Benzene-1,3,5-tricarb­oxy­lic acid–5-(4-pyrid­yl)pyrimidine (1/1)

Jiang, Y.-K.; Hou, G.-G.

doi:10.1107/S1600536811051075

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o6

doi:10.1107/S1600536811051075

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Benzene-1,3,5-tricarboxylic acid–5-(4-pyridyl)pyrimidine (1/1)

Yan-Ke Jiang ^a and Gui-Ge Hou ^b ^*

^aResearch Center of Medical Chemistry & Chemical Biology, Chongqing Technology and Business University, Chongqing 400067, People's Republic of China, and ^bCollege of Pharmacy, Binzhou Medical University, Yantai 264003, People's Republic of China
^*Correspondence e-mail: guigehou@163.com

(Received 24 November 2011; accepted 28 November 2011; online 3 December 2011)

In the pyrimidine molecule of the title compound, C₉H₇N₃·C₉H₆O₆, the pyridine ring is oriented at 33.26 (11)° with respect to the pyrimidine ring. In the benzene-1,3,5-tricarboxylic acid molecule, the three carboxy groups are twisted by 7.92 (9), 8.68 (10) and 17.07 (10)° relative to the benzene ring. Classical O—H⋯N and O—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯N hydrogen bonds occur in the crystal structure.

Related literature

For hydrogen bonding in pyrimidine derivatives, see: Hou et al. (2011 ); Horikoshi et al. (2004 ); Georgiev et al. (2004 ); Santoni et al. (2008 ); Huang & Parquette (2000 ). For co-crystals of organic acids and pyrimidine, see: Bhogala & Nangia(2003 ); Du et al. (2005 ); Hou et al. (2008 ).

Experimental

Crystal data

C₉H₇N₃·C₉H₆O₆
M_r = 367.31
Monoclinic, P 2₁ /c
a = 8.3532 (19) Å
b = 14.865 (3) Å
c = 13.066 (3) Å
β = 98.325 (4)°
V = 1605.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.32 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
8278 measured reflections
2967 independent reflections
2142 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.130
S = 1.04
2967 reflections
256 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3ⁱ	0.95 (3)	1.70 (3)	2.652 (2)	173 (3)
O3—H3A⋯O2ⁱⁱ	0.92 (3)	1.84 (3)	2.720 (2)	161 (3)
O5—H5A⋯N1	0.95 (3)	1.68 (3)	2.626 (2)	177 (3)
C3—H3⋯O3ⁱⁱ	0.93	2.48	3.367 (3)	159
C14—H14⋯N2ⁱⁱⁱ	0.93	2.59	3.335 (3)	137
Symmetry codes: (i) x+1, y, z-1; (ii) -x+2, -y+1, -z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051075/xu5398sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051075/xu5398Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051075/xu5398Isup3.cml

checkCIF report

Comment top

Some pyrimidine derivatives, such as such as 5, 5'-dipyrimidine, 1,2-bis(5'-pyrimidyl)ethyne, 5-(3-pyridyl)pyrimidine (L), 5-phenyl-2-(4-pyrid-yl)pyrimidine, and 4-(pyridin-2-yl)pyrimidine-2-sulfonate, could form strong hydrogen-bond interaction and play an essential role in synthesis of supra-molecular structure (Hou et al., 2011; Horikoshi et al., 2004; Georgiev et al., 2004; Santoni et al., 2008; Huang et al., 2000). The co-crystal sates of acid···pyridine and acid···pyrimidine systems have been reported (Bhogala et al., 2003; Du et al., 2005; Hou et al., 2008). Here we report the co-crystal states of L1 and L2.

The title molecular structure is shown in Fig. 1. The asymmetric unit contains 5-(4-pyridyl)pyrimidine molecule (L1) and a benzene-1,3,5-tricarboxylic acid molecule (L2). In the crystal, L1 and L2 arrange in an alternate disposition along the crystallographic c-axis. A H-bonding driven double chain was generated from O—H···N and O—H···O hydrogen bonds between these molecules (Fig. 2). The asymmetric hydrogen bonds influence the intramolecular coplanar of L2 and different dihedral angles of 7.92 (9), 8.68 (10) and 17.07 (10)° are formed between benzene ring and the carboxyl groups. Pyridine ring is twisted to pyrimidine ring at a dihedral angle of 33.26 (11)°, but nearly coplanar with benzene ring of L2 (the dihedral angle, 12.0 (8)°).

Related literature top

For hydrogen bonding in pyrimidine derivatives, see: Hou et al. (2011); Horikoshi et al. (2004); Georgiev et al. (2004); Santoni et al. (2008); Huang & Parquette (2000). For co-crystals of organic acid and pyrimidine, see: Bhogala & Nangia(2003); Du et al. (2005); Hou et al. (2008).

Experimental top

A CH₂Cl₂ and CH₃CN solution (15 mL, 1:1, v/v) of 5-(4-pyridyl)pyrimidine molecule and benzene-1,3,5-tricarboxylic acid (21.0 mg, 0.1 mmol) was kept at room temperature. Upon slow evaporation of the solvent about 5 days, colorless crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008; molecular graphics: SHELXTL (Sheldrick, 2008; software used to prepare material for publication: SHELXTL (Sheldrick, 2008.

Figures top

	Fig. 1. The structure of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. A view of the hydrogen-bonded double-chain observed in the crystal structure of (1).

Benzene-1,3,5-tricarboxylic acid–5-(4-pyridyl)pyrimidine (1/1) top

Crystal data top

C₉H₇N₃·C₉H₆O₆	F(000) = 760
M_r = 367.31	D_x = 1.520 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1381 reflections
a = 8.3532 (19) Å	θ = 2.5–22.7°
b = 14.865 (3) Å	µ = 0.12 mm⁻¹
c = 13.066 (3) Å	T = 298 K
β = 98.325 (4)°	Block, colourless
V = 1605.4 (6) Å³	0.32 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2142 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 25.5°, θ_min = 2.1°
ϕ and ω scans	h = −10→10
8278 measured reflections	k = −18→17
2967 independent reflections	l = −9→15

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0605P)² + 0.0652P] where P = (F_o² + 2F_c²)/3
2967 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₉H₇N₃·C₉H₆O₆	V = 1605.4 (6) Å³
M_r = 367.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3532 (19) Å	µ = 0.12 mm⁻¹
b = 14.865 (3) Å	T = 298 K
c = 13.066 (3) Å	0.32 × 0.12 × 0.10 mm
β = 98.325 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	2142 reflections with I > 2σ(I)
8278 measured reflections	R_int = 0.042
2967 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
2967 reflections	Δρ_min = −0.21 e Å⁻³
256 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	1.0045 (3)	0.23487 (15)	0.04299 (17)	0.0307 (5)
C2	0.9253 (3)	0.28752 (14)	0.11876 (16)	0.0298 (5)
C3	0.9233 (3)	0.38061 (15)	0.11112 (17)	0.0328 (6)
H3	0.9717	0.4086	0.0598	0.039*
C4	0.8495 (3)	0.43246 (14)	0.17958 (16)	0.0314 (6)
C5	0.7764 (3)	0.38975 (15)	0.25547 (16)	0.0323 (6)
H5	0.7254	0.4239	0.3009	0.039*
C6	0.7787 (3)	0.29718 (15)	0.26421 (16)	0.0314 (5)
C7	0.8537 (3)	0.24592 (15)	0.19591 (16)	0.0315 (6)
H7	0.8559	0.1836	0.2018	0.038*
C8	0.6958 (3)	0.24978 (16)	0.34319 (17)	0.0327 (6)
C9	0.8432 (3)	0.53210 (16)	0.17124 (18)	0.0402 (6)
C10	0.4491 (3)	0.13542 (17)	0.52900 (19)	0.0462 (7)
H10	0.4782	0.1049	0.4723	0.055*
C11	0.3919 (3)	0.08600 (16)	0.60484 (18)	0.0405 (7)
H11	0.3804	0.0239	0.5985	0.049*
C12	0.3513 (3)	0.13035 (15)	0.69125 (16)	0.0302 (5)
C13	0.3600 (3)	0.22316 (15)	0.69197 (17)	0.0319 (6)
H13	0.3274	0.2556	0.7462	0.038*
C14	0.4171 (3)	0.26728 (16)	0.61198 (17)	0.0361 (6)
H14	0.4224	0.3298	0.6137	0.043*
C15	0.3122 (3)	0.07958 (14)	0.78172 (16)	0.0284 (5)
C16	0.2130 (3)	0.11360 (15)	0.84858 (17)	0.0354 (6)
H16	0.1628	0.1689	0.8337	0.043*
C17	0.2625 (3)	−0.00820 (15)	0.95212 (18)	0.0423 (7)
H17	0.2449	−0.0386	1.0117	0.051*
C18	0.3827 (3)	−0.00268 (15)	0.80969 (18)	0.0402 (6)
H18	0.4496	−0.0283	0.7666	0.048*
N1	0.4653 (2)	0.22434 (14)	0.53205 (15)	0.0398 (5)
N2	0.3604 (3)	−0.04710 (13)	0.89448 (16)	0.0470 (6)
N3	0.1871 (2)	0.06964 (12)	0.93362 (14)	0.0380 (5)
O1	1.0171 (2)	0.14904 (10)	0.06445 (13)	0.0432 (5)
H1	1.071 (4)	0.1197 (19)	0.014 (2)	0.082 (10)*
O2	1.0535 (2)	0.26844 (10)	−0.03140 (12)	0.0392 (5)
O3	0.9472 (3)	0.56310 (13)	0.11264 (15)	0.0621 (7)
H3A	0.930 (4)	0.622 (2)	0.095 (2)	0.088 (11)*
O4	0.7531 (2)	0.57872 (11)	0.21148 (14)	0.0605 (6)
O5	0.6348 (2)	0.30593 (11)	0.40541 (13)	0.0446 (5)
H5A	0.572 (4)	0.276 (2)	0.449 (2)	0.093 (11)*
O6	0.6847 (2)	0.16917 (11)	0.34744 (13)	0.0482 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0310 (14)	0.0294 (13)	0.0331 (13)	0.0002 (10)	0.0093 (11)	−0.0013 (10)
C2	0.0296 (14)	0.0323 (13)	0.0289 (12)	−0.0002 (10)	0.0087 (10)	0.0011 (9)
C3	0.0368 (15)	0.0331 (13)	0.0315 (13)	−0.0010 (10)	0.0153 (11)	0.0037 (9)
C4	0.0343 (15)	0.0328 (13)	0.0285 (13)	0.0029 (10)	0.0096 (11)	0.0016 (9)
C5	0.0340 (14)	0.0378 (14)	0.0270 (12)	0.0016 (11)	0.0108 (11)	−0.0009 (10)
C6	0.0283 (14)	0.0376 (13)	0.0293 (13)	−0.0006 (10)	0.0079 (11)	−0.0004 (10)
C7	0.0337 (14)	0.0290 (12)	0.0330 (13)	−0.0006 (10)	0.0092 (11)	0.0006 (9)
C8	0.0343 (15)	0.0370 (14)	0.0280 (13)	−0.0007 (11)	0.0081 (11)	0.0006 (10)
C9	0.0546 (18)	0.0356 (14)	0.0332 (13)	0.0027 (12)	0.0161 (13)	0.0019 (11)
C10	0.0549 (19)	0.0501 (17)	0.0381 (15)	0.0041 (13)	0.0222 (14)	−0.0040 (12)
C11	0.0529 (18)	0.0337 (14)	0.0379 (14)	0.0006 (12)	0.0168 (13)	−0.0050 (10)
C12	0.0283 (14)	0.0316 (13)	0.0318 (13)	−0.0003 (10)	0.0079 (10)	−0.0017 (9)
C13	0.0343 (15)	0.0319 (13)	0.0311 (13)	0.0005 (10)	0.0107 (11)	0.0001 (10)
C14	0.0379 (15)	0.0329 (13)	0.0391 (14)	−0.0021 (11)	0.0110 (12)	0.0022 (10)
C15	0.0292 (14)	0.0245 (12)	0.0326 (13)	−0.0041 (10)	0.0085 (11)	−0.0022 (9)
C16	0.0399 (16)	0.0287 (12)	0.0404 (14)	0.0026 (10)	0.0149 (12)	0.0027 (10)
C17	0.0608 (19)	0.0314 (13)	0.0384 (14)	−0.0028 (12)	0.0197 (13)	0.0047 (11)
C18	0.0528 (18)	0.0288 (13)	0.0435 (15)	0.0004 (12)	0.0224 (13)	−0.0029 (11)
N1	0.0390 (13)	0.0460 (13)	0.0369 (12)	−0.0002 (10)	0.0142 (10)	0.0045 (9)
N2	0.0670 (17)	0.0312 (11)	0.0483 (13)	0.0081 (10)	0.0269 (12)	0.0056 (9)
N3	0.0478 (14)	0.0334 (11)	0.0365 (12)	0.0016 (10)	0.0192 (10)	0.0021 (9)
O1	0.0601 (13)	0.0291 (9)	0.0477 (11)	0.0043 (8)	0.0320 (10)	0.0012 (7)
O2	0.0541 (12)	0.0323 (9)	0.0365 (10)	0.0032 (8)	0.0249 (9)	0.0041 (7)
O3	0.0953 (17)	0.0323 (11)	0.0711 (14)	0.0013 (10)	0.0537 (13)	0.0090 (9)
O4	0.0866 (16)	0.0362 (10)	0.0679 (14)	0.0151 (10)	0.0422 (12)	−0.0003 (9)
O5	0.0600 (13)	0.0422 (10)	0.0386 (10)	−0.0023 (9)	0.0306 (10)	0.0002 (8)
O6	0.0666 (14)	0.0344 (10)	0.0498 (11)	−0.0034 (9)	0.0288 (10)	0.0039 (8)

Geometric parameters (Å, º) top

C1—O2	1.215 (2)	C11—C12	1.391 (3)
C1—O1	1.307 (3)	C11—H11	0.9300
C1—C2	1.490 (3)	C12—C13	1.381 (3)
C2—C3	1.387 (3)	C12—C15	1.478 (3)
C2—C7	1.390 (3)	C13—C14	1.377 (3)
C3—C4	1.390 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—N1	1.335 (3)
C4—C5	1.391 (3)	C14—H14	0.9300
C4—C9	1.485 (3)	C15—C18	1.383 (3)
C5—C6	1.381 (3)	C15—C16	1.384 (3)
C5—H5	0.9300	C16—N3	1.333 (3)
C6—C7	1.389 (3)	C16—H16	0.9300
C6—C8	1.499 (3)	C17—N2	1.322 (3)
C7—H7	0.9300	C17—N3	1.323 (3)
C8—O6	1.204 (3)	C17—H17	0.9300
C8—O5	1.318 (3)	C18—N2	1.326 (3)
C9—O4	1.199 (3)	C18—H18	0.9300
C9—O3	1.321 (3)	O1—H1	0.95 (3)
C10—N1	1.329 (3)	O3—H3A	0.92 (3)
C10—C11	1.374 (3)	O5—H5A	0.95 (3)
C10—H10	0.9300

O2—C1—O1	123.10 (19)	C10—C11—C12	118.9 (2)
O2—C1—C2	123.3 (2)	C10—C11—H11	120.6
O1—C1—C2	113.59 (18)	C12—C11—H11	120.6
C3—C2—C7	119.60 (19)	C13—C12—C11	117.41 (19)
C3—C2—C1	118.57 (18)	C13—C12—C15	121.45 (18)
C7—C2—C1	121.8 (2)	C11—C12—C15	121.0 (2)
C2—C3—C4	120.57 (19)	C14—C13—C12	119.6 (2)
C2—C3—H3	119.7	C14—C13—H13	120.2
C4—C3—H3	119.7	C12—C13—H13	120.2
C3—C4—C5	119.1 (2)	N1—C14—C13	122.9 (2)
C3—C4—C9	121.33 (19)	N1—C14—H14	118.5
C5—C4—C9	119.52 (19)	C13—C14—H14	118.5
C6—C5—C4	120.8 (2)	C18—C15—C16	115.3 (2)
C6—C5—H5	119.6	C18—C15—C12	121.86 (19)
C4—C5—H5	119.6	C16—C15—C12	122.7 (2)
C5—C6—C7	119.71 (19)	N3—C16—C15	122.1 (2)
C5—C6—C8	121.53 (19)	N3—C16—H16	119.0
C7—C6—C8	118.7 (2)	C15—C16—H16	119.0
C6—C7—C2	120.2 (2)	N2—C17—N3	126.6 (2)
C6—C7—H7	119.9	N2—C17—H17	116.7
C2—C7—H7	119.9	N3—C17—H17	116.7
O6—C8—O5	124.2 (2)	N2—C18—C15	123.7 (2)
O6—C8—C6	123.10 (19)	N2—C18—H18	118.1
O5—C8—C6	112.7 (2)	C15—C18—H18	118.1
O4—C9—O3	124.0 (2)	C10—N1—C14	117.28 (19)
O4—C9—C4	124.2 (2)	C17—N2—C18	115.6 (2)
O3—C9—C4	111.8 (2)	C17—N3—C16	116.78 (19)
N1—C10—C11	123.7 (2)	C1—O1—H1	109.3 (17)
N1—C10—H10	118.1	C9—O3—H3A	113.0 (19)
C11—C10—H10	118.1	C8—O5—H5A	111.9 (18)

O2—C1—C2—C3	−7.5 (3)	C3—C4—C9—O3	−16.2 (3)
O1—C1—C2—C3	172.1 (2)	C5—C4—C9—O3	165.7 (2)
O2—C1—C2—C7	172.3 (2)	N1—C10—C11—C12	−1.5 (4)
O1—C1—C2—C7	−8.1 (3)	C10—C11—C12—C13	4.7 (4)
C7—C2—C3—C4	−0.3 (4)	C10—C11—C12—C15	−171.0 (2)
C1—C2—C3—C4	179.4 (2)	C11—C12—C13—C14	−4.1 (3)
C2—C3—C4—C5	−0.5 (3)	C15—C12—C13—C14	171.5 (2)
C2—C3—C4—C9	−178.7 (2)	C12—C13—C14—N1	0.1 (4)
C3—C4—C5—C6	1.0 (3)	C13—C12—C15—C18	−144.0 (2)
C9—C4—C5—C6	179.2 (2)	C11—C12—C15—C18	31.5 (3)
C4—C5—C6—C7	−0.6 (3)	C13—C12—C15—C16	31.0 (3)
C4—C5—C6—C8	−177.9 (2)	C11—C12—C15—C16	−153.5 (2)
C5—C6—C7—C2	−0.3 (3)	C18—C15—C16—N3	−0.3 (4)
C8—C6—C7—C2	177.1 (2)	C12—C15—C16—N3	−175.5 (2)
C3—C2—C7—C6	0.8 (3)	C16—C15—C18—N2	−0.6 (4)
C1—C2—C7—C6	−179.0 (2)	C12—C15—C18—N2	174.7 (2)
C5—C6—C8—O6	173.9 (2)	C11—C10—N1—C14	−2.5 (4)
C7—C6—C8—O6	−3.5 (4)	C13—C14—N1—C10	3.2 (4)
C5—C6—C8—O5	−4.9 (3)	N3—C17—N2—C18	−0.4 (4)
C7—C6—C8—O5	177.7 (2)	C15—C18—N2—C17	0.9 (4)
C3—C4—C9—O4	162.8 (3)	N2—C17—N3—C16	−0.4 (4)
C5—C4—C9—O4	−15.4 (4)	C15—C16—N3—C17	0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.95 (3)	1.70 (3)	2.652 (2)	173 (3)
O3—H3A···O2ⁱⁱ	0.92 (3)	1.84 (3)	2.720 (2)	161 (3)
O5—H5A···N1	0.95 (3)	1.68 (3)	2.626 (2)	177 (3)
C3—H3···O3ⁱⁱ	0.93	2.48	3.367 (3)	159
C14—H14···N2ⁱⁱⁱ	0.93	2.59	3.335 (3)	137

Symmetry codes: (i) x+1, y, z−1; (ii) −x+2, −y+1, −z; (iii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₉H₇N₃·C₉H₆O₆
M_r	367.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.3532 (19), 14.865 (3), 13.066 (3)
β (°)	98.325 (4)
V (Å³)	1605.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.32 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8278, 2967, 2142
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.130, 1.04
No. of reflections	2967
No. of parameters	256
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.95 (3)	1.70 (3)	2.652 (2)	173 (3)
O3—H3A···O2ⁱⁱ	0.92 (3)	1.84 (3)	2.720 (2)	161 (3)
O5—H5A···N1	0.95 (3)	1.68 (3)	2.626 (2)	177 (3)
C3—H3···O3ⁱⁱ	0.93	2.48	3.367 (3)	159
C14—H14···N2ⁱⁱⁱ	0.93	2.59	3.335 (3)	137

Symmetry codes: (i) x+1, y, z−1; (ii) −x+2, −y+1, −z; (iii) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors thank the Scientific Research Project of Chongqing Education Committee, China (KJ100720 and KJTD201020) and Chongqing Technology and Business University, China (2010-56-07) for supporting this work.

References

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