3-Methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole.

In the title compound, C16H16N2, the dihydro-pyrazole ring adopts a shallow envelope conformation, with the C atom bearing the phenyl group displaced by 0.298 (2) Å from the other atoms (r.m.s. deviation = 0.015 Å). The dihedral angles between the four near coplanar atoms of the central ring and the N- and C-bonded phenyl groups are 13.49 (13) and 82.22 (16)°, respectively.

Related literature

For background to pyrazoles, see: Govindaraju et al. (2012 ▶); Jayaroopa et al. (2013 ▶); Kalirajan et al. (2013 ▶); Mariappan et al. (2010 ▶); Shyama et al. (2009 ▶). For related structures, see: Baktır et al. (2011 ▶); Fun et al. (2011 ▶).

Experimental

Crystal data

C16H16N2

M = 236.31

Monoclinic,

a = 18.1224 (17) Å

b = 7.8055 (6) Å

c = 12.5057 (13) Å

β = 132.207 (9)°

V = 1310.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 301 K

0.32 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

11856 measured reflections

2973 independent reflections

2362 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.131

S = 0.91

2973 reflections

165 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.10 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: Mercury.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007575/hb7053sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007575/hb7053Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007575/hb7053Isup3.cml

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

C16H16N2	F(000) = 504
Mr = 236.31	Dx = 1.198 Mg m−3
Monoclinic, Cc	Melting point = 363–365 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 18.1224 (17) Å	Cell parameters from 2973 reflections
b = 7.8055 (6) Å	θ = 3.0–27.6°
c = 12.5057 (13) Å	µ = 0.07 mm−1
β = 132.207 (9)°	T = 301 K
V = 1310.3 (3) Å3	Block, pale yellow
Z = 4	0.32 × 0.20 × 0.18 mm

Oxford Diffraction Xcalibur Eos diffractometer	2362 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.6°, θmin = 3.0°
Detector resolution: 16.0839 pixels mm-1	h = −23→23
ω scans	k = −10→10
11856 measured reflections	l = −16→16
2973 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2973 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.10 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	0.57189 (12)	0.5350 (3)	0.53221 (17)	0.0583 (6)
N2	0.63012 (12)	0.5538 (2)	0.49747 (18)	0.0528 (5)
C1	0.43700 (15)	0.4218 (3)	0.2954 (2)	0.0539 (6)
C2	0.34060 (17)	0.3632 (3)	0.1948 (2)	0.0683 (7)
C3	0.27852 (16)	0.3631 (3)	0.2214 (3)	0.0694 (7)
C4	0.31410 (16)	0.4245 (3)	0.3516 (3)	0.0617 (7)
C5	0.41076 (14)	0.4857 (2)	0.4546 (2)	0.0529 (6)
C6	0.47391 (13)	0.4829 (2)	0.42818 (19)	0.0439 (5)
C7	0.62148 (15)	0.5986 (2)	0.6767 (2)	0.0487 (5)
C8	0.58591 (12)	0.7740 (2)	0.67789 (18)	0.0425 (5)
C9	0.53469 (16)	0.8844 (3)	0.5615 (2)	0.0558 (6)
C10	0.50989 (18)	1.0475 (3)	0.5715 (3)	0.0710 (8)
C11	0.53636 (18)	1.1018 (3)	0.6979 (3)	0.0725 (9)
C12	0.58650 (17)	0.9929 (3)	0.8138 (3)	0.0644 (8)
C13	0.61057 (14)	0.8294 (3)	0.80360 (19)	0.0502 (6)
C14	0.73007 (16)	0.6028 (3)	0.7433 (2)	0.0618 (6)
C15	0.71843 (15)	0.5947 (2)	0.6134 (2)	0.0563 (6)
C16	0.8000 (2)	0.6260 (4)	0.6152 (4)	0.0878 (11)
H1	0.47760	0.42050	0.27480	0.0650*
H2	0.31700	0.32270	0.10660	0.0820*
H3	0.21360	0.32240	0.15260	0.0830*
H4	0.27280	0.42500	0.37110	0.0740*
H5	0.43330	0.52860	0.54160	0.0640*
H7	0.61430	0.51580	0.72810	0.0580*
H9	0.51670	0.84890	0.47570	0.0670*
H10	0.47520	1.12070	0.49240	0.0850*
H11	0.52030	1.21200	0.70480	0.0870*
H12	0.60430	1.02910	0.89940	0.0770*
H13	0.64380	0.75570	0.88220	0.0600*
H14A	0.76320	0.70760	0.79730	0.0740*
H14B	0.76730	0.50530	0.80630	0.0740*
H16A	0.77370	0.62300	0.51830	0.1320*
H16B	0.85000	0.53900	0.67170	0.1320*
H16C	0.82900	0.73640	0.65690	0.1320*

	U11	U22	U33	U12	U13	U23
N1	0.0465 (9)	0.0796 (11)	0.0514 (9)	−0.0147 (8)	0.0339 (8)	−0.0253 (8)
N2	0.0518 (9)	0.0527 (8)	0.0596 (9)	−0.0064 (7)	0.0397 (8)	−0.0083 (7)
C1	0.0477 (11)	0.0618 (11)	0.0449 (9)	0.0008 (8)	0.0281 (9)	−0.0037 (9)
C2	0.0521 (12)	0.0800 (14)	0.0474 (11)	−0.0079 (10)	0.0231 (10)	−0.0109 (10)
C3	0.0457 (11)	0.0665 (13)	0.0668 (14)	−0.0070 (9)	0.0259 (11)	−0.0034 (10)
C4	0.0532 (11)	0.0519 (10)	0.0866 (15)	0.0036 (9)	0.0497 (11)	0.0054 (10)
C5	0.0551 (11)	0.0494 (10)	0.0590 (11)	−0.0021 (8)	0.0403 (10)	−0.0077 (8)
C6	0.0413 (9)	0.0383 (7)	0.0461 (9)	0.0022 (7)	0.0269 (8)	−0.0015 (7)
C7	0.0479 (9)	0.0476 (9)	0.0425 (9)	−0.0016 (7)	0.0271 (8)	−0.0040 (7)
C8	0.0391 (8)	0.0454 (8)	0.0420 (8)	−0.0051 (7)	0.0269 (7)	−0.0026 (7)
C9	0.0574 (11)	0.0567 (11)	0.0491 (10)	0.0004 (8)	0.0341 (9)	0.0071 (8)
C10	0.0650 (14)	0.0544 (11)	0.0800 (16)	0.0095 (10)	0.0431 (13)	0.0199 (11)
C11	0.0664 (14)	0.0499 (12)	0.110 (2)	0.0015 (9)	0.0628 (15)	−0.0042 (12)
C12	0.0686 (14)	0.0652 (13)	0.0789 (15)	−0.0099 (10)	0.0575 (13)	−0.0201 (11)
C13	0.0490 (10)	0.0567 (10)	0.0457 (10)	−0.0039 (8)	0.0322 (9)	−0.0032 (8)
C14	0.0480 (11)	0.0595 (11)	0.0545 (11)	0.0037 (9)	0.0249 (9)	−0.0119 (9)
C15	0.0463 (11)	0.0505 (10)	0.0644 (12)	−0.0024 (8)	0.0340 (10)	−0.0060 (9)
C16	0.0631 (15)	0.105 (2)	0.100 (2)	−0.0193 (14)	0.0567 (15)	−0.0180 (16)

N1—N2	1.393 (4)	C14—C15	1.492 (3)
N1—C6	1.381 (3)	C15—C16	1.484 (6)
N1—C7	1.462 (3)	C1—H1	0.9300
N2—C15	1.284 (3)	C2—H2	0.9300
C1—C2	1.375 (4)	C3—H3	0.9300
C1—C6	1.393 (3)	C4—H4	0.9300
C2—C3	1.371 (5)	C5—H5	0.9300
C3—C4	1.373 (4)	C7—H7	0.9800
C4—C5	1.387 (4)	C9—H9	0.9300
C5—C6	1.388 (4)	C10—H10	0.9300
C7—C8	1.518 (3)	C11—H11	0.9300
C7—C14	1.538 (4)	C12—H12	0.9300
C8—C9	1.381 (3)	C13—H13	0.9300
C8—C13	1.384 (3)	C14—H14A	0.9700
C9—C10	1.383 (4)	C14—H14B	0.9700
C10—C11	1.375 (4)	C16—H16A	0.9600
C11—C12	1.371 (4)	C16—H16B	0.9600
C12—C13	1.382 (4)	C16—H16C	0.9600
N2—N1—C6	120.09 (17)	C2—C3—H3	121.00
N2—N1—C7	112.6 (2)	C4—C3—H3	121.00
C6—N1—C7	126.7 (2)	C3—C4—H4	120.00
N1—N2—C15	107.8 (2)	C5—C4—H4	119.00
C2—C1—C6	120.1 (3)	C4—C5—H5	120.00
C1—C2—C3	121.6 (2)	C6—C5—H5	120.00
C2—C3—C4	118.6 (3)	N1—C7—H7	110.00
C3—C4—C5	121.0 (3)	C8—C7—H7	110.00
C4—C5—C6	120.2 (2)	C14—C7—H7	110.00
N1—C6—C1	120.5 (3)	C8—C9—H9	120.00
N1—C6—C5	121.00 (18)	C10—C9—H9	120.00
C1—C6—C5	118.5 (2)	C9—C10—H10	120.00
N1—C7—C8	113.95 (16)	C11—C10—H10	120.00
N1—C7—C14	100.2 (2)	C10—C11—H11	120.00
C8—C7—C14	111.89 (18)	C12—C11—H11	120.00
C7—C8—C9	122.80 (19)	C11—C12—H12	120.00
C7—C8—C13	118.56 (16)	C13—C12—H12	120.00
C9—C8—C13	118.55 (19)	C8—C13—H13	120.00
C8—C9—C10	120.5 (2)	C12—C13—H13	120.00
C9—C10—C11	120.3 (2)	C7—C14—H14A	111.00
C10—C11—C12	119.7 (2)	C7—C14—H14B	111.00
C11—C12—C13	120.1 (3)	C15—C14—H14A	111.00
C8—C13—C12	120.8 (2)	C15—C14—H14B	111.00
C7—C14—C15	102.47 (18)	H14A—C14—H14B	109.00
N2—C15—C14	113.4 (3)	C15—C16—H16A	109.00
N2—C15—C16	122.1 (2)	C15—C16—H16B	109.00
C14—C15—C16	124.5 (2)	C15—C16—H16C	109.00
C2—C1—H1	120.00	H16A—C16—H16B	110.00
C6—C1—H1	120.00	H16A—C16—H16C	110.00
C1—C2—H2	119.00	H16B—C16—H16C	109.00
C3—C2—H2	119.00
C6—N1—N2—C15	−176.91 (18)	C4—C5—C6—N1	−176.63 (19)
C7—N1—N2—C15	11.2 (2)	C4—C5—C6—C1	1.7 (3)
N2—N1—C6—C1	10.6 (3)	N1—C7—C8—C9	−18.0 (4)
N2—N1—C6—C5	−171.14 (17)	N1—C7—C8—C13	165.6 (2)
C7—N1—C6—C1	−178.8 (2)	C14—C7—C8—C9	94.8 (3)
C7—N1—C6—C5	−0.5 (3)	C14—C7—C8—C13	−81.6 (3)
N2—N1—C7—C8	101.5 (3)	N1—C7—C14—C15	17.20 (19)
N2—N1—C7—C14	−18.2 (2)	C8—C7—C14—C15	−103.93 (19)
C6—N1—C7—C8	−69.7 (3)	C7—C8—C9—C10	−175.5 (3)
C6—N1—C7—C14	170.6 (2)	C13—C8—C9—C10	0.8 (4)
N1—N2—C15—C14	1.8 (2)	C7—C8—C13—C12	175.1 (3)
N1—N2—C15—C16	−179.6 (2)	C9—C8—C13—C12	−1.4 (4)
C6—C1—C2—C3	0.1 (3)	C8—C9—C10—C11	0.3 (5)
C2—C1—C6—N1	177.2 (2)	C9—C10—C11—C12	−0.8 (6)
C2—C1—C6—C5	−1.1 (3)	C10—C11—C12—C13	0.2 (6)
C1—C2—C3—C4	0.5 (4)	C11—C12—C13—C8	0.9 (5)
C2—C3—C4—C5	0.1 (4)	C7—C14—C15—N2	−12.9 (2)
C3—C4—C5—C6	−1.1 (3)	C7—C14—C15—C16	168.6 (2)