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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o321–o322.
Published online 2007 December 21. doi:  10.1107/S1600536807066998
PMCID: PMC2915365

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

Abstract

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 [triangle]); Bodke & Sangapure (2003 [triangle]). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 [triangle], 2006 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o321-scheme1.jpg

Experimental

Crystal data

  • C22H16ClN3O5
  • M r = 437.83
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o321-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066998/nc2080Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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).

Crystal data

C22H16ClN3O5Z = 4
Mr = 437.83F000 = 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 = 0.00–0.00º
c = 15.0957 (14) ŵ = 0.23 mm1
α = 99.201 (2)ºT = 293 (2) K
β = 102.486 (2)ºBlock, colorless
γ = 110.085 (2)º0.30 × 0.20 × 0.20 mm
V = 2068.0 (3) Å3

Data collection

Bruker SMART 4K CCD area-detector diffractometer8066 independent reflections
Radiation source: fine-focus sealed tube5272 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.101
T = 293(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −14→14
Tmin = 0.936, Tmax = 0.956k = −15→15
19990 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.161  w = 1/[σ2(Fo2) + (0.0796P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
8066 reflectionsΔρmax = 0.31 e Å3
556 parametersΔρmin = −0.30 e Å3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

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)
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)
H41−0.1760−0.03360.25330.087*
C42−0.2402 (3)0.0656 (3)0.3268 (2)0.0835 (8)
H42−0.31750.04100.28270.100*
C43−0.2121 (3)0.1473 (3)0.4099 (2)0.0848 (8)
H43−0.27100.17570.42020.102*
C44−0.0984 (2)0.1863 (2)0.47677 (18)0.0721 (7)
H44−0.07970.24110.53190.086*

Atomic displacement parameters (Å2)

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, °)

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—C4−178.63 (18)C16—C17—C22—C21−178.2 (2)
C2—C1—C3—C5−0.1 (4)C25—C23—C24—C260.1 (5)
Cl1—C1—C3—C5179.37 (17)Cl2—C23—C24—C26−179.8 (3)
C1—C2—C4—C6−0.7 (3)C24—C23—C25—C270.5 (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—C280.5 (6)
C2—C4—C6—N1−179.13 (19)C23—C25—C27—C28−1.7 (4)
C3—C5—C6—C40.9 (3)C24—C26—C28—C27−1.7 (5)
C3—C5—C6—N1179.88 (19)C24—C26—C28—N4178.3 (3)
C7—N1—C6—C4−115.8 (2)C25—C27—C28—C262.3 (4)
C13—N1—C6—C476.3 (3)C25—C27—C28—N4−177.8 (2)
C7—N1—C6—C565.2 (3)C29—N4—C28—C26−118.3 (3)
C13—N1—C6—C5−102.8 (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—C27−117.1 (3)
C13—N1—C7—C8−1.3 (2)C35—N4—C29—O6173.9 (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—C964.4 (3)C28—N4—C29—C30174.5 (2)
C13—N2—C8—C70.4 (2)C35—N5—C30—C29−3.2 (2)
C14—N2—C8—C7−173.65 (18)C36—N5—C30—C29180.0 (2)
O1—C7—C8—N2180.0 (2)C35—N5—C30—C31−125.9 (2)
N1—C7—C8—N20.6 (2)C36—N5—C30—C3157.3 (3)
O1—C7—C8—C9−56.3 (3)O6—C29—C30—N5−174.7 (3)
N1—C7—C8—C9124.3 (2)N4—C29—C30—N55.8 (2)
N2—C8—C9—C1064.4 (3)O6—C29—C30—C31−50.9 (3)
C7—C8—C9—C10−51.5 (3)N4—C29—C30—C31129.6 (2)
C11'—O3—C10—O2−11.2 (7)N5—C30—C31—C3259.3 (3)
C11—O3—C10—O215.3 (5)C29—C30—C31—C32−56.9 (3)
C11'—O3—C10—C9168.8 (5)C33—O8—C32—O72.6 (4)
C11—O3—C10—C9−164.6 (4)C33—O8—C32—C31−176.6 (3)
C8—C9—C10—O21.2 (4)C30—C31—C32—O73.9 (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—C34169.7 (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—N50.2 (3)
C11—O3—C11'—C12'104.8 (16)C38—N6—C35—N4−179.5 (2)
C16—N3—C13—N20.7 (3)C36—N5—C35—N6−3.3 (4)
C16—N3—C13—N1−176.20 (18)C30—N5—C35—N6179.8 (2)
C14—N2—C13—N3−4.4 (3)C36—N5—C35—N4176.4 (2)
C8—N2—C13—N3−178.5 (2)C30—N5—C35—N4−0.5 (3)
C14—N2—C13—N1172.86 (17)C29—N4—C35—N6−175.7 (2)
C8—N2—C13—N1−1.2 (2)C28—N4—C35—N63.2 (4)
C7—N1—C13—N3179.0 (2)C29—N4—C35—N54.6 (3)
C6—N1—C13—N3−11.6 (3)C28—N4—C35—N5−176.5 (2)
C7—N1—C13—N21.6 (2)C35—N5—C36—O9−178.3 (2)
C6—N1—C13—N2171.02 (17)C30—N5—C36—O9−1.9 (4)
C13—N2—C14—O4−172.1 (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—C36−177.5 (2)
C18—O5—C15—C16−0.1 (2)O9—C36—C37—C38−178.8 (3)
C18—O5—C15—C14175.8 (2)N5—C36—C37—C38−0.4 (3)
O4—C14—C15—C16172.2 (2)O9—C36—C37—O10−0.6 (4)
N2—C14—C15—C16−6.3 (3)N5—C36—C37—O10177.80 (19)
O4—C14—C15—O5−3.1 (4)O10—C37—C38—N6179.02 (19)
N2—C14—C15—O5178.35 (18)C36—C37—C38—N6−2.6 (4)
O5—C15—C16—N3179.52 (18)O10—C37—C38—C39−0.8 (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—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—C17178.8 (2)N6—C38—C39—C441.3 (4)
C15—C16—C17—C22178.3 (3)C37—C38—C39—C400.3 (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—C410.0 (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—O10179.6 (2)
C15—O5—C18—C17−0.1 (2)C38—C39—C40—O100.2 (2)
C22—C17—C18—C191.3 (3)C37—O10—C40—C41178.9 (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—C420.0 (4)
C16—C17—C18—O50.2 (2)O10—C40—C41—C42−179.6 (2)
O5—C18—C19—C20178.5 (2)C40—C41—C42—C43−0.1 (4)
C17—C18—C19—C20−1.4 (4)C41—C42—C43—C440.3 (5)
C18—C19—C20—C210.1 (4)C42—C43—C44—C39−0.3 (4)
C19—C20—C21—C221.3 (4)C40—C39—C44—C430.2 (4)
C20—C21—C22—C17−1.4 (4)C38—C39—C44—C43179.3 (3)

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2080).

References

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  • Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836–o1838.
  • Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457–o1459.
  • Moneam, M., Geies, A., El-Naggar, G. & Mousa, S. (2004). J. Chin. Chem. Soc.51, 1357–1366.
  • Sheldrick, G. M. (1997). SHELXL97 and SHELXS97 University of Göttingen, Germany.
  • Sheldrick, G. M. (2001). SHELXTL Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.
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