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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o510.
Published online 2009 February 11. doi:  10.1107/S1600536809004243
PMCID: PMC2968674

4-[(2-Benzoyl-4-chlorophenyl)diazenyl]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Abstract

In the title compound, C23H17ClN4O2, the amino H atom forms an intra­molecular hydrogen bond to the exocyclic carbonyl O atom as well as to the O atom of the benzoyl group.

Related literature

For the crystal structure of 1-phenyl-3-methyl-4-(4′-chloro­phenyazo)-pyrazol-5-one, whose amino H atom is intra­molecularly hydrogen-bonded to the carbonyl O atom, see: Golinski et al. (1983 [triangle]).

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Object name is e-65-0o510-scheme1.jpg

Experimental

Crystal data

  • C23H17ClN4O2
  • M r = 416.86
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o510-efi1.jpg
  • a = 25.800 (3) Å
  • b = 12.124 (1) Å
  • c = 13.966 (1) Å
  • β = 119.179 (1)°
  • V = 3813.9 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 120 (2) K
  • 0.35 × 0.25 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.791, T max = 0.862 (expected range = 0.897–0.977)
  • 10753 measured reflections
  • 4346 independent reflections
  • 3309 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.105
  • S = 1.00
  • 4346 reflections
  • 276 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004243/tk2371sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004243/tk2371Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Iranian Research Organization for Science and Technology and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-Amino-5-chlorobenzophenone (2.32 g, 0.01 mol) was suspended in strong hydrochloric acid (20 ml, pH ca. 5) at 273 K. A solution of sodium nitrite (0.69 g in 15 ml water) was added. Following the diazotization, an aqueous solution of 3-methyl-1-phenyl-2-pyrazoline-5-one (1.75 g, 0.01 mol) was added. The compound that separated was collected and recrystallized from ethanol.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.85±0.01 Å; its temperature factors was freely refined.

Figures

Fig. 1.
Thermal displacement plot (Barbour, 2001) of C23H17ClN4O2; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.

Crystal data

C23H17ClN4O2F(000) = 1728
Mr = 416.86Dx = 1.452 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2643 reflections
a = 25.800 (3) Åθ = 2.2–26.9°
b = 12.124 (1) ŵ = 0.23 mm1
c = 13.966 (1) ÅT = 120 K
β = 119.179 (1)°Block, orange
V = 3813.9 (7) Å30.35 × 0.25 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer4346 independent reflections
Radiation source: fine-focus sealed tube3309 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −33→33
Tmin = 0.791, Tmax = 0.862k = −15→12
10753 measured reflectionsl = −18→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.05P)2 + 2.1067P] where P = (Fo2 + 2Fc2)/3
4346 reflections(Δ/σ)max = 0.001
276 parametersΔρmax = 0.30 e Å3
1 restraintΔρmin = −0.30 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.176742 (18)0.72052 (4)0.10069 (4)0.03104 (13)
O10.51920 (5)0.65437 (10)0.64529 (9)0.0270 (3)
O20.42743 (6)0.81878 (10)0.49190 (10)0.0301 (3)
N10.56804 (6)0.48796 (11)0.72365 (11)0.0209 (3)
N20.55349 (6)0.37433 (11)0.70777 (11)0.0208 (3)
N30.42128 (6)0.49431 (11)0.50462 (11)0.0200 (3)
N40.40777 (6)0.59936 (12)0.47918 (11)0.0204 (3)
H40.4336 (7)0.6518 (13)0.5167 (15)0.037 (6)*
C10.62606 (7)0.51899 (15)0.80413 (13)0.0214 (4)
C20.66295 (7)0.44153 (15)0.88027 (13)0.0239 (4)
H20.64890.36910.87990.029*
C30.72042 (8)0.47068 (16)0.95664 (14)0.0279 (4)
H30.74580.41751.00820.034*
C40.74136 (8)0.57598 (16)0.95878 (15)0.0307 (4)
H4A0.78100.59511.01080.037*
C50.70394 (8)0.65311 (16)0.88431 (15)0.0310 (4)
H50.71790.72610.88660.037*
C60.64650 (8)0.62588 (15)0.80647 (14)0.0270 (4)
H60.62130.67940.75520.032*
C70.52131 (7)0.55349 (14)0.65290 (13)0.0204 (3)
C80.47428 (7)0.47380 (14)0.58702 (13)0.0195 (3)
C90.49904 (7)0.36666 (14)0.62833 (13)0.0201 (3)
C100.46871 (7)0.25862 (14)0.59029 (15)0.0246 (4)
H10A0.49620.19920.63230.037*
H10B0.45590.24920.51220.037*
H10C0.43400.25620.60120.037*
C110.35288 (7)0.62787 (14)0.38933 (13)0.0198 (3)
C120.30754 (7)0.55002 (14)0.34178 (13)0.0226 (4)
H120.31400.47700.37000.027*
C130.25322 (7)0.57835 (15)0.25382 (14)0.0241 (4)
H130.22210.52550.22240.029*
C140.24456 (7)0.68414 (15)0.21197 (13)0.0221 (4)
C150.28903 (7)0.76156 (14)0.25581 (13)0.0213 (3)
H150.28220.83360.22520.026*
C160.34421 (7)0.73499 (14)0.34516 (13)0.0200 (3)
C170.39169 (7)0.82058 (14)0.39359 (13)0.0210 (3)
C180.39651 (7)0.90830 (14)0.32340 (13)0.0205 (3)
C190.42522 (7)1.00593 (14)0.37423 (14)0.0251 (4)
H190.43771.01720.44970.030*
C200.43574 (8)1.08644 (15)0.31600 (15)0.0298 (4)
H200.45491.15310.35130.036*
C210.41840 (8)1.07047 (15)0.20623 (15)0.0299 (4)
H210.42571.12590.16620.036*
C220.39037 (8)0.97341 (15)0.15512 (14)0.0273 (4)
H220.37870.96230.07990.033*
C230.37924 (7)0.89228 (14)0.21274 (13)0.0230 (4)
H230.35990.82590.17710.028*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0196 (2)0.0284 (3)0.0321 (2)0.00060 (17)0.00242 (17)0.00243 (19)
O10.0295 (7)0.0183 (7)0.0261 (6)−0.0014 (5)0.0080 (5)0.0012 (5)
O20.0339 (7)0.0233 (7)0.0217 (6)−0.0045 (5)0.0045 (5)−0.0012 (5)
N10.0219 (7)0.0173 (7)0.0210 (7)−0.0018 (6)0.0086 (6)0.0006 (5)
N20.0209 (7)0.0177 (7)0.0238 (7)−0.0010 (6)0.0109 (6)0.0014 (6)
N30.0219 (7)0.0200 (8)0.0204 (7)0.0008 (6)0.0121 (6)0.0028 (6)
N40.0210 (7)0.0181 (8)0.0195 (7)−0.0015 (6)0.0079 (6)0.0013 (6)
C10.0192 (8)0.0252 (9)0.0193 (8)−0.0022 (7)0.0089 (7)−0.0021 (7)
C20.0247 (9)0.0248 (10)0.0229 (8)−0.0011 (7)0.0121 (7)−0.0003 (7)
C30.0263 (9)0.0311 (10)0.0233 (9)0.0028 (8)0.0097 (7)0.0006 (8)
C40.0226 (9)0.0373 (11)0.0264 (9)−0.0057 (8)0.0073 (7)−0.0078 (8)
C50.0309 (10)0.0271 (10)0.0325 (10)−0.0085 (8)0.0133 (8)−0.0061 (8)
C60.0272 (9)0.0239 (10)0.0270 (9)−0.0015 (7)0.0109 (7)0.0012 (7)
C70.0229 (8)0.0209 (9)0.0180 (8)0.0010 (7)0.0105 (7)0.0024 (6)
C80.0209 (8)0.0204 (9)0.0184 (8)−0.0010 (6)0.0106 (7)0.0017 (6)
C90.0193 (8)0.0224 (9)0.0205 (8)0.0006 (7)0.0111 (7)0.0029 (7)
C100.0216 (8)0.0198 (9)0.0295 (9)−0.0019 (7)0.0102 (7)−0.0006 (7)
C110.0184 (8)0.0223 (9)0.0185 (8)0.0008 (6)0.0090 (7)−0.0007 (6)
C120.0245 (8)0.0191 (9)0.0251 (9)−0.0001 (7)0.0129 (7)0.0036 (7)
C130.0211 (8)0.0218 (9)0.0276 (9)−0.0047 (7)0.0106 (7)−0.0006 (7)
C140.0157 (8)0.0261 (9)0.0208 (8)0.0021 (7)0.0062 (6)0.0000 (7)
C150.0214 (8)0.0180 (9)0.0233 (8)0.0026 (6)0.0100 (7)0.0007 (7)
C160.0211 (8)0.0193 (9)0.0205 (8)0.0003 (7)0.0107 (7)−0.0011 (6)
C170.0204 (8)0.0178 (8)0.0212 (8)0.0024 (6)0.0074 (7)−0.0016 (7)
C180.0168 (7)0.0180 (9)0.0229 (8)0.0016 (6)0.0067 (6)0.0008 (7)
C190.0231 (8)0.0214 (9)0.0248 (9)−0.0009 (7)0.0070 (7)−0.0036 (7)
C200.0294 (9)0.0188 (9)0.0353 (10)−0.0049 (7)0.0110 (8)−0.0018 (8)
C210.0300 (10)0.0241 (10)0.0348 (10)−0.0013 (8)0.0151 (8)0.0053 (8)
C220.0266 (9)0.0275 (10)0.0247 (9)0.0021 (7)0.0099 (7)0.0021 (7)
C230.0207 (8)0.0192 (9)0.0247 (9)−0.0007 (7)0.0076 (7)−0.0019 (7)

Geometric parameters (Å, °)

Cl1—C141.738 (2)C10—H10A0.9800
O1—C71.227 (2)C10—H10B0.9800
O2—C171.225 (2)C10—H10C0.9800
N1—C71.378 (2)C11—C121.394 (2)
N1—C11.416 (2)C11—C161.408 (2)
N1—N21.417 (2)C12—C131.383 (2)
N2—C91.301 (2)C12—H120.9500
N3—C81.312 (2)C13—C141.382 (2)
N3—N41.323 (2)C13—H130.9500
N4—C111.402 (2)C14—C151.374 (2)
N4—H40.885 (9)C15—C161.398 (2)
C1—C21.390 (2)C15—H150.9500
C1—C61.393 (2)C16—C171.492 (2)
C2—C31.385 (2)C17—C181.492 (2)
C2—H20.9500C18—C191.393 (2)
C3—C41.381 (3)C18—C231.397 (2)
C3—H30.9500C19—C201.380 (3)
C4—C51.382 (3)C19—H190.9500
C4—H4A0.9500C20—C211.385 (3)
C5—C61.384 (3)C20—H200.9500
C5—H50.9500C21—C221.383 (3)
C6—H60.9500C21—H210.9500
C7—C81.471 (2)C22—C231.387 (2)
C8—C91.438 (2)C22—H220.9500
C9—C101.485 (2)C23—H230.9500
C7—N1—C1129.3 (2)H10B—C10—H10C109.5
C7—N1—N2112.1 (1)C12—C11—N4120.4 (2)
C1—N1—N2118.7 (1)C12—C11—C16119.9 (2)
C9—N2—N1107.2 (1)N4—C11—C16119.7 (1)
C8—N3—N4116.3 (1)C13—C12—C11120.4 (2)
N3—N4—C11119.8 (1)C13—C12—H12119.8
N3—N4—H4121 (1)C11—C12—H12119.8
C11—N4—H4120 (1)C12—C13—C14119.4 (2)
C2—C1—C6120.0 (2)C12—C13—H13120.3
C2—C1—N1119.5 (2)C14—C13—H13120.3
C6—C1—N1120.5 (2)C15—C14—C13121.2 (2)
C3—C2—C1119.6 (2)C15—C14—Cl1118.9 (1)
C3—C2—H2120.2C13—C14—Cl1119.9 (1)
C1—C2—H2120.2C14—C15—C16120.4 (2)
C4—C3—C2120.9 (2)C14—C15—H15119.8
C4—C3—H3119.6C16—C15—H15119.8
C2—C3—H3119.6C15—C16—C11118.6 (2)
C3—C4—C5119.2 (2)C15—C16—C17119.9 (2)
C3—C4—H4A120.4C11—C16—C17121.5 (2)
C5—C4—H4A120.4O2—C17—C18119.4 (2)
C4—C5—C6121.2 (2)O2—C17—C16119.9 (2)
C4—C5—H5119.4C18—C17—C16120.7 (1)
C6—C5—H5119.4C19—C18—C23119.0 (2)
C5—C6—C1119.2 (2)C19—C18—C17117.7 (2)
C5—C6—H6120.4C23—C18—C17122.9 (2)
C1—C6—H6120.4C20—C19—C18120.6 (2)
O1—C7—N1128.6 (2)C20—C19—H19119.7
O1—C7—C8127.8 (2)C18—C19—H19119.7
N1—C7—C8103.7 (1)C19—C20—C21120.2 (2)
N3—C8—C9126.3 (2)C19—C20—H20119.9
N3—C8—C7127.8 (2)C21—C20—H20119.9
C9—C8—C7105.8 (1)C20—C21—C22119.7 (2)
N2—C9—C8111.2 (2)C20—C21—H21120.1
N2—C9—C10122.0 (2)C22—C21—H21120.1
C8—C9—C10126.8 (2)C21—C22—C23120.5 (2)
C9—C10—H10A109.5C21—C22—H22119.7
C9—C10—H10B109.5C23—C22—H22119.7
H10A—C10—H10B109.5C22—C23—C18119.9 (2)
C9—C10—H10C109.5C22—C23—H23120.0
H10A—C10—H10C109.5C18—C23—H23120.0
C7—N1—N2—C90.5 (2)N3—N4—C11—C1214.3 (2)
C1—N1—N2—C9−178.1 (1)N3—N4—C11—C16−164.0 (1)
C8—N3—N4—C11177.4 (1)N4—C11—C12—C13179.4 (2)
C7—N1—C1—C2168.3 (2)C16—C11—C12—C13−2.4 (2)
N2—N1—C1—C2−13.4 (2)C11—C12—C13—C141.2 (3)
C7—N1—C1—C6−12.6 (3)C12—C13—C14—C150.3 (3)
N2—N1—C1—C6165.8 (2)C12—C13—C14—Cl1179.4 (1)
C6—C1—C2—C3−1.4 (3)C13—C14—C15—C16−0.7 (3)
N1—C1—C2—C3177.8 (2)Cl1—C14—C15—C16−179.8 (1)
C1—C2—C3—C40.6 (3)C14—C15—C16—C11−0.5 (2)
C2—C3—C4—C50.8 (3)C14—C15—C16—C17−178.6 (2)
C3—C4—C5—C6−1.4 (3)C12—C11—C16—C152.0 (2)
C4—C5—C6—C10.6 (3)N4—C11—C16—C15−179.8 (1)
C2—C1—C6—C50.8 (3)C12—C11—C16—C17−179.9 (2)
N1—C1—C6—C5−178.4 (2)N4—C11—C16—C17−1.6 (2)
C1—N1—C7—O1−1.6 (3)C15—C16—C17—O2148.1 (2)
N2—N1—C7—O1180.0 (2)C11—C16—C17—O2−30.0 (2)
C1—N1—C7—C8177.7 (2)C15—C16—C17—C18−32.3 (2)
N2—N1—C7—C8−0.7 (2)C11—C16—C17—C18149.6 (2)
N4—N3—C8—C9−179.0 (2)O2—C17—C18—C19−23.7 (2)
N4—N3—C8—C7−1.8 (2)C16—C17—C18—C19156.7 (2)
O1—C7—C8—N32.3 (3)O2—C17—C18—C23149.5 (2)
N1—C7—C8—N3−177.0 (2)C16—C17—C18—C23−30.1 (2)
O1—C7—C8—C9180.0 (2)C23—C18—C19—C200.9 (3)
N1—C7—C8—C90.6 (2)C17—C18—C19—C20174.4 (2)
N1—N2—C9—C8−0.1 (2)C18—C19—C20—C21−0.7 (3)
N1—N2—C9—C10−179.3 (1)C19—C20—C21—C220.1 (3)
N3—C8—C9—N2177.3 (2)C20—C21—C22—C230.3 (3)
C7—C8—C9—N2−0.4 (2)C21—C22—C23—C18−0.1 (3)
N3—C8—C9—C10−3.5 (3)C19—C18—C23—C22−0.5 (2)
C7—C8—C9—C10178.8 (2)C17—C18—C23—C22−173.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4···O10.89 (1)2.06 (2)2.755 (2)135 (2)
N4—H4···O20.89 (1)2.05 (2)2.698 (2)130 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2371).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Golinski, B., Reck, G. & Kutschabsky, L. (1983). Z. Kristallogr.158, 271–278.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography