1-{5-[4-(Hex­yloxy)phen­yl]-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl}ethanone

Abbas, A.; Hussain, S.; Hafeez, N.; Lo, K.M.; Hasan, A.

doi:10.1107/S1600536810033970

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2505

doi:10.1107/S1600536810033970

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1-{5-[4-(Hexyloxy)phenyl]-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl}ethanone

Asghar Abbas,^a ^* Safdar Hussain,^b Noureen Hafeez,^b Kong Mun Lo ^c and Aurangzeb Hasan ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bDepartment of Forensic Medicine & Toxicology, National University of Sciences & Technology, Islamabad, Pakistan, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: profazmi@hotmail.com

(Received 13 August 2010; accepted 23 August 2010; online 4 September 2010)

The crystal structure of the title compound, C₂₃H₂₈N₂O₂, is composed of discrete molecules with bond lengths and angles quite typical for pyrazoline derivatives of this class. The plane containing the pyrazoline unit is nearly planar with the mean plane of the phenyl ring at the 3-position, making a dihedral angle of 1.96 (3)°. The crystal packing is stabilized by weak C—H⋯π interactions involving both of the aromatic rings.

Related literature

For the biological activity and pharmacological properties of 2-pyrazoline derivatives, see: Cottineau et al. (2002 ); Dhal et al. (1975 ); Regaila et al. (1979 ); Rathish et al. (2009 ); Subbaramaiah et al. (2002 ); Manna et al. (2002 ). For the syntheses and crystal structures of 2-pyrazoline derivatives, see: Bai et al. (2009 ); Lu et al. (2008 ); Fahrni et al. (2003 ); Jian et al. (2008 ).

Experimental

Crystal data

C₂₃H₂₈N₂O₂
M_r = 364.47
Monoclinic, P 2₁ /c
a = 5.3937 (8) Å
b = 20.237 (3) Å
c = 18.163 (3) Å
β = 95.144 (2)°
V = 1974.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.3 × 0.2 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.675, T_max = 0.746
18731 measured reflections
4517 independent reflections
3430 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.103
S = 1.03
4517 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7–C12 and C16–C21 aromatic rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg2ⁱ	0.93	2.95	3.6252 (15)	131
C14—H14A⋯Cg2ⁱⁱ	0.97	2.63	3.5024 (14)	151
C19—H19⋯Cg1ⁱⁱⁱ	0.93	2.71	3.4299 (15)	135
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033970/zq2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810033970/zq2055Isup2.hkl

checkCIF report

Comment top

Pyrazoline systems are well known nitrogen-containing heterocyclic compounds which exhibit a wide range of biological activities and pharmacological properties such as anti-hyperglycemic (Cottineau et al., 2002), antifungal (Dhal et al., 1975), anti-diabetic, anaesthetic and analgesic properties (Regaila et al., 1979), anti-inflammation (Rathish et al., 2009), anticancer (Subbaramaiah et al., 2002), and monoamine oxidases inhibitors (Manna et al., 2002).

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit consists of discrete [PhCOCH₃C₆H₄C₃H₃N₂O(CH₂)₅CH₃] entities, devoid of any classical hydrogen bonds. All bond lengths and angles are in the normal range (Bai et al., 2009; Lu et al., 2008). In the pyrazolinyl ring, the C—N and C=N bond lengths of 1.4753 (17) and 1.2856 (17) are comparable with those in similar structures [C—N 1.482 (2)–1.515 (9) Å, C=N 1.291 (2)–1.300 (10) Å] (Fahrni et al., 2003). The N—N bond length of 1.3853 (15) is longer than in the structure of Jian et al. [N–N 1.373 (2)–1.380 (8) Å]. The plane containing the pyrazoline moiety is nearly planar with the mean plane of the phenyl ring C16–C21 making a dihedral angle of 1.96 (3)°.

The crystal packing is stabilized by weak C-H···π interactions involving both of the phenyl rings.

Related literature top

For the biological activity and pharmacological properties of 2-pyrazoline derivatives, see: Cottineau et al. (2002); Dhal et al. (1975); Regaila et al. (1979); Rathish et al. (2009); Subbaramaiah et al. (2002); Manna et al. (2002). For the syntheses and crystal structures of 2-pyrazoline derivatives, see: Bai et al. (2009); Lu et al. (2008); Fahrni et al. (2003); Jian et al. (2008).

Experimental top

A mixture of (E)-3-(4-(hexyloxy)phenyl)-1-phenylprop-2-en-1-one (3.08 g, 10 mmol) and hydrazine hydrate (1.0 g, 20 mmol) was taken in acetic acid (25 ml), and two drops of concentrated hydrochloric acid were added. The mixture was refluxed for 6 h. The precipitated solids were filtered, dried and recrystallized from ethanol. The single crystals were obtained from a mixture of ethyl acetate and dichloromethane by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

1-{5-[4-(Hexyloxy)phenyl]-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl}ethanone top

Crystal data top

C₂₃H₂₈N₂O₂	F(000) = 784
M_r = 364.47	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3895 reflections
a = 5.3937 (8) Å	θ = 2.3–28.1°
b = 20.237 (3) Å	µ = 0.08 mm⁻¹
c = 18.163 (3) Å	T = 100 K
β = 95.144 (2)°	Block, white
V = 1974.6 (5) Å³	0.3 × 0.2 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4517 independent reflections
Radiation source: fine-focus sealed tube	3430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
T_min = 0.675, T_max = 0.746	k = −25→26
18731 measured reflections	l = −23→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0466P)² + 0.4272P] where P = (F_o² + 2F_c²)/3
4517 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₂₈N₂O₂	V = 1974.6 (5) Å³
M_r = 364.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3937 (8) Å	µ = 0.08 mm⁻¹
b = 20.237 (3) Å	T = 100 K
c = 18.163 (3) Å	0.3 × 0.2 × 0.18 mm
β = 95.144 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4517 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3430 reflections with I > 2σ(I)
T_min = 0.675, T_max = 0.746	R_int = 0.042
18731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
4517 reflections	Δρ_min = −0.21 e Å⁻³
246 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.18742 (16)	0.45980 (5)	−0.05993 (5)	0.0179 (2)
O2	0.32678 (19)	0.17097 (5)	0.05044 (5)	0.0271 (2)
N1	0.1119 (2)	0.20218 (6)	0.14456 (6)	0.0191 (3)
N2	−0.0638 (2)	0.18796 (6)	0.19341 (6)	0.0179 (2)
C1	0.5550 (4)	0.54544 (9)	−0.39381 (9)	0.0418 (4)
H1A	0.4064	0.5562	−0.4245	0.063*
H1B	0.6700	0.5234	−0.4229	0.063*
H1C	0.6297	0.5852	−0.3734	0.063*
C2	0.4902 (3)	0.50039 (7)	−0.33153 (7)	0.0249 (3)
H2A	0.6419	0.4891	−0.3014	0.030*
H2B	0.4195	0.4598	−0.3526	0.030*
C3	0.3071 (3)	0.53097 (7)	−0.28225 (7)	0.0249 (3)
H3A	0.3774	0.5716	−0.2613	0.030*
H3B	0.1551	0.5421	−0.3123	0.030*
C4	0.2433 (3)	0.48570 (7)	−0.21971 (7)	0.0225 (3)
H4A	0.3943	0.4769	−0.1881	0.027*
H4B	0.1845	0.4439	−0.2408	0.027*
C5	0.0473 (3)	0.51279 (7)	−0.17220 (7)	0.0209 (3)
H5A	0.1100	0.5529	−0.1480	0.025*
H5B	−0.1010	0.5241	−0.2039	0.025*
C6	−0.0217 (2)	0.46428 (7)	−0.11418 (7)	0.0187 (3)
H6A	−0.1675	0.4796	−0.0916	0.022*
H6B	−0.0584	0.4214	−0.1363	0.022*
C7	0.1846 (2)	0.41158 (6)	−0.00717 (6)	0.0151 (3)
C8	−0.0066 (2)	0.36643 (7)	−0.00220 (7)	0.0165 (3)
H8	−0.1487	0.3685	−0.0351	0.020*
C9	0.0156 (2)	0.31812 (7)	0.05236 (7)	0.0167 (3)
H9	−0.1132	0.2880	0.0558	0.020*
C10	0.2267 (2)	0.31401 (6)	0.10170 (6)	0.0152 (3)
C11	0.4149 (2)	0.36037 (7)	0.09649 (7)	0.0168 (3)
H11	0.5562	0.3586	0.1298	0.020*
C12	0.3957 (2)	0.40882 (7)	0.04292 (7)	0.0165 (3)
H12	0.5230	0.4395	0.0402	0.020*
C13	0.2542 (2)	0.26318 (7)	0.16271 (7)	0.0173 (3)
H13	0.4306	0.2524	0.1742	0.021*
C14	0.1407 (2)	0.28567 (7)	0.23384 (7)	0.0174 (3)
H14A	0.2658	0.2871	0.2756	0.021*
H14B	0.0634	0.3288	0.2274	0.021*
C15	−0.0501 (2)	0.23286 (7)	0.24369 (7)	0.0160 (3)
C16	−0.2154 (2)	0.23144 (7)	0.30378 (7)	0.0163 (3)
C17	−0.3931 (2)	0.18129 (7)	0.30687 (7)	0.0177 (3)
H17	−0.4052	0.1482	0.2712	0.021*
C18	−0.5505 (2)	0.18075 (7)	0.36271 (7)	0.0194 (3)
H18	−0.6679	0.1473	0.3644	0.023*
C19	−0.5348 (2)	0.22987 (7)	0.41648 (7)	0.0193 (3)
H19	−0.6420	0.2295	0.4538	0.023*
C21	−0.1990 (2)	0.28018 (7)	0.35816 (7)	0.0193 (3)
H21	−0.0806	0.3135	0.3571	0.023*
C20	−0.3591 (3)	0.27924 (7)	0.41409 (7)	0.0199 (3)
H20	−0.3478	0.3121	0.4501	0.024*
C22	0.1542 (3)	0.16031 (7)	0.08809 (7)	0.0209 (3)
C23	−0.0247 (3)	0.10362 (7)	0.07542 (8)	0.0259 (3)
H23A	0.0172	0.0784	0.0335	0.039*
H23B	−0.1911	0.1204	0.0662	0.039*
H23C	−0.0145	0.0758	0.1184	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0188 (5)	0.0165 (5)	0.0177 (4)	−0.0025 (4)	−0.0017 (3)	0.0030 (4)
O2	0.0332 (6)	0.0255 (6)	0.0248 (5)	0.0035 (5)	0.0155 (4)	0.0011 (4)
N1	0.0223 (6)	0.0178 (6)	0.0185 (5)	−0.0017 (5)	0.0093 (4)	0.0004 (4)
N2	0.0189 (6)	0.0197 (6)	0.0160 (5)	0.0009 (5)	0.0067 (4)	0.0018 (4)
C1	0.0560 (12)	0.0388 (11)	0.0334 (8)	0.0093 (9)	0.0187 (8)	0.0104 (8)
C2	0.0299 (8)	0.0235 (8)	0.0209 (7)	−0.0010 (6)	0.0005 (6)	0.0014 (6)
C3	0.0329 (8)	0.0212 (8)	0.0205 (6)	−0.0001 (6)	0.0010 (6)	0.0028 (6)
C4	0.0271 (8)	0.0209 (8)	0.0194 (6)	0.0007 (6)	0.0005 (5)	0.0018 (5)
C5	0.0247 (7)	0.0179 (7)	0.0191 (6)	0.0021 (6)	−0.0026 (5)	0.0009 (5)
C6	0.0179 (7)	0.0187 (7)	0.0187 (6)	0.0010 (5)	−0.0024 (5)	−0.0003 (5)
C7	0.0168 (6)	0.0146 (7)	0.0145 (6)	0.0021 (5)	0.0038 (5)	−0.0007 (5)
C8	0.0138 (6)	0.0193 (7)	0.0163 (6)	0.0009 (5)	0.0021 (5)	−0.0024 (5)
C9	0.0147 (6)	0.0187 (7)	0.0175 (6)	−0.0023 (5)	0.0060 (5)	−0.0016 (5)
C10	0.0163 (6)	0.0156 (7)	0.0145 (6)	0.0012 (5)	0.0061 (5)	−0.0005 (5)
C11	0.0145 (6)	0.0217 (7)	0.0144 (6)	0.0013 (5)	0.0023 (5)	−0.0015 (5)
C12	0.0142 (6)	0.0179 (7)	0.0179 (6)	−0.0027 (5)	0.0041 (5)	−0.0012 (5)
C13	0.0167 (7)	0.0189 (7)	0.0168 (6)	0.0010 (5)	0.0040 (5)	0.0015 (5)
C14	0.0186 (7)	0.0184 (7)	0.0156 (6)	−0.0004 (5)	0.0041 (5)	0.0017 (5)
C15	0.0155 (6)	0.0169 (7)	0.0159 (6)	0.0022 (5)	0.0017 (5)	0.0028 (5)
C16	0.0158 (6)	0.0190 (7)	0.0144 (6)	0.0026 (5)	0.0022 (5)	0.0031 (5)
C17	0.0188 (7)	0.0178 (7)	0.0165 (6)	0.0014 (5)	0.0012 (5)	−0.0006 (5)
C18	0.0190 (7)	0.0207 (7)	0.0190 (6)	−0.0014 (6)	0.0036 (5)	0.0035 (5)
C19	0.0185 (7)	0.0240 (8)	0.0160 (6)	0.0039 (6)	0.0057 (5)	0.0042 (5)
C21	0.0191 (7)	0.0188 (7)	0.0201 (6)	−0.0018 (6)	0.0026 (5)	0.0013 (5)
C20	0.0241 (7)	0.0205 (7)	0.0154 (6)	0.0021 (6)	0.0038 (5)	−0.0006 (5)
C22	0.0270 (8)	0.0194 (8)	0.0172 (6)	0.0053 (6)	0.0066 (5)	0.0024 (5)
C23	0.0345 (8)	0.0225 (8)	0.0214 (7)	0.0005 (6)	0.0066 (6)	−0.0027 (6)

Geometric parameters (Å, º) top

O1—C7	1.3688 (15)	C9—C10	1.3867 (17)
O1—C6	1.4325 (14)	C9—H9	0.9300
O2—C22	1.2226 (17)	C10—C11	1.3918 (18)
N1—C22	1.3652 (17)	C10—C13	1.5094 (17)
N1—N2	1.3853 (15)	C11—C12	1.3786 (18)
N1—C13	1.4753 (17)	C11—H11	0.9300
N2—C15	1.2856 (17)	C12—H12	0.9300
C1—C2	1.518 (2)	C13—C14	1.5471 (17)
C1—H1A	0.9600	C13—H13	0.9800
C1—H1B	0.9600	C14—C15	1.5054 (18)
C1—H1C	0.9600	C14—H14A	0.9700
C2—C3	1.523 (2)	C14—H14B	0.9700
C2—H2A	0.9700	C15—C16	1.4701 (17)
C2—H2B	0.9700	C16—C21	1.3932 (18)
C3—C4	1.5225 (19)	C16—C17	1.4008 (19)
C3—H3A	0.9700	C17—C18	1.3795 (18)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.525 (2)	C18—C19	1.3906 (19)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—C20	1.380 (2)
C5—C6	1.5109 (19)	C19—H19	0.9300
C5—H5A	0.9700	C21—C20	1.3912 (18)
C5—H5B	0.9700	C21—H21	0.9300
C6—H6A	0.9700	C20—H20	0.9300
C6—H6B	0.9700	C22—C23	1.504 (2)
C7—C8	1.3868 (18)	C23—H23A	0.9600
C7—C12	1.3934 (17)	C23—H23B	0.9600
C8—C9	1.3896 (18)	C23—H23C	0.9600
C8—H8	0.9300

C7—O1—C6	117.98 (10)	C9—C10—C13	122.44 (12)
C22—N1—N2	121.49 (11)	C11—C10—C13	119.01 (11)
C22—N1—C13	124.64 (11)	C12—C11—C10	121.22 (12)
N2—N1—C13	113.75 (10)	C12—C11—H11	119.4
C15—N2—N1	108.01 (11)	C10—C11—H11	119.4
C2—C1—H1A	109.5	C11—C12—C7	119.64 (12)
C2—C1—H1B	109.5	C11—C12—H12	120.2
H1A—C1—H1B	109.5	C7—C12—H12	120.2
C2—C1—H1C	109.5	N1—C13—C10	113.03 (10)
H1A—C1—H1C	109.5	N1—C13—C14	101.29 (10)
H1B—C1—H1C	109.5	C10—C13—C14	113.09 (11)
C1—C2—C3	113.51 (13)	N1—C13—H13	109.7
C1—C2—H2A	108.9	C10—C13—H13	109.7
C3—C2—H2A	108.9	C14—C13—H13	109.7
C1—C2—H2B	108.9	C15—C14—C13	102.50 (10)
C3—C2—H2B	108.9	C15—C14—H14A	111.3
H2A—C2—H2B	107.7	C13—C14—H14A	111.3
C4—C3—C2	113.33 (12)	C15—C14—H14B	111.3
C4—C3—H3A	108.9	C13—C14—H14B	111.3
C2—C3—H3A	108.9	H14A—C14—H14B	109.2
C4—C3—H3B	108.9	N2—C15—C16	120.89 (12)
C2—C3—H3B	108.9	N2—C15—C14	114.44 (11)
H3A—C3—H3B	107.7	C16—C15—C14	124.65 (11)
C3—C4—C5	114.86 (12)	C21—C16—C17	118.99 (12)
C3—C4—H4A	108.6	C21—C16—C15	120.56 (12)
C5—C4—H4A	108.6	C17—C16—C15	120.45 (12)
C3—C4—H4B	108.6	C18—C17—C16	120.23 (12)
C5—C4—H4B	108.6	C18—C17—H17	119.9
H4A—C4—H4B	107.5	C16—C17—H17	119.9
C6—C5—C4	112.80 (12)	C17—C18—C19	120.54 (13)
C6—C5—H5A	109.0	C17—C18—H18	119.7
C4—C5—H5A	109.0	C19—C18—H18	119.7
C6—C5—H5B	109.0	C20—C19—C18	119.61 (12)
C4—C5—H5B	109.0	C20—C19—H19	120.2
H5A—C5—H5B	107.8	C18—C19—H19	120.2
O1—C6—C5	107.04 (10)	C20—C21—C16	120.27 (13)
O1—C6—H6A	110.3	C20—C21—H21	119.9
C5—C6—H6A	110.3	C16—C21—H21	119.9
O1—C6—H6B	110.3	C19—C20—C21	120.37 (13)
C5—C6—H6B	110.3	C19—C20—H20	119.8
H6A—C6—H6B	108.6	C21—C20—H20	119.8
O1—C7—C8	124.77 (11)	O2—C22—N1	119.85 (13)
O1—C7—C12	115.21 (11)	O2—C22—C23	124.01 (12)
C8—C7—C12	120.00 (12)	N1—C22—C23	116.12 (12)
C7—C8—C9	119.52 (12)	C22—C23—H23A	109.5
C7—C8—H8	120.2	C22—C23—H23B	109.5
C9—C8—H8	120.2	H23A—C23—H23B	109.5
C10—C9—C8	121.11 (12)	C22—C23—H23C	109.5
C10—C9—H9	119.4	H23A—C23—H23C	109.5
C8—C9—H9	119.4	H23B—C23—H23C	109.5
C9—C10—C11	118.49 (12)

C22—N1—N2—C15	175.04 (12)	C9—C10—C13—C14	−86.17 (15)
C13—N1—N2—C15	−1.30 (14)	C11—C10—C13—C14	91.00 (14)
C1—C2—C3—C4	−179.80 (13)	N1—C13—C14—C15	−0.22 (12)
C2—C3—C4—C5	−176.14 (12)	C10—C13—C14—C15	121.03 (11)
C3—C4—C5—C6	176.22 (11)	N1—N2—C15—C16	179.74 (11)
C7—O1—C6—C5	−170.59 (10)	N1—N2—C15—C14	1.13 (15)
C4—C5—C6—O1	70.78 (14)	C13—C14—C15—N2	−0.55 (14)
C6—O1—C7—C8	−0.01 (18)	C13—C14—C15—C16	−179.10 (11)
C6—O1—C7—C12	178.57 (11)	N2—C15—C16—C21	179.85 (12)
O1—C7—C8—C9	177.70 (12)	C14—C15—C16—C21	−1.68 (19)
C12—C7—C8—C9	−0.81 (19)	N2—C15—C16—C17	−0.64 (18)
C7—C8—C9—C10	−0.41 (19)	C14—C15—C16—C17	177.82 (12)
C8—C9—C10—C11	1.34 (19)	C21—C16—C17—C18	0.53 (19)
C8—C9—C10—C13	178.52 (12)	C15—C16—C17—C18	−178.98 (12)
C9—C10—C11—C12	−1.08 (19)	C16—C17—C18—C19	0.04 (19)
C13—C10—C11—C12	−178.36 (12)	C17—C18—C19—C20	−0.43 (19)
C10—C11—C12—C7	−0.12 (19)	C17—C16—C21—C20	−0.71 (19)
O1—C7—C12—C11	−177.58 (11)	C15—C16—C21—C20	178.80 (12)
C8—C7—C12—C11	1.07 (19)	C18—C19—C20—C21	0.2 (2)
C22—N1—C13—C10	63.40 (16)	C16—C21—C20—C19	0.3 (2)
N2—N1—C13—C10	−120.39 (12)	N2—N1—C22—O2	−172.82 (12)
C22—N1—C13—C14	−175.30 (12)	C13—N1—C22—O2	3.1 (2)
N2—N1—C13—C14	0.90 (13)	N2—N1—C22—C23	8.60 (18)
C9—C10—C13—N1	28.19 (17)	C13—N1—C22—C23	−175.47 (12)
C11—C10—C13—N1	−154.64 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C7–C12 and C16–C21 aromatic rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg2ⁱ	0.93	2.95	3.6252 (15)	131
C14—H14A···Cg2ⁱⁱ	0.97	2.63	3.5024 (14)	151
C19—H19···Cg1ⁱⁱⁱ	0.93	2.71	3.4299 (15)	135

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) x+1, y, z; (iii) x−1, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₈N₂O₂
M_r	364.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.3937 (8), 20.237 (3), 18.163 (3)
β (°)	95.144 (2)
V (Å³)	1974.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.2 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.675, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	18731, 4517, 3430
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.103, 1.03
No. of reflections	4517
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C7–C12 and C16–C21 aromatic rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg2ⁱ	0.93	2.95	3.6252 (15)	131
C14—H14A···Cg2ⁱⁱ	0.97	2.63	3.5024 (14)	151
C19—H19···Cg1ⁱⁱⁱ	0.93	2.71	3.4299 (15)	135

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) x+1, y, z; (iii) x−1, −y−1/2, z−1/2.

Acknowledgements

AA is grateful to the HEC-Pakistan for financial support for his PhD program under scholarship No. [IIC–0317109].

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