#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151215.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151215
loop_
_publ_author_name
'Clayden, Jonathan'
'Vallverdú, Lluís'
'Helliwell, Madeleine'
_publ_section_title
;
 Conformational communication between the Ar-CO and Ar-N axes in
 2,2'-disubstituted benzanilides and their derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2106
_journal_page_last               2118
_journal_paper_doi               10.1039/b602912d
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C20 H14 I3 N O'
_chemical_formula_weight         665.02
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            8
_cell_length_a                   17.2130(10)
_cell_length_b                   14.9120(8)
_cell_length_c                   15.6580(9)
_cell_measurement_reflns_used    input
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2835
_cell_measurement_theta_min      2.6045
_cell_volume                     4019.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33041
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    4.674
_exptl_absorpt_correction_T_max  0.4550
_exptl_absorpt_correction_T_min  0.2915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    2.198
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.980
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0237
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0261P)²+9.1515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                4675
_reflns_number_total             4886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b602912d.txt
_cod_data_source_block           s2186na
_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 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7151215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66108(16) 0.15937(19) 0.96707(16) 0.0137(5) Uani 1 1 d . . .
C2 C 0.69037(16) 0.07193(19) 0.96855(17) 0.0153(5) Uani 1 1 d . . .
C3 C 0.76975(17) 0.0567(2) 0.97735(19) 0.0201(6) Uani 1 1 d . . .
H3 H 0.7895 -0.0028 0.9773 0.024 Uiso 1 1 calc R . .
C4 C 0.81978(17) 0.1292(2) 0.9862(2) 0.0210(6) Uani 1 1 d . . .
H4 H 0.8740 0.1192 0.9924 0.025 Uiso 1 1 calc R . .
C5 C 0.79101(17) 0.2162(2) 0.98591(18) 0.0188(6) Uani 1 1 d . . .
H5 H 0.8254 0.2655 0.9930 0.023 Uiso 1 1 calc R . .
C6 C 0.71220(16) 0.23113(19) 0.97529(17) 0.0163(5) Uani 1 1 d . . .
H6 H 0.6929 0.2908 0.9736 0.020 Uiso 1 1 calc R . .
C7 C 0.55250(17) 0.1742(2) 0.86438(18) 0.0184(6) Uani 1 1 d . . .
H7A H 0.4953 0.1815 0.8631 0.022 Uiso 1 1 calc R . .
H7B H 0.5653 0.1155 0.8384 0.022 Uiso 1 1 calc R . .
C8 C 0.59022(18) 0.2484(2) 0.81341(18) 0.0198(6) Uani 1 1 d . . .
C9 C 0.64867(18) 0.2357(2) 0.75321(19) 0.0215(6) Uani 1 1 d . . .
C10 C 0.6846(2) 0.3075(2) 0.7120(2) 0.0276(7) Uani 1 1 d . . .
H10 H 0.7243 0.2973 0.6711 0.033 Uiso 1 1 calc R . .
C11 C 0.6613(2) 0.3942(2) 0.7318(2) 0.0335(8) Uani 1 1 d . . .
H11 H 0.6851 0.4439 0.7043 0.040 Uiso 1 1 calc R . .
C12 C 0.6036(2) 0.4077(2) 0.7915(3) 0.0341(8) Uani 1 1 d . . .
H12 H 0.5882 0.4671 0.8054 0.041 Uiso 1 1 calc R . .
C13 C 0.5681(2) 0.3364(2) 0.8311(2) 0.0271(7) Uani 1 1 d . . .
H13 H 0.5278 0.3473 0.8712 0.033 Uiso 1 1 calc R . .
C14 C 0.53328(16) 0.21090(18) 1.01561(18) 0.0149(5) Uani 1 1 d . . .
C15 C 0.56647(15) 0.2158(2) 1.10425(18) 0.0153(5) Uani 1 1 d . . .
C16 C 0.57571(16) 0.29743(19) 1.14622(19) 0.0178(5) Uani 1 1 d . . .
C17 C 0.60014(19) 0.3006(2) 1.2312(2) 0.0237(6) Uani 1 1 d . . .
H17 H 0.6071 0.3567 1.2590 0.028 Uiso 1 1 calc R . .
C18 C 0.61398(19) 0.2217(2) 1.2745(2) 0.0262(7) Uani 1 1 d . . .
H18 H 0.6300 0.2235 1.3326 0.031 Uiso 1 1 calc R . .
C19 C 0.60475(19) 0.1396(2) 1.2340(2) 0.0248(6) Uani 1 1 d . . .
H19 H 0.6142 0.0855 1.2642 0.030 Uiso 1 1 calc R . .
C20 C 0.58158(17) 0.1370(2) 1.14921(18) 0.0187(5) Uani 1 1 d . . .
H20 H 0.5759 0.0808 1.1214 0.022 Uiso 1 1 calc R . .
I1 I 0.616484(11) -0.039195(12) 0.962300(12) 0.01879(6) Uani 1 1 d . . .
I2 I 0.687428(14) 0.107799(16) 0.718615(15) 0.03325(7) Uani 1 1 d . . .
I3 I 0.555874(12) 0.420112(13) 1.083930(14) 0.02372(6) Uani 1 1 d . . .
N1 N 0.57999(14) 0.17608(16) 0.95376(14) 0.0144(4) Uani 1 1 d . . .
O1 O 0.46630(12) 0.23373(15) 1.00222(14) 0.0220(4) Uani 1 1 d . . .
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'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.2(3) . . ?
C6 C1 N1 119.7(2) . . ?
C2 C1 N1 121.0(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 I1 118.2(2) . . ?
C1 C2 I1 121.3(2) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C8 110.4(2) . . ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C13 117.4(3) . . ?
C9 C8 C7 124.6(3) . . ?
C13 C8 C7 117.9(3) . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 I2 122.1(2) . . ?
C10 C9 I2 116.1(2) . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
O1 C14 N1 122.8(3) . . ?
O1 C14 C15 120.3(3) . . ?
N1 C14 C15 116.8(2) . . ?
C16 C15 C20 118.5(3) . . ?
C16 C15 C14 121.5(3) . . ?
C20 C15 C14 119.7(3) . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 I3 121.6(2) . . ?
C17 C16 I3 117.5(2) . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C14 N1 C1 122.6(2) . . ?
C14 N1 C7 119.5(2) . . ?
C1 N1 C7 116.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.391(4) . ?
C1 C2 1.398(4) . ?
C1 N1 1.433(3) . ?
C2 C3 1.392(4) . ?
C2 I1 2.091(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.478(3) . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.392(4) . ?
C8 C13 1.394(5) . ?
C9 C10 1.395(5) . ?
C9 I2 2.091(3) . ?
C10 C11 1.387(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O1 1.220(3) . ?
C14 N1 1.362(4) . ?
C14 C15 1.503(4) . ?
C15 C16 1.392(4) . ?
C15 C20 1.395(4) . ?
C16 C17 1.397(4) . ?
C16 I3 2.101(3) . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(4) . . . . ?
N1 C1 C2 C3 176.8(3) . . . . ?
C6 C1 C2 I1 177.10(19) . . . . ?
N1 C1 C2 I1 -5.5(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
I1 C2 C3 C4 -176.6(2) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
N1 C1 C6 C5 -178.3(2) . . . . ?
N1 C7 C8 C9 106.2(3) . . . . ?
N1 C7 C8 C13 -70.1(3) . . . . ?
C13 C8 C9 C10 0.4(4) . . . . ?
C7 C8 C9 C10 -175.9(3) . . . . ?
C13 C8 C9 I2 -179.3(2) . . . . ?
C7 C8 C9 I2 4.4(4) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
I2 C9 C10 C11 179.7(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C12 C13 C8 1.2(6) . . . . ?
C9 C8 C13 C12 -1.0(5) . . . . ?
C7 C8 C13 C12 175.6(3) . . . . ?
O1 C14 C15 C16 -64.4(4) . . . . ?
N1 C14 C15 C16 118.8(3) . . . . ?
O1 C14 C15 C20 109.3(3) . . . . ?
N1 C14 C15 C20 -67.5(3) . . . . ?
C20 C15 C16 C17 0.5(4) . . . . ?
C14 C15 C16 C17 174.3(3) . . . . ?
C20 C15 C16 I3 179.2(2) . . . . ?
C14 C15 C16 I3 -7.0(4) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
I3 C16 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C18 C19 C20 C15 -0.8(5) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
C14 C15 C20 C19 -173.4(3) . . . . ?
O1 C14 N1 C1 172.4(3) . . . . ?
C15 C14 N1 C1 -10.9(4) . . . . ?
O1 C14 N1 C7 6.7(4) . . . . ?
C15 C14 N1 C7 -176.5(2) . . . . ?
C6 C1 N1 C14 -69.8(3) . . . . ?
C2 C1 N1 C14 112.8(3) . . . . ?
C6 C1 N1 C7 96.2(3) . . . . ?
C2 C1 N1 C7 -81.2(3) . . . . ?
C8 C7 N1 C14 102.6(3) . . . . ?
C8 C7 N1 C1 -63.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9867913
