Dimethyl 9-benzyl-3-cyano-9H-pyrrolo[1,2-a]benzimidazole-1,2-dicarboxyl­ate

Gu, W.-J.; Jiang, Y.-L.; Wang, B.-X.

doi:10.1107/S1600536809048867

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3155

doi:10.1107/S1600536809048867

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Dimethyl 9-benzyl-3-cyano-9H-pyrrolo[1,2-a]benzimidazole-1,2-dicarboxylate

Wei-Jin Gu,^a Yu-Liang Jiang ^a and Bing-Xiang Wang ^a ^*

^aDepartment of Applied Chemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China
^*Correspondence e-mail: wang.bingxiang@yahoo.com

(Received 4 November 2009; accepted 17 November 2009; online 21 November 2009)

The title compound, C₂₂H₁₇N₃O₄, was prepared through 1,3-dipolar cycloaddition: the dihedral angle between the benzimidazole and benzene rings is 80.93 (6)°. The crystal structure is stabilized by weak π–π interactions between the planar pyrrolobenzimidazole rings (r.m.s. deviation = 0.0293 Å) of neighbouring molecules, forming chains along the c axis. The perpendicular distance is 3.47 (2) Å and the centroid–centroid distances are in the range of 3.590 (3)–3.944 (3) Å.

Related literature

For the use of 1,3-dipolar cycloaddition reactions of azomethine ylides in the construction of five-membered nitrogen heteroaromatic ring systems, see: Berry et al. (2007 ). For the applications of nitrogen heteroaromatic ring systems, see: Ansari & Lal (2009 ); Shen et al. (2006 , 2008 ); Zhang et al. (2009 ). For the synthesis, see: Wang et al. (2000 ).

Experimental

Crystal data

C₂₂H₁₇N₃O₄
M_r = 387.39
Monoclinic, P 2₁ /c
a = 9.8681 (15) Å
b = 24.766 (2) Å
c = 7.6551 (11) Å
β = 91.973 (3)°
V = 1869.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.97, T_max = 0.98
13898 measured reflections
3615 independent reflections
2699 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.125
S = 1.03
3615 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048867/zq2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048867/zq2016Isup2.hkl

checkCIF report

Comment top

1,3-Dipolar cycloadditions of azomethine ylides are one of the most powerful methods for the construction of five membered nitrogen heteroaromatic ring systems, both inter and intramolecularly (Berry et al., 2007). Nitrogen heteroaromatic ring systems, such as benzimidazoles and indolizines, can be utilized as not only a wide variety of biologically active and medicinally significant compounds (Zhang et al., 2009; Ansari et al., 2009), but also organic fluorescence probes (Shen et al., 2006; Shen et al., 2008). In our continuing studies in organic fluorescence probes, we synthesized the title compound (I), dimethyl 4-benzyl-1-cyano-4H-pyrrolo[1, 2 - a] benzimidazole-2,3-dicarboxylate, C₂₂H₁₇N₃O₄.

The crystal structure of (I) reveals that all the bond lengths and angles have normal values. There is one title compound molecule per asymmetric unit. Each molecule contains one pyrrolo-benzimidazole ring A and one benzyl ring B (Fig 1). The rings A and B are almost perpendicular, making a dihedral angle of 80.93 (6)°.

In the crystal structure there are weak π–π interactions between the planar pyrrolo-benzimidazole rings (r.m.s. deviation of 0.0293 Å) of neighbouring molecules. The perpendicular distance is 3.47 (2) Å and the distances Cg1—Cg2ⁱ and Cg2—Cg2ⁱⁱⁱ are 3.590 (3) and 3.944 (3) Å, respectively. (Cg1 is the center of ring C7/C8/C9/C10/N1 and Cg2 is the center of ring C1/C2/C3/C4/C5/C6; i: 2 - x, 2 - y, 2 - z; iii: 2 - x, 2 - y, 1 - z). Through the π–π interactions one-dimensional chains are formed along c axis.

Related literature top

For the use of 1,3-dipolar cycloaddition reactions of azomethine ylides in the construction of five-membered nitrogen heteroaromatic ring systems, see: Berry et al. (2007). For the applications of nitrogen heteroaromatic ring systems, see: Ansari & Lal (2009); Shen et al. (2006, 2008); Zhang et al. (2009). For the synthesis, see: Wang et al. (2000).

Experimental top

Dimethyl 4-benzyl-1-cyano-4H-pyrrolo[1,2-a] benzimidazole-2,3-dicarboxylate was prepared through 1,3-dipolar cycloaddition according to a procedure described in the literature (Wang et al., 2000). Colorless crystals were obtained by recrystallization from a dichloromethane solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at 50% probability level.
	Fig. 2. A view of the packing down b axis.
	Fig. 3. A view of the one-dimensional chains down b axis. Dashed lines indicate weak π–π interaction and all H atoms have been omitted for clarity (i: 2 - x, 2 - y, 2 - z; ii: x, y, 1 + z; iii: 2 - x, 2 - y, 1 - z).

Dimethyl 9-benzyl-3-cyano-9H-pyrrolo[1,2-a]benzimidazole-1,2-dicarboxylate top

Crystal data top

C₂₂H₁₇N₃O₄	F(000) = 808
M_r = 387.39	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1791 reflections
a = 9.8681 (15) Å	θ = 2.6–25.2°
b = 24.766 (2) Å	µ = 0.10 mm⁻¹
c = 7.6551 (11) Å	T = 291 K
β = 91.973 (3)°	Block, colorless
V = 1869.7 (4) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3615 independent reflections
Radiation source: sealed tube	2699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
phi and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
T_min = 0.97, T_max = 0.98	k = −26→30
13898 measured reflections	l = −9→9

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.05P)² + 0.66P] where P = (F_o² + 2F_c²)/3
3615 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₁₇N₃O₄	V = 1869.7 (4) Å³
M_r = 387.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8681 (15) Å	µ = 0.10 mm⁻¹
b = 24.766 (2) Å	T = 291 K
c = 7.6551 (11) Å	0.26 × 0.22 × 0.20 mm
β = 91.973 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3615 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2699 reflections with I > 2σ(I)
T_min = 0.97, T_max = 0.98	R_int = 0.057
13898 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
3615 reflections	Δρ_min = −0.19 e Å⁻³
264 parameters

Special details top

Experimental. 1H-NMR (CDCl₃, 400 MHz) δ: 3.81 (s, 3H, –COOCH₃), 4.00 (s, 3H, –COOCH₃), 5.92 (s, 2H, –CH₂Ph), 7.20–7.41 (m, 8H, ArH), 8.07 (d, 1H, J = 7.9 Hz, ArH)

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

-0.0001(0.0049) x + 11.1526(0.0083)y + 6.8309(0.0017) z = 16.2473 (0.0105)

* 0.0370 (0.0017) C1 * 0.0187 (0.0017) C2 * -0.0329 (0.0017) C3 * -0.0312 (0.0019) C4 * -0.0132 (0.0017) C5 * 0.0115 (0.0017) C6 * 0.0056 (0.0017) C7 * -0.0396 (0.0016) C8 * -0.0420 (0.0016) C9 * 0.0128 (0.0016) C10 * 0.0392 (0.0015) N1 * 0.0341 (0.0015) N2

Rms deviation of fitted atoms = 0.0293

7.9901(0.0063)x + 10.7417(0.0233)y - 3.2379(0.0071)z = 12.8495 (0.0190)

Angle to previous plane (with approximate e.s.d.) = 80.93 (0.06)

* 0.0109 (0.0016) C13 * -0.0131 (0.0017) C14 * 0.0058 (0.0018) C15 * 0.0036 (0.0019) C16 * -0.0055 (0.0019) C17 * -0.0016 (0.0017) C18

Rms deviation of fitted atoms = 0.0078

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	1.0019 (2)	1.00932 (8)	0.7360 (3)	0.0272 (4)
C2	1.0476 (2)	1.05587 (9)	0.6574 (3)	0.0342 (5)
H2	1.1394	1.0634	0.6481	0.041*
C3	0.9480 (3)	1.09034 (10)	0.5935 (3)	0.0403 (6)
H3	0.9727	1.1219	0.5367	0.048*
C4	0.8095 (2)	1.07867 (9)	0.6128 (3)	0.0387 (6)
H4	0.7450	1.1033	0.5710	0.046*
C5	0.7662 (2)	1.03148 (10)	0.6925 (3)	0.0359 (5)
H5	0.6746	1.0239	0.7042	0.043*
C6	0.8651 (2)	0.99690 (9)	0.7526 (3)	0.0283 (5)
C7	0.9829 (2)	0.92732 (8)	0.8653 (3)	0.0252 (4)
C8	1.0572 (2)	0.88306 (9)	0.9310 (3)	0.0283 (5)
C9	1.1957 (2)	0.89723 (9)	0.9075 (3)	0.0301 (5)
C10	1.2040 (2)	0.94775 (9)	0.8330 (3)	0.0288 (5)
C11	1.3184 (2)	0.97791 (9)	0.7903 (3)	0.0333 (5)
C12	0.7257 (2)	0.91558 (10)	0.8516 (3)	0.0326 (5)
H12A	0.6509	0.9402	0.8692	0.039*
H12B	0.7325	0.8913	0.9509	0.039*
C13	0.69949 (19)	0.88336 (9)	0.6848 (3)	0.0292 (5)
C14	0.6168 (2)	0.90361 (10)	0.5555 (3)	0.0394 (6)
H14	0.5747	0.9368	0.5706	0.047*
C15	0.5946 (3)	0.87514 (11)	0.4004 (3)	0.0463 (7)
H15	0.5403	0.8898	0.3108	0.056*
C16	0.6539 (3)	0.82453 (12)	0.3795 (3)	0.0493 (7)
H16	0.6382	0.8055	0.2761	0.059*
C17	0.7340 (3)	0.80288 (12)	0.5082 (3)	0.0466 (6)
H17	0.7729	0.7690	0.4944	0.056*
C18	0.7576 (2)	0.83240 (10)	0.6629 (3)	0.0411 (6)
H18	0.8125	0.8179	0.7521	0.049*
C19	1.0032 (2)	0.83746 (9)	1.0316 (3)	0.0336 (5)
C20	1.0629 (3)	0.76423 (12)	1.2133 (4)	0.0577 (8)
H20A	1.0048	0.7778	1.3013	0.087*
H20B	1.1420	0.7482	1.2682	0.087*
H20C	1.0150	0.7376	1.1441	0.087*
C21	1.3202 (2)	0.86405 (10)	0.9391 (3)	0.0376 (5)
C22	1.4343 (3)	0.78357 (12)	0.8747 (4)	0.0528 (7)
H22A	1.5076	0.7961	0.8061	0.079*
H22B	1.4102	0.7475	0.8400	0.079*
H22C	1.4619	0.7838	0.9962	0.079*
N1	1.07206 (16)	0.96508 (7)	0.8086 (2)	0.0243 (4)
N2	0.85368 (17)	0.94658 (7)	0.8381 (2)	0.0278 (4)
N3	1.41453 (19)	1.00265 (9)	0.7614 (3)	0.0411 (5)
O1	1.10343 (16)	0.80841 (7)	1.1015 (2)	0.0403 (4)
O2	0.88636 (17)	0.82715 (7)	1.0552 (2)	0.0449 (5)
O3	1.31742 (17)	0.81903 (7)	0.8471 (2)	0.0451 (5)
O4	1.4114 (2)	0.87751 (9)	1.0281 (3)	0.0648 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0323 (11)	0.0244 (11)	0.0247 (10)	−0.0022 (9)	−0.0037 (8)	−0.0041 (8)
C2	0.0466 (13)	0.0273 (12)	0.0285 (11)	−0.0057 (10)	0.0002 (10)	−0.0019 (9)
C3	0.0513 (15)	0.0310 (13)	0.0385 (13)	0.0007 (11)	0.0013 (11)	−0.0045 (10)
C4	0.0433 (14)	0.0249 (12)	0.0473 (14)	0.0040 (10)	−0.0059 (11)	−0.0014 (10)
C5	0.0323 (12)	0.0352 (13)	0.0399 (13)	0.0041 (10)	−0.0055 (10)	−0.0037 (10)
C6	0.0274 (10)	0.0230 (11)	0.0343 (11)	0.0022 (9)	−0.0014 (9)	−0.0041 (9)
C7	0.0232 (10)	0.0269 (11)	0.0254 (10)	−0.0068 (8)	0.0006 (8)	−0.0034 (8)
C8	0.0264 (10)	0.0329 (12)	0.0257 (10)	−0.0025 (9)	0.0022 (8)	−0.0034 (9)
C9	0.0301 (11)	0.0342 (13)	0.0255 (10)	−0.0010 (9)	−0.0045 (9)	−0.0033 (9)
C10	0.0238 (10)	0.0337 (13)	0.0284 (10)	0.0024 (9)	−0.0040 (8)	−0.0013 (9)
C11	0.0260 (11)	0.0289 (12)	0.0448 (13)	0.0028 (9)	−0.0003 (10)	−0.0014 (10)
C12	0.0189 (10)	0.0365 (13)	0.0428 (13)	−0.0071 (9)	0.0074 (9)	−0.0026 (10)
C13	0.0175 (9)	0.0341 (12)	0.0361 (12)	−0.0056 (9)	0.0054 (8)	0.0021 (9)
C14	0.0381 (13)	0.0348 (13)	0.0444 (13)	−0.0044 (10)	−0.0116 (10)	−0.0010 (11)
C15	0.0522 (15)	0.0540 (17)	0.0316 (13)	−0.0098 (13)	−0.0143 (11)	0.0006 (11)
C16	0.0535 (16)	0.0536 (17)	0.0406 (14)	−0.0132 (13)	−0.0033 (12)	−0.0178 (12)
C17	0.0485 (15)	0.0460 (15)	0.0457 (15)	−0.0021 (12)	0.0038 (12)	−0.0133 (12)
C18	0.0398 (13)	0.0361 (14)	0.0466 (14)	0.0050 (11)	−0.0073 (11)	−0.0077 (11)
C19	0.0377 (13)	0.0303 (13)	0.0321 (12)	0.0005 (10)	−0.0074 (10)	−0.0015 (9)
C20	0.076 (2)	0.0544 (18)	0.0425 (15)	0.0009 (15)	0.0044 (14)	0.0349 (13)
C21	0.0348 (12)	0.0373 (14)	0.0403 (13)	0.0018 (10)	−0.0031 (10)	0.0009 (11)
C22	0.0480 (15)	0.0571 (18)	0.0535 (16)	0.0282 (13)	0.0064 (13)	−0.0133 (13)
N1	0.0211 (8)	0.0270 (9)	0.0249 (9)	−0.0030 (7)	0.0014 (7)	−0.0028 (7)
N2	0.0221 (8)	0.0295 (10)	0.0319 (9)	−0.0045 (7)	0.0000 (7)	−0.0004 (7)
N3	0.0303 (10)	0.0528 (14)	0.0404 (11)	−0.0052 (10)	0.0049 (8)	0.0129 (10)
O1	0.0418 (9)	0.0435 (10)	0.0356 (9)	0.0077 (8)	0.0030 (7)	0.0184 (7)
O2	0.0395 (10)	0.0547 (11)	0.0399 (9)	−0.0098 (8)	−0.0049 (7)	0.0225 (8)
O3	0.0467 (10)	0.0461 (11)	0.0422 (9)	0.0157 (8)	−0.0041 (8)	−0.0152 (8)
O4	0.0576 (12)	0.0899 (16)	0.0452 (11)	0.0140 (11)	−0.0211 (10)	−0.0184 (11)

Geometric parameters (Å, º) top

C1—C2	1.384 (3)	C12—H12B	0.9700
C1—C6	1.394 (3)	C13—C14	1.357 (3)
C1—N1	1.401 (3)	C13—C18	1.398 (3)
C2—C3	1.379 (3)	C14—C15	1.392 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.410 (4)	C15—C16	1.395 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.392 (3)	C16—C17	1.352 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.366 (3)	C17—C18	1.405 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—N2	1.414 (3)	C18—H18	0.9300
C7—N1	1.365 (3)	C19—O2	1.201 (3)
C7—N2	1.371 (3)	C19—O1	1.321 (3)
C7—C8	1.402 (3)	C20—O1	1.454 (3)
C8—C9	1.429 (3)	C20—H20A	0.9600
C8—C19	1.477 (3)	C20—H20B	0.9600
C9—C10	1.378 (3)	C20—H20C	0.9600
C9—C21	1.491 (3)	C21—O4	1.159 (3)
C10—N1	1.378 (3)	C21—O3	1.318 (3)
C10—C11	1.401 (3)	C22—O3	1.459 (3)
C11—N3	1.157 (3)	C22—H22A	0.9600
C12—N2	1.485 (3)	C22—H22B	0.9600
C12—C13	1.520 (3)	C22—H22C	0.9600
C12—H12A	0.9700

C2—C1—C6	123.7 (2)	C13—C14—H14	119.7
C2—C1—N1	131.3 (2)	C15—C14—H14	119.7
C6—C1—N1	104.97 (17)	C14—C15—C16	119.9 (2)
C3—C2—C1	115.5 (2)	C14—C15—H15	120.0
C3—C2—H2	122.2	C16—C15—H15	120.0
C1—C2—H2	122.2	C17—C16—C15	120.7 (2)
C2—C3—C4	121.2 (2)	C17—C16—H16	119.7
C2—C3—H3	119.4	C15—C16—H16	119.7
C4—C3—H3	119.4	C16—C17—C18	118.9 (3)
C5—C4—C3	122.1 (2)	C16—C17—H17	120.5
C5—C4—H4	118.9	C18—C17—H17	120.5
C3—C4—H4	118.9	C13—C18—C17	121.0 (2)
C6—C5—C4	116.5 (2)	C13—C18—H18	119.5
C6—C5—H5	121.7	C17—C18—H18	119.5
C4—C5—H5	121.7	O2—C19—O1	122.2 (2)
C5—C6—C1	120.9 (2)	O2—C19—C8	127.4 (2)
C5—C6—N2	129.9 (2)	O1—C19—C8	110.4 (2)
C1—C6—N2	109.22 (17)	O1—C20—H20A	109.5
N1—C7—N2	108.65 (18)	O1—C20—H20B	109.5
N1—C7—C8	108.36 (18)	H20A—C20—H20B	109.5
N2—C7—C8	142.99 (19)	O1—C20—H20C	109.5
C7—C8—C9	104.67 (19)	H20A—C20—H20C	109.5
C7—C8—C19	126.24 (19)	H20B—C20—H20C	109.5
C9—C8—C19	128.1 (2)	O4—C21—O3	124.0 (2)
C10—C9—C8	110.22 (19)	O4—C21—C9	123.7 (2)
C10—C9—C21	120.5 (2)	O3—C21—C9	112.17 (19)
C8—C9—C21	129.1 (2)	O3—C22—H22A	109.5
N1—C10—C9	105.65 (18)	O3—C22—H22B	109.5
N1—C10—C11	124.6 (2)	H22A—C22—H22B	109.5
C9—C10—C11	129.77 (19)	O3—C22—H22C	109.5
N3—C11—C10	177.5 (2)	H22A—C22—H22C	109.5
N2—C12—C13	109.47 (17)	H22B—C22—H22C	109.5
N2—C12—H12A	109.8	C7—N1—C10	111.09 (17)
C13—C12—H12A	109.8	C7—N1—C1	110.29 (17)
N2—C12—H12B	109.8	C10—N1—C1	138.55 (18)
C13—C12—H12B	109.8	C7—N2—C6	106.77 (16)
H12A—C12—H12B	108.2	C7—N2—C12	126.79 (18)
C14—C13—C18	119.0 (2)	C6—N2—C12	124.71 (17)
C14—C13—C12	120.0 (2)	C19—O1—C20	115.5 (2)
C18—C13—C12	121.1 (2)	C21—O3—C22	115.44 (19)
C13—C14—C15	120.6 (2)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃O₄
M_r	387.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	9.8681 (15), 24.766 (2), 7.6551 (11)
β (°)	91.973 (3)
V (Å³)	1869.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.97, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	13898, 3615, 2699
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.125, 1.03
No. of reflections	3615
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

C1—N1	1.401 (3)	C10—N1	1.378 (3)
C6—N2	1.414 (3)	C11—N3	1.157 (3)
C7—N1	1.365 (3)	C12—N2	1.485 (3)
C7—N2	1.371 (3)

C2—C1—N1	131.3 (2)	N1—C10—C11	124.6 (2)
C6—C1—N1	104.97 (17)	N3—C11—C10	177.5 (2)
N1—C7—N2	108.65 (18)	N2—C12—C13	109.47 (17)
N1—C7—C8	108.36 (18)	N2—C12—H12A	109.8
N2—C7—C8	142.99 (19)	N2—C12—H12B	109.8
N1—C10—C9	105.65 (18)

Acknowledgements

We thank the Natural Science Foundation of Jiangsu Province of China (grant No. BK2008435) and the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (grant No. 07KJD150101) for financial support.

References

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