2-(4-Chloro­phen­yl)imidazo[1,2-a]pyridine-3-carbaldehyde

Li, Y.-H.; Liu, W.-Y.; Gao, Y.; Wang, Y.-P.

doi:10.1107/S1600536809048302

organic compounds

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Volume 65| Part 12| December 2009| Page o3192

doi:10.1107/S1600536809048302

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2-(4-Chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde

Yun-Hui Li,^a ^* Wen-Yu Liu,^a Yang Gao ^b and Yu-Peng Wang ^a

^aSchool of Chemistry and Environmental Engineering, Changchun University of Science and Technology, Changchun 130022, People's Republic of China, and ^bJilin College of Transportation Vocation and Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: lyunhui@163.com

(Received 31 October 2009; accepted 14 November 2009; online 25 November 2009)

The asymmetric unit of the title compound, C₁₄H₉ClN₂O, contains two molecules with dihedral angles of 33.52 (11) and 34.58 (11)° between their benzene rings and imidazole ring systems. In the crystal, C—H⋯N and C—H⋯O interactions are observed. The crystal examined was found to be a racemic twin.

Related literature

For the synthesis, see: Burkholder et al. (2001 ).

Experimental

Crystal data

C₁₄H₉ClN₂O
M_r = 256.68
Orthorhombic, P n a 2₁
a = 21.3367 (13) Å
b = 7.2391 (4) Å
c = 15.1748 (10) Å
V = 2343.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.35 × 0.29 × 0.28 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.870, T_max = 0.894
12428 measured reflections
4198 independent reflections
3564 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.089
S = 1.03
4198 reflections
325 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1800 Friedel pairs
Flack parameter: 0.40 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.93	2.54	3.442 (3)	163
C12—H12⋯N4ⁱⁱ	0.93	2.59	3.518 (4)	172
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048302/hb5204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048302/hb5204Isup2.hkl

checkCIF report

Related literature top

For the synthesis, see: Burkholder et al. (2001).

Experimental top

To a solution of 2.0 mmol 2-(4-chlorophenyl)H-imidazo[1,2-a]pyridine (Burkholder et al., 2001) in DMF (10 ml) was added phosphoryl trichloride (2.2 mmol) in one portion at room temperature under stirring. The mixture was heated to 353 K and stirred for 5.0 h. After the intermediate was consumed (monitored by TLC), the reaction mixture was extracted, filtered and concentrated in vacuo. The pure product was obtained through silica gel chromatography, and yellow blocks of (I) were obtained by slow evaporation of an ethyl acetate/petroleum ether (1:1) solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level for non-H atoms.

2-(4-Chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde top

Crystal data top

C₁₄H₉ClN₂O	F(000) = 1056
M_r = 256.68	D_x = 1.455 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4265 reflections
a = 21.3367 (13) Å	θ = 1.9–26.0°
b = 7.2391 (4) Å	µ = 0.31 mm⁻¹
c = 15.1748 (10) Å	T = 293 K
V = 2343.9 (2) Å³	Block, yellow
Z = 8	0.35 × 0.29 × 0.28 mm

Data collection top

Bruker APEX CCD diffractometer	4198 independent reflections
Radiation source: fine-focus sealed tube	3564 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −26→26
T_min = 0.870, T_max = 0.894	k = −8→8
12428 measured reflections	l = −15→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0461P)² + 0.2155P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4198 reflections	Δρ_max = 0.22 e Å⁻³
325 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1800 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.40 (5)

Crystal data top

C₁₄H₉ClN₂O	V = 2343.9 (2) Å³
M_r = 256.68	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 21.3367 (13) Å	µ = 0.31 mm⁻¹
b = 7.2391 (4) Å	T = 293 K
c = 15.1748 (10) Å	0.35 × 0.29 × 0.28 mm

Data collection top

Bruker APEX CCD diffractometer	4198 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3564 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.894	R_int = 0.026
12428 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.089	Δρ_max = 0.22 e Å⁻³
S = 1.03	Δρ_min = −0.18 e Å⁻³
4198 reflections	Absolute structure: Flack (1983), 1800 Friedel pairs
325 parameters	Absolute structure parameter: 0.40 (5)
1 restraint

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
Cl1	0.38891 (3)	0.69710 (12)	0.18830 (6)	0.0741 (3)
Cl2	0.86516 (3)	1.12252 (11)	0.50704 (6)	0.0673 (2)
O2	0.48266 (8)	1.0458 (3)	0.48167 (13)	0.0652 (6)
O1	0.76678 (8)	0.5045 (3)	0.22142 (13)	0.0620 (5)
N1	0.73924 (8)	0.6319 (3)	0.39935 (13)	0.0373 (4)
N2	0.64367 (8)	0.7006 (3)	0.45277 (14)	0.0434 (5)
N4	0.60866 (9)	1.2130 (3)	0.24891 (14)	0.0403 (5)
C6	0.57814 (10)	0.6745 (3)	0.32064 (17)	0.0387 (6)
N3	0.51184 (8)	1.1689 (3)	0.30384 (13)	0.0368 (4)
C7	0.63898 (10)	0.6637 (3)	0.36576 (16)	0.0345 (5)
C21	0.61298 (10)	1.1699 (3)	0.33495 (17)	0.0370 (5)
C11	0.83204 (12)	0.6244 (4)	0.48197 (19)	0.0507 (7)
H11	0.8750	0.6038	0.4857	0.061*
C17	0.79144 (11)	1.1336 (4)	0.45777 (19)	0.0467 (6)
C14	0.70483 (10)	0.6813 (3)	0.47280 (16)	0.0400 (6)
C20	0.67494 (10)	1.1586 (3)	0.37871 (17)	0.0376 (6)
C8	0.69729 (10)	0.6195 (3)	0.32942 (16)	0.0360 (5)
C28	0.54724 (10)	1.2129 (3)	0.23030 (16)	0.0384 (6)
C18	0.78521 (11)	1.0860 (4)	0.37049 (19)	0.0489 (6)
H18	0.8198	1.0467	0.3382	0.059*
C22	0.55419 (10)	1.1401 (3)	0.37297 (16)	0.0380 (5)
C19	0.72678 (10)	1.0975 (3)	0.33157 (17)	0.0423 (6)
H19	0.7221	1.0638	0.2728	0.051*
C2	0.51455 (11)	0.7437 (4)	0.1929 (2)	0.0505 (6)
H2	0.5110	0.7846	0.1350	0.061*
C9	0.71397 (11)	0.5482 (3)	0.24447 (17)	0.0434 (6)
H9	0.6819	0.5340	0.2035	0.052*
C5	0.52395 (11)	0.6241 (3)	0.36600 (18)	0.0448 (6)
H5	0.5268	0.5846	0.4242	0.054*
C24	0.44781 (11)	1.1572 (3)	0.30118 (19)	0.0462 (6)
H24	0.4251	1.1274	0.3515	0.055*
C27	0.51591 (12)	1.2473 (4)	0.15048 (19)	0.0492 (6)
H27	0.5384	1.2786	0.1001	0.059*
C13	0.73559 (11)	0.7049 (4)	0.55341 (19)	0.0507 (7)
H13	0.7133	0.7401	0.6033	0.061*
C10	0.80304 (10)	0.6045 (3)	0.40399 (19)	0.0446 (6)
H10	0.8257	0.5727	0.3539	0.054*
C26	0.45240 (12)	1.2345 (4)	0.14768 (19)	0.0526 (7)
H26	0.4314	1.2554	0.0949	0.063*
C1	0.57237 (11)	0.7353 (4)	0.23404 (18)	0.0439 (6)
H1	0.6080	0.7709	0.2032	0.053*
C16	0.74146 (11)	1.1959 (4)	0.5060 (2)	0.0497 (6)
H16	0.7466	1.2286	0.5649	0.060*
C4	0.46599 (12)	0.6322 (4)	0.32548 (19)	0.0497 (6)
H4	0.4300	0.5988	0.3561	0.060*
C23	0.53638 (11)	1.0703 (3)	0.45701 (17)	0.0463 (6)
H23	0.5683	1.0410	0.4963	0.056*
C15	0.68309 (11)	1.2097 (4)	0.46614 (18)	0.0468 (6)
H15	0.6491	1.2536	0.4983	0.056*
C12	0.79878 (12)	0.6758 (4)	0.5579 (2)	0.0513 (7)
H12	0.8197	0.6899	0.6112	0.062*
C25	0.41833 (12)	1.1899 (4)	0.22393 (19)	0.0514 (7)
H25	0.3749	1.1827	0.2212	0.062*
C3	0.46229 (12)	0.6899 (4)	0.23968 (19)	0.0485 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0499 (4)	0.0888 (6)	0.0835 (6)	0.0081 (4)	−0.0283 (4)	−0.0004 (5)
Cl2	0.0459 (3)	0.0834 (5)	0.0725 (5)	−0.0041 (3)	−0.0179 (3)	0.0060 (4)
O2	0.0454 (10)	0.0979 (15)	0.0524 (12)	−0.0022 (10)	0.0123 (9)	0.0151 (11)
O1	0.0459 (10)	0.0937 (16)	0.0462 (12)	0.0041 (10)	0.0086 (9)	−0.0156 (10)
N1	0.0354 (10)	0.0400 (11)	0.0365 (12)	−0.0013 (8)	−0.0023 (9)	−0.0030 (8)
N2	0.0392 (10)	0.0512 (13)	0.0399 (14)	0.0004 (9)	0.0005 (10)	−0.0062 (10)
N4	0.0380 (10)	0.0492 (12)	0.0337 (12)	−0.0002 (9)	0.0021 (9)	−0.0003 (9)
C6	0.0399 (13)	0.0367 (12)	0.0393 (15)	0.0020 (10)	−0.0026 (11)	−0.0046 (11)
N3	0.0343 (10)	0.0400 (10)	0.0361 (12)	0.0006 (8)	−0.0024 (9)	−0.0024 (8)
C7	0.0354 (11)	0.0351 (12)	0.0331 (13)	0.0008 (9)	−0.0014 (10)	−0.0026 (10)
C21	0.0393 (12)	0.0365 (12)	0.0354 (14)	0.0017 (10)	0.0030 (11)	−0.0013 (10)
C11	0.0389 (12)	0.0547 (16)	0.0585 (19)	0.0020 (11)	−0.0094 (13)	−0.0043 (13)
C17	0.0409 (13)	0.0476 (15)	0.0517 (18)	−0.0066 (11)	−0.0098 (13)	0.0087 (12)
C14	0.0388 (12)	0.0448 (14)	0.0364 (15)	0.0006 (11)	0.0010 (11)	−0.0068 (10)
C20	0.0357 (12)	0.0385 (13)	0.0384 (15)	−0.0040 (9)	−0.0001 (10)	0.0044 (11)
C8	0.0366 (12)	0.0379 (12)	0.0337 (13)	−0.0032 (9)	−0.0010 (10)	0.0000 (10)
C28	0.0377 (12)	0.0444 (14)	0.0333 (14)	−0.0012 (10)	0.0025 (10)	−0.0032 (10)
C18	0.0387 (13)	0.0547 (17)	0.0533 (18)	0.0038 (11)	0.0035 (12)	0.0056 (13)
C22	0.0352 (12)	0.0413 (13)	0.0375 (14)	0.0011 (9)	0.0005 (11)	−0.0015 (10)
C19	0.0411 (13)	0.0500 (14)	0.0359 (14)	0.0018 (10)	0.0011 (11)	0.0014 (11)
C2	0.0561 (15)	0.0541 (17)	0.0411 (16)	0.0085 (12)	−0.0045 (14)	0.0009 (13)
C9	0.0438 (13)	0.0479 (15)	0.0385 (14)	−0.0032 (11)	0.0001 (11)	−0.0027 (11)
C5	0.0418 (13)	0.0505 (15)	0.0421 (15)	0.0007 (10)	0.0016 (11)	−0.0004 (12)
C24	0.0359 (12)	0.0513 (15)	0.0513 (17)	−0.0028 (11)	0.0038 (12)	−0.0016 (12)
C27	0.0536 (15)	0.0571 (16)	0.0368 (16)	−0.0002 (12)	−0.0031 (13)	−0.0029 (12)
C13	0.0513 (15)	0.0651 (17)	0.0357 (16)	0.0014 (13)	−0.0052 (13)	−0.0103 (13)
C10	0.0341 (12)	0.0499 (15)	0.0497 (16)	0.0014 (11)	0.0010 (11)	−0.0045 (12)
C26	0.0545 (15)	0.0571 (16)	0.0463 (18)	0.0074 (13)	−0.0121 (14)	−0.0076 (13)
C1	0.0408 (13)	0.0475 (15)	0.0435 (17)	0.0017 (11)	0.0008 (11)	0.0011 (11)
C16	0.0509 (14)	0.0592 (16)	0.0389 (16)	−0.0058 (12)	−0.0078 (13)	−0.0015 (13)
C4	0.0378 (13)	0.0559 (16)	0.0555 (18)	−0.0022 (11)	−0.0025 (12)	−0.0025 (13)
C23	0.0425 (13)	0.0539 (15)	0.0424 (15)	−0.0009 (11)	0.0028 (12)	0.0038 (12)
C15	0.0449 (13)	0.0561 (17)	0.0395 (17)	−0.0011 (11)	0.0036 (12)	0.0015 (12)
C12	0.0503 (15)	0.0621 (17)	0.0414 (16)	−0.0041 (13)	−0.0133 (13)	−0.0032 (13)
C25	0.0402 (13)	0.0579 (17)	0.0560 (18)	0.0024 (12)	−0.0091 (13)	−0.0064 (13)
C3	0.0421 (13)	0.0475 (15)	0.0560 (18)	0.0069 (11)	−0.0129 (13)	−0.0065 (13)

Geometric parameters (Å, º) top

Cl1—C3	1.750 (3)	C28—C27	1.406 (4)
Cl2—C17	1.743 (2)	C18—C19	1.382 (3)
O2—C23	1.219 (3)	C18—H18	0.9300
O1—C9	1.221 (3)	C22—C23	1.424 (3)
N1—C10	1.378 (3)	C19—H19	0.9300
N1—C14	1.382 (3)	C2—C3	1.378 (4)
N1—C8	1.391 (3)	C2—C1	1.384 (3)
N2—C14	1.347 (3)	C2—H2	0.9300
N2—C7	1.351 (3)	C9—H9	0.9300
N4—C28	1.341 (3)	C5—C4	1.382 (3)
N4—C21	1.346 (3)	C5—H5	0.9300
C6—C1	1.391 (4)	C24—C25	1.351 (4)
C6—C5	1.394 (3)	C24—H24	0.9300
C6—C7	1.470 (3)	C27—C26	1.359 (3)
N3—C24	1.369 (3)	C27—H27	0.9300
N3—C28	1.385 (3)	C13—C12	1.366 (3)
N3—C22	1.400 (3)	C13—H13	0.9300
C7—C8	1.398 (3)	C10—H10	0.9300
C21—C22	1.397 (3)	C26—C25	1.404 (4)
C21—C20	1.482 (3)	C26—H26	0.9300
C11—C10	1.343 (4)	C1—H1	0.9300
C11—C12	1.403 (4)	C16—C15	1.389 (3)
C11—H11	0.9300	C16—H16	0.9300
C17—C16	1.370 (4)	C4—C3	1.370 (4)
C17—C18	1.375 (4)	C4—H4	0.9300
C14—C13	1.399 (4)	C23—H23	0.9300
C20—C15	1.388 (4)	C15—H15	0.9300
C20—C19	1.390 (3)	C12—H12	0.9300
C8—C9	1.434 (3)	C25—H25	0.9300

C10—N1—C14	121.4 (2)	C1—C2—H2	120.8
C10—N1—C8	131.7 (2)	O1—C9—C8	125.4 (2)
C14—N1—C8	106.87 (18)	O1—C9—H9	117.3
C14—N2—C7	105.8 (2)	C8—C9—H9	117.3
C28—N4—C21	105.7 (2)	C4—C5—C6	120.8 (3)
C1—C6—C5	118.4 (2)	C4—C5—H5	119.6
C1—C6—C7	122.3 (2)	C6—C5—H5	119.6
C5—C6—C7	119.2 (2)	C25—C24—N3	118.6 (2)
C24—N3—C28	122.3 (2)	C25—C24—H24	120.7
C24—N3—C22	131.1 (2)	N3—C24—H24	120.7
C28—N3—C22	106.61 (18)	C26—C27—C28	119.3 (3)
N2—C7—C8	111.4 (2)	C26—C27—H27	120.4
N2—C7—C6	120.7 (2)	C28—C27—H27	120.4
C8—C7—C6	127.9 (2)	C12—C13—C14	119.2 (2)
N4—C21—C22	112.0 (2)	C12—C13—H13	120.4
N4—C21—C20	120.6 (2)	C14—C13—H13	120.4
C22—C21—C20	127.4 (2)	C11—C10—N1	119.0 (2)
C10—C11—C12	121.3 (2)	C11—C10—H10	120.5
C10—C11—H11	119.4	N1—C10—H10	120.5
C12—C11—H11	119.4	C27—C26—C25	120.4 (3)
C16—C17—C18	121.5 (2)	C27—C26—H26	119.8
C16—C17—Cl2	119.2 (2)	C25—C26—H26	119.8
C18—C17—Cl2	119.3 (2)	C2—C1—C6	121.2 (2)
N2—C14—N1	111.1 (2)	C2—C1—H1	119.4
N2—C14—C13	129.7 (2)	C6—C1—H1	119.4
N1—C14—C13	119.2 (2)	C17—C16—C15	119.2 (3)
C15—C20—C19	118.5 (2)	C17—C16—H16	120.4
C15—C20—C21	121.7 (2)	C15—C16—H16	120.4
C19—C20—C21	119.8 (2)	C3—C4—C5	119.2 (3)
N1—C8—C7	104.9 (2)	C3—C4—H4	120.4
N1—C8—C9	123.3 (2)	C5—C4—H4	120.4
C7—C8—C9	131.1 (2)	O2—C23—C22	125.3 (2)
N4—C28—N3	111.3 (2)	O2—C23—H23	117.3
N4—C28—C27	130.3 (2)	C22—C23—H23	117.3
N3—C28—C27	118.4 (2)	C20—C15—C16	120.7 (2)
C17—C18—C19	118.9 (2)	C20—C15—H15	119.7
C17—C18—H18	120.5	C16—C15—H15	119.7
C19—C18—H18	120.5	C13—C12—C11	120.0 (3)
C21—C22—N3	104.3 (2)	C13—C12—H12	120.0
C21—C22—C23	131.6 (2)	C11—C12—H12	120.0
N3—C22—C23	123.5 (2)	C24—C25—C26	121.0 (2)
C18—C19—C20	121.1 (2)	C24—C25—H25	119.5
C18—C19—H19	119.4	C26—C25—H25	119.5
C20—C19—H19	119.4	C4—C3—C2	122.0 (2)
C3—C2—C1	118.5 (3)	C4—C3—Cl1	119.0 (2)
C3—C2—H2	120.8	C2—C3—Cl1	119.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.93	2.54	3.442 (3)	163
C12—H12···N4ⁱⁱ	0.93	2.59	3.518 (4)	172

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

Experimental details

Crystal data
Chemical formula	C₁₄H₉ClN₂O
M_r	256.68
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	21.3367 (13), 7.2391 (4), 15.1748 (10)
V (Å³)	2343.9 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.35 × 0.29 × 0.28

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.870, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	12428, 4198, 3564
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.089, 1.03
No. of reflections	4198
No. of parameters	325
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18
Absolute structure	Flack (1983), 1800 Friedel pairs
Absolute structure parameter	0.40 (5)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
C11—H11···O2ⁱ	0.93	2.54	3.442 (3)	163
C12—H12···N4ⁱⁱ	0.93	2.59	3.518 (4)	172

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

Acknowledgements

The authors thank Changchun University of Science and Technology for supporting this work.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burkholder, C., Dolbier, W. R., Medebielle, M. & Ait-Mohand, S. (2001). Tetrahedron Lett. 42, 3077–3080. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar