#------------------------------------------------------------------------------
#$Date: 2019-11-25 16:05:06 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241279 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/09/4130946.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_4130946
loop_
_publ_author_name
'Izquierdo, Susana'
'Essafi, Stéphanie'
'Del Rosal, Iker'
'Vidossich, Pietro'
'Pleixats, Roser'
'Vallribera, Adelina'
'Ujaque, Gregori'
'Lledós, Agustí'
'Shafir, Alexandr'
_publ_section_title
;
 Acid Activation in Phenyliodine Dicarboxylates: Direct Observation,
 Structures, and Implications.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12747
_journal_page_last               12750
_journal_paper_doi               10.1021/jacs.6b07999
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C10 H11 B F3 I O4'
_chemical_formula_weight         389.90
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.564(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6550(8)
_cell_length_b                   8.3949(6)
_cell_length_c                   16.7646(13)
_cell_measurement_reflns_used    3661
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.63
_cell_measurement_theta_min      2.36
_cell_volume                     1354.51(18)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12722
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.575
_diffrn_reflns_theta_min         2.356
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    2.405
_exptl_absorpt_correction_T_max  0.795
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.386
_refine_diff_density_min         -2.339
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2991
_reflns_number_total             4220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b07999_si_004.cif
_cod_data_source_block           mo_sif123b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4130946
_shelx_shelxl_version_number     2014/7
_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_min   0.714
_shelx_estimated_absorpt_t_max   0.795
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 0.88436(2) 0.37797(3) 0.22124(2) 0.02238(9) Uani 1 1 d . .
B1 B 1.2750(5) 0.5973(6) 0.1771(3) 0.0259(10) Uani 1 1 d . .
O1 O 0.7358(3) 0.2427(4) 0.15540(16) 0.0290(7) Uani 1 1 d . .
O2 O 0.8886(3) 0.2740(4) 0.06400(18) 0.0374(8) Uani 1 1 d . .
O3 O 1.0148(3) 0.5171(3) 0.31686(16) 0.0246(6) Uani 1 1 d . .
O4 O 1.1477(3) 0.5464(3) 0.21850(15) 0.0224(6) Uani 1 1 d . .
C1 C 0.7819(4) 0.3024(5) 0.3203(2) 0.0241(8) Uani 1 1 d . .
C2 C 0.6417(4) 0.3448(5) 0.3245(2) 0.0253(8) Uani 1 1 d . .
H2 H 0.5935 0.4097 0.2850 0.030 Uiso 1 1 calc R U
C3 C 0.5771(4) 0.2853(5) 0.3906(2) 0.0288(9) Uani 1 1 d . .
H3 H 0.4824 0.3105 0.3962 0.035 Uiso 1 1 calc R U
C4 C 0.6481(4) 0.1913(5) 0.4475(2) 0.0263(9) Uani 1 1 d . .
H4 H 0.6020 0.1526 0.4916 0.032 Uiso 1 1 calc R U
C5 C 0.7857(5) 0.1531(5) 0.4408(2) 0.0281(9) Uani 1 1 d . .
H5 H 0.8336 0.0884 0.4805 0.034 Uiso 1 1 calc R U
C6 C 0.8556(4) 0.2086(5) 0.3763(2) 0.0262(9) Uani 1 1 d . .
H6 H 0.9502 0.1826 0.3712 0.031 Uiso 1 1 calc R U
C7 C 0.7772(4) 0.2222(5) 0.0818(2) 0.0279(9) Uani 1 1 d . .
C8 C 0.6762(5) 0.1323(6) 0.0268(3) 0.0366(11) Uani 1 1 d . .
H8A H 0.6890 0.1619 -0.0287 0.055 Uiso 1 1 calc R U
H8B H 0.5813 0.1583 0.0390 0.055 Uiso 1 1 calc R U
H8C H 0.6921 0.0177 0.0338 0.055 Uiso 1 1 calc R U
C9 C 1.1269(4) 0.5691(5) 0.2925(2) 0.0214(8) Uani 1 1 d . .
C10 C 1.2280(4) 0.6512(5) 0.3496(2) 0.0289(9) Uani 1 1 d . .
H10A H 1.1863 0.6682 0.4004 0.043 Uiso 1 1 calc R U
H10B H 1.2531 0.7542 0.3273 0.043 Uiso 1 1 calc R U
H10C H 1.3116 0.5854 0.3590 0.043 Uiso 1 1 calc R U
F1 F 1.2795(3) 0.7626(3) 0.17598(14) 0.0318(6) Uani 1 1 d . .
F2 F 1.3927(2) 0.5362(4) 0.21785(14) 0.0380(7) Uani 1 1 d . .
F3 F 1.2561(3) 0.5374(3) 0.10092(14) 0.0340(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'
B B 0.0013 0.0007 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 I1 C1 84.62(13)
O1 I1 O3 166.72(10)
C1 I1 O3 82.36(13)
F3 B1 F2 111.6(4)
F3 B1 F1 110.9(4)
F2 B1 F1 110.7(4)
F3 B1 O4 105.6(3)
F2 B1 O4 109.5(3)
F1 B1 O4 108.3(3)
C7 O1 I1 108.5(3)
C9 O3 I1 112.9(2)
C9 O4 B1 126.3(3)
C6 C1 C2 123.9(4)
C6 C1 I1 117.4(3)
C2 C1 I1 118.6(3)
C3 C2 C1 116.0(4)
C4 C3 C2 121.4(4)
C3 C4 C5 120.4(4)
C4 C5 C6 120.7(4)
C1 C6 C5 117.5(4)
O2 C7 O1 120.9(4)
O2 C7 C8 125.1(4)
O1 C7 C8 114.0(4)
O3 C9 O4 117.6(4)
O3 C9 C10 119.2(3)
O4 C9 C10 123.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 O1 2.077(3)
I1 C1 2.098(4)
I1 O3 2.280(3)
B1 F3 1.371(5)
B1 F2 1.378(5)
B1 F1 1.388(5)
B1 O4 1.520(5)
O1 C7 1.338(5)
O2 C7 1.220(5)
O3 C9 1.265(5)
O4 C9 1.286(4)
C1 C6 1.378(6)
C1 C2 1.407(5)
C2 C3 1.405(6)
C3 C4 1.377(6)
C4 C5 1.380(6)
C5 C6 1.400(6)
C7 C8 1.492(6)
C9 C10 1.482(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
F3 B1 O4 C9 175.4(3)
F2 B1 O4 C9 55.0(5)
F1 B1 O4 C9 -65.8(5)
C6 C1 C2 C3 0.0(6)
I1 C1 C2 C3 177.5(3)
C1 C2 C3 C4 0.0(6)
C2 C3 C4 C5 0.1(6)
C3 C4 C5 C6 -0.1(6)
C2 C1 C6 C5 -0.1(6)
I1 C1 C6 C5 -177.6(3)
C4 C5 C6 C1 0.1(6)
I1 O1 C7 O2 2.8(5)
I1 O1 C7 C8 -177.5(3)
I1 O3 C9 O4 4.2(5)
I1 O3 C9 C10 -175.3(3)
B1 O4 C9 O3 -179.4(4)
B1 O4 C9 C10 0.1(6)
