4-[(Z)-(Benzyl­amino)­phenyl­methyl­ene]-5-methyl-2-phenyl-2H-pyrazol-3-one

Jiang, J.-J.; Lü, X.-Q.; Bao, F.; Kang, B.-S.; Ng, S.W.

doi:10.1107/S1600536804013479

4-[(Z)-(Benzylamino)phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3-one

J.-J. Jiang, X.-Q. Lü, F. Bao, B.-S. Kang and S. W. Ng

The NH unit on the exocyclic carbon-carbon double bond in the title compound, C₂₄H₂₁N₃O, lies on the same side of the double bond as the carbonyl unit of the pyrazolonyl ring, and the two interact through an N—H

O hydrogen bond [2.714 (2) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013479/bt6466sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013479/bt6466Isup2.hkl Contains datablock I

CCDC reference: 245281

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.134
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl ....     -P 2yc
PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        79.61 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-I (Johnson, 1976); software used to prepare material for publication: SHELXL97.

5-Methyl-2-phenyl-4-[(Z)-(benzylaminophenylmethylene]-2H-pyrazol-3-one top

Crystal data top

C₂₄H₂₁N₃O	F(000) = 776
M_r = 367.44	D_x = 1.264 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 872 reflections
a = 8.912 (1) Å	θ = 2.5–25.9°
b = 20.769 (3) Å	µ = 0.08 mm⁻¹
c = 10.608 (1) Å	T = 293 K
β = 79.605 (2)°	Prism, yellow
V = 1931.2 (4) Å³	0.50 × 0.38 × 0.14 mm
Z = 4

Data collection top

Bruker SMART area-detector diffractometer	2456 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.2°, θ_min = 2.0°
φ and ω scan	h = −11→11
11972 measured reflections	k = −26→23
4250 independent reflections	l = −10→13

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0631P)² + 0.2452P] where P = (F_o² + 2F_c²)/3
4250 reflections	(Δ/σ)_max = 0.001
258 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

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

	x	y	z	U_iso*/U_eq
O1	0.3582 (2)	0.5724 (1)	0.4401 (1)	0.0632 (4)
N1	0.1820 (2)	0.5698 (1)	0.6325 (1)	0.0516 (4)
N2	0.0823 (2)	0.5248 (1)	0.7012 (1)	0.0549 (4)
N3	0.3726 (2)	0.4549 (1)	0.3266 (1)	0.0533 (4)
C1	0.1996 (2)	0.6307 (1)	0.6869 (2)	0.0531 (5)
C2	0.1373 (2)	0.6415 (1)	0.8149 (2)	0.0678 (6)
C3	0.1592 (3)	0.7011 (1)	0.8682 (2)	0.0861 (8)
C4	0.2420 (3)	0.7489 (1)	0.7963 (3)	0.0920 (8)
C5	0.3014 (3)	0.7374 (1)	0.6718 (2)	0.0876 (7)
C6	0.2809 (3)	0.6789 (1)	0.6160 (2)	0.0706 (6)
C7	0.2635 (2)	0.5435 (1)	0.5216 (2)	0.0493 (4)
C8	0.2155 (2)	0.4776 (1)	0.5234 (2)	0.0461 (4)
C9	0.1021 (2)	0.4711 (1)	0.6363 (2)	0.0495 (4)
C10	0.0063 (2)	0.4144 (1)	0.6839 (2)	0.0689 (6)
C11	0.2801 (2)	0.4337 (1)	0.4296 (2)	0.0449 (4)
C12	0.2546 (2)	0.3635 (1)	0.4431 (2)	0.0481 (4)
C13	0.1705 (2)	0.3309 (1)	0.3667 (2)	0.0655 (5)
C14	0.1533 (3)	0.2654 (1)	0.3789 (3)	0.0864 (8)
C15	0.2203 (3)	0.2322 (1)	0.4658 (3)	0.0904 (8)
C16	0.3037 (3)	0.2645 (1)	0.5415 (2)	0.0848 (7)
C17	0.3209 (2)	0.3298 (1)	0.5312 (2)	0.0647 (5)
C18	0.4638 (2)	0.4171 (1)	0.2261 (2)	0.0495 (4)
C19	0.4168 (2)	0.4230 (1)	0.0969 (2)	0.0423 (4)
C20	0.5198 (2)	0.4028 (1)	−0.0096 (2)	0.0506 (4)
C21	0.4847 (2)	0.4074 (1)	−0.1305 (2)	0.0589 (5)
C22	0.3490 (3)	0.4334 (1)	−0.1470 (2)	0.0616 (5)
C23	0.2459 (2)	0.4532 (1)	−0.0424 (2)	0.0600 (5)
C24	0.2787 (2)	0.4479 (1)	0.0796 (2)	0.0514 (4)
H3n	0.389 (2)	0.496 (1)	0.327 (1)	0.065 (6)*
H2	0.0820	0.6094	0.8639	0.081*
H3	0.1175	0.7090	0.9536	0.103*
H4	0.2568	0.7885	0.8331	0.110*
H5	0.3570	0.7695	0.6230	0.105*
H6	0.3222	0.6720	0.5301	0.085*
H10a	0.0688	0.3819	0.7131	0.103*
H10b	−0.0395	0.3972	0.6158	0.103*
H10c	−0.0723	0.4273	0.7536	0.103*
H13	0.1256	0.3532	0.3071	0.079*
H14	0.0959	0.2433	0.3278	0.104*
H15	0.2089	0.1878	0.4732	0.108*
H16	0.3491	0.2419	0.6004	0.102*
H17	0.3773	0.3516	0.5834	0.078*
H18a	0.4574	0.3722	0.2516	0.059*
H18b	0.5695	0.4302	0.2179	0.059*
H20	0.6135	0.3859	0.0006	0.061*
H21	0.5537	0.3929	−0.2011	0.071*
H22	0.3265	0.4377	−0.2288	0.074*
H23	0.1528	0.4704	−0.0536	0.072*
H24	0.2077	0.4612	0.1500	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.085 (1)	0.055 (1)	0.045 (1)	−0.006 (1)	0.001 (1)	−0.004 (1)
N1	0.060 (1)	0.056 (1)	0.039 (1)	0.009 (1)	−0.008 (1)	−0.004 (1)
N2	0.054 (1)	0.066 (1)	0.044 (1)	0.010 (1)	−0.007 (1)	−0.002 (1)
N3	0.074 (1)	0.046 (1)	0.038 (1)	0.004 (1)	−0.006 (1)	−0.001 (1)
C1	0.059 (1)	0.059 (1)	0.045 (1)	0.020 (1)	−0.020 (1)	−0.013 (1)
C2	0.059 (1)	0.088 (2)	0.057 (1)	0.013 (1)	−0.012 (1)	−0.020 (1)
C3	0.078 (2)	0.115 (2)	0.067 (2)	0.020 (2)	−0.014 (1)	−0.045 (2)
C4	0.110 (2)	0.078 (2)	0.093 (2)	0.014 (2)	−0.029 (2)	−0.035 (2)
C5	0.130 (2)	0.060 (1)	0.077 (2)	0.007 (1)	−0.028 (2)	−0.014 (1)
C6	0.106 (2)	0.056 (1)	0.052 (1)	0.014 (1)	−0.022 (1)	−0.005 (1)
C7	0.058 (1)	0.054 (1)	0.036 (1)	0.009 (1)	−0.010 (1)	−0.002 (1)
C8	0.052 (1)	0.052 (1)	0.036 (1)	0.005 (1)	−0.013 (1)	0.000 (1)
C9	0.047 (1)	0.060 (1)	0.043 (1)	0.006 (1)	−0.012 (1)	0.0042 (1)
C10	0.061 (1)	0.077 (2)	0.065 (1)	−0.002 (1)	−0.003 (1)	0.003 (1)
C11	0.051 (1)	0.051 (1)	0.036 (1)	0.003 (1)	−0.015 (1)	0.002 (1)
C12	0.052 (1)	0.048 (1)	0.044 (1)	0.003 (1)	−0.007 (1)	0.000 (1)
C13	0.066 (1)	0.067 (1)	0.065 (1)	−0.010 (1)	−0.015 (1)	−0.002 (1)
C14	0.089 (2)	0.072 (2)	0.092 (2)	−0.026 (1)	0.000 (2)	−0.016 (1)
C15	0.099 (2)	0.046 (1)	0.111 (2)	0.000 (1)	0.022 (2)	0.001 (1)
C16	0.096 (2)	0.062 (2)	0.091 (2)	0.018 (1)	−0.002 (2)	0.020 (1)
C17	0.077 (1)	0.059 (1)	0.059 (1)	0.010 (1)	−0.017 (1)	0.006 (1)
C18	0.057 (1)	0.051 (1)	0.040 (1)	0.008 (1)	−0.006 (1)	−0.001 (1)
C19	0.052 (1)	0.036 (1)	0.039 (1)	0.001 (1)	−0.007 (1)	0.001 (1)
C20	0.055 (1)	0.050 (1)	0.046 (1)	0.006 (1)	−0.007 (1)	−0.001 (1)
C21	0.077 (1)	0.057 (1)	0.040 (1)	0.000 (1)	−0.004 (1)	−0.003 (1)
C22	0.087 (2)	0.056 (1)	0.047 (1)	−0.005 (1)	−0.026 (1)	0.003 (1)
C23	0.066 (1)	0.056 (1)	0.065 (1)	0.005 (1)	−0.028 (1)	0.002 (1)
C24	0.056 (1)	0.047 (1)	0.051 (1)	0.006 (1)	−0.009 (1)	−0.002 (1)

Geometric parameters (Å, º) top

O1—C7	1.247 (2)	C19—C20	1.386 (2)
N1—C7	1.379 (2)	C20—C21	1.377 (2)
N1—N2	1.399 (2)	C21—C22	1.364 (3)
N1—C1	1.412 (2)	C22—C23	1.369 (3)
N2—C9	1.306 (2)	C23—C24	1.382 (2)
N3—C11	1.321 (2)	N3—H3N	0.87 (2)
N3—C18	1.450 (2)	C2—H2	0.93
C1—C6	1.377 (3)	C3—H3	0.93
C1—C2	1.389 (2)	C4—H4	0.93
C2—C3	1.390 (3)	C5—H5	0.93
C3—C4	1.381 (4)	C6—H6	0.93
C4—C5	1.353 (3)	C10—H10a	0.96
C5—C6	1.377 (3)	C10—H10b	0.96
C7—C8	1.434 (3)	C10—H10c	0.96
C8—C11	1.395 (2)	C13—H13	0.93
C8—C9	1.428 (2)	C14—H14	0.93
C9—C10	1.489 (3)	C15—H15	0.93
C11—C12	1.478 (2)	C16—H16	0.93
C12—C13	1.376 (3)	C17—H17	0.93
C12—C17	1.382 (2)	C18—H18a	0.97
C13—C14	1.373 (3)	C18—H18b	0.97
C14—C15	1.371 (4)	C20—H20	0.93
C15—C16	1.365 (4)	C21—H21	0.93
C16—C17	1.368 (3)	C22—H22	0.93
C18—C19	1.508 (2)	C23—H23	0.93
C19—C24	1.378 (2)	C24—H24	0.93

C7—N1—N2	111.6 (1)	C18—N3—H3n	118 (1)
C7—N1—C1	128.5 (2)	C3—C2—H2	120.6
N2—N1—C1	119.5 (1)	C1—C2—H2	120.6
C9—N2—N1	106.5 (1)	C4—C3—H3	119.5
C11—N3—C18	127.6 (2)	C2—C3—H3	119.5
C6—C1—N1	121.0 (2)	C5—C4—H4	120.4
C2—C1—N1	119.3 (2)	C3—C4—H4	120.4
C6—C1—C2	119.7 (2)	C4—C5—H5	119.5
C3—C2—C1	118.7 (2)	C6—C5—H5	119.5
C4—C3—C2	121.0 (2)	C1—C6—H6	119.9
C5—C4—C3	119.2 (2)	C5—C6—H6	119.9
C4—C5—C6	121.1 (3)	C9—C10—H10a	109.5
C1—C6—C5	120.3 (2)	C9—C10—H10b	109.5
O1—C7—N1	126.0 (2)	H10a—C10—H10b	109.5
O1—C7—C8	129.2 (2)	C9—C10—H10c	109.5
N1—C7—C8	104.9 (2)	H10a—C10—H10c	109.5
C11—C8—C9	132.5 (2)	H10b—C10—H10c	109.5
C11—C8—C7	122.1 (2)	C14—C13—H13	120.2
C9—C8—C7	105.4 (1)	C12—C13—H13	120.2
N2—C9—C8	111.7 (2)	C13—C14—H14	119.8
N2—C9—C10	118.9 (2)	C15—C14—H14	119.8
C8—C9—C10	129.4 (2)	C16—C15—H15	120.0
N3—C11—C8	119.2 (2)	C14—C15—H15	120.0
N3—C11—C12	118.2 (2)	C15—C16—H16	119.8
C8—C11—C12	122.6 (2)	C17—C16—H16	119.8
C13—C12—C11	121.3 (2)	C16—C17—H17	120.0
C17—C12—C11	119.1 (2)	C12—C17—H17	120.0
C13—C12—C17	119.6 (2)	N3—C18—H18a	108.7
C14—C13—C12	119.7 (2)	C19—C18—H18a	108.7
C13—C14—C15	120.4 (2)	N3—C18—H18b	108.7
C16—C15—C14	119.9 (2)	C19—C18—H18b	108.7
C15—C16—C17	120.3 (2)	H18a—C18—H18b	107.6
C16—C17—C12	120.0 (2)	C21—C20—H20	119.7
N3—C18—C19	114.4 (1)	C19—C20—H20	119.7
C24—C19—C18	123.5 (2)	C22—C21—H21	119.9
C20—C19—C18	117.7 (2)	C20—C21—H21	119.9
C24—C19—C20	118.8 (2)	C21—C22—H22	120.1
C21—C20—C19	120.6 (2)	C23—C22—H22	120.1
C22—C21—C20	120.2 (2)	C22—C23—H23	119.7
C21—C22—C23	119.7 (2)	C24—C23—H23	119.7
C22—C23—C24	120.7 (2)	C19—C24—H24	120.0
C19—C24—C23	120.0 (2)	C23—C24—H24	120.0
C11—N3—H3n	114 (1)

C7—N1—N2—C9	0.9 (2)	C18—N3—C11—C12	−4.9 (3)
C1—N1—N2—C9	−172.6 (1)	C9—C8—C11—N3	172.7 (2)
C7—N1—C1—C6	16.2 (3)	C7—C8—C11—N3	−9.7 (2)
N2—N1—C1—C6	−171.6 (2)	C9—C8—C11—C12	−10.0 (3)
C7—N1—C1—C2	−162.0 (2)	C7—C8—C11—C12	167.7 (2)
N2—N1—C1—C2	10.2 (2)	N3—C11—C12—C13	−71.2 (2)
C6—C1—C2—C3	0.0 (3)	C8—C11—C12—C13	111.4 (2)
N1—C1—C2—C3	178.2 (2)	N3—C11—C12—C17	106.6 (2)
C1—C2—C3—C4	−0.4 (3)	C8—C11—C12—C17	−70.8 (2)
C2—C3—C4—C5	0.5 (4)	C17—C12—C13—C14	0.1 (3)
C3—C4—C5—C6	−0.2 (4)	C11—C12—C13—C14	177.9 (2)
C2—C1—C6—C5	0.4 (3)	C12—C13—C14—C15	−0.5 (3)
N1—C1—C6—C5	−177.8 (2)	C13—C14—C15—C16	0.5 (4)
C4—C5—C6—C1	−0.3 (4)	C14—C15—C16—C17	0.0 (4)
N2—N1—C7—O1	178.4 (2)	C15—C16—C17—C12	−0.5 (3)
C1—N1—C7—O1	−8.8 (3)	C13—C12—C17—C16	0.4 (3)
N2—N1—C7—C8	−2.0 (2)	C11—C12—C17—C16	−177.4 (2)
C1—N1—C7—C8	170.8 (2)	C11—N3—C18—C19	113.9 (2)
O1—C7—C8—C11	3.6 (3)	N3—C18—C19—C24	−15.9 (2)
N1—C7—C8—C11	−176.0 (2)	N3—C18—C19—C20	163.3 (2)
O1—C7—C8—C9	−178.2 (2)	C24—C19—C20—C21	−0.1 (3)
N1—C7—C8—C9	2.2 (2)	C18—C19—C20—C21	−179.3 (2)
N1—N2—C9—C8	0.6 (2)	C19—C20—C21—C22	1.4 (3)
N1—N2—C9—C10	−177.8 (2)	C20—C21—C22—C23	−1.8 (3)
C11—C8—C9—N2	176.2 (2)	C21—C22—C23—C24	0.9 (3)
C7—C8—C9—N2	−1.7 (2)	C20—C19—C24—C23	−0.8 (3)
C11—C8—C9—C10	−5.8 (3)	C18—C19—C24—C23	178.4 (2)
C7—C8—C9—C10	176.3 (2)	C22—C23—C24—C19	0.5 (3)
C18—N3—C11—C8	172.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O1	0.87 (2)	1.98 (2)	2.714 (2)	142 (2)

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4-[(Z)-(Benzyl­amino)­phenyl­methyl­ene]-5-methyl-2-phenyl-2H-pyrazol-3-one

Supporting information

Key indicators

checkCIF/PLATON results

4-[(Z)-(Benzylamino)phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3-one