5-Methyl-4-(5-methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)-2-phenyl-1H-pyrazol-3(2H)-one

Powell, G.L.; Rix, B.A.

doi:10.1107/S2414314620001212

5-Methyl-4-(5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-phenyl-1H-pyrazol-3(2H)-one

The title compound, C₂₀H₁₈N₄O₂, known as bispyrazolone, was crystallized from dimethyl sulfoxide. The structure has orthorhombic (Pbca) symmetry at 150 K, and displays both intra- and intermolecular hydrogen bonding through C—H

O and N—H

O contacts, respectively. None of the phenyl and pyrazolone rings in the molecule are coplanar. The dihedral angle between the pyrazolone rings is 66.18 (5)°.

Keywords: crystal structure; pyrazolone rings; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314620001212/wm4125sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314620001212/wm4125Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314620001212/wm4125Isup3.cml Supplementary material

CCDC reference: 1949067

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.113
Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00020 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         55 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   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
   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

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5-Methyl-4-(5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₀H₁₈N₄O₂	D_x = 1.349 Mg m⁻³
M_r = 346.38	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 9599 reflections
a = 8.7438 (1) Å	θ = 4.7–72.3°
b = 18.7561 (2) Å	µ = 0.73 mm⁻¹
c = 20.8005 (2) Å	T = 150 K
V = 3411.27 (6) Å³	Plate, clear colourless
Z = 8	0.27 × 0.21 × 0.03 mm
F(000) = 1456

Data collection top

Rigaku Oxford Diffraction SuperNova, Cu, AtlasS2 CCD diffractometer	3336 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3020 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 5.2387 pixels mm^-1	θ_max = 72.6°, θ_min = 4.3°
ω scans	h = −7→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −22→23
T_min = 0.874, T_max = 1.000	l = −25→24
16964 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	All H-atom parameters refined
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0692P)² + 1.0751P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3336 reflections	Δρ_max = 0.26 e Å⁻³
307 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The H atoms bound to N2 and N4 were located in a difference map and refined. All hydrogen atoms were located in a difference map and were refined isotropically without constraints.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.17850 (10)	0.59409 (5)	0.52406 (4)	0.0228 (2)
O2	0.41464 (11)	0.62429 (5)	0.38211 (4)	0.0254 (2)
N1	0.33303 (11)	0.51616 (5)	0.58208 (5)	0.0197 (2)
N2	0.48738 (12)	0.51224 (6)	0.59817 (5)	0.0203 (2)
H2	0.525 (2)	0.4688 (11)	0.6043 (9)	0.040 (5)*
N3	0.49474 (13)	0.74084 (6)	0.40463 (5)	0.0228 (2)
N4	0.53811 (15)	0.77703 (6)	0.45972 (6)	0.0283 (3)
H4	0.587 (2)	0.8209 (12)	0.4598 (9)	0.043 (5)*
C1	0.30864 (14)	0.57394 (6)	0.54173 (6)	0.0189 (3)
C2	0.45779 (14)	0.60260 (6)	0.52877 (6)	0.0200 (3)
C3	0.56144 (15)	0.56250 (6)	0.56271 (6)	0.0205 (3)
C4	0.73088 (16)	0.56807 (8)	0.56622 (7)	0.0280 (3)
H4A	0.760 (2)	0.5841 (11)	0.6082 (10)	0.047 (5)*
H4B	0.769 (2)	0.6027 (12)	0.5330 (10)	0.048 (5)*
H4C	0.781 (2)	0.5205 (13)	0.5591 (11)	0.057 (6)*
C5	0.46008 (14)	0.67053 (6)	0.42150 (6)	0.0206 (3)
C6	0.48650 (14)	0.66557 (6)	0.48898 (6)	0.0210 (3)
C7	0.53634 (16)	0.73124 (7)	0.50942 (7)	0.0252 (3)
C8	0.5806 (2)	0.75544 (8)	0.57491 (7)	0.0378 (4)
H8A	0.615 (3)	0.7180 (16)	0.6015 (14)	0.088 (9)*
H8B	0.657 (3)	0.7932 (13)	0.5731 (11)	0.060 (6)*
H8C	0.490 (3)	0.7748 (16)	0.5982 (14)	0.086 (9)*
C9	0.22459 (14)	0.47963 (6)	0.62063 (6)	0.0203 (3)
C10	0.26090 (16)	0.46291 (7)	0.68395 (7)	0.0249 (3)
H10	0.3582 (19)	0.4766 (9)	0.7016 (8)	0.028 (4)*
C11	0.15554 (16)	0.42644 (7)	0.72142 (7)	0.0282 (3)
H11	0.1800 (19)	0.4165 (9)	0.7650 (9)	0.030 (4)*
C12	0.01470 (16)	0.40714 (7)	0.69603 (7)	0.0280 (3)
H12	−0.060 (2)	0.3814 (9)	0.7228 (9)	0.033 (4)*
C13	−0.02218 (15)	0.42573 (7)	0.63351 (7)	0.0264 (3)
H13	−0.122 (2)	0.4129 (9)	0.6151 (8)	0.031 (4)*
C14	0.08272 (15)	0.46155 (7)	0.59499 (7)	0.0234 (3)
H14	0.0610 (18)	0.4727 (9)	0.5502 (8)	0.025 (4)*
C15	0.47280 (15)	0.77740 (7)	0.34550 (6)	0.0232 (3)
C16	0.52997 (19)	0.84583 (8)	0.33728 (8)	0.0349 (4)
H16	0.585 (2)	0.8683 (12)	0.3736 (11)	0.056 (6)*
C17	0.5073 (2)	0.88090 (8)	0.27926 (8)	0.0388 (4)
H17	0.552 (2)	0.9301 (11)	0.2736 (10)	0.046 (5)*
C18	0.4295 (2)	0.84888 (8)	0.22973 (7)	0.0368 (4)
H18	0.417 (2)	0.8738 (10)	0.1885 (9)	0.040 (5)*
C19	0.3694 (2)	0.78142 (9)	0.23859 (8)	0.0440 (4)
H19	0.313 (2)	0.7578 (12)	0.2045 (11)	0.054 (6)*
C20	0.3906 (2)	0.74557 (8)	0.29632 (7)	0.0367 (4)
H20	0.352 (2)	0.6986 (12)	0.3029 (10)	0.051 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0240 (5)	0.0187 (4)	0.0256 (5)	0.0027 (3)	−0.0025 (4)	0.0029 (3)
O2	0.0357 (5)	0.0157 (4)	0.0249 (5)	−0.0017 (3)	−0.0066 (4)	0.0006 (3)
N1	0.0195 (5)	0.0171 (5)	0.0225 (5)	0.0002 (4)	−0.0011 (4)	0.0039 (4)
N2	0.0209 (5)	0.0164 (5)	0.0236 (6)	0.0011 (4)	−0.0016 (4)	0.0029 (4)
N3	0.0324 (6)	0.0162 (5)	0.0197 (5)	−0.0033 (4)	−0.0008 (4)	0.0012 (4)
N4	0.0449 (7)	0.0185 (5)	0.0213 (6)	−0.0102 (5)	−0.0016 (5)	0.0012 (4)
C1	0.0256 (6)	0.0143 (5)	0.0167 (6)	0.0014 (4)	−0.0002 (5)	0.0000 (4)
C2	0.0255 (6)	0.0156 (6)	0.0190 (6)	−0.0012 (4)	−0.0001 (5)	0.0005 (5)
C3	0.0248 (6)	0.0167 (5)	0.0200 (6)	−0.0008 (5)	0.0007 (5)	−0.0007 (5)
C4	0.0241 (7)	0.0275 (7)	0.0324 (8)	−0.0017 (5)	−0.0014 (6)	0.0024 (6)
C5	0.0231 (6)	0.0147 (5)	0.0241 (6)	0.0002 (4)	0.0000 (5)	0.0022 (5)
C6	0.0246 (6)	0.0166 (6)	0.0219 (6)	−0.0014 (5)	0.0006 (5)	0.0018 (5)
C7	0.0339 (7)	0.0193 (6)	0.0224 (7)	−0.0040 (5)	0.0005 (5)	0.0014 (5)
C8	0.0647 (11)	0.0249 (7)	0.0238 (7)	−0.0129 (7)	−0.0052 (7)	−0.0002 (6)
C9	0.0236 (6)	0.0141 (5)	0.0233 (6)	0.0005 (4)	0.0021 (5)	0.0019 (4)
C10	0.0266 (6)	0.0227 (6)	0.0255 (7)	−0.0013 (5)	−0.0012 (5)	0.0033 (5)
C11	0.0332 (7)	0.0262 (6)	0.0253 (7)	0.0020 (5)	0.0031 (6)	0.0079 (5)
C12	0.0275 (7)	0.0216 (6)	0.0350 (8)	0.0008 (5)	0.0096 (6)	0.0051 (5)
C13	0.0229 (6)	0.0206 (6)	0.0357 (8)	−0.0004 (5)	0.0013 (6)	0.0010 (5)
C14	0.0245 (6)	0.0198 (6)	0.0258 (7)	0.0009 (5)	−0.0009 (5)	0.0012 (5)
C15	0.0285 (6)	0.0192 (6)	0.0218 (6)	0.0020 (5)	0.0035 (5)	0.0035 (5)
C16	0.0443 (8)	0.0274 (7)	0.0330 (8)	−0.0110 (6)	−0.0079 (7)	0.0083 (6)
C17	0.0509 (9)	0.0276 (7)	0.0381 (9)	−0.0095 (6)	−0.0046 (7)	0.0127 (6)
C18	0.0549 (9)	0.0295 (7)	0.0261 (7)	0.0019 (7)	−0.0006 (7)	0.0088 (6)
C19	0.0753 (12)	0.0302 (7)	0.0265 (8)	−0.0055 (8)	−0.0128 (8)	0.0028 (6)
C20	0.0616 (10)	0.0210 (7)	0.0274 (8)	−0.0076 (7)	−0.0076 (7)	0.0029 (6)

Geometric parameters (Å, º) top

O1—C1	1.2540 (15)	C8—H8C	1.00 (3)
O2—C5	1.2577 (16)	C9—C10	1.3908 (18)
N1—N2	1.3924 (15)	C9—C14	1.3922 (18)
N1—C1	1.3873 (15)	C10—H10	0.962 (17)
N1—C9	1.4182 (16)	C10—C11	1.3870 (19)
N2—H2	0.89 (2)	C11—H11	0.950 (18)
N2—C3	1.3608 (16)	C11—C12	1.388 (2)
N3—N4	1.3848 (15)	C12—H12	0.986 (18)
N3—C5	1.3979 (15)	C12—C13	1.384 (2)
N3—C15	1.4211 (16)	C13—H13	0.982 (18)
N4—H4	0.93 (2)	C13—C14	1.3908 (19)
N4—C7	1.3442 (17)	C14—H14	0.973 (17)
C1—C2	1.4361 (17)	C15—C16	1.3880 (19)
C2—C3	1.3732 (18)	C15—C20	1.385 (2)
C2—C6	1.4638 (17)	C16—H16	0.99 (2)
C3—C4	1.4870 (18)	C16—C17	1.389 (2)
C4—H4A	0.96 (2)	C17—H17	1.01 (2)
C4—H4B	1.01 (2)	C17—C18	1.373 (2)
C4—H4C	1.00 (2)	C18—H18	0.984 (19)
C5—C6	1.4255 (18)	C18—C19	1.382 (2)
C6—C7	1.3739 (18)	C19—H19	0.97 (2)
C7—C8	1.487 (2)	C19—C20	1.389 (2)
C8—H8A	0.94 (3)	C20—H20	0.95 (2)
C8—H8B	0.98 (2)

N2—N1—C9	119.13 (10)	H8A—C8—H8B	110 (2)
C1—N1—N2	109.61 (10)	H8A—C8—H8C	104 (2)
C1—N1—C9	128.07 (10)	H8B—C8—H8C	108 (2)
N1—N2—H2	116.1 (12)	C10—C9—N1	119.46 (11)
C3—N2—N1	107.13 (10)	C10—C9—C14	120.74 (12)
C3—N2—H2	122.7 (12)	C14—C9—N1	119.80 (12)
N4—N3—C5	108.30 (10)	C9—C10—H10	120.3 (10)
N4—N3—C15	121.11 (10)	C11—C10—C9	119.46 (13)
C5—N3—C15	130.03 (11)	C11—C10—H10	120.3 (10)
N3—N4—H4	124.2 (12)	C10—C11—H11	118.9 (10)
C7—N4—N3	108.67 (11)	C10—C11—C12	120.27 (13)
C7—N4—H4	124.8 (12)	C12—C11—H11	120.8 (10)
O1—C1—N1	123.52 (11)	C11—C12—H12	120.1 (10)
O1—C1—C2	131.01 (11)	C13—C12—C11	119.90 (13)
N1—C1—C2	105.45 (10)	C13—C12—H12	120.0 (10)
C1—C2—C6	124.33 (11)	C12—C13—H13	120.7 (10)
C3—C2—C1	107.32 (11)	C12—C13—C14	120.61 (13)
C3—C2—C6	128.27 (12)	C14—C13—H13	118.7 (10)
N2—C3—C2	110.12 (11)	C9—C14—H14	119.2 (10)
N2—C3—C4	119.75 (11)	C13—C14—C9	118.99 (12)
C2—C3—C4	130.11 (12)	C13—C14—H14	121.7 (10)
C3—C4—H4A	109.2 (12)	C16—C15—N3	120.27 (13)
C3—C4—H4B	110.2 (12)	C20—C15—N3	120.08 (12)
C3—C4—H4C	111.4 (13)	C20—C15—C16	119.63 (13)
H4A—C4—H4B	109.6 (17)	C15—C16—H16	118.3 (13)
H4A—C4—H4C	107.4 (18)	C15—C16—C17	119.58 (14)
H4B—C4—H4C	109.1 (17)	C17—C16—H16	122.1 (13)
O2—C5—N3	123.75 (12)	C16—C17—H17	118.7 (11)
O2—C5—C6	130.37 (11)	C18—C17—C16	121.05 (14)
N3—C5—C6	105.88 (10)	C18—C17—H17	120.2 (11)
C5—C6—C2	125.56 (11)	C17—C18—H18	120.2 (11)
C7—C6—C2	127.07 (12)	C17—C18—C19	119.25 (14)
C7—C6—C5	107.31 (11)	C19—C18—H18	120.6 (11)
N4—C7—C6	109.78 (12)	C18—C19—H19	120.9 (13)
N4—C7—C8	120.43 (12)	C18—C19—C20	120.51 (15)
C6—C7—C8	129.77 (12)	C20—C19—H19	118.6 (13)
C7—C8—H8A	113.1 (18)	C15—C20—C19	119.94 (14)
C7—C8—H8B	111.4 (14)	C15—C20—H20	118.5 (13)
C7—C8—H8C	110.3 (16)	C19—C20—H20	121.5 (13)

O1—C1—C2—C3	176.71 (13)	C1—C2—C6—C7	110.02 (16)
O1—C1—C2—C6	−0.3 (2)	C2—C6—C7—N4	−175.33 (13)
O2—C5—C6—C2	−3.0 (2)	C2—C6—C7—C8	3.0 (3)
O2—C5—C6—C7	179.71 (14)	C3—C2—C6—C5	116.89 (15)
N1—N2—C3—C2	5.32 (14)	C3—C2—C6—C7	−66.4 (2)
N1—N2—C3—C4	−175.97 (11)	C5—N3—N4—C7	1.98 (15)
N1—C1—C2—C3	−1.56 (14)	C5—N3—C15—C16	−173.56 (14)
N1—C1—C2—C6	−178.61 (11)	C5—N3—C15—C20	8.1 (2)
N1—C9—C10—C11	−179.24 (12)	C5—C6—C7—N4	1.88 (16)
N1—C9—C14—C13	180.00 (11)	C5—C6—C7—C8	−179.78 (16)
N2—N1—C1—O1	−173.60 (11)	C6—C2—C3—N2	174.55 (12)
N2—N1—C1—C2	4.83 (13)	C6—C2—C3—C4	−4.0 (2)
N2—N1—C9—C10	23.01 (16)	C9—N1—N2—C3	−167.76 (11)
N2—N1—C9—C14	−157.62 (11)	C9—N1—C1—O1	−14.3 (2)
N3—N4—C7—C6	−2.41 (16)	C9—N1—C1—C2	164.12 (12)
N3—N4—C7—C8	179.07 (14)	C9—C10—C11—C12	−0.3 (2)
N3—C5—C6—C2	176.64 (12)	C10—C9—C14—C13	−0.64 (19)
N3—C5—C6—C7	−0.62 (14)	C10—C11—C12—C13	−1.4 (2)
N3—C15—C16—C17	−179.85 (14)	C11—C12—C13—C14	2.2 (2)
N3—C15—C20—C19	−179.98 (15)	C12—C13—C14—C9	−1.17 (19)
N4—N3—C5—O2	178.89 (12)	C14—C9—C10—C11	1.40 (19)
N4—N3—C5—C6	−0.81 (14)	C15—N3—N4—C7	174.20 (12)
N4—N3—C15—C16	16.11 (19)	C15—N3—C5—O2	7.6 (2)
N4—N3—C15—C20	−162.19 (14)	C15—N3—C5—C6	−172.10 (12)
C1—N1—N2—C3	−6.34 (13)	C15—C16—C17—C18	−0.2 (3)
C1—N1—C9—C10	−134.57 (13)	C16—C15—C20—C19	1.7 (3)
C1—N1—C9—C14	44.80 (18)	C16—C17—C18—C19	1.8 (3)
C1—C2—C3—N2	−2.35 (14)	C17—C18—C19—C20	−1.6 (3)
C1—C2—C3—C4	179.11 (13)	C18—C19—C20—C15	−0.1 (3)
C1—C2—C6—C5	−66.70 (18)	C20—C15—C16—C17	−1.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.89 (2)	1.85 (2)	2.7313 (14)	175.1 (18)
N4—H4···O1ⁱⁱ	0.93 (2)	1.81 (2)	2.7321 (15)	169.3 (18)
C20—H20···O2	0.95 (2)	2.23 (2)	2.8988 (17)	126.5 (16)

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

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5-Methyl-4-(5-methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)-2-phenyl-1H-pyrazol-3(2H)-one

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5-Methyl-4-(5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-phenyl-1H-pyrazol-3(2H)-one