4-[(4-Hydroxy­benzyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one monohydrate

The title compound, C₁₈H₁₉N₃O₃, was prepared using 4-hydroxy­benzaldehyde and 4-amino-1,5-dimethyl-2-phenyl­pyrazolidin-3-one. The crystal structure shows that the title compound includes a water mol­ecule, which forms O—H...O hydrogen bonds with adjacent mol­ecules and plays an important role in the stabilization of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.038
• wR factor = 0.103
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

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

4-[(4-Hydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one monohydrate

Crystal data

C18H17N3O2·H2O	Z = 2
Mr = 325.36	F(000) = 344
Triclinic, P1	Dx = 1.327 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.393 (2) Å	Cell parameters from 2426 reflections
b = 8.983 (3) Å	θ = 2.6–27.7°
c = 12.823 (4) Å	µ = 0.09 mm^−1
α = 77.510 (4)°	T = 294 K
β = 82.756 (3)°	Block, yellow
γ = 79.450 (3)°	0.52 × 0.46 × 0.34 mm
V = 814.1 (4) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2843 independent reflections
Radiation source: fine-focus sealed tube	2407 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→8
Tmin = 0.923, Tmax = 0.969	k = −9→10
4423 measured reflections	l = −15→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom, OH from difmap
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 0.1768P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2843 reflections	Δρmax = 0.18 e Å^−3
229 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.082 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.26399 (17)	0.52695 (14)	0.90315 (8)	0.0576 (3)
H1	0.378 (3)	0.564 (2)	0.8955 (14)	0.069*
O2	0.27899 (14)	0.24622 (13)	0.31129 (8)	0.0541 (3)
N1	−0.12979 (16)	0.10579 (14)	0.32655 (9)	0.0448 (3)
N2	0.03441 (16)	0.14615 (14)	0.27238 (9)	0.0456 (3)
N3	0.01376 (17)	0.27017 (13)	0.52394 (9)	0.0423 (3)
C3	0.12160 (19)	0.20989 (16)	0.33732 (11)	0.0411 (3)
C4	−0.00292 (19)	0.21763 (15)	0.43150 (11)	0.0385 (3)
C5	−0.15391 (19)	0.15437 (16)	0.41990 (11)	0.0407 (3)
C6	−0.2620 (2)	0.0577 (2)	0.27261 (14)	0.0587 (4)
H6A	−0.3734	0.0487	0.3192	0.088*
H6B	−0.2116	−0.0405	0.2541	0.088*
H6C	−0.2891	0.1328	0.2086	0.088*
C7	0.1225 (2)	0.07498 (17)	0.18543 (11)	0.0423 (3)
C8	0.1120 (2)	0.15511 (19)	0.08194 (12)	0.0509 (4)
H8	0.0461	0.2548	0.0677	0.061*
C9	0.2005 (3)	0.0857 (2)	−0.00086 (13)	0.0605 (5)
H9	0.1950	0.1395	−0.0713	0.073*
C10	0.2958 (2)	−0.0608 (2)	0.01944 (14)	0.0604 (5)
H10	0.3554	−0.1064	−0.0369	0.073*
C11	0.3035 (3)	−0.1402 (2)	0.12245 (15)	0.0750 (6)
H11	0.3673	−0.2407	0.1363	0.090*
C12	0.2173 (3)	−0.0728 (2)	0.20612 (14)	0.0670 (5)
H12	0.2234	−0.1272	0.2764	0.080*
C13	−0.3242 (2)	0.1400 (2)	0.49238 (13)	0.0551 (4)
H13A	−0.4298	0.1837	0.4529	0.083*
H13B	−0.3249	0.1939	0.5494	0.083*
H13C	−0.3285	0.0328	0.5219	0.083*
C14	0.1537 (2)	0.33078 (16)	0.53119 (11)	0.0437 (4)
H14	0.2430	0.3410	0.4733	0.052*
C15	0.1786 (2)	0.38482 (16)	0.62749 (11)	0.0414 (3)
C16	0.0428 (2)	0.39194 (17)	0.71239 (12)	0.0465 (4)
H16	−0.0707	0.3641	0.7079	0.056*
C17	0.0729 (2)	0.43934 (18)	0.80311 (12)	0.0487 (4)
H17	−0.0195	0.4419	0.8594	0.058*
C18	0.2400 (2)	0.48318 (16)	0.81099 (11)	0.0430 (3)
C19	0.3756 (2)	0.48062 (18)	0.72628 (12)	0.0475 (4)
H19	0.4877	0.5116	0.7299	0.057*
C20	0.3434 (2)	0.43174 (18)	0.63632 (12)	0.0472 (4)
H20	0.4354	0.4303	0.5798	0.057*
O3	0.5794 (2)	0.6307 (2)	0.88721 (11)	0.0819 (5)
H3A	0.641 (4)	0.619 (3)	0.940 (2)	0.123*
H3B	0.642 (4)	0.671 (3)	0.825 (2)	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0618 (7)	0.0780 (8)	0.0433 (6)	−0.0226 (6)	−0.0074 (5)	−0.0233 (5)
O2	0.0496 (6)	0.0716 (8)	0.0504 (6)	−0.0252 (5)	0.0014 (5)	−0.0227 (5)
N1	0.0426 (7)	0.0541 (8)	0.0447 (7)	−0.0147 (5)	−0.0040 (5)	−0.0188 (6)
N2	0.0456 (7)	0.0554 (8)	0.0427 (7)	−0.0166 (6)	−0.0003 (5)	−0.0197 (6)
N3	0.0499 (7)	0.0405 (7)	0.0395 (6)	−0.0065 (5)	−0.0091 (5)	−0.0120 (5)
C3	0.0443 (8)	0.0410 (8)	0.0418 (8)	−0.0096 (6)	−0.0068 (6)	−0.0124 (6)
C4	0.0441 (8)	0.0353 (7)	0.0382 (7)	−0.0055 (6)	−0.0085 (6)	−0.0097 (6)
C5	0.0444 (8)	0.0390 (8)	0.0397 (8)	−0.0055 (6)	−0.0061 (6)	−0.0093 (6)
C6	0.0537 (9)	0.0750 (12)	0.0589 (10)	−0.0199 (8)	−0.0112 (8)	−0.0264 (9)
C7	0.0438 (8)	0.0484 (8)	0.0409 (8)	−0.0130 (6)	−0.0046 (6)	−0.0168 (6)
C8	0.0581 (9)	0.0502 (9)	0.0457 (9)	−0.0055 (7)	−0.0083 (7)	−0.0129 (7)
C9	0.0717 (11)	0.0705 (11)	0.0399 (9)	−0.0122 (9)	−0.0024 (8)	−0.0132 (8)
C10	0.0558 (10)	0.0770 (12)	0.0543 (10)	−0.0061 (9)	−0.0006 (8)	−0.0319 (9)
C11	0.0926 (14)	0.0622 (11)	0.0658 (12)	0.0174 (10)	−0.0149 (10)	−0.0239 (9)
C12	0.0955 (14)	0.0567 (11)	0.0447 (9)	0.0027 (10)	−0.0126 (9)	−0.0105 (8)
C13	0.0473 (9)	0.0696 (11)	0.0521 (9)	−0.0135 (8)	−0.0008 (7)	−0.0188 (8)
C14	0.0481 (8)	0.0440 (8)	0.0413 (8)	−0.0070 (6)	−0.0066 (6)	−0.0126 (6)
C15	0.0491 (8)	0.0368 (7)	0.0408 (8)	−0.0067 (6)	−0.0101 (6)	−0.0095 (6)
C16	0.0450 (8)	0.0510 (9)	0.0486 (8)	−0.0127 (7)	−0.0078 (7)	−0.0146 (7)
C17	0.0480 (8)	0.0567 (9)	0.0442 (8)	−0.0123 (7)	−0.0002 (6)	−0.0149 (7)
C18	0.0510 (8)	0.0431 (8)	0.0376 (7)	−0.0080 (6)	−0.0094 (6)	−0.0103 (6)
C19	0.0463 (8)	0.0548 (9)	0.0470 (8)	−0.0146 (7)	−0.0088 (7)	−0.0142 (7)
C20	0.0487 (8)	0.0528 (9)	0.0430 (8)	−0.0124 (7)	−0.0006 (6)	−0.0142 (7)
O3	0.0759 (9)	0.1298 (13)	0.0526 (8)	−0.0567 (9)	−0.0125 (7)	−0.0079 (8)

Geometric parameters (Å, º)

O1—C18	1.3646 (17)	C10—C11	1.361 (3)
O1—H1	0.94 (2)	C10—H10	0.9300
O2—C3	1.2513 (17)	C11—C12	1.375 (2)
N1—C5	1.3411 (17)	C11—H11	0.9300
N1—N2	1.3882 (17)	C12—H12	0.9300
N1—C6	1.4404 (18)	C13—H13A	0.9600
N2—C3	1.3833 (18)	C13—H13B	0.9600
N2—C7	1.4313 (18)	C13—H13C	0.9600
N3—C14	1.2758 (19)	C14—C15	1.464 (2)
N3—C4	1.3940 (17)	C14—H14	0.9300
C3—C4	1.429 (2)	C15—C20	1.385 (2)
C4—C5	1.379 (2)	C15—C16	1.388 (2)
C5—C13	1.476 (2)	C16—C17	1.378 (2)
C6—H6A	0.9600	C16—H16	0.9300
C6—H6B	0.9600	C17—C18	1.384 (2)
C6—H6C	0.9600	C17—H17	0.9300
C7—C8	1.370 (2)	C18—C19	1.384 (2)
C7—C12	1.370 (2)	C19—C20	1.381 (2)
C8—C9	1.381 (2)	C19—H19	0.9300
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.361 (2)	O3—H3A	0.83 (3)
C9—H9	0.9300	O3—H3B	0.91 (3)
C18—O1—H1	109.6 (11)	C10—C11—C12	120.39 (17)
C5—N1—N2	108.07 (11)	C10—C11—H11	119.8
C5—N1—C6	128.99 (13)	C12—C11—H11	119.8
N2—N1—C6	121.11 (12)	C7—C12—C11	119.68 (16)
C3—N2—N1	109.21 (11)	C7—C12—H12	120.2
C3—N2—C7	125.78 (12)	C11—C12—H12	120.2
N1—N2—C7	120.72 (11)	C5—C13—H13A	109.5
C14—N3—C4	120.46 (13)	C5—C13—H13B	109.5
O2—C3—N2	122.57 (13)	H13A—C13—H13B	109.5
O2—C3—C4	131.95 (13)	C5—C13—H13C	109.5
N2—C3—C4	105.47 (12)	H13A—C13—H13C	109.5
C5—C4—N3	122.10 (13)	H13B—C13—H13C	109.5
C5—C4—C3	107.32 (12)	N3—C14—C15	122.29 (14)
N3—C4—C3	130.54 (13)	N3—C14—H14	118.9
N1—C5—C4	109.71 (12)	C15—C14—H14	118.9
N1—C5—C13	121.28 (13)	C20—C15—C16	117.30 (13)
C4—C5—C13	129.00 (13)	C20—C15—C14	119.80 (14)
N1—C6—H6A	109.5	C16—C15—C14	122.90 (14)
N1—C6—H6B	109.5	C17—C16—C15	121.33 (14)
H6A—C6—H6B	109.5	C17—C16—H16	119.3
N1—C6—H6C	109.5	C15—C16—H16	119.3
H6A—C6—H6C	109.5	C16—C17—C18	120.38 (14)
H6B—C6—H6C	109.5	C16—C17—H17	119.8
C8—C7—C12	120.34 (14)	C18—C17—H17	119.8
C8—C7—N2	119.83 (14)	O1—C18—C19	122.55 (14)
C12—C7—N2	119.83 (13)	O1—C18—C17	118.14 (13)
C7—C8—C9	119.05 (15)	C19—C18—C17	119.31 (13)
C7—C8—H8	120.5	C20—C19—C18	119.45 (14)
C9—C8—H8	120.5	C20—C19—H19	120.3
C10—C9—C8	120.76 (16)	C18—C19—H19	120.3
C10—C9—H9	119.6	C19—C20—C15	122.20 (14)
C8—C9—H9	119.6	C19—C20—H20	118.9
C11—C10—C9	119.77 (16)	C15—C20—H20	118.9
C11—C10—H10	120.1	H3A—O3—H3B	112 (3)
C9—C10—H10	120.1
C5—N1—N2—C3	4.96 (16)	C3—N2—C7—C12	78.3 (2)
C6—N1—N2—C3	170.84 (13)	N1—N2—C7—C12	−75.84 (19)
C5—N1—N2—C7	162.98 (12)	C12—C7—C8—C9	−0.9 (2)
C6—N1—N2—C7	−31.1 (2)	N2—C7—C8—C9	178.87 (14)
N1—N2—C3—O2	174.72 (13)	C7—C8—C9—C10	0.6 (3)
C7—N2—C3—O2	18.1 (2)	C8—C9—C10—C11	0.3 (3)
N1—N2—C3—C4	−4.13 (15)	C9—C10—C11—C12	−0.7 (3)
C7—N2—C3—C4	−160.76 (13)	C8—C7—C12—C11	0.5 (3)
C14—N3—C4—C5	−178.66 (13)	N2—C7—C12—C11	−179.30 (17)
C14—N3—C4—C3	4.3 (2)	C10—C11—C12—C7	0.3 (3)
O2—C3—C4—C5	−176.83 (15)	C4—N3—C14—C15	−178.82 (12)
N2—C3—C4—C5	1.87 (15)	N3—C14—C15—C20	171.94 (14)
O2—C3—C4—N3	0.6 (3)	N3—C14—C15—C16	−8.1 (2)
N2—C3—C4—N3	179.27 (13)	C20—C15—C16—C17	−1.9 (2)
N2—N1—C5—C4	−3.72 (16)	C14—C15—C16—C17	178.16 (14)
C6—N1—C5—C4	−168.13 (15)	C15—C16—C17—C18	0.8 (2)
N2—N1—C5—C13	175.01 (13)	C16—C17—C18—O1	−179.02 (14)
C6—N1—C5—C13	10.6 (2)	C16—C17—C18—C19	0.7 (2)
N3—C4—C5—N1	−176.53 (12)	O1—C18—C19—C20	178.57 (14)
C3—C4—C5—N1	1.14 (16)	C17—C18—C19—C20	−1.2 (2)
N3—C4—C5—C13	4.9 (2)	C18—C19—C20—C15	0.1 (2)
C3—C4—C5—C13	−177.46 (14)	C16—C15—C20—C19	1.5 (2)
C3—N2—C7—C8	−101.49 (18)	C14—C15—C20—C19	−178.60 (14)
N1—N2—C7—C8	104.34 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.94 (2)	1.69 (2)	2.6348 (18)	177.5 (18)
O3—H3A···O1^i	0.83 (3)	2.27 (3)	3.0182 (19)	149 (3)
O3—H3B···O2^ii	0.91 (3)	1.81 (3)	2.7076 (18)	168 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.