(2E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-phenyl­prop-2-en-1-one

Fun, H.-K.; Hemamalini, M.; Malladi, S.; Poojari, P.; Isloor, A.M.

doi:10.1107/S1600536811023282

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1745-o1746

doi:10.1107/S1600536811023282

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(2E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Shridhar Malladi,^b Pradeep Poojari ^b and Arun M Isloor ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, National Institute of Technology, Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 14 June 2011; accepted 15 June 2011; online 18 June 2011)

In the title compound, C₂₄H₁₈N₂O, the pyrazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 18.07 (4), 48.60 (4) and 9.13 (5)° with the phenyl rings. In the crystal, adjacent molecules are connected via intermolecular C—H⋯O hydrogen bonds, forming dimers. Furthermore, the crystal structure is stabilized by weak C—H⋯π and π–π interactions, with centroid–centroid distances of 3.6808 (5) Å.

Related literature

For applications of pyrazoles, see: Patel et al. (2004 ); Isloor et al. (2009 ); Vijesh et al. (2010 ); Sharma et al. (2010 ); Rostom et al. (2003 ); Ghorab et al. (2010 ); Amnekar & Bhusari (2010 ). For the synthetic procedure, see: Sharma et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₄H₁₈N₂O
M_r = 350.40
Triclinic, $[P \overline 1]$
a = 8.1027 (2) Å
b = 9.3157 (2) Å
c = 12.9634 (3) Å
α = 73.630 (1)°
β = 74.713 (1)°
γ = 74.820 (1)°
V = 886.83 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.66 × 0.23 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.949, T_max = 0.988
27273 measured reflections
7371 independent reflections
6190 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.131
S = 1.04
7371 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C20–C25 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.95	2.27	3.2019 (11)	167
C15—H15A⋯Cg2ⁱⁱ	0.95	2.81	3.6171 (9)	143
C2—H2A⋯Cg3ⁱⁱⁱ	0.95	2.63	3.4304 (9)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023282/rz2615sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023282/rz2615Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023282/rz2615Isup3.cml

checkCIF report

Comment top

Pyrazoles are a novel class of heterocyclic compounds possessing wide variety of applications in the agrochemical and pharmaceutical industries (Patel et al., 2004). Derivatives of pyrazoles are found to show good antibacterial (Isloor et al., 2009; Vijesh et al., 2010), anti-inflammatory (Sharma et al., 2010), analgesic (Rostom et al., 2003), anticancer, radioprotective (Ghorab et al., 2010) and anti-convulsant activities (Amnekar et al., 2010). Prompted by these diverse activities of pyrazole derivatives, we have synthesized the title compound to study its crystal structure.

In the title compound (Fig. 1), the pyrazole (N1/N2/C10–C12) group is essentially planar, with a maximum deviation of 0.004 (1) Å for atom C12, and makes dihedral angles of 18.07 (4)°, 48.60 (4)° and 9.13 (5)° with the adjacent C1–C6, C13–C18) and C19–C24 phenyl rings, respectively.

In the crystal structure (Fig. 2), adjacent molecules are connected via intermolecular C12—H12A···O1 (Table 1) hydrogen bonds forming dimers. Furthermore, the crystal structure is stabilized by weak π–π interactions between the pyrazole (N1/N2/C10–C12) and phenyl (C19–C24) rings [Cg···Cg = 3.6808 (5) Å; -x, 2-y, 1-z] and C—H···π (Table 1) interactions, involving the centroids of the C20–C25 (Cg2) and C13–C18 (Cg3) rings.

Related literature top

For applications of pyrazoles, see: Patel et al. (2004); Isloor et al. (2009); Vijesh et al. (2010); Sharma et al. (2010); Rostom et al. (2003); Ghorab et al. (2010); Amnekar et al. (2010). For the synthetic procedure, see: Sharma et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a cold stirred mixture of methanol (20 ml) and sodium hydroxide (12.09 mmol) was added acetophenone (4.03 mmol). The reaction mixture was stirred for 10 min. To this solution was added formyl pyrazole (4.03 mmol) followed by tetrahydrofuran (30 ml). The solution was further stirred for 2 h at 0 °C and then at room temperature for 5 h. It was then poured into ice cold water. The resulting solution was neutralized with diluted HCl. The solid that separated out was filtered, washed with water, dried and crystallized from ethanol. Yield: 1.15 g, 81.5 %. M. p.: 406–408 K (Sharma et al., 2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008; molecular graphics: SHELXTL (Sheldrick, 2008; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

(2E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one top

Crystal data top

C₂₄H₁₈N₂O	Z = 2
M_r = 350.40	F(000) = 368
Triclinic, P1	D_x = 1.312 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1027 (2) Å	Cell parameters from 9964 reflections
b = 9.3157 (2) Å	θ = 2.3–34.3°
c = 12.9634 (3) Å	µ = 0.08 mm⁻¹
α = 73.630 (1)°	T = 100 K
β = 74.713 (1)°	Block, colourless
γ = 74.820 (1)°	0.66 × 0.23 × 0.16 mm
V = 886.83 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7371 independent reflections
Radiation source: fine-focus sealed tube	6190 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 34.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.949, T_max = 0.988	k = −14→14
27273 measured reflections	l = −20→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0751P)² + 0.1576P] where P = (F_o² + 2F_c²)/3
7371 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₁₈N₂O	γ = 74.820 (1)°
M_r = 350.40	V = 886.83 (4) Å³
Triclinic, P1	Z = 2
a = 8.1027 (2) Å	Mo Kα radiation
b = 9.3157 (2) Å	µ = 0.08 mm⁻¹
c = 12.9634 (3) Å	T = 100 K
α = 73.630 (1)°	0.66 × 0.23 × 0.16 mm
β = 74.713 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7371 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6190 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.988	R_int = 0.024
27273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
7371 reflections	Δρ_min = −0.30 e Å⁻³
244 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
O1	0.62674 (8)	0.29923 (7)	0.35790 (5)	0.02264 (13)
N1	−0.05079 (9)	0.77669 (8)	0.50245 (5)	0.01568 (12)
N2	−0.12324 (9)	0.77040 (8)	0.42026 (5)	0.01623 (12)
C1	0.70994 (10)	0.10968 (9)	0.21010 (6)	0.01851 (14)
H1A	0.7701	0.0780	0.2690	0.022*
C2	0.75836 (11)	0.02845 (9)	0.12812 (7)	0.02144 (15)
H2A	0.8514	−0.0584	0.1312	0.026*
C3	0.67086 (12)	0.07414 (10)	0.04162 (7)	0.02281 (16)
H3A	0.7029	0.0177	−0.0137	0.027*
C4	0.53661 (12)	0.20236 (11)	0.03622 (7)	0.02424 (16)
H4A	0.4781	0.2345	−0.0235	0.029*
C5	0.48746 (11)	0.28408 (10)	0.11820 (7)	0.02067 (15)
H5A	0.3953	0.3716	0.1142	0.025*
C6	0.57315 (10)	0.23783 (8)	0.20632 (6)	0.01585 (13)
C7	0.52409 (10)	0.31976 (8)	0.29762 (6)	0.01587 (13)
C8	0.35228 (10)	0.42396 (9)	0.31234 (6)	0.01641 (13)
H8A	0.2708	0.4290	0.2698	0.020*
C9	0.31000 (10)	0.51223 (9)	0.38577 (6)	0.01634 (13)
H9A	0.3974	0.5030	0.4251	0.020*
C10	0.14917 (10)	0.61871 (8)	0.41212 (6)	0.01493 (12)
C11	−0.00317 (10)	0.67559 (8)	0.36519 (6)	0.01476 (12)
C12	0.11129 (10)	0.68879 (8)	0.49939 (6)	0.01588 (13)
H12A	0.1858	0.6770	0.5481	0.019*
C13	−0.04028 (10)	0.65220 (8)	0.26639 (6)	0.01507 (12)
C14	0.08119 (10)	0.67017 (9)	0.16654 (6)	0.01730 (13)
H14A	0.1920	0.6890	0.1640	0.021*
C15	0.04095 (11)	0.66063 (9)	0.07101 (6)	0.02009 (14)
H15A	0.1240	0.6731	0.0037	0.024*
C16	−0.12143 (12)	0.63272 (10)	0.07439 (7)	0.02177 (15)
H16A	−0.1498	0.6271	0.0092	0.026*
C17	−0.24183 (11)	0.61317 (9)	0.17338 (7)	0.02090 (15)
H17A	−0.3518	0.5928	0.1758	0.025*
C18	−0.20240 (10)	0.62324 (9)	0.26905 (6)	0.01804 (14)
H18A	−0.2858	0.6104	0.3362	0.022*
C19	−0.14395 (10)	0.87250 (9)	0.57610 (6)	0.01661 (13)
C20	−0.29759 (11)	0.97422 (9)	0.55476 (7)	0.01987 (14)
H20A	−0.3394	0.9800	0.4915	0.024*
C21	−0.38932 (12)	1.06744 (10)	0.62720 (7)	0.02283 (16)
H21A	−0.4949	1.1362	0.6136	0.027*
C22	−0.32750 (12)	1.06055 (10)	0.71912 (8)	0.02431 (17)
H22A	−0.3906	1.1241	0.7684	0.029*
C23	−0.17285 (12)	0.96010 (12)	0.73845 (8)	0.02685 (18)
H23A	−0.1295	0.9565	0.8007	0.032*
C24	−0.08031 (11)	0.86448 (11)	0.66779 (7)	0.02333 (16)
H24A	0.0245	0.7949	0.6820	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0202 (3)	0.0266 (3)	0.0242 (3)	0.0010 (2)	−0.0109 (2)	−0.0099 (2)
N1	0.0156 (3)	0.0183 (3)	0.0144 (3)	−0.0022 (2)	−0.0034 (2)	−0.0065 (2)
N2	0.0160 (3)	0.0189 (3)	0.0151 (3)	−0.0022 (2)	−0.0045 (2)	−0.0059 (2)
C1	0.0177 (3)	0.0176 (3)	0.0184 (3)	0.0004 (2)	−0.0047 (2)	−0.0039 (2)
C2	0.0221 (4)	0.0182 (3)	0.0214 (3)	0.0009 (3)	−0.0033 (3)	−0.0062 (3)
C3	0.0245 (4)	0.0245 (4)	0.0203 (3)	−0.0032 (3)	−0.0022 (3)	−0.0103 (3)
C4	0.0233 (4)	0.0310 (4)	0.0191 (3)	−0.0001 (3)	−0.0069 (3)	−0.0093 (3)
C5	0.0184 (3)	0.0238 (4)	0.0193 (3)	0.0014 (3)	−0.0069 (3)	−0.0066 (3)
C6	0.0149 (3)	0.0161 (3)	0.0163 (3)	−0.0012 (2)	−0.0042 (2)	−0.0042 (2)
C7	0.0152 (3)	0.0157 (3)	0.0169 (3)	−0.0017 (2)	−0.0048 (2)	−0.0040 (2)
C8	0.0144 (3)	0.0171 (3)	0.0183 (3)	−0.0010 (2)	−0.0046 (2)	−0.0056 (2)
C9	0.0148 (3)	0.0180 (3)	0.0166 (3)	−0.0020 (2)	−0.0041 (2)	−0.0050 (2)
C10	0.0144 (3)	0.0158 (3)	0.0152 (3)	−0.0024 (2)	−0.0035 (2)	−0.0046 (2)
C11	0.0151 (3)	0.0156 (3)	0.0140 (3)	−0.0028 (2)	−0.0035 (2)	−0.0036 (2)
C12	0.0152 (3)	0.0180 (3)	0.0153 (3)	−0.0025 (2)	−0.0036 (2)	−0.0054 (2)
C13	0.0157 (3)	0.0149 (3)	0.0151 (3)	−0.0014 (2)	−0.0049 (2)	−0.0042 (2)
C14	0.0170 (3)	0.0189 (3)	0.0161 (3)	−0.0016 (2)	−0.0040 (2)	−0.0054 (2)
C15	0.0225 (3)	0.0214 (3)	0.0162 (3)	0.0002 (3)	−0.0047 (3)	−0.0076 (3)
C16	0.0265 (4)	0.0213 (3)	0.0207 (3)	−0.0010 (3)	−0.0099 (3)	−0.0087 (3)
C17	0.0226 (4)	0.0206 (3)	0.0231 (4)	−0.0050 (3)	−0.0104 (3)	−0.0048 (3)
C18	0.0180 (3)	0.0190 (3)	0.0182 (3)	−0.0039 (2)	−0.0060 (3)	−0.0037 (2)
C19	0.0165 (3)	0.0183 (3)	0.0160 (3)	−0.0045 (2)	−0.0007 (2)	−0.0070 (2)
C20	0.0200 (3)	0.0191 (3)	0.0196 (3)	−0.0020 (3)	−0.0025 (3)	−0.0065 (3)
C21	0.0220 (4)	0.0198 (3)	0.0249 (4)	−0.0023 (3)	0.0004 (3)	−0.0089 (3)
C22	0.0237 (4)	0.0251 (4)	0.0257 (4)	−0.0073 (3)	0.0036 (3)	−0.0140 (3)
C23	0.0239 (4)	0.0377 (5)	0.0240 (4)	−0.0064 (3)	−0.0012 (3)	−0.0182 (3)
C24	0.0198 (4)	0.0321 (4)	0.0212 (4)	−0.0022 (3)	−0.0038 (3)	−0.0143 (3)

Geometric parameters (Å, º) top

O1—C7	1.2305 (9)	C11—C13	1.4742 (10)
N1—C12	1.3508 (10)	C12—H12A	0.9500
N1—N2	1.3661 (8)	C13—C18	1.3985 (11)
N1—C19	1.4232 (9)	C13—C14	1.4016 (11)
N2—C11	1.3325 (10)	C14—C15	1.3921 (10)
C1—C2	1.3906 (11)	C14—H14A	0.9500
C1—C6	1.3995 (11)	C15—C16	1.3939 (12)
C1—H1A	0.9500	C15—H15A	0.9500
C2—C3	1.3904 (12)	C16—C17	1.3903 (13)
C2—H2A	0.9500	C16—H16A	0.9500
C3—C4	1.3883 (13)	C17—C18	1.3926 (11)
C3—H3A	0.9500	C17—H17A	0.9500
C4—C5	1.3935 (11)	C18—H18A	0.9500
C4—H4A	0.9500	C19—C24	1.3918 (11)
C5—C6	1.3989 (11)	C19—C20	1.3930 (11)
C5—H5A	0.9500	C20—C21	1.3936 (11)
C6—C7	1.4978 (10)	C20—H20A	0.9500
C7—C8	1.4742 (11)	C21—C22	1.3892 (13)
C8—C9	1.3496 (10)	C21—H21A	0.9500
C8—H8A	0.9500	C22—C23	1.3885 (14)
C9—C10	1.4416 (10)	C22—H22A	0.9500
C9—H9A	0.9500	C23—C24	1.3937 (12)
C10—C12	1.3886 (10)	C23—H23A	0.9500
C10—C11	1.4305 (10)	C24—H24A	0.9500

C12—N1—N2	111.99 (6)	N1—C12—H12A	126.2
C12—N1—C19	127.99 (6)	C10—C12—H12A	126.2
N2—N1—C19	119.98 (6)	C18—C13—C14	119.08 (7)
C11—N2—N1	105.17 (6)	C18—C13—C11	120.35 (7)
C2—C1—C6	120.43 (7)	C14—C13—C11	120.39 (7)
C2—C1—H1A	119.8	C15—C14—C13	120.62 (7)
C6—C1—H1A	119.8	C15—C14—H14A	119.7
C3—C2—C1	120.10 (7)	C13—C14—H14A	119.7
C3—C2—H2A	119.9	C14—C15—C16	119.86 (8)
C1—C2—H2A	119.9	C14—C15—H15A	120.1
C4—C3—C2	119.96 (7)	C16—C15—H15A	120.1
C4—C3—H3A	120.0	C17—C16—C15	119.82 (7)
C2—C3—H3A	120.0	C17—C16—H16A	120.1
C3—C4—C5	120.16 (8)	C15—C16—H16A	120.1
C3—C4—H4A	119.9	C16—C17—C18	120.51 (7)
C5—C4—H4A	119.9	C16—C17—H17A	119.7
C4—C5—C6	120.30 (7)	C18—C17—H17A	119.7
C4—C5—H5A	119.8	C17—C18—C13	120.11 (7)
C6—C5—H5A	119.8	C17—C18—H18A	119.9
C5—C6—C1	119.04 (7)	C13—C18—H18A	119.9
C5—C6—C7	122.63 (7)	C24—C19—C20	120.83 (7)
C1—C6—C7	118.34 (6)	C24—C19—N1	119.87 (7)
O1—C7—C8	121.76 (7)	C20—C19—N1	119.30 (7)
O1—C7—C6	119.81 (7)	C19—C20—C21	119.29 (8)
C8—C7—C6	118.43 (6)	C19—C20—H20A	120.4
C9—C8—C7	120.44 (7)	C21—C20—H20A	120.4
C9—C8—H8A	119.8	C22—C21—C20	120.50 (8)
C7—C8—H8A	119.8	C22—C21—H21A	119.7
C8—C9—C10	128.27 (7)	C20—C21—H21A	119.7
C8—C9—H9A	115.9	C23—C22—C21	119.52 (8)
C10—C9—H9A	115.9	C23—C22—H22A	120.2
C12—C10—C11	103.95 (6)	C21—C22—H22A	120.2
C12—C10—C9	123.14 (7)	C22—C23—C24	120.88 (8)
C11—C10—C9	132.89 (7)	C22—C23—H23A	119.6
N2—C11—C10	111.32 (6)	C24—C23—H23A	119.6
N2—C11—C13	117.90 (6)	C19—C24—C23	118.96 (8)
C10—C11—C13	130.69 (7)	C19—C24—H24A	120.5
N1—C12—C10	107.56 (6)	C23—C24—H24A	120.5

C12—N1—N2—C11	0.28 (8)	C11—C10—C12—N1	0.79 (8)
C19—N1—N2—C11	178.30 (7)	C9—C10—C12—N1	−178.05 (7)
C6—C1—C2—C3	−0.03 (13)	N2—C11—C13—C18	−47.06 (10)
C1—C2—C3—C4	0.94 (13)	C10—C11—C13—C18	136.80 (8)
C2—C3—C4—C5	−1.00 (14)	N2—C11—C13—C14	128.07 (8)
C3—C4—C5—C6	0.15 (14)	C10—C11—C13—C14	−48.06 (11)
C4—C5—C6—C1	0.76 (12)	C18—C13—C14—C15	0.52 (11)
C4—C5—C6—C7	−179.03 (8)	C11—C13—C14—C15	−174.68 (7)
C2—C1—C6—C5	−0.82 (12)	C13—C14—C15—C16	−0.10 (12)
C2—C1—C6—C7	178.98 (7)	C14—C15—C16—C17	−0.59 (12)
C5—C6—C7—O1	−162.50 (8)	C15—C16—C17—C18	0.85 (12)
C1—C6—C7—O1	17.72 (11)	C16—C17—C18—C13	−0.43 (12)
C5—C6—C7—C8	17.37 (11)	C14—C13—C18—C17	−0.26 (11)
C1—C6—C7—C8	−162.41 (7)	C11—C13—C18—C17	174.95 (7)
O1—C7—C8—C9	6.89 (12)	C12—N1—C19—C24	−10.42 (12)
C6—C7—C8—C9	−172.98 (7)	N2—N1—C19—C24	171.91 (7)
C7—C8—C9—C10	−179.26 (7)	C12—N1—C19—C20	169.10 (8)
C8—C9—C10—C12	171.25 (8)	N2—N1—C19—C20	−8.57 (11)
C8—C9—C10—C11	−7.21 (14)	C24—C19—C20—C21	−0.83 (12)
N1—N2—C11—C10	0.25 (8)	N1—C19—C20—C21	179.65 (7)
N1—N2—C11—C13	−176.60 (6)	C19—C20—C21—C22	0.74 (13)
C12—C10—C11—N2	−0.66 (9)	C20—C21—C22—C23	0.16 (13)
C9—C10—C11—N2	178.01 (8)	C21—C22—C23—C24	−1.00 (14)
C12—C10—C11—C13	175.68 (8)	C20—C19—C24—C23	0.02 (13)
C9—C10—C11—C13	−5.65 (14)	N1—C19—C24—C23	179.53 (8)
N2—N1—C12—C10	−0.70 (9)	C22—C23—C24—C19	0.91 (14)
C19—N1—C12—C10	−178.53 (7)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C20–C25 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.95	2.27	3.2019 (11)	167
C15—H15A···Cg2ⁱⁱ	0.95	2.81	3.6171 (9)	143
C2—H2A···Cg3ⁱⁱⁱ	0.95	2.63	3.4304 (9)	143

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈N₂O
M_r	350.40
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.1027 (2), 9.3157 (2), 12.9634 (3)
α, β, γ (°)	73.630 (1), 74.713 (1), 74.820 (1)
V (Å³)	886.83 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.66 × 0.23 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.949, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	27273, 7371, 6190
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.794

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.131, 1.04
No. of reflections	7371
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008 and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C20–C25 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.95	2.27	3.2019 (11)	167
C15—H15A···Cg2ⁱⁱ	0.95	2.81	3.6171 (9)	143
C2—H2A···Cg3ⁱⁱⁱ	0.95	2.63	3.4304 (9)	143

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young Scientist's award.

References

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Volume 67| Part 7| July 2011| Pages o1745-o1746

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