1-Benzyl-2-(4-chloro­phen­yl)-4,5-di­phenyl-1H-imidazole

Ghoranneviss, M.; Mohammadi Ziarani, G.; Abbasi, A.; Hantehzadeh, M.R.; Farahani, Z.

doi:10.1107/S1600536808016802

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1233

doi:10.1107/S1600536808016802

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1-Benzyl-2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazole

Mahmood Ghoranneviss,^a Ghodsi Mohammadi Ziarani,^b Alireza Abbasi,^c ^* Mohammad Reza Hantehzadeh ^a and Zahra Farahani ^b

^aPlasma Physics Research Center, Science & Reseach Campus, Islamic Azad University, Tehran, Iran, ^bDepartment of Chemistry, University of Alzahra, Tehran, Iran, and ^cSchool of Chemistry, University College of Science, University of Tehran, Tehran, Iran
^*Correspondence e-mail: aabbasi@khayam.ut.ac.ir

(Received 20 May 2008; accepted 2 June 2008; online 7 June 2008)

The molecular conformation of the title compound, C₂₈H₂₁ClN₂, is stabilized by an intramolecular C—H⋯N hydrogen bond. It has many pharmacological properties, such as being an inhibitor of P38 MAP Kinase, and can play an important role in biochemical processes.

Related literature

For related structures and properties, see: Balalaie et al. (2003 ); Nagarapu et al. (2007 ); Kidwai et al. (2007 ).

Experimental

Crystal data

C₂₈H₂₁ClN₂
M_r = 420.92
Triclinic, $[P \overline 1]$
a = 7.4880 (11) Å
b = 9.2711 (16) Å
c = 16.049 (3) Å
α = 87.169 (13)°
β = 76.704 (12)°
γ = 87.842 (13)°
V = 1082.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 290 (2) K
0.3 × 0.2 × 0.2 mm

Data collection

STOE IPDS-II diffractometer
Absorption correction: none
8769 measured reflections
4246 independent reflections
2814 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.090
S = 0.94
4246 reflections
288 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1	0.93	2.56	2.874 (2)	100

Data collection: X-AREA (Stoe & Cie, 1997 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, 1. DOI: 10.1107/S1600536808016802/bt2715sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016802/bt2715Isup2.hkl

checkCIF report

Comment top

The synthesis, reactions and biological properties of substituted imidazole constitutes a significant part of modern heterocyclic chemistry. Compounds containing an imidazole ring system have many pharmacological properties and play important roles in biochemical processes. Many of substituted diaryl imidazoles are known as inhibitors of P38 MAP Kinase (Balalaie, et al., 2003; Nagarapu, et al., 2007; Kidwai, et al., 2007).

The molecular structure of the title compound and the atom-numbering scheme are shown in Fig. 1. The phenyl rings attached at C2, N2, C9 and C8 enclose dihedral angles of 40.74 (8)°, 85.60 (7)°, 77.10 (6)°, 16.55 (11)°, respectively, with the imidazole ring. An intramolecular hydrogen bond stabilises the molecular conformation. Dipole-dipole and van der Waals interactions are effective in the molecular packing.

Related literature top

For related structures and properties, see: Balalaie et al. (2003); Nagarapu et al. (2007); Kidwai et al. (2007).

Experimental top

A mixture of benzil (2.5 mmol), 4-chlorobenzaldehyde (2.5 mmol), benzylamine (2.5 mmol), ammonium acetate (5 mmol) and activated SBA-sulfonic acid (0.02 g) was heated at 140°C for 6 minutes. The progress of reaction was monitored by TLC. After cooling to room temperature, the mixture was dissolved in hot ethylacetate and the catalyst was removed by filtration. The filtrate was left for crystallization.

Computing details top

Data collection: X-AREA Software (Stoe & Cie, 1997); cell refinement: X-AREA Software (Stoe & Cie, 1997); data reduction: X-AREA Software (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I), with 50% probability displacement ellipsoids. H atoms are shown as circles of arbitrary radii.

(I) top

Crystal data top

C₂₈H₂₁ClN₂	Z = 2
M_r = 420.92	F(000) = 440
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4880 (11) Å	Cell parameters from 6987 reflections
b = 9.2711 (16) Å	θ = 1.2–29.8°
c = 16.049 (3) Å	µ = 0.19 mm⁻¹
α = 87.169 (13)°	T = 290 K
β = 76.704 (12)°	Block, colorless
γ = 87.842 (13)°	0.3 × 0.2 × 0.2 mm
V = 1082.6 (3) Å³

Data collection top

STOE IPDS-II diffractometer	2814 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
Area detector – phi oscillation scans	h = −9→9
8769 measured reflections	k = −11→10
4246 independent reflections	l = −19→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0457P)²] where P = (F_o² + 2F_c²)/3
4246 reflections	(Δ/σ)_max < 0.001
288 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₈H₂₁ClN₂	γ = 87.842 (13)°
M_r = 420.92	V = 1082.6 (3) Å³
Triclinic, P1	Z = 2
a = 7.4880 (11) Å	Mo Kα radiation
b = 9.2711 (16) Å	µ = 0.19 mm⁻¹
c = 16.049 (3) Å	T = 290 K
α = 87.169 (13)°	0.3 × 0.2 × 0.2 mm
β = 76.704 (12)°

Data collection top

STOE IPDS-II diffractometer	2814 reflections with I > 2σ(I)
8769 measured reflections	R_int = 0.034
4246 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.13 e Å⁻³
4246 reflections	Δρ_min = −0.20 e Å⁻³
288 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
Cl1	0.17061 (7)	0.52946 (7)	0.32233 (4)	0.0741 (2)
N1	0.60096 (17)	0.82368 (15)	0.59681 (9)	0.0412 (3)
N2	0.36337 (17)	0.74456 (15)	0.69583 (8)	0.0403 (3)
C1	0.2919 (2)	0.56492 (19)	0.54889 (12)	0.0456 (4)
H1	0.2804	0.5096	0.5997	0.055*
C2	0.4446 (2)	0.75675 (17)	0.61039 (10)	0.0393 (4)
C3	0.9378 (2)	0.9430 (2)	0.61528 (12)	0.0476 (4)
H3	0.9370	0.8959	0.5656	0.057*
C4	0.7878 (2)	0.93196 (18)	0.68467 (11)	0.0413 (4)
C5	0.4409 (2)	0.80553 (19)	0.83352 (11)	0.0419 (4)
C6	0.2487 (2)	0.5939 (2)	0.40748 (12)	0.0492 (5)
C7	0.2308 (2)	0.5117 (2)	0.48201 (12)	0.0491 (4)
H7	0.1784	0.4213	0.4874	0.059*
C8	0.6244 (2)	0.85566 (17)	0.67670 (10)	0.0391 (4)
C9	0.4790 (2)	0.80756 (18)	0.73880 (11)	0.0398 (4)
C10	0.1795 (2)	0.55784 (19)	0.79077 (11)	0.0435 (4)
C11	0.3703 (2)	0.69955 (18)	0.54181 (11)	0.0399 (4)
C12	0.3880 (2)	0.77975 (19)	0.46497 (11)	0.0475 (4)
H12	0.4418	0.8696	0.4587	0.057*
C13	0.5348 (3)	0.7078 (2)	0.87682 (12)	0.0567 (5)
H13	0.6178	0.6416	0.8463	0.068*
C14	0.3263 (3)	0.7273 (2)	0.39788 (12)	0.0530 (5)
H14	0.3373	0.7817	0.3468	0.064*
C15	1.0919 (3)	1.0925 (2)	0.69172 (14)	0.0607 (5)
H15	1.1921	1.1472	0.6939	0.073*
C16	0.1802 (2)	0.6943 (2)	0.73629 (12)	0.0440 (4)
H16A	0.114 (2)	0.6806 (18)	0.6900 (11)	0.046 (5)*
H16B	0.114 (2)	0.7692 (19)	0.7710 (11)	0.046 (5)*
C17	1.0877 (2)	1.0226 (2)	0.61875 (13)	0.0550 (5)
H17	1.1863	1.0290	0.5715	0.066*
C18	0.0320 (3)	0.5323 (2)	0.85851 (13)	0.0625 (5)
H18	−0.0639	0.6003	0.8704	0.075*
C19	0.1645 (4)	0.3071 (3)	0.89254 (17)	0.0854 (8)
H19	0.1596	0.2226	0.9267	0.102*
C20	0.7963 (2)	1.0024 (2)	0.75824 (12)	0.0505 (4)
H20	0.6988	0.9963	0.8060	0.061*
C21	0.3165 (3)	0.9005 (2)	0.88092 (12)	0.0577 (5)
H21	0.2503	0.9662	0.8533	0.069*
C22	0.2891 (3)	0.8988 (3)	0.96904 (13)	0.0699 (6)
H22	0.2046	0.9633	1.0003	0.084*
C23	0.9463 (3)	1.0807 (2)	0.76139 (13)	0.0604 (5)
H23	0.9495	1.1263	0.8113	0.072*
C24	0.3199 (3)	0.4554 (2)	0.77506 (13)	0.0557 (5)
H24	0.4208	0.4706	0.7298	0.067*
C25	0.3117 (4)	0.3305 (3)	0.82608 (17)	0.0747 (6)
H25	0.4072	0.2621	0.8150	0.090*
C26	0.3851 (3)	0.8033 (3)	1.01068 (13)	0.0680 (6)
H26	0.3676	0.8037	1.0699	0.082*
C27	0.5065 (3)	0.7074 (3)	0.96484 (14)	0.0688 (6)
H27	0.5708	0.6412	0.9931	0.083*
C28	0.0251 (4)	0.4068 (3)	0.90890 (15)	0.0820 (7)
H28	−0.0755	0.3905	0.9542	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0667 (3)	0.1008 (5)	0.0631 (3)	−0.0114 (3)	−0.0247 (3)	−0.0313 (3)
N1	0.0440 (7)	0.0441 (8)	0.0370 (8)	−0.0063 (6)	−0.0110 (6)	−0.0032 (6)
N2	0.0392 (7)	0.0453 (8)	0.0374 (8)	−0.0061 (6)	−0.0101 (6)	−0.0014 (6)
C1	0.0421 (9)	0.0474 (11)	0.0493 (10)	−0.0038 (8)	−0.0142 (8)	−0.0024 (8)
C2	0.0399 (8)	0.0402 (10)	0.0396 (9)	−0.0009 (7)	−0.0126 (7)	−0.0028 (7)
C3	0.0473 (9)	0.0531 (11)	0.0429 (10)	−0.0051 (8)	−0.0102 (8)	−0.0057 (8)
C4	0.0445 (9)	0.0407 (10)	0.0407 (9)	−0.0038 (7)	−0.0136 (7)	−0.0021 (7)
C5	0.0408 (8)	0.0473 (10)	0.0383 (9)	−0.0095 (7)	−0.0096 (7)	0.0000 (8)
C6	0.0400 (9)	0.0621 (13)	0.0497 (11)	0.0020 (8)	−0.0156 (8)	−0.0205 (9)
C7	0.0400 (9)	0.0491 (11)	0.0598 (12)	−0.0063 (8)	−0.0124 (8)	−0.0105 (9)
C8	0.0427 (8)	0.0372 (9)	0.0384 (9)	−0.0002 (7)	−0.0109 (7)	−0.0040 (7)
C9	0.0401 (8)	0.0419 (9)	0.0394 (9)	−0.0012 (7)	−0.0128 (7)	−0.0033 (7)
C10	0.0417 (9)	0.0516 (11)	0.0402 (10)	−0.0117 (8)	−0.0136 (8)	−0.0035 (8)
C11	0.0366 (8)	0.0437 (10)	0.0404 (9)	0.0010 (7)	−0.0100 (7)	−0.0064 (8)
C12	0.0558 (10)	0.0434 (11)	0.0443 (10)	−0.0058 (8)	−0.0122 (8)	−0.0055 (8)
C13	0.0580 (11)	0.0655 (13)	0.0497 (12)	0.0048 (9)	−0.0196 (9)	−0.0046 (10)
C14	0.0636 (11)	0.0563 (12)	0.0419 (10)	0.0011 (9)	−0.0174 (9)	−0.0059 (9)
C15	0.0520 (10)	0.0654 (13)	0.0692 (14)	−0.0171 (9)	−0.0200 (10)	−0.0062 (11)
C16	0.0337 (8)	0.0529 (11)	0.0454 (10)	−0.0023 (8)	−0.0083 (8)	−0.0041 (9)
C17	0.0450 (10)	0.0636 (13)	0.0551 (12)	−0.0105 (9)	−0.0080 (9)	−0.0002 (10)
C18	0.0561 (11)	0.0763 (15)	0.0532 (12)	−0.0186 (10)	−0.0061 (9)	−0.0019 (11)
C19	0.140 (2)	0.0633 (16)	0.0644 (16)	−0.0376 (17)	−0.0452 (17)	0.0139 (13)
C20	0.0515 (10)	0.0560 (12)	0.0443 (10)	−0.0104 (8)	−0.0088 (8)	−0.0082 (9)
C21	0.0628 (11)	0.0599 (13)	0.0483 (11)	0.0059 (10)	−0.0092 (9)	−0.0034 (9)
C22	0.0746 (14)	0.0808 (16)	0.0480 (13)	0.0019 (12)	0.0005 (11)	−0.0138 (11)
C23	0.0634 (12)	0.0680 (13)	0.0554 (12)	−0.0141 (10)	−0.0206 (10)	−0.0166 (10)
C24	0.0565 (11)	0.0577 (13)	0.0543 (12)	−0.0039 (9)	−0.0161 (9)	0.0028 (10)
C25	0.0997 (17)	0.0578 (14)	0.0771 (16)	−0.0012 (12)	−0.0425 (14)	0.0001 (12)
C26	0.0800 (14)	0.0880 (17)	0.0359 (11)	−0.0195 (12)	−0.0106 (10)	0.0004 (11)
C27	0.0821 (14)	0.0792 (16)	0.0513 (13)	−0.0035 (12)	−0.0298 (11)	0.0076 (11)
C28	0.0988 (18)	0.092 (2)	0.0522 (14)	−0.0498 (16)	−0.0062 (12)	0.0070 (13)

Geometric parameters (Å, º) top

Cl1—C6	1.7436 (17)	C13—C27	1.379 (3)
N1—C2	1.314 (2)	C13—H13	0.9300
N1—C8	1.381 (2)	C14—H14	0.9300
N2—C2	1.367 (2)	C15—C17	1.373 (3)
N2—C9	1.385 (2)	C15—C23	1.374 (3)
N2—C16	1.459 (2)	C15—H15	0.9300
C1—C7	1.378 (2)	C16—H16A	1.000 (18)
C1—C11	1.388 (2)	C16—H16B	0.960 (17)
C1—H1	0.9300	C17—H17	0.9300
C2—C11	1.471 (2)	C18—C28	1.379 (3)
C3—C17	1.380 (2)	C18—H18	0.9300
C3—C4	1.391 (2)	C19—C28	1.356 (4)
C3—H3	0.9300	C19—C25	1.362 (4)
C4—C20	1.392 (2)	C19—H19	0.9300
C4—C8	1.470 (2)	C20—C23	1.372 (3)
C5—C21	1.378 (2)	C20—H20	0.9300
C5—C13	1.383 (3)	C21—C22	1.381 (3)
C5—C9	1.480 (2)	C21—H21	0.9300
C6—C7	1.369 (3)	C22—C26	1.364 (3)
C6—C14	1.373 (3)	C22—H22	0.9300
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.368 (2)	C24—C25	1.380 (3)
C10—C24	1.377 (2)	C24—H24	0.9300
C10—C18	1.378 (3)	C25—H25	0.9300
C10—C16	1.501 (3)	C26—C27	1.362 (3)
C11—C12	1.390 (2)	C26—H26	0.9300
C12—C14	1.381 (2)	C27—H27	0.9300
C12—H12	0.9300	C28—H28	0.9300

C2—N1—C8	105.97 (13)	C17—C15—C23	119.26 (17)
C2—N2—C9	106.82 (13)	C17—C15—H15	120.4
C2—N2—C16	128.26 (14)	C23—C15—H15	120.4
C9—N2—C16	124.44 (14)	N2—C16—C10	114.03 (14)
C7—C1—C11	121.22 (18)	N2—C16—H16A	107.8 (10)
C7—C1—H1	119.4	C10—C16—H16A	110.3 (10)
C11—C1—H1	119.4	N2—C16—H16B	108.6 (10)
N1—C2—N2	111.47 (14)	C10—C16—H16B	109.0 (10)
N1—C2—C11	123.73 (15)	H16A—C16—H16B	106.7 (13)
N2—C2—C11	124.79 (14)	C15—C17—C3	120.22 (17)
C17—C3—C4	121.31 (16)	C15—C17—H17	119.9
C17—C3—H3	119.3	C3—C17—H17	119.9
C4—C3—H3	119.3	C10—C18—C28	120.7 (2)
C3—C4—C20	117.33 (16)	C10—C18—H18	119.7
C3—C4—C8	119.95 (15)	C28—C18—H18	119.7
C20—C4—C8	122.61 (15)	C28—C19—C25	120.0 (2)
C21—C5—C13	118.12 (17)	C28—C19—H19	120.0
C21—C5—C9	122.19 (16)	C25—C19—H19	120.0
C13—C5—C9	119.68 (15)	C23—C20—C4	121.03 (17)
C7—C6—C14	121.57 (17)	C23—C20—H20	119.5
C7—C6—Cl1	119.75 (15)	C4—C20—H20	119.5
C14—C6—Cl1	118.69 (16)	C5—C21—C22	120.6 (2)
C6—C7—C1	118.92 (17)	C5—C21—H21	119.7
C6—C7—H7	120.5	C22—C21—H21	119.7
C1—C7—H7	120.5	C26—C22—C21	120.6 (2)
C9—C8—N1	109.98 (14)	C26—C22—H22	119.7
C9—C8—C4	129.88 (15)	C21—C22—H22	119.7
N1—C8—C4	120.14 (14)	C20—C23—C15	120.83 (18)
C8—C9—N2	105.76 (14)	C20—C23—H23	119.6
C8—C9—C5	132.19 (15)	C15—C23—H23	119.6
N2—C9—C5	121.91 (14)	C10—C24—C25	120.4 (2)
C24—C10—C18	118.34 (19)	C10—C24—H24	119.8
C24—C10—C16	122.53 (16)	C25—C24—H24	119.8
C18—C10—C16	119.12 (17)	C19—C25—C24	120.3 (2)
C1—C11—C12	118.42 (16)	C19—C25—H25	119.8
C1—C11—C2	122.62 (16)	C24—C25—H25	119.8
C12—C11—C2	118.87 (15)	C27—C26—C22	119.51 (19)
C14—C12—C11	120.65 (17)	C27—C26—H26	120.2
C14—C12—H12	119.7	C22—C26—H26	120.2
C11—C12—H12	119.7	C26—C27—C13	120.5 (2)
C27—C13—C5	120.73 (19)	C26—C27—H27	119.8
C27—C13—H13	119.6	C13—C27—H27	119.8
C5—C13—H13	119.6	C19—C28—C18	120.2 (2)
C6—C14—C12	119.22 (18)	C19—C28—H28	119.9
C6—C14—H14	120.4	C18—C28—H28	119.9
C12—C14—H14	120.4

C8—N1—C2—N2	0.58 (18)	N1—C2—C11—C12	−39.5 (2)
C8—N1—C2—C11	−178.04 (15)	N2—C2—C11—C12	142.03 (17)
C9—N2—C2—N1	−0.62 (19)	C1—C11—C12—C14	0.9 (2)
C16—N2—C2—N1	171.59 (15)	C2—C11—C12—C14	177.51 (15)
C9—N2—C2—C11	177.97 (15)	C21—C5—C13—C27	−1.1 (3)
C16—N2—C2—C11	−9.8 (3)	C9—C5—C13—C27	177.59 (18)
C17—C3—C4—C20	−1.0 (3)	C7—C6—C14—C12	0.0 (3)
C17—C3—C4—C8	175.34 (17)	Cl1—C6—C14—C12	179.73 (13)
C14—C6—C7—C1	0.3 (3)	C11—C12—C14—C6	−0.6 (3)
Cl1—C6—C7—C1	−179.45 (12)	C2—N2—C16—C10	115.85 (19)
C11—C1—C7—C6	0.1 (2)	C9—N2—C16—C10	−73.2 (2)
C2—N1—C8—C9	−0.31 (18)	C24—C10—C16—N2	−28.4 (2)
C2—N1—C8—C4	−179.85 (15)	C18—C10—C16—N2	152.54 (16)
C3—C4—C8—C9	165.88 (18)	C23—C15—C17—C3	0.8 (3)
C20—C4—C8—C9	−17.9 (3)	C4—C3—C17—C15	0.3 (3)
C3—C4—C8—N1	−14.7 (2)	C24—C10—C18—C28	−0.3 (3)
C20—C4—C8—N1	161.51 (16)	C16—C10—C18—C28	178.75 (18)
N1—C8—C9—N2	−0.06 (18)	C3—C4—C20—C23	0.7 (3)
C4—C8—C9—N2	179.42 (16)	C8—C4—C20—C23	−175.60 (17)
N1—C8—C9—C5	175.61 (17)	C13—C5—C21—C22	0.9 (3)
C4—C8—C9—C5	−4.9 (3)	C9—C5—C21—C22	−177.70 (18)
C2—N2—C9—C8	0.40 (18)	C5—C21—C22—C26	0.1 (3)
C16—N2—C9—C8	−172.20 (15)	C4—C20—C23—C15	0.4 (3)
C2—N2—C9—C5	−175.82 (15)	C17—C15—C23—C20	−1.2 (3)
C16—N2—C9—C5	11.6 (2)	C18—C10—C24—C25	0.1 (3)
C21—C5—C9—C8	105.1 (2)	C16—C10—C24—C25	−178.92 (18)
C13—C5—C9—C8	−73.6 (3)	C28—C19—C25—C24	−0.1 (3)
C21—C5—C9—N2	−79.8 (2)	C10—C24—C25—C19	0.1 (3)
C13—C5—C9—N2	101.5 (2)	C21—C22—C26—C27	−1.1 (3)
C7—C1—C11—C12	−0.7 (2)	C22—C26—C27—C13	0.9 (3)
C7—C1—C11—C2	−177.10 (14)	C5—C13—C27—C26	0.2 (3)
N1—C2—C11—C1	136.88 (17)	C25—C19—C28—C18	−0.1 (4)
N2—C2—C11—C1	−41.5 (2)	C10—C18—C28—C19	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.56	2.874 (2)	100

Experimental details

Crystal data
Chemical formula	C₂₈H₂₁ClN₂
M_r	420.92
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	7.4880 (11), 9.2711 (16), 16.049 (3)
α, β, γ (°)	87.169 (13), 76.704 (12), 87.842 (13)
V (Å³)	1082.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	STOE IPDS-II diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8769, 4246, 2814
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.090, 0.94
No. of reflections	4246
No. of parameters	288
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.20

Computer programs: X-AREA Software (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.56	2.874 (2)	100.3

Acknowledgements

This work was supported by a grant from the University of Tehran and the University of Alzahra.

References

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