 
data_A24251O_019
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C13 H10 I S2, B F4'
_chemical_formula_sum
 'C13 H10 B F4 I S2' 
_chemical_formula_weight          444.04

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'
 'S'  'S'   0.1246   0.1234
 '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'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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.
;
 
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'
 
_cell_length_a                    9.2891(4)
_cell_length_b                    10.3259(4)
_cell_length_c                    15.9566(6)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1530.53(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     203(2)
_cell_measurement_reflns_used     9913
_cell_measurement_theta_min       2.54
_cell_measurement_theta_max       27.31
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.927          
_exptl_crystal_F_000              856
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.085
_exptl_crystal_size_mid           0.067
_exptl_crystal_size_min           0.053
_exptl_absorpt_coefficient_mu     2.395
_shelx_estimated_absorpt_T_min    0.822
_shelx_estimated_absorpt_T_max    0.884
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.5988
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       203(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Ius 3.0 microfocus source'
_diffrn_measurement_device_type   'PHOTON II CPAD detector'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             36690
_diffrn_reflns_av_unetI/netI      0.0348
_diffrn_reflns_av_R_equivalents   0.0794
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.537
_diffrn_reflns_theta_max          27.993
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3689
_reflns_number_gt                 2999
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.745
_reflns_Friedel_fraction_max      0.999
_reflns_Friedel_fraction_full     1.000
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX5 software' 
_computing_cell_refinement        'Bruker APEX5 software' 
_computing_data_reduction         'Bruker APEX5 software' 
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0370P)²+1.5389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef        0.0114(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.006(12)
_chemical_absolute_configuration  .
_refine_ls_number_reflns          3689
_refine_ls_number_parameters      228
_refine_ls_number_restraints      150
_refine_ls_R_factor_all           0.0597
_refine_ls_R_factor_gt            0.0336
_refine_ls_wR_factor_ref          0.0997
_refine_ls_wR_factor_gt           0.0781
_refine_ls_goodness_of_fit_ref    1.254
_refine_ls_restrained_S_all       1.274
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.81486(6) 0.84606(5) 0.29575(3) 0.04542(19) Uani 1 1 d . . . . .
C2 C 0.7976(9) 0.6922(7) 0.3853(5) 0.0404(17) Uani 1 1 d . . . . .
H2A H 0.867491 0.623066 0.371452 0.049 Uiso 1 1 calc R U . . .
H2B H 0.820327 0.725301 0.441958 0.049 Uiso 1 1 calc R U . . .
S3 S 0.6186(2) 0.62738(17) 0.38404(11) 0.0343(4) Uani 1 1 d . . . . .
C4 C 0.6059(8) 0.5544(7) 0.2849(5) 0.0342(15) Uani 1 1 d . . . . .
C5 C 0.5114(9) 0.6126(8) 0.2275(5) 0.0415(19) Uani 1 1 d . . . . .
H5 H 0.453424 0.684061 0.243938 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5038(10) 0.5639(9) 0.1460(5) 0.046(2) Uani 1 1 d . . . . .
H6 H 0.442013 0.602452 0.105666 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5889(11) 0.4573(9) 0.1251(5) 0.050(2) Uani 1 1 d . . . . .
H7 H 0.583599 0.423666 0.069762 0.060 Uiso 1 1 calc R U . . .
C8 C 0.6791(10) 0.3999(7) 0.1809(4) 0.0421(17) Uani 1 1 d . . . . .
H8 H 0.735315 0.327490 0.164146 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6896(10) 0.4469(7) 0.2631(4) 0.0354(14) Uani 1 1 d . . . . .
S10 S 0.8070(2) 0.3673(2) 0.33193(12) 0.0452(5) Uani 1 1 d . . . . .
C11 C 0.7196(8) 0.3857(7) 0.4291(5) 0.0376(17) Uani 1 1 d . . . . .
C12 C 0.7345(10) 0.2851(8) 0.4874(5) 0.046(2) Uani 1 1 d . . . . .
H12 H 0.792092 0.211734 0.474430 0.055 Uiso 1 1 calc R U . . .
C13 C 0.6654(12) 0.2930(8) 0.5634(5) 0.051(2) Uani 1 1 d . . . . .
H13 H 0.676326 0.224425 0.602583 0.061 Uiso 1 1 calc R U . . .
C14 C 0.5811(10) 0.3974(8) 0.5842(5) 0.046(2) Uani 1 1 d . . . . .
H14 H 0.533847 0.400293 0.636980 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5654(9) 0.4988(8) 0.5278(5) 0.0393(17) Uani 1 1 d . . . . .
H15 H 0.507123 0.571453 0.541278 0.047 Uiso 1 1 calc R U . . .
C16 C 0.6361(8) 0.4922(7) 0.4512(4) 0.0325(15) Uani 1 1 d . . . . .
B20 B 0.1740(13) 0.5868(10) 0.4154(6) 0.047(2) Uani 1 1 d . U . . .
F21 F 0.1192(18) 0.7057(9) 0.4484(7) 0.069(3) Uani 0.70(2) 1 d D U P A 1
F22 F 0.0761(13) 0.5011(10) 0.4489(7) 0.062(3) Uani 0.70(2) 1 d D U P A 1
F23 F 0.147(2) 0.5966(17) 0.3288(9) 0.077(5) Uani 0.70(2) 1 d D U P A 1
F24 F 0.3074(14) 0.580(2) 0.4285(12) 0.148(6) Uani 0.70(2) 1 d D U P A 1
F31 F 0.219(4) 0.691(2) 0.4528(15) 0.078(8) Uani 0.30(2) 1 d D U P A 2
F32 F 0.149(5) 0.503(3) 0.479(2) 0.106(10) Uani 0.30(2) 1 d D U P A 2
F33 F 0.113(4) 0.585(5) 0.346(2) 0.084(10) Uani 0.30(2) 1 d D U P A 2
F34 F 0.306(3) 0.506(2) 0.3948(19) 0.077(7) Uani 0.30(2) 1 d D U P A 2
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C2 2.142(7) . ?
C2 S3 1.792(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
S3 C4 1.756(7) . ?
S3 C16 1.768(7) . ?
C4 C9 1.398(10) . ?
C4 C5 1.404(11) . ?
C5 C6 1.397(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.359(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(10) . ?
C8 H8 0.9500 . ?
C9 S10 1.753(8) . ?
S10 C11 1.760(8) . ?
C11 C16 1.392(10) . ?
C11 C12 1.401(11) . ?
C12 C13 1.375(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(10) . ?
C15 H15 0.9500 . ?
B20 F33 1.25(3) . ?
B20 F24 1.259(17) . ?
B20 F31 1.30(2) . ?
B20 F32 1.35(3) . ?
B20 F22 1.376(14) . ?
B20 F23 1.408(17) . ?
B20 F21 1.430(14) . ?
B20 F34 1.52(2) . ?
 
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
S3 C2 I1 109.8(4) . . ?
S3 C2 H2A 109.7 . . ?
I1 C2 H2A 109.7 . . ?
S3 C2 H2B 109.7 . . ?
I1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 S3 C16 102.3(3) . . ?
C4 S3 C2 103.4(4) . . ?
C16 S3 C2 101.7(4) . . ?
C9 C4 C5 121.7(7) . . ?
C9 C4 S3 121.8(6) . . ?
C5 C4 S3 116.4(6) . . ?
C6 C5 C4 119.0(8) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C6 C5 118.6(8) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C6 122.5(8) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 120.3(8) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 118.0(8) . . ?
C4 C9 S10 124.2(5) . . ?
C8 C9 S10 117.8(6) . . ?
C9 S10 C11 102.4(4) . . ?
C16 C11 C12 118.2(7) . . ?
C16 C11 S10 124.5(6) . . ?
C12 C11 S10 117.3(6) . . ?
C13 C12 C11 119.7(8) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 121.8(8) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 119.7(8) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.9(8) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C11 121.7(7) . . ?
C15 C16 S3 116.8(6) . . ?
C11 C16 S3 121.4(6) . . ?
F33 B20 F31 125(3) . . ?
F33 B20 F32 125(3) . . ?
F31 B20 F32 104(2) . . ?
F24 B20 F22 123.5(14) . . ?
F24 B20 F23 109.9(13) . . ?
F22 B20 F23 108.1(11) . . ?
F24 B20 F21 109.6(13) . . ?
F22 B20 F21 100.0(10) . . ?
F23 B20 F21 103.7(11) . . ?
F33 B20 F34 99(2) . . ?
F31 B20 F34 107(2) . . ?
F32 B20 F34 87.1(18) . . ?
 
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 C2 S3 C4 67.1(4) . . . . ?
I1 C2 S3 C16 173.0(4) . . . . ?
C16 S3 C4 C9 -39.6(7) . . . . ?
C2 S3 C4 C9 65.8(7) . . . . ?
C16 S3 C4 C5 142.8(6) . . . . ?
C2 S3 C4 C5 -111.9(6) . . . . ?
C9 C4 C5 C6 -1.8(12) . . . . ?
S3 C4 C5 C6 175.9(6) . . . . ?
C4 C5 C6 C7 1.2(12) . . . . ?
C5 C6 C7 C8 -0.3(14) . . . . ?
C6 C7 C8 C9 0.1(13) . . . . ?
C5 C4 C9 C8 1.5(11) . . . . ?
S3 C4 C9 C8 -176.1(6) . . . . ?
C5 C4 C9 S10 -178.7(6) . . . . ?
S3 C4 C9 S10 3.8(10) . . . . ?
C7 C8 C9 C4 -0.6(12) . . . . ?
C7 C8 C9 S10 179.5(7) . . . . ?
C4 C9 S10 C11 32.5(8) . . . . ?
C8 C9 S10 C11 -147.6(7) . . . . ?
C9 S10 C11 C16 -32.4(8) . . . . ?
C9 S10 C11 C12 146.9(7) . . . . ?
C16 C11 C12 C13 1.0(13) . . . . ?
S10 C11 C12 C13 -178.3(7) . . . . ?
C11 C12 C13 C14 0.1(14) . . . . ?
C12 C13 C14 C15 -0.5(14) . . . . ?
C13 C14 C15 C16 -0.2(13) . . . . ?
C14 C15 C16 C11 1.4(12) . . . . ?
C14 C15 C16 S3 -177.2(6) . . . . ?
C12 C11 C16 C15 -1.8(12) . . . . ?
S10 C11 C16 C15 177.5(6) . . . . ?
C12 C11 C16 S3 176.7(6) . . . . ?
S10 C11 C16 S3 -4.0(10) . . . . ?
C4 S3 C16 C15 -141.8(6) . . . . ?
C2 S3 C16 C15 111.5(6) . . . . ?
C4 S3 C16 C11 39.6(7) . . . . ?
C2 S3 C16 C11 -67.1(7) . . . . ?
 
_refine_diff_density_max    1.318
_refine_diff_density_min   -0.720
_refine_diff_density_rms    0.119



