#------------------------------------------------------------------------------
#$Date: 2020-05-23 02:17:50 +0300 (Sat, 23 May 2020) $
#$Revision: 252287 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038405.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_4038405
loop_
_publ_author_name
'Brittain, William David George'
'Cobb, Steven L.'
_publ_section_title
;
 Protecting Group Controlled Remote Regioselective Electrophilic Aromatic
 Halogenation Reactions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03322
_journal_year                    2020
_chemical_formula_moiety         'C15 H6 F4 I N O'
_chemical_formula_sum            'C15 H6 F4 I N O'
_chemical_formula_weight         419.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.865(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.6677(3)
_cell_length_b                   11.0185(7)
_cell_length_c                   13.0170(8)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.55
_cell_measurement_theta_min      2.42
_cell_volume                     669.40(7)
_computing_cell_refinement       'SAINT v8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_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            14627
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         3.130
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.439
_exptl_absorpt_correction_T_max  0.9042
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;    
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1080 before and 0.0394 after correction. 
The Ratio of minimum to maximum transmission is 0.6973. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_description       plank
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1735 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.044(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0163
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0244P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0397
_refine_ls_wR_factor_ref         0.0401
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3752
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03322_si_002.cif
_cod_data_source_block           3f_19srv253
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038405
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.604
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.66971(3) 0.17432(2) 0.27137(2) 0.01861(5) Uani 1 1 d . . . . .
F1 F 1.1776(4) 0.29311(16) 0.48962(14) 0.0264(4) Uani 1 1 d . . . . .
F2 F 0.8655(5) 0.3699(2) 0.64987(14) 0.0369(5) Uani 1 1 d . . . . .
F3 F 0.3700(4) 0.63442(15) 0.45156(14) 0.0275(4) Uani 1 1 d . . . . .
F4 F 0.6754(3) 0.57897(19) 0.28448(12) 0.0249(4) Uani 1 1 d . . . . .
O1 O 1.1095(4) 0.39499(18) 0.30380(15) 0.0175(4) Uani 1 1 d . . . . .
N1 N 0.6164(6) 0.5017(2) 0.55036(19) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.8093(5) 0.3075(2) 0.1689(2) 0.0151(4) Uani 1 1 d . . . . .
C2 C 1.0040(5) 0.3932(2) 0.20146(19) 0.0158(5) Uani 1 1 d . . . . .
C3 C 1.1243(6) 0.4790(2) 0.1347(2) 0.0180(5) Uani 1 1 d . . . . .
H3 H 1.263042 0.535424 0.159259 0.022 Uiso 1 1 calc R . . . .
C4 C 1.0383(6) 0.4798(2) 0.0340(2) 0.0178(5) Uani 1 1 d . . . . .
H4 H 1.120687 0.536527 -0.011942 0.021 Uiso 1 1 calc R . . . .
C5 C 0.7315(6) 0.4018(3) -0.1073(2) 0.0199(5) Uani 1 1 d . . . . .
H5 H 0.810350 0.459854 -0.152753 0.024 Uiso 1 1 calc R . . . .
C6 C 0.5258(6) 0.3230(3) -0.1425(2) 0.0209(5) Uani 1 1 d . . . . .
H6 H 0.462660 0.326590 -0.212135 0.025 Uiso 1 1 calc R . . . .
C7 C 0.4079(6) 0.2369(3) -0.0757(2) 0.0199(5) Uani 1 1 d . . . . .
H7 H 0.263650 0.183114 -0.100569 0.024 Uiso 1 1 calc R . . . .
C8 C 0.4983(5) 0.2293(2) 0.0253(2) 0.0169(5) Uani 1 1 d . . . . .
H8 H 0.417912 0.169801 0.069180 0.020 Uiso 1 1 calc R . . . .
C9 C 0.7108(5) 0.3098(2) 0.06418(19) 0.0144(4) Uani 1 1 d . . . . .
C10 C 0.8287(6) 0.3975(2) -0.0029(2) 0.0161(5) Uani 1 1 d . . . . .
C11 C 0.9342(5) 0.4307(2) 0.37995(19) 0.0155(5) Uani 1 1 d . . . . .
C12 C 0.9811(6) 0.3786(3) 0.4768(2) 0.0192(5) Uani 1 1 d . . . . .
C13 C 0.8178(7) 0.4185(3) 0.5581(2) 0.0238(6) Uani 1 1 d . . . . .
C14 C 0.5754(6) 0.5502(2) 0.4594(2) 0.0203(5) Uani 1 1 d . . . . .
C15 C 0.7267(6) 0.5209(3) 0.3727(2) 0.0173(5) 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'
F F 0.0171 0.0103 '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'
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'
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
C11 O1 C2 119.25(19) . . ?
C14 N1 C13 116.6(3) . . ?
C2 C1 I1 119.76(19) . . ?
C2 C1 C9 118.9(2) . . ?
C9 C1 I1 121.33(19) . . ?
C1 C2 O1 121.3(2) . . ?
C1 C2 C3 122.7(2) . . ?
C3 C2 O1 115.9(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C10 121.0(2) . . ?
C10 C4 H4 119.5 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C10 120.7(3) . . ?
C10 C5 H5 119.7 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C1 122.8(2) . . ?
C8 C9 C10 118.8(2) . . ?
C10 C9 C1 118.4(2) . . ?
C4 C10 C5 120.8(2) . . ?
C4 C10 C9 120.0(2) . . ?
C9 C10 C5 119.2(2) . . ?
O1 C11 C12 116.9(2) . . ?
O1 C11 C15 125.9(2) . . ?
C15 C11 C12 117.0(2) . . ?
F1 C12 C11 120.3(2) . . ?
F1 C12 C13 121.1(3) . . ?
C13 C12 C11 118.5(3) . . ?
F2 C13 C12 118.3(3) . . ?
N1 C13 F2 117.4(3) . . ?
N1 C13 C12 124.3(3) . . ?
F3 C14 C15 118.4(3) . . ?
N1 C14 F3 116.6(3) . . ?
N1 C14 C15 125.1(3) . . ?
F4 C15 C11 121.2(2) . . ?
F4 C15 C14 120.3(2) . . ?
C14 C15 C11 118.5(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
I1 C1 2.094(3) . ?
F1 C12 1.324(3) . ?
F2 C13 1.325(4) . ?
F3 C14 1.337(3) . ?
F4 C15 1.333(3) . ?
O1 C2 1.413(3) . ?
O1 C11 1.353(3) . ?
N1 C13 1.316(4) . ?
N1 C14 1.310(4) . ?
C1 C2 1.373(4) . ?
C1 C9 1.432(3) . ?
C2 C3 1.407(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.365(4) . ?
C4 H4 0.9500 . ?
C4 C10 1.413(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(4) . ?
C5 C10 1.426(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.405(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.418(4) . ?
C9 C10 1.420(4) . ?
C11 C12 1.399(4) . ?
C11 C15 1.390(4) . ?
C12 C13 1.386(4) . ?
C14 C15 1.379(4) . ?
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
C1 C2 O1 C11 -71.8(3) . . . . ?
C3 C2 O1 C11 112.1(3) . . . . ?
C12 C11 O1 C2 149.4(2) . . . . ?
C15 C11 O1 C2 -35.8(4) . . . . ?
