Ethyl 2-methyl-4-phenyl­pyrido[1,2-a]benzimidazole-3-carboxyl­ate

Ge, Y.Q.; Ge, H.Y.; Cao, X.Q.

doi:10.1107/S1600536811039973

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2846

doi:10.1107/S1600536811039973

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Ethyl 2-methyl-4-phenylpyrido[1,2-a]benzimidazole-3-carboxylate

Yan Qing Ge,^a Hai Yan Ge ^a and Xiao Qun Cao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Taishan Medical College, Tai An, 271016, People's Republic of China
^*Correspondence e-mail: xqcao@yahoo.cn

(Received 15 September 2011; accepted 28 September 2011; online 5 October 2011)

The title compound, C₂₁H₁₈N₂O₂, was synthesized using a novel tandem annulation reaction between (1H-benzimidazol-2-yl)(phenyl)methanone and (E)-ethyl 4-bromobut-2-enoate under mild conditions. The dihedral angles between the mean planes of the five-membered imidazole ring and the pyridine, benzene and phenyl rings are 0.45 (6), 1.69 (1) and 70.96 (8)°, respectively. In the crystal, molecules are linked through intermolecular C—H⋯N hydrogen bonds.

Related literature

For applications of nitrogen-containing heterocyclic compounds in the agrochemical and pharmaceutical fields, see: Ge et al. (2009 ). For the synthesis of the title compound, see: Ge et al. (2011 ). For the structure of 2,7,8-trimethyl-3-ethoxycarbonyl-4- phenylpyrido[1,2-a]benzimidazole, see: Ge et al.(2011). Some pyrido[1,2-a]benzimidazole derivatives are of interest for their biological activity, such as antineoplastic activity and central GABA-A receptor modulators for the treatment of anxiety, see: Badawey & Kappe (1999 ).

Experimental

Crystal data

C₂₁H₁₈N₂O₂
M_r = 330.37
Monoclinic, P 2₁ /c
a = 10.1176 (13) Å
b = 14.9136 (18) Å
c = 12.2648 (15) Å
β = 108.487 (2)°
V = 1755.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.26 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.985
8867 measured reflections
3093 independent reflections
2515 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.06
3093 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N2ⁱ	0.93	2.31	3.2092 (18)	164
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811039973/fj2449sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039973/fj2449Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039973/fj2449Isup3.cml

checkCIF report

Comment top

Synthesis of nitrogen-containing heterocyclic compounds has been a subject of great interest due to the wide application in agrochemical and pharmaceutical fields (Ge et al.; 2011). Some pyrido[1,2-a]benzimidazole derivatives have been of interest for their biological activities, such as antineoplastic activity and central GABA-A receptor modulators for the treatment of anxiety (Badawey et al.; 1999). We report here the crystal structure of the title compound, (I) (Fig. 1)

Related literature top

For applications of nitrogen-containing heterocyclic compounds in the agrochemical and pharmaceutical fields, see: Ge et al. (2009). For the synthesis of the title compound, see: Ge et al. (2011). For the structure of 2,7,8-trimethyl-3-ethoxycarbonyl-4- phenylpyrido[1,2-a]benzimidazole, see: Ge et al.(2011). Some pyrido[1,2-a]benzimidazole derivatives are of interest for their biological activity, such as antineoplastic activity and central GABA-A receptor modulators for the treatment of anxiety, see: Badawey & Kappe (1999).

Experimental top

To a 50 ml round-bottomed flask were added (1H-benzo[d]imidazol-2-yl)(phenyl)methanone (1.00 mmol), (E)-ethyl 4-bromobut-2-enoate (2.00 mmol), potassium carbonate (0.28 g, 2.05 mmol) and dry DMF (10 ml). The mixture was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and an product was isolated by column chromatography on silica gel (yield 74%). Crystals of (I) suitable for X-ray diffraction were obtained by allowing a refluxed solution of the product in ethyl acetate to cool slowly to room temperature (without temperature control) and allowing the solvent to evaporate for 3 d

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.

Ethyl 2-methyl-4-phenylpyrido[1,2-a]benzimidazole-3-carboxylate top

Crystal data top

C₂₁H₁₈N₂O₂	F(000) = 696
M_r = 330.37	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4793 reflections
a = 10.1176 (13) Å	θ = 2.2–28.2°
b = 14.9136 (18) Å	µ = 0.08 mm⁻¹
c = 12.2648 (15) Å	T = 298 K
β = 108.487 (2)°	BLOCK, yellow
V = 1755.1 (4) Å³	0.26 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3093 independent reflections
Radiation source: fine-focus sealed tube	2515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.979, T_max = 0.985	k = −10→17
8867 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0406P)² + 0.4084P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3093 reflections	Δρ_max = 0.18 e Å⁻³
227 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0077 (13)

Crystal data top

C₂₁H₁₈N₂O₂	V = 1755.1 (4) Å³
M_r = 330.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1176 (13) Å	µ = 0.08 mm⁻¹
b = 14.9136 (18) Å	T = 298 K
c = 12.2648 (15) Å	0.26 × 0.22 × 0.19 mm
β = 108.487 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3093 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2515 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.985	R_int = 0.021
8867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
3093 reflections	Δρ_min = −0.16 e Å⁻³
227 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	0.10877 (12)	0.07612 (10)	0.79576 (12)	0.0806 (4)
O2	0.26487 (10)	−0.01607 (7)	0.91064 (10)	0.0565 (3)
N1	0.57376 (11)	0.22116 (7)	0.87282 (9)	0.0359 (3)
N2	0.60190 (12)	0.26824 (8)	1.05384 (9)	0.0436 (3)
C1	0.68800 (13)	0.27812 (9)	0.90225 (11)	0.0375 (3)
C2	0.70311 (14)	0.30576 (9)	1.01441 (11)	0.0398 (3)
C3	0.81352 (16)	0.36238 (11)	1.07098 (13)	0.0508 (4)
H3	0.8262	0.3817	1.1457	0.061*
C4	0.90241 (16)	0.38855 (11)	1.01303 (14)	0.0545 (4)
H4	0.9767	0.4260	1.0496	0.065*
C5	0.88497 (16)	0.36077 (11)	0.90058 (14)	0.0540 (4)
H5	0.9473	0.3804	0.8640	0.065*
C6	0.77758 (15)	0.30500 (10)	0.84297 (13)	0.0468 (4)
H6	0.7654	0.2862	0.7681	0.056*
C7	0.52624 (13)	0.21772 (9)	0.96751 (11)	0.0365 (3)
C8	0.40891 (14)	0.16270 (9)	0.95981 (11)	0.0385 (3)
C9	0.35444 (14)	0.15819 (10)	1.05942 (12)	0.0406 (3)
C10	0.42867 (17)	0.11386 (11)	1.15914 (13)	0.0511 (4)
H10	0.5136	0.0872	1.1647	0.061*
C11	0.3766 (2)	0.10917 (13)	1.25066 (14)	0.0637 (5)
H11	0.4261	0.0784	1.3170	0.076*
C12	0.2527 (2)	0.14964 (13)	1.24415 (16)	0.0677 (5)
H12	0.2186	0.1466	1.3061	0.081*
C13	0.17917 (19)	0.19447 (12)	1.14640 (17)	0.0634 (5)
H13	0.0956	0.2225	1.1422	0.076*
C14	0.22908 (16)	0.19811 (11)	1.05370 (14)	0.0517 (4)
H14	0.1778	0.2277	0.9869	0.062*
C15	0.34899 (14)	0.11679 (9)	0.85925 (11)	0.0389 (3)
C16	0.39968 (14)	0.12299 (9)	0.76289 (11)	0.0400 (3)
C17	0.51144 (14)	0.17530 (9)	0.77255 (11)	0.0398 (3)
H17	0.5464	0.1803	0.7112	0.048*
C18	0.33086 (17)	0.07371 (12)	0.65248 (12)	0.0548 (4)
H18A	0.3839	0.0823	0.6008	0.082*
H18B	0.2382	0.0965	0.6179	0.082*
H18C	0.3265	0.0109	0.6682	0.082*
C19	0.22564 (15)	0.05809 (10)	0.85009 (12)	0.0443 (3)
C20	0.15708 (18)	−0.07492 (11)	0.92566 (16)	0.0598 (4)
H20A	0.1769	−0.1366	0.9109	0.072*
H20B	0.0673	−0.0587	0.8717	0.072*
C21	0.15356 (18)	−0.06592 (12)	1.04557 (16)	0.0656 (5)
H21A	0.2437	−0.0800	1.0985	0.098*
H21B	0.0855	−0.1064	1.0572	0.098*
H21C	0.1292	−0.0055	1.0583	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0426 (7)	0.0950 (10)	0.0882 (9)	−0.0126 (6)	−0.0019 (6)	0.0330 (8)
O2	0.0439 (6)	0.0466 (6)	0.0797 (8)	−0.0035 (5)	0.0206 (5)	0.0096 (6)
N1	0.0368 (6)	0.0431 (6)	0.0287 (5)	−0.0039 (5)	0.0119 (5)	0.0010 (5)
N2	0.0455 (7)	0.0532 (7)	0.0345 (6)	−0.0091 (6)	0.0160 (5)	−0.0049 (5)
C1	0.0355 (7)	0.0412 (7)	0.0352 (7)	−0.0016 (6)	0.0105 (6)	0.0041 (6)
C2	0.0404 (7)	0.0438 (8)	0.0347 (7)	−0.0027 (6)	0.0111 (6)	0.0021 (6)
C3	0.0526 (9)	0.0554 (9)	0.0407 (8)	−0.0105 (7)	0.0093 (7)	−0.0024 (7)
C4	0.0449 (8)	0.0561 (10)	0.0555 (10)	−0.0134 (7)	0.0062 (7)	0.0057 (7)
C5	0.0443 (8)	0.0637 (10)	0.0559 (10)	−0.0092 (7)	0.0187 (7)	0.0121 (8)
C6	0.0468 (8)	0.0558 (9)	0.0408 (8)	−0.0046 (7)	0.0182 (7)	0.0061 (7)
C7	0.0375 (7)	0.0438 (8)	0.0295 (6)	−0.0014 (6)	0.0125 (5)	0.0014 (6)
C8	0.0372 (7)	0.0455 (8)	0.0336 (7)	−0.0006 (6)	0.0126 (6)	0.0031 (6)
C9	0.0414 (8)	0.0452 (8)	0.0386 (7)	−0.0096 (6)	0.0176 (6)	−0.0036 (6)
C10	0.0502 (9)	0.0640 (10)	0.0421 (8)	−0.0040 (8)	0.0187 (7)	0.0028 (7)
C11	0.0735 (12)	0.0798 (12)	0.0428 (9)	−0.0143 (10)	0.0257 (8)	0.0046 (8)
C12	0.0809 (13)	0.0801 (13)	0.0603 (11)	−0.0246 (11)	0.0483 (10)	−0.0144 (10)
C13	0.0583 (10)	0.0676 (11)	0.0788 (13)	−0.0100 (9)	0.0425 (10)	−0.0138 (10)
C14	0.0472 (8)	0.0547 (9)	0.0572 (9)	−0.0036 (7)	0.0224 (7)	−0.0012 (7)
C15	0.0365 (7)	0.0430 (8)	0.0362 (7)	−0.0008 (6)	0.0100 (6)	0.0037 (6)
C16	0.0421 (8)	0.0440 (8)	0.0320 (7)	−0.0008 (6)	0.0090 (6)	0.0008 (6)
C17	0.0445 (8)	0.0480 (8)	0.0278 (7)	−0.0012 (6)	0.0129 (6)	0.0000 (6)
C18	0.0591 (10)	0.0625 (10)	0.0397 (8)	−0.0102 (8)	0.0113 (7)	−0.0080 (7)
C19	0.0394 (8)	0.0531 (9)	0.0398 (7)	−0.0045 (7)	0.0115 (6)	−0.0019 (7)
C20	0.0554 (10)	0.0456 (9)	0.0834 (12)	−0.0115 (7)	0.0291 (9)	0.0012 (8)
C21	0.0583 (10)	0.0596 (11)	0.0838 (13)	0.0024 (8)	0.0294 (10)	0.0088 (9)

Geometric parameters (Å, º) top

O1—C19	1.1894 (18)	C10—C11	1.385 (2)
O2—C19	1.3211 (18)	C10—H10	0.9300
O2—C20	1.4564 (18)	C11—C12	1.371 (3)
N1—C17	1.3733 (16)	C11—H11	0.9300
N1—C1	1.3868 (17)	C12—C13	1.368 (3)
N1—C7	1.3917 (16)	C12—H12	0.9300
N2—C7	1.3270 (17)	C13—C14	1.384 (2)
N2—C2	1.3818 (17)	C13—H13	0.9300
C1—C6	1.3887 (19)	C14—H14	0.9300
C1—C2	1.3973 (19)	C15—C16	1.4328 (19)
C2—C3	1.397 (2)	C15—C19	1.4992 (19)
C3—C4	1.368 (2)	C16—C17	1.3477 (19)
C3—H3	0.9300	C16—C18	1.5036 (19)
C4—C5	1.397 (2)	C17—H17	0.9300
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.373 (2)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—H6	0.9300	C20—C21	1.488 (3)
C7—C8	1.4214 (19)	C20—H20A	0.9700
C8—C15	1.3722 (19)	C20—H20B	0.9700
C8—C9	1.4926 (19)	C21—H21A	0.9600
C9—C14	1.383 (2)	C21—H21B	0.9600
C9—C10	1.384 (2)	C21—H21C	0.9600

C19—O2—C20	118.17 (12)	C13—C12—H12	120.0
C17—N1—C1	130.26 (11)	C11—C12—H12	120.0
C17—N1—C7	123.15 (11)	C12—C13—C14	120.04 (16)
C1—N1—C7	106.58 (10)	C12—C13—H13	120.0
C7—N2—C2	104.76 (11)	C14—C13—H13	120.0
N1—C1—C6	131.99 (13)	C9—C14—C13	120.62 (16)
N1—C1—C2	105.00 (11)	C9—C14—H14	119.7
C6—C1—C2	122.99 (13)	C13—C14—H14	119.7
N2—C2—C3	129.47 (13)	C8—C15—C16	122.51 (12)
N2—C2—C1	111.30 (12)	C8—C15—C19	118.60 (12)
C3—C2—C1	119.21 (13)	C16—C15—C19	118.88 (12)
C4—C3—C2	117.93 (14)	C17—C16—C15	118.34 (12)
C4—C3—H3	121.0	C17—C16—C18	119.87 (13)
C2—C3—H3	121.0	C15—C16—C18	121.79 (13)
C3—C4—C5	122.03 (15)	C16—C17—N1	120.08 (12)
C3—C4—H4	119.0	C16—C17—H17	120.0
C5—C4—H4	119.0	N1—C17—H17	120.0
C6—C5—C4	121.30 (14)	C16—C18—H18A	109.5
C6—C5—H5	119.4	C16—C18—H18B	109.5
C4—C5—H5	119.4	H18A—C18—H18B	109.5
C5—C6—C1	116.54 (14)	C16—C18—H18C	109.5
C5—C6—H6	121.7	H18A—C18—H18C	109.5
C1—C6—H6	121.7	H18B—C18—H18C	109.5
N2—C7—N1	112.36 (11)	O1—C19—O2	124.91 (14)
N2—C7—C8	129.73 (12)	O1—C19—C15	124.47 (14)
N1—C7—C8	117.91 (11)	O2—C19—C15	110.62 (12)
C15—C8—C7	117.99 (12)	O2—C20—C21	108.91 (14)
C15—C8—C9	122.73 (12)	O2—C20—H20A	109.9
C7—C8—C9	119.27 (12)	C21—C20—H20A	109.9
C14—C9—C10	118.86 (14)	O2—C20—H20B	109.9
C14—C9—C8	120.66 (13)	C21—C20—H20B	109.9
C10—C9—C8	120.48 (13)	H20A—C20—H20B	108.3
C9—C10—C11	120.09 (16)	C20—C21—H21A	109.5
C9—C10—H10	120.0	C20—C21—H21B	109.5
C11—C10—H10	120.0	H21A—C21—H21B	109.5
C12—C11—C10	120.43 (17)	C20—C21—H21C	109.5
C12—C11—H11	119.8	H21A—C21—H21C	109.5
C10—C11—H11	119.8	H21B—C21—H21C	109.5
C13—C12—C11	119.93 (15)

C17—N1—C1—C6	−2.2 (2)	C15—C8—C9—C10	109.59 (17)
C7—N1—C1—C6	178.59 (15)	C7—C8—C9—C10	−71.49 (18)
C17—N1—C1—C2	179.46 (13)	C14—C9—C10—C11	0.7 (2)
C7—N1—C1—C2	0.20 (14)	C8—C9—C10—C11	−179.29 (14)
C7—N2—C2—C3	−177.76 (15)	C9—C10—C11—C12	−1.2 (3)
C7—N2—C2—C1	0.44 (16)	C10—C11—C12—C13	0.5 (3)
N1—C1—C2—N2	−0.40 (15)	C11—C12—C13—C14	0.7 (3)
C6—C1—C2—N2	−178.98 (13)	C10—C9—C14—C13	0.5 (2)
N1—C1—C2—C3	178.00 (13)	C8—C9—C14—C13	−179.52 (14)
C6—C1—C2—C3	−0.6 (2)	C12—C13—C14—C9	−1.2 (3)
N2—C2—C3—C4	178.25 (15)	C7—C8—C15—C16	−0.4 (2)
C1—C2—C3—C4	0.2 (2)	C9—C8—C15—C16	178.50 (13)
C2—C3—C4—C5	0.3 (2)	C7—C8—C15—C19	179.67 (12)
C3—C4—C5—C6	−0.5 (3)	C9—C8—C15—C19	−1.4 (2)
C4—C5—C6—C1	0.1 (2)	C8—C15—C16—C17	0.7 (2)
N1—C1—C6—C5	−177.72 (14)	C19—C15—C16—C17	−179.38 (13)
C2—C1—C6—C5	0.4 (2)	C8—C15—C16—C18	−178.70 (14)
C2—N2—C7—N1	−0.31 (15)	C19—C15—C16—C18	1.2 (2)
C2—N2—C7—C8	179.29 (14)	C15—C16—C17—N1	−0.1 (2)
C17—N1—C7—N2	−179.25 (12)	C18—C16—C17—N1	179.34 (13)
C1—N1—C7—N2	0.07 (15)	C1—N1—C17—C16	−179.97 (13)
C17—N1—C7—C8	1.10 (19)	C7—N1—C17—C16	−0.8 (2)
C1—N1—C7—C8	−179.58 (12)	C20—O2—C19—O1	−8.9 (2)
N2—C7—C8—C15	179.97 (14)	C20—O2—C19—C15	171.09 (13)
N1—C7—C8—C15	−0.45 (19)	C8—C15—C19—O1	105.81 (18)
N2—C7—C8—C9	1.0 (2)	C16—C15—C19—O1	−74.1 (2)
N1—C7—C8—C9	−179.42 (12)	C8—C15—C19—O2	−74.15 (16)
C15—C8—C9—C14	−70.36 (19)	C16—C15—C19—O2	105.95 (15)
C7—C8—C9—C14	108.56 (16)	C19—O2—C20—C21	−106.00 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N2ⁱ	0.93	2.31	3.2092 (18)	164

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂O₂
M_r	330.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.1176 (13), 14.9136 (18), 12.2648 (15)
β (°)	108.487 (2)
V (Å³)	1755.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.22 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	8867, 3093, 2515
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.06
No. of reflections	3093
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N2ⁱ	0.93	2.31	3.2092 (18)	164

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

This study was supported by the Natural Science Foundation of Shandong Province (Y2007C135).

References

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