#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/41/2224148.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224148
loop_
_publ_author_name
'Khan, F. Nawaz'
'Nithya, P.'
'Krishna Kumar, V.'
'Hathwar, Venkatesha R.'
'Ng, Seik Weng'
_publ_section_title
;
 1-(2-Chloroacetyl)-3-methyl-2,6-diphenylpiperidin-4-one
;
_journal_coeditor_code           CI2956
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2985
_journal_paper_doi               10.1107/S1600536809045358
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H20 Cl N O2'
_chemical_formula_moiety         'C20 H20 Cl N O2'
_chemical_formula_sum            'C20 H20 Cl N O2'
_chemical_formula_weight         341.82
_chemical_name_systematic
;
1-(2-Chloroacetyl)-3-methyl-2,6-diphenylpiperidin-4-one
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.423(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.026(6)
_cell_length_b                   12.417(2)
_cell_length_c                   9.3209(17)
_cell_measurement_reflns_used    1325
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      20.7
_cell_measurement_theta_min      3.0
_cell_volume                     3519.7(11)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14797
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.135
_refine_ls_abs_structure_details 'Flack (1983), 3002 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7013
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0334P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                4933
_reflns_number_total             7013
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2956.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3519.8(11)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2224148
_cod_database_fobs_code          2224148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.50000(3) 0.64105(6) 0.50836(9) 0.0634(2) Uani d . 1 . .
Cl Cl2 0.41803(3) 0.49823(7) 0.15694(9) 0.0608(2) Uani d . 1 . .
O O1 0.63439(8) 0.1780(2) 0.3091(3) 0.0758(7) Uani d . 1 . .
O O2 0.57673(8) 0.53213(18) 0.6705(3) 0.0685(7) Uani d . 1 . .
O O3 0.22780(8) 0.6049(2) 0.4959(3) 0.0728(7) Uani d . 1 . .
O O4 0.32828(7) 0.55176(18) 0.0346(2) 0.0622(6) Uani d . 1 . .
N N1 0.57108(8) 0.3715(2) 0.5510(2) 0.0430(6) Uani d . 1 . .
N N2 0.30973(8) 0.64746(17) 0.2214(2) 0.0405(6) Uani d . 1 . .
C C1 0.61735(10) 0.2246(3) 0.3972(3) 0.0510(8) Uani d . 1 . .
C C2 0.63947(11) 0.3156(3) 0.4873(4) 0.0598(9) Uani d . 1 . .
H H2A 0.6395 0.3782 0.4251 0.072 Uiso calc R 1 . .
H H2B 0.6698 0.2961 0.5258 0.072 Uiso calc R 1 . .
C C3 0.61746(10) 0.3449(3) 0.6139(3) 0.0501(8) Uani d . 1 . .
H H3 0.6313 0.4118 0.6560 0.060 Uiso calc R 1 . .
C C4 0.54533(10) 0.2968(2) 0.4414(3) 0.0422(7) Uani d . 1 . .
H H4 0.5391 0.3344 0.3471 0.051 Uiso calc R 1 . .
C C5 0.57193(10) 0.1944(2) 0.4222(3) 0.0470(8) Uani d . 1 . .
H H5 0.5761 0.1545 0.5146 0.056 Uiso calc R 1 . .
C C6 0.62226(10) 0.2644(3) 0.7379(3) 0.0472(8) Uani d . 1 . .
C C7 0.64743(11) 0.1717(3) 0.7463(4) 0.0602(9) Uani d . 1 . .
H H7 0.6631 0.1574 0.6730 0.072 Uiso calc R 1 . .
C C8 0.64984(12) 0.1004(3) 0.8605(4) 0.0675(10) Uani d . 1 . .
H H8 0.6670 0.0388 0.8640 0.081 Uiso calc R 1 . .
C C9 0.62698(13) 0.1204(3) 0.9686(4) 0.0695(10) Uani d . 1 . .
H H9 0.6279 0.0713 1.0446 0.083 Uiso calc R 1 . .
C C10 0.60264(12) 0.2128(3) 0.9652(4) 0.0698(11) Uani d . 1 . .
H H10 0.5875 0.2274 1.0397 0.084 Uiso calc R 1 . .
C C11 0.60076(11) 0.2835(3) 0.8510(3) 0.0598(9) Uani d . 1 . .
H H11 0.5844 0.3464 0.8501 0.072 Uiso calc R 1 . .
C C12 0.50134(10) 0.2664(2) 0.4800(3) 0.0443(7) Uani d . 1 . .
C C13 0.49875(13) 0.2290(3) 0.6171(4) 0.0621(10) Uani d . 1 . .
H H13 0.5242 0.2204 0.6880 0.074 Uiso calc R 1 . .
C C14 0.45792(15) 0.2039(3) 0.6495(4) 0.0744(12) Uani d . 1 . .
H H14 0.4562 0.1790 0.7423 0.089 Uiso calc R 1 . .
C C15 0.42043(14) 0.2160(3) 0.5452(5) 0.0713(11) Uani d . 1 . .
H H15 0.3932 0.1996 0.5672 0.086 Uiso calc R 1 . .
C C16 0.42293(12) 0.2519(3) 0.4098(5) 0.0649(9) Uani d . 1 . .
H H16 0.3974 0.2601 0.3392 0.078 Uiso calc R 1 . .
C C17 0.46276(10) 0.2760(2) 0.3765(4) 0.0524(8) Uani d . 1 . .
H H17 0.4640 0.2993 0.2826 0.063 Uiso calc R 1 . .
C C18 0.55669(10) 0.4715(2) 0.5775(4) 0.0480(8) Uani d . 1 . .
C C19 0.51356(11) 0.5052(2) 0.4795(4) 0.0570(9) Uani d . 1 . .
H H19A 0.4902 0.4589 0.4985 0.068 Uiso calc R 1 . .
H H19B 0.5158 0.4958 0.3780 0.068 Uiso calc R 1 . .
C C20 0.54732(12) 0.1207(3) 0.3038(4) 0.0682(10) Uani d . 1 . .
H H20A 0.5666 0.0647 0.2840 0.102 Uiso calc R 1 . .
H H20B 0.5371 0.1616 0.2163 0.102 Uiso calc R 1 . .
H H20C 0.5226 0.0893 0.3363 0.102 Uiso calc R 1 . .
C C21 0.32251(10) 0.6907(2) 0.3728(3) 0.0411(7) Uani d . 1 . .
H H21 0.3375 0.6327 0.4347 0.049 Uiso calc R 1 . .
C C22 0.28172(11) 0.7229(3) 0.4345(3) 0.0492(8) Uani d . 1 . .
H H22 0.2696 0.7884 0.3833 0.059 Uiso calc R 1 . .
C C23 0.24657(10) 0.6372(3) 0.4037(4) 0.0510(8) Uani d . 1 . .
C C24 0.23644(11) 0.5946(3) 0.2506(3) 0.0520(8) Uani d . 1 . .
H H24A 0.2054 0.6053 0.2109 0.062 Uiso calc R 1 . .
H H24B 0.2420 0.5177 0.2534 0.062 Uiso calc R 1 . .
C C25 0.26308(10) 0.6470(2) 0.1472(3) 0.0446(7) Uani d . 1 . .
H H25 0.2611 0.5977 0.0641 0.054 Uiso calc R 1 . .
C C26 0.24783(10) 0.7553(2) 0.0823(3) 0.0470(8) Uani d . 1 . .
C C27 0.21257(12) 0.8110(3) 0.1142(4) 0.0613(9) Uani d . 1 . .
H H27 0.1970 0.7822 0.1806 0.074 Uiso calc R 1 . .
C C28 0.20001(14) 0.9089(3) 0.0493(4) 0.0825(12) Uani d . 1 . .
H H28 0.1762 0.9455 0.0730 0.099 Uiso calc R 1 . .
C C29 0.22233(16) 0.9526(3) -0.0500(5) 0.0910(14) Uani d . 1 . .
H H29 0.2141 1.0192 -0.0923 0.109 Uiso calc R 1 . .
C C30 0.25681(15) 0.8972(4) -0.0860(4) 0.0827(12) Uani d . 1 . .
H H30 0.2719 0.9256 -0.1543 0.099 Uiso calc R 1 . .
C C31 0.26915(12) 0.7997(3) -0.0212(4) 0.0644(10) Uani d . 1 . .
H H31 0.2924 0.7624 -0.0474 0.077 Uiso calc R 1 . .
C C32 0.35415(10) 0.7850(2) 0.3844(3) 0.0427(7) Uani d . 1 . .
C C33 0.39264(11) 0.7851(3) 0.4903(3) 0.0525(8) Uani d . 1 . .
H H33 0.3992 0.7256 0.5513 0.063 Uiso calc R 1 . .
C C34 0.42113(12) 0.8708(3) 0.5068(4) 0.0656(10) Uani d . 1 . .
H H34 0.4466 0.8688 0.5787 0.079 Uiso calc R 1 . .
C C35 0.41234(14) 0.9586(3) 0.4187(5) 0.0741(12) Uani d . 1 . .
H H35 0.4318 1.0164 0.4298 0.089 Uiso calc R 1 . .
C C36 0.37464(15) 0.9612(3) 0.3134(5) 0.0749(11) Uani d . 1 . .
H H36 0.3686 1.0211 0.2528 0.090 Uiso calc R 1 . .
C C37 0.34551(13) 0.8754(2) 0.2963(4) 0.0597(9) Uani d . 1 . .
H H37 0.3199 0.8785 0.2249 0.072 Uiso calc R 1 . .
C C38 0.33837(10) 0.5885(2) 0.1586(3) 0.0439(7) Uani d . 1 . .
C C39 0.38335(10) 0.5695(3) 0.2533(3) 0.0506(8) Uani d . 1 . .
H H39A 0.3802 0.5288 0.3395 0.061 Uiso calc R 1 . .
H H39B 0.3967 0.6382 0.2856 0.061 Uiso calc R 1 . .
C C40 0.29396(13) 0.7496(4) 0.5967(4) 0.0788(12) Uani d . 1 . .
H H40A 0.3109 0.6916 0.6477 0.118 Uiso calc R 1 . .
H H40B 0.2677 0.7594 0.6349 0.118 Uiso calc R 1 . .
H H40C 0.3110 0.8146 0.6098 0.118 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 N1 C3 . . 117.4(3) ?
C18 N1 C4 . . 122.9(2) ?
C3 N1 C4 . . 118.7(2) ?
C38 N2 C25 . . 117.2(2) ?
C38 N2 C21 . . 121.6(2) ?
C25 N2 C21 . . 119.9(2) ?
O1 C1 C2 . . 122.1(3) ?
O1 C1 C5 . . 122.0(3) ?
C2 C1 C5 . . 116.0(3) ?
C1 C2 C3 . . 113.0(3) ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
N1 C3 C6 . . 113.0(3) ?
N1 C3 C2 . . 107.3(3) ?
C6 C3 C2 . . 116.3(3) ?
N1 C3 H3 . . 106.6 ?
C6 C3 H3 . . 106.6 ?
C2 C3 H3 . . 106.6 ?
N1 C4 C12 . . 112.0(2) ?
N1 C4 C5 . . 111.4(2) ?
C12 C4 C5 . . 110.3(2) ?
N1 C4 H4 . . 107.6 ?
C12 C4 H4 . . 107.6 ?
C5 C4 H4 . . 107.6 ?
C20 C5 C1 . . 112.7(3) ?
C20 C5 C4 . . 112.1(3) ?
C1 C5 C4 . . 110.3(2) ?
C20 C5 H5 . . 107.1 ?
C1 C5 H5 . . 107.1 ?
C4 C5 H5 . . 107.1 ?
C11 C6 C7 . . 117.0(3) ?
C11 C6 C3 . . 118.8(3) ?
C7 C6 C3 . . 124.2(3) ?
C8 C7 C6 . . 121.5(3) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C9 C8 C7 . . 119.9(3) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C8 C9 C10 . . 119.9(4) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C9 C10 C11 . . 119.5(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C10 C11 C6 . . 122.1(3) ?
C10 C11 H11 . . 118.9 ?
C6 C11 H11 . . 118.9 ?
C13 C12 C17 . . 118.3(3) ?
C13 C12 C4 . . 121.4(3) ?
C17 C12 C4 . . 120.3(3) ?
C12 C13 C14 . . 119.9(4) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C15 C14 C13 . . 120.1(3) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 C14 . . 120.0(4) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.4(4) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C16 C17 C12 . . 121.2(3) ?
C16 C17 H17 . . 119.4 ?
C12 C17 H17 . . 119.4 ?
O2 C18 N1 . . 123.6(3) ?
O2 C18 C19 . . 121.4(3) ?
N1 C18 C19 . . 115.1(3) ?
C18 C19 Cl1 . . 112.2(2) ?
C18 C19 H19A . . 109.2 ?
Cl1 C19 H19A . . 109.2 ?
C18 C19 H19B . . 109.2 ?
Cl1 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
C5 C20 H20A . . 109.5 ?
C5 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C5 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N2 C21 C32 . . 113.1(2) ?
N2 C21 C22 . . 111.3(2) ?
C32 C21 C22 . . 109.9(2) ?
N2 C21 H21 . . 107.4 ?
C32 C21 H21 . . 107.4 ?
C22 C21 H21 . . 107.4 ?
C23 C22 C40 . . 111.8(3) ?
C23 C22 C21 . . 111.2(2) ?
C40 C22 C21 . . 111.4(3) ?
C23 C22 H22 . . 107.4 ?
C40 C22 H22 . . 107.4 ?
C21 C22 H22 . . 107.4 ?
O3 C23 C24 . . 121.7(3) ?
O3 C23 C22 . . 122.3(3) ?
C24 C23 C22 . . 116.0(3) ?
C23 C24 C25 . . 114.3(3) ?
C23 C24 H24A . . 108.7 ?
C25 C24 H24A . . 108.7 ?
C23 C24 H24B . . 108.7 ?
C25 C24 H24B . . 108.7 ?
H24A C24 H24B . . 107.6 ?
N2 C25 C26 . . 112.6(2) ?
N2 C25 C24 . . 107.9(2) ?
C26 C25 C24 . . 117.7(3) ?
N2 C25 H25 . . 105.9 ?
C26 C25 H25 . . 105.9 ?
C24 C25 H25 . . 105.9 ?
C27 C26 C31 . . 117.4(3) ?
C27 C26 C25 . . 124.0(3) ?
C31 C26 C25 . . 118.5(3) ?
C26 C27 C28 . . 121.1(3) ?
C26 C27 H27 . . 119.5 ?
C28 C27 H27 . . 119.5 ?
C29 C28 C27 . . 120.5(4) ?
C29 C28 H28 . . 119.7 ?
C27 C28 H28 . . 119.7 ?
C30 C29 C28 . . 119.3(4) ?
C30 C29 H29 . . 120.3 ?
C28 C29 H29 . . 120.3 ?
C29 C30 C31 . . 119.9(4) ?
C29 C30 H30 . . 120.0 ?
C31 C30 H30 . . 120.0 ?
C30 C31 C26 . . 121.8(3) ?
C30 C31 H31 . . 119.1 ?
C26 C31 H31 . . 119.1 ?
C37 C32 C33 . . 117.3(3) ?
C37 C32 C21 . . 122.4(3) ?
C33 C32 C21 . . 120.2(3) ?
C34 C33 C32 . . 121.6(3) ?
C34 C33 H33 . . 119.2 ?
C32 C33 H33 . . 119.2 ?
C35 C34 C33 . . 120.4(4) ?
C35 C34 H34 . . 119.8 ?
C33 C34 H34 . . 119.8 ?
C34 C35 C36 . . 119.5(3) ?
C34 C35 H35 . . 120.3 ?
C36 C35 H35 . . 120.3 ?
C35 C36 C37 . . 120.6(4) ?
C35 C36 H36 . . 119.7 ?
C37 C36 H36 . . 119.7 ?
C32 C37 C36 . . 120.6(4) ?
C32 C37 H37 . . 119.7 ?
C36 C37 H37 . . 119.7 ?
O4 C38 N2 . . 122.5(3) ?
O4 C38 C39 . . 121.7(3) ?
N2 C38 C39 . . 115.8(3) ?
C38 C39 Cl2 . . 111.4(2) ?
C38 C39 H39A . . 109.3 ?
Cl2 C39 H39A . . 109.3 ?
C38 C39 H39B . . 109.3 ?
Cl2 C39 H39B . . 109.3 ?
H39A C39 H39B . . 108.0 ?
C22 C40 H40A . . 109.5 ?
C22 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C22 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C19 . 1.771(3) ?
Cl2 C39 . 1.769(3) ?
O1 C1 . 1.208(3) ?
O2 C18 . 1.221(4) ?
O3 C23 . 1.198(3) ?
O4 C38 . 1.224(3) ?
N1 C18 . 1.360(4) ?
N1 C3 . 1.480(4) ?
N1 C4 . 1.489(4) ?
N2 C38 . 1.368(3) ?
N2 C25 . 1.475(4) ?
N2 C21 . 1.489(3) ?
C1 C2 . 1.491(5) ?
C1 C5 . 1.520(4) ?
C2 C3 . 1.520(4) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C6 . 1.513(4) ?
C3 H3 . 0.98 ?
C4 C12 . 1.526(4) ?
C4 C5 . 1.546(4) ?
C4 H4 . 0.98 ?
C5 C20 . 1.517(4) ?
C5 H5 . 0.98 ?
C6 C11 . 1.375(4) ?
C6 C7 . 1.384(4) ?
C7 C8 . 1.375(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.365(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.371(5) ?
C9 H9 . 0.93 ?
C10 C11 . 1.372(5) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 C13 . 1.377(4) ?
C12 C17 . 1.386(4) ?
C13 C14 . 1.394(5) ?
C13 H13 . 0.93 ?
C14 C15 . 1.369(5) ?
C14 H14 . 0.93 ?
C15 C16 . 1.354(5) ?
C15 H15 . 0.93 ?
C16 C17 . 1.366(5) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 C19 . 1.522(4) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 C32 . 1.518(4) ?
C21 C22 . 1.543(4) ?
C21 H21 . 0.98 ?
C22 C23 . 1.510(4) ?
C22 C40 . 1.521(4) ?
C22 H22 . 0.98 ?
C23 C24 . 1.496(4) ?
C24 C25 . 1.534(4) ?
C24 H24A . 0.97 ?
C24 H24B . 0.97 ?
C25 C26 . 1.511(4) ?
C25 H25 . 0.98 ?
C26 C27 . 1.376(4) ?
C26 C31 . 1.387(4) ?
C27 C28 . 1.379(5) ?
C27 H27 . 0.93 ?
C28 C29 . 1.373(6) ?
C28 H28 . 0.93 ?
C29 C30 . 1.368(5) ?
C29 H29 . 0.93 ?
C30 C31 . 1.373(5) ?
C30 H30 . 0.93 ?
C31 H31 . 0.93 ?
C32 C37 . 1.385(4) ?
C32 C33 . 1.390(4) ?
C33 C34 . 1.373(4) ?
C33 H33 . 0.93 ?
C34 C35 . 1.360(5) ?
C34 H34 . 0.93 ?
C35 C36 . 1.370(5) ?
C35 H35 . 0.93 ?
C36 C37 . 1.386(5) ?
C36 H36 . 0.93 ?
C37 H37 . 0.93 ?
C38 C39 . 1.515(4) ?
C39 H39A . 0.97 ?
C39 H39B . 0.97 ?
C40 H40A . 0.96 ?
C40 H40B . 0.96 ?
C40 H40C . 0.96 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -166.7(3) ?
C5 C1 C2 C3 . . . . 13.7(4) ?
C18 N1 C3 C6 . . . . 109.4(3) ?
C4 N1 C3 C6 . . . . -81.7(3) ?
C18 N1 C3 C2 . . . . -121.1(3) ?
C4 N1 C3 C2 . . . . 47.8(3) ?
C1 C2 C3 N1 . . . . -57.4(3) ?
C1 C2 C3 C6 . . . . 70.2(4) ?
C18 N1 C4 C12 . . . . -62.3(3) ?
C3 N1 C4 C12 . . . . 129.4(3) ?
C18 N1 C4 C5 . . . . 173.6(3) ?
C3 N1 C4 C5 . . . . 5.3(3) ?
O1 C1 C5 C20 . . . . -13.2(4) ?
C2 C1 C5 C20 . . . . 166.4(3) ?
O1 C1 C5 C4 . . . . -139.4(3) ?
C2 C1 C5 C4 . . . . 40.2(4) ?
N1 C4 C5 C20 . . . . -176.3(3) ?
C12 C4 C5 C20 . . . . 58.6(3) ?
N1 C4 C5 C1 . . . . -49.8(3) ?
C12 C4 C5 C1 . . . . -174.9(2) ?
N1 C3 C6 C11 . . . . -51.3(4) ?
C2 C3 C6 C11 . . . . -176.0(3) ?
N1 C3 C6 C7 . . . . 129.2(3) ?
C2 C3 C6 C7 . . . . 4.5(4) ?
C11 C6 C7 C8 . . . . 1.8(5) ?
C3 C6 C7 C8 . . . . -178.7(3) ?
C6 C7 C8 C9 . . . . 0.2(5) ?
C7 C8 C9 C10 . . . . -1.8(5) ?
C8 C9 C10 C11 . . . . 1.4(6) ?
C9 C10 C11 C6 . . . . 0.7(6) ?
C7 C6 C11 C10 . . . . -2.2(5) ?
C3 C6 C11 C10 . . . . 178.3(3) ?
N1 C4 C12 C13 . . . . -50.8(4) ?
C5 C4 C12 C13 . . . . 74.0(3) ?
N1 C4 C12 C17 . . . . 129.3(3) ?
C5 C4 C12 C17 . . . . -105.9(3) ?
C17 C12 C13 C14 . . . . -1.3(5) ?
C4 C12 C13 C14 . . . . 178.8(3) ?
C12 C13 C14 C15 . . . . 0.3(5) ?
C13 C14 C15 C16 . . . . 0.3(5) ?
C14 C15 C16 C17 . . . . 0.1(5) ?
C15 C16 C17 C12 . . . . -1.1(5) ?
C13 C12 C17 C16 . . . . 1.8(4) ?
C4 C12 C17 C16 . . . . -178.3(3) ?
C3 N1 C18 O2 . . . . -14.2(4) ?
C4 N1 C18 O2 . . . . 177.4(3) ?
C3 N1 C18 C19 . . . . 164.4(3) ?
C4 N1 C18 C19 . . . . -4.0(4) ?
O2 C18 C19 Cl1 . . . . 4.6(4) ?
N1 C18 C19 Cl1 . . . . -174.0(2) ?
C38 N2 C21 C32 . . . . 73.0(3) ?
C25 N2 C21 C32 . . . . -120.2(3) ?
C38 N2 C21 C22 . . . . -162.7(2) ?
C25 N2 C21 C22 . . . . 4.1(3) ?
N2 C21 C22 C23 . . . . 45.2(3) ?
C32 C21 C22 C23 . . . . 171.3(3) ?
N2 C21 C22 C40 . . . . 170.7(3) ?
C32 C21 C22 C40 . . . . -63.2(3) ?
C40 C22 C23 O3 . . . . 7.8(5) ?
C21 C22 C23 O3 . . . . 133.1(3) ?
C40 C22 C23 C24 . . . . -172.2(3) ?
C21 C22 C23 C24 . . . . -46.9(4) ?
O3 C23 C24 C25 . . . . 178.8(3) ?
C22 C23 C24 C25 . . . . -1.2(4) ?
C38 N2 C25 C26 . . . . -111.9(3) ?
C21 N2 C25 C26 . . . . 80.7(3) ?
C38 N2 C25 C24 . . . . 116.5(3) ?
C21 N2 C25 C24 . . . . -50.8(3) ?
C23 C24 C25 N2 . . . . 48.3(3) ?
C23 C24 C25 C26 . . . . -80.4(4) ?
N2 C25 C26 C27 . . . . -124.2(3) ?
C24 C25 C26 C27 . . . . 2.3(4) ?
N2 C25 C26 C31 . . . . 59.0(4) ?
C24 C25 C26 C31 . . . . -174.5(3) ?
C31 C26 C27 C28 . . . . -2.2(5) ?
C25 C26 C27 C28 . . . . -179.0(3) ?
C26 C27 C28 C29 . . . . 0.5(6) ?
C27 C28 C29 C30 . . . . 1.1(7) ?
C28 C29 C30 C31 . . . . -1.0(7) ?
C29 C30 C31 C26 . . . . -0.7(6) ?
C27 C26 C31 C30 . . . . 2.3(5) ?
C25 C26 C31 C30 . . . . 179.3(3) ?
N2 C21 C32 C37 . . . . 53.2(4) ?
C22 C21 C32 C37 . . . . -71.8(4) ?
N2 C21 C32 C33 . . . . -129.5(3) ?
C22 C21 C32 C33 . . . . 105.5(3) ?
C37 C32 C33 C34 . . . . -0.3(4) ?
C21 C32 C33 C34 . . . . -177.7(3) ?
C32 C33 C34 C35 . . . . -0.2(5) ?
C33 C34 C35 C36 . . . . 0.3(5) ?
C34 C35 C36 C37 . . . . 0.1(6) ?
C33 C32 C37 C36 . . . . 0.7(5) ?
C21 C32 C37 C36 . . . . 178.0(3) ?
C35 C36 C37 C32 . . . . -0.6(6) ?
C25 N2 C38 O4 . . . . 12.3(4) ?
C21 N2 C38 O4 . . . . 179.5(3) ?
C25 N2 C38 C39 . . . . -166.5(2) ?
C21 N2 C38 C39 . . . . 0.6(4) ?
O4 C38 C39 Cl2 . . . . 4.0(4) ?
N2 C38 C39 Cl2 . . . . -177.1(2) ?
