1,2,3,4-Tetra-hydro-isoquinoline-2-sulfonamide.

The title compound, C(9)H(12)N(2)O(2)S, is a useful precursor of a variety of modified sulfonamide mol-ecules. Due to the importance of these mol-ecules in biological systems (antibacterials, antidepressants and many other applications), there is a growing inter-est in the discovery of new biologically active compounds. In the title compound, the mol-ecules are linked by N-H⋯O inter-molecular hydrogen bonds involving the sulfonamide function to form an infinite two-dimensional network parallel to the (001) plane.

Related literature

For related literature, see: Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Martinez et al. (2000 ▶); Xiao & Timberlake (2000 ▶); Esteve & Bidal (2002 ▶); Soledade et al. (2006 ▶).

Experimental

Crystal data

C9H12N2O2S

M = 212.27

Monoclinic,

a = 5.275 (1) Å

b = 9.541 (1) Å

c = 10.229 (1) Å

β = 101.80 (5)°

V = 503.93 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 293 (2) K

0.10 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

8285 measured reflections

2210 independent reflections

2106 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.087

S = 1.13

2210 reflections

127 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 979 Friedel pairs

Flack parameter: −0.01 (6)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and CrystalBuilder (DECOMET Laboratory, 2007 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068158/dn2304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068158/dn2304Isup2.hkl

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

C9H12N2O2S	F000 = 224
Mr = 212.27	Dx = 1.399 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71070 Å
Hall symbol: P 2yb	Cell parameters from 6025 reflections
a = 5.275 (1) Å	θ = 2.0–27.5º
b = 9.541 (1) Å	µ = 0.30 mm−1
c = 10.229 (1) Å	T = 293 (2) K
β = 101.80 (5)º	Parallelepipedic, yellow
V = 503.93 (15) Å3	0.10 × 0.10 × 0.10 mm
Z = 2

Nonius KappaCCD diffractometer	2210 independent reflections
Radiation source: fine-focus sealed tube	2106 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 9 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 2.0º
φ and ω scans	h = −6→6
Absorption correction: none	k = −12→11
8285 measured reflections	l = −13→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.0148P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.25 e Å−3
2210 reflections	Δρmin = −0.30 e Å−3
127 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 979 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (6)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.56649 (7)	0.52966 (4)	0.42439 (3)	0.03710 (13)
N1	0.4887 (3)	0.60389 (14)	0.27757 (14)	0.0369 (3)
C3	0.5408 (4)	0.7557 (2)	0.2719 (2)	0.0475 (5)
H3A	0.6993	0.7792	0.3345	0.057*
H3B	0.3998	0.8087	0.2956	0.057*
O2	0.8298 (3)	0.5665 (2)	0.47635 (14)	0.0624 (5)
C6	0.1947 (4)	0.6250 (2)	0.06005 (17)	0.0415 (4)
C7	0.2282 (4)	0.5698 (2)	0.20079 (17)	0.0451 (4)
H7A	0.0985	0.6112	0.2439	0.054*
H7B	0.2038	0.4690	0.1987	0.054*
C8	0.3113 (5)	0.7727 (3)	−0.1068 (2)	0.0608 (6)
H8	0.4195	0.8406	−0.1311	0.073*
C9	0.3522 (4)	0.7280 (2)	0.02630 (18)	0.0442 (4)
C10	0.1146 (5)	0.7182 (3)	−0.2021 (2)	0.0631 (6)
H10	0.0888	0.7499	−0.2898	0.076*
C11	−0.0028 (5)	0.5703 (3)	−0.0374 (2)	0.0611 (6)
H11	−0.1098	0.5009	−0.0146	0.073*
C12	−0.0432 (5)	0.6172 (3)	−0.1677 (2)	0.0669 (7)
H12	−0.1773	0.5802	−0.2317	0.080*
C13	0.5667 (4)	0.7918 (2)	0.1305 (2)	0.0538 (5)
H13A	0.5636	0.8929	0.1200	0.065*
H13B	0.7325	0.7582	0.1162	0.065*
O1	0.4929 (3)	0.38595 (15)	0.40334 (14)	0.0580 (4)
N2	0.4032 (3)	0.59065 (17)	0.52808 (16)	0.0426 (3)
H21	0.4478	0.6796	0.5540	0.051*
H22	0.2355	0.5596	0.5109	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0370 (2)	0.0412 (2)	0.03170 (18)	0.00882 (17)	0.00373 (13)	0.00083 (17)
N1	0.0378 (8)	0.0365 (8)	0.0340 (6)	0.0022 (6)	0.0012 (5)	0.0019 (6)
C3	0.0564 (12)	0.0391 (10)	0.0451 (10)	−0.0060 (8)	0.0055 (9)	0.0004 (8)
O2	0.0313 (7)	0.1054 (14)	0.0475 (7)	0.0094 (7)	0.0011 (5)	0.0075 (8)
C6	0.0424 (10)	0.0444 (9)	0.0356 (8)	0.0066 (8)	0.0029 (7)	0.0031 (7)
C7	0.0430 (9)	0.0500 (11)	0.0385 (8)	−0.0071 (8)	−0.0008 (7)	0.0080 (7)
C8	0.0667 (15)	0.0737 (15)	0.0458 (11)	0.0099 (12)	0.0204 (11)	0.0167 (11)
C9	0.0457 (9)	0.0485 (10)	0.0399 (8)	0.0096 (8)	0.0122 (8)	0.0069 (8)
C10	0.0767 (15)	0.0790 (15)	0.0340 (9)	0.0256 (13)	0.0121 (10)	0.0077 (10)
C11	0.0631 (13)	0.0690 (14)	0.0434 (10)	−0.0081 (11)	−0.0069 (9)	0.0031 (9)
C12	0.0745 (15)	0.0789 (17)	0.0395 (10)	0.0129 (13)	−0.0066 (10)	−0.0040 (10)
C13	0.0525 (12)	0.0564 (13)	0.0514 (11)	−0.0089 (10)	0.0080 (9)	0.0130 (10)
O1	0.0933 (12)	0.0335 (7)	0.0448 (7)	0.0131 (7)	0.0087 (7)	0.0030 (6)
N2	0.0424 (8)	0.0439 (8)	0.0431 (8)	−0.0024 (6)	0.0122 (6)	−0.0091 (7)

S1—O2	1.4261 (16)	C8—C10	1.373 (4)
S1—O1	1.4293 (16)	C8—C9	1.401 (3)
S1—N2	1.6060 (16)	C8—H8	0.9300
S1—N1	1.6350 (14)	C9—C13	1.515 (3)
N1—C7	1.473 (2)	C10—C12	1.366 (4)
N1—C3	1.478 (2)	C10—H10	0.9300
C3—C13	1.520 (3)	C11—C12	1.380 (3)
C3—H3A	0.9700	C11—H11	0.9300
C3—H3B	0.9700	C12—H12	0.9300
C6—C9	1.376 (3)	C13—H13A	0.9700
C6—C11	1.388 (3)	C13—H13B	0.9700
C6—C7	1.509 (2)	N2—H21	0.9059
C7—H7A	0.9700	N2—H22	0.9154
C7—H7B	0.9700
O2—S1—O1	120.43 (11)	C10—C8—C9	121.3 (2)
O2—S1—N2	106.12 (10)	C10—C8—H8	119.4
O1—S1—N2	106.34 (10)	C9—C8—H8	119.4
O2—S1—N1	106.13 (10)	C6—C9—C8	118.7 (2)
O1—S1—N1	105.53 (8)	C6—C9—C13	120.86 (17)
N2—S1—N1	112.45 (9)	C8—C9—C13	120.4 (2)
C7—N1—C3	110.85 (15)	C12—C10—C8	119.7 (2)
C7—N1—S1	115.19 (12)	C12—C10—H10	120.1
C3—N1—S1	116.54 (12)	C8—C10—H10	120.1
N1—C3—C13	108.23 (16)	C12—C11—C6	121.1 (2)
N1—C3—H3A	110.1	C12—C11—H11	119.5
C13—C3—H3A	110.1	C6—C11—H11	119.5
N1—C3—H3B	110.1	C10—C12—C11	119.7 (2)
C13—C3—H3B	110.1	C10—C12—H12	120.1
H3A—C3—H3B	108.4	C11—C12—H12	120.1
C9—C6—C11	119.43 (18)	C9—C13—C3	112.27 (17)
C9—C6—C7	122.01 (17)	C9—C13—H13A	109.1
C11—C6—C7	118.57 (18)	C3—C13—H13A	109.1
N1—C7—C6	110.24 (15)	C9—C13—H13B	109.1
N1—C7—H7A	109.6	C3—C13—H13B	109.1
C6—C7—H7A	109.6	H13A—C13—H13B	107.9
N1—C7—H7B	109.6	S1—N2—H21	113.0
C6—C7—H7B	109.6	S1—N2—H22	112.6
H7A—C7—H7B	108.1	H21—N2—H22	122.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O1i	0.91	2.03	2.928 (2)	173
N2—H22···O2ii	0.92	2.10	2.971 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O1i	0.91	2.03	2.928 (2)	173
N2—H22⋯O2ii	0.92	2.10	2.971 (2)	159

Symmetry codes: (i) ; (ii) .