#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/28/7102867.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_7102867
loop_
_publ_author_name
'Clayden, Jonathan'
'Vallverdú, Lluís'
'Clayton, James'
'Helliwell, Madeleine'
_publ_section_title
;
 Conformational switching between diastereoisomeric atropisomers of
 arenedicarboxamides induced by complexation with Lewis acids.
;
_journal_issue                   5
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              561
_journal_page_last               563
_journal_paper_doi               10.1039/b716105k
_journal_year                    2008
_chemical_formula_moiety         'C26 H34 I2 N2 O2'
_chemical_formula_sum            'C26 H34 I2 N2 O2'
_chemical_formula_weight         660.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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            2
_cell_length_a                   13.0880(10)
_cell_length_b                   13.5460(10)
_cell_length_c                   7.5320(6)
_cell_measurement_reflns_used    5908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.1695
_cell_measurement_theta_min      3.006
_cell_volume                     1335.35(18)
_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    'SIR2004 (Burla et al, 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11386
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    2.379
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.518
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0304
_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)+(0.0420P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                2935
_reflns_number_total             3165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b716105k.txt
_cod_data_source_block           s2456n
_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_Hall     P22ab
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_database_code               7102867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -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 0.4761(3) 0.0503(3) 0.1321(5) 0.0144(7) Uani 1 1 d . . .
C2 C 0.5306(3) 0.1359(3) 0.1813(4) 0.0153(7) Uani 1 1 d . . .
C3 C 0.4806(3) 0.2269(3) 0.1742(5) 0.0186(8) Uani 1 1 d . . .
C4 C 0.3793(3) 0.2358(3) 0.1192(5) 0.0199(8) Uani 1 1 d . . .
H4 H 0.3469 0.2986 0.1163 0.024 Uiso 1 1 calc R . .
C5 C 0.3270(3) 0.1520(3) 0.0691(5) 0.0216(8) Uani 1 1 d . . .
H5 H 0.2580 0.1568 0.0310 0.026 Uiso 1 1 calc R . .
C6 C 0.3743(3) 0.0614(3) 0.0739(5) 0.0176(8) Uani 1 1 d . . .
H6 H 0.3373 0.0046 0.0370 0.021 Uiso 1 1 calc R . .
C7 C 0.6451(3) 0.1393(3) 0.2186(4) 0.0165(7) Uani 1 1 d . . .
C8 C 0.7912(3) 0.1267(3) 0.4203(6) 0.0230(8) Uani 1 1 d . . .
H8 H 0.8000 0.1089 0.5482 0.028 Uiso 1 1 calc R . .
C9 C 0.8279(3) 0.2313(3) 0.4010(6) 0.0272(9) Uani 1 1 d . . .
H9A H 0.8269 0.2500 0.2754 0.041 Uiso 1 1 calc R . .
H9B H 0.8977 0.2366 0.4469 0.041 Uiso 1 1 calc R . .
H9C H 0.7829 0.2754 0.4682 0.041 Uiso 1 1 calc R . .
C10 C 0.8532(3) 0.0528(3) 0.3151(6) 0.0314(10) Uani 1 1 d . . .
H10A H 0.8260 -0.0137 0.3347 0.047 Uiso 1 1 calc R . .
H10B H 0.9247 0.0553 0.3538 0.047 Uiso 1 1 calc R . .
H10C H 0.8492 0.0690 0.1884 0.047 Uiso 1 1 calc R . .
C11 C 0.6121(3) 0.0901(3) 0.5297(5) 0.0196(8) Uani 1 1 d . . .
H11 H 0.5411 0.0847 0.4814 0.023 Uiso 1 1 calc R . .
C12 C 0.6105(3) 0.1694(3) 0.6723(6) 0.0286(10) Uani 1 1 d . . .
H12A H 0.6771 0.1718 0.7315 0.043 Uiso 1 1 calc R . .
H12B H 0.5573 0.1540 0.7596 0.043 Uiso 1 1 calc R . .
H12C H 0.5960 0.2336 0.6176 0.043 Uiso 1 1 calc R . .
C13 C 0.6414(3) -0.0114(3) 0.6021(6) 0.0306(10) Uani 1 1 d . . .
H13A H 0.6294 -0.0616 0.5107 0.046 Uiso 1 1 calc R . .
H13B H 0.5997 -0.0263 0.7069 0.046 Uiso 1 1 calc R . .
H13C H 0.7138 -0.0114 0.6352 0.046 Uiso 1 1 calc R . .
I1 I 0.553652(17) 0.360085(16) 0.24215(3) 0.02416(9) Uani 1 1 d . . .
N1 N 0.6794(2) 0.1173(2) 0.3808(4) 0.0169(7) Uani 1 1 d . . .
O1 O 0.7001(2) 0.16403(19) 0.0953(3) 0.0192(6) 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 118.1(3) . . ?
C2 C1 C1 122.5(4) . 2_655 ?
C6 C1 C1 119.3(4) . 2_655 ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C7 116.2(3) . . ?
C1 C2 C7 124.7(3) . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 I1 115.4(3) . . ?
C2 C3 I1 122.2(3) . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.9(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
O1 C7 N1 123.9(3) . . ?
O1 C7 C2 116.5(3) . . ?
N1 C7 C2 119.5(3) . . ?
N1 C8 C9 111.9(3) . . ?
N1 C8 C10 111.4(3) . . ?
C9 C8 C10 113.7(4) . . ?
N1 C8 H8 106.5 . . ?
C9 C8 H8 106.5 . . ?
C10 C8 H8 106.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 111.6(3) . . ?
N1 C11 C13 110.3(3) . . ?
C12 C11 C13 112.8(3) . . ?
N1 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C13 C11 H11 107.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C11 123.4(3) . . ?
C7 N1 C8 119.4(3) . . ?
C11 N1 C8 117.1(3) . . ?
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 1.411(5) . ?
C1 C6 1.412(5) . ?
C1 C1 1.499(7) 2_655 ?
C2 C3 1.396(5) . ?
C2 C7 1.525(5) . ?
C3 C4 1.394(5) . ?
C3 I1 2.106(4) . ?
C4 C5 1.379(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.223(4) . ?
C7 N1 1.335(4) . ?
C8 N1 1.498(5) . ?
C8 C9 1.503(6) . ?
C8 C10 1.512(6) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N1 1.474(5) . ?
C11 C12 1.519(6) . ?
C11 C13 1.528(6) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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 1.6(5) . . . . ?
C1 C1 C2 C3 178.8(3) 2_655 . . . ?
C6 C1 C2 C7 -169.8(3) . . . . ?
C1 C1 C2 C7 7.4(4) 2_655 . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C7 C2 C3 C4 171.6(3) . . . . ?
C1 C2 C3 I1 -179.5(3) . . . . ?
C7 C2 C3 I1 -7.4(4) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
I1 C3 C4 C5 178.7(3) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
C1 C1 C6 C5 -179.2(3) 2_655 . . . ?
C3 C2 C7 O1 -76.2(4) . . . . ?
C1 C2 C7 O1 95.4(4) . . . . ?
C3 C2 C7 N1 102.7(4) . . . . ?
C1 C2 C7 N1 -85.7(4) . . . . ?
O1 C7 N1 C11 178.3(3) . . . . ?
C2 C7 N1 C11 -0.4(5) . . . . ?
O1 C7 N1 C8 2.5(5) . . . . ?
C2 C7 N1 C8 -176.3(3) . . . . ?
C12 C11 N1 C7 -111.3(4) . . . . ?
C13 C11 N1 C7 122.5(4) . . . . ?
C12 C11 N1 C8 64.7(4) . . . . ?
C13 C11 N1 C8 -61.6(4) . . . . ?
C9 C8 N1 C7 62.5(5) . . . . ?
C10 C8 N1 C7 -66.0(5) . . . . ?
C9 C8 N1 C11 -113.6(4) . . . . ?
C10 C8 N1 C11 117.9(4) . . . . ?
