4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]benzoic acid methanol solvate

Sun, Y.-X.; Xie, X.-H.; Zhang, R.; Zhang, L.-F.; Xu, L.-X.

doi:10.1107/S1600536806039262

4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]benzoic acid methanol solvate

Y.-X. Sun, X.-H. Xie, R. Zhang, L.-F. Zhang and L.-X. Xu

The title compound, C₁₉H₁₇N₃O₃·CH₃OH, was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one and 4-formylbenzoic acid in methanol solution. As expected, the antipyrine derivative adopts a trans configuration about the central C=N bond. In the crystal structure, the molecules are linked into chains along the [01 $\overline{1}$ ] direction by O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039262/ci2176sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039262/ci2176Isup2.hkl Contains datablock I

CCDC reference: 624183

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.059
wR factor = 0.176
Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

4-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]benzoic acid methanol solvate top

Crystal data top

C₁₉H₁₇N₃O₃·CH₄O	Z = 2
M_r = 367.40	F(000) = 388
Triclinic, P1	D_x = 1.313 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4270 (7) Å	Cell parameters from 2860 reflections
b = 10.2516 (8) Å	θ = 2.5–27.0°
c = 10.3014 (8) Å	µ = 0.09 mm⁻¹
α = 74.450 (1)°	T = 295 K
β = 85.673 (1)°	Block, yellow
γ = 75.665 (1)°	0.45 × 0.40 × 0.30 mm
V = 929.20 (12) Å³

Data collection top

Bruker APEX area-detector diffractometer	3760 independent reflections
Radiation source: fine-focus sealed tube	2595 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.959, T_max = 0.973	k = −12→12
6972 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.0943P)² + 0.0586P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
3760 reflections	Δρ_max = 0.38 e Å⁻³
259 parameters	Δρ_min = −0.23 e Å⁻³
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (7)

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	0.35079 (16)	0.70738 (15)	0.57502 (16)	0.0749 (5)
O2	0.58626 (19)	1.38188 (18)	−0.13930 (19)	0.0993 (7)
H2	0.6204	1.4130	−0.2135	0.149*
O3	0.7622 (2)	1.20133 (18)	−0.1431 (2)	0.1165 (8)
N1	0.16205 (17)	0.77815 (16)	0.71427 (16)	0.0571 (4)
N2	0.06437 (17)	0.90351 (16)	0.71706 (15)	0.0557 (4)
N3	0.29010 (17)	1.02808 (17)	0.44551 (16)	0.0544 (4)
C1	0.1194 (2)	0.6504 (2)	0.76516 (19)	0.0550 (5)
C2	0.2234 (2)	0.5341 (2)	0.8248 (2)	0.0667 (6)
H2A	0.3184	0.5401	0.8356	0.080*
C3	0.1848 (3)	0.4084 (2)	0.8685 (2)	0.0801 (7)
H3	0.2551	0.3284	0.9070	0.096*
C4	0.0452 (3)	0.3997 (3)	0.8559 (2)	0.0838 (8)
H4A	0.0199	0.3144	0.8860	0.101*
C5	−0.0575 (3)	0.5170 (3)	0.7988 (3)	0.0880 (8)
H5	−0.1535	0.5115	0.7919	0.106*
C6	−0.0213 (2)	0.6424 (3)	0.7517 (2)	0.0713 (6)
H6	−0.0914	0.7215	0.7109	0.086*
C7	0.2604 (2)	0.8026 (2)	0.6089 (2)	0.0550 (5)
C8	0.22671 (19)	0.9496 (2)	0.55489 (18)	0.0507 (5)
C9	0.1104 (2)	1.0061 (2)	0.62592 (18)	0.0522 (5)
C10	0.0413 (3)	1.1543 (2)	0.6156 (2)	0.0694 (6)
H10A	−0.0632	1.1674	0.6207	0.104*
H10B	0.0682	1.2102	0.5311	0.104*
H10C	0.0740	1.1815	0.6882	0.104*
C11	−0.0097 (3)	0.9152 (2)	0.8436 (2)	0.0766 (7)
H11A	0.0614	0.9019	0.9107	0.115*
H11B	−0.0653	0.8454	0.8721	0.115*
H11C	−0.0744	1.0060	0.8315	0.115*
C12	0.3968 (2)	0.9674 (2)	0.3840 (2)	0.0576 (5)
H12	0.4319	0.8714	0.4143	0.069*
C13	0.4664 (2)	1.0443 (2)	0.26651 (18)	0.0522 (5)
C14	0.4270 (2)	1.1868 (2)	0.2223 (2)	0.0606 (5)
H14	0.3570	1.2371	0.2703	0.073*
C15	0.4889 (2)	1.2563 (2)	0.1090 (2)	0.0617 (5)
H15	0.4606	1.3530	0.0806	0.074*
C16	0.5932 (2)	1.1835 (2)	0.0365 (2)	0.0551 (5)
C17	0.6358 (2)	1.0411 (2)	0.0823 (2)	0.0676 (6)
H17	0.7082	0.9911	0.0360	0.081*
C18	0.5727 (2)	0.9720 (2)	0.1956 (2)	0.0664 (6)
H18	0.6020	0.8754	0.2249	0.080*
C19	0.6566 (2)	1.2541 (2)	−0.0908 (2)	0.0661 (6)
C20	0.7092 (17)	0.5482 (6)	0.5150 (11)	0.0959 (17)	0.675 (3)
H20A	0.7486	0.6294	0.4951	0.144*	0.675 (3)
H20B	0.6493	0.5533	0.4416	0.144*	0.675 (3)
H20C	0.7880	0.4663	0.5272	0.144*	0.675 (3)
O4	0.6226 (3)	0.5419 (3)	0.6354 (3)	0.0911 (8)	0.675 (3)
H4	0.5415	0.5945	0.6178	0.137*	0.675 (3)
C20'	0.695 (4)	0.5868 (14)	0.518 (3)	0.0959 (17)	0.325 (3)
H20D	0.6472	0.6532	0.5675	0.144*	0.325 (3)
H20E	0.6467	0.6086	0.4334	0.144*	0.325 (3)
H20F	0.7954	0.5904	0.5026	0.144*	0.325 (3)
O4'	0.6863 (6)	0.4500 (6)	0.5942 (6)	0.0911 (8)	0.325 (3)
H4'	0.7677	0.3971	0.5977	0.137*	0.325 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0660 (9)	0.0677 (9)	0.0815 (11)	−0.0048 (8)	0.0244 (8)	−0.0200 (8)
O2	0.0749 (11)	0.0813 (12)	0.1000 (14)	0.0070 (9)	0.0276 (10)	0.0157 (10)
O3	0.1074 (14)	0.0849 (12)	0.1093 (15)	0.0127 (11)	0.0646 (12)	0.0049 (10)
N1	0.0476 (9)	0.0594 (10)	0.0560 (10)	−0.0050 (7)	0.0085 (7)	−0.0106 (7)
N2	0.0507 (9)	0.0614 (10)	0.0465 (9)	−0.0039 (8)	0.0084 (7)	−0.0109 (7)
N3	0.0473 (9)	0.0678 (10)	0.0485 (9)	−0.0152 (8)	0.0053 (7)	−0.0161 (7)
C1	0.0547 (11)	0.0613 (12)	0.0437 (10)	−0.0107 (9)	0.0061 (8)	−0.0095 (8)
C2	0.0623 (13)	0.0681 (13)	0.0627 (13)	−0.0068 (11)	0.0014 (10)	−0.0134 (10)
C3	0.100 (2)	0.0635 (14)	0.0655 (15)	−0.0083 (13)	−0.0012 (13)	−0.0083 (11)
C4	0.117 (2)	0.0800 (16)	0.0597 (14)	−0.0447 (16)	0.0058 (14)	−0.0101 (12)
C5	0.0873 (18)	0.110 (2)	0.0696 (15)	−0.0497 (16)	−0.0057 (13)	−0.0016 (14)
C6	0.0607 (13)	0.0861 (15)	0.0586 (13)	−0.0195 (12)	−0.0041 (10)	−0.0015 (11)
C7	0.0441 (10)	0.0662 (12)	0.0522 (11)	−0.0094 (9)	0.0046 (8)	−0.0159 (9)
C8	0.0445 (10)	0.0641 (11)	0.0443 (10)	−0.0139 (8)	0.0011 (8)	−0.0145 (8)
C9	0.0498 (10)	0.0621 (11)	0.0425 (10)	−0.0100 (9)	−0.0009 (8)	−0.0126 (8)
C10	0.0765 (15)	0.0633 (12)	0.0630 (13)	−0.0092 (11)	0.0102 (11)	−0.0170 (10)
C11	0.0797 (15)	0.0779 (14)	0.0566 (13)	−0.0018 (12)	0.0248 (11)	−0.0133 (11)
C12	0.0507 (11)	0.0663 (12)	0.0535 (11)	−0.0137 (9)	0.0041 (9)	−0.0131 (9)
C13	0.0432 (10)	0.0643 (12)	0.0489 (11)	−0.0118 (8)	0.0028 (8)	−0.0160 (9)
C14	0.0514 (11)	0.0653 (12)	0.0642 (13)	−0.0093 (9)	0.0147 (10)	−0.0234 (10)
C15	0.0520 (11)	0.0542 (11)	0.0724 (14)	−0.0060 (9)	0.0108 (10)	−0.0147 (10)
C16	0.0419 (10)	0.0613 (12)	0.0574 (12)	−0.0084 (9)	0.0064 (9)	−0.0128 (9)
C17	0.0623 (13)	0.0628 (13)	0.0682 (14)	−0.0043 (10)	0.0229 (11)	−0.0169 (10)
C18	0.0646 (13)	0.0542 (11)	0.0696 (14)	−0.0048 (10)	0.0145 (11)	−0.0105 (10)
C19	0.0496 (11)	0.0641 (13)	0.0729 (14)	−0.0070 (10)	0.0135 (10)	−0.0079 (10)
C20	0.117 (4)	0.094 (4)	0.088 (2)	−0.031 (5)	0.024 (2)	−0.044 (4)
O4	0.0781 (17)	0.0878 (18)	0.0757 (15)	0.0057 (13)	0.0145 (12)	0.0051 (12)
C20'	0.117 (4)	0.094 (4)	0.088 (2)	−0.031 (5)	0.024 (2)	−0.044 (4)
O4'	0.0781 (17)	0.0878 (18)	0.0757 (15)	0.0057 (13)	0.0145 (12)	0.0051 (12)

Geometric parameters (Å, º) top

O1—C7	1.236 (2)	C10—H10C	0.96
O2—C19	1.294 (3)	C11—H11A	0.96
O2—H2	0.82	C11—H11B	0.96
O3—C19	1.176 (2)	C11—H11C	0.96
N1—C7	1.385 (2)	C12—C13	1.463 (3)
N1—N2	1.389 (2)	C12—H12	0.93
N1—C1	1.419 (2)	C13—C14	1.371 (3)
N2—C9	1.346 (2)	C13—C18	1.378 (3)
N2—C11	1.451 (2)	C14—C15	1.367 (3)
N3—C12	1.268 (2)	C14—H14	0.93
N3—C8	1.387 (2)	C15—C16	1.381 (3)
C1—C6	1.369 (3)	C15—H15	0.93
C1—C2	1.371 (3)	C16—C17	1.372 (3)
C2—C3	1.375 (3)	C16—C19	1.479 (3)
C2—H2A	0.93	C17—C18	1.371 (3)
C3—C4	1.359 (4)	C17—H17	0.93
C3—H3	0.93	C18—H18	0.93
C4—C5	1.363 (4)	C20—O4	1.429 (8)
C4—H4A	0.93	C20—H20A	0.96
C5—C6	1.364 (3)	C20—H20B	0.96
C5—H5	0.93	C20—H20C	0.96
C6—H6	0.93	O4—H4	0.82
C7—C8	1.422 (3)	C20'—O4'	1.429 (10)
C8—C9	1.365 (3)	C20'—H20D	0.96
C9—C10	1.475 (3)	C20'—H20E	0.96
C10—H10A	0.96	C20'—H20F	0.96
C10—H10B	0.96	O4'—H4'	0.82

C19—O2—H2	109.5	H10A—C10—H10C	109.5
C7—N1—N2	108.78 (15)	H10B—C10—H10C	109.5
C7—N1—C1	124.39 (17)	N2—C11—H11A	109.5
N2—N1—C1	120.30 (15)	N2—C11—H11B	109.5
C9—N2—N1	107.88 (15)	H11A—C11—H11B	109.5
C9—N2—C11	125.73 (17)	N2—C11—H11C	109.5
N1—N2—C11	117.89 (16)	H11A—C11—H11C	109.5
C12—N3—C8	119.29 (17)	H11B—C11—H11C	109.5
C6—C1—C2	120.7 (2)	N3—C12—C13	121.75 (19)
C6—C1—N1	120.82 (19)	N3—C12—H12	119.1
C2—C1—N1	118.50 (19)	C13—C12—H12	119.1
C1—C2—C3	118.9 (2)	C14—C13—C18	118.48 (18)
C1—C2—H2A	120.5	C14—C13—C12	122.08 (18)
C3—C2—H2A	120.5	C18—C13—C12	119.43 (18)
C4—C3—C2	120.7 (2)	C15—C14—C13	121.16 (19)
C4—C3—H3	119.6	C15—C14—H14	119.4
C2—C3—H3	119.6	C13—C14—H14	119.4
C3—C4—C5	119.6 (2)	C14—C15—C16	120.27 (19)
C3—C4—H4A	120.2	C14—C15—H15	119.9
C5—C4—H4A	120.2	C16—C15—H15	119.9
C4—C5—C6	120.9 (2)	C17—C16—C15	118.79 (18)
C4—C5—H5	119.6	C17—C16—C19	119.29 (18)
C6—C5—H5	119.6	C15—C16—C19	121.90 (18)
C5—C6—C1	119.2 (2)	C18—C17—C16	120.62 (18)
C5—C6—H6	120.4	C18—C17—H17	119.7
C1—C6—H6	120.4	C16—C17—H17	119.7
O1—C7—N1	122.49 (18)	C17—C18—C13	120.65 (19)
O1—C7—C8	132.01 (18)	C17—C18—H18	119.7
N1—C7—C8	105.46 (16)	C13—C18—H18	119.7
C9—C8—N3	123.20 (17)	O3—C19—O2	122.4 (2)
C9—C8—C7	107.92 (16)	O3—C19—C16	124.0 (2)
N3—C8—C7	128.80 (17)	O2—C19—C16	113.67 (18)
N2—C9—C8	109.54 (17)	O4'—C20'—H20D	109.5
N2—C9—C10	121.53 (17)	O4'—C20'—H20E	109.5
C8—C9—C10	128.90 (18)	H20D—C20'—H20E	109.5
C9—C10—H10A	109.5	O4'—C20'—H20F	109.5
C9—C10—H10B	109.5	H20D—C20'—H20F	109.5
H10A—C10—H10B	109.5	H20E—C20'—H20F	109.5
C9—C10—H10C	109.5	C20'—O4'—H4'	109.5

C7—N1—N2—C9	−6.8 (2)	N1—N2—C9—C8	6.0 (2)
C1—N1—N2—C9	−159.65 (17)	C11—N2—C9—C8	152.85 (19)
C7—N1—N2—C11	−156.69 (18)	N1—N2—C9—C10	−172.21 (17)
C1—N1—N2—C11	50.5 (3)	C11—N2—C9—C10	−25.3 (3)
C7—N1—C1—C6	−113.7 (2)	N3—C8—C9—N2	173.99 (16)
N2—N1—C1—C6	34.8 (3)	C7—C8—C9—N2	−2.9 (2)
C7—N1—C1—C2	64.5 (3)	N3—C8—C9—C10	−8.0 (3)
N2—N1—C1—C2	−147.07 (18)	C7—C8—C9—C10	175.10 (19)
C6—C1—C2—C3	1.4 (3)	C8—N3—C12—C13	178.87 (16)
N1—C1—C2—C3	−176.81 (19)	N3—C12—C13—C14	4.7 (3)
C1—C2—C3—C4	−1.6 (4)	N3—C12—C13—C18	−173.90 (19)
C2—C3—C4—C5	0.3 (4)	C18—C13—C14—C15	1.4 (3)
C3—C4—C5—C6	1.3 (4)	C12—C13—C14—C15	−177.15 (18)
C4—C5—C6—C1	−1.6 (4)	C13—C14—C15—C16	−0.1 (3)
C2—C1—C6—C5	0.2 (3)	C14—C15—C16—C17	−1.7 (3)
N1—C1—C6—C5	178.3 (2)	C14—C15—C16—C19	176.52 (19)
N2—N1—C7—O1	−172.90 (18)	C15—C16—C17—C18	2.0 (3)
C1—N1—C7—O1	−21.4 (3)	C19—C16—C17—C18	−176.2 (2)
N2—N1—C7—C8	4.9 (2)	C16—C17—C18—C13	−0.7 (4)
C1—N1—C7—C8	156.37 (17)	C14—C13—C18—C17	−1.0 (3)
C12—N3—C8—C9	−179.22 (18)	C12—C13—C18—C17	177.58 (19)
C12—N3—C8—C7	−3.0 (3)	C17—C16—C19—O3	−15.6 (4)
O1—C7—C8—C9	176.2 (2)	C15—C16—C19—O3	166.2 (3)
N1—C7—C8—C9	−1.3 (2)	C17—C16—C19—O2	165.5 (2)
O1—C7—C8—N3	−0.5 (4)	C15—C16—C19—O2	−12.7 (3)
N1—C7—C8—N3	−177.98 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ⁱ	0.82	1.75	2.513 (3)	153
O2—H2···O4′ⁱ	0.82	2.00	2.796 (6)	165
O4—H4···O1	0.82	1.89	2.712 (3)	177
C11—H11C···O3ⁱⁱ	0.96	2.27	3.209 (3)	166
C12—H12···O1	0.93	2.26	2.966 (3)	132

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

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4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]benzoic acid methanol solvate

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4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]benzoic acid methanol solvate