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In the title Schiff base compound, C16H15N3OS, there are two intra­molecular hydrogen bonds and one inter­molecular hydrogen bond. The latter results in a one-dimensional chain in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005910/wn2112sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005910/wn2112Isup2.hkl
Contains datablock I

CCDC reference: 640515

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.117
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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,1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(E)-4-(2-Hydroxy-4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one top
Crystal data top
C19H19N3O3F(000) = 712
Mr = 337.37Dx = 1.325 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.0306 (9) ÅCell parameters from 2000 reflections
b = 7.5903 (7) Åθ = 2.1–25.0°
c = 22.248 (2) ŵ = 0.09 mm1
β = 93.021 (2)°T = 293 K
V = 1691.5 (3) Å3Block, colourless
Z = 40.28 × 0.28 × 0.20 mm
Data collection top
Bruker APEX-II area-detector
diffractometer
2980 independent reflections
Radiation source: fine-focus sealed tube2254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.975, Tmax = 0.982k = 99
9918 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0692P)2]
where P = (Fo2 + 2Fc2)/3
2980 reflections(Δ/σ)max < 0.001
230 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
C10.04294 (14)0.50019 (17)0.40731 (7)0.0478 (4)
H10.00870.59290.38560.057*
C20.14097 (14)0.53671 (17)0.45081 (6)0.0465 (3)
C30.18717 (15)0.70877 (18)0.45834 (7)0.0554 (4)
H30.15260.79850.43530.066*
C40.28131 (16)0.7498 (2)0.49834 (7)0.0580 (4)
H40.31060.86540.50220.070*
C50.33287 (15)0.61613 (19)0.53333 (7)0.0512 (4)
C60.28989 (14)0.44426 (18)0.52741 (7)0.0513 (4)
H60.32510.35550.55070.062*
C70.19416 (14)0.40452 (17)0.48671 (6)0.0466 (4)
C80.08607 (13)0.30620 (16)0.35236 (6)0.0442 (3)
C90.13026 (13)0.14130 (17)0.34049 (7)0.0467 (4)
C100.14209 (13)0.42590 (18)0.31028 (7)0.0472 (4)
C110.30298 (14)0.37380 (17)0.22915 (6)0.0476 (4)
C120.26297 (16)0.50168 (19)0.18781 (8)0.0607 (4)
H120.17930.55380.18910.073*
C130.3497 (2)0.5509 (2)0.14433 (8)0.0743 (5)
H130.32370.63650.11620.089*
C140.4742 (2)0.4743 (2)0.14227 (9)0.0749 (5)
H140.53190.50790.11300.090*
C150.51170 (17)0.3489 (2)0.18365 (8)0.0658 (5)
H150.59530.29660.18210.079*
C160.42816 (14)0.29803 (19)0.22767 (7)0.0533 (4)
H160.45560.21380.25600.064*
C170.10232 (17)0.02543 (18)0.37236 (8)0.0639 (5)
H17A0.06260.00080.40970.096*
H17B0.18420.08860.38040.096*
H17C0.04200.09630.34770.096*
C180.19623 (15)0.01017 (19)0.24572 (8)0.0584 (4)
H18A0.18580.10380.26360.088*
H18B0.27340.00970.22200.088*
H18C0.11840.03730.22050.088*
C190.47768 (18)0.5381 (2)0.61056 (8)0.0678 (5)
H19A0.52240.44860.58660.102*
H19B0.53980.59180.63640.102*
H19C0.40580.48610.63460.102*
N10.00144 (11)0.34202 (14)0.39776 (5)0.0476 (3)
N20.21315 (11)0.14334 (13)0.29319 (5)0.0466 (3)
N30.21195 (11)0.31878 (14)0.27256 (6)0.0498 (3)
O10.42580 (11)0.66863 (13)0.57212 (5)0.0664 (3)
O20.15459 (11)0.23513 (13)0.48254 (5)0.0632 (3)
H20.09650.22760.45810.095*
O30.13802 (11)0.58828 (12)0.30592 (5)0.0642 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0563 (9)0.0429 (8)0.0443 (8)0.0034 (6)0.0040 (7)0.0022 (6)
C20.0528 (8)0.0424 (7)0.0442 (8)0.0003 (6)0.0026 (6)0.0003 (6)
C30.0665 (9)0.0421 (8)0.0584 (10)0.0008 (7)0.0119 (8)0.0051 (7)
C40.0705 (10)0.0422 (8)0.0623 (10)0.0062 (7)0.0133 (8)0.0001 (7)
C50.0553 (8)0.0531 (9)0.0457 (8)0.0023 (6)0.0069 (7)0.0035 (7)
C60.0586 (9)0.0467 (8)0.0492 (9)0.0041 (7)0.0067 (7)0.0037 (7)
C70.0554 (8)0.0390 (7)0.0451 (9)0.0000 (6)0.0005 (7)0.0004 (6)
C80.0478 (8)0.0401 (7)0.0447 (8)0.0009 (6)0.0032 (6)0.0009 (6)
C90.0469 (8)0.0423 (8)0.0510 (9)0.0024 (6)0.0037 (7)0.0017 (6)
C100.0509 (8)0.0389 (8)0.0521 (9)0.0002 (6)0.0051 (7)0.0010 (6)
C110.0552 (9)0.0440 (8)0.0440 (8)0.0103 (6)0.0064 (7)0.0038 (6)
C120.0664 (10)0.0561 (9)0.0589 (10)0.0112 (7)0.0038 (8)0.0056 (7)
C130.0984 (14)0.0714 (11)0.0524 (11)0.0279 (10)0.0033 (10)0.0144 (8)
C140.0911 (14)0.0763 (12)0.0593 (11)0.0334 (10)0.0231 (10)0.0080 (9)
C150.0657 (10)0.0620 (10)0.0714 (12)0.0171 (8)0.0199 (9)0.0167 (9)
C160.0576 (9)0.0468 (8)0.0559 (10)0.0064 (6)0.0063 (7)0.0045 (7)
C170.0751 (10)0.0423 (8)0.0759 (12)0.0026 (7)0.0195 (9)0.0081 (7)
C180.0651 (10)0.0478 (8)0.0623 (10)0.0039 (7)0.0048 (8)0.0087 (7)
C190.0730 (11)0.0724 (11)0.0597 (10)0.0007 (8)0.0199 (8)0.0005 (9)
N10.0528 (7)0.0438 (7)0.0462 (7)0.0000 (5)0.0040 (6)0.0007 (5)
N20.0529 (7)0.0345 (6)0.0530 (7)0.0013 (5)0.0074 (6)0.0012 (5)
N30.0575 (7)0.0376 (6)0.0555 (8)0.0008 (5)0.0135 (6)0.0035 (5)
O10.0750 (7)0.0578 (7)0.0686 (8)0.0053 (5)0.0258 (6)0.0002 (5)
O20.0801 (8)0.0406 (6)0.0707 (8)0.0038 (5)0.0227 (6)0.0032 (5)
O30.0839 (8)0.0350 (6)0.0757 (8)0.0004 (5)0.0230 (6)0.0032 (5)
Geometric parameters (Å, º) top
C1—N11.2919 (16)C11—N31.4261 (17)
C1—C21.443 (2)C12—C131.386 (2)
C1—H10.9300C12—H120.9300
C2—C31.3988 (19)C13—C141.380 (3)
C2—C71.4050 (19)C13—H130.9300
C3—C41.367 (2)C14—C151.363 (3)
C3—H30.9300C14—H140.9300
C4—C51.395 (2)C15—C161.377 (2)
C4—H40.9300C15—H150.9300
C5—O11.3628 (16)C16—H160.9300
C5—C61.382 (2)C17—H17A0.9600
C6—C71.3873 (19)C17—H17B0.9600
C6—H60.9300C17—H17C0.9600
C7—O21.3502 (16)C18—N21.4653 (18)
C8—C91.3584 (18)C18—H18A0.9600
C8—N11.3993 (17)C18—H18B0.9600
C8—C101.4400 (19)C18—H18C0.9600
C9—N21.3750 (17)C19—O11.4248 (18)
C9—C171.4845 (19)C19—H19A0.9600
C10—O31.2368 (16)C19—H19B0.9600
C10—N31.3850 (17)C19—H19C0.9600
C11—C121.382 (2)N2—N31.4083 (15)
C11—C161.383 (2)O2—H20.8200
N1—C1—C2121.71 (13)C12—C13—H13119.6
N1—C1—H1119.1C15—C14—C13119.29 (16)
C2—C1—H1119.1C15—C14—H14120.4
C3—C2—C7117.42 (13)C13—C14—H14120.4
C3—C2—C1120.10 (13)C14—C15—C16121.29 (16)
C7—C2—C1122.47 (12)C14—C15—H15119.4
C4—C3—C2122.37 (14)C16—C15—H15119.4
C4—C3—H3118.8C15—C16—C11119.19 (15)
C2—C3—H3118.8C15—C16—H16120.4
C3—C4—C5119.10 (14)C11—C16—H16120.4
C3—C4—H4120.4C9—C17—H17A109.5
C5—C4—H4120.4C9—C17—H17B109.5
O1—C5—C6124.29 (13)H17A—C17—H17B109.5
O1—C5—C4115.26 (13)C9—C17—H17C109.5
C6—C5—C4120.45 (14)H17A—C17—H17C109.5
C5—C6—C7119.83 (13)H17B—C17—H17C109.5
C5—C6—H6120.1N2—C18—H18A109.5
C7—C6—H6120.1N2—C18—H18B109.5
O2—C7—C6117.91 (12)H18A—C18—H18B109.5
O2—C7—C2121.27 (13)N2—C18—H18C109.5
C6—C7—C2120.82 (13)H18A—C18—H18C109.5
C9—C8—N1122.89 (12)H18B—C18—H18C109.5
C9—C8—C10108.20 (12)O1—C19—H19A109.5
N1—C8—C10128.90 (12)O1—C19—H19B109.5
C8—C9—N2110.80 (12)H19A—C19—H19B109.5
C8—C9—C17128.38 (13)O1—C19—H19C109.5
N2—C9—C17120.80 (12)H19A—C19—H19C109.5
O3—C10—N3123.59 (12)H19B—C19—H19C109.5
O3—C10—C8131.86 (13)C1—N1—C8121.26 (12)
N3—C10—C8104.52 (11)C9—N2—N3105.36 (10)
C12—C11—C16120.55 (14)C9—N2—C18119.47 (11)
C12—C11—N3118.85 (13)N3—N2—C18114.75 (12)
C16—C11—N3120.59 (13)C10—N3—N2110.70 (11)
C11—C12—C13118.85 (16)C10—N3—C11126.93 (11)
C11—C12—H12120.6N2—N3—C11120.19 (11)
C13—C12—H12120.6C5—O1—C19117.42 (12)
C14—C13—C12120.81 (17)C7—O2—H2109.5
C14—C13—H13119.6
N1—C1—C2—C3177.64 (13)C12—C13—C14—C150.0 (3)
N1—C1—C2—C72.1 (2)C13—C14—C15—C160.5 (3)
C7—C2—C3—C40.6 (2)C14—C15—C16—C111.1 (2)
C1—C2—C3—C4179.07 (15)C12—C11—C16—C151.4 (2)
C2—C3—C4—C50.5 (2)N3—C11—C16—C15177.35 (13)
C3—C4—C5—O1179.79 (14)C2—C1—N1—C8175.16 (13)
C3—C4—C5—C60.3 (2)C9—C8—N1—C1179.04 (13)
O1—C5—C6—C7179.70 (14)C10—C8—N1—C10.6 (2)
C4—C5—C6—C70.4 (2)C8—C9—N2—N34.06 (16)
C5—C6—C7—O2179.73 (13)C17—C9—N2—N3177.49 (13)
C5—C6—C7—C20.6 (2)C8—C9—N2—C18134.91 (14)
C3—C2—C7—O2179.67 (13)C17—C9—N2—C1846.6 (2)
C1—C2—C7—O20.6 (2)O3—C10—N3—N2172.10 (13)
C3—C2—C7—C60.7 (2)C8—C10—N3—N26.18 (15)
C1—C2—C7—C6178.97 (13)O3—C10—N3—C119.1 (2)
N1—C8—C9—N2179.04 (12)C8—C10—N3—C11169.22 (13)
C10—C8—C9—N20.34 (16)C9—N2—N3—C106.47 (15)
N1—C8—C9—C172.7 (2)C18—N2—N3—C10139.98 (12)
C10—C8—C9—C17178.65 (15)C9—N2—N3—C11170.81 (12)
C9—C8—C10—O3174.52 (15)C18—N2—N3—C1155.67 (17)
N1—C8—C10—O36.9 (3)C12—C11—N3—C1051.3 (2)
C9—C8—C10—N33.57 (15)C16—C11—N3—C10129.95 (15)
N1—C8—C10—N3175.02 (13)C12—C11—N3—N2147.07 (14)
C16—C11—C12—C130.9 (2)C16—C11—N3—N231.65 (19)
N3—C11—C12—C13177.82 (14)C6—C5—O1—C192.5 (2)
C11—C12—C13—C140.2 (3)C4—C5—O1—C19177.59 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O3i0.962.573.5315 (18)175
C1—H1···O30.932.363.0431 (17)130
O2—H2···N10.821.902.6231 (15)147
Symmetry code: (i) x, y1, z.
 

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