Crystal structure of (Z)-4-[1-(4-acetyl­anilino)ethyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

In the solid state, the title compound, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intra­molecular N—H...O hydrogen bond with an S(6) ring motif. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds to generate C(16) chains propagating in the [301] direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.126
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     12.695 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.793 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.80 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Report

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

   1 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
   6 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

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-RED32 (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).

(Z)-4-[1-(4-Acetylanilino)ethylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Crystal data

C20H19N3O2	F(000) = 704
Mr = 333.38	Dx = 1.282 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.8549 (4) Å	Cell parameters from 3705 reflections
b = 11.6070 (5) Å	θ = 2.4–26.7°
c = 13.1591 (5) Å	µ = 0.09 mm^−1
β = 107.425 (3)°	T = 296 K
V = 1727.60 (12) Å^3	Slab, yellow
Z = 4	0.80 × 0.57 × 0.10 mm

Data collection

Stoe IPDS 2 diffractometer	2772 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
ω–scan rotation method	θmax = 26.5°, θmin = 2.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −14→14
Tmin = 0.935, Tmax = 0.991	k = −14→14
25592 measured reflections	l = −16→16
3584 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: mixed
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0592P)^2 + 0.1897P] where P = (Fo^2 + 2Fc^2)/3
3584 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.17 e Å^−3
1 restraint	Δρmin = −0.16 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.68663 (14)	0.70961 (15)	0.55951 (13)	0.0594 (4)
C2	0.78901 (16)	0.70082 (19)	0.64551 (16)	0.0771 (5)
H2	0.7865	0.6647	0.7079	0.093*
C3	0.89330 (18)	0.7453 (2)	0.6381 (2)	0.0931 (7)
H3	0.9614	0.7388	0.6957	0.112*
C4	0.89876 (19)	0.7993 (2)	0.5472 (2)	0.0923 (7)
H4	0.9701	0.8287	0.5427	0.111*
C5	0.79784 (19)	0.8096 (2)	0.46270 (19)	0.0838 (6)
H5	0.8011	0.8472	0.4012	0.101*
C6	0.69112 (16)	0.76487 (17)	0.46756 (16)	0.0698 (5)
H6	0.6234	0.7719	0.4097	0.084*
C7	0.47116 (14)	0.65691 (14)	0.49191 (12)	0.0542 (4)
C8	0.39461 (14)	0.60235 (13)	0.54463 (12)	0.0530 (4)
C9	0.46974 (15)	0.57875 (15)	0.65068 (12)	0.0583 (4)
C10	0.4410 (2)	0.5216 (2)	0.74124 (14)	0.0825 (6)
H10A	0.4126	0.4450	0.7208	0.099*
H10B	0.3811	0.5651	0.7598	0.099*
H10C	0.5107	0.5179	0.8015	0.099*
C11	0.27542 (14)	0.58305 (14)	0.49366 (12)	0.0536 (4)
C12	0.19337 (16)	0.53059 (17)	0.54741 (14)	0.0685 (5)
H12A	0.1621	0.5898	0.5822	0.103*
H12B	0.2356	0.4753	0.5992	0.103*
H12C	0.1296	0.4929	0.4954	0.103*
C13	0.11905 (14)	0.61084 (14)	0.31950 (12)	0.0545 (4)
C14	0.10632 (15)	0.57899 (16)	0.21567 (13)	0.0633 (4)
H14	0.1718	0.5538	0.1968	0.076*
C15	−0.00252 (15)	0.58422 (17)	0.13969 (14)	0.0661 (5)
H15	−0.0096	0.5630	0.0699	0.079*
C16	−0.10156 (14)	0.62055 (15)	0.16568 (13)	0.0595 (4)
C17	−0.08768 (15)	0.65196 (16)	0.27021 (15)	0.0663 (5)
H17	−0.1534	0.6762	0.2892	0.080*
C18	0.02076 (15)	0.64829 (16)	0.34677 (14)	0.0647 (4)
H18	0.0281	0.6708	0.4163	0.078*
C19	−0.22040 (16)	0.63304 (18)	0.08467 (17)	0.0739 (5)
C20	−0.23519 (19)	0.5992 (2)	−0.02808 (16)	0.0863 (6)
H20A	−0.2151	0.5193	−0.0307	0.104*
H20B	−0.1841	0.6453	−0.0560	0.104*
H20C	−0.3158	0.6111	−0.0700	0.104*
N1	0.57996 (12)	0.66251 (12)	0.56781 (10)	0.0576 (3)
N2	0.57755 (13)	0.61356 (13)	0.66442 (11)	0.0639 (4)
N3	0.23507 (12)	0.61234 (13)	0.39067 (11)	0.0586 (4)
O1	0.44674 (10)	0.69356 (12)	0.39873 (9)	0.0673 (3)
O2	−0.30253 (13)	0.67134 (17)	0.11080 (14)	0.1087 (6)
H3A	0.2925 (16)	0.6339 (18)	0.3635 (15)	0.086 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0516 (9)	0.0619 (10)	0.0649 (10)	−0.0006 (7)	0.0176 (7)	−0.0177 (8)
C2	0.0589 (10)	0.0909 (14)	0.0741 (12)	−0.0009 (10)	0.0089 (9)	−0.0204 (10)
C3	0.0577 (11)	0.1136 (18)	0.1009 (17)	−0.0079 (11)	0.0128 (11)	−0.0380 (15)
C4	0.0619 (12)	0.1057 (17)	0.1176 (18)	−0.0214 (11)	0.0397 (12)	−0.0490 (15)
C5	0.0779 (13)	0.0907 (15)	0.0948 (15)	−0.0168 (11)	0.0439 (12)	−0.0234 (12)
C6	0.0608 (10)	0.0796 (12)	0.0721 (11)	−0.0067 (9)	0.0247 (9)	−0.0135 (9)
C7	0.0521 (8)	0.0580 (9)	0.0512 (8)	0.0024 (7)	0.0136 (7)	−0.0054 (7)
C8	0.0568 (9)	0.0529 (9)	0.0501 (8)	0.0012 (7)	0.0170 (7)	−0.0024 (7)
C9	0.0649 (10)	0.0575 (9)	0.0504 (8)	0.0038 (8)	0.0140 (7)	−0.0007 (7)
C10	0.0912 (14)	0.0940 (15)	0.0590 (10)	−0.0028 (12)	0.0177 (10)	0.0137 (10)
C11	0.0579 (9)	0.0505 (9)	0.0537 (8)	0.0007 (7)	0.0186 (7)	−0.0032 (7)
C12	0.0693 (11)	0.0700 (11)	0.0697 (11)	−0.0055 (9)	0.0263 (9)	0.0063 (9)
C13	0.0499 (8)	0.0561 (9)	0.0568 (9)	−0.0027 (7)	0.0148 (7)	0.0001 (7)
C14	0.0529 (9)	0.0800 (12)	0.0587 (9)	0.0079 (8)	0.0195 (7)	−0.0031 (8)
C15	0.0619 (10)	0.0783 (12)	0.0554 (9)	0.0041 (9)	0.0133 (8)	−0.0057 (8)
C16	0.0504 (9)	0.0597 (10)	0.0663 (10)	−0.0039 (7)	0.0145 (7)	0.0045 (8)
C17	0.0525 (9)	0.0752 (12)	0.0760 (11)	0.0051 (8)	0.0267 (8)	0.0036 (9)
C18	0.0620 (10)	0.0753 (12)	0.0602 (9)	0.0041 (9)	0.0233 (8)	−0.0053 (8)
C19	0.0530 (10)	0.0735 (12)	0.0898 (13)	−0.0073 (9)	0.0133 (9)	0.0103 (10)
C20	0.0737 (13)	0.0826 (14)	0.0827 (13)	−0.0088 (11)	−0.0069 (10)	0.0038 (11)
N1	0.0527 (7)	0.0649 (8)	0.0527 (7)	0.0008 (6)	0.0120 (6)	−0.0036 (6)
N2	0.0657 (9)	0.0692 (9)	0.0519 (7)	0.0039 (7)	0.0104 (6)	0.0015 (6)
N3	0.0496 (7)	0.0718 (9)	0.0546 (8)	−0.0041 (6)	0.0158 (6)	−0.0003 (6)
O1	0.0583 (7)	0.0915 (9)	0.0505 (6)	−0.0052 (6)	0.0139 (5)	0.0071 (6)
O2	0.0523 (8)	0.1516 (16)	0.1176 (13)	0.0109 (9)	0.0185 (8)	0.0077 (11)

Geometric parameters (Å, º)

C1—C6	1.385 (3)	C11—C12	1.493 (2)
C1—C2	1.393 (2)	C12—H12A	0.9600
C1—N1	1.412 (2)	C12—H12B	0.9600
C2—C3	1.370 (3)	C12—H12C	0.9600
C2—H2	0.9300	C13—C14	1.380 (2)
C3—C4	1.370 (4)	C13—C18	1.388 (2)
C3—H3	0.9300	C13—N3	1.413 (2)
C4—C5	1.373 (3)	C14—C15	1.377 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.387 (3)	C15—C16	1.383 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.384 (2)
C7—O1	1.2472 (19)	C16—C19	1.498 (2)
C7—N1	1.376 (2)	C17—C18	1.376 (2)
C7—C8	1.443 (2)	C17—H17	0.9300
C8—C11	1.389 (2)	C18—H18	0.9300
C8—C9	1.439 (2)	C19—O2	1.210 (2)
C9—N2	1.300 (2)	C19—C20	1.494 (3)
C9—C10	1.490 (2)	C20—H20A	0.9600
C10—H10A	0.9600	C20—H20B	0.9600
C10—H10B	0.9600	C20—H20C	0.9600
C10—H10C	0.9600	N1—N2	1.4006 (19)
C11—N3	1.339 (2)	N3—H3A	0.895 (15)
C6—C1—C2	119.44 (17)	H12A—C12—H12B	109.5
C6—C1—N1	121.12 (15)	C11—C12—H12C	109.5
C2—C1—N1	119.44 (17)	H12A—C12—H12C	109.5
C3—C2—C1	120.0 (2)	H12B—C12—H12C	109.5
C3—C2—H2	120.0	C14—C13—C18	119.26 (15)
C1—C2—H2	120.0	C14—C13—N3	117.11 (14)
C4—C3—C2	120.9 (2)	C18—C13—N3	123.42 (15)
C4—C3—H3	119.5	C15—C14—C13	120.55 (15)
C2—C3—H3	119.5	C15—C14—H14	119.7
C3—C4—C5	119.3 (2)	C13—C14—H14	119.7
C3—C4—H4	120.3	C14—C15—C16	120.94 (16)
C5—C4—H4	120.3	C14—C15—H15	119.5
C4—C5—C6	121.1 (2)	C16—C15—H15	119.5
C4—C5—H5	119.5	C15—C16—C17	117.95 (15)
C6—C5—H5	119.5	C15—C16—C19	122.73 (16)
C1—C6—C5	119.22 (19)	C17—C16—C19	119.24 (16)
C1—C6—H6	120.4	C18—C17—C16	121.75 (16)
C5—C6—H6	120.4	C18—C17—H17	119.1
O1—C7—N1	126.05 (15)	C16—C17—H17	119.1
O1—C7—C8	128.90 (14)	C17—C18—C13	119.55 (16)
N1—C7—C8	105.04 (13)	C17—C18—H18	120.2
C11—C8—C9	133.02 (15)	C13—C18—H18	120.2
C11—C8—C7	122.26 (14)	O2—C19—C20	120.93 (18)
C9—C8—C7	104.71 (14)	O2—C19—C16	119.9 (2)
N2—C9—C8	111.89 (15)	C20—C19—C16	119.16 (18)
N2—C9—C10	118.56 (15)	C19—C20—H20A	109.5
C8—C9—C10	129.55 (16)	C19—C20—H20B	109.5
C9—C10—H10A	109.5	H20A—C20—H20B	109.5
C9—C10—H10B	109.5	C19—C20—H20C	109.5
H10A—C10—H10B	109.5	H20A—C20—H20C	109.5
C9—C10—H10C	109.5	H20B—C20—H20C	109.5
H10A—C10—H10C	109.5	C7—N1—N2	111.72 (13)
H10B—C10—H10C	109.5	C7—N1—C1	128.96 (14)
N3—C11—C8	116.82 (14)	N2—N1—C1	119.31 (13)
N3—C11—C12	119.81 (15)	C9—N2—N1	106.63 (13)
C8—C11—C12	123.36 (14)	C11—N3—C13	130.49 (14)
C11—C12—H12A	109.5	C11—N3—H3A	113.1 (13)
C11—C12—H12B	109.5	C13—N3—H3A	116.4 (13)
C6—C1—C2—C3	−0.8 (3)	C15—C16—C17—C18	0.4 (3)
N1—C1—C2—C3	179.45 (18)	C19—C16—C17—C18	−176.39 (17)
C1—C2—C3—C4	0.3 (3)	C16—C17—C18—C13	−0.8 (3)
C2—C3—C4—C5	0.5 (3)	C14—C13—C18—C17	0.6 (3)
C3—C4—C5—C6	−0.9 (3)	N3—C13—C18—C17	175.11 (17)
C2—C1—C6—C5	0.5 (3)	C15—C16—C19—O2	−175.8 (2)
N1—C1—C6—C5	−179.81 (16)	C17—C16—C19—O2	0.7 (3)
C4—C5—C6—C1	0.4 (3)	C15—C16—C19—C20	3.4 (3)
O1—C7—C8—C11	−0.1 (3)	C17—C16—C19—C20	179.97 (18)
N1—C7—C8—C11	178.89 (14)	O1—C7—N1—N2	179.96 (15)
O1—C7—C8—C9	−179.84 (17)	C8—C7—N1—N2	0.89 (17)
N1—C7—C8—C9	−0.80 (16)	O1—C7—N1—C1	0.2 (3)
C11—C8—C9—N2	−179.15 (17)	C8—C7—N1—C1	−178.83 (15)
C7—C8—C9—N2	0.49 (19)	C6—C1—N1—C7	3.6 (3)
C11—C8—C9—C10	1.4 (3)	C2—C1—N1—C7	−176.73 (16)
C7—C8—C9—C10	−178.95 (18)	C6—C1—N1—N2	−176.12 (16)
C9—C8—C11—N3	−177.17 (17)	C2—C1—N1—N2	3.6 (2)
C7—C8—C11—N3	3.2 (2)	C8—C9—N2—N1	0.04 (19)
C9—C8—C11—C12	1.8 (3)	C10—C9—N2—N1	179.55 (16)
C7—C8—C11—C12	−177.78 (16)	C7—N1—N2—C9	−0.60 (19)
C18—C13—C14—C15	0.0 (3)	C1—N1—N2—C9	179.15 (14)
N3—C13—C14—C15	−174.80 (16)	C8—C11—N3—C13	−175.30 (16)
C13—C14—C15—C16	−0.5 (3)	C12—C11—N3—C13	5.7 (3)
C14—C15—C16—C17	0.3 (3)	C14—C13—N3—C11	−142.71 (18)
C14—C15—C16—C19	176.95 (17)	C18—C13—N3—C11	42.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.90 (2)	1.88 (2)	2.6527 (18)	144 (2)
C4—H4···O2^i	0.93	2.57	3.403 (2)	150

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