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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o256–o257.
Published online 2010 January 9. doi:  10.1107/S1600536809054695
PMCID: PMC2979672

2-[2-(2,6-Dichloro­anilino)phen­yl]-N′-(4-propyl­cyclo­hexyl­idene)acetohydrazide

Abstract

The asymmetric unit of the title compound, C23H27Cl2N3O, contains two crystallographically independent mol­ecules in which the dihedral angles between the benzene rings are 70.1 (3) and 63.8 (3)°. In each mol­ecule an intra­molecular N—H(...)O hydrogen bond generates an S(7) ring. The atoms of the propyl grouping of one mol­ecule are disordered over two orientations with occupancies of 0.666 (6) and 0.334 (6). The crystal structure is stabilized by N—H(...)O and C—H(...)O hydrogen-bonding inter­actions.

Related literature

For the pharmacological activity and biological properties of diclofenac and its derivatives, see: Gobec et al. (2005 [triangle]); Moser et al. (1990 [triangle]); Sallmann (1986 [triangle]); Sriram et al. (2006 [triangle]); Wittine et al. (2009 [triangle]); Zhang et al. (2009 [triangle]). For comparative bond lengths, see: Allen et al. (1987 [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o256-scheme1.jpg

Experimental

Crystal data

  • C23H27Cl2N3O
  • M r = 432.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o256-efi1.jpg
  • a = 13.0235 (6) Å
  • b = 15.2618 (5) Å
  • c = 26.6255 (12) Å
  • β = 118.098 (3)°
  • V = 4668.4 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 296 K
  • 0.60 × 0.34 × 0.10 mm

Data collection

  • Stoe IPDS 2 diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.842, T max = 0.971
  • 69169 measured reflections
  • 9577 independent reflections
  • 4744 reflections with I > 2σ(I)
  • R int = 0.070

Refinement

  • R[F 2 > 2σ(F 2)] = 0.081
  • wR(F 2) = 0.247
  • S = 1.01
  • 9577 reflections
  • 492 parameters
  • 7 restraints
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054695/hb5287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054695/hb5287Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was also supported by the research fund of İstanbul University (project No. 3041).

supplementary crystallographic information

Comment

Diclofenac, [2-(2,6-dichlorophenylamino)phenyl]acetic acid, has long been widely used for its antipyretic, analgesic, and antiinflammatory activities (Moser et al., 1990; Sallmann, 1986). Besides, diclofenac and its derivatives displayed various biological properties like anticancer (Gobec et al., 2005), antimycobacterial (Sriram et al., 2006), antiviral (Wittine et al., 2009) and insulin-sensitizing activity (Zhang et al., 2009).

In the title compound (I), the asymmetric unit contains two crystallographically independent molecules. Fig. 1 shows the non-disorder molecule. In the molecules A and B, bond lengthsdistances are within the expected range (Allen et al., 1987) and the dihedral angles between the benzene rings are 70.1 (3)° and 63.8 (3)°, respectively. Molecules A and B have a distorted chair conformation with the puckering parameters [Cremer & Pople (1975)]; QT = 0.536 (7) Å, θ = 169.8 (7)°, [var phi] = 350 (5)° and QT = 0.363 (10) Å, θ = 23.4 (14)°, [var phi] = 232 (4)°, respectively. The crystal structure is stabilized by N—H···O, C—H···O and C—H···N hydrogen bonding interactions (Table 1 and Fig. 2).

Experimental

A mixture of 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetohydrazide (0.005 mol) and 4-propylcyclohexanone (0.01 mol) was refluxed in 15 ml ABS. EtOH for 5 h. The precipitate obtained was filtered, dried and purified by recrystallization from EtOH. Yield, 71.8%, m.p. 474.2 - 474.8 K. UV (EtOH) l max = 281.6, 205.0 nm. IR (KBr) n = 3226 (N—H), 1651 (C=O, C=N) cm-1. 1H-NMR (DMSO-d6, 500 MHz) d = 0.91- 0.95 (3H, m, CH3-cyc*.), 1.04–1.16 (1H, m, CH2-cyc.), 1.22–1.29,1.32–1.40 (4H, 2 m, CH2CH2CH3-cyc.), 1.57–1.62 (1H, m, CH-cyc.), 1.88–2.01 (3H, m, CH2-cyc.), 2.21–2.29 (1H, m, CH2-cyc.), 2.38–2.42 (1H, m, CH2-cyc.), 2.95–3.03(1H, m, CH2-cyc.), 3.76, 4.03, 4.07 (2H, s, 2 d, J = 13.6 Hz, CH2CO), 6.30, 6.36 (1H, 2 d, J = 7.81 Hz, Ar—H*), 6.88, 6.92 (1H, 2 t, J = 7.32 Hz, Ar—H), 7.08–7.12 (1H, m, Ar—H), 7.21–7.32 (2H, m, Ar—H), 7.57–7.59 (2H, m, Ar—H), 7.87,8.35 (1H, 2 s, NH), 10.60, 10.62 (1H, 2 s, CONH) p.p.m. (*cyc.= cyclohexylidene, Ar= aromatic). Analysis calculated for C23H27Cl2N3O: C 63.89, H6.25, N 9.72%. Found: C63.23, H 6.37, N 9.61%.

Refinement

H atoms were positioned geometrically with N—H = 0.86 Å, C—H = 0.93 - 0.97 Å and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C, N). The atoms of the propyl moiety of the disorder molecule are disordered over two positions with the site occupation factors 0.666 (6) and 0.334 (6).

Figures

Fig. 1.
View of the non-disorder molecule of (I) with displacement ellipsoids for non-H atoms drawn at the 20% probability level.
Fig. 2.
View of the packing and hydrogen bonding interactions of (I) down the a axis. All hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C23H27Cl2N3OF(000) = 1824
Mr = 432.38Dx = 1.230 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 39814 reflections
a = 13.0235 (6) Åθ = 1.6–27.2°
b = 15.2618 (5) ŵ = 0.30 mm1
c = 26.6255 (12) ÅT = 296 K
β = 118.098 (3)°Prism, colourless
V = 4668.4 (4) Å30.60 × 0.34 × 0.10 mm
Z = 8

Data collection

Stoe IPDS 2 diffractometer9577 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus4744 reflections with I > 2σ(I)
plane graphiteRint = 0.070
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 1.7°
ω scansh = −16→16
Absorption correction: integration (X-RED3; Stoe & Cie, 2002)k = −19→19
Tmin = 0.842, Tmax = 0.971l = −33→33
69169 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.247H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.1324P)2] where P = (Fo2 + 2Fc2)/3
9577 reflections(Δ/σ)max < 0.001
492 parametersΔρmax = 0.44 e Å3
7 restraintsΔρmin = −0.48 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
Cl30.55339 (12)0.47497 (7)0.21299 (7)0.0961 (5)
Cl40.35062 (13)0.76589 (7)0.24245 (6)0.0961 (5)
O20.2070 (3)0.61054 (15)0.27547 (13)0.0687 (10)
N40.3728 (3)0.57460 (19)0.23307 (14)0.0629 (11)
N50.1122 (3)0.50946 (18)0.29889 (14)0.0619 (11)
N60.0476 (3)0.5731 (2)0.30818 (16)0.0723 (13)
C240.4513 (3)0.6241 (2)0.22301 (16)0.0591 (11)
C250.4538 (4)0.7154 (2)0.22791 (19)0.0714 (16)
C260.5337 (5)0.7657 (3)0.2219 (2)0.097 (2)
C270.6145 (5)0.7280 (3)0.2095 (3)0.100 (2)
C280.6163 (4)0.6386 (3)0.2052 (2)0.0875 (19)
C290.5386 (4)0.5878 (3)0.21322 (19)0.0714 (14)
C300.2970 (3)0.5115 (2)0.19509 (19)0.0624 (13)
C310.2774 (4)0.5052 (3)0.1398 (2)0.0832 (17)
C320.1971 (5)0.4428 (5)0.1038 (3)0.123 (3)
C330.1421 (6)0.3871 (5)0.1238 (4)0.141 (4)
C340.1628 (5)0.3935 (3)0.1788 (3)0.103 (3)
C350.2404 (4)0.4557 (2)0.2156 (2)0.0680 (15)
C360.2595 (4)0.4600 (2)0.2751 (2)0.0689 (15)
C370.1899 (3)0.5338 (2)0.28315 (16)0.0544 (11)
C38−0.0211 (5)0.5513 (3)0.3267 (3)0.091 (2)
C39−0.0417 (7)0.4612 (4)0.3418 (4)0.1403 (18)
C40−0.0837 (7)0.4531 (4)0.3797 (4)0.1403 (18)
C41−0.1573 (8)0.5226 (4)0.3871 (4)0.1403 (18)
C42−0.1138 (7)0.6138 (4)0.3802 (4)0.1403 (18)
C43−0.0909 (7)0.6232 (4)0.3349 (4)0.1403 (18)
C44A−0.1851 (13)0.5169 (6)0.4331 (7)0.1405 (3)0.666 (6)
C45A−0.2286 (11)0.4326 (6)0.4477 (6)0.1405 (3)0.666 (6)
C46A−0.3406 (11)0.4181 (7)0.3950 (6)0.1405 (3)0.666 (6)
C46B−0.337 (2)0.3799 (11)0.4379 (11)0.1405 (3)0.334 (6)
C44B−0.276 (2)0.4895 (11)0.3812 (13)0.1405 (3)0.334 (6)
C45B−0.274 (3)0.3976 (12)0.4063 (13)0.1405 (3)0.334 (6)
Cl10.65421 (16)0.86931 (15)0.46429 (9)0.1470 (9)
Cl20.69658 (17)0.55357 (12)0.56388 (8)0.1386 (8)
O10.8618 (2)0.68597 (16)0.67741 (11)0.0660 (9)
N10.7624 (3)0.7387 (2)0.55967 (14)0.0720 (12)
N21.0330 (3)0.73731 (17)0.74608 (13)0.0600 (10)
N31.0550 (3)0.65711 (19)0.77439 (16)0.0744 (11)
C10.6732 (4)0.7070 (4)0.50919 (19)0.0790 (18)
C20.6183 (4)0.7609 (4)0.4604 (2)0.098 (2)
C30.5347 (6)0.7271 (7)0.4093 (3)0.132 (4)
C40.4974 (6)0.6461 (9)0.4068 (4)0.152 (4)
C50.5440 (6)0.5910 (6)0.4539 (4)0.143 (3)
C60.6327 (5)0.6232 (4)0.5040 (2)0.102 (2)
C70.8708 (3)0.7650 (3)0.56500 (17)0.0646 (12)
C80.9009 (4)0.7488 (3)0.52235 (19)0.0817 (19)
C91.0070 (5)0.7718 (4)0.5287 (2)0.0962 (19)
C101.0875 (5)0.8114 (4)0.5773 (3)0.104 (2)
C111.0586 (4)0.8288 (3)0.6199 (2)0.0831 (17)
C120.9510 (3)0.8072 (2)0.61494 (16)0.0616 (12)
C130.9229 (4)0.8264 (2)0.66274 (17)0.0633 (11)
C140.9359 (3)0.7440 (2)0.69641 (16)0.0541 (11)
C151.1410 (4)0.6509 (3)0.82318 (19)0.0729 (16)
C161.1645 (6)0.5615 (3)0.8499 (3)0.129 (3)
C171.1834 (6)0.5634 (4)0.9097 (3)0.136 (3)
C181.2791 (6)0.6281 (4)0.9464 (2)0.105 (3)
C191.2429 (7)0.7183 (4)0.9183 (3)0.136 (3)
C201.2220 (5)0.7205 (4)0.8578 (2)0.117 (2)
C211.3058 (8)0.6285 (7)1.0070 (3)0.161 (4)
C221.4223 (12)0.6681 (8)1.0492 (4)0.211 (6)
C231.5268 (10)0.6037 (11)1.0633 (4)0.233 (8)
H5A0.101800.454900.303300.0740*
H280.670700.612300.196700.1050*
H260.533400.826200.226300.1170*
H270.667300.762500.204100.1190*
H4A0.370500.583100.264500.0760*
H340.124600.356000.192000.1240*
H36A0.341700.469000.300600.0830*
H36B0.237000.404700.285000.0830*
H39A−0.095600.432000.306900.1690*
H310.316600.541600.126500.1000*
H320.181100.439200.066000.1470*
H330.090700.344900.099900.1690*
H41−0.232900.516600.353000.1690*
H42A−0.171800.656900.376300.1690*
H42B−0.043300.627300.414900.1690*
H43A−0.049800.678000.339600.1690*
H43B−0.164700.627900.300400.1690*
H44A−0.243600.561300.426200.1690*0.666 (6)
H44B−0.115800.534400.467300.1690*0.666 (6)
H45A−0.174800.384500.454600.1690*0.666 (6)
H45B−0.240700.440200.480700.1690*0.666 (6)
H46A−0.374300.363600.398000.2110*0.666 (6)
H46B−0.326700.416000.362700.2110*0.666 (6)
H46C−0.393200.465200.390400.2110*0.666 (6)
H39B0.031400.429400.356900.1690*
H40A−0.017000.444000.416800.1690*
H40B−0.128600.399300.370200.1690*
H44C−0.303200.531400.399800.1690*0.334 (6)
H44D−0.332700.488800.341100.1690*0.334 (6)
H45C−0.301800.356300.374900.1690*0.334 (6)
H45D−0.192900.383300.431200.1690*0.334 (6)
H46D−0.362300.319900.432400.2110*0.334 (6)
H46E−0.403800.417800.424500.2110*0.334 (6)
H46F−0.287200.390400.477700.2110*0.334 (6)
H10.751100.742500.588900.0870*
H21.080100.780800.760000.0720*
H30.504700.761500.376600.1590*
H40.438300.625200.372500.1820*
H50.516200.534300.451800.1720*
H80.847500.721700.488900.0980*
H91.025100.760400.499500.1150*
H101.160400.826400.581500.1240*
H111.113200.855900.653100.1000*
H13A0.975200.871200.687500.0760*
H13B0.843800.848200.647200.0760*
H16A1.099200.523500.827400.1560*
H16B1.232900.537100.849500.1560*
H17A1.204600.505300.926000.1630*
H17B1.111400.579900.909600.1630*
H181.350200.610900.945000.1260*
H19A1.172400.736400.919100.1630*
H19B1.303400.760300.940400.1630*
H20A1.190100.777100.841300.1400*
H20B1.295500.713300.857400.1400*
H21A1.303200.568601.018400.1930*
H21B1.244500.660501.010000.1930*
H22A1.420000.682701.084100.2540*
H22B1.434900.721901.033500.2540*
H23A1.549700.576601.099600.3460*
H23B1.591300.635801.064500.3460*
H23C1.503000.559401.034400.3460*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl30.0978 (9)0.0652 (6)0.1428 (12)0.0112 (6)0.0711 (9)0.0132 (7)
Cl40.1193 (10)0.0505 (5)0.1282 (11)−0.0088 (6)0.0662 (9)−0.0128 (6)
O20.096 (2)0.0376 (12)0.093 (2)−0.0001 (12)0.0614 (17)0.0008 (12)
N40.080 (2)0.0532 (16)0.063 (2)−0.0136 (15)0.0398 (17)−0.0040 (14)
N50.078 (2)0.0378 (14)0.081 (2)0.0039 (14)0.0467 (19)0.0030 (14)
N60.091 (2)0.0505 (17)0.094 (3)0.0165 (16)0.059 (2)0.0134 (16)
C240.065 (2)0.0496 (19)0.057 (2)−0.0087 (16)0.0240 (19)0.0042 (16)
C250.083 (3)0.051 (2)0.076 (3)−0.0135 (19)0.034 (2)0.0001 (18)
C260.113 (4)0.063 (3)0.117 (4)−0.032 (3)0.055 (3)−0.003 (3)
C270.094 (4)0.080 (3)0.125 (5)−0.031 (3)0.052 (3)0.007 (3)
C280.074 (3)0.095 (3)0.095 (4)−0.009 (2)0.041 (3)0.011 (3)
C290.069 (2)0.064 (2)0.078 (3)−0.005 (2)0.032 (2)0.010 (2)
C300.068 (2)0.0468 (18)0.079 (3)−0.0026 (17)0.040 (2)−0.0128 (17)
C310.079 (3)0.097 (3)0.083 (3)−0.008 (2)0.046 (3)−0.024 (3)
C320.103 (4)0.167 (6)0.107 (5)−0.020 (4)0.057 (4)−0.079 (4)
C330.099 (4)0.173 (7)0.177 (7)−0.067 (4)0.087 (5)−0.110 (6)
C340.098 (4)0.082 (3)0.164 (6)−0.034 (3)0.090 (4)−0.059 (3)
C350.076 (3)0.0403 (18)0.105 (3)−0.0046 (17)0.057 (2)−0.0143 (19)
C360.083 (3)0.0376 (17)0.107 (3)0.0062 (17)0.062 (3)0.0117 (19)
C370.068 (2)0.0371 (16)0.061 (2)0.0003 (15)0.0329 (19)0.0028 (15)
C380.105 (4)0.065 (3)0.135 (5)0.020 (2)0.083 (4)0.017 (3)
C390.189 (3)0.0902 (17)0.221 (4)0.0279 (19)0.162 (3)0.013 (2)
C400.189 (3)0.0902 (17)0.221 (4)0.0279 (19)0.162 (3)0.013 (2)
C410.189 (3)0.0902 (17)0.221 (4)0.0279 (19)0.162 (3)0.013 (2)
C420.189 (3)0.0902 (17)0.221 (4)0.0279 (19)0.162 (3)0.013 (2)
C430.189 (3)0.0902 (17)0.221 (4)0.0279 (19)0.162 (3)0.013 (2)
C44A0.1887 (7)0.0902 (4)0.2215 (4)0.0279 (4)0.1617 (4)0.0134 (7)
C45A0.1887 (7)0.0902 (4)0.2215 (4)0.0279 (4)0.1617 (4)0.0134 (7)
C46A0.1887 (7)0.0902 (4)0.2215 (4)0.0279 (4)0.1617 (4)0.0134 (7)
C46B0.1887 (7)0.0902 (4)0.2215 (4)0.0279 (4)0.1617 (4)0.0134 (7)
C44B0.1887 (7)0.0902 (4)0.2215 (4)0.0279 (4)0.1617 (4)0.0134 (7)
C45B0.1887 (7)0.0902 (4)0.2215 (4)0.0279 (4)0.1617 (4)0.0134 (7)
Cl10.1150 (12)0.1718 (17)0.1371 (15)0.0079 (11)0.0452 (11)0.0732 (13)
Cl20.1478 (15)0.1123 (11)0.1266 (14)−0.0535 (11)0.0407 (11)−0.0050 (9)
O10.0732 (17)0.0547 (14)0.0643 (17)−0.0151 (12)0.0276 (14)0.0023 (12)
N10.066 (2)0.093 (2)0.056 (2)−0.0175 (18)0.0280 (17)−0.0021 (17)
N20.0691 (19)0.0391 (14)0.063 (2)−0.0077 (13)0.0239 (17)0.0032 (13)
N30.085 (2)0.0406 (15)0.076 (2)−0.0033 (15)0.020 (2)0.0104 (15)
C10.056 (2)0.117 (4)0.058 (3)−0.014 (2)0.022 (2)−0.006 (2)
C20.059 (3)0.159 (5)0.072 (3)−0.006 (3)0.027 (3)0.004 (3)
C30.067 (4)0.229 (9)0.075 (4)−0.003 (5)0.012 (3)0.001 (5)
C40.065 (4)0.262 (11)0.089 (5)−0.022 (6)0.003 (3)−0.054 (7)
C50.094 (4)0.183 (7)0.126 (6)−0.049 (5)0.030 (5)−0.047 (6)
C60.081 (3)0.133 (5)0.083 (4)−0.035 (3)0.031 (3)−0.026 (3)
C70.060 (2)0.072 (2)0.060 (2)−0.0043 (19)0.0268 (19)0.0109 (19)
C80.071 (3)0.112 (4)0.057 (3)−0.012 (2)0.026 (2)0.002 (2)
C90.083 (3)0.135 (4)0.079 (3)0.001 (3)0.045 (3)0.019 (3)
C100.075 (3)0.146 (5)0.092 (4)−0.030 (3)0.041 (3)0.009 (3)
C110.072 (3)0.096 (3)0.069 (3)−0.027 (2)0.023 (2)0.008 (2)
C120.064 (2)0.057 (2)0.056 (2)−0.0109 (17)0.0219 (19)0.0078 (17)
C130.073 (2)0.0442 (18)0.064 (2)−0.0032 (16)0.025 (2)0.0032 (16)
C140.063 (2)0.0405 (17)0.061 (2)−0.0035 (15)0.031 (2)−0.0010 (15)
C150.075 (3)0.054 (2)0.072 (3)−0.0043 (19)0.020 (2)0.0141 (19)
C160.153 (6)0.064 (3)0.102 (5)0.002 (3)0.003 (4)0.030 (3)
C170.109 (4)0.119 (5)0.128 (6)−0.017 (4)0.014 (4)0.058 (4)
C180.125 (5)0.098 (4)0.086 (4)0.006 (3)0.044 (3)0.024 (3)
C190.182 (7)0.097 (4)0.075 (4)−0.002 (4)0.015 (4)−0.001 (3)
C200.121 (4)0.095 (4)0.077 (4)−0.043 (3)0.000 (3)0.026 (3)
C210.168 (8)0.203 (9)0.108 (6)0.030 (7)0.063 (6)0.044 (6)
C220.251 (13)0.250 (13)0.075 (5)−0.011 (11)0.029 (7)−0.008 (6)
C230.150 (8)0.41 (2)0.126 (8)0.031 (11)0.055 (6)0.020 (10)

Geometric parameters (Å, °)

Cl3—C291.733 (5)C44A—H44A0.9700
Cl4—C251.743 (6)C44A—H44B0.9700
Cl1—C21.709 (6)C44B—H44C0.9700
Cl2—C61.765 (6)C44B—H44D0.9700
O2—C371.227 (4)C44B—H411.2000
O1—C141.230 (5)C45A—H45B0.9700
N4—C241.395 (6)C45A—H45A0.9700
N4—C301.409 (5)C45B—H45C0.9700
N5—N61.381 (5)C45B—H45D0.9700
N5—C371.318 (6)C46A—H46C0.9600
N6—C381.253 (8)C46A—H46A0.9600
N4—H4A0.8600C46A—H46B0.9600
N5—H5A0.8600C46B—H46E0.9600
N1—C11.385 (6)C46B—H46F0.9600
N1—C71.409 (6)C46B—H46D0.9600
N2—N31.395 (4)C1—C21.414 (7)
N2—C141.335 (5)C1—C61.365 (9)
N3—C151.257 (6)C2—C31.381 (9)
N1—H10.8600C3—C41.318 (17)
N2—H20.8600C4—C51.390 (15)
C24—C291.395 (7)C5—C61.380 (11)
C24—C251.398 (4)C7—C121.402 (6)
C25—C261.362 (8)C7—C81.387 (7)
C26—C271.369 (10)C8—C91.357 (9)
C27—C281.370 (7)C9—C101.364 (9)
C28—C291.369 (8)C10—C111.379 (9)
C30—C311.374 (7)C11—C121.384 (7)
C30—C351.395 (6)C12—C131.509 (6)
C31—C321.405 (9)C13—C141.507 (5)
C32—C331.371 (11)C15—C201.475 (8)
C33—C341.362 (12)C15—C161.502 (7)
C34—C351.396 (7)C16—C171.492 (10)
C35—C361.485 (7)C17—C181.528 (10)
C36—C371.523 (6)C18—C211.482 (9)
C38—C431.505 (10)C18—C191.531 (9)
C38—C391.492 (9)C19—C201.502 (9)
C39—C401.361 (14)C21—C221.524 (16)
C40—C411.504 (13)C22—C231.57 (2)
C41—C44B1.56 (3)C3—H30.9300
C41—C421.546 (10)C4—H40.9300
C41—C44A1.43 (2)C5—H50.9300
C42—C431.380 (14)C8—H80.9300
C44A—C45A1.528 (17)C9—H90.9300
C44B—C45B1.55 (3)C10—H100.9300
C45A—C46A1.49 (2)C11—H110.9300
C45B—C46B1.45 (5)C13—H13A0.9700
C26—H260.9300C13—H13B0.9700
C27—H270.9300C16—H16A0.9700
C28—H280.9300C16—H16B0.9700
C31—H310.9300C17—H17A0.9700
C32—H320.9300C17—H17B0.9700
C33—H330.9300C18—H180.9800
C34—H340.9300C19—H19A0.9700
C36—H36B0.9700C19—H19B0.9700
C36—H36A0.9700C20—H20A0.9700
C39—H39B0.9700C20—H20B0.9700
C39—H39A0.9700C21—H21A0.9700
C40—H40B0.9700C21—H21B0.9700
C40—H40A0.9700C22—H22A0.9700
C41—H410.9800C22—H22B0.9700
C42—H42B0.9700C23—H23A0.9600
C42—H42A0.9700C23—H23B0.9600
C43—H43A0.9700C23—H23C0.9600
C43—H43B0.9700
C24—N4—C30124.2 (3)C44A—C45A—H45B112.00
N6—N5—C37118.8 (3)C44A—C45A—H45A111.00
N5—N6—C38119.5 (4)C44B—C45B—H45C107.00
C24—N4—H4A118.00C44B—C45B—H45D107.00
C30—N4—H4A118.00C46B—C45B—H45C107.00
C37—N5—H5A121.00C46B—C45B—H45D107.00
N6—N5—H5A121.00H45C—C45B—H45D107.00
C1—N1—C7122.7 (4)C45A—C46A—H46A109.00
N3—N2—C14117.4 (3)H46A—C46A—H46B109.00
N2—N3—C15118.8 (4)H46B—C46A—H46C110.00
C7—N1—H1119.00C45A—C46A—H46C109.00
C1—N1—H1119.00H46A—C46A—H46C109.00
N3—N2—H2121.00C45A—C46A—H46B110.00
C14—N2—H2121.00C45B—C46B—H46D110.00
N4—C24—C25120.6 (4)H46E—C46B—H46F109.00
N4—C24—C29123.8 (3)C45B—C46B—H46E109.00
C25—C24—C29115.3 (4)C45B—C46B—H46F110.00
Cl4—C25—C26119.2 (3)H46D—C46B—H46E109.00
C24—C25—C26122.4 (5)H46D—C46B—H46F109.00
Cl4—C25—C24118.3 (4)N1—C1—C2121.2 (5)
C25—C26—C27120.5 (4)N1—C1—C6122.2 (4)
C26—C27—C28118.9 (6)C2—C1—C6116.6 (5)
C27—C28—C29120.5 (5)Cl1—C2—C3119.2 (5)
Cl3—C29—C28118.1 (4)C1—C2—C3120.7 (6)
C24—C29—C28122.1 (4)Cl1—C2—C1120.1 (4)
Cl3—C29—C24119.8 (4)C2—C3—C4120.1 (8)
N4—C30—C35117.2 (4)C3—C4—C5121.9 (9)
N4—C30—C31122.1 (4)C4—C5—C6117.9 (8)
C31—C30—C35120.7 (4)Cl2—C6—C5118.9 (6)
C30—C31—C32118.8 (5)C1—C6—C5122.6 (6)
C31—C32—C33120.8 (7)Cl2—C6—C1118.5 (4)
C32—C33—C34119.9 (7)N1—C7—C12119.3 (4)
C33—C34—C35121.0 (6)C8—C7—C12119.1 (4)
C30—C35—C36122.5 (4)N1—C7—C8121.5 (4)
C30—C35—C34118.8 (5)C7—C8—C9121.1 (4)
C34—C35—C36118.7 (5)C8—C9—C10121.0 (6)
C35—C36—C37111.8 (3)C9—C10—C11118.7 (6)
O2—C37—N5123.3 (4)C10—C11—C12122.2 (5)
N5—C37—C36115.7 (3)C7—C12—C13121.4 (4)
O2—C37—C36121.0 (4)C11—C12—C13120.7 (4)
N6—C38—C39127.1 (6)C7—C12—C11117.9 (4)
N6—C38—C43117.1 (5)C12—C13—C14109.6 (3)
C39—C38—C43115.8 (7)N2—C14—C13116.2 (3)
C38—C39—C40118.0 (6)O1—C14—N2123.1 (3)
C39—C40—C41122.5 (7)O1—C14—C13120.7 (4)
C42—C41—C44A114.2 (7)N3—C15—C20128.2 (4)
C42—C41—C44B132.8 (10)C16—C15—C20115.6 (5)
C40—C41—C42109.1 (8)N3—C15—C16116.2 (5)
C40—C41—C44A120.1 (8)C15—C16—C17112.5 (5)
C40—C41—C44B114.9 (9)C16—C17—C18111.7 (6)
C41—C42—C43116.1 (7)C17—C18—C19107.3 (5)
C38—C43—C42116.4 (6)C17—C18—C21113.7 (7)
C41—C44A—C45A122.8 (10)C19—C18—C21112.9 (6)
C41—C44B—C45B116 (2)C18—C19—C20113.7 (5)
C44A—C45A—C46A101.6 (11)C15—C20—C19111.7 (5)
C44B—C45B—C46B121 (2)C18—C21—C22116.5 (9)
C25—C26—H26120.00C21—C22—C23112.1 (10)
C27—C26—H26120.00C2—C3—H3120.00
C28—C27—H27121.00C4—C3—H3120.00
C26—C27—H27121.00C3—C4—H4119.00
C29—C28—H28120.00C5—C4—H4119.00
C27—C28—H28120.00C4—C5—H5121.00
C32—C31—H31121.00C6—C5—H5121.00
C30—C31—H31121.00C7—C8—H8119.00
C31—C32—H32120.00C9—C8—H8120.00
C33—C32—H32120.00C8—C9—H9119.00
C32—C33—H33120.00C10—C9—H9119.00
C34—C33—H33120.00C9—C10—H10121.00
C35—C34—H34120.00C11—C10—H10121.00
C33—C34—H34120.00C10—C11—H11119.00
C35—C36—H36B109.00C12—C11—H11119.00
C35—C36—H36A109.00C12—C13—H13A110.00
H36A—C36—H36B108.00C12—C13—H13B110.00
C37—C36—H36B109.00C14—C13—H13A110.00
C37—C36—H36A109.00C14—C13—H13B110.00
C40—C39—H39A108.00H13A—C13—H13B108.00
H39A—C39—H39B107.00C15—C16—H16A109.00
C38—C39—H39B108.00C15—C16—H16B109.00
C40—C39—H39B108.00C17—C16—H16A109.00
C38—C39—H39A108.00C17—C16—H16B109.00
C39—C40—H40A107.00H16A—C16—H16B108.00
C39—C40—H40B107.00C16—C17—H17A109.00
H40A—C40—H40B107.00C16—C17—H17B109.00
C41—C40—H40B107.00C18—C17—H17A109.00
C41—C40—H40A107.00C18—C17—H17B109.00
C44A—C41—H41104.00H17A—C17—H17B108.00
C44B—C41—H4150.00C17—C18—H18108.00
C42—C41—H41104.00C19—C18—H18108.00
C40—C41—H41104.00C21—C18—H18108.00
C43—C42—H42B108.00C18—C19—H19A109.00
C41—C42—H42A108.00C18—C19—H19B109.00
C41—C42—H42B108.00C20—C19—H19A109.00
H42A—C42—H42B107.00C20—C19—H19B109.00
C43—C42—H42A108.00H19A—C19—H19B108.00
C38—C43—H43B108.00C15—C20—H20A109.00
C38—C43—H43A108.00C15—C20—H20B109.00
C42—C43—H43A108.00C19—C20—H20A109.00
C42—C43—H43B108.00C19—C20—H20B109.00
H43A—C43—H43B107.00H20A—C20—H20B108.00
C45A—C44A—H44B107.00C18—C21—H21A108.00
H44A—C44A—H44B107.00C18—C21—H21B108.00
C41—C44A—H44B107.00C22—C21—H21A108.00
C45A—C44A—H44A107.00C22—C21—H21B108.00
C41—C44A—H44A107.00H21A—C21—H21B107.00
C45B—C44B—H41132.00C21—C22—H22A109.00
H41—C44B—H44C119.00C21—C22—H22B109.00
C41—C44B—H44D109.00C23—C22—H22A109.00
C45B—C44B—H44D108.00C23—C22—H22B109.00
H44C—C44B—H44D107.00H22A—C22—H22B108.00
C41—C44B—H44C108.00C22—C23—H23A109.00
H41—C44B—H44D70.00C22—C23—H23B110.00
C45B—C44B—H44C108.00C22—C23—H23C109.00
H45A—C45A—H45B109.00H23A—C23—H23B110.00
C46A—C45A—H45A111.00H23A—C23—H23C109.00
C46A—C45A—H45B111.00H23B—C23—H23C109.00
C24—N4—C30—C35167.8 (4)C38—C39—C40—C4127.6 (14)
C30—N4—C24—C25128.2 (4)C39—C40—C41—C42−36.2 (12)
C30—N4—C24—C29−58.4 (6)C39—C40—C41—C44A−170.9 (11)
C24—N4—C30—C31−13.1 (6)C44A—C41—C42—C43−177.3 (11)
C37—N5—N6—C38−175.4 (5)C40—C41—C42—C4345.1 (11)
N6—N5—C37—O2−1.1 (6)C42—C41—C44A—C45A−179.5 (12)
N6—N5—C37—C36178.6 (4)C40—C41—C44A—C45A−47 (2)
N5—N6—C38—C43−178.8 (6)C41—C42—C43—C38−46.4 (12)
N5—N6—C38—C391.3 (10)C41—C44A—C45A—C46A−62.9 (18)
C1—N1—C7—C8−9.6 (7)C2—C1—C6—Cl2−179.1 (5)
C7—N1—C1—C6115.8 (6)N1—C1—C6—Cl20.1 (8)
C1—N1—C7—C12171.5 (4)N1—C1—C6—C5−179.9 (7)
C7—N1—C1—C2−65.1 (7)N1—C1—C2—Cl1−4.7 (8)
N3—N2—C14—O16.3 (6)N1—C1—C2—C3175.8 (6)
C14—N2—N3—C15−174.7 (5)C6—C1—C2—Cl1174.5 (5)
N3—N2—C14—C13−171.4 (4)C6—C1—C2—C3−5.0 (9)
N2—N3—C15—C203.9 (8)C2—C1—C6—C50.9 (10)
N2—N3—C15—C16−176.3 (5)C1—C2—C3—C46.3 (12)
N4—C24—C25—Cl4−4.0 (5)Cl1—C2—C3—C4−173.2 (7)
C25—C24—C29—C28−4.2 (6)C2—C3—C4—C5−3.3 (14)
N4—C24—C29—Cl30.2 (6)C3—C4—C5—C6−0.8 (14)
N4—C24—C25—C26175.9 (4)C4—C5—C6—C12.0 (12)
C29—C24—C25—Cl4−178.0 (3)C4—C5—C6—Cl2−178.1 (7)
C25—C24—C29—Cl3174.0 (3)C8—C7—C12—C11−1.7 (6)
C29—C24—C25—C261.9 (6)C8—C7—C12—C13−179.9 (4)
N4—C24—C29—C28−178.0 (4)C12—C7—C8—C91.1 (7)
C24—C25—C26—C271.3 (8)N1—C7—C12—C11177.3 (4)
Cl4—C25—C26—C27−178.9 (5)N1—C7—C8—C9−177.8 (5)
C25—C26—C27—C28−2.3 (9)N1—C7—C12—C13−1.0 (6)
C26—C27—C28—C29−0.1 (9)C7—C8—C9—C100.2 (8)
C27—C28—C29—C243.4 (8)C8—C9—C10—C11−0.8 (9)
C27—C28—C29—Cl3−174.8 (5)C9—C10—C11—C120.2 (8)
N4—C30—C31—C32−177.6 (5)C10—C11—C12—C71.1 (7)
C31—C30—C35—C36179.7 (4)C10—C11—C12—C13179.3 (4)
C35—C30—C31—C321.5 (7)C11—C12—C13—C14−100.4 (4)
N4—C30—C35—C34178.7 (4)C7—C12—C13—C1477.9 (5)
N4—C30—C35—C36−1.2 (6)C12—C13—C14—O1−75.5 (5)
C31—C30—C35—C34−0.4 (7)C12—C13—C14—N2102.3 (4)
C30—C31—C32—C33−2.2 (10)N3—C15—C16—C17−131.7 (6)
C31—C32—C33—C341.8 (12)C20—C15—C16—C1748.2 (9)
C32—C33—C34—C35−0.6 (11)N3—C15—C20—C19133.7 (6)
C33—C34—C35—C36179.8 (6)C16—C15—C20—C19−46.1 (8)
C33—C34—C35—C30−0.1 (9)C15—C16—C17—C18−54.2 (9)
C30—C35—C36—C3780.0 (6)C16—C17—C18—C1957.9 (8)
C34—C35—C36—C37−100.0 (5)C16—C17—C18—C21−176.6 (7)
C35—C36—C37—O2−61.9 (5)C17—C18—C19—C20−57.3 (9)
C35—C36—C37—N5118.4 (4)C21—C18—C19—C20176.7 (7)
C39—C38—C43—C4234.4 (11)C17—C18—C21—C22161.5 (8)
N6—C38—C43—C42−145.6 (8)C19—C18—C21—C22−76.0 (11)
N6—C38—C39—C40156.0 (8)C18—C19—C20—C1551.8 (9)
C43—C38—C39—C40−23.9 (12)C18—C21—C22—C23−77.6 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.282.886 (4)128
N2—H2···O2i0.862.243.077 (5)165
N4—H4A···O20.862.322.921 (6)127
N5—H5A···O1ii0.862.213.034 (4)161
C20—H20A···O2i0.972.533.330 (6)139
C36—H36B···O1ii0.972.413.307 (5)155

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5287).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Gobec, S., Brozic, P. & Rizner, T. L. (2005). Bioorg. Med. Chem. Lett.15, 5170–5175. [PubMed]
  • Moser, P., Sallmann, A. & Wiesenberg, I. (1990). J. Med. Chem.33, 2358–2368. [PubMed]
  • Sallmann, A. (1986). Am. J. Chem. 80 (Suppl. 4B), 29–33. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sriram, D., Yogeeswari, P. & Devakaram, R. V. (2006). Bioorg. Med. Chem.14, 3113–3118. [PubMed]
  • Stoe & Cie (2002). X-AREA and X-RED32 Stoe & Cie, Darmstadt, Germany.
  • Wittine, K., Benci, K., Rajic, Z., Zorc, B., Kralj, M., Marjanovic, M., Pavelic, K., De Clercq, E., Andrei, G., Snoeck, R., Balsarini, J. & Mintas, M. (2009). Eur. J. Med. Chem.44, 143–151. [PubMed]
  • Zhang, J., Wang, J., Wu, H., He, Y., Zhu, G., Cui, X. & Tang, L. (2009). Bioorg. Med. Chem. Lett.19, 3324–3327. [PubMed]

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