5-(Anthracen-9-yl)-3-(4-nitro­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole

Dong, B.-L.; Wang, M.-L.; Li, Y.-H.

doi:10.1107/S1600536810038912

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2786

https://doi.org/10.1107/S1600536810038912

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5-(Anthracen-9-yl)-3-(4-nitrophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole

Bao-Li Dong,^a Ming-Liang Wang ^a ^* and Yong-Hua Li ^a

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: wangmlchem@263.net

(Received 25 September 2010; accepted 29 September 2010; online 9 October 2010)

In the title compound, C₂₉H₂₁N₃O₂, the five-membered pyrazoline ring is nearly planar, the maximum deviation being 0.037 (3) Å. The anthracene ring system is approximately perpendicular to the central pyrazoline ring, making a dihedral angle of 86.55 (16)°, whereas the two attached benzene rings are oriented at smaller dihedral angles of 12.9 (2) and 14.7 (2)°with respect to the pyrazoline ring. An intramolecular C—H⋯N hydrogen bond is observed.

Related literature

For applications of pyrazoline derivatives, see: Shaharyar et al. (2006 ); Christoph et al. (2003 ); Parmar et al. (1974 ); Prasad et al. (2005 ). For a related pyrazoline compound, see: Krishna et al. (1999 ).

Experimental

Crystal data

C₂₉H₂₁N₃O₂
M_r = 443.49
Orthorhombic, P c a 2₁
a = 23.023 (5) Å
b = 10.195 (2) Å
c = 9.2005 (18) Å
V = 2159.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
17812 measured reflections
2023 independent reflections
1675 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.095
S = 1.08
2023 reflections
308 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N2	0.93	2.59	3.422 (5)	150

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: https://doi.org/10.1107/S1600536810038912/xu5037sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038912/xu5037Isup2.hkl

checkCIF report

Comment top

The derivatives of pyrazoline are mostly used in medicine, such as antibacterial (Shaharyar et al., 2006), antidepressant (Prasad et al., 2005) and anticonvulsant (Parmar et al., 1974), furthermore they also have application in cell biological study due to their simple structure and favorable photophysical properties (Christoph et al., 2003). Here we report the structure of the title compound (I), a new derivative of pyrazoline.

In the pyrazoline ring, the bond length of C17=N2 [1.287 (4) Å] indicates a to the normal C=N bond (1.28 Å), while the N2—N3 distance [1.366 (4) Å] agrees with the expected values (Krishna et al., 1999). The mean plane of anthryl ring makes dihedral angles of 84.98 (9) and 82.81 (8)°, with the benzene ring and 4-nitrophenyl group, respectively.

Related literature top

For applications of pyrazoline derivatives, see: Shaharyar et al. (2006); Christoph et al. (2003); Parmar et al. (1974); Prasad et al. (2005). For a related pyrazoline compound, see: Krishna et al. (1999).

Experimental top

3-(9-Anthryl)-1-(4-nitrophenylprop)-2-en-1-one (3 mmol, 1.0 g) and phenylhydrazine (6.5 mmol, 0.7 g) were dissolved in 10 ml acetic acid. The mixture was stirred for 8 h at refluxing temperature to give red solid. The product was isolated and recrystallized from ethanol/ethyl acetate (1:1 v/v) mixed solution, red single-crystal of (1) was obtained.

Structure description top

For applications of pyrazoline derivatives, see: Shaharyar et al. (2006); Christoph et al. (2003); Parmar et al. (1974); Prasad et al. (2005). For a related pyrazoline compound, see: Krishna et al. (1999).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. Perspective structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

5-(Anthracen-9-yl)-3-(4-nitrophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole top

Crystal data top

C₂₉H₂₁N₃O₂	F(000) = 928
M_r = 443.49	D_x = 1.364 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2023 reflections
a = 23.023 (5) Å	θ = 2.6–25.0°
b = 10.195 (2) Å	µ = 0.09 mm⁻¹
c = 9.2005 (18) Å	T = 293 K
V = 2159.6 (7) Å³	Prism, red
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Mercury2 diffractometer	1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 25.0°, θ_min = 3.1°
Detector resolution: 13.6612 pixels mm^-1	h = −27→27
CCD_Profile_fitting scans	k = −12→12
17812 measured reflections	l = −10→10
2023 independent 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) = 0.095	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0418P)² + 0.3731P] where P = (F_o² + 2F_c²)/3
2023 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.14 e Å⁻³
2 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₉H₂₁N₃O₂	V = 2159.6 (7) Å³
M_r = 443.49	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 23.023 (5) Å	µ = 0.09 mm⁻¹
b = 10.195 (2) Å	T = 293 K
c = 9.2005 (18) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Mercury2 diffractometer	1675 reflections with I > 2σ(I)
17812 measured reflections	R_int = 0.068
2023 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	2 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.08	Δρ_max = 0.14 e Å⁻³
2023 reflections	Δρ_min = −0.16 e Å⁻³
308 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
N2	0.34781 (11)	0.8437 (3)	0.1581 (3)	0.0417 (7)
C18	0.33011 (15)	0.6798 (3)	−0.0211 (4)	0.0400 (8)
C6	0.48920 (14)	0.7455 (3)	0.3722 (4)	0.0392 (8)
C7	0.49683 (14)	0.8475 (3)	0.2692 (4)	0.0380 (8)
C5	0.53459 (15)	0.7161 (3)	0.4735 (4)	0.0451 (9)
C17	0.36872 (14)	0.7631 (4)	0.0641 (4)	0.0410 (9)
C21	0.25650 (16)	0.5236 (3)	−0.1831 (4)	0.0437 (9)
C9	0.59566 (15)	0.8817 (4)	0.3653 (4)	0.0461 (9)
O1	0.16551 (13)	0.4657 (3)	−0.2656 (4)	0.0673 (9)
C8	0.55013 (14)	0.9175 (3)	0.2655 (4)	0.0394 (9)
C15	0.44934 (13)	0.8788 (3)	0.1582 (4)	0.0408 (8)
H15A	0.4619	0.9549	0.1013	0.049*
N3	0.39237 (12)	0.9097 (3)	0.2234 (4)	0.0434 (7)
C29	0.42219 (16)	1.1131 (3)	0.3361 (4)	0.0437 (9)
H29A	0.4595	1.1022	0.2991	0.052*
C1	0.43743 (16)	0.6694 (3)	0.3833 (4)	0.0464 (9)
H1A	0.4074	0.6842	0.3178	0.056*
C27	0.35497 (16)	1.2377 (4)	0.4779 (5)	0.0594 (11)
H27A	0.3468	1.3096	0.5367	0.071*
C11	0.65023 (17)	0.9509 (4)	0.3584 (5)	0.0613 (12)
H11A	0.6801	0.9270	0.4211	0.074*
C14	0.56258 (15)	1.0242 (3)	0.1698 (5)	0.0482 (9)
H14A	0.5339	1.0515	0.1053	0.058*
C24	0.37940 (15)	1.0216 (3)	0.3050 (4)	0.0409 (9)
C10	0.58675 (16)	0.7836 (4)	0.4662 (4)	0.0506 (10)
H10A	0.6164	0.7624	0.5307	0.061*
N1	0.21739 (15)	0.4423 (3)	−0.2714 (4)	0.0558 (9)
C23	0.35171 (16)	0.5779 (4)	−0.1053 (5)	0.0546 (11)
H23A	0.3915	0.5628	−0.1076	0.066*
C2	0.43091 (17)	0.5761 (4)	0.4868 (5)	0.0564 (11)
H2A	0.3967	0.5277	0.4904	0.068*
C20	0.23398 (15)	0.6237 (4)	−0.1030 (4)	0.0476 (10)
H20A	0.1942	0.6399	−0.1041	0.057*
O2	0.23825 (14)	0.3550 (3)	−0.3453 (4)	0.0887 (11)
C28	0.40961 (17)	1.2200 (4)	0.4218 (5)	0.0509 (10)
H28A	0.4385	1.2810	0.4419	0.061*
C12	0.65894 (18)	1.0493 (4)	0.2635 (6)	0.0689 (13)
H12A	0.6946	1.0921	0.2605	0.083*
C16	0.43391 (13)	0.7676 (4)	0.0517 (4)	0.0453 (9)
H16A	0.4461	0.7885	−0.0466	0.054*
H16B	0.4514	0.6852	0.0810	0.054*
C13	0.61422 (17)	1.0873 (4)	0.1690 (5)	0.0577 (11)
H13A	0.6201	1.1567	0.1051	0.069*
C3	0.47497 (19)	0.5511 (4)	0.5891 (5)	0.0590 (11)
H3A	0.4693	0.4889	0.6617	0.071*
C25	0.32422 (17)	1.0409 (4)	0.3603 (5)	0.0566 (11)
H25A	0.2949	0.9812	0.3393	0.068*
C19	0.27035 (15)	0.7011 (3)	−0.0203 (4)	0.0474 (9)
H19A	0.2549	0.7680	0.0365	0.057*
C4	0.52555 (19)	0.6179 (4)	0.5811 (5)	0.0584 (11)
H4A	0.5550	0.5993	0.6471	0.070*
C22	0.31528 (17)	0.4985 (4)	−0.1856 (5)	0.0572 (11)
H22A	0.3301	0.4294	−0.2403	0.069*
C26	0.31263 (17)	1.1481 (4)	0.4460 (6)	0.0679 (13)
H26A	0.2754	1.1600	0.4829	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0337 (16)	0.0427 (16)	0.0487 (18)	0.0034 (14)	−0.0089 (15)	−0.0072 (16)
C18	0.0364 (18)	0.0455 (19)	0.038 (2)	−0.0010 (16)	−0.0049 (17)	−0.0013 (18)
C6	0.0333 (19)	0.0358 (18)	0.048 (2)	0.0078 (15)	−0.0037 (16)	−0.0067 (18)
C7	0.0317 (18)	0.0382 (18)	0.044 (2)	0.0055 (15)	−0.0054 (16)	−0.0067 (18)
C5	0.046 (2)	0.044 (2)	0.045 (2)	0.0123 (17)	−0.0091 (19)	−0.005 (2)
C17	0.0322 (18)	0.049 (2)	0.041 (2)	0.0033 (16)	−0.0077 (16)	−0.0047 (19)
C21	0.040 (2)	0.052 (2)	0.0393 (19)	−0.0063 (18)	−0.0050 (18)	−0.0046 (19)
C9	0.032 (2)	0.054 (2)	0.052 (2)	0.0026 (17)	−0.0061 (17)	−0.014 (2)
O1	0.0474 (17)	0.081 (2)	0.074 (2)	−0.0142 (15)	−0.0129 (17)	−0.0069 (18)
C8	0.0347 (19)	0.042 (2)	0.042 (2)	0.0047 (15)	−0.0029 (16)	−0.0111 (18)
C15	0.0331 (18)	0.044 (2)	0.045 (2)	0.0027 (15)	−0.0080 (17)	−0.0037 (19)
N3	0.0310 (15)	0.0459 (17)	0.0534 (18)	0.0040 (14)	−0.0084 (15)	−0.0110 (16)
C29	0.041 (2)	0.041 (2)	0.049 (2)	0.0030 (17)	−0.0015 (18)	−0.0050 (19)
C1	0.041 (2)	0.042 (2)	0.056 (2)	0.0045 (17)	−0.0084 (19)	−0.001 (2)
C27	0.055 (3)	0.052 (2)	0.071 (3)	0.002 (2)	0.005 (2)	−0.022 (2)
C11	0.038 (2)	0.074 (3)	0.072 (3)	0.002 (2)	−0.012 (2)	−0.015 (3)
C14	0.040 (2)	0.050 (2)	0.055 (2)	0.0007 (18)	0.0018 (19)	−0.004 (2)
C24	0.040 (2)	0.0387 (19)	0.044 (2)	0.0035 (16)	−0.0075 (17)	−0.0030 (18)
C10	0.038 (2)	0.060 (2)	0.054 (3)	0.0114 (19)	−0.014 (2)	−0.012 (2)
N1	0.054 (2)	0.064 (2)	0.050 (2)	−0.0117 (18)	−0.0066 (18)	−0.003 (2)
C23	0.035 (2)	0.076 (3)	0.053 (2)	0.0052 (19)	−0.0053 (19)	−0.021 (2)
C2	0.054 (2)	0.045 (2)	0.071 (3)	0.0012 (19)	0.001 (2)	0.003 (2)
C20	0.0313 (19)	0.055 (2)	0.056 (2)	0.0010 (17)	−0.0054 (19)	−0.002 (2)
O2	0.075 (2)	0.097 (2)	0.094 (3)	−0.007 (2)	−0.001 (2)	−0.055 (2)
C28	0.048 (2)	0.041 (2)	0.064 (3)	0.0001 (18)	−0.004 (2)	−0.005 (2)
C12	0.048 (3)	0.071 (3)	0.088 (4)	−0.017 (2)	0.002 (3)	−0.012 (3)
C16	0.0333 (19)	0.059 (2)	0.044 (2)	0.0019 (17)	−0.0053 (17)	−0.010 (2)
C13	0.046 (2)	0.060 (3)	0.067 (3)	−0.009 (2)	0.005 (2)	−0.007 (2)
C3	0.071 (3)	0.047 (2)	0.059 (3)	0.013 (2)	0.001 (2)	0.011 (2)
C25	0.039 (2)	0.056 (2)	0.074 (3)	−0.0022 (18)	0.004 (2)	−0.019 (2)
C19	0.040 (2)	0.047 (2)	0.055 (2)	0.0028 (17)	−0.0064 (19)	−0.012 (2)
C4	0.061 (3)	0.056 (2)	0.058 (3)	0.018 (2)	−0.011 (2)	0.005 (2)
C22	0.048 (2)	0.070 (3)	0.053 (2)	0.006 (2)	−0.002 (2)	−0.023 (2)
C26	0.044 (2)	0.073 (3)	0.087 (4)	0.005 (2)	0.013 (2)	−0.029 (3)

Geometric parameters (Å, º) top

N2—C17	1.287 (4)	C27—C26	1.368 (5)
N2—N3	1.366 (4)	C27—C28	1.372 (5)
C18—C23	1.388 (5)	C27—H27A	0.9300
C18—C19	1.393 (5)	C11—C12	1.345 (6)
C18—C17	1.458 (5)	C11—H11A	0.9300
C6—C7	1.417 (5)	C14—C13	1.352 (5)
C6—C1	1.426 (5)	C14—H14A	0.9300
C6—C5	1.432 (5)	C24—C25	1.382 (5)
C7—C8	1.420 (5)	C10—H10A	0.9300
C7—C15	1.530 (5)	N1—O2	1.219 (4)
C5—C10	1.386 (5)	C23—C22	1.380 (5)
C5—C4	1.423 (6)	C23—H23A	0.9300
C17—C16	1.506 (5)	C2—C3	1.407 (6)
C21—C20	1.361 (5)	C2—H2A	0.9300
C21—C22	1.378 (5)	C20—C19	1.379 (5)
C21—N1	1.469 (5)	C20—H20A	0.9300
C9—C10	1.381 (6)	C28—H28A	0.9300
C9—C8	1.440 (5)	C12—C13	1.402 (6)
C9—C11	1.442 (5)	C12—H12A	0.9300
O1—N1	1.219 (4)	C16—H16A	0.9700
C8—C14	1.429 (5)	C16—H16B	0.9700
C15—N3	1.476 (4)	C13—H13A	0.9300
C15—C16	1.540 (5)	C3—C4	1.351 (6)
C15—H15A	0.9800	C3—H3A	0.9300
N3—C24	1.398 (4)	C25—C26	1.374 (5)
C29—C28	1.375 (5)	C25—H25A	0.9300
C29—C24	1.387 (5)	C19—H19A	0.9300
C29—H29A	0.9300	C4—H4A	0.9300
C1—C2	1.354 (5)	C22—H22A	0.9300
C1—H1A	0.9300	C26—H26A	0.9300

C17—N2—N3	109.2 (3)	C25—C24—N3	120.7 (3)
C23—C18—C19	118.3 (3)	C29—C24—N3	120.5 (3)
C23—C18—C17	121.2 (3)	C9—C10—C5	121.4 (3)
C19—C18—C17	120.6 (3)	C9—C10—H10A	119.3
C7—C6—C1	123.4 (3)	C5—C10—H10A	119.3
C7—C6—C5	119.9 (3)	O2—N1—O1	123.6 (3)
C1—C6—C5	116.7 (3)	O2—N1—C21	118.6 (3)
C6—C7—C8	119.5 (3)	O1—N1—C21	117.8 (3)
C6—C7—C15	120.7 (3)	C22—C23—C18	121.3 (3)
C8—C7—C15	119.8 (3)	C22—C23—H23A	119.3
C10—C5—C4	120.7 (4)	C18—C23—H23A	119.3
C10—C5—C6	119.8 (4)	C1—C2—C3	121.2 (4)
C4—C5—C6	119.6 (3)	C1—C2—H2A	119.4
N2—C17—C18	120.4 (3)	C3—C2—H2A	119.4
N2—C17—C16	113.8 (3)	C21—C20—C19	119.7 (3)
C18—C17—C16	125.8 (3)	C21—C20—H20A	120.1
C20—C21—C22	121.5 (3)	C19—C20—H20A	120.1
C20—C21—N1	119.3 (3)	C27—C28—C29	120.9 (4)
C22—C21—N1	119.2 (3)	C27—C28—H28A	119.6
C10—C9—C8	120.3 (3)	C29—C28—H28A	119.6
C10—C9—C11	120.9 (4)	C11—C12—C13	120.0 (4)
C8—C9—C11	118.8 (4)	C11—C12—H12A	120.0
C7—C8—C14	124.8 (3)	C13—C12—H12A	120.0
C7—C8—C9	119.1 (3)	C17—C16—C15	101.8 (3)
C14—C8—C9	116.1 (3)	C17—C16—H16A	111.4
N3—C15—C7	114.1 (3)	C15—C16—H16A	111.4
N3—C15—C16	102.2 (3)	C17—C16—H16B	111.4
C7—C15—C16	115.9 (3)	C15—C16—H16B	111.4
N3—C15—H15A	108.1	H16A—C16—H16B	109.3
C7—C15—H15A	108.1	C14—C13—C12	120.7 (4)
C16—C15—H15A	108.1	C14—C13—H13A	119.6
N2—N3—C24	118.5 (3)	C12—C13—H13A	119.6
N2—N3—C15	112.5 (3)	C4—C3—C2	119.6 (4)
C24—N3—C15	125.6 (3)	C4—C3—H3A	120.2
C28—C29—C24	120.1 (3)	C2—C3—H3A	120.2
C28—C29—H29A	120.0	C26—C25—C24	120.2 (4)
C24—C29—H29A	120.0	C26—C25—H25A	119.9
C2—C1—C6	121.7 (3)	C24—C25—H25A	119.9
C2—C1—H1A	119.1	C20—C19—C18	120.5 (3)
C6—C1—H1A	119.1	C20—C19—H19A	119.7
C26—C27—C28	119.0 (4)	C18—C19—H19A	119.7
C26—C27—H27A	120.5	C3—C4—C5	121.2 (4)
C28—C27—H27A	120.5	C3—C4—H4A	119.4
C12—C11—C9	121.5 (4)	C5—C4—H4A	119.4
C12—C11—H11A	119.2	C21—C22—C23	118.6 (4)
C9—C11—H11A	119.2	C21—C22—H22A	120.7
C13—C14—C8	122.8 (4)	C23—C22—H22A	120.7
C13—C14—H14A	118.6	C27—C26—C25	121.1 (4)
C8—C14—H14A	118.6	C27—C26—H26A	119.5
C25—C24—C29	118.8 (3)	C25—C26—H26A	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N2	0.93	2.59	3.422 (5)	150

Experimental details

Crystal data
Chemical formula	C₂₉H₂₁N₃O₂
M_r	443.49
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	23.023 (5), 10.195 (2), 9.2005 (18)
V (Å³)	2159.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17812, 2023, 1675
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.095, 1.08
No. of reflections	2023
No. of parameters	308
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N2	0.93	2.59	3.422 (5)	149.9

References

Christoph, J. F., Liuchun, Y. & Donald, G. V. (2003). J. Am. Chem. Soc. 125, 3799–3812. Web of Science PubMed Google Scholar
Krishna, R., Velmurugan, D., Murugesan, R., Shanmuga Sundaram, M. & Raghunathan, R. (1999). Acta Cryst. C55, 1676–1677. CSD CrossRef CAS IUCr Journals Google Scholar
Parmar, S. S., Pandey, B. R., Dwivedi, C. & Harbinson, R. D. (1974). J. Pharm. Sci. 63, 1152–1155. CrossRef CAS PubMed Web of Science Google Scholar
Prasad, Y. R., Rao, A. L., Prasoona, K., Murali, K. & Kumar, P. R. (2005). Bioorg. Med. Chem. Lett. 15, 5030–5034. PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Shaharyar, M., Siddiqui, A. A. & Ali, M. A. (2006). Bioorg. Med. Chem. Lett. 16, 4571–4574. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 11| November 2010| Page o2786

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