2-(1H-Benzotriazol-1-yl)-1-(3-methoxy­benzo­yl)ethyl isonicotinate

Wang, W.; Mei, Z.-H.

doi:10.1107/S1600536809001196

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o357

doi:10.1107/S1600536809001196

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2-(1H-Benzotriazol-1-yl)-1-(3-methoxybenzoyl)ethyl isonicotinate

Wei Wang ^a and Zhen-Hua Mei ^a ^*

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, 210009 Nanjing, Jiangsu, People's Republic of China
^*Correspondence e-mail: mzh62@qust.edu.cn

(Received 5 January 2009; accepted 10 January 2009; online 23 January 2009)

In the title compound, C₂₂H₁₈N₄O₄, molecules are linked to each other by C—H⋯N and C—H⋯O intermolecular hydrogen-bonding interactions. The crystal packing is further stabilized by C—H⋯π, and π–π interactions with a distance of 3.783 (3) Å between the centroids of the benzene rings of the benzotriazole system.

Related literature

For general background on benzotriazole and its derivatives, see: Chen & Wu (2005 ). For details of the synthesis, see: Wan et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₈N₄O₄
M_r = 402.40
Triclinic, $[P \overline 1]$
a = 9.4839 (18) Å
b = 10.3611 (19) Å
c = 11.276 (2) Å
α = 109.342 (3)°
β = 102.664 (3)°
γ = 97.985 (3)°
V = 992.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.33 × 0.16 × 0.08 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.969, T_max = 0.992
5605 measured reflections
3819 independent reflections
2822 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.119
S = 1.04
3819 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯N3ⁱ	0.93	2.48	3.328 (3)	151
C9—H9B⋯O1ⁱⁱ	0.97	2.56	3.471 (2)	157
C15—H15A⋯O1ⁱⁱ	0.93	2.46	3.368 (3)	164
C20—H20A⋯Cg3ⁱⁱⁱ	0.93	2.85	3.767	168
C22—H22C⋯Cg4^iv	0.96	2.87	3.530	127
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+1; (iii) x, y, z-1; (iv) x, y+1, z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001196/at2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001196/at2705Isup2.hkl

checkCIF report

Comment top

Benzotriazole and its derivatives exhibit an excellent pharmacological activities, such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). In order to find a new benzotriazole compound with higher bioactivity, the title compound, (I) (Fig. 1), was synthesized and its crystal structure was presented here.

In (I), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring is mostly planar with a dihedral angle of 1.75 (1)° between the N1—N3/C10/C11 triazole and C10—C15 benzene rings. The mean plane makes dihedral angles of 70.93 (1) and 19.8 (1)° with the N4/C17—C21 pyridine and C1—C6 benzene rings, respectively, and the dihedral angle between the latter two aromatic rings is 80.08 (1)°.

In the crystal structure, molecules of (I) are linked to each other by C3—H3B···N3, and further linked by C—H···O intermolecular hydrogen bonding interactions (C9—H9B···O1 and C15—H15A···O1), and stabilized by C—H···π interactions (Table 1). The distances of 3.783 Å between the centroids of the rings C10—C15 related by the symmetry code (-x, 1 - y, 1 - z) suggests a possible π–π interaction.

Related literature top

For general background on benzotriazole and its derivatives, see: Chen & Wu (2005). For details of the synthesis, see: Wan et al. (2006). For bond-length data, see: Allen et al. (1987). Cg3 and Cg4 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

Experimental top

The title compound was prepared according to the literature method of Wan et al. (20067). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of one week.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the a axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(3-methoxybenzoyl)ethyl isonicotinate top

Crystal data top

C₂₂H₁₈N₄O₄	Z = 2
M_r = 402.40	F(000) = 420
Triclinic, P1	D_x = 1.346 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4839 (18) Å	Cell parameters from 1711 reflections
b = 10.3611 (19) Å	θ = 2.6–24.7°
c = 11.276 (2) Å	µ = 0.10 mm⁻¹
α = 109.342 (3)°	T = 293 K
β = 102.664 (3)°	Plate, colourless
γ = 97.985 (3)°	0.33 × 0.16 × 0.08 mm
V = 992.8 (3) Å³

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3819 independent reflections
Radiation source: fine-focus sealed tube	2822 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.1°, θ_min = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→10
T_min = 0.969, T_max = 0.992	l = −12→13
5605 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0502P)² + 0.1574P] where P = (F_o² + 2F_c²)/3
3819 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₁₈N₄O₄	γ = 97.985 (3)°
M_r = 402.40	V = 992.8 (3) Å³
Triclinic, P1	Z = 2
a = 9.4839 (18) Å	Mo Kα radiation
b = 10.3611 (19) Å	µ = 0.10 mm⁻¹
c = 11.276 (2) Å	T = 293 K
α = 109.342 (3)°	0.33 × 0.16 × 0.08 mm
β = 102.664 (3)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3819 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2822 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.992	R_int = 0.013
5605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	Δρ_max = 0.15 e Å⁻³
3819 reflections	Δρ_min = −0.19 e Å⁻³
271 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
O2	0.21549 (13)	0.94145 (12)	0.45684 (11)	0.0511 (3)
O3	0.40290 (15)	1.11047 (14)	0.47141 (13)	0.0639 (4)
N1	0.22089 (16)	0.73861 (15)	0.58935 (14)	0.0498 (4)
C7	0.23974 (18)	1.12532 (18)	0.66726 (18)	0.0474 (4)
C6	0.31816 (18)	1.19911 (18)	0.80934 (17)	0.0457 (4)
C17	0.23003 (19)	0.97219 (18)	0.26265 (17)	0.0481 (4)
C1	0.2728 (2)	1.31472 (19)	0.88006 (18)	0.0526 (5)
H1A	0.1952	1.3441	0.8379	0.063*
C16	0.29418 (19)	1.01773 (19)	0.40669 (18)	0.0487 (4)
O1	0.15281 (15)	1.17332 (14)	0.60783 (13)	0.0691 (4)
C8	0.26559 (19)	0.98062 (18)	0.59616 (17)	0.0474 (4)
H8A	0.3712	0.9811	0.6233	0.057*
N2	0.34386 (18)	0.72584 (18)	0.66902 (16)	0.0642 (5)
C10	0.16172 (19)	0.61663 (18)	0.48299 (17)	0.0457 (4)
C21	0.2851 (2)	1.0500 (2)	0.19695 (19)	0.0556 (5)
H21A	0.3604	1.1310	0.2422	0.067*
C9	0.1742 (2)	0.86971 (18)	0.62674 (18)	0.0498 (4)
H9A	0.1837	0.9040	0.7199	0.060*
H9B	0.0704	0.8535	0.5805	0.060*
C15	0.0363 (2)	0.57215 (19)	0.37579 (18)	0.0524 (5)
H15A	−0.0264	0.6310	0.3634	0.063*
N3	0.36612 (19)	0.60040 (18)	0.61744 (17)	0.0687 (5)
O4	0.28449 (18)	1.49647 (15)	1.07256 (15)	0.0812 (5)
C11	0.2550 (2)	0.52895 (19)	0.50226 (18)	0.0522 (5)
C5	0.4361 (2)	1.1570 (2)	0.87303 (19)	0.0565 (5)
H5A	0.4675	1.0791	0.8273	0.068*
C2	0.3411 (2)	1.38696 (19)	1.01200 (19)	0.0551 (5)
N4	0.1207 (2)	0.8890 (2)	−0.00867 (17)	0.0771 (5)
C3	0.4587 (2)	1.3456 (2)	1.0743 (2)	0.0626 (5)
H3B	0.5059	1.3944	1.1632	0.075*
C12	0.2266 (2)	0.3910 (2)	0.4131 (2)	0.0615 (5)
H12A	0.2887	0.3316	0.4253	0.074*
C14	0.0107 (2)	0.4364 (2)	0.28959 (19)	0.0604 (5)
H14A	−0.0717	0.4024	0.2164	0.072*
C4	0.5054 (2)	1.2319 (2)	1.0041 (2)	0.0670 (6)
H4B	0.5854	1.2052	1.0460	0.080*
C13	0.1044 (2)	0.3469 (2)	0.3078 (2)	0.0627 (5)
H13A	0.0826	0.2555	0.2466	0.075*
C20	0.2260 (2)	1.0049 (2)	0.0634 (2)	0.0680 (6)
H20A	0.2622	1.0593	0.0207	0.082*
C19	0.0693 (3)	0.8157 (3)	0.0559 (2)	0.0825 (7)
H19A	−0.0042	0.7339	0.0076	0.099*
C22	0.3532 (3)	1.5758 (2)	1.2089 (2)	0.0840 (7)
H22A	0.3031	1.6493	1.2391	0.126*
H22B	0.4555	1.6163	1.2223	0.126*
H22C	0.3471	1.5151	1.2570	0.126*
C18	0.1180 (2)	0.8531 (2)	0.1897 (2)	0.0695 (6)
H18A	0.0762	0.7991	0.2302	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0529 (7)	0.0520 (7)	0.0458 (7)	0.0072 (6)	0.0145 (6)	0.0166 (6)
O3	0.0558 (8)	0.0645 (9)	0.0632 (9)	−0.0020 (7)	0.0069 (7)	0.0265 (7)
N1	0.0547 (9)	0.0462 (9)	0.0449 (9)	0.0113 (7)	0.0066 (7)	0.0176 (7)
C7	0.0417 (9)	0.0488 (10)	0.0528 (11)	0.0117 (8)	0.0111 (8)	0.0213 (8)
C6	0.0435 (9)	0.0445 (10)	0.0490 (11)	0.0063 (8)	0.0119 (8)	0.0196 (8)
C17	0.0463 (10)	0.0511 (11)	0.0494 (11)	0.0166 (8)	0.0176 (8)	0.0172 (8)
C1	0.0477 (10)	0.0533 (11)	0.0565 (12)	0.0135 (8)	0.0109 (9)	0.0219 (9)
C16	0.0473 (10)	0.0476 (10)	0.0546 (11)	0.0149 (9)	0.0175 (9)	0.0199 (9)
O1	0.0717 (9)	0.0700 (9)	0.0587 (9)	0.0335 (8)	0.0025 (7)	0.0186 (7)
C8	0.0464 (10)	0.0486 (10)	0.0451 (10)	0.0114 (8)	0.0100 (8)	0.0165 (8)
N2	0.0651 (10)	0.0611 (11)	0.0550 (10)	0.0141 (8)	−0.0021 (8)	0.0197 (8)
C10	0.0511 (10)	0.0447 (10)	0.0426 (10)	0.0100 (8)	0.0128 (8)	0.0187 (8)
C21	0.0563 (11)	0.0538 (11)	0.0557 (12)	0.0126 (9)	0.0174 (9)	0.0185 (9)
C9	0.0546 (10)	0.0456 (10)	0.0479 (10)	0.0106 (8)	0.0146 (8)	0.0162 (8)
C15	0.0529 (11)	0.0565 (11)	0.0493 (11)	0.0154 (9)	0.0121 (9)	0.0221 (9)
N3	0.0723 (11)	0.0633 (11)	0.0633 (11)	0.0238 (9)	0.0017 (9)	0.0226 (9)
O4	0.0977 (11)	0.0704 (10)	0.0664 (10)	0.0311 (9)	0.0243 (9)	0.0088 (8)
C11	0.0577 (11)	0.0528 (11)	0.0476 (11)	0.0157 (9)	0.0101 (9)	0.0226 (9)
C5	0.0577 (11)	0.0552 (11)	0.0558 (12)	0.0196 (9)	0.0119 (9)	0.0196 (9)
C2	0.0593 (11)	0.0491 (11)	0.0535 (12)	0.0076 (9)	0.0178 (9)	0.0154 (9)
N4	0.0788 (12)	0.0912 (14)	0.0529 (11)	0.0082 (11)	0.0183 (10)	0.0213 (10)
C3	0.0667 (13)	0.0630 (13)	0.0483 (12)	0.0062 (10)	0.0070 (10)	0.0178 (10)
C12	0.0742 (13)	0.0531 (12)	0.0641 (13)	0.0248 (10)	0.0225 (11)	0.0245 (10)
C14	0.0603 (12)	0.0626 (13)	0.0485 (11)	0.0075 (10)	0.0118 (9)	0.0135 (9)
C4	0.0646 (13)	0.0745 (14)	0.0564 (13)	0.0205 (11)	0.0018 (10)	0.0258 (11)
C13	0.0761 (14)	0.0468 (11)	0.0595 (13)	0.0099 (10)	0.0231 (11)	0.0120 (9)
C20	0.0751 (14)	0.0726 (15)	0.0586 (13)	0.0117 (12)	0.0235 (11)	0.0266 (11)
C19	0.0799 (16)	0.0866 (17)	0.0563 (14)	−0.0113 (13)	0.0136 (12)	0.0116 (12)
C22	0.1063 (19)	0.0643 (14)	0.0660 (15)	0.0046 (13)	0.0360 (14)	0.0037 (11)
C18	0.0672 (13)	0.0733 (14)	0.0575 (13)	−0.0036 (11)	0.0170 (11)	0.0194 (11)

Geometric parameters (Å, º) top

O2—C16	1.349 (2)	C15—H15A	0.9300
O2—C8	1.434 (2)	N3—C11	1.375 (2)
O3—C16	1.204 (2)	O4—C2	1.363 (2)
N1—N2	1.359 (2)	O4—C22	1.428 (2)
N1—C10	1.362 (2)	C11—C12	1.396 (3)
N1—C9	1.445 (2)	C5—C4	1.375 (3)
C7—O1	1.212 (2)	C5—H5A	0.9300
C7—C6	1.488 (2)	C2—C3	1.382 (3)
C7—C8	1.531 (2)	N4—C19	1.327 (3)
C6—C1	1.384 (2)	N4—C20	1.329 (3)
C6—C5	1.395 (2)	C3—C4	1.376 (3)
C17—C18	1.382 (3)	C3—H3B	0.9300
C17—C21	1.385 (3)	C12—C13	1.361 (3)
C17—C16	1.487 (2)	C12—H12A	0.9300
C1—C2	1.378 (3)	C14—C13	1.403 (3)
C1—H1A	0.9300	C14—H14A	0.9300
C8—C9	1.519 (2)	C4—H4B	0.9300
C8—H8A	0.9800	C13—H13A	0.9300
N2—N3	1.304 (2)	C20—H20A	0.9300
C10—C11	1.387 (2)	C19—C18	1.378 (3)
C10—C15	1.392 (2)	C19—H19A	0.9300
C21—C20	1.375 (3)	C22—H22A	0.9600
C21—H21A	0.9300	C22—H22B	0.9600
C9—H9A	0.9700	C22—H22C	0.9600
C9—H9B	0.9700	C18—H18A	0.9300
C15—C14	1.371 (3)

C16—O2—C8	115.78 (13)	C2—O4—C22	117.93 (18)
N2—N1—C10	109.89 (14)	N3—C11—C10	108.94 (16)
N2—N1—C9	118.99 (14)	N3—C11—C12	130.21 (18)
C10—N1—C9	131.12 (15)	C10—C11—C12	120.83 (17)
O1—C7—C6	122.39 (16)	C4—C5—C6	119.33 (18)
O1—C7—C8	119.34 (16)	C4—C5—H5A	120.3
C6—C7—C8	118.21 (15)	C6—C5—H5A	120.3
C1—C6—C5	119.12 (17)	O4—C2—C1	115.94 (18)
C1—C6—C7	118.39 (15)	O4—C2—C3	124.37 (18)
C5—C6—C7	122.49 (16)	C1—C2—C3	119.69 (18)
C18—C17—C21	117.82 (18)	C19—N4—C20	116.16 (19)
C18—C17—C16	122.72 (18)	C4—C3—C2	119.54 (19)
C21—C17—C16	119.45 (17)	C4—C3—H3B	120.2
C2—C1—C6	120.96 (17)	C2—C3—H3B	120.2
C2—C1—H1A	119.5	C13—C12—C11	117.29 (18)
C6—C1—H1A	119.5	C13—C12—H12A	121.4
O3—C16—O2	123.70 (17)	C11—C12—H12A	121.4
O3—C16—C17	124.81 (18)	C15—C14—C13	122.40 (19)
O2—C16—C17	111.49 (15)	C15—C14—H14A	118.8
O2—C8—C9	106.06 (13)	C13—C14—H14A	118.8
O2—C8—C7	110.80 (14)	C5—C4—C3	121.34 (19)
C9—C8—C7	109.81 (14)	C5—C4—H4B	119.3
O2—C8—H8A	110.0	C3—C4—H4B	119.3
C9—C8—H8A	110.0	C12—C13—C14	121.34 (18)
C7—C8—H8A	110.0	C12—C13—H13A	119.3
N3—N2—N1	109.04 (15)	C14—C13—H13A	119.3
N1—C10—C11	104.25 (15)	N4—C20—C21	124.4 (2)
N1—C10—C15	133.49 (16)	N4—C20—H20A	117.8
C11—C10—C15	122.22 (16)	C21—C20—H20A	117.8
C20—C21—C17	118.61 (19)	N4—C19—C18	124.2 (2)
C20—C21—H21A	120.7	N4—C19—H19A	117.9
C17—C21—H21A	120.7	C18—C19—H19A	117.9
N1—C9—C8	111.93 (14)	O4—C22—H22A	109.5
N1—C9—H9A	109.2	O4—C22—H22B	109.5
C8—C9—H9A	109.2	H22A—C22—H22B	109.5
N1—C9—H9B	109.2	O4—C22—H22C	109.5
C8—C9—H9B	109.2	H22A—C22—H22C	109.5
H9A—C9—H9B	107.9	H22B—C22—H22C	109.5
C14—C15—C10	115.92 (17)	C19—C18—C17	118.8 (2)
C14—C15—H15A	122.0	C19—C18—H18A	120.6
C10—C15—H15A	122.0	C17—C18—H18A	120.6
N2—N3—C11	107.87 (15)

O1—C7—C6—C1	10.4 (3)	N1—C10—C15—C14	−177.61 (19)
C8—C7—C6—C1	−166.80 (16)	C11—C10—C15—C14	−0.4 (3)
O1—C7—C6—C5	−168.84 (18)	N1—N2—N3—C11	−0.5 (2)
C8—C7—C6—C5	13.9 (3)	N2—N3—C11—C10	0.6 (2)
C5—C6—C1—C2	−0.9 (3)	N2—N3—C11—C12	−177.9 (2)
C7—C6—C1—C2	179.82 (17)	N1—C10—C11—N3	−0.4 (2)
C8—O2—C16—O3	2.3 (2)	C15—C10—C11—N3	−178.31 (17)
C8—O2—C16—C17	−177.93 (13)	N1—C10—C11—C12	178.28 (18)
C18—C17—C16—O3	170.73 (19)	C15—C10—C11—C12	0.4 (3)
C21—C17—C16—O3	−8.3 (3)	C1—C6—C5—C4	−0.6 (3)
C18—C17—C16—O2	−9.0 (2)	C7—C6—C5—C4	178.69 (18)
C21—C17—C16—O2	172.00 (15)	C22—O4—C2—C1	−179.05 (18)
C16—O2—C8—C9	−172.79 (13)	C22—O4—C2—C3	1.4 (3)
C16—O2—C8—C7	68.10 (18)	C6—C1—C2—O4	−178.11 (17)
O1—C7—C8—O2	18.0 (2)	C6—C1—C2—C3	1.5 (3)
C6—C7—C8—O2	−164.64 (14)	O4—C2—C3—C4	178.9 (2)
O1—C7—C8—C9	−98.8 (2)	C1—C2—C3—C4	−0.6 (3)
C6—C7—C8—C9	78.53 (19)	N3—C11—C12—C13	178.3 (2)
C10—N1—N2—N3	0.3 (2)	C10—C11—C12—C13	−0.1 (3)
C9—N1—N2—N3	−179.98 (16)	C10—C15—C14—C13	0.2 (3)
N2—N1—C10—C11	0.1 (2)	C6—C5—C4—C3	1.5 (3)
C9—N1—C10—C11	−179.61 (17)	C2—C3—C4—C5	−0.9 (3)
N2—N1—C10—C15	177.64 (19)	C11—C12—C13—C14	−0.1 (3)
C9—N1—C10—C15	−2.1 (3)	C15—C14—C13—C12	0.0 (3)
C18—C17—C21—C20	−0.1 (3)	C19—N4—C20—C21	1.4 (3)
C16—C17—C21—C20	178.95 (17)	C17—C21—C20—N4	−1.5 (3)
N2—N1—C9—C8	79.2 (2)	C20—N4—C19—C18	0.2 (4)
C10—N1—C9—C8	−101.1 (2)	N4—C19—C18—C17	−1.7 (4)
O2—C8—C9—N1	74.36 (17)	C21—C17—C18—C19	1.6 (3)
C7—C8—C9—N1	−165.87 (14)	C16—C17—C18—C19	−177.42 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···N3ⁱ	0.93	2.48	3.328 (3)	151
C9—H9B···O1ⁱⁱ	0.97	2.56	3.471 (2)	157
C15—H15A···O1ⁱⁱ	0.93	2.46	3.368 (3)	164
C20—H20A···Cg3ⁱⁱⁱ	0.93	2.85	3.767	168
C22—H22C···Cg4^iv	0.96	2.87	3.530	127

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₄O₄
M_r	402.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4839 (18), 10.3611 (19), 11.276 (2)
α, β, γ (°)	109.342 (3), 102.664 (3), 97.985 (3)
V (Å³)	992.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.16 × 0.08

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.969, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5605, 3819, 2822
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.119, 1.04
No. of reflections	3819
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···N3ⁱ	0.93	2.484	3.328 (3)	150.92
C9—H9B···O1ⁱⁱ	0.97	2.558	3.471 (2)	157.06
C15—H15A···O1ⁱⁱ	0.93	2.462	3.368 (3)	164.41
C20—H20A···Cg3ⁱⁱⁱ	0.93	2.852	3.767	167.99
C22—H22C···Cg4^iv	0.96	2.871	3.530	126.65

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

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant No. Y2006B07).

References

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