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The mol­ecules of the title compound, C22H18N2, are connected by N—H...N hydrogen bonds, forming cyclic dimers. These dimers are linked by C—H...π hydrogen bonds involving the phenyl rings as acceptors.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008434/hg2185sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008434/hg2185Isup2.hkl
Contains datablock I

CCDC reference: 640362

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • R factor = 0.051
  • wR factor = 0.128
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

4-Benzyl-3,5-diphenyl-1H-pyrazole top
Crystal data top
C22H18N2F(000) = 656
Mr = 310.38Dx = 1.212 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 586 reflections
a = 9.6145 (9) Åθ = 1.1–26.0°
b = 18.755 (4) ŵ = 0.07 mm1
c = 10.887 (5) ÅT = 291 K
β = 119.96 (2)°Block, colourless
V = 1700.8 (9) Å30.25 × 0.20 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
3274 independent reflections
Radiation source: Rotating Anode2271 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Oscillation scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1111
Tmin = 0.98, Tmax = 0.99k = 2321
6059 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.06P)2 + 0.2139P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3274 reflectionsΔρmax = 0.14 e Å3
218 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (3)
Special details top

Experimental. 1H NMR (400 MHz, [D6]DMSO): δ 4.20 (2H, s, CH2), 7.20 (2H, d, J = 7.6 Hz, Ph—H), 7.27 (1H, t, J = 7.3 Hz, Ph—H),7.35–7.59 (10H, m, Ph—H), 7.64 (2H, d, J = 7.5 Hz, Ph—H), 13.41 (1H, s, N—H).

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
xyzUiso*/Ueq
N10.35807 (17)0.94747 (8)0.96026 (15)0.0507 (4)
H10.40650.97991.03650.061*
N20.42902 (16)0.93936 (8)0.88124 (15)0.0494 (4)
C10.34202 (19)0.89014 (9)0.78384 (17)0.0433 (4)
C20.21262 (19)0.86743 (9)0.80114 (17)0.0435 (4)
C30.2282 (2)0.90572 (9)0.91570 (18)0.0461 (4)
C40.1383 (2)0.90519 (9)0.99230 (19)0.0487 (4)
C50.0280 (2)0.90852 (10)0.9211 (2)0.0577 (5)
H50.08490.90990.82260.069*
C60.1092 (3)0.90971 (11)0.9950 (3)0.0721 (6)
H60.22080.91170.94630.087*
C70.0265 (3)0.90804 (12)1.1401 (3)0.0825 (7)
H70.08220.90941.18950.099*
C80.1383 (3)0.90442 (12)1.2133 (3)0.0774 (7)
H80.19420.90301.31180.093*
C90.2202 (3)0.90294 (11)1.1394 (2)0.0615 (5)
H90.33170.90041.18870.074*
C100.0838 (2)0.81386 (9)0.71728 (18)0.0492 (4)
H10A0.02660.80370.76770.059*
H10B0.13440.76990.71290.059*
C110.03673 (19)0.83620 (10)0.56793 (18)0.0472 (4)
C120.1098 (3)0.78487 (13)0.4643 (2)0.0735 (6)
H120.08010.73730.48620.088*
C130.2259 (3)0.8030 (2)0.3294 (3)0.0993 (9)
H130.27300.76770.26060.119*
C140.2726 (3)0.8716 (2)0.2953 (3)0.0997 (10)
H140.35370.88310.20430.120*
C150.2000 (3)0.92397 (15)0.3952 (3)0.0830 (8)
H150.22990.97130.37140.100*
C160.0818 (2)0.90635 (11)0.5320 (2)0.0611 (5)
H160.03290.94200.59970.073*
C170.39434 (19)0.86853 (10)0.68292 (17)0.0465 (4)
C180.3635 (2)0.80186 (11)0.6212 (2)0.0618 (5)
H180.30250.76950.63910.074*
C190.4224 (3)0.78254 (14)0.5328 (2)0.0743 (6)
H190.40000.73750.49160.089*
C200.5129 (3)0.82919 (15)0.5057 (2)0.0764 (7)
H200.55360.81580.44750.092*
C210.5429 (3)0.89542 (14)0.5646 (2)0.0759 (7)
H210.60400.92740.54600.091*
C220.4838 (2)0.91557 (11)0.6514 (2)0.0616 (5)
H220.50400.96130.68940.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0480 (8)0.0555 (9)0.0486 (8)0.0109 (7)0.0241 (7)0.0118 (7)
N20.0445 (8)0.0556 (9)0.0469 (8)0.0093 (7)0.0220 (7)0.0094 (7)
C10.0420 (9)0.0418 (9)0.0408 (9)0.0020 (7)0.0166 (8)0.0016 (7)
C20.0419 (9)0.0395 (9)0.0424 (9)0.0021 (7)0.0161 (8)0.0013 (7)
C30.0409 (9)0.0463 (10)0.0463 (9)0.0041 (8)0.0182 (8)0.0010 (7)
C40.0522 (10)0.0427 (10)0.0545 (11)0.0009 (8)0.0293 (9)0.0017 (8)
C50.0534 (11)0.0513 (11)0.0702 (13)0.0025 (9)0.0322 (10)0.0012 (9)
C60.0668 (13)0.0641 (14)0.1035 (19)0.0010 (10)0.0560 (14)0.0016 (12)
C70.1004 (19)0.0743 (16)0.112 (2)0.0056 (13)0.0829 (18)0.0087 (13)
C80.1002 (18)0.0801 (16)0.0700 (14)0.0119 (13)0.0561 (14)0.0088 (11)
C90.0643 (12)0.0644 (13)0.0589 (12)0.0060 (10)0.0329 (11)0.0055 (9)
C100.0472 (10)0.0416 (10)0.0550 (11)0.0069 (8)0.0225 (9)0.0017 (8)
C110.0378 (8)0.0535 (11)0.0502 (10)0.0052 (8)0.0218 (8)0.0039 (8)
C120.0628 (13)0.0791 (16)0.0685 (14)0.0151 (11)0.0252 (12)0.0233 (11)
C130.0661 (16)0.155 (3)0.0585 (16)0.0270 (18)0.0172 (14)0.0295 (17)
C140.0483 (13)0.185 (3)0.0568 (15)0.0033 (18)0.0191 (12)0.022 (2)
C150.0626 (14)0.107 (2)0.0844 (18)0.0204 (14)0.0407 (15)0.0400 (16)
C160.0572 (11)0.0610 (13)0.0661 (13)0.0040 (9)0.0314 (11)0.0087 (10)
C170.0384 (9)0.0534 (10)0.0395 (9)0.0013 (8)0.0133 (8)0.0004 (7)
C180.0597 (12)0.0631 (13)0.0571 (12)0.0061 (10)0.0250 (10)0.0132 (10)
C190.0744 (15)0.0791 (16)0.0599 (13)0.0084 (12)0.0265 (12)0.0206 (11)
C200.0698 (14)0.108 (2)0.0565 (13)0.0186 (13)0.0355 (12)0.0021 (12)
C210.0721 (14)0.0963 (19)0.0746 (14)0.0016 (13)0.0481 (13)0.0019 (13)
C220.0609 (12)0.0659 (13)0.0635 (12)0.0049 (10)0.0351 (11)0.0051 (9)
Geometric parameters (Å, º) top
N1—C31.342 (2)C11—C121.379 (3)
N1—N21.347 (2)C11—C161.379 (3)
N1—H10.9427C12—C131.372 (4)
N2—C11.338 (2)C12—H120.9300
C1—C21.414 (2)C13—C141.352 (4)
C1—C171.475 (2)C13—H130.9300
C2—C31.381 (2)C14—C151.370 (4)
C2—C101.499 (2)C14—H140.9300
C3—C41.471 (2)C15—C161.388 (3)
C4—C51.387 (3)C15—H150.9300
C4—C91.388 (3)C16—H160.9300
C5—C61.373 (3)C17—C181.380 (3)
C5—H50.9300C17—C221.390 (3)
C6—C71.369 (4)C18—C191.386 (3)
C6—H60.9300C18—H180.9300
C7—C81.375 (4)C19—C201.366 (3)
C7—H70.9300C19—H190.9300
C8—C91.378 (3)C20—C211.361 (3)
C8—H80.9300C20—H200.9300
C9—H90.9300C21—C221.376 (3)
C10—C111.510 (2)C21—H210.9300
C10—H10A0.9700C22—H220.9300
C10—H10B0.9700
N2—N1—H1116.7C12—C11—C16118.31 (19)
C1—N2—N1105.6 (1)C12—C11—C10119.39 (18)
C1—C2—C10129.4 (2)C16—C11—C10122.25 (16)
C2—C10—C11115.2 (1)C13—C12—C11120.9 (3)
C3—N1—H1130.9C13—C12—H12119.6
C3—N1—N2112.3 (1)C11—C12—H12119.6
N2—C1—C2110.23 (14)C14—C13—C12120.7 (3)
N2—C1—C17117.97 (14)C14—C13—H13119.6
C2—C1—C17131.80 (15)C12—C13—H13119.6
C3—C2—C1104.93 (14)C13—C14—C15119.8 (2)
C3—C2—C10125.6 (2)C13—C14—H14120.1
N1—C3—C2106.96 (14)C15—C14—H14120.1
N1—C3—C4120.20 (15)C14—C15—C16120.0 (3)
C2—C3—C4132.77 (15)C14—C15—H15120.0
C5—C4—C9118.52 (17)C16—C15—H15120.0
C5—C4—C3121.53 (16)C11—C16—C15120.3 (2)
C9—C4—C3119.94 (16)C11—C16—H16119.9
C6—C5—C4120.5 (2)C15—C16—H16119.9
C6—C5—H5119.7C18—C17—C22117.62 (17)
C4—C5—H5119.7C18—C17—C1122.79 (16)
C7—C6—C5120.2 (2)C22—C17—C1119.54 (16)
C7—C6—H6119.9C17—C18—C19120.8 (2)
C5—C6—H6119.9C17—C18—H18119.6
C6—C7—C8120.5 (2)C19—C18—H18119.6
C6—C7—H7119.8C20—C19—C18120.5 (2)
C8—C7—H7119.8C20—C19—H19119.8
C7—C8—C9119.5 (2)C18—C19—H19119.8
C7—C8—H8120.3C21—C20—C19119.4 (2)
C9—C8—H8120.3C21—C20—H20120.3
C8—C9—C4120.8 (2)C19—C20—H20120.3
C8—C9—H9119.6C20—C21—C22120.7 (2)
C4—C9—H9119.6C20—C21—H21119.6
C2—C10—H10A108.5C22—C21—H21119.6
C11—C10—H10A108.5C21—C22—C17120.9 (2)
C2—C10—H10B108.5C21—C22—H22119.5
C11—C10—H10B108.5C17—C22—H22119.5
H10A—C10—H10B107.5
C3—N1—N2—C10.64 (19)C3—C2—C10—C11110.60 (19)
N1—N2—C1—C20.66 (18)C1—C2—C10—C1169.5 (2)
N1—N2—C1—C17178.43 (14)C2—C10—C11—C12150.44 (17)
N2—C1—C2—C30.45 (19)C2—C10—C11—C1632.3 (2)
C17—C1—C2—C3178.47 (17)C16—C11—C12—C130.8 (3)
N2—C1—C2—C10179.66 (16)C10—C11—C12—C13176.60 (19)
C17—C1—C2—C101.4 (3)C11—C12—C13—C140.7 (4)
N2—N1—C3—C20.4 (2)C12—C13—C14—C152.0 (4)
N2—N1—C3—C4177.68 (15)C13—C14—C15—C161.7 (4)
C1—C2—C3—N10.05 (18)C12—C11—C16—C151.1 (3)
C10—C2—C3—N1179.95 (16)C10—C11—C16—C15176.23 (16)
C1—C2—C3—C4176.79 (18)C14—C15—C16—C110.1 (3)
C10—C2—C3—C43.1 (3)N2—C1—C17—C18151.80 (18)
N1—C3—C4—C5134.60 (18)C2—C1—C17—C1827.0 (3)
C2—C3—C4—C548.9 (3)N2—C1—C17—C2225.7 (2)
N1—C3—C4—C943.9 (2)C2—C1—C17—C22155.47 (19)
C2—C3—C4—C9132.6 (2)C22—C17—C18—C191.0 (3)
C9—C4—C5—C60.1 (3)C1—C17—C18—C19176.53 (17)
C3—C4—C5—C6178.39 (18)C17—C18—C19—C200.3 (3)
C4—C5—C6—C70.4 (3)C18—C19—C20—C211.0 (3)
C5—C6—C7—C80.7 (4)C19—C20—C21—C220.3 (3)
C6—C7—C8—C90.4 (4)C20—C21—C22—C171.1 (3)
C7—C8—C9—C40.1 (3)C18—C17—C22—C211.7 (3)
C5—C4—C9—C80.4 (3)C1—C17—C22—C21175.91 (18)
C3—C4—C9—C8178.17 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.942.052.854 (2)143
C8—H8···Cg3ii3.002.933.853 (3)153
C12—H12···Cg1iii2.932.753.857 (3)173
C20—H20···Cg2iv2.992.903.705 (3)135
Symmetry codes: (i) x+1, y+2, z+2; (ii) x, y, z+1; (iii) x, y+3/2, z1/2; (iv) x+1, y, z.
 

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