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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1782.
Published online 2010 June 26. doi:  10.1107/S1600536810023779
PMCID: PMC3006855

4-[(9-Ethyl-9H-carbazol-3-yl)methyl­idene­amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Abstract

The imino–carbon double bond in the title Schiff base, C26H24N4O, has an E configuration. The 13-membered carbazolyl fused-ring (r.m.s. deviation = 0.056 Å) is nearly coplanar with five-membered pyrazole ring (r.m.s. deviation = 0.036 Å) [dihedral angle between the two systems = 10.4 (1)°]; the phenyl substituent is twisted by 51.1 (1)° with respect to the five-membered ring.

Related literature

For background to this class of Schiff bases, see: Montalvo-González & Ariza-Castolo (2003 [triangle]).

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Object name is e-66-o1782-scheme1.jpg

Experimental

Crystal data

  • C26H24N4O
  • M r = 408.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1782-efi1.jpg
  • a = 10.4458 (6) Å
  • b = 18.2674 (11) Å
  • c = 10.8989 (6) Å
  • β = 96.127 (1)°
  • V = 2067.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 19772 measured reflections
  • 4756 independent reflections
  • 4000 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.104
  • S = 1.02
  • 4756 reflections
  • 283 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023779/jh2169sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023779/jh2169Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

4-Aminoantipyrine (4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one) possesses a pyrazolone unit, a feature that is important to the design of non-steroidal anti-inflammatory chemicals. Its amino group group allows the chemical to condense with aromatic aldehydes to yield Schiff bases. The crystal structures of a large number of such Schiff bases have been reported. For the Schiff base derived from the benzaldehyde homolog, the phenyl and pyrazoly rings are nearly coplanar (Montalvo-González & Ariza-Castolo, 2003). In the title carbazole-aldehyde analog (Scheme I, Fig. 1), the 13-membered carbazolyl fused-ring is nearly coplanar with 5-membered pyrazolyl ring [dihedral angle between the two systems 10.4 (1) °]. The phenyl substituent is twisted by 51.1 (1) ° with respect to the 5-membered ring.

Experimental

9-Ethylcarbazole-3-carboxaldehyde (0.50 g, 2.2 mmol) and 4-aminoantipyrine (0.45 g, 2.2 mmol) here heated in methanol (15 ml) for 5 h to afford a light yellow precipitate. The solid material was collected and recrystallized from methanol.

Refinement

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

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C26H24N4O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C26H24N4OF(000) = 864
Mr = 408.49Dx = 1.312 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7258 reflections
a = 10.4458 (6) Åθ = 2.2–28.3°
b = 18.2674 (11) ŵ = 0.08 mm1
c = 10.8989 (6) ÅT = 100 K
β = 96.127 (1)°Prism, yellow
V = 2067.8 (2) Å30.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer4000 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 27.5°, θmin = 2.2°
ω scansh = −13→13
19772 measured reflectionsk = −23→23
4756 independent reflectionsl = −14→14

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0525P)2 + 0.720P] where P = (Fo2 + 2Fc2)/3
4756 reflections(Δ/σ)max < 0.001
283 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.25 e Å3

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.

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

xyzUiso*/Ueq
O10.60645 (8)0.54578 (4)0.40022 (8)0.02038 (19)
N11.35714 (9)0.68186 (6)0.65745 (9)0.0206 (2)
N20.75630 (9)0.69353 (6)0.47222 (9)0.0175 (2)
N30.43648 (9)0.70479 (5)0.32066 (9)0.0178 (2)
N40.44409 (9)0.62867 (5)0.33728 (9)0.0179 (2)
C11.36337 (11)0.75748 (7)0.66819 (11)0.0196 (2)
C21.46850 (12)0.80129 (8)0.70917 (12)0.0250 (3)
H21.55080.78050.73300.030*
C31.44906 (13)0.87620 (8)0.71402 (12)0.0269 (3)
H31.51920.90720.74190.032*
C41.32833 (13)0.90704 (7)0.67875 (11)0.0255 (3)
H41.31770.95860.68330.031*
C51.22368 (12)0.86349 (7)0.63713 (11)0.0213 (3)
H51.14200.88480.61260.026*
C61.24060 (11)0.78774 (7)0.63197 (10)0.0178 (2)
C71.15504 (11)0.72649 (6)0.60145 (10)0.0165 (2)
C81.02461 (11)0.72027 (6)0.56055 (10)0.0167 (2)
H80.97370.76290.54340.020*
C90.96945 (11)0.65098 (6)0.54505 (10)0.0172 (2)
C101.04661 (12)0.58849 (6)0.57261 (11)0.0193 (2)
H101.00700.54160.56600.023*
C111.17744 (11)0.59244 (6)0.60877 (11)0.0196 (2)
H111.22830.54960.62410.023*
C121.23104 (11)0.66235 (7)0.62169 (10)0.0179 (2)
C131.46091 (11)0.63045 (7)0.69520 (11)0.0223 (3)
H13A1.54450.65350.68320.027*
H13B1.45090.58640.64200.027*
C141.46196 (15)0.60749 (9)0.82923 (13)0.0357 (3)
H14A1.53180.57230.85010.054*
H14B1.37940.58470.84160.054*
H14C1.47540.65060.88250.054*
C150.83444 (11)0.63985 (6)0.49658 (10)0.0175 (2)
H150.80370.59130.48270.021*
C160.56810 (11)0.60962 (6)0.38971 (10)0.0165 (2)
C170.63052 (11)0.67924 (6)0.42004 (10)0.0163 (2)
C180.54672 (11)0.73382 (6)0.37959 (10)0.0169 (2)
C190.56536 (12)0.81422 (6)0.39240 (11)0.0208 (3)
H19A0.53600.83820.31390.031*
H19B0.65690.82480.41470.031*
H19C0.51550.83270.45710.031*
C200.31008 (11)0.73921 (7)0.31473 (12)0.0221 (3)
H20A0.32030.79140.33390.033*
H20B0.25960.71600.37480.033*
H20C0.26540.73340.23160.033*
C210.35842 (11)0.58088 (6)0.26541 (10)0.0170 (2)
C220.31925 (12)0.59525 (7)0.14157 (11)0.0207 (3)
H220.34820.63800.10340.025*
C230.23735 (12)0.54634 (7)0.07451 (11)0.0217 (3)
H230.21000.5560−0.00990.026*
C240.19515 (11)0.48364 (7)0.12940 (11)0.0209 (3)
H240.13940.45030.08300.025*
C250.23514 (12)0.47000 (7)0.25284 (11)0.0208 (2)
H250.20670.42690.29060.025*
C260.31609 (11)0.51841 (6)0.32186 (11)0.0186 (2)
H260.34220.50900.40660.022*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0190 (4)0.0166 (4)0.0248 (4)0.0015 (3)−0.0012 (3)0.0022 (3)
N10.0129 (5)0.0230 (5)0.0254 (5)0.0016 (4)−0.0005 (4)−0.0015 (4)
N20.0141 (5)0.0215 (5)0.0164 (4)−0.0007 (4)−0.0006 (4)−0.0016 (4)
N30.0157 (5)0.0142 (5)0.0227 (5)0.0007 (4)−0.0022 (4)0.0005 (4)
N40.0160 (5)0.0145 (5)0.0222 (5)−0.0003 (4)−0.0030 (4)0.0019 (4)
C10.0169 (6)0.0236 (6)0.0187 (5)−0.0015 (5)0.0040 (4)−0.0004 (4)
C20.0173 (6)0.0327 (7)0.0250 (6)−0.0050 (5)0.0031 (5)−0.0012 (5)
C30.0263 (6)0.0318 (7)0.0229 (6)−0.0139 (5)0.0040 (5)−0.0009 (5)
C40.0346 (7)0.0208 (6)0.0214 (6)−0.0079 (5)0.0043 (5)0.0010 (5)
C50.0249 (6)0.0203 (6)0.0186 (5)−0.0017 (5)0.0024 (5)0.0018 (4)
C60.0166 (5)0.0219 (6)0.0153 (5)−0.0020 (4)0.0029 (4)0.0001 (4)
C70.0174 (6)0.0171 (5)0.0153 (5)0.0005 (4)0.0027 (4)0.0000 (4)
C80.0162 (5)0.0178 (5)0.0159 (5)0.0017 (4)0.0009 (4)0.0002 (4)
C90.0155 (5)0.0204 (6)0.0154 (5)0.0008 (4)0.0009 (4)−0.0015 (4)
C100.0207 (6)0.0167 (6)0.0201 (5)−0.0003 (4)0.0006 (4)−0.0033 (4)
C110.0190 (6)0.0175 (6)0.0218 (6)0.0042 (4)0.0002 (4)−0.0023 (4)
C120.0142 (5)0.0222 (6)0.0173 (5)0.0018 (4)0.0009 (4)−0.0012 (4)
C130.0141 (5)0.0283 (6)0.0243 (6)0.0055 (5)0.0010 (4)−0.0021 (5)
C140.0337 (8)0.0478 (9)0.0254 (7)0.0170 (7)0.0021 (6)0.0019 (6)
C150.0174 (5)0.0190 (6)0.0159 (5)−0.0016 (4)0.0004 (4)−0.0016 (4)
C160.0142 (5)0.0212 (6)0.0138 (5)−0.0005 (4)0.0002 (4)0.0017 (4)
C170.0157 (5)0.0185 (6)0.0147 (5)−0.0008 (4)0.0011 (4)−0.0008 (4)
C180.0157 (5)0.0198 (6)0.0149 (5)−0.0013 (4)0.0009 (4)−0.0016 (4)
C190.0218 (6)0.0172 (6)0.0226 (6)0.0001 (5)−0.0017 (5)−0.0023 (4)
C200.0167 (6)0.0225 (6)0.0265 (6)0.0028 (5)−0.0001 (5)0.0001 (5)
C210.0128 (5)0.0174 (5)0.0202 (5)−0.0003 (4)0.0000 (4)−0.0006 (4)
C220.0215 (6)0.0188 (6)0.0215 (6)−0.0037 (5)0.0003 (5)0.0039 (4)
C230.0238 (6)0.0216 (6)0.0188 (6)−0.0006 (5)−0.0024 (5)0.0012 (5)
C240.0182 (6)0.0187 (6)0.0251 (6)−0.0020 (5)−0.0001 (5)−0.0036 (5)
C250.0203 (6)0.0168 (6)0.0256 (6)−0.0017 (5)0.0043 (5)0.0025 (5)
C260.0172 (5)0.0199 (6)0.0185 (5)0.0017 (4)0.0020 (4)0.0021 (4)

Geometric parameters (Å, °)

O1—C161.2344 (14)C11—C121.3956 (17)
N1—C121.3799 (15)C11—H110.9500
N1—C11.3873 (16)C13—C141.5187 (18)
N1—C131.4598 (15)C13—H13A0.9900
N2—C151.2853 (15)C13—H13B0.9900
N2—C171.3994 (14)C14—H14A0.9800
N3—C181.3646 (14)C14—H14B0.9800
N3—N41.4034 (13)C14—H14C0.9800
N3—C201.4577 (15)C15—H150.9500
N4—C161.4028 (14)C16—C171.4511 (16)
N4—C211.4237 (14)C17—C181.3682 (16)
C1—C21.3933 (17)C18—C191.4861 (16)
C1—C61.4134 (16)C19—H19A0.9800
C2—C31.385 (2)C19—H19B0.9800
C2—H20.9500C19—H19C0.9800
C3—C41.397 (2)C20—H20A0.9800
C3—H30.9500C20—H20B0.9800
C4—C51.3884 (17)C20—H20C0.9800
C4—H40.9500C21—C261.3907 (16)
C5—C61.3969 (17)C21—C221.3929 (16)
C5—H50.9500C22—C231.3895 (16)
C6—C71.4484 (16)C22—H220.9500
C7—C81.3922 (16)C23—C241.3857 (17)
C7—C121.4192 (16)C23—H230.9500
C8—C91.3935 (16)C24—C251.3880 (17)
C8—H80.9500C24—H240.9500
C9—C101.4112 (16)C25—C261.3881 (16)
C9—C151.4664 (15)C25—H250.9500
C10—C111.3832 (16)C26—H260.9500
C10—H100.9500
C12—N1—C1108.40 (10)C14—C13—H13B109.2
C12—N1—C13124.84 (10)H13A—C13—H13B107.9
C1—N1—C13126.16 (10)C13—C14—H14A109.5
C15—N2—C17119.32 (10)C13—C14—H14B109.5
C18—N3—N4106.92 (9)H14A—C14—H14B109.5
C18—N3—C20124.62 (10)C13—C14—H14C109.5
N4—N3—C20118.15 (9)H14A—C14—H14C109.5
C16—N4—N3109.60 (9)H14B—C14—H14C109.5
C16—N4—C21124.82 (10)N2—C15—C9122.27 (11)
N3—N4—C21120.86 (9)N2—C15—H15118.9
N1—C1—C2128.85 (11)C9—C15—H15118.9
N1—C1—C6109.44 (10)O1—C16—N4123.27 (10)
C2—C1—C6121.70 (12)O1—C16—C17132.33 (11)
C3—C2—C1117.77 (12)N4—C16—C17104.38 (9)
C3—C2—H2121.1C18—C17—N2122.39 (10)
C1—C2—H2121.1C18—C17—C16107.99 (10)
C2—C3—C4121.29 (12)N2—C17—C16129.46 (10)
C2—C3—H3119.4N3—C18—C17110.31 (10)
C4—C3—H3119.4N3—C18—C19121.59 (10)
C5—C4—C3121.00 (12)C17—C18—C19128.09 (10)
C5—C4—H4119.5C18—C19—H19A109.5
C3—C4—H4119.5C18—C19—H19B109.5
C4—C5—C6118.82 (12)H19A—C19—H19B109.5
C4—C5—H5120.6C18—C19—H19C109.5
C6—C5—H5120.6H19A—C19—H19C109.5
C5—C6—C1119.41 (11)H19B—C19—H19C109.5
C5—C6—C7134.17 (11)N3—C20—H20A109.5
C1—C6—C7106.34 (10)N3—C20—H20B109.5
C8—C7—C12119.64 (10)H20A—C20—H20B109.5
C8—C7—C6134.06 (11)N3—C20—H20C109.5
C12—C7—C6106.30 (10)H20A—C20—H20C109.5
C7—C8—C9119.39 (11)H20B—C20—H20C109.5
C7—C8—H8120.3C26—C21—C22120.59 (11)
C9—C8—H8120.3C26—C21—N4118.08 (10)
C8—C9—C10119.31 (10)C22—C21—N4121.33 (10)
C8—C9—C15122.61 (10)C23—C22—C21119.29 (11)
C10—C9—C15118.04 (10)C23—C22—H22120.4
C11—C10—C9122.89 (11)C21—C22—H22120.4
C11—C10—H10118.6C24—C23—C22120.71 (11)
C9—C10—H10118.6C24—C23—H23119.6
C10—C11—C12116.75 (11)C22—C23—H23119.6
C10—C11—H11121.6C23—C24—C25119.35 (11)
C12—C11—H11121.6C23—C24—H24120.3
N1—C12—C11128.71 (11)C25—C24—H24120.3
N1—C12—C7109.39 (10)C26—C25—C24120.92 (11)
C11—C12—C7121.87 (10)C26—C25—H25119.5
N1—C13—C14112.18 (10)C24—C25—H25119.5
N1—C13—H13A109.2C25—C26—C21119.14 (11)
C14—C13—H13A109.2C25—C26—H26120.4
N1—C13—H13B109.2C21—C26—H26120.4
C18—N3—N4—C16−9.38 (12)C8—C7—C12—C11−3.85 (17)
C20—N3—N4—C16−156.12 (10)C6—C7—C12—C11175.87 (11)
C18—N3—N4—C21−166.14 (10)C12—N1—C13—C14−81.94 (15)
C20—N3—N4—C2147.12 (15)C1—N1—C13—C1488.12 (15)
C12—N1—C1—C2175.55 (12)C17—N2—C15—C9176.64 (10)
C13—N1—C1—C24.1 (2)C8—C9—C15—N2−4.26 (18)
C12—N1—C1—C6−3.37 (13)C10—C9—C15—N2178.02 (11)
C13—N1—C1—C6−174.79 (11)N3—N4—C16—O1−170.71 (10)
N1—C1—C2—C3−178.53 (12)C21—N4—C16—O1−15.08 (18)
C6—C1—C2—C30.28 (18)N3—N4—C16—C177.67 (12)
C1—C2—C3—C4−0.18 (19)C21—N4—C16—C17163.30 (10)
C2—C3—C4—C5−0.24 (19)C15—N2—C17—C18−172.81 (11)
C3—C4—C5—C60.56 (18)C15—N2—C17—C161.92 (18)
C4—C5—C6—C1−0.46 (17)O1—C16—C17—C18174.95 (12)
C4—C5—C6—C7175.81 (12)N4—C16—C17—C18−3.22 (12)
N1—C1—C6—C5179.06 (10)O1—C16—C17—N2−0.4 (2)
C2—C1—C6—C50.04 (17)N4—C16—C17—N2−178.54 (11)
N1—C1—C6—C71.84 (13)N4—N3—C18—C177.25 (13)
C2—C1—C6—C7−177.17 (11)C20—N3—C18—C17151.26 (11)
C5—C6—C7—C83.4 (2)N4—N3—C18—C19−173.40 (10)
C1—C6—C7—C8179.98 (12)C20—N3—C18—C19−29.39 (17)
C5—C6—C7—C12−176.29 (13)N2—C17—C18—N3173.21 (10)
C1—C6—C7—C120.32 (12)C16—C17—C18—N3−2.51 (13)
C12—C7—C8—C92.68 (17)N2—C17—C18—C19−6.09 (19)
C6—C7—C8—C9−176.94 (12)C16—C17—C18—C19178.19 (11)
C7—C8—C9—C100.78 (16)C16—N4—C21—C2662.98 (15)
C7—C8—C9—C15−176.91 (10)N3—N4—C21—C26−143.95 (11)
C8—C9—C10—C11−3.41 (17)C16—N4—C21—C22−116.02 (13)
C15—C9—C10—C11174.39 (11)N3—N4—C21—C2237.05 (16)
C9—C10—C11—C122.29 (18)C26—C21—C22—C23−0.13 (18)
C1—N1—C12—C11−174.53 (12)N4—C21—C22—C23178.84 (11)
C13—N1—C12—C11−2.97 (19)C21—C22—C23—C24−0.31 (19)
C1—N1—C12—C73.58 (13)C22—C23—C24—C250.22 (19)
C13—N1—C12—C7175.14 (10)C23—C24—C25—C260.31 (18)
C10—C11—C12—N1179.23 (11)C24—C25—C26—C21−0.74 (18)
C10—C11—C12—C71.34 (17)C22—C21—C26—C250.65 (18)
C8—C7—C12—N1177.90 (10)N4—C21—C26—C25−178.36 (10)
C6—C7—C12—N1−2.39 (13)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2169).

References

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  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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