#------------------------------------------------------------------------------
#$Date: 2023-05-05 01:58:20 +0200 (Fri 05 de May de 2023) $
#$Revision: 283011 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/14/7131413.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_7131413
loop_
_publ_author_name
'Thai, Phong'
'Frey, Brandon L.'
'Figgins, Matthew T.'
'Thompson, Richard R.'
'Carmieli, Raanan'
'Powers, David C.'
_publ_section_title
;
 Selective multi-electron aggregation at a hypervalent iodine center by
 sequential disproportionation.
;
_journal_issue                   29
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4308
_journal_page_last               4311
_journal_paper_doi               10.1039/d3cc00549f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C10 H14 I O3 S, B F4'
_chemical_formula_sum            'C10 H14 B F4 I O3 S'
_chemical_formula_weight         427.98
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.647(2)
_cell_length_b                   10.259(3)
_cell_length_c                   24.055(1)
_cell_measurement_reflns_used    3850
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      23.778
_cell_measurement_theta_min      2.158
_cell_volume                     1393.6(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7549
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        23.819
_diffrn_reflns_theta_max         23.819
_diffrn_reflns_theta_min         2.609
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.496
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.5276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1101 before and 0.0751 after correction.
The Ratio of minimum to maximum transmission is 0.7082.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.627
_refine_diff_density_min         -1.320
_refine_diff_density_rms         0.200
_refine_ls_abs_structure_details
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.243
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0537
_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)+(0.0249P)²+12.0505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2048
_reflns_number_total             2135
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc00549f2.cif
_cod_data_source_block           blf_pt_oxidizedproduct_0m
_cod_depositor_comments
'Adding full bibliography for 7131411--7131416.cif.'
_cod_original_cell_volume        1393.7(6)
_cod_database_code               7131413
_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_max   0.975
_shelx_estimated_absorpt_t_min   0.885
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C5 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
3. Rigid body (RIGU) restrains
 C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Free rotating group:
 O3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 -0.02299(16) 0.35260(9) 0.58455(4) 0.0234(3) Uani 1 1 d . . . . .
S1 S -0.0108(7) 0.6204(3) 0.66524(14) 0.0172(8) Uani 1 1 d . . . . .
O1 O -0.1194(18) 0.7459(9) 0.6697(4) 0.020(2) Uani 1 1 d . . . . .
O2 O -0.1674(17) 0.5093(10) 0.6528(4) 0.020(2) Uani 1 1 d . . . . .
O3 O 0.131(2) 0.2541(11) 0.5266(5) 0.031(3) Uani 1 1 d G . . . .
H3 H 0.2023 0.2028 0.5500 0.046 Uiso 1 1 d G U . . .
C1 C 0.214(2) 0.5105(15) 0.5757(7) 0.019(4) Uani 1 1 d . . . . .
C2 C 0.198(3) 0.6202(15) 0.6091(6) 0.018(4) Uani 1 1 d . . . . .
C3 C 0.339(3) 0.7256(14) 0.6009(6) 0.020(4) Uani 1 1 d . . . . .
H3A H 0.3245 0.7999 0.6242 0.024 Uiso 1 1 calc R U . . .
C4 C 0.505(3) 0.7241(12) 0.5579(6) 0.022(3) Uani 1 1 d . . . . .
H4 H 0.6043 0.7973 0.5514 0.026 Uiso 1 1 calc R U . . .
C5 C 0.522(3) 0.6145(12) 0.5251(6) 0.020(3) Uani 1 1 d . U . . .
H5 H 0.6360 0.6123 0.4961 0.024 Uiso 1 1 calc R U . . .
C6 C 0.378(3) 0.5082(14) 0.5332(7) 0.020(3) Uani 1 1 d . U . . .
H6 H 0.3916 0.4339 0.5098 0.024 Uiso 1 1 calc R U . . .
C7 C 0.147(3) 0.5838(14) 0.7293(6) 0.018(3) Uani 1 1 d . . . . .
C8 C 0.286(3) 0.4542(14) 0.7216(7) 0.023(4) Uani 1 1 d . . . . .
H8A H 0.1779 0.3862 0.7083 0.034 Uiso 1 1 calc R U . . .
H8B H 0.3546 0.4276 0.7572 0.034 Uiso 1 1 calc R U . . .
H8C H 0.4128 0.4671 0.6943 0.034 Uiso 1 1 calc R U . . .
C9 C -0.046(3) 0.5692(14) 0.7737(6) 0.023(4) Uani 1 1 d . . . . .
H9A H -0.1255 0.6531 0.7791 0.035 Uiso 1 1 calc R U . . .
H9B H 0.0266 0.5414 0.8088 0.035 Uiso 1 1 calc R U . . .
H9C H -0.1612 0.5038 0.7616 0.035 Uiso 1 1 calc R U . . .
C10 C 0.319(3) 0.6988(13) 0.7417(7) 0.022(4) Uani 1 1 d . . . . .
H10A H 0.4407 0.7028 0.7127 0.033 Uiso 1 1 calc R U . . .
H10B H 0.3940 0.6853 0.7779 0.033 Uiso 1 1 calc R U . . .
H10C H 0.2297 0.7808 0.7422 0.033 Uiso 1 1 calc R U . . .
F1 F 0.484(2) 0.2200(7) 0.6186(4) 0.034(2) Uani 1 1 d . . . . .
F2 F 0.4140(16) 0.0535(9) 0.5572(4) 0.033(2) Uani 1 1 d . . . . .
F3 F 0.7836(16) 0.0880(10) 0.5929(4) 0.037(2) Uani 1 1 d . . . . .
F4 F 0.492(2) 0.0090(8) 0.6485(4) 0.039(2) Uani 1 1 d . . . . .
B1 B 0.546(4) 0.095(2) 0.6046(8) 0.033(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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O3 I1 O2 169.4(4) . . ?
O3 I1 C1 92.6(6) . . ?
C1 I1 O2 76.9(5) . . ?
O1 S1 O2 117.1(6) . . ?
O1 S1 C2 109.8(7) . . ?
O1 S1 C7 109.4(7) . . ?
O2 S1 C2 103.9(7) . . ?
O2 S1 C7 107.9(7) . . ?
C2 S1 C7 108.4(7) . . ?
S1 O2 I1 116.5(5) . . ?
I1 O3 H3 93.4 . . ?
C2 C1 I1 121.7(11) . . ?
C6 C1 I1 119.1(11) . . ?
C6 C1 C2 119.0(14) . . ?
C1 C2 S1 118.6(12) . . ?
C3 C2 S1 119.6(12) . . ?
C3 C2 C1 121.8(14) . . ?
C2 C3 H3A 120.2 . . ?
C2 C3 C4 119.5(14) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(14) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(15) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.3(14) . . ?
C5 C6 H6 120.4 . . ?
C8 C7 S1 108.8(11) . . ?
C8 C7 C10 110.9(13) . . ?
C9 C7 S1 105.2(11) . . ?
C9 C7 C8 111.0(12) . . ?
C9 C7 C10 112.5(13) . . ?
C10 C7 S1 108.1(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F1 B1 F2 110.0(15) . . ?
F1 B1 F4 110.2(15) . . ?
F3 B1 F1 110.3(16) . . ?
F3 B1 F2 109.5(15) . . ?
F3 B1 F4 109.5(15) . . ?
F4 B1 F2 107.4(15) . . ?
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 O2 2.438(10) . ?
I1 O3 1.928(11) . ?
I1 C1 2.111(14) . ?
S1 O1 1.430(10) . ?
S1 O2 1.474(10) . ?
S1 C2 1.794(15) . ?
S1 C7 1.819(15) . ?
O3 H3 0.8699 . ?
C1 C2 1.38(2) . ?
C1 C6 1.38(2) . ?
C2 C3 1.36(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.40(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.37(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.55(2) . ?
C7 C9 1.53(2) . ?
C7 C10 1.56(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
F1 B1 1.37(2) . ?
F2 B1 1.43(2) . ?
F3 B1 1.37(2) . ?
F4 B1 1.41(2) . ?
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
I1 C1 C2 S1 6.0(17) . . . . ?
I1 C1 C2 C3 -175.2(11) . . . . ?
I1 C1 C6 C5 175.8(11) . . . . ?
S1 C2 C3 C4 178.6(11) . . . . ?
O1 S1 O2 I1 137.2(6) . . . . ?
O1 S1 C2 C1 -140.8(12) . . . . ?
O1 S1 C2 C3 40.4(14) . . . . ?
O1 S1 C7 C8 -174.1(10) . . . . ?
O1 S1 C7 C9 67.0(11) . . . . ?
O1 S1 C7 C10 -53.5(12) . . . . ?
O2 S1 C2 C1 -14.9(14) . . . . ?
O2 S1 C2 C3 166.3(12) . . . . ?
O2 S1 C7 C8 57.6(12) . . . . ?
O2 S1 C7 C9 -61.4(11) . . . . ?
O2 S1 C7 C10 178.2(10) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 S1 O2 I1 15.9(8) . . . . ?
C2 S1 C7 C8 -54.3(12) . . . . ?
C2 S1 C7 C9 -173.3(9) . . . . ?
C2 S1 C7 C10 66.3(12) . . . . ?
C2 C1 C6 C5 0(2) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C4 C5 C6 C1 -1(2) . . . . ?
C6 C1 C2 S1 -178.4(11) . . . . ?
C6 C1 C2 C3 0(2) . . . . ?
C7 S1 O2 I1 -99.0(7) . . . . ?
C7 S1 C2 C1 99.7(13) . . . . ?
C7 S1 C2 C3 -79.1(13) . . . . ?
