#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/29/4102935.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_4102935
loop_
_publ_author_name
'Achim Bruch'
'Andrea Ambrosius'
'Roland Fröhlich'
'Armido Studer'
'David B. Guthrie'
'Hanmo Zhang'
'Dennis P. Curran'
_publ_section_title
;
 Memory of Axial Chirality in Aryl Radical Phosphanylations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11452
_journal_page_last               11454
_journal_paper_doi               10.1021/ja105070k
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H18 I N O'
_chemical_formula_weight         379.22
_chemical_name_systematic
; 
 ? 
;
_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                   9.1093(3)
_cell_length_b                   10.1239(3)
_cell_length_c                   17.6114(5)
_cell_measurement_reflns_used    3299
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.41
_cell_volume                     1624.15(9)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10409
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_T_max  0.9080
_exptl_absorpt_correction_T_min  0.5898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       0.0040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0326
_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)+(0.0276P)²+1.4818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                3252
_reflns_number_total             3920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105070k_si_002.cif
_cod_data_source_block           stu4819
_cod_database_code               4102935
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_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
N1 N 0.8983(3) 0.9443(3) 0.83683(17) 0.0343(7) Uani 1 1 d .
C1 C 0.8931(4) 1.0583(4) 0.8768(3) 0.0459(10) Uani 1 1 d .
O1 O 0.8786(4) 1.1660(3) 0.8458(2) 0.0668(9) Uani 1 1 d .
C2 C 0.9095(5) 1.0477(4) 0.9624(2) 0.0518(11) Uani 1 1 d .
H2A H 0.8721 1.1273 0.9861 0.078 Uiso 1 1 calc R
H2B H 1.0124 1.0369 0.9752 0.078 Uiso 1 1 calc R
H2C H 0.8546 0.9720 0.9806 0.078 Uiso 1 1 calc R
C4 C 0.9147(4) 0.8173(4) 0.8714(2) 0.0304(8) Uani 1 1 d .
C5 C 1.0552(4) 0.7626(4) 0.8796(2) 0.0329(8) Uani 1 1 d .
I1 I 1.24033(2) 0.87117(3) 0.846666(15) 0.04953(10) Uani 1 1 d .
C6 C 1.0751(4) 0.6383(4) 0.9097(2) 0.0389(8) Uani 1 1 d .
H6 H 1.1703 0.6036 0.9146 0.047 Uiso 1 1 calc R
C7 C 0.9552(5) 0.5644(4) 0.9328(2) 0.0420(9) Uani 1 1 d .
C8 C 0.8162(4) 0.6201(4) 0.9253(2) 0.0421(8) Uani 1 1 d .
H8 H 0.7343 0.5710 0.9415 0.051 Uiso 1 1 calc R
C9 C 0.7930(4) 0.7454(4) 0.8948(2) 0.0344(8) Uani 1 1 d .
C10 C 0.6376(4) 0.7983(4) 0.8897(2) 0.0435(10) Uani 1 1 d .
H10A H 0.6003 0.7849 0.8387 0.065 Uiso 1 1 calc R
H10B H 0.6374 0.8919 0.9014 0.065 Uiso 1 1 calc R
H10C H 0.5756 0.7518 0.9256 0.065 Uiso 1 1 calc R
C11 C 0.9748(6) 0.4266(4) 0.9644(3) 0.0633(13) Uani 1 1 d .
H11A H 0.9544 0.3623 0.9249 0.095 Uiso 1 1 calc R
H11B H 0.9076 0.4135 1.0064 0.095 Uiso 1 1 calc R
H11C H 1.0750 0.4158 0.9820 0.095 Uiso 1 1 calc R
C3 C 0.8980(4) 0.9495(4) 0.7525(2) 0.0411(9) Uani 1 1 d .
H3A H 0.9734 0.8893 0.7329 0.049 Uiso 1 1 calc R
H3B H 0.9233 1.0391 0.7360 0.049 Uiso 1 1 calc R
C12 C 0.7515(4) 0.9118(3) 0.71939(17) 0.0368(7) Uani 1 1 d .
C13 C 0.7290(5) 0.7867(4) 0.6889(2) 0.0450(9) Uani 1 1 d .
H13 H 0.8071 0.7261 0.6867 0.054 Uiso 1 1 calc R
C14 C 0.5915(5) 0.7509(5) 0.6616(3) 0.0546(11) Uani 1 1 d .
H14 H 0.5767 0.6659 0.6415 0.066 Uiso 1 1 calc R
C15 C 0.4775(5) 0.8386(5) 0.6640(3) 0.0572(12) Uani 1 1 d .
H15 H 0.3844 0.8135 0.6460 0.069 Uiso 1 1 calc R
C16 C 0.4988(5) 0.9637(5) 0.6928(3) 0.0511(11) Uani 1 1 d .
H16 H 0.4208 1.0245 0.6936 0.061 Uiso 1 1 calc R
C17 C 0.6353(4) 0.9996(4) 0.7205(2) 0.0425(9) Uani 1 1 d .
H17 H 0.6491 1.0849 0.7404 0.051 Uiso 1 1 calc R
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
C1 N1 C4 123.3(3)
C1 N1 C3 119.4(3)
C4 N1 C3 117.2(3)
O1 C1 N1 122.0(4)
O1 C1 C2 121.1(4)
N1 C1 C2 116.9(4)
C9 C4 C5 119.4(3)
C9 C4 N1 120.9(3)
C5 C4 N1 119.7(3)
C6 C5 C4 121.4(3)
C6 C5 I1 118.7(3)
C4 C5 I1 119.9(3)
C5 C6 C7 120.2(3)
C6 C7 C8 118.1(3)
C6 C7 C11 120.9(4)
C8 C7 C11 121.0(4)
C7 C8 C9 122.9(3)
C4 C9 C8 118.1(3)
C4 C9 C10 122.9(3)
C8 C9 C10 119.1(3)
N1 C3 C12 112.3(3)
C17 C12 C13 118.6(4)
C17 C12 C3 120.7(3)
C13 C12 C3 120.7(4)
C14 C13 C12 120.2(4)
C15 C14 C13 120.3(4)
C14 C15 C16 120.1(4)
C15 C16 C17 119.8(4)
C12 C17 C16 120.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.353(5)
N1 C4 1.430(5)
N1 C3 1.486(5)
C1 O1 1.227(5)
C1 C2 1.518(6)
C4 C9 1.389(5)
C4 C5 1.402(5)
C5 C6 1.377(5)
C5 I1 2.095(4)
C6 C7 1.385(5)
C7 C8 1.393(6)
C7 C11 1.512(6)
C8 C9 1.394(6)
C9 C10 1.516(5)
C3 C12 1.505(5)
C12 C17 1.383(5)
C12 C13 1.391(5)
C13 C14 1.390(6)
C14 C15 1.367(6)
C15 C16 1.378(6)
C16 C17 1.384(6)
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
C4 N1 C1 O1 -179.8(4)
C3 N1 C1 O1 4.8(6)
C4 N1 C1 C2 1.5(6)
C3 N1 C1 C2 -173.9(3)
C1 N1 C4 C9 88.6(5)
C3 N1 C4 C9 -95.9(4)
C1 N1 C4 C5 -93.5(4)
C3 N1 C4 C5 82.0(4)
C9 C4 C5 C6 0.7(6)
N1 C4 C5 C6 -177.3(3)
C9 C4 C5 I1 -178.8(3)
N1 C4 C5 I1 3.3(5)
C4 C5 C6 C7 -0.1(5)
I1 C5 C6 C7 179.4(3)
C5 C6 C7 C8 -0.7(5)
C5 C6 C7 C11 178.7(4)
C6 C7 C8 C9 0.9(6)
C11 C7 C8 C9 -178.5(4)
C5 C4 C9 C8 -0.5(5)
N1 C4 C9 C8 177.4(3)
C5 C4 C9 C10 178.6(4)
N1 C4 C9 C10 -3.5(5)
C7 C8 C9 C4 -0.3(5)
C7 C8 C9 C10 -179.4(4)
C1 N1 C3 C12 -104.4(4)
C4 N1 C3 C12 79.9(4)
N1 C3 C12 C17 76.6(5)
N1 C3 C12 C13 -101.6(4)
C17 C12 C13 C14 -1.2(5)
C3 C12 C13 C14 177.1(4)
C12 C13 C14 C15 0.5(6)
C13 C14 C15 C16 0.7(7)
C14 C15 C16 C17 -1.1(7)
C13 C12 C17 C16 0.8(6)
C3 C12 C17 C16 -177.5(4)
C15 C16 C17 C12 0.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660132
