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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/16/4101615.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_4101615
loop_
_publ_author_name
'Guthrie, David B.'
'Geib, Steven J.'
'Curran, Dennis P.'
_publ_section_title
;
 Radical and Heck cyclizations of diastereomeric o-haloanilide
 atropisomers.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              115
_journal_page_last               122
_journal_paper_doi               10.1021/ja108795x
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C16 H18 I N O3'
_chemical_formula_weight         399.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 94.332(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7112(15)
_cell_length_b                   11.6237(17)
_cell_length_c                   14.127(2)
_cell_measurement_reflns_used    5306
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1590.1(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      203(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15074
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    2.023
_exptl_absorpt_correction_T_max  0.6760
_exptl_absorpt_correction_T_min  0.5462
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.623
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                3144
_reflns_number_total             3655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja108795x_si_004.cif
_cod_data_source_block           dgc922s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4101615
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
I I 0.72654(2) 0.845623(19) 0.818067(16) 0.04560(12) Uani 1 1 d . . .
N N 0.8461(2) 0.58283(19) 0.85798(15) 0.0260(5) Uani 1 1 d . . .
O1 O 0.7107(2) 0.3853(2) 0.55234(14) 0.0362(5) Uani 1 1 d . . .
C1 C 0.6255(3) 0.6898(3) 0.84230(19) 0.0316(6) Uani 1 1 d . . .
O2 O 0.7856(3) 0.3469(2) 0.40915(19) 0.0590(8) Uani 1 1 d . . .
C2 C 0.4822(3) 0.6924(3) 0.8437(2) 0.0413(7) Uani 1 1 d . . .
H2 H 0.437(3) 0.762(3) 0.834(2) 0.031(8) Uiso 1 1 d . . .
O3 O 1.0604(2) 0.60724(19) 0.92997(15) 0.0345(5) Uani 1 1 d . . .
C3 C 0.4116(3) 0.5925(4) 0.8640(2) 0.0449(8) Uani 1 1 d . . .
H3 H 0.318(5) 0.591(4) 0.874(3) 0.056(12) Uiso 1 1 d . . .
C4 C 0.4839(3) 0.4920(3) 0.8833(3) 0.0431(8) Uani 1 1 d . . .
H4 H 0.435(4) 0.431(4) 0.900(3) 0.047(11) Uiso 1 1 d . . .
C5 C 0.6260(3) 0.4895(3) 0.8826(2) 0.0360(7) Uani 1 1 d . . .
H5 H 0.674(4) 0.432(3) 0.891(3) 0.043(10) Uiso 1 1 d . . .
C6 C 0.6994(3) 0.5884(2) 0.86170(18) 0.0281(6) Uani 1 1 d . . .
C7 C 0.9011(3) 0.5290(3) 0.77395(19) 0.0295(6) Uani 1 1 d . . .
H7 H 0.996(4) 0.539(3) 0.785(3) 0.042(10) Uiso 1 1 d . . .
C8 C 0.8440(4) 0.5843(3) 0.6814(2) 0.0361(7) Uani 1 1 d . . .
H8A H 0.870(5) 0.665(3) 0.678(3) 0.061(13) Uiso 1 1 d . . .
H8B H 0.737(4) 0.581(3) 0.677(2) 0.031(8) Uiso 1 1 d . . .
C9 C 0.8955(4) 0.5206(3) 0.5981(2) 0.0342(6) Uani 1 1 d . . .
H9A H 0.860(4) 0.547(3) 0.545(3) 0.046(11) Uiso 1 1 d . . .
H9B H 0.991(4) 0.523(4) 0.604(3) 0.055(11) Uiso 1 1 d . . .
C10 C 0.8543(3) 0.3950(3) 0.5946(2) 0.0316(6) Uani 1 1 d . . .
H10 H 0.907(4) 0.355(3) 0.551(3) 0.027(8) Uiso 1 1 d . . .
C11 C 0.8571(3) 0.3412(2) 0.6908(2) 0.0329(6) Uani 1 1 d . . .
H11 H 0.847(3) 0.250(3) 0.693(2) 0.030(8) Uiso 1 1 d . . .
C12 C 0.8785(3) 0.4013(3) 0.7708(2) 0.0339(6) Uani 1 1 d . . .
H12 H 0.889(4) 0.363(3) 0.833(3) 0.043(10) Uiso 1 1 d . . .
C13 C 0.6926(4) 0.3610(3) 0.4594(2) 0.0362(7) Uani 1 1 d . . .
C14 C 0.5431(4) 0.3552(4) 0.4269(3) 0.0536(10) Uani 1 1 d . . .
H14A H 0.5141 0.4281 0.3985 0.080 Uiso 1 1 calc R . .
H14B H 0.4896 0.3395 0.4807 0.080 Uiso 1 1 calc R . .
H14C H 0.5282 0.2943 0.3803 0.080 Uiso 1 1 calc R . .
C15 C 0.9352(3) 0.6154(2) 0.93288(19) 0.0265(5) Uani 1 1 d . . .
C16 C 0.8715(4) 0.6607(3) 1.0199(2) 0.0347(7) Uani 1 1 d . . .
H16A H 0.8341 0.5970 1.0543 0.052 Uiso 1 1 calc R . .
H16B H 0.7980 0.7142 1.0007 0.052 Uiso 1 1 calc R . .
H16C H 0.9416 0.6998 1.0606 0.052 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N C6 122.2(2) . . ?
C15 N C7 119.5(2) . . ?
C6 N C7 118.0(2) . . ?
C13 O1 C10 117.4(2) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 I 117.6(2) . . ?
C6 C1 I 121.3(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 119(2) . . ?
C3 C2 H2 122(2) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 116(3) . . ?
C2 C3 H3 124(3) . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 117(3) . . ?
C5 C4 H4 122(3) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 125(3) . . ?
C6 C5 H5 114(3) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 N 119.7(3) . . ?
C1 C6 N 122.0(3) . . ?
N C7 C12 112.4(2) . . ?
N C7 C8 112.4(2) . . ?
C12 C7 C8 110.4(2) . . ?
N C7 H7 103(2) . . ?
C12 C7 H7 106(2) . . ?
C8 C7 H7 113(2) . . ?
C9 C8 C7 110.0(3) . . ?
C9 C8 H8A 110(3) . . ?
C7 C8 H8A 112(3) . . ?
C9 C8 H8B 109.1(18) . . ?
C7 C8 H8B 109.2(18) . . ?
H8A C8 H8B 107(4) . . ?
C8 C9 C10 113.4(3) . . ?
C8 C9 H9A 112(3) . . ?
C10 C9 H9A 103(3) . . ?
C8 C9 H9B 108(3) . . ?
C10 C9 H9B 107(3) . . ?
H9A C9 H9B 114(4) . . ?
O1 C10 C11 106.7(2) . . ?
O1 C10 C9 109.0(3) . . ?
C11 C10 C9 112.7(2) . . ?
O1 C10 H10 104(2) . . ?
C11 C10 H10 114(2) . . ?
C9 C10 H10 110.2(19) . . ?
C12 C11 C10 123.0(3) . . ?
C12 C11 H11 120.1(17) . . ?
C10 C11 H11 116.8(17) . . ?
C11 C12 C7 123.8(3) . . ?
C11 C12 H12 121(2) . . ?
C7 C12 H12 115(2) . . ?
O2 C13 O1 123.9(3) . . ?
O2 C13 C14 124.7(3) . . ?
O1 C13 C14 111.3(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 N 121.6(3) . . ?
O3 C15 C16 121.5(3) . . ?
N C15 C16 116.8(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
I C1 2.101(3) . ?
N C15 1.369(3) . ?
N C6 1.432(3) . ?
N C7 1.477(3) . ?
O1 C13 1.341(4) . ?
O1 C10 1.479(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.396(4) . ?
O2 C13 1.202(4) . ?
C2 C3 1.389(6) . ?
C2 H2 0.92(3) . ?
O3 C15 1.223(3) . ?
C3 C4 1.379(6) . ?
C3 H3 0.93(5) . ?
C4 C5 1.381(4) . ?
C4 H4 0.90(4) . ?
C5 C6 1.396(4) . ?
C5 H5 0.82(4) . ?
C7 C12 1.500(4) . ?
C7 C8 1.524(4) . ?
C7 H7 0.93(4) . ?
C8 C9 1.507(4) . ?
C8 H8A 0.97(4) . ?
C8 H8B 1.03(3) . ?
C9 C10 1.515(4) . ?
C9 H9A 0.86(4) . ?
C9 H9B 0.93(4) . ?
C10 C11 1.494(4) . ?
C10 H10 0.95(4) . ?
C11 C12 1.332(4) . ?
C11 H11 1.06(3) . ?
C12 H12 0.98(4) . ?
C13 C14 1.491(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.512(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139114083
