# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo_20190821f_0m
_database_code_depnum_ccdc_archive 'CCDC 1952616'
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H16 Br N O2 S'
_chemical_formula_weight         498.38

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9131(3)
_cell_length_b                   9.8841(5)
_cell_length_c                   26.9679(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.765(2)
_cell_angle_gamma                90
_cell_volume                     2108.26(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9661
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.075
_shelx_estimated_absorpt_T_min   0.670
_shelx_estimated_absorpt_T_max   0.682
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            92260
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4819
_reflns_number_gt                4151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0387P)²+2.1925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4819
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.07553(5) 0.24453(4) 0.81966(2) 0.07207(14) Uani 1 1 d . . . . .
C1 C 0.8092(3) 0.6851(2) 0.59958(8) 0.0327(4) Uani 1 1 d . . . . .
C2 C 0.9685(3) 0.7357(2) 0.61506(10) 0.0441(5) Uani 1 1 d . . . . .
H2 H 1.035554 0.686489 0.637510 0.053 Uiso 1 1 calc R U . . .
C3 C 1.0258(4) 0.8572(3) 0.59728(11) 0.0521(6) Uani 1 1 d . . . . .
H3 H 1.131175 0.889616 0.607809 0.062 Uiso 1 1 calc R U . . .
C4 C 0.9270(4) 0.9317(3) 0.56368(10) 0.0529(7) Uani 1 1 d . . . . .
H4 H 0.966785 1.013794 0.551882 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7713(4) 0.8850(2) 0.54779(9) 0.0468(6) Uani 1 1 d . . . . .
H5 H 0.706764 0.936028 0.525270 0.056 Uiso 1 1 calc R U . . .
C6 C 0.7079(3) 0.7615(2) 0.56497(8) 0.0355(5) Uani 1 1 d . . . . .
C7 C 0.5466(3) 0.7054(2) 0.54869(8) 0.0344(4) Uani 1 1 d . . . . .
C8 C 0.4228(3) 0.7588(3) 0.51487(10) 0.0472(6) Uani 1 1 d . . . . .
H8 H 0.439189 0.842623 0.500094 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2791(3) 0.6859(3) 0.50420(10) 0.0523(7) Uani 1 1 d . . . . .
H9 H 0.198954 0.722676 0.482154 0.063 Uiso 1 1 calc R U . . .
C10 C 0.2463(3) 0.5573(3) 0.52502(9) 0.0455(6) Uani 1 1 d . . . . .
H10 H 0.147784 0.510194 0.516597 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3643(3) 0.5044(2) 0.55802(8) 0.0348(5) Uani 1 1 d . . . . .
C12 C 0.5092(3) 0.5815(2) 0.56837(7) 0.0311(4) Uani 1 1 d . . . . .
C13 C 0.6173(3) 0.5144(2) 0.60360(7) 0.0294(4) Uani 1 1 d . . . . .
C14 C 0.5320(3) 0.3861(2) 0.61644(8) 0.0315(4) Uani 1 1 d . . . . .
C15 C 0.3855(3) 0.3804(2) 0.58867(8) 0.0349(5) Uani 1 1 d . . . . .
C16 C 0.5956(3) 0.2936(2) 0.65582(9) 0.0345(5) Uani 1 1 d . . . . .
C17 C 0.5816(3) 0.3328(3) 0.70461(9) 0.0434(5) Uani 1 1 d . . . . .
H17 H 0.534782 0.416433 0.711969 0.052 Uiso 1 1 calc R U . . .
C18 C 0.6372(4) 0.2477(3) 0.74292(12) 0.0619(9) Uani 1 1 d . . . . .
H18 H 0.625653 0.273524 0.775800 0.074 Uiso 1 1 calc R U . . .
C19 C 0.7091(4) 0.1257(3) 0.73182(15) 0.0736(11) Uani 1 1 d . . . . .
H19 H 0.747456 0.068880 0.757244 0.088 Uiso 1 1 calc R U . . .
C20 C 0.7245(4) 0.0873(3) 0.68358(17) 0.0746(11) Uani 1 1 d . . . . .
H20 H 0.773534 0.004303 0.676488 0.090 Uiso 1 1 calc R U . . .
C21 C 0.6684(4) 0.1697(3) 0.64506(12) 0.0544(7) Uani 1 1 d . . . . .
H21 H 0.679295 0.142412 0.612308 0.065 Uiso 1 1 calc R U . . .
C22 C 0.1815(3) 0.2388(2) 0.65223(9) 0.0358(5) Uani 1 1 d . . . . .
C23 C 0.0807(3) 0.3403(2) 0.67084(10) 0.0407(5) Uani 1 1 d . . . . .
H23 H 0.035550 0.406769 0.649954 0.049 Uiso 1 1 calc R U . . .
C24 C 0.0482(3) 0.3412(2) 0.72079(10) 0.0444(6) Uani 1 1 d . . . . .
H24 H -0.017727 0.409239 0.734117 0.053 Uiso 1 1 calc R U . . .
C25 C 0.1151(3) 0.2397(2) 0.75088(10) 0.0420(5) Uani 1 1 d . . . . .
C26 C 0.2085(3) 0.1361(3) 0.73193(10) 0.0457(6) Uani 1 1 d . . . . .
H26 H 0.247610 0.066468 0.752436 0.055 Uiso 1 1 calc R U . . .
C27 C 0.2439(3) 0.1361(2) 0.68192(10) 0.0424(5) Uani 1 1 d . . . . .
H27 H 0.309102 0.067606 0.668613 0.051 Uiso 1 1 calc R U . . .
N1 N 0.7628(2) 0.56072(18) 0.61956(7) 0.0324(4) Uani 1 1 d . . . . .
O1 O 0.0931(3) 0.2899(2) 0.56018(8) 0.0644(6) Uani 1 1 d . . . . .
O2 O 0.3204(3) 0.1223(2) 0.57759(7) 0.0582(5) Uani 1 1 d . . . . .
S1 S 0.23779(8) 0.24688(6) 0.58951(2) 0.04327(16) Uani 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
Br1 C25 1.891(3) . ?
C1 N1 1.396(3) . ?
C1 C2 1.407(3) . ?
C1 C6 1.427(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.448(3) . ?
C7 C12 1.371(3) . ?
C7 C8 1.420(3) . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.417(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(3) . ?
C11 C15 1.485(3) . ?
C12 C13 1.422(3) . ?
C13 N1 1.300(3) . ?
C13 C14 1.482(3) . ?
C14 C15 1.362(3) . ?
C14 C16 1.478(3) . ?
C15 S1 1.763(2) . ?
C16 C17 1.379(3) . ?
C16 C21 1.388(4) . ?
C17 C18 1.393(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.375(3) . ?
C22 C23 1.385(3) . ?
C22 S1 1.764(2) . ?
C23 C24 1.379(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(4) . ?
C26 C27 1.386(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
O1 S1 1.436(2) . ?
O2 S1 1.435(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
N1 C1 C2 116.2(2) . . ?
N1 C1 C6 124.73(19) . . ?
C2 C1 C6 119.0(2) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 123.6(2) . . ?
C1 C6 C7 117.84(19) . . ?
C12 C7 C8 115.4(2) . . ?
C12 C7 C6 115.09(19) . . ?
C8 C7 C6 129.5(2) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 123.4(2) . . ?
C8 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C11 C10 C9 118.0(2) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C10 C11 C12 117.3(2) . . ?
C10 C11 C15 137.6(2) . . ?
C12 C11 C15 105.12(18) . . ?
C7 C12 C11 126.5(2) . . ?
C7 C12 C13 122.9(2) . . ?
C11 C12 C13 110.60(19) . . ?
N1 C13 C12 124.40(19) . . ?
N1 C13 C14 128.97(19) . . ?
C12 C13 C14 106.62(17) . . ?
C15 C14 C16 129.40(19) . . ?
C15 C14 C13 107.04(18) . . ?
C16 C14 C13 123.35(18) . . ?
C14 C15 C11 110.59(19) . . ?
C14 C15 S1 125.26(17) . . ?
C11 C15 S1 124.14(16) . . ?
C17 C16 C21 119.6(2) . . ?
C17 C16 C14 118.4(2) . . ?
C21 C16 C14 122.0(2) . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 119.2(3) . . ?
C20 C21 H21 120.4 . . ?
C16 C21 H21 120.4 . . ?
C27 C22 C23 121.6(2) . . ?
C27 C22 S1 119.64(19) . . ?
C23 C22 S1 118.70(18) . . ?
C24 C23 C22 119.1(2) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 119.2(2) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C26 C25 C24 121.6(2) . . ?
C26 C25 Br1 119.46(19) . . ?
C24 C25 Br1 119.0(2) . . ?
C25 C26 C27 119.4(2) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C22 C27 C26 119.1(2) . . ?
C22 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C13 N1 C1 115.04(18) . . ?
O2 S1 O1 119.45(14) . . ?
O2 S1 C15 109.41(12) . . ?
O1 S1 C15 106.78(12) . . ?
O2 S1 C22 107.85(12) . . ?
O1 S1 C22 108.73(13) . . ?
C15 S1 C22 103.47(10) . . ?

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.054

