Ethyl 2-[1-(4-chloro­phen­yl)-2,5-dioxo-1,2,3,5-tetra­hydro­imidazo[1′,2′:1,2]pyrimidino[5,4-b][1]benzofuran-3-yl]acetate

Hu, Y.-G.; Zhu, Z.-R.; Chen, Y.-L.

doi:10.1107/S1600536807066998

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages o321-o322

https://doi.org/10.1107/S1600536807066998

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Ethyl 2-[1-(4-chlorophenyl)-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1′,2′:1,2]pyrimidino[5,4-b][1]benzofuran-3-yl]acetate

Yang-Gen Hu,^a ^* Zheng-Rong Zhu ^b and Yu-Lu Chen ^c

^aDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, ^bDepartment of Medicine, Xiangfan Vocational and Technical College, Xiangfan 441021, People's Republic of China, and ^cDepartment of Chemistry, Xianning Vocational and Technical College, Xianning 437100, People's Republic of China
^*Correspondence e-mail: huyangg111@yahoo.com.cn

(Received 16 November 2007; accepted 14 December 2007; online 21 December 2007)

The asymmetric unit of the title compound, C₂₂H₁₆ClN₃O₅, consists of two crystallographically independent molecules. The fused rings of the imidazo[1,2-a]benzo[4,5]furo[3,2-d]pyrimidine system are nearly coplanar and the chlorophenyl rings are twisted with respect to the two pyrimidinone ring systems by 71.00 (2) and 62.59 (2)°. The C atoms of the ethyl side chain are disordered and were refined using a split model. In the crystal structure, the molecules are connected via weak intra- and intermolecular C—H⋯O interactions are present. The ethyl group in one molecule is disordered over two positions, with site occupancy factors 0.55 and 0.45; in the other molecule only the methyl group is disordered over two positions, with site occupancy factors 0.6 and 0.4.

Related literature

For related literature on the synthesis and biological activity, see Moneam et al. (2004 ); Bodke & Sangapure (2003 ). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 , 2006 , 2007 ).

Experimental

Crystal data

C₂₂H₁₆ClN₃O₅
M_r = 437.83
Triclinic, $[P \overline 1]$
a = 11.9711 (11) Å
b = 12.9079 (12) Å
c = 15.0957 (14) Å
α = 99.201 (2)°
β = 102.486 (2)°
γ = 110.085 (2)°
V = 2068.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.936, T_max = 0.956
19990 measured reflections
8066 independent reflections
5272 reflections with I > 2σ(I)
R_int = 0.101

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.161
S = 0.99
8066 reflections
556 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C31—H31B⋯O9	0.97	2.48	3.069 (3)	119
C30—H30⋯O4	0.98	2.28	3.071 (3)	137
C4—H4⋯O1ⁱ	0.93	2.60	3.333 (3)	136
C2—H2⋯O10ⁱⁱ	0.93	2.49	3.399 (3)	165
Symmetry codes: (i) -x+2, -y, -z+2; (ii) x+1, y, z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2001 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807066998/nc2080sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066998/nc2080Isup2.hkl

checkCIF report

Comment top

The derivatives of benzofuropyrimidine play an important role in many natural products, antibiotics and drugs (Moneam et al., 2004 and Bodke et al., 2003). As a part of our ongoing investigations on the preparation of derivatives of heterocyclic compounds (Hu et al., 2005, 2006, 2007)) we have synthesized and structurally characterized characterized the title compound. In the crystal structure of the title compound two crystallographically independent molecules are found in the asymmetric unit. All ring atoms of the imidazo[1,2-a]benzo[4,5]furo[3,2-d]pyrimidine system are essentially coplanar, with maximum deviations of -0.071 (1)Å and 0.092 (2))Å for O5 and C30. The benzene rings C1—C6 and C23—C28 are twisted with respect to the two pyrimidinone ring systems by 71.00 (2)° and 62.59 (2)°, respectively. In the crystal structure the molecules are connected via weak intramolecular and intermolecular C—H···O interactions.

Related literature top

For related literature on the synthesis and biological activity, see Moneam et al. (2004) and Bodke & Sangapure (2003). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007).

Experimental top

Ethyl-3-((4-chlorophenylimino)methyleneamino)benzofuran-2-carboxylate (3 mmol) were dissolved in 5 ml of dichloromethane. Afterwards diethyl-2-(aminomethyl)succinate(3 mmol) are added and the reaction mixture was stirred for 2 h. The solvent was removed under reduced pressure and 10 ml of anhydrous ethanol with several drops of EtONa dissolved in EtOH were added. The mixture was stirred for 6 h at room temperature. Afterwards the solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give 1.09 g of the title compound 1.09 g. Crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of the solvent from a solution of the title compound in a mixture ethanol and dichloromethane (1:2 v/v)at room temperature.

Structure description top

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

Fig. 1. Molecular structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level (The disordered C atoms with minor occupancy are only refined isotropic).

Ethyl 2-[1-(4-chlorophenyl)-2,5-dioxo-1,2,3,5- tetrahydroimidazo[1',2':1,2]pyrimidino[5,4-b][1]benzofuran-3-yl]acetate top

Crystal data top

C₂₂H₁₆ClN₃O₅	Z = 4
M_r = 437.83	F(000) = 904
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.9711 (11) Å	Cell parameters from 5946 reflections
b = 12.9079 (12) Å	θ = 0.0–0.0°
c = 15.0957 (14) Å	µ = 0.23 mm⁻¹
α = 99.201 (2)°	T = 293 K
β = 102.486 (2)°	Block, colorless
γ = 110.085 (2)°	0.30 × 0.20 × 0.20 mm
V = 2068.0 (3) Å³

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	8066 independent reflections
Radiation source: fine-focus sealed tube	5272 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.101
φ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
T_min = 0.936, T_max = 0.956	k = −15→15
19990 measured reflections	l = −18→18

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) = 0.161	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0796P)²] where P = (F_o² + 2F_c²)/3
8066 reflections	(Δ/σ)_max = 0.001
556 parameters	Δρ_max = 0.31 e Å⁻³
4 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₂H₁₆ClN₃O₅	γ = 110.085 (2)°
M_r = 437.83	V = 2068.0 (3) Å³
Triclinic, P1	Z = 4
a = 11.9711 (11) Å	Mo Kα radiation
b = 12.9079 (12) Å	µ = 0.23 mm⁻¹
c = 15.0957 (14) Å	T = 293 K
α = 99.201 (2)°	0.30 × 0.20 × 0.20 mm
β = 102.486 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	8066 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	5272 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.956	R_int = 0.101
19990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	4 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 0.99	Δρ_max = 0.31 e Å⁻³
8066 reflections	Δρ_min = −0.30 e Å⁻³
556 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	Occ. (<1)
Cl1	1.31245 (7)	0.33661 (9)	1.33809 (5)	0.1148 (4)
O1	1.04953 (14)	0.13649 (13)	0.87225 (11)	0.0619 (4)
O2	0.9535 (2)	0.34943 (16)	0.87703 (14)	0.0966 (6)
O3	0.9297 (3)	0.37601 (19)	0.73355 (16)	0.1144 (8)
O4	0.57242 (14)	0.06236 (15)	0.74406 (11)	0.0699 (5)
O5	0.45393 (13)	0.10771 (13)	0.89127 (12)	0.0662 (5)
N1	0.93085 (15)	0.15775 (15)	0.96988 (11)	0.0491 (4)
N2	0.75138 (15)	0.12384 (14)	0.86505 (11)	0.0501 (4)
N3	0.76535 (15)	0.16729 (14)	1.02776 (12)	0.0499 (4)
C1	1.1999 (2)	0.2852 (3)	1.23024 (16)	0.0674 (7)
C2	1.1089 (2)	0.1778 (3)	1.20875 (17)	0.0701 (7)
H2	1.1070	0.1341	1.2522	0.084*
C3	1.2039 (2)	0.3521 (2)	1.16775 (18)	0.0702 (7)
H3	1.2661	0.4249	1.1833	0.084*
C4	1.0204 (2)	0.1351 (2)	1.12231 (16)	0.0593 (6)
H4	0.9589	0.0621	1.1067	0.071*
C5	1.1140 (2)	0.3096 (2)	1.08130 (16)	0.0597 (6)
H5	1.1147	0.3539	1.0384	0.072*
C6	1.02376 (18)	0.20104 (19)	1.05954 (14)	0.0478 (5)
C7	0.9533 (2)	0.13632 (18)	0.88426 (15)	0.0508 (5)
C8	0.8342 (2)	0.11147 (19)	0.80869 (14)	0.0544 (5)
H8	0.8018	0.0320	0.7721	0.065*
C9	0.8532 (2)	0.1886 (2)	0.74351 (16)	0.0681 (7)
H9A	0.9018	0.1687	0.7051	0.082*
H9B	0.7729	0.1755	0.7019	0.082*
C10	0.9175 (3)	0.3124 (2)	0.7934 (2)	0.0736 (7)
C11	1.0346 (8)	0.5111 (6)	0.7868 (6)	0.119 (2)*	0.55
H11A	1.0085	0.5404	0.8384	0.142*	0.55
H11B	1.1136	0.5068	0.8139	0.142*	0.55
C12	1.0553 (14)	0.5882 (12)	0.7364 (11)	0.245 (6)*	0.55
H12A	1.1141	0.6608	0.7765	0.367*	0.55
H12B	0.9786	0.5946	0.7087	0.367*	0.55
H12C	1.0881	0.5646	0.6878	0.367*	0.55
C11'	0.9661 (9)	0.4899 (7)	0.7637 (6)	0.110 (3)*	0.45
H11C	1.0471	0.5202	0.8100	0.132*	0.45
H11D	0.9082	0.5046	0.7949	0.132*	0.45
C12'	0.9739 (10)	0.5526 (9)	0.6900 (7)	0.133 (3)*	0.45
H12D	0.9923	0.6313	0.7167	0.199*	0.45
H12E	0.8960	0.5201	0.6414	0.199*	0.45
H12F	1.0386	0.5470	0.6639	0.199*	0.45
C13	0.81092 (18)	0.15222 (17)	0.95896 (14)	0.0466 (5)
C14	0.6245 (2)	0.09868 (18)	0.82764 (16)	0.0542 (5)
C15	0.57554 (19)	0.12095 (18)	0.90383 (17)	0.0554 (6)
C16	0.64103 (18)	0.14966 (17)	0.99573 (15)	0.0501 (5)
C17	0.5567 (2)	0.15575 (18)	1.04862 (17)	0.0561 (6)
C18	0.4440 (2)	0.12948 (19)	0.9808 (2)	0.0629 (6)
C19	0.3374 (2)	0.1262 (2)	1.0028 (3)	0.0780 (8)
H19	0.2639	0.1101	0.9568	0.094*
C20	0.3456 (3)	0.1477 (2)	1.0958 (3)	0.0878 (9)
H20	0.2753	0.1462	1.1133	0.105*
C21	0.4549 (3)	0.1721 (2)	1.1657 (2)	0.0806 (8)
H21	0.4557	0.1847	1.2282	0.097*
C22	0.5627 (2)	0.1776 (2)	1.14290 (19)	0.0680 (7)
H22	0.6365	0.1955	1.1893	0.082*
Cl2	0.33863 (8)	0.57533 (6)	1.01490 (5)	0.0883 (3)
O6	0.60082 (18)	0.31763 (18)	0.75069 (12)	0.0853 (6)
O7	0.51473 (18)	0.37899 (16)	0.54234 (14)	0.0860 (6)
O8	0.6390 (2)	0.34225 (18)	0.46363 (15)	0.0954 (6)
O9	0.30452 (17)	0.02466 (16)	0.42624 (12)	0.0829 (5)
O10	0.05213 (15)	0.02539 (13)	0.36962 (10)	0.0639 (4)
N4	0.39254 (18)	0.28569 (17)	0.69552 (12)	0.0623 (5)
N5	0.33882 (17)	0.15994 (16)	0.55839 (11)	0.0565 (5)
N6	0.18881 (18)	0.22927 (16)	0.59442 (12)	0.0577 (5)
C23	0.3552 (2)	0.49233 (19)	0.92003 (15)	0.0602 (6)
C24	0.2838 (3)	0.3782 (2)	0.8923 (2)	0.0984 (11)
H24	0.2273	0.3460	0.9238	0.118*
C25	0.4375 (2)	0.5398 (2)	0.87435 (18)	0.0711 (7)
H25	0.4863	0.6177	0.8940	0.085*
C26	0.2960 (3)	0.3113 (2)	0.8176 (2)	0.1000 (11)
H26	0.2471	0.2335	0.7982	0.120*
C27	0.4491 (2)	0.4730 (2)	0.79872 (17)	0.0660 (6)
H27	0.5040	0.5057	0.7662	0.079*
C28	0.3791 (2)	0.3579 (2)	0.77187 (14)	0.0583 (6)
C29	0.4996 (3)	0.2693 (2)	0.69287 (16)	0.0666 (6)
C30	0.4674 (2)	0.1778 (2)	0.60375 (15)	0.0630 (6)
H30	0.4684	0.1079	0.6207	0.076*
C31	0.5563 (2)	0.2119 (2)	0.54537 (17)	0.0671 (7)
H31A	0.6383	0.2207	0.5808	0.081*
H31B	0.5290	0.1509	0.4890	0.081*
C32	0.5654 (2)	0.3198 (2)	0.51802 (17)	0.0653 (6)
C33	0.6636 (4)	0.4482 (3)	0.4349 (3)	0.1105 (11)
H33A	0.5884	0.4439	0.3915	0.133*	0.60
H33B	0.6872	0.5108	0.4894	0.133*	0.60
H33C	0.6374	0.4331	0.3671	0.133*	0.40
H33D	0.6199	0.4907	0.4606	0.133*	0.40
C34	0.7589 (6)	0.4693 (6)	0.3917 (5)	0.121 (2)*	0.60
H34A	0.7734	0.5397	0.3737	0.181*	0.60
H34B	0.7350	0.4081	0.3371	0.181*	0.60
H34C	0.8337	0.4746	0.4349	0.181*	0.60
C34'	0.7928 (10)	0.5093 (10)	0.4709 (9)	0.131 (3)*	0.40
H34D	0.8153	0.5811	0.4547	0.197*	0.40
H34E	0.8344	0.4660	0.4447	0.197*	0.40
H34F	0.8171	0.5224	0.5380	0.197*	0.40
C35	0.2970 (2)	0.22450 (19)	0.61329 (14)	0.0548 (5)
C36	0.2644 (2)	0.0824 (2)	0.47202 (15)	0.0610 (6)
C37	0.1460 (2)	0.08853 (19)	0.45146 (14)	0.0554 (6)
C38	0.1131 (2)	0.15856 (18)	0.50819 (14)	0.0540 (5)
C39	−0.0124 (2)	0.14175 (19)	0.45958 (15)	0.0577 (6)
C40	−0.0446 (2)	0.0603 (2)	0.37588 (15)	0.0604 (6)
C41	−0.1572 (2)	0.0209 (2)	0.30865 (18)	0.0729 (7)
H41	−0.1760	−0.0336	0.2533	0.087*
C42	−0.2402 (3)	0.0656 (3)	0.3268 (2)	0.0835 (8)
H42	−0.3175	0.0410	0.2827	0.100*
C43	−0.2121 (3)	0.1473 (3)	0.4099 (2)	0.0848 (8)
H43	−0.2710	0.1757	0.4202	0.102*
C44	−0.0984 (2)	0.1863 (2)	0.47677 (18)	0.0721 (7)
H44	−0.0797	0.2411	0.5319	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0536 (9)	0.0706 (11)	0.0622 (10)	0.0248 (8)	0.0234 (8)	0.0090 (8)
O2	0.1407 (19)	0.0624 (12)	0.0714 (13)	0.0299 (12)	0.0240 (12)	0.0086 (10)
O3	0.192 (2)	0.0956 (16)	0.1072 (17)	0.0835 (17)	0.0784 (17)	0.0547 (14)
O4	0.0623 (10)	0.0782 (11)	0.0519 (10)	0.0264 (9)	−0.0050 (8)	0.0026 (8)
O5	0.0427 (9)	0.0667 (11)	0.0782 (12)	0.0215 (8)	0.0064 (8)	0.0044 (9)
N1	0.0384 (9)	0.0599 (11)	0.0444 (10)	0.0173 (8)	0.0102 (8)	0.0080 (8)
N2	0.0433 (10)	0.0540 (11)	0.0447 (10)	0.0175 (8)	0.0056 (8)	0.0043 (8)
N3	0.0424 (10)	0.0547 (11)	0.0487 (10)	0.0186 (8)	0.0116 (8)	0.0065 (8)
C1	0.0496 (14)	0.099 (2)	0.0466 (13)	0.0293 (15)	0.0102 (11)	0.0039 (13)
C2	0.0592 (15)	0.105 (2)	0.0593 (15)	0.0387 (16)	0.0222 (12)	0.0355 (15)
C3	0.0531 (14)	0.0731 (17)	0.0635 (16)	0.0109 (13)	0.0112 (12)	0.0005 (14)
C4	0.0471 (13)	0.0697 (15)	0.0615 (14)	0.0203 (11)	0.0161 (11)	0.0235 (12)
C5	0.0535 (13)	0.0648 (15)	0.0526 (13)	0.0149 (12)	0.0147 (11)	0.0125 (11)
C6	0.0362 (11)	0.0581 (13)	0.0473 (12)	0.0176 (10)	0.0132 (9)	0.0091 (10)
C7	0.0494 (13)	0.0468 (12)	0.0542 (13)	0.0175 (10)	0.0170 (10)	0.0082 (10)
C8	0.0577 (13)	0.0524 (13)	0.0455 (12)	0.0210 (11)	0.0109 (10)	−0.0003 (10)
C9	0.0752 (16)	0.0773 (17)	0.0474 (13)	0.0275 (14)	0.0158 (12)	0.0126 (12)
C10	0.094 (2)	0.0767 (18)	0.0711 (18)	0.0465 (16)	0.0363 (16)	0.0297 (16)
Cl1	0.0850 (5)	0.1759 (9)	0.0525 (4)	0.0461 (6)	−0.0078 (4)	−0.0043 (5)
Cl2	0.1290 (6)	0.0651 (4)	0.0637 (4)	0.0356 (4)	0.0326 (4)	−0.0032 (3)
C13	0.0412 (11)	0.0471 (12)	0.0471 (12)	0.0167 (9)	0.0087 (9)	0.0073 (9)
C14	0.0473 (13)	0.0504 (13)	0.0558 (14)	0.0199 (10)	0.0018 (11)	0.0054 (11)
C15	0.0397 (12)	0.0516 (13)	0.0667 (15)	0.0193 (10)	0.0049 (11)	0.0050 (11)
C16	0.0412 (12)	0.0434 (11)	0.0613 (14)	0.0152 (10)	0.0138 (10)	0.0065 (10)
C17	0.0496 (13)	0.0452 (12)	0.0741 (16)	0.0182 (10)	0.0226 (12)	0.0115 (11)
C18	0.0448 (13)	0.0472 (13)	0.0938 (19)	0.0186 (11)	0.0201 (13)	0.0095 (13)
C19	0.0520 (15)	0.0600 (16)	0.119 (3)	0.0214 (13)	0.0288 (16)	0.0111 (16)
C20	0.0663 (19)	0.0630 (17)	0.147 (3)	0.0259 (15)	0.058 (2)	0.0223 (18)
C21	0.091 (2)	0.0616 (16)	0.107 (2)	0.0325 (15)	0.0614 (19)	0.0195 (16)
C22	0.0696 (16)	0.0587 (15)	0.0837 (18)	0.0268 (13)	0.0360 (14)	0.0174 (13)
O6	0.0730 (12)	0.1010 (15)	0.0600 (11)	0.0287 (11)	0.0006 (10)	−0.0005 (10)
O7	0.1001 (14)	0.0830 (13)	0.0992 (14)	0.0507 (12)	0.0493 (12)	0.0276 (11)
O8	0.1111 (15)	0.1048 (15)	0.1158 (16)	0.0615 (13)	0.0718 (14)	0.0542 (13)
O9	0.0913 (13)	0.0927 (13)	0.0578 (10)	0.0419 (11)	0.0205 (9)	−0.0109 (9)
O10	0.0740 (11)	0.0617 (10)	0.0391 (8)	0.0171 (9)	0.0094 (7)	−0.0014 (7)
N4	0.0625 (12)	0.0733 (13)	0.0381 (10)	0.0208 (11)	0.0107 (9)	−0.0018 (9)
N5	0.0635 (12)	0.0642 (12)	0.0383 (9)	0.0241 (10)	0.0154 (9)	0.0052 (9)
N6	0.0643 (12)	0.0587 (12)	0.0380 (10)	0.0169 (10)	0.0137 (9)	−0.0016 (8)
C23	0.0785 (16)	0.0492 (13)	0.0424 (12)	0.0186 (12)	0.0139 (12)	0.0030 (10)
C24	0.138 (3)	0.0559 (16)	0.0803 (19)	−0.0014 (16)	0.071 (2)	−0.0027 (14)
C25	0.0845 (18)	0.0469 (13)	0.0637 (16)	0.0110 (13)	0.0172 (14)	0.0046 (12)
C26	0.136 (3)	0.0497 (15)	0.0815 (19)	−0.0077 (16)	0.062 (2)	−0.0109 (14)
C27	0.0678 (16)	0.0626 (15)	0.0563 (14)	0.0110 (13)	0.0219 (12)	0.0129 (12)
C28	0.0645 (14)	0.0604 (14)	0.0349 (11)	0.0135 (12)	0.0120 (10)	0.0003 (10)
C29	0.0718 (17)	0.0749 (17)	0.0451 (13)	0.0251 (14)	0.0111 (13)	0.0103 (12)
C30	0.0751 (16)	0.0696 (16)	0.0451 (12)	0.0333 (13)	0.0138 (12)	0.0102 (11)
C31	0.0692 (16)	0.0772 (17)	0.0634 (15)	0.0387 (14)	0.0210 (13)	0.0162 (13)
C32	0.0615 (15)	0.0785 (17)	0.0585 (14)	0.0319 (14)	0.0190 (12)	0.0128 (13)
C33	0.124 (3)	0.115 (3)	0.137 (3)	0.060 (2)	0.076 (3)	0.068 (2)
C35	0.0649 (15)	0.0541 (13)	0.0360 (11)	0.0154 (11)	0.0165 (10)	0.0022 (10)
C36	0.0791 (17)	0.0609 (14)	0.0376 (11)	0.0253 (13)	0.0172 (11)	0.0031 (10)
C37	0.0633 (14)	0.0549 (13)	0.0383 (11)	0.0169 (11)	0.0120 (10)	0.0041 (10)
C38	0.0638 (14)	0.0529 (13)	0.0378 (11)	0.0145 (11)	0.0176 (10)	0.0061 (10)
C39	0.0596 (14)	0.0564 (14)	0.0467 (12)	0.0116 (11)	0.0160 (11)	0.0098 (10)
C40	0.0661 (15)	0.0603 (14)	0.0457 (13)	0.0150 (12)	0.0168 (11)	0.0106 (11)
C41	0.0701 (17)	0.0689 (17)	0.0529 (14)	0.0080 (14)	0.0033 (13)	0.0072 (12)
C42	0.0649 (17)	0.091 (2)	0.0719 (18)	0.0135 (16)	0.0039 (14)	0.0195 (16)
C43	0.0637 (17)	0.098 (2)	0.090 (2)	0.0275 (16)	0.0249 (16)	0.0241 (18)
C44	0.0684 (17)	0.0766 (17)	0.0650 (16)	0.0225 (14)	0.0235 (14)	0.0090 (13)

Geometric parameters (Å, º) top

Cl1—C1	1.732 (2)	Cl2—C23	1.737 (2)
O1—C7	1.204 (2)	O6—C29	1.212 (3)
O2—C10	1.199 (3)	O7—C32	1.188 (3)
O3—C10	1.313 (3)	O8—C32	1.322 (3)
O3—C11'	1.348 (8)	O8—C33	1.454 (4)
O3—C11	1.695 (8)	O9—C36	1.220 (3)
O4—C14	1.213 (3)	O10—C37	1.379 (2)
O5—C15	1.373 (2)	O10—C40	1.395 (3)
O5—C18	1.375 (3)	N4—C29	1.377 (3)
N1—C7	1.381 (3)	N4—C35	1.387 (3)
N1—C13	1.384 (2)	N4—C28	1.436 (3)
N1—C6	1.436 (2)	N5—C35	1.370 (3)
N2—C13	1.367 (3)	N5—C36	1.401 (3)
N2—C14	1.401 (3)	N5—C30	1.463 (3)
N2—C8	1.471 (3)	N6—C35	1.290 (3)
N3—C13	1.291 (3)	N6—C38	1.375 (3)
N3—C16	1.386 (3)	C23—C25	1.355 (3)
C1—C2	1.370 (4)	C23—C24	1.363 (3)
C1—C3	1.375 (4)	C24—C26	1.374 (4)
C2—C4	1.379 (3)	C24—H24	0.9300
C2—H2	0.9300	C25—C27	1.379 (3)
C3—C5	1.386 (3)	C25—H25	0.9300
C3—H3	0.9300	C26—C28	1.359 (4)
C4—C6	1.369 (3)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.370 (3)
C5—C6	1.378 (3)	C27—H27	0.9300
C5—H5	0.9300	C29—C30	1.519 (3)
C7—C8	1.517 (3)	C30—C31	1.520 (3)
C8—C9	1.505 (3)	C30—H30	0.9800
C8—H8	0.9800	C31—C32	1.490 (4)
C9—C10	1.495 (4)	C31—H31A	0.9700
C9—H9A	0.9700	C31—H31B	0.9700
C9—H9B	0.9700	C33—C34	1.402 (7)
C11—C12	1.335 (13)	C33—C34'	1.405 (11)
C11—H11A	0.9700	C33—H33A	0.9700
C11—H11B	0.9700	C33—H33B	0.9700
C12—H12A	0.9600	C33—H33C	0.9700
C12—H12B	0.9600	C33—H33D	0.9700
C12—H12C	0.9600	C34—H34A	0.9600
C11'—C12'	1.478 (1)	C34—H34B	0.9600
C11'—H11C	0.9700	C34—H34C	0.9600
C11'—H11D	0.9700	C34'—H34D	0.9600
C12'—H12D	0.9600	C34'—H34E	0.9600
C12'—H12E	0.9600	C34'—H34F	0.9600
C12'—H12F	0.9600	C36—C37	1.417 (3)
C14—C15	1.432 (3)	C37—C38	1.359 (3)
C15—C16	1.357 (3)	C38—C39	1.446 (3)
C16—C17	1.430 (3)	C39—C44	1.391 (3)
C17—C22	1.387 (3)	C39—C40	1.392 (3)
C17—C18	1.400 (3)	C40—C41	1.371 (3)
C18—C19	1.375 (3)	C41—C42	1.361 (4)
C19—C20	1.361 (4)	C41—H41	0.9300
C19—H19	0.9300	C42—C43	1.396 (4)
C20—C21	1.392 (4)	C42—H42	0.9300
C20—H20	0.9300	C43—C44	1.377 (4)
C21—C22	1.387 (3)	C43—H43	0.9300
C21—H21	0.9300	C44—H44	0.9300
C22—H22	0.9300

C10—O3—C11'	120.0 (4)	C35—N5—C30	111.52 (17)
C10—O3—C11	111.5 (4)	C36—N5—C30	124.84 (18)
C15—O5—C18	104.37 (17)	C35—N6—C38	111.59 (18)
C7—N1—C13	111.36 (17)	C25—C23—C24	120.5 (2)
C7—N1—C6	125.24 (16)	C25—C23—Cl2	120.77 (18)
C13—N1—C6	122.46 (16)	C24—C23—Cl2	118.7 (2)
C13—N2—C14	124.04 (18)	C23—C24—C26	119.5 (3)
C13—N2—C8	111.30 (16)	C23—C24—H24	120.3
C14—N2—C8	124.37 (17)	C26—C24—H24	120.3
C13—N3—C16	111.37 (17)	C23—C25—C27	120.1 (2)
C2—C1—C3	121.4 (2)	C23—C25—H25	119.9
C2—C1—Cl1	119.1 (2)	C27—C25—H25	119.9
C3—C1—Cl1	119.6 (2)	C28—C26—C24	120.5 (2)
C1—C2—C4	119.5 (2)	C28—C26—H26	119.8
C1—C2—H2	120.2	C24—C26—H26	119.8
C4—C2—H2	120.2	C28—C27—C25	119.4 (2)
C1—C3—C5	119.0 (2)	C28—C27—H27	120.3
C1—C3—H3	120.5	C25—C27—H27	120.3
C5—C3—H3	120.5	C26—C28—C27	120.0 (2)
C6—C4—C2	119.5 (2)	C26—C28—N4	119.4 (2)
C6—C4—H4	120.2	C27—C28—N4	120.6 (2)
C2—C4—H4	120.2	O6—C29—N4	126.9 (2)
C6—C5—C3	119.4 (2)	O6—C29—C30	125.9 (2)
C6—C5—H5	120.3	N4—C29—C30	107.2 (2)
C3—C5—H5	120.3	N5—C30—C29	101.64 (18)
C4—C6—C5	121.1 (2)	N5—C30—C31	114.95 (18)
C4—C6—N1	119.9 (2)	C29—C30—C31	113.2 (2)
C5—C6—N1	118.99 (19)	N5—C30—H30	108.9
O1—C7—N1	126.02 (19)	C29—C30—H30	108.9
O1—C7—C8	126.6 (2)	C31—C30—H30	108.9
N1—C7—C8	107.38 (17)	C32—C31—C30	113.7 (2)
N2—C8—C9	115.14 (18)	C32—C31—H31A	108.8
N2—C8—C7	101.66 (16)	C30—C31—H31A	108.8
C9—C8—C7	112.54 (19)	C32—C31—H31B	108.8
N2—C8—H8	109.1	C30—C31—H31B	108.8
C9—C8—H8	109.1	H31A—C31—H31B	107.7
C7—C8—H8	109.1	O7—C32—O8	124.1 (3)
C10—C9—C8	113.5 (2)	O7—C32—C31	124.9 (2)
C10—C9—H9A	108.9	O8—C32—C31	111.0 (2)
C8—C9—H9A	108.9	C34—C33—C34'	48.1 (5)
C10—C9—H9B	108.9	C34—C33—O8	111.2 (4)
C8—C9—H9B	108.9	C34'—C33—O8	105.2 (5)
H9A—C9—H9B	107.7	C34—C33—H33A	109.4
O2—C10—O3	124.1 (3)	C34'—C33—H33A	144.3
O2—C10—C9	124.8 (2)	O8—C33—H33A	109.4
O3—C10—C9	111.1 (3)	C34—C33—H33B	109.4
C12—C11—O3	119.2 (9)	C34'—C33—H33B	67.0
C12—C11—H11A	107.5	O8—C33—H33B	109.4
O3—C11—H11A	107.5	H33A—C33—H33B	108.0
C12—C11—H11B	107.5	C34—C33—H33C	64.0
O3—C11—H11B	107.5	C34'—C33—H33C	110.7
H11A—C11—H11B	107.0	O8—C33—H33C	110.7
C11—C12—H12A	109.5	H33A—C33—H33C	48.4
C11—C12—H12B	109.5	H33B—C33—H33C	138.7
H12A—C12—H12B	109.5	C34—C33—H33D	137.0
C11—C12—H12C	109.5	C34'—C33—H33D	110.7
H12A—C12—H12C	109.5	O8—C33—H33D	110.7
H12B—C12—H12C	109.5	H33A—C33—H33D	64.3
O3—C11'—C12'	115.4 (8)	H33B—C33—H33D	46.0
O3—C11'—H11C	108.4	H33C—C33—H33D	108.8
C12'—C11'—H11C	108.4	C33—C34—H34A	109.5
O3—C11'—H11D	108.4	H33C—C34—H34A	96.0
C12'—C11'—H11D	108.4	C33—C34—H34B	109.5
H11C—C11'—H11D	107.5	H33C—C34—H34B	78.0
C11'—C12'—H12D	109.5	H34A—C34—H34B	109.5
C11'—C12'—H12E	109.5	C33—C34—H34C	109.5
H12D—C12'—H12E	109.5	H33C—C34—H34C	148.2
C11'—C12'—H12F	109.5	H34A—C34—H34C	109.5
H12D—C12'—H12F	109.5	H34B—C34—H34C	109.5
H12E—C12'—H12F	109.5	C33—C34'—H34D	109.5
N3—C13—N2	127.63 (18)	C33—C34'—H34E	109.5
N3—C13—N1	124.03 (18)	H34D—C34'—H34E	109.5
N2—C13—N1	108.28 (17)	C33—C34'—H34F	109.5
O4—C14—N2	122.0 (2)	H34D—C34'—H34F	109.5
O4—C14—C15	129.9 (2)	H34E—C34'—H34F	109.5
N2—C14—C15	108.12 (18)	N6—C35—N5	127.52 (19)
C16—C15—O5	112.7 (2)	N6—C35—N4	124.65 (19)
C16—C15—C14	124.07 (19)	N5—C35—N4	107.8 (2)
O5—C15—C14	123.1 (2)	O9—C36—N5	121.5 (2)
C15—C16—N3	124.42 (19)	O9—C36—C37	129.9 (2)
C15—C16—C17	106.63 (19)	N5—C36—C37	108.56 (19)
N3—C16—C17	128.9 (2)	C38—C37—O10	112.6 (2)
C22—C17—C18	119.5 (2)	C38—C37—C36	124.3 (2)
C22—C17—C16	136.0 (2)	O10—C37—C36	123.08 (19)
C18—C17—C16	104.5 (2)	C37—C38—N6	124.4 (2)
C19—C18—O5	125.1 (2)	C37—C38—C39	106.41 (19)
C19—C18—C17	123.2 (3)	N6—C38—C39	129.2 (2)
O5—C18—C17	111.80 (19)	C44—C39—C40	118.8 (2)
C20—C19—C18	116.3 (3)	C44—C39—C38	136.1 (2)
C20—C19—H19	121.9	C40—C39—C38	105.1 (2)
C18—C19—H19	121.9	C41—C40—C39	123.6 (2)
C19—C20—C21	122.7 (3)	C41—C40—O10	125.0 (2)
C19—C20—H20	118.7	C39—C40—O10	111.4 (2)
C21—C20—H20	118.7	C42—C41—C40	116.7 (2)
C22—C21—C20	120.7 (3)	C42—C41—H41	121.6
C22—C21—H21	119.7	C40—C41—H41	121.6
C20—C21—H21	119.7	C41—C42—C43	121.7 (3)
C21—C22—C17	117.8 (3)	C41—C42—H42	119.2
C21—C22—H22	121.1	C43—C42—H42	119.2
C17—C22—H22	121.1	C44—C43—C42	121.0 (3)
C32—O8—C33	118.0 (2)	C44—C43—H43	119.5
C37—O10—C40	104.51 (16)	C42—C43—H43	119.5
C29—N4—C35	111.43 (18)	C43—C44—C39	118.2 (2)
C29—N4—C28	125.47 (19)	C43—C44—H44	120.9
C35—N4—C28	123.10 (19)	C39—C44—H44	120.9
C35—N5—C36	123.56 (19)

C3—C1—C2—C4	0.9 (4)	C18—C17—C22—C21	0.1 (3)
Cl1—C1—C2—C4	−178.63 (18)	C16—C17—C22—C21	−178.2 (2)
C2—C1—C3—C5	−0.1 (4)	C25—C23—C24—C26	0.1 (5)
Cl1—C1—C3—C5	179.37 (17)	Cl2—C23—C24—C26	−179.8 (3)
C1—C2—C4—C6	−0.7 (3)	C24—C23—C25—C27	0.5 (4)
C1—C3—C5—C6	−0.7 (3)	Cl2—C23—C25—C27	−179.56 (19)
C2—C4—C6—C5	−0.1 (3)	C23—C24—C26—C28	0.5 (6)
C2—C4—C6—N1	−179.13 (19)	C23—C25—C27—C28	−1.7 (4)
C3—C5—C6—C4	0.9 (3)	C24—C26—C28—C27	−1.7 (5)
C3—C5—C6—N1	179.88 (19)	C24—C26—C28—N4	178.3 (3)
C7—N1—C6—C4	−115.8 (2)	C25—C27—C28—C26	2.3 (4)
C13—N1—C6—C4	76.3 (3)	C25—C27—C28—N4	−177.8 (2)
C7—N1—C6—C5	65.2 (3)	C29—N4—C28—C26	−118.3 (3)
C13—N1—C6—C5	−102.8 (2)	C35—N4—C28—C26	62.9 (3)
C13—N1—C7—O1	179.2 (2)	C29—N4—C28—C27	61.7 (3)
C6—N1—C7—O1	10.2 (3)	C35—N4—C28—C27	−117.1 (3)
C13—N1—C7—C8	−1.3 (2)	C35—N4—C29—O6	173.9 (3)
C6—N1—C7—C8	−170.42 (19)	C28—N4—C29—O6	−5.0 (4)
C13—N2—C8—C9	−121.6 (2)	C35—N4—C29—C30	−6.6 (3)
C14—N2—C8—C9	64.4 (3)	C28—N4—C29—C30	174.5 (2)
C13—N2—C8—C7	0.4 (2)	C35—N5—C30—C29	−3.2 (2)
C14—N2—C8—C7	−173.65 (18)	C36—N5—C30—C29	180.0 (2)
O1—C7—C8—N2	180.0 (2)	C35—N5—C30—C31	−125.9 (2)
N1—C7—C8—N2	0.6 (2)	C36—N5—C30—C31	57.3 (3)
O1—C7—C8—C9	−56.3 (3)	O6—C29—C30—N5	−174.7 (3)
N1—C7—C8—C9	124.3 (2)	N4—C29—C30—N5	5.8 (2)
N2—C8—C9—C10	64.4 (3)	O6—C29—C30—C31	−50.9 (3)
C7—C8—C9—C10	−51.5 (3)	N4—C29—C30—C31	129.6 (2)
C11'—O3—C10—O2	−11.2 (7)	N5—C30—C31—C32	59.3 (3)
C11—O3—C10—O2	15.3 (5)	C29—C30—C31—C32	−56.9 (3)
C11'—O3—C10—C9	168.8 (5)	C33—O8—C32—O7	2.6 (4)
C11—O3—C10—C9	−164.6 (4)	C33—O8—C32—C31	−176.6 (3)
C8—C9—C10—O2	1.2 (4)	C30—C31—C32—O7	3.9 (4)
C8—C9—C10—O3	−178.8 (2)	C30—C31—C32—O8	−176.9 (2)
C10—O3—C11—C12	−177.8 (9)	C32—O8—C33—C34	169.7 (4)
C11'—O3—C11—C12	−62.6 (14)	C32—O8—C33—C34'	119.3 (6)
C10—O3—C11'—C12'	−178.7 (6)	C38—N6—C35—N5	0.2 (3)
C11—O3—C11'—C12'	104.8 (16)	C38—N6—C35—N4	−179.5 (2)
C16—N3—C13—N2	0.7 (3)	C36—N5—C35—N6	−3.3 (4)
C16—N3—C13—N1	−176.20 (18)	C30—N5—C35—N6	179.8 (2)
C14—N2—C13—N3	−4.4 (3)	C36—N5—C35—N4	176.4 (2)
C8—N2—C13—N3	−178.5 (2)	C30—N5—C35—N4	−0.5 (3)
C14—N2—C13—N1	172.86 (17)	C29—N4—C35—N6	−175.7 (2)
C8—N2—C13—N1	−1.2 (2)	C28—N4—C35—N6	3.2 (4)
C7—N1—C13—N3	179.0 (2)	C29—N4—C35—N5	4.6 (3)
C6—N1—C13—N3	−11.6 (3)	C28—N4—C35—N5	−176.5 (2)
C7—N1—C13—N2	1.6 (2)	C35—N5—C36—O9	−178.3 (2)
C6—N1—C13—N2	171.02 (17)	C30—N5—C36—O9	−1.9 (4)
C13—N2—C14—O4	−172.1 (2)	C35—N5—C36—C37	3.1 (3)
C8—N2—C14—O4	1.2 (3)	C30—N5—C36—C37	179.5 (2)
C13—N2—C14—C15	6.6 (3)	C40—O10—C37—C38	0.9 (2)
C8—N2—C14—C15	179.83 (19)	C40—O10—C37—C36	−177.5 (2)
C18—O5—C15—C16	−0.1 (2)	O9—C36—C37—C38	−178.8 (3)
C18—O5—C15—C14	175.8 (2)	N5—C36—C37—C38	−0.4 (3)
O4—C14—C15—C16	172.2 (2)	O9—C36—C37—O10	−0.6 (4)
N2—C14—C15—C16	−6.3 (3)	N5—C36—C37—O10	177.80 (19)
O4—C14—C15—O5	−3.1 (4)	O10—C37—C38—N6	179.02 (19)
N2—C14—C15—O5	178.35 (18)	C36—C37—C38—N6	−2.6 (4)
O5—C15—C16—N3	179.52 (18)	O10—C37—C38—C39	−0.8 (3)
C14—C15—C16—N3	3.7 (3)	C36—C37—C38—C39	177.6 (2)
O5—C15—C16—C17	0.2 (2)	C35—N6—C38—C37	2.6 (3)
C14—C15—C16—C17	−175.6 (2)	C35—N6—C38—C39	−177.6 (2)
C13—N3—C16—C15	−0.4 (3)	C37—C38—C39—C44	−178.9 (3)
C13—N3—C16—C17	178.8 (2)	N6—C38—C39—C44	1.3 (4)
C15—C16—C17—C22	178.3 (3)	C37—C38—C39—C40	0.3 (2)
N3—C16—C17—C22	−1.0 (4)	N6—C38—C39—C40	−179.5 (2)
C15—C16—C17—C18	−0.2 (2)	C44—C39—C40—C41	0.0 (4)
N3—C16—C17—C18	−179.5 (2)	C38—C39—C40—C41	−179.4 (2)
C15—O5—C18—C19	−180.0 (2)	C44—C39—C40—O10	179.6 (2)
C15—O5—C18—C17	−0.1 (2)	C38—C39—C40—O10	0.2 (2)
C22—C17—C18—C19	1.3 (3)	C37—O10—C40—C41	178.9 (2)
C16—C17—C18—C19	−179.9 (2)	C37—O10—C40—C39	−0.7 (2)
C22—C17—C18—O5	−178.6 (2)	C39—C40—C41—C42	0.0 (4)
C16—C17—C18—O5	0.2 (2)	O10—C40—C41—C42	−179.6 (2)
O5—C18—C19—C20	178.5 (2)	C40—C41—C42—C43	−0.1 (4)
C17—C18—C19—C20	−1.4 (4)	C41—C42—C43—C44	0.3 (5)
C18—C19—C20—C21	0.1 (4)	C42—C43—C44—C39	−0.3 (4)
C19—C20—C21—C22	1.3 (4)	C40—C39—C44—C43	0.2 (4)
C20—C21—C22—C17	−1.4 (4)	C38—C39—C44—C43	179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31B···O9	0.97	2.48	3.069 (3)	119
C30—H30···O4	0.98	2.28	3.071 (3)	137
C4—H4···O1ⁱ	0.93	2.60	3.333 (3)	136
C2—H2···O10ⁱⁱ	0.93	2.49	3.399 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆ClN₃O₅
M_r	437.83
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.9711 (11), 12.9079 (12), 15.0957 (14)
α, β, γ (°)	99.201 (2), 102.486 (2), 110.085 (2)
V (Å³)	2068.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.936, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	19990, 8066, 5272
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.161, 0.99
No. of reflections	8066
No. of parameters	556
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.30

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31B···O9	0.97	2.48	3.069 (3)	119
C30—H30···O4	0.98	2.28	3.071 (3)	137
C4—H4···O1ⁱ	0.93	2.60	3.333 (3)	136
C2—H2···O10ⁱⁱ	0.93	2.49	3.399 (3)	165

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

Acknowledgements

The authors gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (grant No. D200724001) and the Science Research Project of Yunyang Medical College (grant No. 2006QDJ16).

References

Bodke, Y. & Sangapure, S. S. (2003). J. Indian Chem. Soc. 80, 187–189. CAS Google Scholar
Bruker (2001). SMART (Version 5.628) and SAINT-Plus (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, Y.-G., Li, G.-H., Tian, J.-H., Ding, M.-W. & He, H.-W. (2005). Acta Cryst. E61, o3266–o3268. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836–o1838. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457–o1459. Web of Science CSD CrossRef IUCr Journals Google Scholar
Moneam, M., Geies, A., El-Naggar, G. & Mousa, S. (2004). J. Chin. Chem. Soc. 51, 1357–1366. Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 1| January 2008| Pages o321-o322

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-[1-(4-chloro­phen­yl)-2,5-dioxo-1,2,3,5-tetra­hydro­imidazo[1′,2′:1,2]pyrimidino[5,4-b][1]benzo­furan-3-yl]acetate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 2-[1-(4-chlorophenyl)-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1′,2′:1,2]pyrimidino[5,4-b][1]benzofuran-3-yl]acetate