Ethyl 3-(4-methyl­benzene­sulfonamido)thieno[2,3-b]pyridine-2-carboxyl­ate

Zhang, W.; Zheng, R.; Song, H.; Yang, S.-Y.; Yu, L.-T.

doi:10.1107/S1600536809000269

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o257

doi:10.1107/S1600536809000269

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Ethyl 3-(4-methylbenzenesulfonamido)thieno[2,3-b]pyridine-2-carboxylate

Wen-qin Zhang,^a Ren-lin Zheng,^a Hang Song,^b Sheng-Yong Yang ^a and Luo-Ting Yu ^a ^*

^aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, and ^bDepartment of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China
^*Correspondence e-mail: yuluot@yahoo.com.cn

(Received 14 December 2008; accepted 5 January 2009; online 8 January 2009)

The thieno[2,3-b]pyridine ring system of the title compound, C₁₇H₁₆N₂O₄S₂, is essentially planar, the amino and carbonyl groups being nearly coplanar with the heterocyclic ring system. There are two N—H⋯O hydrogen-bonding interactions involving the same N—H donor set and two different acceptors, one in an intramolecular bond helping to fix the molecular geometry and the other defining a dimeric structure around the symmetry centre at (0, $[{\script{1\over 2}}]$ , $[{\script{1\over 2}}]$ ).

Related literature

For general background, see: Litvinov et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₆N₂O₄S₂
M_r = 376.46
Orthorhombic, P b c a
a = 14.809 (4) Å
b = 11.892 (3) Å
c = 19.494 (5) Å
V = 3433.1 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 (2) K
0.46 × 0.44 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: spherical [modified Dwiggins (1975 ) interpolation procedure] T_min = 0.861, T_max = 0.872
3590 measured reflections
3075 independent reflections
2032 reflections with I > 2σ(I)
R_int = 0.005
3 standard reflections every 200 reflections intensity decay: 3.0%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.186
S = 1.13
3075 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.95 (3)	2.22 (3)	2.867 (4)	125 (3)
N1—H1N⋯O2ⁱ	0.95 (3)	2.21 (3)	3.033 (4)	145 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000269/bg2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000269/bg2232Isup2.hkl

checkCIF report

Comment top

Thieno[2,3-b]pyridine derivatives are of great importance owing to their wide biological properties (Litvinov et al.,2005). The title compound is one of the key intermediates in our synthetic investigations of antitumor drugs. We report here its crystal structure.

The thieno[2,3-b]pyridine ring system of the title compound C₁₇H₁₆N₂O₄S₂, (Fig.1) is essentially planar, with the amino and the carbonyl groups being nearly coplanar with the heterocyclic ring system.

There are two main N-H···O H-bonding interactions (Table 1), involving the same N1-H1N donor set and two different acceptors, O4 (in an intramolecular bond fixing the molecular geometry) and O2 ⁱ, i: -x, -y+1, -z+1, defining a dimeric structure around the symmetry centre at (0,0.5,0.5) (Fig.2)

Related literature top

For general background, see: Litvinov et al. (2005). For related literature, see: Dwiggins (1975).

Experimental top

A solution of ethyl 3-amino-4H-thieno[2,3-b]pyridine -2-carboxylate(2 g, 9 mmol), p-toluenesulfonyl chloride (5.2 g, 27 mmol) and pyridine (3.7 ml, 45 mmol) in dichloromethane (100 ml) was stirred until the reaction was complete. The reaction mixture was washed twice with a saturated aqueous solution of CuSO₄ and once with water. The organic layer was dried and concentrated in vacuum and the resulting residue was purified by crystallization from dichloromethane to yield a white solid (3.1 g, 91%). Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of dichloromethane and petroleum (1:2).

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. View of the dimeric structure in the title compound. Hydrogen bonds are shown as hollow bonds (intermolecular ones as dashed lines, intramolecular ones in full lining). Symmetry code: (i) -x, -y+1, -z+1.

Ethyl 3-(4-methylbenzenesulfonamido)thieno[2,3-b]pyridine-2-carboxylate top

Crystal data top

C₁₇H₁₆N₂O₄S₂	F(000) = 1568
M_r = 376.46	D_x = 1.457 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 24 reflections
a = 14.809 (4) Å	θ = 4.5–7.7°
b = 11.892 (3) Å	µ = 0.34 mm⁻¹
c = 19.494 (5) Å	T = 293 K
V = 3433.1 (15) Å³	Block, colourless
Z = 8	0.46 × 0.44 × 0.42 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.005
Graphite monochromator	θ_max = 25.6°, θ_min = 2.1°
ω/2θ scans	h = −17→10
Absorption correction: for a sphere (interpolation; International Tables for X-ray Crystallography, 1959, Vol II, p. 302; 1992, Vol. C, p. 523); Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification.	k = −2→14
T_min = 0.861, T_max = 0.872	l = −13→23
3590 measured reflections	3 standard reflections every 200 reflections
3075 independent reflections	intensity decay: 3.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.186	w = 1/[σ²(F_o²) + (0.0996P)² + 1.4444P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
3075 reflections	Δρ_max = 0.36 e Å⁻³
233 parameters	Δρ_min = −0.74 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0175 (17)

Crystal data top

C₁₇H₁₆N₂O₄S₂	V = 3433.1 (15) Å³
M_r = 376.46	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.809 (4) Å	µ = 0.34 mm⁻¹
b = 11.892 (3) Å	T = 293 K
c = 19.494 (5) Å	0.46 × 0.44 × 0.42 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2032 reflections with I > 2σ(I)
Absorption correction: for a sphere (interpolation; International Tables for X-ray Crystallography, 1959, Vol II, p. 302; 1992, Vol. C, p. 523); Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification.	R_int = 0.005
T_min = 0.861, T_max = 0.872	3 standard reflections every 200 reflections
3590 measured reflections	intensity decay: 3.0%
3075 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.186	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.36 e Å⁻³
3075 reflections	Δρ_min = −0.74 e Å⁻³
233 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.09964 (6)	0.61780 (8)	0.44511 (5)	0.0446 (3)
S2	−0.09888 (7)	0.97224 (9)	0.42142 (5)	0.0519 (3)
O1	0.14122 (18)	0.6604 (2)	0.38494 (13)	0.0557 (7)
O2	0.09322 (18)	0.4988 (2)	0.45432 (15)	0.0578 (8)
O3	−0.12382 (18)	0.9327 (2)	0.56425 (12)	0.0497 (7)
O4	−0.0664 (2)	0.7593 (3)	0.57213 (13)	0.0617 (8)
N1	−0.0053 (2)	0.6628 (3)	0.44558 (15)	0.0422 (7)
H1N	−0.033 (3)	0.642 (3)	0.4875 (12)	0.067 (13)*
N2	−0.0759 (3)	0.9677 (3)	0.28514 (19)	0.0651 (10)
C1	0.2655 (4)	0.8311 (6)	0.6960 (4)	0.129 (3)
H1A	0.2173	0.8723	0.7172	0.194*
H1B	0.3126	0.8821	0.6828	0.194*
H1C	0.2890	0.7769	0.7278	0.194*
C2	0.2296 (3)	0.7703 (6)	0.6323 (3)	0.0842 (18)
C3	0.2462 (3)	0.8165 (5)	0.5677 (3)	0.0783 (15)
H3	0.2827	0.8798	0.5635	0.094*
C4	0.2083 (3)	0.7678 (3)	0.5100 (2)	0.0578 (11)
H4	0.2197	0.7975	0.4668	0.069*
C5	0.1529 (2)	0.6741 (3)	0.51725 (19)	0.0469 (9)
C6	0.1372 (3)	0.6279 (4)	0.5808 (2)	0.0622 (11)
H6	0.1006	0.5646	0.5850	0.075*
C7	0.1755 (3)	0.6751 (5)	0.6376 (2)	0.0826 (16)
H7	0.1652	0.6433	0.6805	0.099*
C8	−0.0288 (2)	0.7731 (3)	0.42354 (17)	0.0399 (8)
C9	−0.0649 (2)	0.8527 (3)	0.46538 (18)	0.0417 (8)
C10	−0.0648 (2)	0.9136 (4)	0.34493 (19)	0.0495 (10)
C11	−0.0285 (2)	0.8071 (3)	0.35295 (17)	0.0434 (9)
C12	−0.0836 (2)	0.8412 (4)	0.53894 (18)	0.0446 (9)
C13	−0.1472 (3)	0.9290 (3)	0.63719 (18)	0.0524 (10)
H13A	−0.0931	0.9208	0.6648	0.063*
H13B	−0.1867	0.8657	0.6464	0.063*
C14	−0.1939 (3)	1.0370 (4)	0.6541 (2)	0.0623 (11)
H14A	−0.1538	1.0988	0.6456	0.093*
H14B	−0.2112	1.0367	0.7016	0.093*
H14C	−0.2468	1.0446	0.6260	0.093*
C15	−0.0523 (3)	0.9075 (5)	0.2299 (2)	0.0724 (14)
H15	−0.0606	0.9403	0.1870	0.087*
C16	−0.0170 (3)	0.8024 (5)	0.2319 (2)	0.0662 (13)
H16	−0.0015	0.7670	0.1910	0.079*
C17	−0.0036 (2)	0.7466 (4)	0.29326 (19)	0.0511 (10)
H17	0.0202	0.6743	0.2952	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0471 (6)	0.0449 (6)	0.0417 (6)	0.0037 (4)	0.0058 (4)	−0.0009 (4)
S2	0.0528 (6)	0.0546 (7)	0.0483 (6)	0.0089 (5)	−0.0010 (4)	0.0069 (5)
O1	0.0528 (15)	0.0707 (19)	0.0435 (16)	0.0033 (14)	0.0104 (12)	0.0073 (13)
O2	0.0690 (19)	0.0428 (17)	0.0617 (19)	0.0040 (13)	0.0060 (13)	−0.0015 (13)
O3	0.0542 (15)	0.0584 (17)	0.0365 (14)	0.0043 (13)	0.0087 (11)	−0.0027 (12)
O4	0.084 (2)	0.066 (2)	0.0350 (15)	0.0072 (16)	0.0038 (14)	0.0072 (14)
N1	0.0420 (16)	0.0428 (17)	0.0418 (17)	−0.0035 (13)	0.0015 (13)	0.0029 (13)
N2	0.072 (2)	0.075 (3)	0.048 (2)	0.0039 (19)	−0.0066 (17)	0.0199 (19)
C1	0.093 (4)	0.175 (7)	0.120 (5)	0.051 (4)	−0.052 (4)	−0.086 (5)
C2	0.047 (3)	0.123 (5)	0.083 (4)	0.031 (3)	−0.024 (2)	−0.047 (3)
C3	0.053 (3)	0.084 (4)	0.098 (4)	0.010 (2)	−0.017 (3)	−0.028 (3)
C4	0.050 (2)	0.049 (2)	0.074 (3)	0.0013 (18)	−0.005 (2)	−0.002 (2)
C5	0.043 (2)	0.050 (2)	0.048 (2)	0.0082 (17)	0.0021 (16)	0.0002 (17)
C6	0.053 (2)	0.079 (3)	0.055 (3)	−0.001 (2)	−0.0040 (19)	0.007 (2)
C7	0.058 (3)	0.140 (5)	0.050 (3)	0.026 (3)	−0.010 (2)	−0.012 (3)
C8	0.0349 (17)	0.053 (2)	0.0318 (18)	−0.0077 (15)	−0.0022 (14)	0.0041 (15)
C9	0.0363 (17)	0.055 (2)	0.0337 (18)	0.0026 (16)	−0.0032 (14)	0.0031 (16)
C10	0.0427 (19)	0.065 (3)	0.041 (2)	−0.0023 (18)	−0.0064 (16)	0.0121 (18)
C11	0.0354 (17)	0.063 (2)	0.0315 (19)	−0.0086 (16)	−0.0014 (14)	0.0019 (17)
C12	0.0399 (19)	0.063 (2)	0.0313 (19)	−0.0064 (17)	−0.0003 (14)	0.0004 (18)
C13	0.059 (2)	0.063 (3)	0.034 (2)	−0.003 (2)	0.0059 (17)	−0.0042 (18)
C14	0.068 (3)	0.068 (3)	0.051 (3)	−0.007 (2)	0.012 (2)	−0.011 (2)
C15	0.071 (3)	0.106 (4)	0.040 (3)	−0.005 (3)	−0.009 (2)	0.023 (3)
C16	0.060 (3)	0.108 (4)	0.030 (2)	−0.024 (3)	−0.0005 (17)	0.003 (2)
C17	0.050 (2)	0.061 (3)	0.042 (2)	−0.0113 (18)	0.0022 (16)	−0.0028 (17)

Geometric parameters (Å, º) top

S1—O1	1.418 (3)	C4—H4	0.9300
S1—O2	1.430 (3)	C5—C6	1.375 (6)
S1—N1	1.643 (3)	C6—C7	1.366 (6)
S1—C5	1.746 (4)	C6—H6	0.9300
S2—C10	1.722 (4)	C7—H7	0.9300
S2—C9	1.734 (4)	C8—C9	1.359 (5)
O3—C12	1.335 (5)	C8—C11	1.434 (5)
O3—C13	1.464 (4)	C9—C12	1.467 (5)
O4—C12	1.197 (5)	C10—C11	1.384 (6)
N1—C8	1.423 (5)	C11—C17	1.417 (5)
N1—H1N	0.95 (3)	C13—C14	1.496 (6)
N2—C15	1.340 (6)	C13—H13A	0.9700
N2—C10	1.342 (5)	C13—H13B	0.9700
C1—C2	1.532 (7)	C14—H14A	0.9600
C1—H1A	0.9600	C14—H14B	0.9600
C1—H1B	0.9600	C14—H14C	0.9600
C1—H1C	0.9600	C15—C16	1.355 (7)
C2—C7	1.390 (8)	C15—H15	0.9300
C2—C3	1.395 (8)	C16—C17	1.383 (6)
C3—C4	1.385 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.390 (5)

O1—S1—O2	119.11 (18)	C9—C8—N1	123.8 (3)
O1—S1—N1	107.37 (16)	C9—C8—C11	112.4 (3)
O2—S1—N1	105.00 (16)	N1—C8—C11	123.3 (3)
O1—S1—C5	109.43 (18)	C8—C9—C12	126.6 (3)
O2—S1—C5	107.97 (18)	C8—C9—S2	112.9 (3)
N1—S1—C5	107.34 (16)	C12—C9—S2	120.3 (3)
C10—S2—C9	90.63 (18)	N2—C10—C11	125.8 (4)
C12—O3—C13	116.1 (3)	N2—C10—S2	121.5 (4)
C8—N1—S1	122.0 (2)	C11—C10—S2	112.7 (3)
C8—N1—H1N	114 (3)	C10—C11—C17	118.2 (3)
S1—N1—H1N	109 (3)	C10—C11—C8	111.4 (3)
C15—N2—C10	114.2 (4)	C17—C11—C8	130.2 (4)
C2—C1—H1A	109.5	O4—C12—O3	124.0 (3)
C2—C1—H1B	109.5	O4—C12—C9	124.4 (4)
H1A—C1—H1B	109.5	O3—C12—C9	111.7 (3)
C2—C1—H1C	109.5	O3—C13—C14	107.3 (3)
H1A—C1—H1C	109.5	O3—C13—H13A	110.3
H1B—C1—H1C	109.5	C14—C13—H13A	110.3
C7—C2—C3	119.4 (5)	O3—C13—H13B	110.3
C7—C2—C1	121.5 (7)	C14—C13—H13B	110.3
C3—C2—C1	118.9 (6)	H13A—C13—H13B	108.5
C4—C3—C2	119.7 (5)	C13—C14—H14A	109.5
C4—C3—H3	120.1	C13—C14—H14B	109.5
C2—C3—H3	120.1	H14A—C14—H14B	109.5
C3—C4—C5	119.5 (5)	C13—C14—H14C	109.5
C3—C4—H4	120.3	H14A—C14—H14C	109.5
C5—C4—H4	120.3	H14B—C14—H14C	109.5
C6—C5—C4	120.8 (4)	N2—C15—C16	124.8 (4)
C6—C5—S1	119.7 (3)	N2—C15—H15	117.6
C4—C5—S1	119.5 (3)	C16—C15—H15	117.6
C7—C6—C5	119.7 (5)	C15—C16—C17	121.6 (4)
C7—C6—H6	120.1	C15—C16—H16	119.2
C5—C6—H6	120.1	C17—C16—H16	119.2
C6—C7—C2	120.9 (5)	C16—C17—C11	115.4 (4)
C6—C7—H7	119.6	C16—C17—H17	122.3
C2—C7—H7	119.6	C11—C17—H17	122.3

O1—S1—N1—C8	−38.8 (3)	C10—S2—C9—C12	−174.1 (3)
O2—S1—N1—C8	−166.5 (3)	C15—N2—C10—C11	3.0 (6)
C5—S1—N1—C8	78.8 (3)	C15—N2—C10—S2	−175.2 (3)
C7—C2—C3—C4	0.5 (7)	C9—S2—C10—N2	178.1 (4)
C1—C2—C3—C4	−174.8 (4)	C9—S2—C10—C11	−0.3 (3)
C2—C3—C4—C5	0.9 (7)	N2—C10—C11—C17	−2.6 (6)
C3—C4—C5—C6	−1.5 (6)	S2—C10—C11—C17	175.8 (3)
C3—C4—C5—S1	176.2 (3)	N2—C10—C11—C8	−178.3 (4)
O1—S1—C5—C6	−166.5 (3)	S2—C10—C11—C8	0.0 (4)
O2—S1—C5—C6	−35.5 (4)	C9—C8—C11—C10	0.4 (4)
N1—S1—C5—C6	77.3 (4)	N1—C8—C11—C10	172.4 (3)
O1—S1—C5—C4	15.8 (4)	C9—C8—C11—C17	−174.7 (3)
O2—S1—C5—C4	146.9 (3)	N1—C8—C11—C17	−2.7 (6)
N1—S1—C5—C4	−100.4 (3)	C13—O3—C12—O4	−0.1 (5)
C4—C5—C6—C7	0.7 (7)	C13—O3—C12—C9	178.8 (3)
S1—C5—C6—C7	−176.9 (3)	C8—C9—C12—O4	2.4 (6)
C5—C6—C7—C2	0.6 (7)	S2—C9—C12—O4	176.2 (3)
C3—C2—C7—C6	−1.2 (7)	C8—C9—C12—O3	−176.5 (3)
C1—C2—C7—C6	173.9 (4)	S2—C9—C12—O3	−2.7 (4)
S1—N1—C8—C9	−115.8 (4)	C12—O3—C13—C14	−178.0 (3)
S1—N1—C8—C11	73.0 (4)	C10—N2—C15—C16	−2.2 (7)
N1—C8—C9—C12	1.5 (6)	N2—C15—C16—C17	1.0 (7)
C11—C8—C9—C12	173.5 (3)	C15—C16—C17—C11	−0.4 (6)
N1—C8—C9—S2	−172.6 (3)	C10—C11—C17—C16	1.1 (5)
C11—C8—C9—S2	−0.6 (4)	C8—C11—C17—C16	175.9 (4)
C10—S2—C9—C8	0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.95 (3)	2.22 (3)	2.867 (4)	125 (3)
N1—H1N···O2ⁱ	0.95 (3)	2.21 (3)	3.033 (4)	145 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₄S₂
M_r	376.46
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	14.809 (4), 11.892 (3), 19.494 (5)
V (Å³)	3433.1 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.46 × 0.44 × 0.42

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	For a sphere (interpolation; International Tables for X-ray Crystallography, 1959, Vol II, p. 302; 1992, Vol. C, p. 523); Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification.
T_min, T_max	0.861, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	3590, 3075, 2032
R_int	0.005
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.186, 1.13
No. of reflections	3075
No. of parameters	233
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.74

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.95 (3)	2.22 (3)	2.867 (4)	125 (3)
N1—H1N···O2ⁱ	0.95 (3)	2.21 (3)	3.033 (4)	145 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The project was sponsored by the Scientific Research Foundation for Returned Overseas Chinese Scholars (No. 20071108–18–14), State Education Ministry.

References

Dwiggins, C. W. (1975). Acta Cryst. A31, 146–148. CrossRef IUCr Journals Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Meeting, Pittsburgh, Abstract PA 104. Google Scholar
Litvinov, V. P., Dotsenko, V. V. & Krivokolysko, S. G. (2005). Russ. Chem. Bull. 54, 864–904. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar