PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o407.
Published online 2008 January 9. doi:  10.1107/S1600536807068377
PMCID: PMC2960223

2-Anilino-3-benzoyl-4-(2,5-dichloro­phen­yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetra­hydro-4H-benzo[b]pyran

Abstract

The title compound, C30H25Cl2NO3, was prepared by the reaction of 3-oxo-N,3-diphenyl­propane­thio­amide, 2,5-dichloro­benzaldehyde and 5,5-dimethyl-1,3-cyclo­hexa­nedione (1:1:1) in ethanol. The cyclohexene ring adopts a half-chair conformation. The crystal structure exhibits intra­molecular N—H(...)O and C—H(...)O, and inter­molecular C—H(...)O inter­actions.

Related literature

For various biological activities, see: Hassanien et al. (1999 [triangle]); Jiang et al. (2001 [triangle]); Hamann et al. (1998 [triangle]). For other aspects of our research, see: Li et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o407-scheme1.jpg

Experimental

Crystal data

  • C30H25Cl2NO3
  • M r = 518.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o407-efi1.jpg
  • a = 12.844 (3) Å
  • b = 9.256 (2) Å
  • c = 22.557 (5) Å
  • β = 103.365 (4)°
  • V = 2609.1 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 294 (2) K
  • 0.20 × 0.14 × 0.12 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.946, T max = 0.967
  • 14359 measured reflections
  • 5336 independent reflections
  • 2754 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.123
  • S = 1.02
  • 5336 reflections
  • 331 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [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 (Bruker, 1999 [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/S1600536807068377/ob2103sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068377/ob2103Isup2.hkl

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

Acknowledgments

This project was supported by the National Science Found­ation of China (No. 20572057), the Natural Science Foundation of Shandong Province (Y2006B11) and the Doctoral Foundation of Qingdao University of Science and Technology.

supplementary crystallographic information

Comment

Many 4H-benzo[b]pyran derivatives have been reported to show various biological activities (Hassanien et al.,1999), such as the cure of lower blood sugar (Jiang et al., 2001), mammary cancer and ovarian cancer (Hamann et al.,1998). In the course of our systematic studies aimed at the synthesis of new bioactive compounds (Li et al., 2006), the title compound, (I), was synthesized and its structure is reported here.

In (I), (Fig. 1), the six-membered ring C1—C5/C9 adopts a half-chair conformation with the largest derivation of C3 by 0.369 (3) Å. The phenyl ring C25—C30 is approximately perpendicular to the pyran ring O2/C5—C9, their dihedral angle being 88.51 (8)°. The dihedral angle between the phenyl ring C19—C24 and pyran ring is 67.70 (8) °. In the crystal structure, there are intramolecular N1—H1···O3 and C13—H13···O2 interactions (Table 1). Molecules are linked into chains along the b axis by intermolecular C28—H28···O3ii interactions (Fig. 2). Then the other intermolecular interactions C4—H4B···O1 i connect the chains to a two-dimensional network.

Experimental

The title compound (I) was obtained as follows: 3-oxo-N,3- diphenylpropanethioamide (1 mmol, 0.255 g), 2,5-dichlorobenzaldehyde (1 mmol, 0.161 g), and 5,5-dimethyl-1,3-cyclohexanedione (1 mmol, 0.140 g) were dissolved in ethanol (10 ml), and the solution was refluxed for 10 h in the presence of triethylamine (1 mmol, 0.101 g). Upon cooling, the product was collected by filtration and recrystallized from ethanol and tetrahydrofuran (4:1) (; yield 33%, m.p. 467 K).

Refinement

The H atom attached to N1 was located in a difference Fourier map and refined isotropically with N—H = 0.95 (3) Å. All other H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(CH, CH2) or 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of (I), showing displacement ellipsoids at the 35% probability level.
Fig. 2.
A packing diagram of (I), viewed down the a axis. The C—H···O interactions are shown as dashed lines.

Crystal data

C30H25Cl2NO3F000 = 1080
Mr = 518.41Dx = 1.320 Mg m3Dm = 1.320 Mg m3Dm measured by not measured
Monoclinic, P21/nMelting point: 467 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 12.844 (3) ÅCell parameters from 2650 reflections
b = 9.256 (2) Åθ = 2.4–23.6º
c = 22.557 (5) ŵ = 0.28 mm1
β = 103.365 (4)ºT = 294 (2) K
V = 2609.1 (10) Å3Block, colorless
Z = 40.20 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer5336 independent reflections
Radiation source: fine-focus sealed tube2754 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
T = 294(2) Kθmax = 26.4º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −16→15
Tmin = 0.946, Tmax = 0.967k = −10→11
14359 measured reflectionsl = −28→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123  w = 1/[σ2(Fo2) + (0.0411P)2 + 0.4267P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
5336 reflectionsΔρmax = 0.20 e Å3
331 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Cl11.02394 (6)0.53547 (9)0.14792 (4)0.0680 (3)
Cl20.63077 (9)0.80839 (10)−0.03029 (4)0.1032 (4)
N11.01125 (19)0.1076 (3)0.12728 (11)0.0550 (7)
O10.65405 (15)0.5247 (2)0.17605 (9)0.0658 (6)
O20.96352 (13)0.23945 (17)0.20044 (7)0.0447 (5)
O30.91053 (15)0.1391 (2)0.01577 (8)0.0587 (5)
C10.7347 (2)0.4727 (3)0.20864 (12)0.0452 (7)
C20.7538 (2)0.4781 (3)0.27707 (12)0.0560 (8)
H2A0.71920.39540.29070.067*
H2B0.72020.56440.28840.067*
C30.8716 (2)0.4783 (3)0.31028 (12)0.0502 (7)
C40.9243 (2)0.3467 (3)0.28778 (11)0.0463 (7)
H4A1.00150.35610.30080.056*
H4B0.90360.26010.30630.056*
C50.89396 (19)0.3311 (2)0.22046 (11)0.0383 (6)
C60.9429 (2)0.2043 (3)0.13997 (12)0.0416 (6)
C70.86258 (19)0.2673 (3)0.09639 (11)0.0398 (6)
C80.79466 (19)0.3875 (3)0.11449 (11)0.0392 (6)
H80.71950.36160.09820.047*
C90.81208 (19)0.3949 (2)0.18249 (11)0.0369 (6)
C100.9257 (2)0.6182 (3)0.29677 (15)0.0734 (10)
H10A0.89280.69920.31180.110*
H10B0.91770.62780.25360.110*
H10C1.00030.61520.31650.110*
C110.8814 (3)0.4667 (4)0.37879 (13)0.0771 (10)
H11A0.84550.38100.38750.116*
H11B0.84930.54990.39270.116*
H11C0.95560.46190.39940.116*
C121.0879 (2)0.0194 (3)0.16614 (13)0.0485 (7)
C131.0736 (2)−0.0379 (3)0.21985 (14)0.0609 (8)
H131.0137−0.01310.23420.073*
C141.1488 (3)−0.1329 (3)0.25254 (15)0.0770 (11)
H141.1393−0.17190.28890.092*
C151.2367 (3)−0.1695 (4)0.2314 (2)0.0991 (15)
H151.2879−0.23160.25380.119*
C161.2491 (3)−0.1147 (5)0.1776 (2)0.1075 (15)
H161.3078−0.14230.16270.129*
C171.1760 (2)−0.0190 (4)0.14480 (16)0.0781 (10)
H171.18610.01940.10850.094*
C180.8497 (2)0.2257 (3)0.03393 (12)0.0457 (7)
C190.7627 (2)0.2933 (3)−0.01376 (12)0.0455 (7)
C200.6553 (2)0.2647 (3)−0.01880 (14)0.0599 (8)
H200.63430.20050.00790.072*
C210.5790 (2)0.3324 (4)−0.06390 (15)0.0722 (10)
H210.50680.3133−0.06720.087*
C220.6089 (3)0.4266 (4)−0.10348 (15)0.0785 (11)
H220.55720.4719−0.13340.094*
C230.7149 (3)0.4542 (4)−0.09893 (14)0.0781 (10)
H230.73540.5180−0.12600.094*
C240.7915 (2)0.3877 (3)−0.05430 (13)0.0639 (9)
H240.86360.4068−0.05160.077*
C250.8126 (2)0.5352 (3)0.08756 (11)0.0428 (6)
C260.9106 (2)0.6062 (3)0.09834 (13)0.0530 (7)
C270.9232 (3)0.7360 (3)0.07054 (15)0.0687 (9)
H270.98960.78120.07880.082*
C280.8378 (3)0.7983 (3)0.03080 (16)0.0782 (10)
H280.84610.88490.01150.094*
C290.7397 (3)0.7304 (3)0.01996 (14)0.0666 (9)
C300.7271 (2)0.6016 (3)0.04800 (12)0.0542 (8)
H300.66000.55820.04030.065*
H10.998 (2)0.096 (3)0.0845 (13)0.073 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0498 (4)0.0769 (6)0.0765 (6)−0.0138 (4)0.0127 (4)0.0079 (4)
Cl20.1407 (9)0.0856 (7)0.0772 (6)0.0470 (6)0.0125 (6)0.0360 (5)
N10.0586 (15)0.0595 (16)0.0444 (15)0.0226 (13)0.0066 (13)−0.0016 (13)
O10.0536 (12)0.0750 (14)0.0651 (14)0.0274 (11)0.0058 (11)−0.0011 (11)
O20.0443 (11)0.0443 (11)0.0423 (11)0.0114 (9)0.0037 (9)−0.0008 (9)
O30.0700 (13)0.0590 (13)0.0473 (12)0.0196 (11)0.0141 (10)−0.0010 (10)
C10.0425 (16)0.0382 (15)0.0537 (18)0.0032 (13)0.0086 (14)0.0007 (13)
C20.0557 (18)0.0582 (19)0.0551 (19)0.0103 (15)0.0147 (15)−0.0021 (15)
C30.0611 (18)0.0421 (16)0.0461 (17)0.0019 (14)0.0100 (14)−0.0056 (13)
C40.0510 (17)0.0405 (16)0.0440 (16)0.0019 (13)0.0042 (13)0.0015 (13)
C50.0401 (15)0.0287 (14)0.0458 (16)−0.0009 (12)0.0094 (13)−0.0019 (12)
C60.0412 (15)0.0384 (15)0.0443 (16)0.0036 (13)0.0080 (13)−0.0006 (13)
C70.0403 (15)0.0366 (14)0.0406 (15)0.0029 (12)0.0055 (12)0.0016 (12)
C80.0368 (14)0.0372 (14)0.0414 (15)0.0022 (12)0.0042 (12)0.0033 (12)
C90.0350 (14)0.0319 (14)0.0423 (15)0.0018 (11)0.0057 (12)0.0014 (12)
C100.089 (2)0.0463 (18)0.080 (2)−0.0088 (17)0.0093 (19)−0.0055 (17)
C110.099 (3)0.081 (2)0.0485 (19)0.012 (2)0.0121 (18)−0.0085 (17)
C120.0424 (16)0.0452 (16)0.0513 (18)0.0116 (13)−0.0026 (14)−0.0085 (14)
C130.063 (2)0.0516 (18)0.062 (2)0.0130 (16)0.0028 (17)0.0004 (16)
C140.098 (3)0.053 (2)0.064 (2)0.017 (2)−0.013 (2)−0.0009 (17)
C150.091 (3)0.093 (3)0.090 (3)0.049 (2)−0.026 (3)−0.016 (2)
C160.064 (2)0.142 (4)0.108 (4)0.052 (3)0.003 (3)−0.019 (3)
C170.059 (2)0.101 (3)0.072 (2)0.031 (2)0.0102 (18)−0.003 (2)
C180.0461 (16)0.0393 (16)0.0509 (17)0.0018 (13)0.0092 (14)0.0022 (14)
C190.0503 (17)0.0451 (16)0.0396 (16)0.0039 (13)0.0071 (14)−0.0016 (13)
C200.0542 (19)0.063 (2)0.059 (2)−0.0079 (16)0.0060 (16)−0.0017 (16)
C210.0470 (19)0.093 (3)0.068 (2)−0.0026 (18)−0.0047 (18)−0.015 (2)
C220.070 (2)0.104 (3)0.052 (2)0.024 (2)−0.0052 (19)0.003 (2)
C230.073 (2)0.104 (3)0.057 (2)0.023 (2)0.0143 (18)0.0295 (19)
C240.0537 (19)0.082 (2)0.0557 (19)0.0118 (17)0.0119 (16)0.0130 (17)
C250.0522 (17)0.0346 (14)0.0424 (16)0.0066 (13)0.0129 (13)0.0047 (12)
C260.0608 (19)0.0441 (17)0.0558 (18)−0.0024 (15)0.0170 (15)0.0015 (14)
C270.086 (2)0.050 (2)0.077 (2)−0.0123 (18)0.032 (2)0.0047 (18)
C280.129 (3)0.0416 (19)0.073 (2)0.005 (2)0.041 (2)0.0112 (17)
C290.099 (3)0.0466 (19)0.0545 (19)0.0207 (19)0.0191 (19)0.0126 (16)
C300.0639 (19)0.0459 (17)0.0520 (18)0.0113 (15)0.0119 (15)0.0059 (14)

Geometric parameters (Å, °)

Cl1—C261.745 (3)C12—C131.373 (4)
Cl2—C291.741 (3)C12—C171.374 (4)
N1—C61.330 (3)C13—C141.386 (4)
N1—C121.417 (3)C13—H130.9300
N1—H10.95 (3)C14—C151.366 (5)
O1—C11.222 (3)C14—H140.9300
O2—C61.367 (3)C15—C161.359 (5)
O2—C51.381 (3)C15—H150.9300
O3—C181.252 (3)C16—C171.376 (5)
C1—C91.458 (3)C16—H160.9300
C1—C21.507 (4)C17—H170.9300
C2—C31.525 (4)C18—C191.498 (3)
C2—H2A0.9700C19—C241.376 (4)
C2—H2B0.9700C19—C201.383 (4)
C3—C111.525 (4)C20—C211.388 (4)
C3—C101.533 (4)C20—H200.9300
C3—C41.536 (4)C21—C221.366 (4)
C4—C51.485 (3)C21—H210.9300
C4—H4A0.9700C22—C231.365 (4)
C4—H4B0.9700C22—H220.9300
C5—C91.331 (3)C23—C241.380 (4)
C6—C71.379 (3)C23—H230.9300
C7—C181.433 (4)C24—H240.9300
C7—C81.527 (3)C25—C301.388 (3)
C8—C91.499 (3)C25—C261.391 (3)
C8—C251.535 (3)C26—C271.382 (4)
C8—H80.9800C27—C281.373 (4)
C10—H10A0.9600C27—H270.9300
C10—H10B0.9600C28—C291.379 (4)
C10—H10C0.9600C28—H280.9300
C11—H11A0.9600C29—C301.377 (4)
C11—H11B0.9600C30—H300.9300
C11—H11C0.9600
C6—N1—C12130.8 (3)C13—C12—N1123.5 (3)
C6—N1—H1108.8 (17)C17—C12—N1116.3 (3)
C12—N1—H1120.2 (17)C12—C13—C14119.7 (3)
C6—O2—C5118.79 (18)C12—C13—H13120.2
O1—C1—C9120.9 (2)C14—C13—H13120.2
O1—C1—C2121.2 (2)C15—C14—C13120.2 (4)
C9—C1—C2117.8 (2)C15—C14—H14119.9
C1—C2—C3114.3 (2)C13—C14—H14119.9
C1—C2—H2A108.7C16—C15—C14119.7 (4)
C3—C2—H2A108.7C16—C15—H15120.1
C1—C2—H2B108.7C14—C15—H15120.1
C3—C2—H2B108.7C15—C16—C17121.0 (4)
H2A—C2—H2B107.6C15—C16—H16119.5
C11—C3—C2109.7 (2)C17—C16—H16119.5
C11—C3—C10109.0 (2)C12—C17—C16119.5 (4)
C2—C3—C10110.3 (2)C12—C17—H17120.2
C11—C3—C4109.9 (2)C16—C17—H17120.2
C2—C3—C4107.5 (2)O3—C18—C7123.7 (2)
C10—C3—C4110.5 (2)O3—C18—C19116.8 (2)
C5—C4—C3112.6 (2)C7—C18—C19119.4 (2)
C5—C4—H4A109.1C24—C19—C20118.9 (3)
C3—C4—H4A109.1C24—C19—C18118.1 (3)
C5—C4—H4B109.1C20—C19—C18123.0 (3)
C3—C4—H4B109.1C19—C20—C21119.7 (3)
H4A—C4—H4B107.8C19—C20—H20120.1
C9—C5—O2122.5 (2)C21—C20—H20120.1
C9—C5—C4126.6 (2)C22—C21—C20120.6 (3)
O2—C5—C4110.9 (2)C22—C21—H21119.7
N1—C6—O2112.9 (2)C20—C21—H21119.7
N1—C6—C7123.6 (3)C23—C22—C21119.8 (3)
O2—C6—C7123.4 (2)C23—C22—H22120.1
C6—C7—C18119.0 (2)C21—C22—H22120.1
C6—C7—C8119.8 (2)C22—C23—C24120.2 (3)
C18—C7—C8121.1 (2)C22—C23—H23119.9
C9—C8—C7110.32 (19)C24—C23—H23119.9
C9—C8—C25111.3 (2)C19—C24—C23120.8 (3)
C7—C8—C25113.3 (2)C19—C24—H24119.6
C9—C8—H8107.2C23—C24—H24119.6
C7—C8—H8107.2C30—C25—C26116.9 (2)
C25—C8—H8107.2C30—C25—C8118.7 (2)
C5—C9—C1118.0 (2)C26—C25—C8124.3 (2)
C5—C9—C8123.1 (2)C27—C26—C25121.8 (3)
C1—C9—C8118.8 (2)C27—C26—Cl1116.7 (2)
C3—C10—H10A109.5C25—C26—Cl1121.5 (2)
C3—C10—H10B109.5C28—C27—C26120.2 (3)
H10A—C10—H10B109.5C28—C27—H27119.9
C3—C10—H10C109.5C26—C27—H27119.9
H10A—C10—H10C109.5C27—C28—C29118.9 (3)
H10B—C10—H10C109.5C27—C28—H28120.5
C3—C11—H11A109.5C29—C28—H28120.5
C3—C11—H11B109.5C30—C29—C28120.9 (3)
H11A—C11—H11B109.5C30—C29—Cl2119.7 (3)
C3—C11—H11C109.5C28—C29—Cl2119.4 (3)
H11A—C11—H11C109.5C29—C30—C25121.3 (3)
H11B—C11—H11C109.5C29—C30—H30119.4
C13—C12—C17119.9 (3)C25—C30—H30119.4
O1—C1—C2—C3−152.1 (3)C12—C13—C14—C150.0 (5)
C9—C1—C2—C332.0 (3)C13—C14—C15—C16−1.4 (6)
C1—C2—C3—C11−173.7 (2)C14—C15—C16—C172.1 (6)
C1—C2—C3—C1066.2 (3)C13—C12—C17—C160.0 (5)
C1—C2—C3—C4−54.2 (3)N1—C12—C17—C16−174.3 (3)
C11—C3—C4—C5165.2 (2)C15—C16—C17—C12−1.4 (6)
C2—C3—C4—C545.8 (3)C6—C7—C18—O3−3.2 (4)
C10—C3—C4—C5−74.5 (3)C8—C7—C18—O3172.1 (2)
C6—O2—C5—C9−5.1 (3)C6—C7—C18—C19179.9 (2)
C6—O2—C5—C4175.3 (2)C8—C7—C18—C19−4.8 (4)
C3—C4—C5—C9−16.4 (4)O3—C18—C19—C24−67.0 (3)
C3—C4—C5—O2163.2 (2)C7—C18—C19—C24110.1 (3)
C12—N1—C6—O212.1 (4)O3—C18—C19—C20112.9 (3)
C12—N1—C6—C7−170.6 (3)C7—C18—C19—C20−70.0 (4)
C5—O2—C6—N1−175.5 (2)C24—C19—C20—C21−0.7 (4)
C5—O2—C6—C77.2 (3)C18—C19—C20—C21179.5 (3)
N1—C6—C7—C181.1 (4)C19—C20—C21—C220.1 (5)
O2—C6—C7—C18178.2 (2)C20—C21—C22—C230.3 (5)
N1—C6—C7—C8−174.3 (2)C21—C22—C23—C24−0.3 (5)
O2—C6—C7—C82.8 (4)C20—C19—C24—C230.7 (5)
C6—C7—C8—C9−13.0 (3)C18—C19—C24—C23−179.5 (3)
C18—C7—C8—C9171.7 (2)C22—C23—C24—C19−0.2 (5)
C6—C7—C8—C25112.6 (3)C9—C8—C25—C30−117.1 (3)
C18—C7—C8—C25−62.7 (3)C7—C8—C25—C30117.9 (3)
O2—C5—C9—C1171.3 (2)C9—C8—C25—C2665.4 (3)
C4—C5—C9—C1−9.1 (4)C7—C8—C25—C26−59.7 (3)
O2—C5—C9—C8−7.2 (4)C30—C25—C26—C27−0.7 (4)
C4—C5—C9—C8172.3 (2)C8—C25—C26—C27176.9 (3)
O1—C1—C9—C5−174.8 (2)C30—C25—C26—Cl1179.1 (2)
C2—C1—C9—C51.2 (3)C8—C25—C26—Cl1−3.3 (4)
O1—C1—C9—C83.8 (4)C25—C26—C27—C28−0.3 (5)
C2—C1—C9—C8179.8 (2)Cl1—C26—C27—C28179.8 (2)
C7—C8—C9—C515.5 (3)C26—C27—C28—C291.0 (5)
C25—C8—C9—C5−111.2 (3)C27—C28—C29—C30−0.5 (5)
C7—C8—C9—C1−163.1 (2)C27—C28—C29—Cl2179.9 (3)
C25—C8—C9—C170.2 (3)C28—C29—C30—C25−0.6 (5)
C6—N1—C12—C1334.3 (5)Cl2—C29—C30—C25179.0 (2)
C6—N1—C12—C17−151.7 (3)C26—C25—C30—C291.2 (4)
C17—C12—C13—C140.7 (4)C8—C25—C30—C29−176.6 (3)
N1—C12—C13—C14174.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O30.95 (3)1.74 (3)2.565 (3)144 (3)
C4—H4B···O1i0.972.363.308 (3)164
C13—H13···O20.932.502.915 (3)108
C28—H28···O3ii0.932.493.329 (4)150

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OB2103).

References

  • Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT and SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hamann, L. G., Higuchi, R. I., Zhi, L. & Edwards, J. P. (1998). J. Med. Chem.41, 623–639. [PubMed]
  • Hassanien, A. A., Zahran, M. A., El-Gaby, M. S. A. & Ghorab, M. M. (1999). J. Ind. Chem. Soc.76, 350–354.
  • Jiang, H., Wang, L. J. & Zhao, Z. X. (2001). J. Beihua Univ.12, 489–490.
  • Li, M., Sun, E.-T. & Wen, L.-R. (2006). Acta Cryst. E62, o5607–o5608.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • 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