5-(Anthracen-9-yl)-3-(4-nitro-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

In the title compound, C(29)H(21)N(3)O(2), 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 intra-molecular 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 = 443.49

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.095

S = 1.08

2023 reflections

308 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

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 .

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038912/xu5037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038912/xu5037Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H21N3O2	F(000) = 928
Mr = 443.49	Dx = 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

Rigaku Mercury2 diffractometer	1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
graphite	θmax = 25.0°, θmin = 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 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(Fo2) + (0.0418P)2 + 0.3731P] where P = (Fo2 + 2Fc2)/3
2023 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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