Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021812/hg2234sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021812/hg2234Isup2.hkl |
CCDC reference: 651410
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.079
- wR factor = 0.213
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H1 .. H2 .. 1.64 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H1 .. H2 .. 1.64 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C20 - C23 ... 1.43 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. N3 .. 2.70 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Hydrazine hydrate (85%) (7.06 g, 12.0 mmol) was added to a solution of 4-(2-benzoyl-3-oxo-3-phenylpropyl)benzonitrile (3.40 g, 10.0 mmol) in 20 ml e thanol. The mixture was refluxed for two hours, then cooled to room temperature to give colourless microcrystals. The crystals were filtered, washed with a minimum amount of cold ethanol and dried under vacuum (yield, of 3.2 g). Crystals were obtained by slow evaporation of a ethanol solution of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.25 (3〈i〉H, t, J=7.0 Hz, CH3), 3.73 (3H, q, J=7.0 Hz, CH2), 4.16 (2〈i〉H, s, CH2), 7.22 (4H, d, J=8.0 Hz, benzonitrile-H), 7.36 (12H, m, Ph—H), 7.41 (8H, m,Ph—H), 7.54 (4H, d, J=8.0 Hz, benzonitrile-H), 10.5 (2H,br, N—H) p.p.m.
The imino H atom was located in a difference Fourier map and refined as riding on N2, with N–H = 0.91 Å and Uiso(H) = 1.2Ueq(N2). The hydroxy H atom was located in a difference Fourier map and refined as riding on O1, with O–H = 0.77 Å and Uiso(H) = 1.2Ueq(O1). The aromatic H atoms were constrained to an ideal geometry, with C—H distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C). The methyl H atoms were rotated to fit the electron density, with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C). The methylene H atoms were constrained to ideal geometry, with C—H distances of 0.97 Å and Uiso(H) = 1.2Ueq(C).The largest peak and deepest hole on the final difference Fourier map corresponded to 0.33 and -0.45 e.Å-3, and were located 0.56 and 1.55 Å from the C24 and H1 atom, respectively.
Substituted pyrazole tends to form cyclic poly-membered clusters through intermolecular N—H···N hydrogen bonds (Haghiri et al., 2003). Huang et al. report a 4-benzyl substituted 3,5-diphenyl-1H-pyrazole, in which two pyrazole molecules are connected by N—H···N hydrogen bonds (Huang et al., 2007). In the present paper, we report another substituted pyrazole, 4-((3,5-diphenyl-1H-pyrazol-4-yl)methyl)benzonitrile (Fig. 1). In the unit cell, two pyrazole molecules are bridged by one ethanol molecule through N—H···O and O–H···N hydrogen bonds forming a dimer. These dimers are linked by C—H···N hydrogen bonds between the phenyl group and benzonitrile, C—H···π hydrogen bonds between the phenyl groups and π···π interactions between benzonitrile planes as showed in Fig.2. The centroid-centroid contact between two benzonitrile molecules is 4.320 (1) Å.
For related literature, see: Haghiri et al. (2003); Huang et al. (2007).
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 (Bruker, 2001); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom numbering scheme. | |
Fig. 2. Crystal packing for title compound. |
C23H17N3·0.5C2H6O | F(000) = 756 |
Mr = 358.43 | Dx = 1.230 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb | Cell parameters from 582 reflections |
a = 6.1301 (12) Å | θ = 1.2–27.5° |
b = 34.541 (7) Å | µ = 0.08 mm−1 |
c = 9.4459 (19) Å | T = 291 K |
β = 104.52 (3)° | Block, colorless |
V = 1936.2 (7) Å3 | 0.25 × 0.18 × 0.15 mm |
Z = 4 |
Rigaku RAXIS RAPID IP diffractometer | 4500 independent reflections |
Radiation source: Rotating Anode | 3819 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Oscillation scans | θmax = 27.5°, θmin = 1.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −7→7 |
Tmin = 0.98, Tmax = 0.99 | k = 0→44 |
5538 measured reflections | l = 0→12 |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.199P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3 |
4500 reflections | (Δ/σ)max = 0.001 |
256 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
C23H17N3·0.5C2H6O | V = 1936.2 (7) Å3 |
Mr = 358.43 | Z = 4 |
Monoclinic, P21/m | Mo Kα radiation |
a = 6.1301 (12) Å | µ = 0.08 mm−1 |
b = 34.541 (7) Å | T = 291 K |
c = 9.4459 (19) Å | 0.25 × 0.18 × 0.15 mm |
β = 104.52 (3)° |
Rigaku RAXIS RAPID IP diffractometer | 4500 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3819 reflections with I > 2σ(I) |
Tmin = 0.98, Tmax = 0.99 | Rint = 0.038 |
5538 measured reflections |
R[F2 > 2σ(F2)] = 0.079 | 0 restraints |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.33 e Å−3 |
4500 reflections | Δρmin = −0.45 e Å−3 |
256 parameters |
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 | Occ. (<1) | |
C1 | 0.1507 (2) | 0.17406 (4) | 0.55204 (15) | 0.0431 (3) | |
C2 | −0.0612 (3) | 0.17793 (4) | 0.43839 (15) | 0.0448 (4) | |
C3 | −0.2417 (3) | 0.19860 (5) | 0.45897 (18) | 0.0503 (4) | |
H3 | −0.2270 | 0.2121 | 0.5460 | 0.060* | |
C4 | −0.4435 (3) | 0.20000 (6) | 0.3553 (2) | 0.0627 (5) | |
H4 | −0.5630 | 0.2141 | 0.3731 | 0.075* | |
C5 | −0.4694 (4) | 0.18040 (7) | 0.2239 (2) | 0.0689 (5) | |
H5 | −0.6062 | 0.1809 | 0.1536 | 0.083* | |
C6 | −0.2842 (4) | 0.15971 (7) | 0.1993 (2) | 0.0692 (5) | |
H6 | −0.2973 | 0.1473 | 0.1102 | 0.083* | |
C7 | −0.0844 (3) | 0.15756 (6) | 0.30514 (18) | 0.0599 (5) | |
H7 | 0.0345 | 0.1429 | 0.2894 | 0.072* | |
C8 | 0.2659 (2) | 0.14007 (5) | 0.60830 (15) | 0.0441 (3) | |
C9 | 0.4582 (2) | 0.15295 (4) | 0.71101 (15) | 0.0434 (3) | |
C10 | 0.6524 (3) | 0.13115 (4) | 0.80378 (16) | 0.0454 (4) | |
C11 | 0.8684 (3) | 0.14761 (5) | 0.83408 (16) | 0.0493 (4) | |
H11 | 0.8897 | 0.1717 | 0.7959 | 0.059* | |
C12 | 1.0487 (3) | 0.12795 (6) | 0.92064 (19) | 0.0601 (5) | |
H12 | 1.1910 | 0.1392 | 0.9421 | 0.072* | |
C13 | 1.0214 (4) | 0.09147 (7) | 0.9765 (2) | 0.0699 (6) | |
H13 | 1.1441 | 0.0782 | 1.0338 | 0.084* | |
C14 | 0.8116 (4) | 0.07567 (7) | 0.9456 (3) | 0.0749 (6) | |
H14 | 0.7921 | 0.0513 | 0.9826 | 0.090* | |
C15 | 0.6261 (3) | 0.09482 (5) | 0.86047 (19) | 0.0568 (4) | |
H15 | 0.4843 | 0.0834 | 0.8413 | 0.068* | |
C16 | 0.1811 (3) | 0.09973 (5) | 0.56892 (16) | 0.0469 (4) | |
H16B | 0.0213 | 0.1013 | 0.5220 | 0.056* | |
H16C | 0.1967 | 0.0853 | 0.6590 | 0.056* | |
C17 | 0.2924 (2) | 0.07649 (4) | 0.47008 (14) | 0.0435 (3) | |
C18 | 0.4823 (3) | 0.08927 (5) | 0.42526 (18) | 0.0506 (4) | |
H18 | 0.5419 | 0.1136 | 0.4548 | 0.061* | |
C19 | 0.5828 (3) | 0.06676 (5) | 0.33870 (19) | 0.0568 (4) | |
H19 | 0.7059 | 0.0761 | 0.3083 | 0.068* | |
C20 | 0.4983 (3) | 0.03003 (5) | 0.29748 (18) | 0.0532 (4) | |
C21 | 0.3082 (3) | 0.01678 (5) | 0.3381 (2) | 0.0601 (5) | |
H21 | 0.2481 | −0.0074 | 0.3076 | 0.072* | |
C22 | 0.2100 (3) | 0.03981 (5) | 0.42376 (19) | 0.0554 (4) | |
H22 | 0.0844 | 0.0306 | 0.4516 | 0.066* | |
C23 | 0.6143 (3) | 0.00582 (6) | 0.2168 (2) | 0.0618 (5) | |
N1 | 0.2632 (2) | 0.20491 (4) | 0.62334 (13) | 0.0475 (3) | |
N2 | 0.4512 (2) | 0.19150 (4) | 0.71881 (13) | 0.0475 (3) | |
H2 | 0.5363 | 0.2094 | 0.7792 | 0.105 (10)* | |
N3 | 0.7146 (4) | −0.01378 (7) | 0.1585 (2) | 0.0833 (6) | |
O1 | 0.7504 (4) | 0.2500 | 0.8444 (3) | 0.0823 (7) | |
H1 | 0.6334 | 0.2500 | 0.8613 | 0.18 (3)* | |
C24 | 0.8776 (18) | 0.2500 | 0.9996 (6) | 0.163 (3) | |
H24A | 0.8465 | 0.2729 | 1.0505 | 0.196* | 0.50 |
H24B | 0.8465 | 0.2271 | 1.0505 | 0.196* | 0.50 |
C25 | 1.1059 (16) | 0.2500 | 0.9826 (17) | 0.303 (9) | |
H25A | 1.1067 | 0.2398 | 0.8881 | 0.455* | 0.50 |
H25B | 1.1993 | 0.2342 | 1.0572 | 0.455* | 0.50 |
H25C | 1.1631 | 0.2760 | 0.9911 | 0.455* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0417 (8) | 0.0438 (8) | 0.0423 (7) | −0.0021 (5) | 0.0078 (5) | −0.0025 (5) |
C2 | 0.0454 (8) | 0.0420 (7) | 0.0467 (7) | −0.0016 (6) | 0.0110 (5) | −0.0011 (5) |
C3 | 0.0501 (9) | 0.0412 (8) | 0.0571 (8) | 0.0015 (6) | 0.0088 (6) | 0.0014 (5) |
C4 | 0.0541 (10) | 0.0592 (11) | 0.0710 (10) | 0.0064 (8) | 0.0084 (7) | 0.0025 (8) |
C5 | 0.0619 (12) | 0.0676 (13) | 0.0693 (11) | −0.0075 (9) | 0.0015 (8) | 0.0009 (8) |
C6 | 0.0777 (14) | 0.0682 (13) | 0.0570 (9) | −0.0025 (10) | 0.0080 (8) | −0.0080 (8) |
C7 | 0.0664 (11) | 0.0596 (11) | 0.0527 (9) | 0.0001 (8) | 0.0129 (7) | −0.0047 (7) |
C8 | 0.0424 (8) | 0.0438 (8) | 0.0458 (7) | −0.0031 (5) | 0.0106 (5) | −0.0035 (5) |
C9 | 0.0427 (8) | 0.0419 (7) | 0.0459 (7) | −0.0031 (5) | 0.0118 (5) | −0.0037 (5) |
C10 | 0.0461 (8) | 0.0409 (7) | 0.0480 (7) | 0.0044 (5) | 0.0099 (5) | −0.0078 (5) |
C11 | 0.0436 (8) | 0.0556 (9) | 0.0483 (7) | −0.0001 (6) | 0.0105 (5) | −0.0020 (6) |
C12 | 0.0439 (9) | 0.0719 (12) | 0.0602 (9) | 0.0070 (7) | 0.0048 (6) | −0.0058 (7) |
C13 | 0.0653 (12) | 0.0716 (13) | 0.0684 (11) | 0.0233 (10) | 0.0085 (8) | 0.0016 (8) |
C14 | 0.0811 (15) | 0.0581 (12) | 0.0815 (12) | 0.0106 (10) | 0.0128 (10) | 0.0108 (9) |
C15 | 0.0584 (10) | 0.0460 (9) | 0.0627 (9) | −0.0032 (7) | 0.0089 (7) | −0.0034 (6) |
C16 | 0.0397 (8) | 0.0448 (8) | 0.0521 (8) | −0.0028 (5) | 0.0037 (5) | −0.0045 (5) |
C17 | 0.0407 (8) | 0.0377 (7) | 0.0477 (7) | −0.0010 (5) | 0.0030 (5) | −0.0011 (5) |
C18 | 0.0523 (9) | 0.0401 (8) | 0.0589 (8) | −0.0070 (6) | 0.0128 (6) | −0.0081 (5) |
C19 | 0.0620 (10) | 0.0465 (9) | 0.0630 (9) | −0.0055 (7) | 0.0179 (7) | −0.0041 (7) |
C20 | 0.0582 (10) | 0.0408 (8) | 0.0577 (8) | 0.0018 (7) | 0.0088 (6) | −0.0055 (6) |
C21 | 0.0592 (10) | 0.0435 (9) | 0.0736 (10) | −0.0090 (7) | 0.0090 (7) | −0.0153 (7) |
C22 | 0.0515 (9) | 0.0458 (9) | 0.0671 (9) | −0.0064 (7) | 0.0116 (6) | −0.0069 (6) |
C23 | 0.0682 (12) | 0.0465 (9) | 0.0722 (10) | 0.0033 (8) | 0.0201 (8) | −0.0055 (7) |
N1 | 0.0451 (7) | 0.0426 (7) | 0.0512 (7) | −0.0005 (5) | 0.0053 (5) | −0.0063 (5) |
N2 | 0.0458 (7) | 0.0431 (7) | 0.0509 (7) | −0.0007 (5) | 0.0070 (5) | −0.0068 (5) |
N3 | 0.0951 (16) | 0.0631 (12) | 0.0988 (13) | 0.0049 (10) | 0.0375 (11) | −0.0144 (10) |
O1 | 0.0603 (14) | 0.0570 (13) | 0.1096 (17) | 0.000 | −0.0159 (10) | 0.000 |
C24 | 0.250 (10) | 0.109 (5) | 0.098 (3) | 0.000 | −0.015 (4) | 0.000 |
C25 | 0.108 (6) | 0.219 (12) | 0.469 (19) | 0.000 | −0.142 (9) | 0.000 |
C1—N1 | 1.354 (2) | C14—H14 | 0.9300 |
C1—C8 | 1.404 (2) | C15—H15 | 0.9300 |
C1—C2 | 1.469 (2) | C16—C17 | 1.517 (2) |
C2—C3 | 1.371 (2) | C16—H16B | 0.9700 |
C2—C7 | 1.418 (2) | C16—H16C | 0.9700 |
C3—C4 | 1.372 (2) | C17—C22 | 1.393 (2) |
C3—H3 | 0.9300 | C17—C18 | 1.406 (2) |
C4—C5 | 1.387 (3) | C18—C19 | 1.380 (2) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.410 (4) | C19—C20 | 1.389 (2) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.375 (3) | C20—C21 | 1.393 (3) |
C6—H6 | 0.9300 | C20—C23 | 1.434 (2) |
C7—H7 | 0.9300 | C21—C22 | 1.376 (3) |
C8—C9 | 1.398 (2) | C21—H21 | 0.9300 |
C8—C16 | 1.501 (2) | C22—H22 | 0.9300 |
C9—N2 | 1.335 (2) | C23—N3 | 1.144 (3) |
C9—C10 | 1.493 (2) | N1—N2 | 1.355 (2) |
C10—C15 | 1.390 (2) | N2—H2 | 0.910 |
C10—C11 | 1.403 (2) | O1—C24 | 1.478 (6) |
C11—C12 | 1.378 (2) | O1—H1 | 0.77 |
C11—H11 | 0.9300 | C24—C25 | 1.448 (15) |
C12—C13 | 1.393 (3) | C24—H24A | 0.9700 |
C12—H12 | 0.9300 | C24—H24B | 0.9700 |
C13—C14 | 1.359 (4) | C25—H25A | 0.9600 |
C13—H13 | 0.9300 | C25—H25B | 0.9600 |
C14—C15 | 1.385 (3) | C25—H25C | 0.9600 |
N1—C1—C8 | 108.95 (13) | C10—C15—H15 | 120.1 |
N1—C1—C2 | 122.61 (13) | C8—C16—C17 | 117.6 (1) |
C8—C1—C2 | 128.41 (13) | C8—C16—H16B | 107.9 |
C3—C2—C7 | 118.65 (16) | C17—C16—H16B | 107.9 |
C3—C2—C1 | 122.74 (13) | C8—C16—H16C | 107.9 |
C7—C2—C1 | 118.50 (14) | C17—C16—H16C | 107.9 |
C2—C3—C4 | 122.14 (16) | H16B—C16—H16C | 107.2 |
C2—C3—H3 | 118.9 | C22—C17—C18 | 116.97 (14) |
C4—C3—H3 | 118.9 | C22—C17—C16 | 119.40 (14) |
C3—C4—C5 | 120.13 (19) | C18—C17—C16 | 123.60 (13) |
C3—C4—H4 | 119.9 | C19—C18—C17 | 121.86 (15) |
C5—C4—H4 | 119.9 | C19—C18—H18 | 119.1 |
C4—C5—C6 | 118.58 (19) | C17—C18—H18 | 119.1 |
C4—C5—H5 | 120.7 | C18—C19—C20 | 119.35 (17) |
C6—C5—H5 | 120.7 | C18—C19—H19 | 120.3 |
C7—C6—C5 | 121.01 (18) | C20—C19—H19 | 120.3 |
C7—C6—H6 | 119.5 | C19—C20—C21 | 120.14 (16) |
C5—C6—H6 | 119.5 | C19—C20—C23 | 118.81 (17) |
C6—C7—C2 | 119.43 (18) | C21—C20—C23 | 121.03 (16) |
C6—C7—H7 | 120.3 | C22—C21—C20 | 119.45 (16) |
C2—C7—H7 | 120.3 | C22—C21—H21 | 120.3 |
C9—C8—C1 | 104.66 (14) | C20—C21—H21 | 120.3 |
C9—C8—C16 | 130.29 (14) | C21—C22—C17 | 122.19 (16) |
C1—C8—C16 | 124.91 (14) | C21—C22—H22 | 118.9 |
N2—C9—C8 | 108.83 (14) | C17—C22—H22 | 118.9 |
N2—C9—C10 | 120.16 (13) | N3—C23—C20 | 176.7 (2) |
C8—C9—C10 | 131.01 (14) | C1—N1—N2 | 107.7 (1) |
C15—C10—C11 | 118.84 (15) | C9—N2—N1 | 109.7 (1) |
C15—C10—C9 | 121.93 (15) | C9—N2—H2 | 134 |
C11—C10—C9 | 119.23 (14) | N1—N2—H2 | 116 |
C12—C11—C10 | 119.81 (17) | C24—O1—H1 | 95 |
C12—C11—H11 | 120.1 | C25—C24—O1 | 100.0 (7) |
C10—C11—H11 | 120.1 | C25—C24—H24A | 111.8 |
C11—C12—C13 | 121.05 (18) | O1—C24—H24A | 111.8 |
C11—C12—H12 | 119.5 | C25—C24—H24B | 111.8 |
C13—C12—H12 | 119.5 | O1—C24—H24B | 111.8 |
C14—C13—C12 | 118.64 (19) | H24A—C24—H24B | 109.5 |
C14—C13—H13 | 120.7 | C24—C25—H25A | 109.5 |
C12—C13—H13 | 120.7 | C24—C25—H25B | 109.5 |
C13—C14—C15 | 121.9 (2) | H25A—C25—H25B | 109.5 |
C13—C14—H14 | 119.1 | C24—C25—H25C | 109.5 |
C15—C14—H14 | 119.1 | H25A—C25—H25C | 109.5 |
C14—C15—C10 | 119.80 (19) | H25B—C25—H25C | 109.5 |
C14—C15—H15 | 120.1 | ||
N1—C1—C2—C3 | −51.3 (2) | C10—C11—C12—C13 | 1.4 (3) |
C8—C1—C2—C3 | 126.61 (17) | C11—C12—C13—C14 | −0.9 (3) |
N1—C1—C2—C7 | 132.54 (17) | C12—C13—C14—C15 | 0.1 (3) |
C8—C1—C2—C7 | −49.6 (2) | C13—C14—C15—C10 | 0.3 (3) |
C7—C2—C3—C4 | 0.3 (3) | C11—C10—C15—C14 | 0.2 (2) |
C1—C2—C3—C4 | −175.85 (17) | C9—C10—C15—C14 | 179.78 (16) |
C2—C3—C4—C5 | −0.6 (3) | C9—C8—C16—C17 | −78.51 (19) |
C3—C4—C5—C6 | −0.9 (3) | C1—C8—C16—C17 | 106.47 (16) |
C4—C5—C6—C7 | 2.6 (3) | C8—C16—C17—C22 | −176.18 (14) |
C5—C6—C7—C2 | −2.9 (3) | C8—C16—C17—C18 | 6.1 (2) |
C3—C2—C7—C6 | 1.4 (3) | C22—C17—C18—C19 | 0.3 (2) |
C1—C2—C7—C6 | 177.75 (17) | C16—C17—C18—C19 | 178.05 (15) |
N1—C1—C8—C9 | −3.01 (16) | C17—C18—C19—C20 | −1.7 (3) |
C2—C1—C8—C9 | 178.87 (13) | C18—C19—C20—C21 | 2.7 (3) |
N1—C1—C8—C16 | 173.06 (13) | C18—C19—C20—C23 | −175.38 (17) |
C2—C1—C8—C16 | −5.1 (2) | C19—C20—C21—C22 | −2.3 (3) |
C1—C8—C9—N2 | 2.43 (15) | C23—C20—C21—C22 | 175.70 (17) |
C16—C8—C9—N2 | −173.35 (14) | C20—C21—C22—C17 | 0.9 (3) |
C1—C8—C9—C10 | −177.27 (14) | C18—C17—C22—C21 | 0.1 (2) |
C16—C8—C9—C10 | 7.0 (2) | C16—C17—C22—C21 | −177.77 (16) |
N2—C9—C10—C15 | 145.60 (15) | C8—C1—N1—N2 | 2.50 (16) |
C8—C9—C10—C15 | −34.7 (2) | C2—C1—N1—N2 | −179.25 (12) |
N2—C9—C10—C11 | −34.83 (19) | C8—C9—N2—N1 | −1.00 (16) |
C8—C9—C10—C11 | 144.84 (15) | C10—C9—N2—N1 | 178.74 (12) |
C15—C10—C11—C12 | −1.0 (2) | C1—N1—N2—C9 | −0.93 (16) |
C9—C10—C11—C12 | 179.42 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.77 | 2.53 | 2.786 (2) | 102 |
O1—H1···N2i | 0.77 | 2.53 | 2.786 (2) | 102 |
N2—H2···O1 | 0.91 | 1.91 | 2.786 (2) | 160 |
C15—H15···N3ii | 0.93 | 2.70 | 3.470 (3) | 141 |
C6—H6···Cg1iii | 0.93 | 2.72 | 3.601 (2) | 159 |
Symmetry codes: (i) x, −y+1/2, z; (ii) −x+1, −y, −z+1; (iii) x−1, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C23H17N3·0.5C2H6O |
Mr | 358.43 |
Crystal system, space group | Monoclinic, P21/m |
Temperature (K) | 291 |
a, b, c (Å) | 6.1301 (12), 34.541 (7), 9.4459 (19) |
β (°) | 104.52 (3) |
V (Å3) | 1936.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Rigaku RAXIS RAPID IP |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.98, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5538, 4500, 3819 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.079, 0.214, 1.08 |
No. of reflections | 4500 |
No. of parameters | 256 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.45 |
Computer programs: RAPID-AUTO (Rigaku, 1999), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.77 | 2.53 | 2.786 (2) | 102 |
O1—H1···N2i | 0.77 | 2.53 | 2.786 (2) | 102 |
N2—H2···O1 | 0.91 | 1.91 | 2.786 (2) | 160 |
C15—H15···N3ii | 0.93 | 2.70 | 3.470 (3) | 141 |
C6—H6···Cg1iii | 0.93 | 2.72 | 3.601 (2) | 159 |
Symmetry codes: (i) x, −y+1/2, z; (ii) −x+1, −y, −z+1; (iii) x−1, y, z−1. |
Substituted pyrazole tends to form cyclic poly-membered clusters through intermolecular N—H···N hydrogen bonds (Haghiri et al., 2003). Huang et al. report a 4-benzyl substituted 3,5-diphenyl-1H-pyrazole, in which two pyrazole molecules are connected by N—H···N hydrogen bonds (Huang et al., 2007). In the present paper, we report another substituted pyrazole, 4-((3,5-diphenyl-1H-pyrazol-4-yl)methyl)benzonitrile (Fig. 1). In the unit cell, two pyrazole molecules are bridged by one ethanol molecule through N—H···O and O–H···N hydrogen bonds forming a dimer. These dimers are linked by C—H···N hydrogen bonds between the phenyl group and benzonitrile, C—H···π hydrogen bonds between the phenyl groups and π···π interactions between benzonitrile planes as showed in Fig.2. The centroid-centroid contact between two benzonitrile molecules is 4.320 (1) Å.