#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151214.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_7151214
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 H15 I2 N O'
_chemical_formula_weight         539.13
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.4550(10)
_cell_angle_beta                 101.4960(10)
_cell_angle_gamma                106.2000(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0770(8)
_cell_length_b                   10.3330(9)
_cell_length_c                   10.9250(9)
_cell_measurement_reflns_used    input
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2615
_cell_measurement_theta_min      2.403
_cell_volume                     951.82(14)
_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 0.918
_diffrn_measured_fraction_theta_max 0.918
_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  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8260
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    3.310
_exptl_absorpt_correction_T_max  0.7331
_exptl_absorpt_correction_T_min  0.5573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0173
_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)+(0.0187P)²+0.6034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0438
_reflns_number_gt                4084
_reflns_number_total             4336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b602912d.txt
_cod_data_source_block           s2040ma
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7151214
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.6867(2) 0.26531(19) 0.24832(17) 0.0170(3) Uani 1 1 d . . .
C2 C 0.5936(2) 0.1490(2) 0.16307(18) 0.0193(4) Uani 1 1 d . . .
H2 H 0.6419 0.0981 0.1157 0.023 Uiso 1 1 calc R . .
C3 C 0.4309(2) 0.1067(2) 0.14662(19) 0.0226(4) Uani 1 1 d . . .
H3 H 0.3685 0.0249 0.0910 0.027 Uiso 1 1 calc R . .
C4 C 0.3594(2) 0.1840(2) 0.21137(19) 0.0228(4) Uani 1 1 d . . .
H4 H 0.2477 0.1569 0.1979 0.027 Uiso 1 1 calc R . .
C5 C 0.4508(2) 0.3004(2) 0.29549(18) 0.0194(4) Uani 1 1 d . . .
H5 H 0.4018 0.3535 0.3396 0.023 Uiso 1 1 calc R . .
C6 C 0.6145(2) 0.34027(18) 0.31585(17) 0.0176(4) Uani 1 1 d . . .
C7 C 0.8352(2) 0.4060(2) 0.0653(2) 0.0241(4) Uani 1 1 d . . .
C8 C 0.8503(3) 0.3096(2) -0.0244(2) 0.0346(5) Uani 1 1 d . . .
H8 H 0.9182 0.2565 -0.0004 0.042 Uiso 1 1 calc R . .
C9 C 0.7676(4) 0.2903(3) -0.1479(3) 0.0560(8) Uani 1 1 d . . .
H9 H 0.7786 0.2238 -0.2088 0.067 Uiso 1 1 calc R . .
C10 C 0.6686(4) 0.3668(5) -0.1840(3) 0.0719(12) Uani 1 1 d . . .
H10 H 0.6109 0.3525 -0.2694 0.086 Uiso 1 1 calc R . .
C11 C 0.6535(4) 0.4643(5) -0.0956(4) 0.0715(12) Uani 1 1 d . . .
H11 H 0.5861 0.5176 -0.1203 0.086 Uiso 1 1 calc R . .
C12 C 0.7372(3) 0.4840(3) 0.0294(3) 0.0441(7) Uani 1 1 d . . .
H12 H 0.7272 0.5511 0.0903 0.053 Uiso 1 1 calc R . .
C13 C 0.8650(2) 0.1140(2) 0.37035(18) 0.0190(4) Uani 1 1 d . . .
C14 C 0.8112(2) 0.1355(2) 0.47923(19) 0.0240(4) Uani 1 1 d . . .
H14 H 0.8263 0.2261 0.5179 0.029 Uiso 1 1 calc R . .
C15 C 0.7360(3) 0.0262(2) 0.5315(2) 0.0306(5) Uani 1 1 d . . .
H15 H 0.6994 0.0417 0.6055 0.037 Uiso 1 1 calc R . .
C16 C 0.7142(3) -0.1056(2) 0.4756(2) 0.0354(5) Uani 1 1 d . . .
H16 H 0.6622 -0.1806 0.5113 0.043 Uiso 1 1 calc R . .
C17 C 0.7676(3) -0.1293(2) 0.3683(2) 0.0298(5) Uani 1 1 d . . .
H17 H 0.7526 -0.2201 0.3303 0.036 Uiso 1 1 calc R . .
C18 C 0.8433(2) -0.0194(2) 0.31640(18) 0.0211(4) Uani 1 1 d . . .
C19 C 0.9468(2) 0.23423(19) 0.31542(18) 0.0189(4) Uani 1 1 d . . .
C20 C 0.9240(2) 0.4242(2) 0.2011(2) 0.0252(4) Uani 1 1 d . . .
H20A H 1.0360 0.4320 0.2042 0.030 Uiso 1 1 calc R . .
H20B H 0.9206 0.5097 0.2479 0.030 Uiso 1 1 calc R . .
I1 I 0.746497(14) 0.506406(12) 0.458577(12) 0.02124(4) Uani 1 1 d . . .
I2 I 0.913197(15) -0.063571(13) 0.149117(12) 0.02448(4) Uani 1 1 d . . .
N1 N 0.85497(18) 0.30757(16) 0.26254(16) 0.0189(3) Uani 1 1 d . . .
O1 O 1.08924(16) 0.26440(15) 0.32117(15) 0.0269(3) 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
C2 C1 C6 119.23(17) . . ?
C2 C1 N1 119.31(16) . . ?
C6 C1 N1 121.44(17) . . ?
C3 C2 C1 120.49(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.97(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.90(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.26(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.07(17) . . ?
C5 C6 I1 118.02(14) . . ?
C1 C6 I1 121.78(13) . . ?
C8 C7 C12 119.5(2) . . ?
C8 C7 C20 119.9(2) . . ?
C12 C7 C20 120.6(2) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.0(3) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C18 C13 C14 118.65(19) . . ?
C18 C13 C19 121.62(17) . . ?
C14 C13 C19 119.72(17) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 120.94(19) . . ?
C17 C18 I2 117.22(15) . . ?
C13 C18 I2 121.77(15) . . ?
O1 C19 N1 122.87(18) . . ?
O1 C19 C13 121.05(18) . . ?
N1 C19 C13 116.06(16) . . ?
N1 C20 C7 111.08(16) . . ?
N1 C20 H20A 109.4 . . ?
C7 C20 H20A 109.4 . . ?
N1 C20 H20B 109.4 . . ?
C7 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C19 N1 C1 122.13(16) . . ?
C19 N1 C20 119.82(16) . . ?
C1 N1 C20 117.51(16) . . ?
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 C2 1.390(3) . ?
C1 C6 1.393(3) . ?
C1 N1 1.438(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 I1 2.1007(19) . ?
C7 C8 1.383(3) . ?
C7 C12 1.385(3) . ?
C7 C20 1.507(3) . ?
C8 C9 1.373(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.390(3) . ?
C13 C14 1.395(3) . ?
C13 C19 1.503(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 I2 2.102(2) . ?
C19 O1 1.229(2) . ?
C19 N1 1.359(2) . ?
C20 N1 1.482(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
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 -0.9(3) . . . . ?
N1 C1 C2 C3 -179.38(18) . . . . ?
C1 C2 C3 C4 2.8(3) . . . . ?
C2 C3 C4 C5 -2.2(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?
C4 C5 C6 I1 -173.76(15) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
N1 C1 C6 C5 176.88(17) . . . . ?
C2 C1 C6 I1 174.19(14) . . . . ?
N1 C1 C6 I1 -7.4(2) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
C20 C7 C8 C9 178.7(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C20 C7 C12 C11 -178.7(2) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
C19 C13 C14 C15 -179.79(18) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.5(3) . . . . ?
C16 C17 C18 I2 -177.67(18) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C19 C13 C18 C17 179.94(19) . . . . ?
C14 C13 C18 I2 178.00(14) . . . . ?
C19 C13 C18 I2 -3.0(2) . . . . ?
C18 C13 C19 O1 -69.6(3) . . . . ?
C14 C13 C19 O1 109.4(2) . . . . ?
C18 C13 C19 N1 111.8(2) . . . . ?
C14 C13 C19 N1 -69.2(2) . . . . ?
C8 C7 C20 N1 -72.3(2) . . . . ?
C12 C7 C20 N1 107.2(2) . . . . ?
O1 C19 N1 C1 175.38(18) . . . . ?
C13 C19 N1 C1 -6.0(3) . . . . ?
O1 C19 N1 C20 4.1(3) . . . . ?
C13 C19 N1 C20 -177.32(17) . . . . ?
C2 C1 N1 C19 -68.5(2) . . . . ?
C6 C1 N1 C19 113.1(2) . . . . ?
C2 C1 N1 C20 103.0(2) . . . . ?
C6 C1 N1 C20 -75.4(2) . . . . ?
C7 C20 N1 C19 123.03(19) . . . . ?
C7 C20 N1 C1 -48.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9694281
