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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810038912/xu5037sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810038912/xu5037Isup2.hkl Contains datablock I

CCDC reference: 799578

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.044
wR factor = 0.095
Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.57
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          5
PLAT410_ALERT_2_C Short Intra H...H Contact  H14A   ..  H15A    ..       1.93 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2023
           Count of symmetry unique reflns         2028
           Completeness (_total/calc)             99.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT792_ALERT_1_G The Model has Chirality at C15     (Verify) ....          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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

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).