Bis(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carb­oxy­lic acid) monohydrate

Lin, J.R.

doi:10.1107/S1600536810026243

organic compounds

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Volume 66| Part 8| August 2010| Page o1967

https://doi.org/10.1107/S1600536810026243

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Bis(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid) monohydrate

Jin Rui Lin ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: linjinrui23@163.com

(Received 19 May 2010; accepted 3 July 2010; online 10 July 2010)

The crystal structure of the title compound, 2C₁₀H₉N₃O₂·H₂O, synthesized from azidobenzene and ethyl acetylacetate, is stabilized by O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

The title compound was studied as part of our search for phase transition materials, see: Li et al. (2008 ); Zhang et al. (2009 ). For the preparation, see: El Khadem et al. (1968 ). For the biological activity of triazoles, see: Olesen et al. (2003 ) Tian et al. (2005 ). For a related structure, see: Lin (2008 ).

Experimental

Crystal data

2C₁₀H₉N₃O₂·H₂O
M_r = 424.42
Monoclinic, P 2₁ /c
a = 6.7419 (13) Å
b = 15.842 (3) Å
c = 19.643 (4) Å
β = 99.82 (3)°
V = 2067.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.42 × 0.38 × 0.35 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.947, T_max = 0.951
20838 measured reflections
4733 independent reflections
3206 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.172
S = 0.87
4733 reflections
292 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N3ⁱ	0.82	1.89	2.704 (2)	170
O1—H1⋯O5	0.82	1.79	2.599 (2)	168
O5—H5A⋯O2ⁱⁱ	0.85 (4)	2.07 (4)	2.914 (3)	171 (3)
O5—H5B⋯N6ⁱⁱⁱ	0.83 (4)	2.20 (4)	3.015 (3)	171 (4)
Symmetry codes: (i) x-1, y, z+1; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810026243/jh2161sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026243/jh2161Isup2.hkl

checkCIF report

Comment top

Many triazole-related molecules have received much attention because of their biological activities (Olesen et al., 2003; Tian et al., 2005). Most non-hydrogen atoms of the triazole Ring were coplanar, with the mean deviation from plane of 0.363 (142)° and C11—C16—N4—N5 torsion angle of 57.202 (259)°. The weak π-π packing interactions of the triazole and phenyl ring planes with Cg—Cg distances from 4.2017 Å to 5.0920 Å (Cg is the centroid of the triazole or the phenyl ring planes) stabilized the crystal structure. Because of changes in the external environment, the title compound crystallize in different space group (Lin et al., 2008) and there is a water molecular in the asymmetric unit which transform the method of connection of hydrogen bonds.

As a continuation of our study of phase transition materials, including organicligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009),the dielectric constant of 5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid hydrate compound as a function of temperature indicates that the permittivity is basically temperature-independent (dielectric constant equaling to 5.2 to 8.2), suggesting that there may be no distinct phase transition occurred within the measured temperature range.

Related literature top

The title compound was studied as part of our search for phase transition materials, see: Li et al. (2008); Zhang et al. (2009). For the preparation, see: El Khadem et al. (1968). For the biological activity of triazoles, see: Olesen et al. (2003) Tian et al. (2005). For a related structure, see: Lin (2008).

Experimental top

The title compound was prepared from azidobenzene according to the reported method (El Khadem et al., 1968). The colourless prisms (average size: 0.8×0.8×2.0 mm) were obtained by slow evaporation from ethanol solution at room temperature for 3 days.

Structure description top

The title compound was studied as part of our search for phase transition materials, see: Li et al. (2008); Zhang et al. (2009). For the preparation, see: El Khadem et al. (1968). For the biological activity of triazoles, see: Olesen et al. (2003) Tian et al. (2005). For a related structure, see: Lin (2008).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the packing of the title compound, stacking along the a axis.

Bis(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid) monohydrate top

Crystal data top

2C₁₀H₉N₃O₂·H₂O	F(000) = 888
M_r = 424.42	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8429 reflections
a = 6.7419 (13) Å	θ = 3.1–27.7°
b = 15.842 (3) Å	µ = 0.10 mm⁻¹
c = 19.643 (4) Å	T = 293 K
β = 99.82 (3)°	Prism, colorless
V = 2067.2 (7) Å³	0.42 × 0.38 × 0.35 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	4733 independent reflections
Radiation source: fine-focus sealed tube	3206 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
T_min = 0.947, T_max = 0.951	l = −25→25
20838 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ²(F_o²) + (0.1083P)² + 0.6293P] where P = (F_o² + 2F_c²)/3
4733 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

2C₁₀H₉N₃O₂·H₂O	V = 2067.2 (7) Å³
M_r = 424.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.7419 (13) Å	µ = 0.10 mm⁻¹
b = 15.842 (3) Å	T = 293 K
c = 19.643 (4) Å	0.42 × 0.38 × 0.35 mm
β = 99.82 (3)°

Data collection top

Rigaku SCXmini diffractometer	4733 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3206 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.951	R_int = 0.056
20838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	Δρ_max = 0.21 e Å⁻³
4733 reflections	Δρ_min = −0.19 e Å⁻³
292 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
O4	−0.2245 (3)	0.25435 (10)	1.04831 (9)	0.0616 (5)
H4	−0.3031	0.2478	1.0754	0.092*
N1	0.3101 (2)	0.21148 (10)	0.20357 (8)	0.0427 (4)
O1	0.2105 (2)	0.44007 (10)	0.09705 (9)	0.0604 (5)
H1	0.2133	0.4802	0.0709	0.091*
O2	0.4704 (3)	0.39675 (10)	0.05055 (9)	0.0658 (5)
N3	0.4944 (3)	0.25050 (10)	0.13134 (10)	0.0505 (5)
O3	−0.1197 (3)	0.12701 (11)	1.08533 (9)	0.0725 (5)
N6	0.0253 (3)	0.25962 (11)	0.95482 (10)	0.0515 (5)
N4	0.2420 (2)	0.17006 (10)	0.93228 (9)	0.0426 (4)
C17	0.1698 (3)	0.13594 (13)	0.98605 (10)	0.0416 (5)
N5	0.1530 (3)	0.24561 (11)	0.91340 (10)	0.0542 (5)
C16	0.3809 (3)	0.13618 (13)	0.89167 (10)	0.0427 (5)
C7	0.2327 (3)	0.28716 (12)	0.18016 (10)	0.0387 (4)
C9	0.3516 (3)	0.38637 (12)	0.08889 (11)	0.0438 (5)
C8	0.3532 (3)	0.31110 (12)	0.13320 (10)	0.0407 (4)
C6	0.2526 (3)	0.15587 (12)	0.25486 (10)	0.0406 (4)
C18	0.0303 (3)	0.19342 (12)	0.99957 (10)	0.0397 (4)
C19	−0.1097 (3)	0.18755 (13)	1.04937 (10)	0.0435 (5)
N2	0.4702 (3)	0.18997 (11)	0.17417 (10)	0.0544 (5)
C4	0.0066 (4)	0.07727 (15)	0.30104 (13)	0.0555 (6)
H4A	−0.1262	0.0602	0.2992	0.067*
C3	0.1503 (4)	0.04942 (14)	0.35351 (12)	0.0539 (6)
H3	0.1157	0.0135	0.3871	0.065*
C1	0.3999 (3)	0.12818 (13)	0.30735 (11)	0.0468 (5)
H1A	0.5329	0.1452	0.3096	0.056*
C11	0.5459 (3)	0.18340 (15)	0.88273 (12)	0.0535 (5)
H11	0.5721	0.2350	0.9051	0.064*
C5	0.0549 (3)	0.13048 (14)	0.25048 (11)	0.0495 (5)
H5	−0.0435	0.1487	0.2144	0.059*
C10	0.0630 (3)	0.32936 (14)	0.20576 (12)	0.0515 (5)
H10A	−0.0615	0.3140	0.1770	0.077*
H10B	0.0802	0.3895	0.2044	0.077*
H10C	0.0606	0.3119	0.2524	0.077*
C15	0.3431 (4)	0.05856 (14)	0.86021 (12)	0.0542 (6)
H15	0.2322	0.0268	0.8671	0.065*
C2	0.3460 (4)	0.07454 (14)	0.35661 (12)	0.0528 (5)
H2	0.4441	0.0552	0.3924	0.063*
C13	0.6347 (4)	0.0763 (2)	0.80763 (13)	0.0709 (8)
H13	0.7194	0.0565	0.7784	0.085*
C20	0.2496 (4)	0.05710 (17)	1.02157 (13)	0.0694 (8)
H20A	0.2171	0.0100	0.9909	0.104*
H20B	0.1901	0.0490	1.0621	0.104*
H20C	0.3931	0.0614	1.0346	0.104*
C12	0.6716 (4)	0.1527 (2)	0.83991 (14)	0.0705 (7)
H12	0.7827	0.1843	0.8329	0.085*
C14	0.4724 (4)	0.02880 (17)	0.81842 (12)	0.0644 (7)
H14	0.4496	−0.0237	0.7974	0.077*
O5	0.2055 (3)	0.58080 (13)	0.02879 (12)	0.0749 (6)
H5A	0.290 (5)	0.591 (2)	0.0025 (18)	0.098 (11)*
H5B	0.131 (6)	0.622 (3)	0.0310 (19)	0.111 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0721 (11)	0.0477 (9)	0.0777 (11)	0.0177 (8)	0.0487 (9)	0.0112 (8)
N1	0.0477 (9)	0.0344 (9)	0.0519 (10)	0.0046 (7)	0.0252 (8)	0.0031 (7)
O1	0.0609 (10)	0.0480 (9)	0.0805 (12)	0.0167 (8)	0.0356 (9)	0.0221 (8)
O2	0.0814 (12)	0.0502 (9)	0.0792 (11)	0.0107 (8)	0.0519 (10)	0.0132 (8)
N3	0.0571 (11)	0.0373 (9)	0.0654 (12)	0.0075 (8)	0.0342 (9)	0.0056 (8)
O3	0.0995 (14)	0.0625 (11)	0.0671 (11)	0.0289 (10)	0.0472 (10)	0.0255 (9)
N6	0.0569 (11)	0.0385 (9)	0.0674 (12)	0.0102 (8)	0.0337 (9)	0.0083 (8)
N4	0.0434 (9)	0.0380 (9)	0.0496 (10)	0.0080 (7)	0.0168 (7)	0.0025 (7)
C17	0.0434 (10)	0.0429 (11)	0.0397 (10)	0.0091 (8)	0.0107 (8)	0.0019 (8)
N5	0.0615 (11)	0.0382 (10)	0.0722 (13)	0.0129 (8)	0.0377 (10)	0.0119 (8)
C16	0.0426 (10)	0.0445 (11)	0.0434 (10)	0.0126 (9)	0.0143 (8)	0.0035 (8)
C7	0.0409 (10)	0.0353 (10)	0.0428 (10)	0.0008 (8)	0.0154 (8)	−0.0040 (8)
C9	0.0457 (11)	0.0377 (10)	0.0518 (12)	0.0008 (9)	0.0193 (9)	−0.0020 (8)
C8	0.0440 (10)	0.0341 (10)	0.0482 (11)	0.0017 (8)	0.0194 (9)	−0.0038 (8)
C6	0.0492 (11)	0.0319 (9)	0.0452 (11)	0.0011 (8)	0.0209 (9)	−0.0006 (8)
C18	0.0414 (10)	0.0377 (10)	0.0415 (10)	0.0045 (8)	0.0115 (8)	0.0006 (8)
C19	0.0514 (11)	0.0403 (11)	0.0414 (11)	0.0072 (9)	0.0155 (9)	0.0002 (8)
N2	0.0628 (12)	0.0400 (10)	0.0702 (12)	0.0116 (8)	0.0394 (10)	0.0097 (8)
C4	0.0495 (12)	0.0546 (13)	0.0659 (15)	−0.0092 (10)	0.0195 (11)	0.0070 (11)
C3	0.0665 (14)	0.0445 (12)	0.0555 (13)	−0.0007 (10)	0.0238 (11)	0.0096 (10)
C1	0.0434 (11)	0.0413 (11)	0.0586 (13)	0.0047 (9)	0.0169 (9)	−0.0021 (9)
C11	0.0489 (12)	0.0584 (13)	0.0560 (13)	0.0021 (10)	0.0169 (10)	−0.0043 (10)
C5	0.0487 (12)	0.0498 (12)	0.0508 (12)	−0.0049 (9)	0.0106 (9)	0.0055 (10)
C10	0.0534 (12)	0.0492 (12)	0.0579 (13)	0.0065 (10)	0.0271 (10)	−0.0006 (10)
C15	0.0613 (13)	0.0449 (12)	0.0584 (14)	0.0085 (10)	0.0157 (11)	−0.0012 (10)
C2	0.0604 (13)	0.0459 (12)	0.0528 (13)	0.0092 (10)	0.0120 (10)	0.0075 (10)
C13	0.0699 (17)	0.090 (2)	0.0589 (15)	0.0279 (15)	0.0283 (13)	−0.0044 (14)
C20	0.0859 (18)	0.0688 (16)	0.0585 (15)	0.0407 (14)	0.0265 (13)	0.0226 (12)
C12	0.0535 (14)	0.091 (2)	0.0744 (17)	0.0013 (13)	0.0306 (12)	−0.0034 (15)
C14	0.0805 (17)	0.0569 (14)	0.0582 (14)	0.0247 (13)	0.0186 (12)	−0.0081 (11)
O5	0.0685 (12)	0.0576 (11)	0.1075 (16)	0.0208 (10)	0.0409 (11)	0.0379 (10)

Geometric parameters (Å, º) top

O4—C19	1.309 (2)	C4—C3	1.362 (3)
O4—H4	0.8200	C4—C5	1.383 (3)
N1—N2	1.352 (2)	C4—H4A	0.9300
N1—C7	1.356 (3)	C3—C2	1.370 (3)
N1—C6	1.440 (2)	C3—H3	0.9300
O1—C9	1.306 (2)	C1—C2	1.382 (3)
O1—H1	0.8200	C1—H1A	0.9300
O2—C9	1.201 (2)	C11—C12	1.381 (3)
N3—N2	1.304 (2)	C11—H11	0.9300
N3—C8	1.357 (2)	C5—H5	0.9300
O3—C19	1.200 (2)	C10—H10A	0.9600
N6—N5	1.300 (2)	C10—H10B	0.9600
N6—C18	1.365 (3)	C10—H10C	0.9600
N4—C17	1.349 (2)	C15—C14	1.378 (3)
N4—N5	1.362 (2)	C15—H15	0.9300
N4—C16	1.434 (2)	C2—H2	0.9300
C17—C18	1.367 (3)	C13—C12	1.370 (4)
C17—C20	1.486 (3)	C13—C14	1.373 (4)
C16—C11	1.376 (3)	C13—H13	0.9300
C16—C15	1.380 (3)	C20—H20A	0.9600
C7—C8	1.382 (3)	C20—H20B	0.9600
C7—C10	1.485 (3)	C20—H20C	0.9600
C9—C8	1.475 (3)	C12—H12	0.9300
C6—C1	1.376 (3)	C14—H14	0.9300
C6—C5	1.381 (3)	O5—H5A	0.85 (4)
C18—C19	1.474 (3)	O5—H5B	0.83 (4)

C19—O4—H4	109.5	C4—C3—H3	120.2
N2—N1—C7	111.55 (15)	C2—C3—H3	120.2
N2—N1—C6	118.32 (15)	C6—C1—C2	118.6 (2)
C7—N1—C6	130.07 (16)	C6—C1—H1A	120.7
C9—O1—H1	109.5	C2—C1—H1A	120.7
N2—N3—C8	109.73 (16)	C16—C11—C12	118.7 (2)
N5—N6—C18	109.01 (16)	C16—C11—H11	120.7
C17—N4—N5	111.38 (15)	C12—C11—H11	120.7
C17—N4—C16	129.99 (17)	C6—C5—C4	118.4 (2)
N5—N4—C16	118.46 (16)	C6—C5—H5	120.8
N4—C17—C18	103.72 (17)	C4—C5—H5	120.8
N4—C17—C20	123.68 (18)	C7—C10—H10A	109.5
C18—C17—C20	132.41 (19)	C7—C10—H10B	109.5
N6—N5—N4	106.70 (16)	H10A—C10—H10B	109.5
C11—C16—C15	121.2 (2)	C7—C10—H10C	109.5
C11—C16—N4	119.10 (19)	H10A—C10—H10C	109.5
C15—C16—N4	119.62 (19)	H10B—C10—H10C	109.5
N1—C7—C8	103.45 (16)	C14—C15—C16	119.0 (2)
N1—C7—C10	123.88 (17)	C14—C15—H15	120.5
C8—C7—C10	132.61 (18)	C16—C15—H15	120.5
O2—C9—O1	124.44 (19)	C3—C2—C1	120.9 (2)
O2—C9—C8	122.83 (18)	C3—C2—H2	119.6
O1—C9—C8	112.72 (17)	C1—C2—H2	119.6
N3—C8—C7	108.59 (17)	C12—C13—C14	120.0 (2)
N3—C8—C9	119.39 (17)	C12—C13—H13	120.0
C7—C8—C9	132.02 (17)	C14—C13—H13	120.0
C1—C6—C5	121.31 (19)	C17—C20—H20A	109.5
C1—C6—N1	118.25 (18)	C17—C20—H20B	109.5
C5—C6—N1	120.44 (19)	H20A—C20—H20B	109.5
N6—C18—C17	109.19 (17)	C17—C20—H20C	109.5
N6—C18—C19	121.87 (17)	H20A—C20—H20C	109.5
C17—C18—C19	128.80 (18)	H20B—C20—H20C	109.5
O3—C19—O4	124.27 (19)	C13—C12—C11	120.7 (3)
O3—C19—C18	123.24 (18)	C13—C12—H12	119.6
O4—C19—C18	112.46 (17)	C11—C12—H12	119.6
N3—N2—N1	106.67 (15)	C13—C14—C15	120.4 (2)
C3—C4—C5	121.1 (2)	C13—C14—H14	119.8
C3—C4—H4A	119.4	C15—C14—H14	119.8
C5—C4—H4A	119.4	H5A—O5—H5B	112 (3)
C4—C3—C2	119.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3ⁱ	0.82	1.89	2.704 (2)	170
O1—H1···O5	0.82	1.79	2.599 (2)	168
O5—H5A···O2ⁱⁱ	0.85 (4)	2.07 (4)	2.914 (3)	171 (3)
O5—H5B···N6ⁱⁱⁱ	0.83 (4)	2.20 (4)	3.015 (3)	171 (4)

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

Experimental details

Crystal data
Chemical formula	2C₁₀H₉N₃O₂·H₂O
M_r	424.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.7419 (13), 15.842 (3), 19.643 (4)
β (°)	99.82 (3)
V (Å³)	2067.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.42 × 0.38 × 0.35

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.947, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	20838, 4733, 3206
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.172, 0.87
No. of reflections	4733
No. of parameters	292
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3ⁱ	0.82	1.89	2.704 (2)	169.9
O1—H1···O5	0.82	1.79	2.599 (2)	167.7
O5—H5A···O2ⁱⁱ	0.85 (4)	2.07 (4)	2.914 (3)	171 (3)
O5—H5B···N6ⁱⁱⁱ	0.83 (4)	2.20 (4)	3.015 (3)	171 (4)

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

Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

References

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