12B	0.9800
C1—C2	1.463 (4)	C12—H12C	0.9800
C2—C7	1.413 (4)	C13—C14	1.377 (5)
C2—C3	1.398 (4)	C13—C18	1.381 (4)
C3—C4	1.385 (4)	C14—C15	1.387 (5)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.385 (5)	C15—C16	1.395 (5)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.392 (5)	C16—C17	1.367 (5)
C5—H5	0.9500	C17—C18	1.382 (4)
C6—C7	1.390 (4)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
O1—S1—O2	121.6 (3)	C9—C8—H8B	108.8
O1—S1—N1	107.85 (18)	H8A—C8—H8B	107.7
O2—S1—N1	104.8 (2)	C10—C9—C8	108.2 (2)
O1—S1—C16	107.07 (16)	C10—C9—H9A	110.1
O2—S1—C16	105.50 (19)	C8—C9—H9A	110.1
N1—S1—C16	109.67 (15)	C10—C9—H9B	110.1
S1—N1—H1	116 (3)	C8—C9—H9B	110.1
S1—N1—H2	109 (3)	H9A—C9—H9B	108.4
H1—N1—H2	116 (4)	C1—C10—C11	106.4 (3)
N3—N2—C1	111.1 (2)	C1—C10—C9	120.5 (3)
N3—N2—C13	118.3 (2)	C11—C10—C9	133.1 (3)
C1—N2—C13	130.1 (3)	N3—C11—C10	110.7 (3)
C11—N3—N2	105.6 (3)	N3—C11—C12	120.8 (3)
N2—C1—C10	106.2 (3)	C10—C11—C12	128.5 (3)
N2—C1—C2	130.0 (3)	C11—C12—H12A	109.5
C10—C1—C2	123.8 (3)	C11—C12—H12B	109.5
C7—C2—C3	119.8 (3)	H12A—C12—H12B	109.5
C7—C2—C1	115.0 (3)	C11—C12—H12C	109.5
C3—C2—C1	125.2 (3)	H12A—C12—H12C	109.5
C4—C3—C2	120.7 (3)	H12B—C12—H12C	109.5
C4—C3—H3	119.6	C14—C13—C18	120.8 (3)
C2—C3—H3	119.6	C14—C13—N2	119.3 (3)
C5—C4—C3	119.8 (3)	C18—C13—N2	119.9 (3)
C5—C4—H4	120.1	C13—C14—C15	119.6 (3)
C3—C4—H4	120.1	C13—C14—H14	120.2
C4—C5—C6	119.9 (3)	C15—C14—H14	120.2
C4—C5—H5	120.1	C14—C15—C16	119.2 (3)
C6—C5—H5	120.1	C14—C15—H15	120.4
C7—C6—C5	121.4 (3)	C16—C15—H15	120.4
C7—C6—H6	119.3	C17—C16—C15	120.8 (3)
C5—C6—H6	119.3	C17—C16—S1	118.7 (3)
C6—C7—C2	118.4 (3)	C15—C16—S1	120.5 (3)
C6—C7—C8	121.2 (3)	C16—C17—C18	119.8 (3)
C2—C7—C8	120.4 (3)	C16—C17—H17	120.1
C7—C8—C9	113.8 (3)	C18—C17—H17	120.1
C7—C8—H8A	108.8	C17—C18—C13	119.8 (3)
C9—C8—H8A	108.8	C17—C18—H18	120.1
C7—C8—H8B	108.8	C13—C18—H18	120.1
C1—N2—N3—C11	−0.4 (4)	C8—C9—C10—C1	34.6 (4)
C13—N2—N3—C11	−173.2 (3)	C8—C9—C10—C11	−147.1 (4)
N3—N2—C1—C10	1.3 (4)	N2—N3—C11—C10	−0.7 (4)
C13—N2—C1—C10	173.0 (3)	N2—N3—C11—C12	177.0 (4)
N3—N2—C1—C2	−179.2 (3)	C1—C10—C11—N3	1.5 (4)
C13—N2—C1—C2	−7.5 (6)	C9—C10—C11—N3	−177.0 (4)
N2—C1—C2—C7	163.9 (3)	C1—C10—C11—C12	−176.0 (4)
C10—C1—C2—C7	−16.6 (5)	C9—C10—C11—C12	5.5 (7)
N2—C1—C2—C3	−17.6 (5)	N3—N2—C13—C14	−63.9 (5)
C10—C1—C2—C3	161.8 (3)	C1—N2—C13—C14	124.9 (4)
C7—C2—C3—C4	−2.2 (5)	N3—N2—C13—C18	114.7 (4)
C1—C2—C3—C4	179.4 (3)	C1—N2—C13—C18	−56.5 (5)
C2—C3—C4—C5	−0.4 (5)	C18—C13—C14—C15	0.2 (6)
C3—C4—C5—C6	2.2 (5)	N2—C13—C14—C15	178.8 (3)
C4—C5—C6—C7	−1.5 (5)	C13—C14—C15—C16	−0.3 (6)
C5—C6—C7—C2	−1.1 (5)	C14—C15—C16—C17	0.3 (6)
C5—C6—C7—C8	−179.7 (3)	C14—C15—C16—S1	−178.1 (3)
C3—C2—C7—C6	2.9 (4)	O1—S1—C16—C17	18.0 (3)
C1—C2—C7—C6	−178.5 (3)	O2—S1—C16—C17	148.8 (3)
C3—C2—C7—C8	−178.5 (3)	N1—S1—C16—C17	−98.8 (3)
C1—C2—C7—C8	0.1 (4)	O1—S1—C16—C15	−163.6 (3)
C6—C7—C8—C9	−148.2 (3)	O2—S1—C16—C15	−32.7 (4)
C2—C7—C8—C9	33.2 (4)	N1—S1—C16—C15	79.7 (3)
C7—C8—C9—C10	−48.0 (4)	C15—C16—C17—C18	−0.3 (5)
N2—C1—C10—C11	−1.6 (4)	S1—C16—C17—C18	178.2 (3)
C2—C1—C10—C11	178.8 (3)	C16—C17—C18—C13	0.2 (5)
N2—C1—C10—C9	177.1 (3)	C14—C13—C18—C17	−0.2 (5)
C2—C1—C10—C9	−2.5 (5)	N2—C13—C18—C17	−178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.88 (1)	2.05 (1)	2.925 (4)	173 (5)
N1—H2···O2ii	0.88 (1)	1.95 (2)	2.806 (4)	165 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.88 (1)	2.05 (1)	2.925 (4)	173 (5)
N1—H2⋯O2ii	0.88 (1)	1.95 (2)	2.806 (4)	165 (4)

Symmetry codes: (i) ; (ii) .