#------------------------------------------------------------------------------
#$Date: 2025-07-06 17:12:50 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300732 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/02/7250218.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_7250218
loop_
_publ_author_name
'Höfmann, Lea'
'Wölper, Christoph'
'Huber, Alexander'
'Siera, Hannah'
'Daniliuc, Constantin G.'
'Haberhauer, Gebhard'
'Voskuhl, Jens'
_publ_section_title
;
 Tuning carbonyl interactions in dibenzochalcogenophenes
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              2902
_journal_page_last               2909
_journal_paper_doi               10.1039/D4CE01248H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_sum            'C20 H12 F3 I O4 S'
_chemical_formula_weight         532.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2025-04-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.40(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.160(5)
_cell_length_b                   15.349(7)
_cell_length_c                   13.056(6)
_cell_measurement_reflns_used    5996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.07
_cell_measurement_theta_min      2.51
_cell_volume                     1920.4(16)
_computing_cell_refinement       'BRUKER APEX3(v2019.1-0)'
_computing_data_collection       'BRUKER APEX3(v2019.1-0)'
_computing_data_reduction        'BRUKER APEX3(v2019.1-0)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'BRUKER APEX3(v2019.1-0)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 KAPPA II (APEX II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            137648
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.333
_diffrn_reflns_theta_min         2.506
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.830
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.992
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         7402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0447P)²+1.3269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6346
_reflns_number_total             7402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01248h2.cif
_cod_data_source_block           lh_075_2m_neu
_cod_depositor_comments
'Adding full bibliography for 7250216--7250224.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7250218
_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_min   0.545
_shelx_estimated_absorpt_t_max   0.859
loop_
_space_group_symop_operation_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_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 0.57028(2) 0.15468(2) 0.94665(2) 0.02787(5) Uani 1 1 d . . . . .
O1 O 0.3261(2) 0.20173(12) 0.79519(15) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.4887(2) 0.05156(13) 0.84285(17) 0.0277(4) Uani 1 1 d . . . . .
C2 C 0.3684(2) 0.05796(14) 0.75377(18) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.3192(3) -0.01809(16) 0.6957(2) 0.0377(5) Uani 1 1 d . . . . .
H3 H 0.234989 -0.017095 0.635597 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3929(3) -0.09548(16) 0.7255(2) 0.0409(5) Uani 1 1 d . . . . .
H4 H 0.357218 -0.147181 0.686018 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5165(3) -0.09884(15) 0.8107(2) 0.0363(5) Uani 1 1 d . . . . .
H5 H 0.567153 -0.151917 0.828022 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5676(2) -0.02351(13) 0.87228(17) 0.0297(4) Uani 1 1 d . . . . .
C7 C 0.6967(2) -0.01743(14) 0.96432(18) 0.0308(4) Uani 1 1 d . . . . .
C8 C 0.7926(3) -0.08482(17) 1.0041(2) 0.0427(6) Uani 1 1 d . . . . .
H8 H 0.775055 -0.140759 0.971230 0.051 Uiso 1 1 calc R U . . .
C9 C 0.9122(3) -0.0705(2) 1.0906(3) 0.0518(7) Uani 1 1 d . . . . .
H9 H 0.976933 -0.116658 1.116861 0.062 Uiso 1 1 calc R U . . .
C10 C 0.9394(3) 0.0101(2) 1.1398(3) 0.0511(7) Uani 1 1 d . . . . .
H10 H 1.023125 0.018809 1.199048 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8466(3) 0.07871(18) 1.1044(2) 0.0418(5) Uani 1 1 d . . . . .
H11 H 0.864131 0.134133 1.138635 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7278(2) 0.06284(14) 1.01715(18) 0.0305(4) Uani 1 1 d . . . . .
C13 C 0.2982(3) 0.14397(15) 0.7264(2) 0.0325(4) Uani 1 1 d . . . . .
C14 C 0.1993(2) 0.15918(14) 0.6160(2) 0.0321(4) Uani 1 1 d . . . . .
C15 C 0.0714(3) 0.19950(19) 0.6017(2) 0.0426(6) Uani 1 1 d . . . . .
H15 H 0.046138 0.215576 0.662926 0.051 Uiso 1 1 calc R U . . .
C16 C -0.0182(3) 0.2159(2) 0.4981(3) 0.0493(7) Uani 1 1 d . . . . .
H16 H -0.105882 0.242654 0.488159 0.059 Uiso 1 1 calc R U . . .
C17 C 0.0185(3) 0.19377(19) 0.4088(2) 0.0454(6) Uani 1 1 d . . . . .
H17 H -0.044273 0.204862 0.337790 0.055 Uiso 1 1 calc R U . . .
C18 C 0.1461(3) 0.15559(18) 0.4221(2) 0.0433(6) Uani 1 1 d . . . . .
H18 H 0.172556 0.142375 0.360566 0.052 Uiso 1 1 calc R U . . .
C19 C 0.2352(3) 0.13665(18) 0.5252(2) 0.0375(5) Uani 1 1 d . . . . .
H19 H 0.321345 0.108140 0.534362 0.045 Uiso 1 1 calc R U . . .
S1 S 0.68553(5) 0.31968(3) 1.17784(4) 0.02695(10) Uani 1 1 d . . . . .
F1 F 0.6521(3) 0.48797(13) 1.1595(2) 0.0860(8) Uani 1 1 d . . . . .
F2 F 0.8141(3) 0.43961(14) 1.1063(2) 0.0716(6) Uani 1 1 d . . . . .
F3 F 0.6012(3) 0.4200(2) 1.00930(18) 0.0919(9) Uani 1 1 d . . . . .
O2 O 0.7762(3) 0.33477(16) 1.28632(17) 0.0537(6) Uani 1 1 d . . . . .
O3 O 0.54252(19) 0.30779(13) 1.16772(18) 0.0441(4) Uani 1 1 d . . . . .
O4 O 0.7371(2) 0.25911(13) 1.1163(2) 0.0490(5) Uani 1 1 d . . . . .
C20 C 0.6894(3) 0.42249(18) 1.1106(2) 0.0451(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'
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
C1 I1 C12 81.65(9) . . ?
C6 C1 C2 124.2(2) . . ?
C6 C1 I1 112.73(16) . . ?
C2 C1 I1 123.11(16) . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 C13 119.0(2) . . ?
C3 C2 C13 123.9(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 117.2(2) . . ?
C1 C6 C7 117.08(19) . . ?
C5 C6 C7 125.8(2) . . ?
C12 C7 C8 117.0(2) . . ?
C12 C7 C6 117.26(19) . . ?
C8 C7 C6 125.8(2) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 117.0(3) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C11 C12 C7 123.8(2) . . ?
C11 C12 I1 125.02(18) . . ?
C7 C12 I1 111.15(16) . . ?
O1 C13 C14 121.2(2) . . ?
O1 C13 C2 119.4(2) . . ?
C14 C13 C2 119.4(2) . . ?
C19 C14 C15 119.4(2) . . ?
C19 C14 C13 120.3(2) . . ?
C15 C14 C13 120.2(2) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O3 S1 O2 114.46(15) . . ?
O3 S1 O4 114.53(13) . . ?
O2 S1 O4 115.09(15) . . ?
O3 S1 C20 104.58(14) . . ?
O2 S1 C20 103.22(15) . . ?
O4 S1 C20 102.83(14) . . ?
F1 C20 F2 107.8(3) . . ?
F1 C20 F3 107.4(3) . . ?
F2 C20 F3 107.7(3) . . ?
F1 C20 S1 112.0(2) . . ?
F2 C20 S1 111.8(2) . . ?
F3 C20 S1 110.0(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 2.069(2) . ?
I1 C12 2.102(2) . ?
O1 C13 1.226(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.391(3) . ?
C2 C13 1.486(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.458(3) . ?
C7 C12 1.396(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.375(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9500 . ?
C13 C14 1.477(3) . ?
C14 C19 1.394(4) . ?
C14 C15 1.395(3) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S1 O3 1.426(2) . ?
S1 O2 1.429(2) . ?
S1 O4 1.437(2) . ?
S1 C20 1.813(3) . ?
F1 C20 1.312(3) . ?
F2 C20 1.313(4) . ?
F3 C20 1.329(4) . ?
