(Morpholin-4-yl)[2-(morpholin-4-yl)-3,5-dinitro­phen­yl]methanone

Gao, C.; Xiong, Y.; Xia, Y.; Yu, L.-T.

doi:10.1107/S1600536812000426

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o376

doi:10.1107/S1600536812000426

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(Morpholin-4-yl)[2-(morpholin-4-yl)-3,5-dinitrophenyl]methanone

Chao Gao,^a Ying Xiong,^a Yong Xia ^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
^*Correspondence e-mail: yuluot@scu.edu.cn

(Received 30 December 2011; accepted 5 January 2012; online 14 January 2012)

In the title compound, C₁₅H₁₈N₄O₇, the morpholine rings adopt chair conformations. The benzene ring forms dihedral angles of 55.94 (7) and 63.19 (7)° with the planes through the C atoms of the two morpholine rings.

Related literature

For the biological activity of benzamide derivatives, see: Christophe et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₈N₄O₇
M_r = 366.33
Monoclinic, P 2₁ /c
a = 10.2640 (4) Å
b = 21.5488 (7) Å
c = 8.0061 (3) Å
β = 108.587 (4)°
V = 1678.40 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.38 × 0.35 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.994, T_max = 1.000
7068 measured reflections
3422 independent reflections
2440 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.110
S = 1.03
3422 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000426/nc2263sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000426/nc2263Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000426/nc2263Isup3.cml

checkCIF report

Comment top

Benzamide derivatives are of great importance owing to their antibacterial properties (Christophe et al., 2009). The title compound is one of the key intermediates in our synthetic investigations of antibacterial drugs. Therefore, its crystal structure was determined.

In the crystal structure of the title compound, C₁₅H₁₈N₄O₇, the morpholine rings adopt a chair conformation. The benzene ring forms dihedral angles of 55.94 (7)° and 63.19 (7)° with the two morpholine rings.

Related literature top

For the biological activity of benzamide derivatives, see: Christophe et al. (2009).

Experimental top

3.42 g (12.9 mmol) of 2-chloro-3,5-dinitrobenzoyl chloride was added to a solution of 2.36 g (27.1 mmol) morpholine in 20 ml of dichloromethane and 1.82 g (17.9 mmol) triethylamine. The mixture was stirred for 2 h at room temperature extracted with water and dichloromethane and the organic solvent was evaporated and the title compound was recrystallized from ethanol (yield 4.25 g, 90%). Crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent from a solution of the title compound in acetonitrile.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level.

(Morpholin-4-yl)[2-(morpholin-4-yl)-3,5-dinitrophenyl]methanone top

Crystal data top

C₁₅H₁₈N₄O₇	F(000) = 768
M_r = 366.33	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 10.2640 (4) Å	Cell parameters from 2613 reflections
b = 21.5488 (7) Å	θ = 3.0–29.0°
c = 8.0061 (3) Å	µ = 0.12 mm⁻¹
β = 108.587 (4)°	T = 293 K
V = 1678.40 (10) Å³	Block, yellow
Z = 4	0.38 × 0.35 × 0.35 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3422 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2440 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.0°
ω scans	h = −12→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −26→18
T_min = 0.994, T_max = 1.000	l = −9→10
7068 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) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0426P)² + 0.3019P] where P = (F_o² + 2F_c²)/3
3422 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₈N₄O₇	V = 1678.40 (10) Å³
M_r = 366.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2640 (4) Å	µ = 0.12 mm⁻¹
b = 21.5488 (7) Å	T = 293 K
c = 8.0061 (3) Å	0.38 × 0.35 × 0.35 mm
β = 108.587 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3422 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	2440 reflections with I > 2σ(I)
T_min = 0.994, T_max = 1.000	R_int = 0.017
7068 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
3422 reflections	Δρ_min = −0.20 e Å⁻³
235 parameters

Special details top

Experimental. CrysAlisPro (Oxford Diffraction, 2006). Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.38171 (14)	0.03743 (7)	0.58276 (17)	0.0608 (4)
O2	0.58939 (14)	0.11924 (7)	0.02632 (18)	0.0588 (4)
O3	0.27069 (12)	0.25026 (6)	0.21720 (17)	0.0468 (3)
O4	−0.13992 (17)	0.22884 (9)	−0.4060 (2)	0.0884 (6)
O5	−0.30029 (15)	0.16911 (8)	−0.38749 (19)	0.0723 (5)
O6	−0.11367 (15)	0.07133 (8)	0.3247 (2)	0.0697 (5)
O7	−0.17948 (18)	0.01161 (7)	0.0962 (2)	0.0825 (5)
N1	−0.18359 (16)	0.18932 (8)	−0.3309 (2)	0.0500 (4)
N2	−0.12006 (16)	0.05713 (8)	0.1748 (2)	0.0510 (4)
N3	0.17106 (14)	0.09335 (6)	0.30645 (17)	0.0375 (4)
N4	0.36454 (13)	0.17369 (6)	0.09991 (17)	0.0342 (3)
C1	−0.09372 (17)	0.16569 (8)	−0.1628 (2)	0.0361 (4)
C2	−0.14151 (17)	0.12014 (8)	−0.0794 (2)	0.0373 (4)
H2	−0.2291	0.1036	−0.1289	0.045*
C3	−0.05571 (17)	0.09943 (8)	0.0810 (2)	0.0342 (4)
C4	0.07972 (16)	0.12074 (7)	0.1600 (2)	0.0307 (4)
C5	0.12146 (16)	0.16958 (7)	0.0703 (2)	0.0306 (4)
C6	0.03563 (17)	0.19131 (8)	−0.0891 (2)	0.0357 (4)
H6	0.0648	0.2232	−0.1471	0.043*
C7	0.25205 (19)	0.12947 (9)	0.4592 (2)	0.0464 (5)
H7A	0.2059	0.1302	0.5476	0.056*
H7B	0.2613	0.1719	0.4238	0.056*
C8	0.3922 (2)	0.10043 (11)	0.5348 (3)	0.0563 (6)
H8A	0.4402	0.1024	0.4485	0.068*
H8B	0.4451	0.1236	0.6379	0.068*
C9	0.3045 (2)	0.00286 (10)	0.4328 (3)	0.0570 (5)
H9A	0.2990	−0.0400	0.4668	0.068*
H9B	0.3515	0.0037	0.3452	0.068*
C10	0.16127 (19)	0.02827 (8)	0.3529 (3)	0.0460 (5)
H10A	0.1125	0.0047	0.2485	0.055*
H10B	0.1110	0.0249	0.4366	0.055*
C11	0.25990 (16)	0.20097 (8)	0.1370 (2)	0.0317 (4)
C12	0.49371 (17)	0.20777 (9)	0.1316 (3)	0.0456 (5)
H12A	0.5083	0.2348	0.2329	0.055*
H12B	0.4886	0.2334	0.0301	0.055*
C13	0.61214 (19)	0.16320 (11)	0.1647 (3)	0.0594 (6)
H13A	0.6957	0.1862	0.1754	0.071*
H13B	0.6246	0.1416	0.2749	0.071*
C14	0.4726 (2)	0.08302 (9)	0.0182 (3)	0.0493 (5)
H14A	0.4871	0.0625	0.1305	0.059*
H14B	0.4603	0.0513	−0.0714	0.059*
C15	0.34554 (18)	0.12219 (8)	−0.0241 (2)	0.0419 (4)
H15A	0.3240	0.1383	−0.1429	0.050*
H15B	0.2688	0.0968	−0.0189	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0474 (8)	0.0784 (11)	0.0501 (8)	0.0055 (7)	0.0066 (7)	0.0204 (8)
O2	0.0462 (8)	0.0699 (10)	0.0680 (9)	0.0094 (7)	0.0290 (7)	−0.0044 (8)
O3	0.0433 (7)	0.0360 (7)	0.0618 (8)	−0.0055 (6)	0.0177 (6)	−0.0154 (6)
O4	0.0654 (11)	0.1098 (14)	0.0752 (11)	−0.0167 (10)	0.0017 (9)	0.0537 (11)
O5	0.0423 (8)	0.0936 (12)	0.0631 (9)	−0.0114 (8)	−0.0086 (7)	0.0163 (8)
O6	0.0582 (10)	0.0991 (13)	0.0616 (10)	0.0069 (8)	0.0327 (8)	0.0293 (9)
O7	0.0735 (11)	0.0540 (10)	0.1152 (14)	−0.0298 (9)	0.0236 (10)	0.0129 (10)
N1	0.0393 (9)	0.0576 (11)	0.0462 (9)	−0.0007 (8)	0.0038 (7)	0.0108 (8)
N2	0.0357 (9)	0.0519 (11)	0.0666 (11)	0.0001 (8)	0.0183 (8)	0.0201 (9)
N3	0.0382 (8)	0.0352 (8)	0.0352 (7)	−0.0014 (6)	0.0062 (6)	0.0034 (6)
N4	0.0290 (7)	0.0343 (8)	0.0393 (8)	−0.0048 (6)	0.0111 (6)	−0.0061 (6)
C1	0.0323 (9)	0.0381 (10)	0.0361 (9)	0.0012 (7)	0.0084 (7)	0.0040 (8)
C2	0.0268 (8)	0.0387 (10)	0.0446 (10)	−0.0034 (7)	0.0090 (7)	−0.0009 (8)
C3	0.0336 (9)	0.0305 (9)	0.0423 (9)	−0.0025 (7)	0.0176 (8)	0.0024 (8)
C4	0.0300 (8)	0.0306 (9)	0.0325 (8)	0.0006 (7)	0.0114 (7)	−0.0032 (7)
C5	0.0295 (8)	0.0279 (8)	0.0356 (8)	−0.0003 (7)	0.0122 (7)	−0.0014 (7)
C6	0.0332 (9)	0.0343 (9)	0.0406 (9)	−0.0020 (7)	0.0131 (7)	0.0048 (8)
C7	0.0502 (11)	0.0525 (12)	0.0341 (9)	−0.0053 (9)	0.0100 (8)	−0.0001 (8)
C8	0.0444 (11)	0.0781 (16)	0.0420 (11)	−0.0116 (11)	0.0076 (9)	0.0061 (11)
C9	0.0494 (12)	0.0536 (13)	0.0646 (13)	0.0120 (10)	0.0134 (10)	0.0161 (11)
C10	0.0458 (11)	0.0374 (10)	0.0510 (11)	0.0012 (8)	0.0102 (9)	0.0137 (9)
C11	0.0320 (9)	0.0291 (9)	0.0334 (8)	−0.0023 (7)	0.0097 (7)	0.0018 (7)
C12	0.0339 (10)	0.0499 (12)	0.0546 (11)	−0.0099 (8)	0.0163 (8)	−0.0076 (9)
C13	0.0320 (10)	0.0768 (16)	0.0670 (13)	0.0005 (10)	0.0125 (10)	−0.0057 (12)
C14	0.0572 (13)	0.0440 (11)	0.0521 (11)	0.0086 (10)	0.0252 (10)	0.0016 (9)
C15	0.0421 (10)	0.0372 (10)	0.0477 (10)	−0.0012 (8)	0.0164 (8)	−0.0102 (8)

Geometric parameters (Å, º) top

O1—C8	1.424 (2)	C5—C6	1.381 (2)
O1—C9	1.420 (2)	C5—C11	1.509 (2)
O2—C13	1.419 (2)	C6—H6	0.9300
O2—C14	1.414 (2)	C7—H7A	0.9700
O3—C11	1.2275 (19)	C7—H7B	0.9700
O4—N1	1.208 (2)	C7—C8	1.507 (3)
O5—N1	1.218 (2)	C8—H8A	0.9700
O6—N2	1.220 (2)	C8—H8B	0.9700
O7—N2	1.219 (2)	C9—H9A	0.9700
N1—C1	1.460 (2)	C9—H9B	0.9700
N2—C3	1.465 (2)	C9—C10	1.507 (2)
N3—C4	1.379 (2)	C10—H10A	0.9700
N3—C7	1.464 (2)	C10—H10B	0.9700
N3—C10	1.463 (2)	C12—H12A	0.9700
N4—C11	1.338 (2)	C12—H12B	0.9700
N4—C12	1.465 (2)	C12—C13	1.505 (3)
N4—C15	1.460 (2)	C13—H13A	0.9700
C1—C2	1.363 (2)	C13—H13B	0.9700
C1—C6	1.384 (2)	C14—H14A	0.9700
C2—H2	0.9300	C14—H14B	0.9700
C2—C3	1.379 (2)	C14—C15	1.499 (2)
C3—C4	1.408 (2)	C15—H15A	0.9700
C4—C5	1.415 (2)	C15—H15B	0.9700

C9—O1—C8	109.99 (14)	C7—C8—H8B	109.4
C14—O2—C13	109.29 (14)	H8A—C8—H8B	108.0
O4—N1—O5	122.95 (17)	O1—C9—H9A	109.2
O4—N1—C1	118.63 (16)	O1—C9—H9B	109.2
O5—N1—C1	118.41 (16)	O1—C9—C10	111.99 (17)
O6—N2—C3	117.18 (17)	H9A—C9—H9B	107.9
O7—N2—O6	124.81 (18)	C10—C9—H9A	109.2
O7—N2—C3	117.97 (18)	C10—C9—H9B	109.2
C4—N3—C7	122.26 (14)	N3—C10—C9	108.64 (15)
C4—N3—C10	122.91 (14)	N3—C10—H10A	110.0
C10—N3—C7	111.36 (14)	N3—C10—H10B	110.0
C11—N4—C12	119.16 (14)	C9—C10—H10A	110.0
C11—N4—C15	122.84 (13)	C9—C10—H10B	110.0
C15—N4—C12	114.60 (13)	H10A—C10—H10B	108.3
C2—C1—N1	118.85 (15)	O3—C11—N4	123.45 (15)
C2—C1—C6	121.64 (15)	O3—C11—C5	119.39 (15)
C6—C1—N1	119.47 (15)	N4—C11—C5	117.13 (14)
C1—C2—H2	121.1	N4—C12—H12A	109.6
C1—C2—C3	117.78 (15)	N4—C12—H12B	109.6
C3—C2—H2	121.1	N4—C12—C13	110.25 (16)
C2—C3—N2	114.83 (15)	H12A—C12—H12B	108.1
C2—C3—C4	123.97 (15)	C13—C12—H12A	109.6
C4—C3—N2	120.94 (15)	C13—C12—H12B	109.6
N3—C4—C3	123.28 (15)	O2—C13—C12	111.48 (16)
N3—C4—C5	121.07 (14)	O2—C13—H13A	109.3
C3—C4—C5	115.44 (14)	O2—C13—H13B	109.3
C4—C5—C11	123.82 (14)	C12—C13—H13A	109.3
C6—C5—C4	120.93 (14)	C12—C13—H13B	109.3
C6—C5—C11	115.25 (14)	H13A—C13—H13B	108.0
C1—C6—H6	120.0	O2—C14—H14A	109.4
C5—C6—C1	120.07 (15)	O2—C14—H14B	109.4
C5—C6—H6	120.0	O2—C14—C15	111.31 (16)
N3—C7—H7A	109.8	H14A—C14—H14B	108.0
N3—C7—H7B	109.8	C15—C14—H14A	109.4
N3—C7—C8	109.28 (16)	C15—C14—H14B	109.4
H7A—C7—H7B	108.3	N4—C15—C14	110.89 (15)
C8—C7—H7A	109.8	N4—C15—H15A	109.5
C8—C7—H7B	109.8	N4—C15—H15B	109.5
O1—C8—C7	111.10 (16)	C14—C15—H15A	109.5
O1—C8—H8A	109.4	C14—C15—H15B	109.5
O1—C8—H8B	109.4	H15A—C15—H15B	108.0
C7—C8—H8A	109.4

O1—C9—C10—N3	57.5 (2)	C4—N3—C10—C9	144.78 (16)
O2—C14—C15—N4	−54.3 (2)	C4—C5—C6—C1	0.6 (2)
O4—N1—C1—C2	−178.60 (18)	C4—C5—C11—O3	−97.7 (2)
O4—N1—C1—C6	3.5 (3)	C4—C5—C11—N4	84.29 (19)
O5—N1—C1—C2	2.8 (3)	C6—C1—C2—C3	−0.9 (3)
O5—N1—C1—C6	−175.07 (18)	C6—C5—C11—O3	83.08 (19)
O6—N2—C3—C2	−124.82 (18)	C6—C5—C11—N4	−94.98 (18)
O6—N2—C3—C4	49.6 (2)	C7—N3—C4—C3	−131.89 (17)
O7—N2—C3—C2	52.9 (2)	C7—N3—C4—C5	53.6 (2)
O7—N2—C3—C4	−132.64 (19)	C7—N3—C10—C9	−55.9 (2)
N1—C1—C2—C3	−178.74 (15)	C8—O1—C9—C10	−59.5 (2)
N1—C1—C6—C5	179.70 (15)	C9—O1—C8—C7	59.2 (2)
N2—C3—C4—N3	16.1 (2)	C10—N3—C4—C3	25.3 (2)
N2—C3—C4—C5	−169.09 (15)	C10—N3—C4—C5	−149.27 (16)
N3—C4—C5—C6	171.26 (15)	C10—N3—C7—C8	56.40 (19)
N3—C4—C5—C11	−8.0 (2)	C11—N4—C12—C13	153.48 (16)
N3—C7—C8—O1	−57.6 (2)	C11—N4—C15—C14	−154.09 (16)
N4—C12—C13—O2	54.2 (2)	C11—C5—C6—C1	179.86 (15)
C1—C2—C3—N2	171.64 (16)	C12—N4—C11—O3	−9.5 (2)
C1—C2—C3—C4	−2.6 (3)	C12—N4—C11—C5	168.46 (14)
C2—C1—C6—C5	1.9 (3)	C12—N4—C15—C14	47.0 (2)
C2—C3—C4—N3	−170.01 (15)	C13—O2—C14—C15	62.6 (2)
C2—C3—C4—C5	4.8 (2)	C14—O2—C13—C12	−62.8 (2)
C3—C4—C5—C6	−3.7 (2)	C15—N4—C11—O3	−167.52 (16)
C3—C4—C5—C11	177.09 (14)	C15—N4—C11—C5	10.4 (2)
C4—N3—C7—C8	−144.08 (16)	C15—N4—C12—C13	−46.8 (2)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈N₄O₇
M_r	366.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.2640 (4), 21.5488 (7), 8.0061 (3)
β (°)	108.587 (4)
V (Å³)	1678.40 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.38 × 0.35 × 0.35

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)
T_min, T_max	0.994, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7068, 3422, 2440
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.110, 1.03
No. of reflections	3422
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Christophe, T., Jackson, M., Jeon, H. K., Fenistein, D., Contreras-Dominguez, M., Kim, J., Genovesio, A., Carralot, J. P., Ewann, F., Kim, E. H., Lee, S. Y., Kang, S., Seo, M. J., Park, E. J., Skovierova, H., Pham, H., Riccardi, G., Nam, J. Y., Marsollier, L., Kempf, M., Joly-Guillou, M. L., Oh, T., Shin, W. K., No, Z., Nehrbass, U., Brosch, R., Cole, S. T. & Brodin, P. (2009). PLoS Pathog. 5, 1–10. Web of Science CrossRef Google Scholar
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Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar