4-Benzoyl-N-methyl-1,5-di­phenyl-1H-pyrazole-3-carbox­amide

The title compound, C₂₄H₁₉N₃O₂, is a derivative of 1H-pyrazole-3-carboxyl­ic acid. The four rings in the structure are not coplanar. The dihedral angle between the mean planes of the pyrazole ring and the carbox­amide group is 26.79 (3)°. Molecules are linked by C—H...O, π–π and C—H...π interactions. In the latter interactions, C...centroid distances are 3.659 (4) and 3.816 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.058
• wR factor = 0.133
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H3     ..  H14     ..       2.09 Ang.

Alert level C
DIFMN02_ALERT_2_C  The minimum difference density is < -0.1*ZMAX*0.75
            _refine_diff_density_min given =     -0.672
            Test value =     -0.600
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.107
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............      -0.67 e/A   3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  CG3     ..       2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  CG4     ..       3.06 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (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).

4-Benzoyl-N-methyl-1,5-diphenyl-1H-pyrazole-3-carboxamide

Crystal data

C24H19N3O2	F(000) = 800
Mr = 381.42	Dx = 1.312 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6124 reflections
a = 8.6587 (10) Å	θ = 2.0–26.3°
b = 20.5881 (19) Å	µ = 0.09 mm^−1
c = 11.0082 (13) Å	T = 293 K
β = 100.187 (9)°	Prism, colourless
V = 1931.5 (4) Å^3	0.29 × 0.17 × 0.09 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	3400 independent reflections
Radiation source: sealed X-ray tube	1440 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.107
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 2.0°
w rotation scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
Tmin = 0.983, Tmax = 0.992	l = −13→13
20198 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0427P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3400 reflections	Δρmax = 0.49 e Å^−3
251 parameters	Δρmin = −0.67 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0091 (11)

Special details

Experimental. Solvents were dried by refluxing with the appropriate drying agents and distilled before use. All other reagents were purchased from Merck, Fluka, Aldrich and Acros Chemical Co., and used without further purification. Experiments were followed by TLC using DC Alufolien Kieselgel 60 F₂₅₄ Merck and a Camag TLC lamp (254/366 nm). After completion of the reactions, solvents were evaporated with a rotary evaporator (Buchi RE model 111). The melting point was determined on an Electrothermal 9200 apparatus and is uncorrected. Microanalysis was performed with a Carlo Erba Elemental Analyser Model 1108.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3468 (3)	0.20355 (13)	0.6187 (3)	0.0674 (9)
O2	0.1797 (3)	0.06184 (13)	0.7844 (3)	0.0650 (8)
N1	0.0017 (3)	0.26731 (14)	0.6910 (3)	0.0489 (8)
N2	−0.0980 (3)	0.23662 (14)	0.7561 (3)	0.0469 (8)
N3	0.2076 (3)	0.28783 (15)	0.5345 (3)	0.0542 (6)
H3	0.1203	0.3087	0.5246	0.065*
C1	−0.0670 (4)	0.17140 (17)	0.7696 (3)	0.0434 (9)
C2	0.0577 (4)	0.15942 (17)	0.7102 (3)	0.0452 (10)
C3	0.0941 (4)	0.21977 (18)	0.6635 (3)	0.0456 (10)
C4	0.2293 (4)	0.2360 (2)	0.6035 (4)	0.0542 (6)
C5	0.3339 (4)	0.30893 (19)	0.4755 (4)	0.0542 (6)
H5A	0.3032	0.3476	0.4287	0.081*
H5B	0.3584	0.2754	0.4213	0.081*
H5C	0.4246	0.3179	0.5370	0.081*
C6	0.1321 (4)	0.09558 (19)	0.6940 (4)	0.0508 (10)
C7	0.1501 (4)	0.07440 (18)	0.5681 (4)	0.0502 (10)
C8	0.0698 (5)	0.1029 (2)	0.4638 (4)	0.0635 (12)
H8	0.0004	0.1366	0.4706	0.076*
C9	0.0905 (5)	0.0822 (2)	0.3471 (4)	0.0716 (13)
H9	0.0367	0.1025	0.2767	0.086*
C10	0.1893 (5)	0.0324 (2)	0.3370 (5)	0.0714 (13)
H10	0.2031	0.0181	0.2595	0.086*
C11	0.2691 (5)	0.0031 (2)	0.4413 (5)	0.0781 (14)
H11	0.3374	−0.0309	0.4337	0.094*
C12	0.2500 (5)	0.0232 (2)	0.5567 (4)	0.0664 (13)
H12	0.3037	0.0024	0.6267	0.080*
C13	−0.1578 (4)	0.12776 (17)	0.8364 (3)	0.0439 (10)
C14	−0.0810 (4)	0.09463 (18)	0.9396 (4)	0.0543 (11)
H14	0.0262	0.1006	0.9657	0.065*
C15	−0.1623 (5)	0.05295 (19)	1.0038 (4)	0.0612 (11)
H15	−0.1098	0.0311	1.0729	0.073*
C16	−0.3193 (5)	0.0439 (2)	0.9659 (4)	0.0667 (13)
H16	−0.3735	0.0156	1.0092	0.080*
C17	−0.3988 (5)	0.0763 (2)	0.8637 (4)	0.0645 (12)
H17	−0.5060	0.0700	0.8385	0.077*
C18	−0.3182 (4)	0.11816 (18)	0.7995 (4)	0.0529 (11)
H18	−0.3717	0.1401	0.7309	0.063*
C19	−0.2127 (4)	0.27546 (18)	0.8027 (4)	0.0456 (9)
C20	−0.2435 (4)	0.26439 (19)	0.9188 (4)	0.0551 (11)
H20	−0.1899	0.2321	0.9684	0.066*
C21	−0.3560 (5)	0.3021 (2)	0.9614 (4)	0.0630 (12)
H21	−0.3789	0.2947	1.0397	0.076*
C22	−0.4336 (5)	0.3502 (2)	0.8885 (5)	0.0738 (14)
H22	−0.5100	0.3748	0.9168	0.089*
C23	−0.3980 (5)	0.3620 (2)	0.7735 (5)	0.0757 (14)
H23	−0.4484	0.3954	0.7253	0.091*
C24	−0.2877 (5)	0.3243 (2)	0.7288 (4)	0.0612 (11)
H24	−0.2646	0.3318	0.6507	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0522 (16)	0.070 (2)	0.086 (2)	0.0114 (14)	0.0271 (15)	0.0208 (16)
O2	0.0739 (19)	0.063 (2)	0.060 (2)	0.0165 (15)	0.0151 (16)	0.0100 (16)
N1	0.0545 (18)	0.045 (2)	0.051 (2)	−0.0045 (16)	0.0203 (17)	0.0016 (16)
N2	0.0472 (18)	0.045 (2)	0.052 (2)	0.0000 (16)	0.0183 (16)	0.0001 (16)
N3	0.0412 (11)	0.0658 (16)	0.0593 (15)	0.0054 (10)	0.0193 (10)	0.0219 (11)
C1	0.044 (2)	0.040 (2)	0.048 (3)	−0.0020 (17)	0.0133 (19)	−0.0010 (19)
C2	0.047 (2)	0.043 (2)	0.047 (3)	0.0006 (18)	0.0119 (19)	0.0015 (18)
C3	0.044 (2)	0.045 (2)	0.049 (3)	0.0030 (18)	0.0137 (19)	0.0007 (19)
C4	0.0412 (11)	0.0658 (16)	0.0593 (15)	0.0054 (10)	0.0193 (10)	0.0219 (11)
C5	0.0412 (11)	0.0658 (16)	0.0593 (15)	0.0054 (10)	0.0193 (10)	0.0219 (11)
C6	0.046 (2)	0.048 (3)	0.060 (3)	0.0019 (18)	0.014 (2)	0.003 (2)
C7	0.053 (2)	0.048 (3)	0.052 (3)	0.0031 (19)	0.017 (2)	0.001 (2)
C8	0.074 (3)	0.057 (3)	0.058 (3)	0.019 (2)	0.006 (2)	−0.002 (2)
C9	0.089 (3)	0.065 (3)	0.056 (3)	0.018 (3)	0.002 (3)	−0.002 (2)
C10	0.085 (3)	0.067 (3)	0.064 (3)	0.009 (3)	0.019 (3)	−0.011 (3)
C11	0.094 (4)	0.069 (3)	0.074 (4)	0.030 (3)	0.020 (3)	−0.008 (3)
C12	0.077 (3)	0.060 (3)	0.063 (3)	0.023 (2)	0.015 (3)	0.002 (2)
C13	0.043 (2)	0.041 (2)	0.049 (3)	0.0000 (17)	0.0109 (19)	−0.0016 (19)
C14	0.050 (2)	0.057 (3)	0.058 (3)	−0.001 (2)	0.015 (2)	0.001 (2)
C15	0.068 (3)	0.059 (3)	0.059 (3)	−0.001 (2)	0.018 (2)	0.010 (2)
C16	0.065 (3)	0.064 (3)	0.078 (4)	−0.012 (2)	0.031 (3)	0.007 (3)
C17	0.047 (2)	0.066 (3)	0.083 (4)	−0.013 (2)	0.019 (3)	0.000 (3)
C18	0.048 (2)	0.055 (3)	0.056 (3)	0.0020 (19)	0.011 (2)	−0.004 (2)
C19	0.045 (2)	0.045 (2)	0.048 (3)	0.0004 (18)	0.010 (2)	−0.006 (2)
C20	0.054 (2)	0.061 (3)	0.054 (3)	−0.001 (2)	0.019 (2)	−0.006 (2)
C21	0.067 (3)	0.065 (3)	0.062 (3)	−0.003 (2)	0.025 (2)	−0.013 (2)
C22	0.065 (3)	0.074 (4)	0.087 (4)	0.006 (2)	0.026 (3)	−0.023 (3)
C23	0.079 (3)	0.063 (3)	0.087 (4)	0.023 (3)	0.021 (3)	−0.002 (3)
C24	0.064 (3)	0.060 (3)	0.060 (3)	0.008 (2)	0.014 (2)	0.001 (2)

Geometric parameters (Å, º)

O1—C4	1.204 (4)	C11—C12	1.374 (5)
O2—C6	1.224 (4)	C11—H11	0.9300
N1—C3	1.332 (4)	C12—H12	0.9300
N1—N2	1.370 (4)	C13—C14	1.390 (5)
N2—C1	1.372 (4)	C13—C18	1.391 (5)
N2—C19	1.439 (4)	C14—C15	1.381 (5)
N3—C4	1.304 (4)	C14—H14	0.9300
N3—C5	1.434 (4)	C15—C16	1.363 (5)
N3—H3	0.8600	C15—H15	0.9300
C1—C2	1.380 (4)	C16—C17	1.383 (6)
C1—C13	1.473 (5)	C16—H16	0.9300
C2—C3	1.402 (5)	C17—C18	1.379 (5)
C2—C6	1.488 (5)	C17—H17	0.9300
C3—C4	1.480 (5)	C18—H18	0.9300
C5—H5A	0.9600	C19—C20	1.370 (5)
C5—H5B	0.9600	C19—C24	1.381 (5)
C5—H5C	0.9600	C20—C21	1.391 (5)
C6—C7	1.487 (5)	C20—H20	0.9300
C7—C8	1.365 (5)	C21—C22	1.374 (6)
C7—C12	1.384 (5)	C21—H21	0.9300
C8—C9	1.394 (5)	C22—C23	1.376 (6)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.353 (5)	C23—C24	1.386 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.371 (6)	C24—H24	0.9300
C10—H10	0.9300
C3—N1—N2	103.9 (3)	C10—C11—H11	119.4
N1—N2—C1	112.3 (3)	C12—C11—H11	119.4
N1—N2—C19	118.0 (3)	C11—C12—C7	119.5 (4)
C1—N2—C19	129.7 (3)	C11—C12—H12	120.2
C4—N3—C5	118.0 (3)	C7—C12—H12	120.2
C4—N3—H3	121.0	C14—C13—C18	118.5 (3)
C5—N3—H3	121.0	C14—C13—C1	119.2 (3)
N2—C1—C2	106.1 (3)	C18—C13—C1	122.3 (3)
N2—C1—C13	122.7 (3)	C15—C14—C13	120.7 (4)
C2—C1—C13	131.2 (3)	C15—C14—H14	119.7
C1—C2—C3	105.1 (3)	C13—C14—H14	119.7
C1—C2—C6	127.3 (3)	C16—C15—C14	120.0 (4)
C3—C2—C6	127.5 (3)	C16—C15—H15	120.0
N1—C3—C2	112.6 (3)	C14—C15—H15	120.0
N1—C3—C4	119.3 (3)	C15—C16—C17	120.6 (4)
C2—C3—C4	127.6 (3)	C15—C16—H16	119.7
O1—C4—N3	124.4 (3)	C17—C16—H16	119.7
O1—C4—C3	121.9 (4)	C18—C17—C16	119.7 (4)
N3—C4—C3	113.6 (3)	C18—C17—H17	120.2
N3—C5—H5A	109.5	C16—C17—H17	120.2
N3—C5—H5B	109.5	C17—C18—C13	120.6 (4)
H5A—C5—H5B	109.5	C17—C18—H18	119.7
N3—C5—H5C	109.5	C13—C18—H18	119.7
H5A—C5—H5C	109.5	C20—C19—C24	121.5 (4)
H5B—C5—H5C	109.5	C20—C19—N2	120.0 (3)
O2—C6—C7	121.0 (4)	C24—C19—N2	118.5 (3)
O2—C6—C2	119.7 (4)	C19—C20—C21	119.0 (4)
C7—C6—C2	119.3 (4)	C19—C20—H20	120.5
C8—C7—C12	119.0 (4)	C21—C20—H20	120.5
C8—C7—C6	122.5 (4)	C22—C21—C20	120.3 (4)
C12—C7—C6	118.6 (4)	C22—C21—H21	119.8
C7—C8—C9	121.0 (4)	C20—C21—H21	119.8
C7—C8—H8	119.5	C21—C22—C23	119.9 (4)
C9—C8—H8	119.5	C21—C22—H22	120.1
C10—C9—C8	119.6 (4)	C23—C22—H22	120.1
C10—C9—H9	120.2	C22—C23—C24	120.6 (4)
C8—C9—H9	120.2	C22—C23—H23	119.7
C9—C10—C11	119.8 (4)	C24—C23—H23	119.7
C9—C10—H10	120.1	C19—C24—C23	118.7 (4)
C11—C10—H10	120.1	C19—C24—H24	120.7
C10—C11—C12	121.1 (4)	C23—C24—H24	120.7
C3—N1—N2—C1	0.6 (4)	C6—C7—C8—C9	179.4 (4)
C3—N1—N2—C19	178.6 (3)	C7—C8—C9—C10	1.2 (7)
N1—N2—C1—C2	−0.3 (4)	C8—C9—C10—C11	−0.5 (7)
C19—N2—C1—C2	−178.1 (3)	C9—C10—C11—C12	0.4 (7)
N1—N2—C1—C13	179.8 (3)	C10—C11—C12—C7	−0.9 (7)
C19—N2—C1—C13	2.1 (6)	C8—C7—C12—C11	1.5 (6)
N2—C1—C2—C3	−0.1 (4)	C6—C7—C12—C11	−179.6 (4)
C13—C1—C2—C3	179.7 (4)	N2—C1—C13—C14	−119.5 (4)
N2—C1—C2—C6	−177.4 (3)	C2—C1—C13—C14	60.7 (6)
C13—C1—C2—C6	2.4 (7)	N2—C1—C13—C18	60.8 (5)
N2—N1—C3—C2	−0.6 (4)	C2—C1—C13—C18	−119.0 (4)
N2—N1—C3—C4	−173.6 (3)	C18—C13—C14—C15	0.2 (6)
C1—C2—C3—N1	0.5 (4)	C1—C13—C14—C15	−179.5 (4)
C6—C2—C3—N1	177.8 (4)	C13—C14—C15—C16	0.1 (6)
C1—C2—C3—C4	172.8 (4)	C14—C15—C16—C17	−0.3 (6)
C6—C2—C3—C4	−9.9 (6)	C15—C16—C17—C18	0.1 (7)
C5—N3—C4—O1	−2.0 (7)	C16—C17—C18—C13	0.2 (6)
C5—N3—C4—C3	178.0 (3)	C14—C13—C18—C17	−0.4 (6)
N1—C3—C4—O1	150.4 (4)	C1—C13—C18—C17	179.3 (3)
C2—C3—C4—O1	−21.4 (7)	N1—N2—C19—C20	−138.7 (4)
N1—C3—C4—N3	−29.5 (5)	C1—N2—C19—C20	39.0 (6)
C2—C3—C4—N3	158.6 (4)	N1—N2—C19—C24	40.1 (5)
C1—C2—C6—O2	−54.2 (6)	C1—N2—C19—C24	−142.2 (4)
C3—C2—C6—O2	129.1 (4)	C24—C19—C20—C21	1.9 (6)
C1—C2—C6—C7	127.0 (4)	N2—C19—C20—C21	−179.3 (3)
C3—C2—C6—C7	−49.7 (5)	C19—C20—C21—C22	−0.8 (6)
O2—C6—C7—C8	165.3 (4)	C20—C21—C22—C23	−1.1 (7)
C2—C6—C7—C8	−15.9 (5)	C21—C22—C23—C24	1.9 (7)
O2—C6—C7—C12	−13.5 (6)	C20—C19—C24—C23	−1.0 (6)
C2—C6—C7—C12	165.3 (3)	N2—C19—C24—C23	−179.8 (4)
C12—C7—C8—C9	−1.7 (6)	C22—C23—C24—C19	−0.9 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1	0.86	2.41	2.723 (4)	102
C5—H5A···O2^i	0.96	2.56	3.506 (5)	170
C10—H10···Cg3^ii	0.93	2.83	3.659 (4)	149
C8—H8···Cg4^iii	0.93	3.06	3.816 (4)	139

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z; (iii) x, −y−1/2, z−3/2.