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The title compound, C21H18N4O, was synthesized by condensation of quinoline-2-carbaldehyde and 4-amino­anti­pyrine. The mean planes of the pyrazole and phenyl rings make a dihedral angle of 55.7 (3)°. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014985/cv2219sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014985/cv2219Isup2.hkl
Contains datablock I

CCDC reference: 647176

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.059
  • wR factor = 0.165
  • Data-to-parameter ratio = 15.5

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 a R-AXIS-IV. 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 27.00 From the CIF: _diffrn_reflns_theta_full 27.00 From the CIF: _reflns_number_total 3655 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3957 Completeness (_total/calc) 92.37% 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 ..... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H18 N4 O
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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-[(1E)-(2-quinolyl)methylideneamino]- 1H-pyrazol-3(2H)-one top
Crystal data top
C21H18N4OF(000) = 720
Mr = 342.39Dx = 1.254 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 396 reflections
a = 12.935 (3) Åθ = 2–25.1°
b = 7.1220 (14) ŵ = 0.08 mm1
c = 20.465 (4) ÅT = 291 K
β = 105.88 (3)°Prismatic, orange
V = 1813.4 (6) Å30.20 × 0.18 × 0.17 mm
Z = 4
Data collection top
Rigaku R-AXIS-IV
diffractometer
3655 independent reflections
Radiation source: fine-focus sealed tube2472 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 0 pixels mm-1θmax = 27.0°, θmin = 1.7°
Oscillation frames scansh = 016
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.984, Tmax = 0.987l = 2624
5958 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.082P)2 + 0.249P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3655 reflectionsΔρmax = 0.29 e Å3
236 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0102 (18)
Special details top

Experimental. Analysis calculated for C21H18N4O1: C, 73.67; H, 5.30; N, 16.36. Found (%): C, 73.58; H, 5.26; N, 16.11.

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
O11.34005 (14)0.8905 (2)0.12424 (9)0.0633 (5)
N11.39316 (16)1.3260 (2)0.20062 (10)0.0499 (5)
N21.42553 (15)1.1592 (2)0.17535 (10)0.0491 (5)
N31.13568 (15)1.1294 (2)0.12529 (9)0.0470 (5)
N40.96369 (15)0.7576 (2)0.05078 (10)0.0482 (5)
C11.33445 (18)1.0529 (3)0.14400 (11)0.0466 (5)
C21.24482 (18)1.1698 (3)0.14559 (11)0.0423 (5)
C31.28438 (18)1.3342 (3)0.17756 (11)0.0441 (5)
C41.2224 (2)1.5018 (3)0.18759 (13)0.0607 (7)
H4A1.27091.59640.21160.091*
H4B1.17351.46750.21340.091*
H4C1.18261.55000.14420.091*
C51.4653 (2)1.4871 (3)0.20993 (14)0.0649 (7)
H5A1.43381.59110.22730.097*
H5B1.47701.52100.16710.097*
H5C1.53281.45520.24150.097*
C61.52433 (18)1.0716 (3)0.21057 (11)0.0446 (5)
C71.56376 (19)1.0780 (3)0.28059 (12)0.0528 (6)
H7A1.52841.14770.30630.063*
C81.6556 (2)0.9801 (4)0.31174 (14)0.0622 (7)
H8A1.68300.98460.35870.075*
C91.7075 (2)0.8751 (4)0.27347 (16)0.0692 (8)
H9A1.76910.80760.29480.083*
C101.6680 (2)0.8704 (4)0.20377 (16)0.0701 (8)
H10A1.70330.80020.17810.084*
C111.5770 (2)0.9684 (3)0.17212 (14)0.0595 (6)
H11A1.55080.96570.12500.071*
C121.10228 (18)0.9729 (3)0.09698 (11)0.0481 (5)
H12A1.15150.88710.08890.058*
C130.98779 (18)0.9264 (3)0.07711 (11)0.0439 (5)
C140.9095 (2)1.0564 (3)0.08537 (13)0.0544 (6)
H14A0.93011.17390.10430.065*
C150.8048 (2)1.0080 (3)0.06554 (13)0.0598 (7)
H15A0.75261.09220.07080.072*
C160.77453 (19)0.8293 (3)0.03683 (11)0.0505 (6)
C170.85733 (19)0.7074 (3)0.03051 (11)0.0469 (5)
C180.8308 (2)0.5280 (3)0.00129 (12)0.0560 (6)
H18A0.88480.44780.00380.067*
C190.7264 (2)0.4724 (4)0.01941 (13)0.0654 (7)
H19A0.70960.35320.03780.078*
C200.6438 (2)0.5923 (4)0.01339 (14)0.0691 (8)
H20A0.57270.55260.02820.083*
C210.6669 (2)0.7667 (4)0.01404 (14)0.0640 (7)
H21A0.61140.84530.01780.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0595 (11)0.0411 (8)0.0806 (13)0.0016 (7)0.0045 (9)0.0197 (8)
N10.0559 (13)0.0349 (9)0.0570 (12)0.0013 (8)0.0123 (9)0.0100 (8)
N20.0492 (11)0.0366 (9)0.0568 (12)0.0012 (8)0.0062 (9)0.0109 (8)
N30.0518 (12)0.0417 (9)0.0450 (11)0.0008 (8)0.0088 (9)0.0003 (8)
N40.0538 (12)0.0412 (9)0.0479 (11)0.0019 (8)0.0113 (9)0.0008 (8)
C10.0527 (14)0.0376 (10)0.0466 (13)0.0013 (9)0.0087 (10)0.0067 (9)
C20.0475 (13)0.0374 (10)0.0395 (12)0.0002 (9)0.0076 (9)0.0011 (8)
C30.0505 (14)0.0396 (10)0.0406 (12)0.0005 (9)0.0096 (10)0.0019 (9)
C40.0675 (17)0.0477 (12)0.0661 (17)0.0059 (12)0.0171 (13)0.0126 (11)
C50.0638 (16)0.0427 (12)0.0809 (19)0.0105 (12)0.0073 (14)0.0096 (12)
C60.0446 (12)0.0382 (10)0.0501 (13)0.0037 (9)0.0116 (10)0.0039 (9)
C70.0516 (14)0.0525 (12)0.0546 (15)0.0024 (11)0.0152 (11)0.0040 (10)
C80.0565 (15)0.0646 (15)0.0610 (16)0.0019 (12)0.0085 (12)0.0054 (12)
C90.0525 (16)0.0599 (15)0.090 (2)0.0081 (12)0.0114 (15)0.0088 (14)
C100.0650 (18)0.0644 (15)0.086 (2)0.0132 (13)0.0291 (16)0.0068 (14)
C110.0642 (16)0.0577 (14)0.0579 (15)0.0053 (12)0.0190 (13)0.0068 (11)
C120.0508 (14)0.0418 (11)0.0491 (13)0.0001 (10)0.0090 (10)0.0009 (9)
C130.0506 (13)0.0406 (10)0.0392 (12)0.0030 (9)0.0100 (10)0.0016 (9)
C140.0574 (15)0.0419 (11)0.0639 (16)0.0014 (10)0.0164 (12)0.0083 (10)
C150.0576 (16)0.0548 (13)0.0699 (17)0.0048 (12)0.0223 (13)0.0080 (12)
C160.0526 (15)0.0565 (13)0.0441 (13)0.0051 (11)0.0160 (11)0.0020 (10)
C170.0541 (15)0.0462 (11)0.0404 (12)0.0056 (10)0.0130 (10)0.0001 (9)
C180.0661 (16)0.0485 (12)0.0537 (15)0.0081 (11)0.0168 (12)0.0076 (10)
C190.0792 (19)0.0606 (15)0.0582 (16)0.0234 (14)0.0219 (14)0.0110 (12)
C200.0599 (17)0.0872 (19)0.0617 (17)0.0279 (15)0.0190 (13)0.0123 (14)
C210.0525 (16)0.0794 (17)0.0639 (17)0.0059 (13)0.0222 (13)0.0091 (13)
Geometric parameters (Å, º) top
O1—C11.234 (2)C8—H8A0.9300
N1—C31.357 (3)C9—C101.378 (4)
N1—N21.404 (2)C9—H9A0.9300
N1—C51.458 (3)C10—C111.369 (4)
N2—C11.400 (3)C10—H10A0.9300
N2—C61.428 (3)C11—H11A0.9300
N3—C121.276 (3)C12—C131.462 (3)
N3—C21.388 (3)C12—H12A0.9300
N4—C131.319 (3)C13—C141.416 (3)
N4—C171.371 (3)C14—C151.349 (4)
C1—C21.435 (3)C14—H14A0.9300
C2—C31.370 (3)C15—C161.412 (3)
C3—C41.484 (3)C15—H15A0.9300
C4—H4A0.9600C16—C171.412 (3)
C4—H4B0.9600C16—C211.414 (3)
C4—H4C0.9600C17—C181.413 (3)
C5—H5A0.9600C18—C191.359 (4)
C5—H5B0.9600C18—H18A0.9300
C5—H5C0.9600C19—C201.399 (4)
C6—C71.384 (3)C19—H19A0.9300
C6—C111.385 (3)C20—C211.362 (4)
C7—C81.375 (3)C20—H20A0.9300
C7—H7A0.9300C21—H21A0.9300
C8—C91.382 (4)
C3—N1—N2107.04 (16)C10—C9—H9A120.0
C3—N1—C5125.28 (18)C8—C9—H9A120.0
N2—N1—C5117.96 (19)C11—C10—C9120.3 (3)
C1—N2—N1109.14 (18)C11—C10—H10A119.8
C1—N2—C6121.35 (16)C9—C10—H10A119.8
N1—N2—C6119.97 (17)C10—C11—C6119.7 (2)
C12—N3—C2120.48 (19)C10—C11—H11A120.2
C13—N4—C17117.79 (19)C6—C11—H11A120.2
O1—C1—N2122.7 (2)N3—C12—C13121.0 (2)
O1—C1—C2132.2 (2)N3—C12—H12A119.5
N2—C1—C2105.06 (17)C13—C12—H12A119.5
C3—C2—N3122.44 (19)N4—C13—C14123.2 (2)
C3—C2—C1107.93 (19)N4—C13—C12115.4 (2)
N3—C2—C1129.40 (18)C14—C13—C12121.43 (19)
N1—C3—C2110.24 (18)C15—C14—C13119.3 (2)
N1—C3—C4122.30 (19)C15—C14—H14A120.3
C2—C3—C4127.5 (2)C13—C14—H14A120.3
C3—C4—H4A109.5C14—C15—C16119.8 (2)
C3—C4—H4B109.5C14—C15—H15A120.1
H4A—C4—H4B109.5C16—C15—H15A120.1
C3—C4—H4C109.5C17—C16—C15117.5 (2)
H4A—C4—H4C109.5C17—C16—C21118.6 (2)
H4B—C4—H4C109.5C15—C16—C21123.8 (2)
N1—C5—H5A109.5N4—C17—C16122.39 (19)
N1—C5—H5B109.5N4—C17—C18118.1 (2)
H5A—C5—H5B109.5C16—C17—C18119.5 (2)
N1—C5—H5C109.5C19—C18—C17120.1 (2)
H5A—C5—H5C109.5C19—C18—H18A120.0
H5B—C5—H5C109.5C17—C18—H18A120.0
C7—C6—C11120.4 (2)C18—C19—C20120.8 (2)
C7—C6—N2122.3 (2)C18—C19—H19A119.6
C11—C6—N2117.2 (2)C20—C19—H19A119.6
C8—C7—C6119.4 (2)C21—C20—C19120.4 (3)
C8—C7—H7A120.3C21—C20—H20A119.8
C6—C7—H7A120.3C19—C20—H20A119.8
C7—C8—C9120.3 (3)C20—C21—C16120.5 (3)
C7—C8—H8A119.9C20—C21—H21A119.7
C9—C8—H8A119.9C16—C21—H21A119.7
C10—C9—C8120.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O10.932.353.029 (3)130
C19—H19A···O1i0.932.443.318 (3)159
Symmetry code: (i) x+2, y+1, z.
 

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