1,5-Dimethyl-2-phenyl-4-{[(E)-3,4,5-trimethoxybenzylidene]amino}-1H-pyrazol-3(2H)-one.

In the title compound, C(21)H(23)N(3)O(4), the pyrazole ring forms dihedral angles of 21.58 (8) and 66.64 (7)° with the benzene and phenyl rings, respectively. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Atwood & Harvey (2001 ▶); Che & Huang (2003 ▶). For the applications of metal–Schiff base complexes, see: Drozdzak et al. (2005 ▶); Adsule et al. (2006 ▶); Yuan et al. (2007 ▶). For a related structure, see: Sun et al. (2007 ▶).

Experimental

Crystal data

C21H23N3O4

M = 381.42

Monoclinic,

a = 12.3644 (12) Å

b = 14.0075 (16) Å

c = 11.2682 (11) Å

β = 96.4680 (1)°

V = 1939.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.17 × 0.13 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.988

10089 measured reflections

3422 independent reflections

2084 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.098

S = 0.99

3422 reflections

258 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002934X/lh5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002934X/lh5091Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H23N3O4	F(000) = 808
Mr = 381.42	Dx = 1.306 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2128 reflections
a = 12.3644 (12) Å	θ = 2.2–25.3°
b = 14.0075 (16) Å	µ = 0.09 mm−1
c = 11.2682 (11) Å	T = 298 K
β = 96.4680 (1)°	Block, yellow
V = 1939.2 (3) Å3	0.40 × 0.17 × 0.13 mm
Z = 4

Siemens SMART CCD diffractometer	3422 independent reflections
Radiation source: fine-focus sealed tube	2084 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.964, Tmax = 0.988	k = −16→12
10089 measured reflections	l = −13→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.039P)2] where P = (Fo2 + 2Fc2)/3
3422 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.58862 (12)	0.17160 (11)	0.75617 (14)	0.0483 (4)
N2	0.55362 (12)	0.07674 (11)	0.73659 (14)	0.0488 (4)
N3	0.38480 (12)	0.18932 (11)	0.49987 (13)	0.0456 (4)
O1	0.56035 (11)	0.31372 (9)	0.65254 (13)	0.0616 (4)
O2	0.14379 (11)	0.51801 (9)	0.24428 (12)	0.0597 (4)
O3	0.06093 (10)	0.38623 (9)	0.08868 (12)	0.0555 (4)
O4	0.12137 (12)	0.20441 (10)	0.10776 (12)	0.0641 (4)
C1	0.53561 (15)	0.22988 (14)	0.66664 (17)	0.0451 (5)
C2	0.45678 (14)	0.16819 (13)	0.60050 (16)	0.0415 (5)
C3	0.46934 (14)	0.07841 (13)	0.64717 (17)	0.0425 (5)
C4	0.40708 (16)	−0.00978 (13)	0.61267 (19)	0.0568 (6)
H4A	0.4568	−0.0613	0.6042	0.085*
H4B	0.3628	0.0004	0.5382	0.085*
H4C	0.3614	−0.0255	0.6733	0.085*
C5	0.55506 (17)	0.01888 (15)	0.8440 (2)	0.0682 (7)
H5A	0.5077	0.0468	0.8963	0.102*
H5B	0.6278	0.0162	0.8838	0.102*
H5C	0.5306	−0.0445	0.8227	0.102*
C6	0.70012 (16)	0.18510 (13)	0.80311 (17)	0.0460 (5)
C7	0.72641 (19)	0.24765 (15)	0.89492 (19)	0.0645 (6)
H7	0.6722	0.2807	0.9286	0.077*
C8	0.8353 (2)	0.26125 (18)	0.9374 (2)	0.0788 (8)
H8	0.8544	0.3047	0.9985	0.095*
C9	0.9143 (2)	0.2109 (2)	0.8894 (3)	0.0798 (8)
H9	0.9871	0.2200	0.9182	0.096*
C10	0.88698 (18)	0.14758 (18)	0.7999 (2)	0.0765 (7)
H10	0.9411	0.1129	0.7683	0.092*
C11	0.78040 (17)	0.13441 (15)	0.7557 (2)	0.0613 (6)
H11	0.7622	0.0913	0.6939	0.074*
C12	0.36413 (15)	0.27582 (14)	0.47241 (17)	0.0478 (5)
H12	0.3986	0.3235	0.5201	0.057*
C13	0.28837 (15)	0.30404 (13)	0.36894 (16)	0.0429 (5)
C14	0.25703 (15)	0.39875 (13)	0.35636 (17)	0.0463 (5)
H14	0.2868	0.4437	0.4114	0.056*
C15	0.18193 (15)	0.42704 (13)	0.26269 (17)	0.0439 (5)
C16	0.13902 (15)	0.36017 (14)	0.17957 (17)	0.0446 (5)
C17	0.17022 (15)	0.26509 (14)	0.19268 (16)	0.0460 (5)
C18	0.24460 (15)	0.23685 (14)	0.28662 (16)	0.0461 (5)
H18	0.2653	0.1731	0.2947	0.055*
C19	0.17650 (18)	0.58758 (14)	0.33332 (19)	0.0658 (6)
H19A	0.1578	0.5659	0.4092	0.099*
H19B	0.1400	0.6468	0.3129	0.099*
H19C	0.2538	0.5970	0.3379	0.099*
C20	0.10337 (18)	0.41981 (17)	−0.01563 (19)	0.0735 (7)
H20A	0.1388	0.4801	0.0009	0.110*
H20B	0.0450	0.4275	−0.0787	0.110*
H20C	0.1549	0.3745	−0.0396	0.110*
C21	0.12836 (19)	0.10573 (14)	0.1296 (2)	0.0703 (7)
H21A	0.2030	0.0859	0.1341	0.105*
H21B	0.0864	0.0722	0.0660	0.105*
H21C	0.1005	0.0917	0.2038	0.105*

	U11	U22	U33	U12	U13	U23
N1	0.0450 (10)	0.0437 (10)	0.0528 (11)	−0.0016 (8)	−0.0099 (8)	0.0052 (8)
N2	0.0480 (10)	0.0402 (10)	0.0556 (11)	−0.0017 (8)	−0.0053 (8)	0.0121 (9)
N3	0.0477 (10)	0.0446 (10)	0.0427 (10)	0.0030 (7)	−0.0027 (8)	0.0051 (8)
O1	0.0657 (10)	0.0377 (9)	0.0756 (11)	−0.0008 (7)	−0.0176 (8)	0.0059 (7)
O2	0.0717 (10)	0.0454 (9)	0.0582 (9)	0.0105 (7)	−0.0101 (8)	0.0030 (7)
O3	0.0515 (9)	0.0663 (10)	0.0453 (9)	0.0047 (7)	−0.0093 (7)	0.0096 (7)
O4	0.0802 (11)	0.0523 (10)	0.0538 (9)	−0.0018 (7)	−0.0188 (8)	−0.0043 (8)
C1	0.0445 (12)	0.0400 (12)	0.0493 (13)	0.0061 (9)	−0.0022 (9)	0.0020 (10)
C2	0.0419 (11)	0.0415 (12)	0.0397 (12)	0.0043 (9)	−0.0018 (9)	0.0029 (9)
C3	0.0392 (11)	0.0427 (12)	0.0450 (12)	0.0038 (9)	0.0019 (9)	0.0027 (10)
C4	0.0553 (13)	0.0479 (13)	0.0663 (15)	−0.0039 (10)	0.0024 (11)	0.0001 (11)
C5	0.0662 (15)	0.0656 (15)	0.0695 (16)	−0.0030 (12)	−0.0064 (12)	0.0279 (13)
C6	0.0470 (12)	0.0438 (12)	0.0441 (12)	−0.0020 (10)	−0.0088 (10)	0.0079 (10)
C7	0.0706 (16)	0.0645 (15)	0.0557 (14)	0.0010 (12)	−0.0050 (12)	−0.0033 (12)
C8	0.089 (2)	0.0772 (18)	0.0617 (16)	−0.0245 (16)	−0.0266 (15)	−0.0002 (14)
C9	0.0563 (16)	0.085 (2)	0.091 (2)	−0.0145 (14)	−0.0253 (15)	0.0310 (17)
C10	0.0463 (15)	0.0813 (18)	0.101 (2)	0.0010 (12)	0.0043 (14)	0.0130 (16)
C11	0.0518 (14)	0.0638 (15)	0.0668 (16)	0.0008 (11)	−0.0005 (12)	−0.0037 (12)
C12	0.0491 (12)	0.0481 (13)	0.0437 (12)	0.0007 (10)	−0.0051 (9)	0.0011 (10)
C13	0.0425 (11)	0.0478 (12)	0.0367 (11)	0.0008 (9)	−0.0027 (9)	0.0051 (10)
C14	0.0513 (12)	0.0453 (12)	0.0403 (12)	−0.0034 (9)	−0.0038 (9)	0.0006 (9)
C15	0.0455 (12)	0.0415 (11)	0.0437 (12)	0.0031 (9)	0.0001 (9)	0.0061 (10)
C16	0.0407 (11)	0.0524 (13)	0.0387 (12)	0.0022 (9)	−0.0039 (9)	0.0072 (10)
C17	0.0500 (12)	0.0494 (13)	0.0372 (12)	−0.0040 (10)	−0.0012 (10)	−0.0016 (10)
C18	0.0515 (12)	0.0425 (12)	0.0429 (12)	0.0027 (9)	−0.0010 (10)	0.0035 (10)
C19	0.0833 (17)	0.0464 (13)	0.0663 (15)	0.0053 (12)	0.0020 (13)	−0.0007 (12)
C20	0.0790 (17)	0.0973 (19)	0.0432 (14)	0.0217 (14)	0.0019 (12)	0.0140 (13)
C21	0.0875 (18)	0.0523 (15)	0.0675 (16)	−0.0072 (12)	−0.0063 (13)	−0.0076 (12)

N1—C1	1.402 (2)	C8—C9	1.364 (3)
N1—N2	1.407 (2)	C8—H8	0.9300
N1—C6	1.432 (2)	C9—C10	1.357 (3)
N2—C3	1.366 (2)	C9—H9	0.9300
N2—C5	1.455 (2)	C10—C11	1.368 (3)
N3—C12	1.269 (2)	C10—H10	0.9300
N3—C2	1.392 (2)	C11—H11	0.9300
O1—C1	1.228 (2)	C12—C13	1.465 (3)
O2—C15	1.367 (2)	C12—H12	0.9300
O2—C19	1.424 (2)	C13—C14	1.385 (2)
O3—C16	1.375 (2)	C13—C18	1.388 (2)
O3—C20	1.420 (2)	C14—C15	1.383 (3)
O4—C17	1.368 (2)	C14—H14	0.9300
O4—C21	1.405 (2)	C15—C16	1.387 (3)
C1—C2	1.445 (3)	C16—C17	1.390 (3)
C2—C3	1.365 (2)	C17—C18	1.380 (2)
C3—C4	1.484 (2)	C18—H18	0.9300
C4—H4A	0.9600	C19—H19A	0.9600
C4—H4B	0.9600	C19—H19B	0.9600
C4—H4C	0.9600	C19—H19C	0.9600
C5—H5A	0.9600	C20—H20A	0.9600
C5—H5B	0.9600	C20—H20B	0.9600
C5—H5C	0.9600	C20—H20C	0.9600
C6—C7	1.367 (3)	C21—H21A	0.9600
C6—C11	1.376 (3)	C21—H21B	0.9600
C7—C8	1.391 (3)	C21—H21C	0.9600
C7—H7	0.9300
C1—N1—N2	109.06 (15)	C9—C10—H10	119.7
C1—N1—C6	122.78 (15)	C11—C10—H10	119.7
N2—N1—C6	116.67 (14)	C10—C11—C6	119.8 (2)
C3—N2—N1	107.16 (14)	C10—C11—H11	120.1
C3—N2—C5	124.06 (15)	C6—C11—H11	120.1
N1—N2—C5	114.90 (16)	N3—C12—C13	122.99 (18)
C12—N3—C2	119.61 (16)	N3—C12—H12	118.5
C15—O2—C19	117.73 (15)	C13—C12—H12	118.5
C16—O3—C20	114.23 (15)	C14—C13—C18	119.85 (18)
C17—O4—C21	118.35 (16)	C14—C13—C12	119.09 (18)
O1—C1—N1	123.15 (18)	C18—C13—C12	121.01 (17)
O1—C1—C2	131.93 (18)	C15—C14—C13	120.58 (18)
N1—C1—C2	104.86 (16)	C15—C14—H14	119.7
C3—C2—N3	122.96 (17)	C13—C14—H14	119.7
C3—C2—C1	108.14 (16)	O2—C15—C14	125.01 (18)
N3—C2—C1	128.69 (17)	O2—C15—C16	115.34 (17)
C2—C3—N2	110.13 (16)	C14—C15—C16	119.65 (17)
C2—C3—C4	129.25 (18)	O3—C16—C15	120.43 (17)
N2—C3—C4	120.61 (17)	O3—C16—C17	119.79 (18)
C3—C4—H4A	109.5	C15—C16—C17	119.65 (18)
C3—C4—H4B	109.5	O4—C17—C18	124.20 (18)
H4A—C4—H4B	109.5	O4—C17—C16	115.18 (17)
C3—C4—H4C	109.5	C18—C17—C16	120.62 (18)
H4A—C4—H4C	109.5	C17—C18—C13	119.64 (18)
H4B—C4—H4C	109.5	C17—C18—H18	120.2
N2—C5—H5A	109.5	C13—C18—H18	120.2
N2—C5—H5B	109.5	O2—C19—H19A	109.5
H5A—C5—H5B	109.5	O2—C19—H19B	109.5
N2—C5—H5C	109.5	H19A—C19—H19B	109.5
H5A—C5—H5C	109.5	O2—C19—H19C	109.5
H5B—C5—H5C	109.5	H19A—C19—H19C	109.5
C7—C6—C11	120.3 (2)	H19B—C19—H19C	109.5
C7—C6—N1	120.07 (19)	O3—C20—H20A	109.5
C11—C6—N1	119.66 (18)	O3—C20—H20B	109.5
C6—C7—C8	119.1 (2)	H20A—C20—H20B	109.5
C6—C7—H7	120.4	O3—C20—H20C	109.5
C8—C7—H7	120.4	H20A—C20—H20C	109.5
C9—C8—C7	120.1 (2)	H20B—C20—H20C	109.5
C9—C8—H8	120.0	O4—C21—H21A	109.5
C7—C8—H8	120.0	O4—C21—H21B	109.5
C10—C9—C8	120.2 (2)	H21A—C21—H21B	109.5
C10—C9—H9	119.9	O4—C21—H21C	109.5
C8—C9—H9	119.9	H21A—C21—H21C	109.5
C9—C10—C11	120.5 (2)	H21B—C21—H21C	109.5
C1—N1—N2—C3	−8.40 (19)	C8—C9—C10—C11	0.9 (4)
C6—N1—N2—C3	−152.94 (16)	C9—C10—C11—C6	−0.6 (4)
C1—N1—N2—C5	−150.54 (16)	C7—C6—C11—C10	−0.8 (3)
C6—N1—N2—C5	64.9 (2)	N1—C6—C11—C10	179.61 (18)
N2—N1—C1—O1	−170.55 (17)	C2—N3—C12—C13	−179.20 (16)
C6—N1—C1—O1	−28.6 (3)	N3—C12—C13—C14	169.61 (17)
N2—N1—C1—C2	6.95 (19)	N3—C12—C13—C18	−7.8 (3)
C6—N1—C1—C2	148.88 (17)	C18—C13—C14—C15	0.3 (3)
C12—N3—C2—C3	168.73 (17)	C12—C13—C14—C15	−177.09 (17)
C12—N3—C2—C1	−17.2 (3)	C19—O2—C15—C14	−5.6 (3)
O1—C1—C2—C3	174.1 (2)	C19—O2—C15—C16	173.74 (17)
N1—C1—C2—C3	−3.0 (2)	C13—C14—C15—O2	178.25 (17)
O1—C1—C2—N3	−0.6 (3)	C13—C14—C15—C16	−1.1 (3)
N1—C1—C2—N3	−177.84 (17)	C20—O3—C16—C15	88.4 (2)
N3—C2—C3—N2	173.05 (16)	C20—O3—C16—C17	−95.6 (2)
C1—C2—C3—N2	−2.1 (2)	O2—C15—C16—O3	−2.1 (3)
N3—C2—C3—C4	−6.2 (3)	C14—C15—C16—O3	177.30 (16)
C1—C2—C3—C4	178.61 (18)	O2—C15—C16—C17	−178.04 (16)
N1—N2—C3—C2	6.4 (2)	C14—C15—C16—C17	1.3 (3)
C5—N2—C3—C2	144.21 (18)	C21—O4—C17—C18	14.1 (3)
N1—N2—C3—C4	−174.22 (15)	C21—O4—C17—C16	−165.26 (17)
C5—N2—C3—C4	−36.4 (3)	O3—C16—C17—O4	2.5 (3)
C1—N1—C6—C7	86.2 (2)	C15—C16—C17—O4	178.47 (17)
N2—N1—C6—C7	−134.48 (18)	O3—C16—C17—C18	−176.90 (16)
C1—N1—C6—C11	−94.1 (2)	C15—C16—C17—C18	−0.9 (3)
N2—N1—C6—C11	45.2 (2)	O4—C17—C18—C13	−179.14 (17)
C11—C6—C7—C8	1.8 (3)	C16—C17—C18—C13	0.2 (3)
N1—C6—C7—C8	−178.59 (18)	C14—C13—C18—C17	0.1 (3)
C6—C7—C8—C9	−1.5 (3)	C12—C13—C18—C17	177.48 (17)
C7—C8—C9—C10	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5C···O1i	0.96	2.31	3.211 (2)	155
C9—H9···O4ii	0.93	2.56	3.346 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5C⋯O1i	0.96	2.31	3.211 (2)	155
C9—H9⋯O4ii	0.93	2.56	3.346 (3)	142

Symmetry codes: (i) ; (ii) .