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The title compound, C28H22N4O2, was synthesized by the reaction of 4-benzoyl-3-methyl-1-phenyl­pyrazol-5-one and 1-naphthoylhydrazide. The mol­ecules are connected via inter­molecular N—H...N hydrogen bonds into a one-dimensional chain structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012883/hg2213sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012883/hg2213Isup2.hkl
Contains datablock I

CCDC reference: 643031

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.123
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.93 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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.

2'-[(Phenyl)(1-phenyl-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-4-ylidene)methyl]- 1-naphthohydrazide top
Crystal data top
C28H22N4O2F(000) = 936
Mr = 446.50Dx = 1.287 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5044 reflections
a = 8.2430 (5) Åθ = 2.5–21.7°
b = 21.8718 (13) ŵ = 0.08 mm1
c = 12.9224 (8) ÅT = 273 K
β = 98.533 (2)°Block, yellow
V = 2304.0 (2) Å30.36 × 0.24 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4985 independent reflections
Radiation source: fine-focus sealed tube3365 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 109
Tmin = 0.971, Tmax = 0.990k = 2727
29318 measured reflectionsl = 1616
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)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.123H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.5093P]
where P = (Fo2 + 2Fc2)/3
4985 reflections(Δ/σ)max < 0.001
309 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Experimental. Spectroscopic analysis: IR (KBr, ν cm-1): 3126, 1686, 1635, 1608, 1589, 1522, 1493, 1375, 1288, 1255, 1178, 1130, 999, 956, 802, 750, 696.

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
O10.92393 (15)0.65456 (6)0.70006 (10)0.0610 (4)
O20.67124 (14)0.47842 (6)0.68958 (11)0.0623 (4)
N11.05736 (16)0.57344 (6)0.78086 (11)0.0476 (4)
H11.15080.55780.80560.057*
N20.91347 (16)0.54358 (6)0.79558 (12)0.0506 (4)
H20.89110.50880.76570.061*
N30.43229 (16)0.49151 (6)0.76315 (11)0.0440 (3)
N40.38278 (15)0.52339 (6)0.84703 (10)0.0420 (3)
C10.59438 (19)0.50180 (7)0.75564 (14)0.0448 (4)
C20.64984 (18)0.54400 (7)0.83993 (13)0.0407 (4)
C30.50954 (18)0.55454 (7)0.89166 (12)0.0397 (4)
C40.4886 (2)0.59411 (8)0.98269 (13)0.0519 (4)
H4A0.47460.63580.96000.078*
H4B0.58410.59091.03490.078*
H4C0.39380.58111.01180.078*
C50.31633 (19)0.45598 (7)0.69691 (13)0.0435 (4)
C60.1942 (2)0.42561 (9)0.73836 (15)0.0581 (5)
H60.18910.42770.80970.070*
C70.0796 (3)0.39208 (11)0.67284 (17)0.0747 (6)
H70.00370.37180.70020.090*
C80.0877 (3)0.38838 (10)0.56762 (17)0.0710 (6)
H80.01160.36500.52430.085*
C90.2079 (2)0.41924 (9)0.52662 (16)0.0625 (5)
H90.21240.41710.45520.075*
C100.3226 (2)0.45351 (8)0.59059 (14)0.0530 (4)
H100.40340.47480.56240.064*
C110.80892 (18)0.56723 (7)0.85468 (12)0.0403 (4)
C120.86981 (19)0.61493 (7)0.93172 (13)0.0434 (4)
C130.7965 (2)0.67187 (8)0.92616 (16)0.0580 (5)
H130.70820.67990.87430.070*
C140.8536 (3)0.71670 (10)0.9971 (2)0.0819 (7)
H140.80330.75490.99340.098*
C150.9834 (4)0.70535 (15)1.0726 (2)0.0953 (9)
H151.02100.73571.12060.114*
C161.0595 (3)0.64920 (15)1.07834 (17)0.0890 (8)
H161.14900.64191.12970.107*
C171.0033 (2)0.60362 (10)1.00779 (15)0.0620 (5)
H171.05470.56571.01150.074*
C181.0511 (2)0.62698 (8)0.72793 (13)0.0435 (4)
C191.21534 (19)0.64768 (7)0.70523 (13)0.0437 (4)
C201.2908 (2)0.61460 (9)0.63651 (14)0.0564 (5)
H201.24220.57870.60820.068*
C211.4397 (3)0.63367 (12)0.60792 (18)0.0759 (6)
H211.48970.61050.56120.091*
C221.5115 (3)0.68635 (12)0.6487 (2)0.0798 (7)
H221.61110.69880.62990.096*
C231.4366 (2)0.72209 (9)0.71899 (17)0.0631 (5)
C241.5073 (3)0.77700 (13)0.7617 (3)0.0989 (9)
H241.60400.79110.74110.119*
C251.4369 (4)0.80912 (13)0.8316 (3)0.1159 (11)
H251.48460.84550.85820.139*
C261.2925 (3)0.78851 (12)0.8650 (2)0.0956 (8)
H261.24690.81070.91500.115*
C271.2182 (3)0.73636 (9)0.82526 (16)0.0659 (5)
H271.12190.72320.84760.079*
C281.2876 (2)0.70206 (8)0.74968 (14)0.0494 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0380 (7)0.0692 (8)0.0734 (9)0.0086 (6)0.0005 (6)0.0073 (7)
O20.0410 (7)0.0678 (8)0.0821 (9)0.0121 (6)0.0226 (7)0.0306 (7)
N10.0267 (7)0.0490 (8)0.0673 (9)0.0025 (6)0.0073 (6)0.0000 (7)
N20.0310 (7)0.0436 (7)0.0787 (10)0.0073 (6)0.0133 (7)0.0132 (7)
N30.0303 (7)0.0512 (8)0.0510 (8)0.0061 (6)0.0074 (6)0.0096 (6)
N40.0297 (7)0.0508 (8)0.0454 (8)0.0011 (6)0.0047 (6)0.0030 (6)
C10.0307 (9)0.0456 (9)0.0587 (11)0.0046 (7)0.0084 (8)0.0058 (8)
C20.0296 (8)0.0416 (8)0.0504 (9)0.0015 (6)0.0046 (7)0.0029 (7)
C30.0315 (8)0.0441 (8)0.0423 (9)0.0012 (7)0.0016 (7)0.0016 (7)
C40.0425 (10)0.0619 (11)0.0511 (10)0.0007 (8)0.0059 (8)0.0056 (8)
C50.0305 (8)0.0459 (9)0.0529 (10)0.0033 (7)0.0024 (7)0.0055 (7)
C60.0476 (11)0.0721 (12)0.0534 (11)0.0196 (9)0.0038 (8)0.0037 (9)
C70.0571 (13)0.0938 (16)0.0717 (14)0.0376 (12)0.0052 (11)0.0055 (12)
C80.0544 (13)0.0856 (15)0.0690 (14)0.0204 (11)0.0045 (10)0.0205 (11)
C90.0533 (12)0.0770 (13)0.0556 (11)0.0039 (10)0.0031 (9)0.0150 (10)
C100.0445 (10)0.0591 (11)0.0572 (11)0.0070 (8)0.0132 (8)0.0105 (9)
C110.0312 (8)0.0385 (8)0.0507 (9)0.0002 (6)0.0043 (7)0.0037 (7)
C120.0316 (9)0.0510 (9)0.0475 (9)0.0085 (7)0.0057 (7)0.0024 (7)
C130.0580 (12)0.0493 (10)0.0674 (12)0.0044 (9)0.0114 (10)0.0077 (9)
C140.0907 (18)0.0636 (13)0.0969 (18)0.0204 (12)0.0317 (15)0.0284 (12)
C150.092 (2)0.116 (2)0.0825 (18)0.0469 (17)0.0281 (15)0.0492 (16)
C160.0608 (15)0.148 (3)0.0557 (13)0.0339 (16)0.0010 (11)0.0192 (15)
C170.0431 (11)0.0832 (13)0.0581 (12)0.0081 (10)0.0020 (9)0.0012 (10)
C180.0339 (9)0.0491 (9)0.0458 (9)0.0009 (7)0.0005 (7)0.0061 (7)
C190.0358 (9)0.0489 (9)0.0454 (9)0.0027 (7)0.0026 (7)0.0050 (7)
C200.0512 (11)0.0626 (11)0.0570 (11)0.0089 (9)0.0133 (9)0.0018 (9)
C210.0606 (14)0.0975 (17)0.0758 (15)0.0176 (13)0.0305 (11)0.0156 (13)
C220.0482 (12)0.1025 (18)0.0915 (17)0.0027 (12)0.0204 (12)0.0336 (15)
C230.0422 (11)0.0658 (12)0.0782 (14)0.0077 (9)0.0016 (10)0.0221 (11)
C240.0704 (17)0.0843 (17)0.134 (2)0.0323 (14)0.0122 (16)0.0217 (17)
C250.100 (2)0.0738 (17)0.160 (3)0.0278 (16)0.029 (2)0.0190 (19)
C260.0821 (18)0.0805 (16)0.114 (2)0.0008 (14)0.0204 (15)0.0364 (15)
C270.0539 (12)0.0664 (12)0.0721 (13)0.0027 (10)0.0079 (10)0.0157 (10)
C280.0382 (10)0.0510 (10)0.0552 (10)0.0004 (8)0.0055 (8)0.0099 (8)
Geometric parameters (Å, º) top
O1—C181.2169 (19)C12—C131.381 (2)
O2—C11.2458 (19)C12—C171.384 (2)
N1—C181.353 (2)C13—C141.377 (3)
N1—N21.3916 (17)C13—H130.9300
N1—H10.8600C14—C151.359 (4)
N2—C111.338 (2)C14—H140.9300
N2—H20.8600C15—C161.376 (4)
N3—C11.373 (2)C15—H150.9300
N3—N41.3997 (18)C16—C171.384 (3)
N3—C51.417 (2)C16—H160.9300
N4—C31.3076 (19)C17—H170.9300
C1—C21.449 (2)C18—C191.497 (2)
C2—C111.393 (2)C19—C201.365 (2)
C2—C31.438 (2)C19—C281.413 (2)
C3—C41.491 (2)C20—C211.397 (3)
C4—H4A0.9600C20—H200.9300
C4—H4B0.9600C21—C221.365 (3)
C4—H4C0.9600C21—H210.9300
C5—C61.379 (2)C22—C231.408 (3)
C5—C101.384 (2)C22—H220.9300
C6—C71.382 (3)C23—C241.411 (3)
C6—H60.9300C23—C281.415 (3)
C7—C81.374 (3)C24—C251.343 (4)
C7—H70.9300C24—H240.9300
C8—C91.369 (3)C25—C261.399 (4)
C8—H80.9300C25—H250.9300
C9—C101.381 (2)C26—C271.359 (3)
C9—H90.9300C26—H260.9300
C10—H100.9300C27—C281.418 (3)
C11—C121.477 (2)C27—H270.9300
C18—N1—N2120.40 (13)C14—C13—C12120.2 (2)
C18—N1—H1119.8C14—C13—H13119.9
N2—N1—H1119.8C12—C13—H13119.9
C11—N2—N1122.07 (13)C15—C14—C13120.2 (2)
C11—N2—H2119.0C15—C14—H14119.9
N1—N2—H2119.0C13—C14—H14119.9
C1—N3—N4111.83 (12)C14—C15—C16120.4 (2)
C1—N3—C5128.59 (13)C14—C15—H15119.8
N4—N3—C5119.54 (12)C16—C15—H15119.8
C3—N4—N3107.18 (12)C15—C16—C17120.1 (2)
O2—C1—N3125.49 (15)C15—C16—H16119.9
O2—C1—C2129.85 (15)C17—C16—H16119.9
N3—C1—C2104.66 (13)C16—C17—C12119.5 (2)
C11—C2—C3133.14 (15)C16—C17—H17120.2
C11—C2—C1121.39 (14)C12—C17—H17120.2
C3—C2—C1105.42 (13)O1—C18—N1123.01 (15)
N4—C3—C2110.89 (13)O1—C18—C19123.81 (15)
N4—C3—C4118.18 (14)N1—C18—C19113.15 (14)
C2—C3—C4130.93 (14)C20—C19—C28120.35 (16)
C3—C4—H4A109.5C20—C19—C18118.66 (16)
C3—C4—H4B109.5C28—C19—C18120.91 (15)
H4A—C4—H4B109.5C19—C20—C21121.12 (19)
C3—C4—H4C109.5C19—C20—H20119.4
H4A—C4—H4C109.5C21—C20—H20119.4
H4B—C4—H4C109.5C22—C21—C20119.9 (2)
C6—C5—C10120.25 (15)C22—C21—H21120.1
C6—C5—N3119.70 (15)C20—C21—H21120.1
C10—C5—N3120.02 (15)C21—C22—C23120.72 (19)
C5—C6—C7119.33 (18)C21—C22—H22119.6
C5—C6—H6120.3C23—C22—H22119.6
C7—C6—H6120.3C22—C23—C24122.0 (2)
C8—C7—C6120.57 (19)C22—C23—C28119.38 (19)
C8—C7—H7119.7C24—C23—C28118.6 (2)
C6—C7—H7119.7C25—C24—C23120.9 (3)
C9—C8—C7119.88 (18)C25—C24—H24119.5
C9—C8—H8120.1C23—C24—H24119.5
C7—C8—H8120.1C24—C25—C26120.8 (3)
C8—C9—C10120.43 (19)C24—C25—H25119.6
C8—C9—H9119.8C26—C25—H25119.6
C10—C9—H9119.8C27—C26—C25120.6 (3)
C9—C10—C5119.52 (17)C27—C26—H26119.7
C9—C10—H10120.2C25—C26—H26119.7
C5—C10—H10120.2C26—C27—C28120.0 (2)
N2—C11—C2117.00 (14)C26—C27—H27120.0
N2—C11—C12118.33 (14)C28—C27—H27120.0
C2—C11—C12124.66 (14)C19—C28—C23118.54 (17)
C13—C12—C17119.57 (17)C19—C28—C27122.44 (17)
C13—C12—C11119.95 (15)C23—C28—C27119.01 (18)
C17—C12—C11120.46 (16)
C18—N1—N2—C1166.3 (2)N2—C11—C12—C1756.8 (2)
C1—N3—N4—C31.12 (18)C2—C11—C12—C17122.06 (19)
C5—N3—N4—C3176.83 (14)C17—C12—C13—C141.3 (3)
N4—N3—C1—O2178.63 (16)C11—C12—C13—C14179.39 (17)
C5—N3—C1—O23.7 (3)C12—C13—C14—C150.5 (3)
N4—N3—C1—C20.97 (18)C13—C14—C15—C160.5 (4)
C5—N3—C1—C2176.75 (15)C14—C15—C16—C170.7 (4)
O2—C1—C2—C113.1 (3)C15—C16—C17—C120.1 (3)
N3—C1—C2—C11177.33 (14)C13—C12—C17—C161.1 (3)
O2—C1—C2—C3179.10 (18)C11—C12—C17—C16179.19 (17)
N3—C1—C2—C30.48 (17)N2—N1—C18—O17.5 (2)
N3—N4—C3—C20.76 (17)N2—N1—C18—C19171.12 (14)
N3—N4—C3—C4178.58 (13)O1—C18—C19—C20110.8 (2)
C11—C2—C3—N4177.62 (17)N1—C18—C19—C2067.8 (2)
C1—C2—C3—N40.18 (18)O1—C18—C19—C2866.0 (2)
C11—C2—C3—C41.6 (3)N1—C18—C19—C28115.42 (17)
C1—C2—C3—C4179.05 (16)C28—C19—C20—C210.5 (3)
C1—N3—C5—C6147.38 (18)C18—C19—C20—C21176.37 (17)
N4—N3—C5—C635.1 (2)C19—C20—C21—C220.2 (3)
C1—N3—C5—C1034.8 (3)C20—C21—C22—C230.4 (3)
N4—N3—C5—C10142.78 (16)C21—C22—C23—C24179.4 (2)
C10—C5—C6—C70.8 (3)C21—C22—C23—C281.8 (3)
N3—C5—C6—C7178.68 (18)C22—C23—C24—C25177.4 (3)
C5—C6—C7—C80.7 (3)C28—C23—C24—C251.3 (4)
C6—C7—C8—C91.5 (4)C23—C24—C25—C260.8 (5)
C7—C8—C9—C100.8 (3)C24—C25—C26—C271.7 (5)
C8—C9—C10—C50.7 (3)C25—C26—C27—C280.4 (4)
C6—C5—C10—C91.5 (3)C20—C19—C28—C231.8 (2)
N3—C5—C10—C9179.35 (16)C18—C19—C28—C23174.96 (15)
N1—N2—C11—C2161.43 (15)C20—C19—C28—C27176.81 (17)
N1—N2—C11—C1219.6 (2)C18—C19—C28—C276.4 (2)
C3—C2—C11—N2175.35 (16)C22—C23—C28—C192.5 (3)
C1—C2—C11—N27.5 (2)C24—C23—C28—C19178.76 (18)
C3—C2—C11—C123.5 (3)C22—C23—C28—C27176.21 (18)
C1—C2—C11—C12173.60 (15)C24—C23—C28—C272.6 (3)
N2—C11—C12—C13121.29 (18)C26—C27—C28—C19179.67 (19)
C2—C11—C12—C1359.9 (2)C26—C27—C28—C231.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.862.052.9059 (18)173
N2—H2···O20.862.042.6613 (18)128
Symmetry code: (i) x+1, y, z.
 

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