Gliclazide impurity F: N-[(perhydro-cyclo-penta-[c]pyrrol-2-yl)amino-carbon-yl]-o-toluene-sulfonamide.

The title compound, C(15)H(21)N(3)O(3)S, is known to be an impurity of gliclazide [systematic name: N-(hexa-hydro-1H-cyclopenta[c]pyrrol-2-ylcarbamo-yl)-4-methyl-benzene-sulfonamide], a sul-fonyl-urea anti-diabetic drug. Gliclazide has a p-tolyl group substituting the sulfonamide functionality, while the title mol-ecule contains an o-tolyl group. Both five-membered fused rings adopt envelope conformations. In the crystal, N-H⋯O hydrogen bonds are formed between HN(C=O)NH groups, building centrosymmetric dimers. These dimers are further linked through N-H⋯O(sulfon-yl) contacts, forming chains in [100].

Related literature

For general background to gliclazide and the impurities of gliclazide, see: Lebovitz & Feinglos (1983 ▶). For the crystal structure of gliclazide, see: Parvez et al. (1999 ▶); Winters et al. (1994 ▶).

Experimental

Crystal data

C15H21N3O3S

M = 323.41

Monoclinic,

a = 10.891 (7) Å

b = 11.226 (7) Å

c = 13.477 (9) Å

β = 95.509 (9)°

V = 1640.2 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ▶) T min = 0.959, T max = 0.979

16805 measured reflections

3904 independent reflections

3461 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.04

3904 reflections

208 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054985/bh2389sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054985/bh2389Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054985/bh2389Isup3.cml

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

C15H21N3O3S	F(000) = 688
Mr = 323.41	Dx = 1.310 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5900 reflections
a = 10.891 (7) Å	θ = 1.5–27.9°
b = 11.226 (7) Å	µ = 0.21 mm−1
c = 13.477 (9) Å	T = 113 K
β = 95.509 (9)°	Prism, colourless
V = 1640.2 (18) Å3	0.20 × 0.18 × 0.10 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	3904 independent reflections
Radiation source: rotating anode	3461 reflections with I > 2σ(I)
multilayer	Rint = 0.070
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 1.9°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −14→13
Tmin = 0.959, Tmax = 0.979	l = −17→17
16805 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.7703P] where P = (Fo2 + 2Fc2)/3
3904 reflections	(Δ/σ)max = 0.002
208 parameters	Δρmax = 0.30 e Å−3
3 restraints	Δρmin = −0.51 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
S1	0.88574 (3)	0.63900 (3)	1.09521 (2)	0.01593 (11)
O1	0.83163 (10)	0.75502 (10)	1.08708 (8)	0.0226 (2)
O2	1.01217 (9)	0.62502 (10)	1.07406 (8)	0.0209 (2)
O3	0.62260 (9)	0.57766 (10)	1.07603 (8)	0.0205 (2)
N1	0.80984 (11)	0.54879 (12)	1.01545 (9)	0.0174 (3)
N2	0.63131 (12)	0.47495 (13)	0.93204 (9)	0.0222 (3)
N3	0.69959 (11)	0.44335 (12)	0.85221 (9)	0.0179 (3)
C1	1.01300 (15)	0.40745 (16)	1.19750 (12)	0.0251 (3)
H1A	0.9694	0.3882	1.1324	0.038*
H1B	1.0329	0.3337	1.2345	0.038*
H1C	1.0893	0.4503	1.1879	0.038*
C2	0.93199 (14)	0.48450 (14)	1.25551 (11)	0.0190 (3)
C3	0.91819 (16)	0.45650 (16)	1.35526 (12)	0.0250 (3)
H3	0.9612	0.3899	1.3850	0.030*
C4	0.84335 (16)	0.52348 (17)	1.41160 (12)	0.0288 (4)
H4	0.8377	0.5035	1.4795	0.035*
C5	0.77680 (16)	0.61910 (17)	1.36998 (12)	0.0266 (4)
H5	0.7238	0.6632	1.4083	0.032*
C6	0.78836 (15)	0.64984 (15)	1.27155 (11)	0.0211 (3)
H6	0.7428	0.7150	1.2420	0.025*
C7	0.86715 (13)	0.58463 (14)	1.21606 (10)	0.0165 (3)
C8	0.68259 (13)	0.53668 (14)	1.01056 (10)	0.0169 (3)
C9	0.70155 (15)	0.31371 (15)	0.83580 (12)	0.0235 (3)
H9A	0.6184	0.2788	0.8382	0.028*
H9B	0.7598	0.2739	0.8862	0.028*
C10	0.74462 (16)	0.30259 (17)	0.73176 (13)	0.0289 (4)
H10	0.8364	0.2946	0.7354	0.035*
C11	0.68091 (18)	0.20163 (19)	0.66902 (16)	0.0389 (5)
H11A	0.7340	0.1726	0.6185	0.047*
H11B	0.6607	0.1341	0.7118	0.047*
C12	0.56419 (18)	0.25961 (19)	0.61967 (14)	0.0358 (4)
H12A	0.5304	0.2138	0.5605	0.043*
H12B	0.5003	0.2661	0.6669	0.043*
C13	0.6079 (2)	0.3821 (2)	0.58998 (13)	0.0386 (5)
H13A	0.5380	0.4386	0.5806	0.046*
H13B	0.6484	0.3777	0.5274	0.046*
C14	0.70093 (17)	0.42092 (17)	0.67816 (12)	0.0294 (4)
H14	0.7720	0.4652	0.6541	0.035*
C15	0.64125 (16)	0.49198 (16)	0.75762 (11)	0.0238 (3)
H15A	0.6586	0.5782	0.7520	0.029*
H15B	0.5508	0.4797	0.7519	0.029*
H1	0.8539 (17)	0.5085 (18)	0.9741 (13)	0.038 (6)*
H2	0.5498 (9)	0.4609 (18)	0.9291 (15)	0.031 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01388 (18)	0.0184 (2)	0.01533 (18)	−0.00225 (13)	0.00034 (13)	0.00038 (12)
O1	0.0254 (6)	0.0186 (6)	0.0233 (5)	−0.0009 (5)	−0.0007 (4)	0.0021 (4)
O2	0.0125 (5)	0.0291 (6)	0.0212 (5)	−0.0041 (4)	0.0017 (4)	0.0003 (4)
O3	0.0147 (5)	0.0292 (6)	0.0180 (5)	0.0003 (4)	0.0028 (4)	−0.0054 (4)
N1	0.0125 (6)	0.0234 (7)	0.0162 (6)	−0.0016 (5)	0.0014 (4)	−0.0045 (5)
N2	0.0130 (6)	0.0359 (8)	0.0181 (6)	−0.0031 (5)	0.0037 (5)	−0.0082 (5)
N3	0.0158 (6)	0.0229 (7)	0.0155 (6)	−0.0003 (5)	0.0036 (5)	−0.0040 (5)
C1	0.0235 (8)	0.0263 (9)	0.0257 (8)	0.0063 (7)	0.0045 (6)	0.0044 (6)
C2	0.0158 (7)	0.0215 (8)	0.0192 (7)	−0.0010 (6)	−0.0007 (5)	0.0007 (6)
C3	0.0256 (8)	0.0292 (9)	0.0199 (7)	0.0010 (7)	−0.0005 (6)	0.0062 (6)
C4	0.0303 (9)	0.0399 (11)	0.0163 (7)	−0.0038 (8)	0.0029 (6)	0.0014 (7)
C5	0.0245 (8)	0.0366 (10)	0.0192 (7)	0.0001 (7)	0.0043 (6)	−0.0064 (7)
C6	0.0193 (7)	0.0225 (8)	0.0212 (7)	0.0002 (6)	0.0008 (6)	−0.0034 (6)
C7	0.0148 (6)	0.0188 (7)	0.0153 (6)	−0.0038 (6)	−0.0011 (5)	−0.0012 (5)
C8	0.0138 (6)	0.0204 (8)	0.0165 (6)	−0.0002 (6)	0.0018 (5)	0.0003 (5)
C9	0.0210 (7)	0.0224 (8)	0.0265 (8)	0.0013 (6)	−0.0010 (6)	−0.0019 (6)
C10	0.0202 (7)	0.0357 (10)	0.0308 (9)	0.0020 (7)	0.0027 (6)	−0.0136 (7)
C11	0.0335 (10)	0.0372 (11)	0.0447 (11)	0.0047 (8)	−0.0033 (8)	−0.0228 (9)
C12	0.0309 (9)	0.0407 (11)	0.0347 (9)	−0.0030 (8)	−0.0015 (7)	−0.0179 (8)
C13	0.0440 (11)	0.0524 (13)	0.0187 (8)	−0.0078 (10)	0.0001 (7)	−0.0064 (8)
C14	0.0323 (9)	0.0363 (10)	0.0204 (7)	−0.0092 (8)	0.0070 (7)	−0.0059 (7)
C15	0.0295 (8)	0.0234 (9)	0.0181 (7)	−0.0013 (7)	−0.0002 (6)	−0.0003 (6)

S1—O1	1.4295 (14)	C5—H5	0.9500
S1—O2	1.4413 (14)	C6—C7	1.398 (2)
S1—N1	1.6413 (14)	C6—H6	0.9500
S1—C7	1.7690 (18)	C9—C10	1.526 (2)
O3—C8	1.2360 (18)	C9—H9A	0.9900
N1—C8	1.388 (2)	C9—H9B	0.9900
N1—H1	0.893 (7)	C10—C11	1.539 (2)
N2—C8	1.341 (2)	C10—C14	1.564 (3)
N2—N3	1.4107 (17)	C10—H10	1.0000
N2—H2	0.898 (9)	C11—C12	1.523 (3)
N3—C9	1.473 (2)	C11—H11A	0.9900
N3—C15	1.474 (2)	C11—H11B	0.9900
C1—C2	1.507 (2)	C12—C13	1.521 (3)
C1—H1A	0.9800	C12—H12A	0.9900
C1—H1B	0.9800	C12—H12B	0.9900
C1—H1C	0.9800	C13—C14	1.548 (3)
C2—C3	1.403 (2)	C13—H13A	0.9900
C2—C7	1.405 (2)	C13—H13B	0.9900
C3—C4	1.388 (2)	C14—C15	1.529 (2)
C3—H3	0.9500	C14—H14	1.0000
C4—C5	1.384 (3)	C15—H15A	0.9900
C4—H4	0.9500	C15—H15B	0.9900
C5—C6	1.388 (2)
O1—S1—O2	118.60 (7)	N3—C9—C10	103.24 (13)
O1—S1—N1	109.51 (8)	N3—C9—H9A	111.1
O2—S1—N1	103.53 (7)	C10—C9—H9A	111.1
O1—S1—C7	107.59 (7)	N3—C9—H9B	111.1
O2—S1—C7	109.91 (7)	C10—C9—H9B	111.1
N1—S1—C7	107.17 (8)	H9A—C9—H9B	109.1
C8—N1—S1	121.96 (10)	C9—C10—C11	113.77 (16)
C8—N1—H1	121.0 (14)	C9—C10—C14	104.37 (13)
S1—N1—H1	117.1 (14)	C11—C10—C14	105.70 (15)
C8—N2—N3	121.44 (13)	C9—C10—H10	110.9
C8—N2—H2	117.4 (13)	C11—C10—H10	110.9
N3—N2—H2	120.9 (13)	C14—C10—H10	110.9
N2—N3—C9	112.29 (12)	C12—C11—C10	103.80 (16)
N2—N3—C15	110.58 (13)	C12—C11—H11A	111.0
C9—N3—C15	104.33 (12)	C10—C11—H11A	111.0
C2—C1—H1A	109.5	C12—C11—H11B	111.0
C2—C1—H1B	109.5	C10—C11—H11B	111.0
H1A—C1—H1B	109.5	H11A—C11—H11B	109.0
C2—C1—H1C	109.5	C13—C12—C11	103.40 (17)
H1A—C1—H1C	109.5	C13—C12—H12A	111.1
H1B—C1—H1C	109.5	C11—C12—H12A	111.1
C3—C2—C7	116.48 (14)	C13—C12—H12B	111.1
C3—C2—C1	119.38 (15)	C11—C12—H12B	111.1
C7—C2—C1	124.14 (14)	H12A—C12—H12B	109.0
C4—C3—C2	121.70 (16)	C12—C13—C14	104.54 (16)
C4—C3—H3	119.1	C12—C13—H13A	110.8
C2—C3—H3	119.1	C14—C13—H13A	110.8
C5—C4—C3	120.74 (15)	C12—C13—H13B	110.8
C5—C4—H4	119.6	C14—C13—H13B	110.8
C3—C4—H4	119.6	H13A—C13—H13B	108.9
C4—C5—C6	119.22 (15)	C15—C14—C13	113.18 (16)
C4—C5—H5	120.4	C15—C14—C10	104.51 (14)
C6—C5—H5	120.4	C13—C14—C10	105.24 (16)
C5—C6—C7	119.84 (16)	C15—C14—H14	111.2
C5—C6—H6	120.1	C13—C14—H14	111.2
C7—C6—H6	120.1	C10—C14—H14	111.2
C6—C7—C2	121.92 (14)	N3—C15—C14	103.62 (14)
C6—C7—S1	116.24 (12)	N3—C15—H15A	111.0
C2—C7—S1	121.79 (11)	C14—C15—H15A	111.0
O3—C8—N2	123.16 (14)	N3—C15—H15B	111.0
O3—C8—N1	121.58 (14)	C14—C15—H15B	111.0
N2—C8—N1	115.24 (13)	H15A—C15—H15B	109.0
O1—S1—N1—C8	−51.88 (14)	N3—N2—C8—O3	171.41 (14)
O2—S1—N1—C8	−179.30 (12)	N3—N2—C8—N1	−10.5 (2)
C7—S1—N1—C8	64.54 (14)	S1—N1—C8—O3	−12.1 (2)
C8—N2—N3—C9	122.19 (16)	S1—N1—C8—N2	169.83 (12)
C8—N2—N3—C15	−121.73 (16)	N2—N3—C9—C10	163.97 (12)
C7—C2—C3—C4	0.7 (2)	C15—N3—C9—C10	44.19 (15)
C1—C2—C3—C4	−179.07 (16)	N3—C9—C10—C11	−142.41 (15)
C2—C3—C4—C5	1.7 (3)	N3—C9—C10—C14	−27.70 (16)
C3—C4—C5—C6	−1.9 (3)	C9—C10—C11—C12	87.0 (2)
C4—C5—C6—C7	−0.3 (2)	C14—C10—C11—C12	−26.96 (19)
C5—C6—C7—C2	2.8 (2)	C10—C11—C12—C13	41.04 (19)
C5—C6—C7—S1	−174.57 (12)	C11—C12—C13—C14	−39.17 (19)
C3—C2—C7—C6	−2.9 (2)	C12—C13—C14—C15	−91.52 (19)
C1—C2—C7—C6	176.81 (15)	C12—C13—C14—C10	22.00 (19)
C3—C2—C7—S1	174.32 (12)	C9—C10—C14—C15	2.29 (17)
C1—C2—C7—S1	−5.9 (2)	C11—C10—C14—C15	122.56 (15)
O1—S1—C7—C6	10.97 (14)	C9—C10—C14—C13	−117.18 (15)
O2—S1—C7—C6	141.43 (12)	C11—C10—C14—C13	3.09 (18)
N1—S1—C7—C6	−106.71 (13)	N2—N3—C15—C14	−163.62 (13)
O1—S1—C7—C2	−166.44 (12)	C9—N3—C15—C14	−42.68 (16)
O2—S1—C7—C2	−35.98 (14)	C13—C14—C15—N3	137.91 (16)
N1—S1—C7—C2	75.88 (14)	C10—C14—C15—N3	23.94 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.90 (1)	1.92 (1)	2.820 (2)	177 (2)
N1—H1···O2ii	0.89 (1)	2.23 (1)	3.077 (2)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.90 (1)	1.92 (1)	2.820 (2)	177 (2)
N1—H1⋯O2ii	0.89 (1)	2.23 (1)	3.077 (2)	158 (2)

Symmetry codes: (i) ; (ii) .