A second monoclinic polymorph of 4-(2-hydr­oxy-4-methoxy­benzyl­ideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Zhu, Z.-F.; Shen, X.-H.; Tang, X.-G.

doi:10.1107/S1600536808029498

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o1965-o1966

doi:10.1107/S1600536808029498

Open

access

A second monoclinic polymorph of 4-(2-hydroxy-4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Zhao-Fu Zhu,^a ^* Xi-Hai Shen ^a and Xiao-Guang Tang ^a

^aDepartment of Chemistry, Hebei Normal College of Science and Technology, Qinhuangdao 066600, People's Republic of China
^*Correspondence e-mail: zhaofu_zhu@163.com

(Received 13 September 2008; accepted 15 September 2008; online 20 September 2008)

The title compound, C₁₉H₁₉N₃O₃, prepared by condensing 4-aminoantipyrine and 4-methoxy-2-hydroxybenzaldehyde in methanol, is the second monoclinic polymorph of this compound which crystallizes in the space group C2/c. The structure was previously reported [Wang, Zhang, Yan, Zheng & Yang (2007 ). Acta Cryst. E63, o1245–o1246] in the space group P2₁/c. The hydroxyl group is disordered over two positions with occupancies of 0.787 (4) and 0.213 (4). The triply substituted benzene ring and the phenyl ring form dihedral angles of 12.2 (2) and 53.7 (2)°, respectively, with the pyrazolone ring; the corresponding values in the P2₁/c polymorph are 7.5 (2) and 42.6 (2)°. Intramolecular O—H⋯N and C—H⋯O hydrogen bonds are observed in the major disorder component. Adjacent molecules are linked through intermolecular O—H⋯O hydrogen bonds, forming dimers.

Related literature

For the P2₁/c polymorph of the title compound, see: Wang et al. (2007). For related structures, see: Duan et al. (2006 ); Jing et al. (2006 ); Sun et al. (2006 ); Wen (2005 ); Zhang et al. (2007 ); Zheng et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₉N₃O₃
M_r = 337.37
Monoclinic, C 2/c
a = 30.581 (3) Å
b = 6.906 (2) Å
c = 17.059 (3) Å
β = 110.500 (2)°
V = 3374.6 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.973, T_max = 0.976
9315 measured reflections
3634 independent reflections
2355 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.145
S = 1.01
3634 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.605 (2)	147
O1′—H1′⋯O3ⁱ	0.82	1.80	2.609 (6)	169
C7—H7⋯O3	0.93	2.33	3.006 (5)	129
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029498/ci2671sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029498/ci2671Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title compound has been previously reported by Wang et al. (2007) in the monoclinic space group P2₁/c. We report here the structure of the second monoclinic polymorph of the title compound, in the space group C2/c.

In the title molecule (Fig. 1), the pyrazolone ring makes dihedral angles of 12.2 (2) and 53.7 (2)°, respectively, with the triply substituted C1–C6 benzene ring and the unsubstituted C13—C18 benzene ring; the corresponding values in the P2₁/c polymorph are 7.5 (2) and 42.6 (2)°. The bond lengths and angles are within normal ranges and comparable with those in related similar compounds (Duan et al., 2006; Jing et al., 2006; Zheng et al., 2006; Sun et al., 2006; Zhang et al., 2007; Wen, 2005). Intramolecular O—H···N and C—H···O hydrogen bonds (Table 1) are observed in the molecular structure.

Related literature top

For the P2₁/c polymorph of the title compound, see: Wang et al. (2007). For related literature, see: Duan et al. (2006); Jing et al. (2006); Sun et al. (2006); Wen (2005); Zhang et al. (2007); Zheng et al. (2006).

Experimental top

4-Methoxy-2-hydroxybenzaldehyde (152.1 mg, 1.0 mmol) and 4-aminoantipyrine (203.2 mg, 1.0 mmol) were added in methanol (60 ml). The mixture was refluxed for 30 min, then cooled to room temperature, yielding colourless solution. Colourless single crystals were formed when the solution was evaporated in air for several days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellisoids. Only the major disorder component is shown. Intramolecular hydrogen bonds are shown as dashed lines.

4-(2-hydroxy-4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H- pyrazol-3(2H)-one top

Crystal data top

C₁₉H₁₉N₃O₃	F(000) = 1424
M_r = 337.37	D_x = 1.328 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2554 reflections
a = 30.581 (3) Å	θ = 2.4–25.6°
b = 6.906 (2) Å	µ = 0.09 mm⁻¹
c = 17.059 (3) Å	T = 298 K
β = 110.500 (2)°	Block, colourless
V = 3374.6 (12) Å³	0.30 × 0.28 × 0.27 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3634 independent reflections
Radiation source: fine-focus sealed tube	2355 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −36→38
T_min = 0.973, T_max = 0.976	k = −8→8
9315 measured reflections	l = −20→21

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.071P)² + 0.6977P] where P = (F_o² + 2F_c²)/3
3634 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₉N₃O₃	V = 3374.6 (12) Å³
M_r = 337.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.581 (3) Å	µ = 0.09 mm⁻¹
b = 6.906 (2) Å	T = 298 K
c = 17.059 (3) Å	0.30 × 0.28 × 0.27 mm
β = 110.500 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3634 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2355 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.976	R_int = 0.037
9315 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
3634 reflections	Δρ_min = −0.20 e Å⁻³
241 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.13337 (6)	0.6567 (2)	0.02029 (14)	0.0720 (7)	0.787 (4)
H1	0.1613	0.6337	0.0427	0.108*	0.787 (4)
O1'	0.1955 (2)	1.2396 (10)	−0.0333 (4)	0.071 (3)	0.213 (4)
H1'	0.1891	1.3241	−0.0693	0.106*	0.213 (4)
O2	0.03260 (5)	1.1507 (2)	−0.13459 (11)	0.0834 (5)
O3	0.31552 (5)	0.96750 (18)	0.13504 (9)	0.0628 (4)
N1	0.22230 (5)	0.7333 (2)	0.08331 (9)	0.0483 (4)
N2	0.32298 (5)	0.5274 (2)	0.23447 (9)	0.0494 (4)
N3	0.34320 (5)	0.6934 (2)	0.21511 (9)	0.0491 (4)
C1	0.16608 (6)	0.9540 (2)	−0.00342 (11)	0.0450 (4)
C2	0.12777 (7)	0.8350 (3)	−0.01178 (12)	0.0505 (5)
H2	0.1327	0.7125	0.0124	0.061*	0.213 (4)
C3	0.08307 (7)	0.8956 (3)	−0.05505 (13)	0.0586 (5)
H3	0.0580	0.8144	−0.0601	0.070*
C4	0.07548 (7)	1.0762 (3)	−0.09092 (13)	0.0573 (5)
C5	0.11288 (7)	1.1968 (3)	−0.08392 (12)	0.0586 (5)
H5	0.1078	1.3190	−0.1084	0.070*
C6	0.15705 (6)	1.1355 (3)	−0.04112 (12)	0.0511 (5)
H6	0.1820	1.2171	−0.0369	0.061*	0.787 (4)
C7	0.21326 (6)	0.8961 (2)	0.04376 (11)	0.0468 (4)
H7	0.2378	0.9780	0.0458	0.056*
C8	0.26761 (6)	0.6861 (2)	0.13421 (10)	0.0437 (4)
C9	0.27825 (6)	0.5207 (2)	0.18071 (11)	0.0458 (4)
C10	0.24772 (7)	0.3533 (3)	0.17836 (14)	0.0658 (6)
H10A	0.2179	0.3725	0.1351	0.099*
H10B	0.2436	0.3411	0.2314	0.099*
H10C	0.2618	0.2375	0.1670	0.099*
C11	0.35235 (7)	0.3601 (3)	0.26802 (13)	0.0625 (6)
H11A	0.3354	0.2677	0.2883	0.094*
H11B	0.3798	0.4001	0.3132	0.094*
H11C	0.3613	0.3019	0.2248	0.094*
C12	0.30866 (6)	0.8026 (2)	0.15627 (11)	0.0468 (4)
C13	0.38321 (6)	0.7784 (2)	0.27470 (11)	0.0460 (4)
C14	0.39069 (7)	0.7743 (3)	0.35949 (12)	0.0559 (5)
H14	0.3703	0.7077	0.3795	0.067*
C15	0.42859 (8)	0.8700 (3)	0.41369 (14)	0.0673 (6)
H15	0.4341	0.8665	0.4709	0.081*
C16	0.45828 (8)	0.9701 (3)	0.38483 (15)	0.0717 (6)
H16	0.4836	1.0358	0.4221	0.086*
C17	0.45062 (7)	0.9736 (3)	0.30043 (15)	0.0672 (6)
H17	0.4708	1.0424	0.2807	0.081*
C18	0.41342 (7)	0.8764 (3)	0.24504 (13)	0.0545 (5)
H18	0.4087	0.8768	0.1881	0.065*
C19	−0.00684 (9)	1.0308 (4)	−0.1448 (3)	0.1287 (14)
H19A	−0.0037	0.9120	−0.1715	0.193*
H19B	−0.0347	1.0966	−0.1788	0.193*
H19C	−0.0088	1.0030	−0.0910	0.193*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0605 (11)	0.0448 (11)	0.1057 (17)	−0.0043 (9)	0.0229 (11)	0.0205 (10)
O1'	0.056 (4)	0.064 (4)	0.079 (5)	−0.012 (3)	0.005 (3)	0.032 (4)
O2	0.0526 (8)	0.0619 (9)	0.1159 (14)	0.0025 (7)	0.0047 (8)	0.0090 (9)
O3	0.0643 (8)	0.0470 (8)	0.0663 (9)	−0.0092 (7)	0.0094 (7)	0.0151 (6)
N1	0.0518 (9)	0.0447 (8)	0.0470 (9)	−0.0007 (7)	0.0155 (7)	0.0007 (7)
N2	0.0561 (9)	0.0376 (8)	0.0509 (9)	−0.0017 (7)	0.0142 (8)	0.0053 (7)
N3	0.0541 (9)	0.0402 (8)	0.0483 (9)	−0.0070 (7)	0.0119 (7)	0.0041 (7)
C1	0.0505 (10)	0.0432 (9)	0.0406 (10)	−0.0025 (8)	0.0150 (8)	−0.0014 (8)
C2	0.0557 (11)	0.0404 (10)	0.0556 (11)	−0.0029 (8)	0.0197 (9)	0.0005 (8)
C3	0.0488 (11)	0.0479 (11)	0.0750 (14)	−0.0069 (9)	0.0167 (10)	−0.0035 (10)
C4	0.0524 (11)	0.0494 (11)	0.0630 (13)	0.0029 (9)	0.0114 (10)	−0.0009 (9)
C5	0.0618 (12)	0.0461 (11)	0.0608 (13)	−0.0010 (9)	0.0125 (10)	0.0087 (9)
C6	0.0530 (11)	0.0479 (10)	0.0497 (11)	−0.0073 (9)	0.0147 (9)	0.0031 (8)
C7	0.0526 (10)	0.0454 (10)	0.0425 (10)	−0.0047 (8)	0.0167 (8)	−0.0021 (8)
C8	0.0513 (10)	0.0394 (9)	0.0404 (9)	−0.0015 (8)	0.0162 (8)	−0.0020 (7)
C9	0.0541 (10)	0.0410 (9)	0.0442 (10)	−0.0015 (8)	0.0195 (9)	−0.0011 (8)
C10	0.0708 (13)	0.0508 (11)	0.0740 (14)	−0.0116 (10)	0.0229 (12)	0.0091 (10)
C11	0.0688 (13)	0.0471 (11)	0.0632 (13)	0.0063 (10)	0.0127 (11)	0.0108 (9)
C12	0.0562 (11)	0.0402 (9)	0.0413 (10)	−0.0026 (8)	0.0138 (9)	0.0011 (8)
C13	0.0453 (10)	0.0397 (9)	0.0487 (11)	0.0024 (8)	0.0111 (9)	−0.0004 (8)
C14	0.0554 (11)	0.0612 (12)	0.0505 (11)	−0.0039 (10)	0.0180 (10)	0.0004 (9)
C15	0.0663 (13)	0.0772 (14)	0.0496 (12)	−0.0062 (12)	0.0091 (11)	−0.0061 (10)
C16	0.0600 (13)	0.0742 (15)	0.0689 (15)	−0.0139 (11)	0.0075 (11)	−0.0059 (12)
C17	0.0565 (12)	0.0623 (13)	0.0838 (16)	−0.0101 (10)	0.0255 (12)	0.0009 (12)
C18	0.0590 (11)	0.0527 (11)	0.0536 (11)	−0.0026 (9)	0.0223 (10)	0.0005 (9)
C19	0.0503 (14)	0.087 (2)	0.211 (4)	−0.0084 (14)	−0.0024 (18)	0.023 (2)

Geometric parameters (Å, º) top

O1—C2	1.333 (2)	C7—H7	0.93
O1—H1	0.82	C8—C9	1.363 (2)
O1'—C6	1.345 (6)	C8—C12	1.426 (2)
O1'—H1'	0.82	C9—C10	1.478 (2)
O2—C4	1.362 (2)	C10—H10A	0.96
O2—C19	1.422 (3)	C10—H10B	0.96
O3—C12	1.235 (2)	C10—H10C	0.96
N1—C7	1.291 (2)	C11—H11A	0.96
N1—C8	1.392 (2)	C11—H11B	0.96
N2—C9	1.355 (2)	C11—H11C	0.96
N2—N3	1.3959 (19)	C13—C18	1.376 (3)
N2—C11	1.452 (2)	C13—C14	1.383 (3)
N3—C12	1.396 (2)	C14—C15	1.373 (3)
N3—C13	1.416 (2)	C14—H14	0.93
C1—C6	1.392 (2)	C15—C16	1.363 (3)
C1—C2	1.397 (2)	C15—H15	0.93
C1—C7	1.441 (2)	C16—C17	1.376 (3)
C2—C3	1.372 (3)	C16—H16	0.93
C2—H2	0.93	C17—C18	1.373 (3)
C3—C4	1.373 (3)	C17—H17	0.93
C3—H3	0.93	C18—H18	0.93
C4—C5	1.386 (3)	C19—H19A	0.96
C5—C6	1.359 (3)	C19—H19B	0.96
C5—H5	0.93	C19—H19C	0.96
C6—H6	0.93

C2—O1—H1	109.5	C8—C9—C10	128.31 (17)
C6—O1'—H1'	109.5	C9—C10—H10A	109.5
C4—O2—C19	117.40 (17)	C9—C10—H10B	109.5
C7—N1—C8	120.96 (15)	H10A—C10—H10B	109.5
C9—N2—N3	107.07 (13)	C9—C10—H10C	109.5
C9—N2—C11	125.34 (14)	H10A—C10—H10C	109.5
N3—N2—C11	118.86 (14)	H10B—C10—H10C	109.5
N2—N3—C12	109.12 (13)	N2—C11—H11A	109.5
N2—N3—C13	120.92 (14)	N2—C11—H11B	109.5
C12—N3—C13	122.55 (14)	H11A—C11—H11B	109.5
C6—C1—C2	117.34 (16)	N2—C11—H11C	109.5
C6—C1—C7	120.37 (16)	H11A—C11—H11C	109.5
C2—C1—C7	122.27 (16)	H11B—C11—H11C	109.5
O1—C2—C3	117.58 (18)	O3—C12—N3	123.06 (16)
O1—C2—C1	121.24 (18)	O3—C12—C8	131.86 (17)
C3—C2—C1	121.16 (17)	N3—C12—C8	105.01 (14)
C3—C2—H2	119.4	C18—C13—C14	120.51 (17)
C1—C2—H2	119.4	C18—C13—N3	117.56 (17)
C2—C3—C4	119.87 (18)	C14—C13—N3	121.82 (17)
C2—C3—H3	120.1	C15—C14—C13	119.09 (19)
C4—C3—H3	120.1	C15—C14—H14	120.5
O2—C4—C3	124.53 (18)	C13—C14—H14	120.5
O2—C4—C5	115.33 (17)	C16—C15—C14	120.8 (2)
C3—C4—C5	120.14 (18)	C16—C15—H15	119.6
C6—C5—C4	119.62 (17)	C14—C15—H15	119.6
C6—C5—H5	120.2	C15—C16—C17	119.7 (2)
C4—C5—H5	120.2	C15—C16—H16	120.1
O1'—C6—C5	123.9 (3)	C17—C16—H16	120.1
O1'—C6—C1	114.2 (3)	C18—C17—C16	120.5 (2)
C5—C6—C1	121.86 (17)	C18—C17—H17	119.7
C5—C6—H6	119.1	C16—C17—H17	119.7
C1—C6—H6	119.1	C17—C18—C13	119.2 (2)
N1—C7—C1	121.53 (17)	C17—C18—H18	120.4
N1—C7—H7	119.2	C13—C18—H18	120.4
C1—C7—H7	119.2	O2—C19—H19A	109.5
C9—C8—N1	122.81 (16)	O2—C19—H19B	109.5
C9—C8—C12	108.09 (15)	H19A—C19—H19B	109.5
N1—C8—C12	128.62 (15)	O2—C19—H19C	109.5
N2—C9—C8	110.13 (15)	H19A—C19—H19C	109.5
N2—C9—C10	121.55 (16)	H19B—C19—H19C	109.5

C9—N2—N3—C12	7.87 (18)	C11—N2—C9—C8	−153.47 (18)
C11—N2—N3—C12	157.19 (16)	N3—N2—C9—C10	174.23 (17)
C9—N2—N3—C13	158.51 (16)	C11—N2—C9—C10	27.5 (3)
C11—N2—N3—C13	−52.2 (2)	N1—C8—C9—N2	−169.67 (15)
C6—C1—C2—O1	178.03 (19)	C12—C8—C9—N2	3.0 (2)
C7—C1—C2—O1	−3.5 (3)	N1—C8—C9—C10	9.3 (3)
C6—C1—C2—C3	−0.4 (3)	C12—C8—C9—C10	−177.97 (18)
C7—C1—C2—C3	178.12 (18)	N2—N3—C12—O3	171.32 (17)
O1—C2—C3—C4	−178.5 (2)	C13—N3—C12—O3	21.3 (3)
C1—C2—C3—C4	−0.1 (3)	N2—N3—C12—C8	−5.92 (18)
C19—O2—C4—C3	−1.2 (4)	C13—N3—C12—C8	−155.98 (16)
C19—O2—C4—C5	178.8 (2)	C9—C8—C12—O3	−175.1 (2)
C2—C3—C4—O2	−179.54 (19)	N1—C8—C12—O3	−2.9 (3)
C2—C3—C4—C5	0.4 (3)	C9—C8—C12—N3	1.84 (19)
O2—C4—C5—C6	179.70 (19)	N1—C8—C12—N3	174.00 (16)
C3—C4—C5—C6	−0.2 (3)	N2—N3—C13—C18	150.64 (16)
C4—C5—C6—O1'	177.8 (5)	C12—N3—C13—C18	−62.7 (2)
C4—C5—C6—C1	−0.2 (3)	N2—N3—C13—C14	−33.2 (2)
C2—C1—C6—O1'	−177.6 (4)	C12—N3—C13—C14	113.5 (2)
C7—C1—C6—O1'	3.8 (5)	C18—C13—C14—C15	0.2 (3)
C2—C1—C6—C5	0.6 (3)	N3—C13—C14—C15	−175.85 (18)
C7—C1—C6—C5	−177.99 (18)	C13—C14—C15—C16	0.8 (3)
C8—N1—C7—C1	−174.67 (15)	C14—C15—C16—C17	−0.8 (3)
C6—C1—C7—N1	175.94 (17)	C15—C16—C17—C18	−0.3 (3)
C2—C1—C7—N1	−2.5 (3)	C16—C17—C18—C13	1.3 (3)
C7—N1—C8—C9	176.18 (17)	C14—C13—C18—C17	−1.3 (3)
C7—N1—C8—C12	5.1 (3)	N3—C13—C18—C17	174.94 (18)
N3—N2—C9—C8	−6.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.605 (2)	147
O1′—H1′···O3ⁱ	0.82	1.80	2.609 (6)	169
C7—H7···O3	0.93	2.33	3.006 (5)	129

Symmetry code: (i) −x+1/2, −y+5/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₃O₃
M_r	337.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	30.581 (3), 6.906 (2), 17.059 (3)
β (°)	110.500 (2)
V (Å³)	3374.6 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.28 × 0.27

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.973, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	9315, 3634, 2355
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.145, 1.02
No. of reflections	3634
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.605 (2)	147
O1'—H1'···O3ⁱ	0.82	1.80	2.609 (6)	169
C7—H7···O3	0.93	2.33	3.006 (5)	129

Symmetry code: (i) −x+1/2, −y+5/2, −z.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duan, Z.-Y., Li, G., Zhang, W.-J., Han, E.-S. & Du, F.-Y. (2006). Acta Cryst. E62, o3103–o3104. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jing, Z.-L., Guo, M.-J., Chen, X. & Ming, Y. (2006). Acta Cryst. E62, o313–o315. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y.-X., Zhang, R., Wang, B.-L., Ding, D.-J. & Liu, S. (2006). Acta Cryst. E62, o4613–o4615. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, L.-G., Zhang, C.-N., Yan, G.-B., Zheng, Y.-F. & Yang, M.-H. (2007). Acta Cryst. E63, o1245–o1246. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wen, P. (2005). Acta Cryst. E61, o2918–o2920. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, C.-N., Yang, M.-H., Yan, G.-B. & Zhou, Y.-M. (2007). Acta Cryst. E63, o1247–o1248. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Y.-F., Yan, G.-B. & Gu, Y.-B. (2006). Acta Cryst. E62, o5134–o5135. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o1965-o1966

doi:10.1107/S1600536808029498

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A second monoclinic polymorph of 4-(2-hydr­­oxy-4-meth­oxy­benzyl­­idene­amino)-1,5-di­methyl-2-phenyl-1H-pyrazol-3(2H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

A second monoclinic polymorph of 4-(2-hydroxy-4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one