# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20240527_lixw_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2360579'
loop_
_audit_author_name
_audit_author_address
'thiophene-internal olefin-oxidative Heck'
;Guangdong University of Technology
China
;
_audit_update_record             
;
2024-06-05 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_audit_creation_date             2024-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Br N O2 S'
_chemical_formula_sum            'C10 H8 Br N O2 S'
_chemical_formula_weight         286.14
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   3.99710(10)
_cell_length_b                   7.0195(2)
_cell_length_c                   40.9871(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1150.00(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9171
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.734
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0991 before and 0.0745 after correction.
The Ratio of minimum to maximum transmission is 0.7107.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            7436
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.277
_diffrn_reflns_theta_min         2.944
_diffrn_ambient_temperature      297.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.936
_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_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                2194
_reflns_number_total             2426
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 791 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_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.060
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br 0.29275(13) 1.11344(7) 0.47272(2) 0.06629(19) Uani 1 1 d . . . . .
S002 S 0.5734(3) 0.71879(16) 0.45352(2) 0.0516(3) Uani 1 1 d . . . . .
O2 O 0.1619(10) 0.3715(5) 0.30656(7) 0.0706(9) Uani 1 1 d . . . . .
O1 O 0.3528(13) 0.6452(5) 0.28623(8) 0.0911(13) Uani 1 1 d . . . . .
N1 N 0.8547(12) 0.3235(5) 0.39979(11) 0.0662(11) Uani 1 1 d . . . . .
C2 C 0.3651(10) 0.9456(5) 0.40898(9) 0.0429(8) Uani 1 1 d . . . . .
H2 H 0.277337 1.052680 0.398726 0.051 Uiso 1 1 calc R . . . .
C4 C 0.5907(9) 0.6453(5) 0.41346(8) 0.0401(7) Uani 1 1 d . . . . .
C1 C 0.4068(10) 0.9316(5) 0.44157(9) 0.0469(9) Uani 1 1 d . . . . .
C3 C 0.4692(9) 0.7798(5) 0.39203(8) 0.0384(7) Uani 1 1 d . . . . .
C6 C 0.4490(10) 0.7578(5) 0.35598(9) 0.0428(8) Uani 1 1 d . . . . .
C5 C 0.7340(11) 0.4643(5) 0.40571(9) 0.0465(8) Uani 1 1 d . . . . .
C8 C 0.3406(10) 0.5922(5) 0.34402(9) 0.0460(8) Uani 1 1 d . . . . .
H8 H 0.292230 0.496820 0.359049 0.055 Uiso 1 1 calc R . . . .
C9 C 0.2900(12) 0.5455(6) 0.30923(9) 0.0547(10) Uani 1 1 d . . . . .
C7 C 0.5433(14) 0.9299(6) 0.33654(11) 0.0643(12) Uani 1 1 d . . . . .
H7A H 0.479385 1.042671 0.348219 0.096 Uiso 1 1 calc GR . . . .
H7B H 0.430395 0.926795 0.315873 0.096 Uiso 1 1 calc GR . . . .
H7C H 0.780821 0.930614 0.333038 0.096 Uiso 1 1 calc GR . . . .
C10 C 0.0847(19) 0.3066(9) 0.27406(12) 0.0888(19) Uani 1 1 d . . . . .
H10A H 0.284150 0.308171 0.261021 0.133 Uiso 1 1 calc GR . . . .
H10B H -0.079539 0.389283 0.264487 0.133 Uiso 1 1 calc GR . . . .
H10C H -0.001988 0.179209 0.275038 0.133 Uiso 1 1 calc GR . . . .


_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
Br1 C1 1.862(4) . ?
S002 C4 1.722(4) . ?
S002 C1 1.707(4) . ?
O2 C9 1.329(5) . ?
O2 C10 1.441(6) . ?
O1 C9 1.201(5) . ?
N1 C5 1.127(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.350(5) . ?
C2 C3 1.418(5) . ?
C4 C3 1.378(5) . ?
C4 C5 1.430(5) . ?
C3 C6 1.488(5) . ?
C6 C8 1.334(5) . ?
C6 C7 1.495(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.477(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 S002 C4 90.24(17) . . ?
C9 O2 C10 116.7(4) . . ?
C1 C2 H2 123.6 . . ?
C1 C2 C3 112.9(3) . . ?
C3 C2 H2 123.6 . . ?
C3 C4 S002 112.9(3) . . ?
C3 C4 C5 127.5(3) . . ?
C5 C4 S002 119.6(3) . . ?
S002 C1 Br1 119.9(2) . . ?
C2 C1 Br1 126.8(3) . . ?
C2 C1 S002 113.3(3) . . ?
C2 C3 C6 123.8(3) . . ?
C4 C3 C2 110.7(3) . . ?
C4 C3 C6 125.5(3) . . ?
C3 C6 C7 115.6(4) . . ?
C8 C6 C3 118.2(3) . . ?
C8 C6 C7 126.2(3) . . ?
N1 C5 C4 178.3(5) . . ?
C6 C8 H8 116.8 . . ?
C6 C8 C9 126.3(4) . . ?
C9 C8 H8 116.8 . . ?
O2 C9 C8 109.6(3) . . ?
O1 C9 O2 123.5(4) . . ?
O1 C9 C8 126.9(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
