PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1078.
Published online 2009 April 22. doi:  10.1107/S1600536809013166
PMCID: PMC2977757

4′-Chloro-3′,5′-dimethoxy­acetanilide

Abstract

The title compound, C10H12ClNO3, crystallizes with four independent mol­ecules in the asymmetric unit which are linked by inter­molecular N—H(...)O hydrogen bonds.

Related literature

The natural pyran­oacridone acronycine, which can be synthesized from the title compound, exhibits a broad spectrum of activity against numerous experimental tumor models, see: Nguyen et al. (2006 [triangle]). For a related structure, see: Lai et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1078-scheme1.jpg

Experimental

Crystal data

  • C10H12ClNO3
  • M r = 229.66
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1078-efi1.jpg
  • a = 11.1373 (14) Å
  • b = 15.1159 (19) Å
  • c = 14.2802 (18) Å
  • β = 111.9280 (10)°
  • V = 2230.1 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.33 mm−1
  • T = 296 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.908, T max = 0.937
  • 11396 measured reflections
  • 6377 independent reflections
  • 5985 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.105
  • S = 1.07
  • 6377 reflections
  • 570 parameters
  • 38 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.18 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2293 Friedel pairs
  • Flack parameter: −0.02 (5)

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013166/fl2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013166/fl2238Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge support from the Excellent Youth Teacher Fund Research Project of Shanghai (No. Z-2008–25), the Special Project of Shanghai Nanotechnology (No. 0852 nm02400) and the Special Project of the Science and Technology Commission of Shanghai Municipality (No. 071605213).

supplementary crystallographic information

Comment

The natural pyranoacridone acronycine was shown to exhibit a broad spectrum of activity against numerous experimental tumor models, including sarcoma, myeloma, carcinoma, and melanoma (Nguyen et al., 2006). The title compound, (I, Fig. 1), can be used as an intermediate in the synthesis of acronycine derivatives. In this paper, we present the X-ray crystallographic analysis of (I), which crystallizes in the monoclinic space group P2(1) with four molecules in the asymmetric unit.

It is interesting to note that there are four independent molecules in the asymmetric unit which is different from a similar structure (Lai et al., 2007) that has two molecules in the asymmetric unit. The dihedral angle between the acetamide groups and the benzene rings is 3.786 (3)°, 15.359 (4)°, 18.189 (3)° and 32.301 (6)° respectively. The torsion angles of the methoxy groups with respect to the benzene rings also vary (from 2.57 (1) to -15.43 (1)°. The molecules are linked into stacks by internolecular N-H···O hydrogen bonding (Fig. 2 and Table 1) with packing between the stacks stabilized by van der Waals forces.

Experimental

To a solution of 3,5-dimethoxyanilide (195 mg, 1.0 mmol) in dry CH2Cl2 (4 ml) cooled with an ice-water bath was added N-chlorobutanimide (147 mg, 1.1 mmol) in portions. After 2 h, the reaction was warmed to room temperature and stirred for 30 min and then filtered. The resulting solution was evaporated to give a white solid which was further purified by column chromatography (CH2Cl2) to give (I) (yield 75%, m. p. 493 K). Single crystals of (I) were obtained by slow evaporation of a petroleum ether-ethyl acetate solution. After one week, single crystals suitable for X-ray diffraction were obtained respectively.

Refinement

All the H atoms were placed in geometrically idealized positions and constrained to ride their parent atoms, with N—H = 0.840–0.895 Å, Uiso(H) = 1.2Ueq(N) and C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
Fig. 2.
The crystal packing of (I), viewed along the a-axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C10H12ClNO3Dx = 1.368 Mg m3
Mr = 229.66Melting point: 493 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.1373 (14) ÅCell parameters from 7547 reflections
b = 15.1159 (19) Åθ = 2.4–27.2°
c = 14.2802 (18) ŵ = 0.33 mm1
β = 111.928 (1)°T = 296 K
V = 2230.1 (5) Å3Block, colourless
Z = 80.30 × 0.20 × 0.20 mm
F(000) = 960

Data collection

Bruker SMART CCD area-detector diffractometer6377 independent reflections
Radiation source: fine-focus sealed tube5985 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −12→13
Tmin = 0.908, Tmax = 0.937k = −13→17
11396 measured reflectionsl = −16→16

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035w = 1/[σ2(Fo2) + (0.0603P)2 + 0.5909P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.25 e Å3
6377 reflectionsΔρmin = −0.17 e Å3
570 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
38 restraintsExtinction coefficient: 0.0059 (8)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2293 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.02 (5)

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*/Ueq
Cl10.50814 (9)0.60141 (6)0.49262 (8)0.0642 (3)
O10.2442 (2)0.54965 (16)0.3810 (2)0.0611 (6)
O20.1586 (3)0.97634 (19)0.3086 (2)0.0662 (7)
O30.5250 (2)0.78822 (18)0.4969 (2)0.0568 (6)
N10.0655 (3)0.8428 (2)0.3098 (2)0.0503 (7)
C10.1754 (3)0.7879 (2)0.3532 (2)0.0421 (7)
C20.2992 (3)0.8216 (2)0.4038 (2)0.0424 (7)
H20.31330.88240.40970.051*
C30.4001 (3)0.7634 (2)0.4448 (2)0.0421 (7)
C40.3794 (3)0.6724 (2)0.4367 (2)0.0440 (7)
C50.2560 (3)0.6400 (2)0.3866 (2)0.0455 (7)
C60.1529 (3)0.6973 (2)0.3435 (2)0.0462 (7)
H60.07010.67550.30860.055*
C70.1193 (4)0.5133 (3)0.3338 (4)0.0762 (12)
H7A0.06530.53200.36910.114*
H7B0.12490.44990.33500.114*
H7C0.08260.53330.26510.114*
C80.0608 (3)0.9307 (3)0.2914 (3)0.0535 (8)
C9−0.0731 (4)0.9684 (3)0.2456 (4)0.0721 (12)
H9A−0.06791.03160.24050.108*
H9B−0.12070.95410.28740.108*
H9C−0.11630.94380.17950.108*
C100.5538 (4)0.8806 (3)0.5012 (3)0.0665 (11)
H10A0.52790.90370.43390.100*
H10B0.64510.88930.53610.100*
H10C0.50770.91080.53660.100*
Cl20.55954 (10)−0.15609 (7)0.01677 (8)0.0650 (3)
O40.3842 (2)−0.20909 (15)0.11098 (18)0.0527 (6)
O50.3629 (2)0.21934 (17)0.1938 (2)0.0605 (6)
O60.5970 (3)0.03091 (19)0.0383 (2)0.0683 (7)
N20.3041 (3)0.07914 (18)0.2169 (2)0.0441 (6)
C110.3702 (3)0.0277 (2)0.1693 (2)0.0399 (7)
C120.3470 (3)−0.0642 (2)0.1676 (2)0.0420 (7)
H120.2938−0.08700.19860.050*
C130.4040 (3)−0.1200 (2)0.1194 (2)0.0415 (7)
C140.4881 (3)−0.0857 (2)0.0775 (2)0.0460 (7)
C150.5123 (3)0.0043 (2)0.0808 (2)0.0457 (7)
C160.4517 (3)0.0612 (2)0.1258 (2)0.0460 (7)
H160.46620.12180.12640.055*
C170.6186 (5)0.1241 (3)0.0333 (4)0.0850 (15)
H17A0.53690.15390.00390.128*
H17B0.66890.1342−0.00750.128*
H17C0.66430.14660.10010.128*
C180.3005 (3)0.1681 (2)0.2249 (3)0.0502 (8)
C190.2165 (4)0.2013 (3)0.2789 (3)0.0629 (10)
H19A0.26910.21300.34830.094*
H19B0.15290.15730.27570.094*
H19C0.17380.25470.24740.094*
C200.2957 (4)−0.2457 (3)0.1515 (3)0.0606 (10)
H20A0.3300−0.23880.22360.091*
H20B0.2834−0.30740.13490.091*
H20C0.2142−0.21550.12330.091*
Cl30.01359 (8)−0.00462 (6)1.02777 (6)0.0524 (2)
O70.0568 (2)0.18003 (16)1.00635 (18)0.0531 (6)
O80.1927 (2)0.27104 (18)0.73842 (19)0.0609 (7)
O90.1311 (3)−0.10568 (15)0.91356 (18)0.0538 (6)
N30.3026 (3)0.1427 (2)0.7915 (2)0.0451 (6)
C210.2327 (3)0.1090 (2)0.8477 (2)0.0392 (7)
C220.1802 (3)0.1657 (2)0.8994 (2)0.0423 (7)
H220.19040.22660.89720.051*
C230.1126 (3)0.1297 (2)0.9542 (2)0.0412 (7)
C240.0979 (3)0.0387 (2)0.9583 (2)0.0389 (6)
C250.1523 (3)−0.0168 (2)0.9073 (2)0.0405 (7)
C260.2202 (3)0.0183 (2)0.8522 (2)0.0428 (7)
H260.2570−0.01890.81850.051*
C270.1790 (5)−0.1637 (3)0.8574 (3)0.0682 (11)
H27A0.1397−0.14940.78690.102*
H27B0.1584−0.22370.86780.102*
H27C0.2712−0.15720.87950.102*
C280.2784 (3)0.2203 (2)0.7393 (2)0.0454 (7)
C290.3613 (3)0.2385 (3)0.6798 (3)0.0573 (9)
H29A0.31430.22420.61020.086*
H29B0.43830.20310.70550.086*
H29C0.38460.30000.68560.086*
C300.0697 (4)0.2730 (2)1.0017 (3)0.0606 (9)
H30A0.15960.28871.03070.091*
H30B0.02400.30141.03860.091*
H30C0.03420.29190.93250.091*
Cl41.03856 (8)0.29948 (8)0.49008 (8)0.0684 (3)
O100.8345 (2)0.17496 (18)0.3899 (2)0.0619 (7)
O110.4972 (2)0.53597 (17)0.23430 (19)0.0573 (6)
O120.9289 (2)0.47290 (17)0.47789 (18)0.0566 (6)
N40.4909 (2)0.38854 (19)0.2602 (2)0.0429 (6)
C310.6224 (3)0.3698 (2)0.3182 (2)0.0361 (6)
C320.6607 (3)0.2822 (2)0.3235 (2)0.0430 (7)
H320.60140.23860.28990.052*
C330.7887 (3)0.2602 (2)0.3797 (2)0.0457 (7)
C340.8772 (3)0.3252 (2)0.4263 (2)0.0437 (7)
C350.8372 (3)0.4127 (2)0.4242 (2)0.0410 (7)
C360.7081 (3)0.4349 (2)0.3696 (2)0.0403 (7)
H360.68030.49310.36790.048*
C370.8871 (4)0.5614 (3)0.4803 (3)0.0678 (11)
H37A0.86200.58700.41420.102*
H37B0.95660.59530.52710.102*
H37C0.81460.56180.50120.102*
C380.4380 (3)0.4664 (2)0.2209 (2)0.0426 (7)
C390.2963 (3)0.4632 (3)0.1571 (3)0.0570 (9)
H39A0.25580.51710.16540.086*
H39B0.25720.41400.17740.086*
H39C0.28500.45650.08740.086*
C400.7423 (4)0.1055 (3)0.3627 (3)0.0641 (10)
H40A0.68100.11470.39450.096*
H40B0.78560.05000.38450.096*
H40C0.69770.10480.29070.096*
H3A0.361 (3)0.109 (2)0.786 (2)0.039 (8)*
H2A0.261 (3)0.047 (2)0.247 (3)0.055 (10)*
H1A−0.008 (4)0.819 (3)0.295 (3)0.055 (11)*
H4A0.440 (3)0.346 (3)0.235 (3)0.050 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0549 (5)0.0394 (5)0.0880 (6)0.0025 (4)0.0147 (4)0.0066 (5)
O10.0557 (13)0.0326 (14)0.0833 (16)−0.0071 (11)0.0123 (12)−0.0004 (12)
O20.0690 (16)0.0501 (17)0.0882 (18)0.0024 (13)0.0392 (14)0.0134 (14)
O30.0495 (12)0.0405 (15)0.0749 (15)−0.0088 (11)0.0167 (11)−0.0075 (12)
N10.0492 (16)0.0429 (17)0.0614 (17)0.0034 (14)0.0237 (14)0.0054 (14)
C10.0497 (16)0.0368 (19)0.0453 (16)0.0035 (14)0.0241 (13)0.0041 (14)
C20.0546 (17)0.0311 (17)0.0483 (16)−0.0007 (14)0.0271 (14)−0.0018 (13)
C30.0442 (16)0.0391 (19)0.0463 (16)−0.0040 (14)0.0206 (14)−0.0050 (14)
C40.0514 (17)0.0325 (17)0.0494 (17)−0.0002 (14)0.0204 (14)−0.0004 (14)
C50.0557 (18)0.0305 (17)0.0524 (18)−0.0046 (14)0.0227 (15)0.0050 (14)
C60.0453 (16)0.041 (2)0.0520 (17)−0.0029 (15)0.0184 (14)−0.0011 (15)
C70.065 (2)0.039 (2)0.116 (3)−0.0170 (19)0.025 (2)−0.006 (2)
C80.0609 (19)0.049 (2)0.062 (2)0.0056 (18)0.0365 (17)0.0046 (18)
C90.071 (2)0.058 (3)0.095 (3)0.019 (2)0.041 (2)0.018 (2)
C100.064 (2)0.043 (2)0.089 (3)−0.0149 (18)0.024 (2)−0.008 (2)
Cl20.0837 (6)0.0467 (5)0.0848 (6)0.0072 (5)0.0548 (5)0.0030 (5)
O40.0759 (15)0.0264 (12)0.0671 (14)−0.0033 (11)0.0398 (12)−0.0016 (11)
O50.0622 (14)0.0320 (14)0.0868 (18)−0.0095 (12)0.0270 (13)−0.0055 (13)
O60.0870 (18)0.0430 (15)0.0985 (19)−0.0058 (14)0.0619 (16)0.0053 (14)
N20.0515 (14)0.0282 (15)0.0535 (15)−0.0054 (12)0.0206 (12)−0.0033 (11)
C110.0403 (15)0.0311 (17)0.0436 (15)−0.0012 (12)0.0101 (12)−0.0014 (13)
C120.0457 (15)0.0331 (18)0.0474 (16)−0.0024 (14)0.0175 (13)0.0006 (14)
C130.0505 (16)0.0300 (17)0.0429 (15)−0.0021 (13)0.0160 (13)0.0027 (13)
C140.0504 (16)0.0415 (19)0.0465 (16)0.0045 (15)0.0186 (14)0.0042 (14)
C150.0467 (16)0.0377 (18)0.0533 (17)−0.0019 (14)0.0192 (14)0.0093 (15)
C160.0492 (16)0.0326 (18)0.0502 (16)−0.0017 (14)0.0117 (14)0.0044 (14)
C170.121 (4)0.055 (3)0.106 (3)−0.027 (3)0.074 (3)0.002 (3)
C180.0464 (16)0.0361 (19)0.060 (2)0.0015 (15)0.0103 (15)−0.0037 (16)
C190.074 (2)0.040 (2)0.078 (2)0.0051 (18)0.032 (2)−0.0058 (19)
C200.086 (3)0.039 (2)0.073 (2)−0.0149 (19)0.048 (2)−0.0115 (17)
Cl30.0530 (4)0.0560 (6)0.0536 (4)−0.0101 (4)0.0260 (4)−0.0017 (4)
O70.0646 (14)0.0405 (14)0.0654 (14)0.0032 (11)0.0370 (12)−0.0089 (11)
O80.0659 (15)0.0546 (17)0.0636 (15)0.0218 (13)0.0259 (12)0.0196 (13)
O90.0757 (15)0.0296 (13)0.0619 (14)−0.0054 (11)0.0325 (12)−0.0049 (10)
N30.0457 (14)0.0422 (17)0.0514 (15)0.0054 (13)0.0230 (12)0.0058 (12)
C210.0375 (14)0.0394 (18)0.0391 (14)0.0013 (13)0.0123 (12)0.0017 (14)
C220.0469 (16)0.0300 (17)0.0499 (17)0.0006 (13)0.0180 (14)0.0005 (13)
C230.0390 (14)0.0423 (19)0.0407 (15)0.0026 (13)0.0132 (12)−0.0074 (13)
C240.0391 (14)0.0415 (18)0.0357 (14)−0.0034 (13)0.0135 (12)0.0009 (13)
C250.0463 (15)0.0326 (17)0.0396 (14)−0.0005 (13)0.0125 (12)−0.0005 (13)
C260.0477 (16)0.0401 (19)0.0419 (15)0.0062 (14)0.0181 (13)−0.0024 (13)
C270.102 (3)0.035 (2)0.078 (3)0.005 (2)0.046 (2)−0.0047 (19)
C280.0445 (15)0.044 (2)0.0424 (15)−0.0005 (15)0.0109 (13)0.0064 (15)
C290.0567 (19)0.056 (2)0.061 (2)−0.0024 (18)0.0250 (17)0.0147 (18)
C300.077 (2)0.036 (2)0.075 (2)0.0081 (17)0.036 (2)−0.0091 (18)
Cl40.0425 (4)0.0693 (7)0.0779 (6)0.0103 (4)0.0048 (4)0.0099 (5)
O100.0555 (14)0.0418 (15)0.0805 (17)0.0127 (12)0.0163 (12)0.0019 (13)
O110.0465 (12)0.0368 (13)0.0775 (16)−0.0083 (11)0.0106 (11)0.0043 (12)
O120.0441 (12)0.0495 (16)0.0607 (13)−0.0096 (11)0.0018 (10)0.0048 (11)
N40.0352 (12)0.0349 (16)0.0527 (15)−0.0069 (12)0.0097 (11)−0.0019 (12)
C310.0365 (13)0.0358 (18)0.0352 (13)−0.0004 (12)0.0124 (11)0.0028 (12)
C320.0430 (15)0.0372 (18)0.0457 (16)0.0001 (13)0.0128 (13)−0.0035 (14)
C330.0473 (16)0.043 (2)0.0460 (16)0.0074 (15)0.0168 (14)0.0003 (14)
C340.0389 (15)0.048 (2)0.0422 (15)0.0054 (14)0.0124 (12)0.0085 (14)
C350.0404 (15)0.0426 (19)0.0367 (14)−0.0075 (14)0.0106 (12)0.0024 (13)
C360.0402 (14)0.0378 (17)0.0393 (14)−0.0004 (14)0.0106 (12)0.0056 (13)
C370.060 (2)0.047 (2)0.073 (2)−0.0112 (18)−0.0012 (18)−0.0011 (19)
C380.0385 (15)0.0393 (19)0.0488 (16)−0.0008 (14)0.0149 (13)−0.0010 (14)
C390.0402 (16)0.047 (2)0.075 (2)−0.0010 (15)0.0111 (16)−0.0036 (18)
C400.074 (2)0.045 (2)0.070 (2)0.008 (2)0.0227 (19)−0.0044 (19)

Geometric parameters (Å, °)

Cl1—C41.729 (3)Cl3—C241.729 (3)
O1—C51.371 (4)O7—C231.366 (4)
O1—C71.412 (5)O7—C301.417 (4)
O2—C81.234 (4)O8—C281.220 (4)
O3—C31.363 (4)O9—C251.372 (4)
O3—C101.428 (5)O9—C271.420 (4)
N1—C81.351 (5)N3—C281.361 (4)
N1—C11.416 (4)N3—C211.405 (4)
N1—H1A0.85 (4)N3—H3A0.86 (3)
C1—C61.390 (5)C21—C261.383 (5)
C1—C21.392 (4)C21—C221.394 (4)
C2—C31.375 (4)C22—C231.384 (4)
C2—H20.9300C22—H220.9300
C3—C41.393 (5)C23—C241.389 (5)
C4—C51.381 (5)C24—C251.390 (4)
C5—C61.385 (5)C25—C261.384 (4)
C6—H60.9300C26—H260.9300
C7—H7A0.9600C27—H27A0.9600
C7—H7B0.9600C27—H27B0.9600
C7—H7C0.9600C27—H27C0.9600
C8—C91.500 (5)C28—C291.495 (5)
C9—H9A0.9600C29—H29A0.9600
C9—H9B0.9600C29—H29B0.9600
C9—H9C0.9600C29—H29C0.9600
C10—H10A0.9600C30—H30A0.9600
C10—H10B0.9600C30—H30B0.9600
C10—H10C0.9600C30—H30C0.9600
Cl2—C141.741 (3)Cl4—C341.729 (3)
O4—C131.362 (4)O10—C331.373 (4)
O4—C201.428 (4)O10—C401.418 (5)
O5—C181.229 (4)O11—C381.219 (4)
O6—C151.359 (4)O12—C351.369 (4)
O6—C171.436 (5)O12—C371.421 (5)
N2—C181.351 (4)N4—C381.341 (4)
N2—C111.408 (4)N4—C311.416 (4)
N2—H2A0.895 (18)N4—H4A0.84 (4)
C11—C161.374 (5)C31—C361.376 (4)
C11—C121.411 (5)C31—C321.385 (5)
C12—C131.384 (5)C32—C331.390 (4)
C12—H120.9300C32—H320.9300
C13—C141.388 (4)C33—C341.375 (5)
C14—C151.385 (5)C34—C351.392 (5)
C15—C161.390 (5)C35—C361.397 (4)
C16—H160.9300C36—H360.9300
C17—H17A0.9600C37—H37A0.9600
C17—H17B0.9600C37—H37B0.9600
C17—H17C0.9600C37—H37C0.9600
C18—C191.504 (5)C38—C391.500 (4)
C19—H19A0.9600C39—H39A0.9600
C19—H19B0.9600C39—H39B0.9600
C19—H19C0.9600C39—H39C0.9600
C20—H20A0.9600C40—H40A0.9600
C20—H20B0.9600C40—H40B0.9600
C20—H20C0.9600C40—H40C0.9600
C5—O1—C7118.1 (3)C23—O7—C30116.9 (3)
C3—O3—C10117.4 (3)C25—O9—C27117.2 (3)
C8—N1—C1128.7 (3)C28—N3—C21125.9 (3)
C8—N1—H1A113 (3)C28—N3—H3A117 (2)
C1—N1—H1A118 (3)C21—N3—H3A116 (2)
C6—C1—C2121.3 (3)C26—C21—C22120.9 (3)
C6—C1—N1116.1 (3)C26—C21—N3118.3 (3)
C2—C1—N1122.6 (3)C22—C21—N3120.7 (3)
C3—C2—C1118.7 (3)C23—C22—C21118.9 (3)
C3—C2—H2120.7C23—C22—H22120.6
C1—C2—H2120.7C21—C22—H22120.6
O3—C3—C2124.2 (3)O7—C23—C22122.9 (3)
O3—C3—C4115.0 (3)O7—C23—C24116.4 (3)
C2—C3—C4120.9 (3)C22—C23—C24120.7 (3)
C5—C4—C3119.7 (3)C23—C24—C25119.6 (3)
C5—C4—Cl1120.9 (3)C23—C24—Cl3119.8 (2)
C3—C4—Cl1119.4 (2)C25—C24—Cl3120.6 (3)
O1—C5—C4116.0 (3)O9—C25—C26123.8 (3)
O1—C5—C6123.5 (3)O9—C25—C24115.9 (3)
C4—C5—C6120.5 (3)C26—C25—C24120.2 (3)
C5—C6—C1118.9 (3)C21—C26—C25119.6 (3)
C5—C6—H6120.5C21—C26—H26120.2
C1—C6—H6120.5C25—C26—H26120.2
O1—C7—H7A109.5O9—C27—H27A109.5
O1—C7—H7B109.5O9—C27—H27B109.5
H7A—C7—H7B109.5H27A—C27—H27B109.5
O1—C7—H7C109.5O9—C27—H27C109.5
H7A—C7—H7C109.5H27A—C27—H27C109.5
H7B—C7—H7C109.5H27B—C27—H27C109.5
O2—C8—N1122.9 (3)O8—C28—N3122.8 (3)
O2—C8—C9122.3 (4)O8—C28—C29121.6 (3)
N1—C8—C9114.8 (3)N3—C28—C29115.6 (3)
C8—C9—H9A109.5C28—C29—H29A109.5
C8—C9—H9B109.5C28—C29—H29B109.5
H9A—C9—H9B109.5H29A—C29—H29B109.5
C8—C9—H9C109.5C28—C29—H29C109.5
H9A—C9—H9C109.5H29A—C29—H29C109.5
H9B—C9—H9C109.5H29B—C29—H29C109.5
O3—C10—H10A109.5O7—C30—H30A109.5
O3—C10—H10B109.5O7—C30—H30B109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
O3—C10—H10C109.5O7—C30—H30C109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
C13—O4—C20117.4 (3)C33—O10—C40117.6 (3)
C15—O6—C17118.0 (3)C35—O12—C37117.2 (3)
C18—N2—C11128.9 (3)C38—N4—C31128.1 (3)
C18—N2—H2A118 (2)C38—N4—H4A112 (3)
C11—N2—H2A113 (2)C31—N4—H4A119 (3)
C16—C11—N2124.6 (3)C36—C31—C32121.1 (3)
C16—C11—C12120.1 (3)C36—C31—N4121.9 (3)
N2—C11—C12115.3 (3)C32—C31—N4117.0 (3)
C13—C12—C11119.7 (3)C31—C32—C33119.3 (3)
C13—C12—H12120.2C31—C32—H32120.4
C11—C12—H12120.2C33—C32—H32120.4
O4—C13—C12123.9 (3)O10—C33—C34116.6 (3)
O4—C13—C14116.4 (3)O10—C33—C32123.1 (3)
C12—C13—C14119.7 (3)C34—C33—C32120.2 (3)
C15—C14—C13120.4 (3)C33—C34—C35120.2 (3)
C15—C14—Cl2119.9 (2)C33—C34—Cl4120.7 (3)
C13—C14—Cl2119.6 (3)C35—C34—Cl4119.1 (2)
O6—C15—C14115.7 (3)O12—C35—C34117.0 (3)
O6—C15—C16124.1 (3)O12—C35—C36123.4 (3)
C14—C15—C16120.1 (3)C34—C35—C36119.7 (3)
C11—C16—C15119.9 (3)C31—C36—C35119.3 (3)
C11—C16—H16120.1C31—C36—H36120.3
C15—C16—H16120.1C35—C36—H36120.3
O6—C17—H17A109.5O12—C37—H37A109.5
O6—C17—H17B109.5O12—C37—H37B109.5
H17A—C17—H17B109.5H37A—C37—H37B109.5
O6—C17—H17C109.5O12—C37—H37C109.5
H17A—C17—H17C109.5H37A—C37—H37C109.5
H17B—C17—H17C109.5H37B—C37—H37C109.5
O5—C18—N2123.9 (3)O11—C38—N4124.3 (3)
O5—C18—C19121.3 (3)O11—C38—C39120.5 (3)
N2—C18—C19114.8 (3)N4—C38—C39115.1 (3)
C18—C19—H19A109.5C38—C39—H39A109.5
C18—C19—H19B109.5C38—C39—H39B109.5
H19A—C19—H19B109.5H39A—C39—H39B109.5
C18—C19—H19C109.5C38—C39—H39C109.5
H19A—C19—H19C109.5H39A—C39—H39C109.5
H19B—C19—H19C109.5H39B—C39—H39C109.5
O4—C20—H20A109.5O10—C40—H40A109.5
O4—C20—H20B109.5O10—C40—H40B109.5
H20A—C20—H20B109.5H40A—C40—H40B109.5
O4—C20—H20C109.5O10—C40—H40C109.5
H20A—C20—H20C109.5H40A—C40—H40C109.5
H20B—C20—H20C109.5H40B—C40—H40C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O11i0.86 (3)2.03 (4)2.886 (4)176 (3)
N2—H2A···O2ii0.90 (2)1.99 (2)2.887 (4)178 (3)
N1—H1A···O8iii0.85 (4)2.06 (4)2.906 (4)176 (4)
N4—H4A···O50.84 (4)2.10 (4)2.909 (4)163 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2238).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Lai, Q.-L., Zhao, Q.-J., Liu, Z. & Shen, J.-S. (2007). Acta Cryst. E63, o2782.
  • Nguyen, T. M., Sittisombut, C., Boutefnouchet, S., Lallemand, M.-C., Michel, S., Kock, M., Tillequin, F., Mazinghien, R., Lansiaux, A., David-Cordonnier, M.-H., Pfeiffer, B., Kraus-Berthier, L., Léonce, S. & Pierré, A. (2006). J. Med. Chem. 49, 3383–3394. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography