Gliclazide impurity F: N-[(perhydro­cyclo­penta­[c]pyrrol-2-yl)amino­carbon­yl]-o-toluene­sulfonamide

Wu, D.; Wang, X.; Pang, D.; Su, W.; Sun, Y.

doi:10.1107/S1600536811054985

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o446

doi:10.1107/S1600536811054985

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Gliclazide impurity F: N-[(perhydrocyclopenta[c]pyrrol-2-yl)aminocarbonyl]-o-toluenesulfonamide

Di Wu,^a Xueyuan Wang,^b Dongying Pang,^b Wei Su ^c ^* and Yan Sun ^c

^aDepartment of Chemistry, School of Science, Tianjin University, Tianjin 300072, People's Republic of China, ^bTianJin Centralpharm Limited Company, Tianjin 300072, People's Republic of China, and ^cHigh Pressure Adsorption Laboratory, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: sytju@163.com

(Received 11 October 2011; accepted 21 December 2011; online 18 January 2012)

The title compound, C₁₅H₂₁N₃O₃S, is known to be an impurity of gliclazide [systematic name: N-(hexahydro-1H-cyclopenta[c]pyrrol-2-ylcarbamoyl)-4-methylbenzenesulfonamide], a sulfonylurea antidiabetic drug. Gliclazide has a p-tolyl group substituting the sulfonamide functionality, while the title molecule 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(sulfonyl) 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_r = 323.41
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.113
S = 1.04
3904 reflections
208 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.51 e Å⁻³

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) -x+1, -y+1, -z+2; (ii) -x+2, -y+1, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054985/bh2389sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811054985/bh2389Isup3.cml

checkCIF report

Comment top

Gliclazide Impurity F is one of the gliclazide impurities, as described in the European Pharmacopoeia. Gliclazide is a second-generation sulfonylurea oral hypoglycemic agent, which can reduce blood sugar and improve blood clotting function (Lebovitz & Feinglos, 1983). It not only can improve the metabolism of diabetic patients, but also improve or delay the incidence of vascular complications of diabetes.

The reason for the existence of this impurity is mainly due to the generation of ortho-isomeride during the production process of raw material, 4-methylphenylsulfonylurea or ethyl-[(4-methylphenyl)sulfonyl]carbamate. In the liquid chromatography separation experiments, the ortho gliclazide derivative has frequently been used as working sample. In this paper, we report the crystal structure of this compound.

The molecular structure is shown in Fig. 1. Molecular dimensions are within the normal ranges. The similar corresponding bond distances and angles have been reported in structure of gliclazide (Parvez et al., 1999; Winters et al., 1994). The methyl position of toluenesulfonyl moiety is the important difference between the two structures. The mean bond distances in the o-toluenesulfonyl moiety are C—C_aromatic = 1.507 (2), S=O = 1.4354 (14), Csp²-Csp²=1.394 (3) and S—Csp² = 1.7690 (18) Å, the aromatic ring being essentially planar. The mean values of the bond distances in the perhydrocyclopenta[c]pyrrole moiety in the title compound are Csp³-Csp³ =1.536 (3) and Csp³-N=1.473 (2) Å. The pyrrole (N3, C9, C10, C14, C15) ring and the fused five-membered cyclopentane (C10···C14) adopt N3- and C12- envelope conformations, respectively, with N3 0.624 and C12 0.611Å out of the planes of the remaining atoms of the corresponding rings.

The molecules are linked into dimers by intermolecular hydrogen bonds involving amino H-atoms. Intermolecular contacts between symmetry-related dimers form chains in the [100] direction.

Related literature top

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 top

A 1000 ml reactor fitted with an electric heater in the bottom, a mechanical stirrer, a thermometer and a condenser was loaded with urea (100 g) and sodium hydroxide (5 g). Slow heating and addition of o-toluenesulfonamide (48 g) after the reactants changed the mixture to the molten state. When the reaction was completed after 6 h, water and hydrochloric acid were added until pH = 7. After filtering, draining and vacuum drying, the o-toluene sulfonylurea was obtained (yield 90%). The o-toluene sulfonylurea was added to the equal amount of azolidine hydrochloride in acetonitrile under reflux for 6 h. Then, the desired products were obtained after cooling down, and filtered (yield 86%). Finally, the products were recrystallized from methanol.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); 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).

Figures top

Fig. 1. The title molecule with displacement ellipsoids for non-H atoms at the 50% probability level.

1-(2-Methylphenylsulfonyl)-3-(perhydrocyclopenta[c]pyrrol-2-yl)urea top

Crystal data top

C₁₅H₂₁N₃O₃S	F(000) = 688
M_r = 323.41	D_x = 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

Data collection top

Rigaku Saturn724 CCD diffractometer	3904 independent reflections
Radiation source: rotating anode	3461 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.070
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 1.9°
ω and ϕ scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −14→13
T_min = 0.959, T_max = 0.979	l = −17→17
16805 measured reflections

Refinement top

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(F_o²) + (0.0562P)² + 0.7703P] where P = (F_o² + 2F_c²)/3
3904 reflections	(Δ/σ)_max = 0.002
208 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.51 e Å⁻³
0 constraints

Crystal data top

C₁₅H₂₁N₃O₃S	V = 1640.2 (18) Å³
M_r = 323.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.891 (7) Å	µ = 0.21 mm⁻¹
b = 11.226 (7) Å	T = 113 K
c = 13.477 (9) Å	0.20 × 0.18 × 0.10 mm
β = 95.509 (9)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3904 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	3461 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.979	R_int = 0.070
16805 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.30 e Å⁻³
3904 reflections	Δρ_min = −0.51 e Å⁻³
208 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁N₃O₃S
M_r	323.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	10.891 (7), 11.226 (7), 13.477 (9)
β (°)	95.509 (9)
V (Å³)	1640.2 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2002)
T_min, T_max	0.959, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	16805, 3904, 3461
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.113, 1.04
No. of reflections	3904
No. of parameters	208
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.51

Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.898 (9)	1.922 (13)	2.820 (2)	177 (2)
N1—H1···O2ⁱⁱ	0.893 (7)	2.231 (11)	3.077 (2)	158 (2)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+2.

Acknowledgements

This study was supported by the Tianjin Natural Science Foundation (10JCZDJC23900).

References

Lebovitz, H. E. & Feinglos, M. N. (1983). Diabetes Mellitus: Theory and Practices, 3rd ed., edited by M. Ellenberg & H. Rifkin, pp. 591–610. New York: Medical Examination Publishing. Google Scholar
Parvez, M., Arayne, M. S., Zaman, M. K. & Sultana, N. (1999). Acta Cryst. C55, 74–75. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Winters, C., Shields, L., Timmins, P. & York, P. (1994). J. Pharm. Sci. 83, 300–304. CSD CrossRef CAS PubMed Web of Science Google Scholar

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Volume 68| Part 2| February 2012| Page o446

doi:10.1107/S1600536811054985

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Gliclazide impurity F: N-[(perhydro­cyclo­penta­[c]pyrrol-2-yl)amino­carbon­yl]-o-toluene­sulfonamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Gliclazide impurity F: N-[(perhydrocyclopenta[c]pyrrol-2-yl)aminocarbonyl]-o-toluenesulfonamide