4-((E)-{2-[N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carboximido­yl]benzyl­idene}amino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Potgieter, K.; Hosten, E.; Gerber, T.; Betz, R.

doi:10.1107/S1600536811039158

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages o2785-o2786

https://doi.org/10.1107/S1600536811039158

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4-((E)-{2-[N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carboximidoyl]benzylidene}amino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Kim Potgieter,^a Eric Hosten,^a Thomas Gerber ^a and Richard Betz ^a ^*

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 20 September 2011; accepted 23 September 2011; online 30 September 2011)

The title compound, C₃₀H₂₈N₆O₂, is a symmetric diimine derived from ortho-dibenzaldehyde. Both C=N bonds are (E)-configured. The terminal N-bonded phenyl groups adopt staggered conformations relative to their respective parent heterocycles, the relevant least-squares planes intersect at angles of 32.35 (11) and 38.59 (10)°. In the crystal, C—H⋯O contacts connect the molecules into chains along the b axis and give rise to a C¹₁(14)C¹₁(14) and a R²₂(12) pattern on different levels of graph-set analysis. The shortest intercentroid distance between two centroids was found at 4.2074 (11) Å between the two five-membered heterocycles.

Related literature

For the crystal structure of another diimine capable of acting as a chelate ligand, see: Yumata et al. (2011 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ). For details on puckering analysis, see: Cremer & Pople (1975 ). For general information about the chelate effect, see: Gade (1998 ).

Experimental

Crystal data

C₃₀H₂₈N₆O₂
M_r = 504.58
Monoclinic, P 2₁
a = 12.6048 (2) Å
b = 7.3389 (2) Å
c = 14.3877 (3) Å
β = 107.622 (1)°
V = 1268.48 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.33 × 0.15 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
12317 measured reflections
3399 independent reflections
2806 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.079
S = 1.01
3399 reflections
347 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C45—H45A⋯O2ⁱ	0.98	2.59	3.535 (2)	161
C55—H55A⋯O1ⁱⁱ	0.98	2.61	3.536 (3)	158
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811039158/bh2383sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536811039158/bh2383Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811039158/bh2383Isup3.hkl

checkCIF report

Comment top

Chelate ligands have found widespread use in coordination chemistry due to the enhanced thermodynamic stability of resultant coordination compounds in relation to metal complexes exclusively applying comparable monodentate ligands (Gade, 1998). In our continuous efforts in elucidating the rules guiding the formation of coordination compounds applying nitrogen-containing chelate ligands, we determined the structure of the title compound to allow for comparative studies in envisioned coordination compounds. Structural information about another diimine capable of acting as a chelate ligand is apparent in the literature (Yumata et al., 2011).

Both C=N double bonds are (E)-configured. The least-squares planes defined by the five-membered heterocycles on the one hand and the central phenyl moiety on the other hand enclose angles of 3.16 (10) and 4.47 (10)°, respectively. The nitrogen-bonded phenyl moieties adopt staggered conformations relative to their respective parent heterocycles, the relevant least-squares planes intersect at angles of 32.35 (11) and 38.59 (10)°. A conformation analysis of the five-membered heterocycles (Cremer & Pople, 1975) is invariably precluded by the small puckering amplitude (Fig. 1).

In the crystal, C–H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii are present. These are observed between H atoms of the methyl groups and the ketonic O atoms. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these interactions is C¹₁(14)C¹₁(14) on the unitary level and emphasizes the presence of two antidromic chains whereas a R²₂(12) descriptor on the binary level highlights the existence of cyclic patterns. In total, the molecules are connected to infinite chains along the crystallographic b axis. The shortest intercentroid distance between two centers of gravity was found at 4.2074 (11) Å (Fig. 2).

The packing of the title compound in the crystal is shown in Figure 3.

Related literature top

For the crystal structure of another diimine capable of acting as a chelate ligand, see: Yumata et al. (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For details on puckering analysis, see: Cremer & Pople (1975). For general information about the chelate effect, see: Gade (1998).

Experimental top

A solution of 0.99 g of phthalaldehyde in 20 cm³ of methanol was added dropwise to a stirred solution of 3.00 g of 4-aminoantipyrine in 30 cm³ of methanol. The solution was refluxed under nitrogen for 15 minutes. Upon cooling, a yellow precipitate formed which was filtered and dried under reduced pressure. The product was recrystallized from methanol to produce yellow crystals.

Structure description top

The packing of the title compound in the crystal is shown in Figure 3.

For the crystal structure of another diimine capable of acting as a chelate ligand, see: Yumata et al. (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For details on puckering analysis, see: Cremer & Pople (1975). For general information about the chelate effect, see: Gade (1998).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 - 1 0]. Symmetry operators: ⁱ x, y - 1, z; ⁱⁱ x, y + 1, z.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

4-((E)-{2-[N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H- pyrazol-4-yl)carboximidoyl]benzylidene}amino)-1,5-dimethyl-2-phenyl- 2,3-dihydro-1H-pyrazol-3-one top

Crystal data top

C₃₀H₂₈N₆O₂	F(000) = 532
M_r = 504.58	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5101 reflections
a = 12.6048 (2) Å	θ = 2.6–28.2°
b = 7.3389 (2) Å	µ = 0.09 mm⁻¹
c = 14.3877 (3) Å	T = 200 K
β = 107.622 (1)°	Rod, yellow
V = 1268.48 (5) Å³	0.33 × 0.15 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	2806 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 28.3°, θ_min = 2.6°
φ and ω scans	h = −16→16
12317 measured reflections	k = −9→9
3399 independent reflections	l = −19→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0471P)²] where P = (F_o² + 2F_c²)/3
3399 reflections	(Δ/σ)_max < 0.001
347 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³
0 constraints

Crystal data top

C₃₀H₂₈N₆O₂	V = 1268.48 (5) Å³
M_r = 504.58	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 12.6048 (2) Å	µ = 0.09 mm⁻¹
b = 7.3389 (2) Å	T = 200 K
c = 14.3877 (3) Å	0.33 × 0.15 × 0.08 mm
β = 107.622 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2806 reflections with I > 2σ(I)
12317 measured reflections	R_int = 0.032
3399 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
3399 reflections	Δρ_min = −0.18 e Å⁻³
347 parameters

Special details top

Refinement. Due to the absence of a strong anomalous scatterer, the Flack parameter is meaningless. Thus, Friedel opposites (2450 pairs) have been merged and the item was removed from the CIF.

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

	x	y	z	U_iso*/U_eq
O1	0.22361 (12)	−0.1543 (2)	0.36994 (11)	0.0389 (3)
O2	0.08533 (11)	0.2814 (2)	0.22952 (10)	0.0368 (3)
N1	0.43019 (13)	−0.2449 (2)	0.30112 (11)	0.0319 (4)
N2	0.24983 (12)	0.3960 (2)	0.11404 (11)	0.0307 (4)
N3	0.26332 (13)	−0.4405 (2)	0.44041 (11)	0.0313 (4)
N4	0.34923 (13)	−0.5696 (2)	0.45284 (12)	0.0329 (4)
N5	0.01135 (12)	0.5670 (2)	0.17718 (11)	0.0290 (3)
N6	0.02704 (13)	0.7000 (2)	0.11152 (11)	0.0307 (4)
C1	0.38269 (15)	−0.1028 (3)	0.25442 (13)	0.0300 (4)
H1	0.3122	−0.0659	0.2590	0.036*
C2	0.28998 (15)	0.2528 (3)	0.16189 (13)	0.0287 (4)
H2	0.2550	0.2004	0.2054	0.034*
C11	0.43573 (14)	0.0033 (3)	0.19412 (12)	0.0271 (4)
C12	0.39117 (14)	0.1687 (3)	0.14939 (12)	0.0268 (4)
C13	0.44707 (14)	0.2614 (3)	0.09350 (13)	0.0320 (4)
H13	0.4179	0.3738	0.0638	0.038*
C14	0.54326 (16)	0.1942 (3)	0.08029 (14)	0.0362 (5)
H14	0.5793	0.2586	0.0411	0.043*
C15	0.58734 (15)	0.0316 (3)	0.12471 (14)	0.0353 (5)
H15	0.6542	−0.0152	0.1165	0.042*
C16	0.53411 (15)	−0.0616 (3)	0.18057 (13)	0.0331 (5)
H16	0.5650	−0.1728	0.2106	0.040*
C21	0.19608 (15)	−0.4426 (3)	0.50392 (12)	0.0291 (4)
C22	0.23326 (16)	−0.5253 (3)	0.59461 (13)	0.0366 (5)
H22	0.3059	−0.5760	0.6168	0.044*
C23	0.16325 (18)	−0.5334 (3)	0.65265 (14)	0.0410 (5)
H23	0.1877	−0.5922	0.7143	0.049*
C24	0.05832 (18)	−0.4567 (3)	0.62151 (15)	0.0404 (5)
H24	0.0104	−0.4637	0.6612	0.048*
C25	0.02366 (17)	−0.3697 (3)	0.53213 (14)	0.0387 (5)
H25	−0.0478	−0.3143	0.5112	0.046*
C26	0.09157 (15)	−0.3625 (3)	0.47301 (14)	0.0331 (4)
H26	0.0670	−0.3030	0.4115	0.040*
C31	−0.09471 (14)	0.5517 (3)	0.19288 (12)	0.0266 (4)
C32	−0.19051 (15)	0.6147 (3)	0.12384 (13)	0.0308 (4)
H32	−0.1866	0.6711	0.0655	0.037*
C33	−0.29113 (15)	0.5939 (3)	0.14162 (15)	0.0371 (5)
H33	−0.3572	0.6365	0.0950	0.044*
C34	−0.29758 (16)	0.5124 (3)	0.22569 (16)	0.0398 (5)
H34	−0.3677	0.4997	0.2369	0.048*
C35	−0.20286 (16)	0.4491 (3)	0.29363 (15)	0.0389 (5)
H35	−0.2074	0.3923	0.3516	0.047*
C36	−0.10063 (15)	0.4686 (3)	0.27696 (13)	0.0315 (4)
H36	−0.0349	0.4248	0.3235	0.038*
C41	0.27970 (16)	−0.2948 (3)	0.38473 (13)	0.0308 (4)
C42	0.37715 (15)	−0.3447 (3)	0.35641 (13)	0.0300 (4)
C43	0.41402 (15)	−0.5094 (3)	0.39719 (13)	0.0312 (4)
C44	0.51017 (17)	−0.6187 (3)	0.38933 (15)	0.0396 (5)
H44A	0.4831	−0.7214	0.3449	0.059*
H44B	0.5521	−0.6650	0.4539	0.059*
H44C	0.5587	−0.5419	0.3640	0.059*
C45	0.31200 (19)	−0.7619 (3)	0.44471 (16)	0.0425 (5)
H45A	0.2540	−0.7801	0.3823	0.064*
H45B	0.2821	−0.7909	0.4984	0.064*
H45C	0.3753	−0.8419	0.4480	0.064*
C51	0.08748 (14)	0.4251 (3)	0.18620 (13)	0.0275 (4)
C52	0.15879 (14)	0.4847 (3)	0.12943 (12)	0.0271 (4)
C53	0.12091 (14)	0.6489 (3)	0.08866 (13)	0.0293 (4)
C54	0.16732 (17)	0.7650 (3)	0.02611 (16)	0.0416 (5)
H54A	0.1097	0.7886	−0.0358	0.062*
H54B	0.2302	0.7024	0.0135	0.062*
H54C	0.1927	0.8808	0.0593	0.062*
C55	0.01693 (18)	0.8901 (3)	0.14159 (16)	0.0388 (5)
H55A	0.0748	0.9148	0.2033	0.058*
H55B	−0.0566	0.9082	0.1502	0.058*
H55C	0.0259	0.9734	0.0913	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0467 (8)	0.0251 (8)	0.0483 (8)	0.0089 (6)	0.0195 (7)	0.0109 (7)
O2	0.0414 (7)	0.0240 (7)	0.0490 (8)	0.0088 (6)	0.0198 (6)	0.0133 (7)
N1	0.0374 (8)	0.0270 (9)	0.0305 (8)	0.0042 (7)	0.0091 (7)	0.0037 (7)
N2	0.0318 (8)	0.0291 (9)	0.0310 (8)	0.0045 (7)	0.0092 (6)	0.0042 (7)
N3	0.0403 (8)	0.0223 (8)	0.0312 (8)	0.0030 (7)	0.0107 (7)	0.0050 (7)
N4	0.0438 (9)	0.0217 (9)	0.0321 (8)	0.0054 (7)	0.0100 (7)	0.0052 (7)
N5	0.0335 (8)	0.0206 (8)	0.0336 (8)	0.0058 (7)	0.0114 (6)	0.0068 (7)
N6	0.0366 (8)	0.0204 (8)	0.0344 (8)	0.0042 (7)	0.0099 (7)	0.0059 (7)
C1	0.0315 (9)	0.0276 (11)	0.0315 (9)	0.0026 (8)	0.0105 (8)	0.0007 (9)
C2	0.0312 (9)	0.0277 (10)	0.0281 (9)	0.0025 (8)	0.0104 (7)	0.0032 (8)
C11	0.0296 (8)	0.0264 (10)	0.0245 (8)	0.0011 (8)	0.0070 (7)	−0.0017 (8)
C12	0.0282 (8)	0.0273 (10)	0.0239 (8)	0.0002 (8)	0.0066 (7)	−0.0012 (8)
C13	0.0335 (9)	0.0291 (10)	0.0332 (10)	−0.0002 (8)	0.0098 (8)	0.0048 (9)
C14	0.0336 (10)	0.0413 (12)	0.0359 (10)	−0.0052 (9)	0.0139 (8)	0.0003 (10)
C15	0.0284 (9)	0.0426 (13)	0.0364 (10)	0.0035 (9)	0.0122 (8)	−0.0048 (10)
C16	0.0323 (9)	0.0329 (12)	0.0336 (10)	0.0062 (9)	0.0091 (8)	−0.0001 (9)
C21	0.0390 (9)	0.0216 (9)	0.0264 (9)	−0.0042 (8)	0.0096 (7)	−0.0013 (8)
C22	0.0444 (10)	0.0319 (11)	0.0301 (9)	−0.0030 (10)	0.0063 (8)	0.0033 (9)
C23	0.0595 (12)	0.0352 (12)	0.0276 (9)	−0.0059 (11)	0.0123 (9)	0.0027 (9)
C24	0.0546 (12)	0.0329 (12)	0.0384 (11)	−0.0105 (10)	0.0214 (9)	−0.0036 (10)
C25	0.0432 (11)	0.0308 (11)	0.0433 (11)	−0.0034 (10)	0.0150 (9)	−0.0026 (10)
C26	0.0415 (10)	0.0262 (10)	0.0297 (9)	−0.0016 (9)	0.0078 (8)	0.0022 (8)
C31	0.0299 (8)	0.0205 (9)	0.0293 (9)	0.0045 (8)	0.0087 (7)	−0.0040 (8)
C32	0.0386 (10)	0.0265 (10)	0.0260 (9)	0.0090 (9)	0.0081 (8)	−0.0019 (8)
C33	0.0336 (9)	0.0340 (12)	0.0395 (10)	0.0091 (9)	0.0049 (8)	−0.0032 (9)
C34	0.0349 (10)	0.0364 (12)	0.0521 (12)	0.0032 (9)	0.0191 (9)	−0.0012 (10)
C35	0.0481 (11)	0.0319 (11)	0.0404 (11)	0.0060 (10)	0.0189 (9)	0.0049 (10)
C36	0.0360 (9)	0.0258 (10)	0.0310 (9)	0.0048 (8)	0.0076 (8)	0.0023 (8)
C41	0.0381 (10)	0.0243 (10)	0.0278 (9)	−0.0006 (8)	0.0063 (8)	0.0004 (8)
C42	0.0351 (9)	0.0259 (10)	0.0265 (9)	0.0018 (8)	0.0059 (8)	0.0015 (8)
C43	0.0385 (10)	0.0273 (10)	0.0247 (8)	0.0030 (9)	0.0049 (8)	−0.0009 (8)
C44	0.0460 (11)	0.0332 (12)	0.0383 (11)	0.0103 (10)	0.0105 (9)	0.0043 (9)
C45	0.0575 (13)	0.0220 (11)	0.0477 (12)	0.0051 (10)	0.0155 (10)	0.0060 (10)
C51	0.0307 (9)	0.0218 (10)	0.0282 (9)	0.0032 (8)	0.0061 (7)	0.0010 (8)
C52	0.0297 (8)	0.0235 (9)	0.0263 (8)	0.0027 (8)	0.0059 (7)	0.0018 (8)
C53	0.0312 (9)	0.0264 (10)	0.0288 (9)	0.0011 (8)	0.0071 (7)	0.0021 (9)
C54	0.0453 (11)	0.0335 (12)	0.0472 (12)	0.0035 (10)	0.0158 (10)	0.0145 (11)
C55	0.0514 (12)	0.0197 (10)	0.0451 (12)	0.0061 (9)	0.0142 (10)	0.0041 (9)

Geometric parameters (Å, º) top

O1—C41	1.232 (2)	C23—H23	0.9500
O2—C51	1.229 (2)	C24—C25	1.383 (3)
N1—C1	1.286 (3)	C24—H24	0.9500
N1—C42	1.392 (2)	C25—C26	1.378 (3)
N2—C2	1.274 (2)	C25—H25	0.9500
N2—C52	1.394 (2)	C26—H26	0.9500
N3—C41	1.389 (2)	C31—C36	1.377 (3)
N3—N4	1.409 (2)	C31—C32	1.390 (2)
N3—C21	1.422 (2)	C32—C33	1.376 (3)
N4—C43	1.378 (2)	C32—H32	0.9500
N4—C45	1.481 (3)	C33—C34	1.374 (3)
N5—C51	1.395 (2)	C33—H33	0.9500
N5—N6	1.413 (2)	C34—C35	1.375 (3)
N5—C31	1.426 (2)	C34—H34	0.9500
N6—C53	1.373 (2)	C35—C36	1.388 (3)
N6—C55	1.478 (3)	C35—H35	0.9500
C1—C11	1.469 (3)	C36—H36	0.9500
C1—H1	0.9500	C41—C42	1.453 (3)
C2—C12	1.476 (3)	C42—C43	1.362 (3)
C2—H2	0.9500	C43—C44	1.486 (3)
C11—C16	1.396 (2)	C44—H44A	0.9800
C11—C12	1.408 (3)	C44—H44B	0.9800
C12—C13	1.396 (3)	C44—H44C	0.9800
C13—C14	1.374 (3)	C45—H45A	0.9800
C13—H13	0.9500	C45—H45B	0.9800
C14—C15	1.388 (3)	C45—H45C	0.9800
C14—H14	0.9500	C51—C52	1.453 (3)
C15—C16	1.375 (3)	C52—C53	1.362 (3)
C15—H15	0.9500	C53—C54	1.482 (3)
C16—H16	0.9500	C54—H54A	0.9800
C21—C22	1.386 (3)	C54—H54B	0.9800
C21—C26	1.387 (3)	C54—H54C	0.9800
C22—C23	1.388 (3)	C55—H55A	0.9800
C22—H22	0.9500	C55—H55B	0.9800
C23—C24	1.381 (3)	C55—H55C	0.9800

C1—N1—C42	119.80 (16)	C32—C31—N5	120.91 (16)
C2—N2—C52	120.71 (16)	C33—C32—C31	118.70 (17)
C41—N3—N4	110.38 (14)	C33—C32—H32	120.7
C41—N3—C21	126.90 (16)	C31—C32—H32	120.7
N4—N3—C21	119.75 (15)	C34—C33—C32	121.04 (18)
C43—N4—N3	106.19 (15)	C34—C33—H33	119.5
C43—N4—C45	119.27 (17)	C32—C33—H33	119.5
N3—N4—C45	114.69 (16)	C33—C34—C35	120.20 (18)
C51—N5—N6	110.25 (14)	C33—C34—H34	119.9
C51—N5—C31	125.29 (16)	C35—C34—H34	119.9
N6—N5—C31	119.20 (14)	C34—C35—C36	119.62 (19)
C53—N6—N5	106.08 (14)	C34—C35—H35	120.2
C53—N6—C55	119.00 (17)	C36—C35—H35	120.2
N5—N6—C55	114.48 (15)	C31—C36—C35	119.86 (17)
N1—C1—C11	121.03 (17)	C31—C36—H36	120.1
N1—C1—H1	119.5	C35—C36—H36	120.1
C11—C1—H1	119.5	O1—C41—N3	124.51 (18)
N2—C2—C12	119.71 (17)	O1—C41—C42	130.71 (19)
N2—C2—H2	120.1	N3—C41—C42	104.68 (16)
C12—C2—H2	120.1	C43—C42—N1	123.54 (18)
C16—C11—C12	118.59 (17)	C43—C42—C41	108.06 (17)
C16—C11—C1	118.93 (17)	N1—C42—C41	128.35 (17)
C12—C11—C1	122.48 (16)	C42—C43—N4	110.47 (17)
C13—C12—C11	118.83 (17)	C42—C43—C44	128.76 (19)
C13—C12—C2	118.15 (17)	N4—C43—C44	120.76 (18)
C11—C12—C2	122.98 (17)	C43—C44—H44A	109.5
C14—C13—C12	121.67 (19)	C43—C44—H44B	109.5
C14—C13—H13	119.2	H44A—C44—H44B	109.5
C12—C13—H13	119.2	C43—C44—H44C	109.5
C13—C14—C15	119.46 (19)	H44A—C44—H44C	109.5
C13—C14—H14	120.3	H44B—C44—H44C	109.5
C15—C14—H14	120.3	N4—C45—H45A	109.5
C16—C15—C14	119.93 (18)	N4—C45—H45B	109.5
C16—C15—H15	120.0	H45A—C45—H45B	109.5
C14—C15—H15	120.0	N4—C45—H45C	109.5
C15—C16—C11	121.53 (19)	H45A—C45—H45C	109.5
C15—C16—H16	119.2	H45B—C45—H45C	109.5
C11—C16—H16	119.2	O2—C51—N5	124.56 (17)
C22—C21—C26	120.34 (18)	O2—C51—C52	130.96 (17)
C22—C21—N3	120.80 (17)	N5—C51—C52	104.37 (16)
C26—C21—N3	118.84 (16)	C53—C52—N2	122.88 (17)
C21—C22—C23	119.34 (19)	C53—C52—C51	108.21 (16)
C21—C22—H22	120.3	N2—C52—C51	128.89 (17)
C23—C22—H22	120.3	C52—C53—N6	110.71 (17)
C24—C23—C22	120.54 (19)	C52—C53—C54	128.22 (18)
C24—C23—H23	119.7	N6—C53—C54	121.06 (17)
C22—C23—H23	119.7	C53—C54—H54A	109.5
C23—C24—C25	119.46 (19)	C53—C54—H54B	109.5
C23—C24—H24	120.3	H54A—C54—H54B	109.5
C25—C24—H24	120.3	C53—C54—H54C	109.5
C26—C25—C24	120.7 (2)	H54A—C54—H54C	109.5
C26—C25—H25	119.6	H54B—C54—H54C	109.5
C24—C25—H25	119.6	N6—C55—H55A	109.5
C25—C26—C21	119.52 (18)	N6—C55—H55B	109.5
C25—C26—H26	120.2	H55A—C55—H55B	109.5
C21—C26—H26	120.2	N6—C55—H55C	109.5
C36—C31—C32	120.58 (17)	H55A—C55—H55C	109.5
C36—C31—N5	118.48 (15)	H55B—C55—H55C	109.5

C41—N3—N4—C43	−5.0 (2)	C31—C32—C33—C34	0.0 (3)
C21—N3—N4—C43	−166.77 (16)	C32—C33—C34—C35	−0.4 (3)
C41—N3—N4—C45	−138.91 (17)	C33—C34—C35—C36	0.3 (3)
C21—N3—N4—C45	59.3 (2)	C32—C31—C36—C35	−0.6 (3)
C51—N5—N6—C53	−6.49 (19)	N5—C31—C36—C35	−178.99 (19)
C31—N5—N6—C53	−162.23 (16)	C34—C35—C36—C31	0.2 (3)
C51—N5—N6—C55	−139.77 (17)	N4—N3—C41—O1	−172.85 (17)
C31—N5—N6—C55	64.5 (2)	C21—N3—C41—O1	−12.7 (3)
C42—N1—C1—C11	−178.92 (16)	N4—N3—C41—C42	3.94 (19)
C52—N2—C2—C12	−175.70 (16)	C21—N3—C41—C42	164.11 (16)
N1—C1—C11—C16	6.0 (3)	C1—N1—C42—C43	170.82 (18)
N1—C1—C11—C12	−173.96 (17)	C1—N1—C42—C41	−12.0 (3)
C16—C11—C12—C13	−0.1 (2)	O1—C41—C42—C43	175.1 (2)
C1—C11—C12—C13	179.78 (17)	N3—C41—C42—C43	−1.43 (19)
C16—C11—C12—C2	−177.71 (17)	O1—C41—C42—N1	−2.4 (3)
C1—C11—C12—C2	2.2 (3)	N3—C41—C42—N1	−178.94 (17)
N2—C2—C12—C13	7.2 (3)	N1—C42—C43—N4	176.02 (17)
N2—C2—C12—C11	−175.19 (17)	C41—C42—C43—N4	−1.6 (2)
C11—C12—C13—C14	0.8 (3)	N1—C42—C43—C44	−2.9 (3)
C2—C12—C13—C14	178.47 (16)	C41—C42—C43—C44	179.46 (18)
C12—C13—C14—C15	−1.0 (3)	N3—N4—C43—C42	4.0 (2)
C13—C14—C15—C16	0.6 (3)	C45—N4—C43—C42	135.41 (18)
C14—C15—C16—C11	0.0 (3)	N3—N4—C43—C44	−176.99 (16)
C12—C11—C16—C15	−0.2 (3)	C45—N4—C43—C44	−45.6 (3)
C1—C11—C16—C15	179.84 (17)	N6—N5—C51—O2	−171.39 (17)
C41—N3—C21—C22	−137.5 (2)	C31—N5—C51—O2	−17.5 (3)
N4—N3—C21—C22	21.0 (3)	N6—N5—C51—C52	5.15 (19)
C41—N3—C21—C26	43.5 (3)	C31—N5—C51—C52	159.09 (16)
N4—N3—C21—C26	−158.03 (17)	C2—N2—C52—C53	172.22 (17)
C26—C21—C22—C23	2.5 (3)	C2—N2—C52—C51	−9.2 (3)
N3—C21—C22—C23	−176.58 (19)	O2—C51—C52—C53	174.31 (19)
C21—C22—C23—C24	−1.3 (3)	N5—C51—C52—C53	−1.92 (19)
C22—C23—C24—C25	−0.7 (3)	O2—C51—C52—N2	−4.4 (3)
C23—C24—C25—C26	1.5 (3)	N5—C51—C52—N2	179.37 (17)
C24—C25—C26—C21	−0.4 (3)	N2—C52—C53—N6	176.71 (16)
C22—C21—C26—C25	−1.6 (3)	C51—C52—C53—N6	−2.1 (2)
N3—C21—C26—C25	177.43 (18)	N2—C52—C53—C54	−2.3 (3)
C51—N5—C31—C36	49.2 (3)	C51—C52—C53—C54	178.90 (19)
N6—N5—C31—C36	−159.00 (17)	N5—N6—C53—C52	5.20 (19)
C51—N5—C31—C32	−129.2 (2)	C55—N6—C53—C52	135.95 (18)
N6—N5—C31—C32	22.7 (3)	N5—N6—C53—C54	−175.71 (17)
C36—C31—C32—C33	0.5 (3)	C55—N6—C53—C54	−45.0 (3)
N5—C31—C32—C33	178.85 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C45—H45A···O2ⁱ	0.98	2.59	3.535 (2)	161
C55—H55A···O1ⁱⁱ	0.98	2.61	3.536 (3)	158

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₈N₆O₂
M_r	504.58
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	200
a, b, c (Å)	12.6048 (2), 7.3389 (2), 14.3877 (3)
β (°)	107.622 (1)
V (Å³)	1268.48 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.15 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12317, 3399, 2806
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.079, 1.01
No. of reflections	3399
No. of parameters	347
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C45—H45A···O2ⁱ	0.98	2.59	3.535 (2)	160.9
C55—H55A···O1ⁱⁱ	0.98	2.61	3.536 (3)	158.1

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Acknowledgements

The authors thank Mr John Robbins for financial and logistical support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gade, L. H. (1998). Koordinationschemie, 1. Auflage, Weinheim: Wiley–VCH. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yumata, N., Gerber, T., Hosten, E. & Betz, R. (2011). Acta Cryst. E67, o2175. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 10| October 2011| Pages o2785-o2786

https://doi.org/10.1107/S1600536811039158

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-((E)-{2-[N-(1,5-Di­methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)carboximido­yl]benzyl­­idene}amino)-1,5-di­methyl-2-phenyl-2,3-di­hydro-1H-pyrazol-3-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-((E)-{2-[N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carboximidoyl]benzylidene}amino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one