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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890

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

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[Moneam, M., Geies, A., El-Naggar, G. & Mousa, S. (2004). J. Chin. Chem. Soc. 51, 1357-1366.]); Bodke & Sangapure (2003[Bodke, Y. & Sangapure, S. S. (2003). J. Indian Chem. Soc. 80, 187-189.]). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005[Hu, Y.-G., Li, G.-H., Tian, J.-H., Ding, M.-W. & He, H.-W. (2005). Acta Cryst. E61, o3266-o3268.], 2006[Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457-o1459.], 2007[Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836-o1838.]).

[Scheme 1]

Experimental

Crystal data
  • C22H16ClN3O5

  • Mr = 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[Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.936, Tmax = 0.956

  • 19990 measured reflections

  • 8066 independent reflections

  • 5272 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2001). SMART (Version 5.628) and SAINT-Plus (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART (Version 5.628) and SAINT-Plus (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2001[Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.]).

Supporting information


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.

Refinement top

All H-atoms were positioned with idealized geometry and refined isotropic (Uiso(H)= 1.5Ueq(C)for methyl H atoms and Uiso(H) =1.2Ueq(C) for all other H atoms) using a riding model with C—H = 0.93°, 0.97° and = 0.96 Å. The carbon atoms C11, C12 and c34 are disordered over two sites, and were refined using a split model with fixed s.o.f. of 0.55/0.45 for C11/C11' and C12 C12' and of 0.60/0.40 for C34/C34', respectively.

Structure description 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.

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).

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
[Figure 1] 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
C22H16ClN3O5Z = 4
Mr = 437.83F(000) = 904
Triclinic, P1Dx = 1.406 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.9711 (11) ÅCell parameters from 5946 reflections
b = 12.9079 (12) Åθ = 0.0–0.0°
c = 15.0957 (14) ŵ = 0.23 mm1
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 tube5272 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.101
φ and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1414
Tmin = 0.936, Tmax = 0.956k = 1515
19990 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0796P)2]
where P = (Fo2 + 2Fc2)/3
8066 reflections(Δ/σ)max = 0.001
556 parametersΔρmax = 0.31 e Å3
4 restraintsΔρmin = 0.30 e Å3
Crystal data top
C22H16ClN3O5γ = 110.085 (2)°
Mr = 437.83V = 2068.0 (3) Å3
Triclinic, P1Z = 4
a = 11.9711 (11) ÅMo Kα radiation
b = 12.9079 (12) ŵ = 0.23 mm1
c = 15.0957 (14) ÅT = 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)
Tmin = 0.936, Tmax = 0.956Rint = 0.101
19990 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0564 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 0.99Δρmax = 0.31 e Å3
8066 reflectionsΔρmin = 0.30 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cl11.31245 (7)0.33661 (9)1.33809 (5)0.1148 (4)
O11.04953 (14)0.13649 (13)0.87225 (11)0.0619 (4)
O20.9535 (2)0.34943 (16)0.87703 (14)0.0966 (6)
O30.9297 (3)0.37601 (19)0.73355 (16)0.1144 (8)
O40.57242 (14)0.06236 (15)0.74406 (11)0.0699 (5)
O50.45393 (13)0.10771 (13)0.89127 (12)0.0662 (5)
N10.93085 (15)0.15775 (15)0.96988 (11)0.0491 (4)
N20.75138 (15)0.12384 (14)0.86505 (11)0.0501 (4)
N30.76535 (15)0.16729 (14)1.02776 (12)0.0499 (4)
C11.1999 (2)0.2852 (3)1.23024 (16)0.0674 (7)
C21.1089 (2)0.1778 (3)1.20875 (17)0.0701 (7)
H21.10700.13411.25220.084*
C31.2039 (2)0.3521 (2)1.16775 (18)0.0702 (7)
H31.26610.42491.18330.084*
C41.0204 (2)0.1351 (2)1.12231 (16)0.0593 (6)
H40.95890.06211.10670.071*
C51.1140 (2)0.3096 (2)1.08130 (16)0.0597 (6)
H51.11470.35391.03840.072*
C61.02376 (18)0.20104 (19)1.05954 (14)0.0478 (5)
C70.9533 (2)0.13632 (18)0.88426 (15)0.0508 (5)
C80.8342 (2)0.11147 (19)0.80869 (14)0.0544 (5)
H80.80180.03200.77210.065*
C90.8532 (2)0.1886 (2)0.74351 (16)0.0681 (7)
H9A0.90180.16870.70510.082*
H9B0.77290.17550.70190.082*
C100.9175 (3)0.3124 (2)0.7934 (2)0.0736 (7)
C111.0346 (8)0.5111 (6)0.7868 (6)0.119 (2)*0.55
H11A1.00850.54040.83840.142*0.55
H11B1.11360.50680.81390.142*0.55
C121.0553 (14)0.5882 (12)0.7364 (11)0.245 (6)*0.55
H12A1.11410.66080.77650.367*0.55
H12B0.97860.59460.70870.367*0.55
H12C1.08810.56460.68780.367*0.55
C11'0.9661 (9)0.4899 (7)0.7637 (6)0.110 (3)*0.45
H11C1.04710.52020.81000.132*0.45
H11D0.90820.50460.79490.132*0.45
C12'0.9739 (10)0.5526 (9)0.6900 (7)0.133 (3)*0.45
H12D0.99230.63130.71670.199*0.45
H12E0.89600.52010.64140.199*0.45
H12F1.03860.54700.66390.199*0.45
C130.81092 (18)0.15222 (17)0.95896 (14)0.0466 (5)
C140.6245 (2)0.09868 (18)0.82764 (16)0.0542 (5)
C150.57554 (19)0.12095 (18)0.90383 (17)0.0554 (6)
C160.64103 (18)0.14966 (17)0.99573 (15)0.0501 (5)
C170.5567 (2)0.15575 (18)1.04862 (17)0.0561 (6)
C180.4440 (2)0.12948 (19)0.9808 (2)0.0629 (6)
C190.3374 (2)0.1262 (2)1.0028 (3)0.0780 (8)
H190.26390.11010.95680.094*
C200.3456 (3)0.1477 (2)1.0958 (3)0.0878 (9)
H200.27530.14621.11330.105*
C210.4549 (3)0.1721 (2)1.1657 (2)0.0806 (8)
H210.45570.18471.22820.097*
C220.5627 (2)0.1776 (2)1.14290 (19)0.0680 (7)
H220.63650.19551.18930.082*
Cl20.33863 (8)0.57533 (6)1.01490 (5)0.0883 (3)
O60.60082 (18)0.31763 (18)0.75069 (12)0.0853 (6)
O70.51473 (18)0.37899 (16)0.54234 (14)0.0860 (6)
O80.6390 (2)0.34225 (18)0.46363 (15)0.0954 (6)
O90.30452 (17)0.02466 (16)0.42624 (12)0.0829 (5)
O100.05213 (15)0.02539 (13)0.36962 (10)0.0639 (4)
N40.39254 (18)0.28569 (17)0.69552 (12)0.0623 (5)
N50.33882 (17)0.15994 (16)0.55839 (11)0.0565 (5)
N60.18881 (18)0.22927 (16)0.59442 (12)0.0577 (5)
C230.3552 (2)0.49233 (19)0.92003 (15)0.0602 (6)
C240.2838 (3)0.3782 (2)0.8923 (2)0.0984 (11)
H240.22730.34600.92380.118*
C250.4375 (2)0.5398 (2)0.87435 (18)0.0711 (7)
H250.48630.61770.89400.085*
C260.2960 (3)0.3113 (2)0.8176 (2)0.1000 (11)
H260.24710.23350.79820.120*
C270.4491 (2)0.4730 (2)0.79872 (17)0.0660 (6)
H270.50400.50570.76620.079*
C280.3791 (2)0.3579 (2)0.77187 (14)0.0583 (6)
C290.4996 (3)0.2693 (2)0.69287 (16)0.0666 (6)
C300.4674 (2)0.1778 (2)0.60375 (15)0.0630 (6)
H300.46840.10790.62070.076*
C310.5563 (2)0.2119 (2)0.54537 (17)0.0671 (7)
H31A0.63830.22070.58080.081*
H31B0.52900.15090.48900.081*
C320.5654 (2)0.3198 (2)0.51802 (17)0.0653 (6)
C330.6636 (4)0.4482 (3)0.4349 (3)0.1105 (11)
H33A0.58840.44390.39150.133*0.60
H33B0.68720.51080.48940.133*0.60
H33C0.63740.43310.36710.133*0.40
H33D0.61990.49070.46060.133*0.40
C340.7589 (6)0.4693 (6)0.3917 (5)0.121 (2)*0.60
H34A0.77340.53970.37370.181*0.60
H34B0.73500.40810.33710.181*0.60
H34C0.83370.47460.43490.181*0.60
C34'0.7928 (10)0.5093 (10)0.4709 (9)0.131 (3)*0.40
H34D0.81530.58110.45470.197*0.40
H34E0.83440.46600.44470.197*0.40
H34F0.81710.52240.53800.197*0.40
C350.2970 (2)0.22450 (19)0.61329 (14)0.0548 (5)
C360.2644 (2)0.0824 (2)0.47202 (15)0.0610 (6)
C370.1460 (2)0.08853 (19)0.45146 (14)0.0554 (6)
C380.1131 (2)0.15856 (18)0.50819 (14)0.0540 (5)
C390.0124 (2)0.14175 (19)0.45958 (15)0.0577 (6)
C400.0446 (2)0.0603 (2)0.37588 (15)0.0604 (6)
C410.1572 (2)0.0209 (2)0.30865 (18)0.0729 (7)
H410.17600.03360.25330.087*
C420.2402 (3)0.0656 (3)0.3268 (2)0.0835 (8)
H420.31750.04100.28270.100*
C430.2121 (3)0.1473 (3)0.4099 (2)0.0848 (8)
H430.27100.17570.42020.102*
C440.0984 (2)0.1863 (2)0.47677 (18)0.0721 (7)
H440.07970.24110.53190.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0536 (9)0.0706 (11)0.0622 (10)0.0248 (8)0.0234 (8)0.0090 (8)
O20.1407 (19)0.0624 (12)0.0714 (13)0.0299 (12)0.0240 (12)0.0086 (10)
O30.192 (2)0.0956 (16)0.1072 (17)0.0835 (17)0.0784 (17)0.0547 (14)
O40.0623 (10)0.0782 (11)0.0519 (10)0.0264 (9)0.0050 (8)0.0026 (8)
O50.0427 (9)0.0667 (11)0.0782 (12)0.0215 (8)0.0064 (8)0.0044 (9)
N10.0384 (9)0.0599 (11)0.0444 (10)0.0173 (8)0.0102 (8)0.0080 (8)
N20.0433 (10)0.0540 (11)0.0447 (10)0.0175 (8)0.0056 (8)0.0043 (8)
N30.0424 (10)0.0547 (11)0.0487 (10)0.0186 (8)0.0116 (8)0.0065 (8)
C10.0496 (14)0.099 (2)0.0466 (13)0.0293 (15)0.0102 (11)0.0039 (13)
C20.0592 (15)0.105 (2)0.0593 (15)0.0387 (16)0.0222 (12)0.0355 (15)
C30.0531 (14)0.0731 (17)0.0635 (16)0.0109 (13)0.0112 (12)0.0005 (14)
C40.0471 (13)0.0697 (15)0.0615 (14)0.0203 (11)0.0161 (11)0.0235 (12)
C50.0535 (13)0.0648 (15)0.0526 (13)0.0149 (12)0.0147 (11)0.0125 (11)
C60.0362 (11)0.0581 (13)0.0473 (12)0.0176 (10)0.0132 (9)0.0091 (10)
C70.0494 (13)0.0468 (12)0.0542 (13)0.0175 (10)0.0170 (10)0.0082 (10)
C80.0577 (13)0.0524 (13)0.0455 (12)0.0210 (11)0.0109 (10)0.0003 (10)
C90.0752 (16)0.0773 (17)0.0474 (13)0.0275 (14)0.0158 (12)0.0126 (12)
C100.094 (2)0.0767 (18)0.0711 (18)0.0465 (16)0.0363 (16)0.0297 (16)
Cl10.0850 (5)0.1759 (9)0.0525 (4)0.0461 (6)0.0078 (4)0.0043 (5)
Cl20.1290 (6)0.0651 (4)0.0637 (4)0.0356 (4)0.0326 (4)0.0032 (3)
C130.0412 (11)0.0471 (12)0.0471 (12)0.0167 (9)0.0087 (9)0.0073 (9)
C140.0473 (13)0.0504 (13)0.0558 (14)0.0199 (10)0.0018 (11)0.0054 (11)
C150.0397 (12)0.0516 (13)0.0667 (15)0.0193 (10)0.0049 (11)0.0050 (11)
C160.0412 (12)0.0434 (11)0.0613 (14)0.0152 (10)0.0138 (10)0.0065 (10)
C170.0496 (13)0.0452 (12)0.0741 (16)0.0182 (10)0.0226 (12)0.0115 (11)
C180.0448 (13)0.0472 (13)0.0938 (19)0.0186 (11)0.0201 (13)0.0095 (13)
C190.0520 (15)0.0600 (16)0.119 (3)0.0214 (13)0.0288 (16)0.0111 (16)
C200.0663 (19)0.0630 (17)0.147 (3)0.0259 (15)0.058 (2)0.0223 (18)
C210.091 (2)0.0616 (16)0.107 (2)0.0325 (15)0.0614 (19)0.0195 (16)
C220.0696 (16)0.0587 (15)0.0837 (18)0.0268 (13)0.0360 (14)0.0174 (13)
O60.0730 (12)0.1010 (15)0.0600 (11)0.0287 (11)0.0006 (10)0.0005 (10)
O70.1001 (14)0.0830 (13)0.0992 (14)0.0507 (12)0.0493 (12)0.0276 (11)
O80.1111 (15)0.1048 (15)0.1158 (16)0.0615 (13)0.0718 (14)0.0542 (13)
O90.0913 (13)0.0927 (13)0.0578 (10)0.0419 (11)0.0205 (9)0.0109 (9)
O100.0740 (11)0.0617 (10)0.0391 (8)0.0171 (9)0.0094 (7)0.0014 (7)
N40.0625 (12)0.0733 (13)0.0381 (10)0.0208 (11)0.0107 (9)0.0018 (9)
N50.0635 (12)0.0642 (12)0.0383 (9)0.0241 (10)0.0154 (9)0.0052 (9)
N60.0643 (12)0.0587 (12)0.0380 (10)0.0169 (10)0.0137 (9)0.0016 (8)
C230.0785 (16)0.0492 (13)0.0424 (12)0.0186 (12)0.0139 (12)0.0030 (10)
C240.138 (3)0.0559 (16)0.0803 (19)0.0014 (16)0.071 (2)0.0027 (14)
C250.0845 (18)0.0469 (13)0.0637 (16)0.0110 (13)0.0172 (14)0.0046 (12)
C260.136 (3)0.0497 (15)0.0815 (19)0.0077 (16)0.062 (2)0.0109 (14)
C270.0678 (16)0.0626 (15)0.0563 (14)0.0110 (13)0.0219 (12)0.0129 (12)
C280.0645 (14)0.0604 (14)0.0349 (11)0.0135 (12)0.0120 (10)0.0003 (10)
C290.0718 (17)0.0749 (17)0.0451 (13)0.0251 (14)0.0111 (13)0.0103 (12)
C300.0751 (16)0.0696 (16)0.0451 (12)0.0333 (13)0.0138 (12)0.0102 (11)
C310.0692 (16)0.0772 (17)0.0634 (15)0.0387 (14)0.0210 (13)0.0162 (13)
C320.0615 (15)0.0785 (17)0.0585 (14)0.0319 (14)0.0190 (12)0.0128 (13)
C330.124 (3)0.115 (3)0.137 (3)0.060 (2)0.076 (3)0.068 (2)
C350.0649 (15)0.0541 (13)0.0360 (11)0.0154 (11)0.0165 (10)0.0022 (10)
C360.0791 (17)0.0609 (14)0.0376 (11)0.0253 (13)0.0172 (11)0.0031 (10)
C370.0633 (14)0.0549 (13)0.0383 (11)0.0169 (11)0.0120 (10)0.0041 (10)
C380.0638 (14)0.0529 (13)0.0378 (11)0.0145 (11)0.0176 (10)0.0061 (10)
C390.0596 (14)0.0564 (14)0.0467 (12)0.0116 (11)0.0160 (11)0.0098 (10)
C400.0661 (15)0.0603 (14)0.0457 (13)0.0150 (12)0.0168 (11)0.0106 (11)
C410.0701 (17)0.0689 (17)0.0529 (14)0.0080 (14)0.0033 (13)0.0072 (12)
C420.0649 (17)0.091 (2)0.0719 (18)0.0135 (16)0.0039 (14)0.0195 (16)
C430.0637 (17)0.098 (2)0.090 (2)0.0275 (16)0.0249 (16)0.0241 (18)
C440.0684 (17)0.0766 (17)0.0650 (16)0.0225 (14)0.0235 (14)0.0090 (13)
Geometric parameters (Å, º) top
Cl1—C11.732 (2)Cl2—C231.737 (2)
O1—C71.204 (2)O6—C291.212 (3)
O2—C101.199 (3)O7—C321.188 (3)
O3—C101.313 (3)O8—C321.322 (3)
O3—C11'1.348 (8)O8—C331.454 (4)
O3—C111.695 (8)O9—C361.220 (3)
O4—C141.213 (3)O10—C371.379 (2)
O5—C151.373 (2)O10—C401.395 (3)
O5—C181.375 (3)N4—C291.377 (3)
N1—C71.381 (3)N4—C351.387 (3)
N1—C131.384 (2)N4—C281.436 (3)
N1—C61.436 (2)N5—C351.370 (3)
N2—C131.367 (3)N5—C361.401 (3)
N2—C141.401 (3)N5—C301.463 (3)
N2—C81.471 (3)N6—C351.290 (3)
N3—C131.291 (3)N6—C381.375 (3)
N3—C161.386 (3)C23—C251.355 (3)
C1—C21.370 (4)C23—C241.363 (3)
C1—C31.375 (4)C24—C261.374 (4)
C2—C41.379 (3)C24—H240.9300
C2—H20.9300C25—C271.379 (3)
C3—C51.386 (3)C25—H250.9300
C3—H30.9300C26—C281.359 (4)
C4—C61.369 (3)C26—H260.9300
C4—H40.9300C27—C281.370 (3)
C5—C61.378 (3)C27—H270.9300
C5—H50.9300C29—C301.519 (3)
C7—C81.517 (3)C30—C311.520 (3)
C8—C91.505 (3)C30—H300.9800
C8—H80.9800C31—C321.490 (4)
C9—C101.495 (4)C31—H31A0.9700
C9—H9A0.9700C31—H31B0.9700
C9—H9B0.9700C33—C341.402 (7)
C11—C121.335 (13)C33—C34'1.405 (11)
C11—H11A0.9700C33—H33A0.9700
C11—H11B0.9700C33—H33B0.9700
C12—H12A0.9600C33—H33C0.9700
C12—H12B0.9600C33—H33D0.9700
C12—H12C0.9600C34—H34A0.9600
C11'—C12'1.478 (1)C34—H34B0.9600
C11'—H11C0.9700C34—H34C0.9600
C11'—H11D0.9700C34'—H34D0.9600
C12'—H12D0.9600C34'—H34E0.9600
C12'—H12E0.9600C34'—H34F0.9600
C12'—H12F0.9600C36—C371.417 (3)
C14—C151.432 (3)C37—C381.359 (3)
C15—C161.357 (3)C38—C391.446 (3)
C16—C171.430 (3)C39—C441.391 (3)
C17—C221.387 (3)C39—C401.392 (3)
C17—C181.400 (3)C40—C411.371 (3)
C18—C191.375 (3)C41—C421.361 (4)
C19—C201.361 (4)C41—H410.9300
C19—H190.9300C42—C431.396 (4)
C20—C211.392 (4)C42—H420.9300
C20—H200.9300C43—C441.377 (4)
C21—C221.387 (3)C43—H430.9300
C21—H210.9300C44—H440.9300
C22—H220.9300
C10—O3—C11'120.0 (4)C35—N5—C30111.52 (17)
C10—O3—C11111.5 (4)C36—N5—C30124.84 (18)
C15—O5—C18104.37 (17)C35—N6—C38111.59 (18)
C7—N1—C13111.36 (17)C25—C23—C24120.5 (2)
C7—N1—C6125.24 (16)C25—C23—Cl2120.77 (18)
C13—N1—C6122.46 (16)C24—C23—Cl2118.7 (2)
C13—N2—C14124.04 (18)C23—C24—C26119.5 (3)
C13—N2—C8111.30 (16)C23—C24—H24120.3
C14—N2—C8124.37 (17)C26—C24—H24120.3
C13—N3—C16111.37 (17)C23—C25—C27120.1 (2)
C2—C1—C3121.4 (2)C23—C25—H25119.9
C2—C1—Cl1119.1 (2)C27—C25—H25119.9
C3—C1—Cl1119.6 (2)C28—C26—C24120.5 (2)
C1—C2—C4119.5 (2)C28—C26—H26119.8
C1—C2—H2120.2C24—C26—H26119.8
C4—C2—H2120.2C28—C27—C25119.4 (2)
C1—C3—C5119.0 (2)C28—C27—H27120.3
C1—C3—H3120.5C25—C27—H27120.3
C5—C3—H3120.5C26—C28—C27120.0 (2)
C6—C4—C2119.5 (2)C26—C28—N4119.4 (2)
C6—C4—H4120.2C27—C28—N4120.6 (2)
C2—C4—H4120.2O6—C29—N4126.9 (2)
C6—C5—C3119.4 (2)O6—C29—C30125.9 (2)
C6—C5—H5120.3N4—C29—C30107.2 (2)
C3—C5—H5120.3N5—C30—C29101.64 (18)
C4—C6—C5121.1 (2)N5—C30—C31114.95 (18)
C4—C6—N1119.9 (2)C29—C30—C31113.2 (2)
C5—C6—N1118.99 (19)N5—C30—H30108.9
O1—C7—N1126.02 (19)C29—C30—H30108.9
O1—C7—C8126.6 (2)C31—C30—H30108.9
N1—C7—C8107.38 (17)C32—C31—C30113.7 (2)
N2—C8—C9115.14 (18)C32—C31—H31A108.8
N2—C8—C7101.66 (16)C30—C31—H31A108.8
C9—C8—C7112.54 (19)C32—C31—H31B108.8
N2—C8—H8109.1C30—C31—H31B108.8
C9—C8—H8109.1H31A—C31—H31B107.7
C7—C8—H8109.1O7—C32—O8124.1 (3)
C10—C9—C8113.5 (2)O7—C32—C31124.9 (2)
C10—C9—H9A108.9O8—C32—C31111.0 (2)
C8—C9—H9A108.9C34—C33—C34'48.1 (5)
C10—C9—H9B108.9C34—C33—O8111.2 (4)
C8—C9—H9B108.9C34'—C33—O8105.2 (5)
H9A—C9—H9B107.7C34—C33—H33A109.4
O2—C10—O3124.1 (3)C34'—C33—H33A144.3
O2—C10—C9124.8 (2)O8—C33—H33A109.4
O3—C10—C9111.1 (3)C34—C33—H33B109.4
C12—C11—O3119.2 (9)C34'—C33—H33B67.0
C12—C11—H11A107.5O8—C33—H33B109.4
O3—C11—H11A107.5H33A—C33—H33B108.0
C12—C11—H11B107.5C34—C33—H33C64.0
O3—C11—H11B107.5C34'—C33—H33C110.7
H11A—C11—H11B107.0O8—C33—H33C110.7
C11—C12—H12A109.5H33A—C33—H33C48.4
C11—C12—H12B109.5H33B—C33—H33C138.7
H12A—C12—H12B109.5C34—C33—H33D137.0
C11—C12—H12C109.5C34'—C33—H33D110.7
H12A—C12—H12C109.5O8—C33—H33D110.7
H12B—C12—H12C109.5H33A—C33—H33D64.3
O3—C11'—C12'115.4 (8)H33B—C33—H33D46.0
O3—C11'—H11C108.4H33C—C33—H33D108.8
C12'—C11'—H11C108.4C33—C34—H34A109.5
O3—C11'—H11D108.4H33C—C34—H34A96.0
C12'—C11'—H11D108.4C33—C34—H34B109.5
H11C—C11'—H11D107.5H33C—C34—H34B78.0
C11'—C12'—H12D109.5H34A—C34—H34B109.5
C11'—C12'—H12E109.5C33—C34—H34C109.5
H12D—C12'—H12E109.5H33C—C34—H34C148.2
C11'—C12'—H12F109.5H34A—C34—H34C109.5
H12D—C12'—H12F109.5H34B—C34—H34C109.5
H12E—C12'—H12F109.5C33—C34'—H34D109.5
N3—C13—N2127.63 (18)C33—C34'—H34E109.5
N3—C13—N1124.03 (18)H34D—C34'—H34E109.5
N2—C13—N1108.28 (17)C33—C34'—H34F109.5
O4—C14—N2122.0 (2)H34D—C34'—H34F109.5
O4—C14—C15129.9 (2)H34E—C34'—H34F109.5
N2—C14—C15108.12 (18)N6—C35—N5127.52 (19)
C16—C15—O5112.7 (2)N6—C35—N4124.65 (19)
C16—C15—C14124.07 (19)N5—C35—N4107.8 (2)
O5—C15—C14123.1 (2)O9—C36—N5121.5 (2)
C15—C16—N3124.42 (19)O9—C36—C37129.9 (2)
C15—C16—C17106.63 (19)N5—C36—C37108.56 (19)
N3—C16—C17128.9 (2)C38—C37—O10112.6 (2)
C22—C17—C18119.5 (2)C38—C37—C36124.3 (2)
C22—C17—C16136.0 (2)O10—C37—C36123.08 (19)
C18—C17—C16104.5 (2)C37—C38—N6124.4 (2)
C19—C18—O5125.1 (2)C37—C38—C39106.41 (19)
C19—C18—C17123.2 (3)N6—C38—C39129.2 (2)
O5—C18—C17111.80 (19)C44—C39—C40118.8 (2)
C20—C19—C18116.3 (3)C44—C39—C38136.1 (2)
C20—C19—H19121.9C40—C39—C38105.1 (2)
C18—C19—H19121.9C41—C40—C39123.6 (2)
C19—C20—C21122.7 (3)C41—C40—O10125.0 (2)
C19—C20—H20118.7C39—C40—O10111.4 (2)
C21—C20—H20118.7C42—C41—C40116.7 (2)
C22—C21—C20120.7 (3)C42—C41—H41121.6
C22—C21—H21119.7C40—C41—H41121.6
C20—C21—H21119.7C41—C42—C43121.7 (3)
C21—C22—C17117.8 (3)C41—C42—H42119.2
C21—C22—H22121.1C43—C42—H42119.2
C17—C22—H22121.1C44—C43—C42121.0 (3)
C32—O8—C33118.0 (2)C44—C43—H43119.5
C37—O10—C40104.51 (16)C42—C43—H43119.5
C29—N4—C35111.43 (18)C43—C44—C39118.2 (2)
C29—N4—C28125.47 (19)C43—C44—H44120.9
C35—N4—C28123.10 (19)C39—C44—H44120.9
C35—N5—C36123.56 (19)
C3—C1—C2—C40.9 (4)C18—C17—C22—C210.1 (3)
Cl1—C1—C2—C4178.63 (18)C16—C17—C22—C21178.2 (2)
C2—C1—C3—C50.1 (4)C25—C23—C24—C260.1 (5)
Cl1—C1—C3—C5179.37 (17)Cl2—C23—C24—C26179.8 (3)
C1—C2—C4—C60.7 (3)C24—C23—C25—C270.5 (4)
C1—C3—C5—C60.7 (3)Cl2—C23—C25—C27179.56 (19)
C2—C4—C6—C50.1 (3)C23—C24—C26—C280.5 (6)
C2—C4—C6—N1179.13 (19)C23—C25—C27—C281.7 (4)
C3—C5—C6—C40.9 (3)C24—C26—C28—C271.7 (5)
C3—C5—C6—N1179.88 (19)C24—C26—C28—N4178.3 (3)
C7—N1—C6—C4115.8 (2)C25—C27—C28—C262.3 (4)
C13—N1—C6—C476.3 (3)C25—C27—C28—N4177.8 (2)
C7—N1—C6—C565.2 (3)C29—N4—C28—C26118.3 (3)
C13—N1—C6—C5102.8 (2)C35—N4—C28—C2662.9 (3)
C13—N1—C7—O1179.2 (2)C29—N4—C28—C2761.7 (3)
C6—N1—C7—O110.2 (3)C35—N4—C28—C27117.1 (3)
C13—N1—C7—C81.3 (2)C35—N4—C29—O6173.9 (3)
C6—N1—C7—C8170.42 (19)C28—N4—C29—O65.0 (4)
C13—N2—C8—C9121.6 (2)C35—N4—C29—C306.6 (3)
C14—N2—C8—C964.4 (3)C28—N4—C29—C30174.5 (2)
C13—N2—C8—C70.4 (2)C35—N5—C30—C293.2 (2)
C14—N2—C8—C7173.65 (18)C36—N5—C30—C29180.0 (2)
O1—C7—C8—N2180.0 (2)C35—N5—C30—C31125.9 (2)
N1—C7—C8—N20.6 (2)C36—N5—C30—C3157.3 (3)
O1—C7—C8—C956.3 (3)O6—C29—C30—N5174.7 (3)
N1—C7—C8—C9124.3 (2)N4—C29—C30—N55.8 (2)
N2—C8—C9—C1064.4 (3)O6—C29—C30—C3150.9 (3)
C7—C8—C9—C1051.5 (3)N4—C29—C30—C31129.6 (2)
C11'—O3—C10—O211.2 (7)N5—C30—C31—C3259.3 (3)
C11—O3—C10—O215.3 (5)C29—C30—C31—C3256.9 (3)
C11'—O3—C10—C9168.8 (5)C33—O8—C32—O72.6 (4)
C11—O3—C10—C9164.6 (4)C33—O8—C32—C31176.6 (3)
C8—C9—C10—O21.2 (4)C30—C31—C32—O73.9 (4)
C8—C9—C10—O3178.8 (2)C30—C31—C32—O8176.9 (2)
C10—O3—C11—C12177.8 (9)C32—O8—C33—C34169.7 (4)
C11'—O3—C11—C1262.6 (14)C32—O8—C33—C34'119.3 (6)
C10—O3—C11'—C12'178.7 (6)C38—N6—C35—N50.2 (3)
C11—O3—C11'—C12'104.8 (16)C38—N6—C35—N4179.5 (2)
C16—N3—C13—N20.7 (3)C36—N5—C35—N63.3 (4)
C16—N3—C13—N1176.20 (18)C30—N5—C35—N6179.8 (2)
C14—N2—C13—N34.4 (3)C36—N5—C35—N4176.4 (2)
C8—N2—C13—N3178.5 (2)C30—N5—C35—N40.5 (3)
C14—N2—C13—N1172.86 (17)C29—N4—C35—N6175.7 (2)
C8—N2—C13—N11.2 (2)C28—N4—C35—N63.2 (4)
C7—N1—C13—N3179.0 (2)C29—N4—C35—N54.6 (3)
C6—N1—C13—N311.6 (3)C28—N4—C35—N5176.5 (2)
C7—N1—C13—N21.6 (2)C35—N5—C36—O9178.3 (2)
C6—N1—C13—N2171.02 (17)C30—N5—C36—O91.9 (4)
C13—N2—C14—O4172.1 (2)C35—N5—C36—C373.1 (3)
C8—N2—C14—O41.2 (3)C30—N5—C36—C37179.5 (2)
C13—N2—C14—C156.6 (3)C40—O10—C37—C380.9 (2)
C8—N2—C14—C15179.83 (19)C40—O10—C37—C36177.5 (2)
C18—O5—C15—C160.1 (2)O9—C36—C37—C38178.8 (3)
C18—O5—C15—C14175.8 (2)N5—C36—C37—C380.4 (3)
O4—C14—C15—C16172.2 (2)O9—C36—C37—O100.6 (4)
N2—C14—C15—C166.3 (3)N5—C36—C37—O10177.80 (19)
O4—C14—C15—O53.1 (4)O10—C37—C38—N6179.02 (19)
N2—C14—C15—O5178.35 (18)C36—C37—C38—N62.6 (4)
O5—C15—C16—N3179.52 (18)O10—C37—C38—C390.8 (3)
C14—C15—C16—N33.7 (3)C36—C37—C38—C39177.6 (2)
O5—C15—C16—C170.2 (2)C35—N6—C38—C372.6 (3)
C14—C15—C16—C17175.6 (2)C35—N6—C38—C39177.6 (2)
C13—N3—C16—C150.4 (3)C37—C38—C39—C44178.9 (3)
C13—N3—C16—C17178.8 (2)N6—C38—C39—C441.3 (4)
C15—C16—C17—C22178.3 (3)C37—C38—C39—C400.3 (2)
N3—C16—C17—C221.0 (4)N6—C38—C39—C40179.5 (2)
C15—C16—C17—C180.2 (2)C44—C39—C40—C410.0 (4)
N3—C16—C17—C18179.5 (2)C38—C39—C40—C41179.4 (2)
C15—O5—C18—C19180.0 (2)C44—C39—C40—O10179.6 (2)
C15—O5—C18—C170.1 (2)C38—C39—C40—O100.2 (2)
C22—C17—C18—C191.3 (3)C37—O10—C40—C41178.9 (2)
C16—C17—C18—C19179.9 (2)C37—O10—C40—C390.7 (2)
C22—C17—C18—O5178.6 (2)C39—C40—C41—C420.0 (4)
C16—C17—C18—O50.2 (2)O10—C40—C41—C42179.6 (2)
O5—C18—C19—C20178.5 (2)C40—C41—C42—C430.1 (4)
C17—C18—C19—C201.4 (4)C41—C42—C43—C440.3 (5)
C18—C19—C20—C210.1 (4)C42—C43—C44—C390.3 (4)
C19—C20—C21—C221.3 (4)C40—C39—C44—C430.2 (4)
C20—C21—C22—C171.4 (4)C38—C39—C44—C43179.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C31—H31B···O90.972.483.069 (3)119
C30—H30···O40.982.283.071 (3)137
C4—H4···O1i0.932.603.333 (3)136
C2—H2···O10ii0.932.493.399 (3)165
Symmetry codes: (i) x+2, y, z+2; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC22H16ClN3O5
Mr437.83
Crystal system, space groupTriclinic, 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)
V3)2068.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 4K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.936, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
19990, 8066, 5272
Rint0.101
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.161, 0.99
No. of reflections8066
No. of parameters556
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C31—H31B···O90.972.483.069 (3)119
C30—H30···O40.982.283.071 (3)137
C4—H4···O1i0.932.603.333 (3)136
C2—H2···O10ii0.932.493.399 (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

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

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