# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1992564'
loop_
_audit_author_name
_audit_author_address
'Maria del Carmen Munoz Roca'
;Departament de Fisica Aplicada, Universitat Politecnica de Valencia
Spain
;
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br N O2 S'
_chemical_formula_weight         414.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   7.4286(4)
_cell_length_b                   7.2641(3)
_cell_length_c                   17.1612(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.473(2)
_cell_angle_gamma                90
_cell_volume                     920.15(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    6139
_cell_measurement_theta_min      2.7595
_cell_measurement_theta_max      27.4642

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.360
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Empirical absorption correction'

_exptl_special_details           
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker S8 x-ray diffraction'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31130
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.760
_diffrn_reflns_theta_max         29.124
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4915
_reflns_number_gt                3393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.991

_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       'APEX3, Bruker'
_computing_cell_refinement       'APEX3, Bruker'
_computing_data_reduction        'APEX3, Bruker'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0710P)²+0.2898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4915
_refine_ls_number_parameters     258
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.003
_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
Br Br 1.33506(8) 0.27415(14) 1.00487(4) 0.0837(3) Uani 1 1 d . . . . .
S S 0.15589(14) 0.3046(2) 0.59344(6) 0.0423(3) Uani 1 1 d . . . . .
O1 O 0.0572(6) 0.4712(7) 0.5992(3) 0.0598(12) Uani 1 1 d . . . . .
O2 O 0.0581(6) 0.1360(7) 0.5950(3) 0.0598(12) Uani 1 1 d . . . . .
N N 0.3285(5) 0.3024(7) 0.6650(2) 0.0413(8) Uani 1 1 d . . . . .
C1 C 0.6371(6) 0.3469(7) 0.7733(3) 0.0392(11) Uani 1 1 d . . . . .
C2 C 0.6568(6) 0.3143(9) 0.6869(3) 0.0398(10) Uani 1 1 d . . . . .
C3 C 0.4809(5) 0.3088(7) 0.6355(3) 0.0354(9) Uani 1 1 d . . . . .
C4 C 0.4707(5) 0.3131(7) 0.5488(2) 0.0334(8) Uani 1 1 d . . . . .
C5 C 0.6091(6) 0.3135(9) 0.5009(3) 0.0444(11) Uani 1 1 d . . . . .
H5 H 0.7315 0.3137 0.5221 0.053 Uiso 1 1 calc R U . . .
C6 C 0.5600(7) 0.3135(9) 0.4203(3) 0.0472(12) Uani 1 1 d . . . . .
H6 H 0.6515 0.3144 0.3867 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3822(7) 0.3123(8) 0.3882(3) 0.0463(11) Uani 1 1 d . . . . .
H7 H 0.3546 0.3119 0.3334 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2426(6) 0.3116(8) 0.4356(3) 0.0426(10) Uani 1 1 d . . . . .
H8 H 0.1205 0.3117 0.4142 0.051 Uiso 1 1 calc R U . . .
C9 C 0.2911(5) 0.3107(7) 0.5154(2) 0.0347(9) Uani 1 1 d . . . . .
C10 C 0.8111(6) 0.3210(8) 0.8277(3) 0.0405(11) Uani 1 1 d . . . . .
C11 C 0.9796(7) 0.3641(9) 0.8053(3) 0.0512(14) Uani 1 1 d . . . . .
H11 H 0.9881 0.4047 0.7538 0.061 Uiso 1 1 calc R U . . .
C12 C 1.1362(7) 0.3486(8) 0.8575(4) 0.0541(15) Uani 1 1 d . . . . .
H12 H 1.2497 0.3773 0.8414 0.065 Uiso 1 1 calc R U . . .
C13 C 1.1234(6) 0.2912(9) 0.9323(3) 0.0483(11) Uani 1 1 d . . . . .
C14 C 0.9578(8) 0.2452(13) 0.9558(3) 0.0664(19) Uani 1 1 d . . . . .
H14 H 0.9502 0.2042 1.0072 0.080 Uiso 1 1 calc R U . . .
C15 C 0.8040(7) 0.2594(12) 0.9037(3) 0.0586(16) Uani 1 1 d . . . . .
H15 H 0.6916 0.2267 0.9200 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5539(7) 0.5260(7) 0.7854(3) 0.0396(11) Uani 1 1 d . . . . .
C17 C 0.4845(9) 0.6711(8) 0.7945(3) 0.0488(13) Uani 1 1 d . . . . .
C18 C 0.3891(14) 0.8399(10) 0.8048(5) 0.075(2) Uani 1 1 d . . . . .
C19 C 0.2016(16) 0.8648(15) 0.7676(7) 0.099(3) Uani 1 1 d . . . . .
C20 C 0.241(2) 0.8420(15) 0.8544(7) 0.125(5) Uani 1 1 d D . . . .
H1 H 0.568(7) 0.248(9) 0.786(3) 0.043(14) Uiso 1 1 d . . . . .
H2B H 0.727(7) 0.403(7) 0.666(3) 0.029(13) Uiso 1 1 d . . . . .
H2A H 0.715(9) 0.207(10) 0.685(4) 0.056(19) Uiso 1 1 d . . . . .
H19A H 0.146(13) 0.975(15) 0.743(6) 0.12(3) Uiso 1 1 d . . . . .
H18 H 0.459(14) 0.926(16) 0.807(6) 0.11(4) Uiso 1 1 d . . . . .
H19B H 0.137(11) 0.763(16) 0.732(5) 0.10(3) Uiso 1 1 d D . . . .
H20A H 0.158(16) 0.751(16) 0.850(5) 0.20(7) Uiso 1 1 d D . . . .
H20B H 0.240(11) 0.951(13) 0.882(5) 0.09(3) Uiso 1 1 d . . . . .


_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
Br C13 1.896(4) . ?
S O1 1.424(5) . ?
S O2 1.426(5) . ?
S N 1.673(4) . ?
S C9 1.763(4) . ?
N C3 1.293(5) . ?
C1 C16 1.465(7) . ?
C1 C10 1.519(7) . ?
C1 C2 1.524(7) . ?
C2 C3 1.492(6) . ?
C3 C4 1.481(6) . ?
C4 C5 1.388(6) . ?
C4 C9 1.392(6) . ?
C5 C6 1.389(7) . ?
C6 C7 1.372(7) . ?
C7 C8 1.388(7) . ?
C8 C9 1.376(6) . ?
C10 C15 1.385(7) . ?
C10 C11 1.386(7) . ?
C11 C12 1.391(8) . ?
C12 C13 1.364(8) . ?
C13 C14 1.378(8) . ?
C14 C15 1.372(7) . ?
C16 C17 1.191(8) . ?
C17 C18 1.437(9) . ?
C18 C20 1.463(14) . ?
C18 C19 1.477(15) . ?
C19 C20 1.495(17) . ?

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
O1 S O2 117.5(2) . . ?
O1 S N 108.4(3) . . ?
O2 S N 109.1(3) . . ?
O1 S C9 112.0(3) . . ?
O2 S C9 111.8(3) . . ?
N S C9 95.92(18) . . ?
C3 N S 110.1(3) . . ?
C16 C1 C10 111.5(4) . . ?
C16 C1 C2 111.3(4) . . ?
C10 C1 C2 114.2(4) . . ?
C3 C2 C1 113.9(4) . . ?
N C3 C4 116.5(4) . . ?
N C3 C2 121.1(4) . . ?
C4 C3 C2 122.4(3) . . ?
C5 C4 C9 119.7(4) . . ?
C5 C4 C3 129.7(4) . . ?
C9 C4 C3 110.6(3) . . ?
C4 C5 C6 117.5(4) . . ?
C7 C6 C5 122.2(4) . . ?
C6 C7 C8 120.9(5) . . ?
C9 C8 C7 117.0(4) . . ?
C8 C9 C4 122.8(4) . . ?
C8 C9 S 130.4(3) . . ?
C4 C9 S 106.8(3) . . ?
C15 C10 C11 117.8(5) . . ?
C15 C10 C1 119.9(4) . . ?
C11 C10 C1 122.2(4) . . ?
C10 C11 C12 121.3(5) . . ?
C13 C12 C11 119.3(5) . . ?
C12 C13 C14 120.6(5) . . ?
C12 C13 Br 119.8(4) . . ?
C14 C13 Br 119.6(4) . . ?
C15 C14 C13 119.8(5) . . ?
C14 C15 C10 121.3(5) . . ?
C17 C16 C1 179.2(6) . . ?
C16 C17 C18 176.1(7) . . ?
C17 C18 C20 119.5(7) . . ?
C17 C18 C19 120.4(8) . . ?
C20 C18 C19 61.1(8) . . ?
C18 C19 C20 59.0(8) . . ?
C18 C20 C19 59.9(6) . . ?

_refine_diff_density_max         0.922
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.055

_shelxl_version_number           2014-1



