#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221356.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_2221356
loop_
_publ_author_name
'Parthiban, P.'
'Ramkumar, V.'
'Santan, H. D.'
'Kim, Jong Tae'
'Jeong, Yeon Tae'
_publ_section_title
;
 2,4-Bis(3-chlorophenyl)-3-azabicyclo[3.3.1]nonan-9-one
;
_journal_coeditor_code           GW2060
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o840
_journal_paper_doi               10.1107/S1600536809009945
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H19 Cl2 N O'
_chemical_formula_moiety         'C20 H19 Cl2 N O'
_chemical_formula_sum            'C20 H19 Cl2 N O'
_chemical_formula_weight         360.26
_chemical_name_systematic
;
2,4-Bis(3-chlorophenyl)-3-azabicyclo[3.3.1]nonan-9-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9950(14)
_cell_length_b                   12.180(2)
_cell_length_c                   20.770(4)
_cell_measurement_reflns_used    5421
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.53
_cell_measurement_theta_min      2.55
_cell_volume                     1769.6(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23614
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.9224
_exptl_absorpt_correction_T_min  0.8751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.246
_refine_ls_abs_structure_details 'Flack (1983), 1756 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0341P)²+0.181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                2762
_reflns_number_total             4284
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2060.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2221356
_cod_database_fobs_code          2221356
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C C1 0.1155(3) 0.91094(15) 0.96470(9) 0.0351(5) Uani d . 1 . .
H H1 0.0839 0.8690 1.0035 0.042 Uiso calc R 1 . .
C C2 -0.0754(3) 0.94712(17) 0.93253(10) 0.0425(5) Uani d . 1 . .
H H2 -0.1483 0.9910 0.9635 0.051 Uiso calc R 1 . .
C C3 -0.0574(3) 1.01301(18) 0.86920(11) 0.0522(6) Uani d . 1 . .
H H3A -0.1829 1.0398 0.8571 0.063 Uiso calc R 1 . .
H H3B 0.0236 1.0763 0.8768 0.063 Uiso calc R 1 . .
C C4 0.0248(4) 0.94740(18) 0.81344(10) 0.0517(6) Uani d . 1 . .
H H4A 0.0035 0.9874 0.7737 0.062 Uiso calc R 1 . .
H H4B 0.1617 0.9400 0.8193 0.062 Uiso calc R 1 . .
C C5 -0.0633(3) 0.83391(19) 0.80751(10) 0.0493(6) Uani d . 1 . .
H H5A 0.0141 0.7906 0.7782 0.059 Uiso calc R 1 . .
H H5B -0.1894 0.8411 0.7886 0.059 Uiso calc R 1 . .
C C6 -0.0815(3) 0.77124(16) 0.87165(10) 0.0405(5) Uani d . 1 . .
H H6 -0.1583 0.7050 0.8646 0.049 Uiso calc R 1 . .
C C7 0.1088(3) 0.73829(16) 0.90524(9) 0.0373(5) Uani d . 1 . .
H H7 0.0767 0.7017 0.9459 0.045 Uiso calc R 1 . .
C C8 -0.1852(3) 0.84501(17) 0.91799(9) 0.0417(5) Uani d . 1 . .
C C9 0.2390(3) 1.00628(15) 0.98456(9) 0.0353(5) Uani d . 1 . .
C C10 0.3661(3) 1.05578(17) 0.94271(10) 0.0485(6) Uani d . 1 . .
H H10 0.3780 1.0292 0.9009 0.058 Uiso calc R 1 . .
C C11 0.4763(4) 1.14476(18) 0.96219(12) 0.0589(7) Uani d . 1 . .
H H11 0.5609 1.1773 0.9334 0.071 Uiso calc R 1 . .
C C12 0.4608(3) 1.18510(18) 1.02405(11) 0.0514(6) Uani d . 1 . .
H H12 0.5330 1.2452 1.0372 0.062 Uiso calc R 1 . .
C C13 0.3367(3) 1.13481(15) 1.06568(10) 0.0430(5) Uani d . 1 . .
C C14 0.2249(3) 1.04678(16) 1.04695(9) 0.0399(5) Uani d . 1 . .
H H14 0.1404 1.0148 1.0760 0.048 Uiso calc R 1 . .
C C15 0.2255(3) 0.65933(15) 0.86531(10) 0.0388(5) Uani d . 1 . .
C C16 0.2048(3) 0.54727(17) 0.87560(12) 0.0543(6) Uani d . 1 . .
H H16 0.1230 0.5222 0.9077 0.065 Uiso calc R 1 . .
C C17 0.3056(4) 0.47232(18) 0.83825(15) 0.0679(8) Uani d . 1 . .
H H17 0.2895 0.3975 0.8453 0.081 Uiso calc R 1 . .
C C18 0.4283(4) 0.5073(2) 0.79115(13) 0.0619(7) Uani d . 1 . .
H H18 0.4961 0.4570 0.7664 0.074 Uiso calc R 1 . .
C C19 0.4494(3) 0.61781(19) 0.78124(12) 0.0514(6) Uani d . 1 . .
C C20 0.3510(3) 0.69381(17) 0.81787(10) 0.0457(5) Uani d . 1 . .
H H20 0.3692 0.7684 0.8106 0.055 Uiso calc R 1 . .
Cl Cl1 0.32230(11) 1.18133(5) 1.14500(3) 0.0681(2) Uani d . 1 . .
Cl Cl2 0.60281(11) 0.66335(6) 0.72080(3) 0.0794(2) Uani d . 1 . .
N N1 0.2172(3) 0.83753(13) 0.92051(8) 0.0358(4) Uani d . 1 . .
O O1 -0.3405(2) 0.82264(14) 0.94107(7) 0.0583(4) Uani d . 1 . .
H H1A 0.324(3) 0.8184(15) 0.9342(9) 0.033(6) Uiso d . 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
N1 C1 C9 . . 111.35(16) ?
N1 C1 C2 . . 108.66(16) ?
C9 C1 C2 . . 113.05(16) ?
N1 C1 H1 . . 107.9 ?
C9 C1 H1 . . 107.9 ?
C2 C1 H1 . . 107.9 ?
C8 C2 C3 . . 107.59(18) ?
C8 C2 C1 . . 107.01(16) ?
C3 C2 C1 . . 116.25(17) ?
C8 C2 H2 . . 108.6 ?
C3 C2 H2 . . 108.6 ?
C1 C2 H2 . . 108.6 ?
C4 C3 C2 . . 113.96(17) ?
C4 C3 H3A . . 108.8 ?
C2 C3 H3A . . 108.8 ?
C4 C3 H3B . . 108.8 ?
C2 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
C5 C4 C3 . . 112.78(19) ?
C5 C4 H4A . . 109.0 ?
C3 C4 H4A . . 109.0 ?
C5 C4 H4B . . 109.0 ?
C3 C4 H4B . . 109.0 ?
H4A C4 H4B . . 107.8 ?
C4 C5 C6 . . 114.49(17) ?
C4 C5 H5A . . 108.6 ?
C6 C5 H5A . . 108.6 ?
C4 C5 H5B . . 108.6 ?
C6 C5 H5B . . 108.6 ?
H5A C5 H5B . . 107.6 ?
C8 C6 C5 . . 107.32(17) ?
C8 C6 C7 . . 106.25(16) ?
C5 C6 C7 . . 116.39(17) ?
C8 C6 H6 . . 108.9 ?
C5 C6 H6 . . 108.9 ?
C7 C6 H6 . . 108.9 ?
N1 C7 C15 . . 111.44(16) ?
N1 C7 C6 . . 109.14(16) ?
C15 C7 C6 . . 112.37(16) ?
N1 C7 H7 . . 107.9 ?
C15 C7 H7 . . 107.9 ?
C6 C7 H7 . . 107.9 ?
O1 C8 C2 . . 124.5(2) ?
O1 C8 C6 . . 123.3(2) ?
C2 C8 C6 . . 112.28(17) ?
C10 C9 C14 . . 118.52(19) ?
C10 C9 C1 . . 122.25(18) ?
C14 C9 C1 . . 119.23(18) ?
C9 C10 C11 . . 120.9(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C12 C11 C10 . . 120.3(2) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C13 C12 C11 . . 118.6(2) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
C12 C13 C14 . . 121.8(2) ?
C12 C13 Cl1 . . 119.18(17) ?
C14 C13 Cl1 . . 118.97(16) ?
C13 C14 C9 . . 119.79(19) ?
C13 C14 H14 . . 120.1 ?
C9 C14 H14 . . 120.1 ?
C16 C15 C20 . . 118.3(2) ?
C16 C15 C7 . . 119.01(19) ?
C20 C15 C7 . . 122.72(18) ?
C15 C16 C17 . . 120.4(2) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C18 C17 C16 . . 120.8(2) ?
C18 C17 H17 . . 119.6 ?
C16 C17 H17 . . 119.6 ?
C19 C18 C17 . . 118.7(2) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C18 C19 C20 . . 121.5(2) ?
C18 C19 Cl2 . . 119.17(19) ?
C20 C19 Cl2 . . 119.36(18) ?
C19 C20 C15 . . 120.3(2) ?
C19 C20 H20 . . 119.9 ?
C15 C20 H20 . . 119.9 ?
C7 N1 C1 . . 112.88(15) ?
C7 N1 H1A . . 108.0(14) ?
C1 N1 H1A . . 113.0(14) ?
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
C1 N1 . 1.465(2) ?
C1 C9 . 1.505(3) ?
C1 C2 . 1.557(3) ?
C1 H1 . 0.9800 ?
C2 C8 . 1.493(3) ?
C2 C3 . 1.546(3) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.520(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.518(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.541(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C8 . 1.503(3) ?
C6 C7 . 1.556(3) ?
C6 H6 . 0.9800 ?
C7 N1 . 1.462(3) ?
C7 C15 . 1.510(3) ?
C7 H7 . 0.9800 ?
C8 O1 . 1.218(2) ?
C9 C10 . 1.382(3) ?
C9 C14 . 1.390(3) ?
C10 C11 . 1.390(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.369(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.383(3) ?
C13 Cl1 . 1.745(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.389(3) ?
C15 C20 . 1.385(3) ?
C16 C17 . 1.390(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.370(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.369(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.382(3) ?
C19 Cl2 . 1.742(3) ?
C20 H20 . 0.9300 ?
N1 H1A . 0.83(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 1_655 0.83(2) 2.35(2) 3.129(3) 155.4(18)
C7 H7 O1 4_567 0.98 2.44 3.296(2) 146
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
N1 C1 C2 C8 . . . . 58.1(2) ?
C9 C1 C2 C8 . . . . -177.77(16) ?
N1 C1 C2 C3 . . . . -62.1(2) ?
C9 C1 C2 C3 . . . . 62.0(2) ?
C8 C2 C3 C4 . . . . -53.3(2) ?
C1 C2 C3 C4 . . . . 66.6(3) ?
C2 C3 C4 C5 . . . . 45.2(3) ?
C3 C4 C5 C6 . . . . -45.3(3) ?
C4 C5 C6 C8 . . . . 52.9(2) ?
C4 C5 C6 C7 . . . . -65.9(2) ?
C8 C6 C7 N1 . . . . -58.4(2) ?
C5 C6 C7 N1 . . . . 60.9(2) ?
C8 C6 C7 C15 . . . . 177.42(16) ?
C5 C6 C7 C15 . . . . -63.2(2) ?
C3 C2 C8 O1 . . . . -116.6(2) ?
C1 C2 C8 O1 . . . . 117.8(2) ?
C3 C2 C8 C6 . . . . 63.9(2) ?
C1 C2 C8 C6 . . . . -61.7(2) ?
C5 C6 C8 O1 . . . . 117.0(2) ?
C7 C6 C8 O1 . . . . -117.9(2) ?
C5 C6 C8 C2 . . . . -63.6(2) ?
C7 C6 C8 C2 . . . . 61.6(2) ?
N1 C1 C9 C10 . . . . 36.4(3) ?
C2 C1 C9 C10 . . . . -86.3(2) ?
N1 C1 C9 C14 . . . . -143.97(18) ?
C2 C1 C9 C14 . . . . 93.4(2) ?
C14 C9 C10 C11 . . . . -0.6(3) ?
C1 C9 C10 C11 . . . . 179.1(2) ?
C9 C10 C11 C12 . . . . 0.2(4) ?
C10 C11 C12 C13 . . . . 0.8(4) ?
C11 C12 C13 C14 . . . . -1.3(3) ?
C11 C12 C13 Cl1 . . . . 177.49(19) ?
C12 C13 C14 C9 . . . . 0.9(3) ?
Cl1 C13 C14 C9 . . . . -177.89(16) ?
C10 C9 C14 C13 . . . . 0.0(3) ?
C1 C9 C14 C13 . . . . -179.61(17) ?
N1 C7 C15 C16 . . . . 143.69(19) ?
C6 C7 C15 C16 . . . . -93.5(2) ?
N1 C7 C15 C20 . . . . -37.3(3) ?
C6 C7 C15 C20 . . . . 85.5(2) ?
C20 C15 C16 C17 . . . . -1.1(3) ?
C7 C15 C16 C17 . . . . 177.9(2) ?
C15 C16 C17 C18 . . . . 0.7(4) ?
C16 C17 C18 C19 . . . . -0.3(4) ?
C17 C18 C19 C20 . . . . 0.5(4) ?
C17 C18 C19 Cl2 . . . . -179.20(19) ?
C18 C19 C20 C15 . . . . -1.0(4) ?
Cl2 C19 C20 C15 . . . . 178.72(16) ?
C16 C15 C20 C19 . . . . 1.3(3) ?
C7 C15 C20 C19 . . . . -177.8(2) ?
C15 C7 N1 C1 . . . . -174.09(16) ?
C6 C7 N1 C1 . . . . 61.2(2) ?
C9 C1 N1 C7 . . . . 174.24(16) ?
C2 C1 N1 C7 . . . . -60.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741994
