(Z)-3-(9-Anthr­yl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolyl­prop-2-en-1-one

Wang, G.-Z.; Fang, B.; Zhou, C.-H.

doi:10.1107/S1600536809039221

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2619

https://doi.org/10.1107/S1600536809039221

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(Z)-3-(9-Anthryl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolylprop-2-en-1-one

Guang-Zhou Wang,^a Bo Fang ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic and Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 24 September 2009; accepted 27 September 2009; online 3 October 2009)

In the title molecule, C₂₇H₁₉N₃O₃, the imidazole and benzene rings make dihedral angles of 64.72 (4) and 64.02 (4)°, respectively, with the anthracene ring system (r.m.s. deviation = 0.043 Å). The nitro group is coplanar with the imidazole ring [dihedral angle = 1.1 (1)°]. The crystal packing is stabilized by weak π–π interactions with centroid–centroid distances of 3.7342 (10) and 3.7627 (9) Å.

Related literature

For the crystal structures of the chloro and bromo analogues, see: Wang et al. (2009 ); Lu et al. (2009 ). For general background to chalcones, see: Vogel et al. (2008 ). For the synthesis, see: Erhardt et al. (1985 ).

Experimental

Crystal data

C₂₇H₁₉N₃O₃
M_r = 433.45
Triclinic, $[P \overline 1]$
a = 7.9335 (9) Å
b = 11.2626 (13) Å
c = 13.0291 (15) Å
α = 75.454 (2)°
β = 85.763 (2)°
γ = 71.059 (2)°
V = 1065.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.36 × 0.23 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.968, T_max = 0.991
12116 measured reflections
4621 independent reflections
3646 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.127
S = 1.05
4621 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809039221/ci2921sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039221/ci2921Isup2.hkl

checkCIF report

Comment top

Chalcones or 1,3-diaryl-2-propen-1-ones are natural or synthetic compounds belonging to the flavonoid family (Vogel et al., 2008). They exhibit diverse kinds of biological activities. Hence, chalcones are considered as an important class of therapeutic agents. A series of chalcone derivatives containing a imidazole ring have been synthesized in our lab and crystal structues of some of them have been reported (Lu et al., 2009; Wang et al., 2009). We report here the crystal structure of the title compound.

In the molecular structure of the title compound (Fig. 1), the imidazole and benzene ring of the tolyl group form dihedral angles of 64.72 (4)° and 64.02 (4)°, respectively, with the anthracene ring system (r.m.s. deviation 0.043 Å). The nitro group is coplanar with the imidazole ring [dihedral angle 1.1 (1)°].

The crystal structure is stabilized by weak π-π interactions between imidazole and benzene ring of the tolyl group (centroid to centroid distance = 3.7627 (9) Å) and those between the rings of the anthracene ring system (centroid to centroid distance = 3.7342 (10) Å).

Related literature top

For the crystal structures of the chloro and bromo analogues, see: Wang et al. (2009); Lu et al. (2009). For general background to chalcones, see: Vogel et al. (2008). For the synthesis, see: Erhardt et al. (1985).

Experimental top

The title compound was synthesized according to the procedure of Erhardt et al. (1985). Single crystals suitable for X-ray analysis was grown from a chloroform solution by slow evaporation at room temperature.

Structure description top

For the crystal structures of the chloro and bromo analogues, see: Wang et al. (2009); Lu et al. (2009). For general background to chalcones, see: Vogel et al. (2008). For the synthesis, see: Erhardt et al. (1985).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(Z)-3-(9-Anthryl)-2-(4-nitro-1H-imidazol-1-yl)-1-p- tolylprop-2-en-1-one top

Crystal data top

C₂₇H₁₉N₃O₃	Z = 2
M_r = 433.45	F(000) = 452
Triclinic, P1	D_x = 1.351 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9335 (9) Å	Cell parameters from 5053 reflections
b = 11.2626 (13) Å	θ = 2.2–28.1°
c = 13.0291 (15) Å	µ = 0.09 mm⁻¹
α = 75.454 (2)°	T = 298 K
β = 85.763 (2)°	Plate, yellow
γ = 71.059 (2)°	0.36 × 0.23 × 0.10 mm
V = 1065.8 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4621 independent reflections
Radiation source: fine-focus sealed tube	3646 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→10
T_min = 0.968, T_max = 0.991	k = −14→14
12116 measured reflections	l = −16→16

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) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0696P)² + 0.061P] where P = (F_o² + 2F_c²)/3
4621 reflections	(Δ/σ)_max = 0.012
299 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₇H₁₉N₃O₃	γ = 71.059 (2)°
M_r = 433.45	V = 1065.8 (2) Å³
Triclinic, P1	Z = 2
a = 7.9335 (9) Å	Mo Kα radiation
b = 11.2626 (13) Å	µ = 0.09 mm⁻¹
c = 13.0291 (15) Å	T = 298 K
α = 75.454 (2)°	0.36 × 0.23 × 0.10 mm
β = 85.763 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4621 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3646 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.991	R_int = 0.030
12116 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
4621 reflections	Δρ_min = −0.23 e Å⁻³
299 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
C1	0.8022 (2)	0.80103 (14)	0.10371 (11)	0.0625 (4)
C2	0.9235 (2)	0.68461 (16)	0.09495 (12)	0.0655 (4)
H2	1.0443	0.6760	0.0895	0.079*
C3	0.86855 (18)	0.58070 (13)	0.09409 (10)	0.0542 (3)
H3	0.9521	0.5032	0.0871	0.065*
C4	0.68960 (16)	0.59098 (11)	0.10360 (9)	0.0443 (3)
C5	0.56700 (18)	0.70796 (12)	0.11149 (10)	0.0525 (3)
H5	0.4464	0.7164	0.1176	0.063*
C6	0.6231 (2)	0.81227 (13)	0.11031 (11)	0.0604 (4)
H6	0.5394	0.8911	0.1140	0.073*
C7	0.8646 (3)	0.91345 (19)	0.10604 (18)	0.1030 (7)
H7A	0.9884	0.8938	0.0878	0.155*
H7B	0.8486	0.9288	0.1759	0.155*
H7C	0.7964	0.9893	0.0559	0.155*
C8	0.63944 (15)	0.47439 (11)	0.10306 (9)	0.0429 (3)
C9	0.53578 (15)	0.42485 (10)	0.19465 (9)	0.0401 (3)
C10	0.51789 (15)	0.46279 (11)	0.28466 (9)	0.0424 (3)
H10	0.5567	0.5329	0.2825	0.051*
C11	0.55904 (19)	0.21206 (12)	0.15682 (10)	0.0547 (3)
H11	0.6800	0.1879	0.1413	0.066*
C12	0.29544 (19)	0.21363 (13)	0.18201 (9)	0.0522 (3)
C13	0.29627 (17)	0.32641 (12)	0.20011 (9)	0.0479 (3)
H13	0.2010	0.3902	0.2198	0.057*
C14	0.44576 (16)	0.41062 (12)	0.38765 (9)	0.0442 (3)
C15	0.31154 (16)	0.49758 (13)	0.43426 (9)	0.0497 (3)
C16	0.23060 (19)	0.62857 (14)	0.38169 (12)	0.0604 (4)
H16	0.2649	0.6593	0.3130	0.072*
C17	0.1035 (2)	0.71059 (18)	0.42967 (15)	0.0772 (5)
H17	0.0528	0.7965	0.3936	0.093*
C18	0.0482 (2)	0.6666 (2)	0.53315 (16)	0.0844 (6)
H18	−0.0377	0.7238	0.5655	0.101*
C19	0.1187 (2)	0.5429 (2)	0.58552 (13)	0.0770 (5)
H19	0.0799	0.5152	0.6538	0.092*
C20	0.25212 (18)	0.45250 (17)	0.53893 (10)	0.0587 (4)
C21	0.3253 (2)	0.32471 (18)	0.59118 (10)	0.0668 (4)
H21	0.2843	0.2958	0.6585	0.080*
C22	0.4581 (2)	0.23721 (15)	0.54715 (10)	0.0609 (4)
C23	0.5358 (3)	0.10705 (19)	0.60296 (13)	0.0849 (5)
H23	0.4934	0.0776	0.6698	0.102*
C24	0.6697 (3)	0.02531 (18)	0.56107 (15)	0.0961 (6)
H24	0.7168	−0.0604	0.5983	0.115*
C25	0.7395 (3)	0.06850 (16)	0.46106 (13)	0.0800 (5)
H25	0.8346	0.0116	0.4339	0.096*
C26	0.6691 (2)	0.19203 (13)	0.40416 (11)	0.0588 (4)
H26	0.7175	0.2190	0.3386	0.071*
C27	0.52314 (18)	0.28088 (13)	0.44281 (9)	0.0495 (3)
N1	0.46726 (13)	0.32578 (9)	0.18306 (7)	0.0428 (2)
N2	0.45809 (17)	0.14128 (11)	0.15594 (9)	0.0602 (3)
N4	0.1423 (2)	0.17060 (15)	0.18753 (10)	0.0718 (4)
O1	0.69016 (12)	0.41643 (9)	0.03388 (7)	0.0576 (3)
O2	0.1606 (2)	0.06711 (14)	0.16772 (11)	0.1051 (5)
O3	0.00028 (18)	0.24220 (15)	0.21342 (12)	0.0975 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0851 (10)	0.0617 (9)	0.0534 (8)	−0.0413 (8)	0.0181 (7)	−0.0175 (7)
C2	0.0631 (9)	0.0805 (10)	0.0669 (9)	−0.0393 (8)	0.0181 (7)	−0.0256 (8)
C3	0.0561 (8)	0.0585 (8)	0.0523 (7)	−0.0224 (6)	0.0110 (6)	−0.0185 (6)
C4	0.0526 (7)	0.0487 (7)	0.0330 (6)	−0.0207 (5)	0.0039 (5)	−0.0070 (5)
C5	0.0549 (7)	0.0518 (7)	0.0487 (7)	−0.0175 (6)	0.0043 (6)	−0.0088 (6)
C6	0.0793 (10)	0.0476 (7)	0.0520 (8)	−0.0192 (7)	0.0090 (7)	−0.0113 (6)
C7	0.1274 (17)	0.0883 (13)	0.1247 (16)	−0.0694 (13)	0.0351 (14)	−0.0441 (12)
C8	0.0430 (6)	0.0459 (6)	0.0378 (6)	−0.0122 (5)	−0.0015 (5)	−0.0083 (5)
C9	0.0436 (6)	0.0390 (6)	0.0385 (6)	−0.0150 (5)	−0.0023 (5)	−0.0078 (5)
C10	0.0473 (6)	0.0432 (6)	0.0399 (6)	−0.0189 (5)	−0.0012 (5)	−0.0094 (5)
C11	0.0663 (8)	0.0466 (7)	0.0539 (7)	−0.0195 (6)	0.0048 (6)	−0.0160 (6)
C12	0.0684 (9)	0.0562 (8)	0.0393 (6)	−0.0335 (7)	−0.0051 (6)	−0.0049 (5)
C13	0.0509 (7)	0.0533 (7)	0.0419 (6)	−0.0211 (6)	−0.0030 (5)	−0.0089 (5)
C14	0.0501 (7)	0.0566 (7)	0.0347 (6)	−0.0276 (6)	−0.0006 (5)	−0.0122 (5)
C15	0.0491 (7)	0.0693 (9)	0.0428 (6)	−0.0290 (6)	0.0004 (5)	−0.0216 (6)
C16	0.0582 (8)	0.0705 (9)	0.0604 (8)	−0.0221 (7)	0.0010 (6)	−0.0276 (7)
C17	0.0632 (9)	0.0857 (11)	0.0916 (12)	−0.0160 (8)	−0.0031 (8)	−0.0463 (10)
C18	0.0562 (9)	0.1257 (17)	0.0902 (13)	−0.0252 (10)	0.0098 (9)	−0.0667 (13)
C19	0.0564 (9)	0.1382 (17)	0.0592 (9)	−0.0450 (10)	0.0129 (7)	−0.0491 (11)
C20	0.0508 (7)	0.0984 (11)	0.0442 (7)	−0.0399 (7)	0.0042 (6)	−0.0274 (7)
C21	0.0708 (9)	0.1096 (13)	0.0367 (7)	−0.0552 (9)	0.0048 (6)	−0.0134 (8)
C22	0.0771 (10)	0.0761 (9)	0.0401 (7)	−0.0446 (8)	−0.0072 (6)	−0.0034 (6)
C23	0.1265 (16)	0.0850 (12)	0.0485 (8)	−0.0569 (12)	−0.0116 (9)	0.0089 (8)
C24	0.151 (2)	0.0634 (10)	0.0639 (11)	−0.0333 (12)	−0.0260 (12)	0.0091 (9)
C25	0.1040 (13)	0.0594 (9)	0.0676 (10)	−0.0148 (9)	−0.0201 (9)	−0.0081 (8)
C26	0.0715 (9)	0.0565 (8)	0.0480 (7)	−0.0221 (7)	−0.0097 (6)	−0.0065 (6)
C27	0.0603 (8)	0.0576 (8)	0.0378 (6)	−0.0308 (6)	−0.0062 (5)	−0.0065 (5)
N1	0.0501 (6)	0.0427 (5)	0.0385 (5)	−0.0179 (4)	−0.0008 (4)	−0.0105 (4)
N2	0.0837 (9)	0.0513 (6)	0.0546 (7)	−0.0321 (6)	0.0017 (6)	−0.0150 (5)
N4	0.0921 (10)	0.0831 (9)	0.0569 (7)	−0.0572 (9)	−0.0091 (7)	−0.0046 (7)
O1	0.0656 (6)	0.0654 (6)	0.0495 (5)	−0.0253 (5)	0.0130 (4)	−0.0253 (5)
O2	0.1427 (12)	0.1039 (10)	0.1091 (10)	−0.0885 (10)	−0.0031 (9)	−0.0309 (8)
O3	0.0747 (8)	0.1167 (11)	0.1149 (11)	−0.0555 (8)	0.0020 (7)	−0.0195 (8)

Geometric parameters (Å, º) top

C1—C2	1.378 (2)	C13—H13	0.93
C1—C6	1.383 (2)	C14—C27	1.4085 (18)
C1—C7	1.509 (2)	C14—C15	1.4099 (17)
C2—C3	1.3779 (19)	C15—C16	1.414 (2)
C2—H2	0.93	C15—C20	1.4327 (18)
C3—C4	1.3852 (18)	C16—C17	1.361 (2)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.3835 (18)	C17—C18	1.405 (3)
C4—C8	1.4923 (16)	C17—H17	0.93
C5—C6	1.3814 (18)	C18—C19	1.339 (3)
C5—H5	0.93	C18—H18	0.93
C6—H6	0.93	C19—C20	1.429 (2)
C7—H7A	0.96	C19—H19	0.93
C7—H7B	0.96	C20—C21	1.377 (2)
C7—H7C	0.96	C21—C22	1.390 (2)
C8—O1	1.2133 (13)	C21—H21	0.93
C8—C9	1.4933 (16)	C22—C23	1.415 (2)
C9—C10	1.3289 (15)	C22—C27	1.4426 (18)
C9—N1	1.4332 (14)	C23—C24	1.344 (3)
C10—C14	1.4772 (15)	C23—H23	0.93
C10—H10	0.93	C24—C25	1.411 (3)
C11—N2	1.3029 (17)	C24—H24	0.93
C11—N1	1.3657 (16)	C25—C26	1.355 (2)
C11—H11	0.93	C25—H25	0.93
C12—C13	1.3510 (17)	C26—C27	1.418 (2)
C12—N2	1.3551 (18)	C26—H26	0.93
C12—N4	1.4381 (18)	N4—O2	1.2174 (17)
C13—N1	1.3563 (15)	N4—O3	1.2346 (18)

C2—C1—C6	118.62 (13)	C14—C15—C20	119.28 (13)
C2—C1—C7	120.37 (15)	C16—C15—C20	117.91 (12)
C6—C1—C7	121.01 (15)	C17—C16—C15	121.32 (15)
C1—C2—C3	120.94 (14)	C17—C16—H16	119.3
C1—C2—H2	119.5	C15—C16—H16	119.3
C3—C2—H2	119.5	C16—C17—C18	120.57 (18)
C2—C3—C4	120.40 (13)	C16—C17—H17	119.7
C2—C3—H3	119.8	C18—C17—H17	119.7
C4—C3—H3	119.8	C19—C18—C17	120.34 (16)
C5—C4—C3	118.92 (12)	C19—C18—H18	119.8
C5—C4—C8	123.45 (11)	C17—C18—H18	119.8
C3—C4—C8	117.62 (11)	C18—C19—C20	121.48 (16)
C6—C5—C4	120.24 (13)	C18—C19—H19	119.3
C6—C5—H5	119.9	C20—C19—H19	119.3
C4—C5—H5	119.9	C21—C20—C19	122.36 (14)
C5—C6—C1	120.85 (13)	C21—C20—C15	119.29 (13)
C5—C6—H6	119.6	C19—C20—C15	118.35 (15)
C1—C6—H6	119.6	C20—C21—C22	122.53 (12)
C1—C7—H7A	109.5	C20—C21—H21	118.7
C1—C7—H7B	109.5	C22—C21—H21	118.7
H7A—C7—H7B	109.5	C21—C22—C23	121.93 (14)
C1—C7—H7C	109.5	C21—C22—C27	119.26 (13)
H7A—C7—H7C	109.5	C23—C22—C27	118.78 (16)
H7B—C7—H7C	109.5	C24—C23—C22	121.12 (16)
O1—C8—C4	121.31 (10)	C24—C23—H23	119.4
O1—C8—C9	120.52 (11)	C22—C23—H23	119.4
C4—C8—C9	118.02 (10)	C23—C24—C25	120.55 (16)
C10—C9—N1	121.36 (10)	C23—C24—H24	119.7
C10—C9—C8	122.61 (10)	C25—C24—H24	119.7
N1—C9—C8	115.87 (9)	C26—C25—C24	120.61 (18)
C9—C10—C14	129.89 (10)	C26—C25—H25	119.7
C9—C10—H10	115.1	C24—C25—H25	119.7
C14—C10—H10	115.1	C25—C26—C27	121.12 (14)
N2—C11—N1	112.40 (13)	C25—C26—H26	119.4
N2—C11—H11	123.8	C27—C26—H26	119.4
N1—C11—H11	123.8	C14—C27—C26	123.60 (11)
C13—C12—N2	112.85 (11)	C14—C27—C22	118.59 (13)
C13—C12—N4	125.76 (14)	C26—C27—C22	117.70 (12)
N2—C12—N4	121.39 (13)	C13—N1—C11	106.73 (10)
C12—C13—N1	104.50 (11)	C13—N1—C9	125.53 (10)
C12—C13—H13	127.7	C11—N1—C9	127.71 (11)
N1—C13—H13	127.7	C11—N2—C12	103.51 (11)
C27—C14—C15	121.01 (11)	O2—N4—O3	124.53 (15)
C27—C14—C10	120.56 (11)	O2—N4—C12	118.72 (16)
C15—C14—C10	118.04 (11)	O3—N4—C12	116.74 (13)
C14—C15—C16	122.80 (11)

C6—C1—C2—C3	−0.8 (2)	C14—C15—C20—C19	178.69 (11)
C7—C1—C2—C3	179.16 (15)	C16—C15—C20—C19	−1.83 (17)
C1—C2—C3—C4	−0.9 (2)	C19—C20—C21—C22	−178.42 (12)
C2—C3—C4—C5	1.47 (19)	C15—C20—C21—C22	1.3 (2)
C2—C3—C4—C8	−179.46 (11)	C20—C21—C22—C23	178.14 (14)
C3—C4—C5—C6	−0.28 (18)	C20—C21—C22—C27	0.1 (2)
C8—C4—C5—C6	−179.29 (11)	C21—C22—C23—C24	−176.94 (16)
C4—C5—C6—C1	−1.5 (2)	C27—C22—C23—C24	1.1 (3)
C2—C1—C6—C5	2.0 (2)	C22—C23—C24—C25	1.6 (3)
C7—C1—C6—C5	−177.96 (14)	C23—C24—C25—C26	−2.0 (3)
C5—C4—C8—O1	127.74 (13)	C24—C25—C26—C27	−0.5 (2)
C3—C4—C8—O1	−51.28 (16)	C15—C14—C27—C26	−174.16 (11)
C5—C4—C8—C9	−56.71 (15)	C10—C14—C27—C26	−1.40 (18)
C3—C4—C8—C9	124.27 (12)	C15—C14—C27—C22	2.01 (17)
O1—C8—C9—C10	161.69 (12)	C10—C14—C27—C22	174.76 (11)
C4—C8—C9—C10	−13.90 (17)	C25—C26—C27—C14	179.39 (13)
O1—C8—C9—N1	−13.70 (16)	C25—C26—C27—C22	3.2 (2)
C4—C8—C9—N1	170.72 (10)	C21—C22—C27—C14	−1.75 (18)
N1—C9—C10—C14	5.68 (19)	C23—C22—C27—C14	−179.84 (13)
C8—C9—C10—C14	−169.46 (11)	C21—C22—C27—C26	174.64 (12)
N2—C12—C13—N1	0.92 (14)	C23—C22—C27—C26	−3.45 (19)
N4—C12—C13—N1	−178.45 (11)	C12—C13—N1—C11	−0.61 (13)
C9—C10—C14—C27	59.15 (18)	C12—C13—N1—C9	−178.63 (10)
C9—C10—C14—C15	−127.88 (14)	N2—C11—N1—C13	0.13 (14)
C27—C14—C15—C16	179.91 (11)	N2—C11—N1—C9	178.09 (10)
C10—C14—C15—C16	6.98 (17)	C10—C9—N1—C13	54.97 (16)
C27—C14—C15—C20	−0.64 (17)	C8—C9—N1—C13	−129.58 (11)
C10—C14—C15—C20	−173.57 (10)	C10—C9—N1—C11	−122.63 (14)
C14—C15—C16—C17	−178.85 (12)	C8—C9—N1—C11	52.83 (15)
C20—C15—C16—C17	1.70 (19)	N1—C11—N2—C12	0.41 (14)
C15—C16—C17—C18	−0.4 (2)	C13—C12—N2—C11	−0.83 (14)
C16—C17—C18—C19	−0.7 (2)	N4—C12—N2—C11	178.56 (11)
C17—C18—C19—C20	0.5 (2)	C13—C12—N4—O2	178.97 (13)
C18—C19—C20—C21	−179.54 (14)	N2—C12—N4—O2	−0.34 (19)
C18—C19—C20—C15	0.8 (2)	C13—C12—N4—O3	−1.7 (2)
C14—C15—C20—C21	−1.03 (17)	N2—C12—N4—O3	178.98 (13)
C16—C15—C20—C21	178.45 (12)

Experimental details

Crystal data
Chemical formula	C₂₇H₁₉N₃O₃
M_r	433.45
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.9335 (9), 11.2626 (13), 13.0291 (15)
α, β, γ (°)	75.454 (2), 85.763 (2), 71.059 (2)
V (Å³)	1065.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.23 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.968, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	12116, 4621, 3646
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.05
No. of reflections	4621
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.23

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.

References

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