3,5-Bis(4-methyl-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

In the title compound, C(23)H(22)N(2), the dihedral angle between the methyl-benzene groups is 77.62 (6)°, and the dihedral angle between the envelope-shaped pyrazole ring [in which one C atom displaced by 0.109 (1) Å from the mean plane of the other four atoms] and the phenyl ring is 17.57 (7)°. The dihedral angles between the phenyl ring and the two methyl-benzene rings are 13.24 (6) and 81.02 (7)°. In the crystal, weak C-H⋯π inter-actions link the mol-ecules.

Related literature

For related structures and background references, see: Jasinski et al. (2010) ▶; Samshuddin et al. (2010 ▶).

Experimental

Crystal data

C23H22N2

M = 326.43

Monoclinic,

a = 5.8113 (3) Å

b = 10.6959 (5) Å

c = 28.4455 (13) Å

β = 94.983 (4)°

V = 1761.41 (15) Å3

Z = 4

Cu Kα radiation

μ = 0.55 mm−1

T = 123 K

0.53 × 0.11 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.736, T max = 1.000

12872 measured reflections

3615 independent reflections

3096 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.03

3615 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011494/hb5825sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011494/hb5825Isup2.hkl

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

C23H22N2	F(000) = 696
Mr = 326.43	Dx = 1.231 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 6406 reflections
a = 5.8113 (3) Å	θ = 4.4–75.5°
b = 10.6959 (5) Å	µ = 0.55 mm−1
c = 28.4455 (13) Å	T = 123 K
β = 94.983 (4)°	Needle, yellow
V = 1761.41 (15) Å3	0.53 × 0.11 × 0.07 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini CCD diffractometer	3615 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3096 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 4.4°
ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO;Oxford Diffraction, 2007)	k = −13→13
Tmin = 0.736, Tmax = 1.000	l = −34→35
12872 measured 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.4363P] where P = (Fo2 + 2Fc2)/3
3615 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N1	0.03560 (19)	0.23302 (10)	0.66268 (4)	0.0274 (3)
N2	0.24215 (19)	0.20597 (10)	0.68799 (4)	0.0255 (3)
C1	0.2985 (2)	0.29796 (11)	0.71599 (4)	0.0246 (3)
C2	0.1238 (2)	0.40318 (12)	0.71220 (4)	0.0269 (4)
C3	−0.0306 (2)	0.36569 (12)	0.66740 (5)	0.0257 (3)
C4	−0.0433 (2)	0.15597 (12)	0.62528 (4)	0.0253 (3)
C5	−0.2649 (2)	0.17337 (14)	0.60319 (5)	0.0331 (4)
C6	−0.3486 (3)	0.09418 (15)	0.56701 (5)	0.0355 (4)
C7	−0.2145 (3)	−0.00281 (14)	0.55219 (5)	0.0380 (5)
C8	0.0064 (3)	−0.01954 (15)	0.57400 (5)	0.0374 (4)
C9	0.0931 (2)	0.05842 (13)	0.61021 (5)	0.0297 (4)
C10	0.5036 (2)	0.29188 (12)	0.74964 (4)	0.0243 (3)
C11	0.5501 (2)	0.38492 (12)	0.78377 (5)	0.0276 (4)
C12	0.7391 (2)	0.37447 (12)	0.81698 (5)	0.0282 (4)
C13	0.8878 (2)	0.27223 (12)	0.81727 (5)	0.0272 (4)
C14	0.8428 (2)	0.18087 (12)	0.78254 (5)	0.0289 (4)
C15	0.6556 (2)	0.18988 (12)	0.74930 (5)	0.0266 (4)
C16	1.0901 (3)	0.26048 (14)	0.85368 (5)	0.0342 (4)
C17	0.0167 (2)	0.44225 (12)	0.62430 (4)	0.0247 (3)
C18	0.2099 (2)	0.41944 (13)	0.59980 (5)	0.0302 (4)
C19	0.2591 (2)	0.49430 (14)	0.56221 (5)	0.0317 (4)
C20	0.1173 (3)	0.59488 (12)	0.54784 (5)	0.0294 (4)
C21	−0.0768 (3)	0.61616 (12)	0.57187 (5)	0.0314 (4)
C22	−0.1273 (2)	0.54094 (12)	0.60961 (5)	0.0285 (4)
C23	0.1766 (3)	0.67715 (14)	0.50757 (5)	0.0388 (4)
H2A	0.19920	0.48500	0.70820	0.0320*
H2B	0.03430	0.40650	0.74020	0.0320*
H3A	−0.19730	0.37210	0.67330	0.0310*
H5A	−0.35870	0.23960	0.61290	0.0400*
H6A	−0.49980	0.10670	0.55220	0.0430*
H7A	−0.27280	−0.05700	0.52750	0.0460*
H8A	0.09980	−0.08560	0.56390	0.0450*
H9A	0.24470	0.04570	0.62480	0.0360*
H11A	0.45170	0.45570	0.78420	0.0330*
H12A	0.76760	0.43840	0.83990	0.0340*
H14A	0.94320	0.11100	0.78180	0.0350*
H15A	0.62960	0.12660	0.72600	0.0320*
H16A	1.04610	0.29080	0.88410	0.0510*
H16B	1.21930	0.31040	0.84400	0.0510*
H16C	1.13670	0.17260	0.85660	0.0510*
H18A	0.30930	0.35160	0.60900	0.0360*
H19A	0.39150	0.47680	0.54600	0.0380*
H21A	−0.17720	0.68340	0.56240	0.0380*
H22A	−0.26150	0.55730	0.62540	0.0340*
H23A	0.05160	0.73740	0.50010	0.0580*
H23B	0.19620	0.62540	0.47980	0.0580*
H23C	0.32050	0.72220	0.51660	0.0580*

	U11	U22	U33	U12	U13	U23
N1	0.0281 (6)	0.0256 (5)	0.0276 (6)	0.0039 (4)	−0.0019 (4)	0.0005 (4)
N2	0.0263 (5)	0.0264 (5)	0.0234 (5)	0.0016 (4)	−0.0005 (4)	0.0017 (4)
C1	0.0293 (6)	0.0236 (6)	0.0213 (6)	0.0016 (5)	0.0049 (5)	0.0019 (4)
C2	0.0328 (7)	0.0254 (6)	0.0229 (6)	0.0042 (5)	0.0047 (5)	0.0007 (5)
C3	0.0249 (6)	0.0254 (6)	0.0270 (6)	0.0035 (5)	0.0043 (5)	0.0009 (5)
C4	0.0276 (6)	0.0256 (6)	0.0228 (6)	−0.0036 (5)	0.0028 (5)	0.0033 (5)
C5	0.0301 (7)	0.0363 (7)	0.0325 (7)	0.0025 (5)	0.0007 (5)	0.0029 (6)
C6	0.0296 (7)	0.0454 (8)	0.0301 (7)	−0.0057 (6)	−0.0047 (6)	0.0062 (6)
C7	0.0461 (9)	0.0390 (8)	0.0277 (7)	−0.0096 (6)	−0.0038 (6)	−0.0025 (6)
C8	0.0430 (8)	0.0361 (7)	0.0326 (7)	0.0022 (6)	0.0003 (6)	−0.0061 (6)
C9	0.0286 (7)	0.0318 (7)	0.0282 (7)	0.0003 (5)	−0.0002 (5)	−0.0008 (5)
C10	0.0283 (6)	0.0243 (6)	0.0206 (6)	−0.0009 (5)	0.0036 (5)	0.0032 (5)
C11	0.0341 (7)	0.0242 (6)	0.0247 (6)	0.0025 (5)	0.0040 (5)	0.0012 (5)
C12	0.0366 (7)	0.0266 (6)	0.0213 (6)	−0.0036 (5)	0.0028 (5)	−0.0014 (5)
C13	0.0292 (7)	0.0286 (6)	0.0237 (6)	−0.0043 (5)	0.0019 (5)	0.0050 (5)
C14	0.0299 (7)	0.0250 (6)	0.0316 (7)	0.0025 (5)	0.0013 (5)	0.0023 (5)
C15	0.0315 (7)	0.0229 (6)	0.0252 (6)	−0.0009 (5)	0.0020 (5)	−0.0011 (5)
C16	0.0350 (7)	0.0342 (7)	0.0320 (7)	−0.0050 (6)	−0.0044 (6)	0.0026 (6)
C17	0.0247 (6)	0.0267 (6)	0.0224 (6)	0.0011 (5)	0.0000 (5)	−0.0009 (5)
C18	0.0271 (7)	0.0344 (7)	0.0292 (7)	0.0067 (5)	0.0027 (5)	0.0020 (5)
C19	0.0290 (7)	0.0390 (7)	0.0277 (7)	−0.0002 (5)	0.0060 (5)	−0.0015 (5)
C20	0.0377 (7)	0.0288 (6)	0.0210 (6)	−0.0067 (5)	−0.0018 (5)	−0.0020 (5)
C21	0.0393 (8)	0.0260 (6)	0.0282 (7)	0.0052 (5)	−0.0017 (6)	0.0008 (5)
C22	0.0292 (7)	0.0291 (6)	0.0272 (6)	0.0051 (5)	0.0031 (5)	−0.0018 (5)
C23	0.0546 (9)	0.0354 (7)	0.0264 (7)	−0.0087 (6)	0.0034 (6)	0.0017 (6)

N1—N2	1.3758 (16)	C20—C21	1.388 (2)
N1—C3	1.4794 (17)	C20—C23	1.508 (2)
N1—C4	1.3916 (16)	C21—C22	1.393 (2)
N2—C1	1.2901 (16)	C2—H2A	0.9900
C1—C2	1.5132 (17)	C2—H2B	0.9900
C1—C10	1.4639 (16)	C3—H3A	1.0000
C2—C3	1.5464 (18)	C5—H5A	0.9500
C3—C17	1.5191 (18)	C6—H6A	0.9500
C4—C5	1.3955 (17)	C7—H7A	0.9500
C4—C9	1.3999 (18)	C8—H8A	0.9500
C5—C6	1.388 (2)	C9—H9A	0.9500
C6—C7	1.385 (2)	C11—H11A	0.9500
C7—C8	1.388 (2)	C12—H12A	0.9500
C8—C9	1.386 (2)	C14—H14A	0.9500
C10—C11	1.4001 (18)	C15—H15A	0.9500
C10—C15	1.4043 (18)	C16—H16A	0.9800
C11—C12	1.3896 (18)	C16—H16B	0.9800
C12—C13	1.3934 (18)	C16—H16C	0.9800
C13—C14	1.3980 (19)	C18—H18A	0.9500
C13—C16	1.503 (2)	C19—H19A	0.9500
C14—C15	1.3813 (18)	C21—H21A	0.9500
C17—C18	1.3935 (17)	C22—H22A	0.9500
C17—C22	1.3887 (18)	C23—H23A	0.9800
C18—C19	1.385 (2)	C23—H23B	0.9800
C19—C20	1.395 (2)	C23—H23C	0.9800
N2—N1—C3	112.10 (10)	H2A—C2—H2B	109.00
N2—N1—C4	119.35 (10)	N1—C3—H3A	110.00
C3—N1—C4	124.50 (11)	C2—C3—H3A	110.00
N1—N2—C1	109.02 (10)	C17—C3—H3A	110.00
N2—C1—C2	112.98 (10)	C4—C5—H5A	120.00
N2—C1—C10	121.23 (11)	C6—C5—H5A	120.00
C2—C1—C10	125.64 (10)	C5—C6—H6A	120.00
C1—C2—C3	101.74 (10)	C7—C6—H6A	120.00
N1—C3—C2	100.76 (10)	C6—C7—H7A	121.00
N1—C3—C17	112.15 (11)	C8—C7—H7A	121.00
C2—C3—C17	113.12 (10)	C7—C8—H8A	119.00
N1—C4—C5	119.68 (12)	C9—C8—H8A	119.00
N1—C4—C9	121.18 (11)	C4—C9—H9A	120.00
C5—C4—C9	119.11 (12)	C8—C9—H9A	120.00
C4—C5—C6	120.19 (13)	C10—C11—H11A	120.00
C5—C6—C7	120.84 (15)	C12—C11—H11A	120.00
C6—C7—C8	118.92 (14)	C11—C12—H12A	119.00
C7—C8—C9	121.14 (14)	C13—C12—H12A	119.00
C4—C9—C8	119.81 (12)	C13—C14—H14A	119.00
C1—C10—C11	121.26 (11)	C15—C14—H14A	119.00
C1—C10—C15	120.46 (11)	C10—C15—H15A	120.00
C11—C10—C15	118.25 (11)	C14—C15—H15A	120.00
C10—C11—C12	120.52 (11)	C13—C16—H16A	109.00
C11—C12—C13	121.35 (12)	C13—C16—H16B	109.00
C12—C13—C14	117.81 (12)	C13—C16—H16C	109.00
C12—C13—C16	121.15 (12)	H16A—C16—H16B	109.00
C14—C13—C16	121.04 (11)	H16A—C16—H16C	110.00
C13—C14—C15	121.52 (12)	H16B—C16—H16C	109.00
C10—C15—C14	120.53 (12)	C17—C18—H18A	120.00
C3—C17—C18	121.29 (11)	C19—C18—H18A	120.00
C3—C17—C22	120.40 (11)	C18—C19—H19A	119.00
C18—C17—C22	118.25 (12)	C20—C19—H19A	120.00
C17—C18—C19	120.94 (12)	C20—C21—H21A	119.00
C18—C19—C20	121.05 (12)	C22—C21—H21A	119.00
C19—C20—C21	117.84 (13)	C17—C22—H22A	120.00
C19—C20—C23	120.31 (14)	C21—C22—H22A	120.00
C21—C20—C23	121.85 (13)	C20—C23—H23A	110.00
C20—C21—C22	121.30 (13)	C20—C23—H23B	109.00
C17—C22—C21	120.61 (12)	C20—C23—H23C	110.00
C1—C2—H2A	111.00	H23A—C23—H23B	109.00
C1—C2—H2B	111.00	H23A—C23—H23C	109.00
C3—C2—H2A	111.00	H23B—C23—H23C	109.00
C3—C2—H2B	111.00
C3—N1—N2—C1	12.24 (14)	N1—C4—C9—C8	177.64 (13)
C4—N1—N2—C1	170.61 (11)	C5—C4—C9—C8	−0.4 (2)
N2—N1—C3—C2	−18.27 (13)	C4—C5—C6—C7	−0.1 (2)
N2—N1—C3—C17	102.32 (12)	C5—C6—C7—C8	−0.3 (2)
C4—N1—C3—C2	−175.32 (11)	C6—C7—C8—C9	0.3 (2)
C4—N1—C3—C17	−54.74 (15)	C7—C8—C9—C4	0.0 (2)
N2—N1—C4—C5	172.10 (12)	C1—C10—C11—C12	176.68 (12)
N2—N1—C4—C9	−5.93 (18)	C15—C10—C11—C12	−1.44 (19)
C3—N1—C4—C5	−32.39 (18)	C1—C10—C15—C14	−176.72 (12)
C3—N1—C4—C9	149.59 (12)	C11—C10—C15—C14	1.41 (19)
N1—N2—C1—C2	0.12 (14)	C10—C11—C12—C13	0.3 (2)
N1—N2—C1—C10	175.95 (10)	C11—C12—C13—C14	0.90 (19)
N2—C1—C2—C3	−11.25 (13)	C11—C12—C13—C16	−179.14 (13)
C10—C1—C2—C3	173.14 (11)	C12—C13—C14—C15	−0.93 (19)
N2—C1—C10—C11	−172.36 (12)	C16—C13—C14—C15	179.11 (13)
N2—C1—C10—C15	5.72 (18)	C13—C14—C15—C10	−0.2 (2)
C2—C1—C10—C11	2.91 (18)	C3—C17—C18—C19	−176.21 (12)
C2—C1—C10—C15	−179.01 (11)	C22—C17—C18—C19	0.94 (19)
C1—C2—C3—N1	16.33 (11)	C3—C17—C22—C21	176.07 (12)
C1—C2—C3—C17	−103.56 (11)	C18—C17—C22—C21	−1.10 (19)
N1—C3—C17—C18	−36.48 (16)	C17—C18—C19—C20	0.2 (2)
N1—C3—C17—C22	146.44 (12)	C18—C19—C20—C21	−1.1 (2)
C2—C3—C17—C18	76.66 (15)	C18—C19—C20—C23	178.58 (13)
C2—C3—C17—C22	−100.43 (13)	C19—C20—C21—C22	1.0 (2)
N1—C4—C5—C6	−177.62 (13)	C23—C20—C21—C22	−178.74 (13)
C9—C4—C5—C6	0.5 (2)	C20—C21—C22—C17	0.2 (2)

Cg2, Cg3 and Cg4 are the centroids of the C4–C9, C10–C15 and C17–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cg3i	0.99	2.74	3.5766 (13)	142
C12—H12A···Cg2ii	0.95	2.69	3.5485 (15)	150
C16—H16C···Cg4iii	0.98	2.81	3.6144 (17)	140
C23—H23B···Cg4iv	0.98	2.77	3.5742 (16)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C4–C9, C10–C15 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯Cg3i	0.99	2.74	3.5766 (13)	142
C12—H12A⋯Cg2ii	0.95	2.69	3.5485 (15)	150
C16—H16C⋯Cg4iii	0.98	2.81	3.6144 (17)	140
C23—H23B⋯Cg4iv	0.98	2.77	3.5742 (16)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .