The title compound, C
24H
18N
2O
3, is a derivative of 1
H-pyrazole-3-carboxylic acid. The pyrazole substituted N atom deviates by 0.0037 (11) Å from the pyrazole ring. The molecules are connected by C—H
O, π—π and C—H
π(phenyl) interactions. In the C—H
π interaction, the C
Cg distance is 3.6514 (19) Å (
Cg is the ring centroid), with a C—H
π angle of 147.6 (11)°.
Supporting information
CCDC reference: 236055
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.045
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.134
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C4 = 5.29 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SX-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Methyl 4-benzoyl-1,5-diphenyl-1
H-pyrazole-3-carboxylate
top
Crystal data top
C24H18N2O3 | F(000) = 800 |
Mr = 382.40 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20375 reflections |
a = 8.6467 (6) Å | θ = 2.0–29.5° |
b = 20.5855 (13) Å | µ = 0.09 mm−1 |
c = 10.9985 (8) Å | T = 293 K |
β = 100.297 (6)° | Prism, colourless |
V = 1926.2 (2) Å3 | 0.50 × 0.36 × 0.19 mm |
Z = 4 | |
Data collection top
Stoe IPDS 2 diffractometer | 3385 independent reflections |
Radiation source: sealed X-ray tube | 2148 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.134 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 2.0° |
φ scans | h = −10→10 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −24→24 |
Tmin = 0.948, Tmax = 0.982 | l = −13→13 |
37508 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | All H-atom parameters refined |
wR(F2) = 0.045 | w = 1/[σ2(Fo2) + (0.0121P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
3385 reflections | Δρmax = 0.13 e Å−3 |
335 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0090 (4) |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O1 | −0.34673 (11) | 0.70366 (5) | 0.88187 (9) | 0.0595 (3) | |
O2 | −0.20483 (10) | 0.78817 (5) | 0.96654 (9) | 0.0572 (3) | |
O3 | −0.17917 (11) | 0.56173 (5) | 0.71550 (9) | 0.0553 (3) | |
N1 | 0.09818 (12) | 0.73669 (5) | 0.74424 (9) | 0.0365 (3) | |
N2 | −0.00082 (12) | 0.76718 (5) | 0.80882 (9) | 0.0389 (3) | |
C1 | −0.09371 (14) | 0.72013 (6) | 0.83661 (11) | 0.0363 (3) | |
C2 | −0.05709 (14) | 0.65941 (6) | 0.79023 (11) | 0.0364 (3) | |
C3 | 0.06721 (14) | 0.67144 (6) | 0.73022 (11) | 0.0352 (3) | |
C4 | −0.22881 (16) | 0.73551 (7) | 0.89646 (12) | 0.0425 (3) | |
C5 | −0.3344 (2) | 0.80831 (12) | 1.0251 (2) | 0.0704 (6) | |
H5A | −0.3009 (19) | 0.8498 (9) | 1.0655 (15) | 0.090 (6)* | |
H5B | −0.431 (2) | 0.8116 (8) | 0.9608 (15) | 0.093 (6)* | |
H5C | −0.354 (2) | 0.7749 (10) | 1.0848 (18) | 0.115 (8)* | |
C6 | −0.13252 (15) | 0.59555 (6) | 0.80590 (13) | 0.0402 (3) | |
C7 | −0.14970 (15) | 0.57401 (6) | 0.93156 (12) | 0.0399 (3) | |
C8 | −0.24976 (19) | 0.52308 (7) | 0.94402 (15) | 0.0560 (4) | |
H8 | −0.3091 (17) | 0.5049 (7) | 0.8674 (14) | 0.076 (5)* | |
C9 | −0.2697 (2) | 0.50265 (8) | 1.05931 (16) | 0.0667 (5) | |
H9 | −0.3415 (19) | 0.4659 (8) | 1.0655 (14) | 0.087 (5)* | |
C10 | −0.1890 (2) | 0.53203 (8) | 1.16331 (17) | 0.0613 (5) | |
H10 | −0.2042 (17) | 0.5177 (7) | 1.2456 (14) | 0.071 (5)* | |
C11 | −0.0894 (2) | 0.58216 (9) | 1.15251 (15) | 0.0652 (5) | |
H11 | −0.0339 (19) | 0.6028 (7) | 1.2264 (14) | 0.080 (5)* | |
C12 | −0.06882 (19) | 0.60292 (8) | 1.03714 (14) | 0.0559 (4) | |
H12 | 0.0007 (17) | 0.6365 (7) | 1.0292 (12) | 0.061 (4)* | |
C13 | 0.21291 (15) | 0.77547 (6) | 0.69826 (12) | 0.0369 (3) | |
C14 | 0.28754 (17) | 0.82445 (7) | 0.77186 (14) | 0.0501 (4) | |
H14 | 0.2558 (15) | 0.8324 (6) | 0.8514 (12) | 0.056 (4)* | |
C15 | 0.3977 (2) | 0.86196 (9) | 0.72680 (17) | 0.0641 (5) | |
H15 | 0.4432 (18) | 0.8951 (8) | 0.7767 (14) | 0.076 (5)* | |
C16 | 0.4332 (2) | 0.85036 (9) | 0.61206 (17) | 0.0640 (5) | |
H16 | 0.5137 (19) | 0.8764 (8) | 0.5828 (14) | 0.086 (5)* | |
C17 | 0.35633 (18) | 0.80223 (8) | 0.53947 (16) | 0.0549 (4) | |
H17 | 0.3824 (17) | 0.7945 (7) | 0.4576 (13) | 0.071 (5)* | |
C18 | 0.24444 (17) | 0.76467 (7) | 0.58165 (13) | 0.0436 (4) | |
H18 | 0.1853 (15) | 0.7322 (6) | 0.5279 (12) | 0.052 (4)* | |
C19 | 0.15771 (15) | 0.62722 (6) | 0.66364 (11) | 0.0364 (3) | |
C20 | 0.08115 (18) | 0.59455 (7) | 0.56014 (13) | 0.0438 (4) | |
H20 | −0.0301 (17) | 0.6017 (6) | 0.5356 (11) | 0.055 (4)* | |
C21 | 0.16214 (19) | 0.55299 (7) | 0.49587 (14) | 0.0510 (4) | |
H21 | 0.1065 (17) | 0.5308 (7) | 0.4205 (13) | 0.069 (5)* | |
C22 | 0.3199 (2) | 0.54393 (8) | 0.53373 (16) | 0.0574 (4) | |
H22 | 0.3780 (16) | 0.5154 (7) | 0.4871 (12) | 0.065 (4)* | |
C23 | 0.39875 (19) | 0.57638 (8) | 0.63600 (15) | 0.0549 (4) | |
H23 | 0.5123 (18) | 0.5703 (7) | 0.6621 (12) | 0.065 (4)* | |
C24 | 0.31827 (17) | 0.61820 (7) | 0.70064 (14) | 0.0446 (4) | |
H24 | 0.3693 (14) | 0.6397 (6) | 0.7700 (11) | 0.041 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0434 (6) | 0.0619 (7) | 0.0784 (7) | −0.0109 (5) | 0.0248 (5) | −0.0197 (6) |
O2 | 0.0438 (6) | 0.0643 (7) | 0.0679 (7) | −0.0065 (5) | 0.0218 (5) | −0.0295 (6) |
O3 | 0.0660 (7) | 0.0507 (6) | 0.0508 (6) | −0.0157 (5) | 0.0144 (5) | −0.0116 (5) |
N1 | 0.0368 (6) | 0.0358 (7) | 0.0394 (6) | −0.0004 (5) | 0.0139 (5) | −0.0014 (5) |
N2 | 0.0391 (6) | 0.0394 (7) | 0.0404 (6) | 0.0019 (6) | 0.0133 (5) | −0.0023 (5) |
C1 | 0.0342 (7) | 0.0390 (8) | 0.0366 (8) | −0.0015 (6) | 0.0091 (6) | −0.0017 (6) |
C2 | 0.0361 (8) | 0.0359 (8) | 0.0378 (8) | −0.0024 (6) | 0.0078 (6) | −0.0011 (6) |
C3 | 0.0364 (7) | 0.0321 (8) | 0.0372 (8) | −0.0005 (6) | 0.0073 (6) | −0.0006 (6) |
C4 | 0.0404 (8) | 0.0453 (9) | 0.0427 (8) | 0.0001 (7) | 0.0097 (7) | −0.0028 (7) |
C5 | 0.0474 (11) | 0.0907 (16) | 0.0773 (14) | −0.0005 (11) | 0.0223 (11) | −0.0403 (13) |
C6 | 0.0356 (8) | 0.0383 (8) | 0.0481 (9) | 0.0003 (6) | 0.0108 (7) | −0.0032 (7) |
C7 | 0.0386 (8) | 0.0344 (8) | 0.0479 (9) | −0.0024 (6) | 0.0106 (7) | 0.0005 (6) |
C8 | 0.0644 (11) | 0.0516 (10) | 0.0519 (10) | −0.0184 (8) | 0.0099 (9) | −0.0007 (8) |
C9 | 0.0787 (12) | 0.0569 (11) | 0.0664 (12) | −0.0255 (10) | 0.0178 (10) | 0.0092 (9) |
C10 | 0.0763 (12) | 0.0559 (11) | 0.0534 (11) | −0.0058 (9) | 0.0158 (10) | 0.0121 (9) |
C11 | 0.0833 (13) | 0.0628 (11) | 0.0458 (10) | −0.0186 (10) | 0.0016 (9) | 0.0035 (9) |
C12 | 0.0619 (10) | 0.0524 (10) | 0.0508 (10) | −0.0204 (8) | 0.0034 (8) | 0.0055 (8) |
C13 | 0.0353 (7) | 0.0348 (8) | 0.0420 (8) | 0.0014 (6) | 0.0110 (6) | 0.0059 (6) |
C14 | 0.0570 (10) | 0.0463 (9) | 0.0487 (9) | −0.0083 (8) | 0.0144 (8) | 0.0007 (7) |
C15 | 0.0661 (11) | 0.0533 (11) | 0.0720 (12) | −0.0204 (9) | 0.0101 (10) | 0.0021 (9) |
C16 | 0.0573 (11) | 0.0605 (12) | 0.0786 (13) | −0.0071 (9) | 0.0239 (10) | 0.0201 (10) |
C17 | 0.0578 (10) | 0.0567 (10) | 0.0566 (10) | 0.0074 (8) | 0.0273 (9) | 0.0162 (8) |
C18 | 0.0455 (9) | 0.0435 (9) | 0.0438 (9) | 0.0037 (8) | 0.0131 (7) | 0.0047 (7) |
C19 | 0.0379 (8) | 0.0339 (8) | 0.0395 (8) | 0.0004 (6) | 0.0129 (6) | 0.0020 (6) |
C20 | 0.0386 (9) | 0.0443 (9) | 0.0496 (9) | 0.0024 (7) | 0.0108 (7) | −0.0037 (7) |
C21 | 0.0554 (10) | 0.0498 (9) | 0.0504 (10) | 0.0024 (8) | 0.0161 (8) | −0.0093 (8) |
C22 | 0.0571 (11) | 0.0534 (10) | 0.0680 (11) | 0.0082 (9) | 0.0280 (9) | −0.0102 (9) |
C23 | 0.0377 (9) | 0.0588 (10) | 0.0712 (11) | 0.0094 (8) | 0.0180 (9) | 0.0029 (9) |
C24 | 0.0396 (9) | 0.0458 (9) | 0.0486 (9) | −0.0010 (7) | 0.0083 (7) | −0.0007 (8) |
Geometric parameters (Å, º) top
O1—C4 | 1.1986 (15) | C11—C12 | 1.380 (2) |
O2—C4 | 1.3248 (15) | C11—H11 | 0.965 (16) |
O2—C5 | 1.4494 (17) | C12—H12 | 0.930 (14) |
O3—C6 | 1.2218 (15) | C13—C18 | 1.3761 (17) |
N1—N2 | 1.3596 (13) | C13—C14 | 1.3790 (18) |
N1—C3 | 1.3727 (15) | C14—C15 | 1.385 (2) |
N1—C13 | 1.4342 (15) | C14—H14 | 0.976 (13) |
N2—C1 | 1.3284 (15) | C15—C16 | 1.372 (2) |
C1—C2 | 1.4073 (16) | C15—H15 | 0.918 (16) |
C1—C4 | 1.4741 (17) | C16—C17 | 1.368 (2) |
C2—C3 | 1.3806 (16) | C16—H16 | 0.978 (16) |
C2—C6 | 1.4910 (17) | C17—C18 | 1.382 (2) |
C3—C19 | 1.4773 (17) | C17—H17 | 0.979 (14) |
C5—H5A | 0.981 (18) | C18—H18 | 0.975 (13) |
C5—H5B | 0.993 (18) | C19—C20 | 1.3845 (18) |
C5—H5C | 0.984 (19) | C19—C24 | 1.3876 (18) |
C6—C7 | 1.4840 (17) | C20—C21 | 1.3780 (19) |
C7—C12 | 1.3789 (19) | C20—H20 | 0.963 (14) |
C7—C8 | 1.3817 (18) | C21—C22 | 1.366 (2) |
C8—C9 | 1.376 (2) | C21—H21 | 0.992 (14) |
C8—H8 | 0.979 (15) | C22—C23 | 1.379 (2) |
C9—C10 | 1.369 (2) | C22—H22 | 0.976 (14) |
C9—H9 | 0.989 (17) | C23—C24 | 1.3812 (19) |
C10—C11 | 1.363 (2) | C23—H23 | 0.980 (15) |
C10—H10 | 0.982 (14) | C24—H24 | 0.923 (12) |
| | | |
C4—O2—C5 | 116.08 (12) | C12—C11—H11 | 120.8 (9) |
N2—N1—C3 | 112.46 (10) | C7—C12—C11 | 120.74 (15) |
N2—N1—C13 | 117.84 (10) | C7—C12—H12 | 118.7 (9) |
C3—N1—C13 | 129.67 (10) | C11—C12—H12 | 120.6 (9) |
C1—N2—N1 | 104.28 (10) | C18—C13—C14 | 121.02 (13) |
N2—C1—C2 | 112.32 (10) | C18—C13—N1 | 120.23 (12) |
N2—C1—C4 | 120.41 (11) | C14—C13—N1 | 118.73 (12) |
C2—C1—C4 | 126.89 (12) | C13—C14—C15 | 118.50 (15) |
C3—C2—C1 | 105.00 (10) | C13—C14—H14 | 118.2 (8) |
C3—C2—C6 | 127.40 (11) | C15—C14—H14 | 123.2 (8) |
C1—C2—C6 | 127.57 (11) | C16—C15—C14 | 120.89 (17) |
N1—C3—C2 | 105.95 (10) | C16—C15—H15 | 122.4 (10) |
N1—C3—C19 | 123.28 (11) | C14—C15—H15 | 116.7 (10) |
C2—C3—C19 | 130.77 (11) | C17—C16—C15 | 119.84 (16) |
O1—C4—O2 | 124.50 (12) | C17—C16—H16 | 120.4 (9) |
O1—C4—C1 | 123.07 (13) | C15—C16—H16 | 119.8 (9) |
O2—C4—C1 | 112.42 (12) | C16—C17—C18 | 120.38 (15) |
O2—C5—H5A | 105.1 (10) | C16—C17—H17 | 119.1 (9) |
O2—C5—H5B | 108.6 (10) | C18—C17—H17 | 120.5 (9) |
H5A—C5—H5B | 113.8 (14) | C13—C18—C17 | 119.32 (15) |
O2—C5—H5C | 109.4 (12) | C13—C18—H18 | 120.4 (8) |
H5A—C5—H5C | 112.1 (15) | C17—C18—H18 | 120.2 (7) |
H5B—C5—H5C | 107.7 (16) | C20—C19—C24 | 118.84 (12) |
O3—C6—C7 | 120.94 (12) | C20—C19—C3 | 119.29 (12) |
O3—C6—C2 | 119.74 (12) | C24—C19—C3 | 121.86 (12) |
C7—C6—C2 | 119.32 (12) | C21—C20—C19 | 120.74 (14) |
C12—C7—C8 | 118.44 (14) | C21—C20—H20 | 121.7 (8) |
C12—C7—C6 | 122.36 (12) | C19—C20—H20 | 117.6 (8) |
C8—C7—C6 | 119.20 (13) | C22—C21—C20 | 119.98 (15) |
C9—C8—C7 | 120.48 (16) | C22—C21—H21 | 120.1 (8) |
C9—C8—H8 | 122.9 (9) | C20—C21—H21 | 119.9 (9) |
C7—C8—H8 | 116.5 (9) | C21—C22—C23 | 120.24 (15) |
C10—C9—C8 | 120.39 (16) | C21—C22—H22 | 120.1 (9) |
C10—C9—H9 | 120.8 (9) | C23—C22—H22 | 119.6 (8) |
C8—C9—H9 | 118.8 (9) | C22—C23—C24 | 120.04 (15) |
C11—C10—C9 | 119.80 (16) | C22—C23—H23 | 120.0 (8) |
C11—C10—H10 | 119.8 (9) | C24—C23—H23 | 119.9 (8) |
C9—C10—H10 | 120.3 (9) | C23—C24—C19 | 120.14 (15) |
C10—C11—C12 | 120.13 (17) | C23—C24—H24 | 120.9 (8) |
C10—C11—H11 | 119.1 (9) | C19—C24—H24 | 119.0 (8) |
| | | |
C3—N1—N2—C1 | 0.67 (14) | C6—C7—C8—C9 | −179.09 (14) |
C13—N1—N2—C1 | 178.78 (11) | C7—C8—C9—C10 | −0.8 (3) |
N1—N2—C1—C2 | −0.39 (14) | C8—C9—C10—C11 | 0.6 (3) |
N1—N2—C1—C4 | −173.71 (11) | C9—C10—C11—C12 | −0.6 (3) |
N2—C1—C2—C3 | −0.02 (15) | C8—C7—C12—C11 | −1.1 (2) |
C4—C1—C2—C3 | 172.77 (13) | C6—C7—C12—C11 | 179.10 (14) |
N2—C1—C2—C6 | 178.19 (12) | C10—C11—C12—C7 | 0.8 (3) |
C4—C1—C2—C6 | −9.0 (2) | N2—N1—C13—C18 | −138.75 (12) |
N2—N1—C3—C2 | −0.70 (14) | C3—N1—C13—C18 | 39.0 (2) |
C13—N1—C3—C2 | −178.53 (12) | N2—N1—C13—C14 | 39.72 (18) |
N2—N1—C3—C19 | 179.97 (11) | C3—N1—C13—C14 | −142.55 (13) |
C13—N1—C3—C19 | 2.1 (2) | C18—C13—C14—C15 | −1.2 (2) |
C1—C2—C3—N1 | 0.42 (13) | N1—C13—C14—C15 | −179.70 (13) |
C6—C2—C3—N1 | −177.79 (12) | C13—C14—C15—C16 | −0.7 (2) |
C1—C2—C3—C19 | 179.68 (13) | C14—C15—C16—C17 | 1.7 (3) |
C6—C2—C3—C19 | 1.5 (2) | C15—C16—C17—C18 | −0.8 (2) |
C5—O2—C4—O1 | −1.9 (2) | C14—C13—C18—C17 | 2.1 (2) |
C5—O2—C4—C1 | 177.66 (15) | N1—C13—C18—C17 | −179.48 (13) |
N2—C1—C4—O1 | 150.13 (14) | C16—C17—C18—C13 | −1.0 (2) |
C2—C1—C4—O1 | −22.1 (2) | N1—C3—C19—C20 | −119.06 (14) |
N2—C1—C4—O2 | −29.48 (18) | C2—C3—C19—C20 | 61.79 (19) |
C2—C1—C4—O2 | 158.25 (12) | N1—C3—C19—C24 | 59.86 (18) |
C3—C2—C6—O3 | −52.9 (2) | C2—C3—C19—C24 | −119.29 (16) |
C1—C2—C6—O3 | 129.28 (14) | C24—C19—C20—C21 | 1.0 (2) |
C3—C2—C6—C7 | 127.07 (14) | C3—C19—C20—C21 | 179.94 (13) |
C1—C2—C6—C7 | −50.75 (19) | C19—C20—C21—C22 | −0.3 (2) |
O3—C6—C7—C12 | 165.08 (14) | C20—C21—C22—C23 | −0.2 (2) |
C2—C6—C7—C12 | −14.89 (19) | C21—C22—C23—C24 | 0.0 (2) |
O3—C6—C7—C8 | −14.74 (19) | C22—C23—C24—C19 | 0.6 (2) |
C2—C6—C7—C8 | 165.29 (13) | C20—C19—C24—C23 | −1.1 (2) |
C12—C7—C8—C9 | 1.1 (2) | C3—C19—C24—C23 | 179.96 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O3i | 0.981 (18) | 2.556 (19) | 3.513 (2) | 165.1 (13) |
C21—H21···O3ii | 0.992 (14) | 2.569 (14) | 3.3355 (18) | 134.0 (11) |
C10—H10···Cg4iii | 0.982 (14) | 2.783 (15) | 3.6514 (19) | 147.6 (11) |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+1, −z+1; (iii) −x+2, −y+1, −z. |