organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-[4-(2-Chloro­acet­yl)phen­yl]-2-methyl-1-(pyrrolidin-1-yl)propan-1-one

aSecurity and Environment Engineering College, Capital University of Economics and Business, Beijing 10070, People's Republic of China
*Correspondence e-mail: nanoren@126.com

(Received 30 June 2013; accepted 22 July 2013; online 27 July 2013)

The asymmetric unit of the title compound, C16H20ClNO2, contains two mol­ecules in which the dihedral angles between the benzene ring and the plane of the amide unit are 77.4 (1) and 81.1 (1)°. In both mol­ecules, the five-membered ring adopts an envelope conformation with one of the β-C atoms as the flap. In the crystal, mol­ecules are connected via C—H⋯O hydrogen bonds, forming chains along the b-axis direction. These chains are further linked by C—H⋯π inter­actions, forming a three-dimensional network.

Related literature

For background to applications of the title compound, see: Krauss et al. (2001[Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (2001). US Patent No. 6242606.]). For the synthetic procedure of the title compound, see: Krauss et al. (1995[Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (1995). WO Patent No. 9500480.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20ClNO2

  • Mr = 293.78

  • Monoclinic, P c

  • a = 8.7380 (17) Å

  • b = 6.1660 (12) Å

  • c = 28.670 (6) Å

  • β = 95.95 (3)°

  • V = 1536.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.929, Tmax = 0.976

  • 5766 measured reflections

  • 3048 independent reflections

  • 1538 reflections with I > 2σ(I)

  • Rint = 0.093

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.069

  • S = 0.92

  • 3048 reflections

  • 361 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.19 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 200 Friedel pairs

  • Absolute structure parameter: 0.06 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C9–C14 and C25–C30 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4A⋯O1i 0.97 2.53 3.427 (9) 153
C32—H32B⋯O1i 0.97 2.35 3.136 (8) 138
C18—H18BCg4ii 0.97 2.73 3.448 (7) 131
C4—H4BCg2 0.97 2.89 3.728 (9) 145
C23—H23BCg2iii 0.96 2.98 3.932 (6) 171
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z; (iii) [x, -y+1, z-{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf–Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound (I) is an important intermediate in the synthesis of [(piperidinoalkanoyl)phenyl]propionates, which can be utilized to synthesize antihistaminics (Krauss et al., 2001).

The molecular structure of (I) is shown in Fig. 1. There is a intermolecular contact C—H···O in the title compound, forming molecular chains (Table 1, Fig. 2). The crystal packing is further controlled by C—H···π interactions [C18—H18B···Cg4 distance of 2.730 Å, C4—H4B···Cg2 distance of 2.890 Å and C23—H23B···Cg2 distance of 2.980 Å (Cg4 and Cg2 are the centroids of the rings defined by the atoms C25—C30 and C9—C14, respectively)].

The dihedral angles between the benzene ring and the plane of the amide are 77.4 (1)° and 81.1 (1)°, respectively. The conformation of 5-memebred rings are both envelope with the tip atoms C3 and C18, respectively.

Related literature top

For background to applications of the title compound, see: Krauss et al. (2001). For the synthetic procedure of the title compound, see: Krauss et al. (1995).

Experimental top

The title compound, (I) was prepared by a method reported in literature (Krauss et al., 1995). The crystals were obtained by dissolving (I) (0.1 g) in methanol (30 ml) and evaporating the solvent slowly at room temperature for about 8 d.

Refinement top

All H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93 Å for aromatic H, 0.96 Å for alkyl H and 0.97 Å for other H, respectively. The Uiso(H) = xUeq(C), where x = 1.2 for aromatic H and x = 1.5 for other H.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of (I) showing C—H···O interactions.
2-[4-(2-Chloroacetyl)phenyl]-2-methyl-1-(pyrrolidin-1-yl)propan-1-one top
Crystal data top
C16H20ClNO2F(000) = 624
Mr = 293.78Dx = 1.270 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 25 reflections
a = 8.7380 (17) Åθ = 9–12°
b = 6.1660 (12) ŵ = 0.25 mm1
c = 28.670 (6) ÅT = 293 K
β = 95.95 (3)°Block, colourless
V = 1536.4 (5) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1538 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.093
Graphite monochromatorθmax = 25.5°, θmin = 1.4°
ω/2θ scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 77
Tmin = 0.929, Tmax = 0.976l = 3434
5766 measured reflections3 standard reflections every 200 reflections
3048 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
3048 reflectionsΔρmax = 0.16 e Å3
361 parametersΔρmin = 0.19 e Å3
2 restraintsAbsolute structure: Flack (1983), 200 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (7)
Crystal data top
C16H20ClNO2V = 1536.4 (5) Å3
Mr = 293.78Z = 4
Monoclinic, PcMo Kα radiation
a = 8.7380 (17) ŵ = 0.25 mm1
b = 6.1660 (12) ÅT = 293 K
c = 28.670 (6) Å0.30 × 0.20 × 0.10 mm
β = 95.95 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1538 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.093
Tmin = 0.929, Tmax = 0.9763 standard reflections every 200 reflections
5766 measured reflections intensity decay: 1%
3048 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.069Δρmax = 0.16 e Å3
S = 0.92Δρmin = 0.19 e Å3
3048 reflectionsAbsolute structure: Flack (1983), 200 Friedel pairs
361 parametersAbsolute structure parameter: 0.06 (7)
2 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2012 (2)0.1803 (4)0.78932 (8)0.1097 (8)
O10.4889 (5)0.9996 (8)0.5934 (2)0.0921 (17)
N10.3621 (6)0.7027 (9)0.5710 (2)0.0691 (16)
C10.3014 (8)0.8012 (16)0.5260 (2)0.088 (2)
H1A0.38510.83590.50760.105*
H1B0.24630.93390.53150.105*
O20.1115 (6)0.5903 (12)0.75207 (18)0.116 (2)
C20.1938 (8)0.6382 (13)0.5003 (2)0.092 (2)
H2A0.09120.69790.49350.110*
H2B0.23160.59320.47120.110*
C30.1942 (9)0.4580 (16)0.5331 (3)0.116 (3)
H3A0.09110.44090.54220.140*
H3B0.21940.32640.51700.140*
C40.2949 (9)0.4789 (11)0.5729 (3)0.086 (2)
H4A0.37530.37010.57360.103*
H4B0.24130.46230.60070.103*
C50.4534 (7)0.8096 (11)0.6038 (3)0.0638 (18)
C60.5056 (6)0.7068 (10)0.6500 (2)0.0571 (17)
C70.6227 (6)0.5225 (11)0.6410 (2)0.0712 (19)
H7A0.57140.41300.62140.107*
H7B0.66240.45910.67040.107*
H7C0.70590.58240.62580.107*
C80.5976 (8)0.8805 (11)0.6806 (3)0.090 (3)
H8A0.53050.99790.68680.136*
H8B0.68010.93450.66410.136*
H8C0.63920.81640.70970.136*
C90.3701 (7)0.6353 (10)0.6749 (2)0.0584 (18)
C100.2419 (7)0.7633 (11)0.6742 (2)0.0719 (19)
H10A0.23800.89380.65790.086*
C110.1172 (7)0.7011 (13)0.6976 (2)0.074 (2)
H11A0.03150.79100.69670.089*
C120.1183 (7)0.5080 (11)0.7223 (2)0.0623 (18)
C130.2467 (6)0.3841 (11)0.7243 (2)0.0655 (18)
H13A0.25270.25830.74230.079*
C140.3707 (7)0.4430 (10)0.6996 (2)0.0589 (17)
H14A0.45490.35070.69990.071*
C150.0202 (8)0.4508 (12)0.7470 (3)0.070 (2)
C160.0287 (7)0.2273 (13)0.7645 (2)0.085 (2)
H16A0.05760.20080.78790.102*
H16B0.02120.12670.73880.102*
Cl20.9469 (2)0.0349 (6)0.60136 (9)0.1388 (12)
O30.2684 (5)0.5797 (7)0.34112 (17)0.0727 (14)
O40.8000 (6)0.2310 (11)0.5262 (2)0.118 (2)
N20.1664 (5)0.3029 (8)0.37657 (18)0.0543 (14)
C170.0265 (6)0.4269 (12)0.3801 (2)0.0656 (19)
H17A0.03100.44520.34960.079*
H17B0.04980.56860.39370.079*
C180.0630 (7)0.2889 (14)0.4121 (3)0.082 (2)
H18A0.05770.35260.44320.098*
H18B0.17020.27860.39960.098*
C190.0076 (7)0.0773 (13)0.4142 (3)0.102 (3)
H19A0.05620.02260.39460.123*
H19B0.01510.02390.44620.123*
C200.1608 (6)0.0860 (10)0.3983 (3)0.075 (2)
H20A0.17390.02750.37570.090*
H20B0.23990.07130.42450.090*
C210.2787 (6)0.3879 (9)0.3547 (2)0.0419 (13)
C220.4252 (6)0.2566 (8)0.3476 (2)0.0453 (15)
C230.3801 (6)0.0863 (10)0.3114 (2)0.0582 (16)
H23A0.46860.00070.30620.087*
H23B0.34060.15470.28250.087*
H23C0.30240.00550.32220.087*
C240.5426 (6)0.4097 (10)0.32785 (19)0.0579 (17)
H24A0.63370.32960.32290.087*
H24B0.56870.52480.34980.087*
H24C0.49840.46970.29860.087*
C250.5000 (5)0.1729 (9)0.3944 (2)0.0421 (14)
C260.5181 (5)0.3049 (11)0.4325 (2)0.0515 (15)
H26A0.47200.44090.43040.062*
C270.6012 (6)0.2468 (10)0.4738 (2)0.0613 (18)
H27A0.61710.34590.49820.074*
C280.6630 (6)0.0328 (12)0.4789 (3)0.0585 (17)
C290.6428 (6)0.0986 (11)0.4393 (2)0.0636 (18)
H29A0.68640.23630.44070.076*
C300.5624 (6)0.0338 (9)0.3990 (2)0.0535 (16)
H30A0.54850.12950.37380.064*
C310.7586 (8)0.0398 (15)0.5211 (3)0.072 (2)
C320.8049 (7)0.1175 (18)0.5571 (2)0.094 (3)
H32B0.71440.16020.57170.112*
H32A0.84220.24530.54210.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0799 (12)0.1040 (16)0.150 (2)0.0129 (14)0.0365 (12)0.0288 (18)
O10.089 (3)0.035 (2)0.150 (5)0.015 (2)0.002 (3)0.012 (3)
N10.073 (4)0.041 (3)0.094 (5)0.013 (3)0.009 (3)0.014 (3)
C10.086 (5)0.100 (6)0.078 (6)0.023 (5)0.007 (4)0.024 (5)
O20.108 (4)0.134 (6)0.113 (4)0.076 (4)0.045 (3)0.035 (4)
C20.097 (6)0.073 (6)0.102 (6)0.004 (5)0.005 (5)0.016 (5)
C30.133 (7)0.097 (7)0.106 (7)0.033 (6)0.046 (6)0.001 (6)
C40.124 (6)0.035 (4)0.097 (6)0.017 (4)0.000 (5)0.008 (4)
C50.056 (4)0.040 (4)0.093 (5)0.001 (4)0.003 (3)0.010 (4)
C60.055 (4)0.036 (3)0.077 (5)0.002 (3)0.006 (3)0.006 (4)
C70.077 (4)0.044 (4)0.093 (5)0.007 (4)0.007 (4)0.000 (4)
C80.097 (6)0.045 (4)0.123 (7)0.004 (4)0.017 (5)0.022 (5)
C90.074 (4)0.034 (3)0.065 (4)0.019 (3)0.002 (4)0.008 (3)
C100.093 (5)0.038 (4)0.083 (5)0.022 (4)0.004 (4)0.002 (4)
C110.076 (5)0.071 (5)0.075 (6)0.036 (4)0.009 (4)0.006 (5)
C120.066 (4)0.052 (4)0.068 (5)0.025 (4)0.003 (4)0.011 (4)
C130.071 (4)0.051 (4)0.076 (5)0.027 (4)0.010 (4)0.010 (4)
C140.065 (4)0.036 (4)0.077 (5)0.019 (3)0.015 (3)0.002 (3)
C150.069 (4)0.067 (5)0.074 (5)0.038 (4)0.003 (4)0.003 (4)
C160.072 (4)0.088 (6)0.101 (6)0.009 (5)0.032 (4)0.026 (5)
Cl20.0863 (14)0.218 (3)0.1052 (16)0.0096 (19)0.0210 (11)0.042 (2)
O30.079 (3)0.026 (2)0.115 (4)0.009 (2)0.024 (3)0.009 (3)
O40.132 (5)0.101 (5)0.114 (5)0.051 (4)0.014 (4)0.024 (4)
N20.037 (2)0.032 (2)0.098 (4)0.002 (2)0.021 (3)0.007 (3)
C170.046 (4)0.070 (5)0.083 (5)0.015 (4)0.016 (3)0.006 (4)
C180.050 (4)0.092 (6)0.106 (6)0.004 (4)0.020 (4)0.011 (5)
C190.086 (6)0.083 (6)0.145 (8)0.016 (5)0.046 (6)0.041 (6)
C200.060 (4)0.038 (4)0.130 (7)0.003 (3)0.027 (4)0.019 (4)
C210.053 (3)0.031 (3)0.042 (3)0.001 (3)0.005 (3)0.001 (3)
C220.035 (3)0.031 (3)0.071 (4)0.012 (3)0.013 (3)0.003 (3)
C230.072 (4)0.041 (3)0.063 (4)0.000 (3)0.014 (3)0.005 (4)
C240.071 (4)0.047 (3)0.060 (4)0.008 (3)0.025 (3)0.005 (3)
C250.038 (3)0.034 (3)0.056 (4)0.006 (3)0.013 (3)0.002 (3)
C260.038 (3)0.050 (3)0.067 (4)0.008 (3)0.007 (3)0.001 (4)
C270.050 (3)0.055 (4)0.080 (5)0.000 (3)0.013 (3)0.011 (4)
C280.036 (3)0.058 (4)0.085 (5)0.012 (3)0.023 (3)0.004 (4)
C290.048 (4)0.037 (3)0.109 (6)0.000 (3)0.023 (4)0.007 (4)
C300.063 (4)0.030 (3)0.067 (5)0.002 (3)0.007 (3)0.007 (3)
C310.059 (4)0.082 (6)0.076 (5)0.004 (4)0.007 (4)0.008 (5)
C320.055 (4)0.150 (8)0.076 (5)0.012 (5)0.006 (4)0.020 (6)
Geometric parameters (Å, º) top
Cl1—C161.756 (6)Cl2—C321.757 (7)
O1—C51.256 (8)O3—C211.246 (7)
N1—C51.341 (8)O4—C311.237 (9)
N1—C11.475 (8)N2—C211.326 (6)
N1—C41.502 (8)N2—C171.454 (7)
C1—C21.515 (10)N2—C201.479 (8)
C1—H1A0.9700C17—C181.526 (8)
C1—H1B0.9700C17—H17A0.9700
O2—C151.192 (8)C17—H17B0.9700
C2—C31.455 (11)C18—C191.442 (10)
C2—H2A0.9700C18—H18A0.9700
C2—H2B0.9700C18—H18B0.9700
C3—C41.375 (9)C19—C201.459 (7)
C3—H3A0.9700C19—H19A0.9700
C3—H3B0.9700C19—H19B0.9700
C4—H4A0.9700C20—H20A0.9700
C4—H4B0.9700C20—H20B0.9700
C5—C61.497 (10)C21—C221.547 (7)
C6—C91.510 (8)C22—C231.501 (8)
C6—C81.554 (9)C22—C251.521 (8)
C6—C71.568 (8)C22—C241.543 (7)
C7—H7A0.9600C23—H23A0.9600
C7—H7B0.9600C23—H23B0.9600
C7—H7C0.9600C23—H23C0.9600
C8—H8A0.9600C24—H24A0.9600
C8—H8B0.9600C24—H24B0.9600
C8—H8C0.9600C24—H24C0.9600
C9—C101.369 (7)C25—C261.357 (8)
C9—C141.381 (9)C25—C301.387 (7)
C10—C111.391 (8)C26—C271.371 (8)
C10—H10A0.9300C26—H26A0.9300
C11—C121.384 (9)C27—C281.428 (9)
C11—H11A0.9300C27—H27A0.9300
C12—C131.353 (7)C28—C291.390 (9)
C12—C151.507 (9)C28—C311.468 (10)
C13—C141.401 (8)C29—C301.349 (8)
C13—H13A0.9300C29—H29A0.9300
C14—H14A0.9300C30—H30A0.9300
C15—C161.471 (10)C31—C321.442 (11)
C16—H16A0.9700C32—H32B0.9700
C16—H16B0.9700C32—H32A0.9700
C5—N1—C1123.0 (6)C21—N2—C17119.6 (5)
C5—N1—C4129.2 (6)C21—N2—C20128.0 (4)
C1—N1—C4107.7 (6)C17—N2—C20112.4 (4)
N1—C1—C2107.5 (6)N2—C17—C18103.6 (5)
N1—C1—H1A110.2N2—C17—H17A111.0
C2—C1—H1A110.2C18—C17—H17A111.0
N1—C1—H1B110.2N2—C17—H17B111.0
C2—C1—H1B110.2C18—C17—H17B111.0
H1A—C1—H1B108.5H17A—C17—H17B109.0
C3—C2—C1103.5 (6)C19—C18—C17106.6 (6)
C3—C2—H2A111.1C19—C18—H18A110.4
C1—C2—H2A111.1C17—C18—H18A110.4
C3—C2—H2B111.1C19—C18—H18B110.4
C1—C2—H2B111.1C17—C18—H18B110.4
H2A—C2—H2B109.0H18A—C18—H18B108.6
C4—C3—C2115.1 (7)C18—C19—C20110.9 (6)
C4—C3—H3A108.5C18—C19—H19A109.5
C2—C3—H3A108.5C20—C19—H19A109.5
C4—C3—H3B108.5C18—C19—H19B109.5
C2—C3—H3B108.5C20—C19—H19B109.5
H3A—C3—H3B107.5H19A—C19—H19B108.1
C3—C4—N1105.9 (7)C19—C20—N2103.7 (5)
C3—C4—H4A110.5C19—C20—H20A111.0
N1—C4—H4A110.5N2—C20—H20A111.0
C3—C4—H4B110.5C19—C20—H20B111.0
N1—C4—H4B110.5N2—C20—H20B111.0
H4A—C4—H4B108.7H20A—C20—H20B109.0
O1—C5—N1115.9 (7)O3—C21—N2119.4 (5)
O1—C5—C6123.0 (7)O3—C21—C22119.3 (5)
N1—C5—C6121.1 (6)N2—C21—C22121.3 (5)
C5—C6—C9111.1 (5)C23—C22—C25115.5 (5)
C5—C6—C8107.4 (5)C23—C22—C24108.1 (5)
C9—C6—C8108.7 (6)C25—C22—C24106.8 (4)
C5—C6—C7107.8 (6)C23—C22—C21107.2 (4)
C9—C6—C7115.0 (5)C25—C22—C21110.3 (5)
C8—C6—C7106.5 (5)C24—C22—C21108.6 (4)
C6—C7—H7A109.5C22—C23—H23A109.5
C6—C7—H7B109.5C22—C23—H23B109.5
H7A—C7—H7B109.5H23A—C23—H23B109.5
C6—C7—H7C109.5C22—C23—H23C109.5
H7A—C7—H7C109.5H23A—C23—H23C109.5
H7B—C7—H7C109.5H23B—C23—H23C109.5
C6—C8—H8A109.5C22—C24—H24A109.5
C6—C8—H8B109.5C22—C24—H24B109.5
H8A—C8—H8B109.5H24A—C24—H24B109.5
C6—C8—H8C109.5C22—C24—H24C109.5
H8A—C8—H8C109.5H24A—C24—H24C109.5
H8B—C8—H8C109.5H24B—C24—H24C109.5
C10—C9—C14117.5 (6)C26—C25—C30117.5 (6)
C10—C9—C6120.4 (6)C26—C25—C22120.7 (5)
C14—C9—C6122.1 (5)C30—C25—C22121.6 (6)
C9—C10—C11121.0 (6)C25—C26—C27123.0 (6)
C9—C10—H10A119.5C25—C26—H26A118.5
C11—C10—H10A119.5C27—C26—H26A118.5
C12—C11—C10121.3 (6)C26—C27—C28119.4 (7)
C12—C11—H11A119.4C26—C27—H27A120.3
C10—C11—H11A119.4C28—C27—H27A120.3
C13—C12—C11118.0 (6)C29—C28—C27116.1 (6)
C13—C12—C15123.4 (6)C29—C28—C31120.6 (6)
C11—C12—C15118.6 (6)C27—C28—C31122.9 (7)
C12—C13—C14120.9 (6)C30—C29—C28122.5 (6)
C12—C13—H13A119.6C30—C29—H29A118.7
C14—C13—H13A119.6C28—C29—H29A118.7
C9—C14—C13121.3 (6)C29—C30—C25121.2 (6)
C9—C14—H14A119.4C29—C30—H30A119.4
C13—C14—H14A119.4C25—C30—H30A119.4
O2—C15—C16125.2 (7)O4—C31—C32120.0 (8)
O2—C15—C12118.0 (7)O4—C31—C28121.4 (8)
C16—C15—C12116.8 (6)C32—C31—C28118.6 (7)
C15—C16—Cl1111.6 (5)C31—C32—Cl2116.5 (7)
C15—C16—H16A109.3C31—C32—H32B108.2
Cl1—C16—H16A109.3Cl2—C32—H32B108.2
C15—C16—H16B109.3C31—C32—H32A108.2
Cl1—C16—H16B109.3Cl2—C32—H32A108.2
H16A—C16—H16B108.0H32B—C32—H32A107.3
C5—N1—C1—C2175.6 (6)C21—N2—C17—C18173.2 (6)
C4—N1—C1—C20.9 (9)C20—N2—C17—C188.0 (7)
N1—C1—C2—C32.2 (9)N2—C17—C18—C1915.1 (8)
C1—C2—C3—C45.1 (11)C17—C18—C19—C2017.4 (10)
C2—C3—C4—N15.7 (11)C18—C19—C20—N212.2 (10)
C5—N1—C4—C3172.3 (7)C21—N2—C20—C19176.7 (7)
C1—N1—C4—C33.9 (9)C17—N2—C20—C192.0 (8)
C1—N1—C5—O12.0 (10)C17—N2—C21—O36.2 (9)
C4—N1—C5—O1177.7 (7)C20—N2—C21—O3175.2 (7)
C1—N1—C5—C6176.8 (6)C17—N2—C21—C22176.3 (5)
C4—N1—C5—C61.1 (11)C20—N2—C21—C222.3 (9)
O1—C5—C6—C9121.9 (7)O3—C21—C22—C23110.9 (6)
N1—C5—C6—C956.8 (8)N2—C21—C22—C2371.6 (7)
O1—C5—C6—C83.2 (10)O3—C21—C22—C25122.5 (6)
N1—C5—C6—C8175.5 (6)N2—C21—C22—C2555.0 (7)
O1—C5—C6—C7111.2 (7)O3—C21—C22—C245.7 (8)
N1—C5—C6—C770.0 (8)N2—C21—C22—C24171.8 (5)
C5—C6—C9—C1040.4 (8)C23—C22—C25—C26167.0 (4)
C8—C6—C9—C1077.6 (7)C24—C22—C25—C2672.6 (6)
C7—C6—C9—C10163.2 (6)C21—C22—C25—C2645.2 (6)
C5—C6—C9—C14140.6 (6)C23—C22—C25—C3017.9 (7)
C8—C6—C9—C14101.4 (7)C24—C22—C25—C30102.4 (6)
C7—C6—C9—C1417.8 (9)C21—C22—C25—C30139.7 (5)
C14—C9—C10—C110.1 (9)C30—C25—C26—C273.5 (8)
C6—C9—C10—C11179.0 (6)C22—C25—C26—C27171.7 (5)
C9—C10—C11—C120.2 (10)C25—C26—C27—C284.8 (9)
C10—C11—C12—C132.2 (10)C26—C27—C28—C294.5 (8)
C10—C11—C12—C15179.8 (7)C26—C27—C28—C31177.4 (6)
C11—C12—C13—C144.1 (10)C27—C28—C29—C303.6 (9)
C15—C12—C13—C14178.5 (6)C31—C28—C29—C30176.6 (6)
C10—C9—C14—C132.0 (9)C28—C29—C30—C252.6 (9)
C6—C9—C14—C13177.0 (6)C26—C25—C30—C292.3 (8)
C12—C13—C14—C94.1 (10)C22—C25—C30—C29172.9 (5)
C13—C12—C15—O2163.2 (7)C29—C28—C31—O413.5 (10)
C11—C12—C15—O214.2 (10)C27—C28—C31—O4174.0 (7)
C13—C12—C15—C1614.7 (10)C29—C28—C31—C32166.1 (6)
C11—C12—C15—C16167.9 (7)C27—C28—C31—C326.4 (9)
O2—C15—C16—Cl15.8 (11)O4—C31—C32—Cl211.1 (10)
C12—C15—C16—Cl1176.5 (5)C28—C31—C32—Cl2168.6 (5)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg4 are the centroids of the C9–C14 and C25–C30 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.972.533.427 (9)153
C32—H32B···O1i0.972.353.136 (8)138
C18—H18B···Cg4ii0.972.733.448 (7)131
C4—H4B···Cg20.972.893.728 (9)145
C23—H23B···Cg2iii0.962.983.932 (6)171
Symmetry codes: (i) x, y1, z; (ii) x1, y, z; (iii) x, y+1, z1/2.
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg4 are the centroids of the C9–C14 and C25–C30 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.972.533.427 (9)153
C32—H32B···O1i0.972.353.136 (8)138
C18—H18B···Cg4ii0.972.733.448 (7)131
C4—H4B···Cg20.972.893.728 (9)145
C23—H23B···Cg2iii0.962.983.932 (6)171
Symmetry codes: (i) x, y1, z; (ii) x1, y, z; (iii) x, y+1, z1/2.
 

Acknowledgements

This study was supported financially by the Scientific Research Project of Beijing Education Commission and the Scientific Research Level Project of Beijing Education Commission Foundation. The author thanks the Center of Testing and Analysis, Beijing University of Science and Technology, for the data collection.

References

First citationEnraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationKrauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (1995). WO Patent No. 9500480.
First citationKrauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (2001). US Patent No. 6242606.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds