1,5-Dimethyl-4-[(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)amino]-2-phenyl-1H-pyrazol-3(2H)-one monohydrate

Mol­ecules of the title compound, C₁₉H₁₆N₄O₂·H₂O, are linked into a one-dimensional ladder structure by a combination of inter­molecular O—H...O and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.067
• wR factor = 0.149
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.92

Author Response: This problem has arisen because there is not good quality crystals and the ata collected with an old R-AXIS-IV. Several samples were screened. The selected sample exhibited the strongest diffraction behavior. Hence the precision of the structure is lowered.Validation issues a number of other alerts which are related to this issue.

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full          25.00
           From the CIF: _reflns_number_total               2852
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3114
           Completeness (_total/calc)             91.59%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.92
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT245_ALERT_2_C U(iso) H3E     Smaller than U(eq) O3      by ...       0.02 AngSq
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C7     -   C8     ...       1.53 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

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Computing details

Data collection: RAXIS (Rigaku,1996); cell refinement: RAXIS; data reduction: RAXIS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation, 1999); software used to prepare material for publication: TEXSAN.

1,5-Dimethyl-2-phenyl-4-[(2-oxo-2,3-dihydro-1H-indol-3-ylidene)amino]- 1H-pyrazol-3(2H)-one monohydrate

Crystal data

C19H16N4O2·H2O	F(000) = 1472
Mr = 350.37	Dx = 1.318 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 320 reflections
a = 17.587 (4) Å	θ = 2–25.1°
b = 7.2102 (14) Å	µ = 0.09 mm^−1
c = 28.973 (6) Å	T = 291 K
β = 106.00 (3)°	Prism, red
V = 3531.8 (12) Å^3	0.20 × 0.18 × 0.17 mm
Z = 8

Data collection

Rigaku R-AXIS-IV diffractometer	2852 independent reflections
Radiation source: fine-focus sealed tube	1876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 0 pixels mm^-1	θmax = 25.0°, θmin = 1.5°
Oscillation frames scans	h = −20→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→8
Tmin = 0.982, Tmax = 0.985	l = −33→34
4696 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0681P)^2 + 0.2329P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2852 reflections	Δρmax = 0.21 e Å^−3
248 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (4)

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	0.64010 (13)	0.0278 (4)	0.08458 (9)	0.0580 (8)
O2	0.94003 (12)	−0.1702 (3)	0.12203 (8)	0.0433 (7)
O3	0.97624 (18)	0.5796 (7)	0.05820 (14)	0.1102 (18)
N1	0.66632 (15)	−0.0214 (4)	0.01197 (10)	0.0398 (8)
N2	0.80549 (13)	0.1083 (4)	0.11781 (9)	0.0350 (7)
N3	1.00266 (14)	0.2385 (4)	0.18341 (9)	0.0328 (7)
N4	1.01800 (13)	0.0668 (4)	0.16424 (9)	0.0325 (7)
C1	0.73345 (17)	−0.0174 (5)	−0.00555 (11)	0.0334 (8)
C2	0.7357 (2)	−0.0526 (5)	−0.05154 (12)	0.0469 (10)
H2A	0.6904	−0.0868	−0.0752	0.056*
C3	0.8083 (2)	−0.0351 (6)	−0.06141 (13)	0.0574 (11)
H3A	0.8116	−0.0575	−0.0924	0.069*
C4	0.8761 (2)	0.0150 (6)	−0.02602 (14)	0.0589 (12)
H4A	0.9238	0.0279	−0.0337	0.071*
C5	0.87282 (18)	0.0462 (6)	0.02104 (13)	0.0451 (10)
H5A	0.9182	0.0792	0.0448	0.054*
C6	0.80098 (16)	0.0272 (5)	0.03169 (11)	0.0321 (8)
C7	0.77438 (16)	0.0546 (4)	0.07472 (11)	0.0302 (8)
C8	0.68499 (18)	0.0202 (5)	0.05913 (12)	0.0394 (9)
C9	0.94695 (17)	−0.0099 (5)	0.13718 (11)	0.0324 (8)
C10	0.88833 (16)	0.1307 (5)	0.13606 (10)	0.0291 (8)
C11	0.92315 (17)	0.2745 (5)	0.16394 (10)	0.0314 (8)
C12	0.88752 (19)	0.4497 (5)	0.17483 (13)	0.0462 (10)
H12A	0.8320	0.4507	0.1585	0.069*
H12B	0.9128	0.5530	0.1643	0.069*
H12C	0.8946	0.4588	0.2088	0.069*
C13	1.06280 (19)	0.3819 (5)	0.18476 (14)	0.0522 (11)
H13A	1.0485	0.4937	0.1982	0.078*
H13B	1.0659	0.4059	0.1527	0.078*
H13C	1.1132	0.3394	0.2042	0.078*
C14	1.08353 (16)	−0.0398 (4)	0.19214 (11)	0.0296 (8)
C15	1.12447 (17)	−0.1513 (5)	0.16838 (12)	0.0351 (8)
H15A	1.1108	−0.1540	0.1350	0.042*
C16	1.18659 (17)	−0.2598 (5)	0.19532 (13)	0.0438 (9)
H16A	1.2142	−0.3365	0.1798	0.053*
C17	1.20727 (17)	−0.2544 (5)	0.24464 (13)	0.0419 (9)
H17A	1.2489	−0.3270	0.2623	0.050*
C18	1.16630 (18)	−0.1412 (5)	0.26811 (12)	0.0386 (9)
H18A	1.1805	−0.1370	0.3015	0.046*
C19	1.10402 (16)	−0.0343 (5)	0.24156 (11)	0.0352 (8)
H19A	1.0760	0.0412	0.2571	0.042*
H1B	0.616 (2)	−0.034 (6)	−0.0094 (14)	0.068 (12)*
H3F	1.028 (3)	0.543 (7)	0.0627 (16)	0.106 (17)*
H3E	0.969 (3)	0.632 (8)	0.0787 (18)	0.087 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0337 (12)	0.086 (2)	0.0570 (17)	0.0012 (13)	0.0173 (12)	−0.0171 (15)
O2	0.0429 (13)	0.0347 (16)	0.0485 (15)	0.0000 (11)	0.0064 (11)	−0.0138 (12)
O3	0.0390 (17)	0.182 (5)	0.095 (3)	0.024 (2)	−0.0056 (17)	−0.090 (3)
N1	0.0280 (14)	0.049 (2)	0.0359 (18)	0.0023 (13)	−0.0019 (13)	−0.0053 (14)
N2	0.0285 (13)	0.0405 (18)	0.0348 (17)	0.0001 (12)	0.0065 (12)	−0.0024 (14)
N3	0.0333 (13)	0.0261 (16)	0.0353 (16)	−0.0033 (12)	0.0031 (11)	−0.0004 (13)
N4	0.0288 (13)	0.0300 (17)	0.0357 (16)	0.0014 (12)	0.0038 (11)	−0.0033 (13)
C1	0.0376 (17)	0.030 (2)	0.030 (2)	0.0034 (15)	0.0043 (14)	0.0046 (15)
C2	0.049 (2)	0.054 (3)	0.031 (2)	−0.0053 (18)	−0.0014 (16)	0.0038 (18)
C3	0.078 (3)	0.061 (3)	0.032 (2)	−0.002 (2)	0.013 (2)	0.005 (2)
C4	0.058 (2)	0.076 (3)	0.050 (3)	−0.001 (2)	0.026 (2)	0.012 (2)
C5	0.0367 (17)	0.057 (3)	0.041 (2)	−0.0019 (17)	0.0096 (15)	0.0073 (19)
C6	0.0346 (17)	0.029 (2)	0.0316 (18)	0.0044 (14)	0.0075 (14)	0.0032 (15)
C7	0.0310 (15)	0.0287 (19)	0.0301 (19)	0.0023 (14)	0.0068 (13)	0.0001 (15)
C8	0.0289 (16)	0.044 (2)	0.042 (2)	0.0035 (16)	0.0045 (15)	−0.0064 (17)
C9	0.0340 (16)	0.036 (2)	0.0279 (18)	−0.0059 (15)	0.0101 (13)	−0.0063 (16)
C10	0.0266 (15)	0.034 (2)	0.0277 (18)	−0.0013 (14)	0.0088 (13)	−0.0004 (15)
C11	0.0380 (17)	0.030 (2)	0.0247 (18)	0.0047 (15)	0.0056 (14)	0.0041 (15)
C12	0.054 (2)	0.036 (2)	0.044 (2)	0.0049 (17)	0.0058 (17)	−0.0022 (18)
C13	0.046 (2)	0.039 (3)	0.065 (3)	−0.0128 (17)	0.0060 (18)	0.000 (2)
C14	0.0252 (14)	0.0260 (19)	0.037 (2)	−0.0071 (13)	0.0070 (13)	−0.0030 (15)
C15	0.0321 (16)	0.039 (2)	0.0357 (19)	−0.0040 (15)	0.0115 (14)	−0.0014 (16)
C16	0.0363 (18)	0.040 (2)	0.061 (3)	−0.0013 (16)	0.0234 (17)	−0.012 (2)
C17	0.0302 (17)	0.038 (2)	0.054 (2)	0.0009 (16)	0.0063 (16)	0.0032 (19)
C18	0.0381 (17)	0.044 (2)	0.0315 (19)	−0.0016 (17)	0.0060 (15)	0.0049 (17)
C19	0.0317 (16)	0.042 (2)	0.033 (2)	0.0018 (15)	0.0107 (14)	−0.0076 (16)

Geometric parameters (Å, º)

O1—C8	1.221 (4)	C5—H5A	0.9300
O2—C9	1.231 (4)	C6—C7	1.461 (4)
O3—H3F	0.92 (5)	C7—C8	1.531 (4)
O3—H3E	0.75 (5)	C9—C10	1.440 (4)
N1—C8	1.348 (4)	C10—C11	1.353 (4)
N1—C1	1.408 (4)	C11—C12	1.482 (5)
N1—H1B	0.93 (4)	C12—H12A	0.9600
N2—C7	1.277 (4)	C12—H12B	0.9600
N2—C10	1.415 (4)	C12—H12C	0.9600
N3—C11	1.381 (4)	C13—H13A	0.9600
N3—N4	1.413 (4)	C13—H13B	0.9600
N3—C13	1.471 (4)	C13—H13C	0.9600
N4—C9	1.393 (4)	C14—C19	1.377 (4)
N4—C14	1.435 (4)	C14—C15	1.383 (4)
C1—C2	1.368 (5)	C15—C16	1.395 (4)
C1—C6	1.404 (4)	C15—H15A	0.9300
C2—C3	1.390 (5)	C16—C17	1.375 (5)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.389 (5)	C17—C18	1.385 (5)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.399 (5)	C18—C19	1.386 (4)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.388 (4)	C19—H19A	0.9300
H3F—O3—H3E	115 (4)	N4—C9—C10	105.0 (3)
C8—N1—C1	111.5 (3)	C11—C10—N2	124.1 (3)
C8—N1—H1B	128 (2)	C11—C10—C9	108.8 (2)
C1—N1—H1B	120 (2)	N2—C10—C9	125.8 (3)
C7—N2—C10	121.3 (3)	C10—C11—N3	109.9 (3)
C11—N3—N4	106.6 (2)	C10—C11—C12	129.2 (3)
C11—N3—C13	121.2 (3)	N3—C11—C12	120.9 (3)
N4—N3—C13	114.3 (3)	C11—C12—H12A	109.5
C9—N4—N3	109.3 (2)	C11—C12—H12B	109.5
C9—N4—C14	124.1 (3)	H12A—C12—H12B	109.5
N3—N4—C14	117.3 (2)	C11—C12—H12C	109.5
C2—C1—C6	123.1 (3)	H12A—C12—H12C	109.5
C2—C1—N1	126.8 (3)	H12B—C12—H12C	109.5
C6—C1—N1	110.1 (3)	N3—C13—H13A	109.5
C1—C2—C3	117.3 (3)	N3—C13—H13B	109.5
C1—C2—H2A	121.4	H13A—C13—H13B	109.5
C3—C2—H2A	121.4	N3—C13—H13C	109.5
C4—C3—C2	121.5 (4)	H13A—C13—H13C	109.5
C4—C3—H3A	119.2	H13B—C13—H13C	109.5
C2—C3—H3A	119.2	C19—C14—C15	120.7 (3)
C3—C4—C5	120.3 (4)	C19—C14—N4	120.6 (3)
C3—C4—H4A	119.9	C15—C14—N4	118.6 (3)
C5—C4—H4A	119.9	C14—C15—C16	118.9 (3)
C6—C5—C4	119.0 (3)	C14—C15—H15A	120.6
C6—C5—H5A	120.5	C16—C15—H15A	120.6
C4—C5—H5A	120.5	C17—C16—C15	120.5 (3)
C5—C6—C1	118.7 (3)	C17—C16—H16A	119.7
C5—C6—C7	134.6 (3)	C15—C16—H16A	119.7
C1—C6—C7	106.5 (3)	C16—C17—C18	120.2 (3)
N2—C7—C6	136.3 (3)	C16—C17—H17A	119.9
N2—C7—C8	117.8 (3)	C18—C17—H17A	119.9
C6—C7—C8	105.7 (3)	C17—C18—C19	119.6 (3)
O1—C8—N1	127.2 (3)	C17—C18—H18A	120.2
O1—C8—C7	126.6 (3)	C19—C18—H18A	120.2
N1—C8—C7	106.2 (3)	C14—C19—C18	120.1 (3)
O2—C9—N4	124.0 (3)	C14—C19—H19A	120.0
O2—C9—C10	130.8 (3)	C18—C19—H19A	120.0
C11—N3—N4—C9	−5.9 (3)	C14—N4—C9—O2	−23.3 (5)
C13—N3—N4—C9	−142.7 (3)	N3—N4—C9—C10	6.2 (3)
C11—N3—N4—C14	−154.1 (3)	C14—N4—C9—C10	151.6 (3)
C13—N3—N4—C14	69.2 (3)	C7—N2—C10—C11	138.1 (3)
C8—N1—C1—C2	−180.0 (3)	C7—N2—C10—C9	−56.4 (4)
C8—N1—C1—C6	0.7 (4)	O2—C9—C10—C11	170.3 (4)
C6—C1—C2—C3	−2.7 (5)	N4—C9—C10—C11	−4.2 (4)
N1—C1—C2—C3	178.1 (4)	O2—C9—C10—N2	2.8 (6)
C1—C2—C3—C4	0.3 (6)	N4—C9—C10—N2	−171.6 (3)
C2—C3—C4—C5	1.1 (6)	N2—C10—C11—N3	168.3 (3)
C3—C4—C5—C6	−0.3 (6)	C9—C10—C11—N3	0.6 (4)
C4—C5—C6—C1	−1.9 (5)	N2—C10—C11—C12	−11.3 (5)
C4—C5—C6—C7	−177.1 (4)	C9—C10—C11—C12	−178.9 (3)
C2—C1—C6—C5	3.5 (5)	N4—N3—C11—C10	3.2 (3)
N1—C1—C6—C5	−177.1 (3)	C13—N3—C11—C10	136.3 (3)
C2—C1—C6—C7	180.0 (3)	N4—N3—C11—C12	−177.2 (3)
N1—C1—C6—C7	−0.7 (4)	C13—N3—C11—C12	−44.1 (4)
C10—N2—C7—C6	−10.4 (6)	C9—N4—C14—C19	−110.3 (4)
C10—N2—C7—C8	175.5 (3)	N3—N4—C14—C19	32.7 (4)
C5—C6—C7—N2	1.6 (7)	C9—N4—C14—C15	68.2 (4)
C1—C6—C7—N2	−174.1 (4)	N3—N4—C14—C15	−148.9 (3)
C5—C6—C7—C8	176.1 (4)	C19—C14—C15—C16	0.5 (5)
C1—C6—C7—C8	0.4 (3)	N4—C14—C15—C16	−177.9 (3)
C1—N1—C8—O1	−179.8 (4)	C14—C15—C16—C17	−0.7 (5)
C1—N1—C8—C7	−0.4 (4)	C15—C16—C17—C18	0.2 (5)
N2—C7—C8—O1	−4.9 (5)	C16—C17—C18—C19	0.4 (5)
C6—C7—C8—O1	179.4 (4)	C15—C14—C19—C18	0.0 (5)
N2—C7—C8—N1	175.7 (3)	N4—C14—C19—C18	178.5 (3)
C6—C7—C8—N1	0.0 (4)	C17—C18—C19—C14	−0.5 (5)
N3—N4—C9—O2	−168.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3^i	0.93 (4)	1.87 (4)	2.790 (4)	171 (4)
O3—H3F···O1^ii	0.92 (5)	1.91 (5)	2.796 (4)	163 (5)
O3—H3E···O2^iii	0.75 (5)	2.05 (5)	2.780 (5)	165 (6)

Symmetry codes: (i) −x+3/2, −y+1/2, −z; (ii) x+1/2, y+1/2, z; (iii) x, y+1, z.