# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_LXMCYCZ2
_database_code_depnum_ccdc_archive 'CCDC 2090356'
loop_
_audit_author_name
_audit_author_address
MengLi
;Nanjing Tech University
China
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Br N2 O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         541.45

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7302(10)
_cell_length_b                   10.4685(12)
_cell_length_c                   14.6224(14)
_cell_angle_alpha                89.908(7)
_cell_angle_beta                 84.866(6)
_cell_angle_gamma                69.947(6)
_cell_volume                     1249.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3463
_cell_measurement_theta_min      2.9050
_cell_measurement_theta_max      25.6052
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556

_exptl_absorpt_coefficient_mu    1.763
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.72

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9221
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_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       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4595
_reflns_number_gt                2757
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1351
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_number_reflns         4595
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+2.7559P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.507
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.22553(9) -0.11568(7) 0.50434(5) 0.0828(3) Uani d . . . 1 . .
C C1 0.5628(6) 0.5542(5) 0.6545(3) 0.0499(12) Uani d . . . 1 . .
H H1 0.459128 0.620299 0.663891 0.06 Uiso calc U . R 1 . .
C C2 0.6442(6) 0.5321(5) 0.5672(3) 0.0538(13) Uani d . . . 1 . .
H H2 0.596092 0.581465 0.518039 0.065 Uiso calc U . R 1 . .
C C3 0.7966(6) 0.4363(5) 0.5554(3) 0.0447(11) Uani d . . . 1 . .
C C4 0.8711(6) 0.3620(5) 0.6264(3) 0.0517(12) Uani d . . . 1 . .
H H4 0.976321 0.298333 0.616597 0.062 Uiso calc U . R 1 . .
C C5 0.7874(6) 0.3835(5) 0.7121(3) 0.0495(12) Uani d . . . 1 . .
H H5 0.835837 0.332102 0.760515 0.059 Uiso calc U . R 1 . .
C C6 0.6318(5) 0.4804(4) 0.7281(3) 0.0386(10) Uani d . . . 1 . .
C C7 0.5506(5) 0.5003(4) 0.8234(3) 0.0437(11) Uani d . . . 1 . .
H H7 0.622873 0.504016 0.870124 0.052 Uiso calc U . R 1 . .
C C8 0.3760(5) 0.5852(4) 0.8477(3) 0.0381(10) Uani d . . . 1 . .
H H8 0.313011 0.623912 0.795921 0.046 Uiso calc U . R 1 . .
C C9 0.4241(5) 0.4339(4) 0.8560(3) 0.0409(11) Uani d . . . 1 . .
H H9 0.429701 0.400609 0.918705 0.049 Uiso calc U . R 1 . .
C C10 0.3686(6) 0.3572(4) 0.7901(3) 0.0450(11) Uani d . . . 1 . .
H H10 0.365452 0.386377 0.729931 0.054 Uiso calc U . R 1 . .
C C11 0.3228(5) 0.2508(4) 0.8075(3) 0.0426(11) Uani d . . . 1 . .
C C12 0.3169(9) 0.1963(7) 0.9028(3) 0.087(2) Uani d . . . 1 . .
H H12A 0.351684 0.249396 0.944478 0.13 Uiso calc U . R 1 . .
H H12B 0.388348 0.103191 0.902274 0.13 Uiso calc U . R 1 . .
H H12C 0.206868 0.201704 0.922457 0.13 Uiso calc U . R 1 . .
C C13 0.2833(5) 0.1730(4) 0.7334(3) 0.0372(10) Uani d . . . 1 . .
C C14 0.1903(6) 0.0901(5) 0.7509(3) 0.0517(12) Uani d . . . 1 . .
H H14 0.141351 0.089724 0.809989 0.062 Uiso calc U . R 1 . .
C C15 0.1681(6) 0.0075(5) 0.6827(4) 0.0574(13) Uani d . . . 1 . .
H H15 0.106197 -0.048014 0.696483 0.069 Uiso calc U . R 1 . .
C C16 0.2381(6) 0.0084(5) 0.5950(3) 0.0487(12) Uani d . . . 1 . .
C C17 0.3222(6) 0.0952(5) 0.5737(3) 0.0457(11) Uani d . . . 1 . .
H H17 0.363882 0.099616 0.513498 0.055 Uiso calc U . R 1 . .
C C18 0.3448(5) 0.1758(5) 0.6419(3) 0.0438(11) Uani d . . . 1 . .
H H18 0.402687 0.233936 0.626674 0.053 Uiso calc U . R 1 . .
C C19 0.3753(7) 0.7979(5) 0.9142(4) 0.0603(14) Uani d . . . 1 . .
H H19A 0.490038 0.775959 0.895954 0.09 Uiso calc U . R 1 . .
H H19B 0.346379 0.852737 0.969925 0.09 Uiso calc U . R 1 . .
H H19C 0.312945 0.847465 0.86668 0.09 Uiso calc U . R 1 . .
C C20 0.0128(5) 0.7466(4) 0.9098(3) 0.0388(10) Uani d . . . 1 . .
C C21 -0.0240(6) 0.6547(5) 0.8556(3) 0.0459(11) Uani d . . . 1 . .
H H21 0.024001 0.561768 0.863649 0.055 Uiso calc U . R 1 . .
C C22 -0.1315(6) 0.7011(5) 0.7900(3) 0.0514(12) Uani d . . . 1 . .
H H22 -0.155131 0.63869 0.753622 0.062 Uiso calc U . R 1 . .
C C23 -0.2050(6) 0.8380(5) 0.7768(3) 0.0507(12) Uani d . . . 1 . .
C C24 -0.1681(6) 0.9287(5) 0.8318(3) 0.0523(13) Uani d . . . 1 . .
H H24 -0.218097 1.021542 0.824351 0.063 Uiso calc U . R 1 . .
C C25 -0.0591(6) 0.8849(5) 0.8975(3) 0.0484(12) Uani d . . . 1 . .
H H25 -0.034152 0.947421 0.93312 0.058 Uiso calc U . R 1 . .
C C26 -0.3210(7) 0.8860(6) 0.7040(4) 0.0785(18) Uani d . . . 1 . .
H H26A -0.306463 0.964549 0.676023 0.118 Uiso calc U . R 1 . .
H H26B -0.431616 0.909264 0.73137 0.118 Uiso calc U . R 1 . .
H H26C -0.299105 0.814835 0.658208 0.118 Uiso calc U . R 1 . .
N N1 0.8843(6) 0.4131(5) 0.4625(3) 0.0581(11) Uani d . . . 1 . .
N N2 0.3394(4) 0.6716(3) 0.9297(2) 0.0401(9) Uani d . . . 1 . .
O O1 0.1683(4) 0.5554(3) 1.0147(2) 0.0515(8) Uani d . . . 1 . .
O O2 0.1353(4) 0.7920(3) 1.0573(2) 0.0568(9) Uani d . . . 1 . .
O O3 0.8104(5) 0.4668(5) 0.3983(3) 0.0923(14) Uani d . . . 1 . .
O O4 1.0272(5) 0.3403(4) 0.4544(3) 0.0778(12) Uani d . . . 1 . .
S S1 0.16163(15) 0.68837(12) 0.98786(7) 0.0438(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C16 . 1.893(5) ?
C1 C2 . 1.383(6) ?
C1 C6 . 1.383(6) ?
C2 C3 . 1.361(6) ?
C3 C4 . 1.370(6) ?
C3 N1 . 1.476(6) ?
C4 C5 . 1.372(6) ?
C5 C6 . 1.389(6) ?
C6 C7 . 1.487(6) ?
C7 C8 . 1.488(6) ?
C7 C9 . 1.537(6) ?
C8 N2 . 1.448(5) ?
C8 C9 . 1.500(6) ?
C9 C10 . 1.471(6) ?
C10 C11 . 1.323(6) ?
C11 C13 . 1.490(6) ?
C11 C12 . 1.509(6) ?
C13 C14 . 1.387(6) ?
C13 C18 . 1.400(6) ?
C14 C15 . 1.389(7) ?
C15 C16 . 1.372(6) ?
C16 C17 . 1.370(6) ?
C17 C18 . 1.377(6) ?
C19 N2 . 1.473(6) ?
C20 C21 . 1.384(6) ?
C20 C25 . 1.386(6) ?
C20 S1 . 1.755(4) ?
C21 C22 . 1.373(6) ?
C22 C23 . 1.376(6) ?
C23 C24 . 1.382(7) ?
C23 C26 . 1.501(7) ?
C24 C25 . 1.379(6) ?
N1 O3 . 1.213(5) ?
N1 O4 . 1.213(5) ?
N2 S1 . 1.655(4) ?
O1 S1 . 1.429(3) ?
O2 S1 . 1.432(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.6(4) ?
C3 C2 C1 . . 118.2(4) ?
C2 C3 C4 . . 122.4(4) ?
C2 C3 N1 . . 118.3(4) ?
C4 C3 N1 . . 119.3(4) ?
C3 C4 C5 . . 118.6(4) ?
C4 C5 C6 . . 121.3(4) ?
C1 C6 C5 . . 117.9(4) ?
C1 C6 C7 . . 123.9(4) ?
C5 C6 C7 . . 118.2(4) ?
C6 C7 C8 . . 123.6(4) ?
C6 C7 C9 . . 122.3(4) ?
C8 C7 C9 . . 59.4(3) ?
N2 C8 C7 . . 116.9(4) ?
N2 C8 C9 . . 119.8(4) ?
C7 C8 C9 . . 61.9(3) ?
C10 C9 C8 . . 118.7(4) ?
C10 C9 C7 . . 120.0(4) ?
C8 C9 C7 . . 58.7(3) ?
C11 C10 C9 . . 126.7(4) ?
C10 C11 C13 . . 122.0(4) ?
C10 C11 C12 . . 121.9(5) ?
C13 C11 C12 . . 116.0(4) ?
C14 C13 C18 . . 116.3(4) ?
C14 C13 C11 . . 122.5(4) ?
C18 C13 C11 . . 121.1(4) ?
C13 C14 C15 . . 122.0(4) ?
C16 C15 C14 . . 119.5(5) ?
C17 C16 C15 . . 120.2(5) ?
C17 C16 Br1 . . 119.9(4) ?
C15 C16 Br1 . . 119.8(4) ?
C16 C17 C18 . . 119.8(4) ?
C17 C18 C13 . . 122.0(4) ?
C21 C20 C25 . . 119.8(4) ?
C21 C20 S1 . . 120.2(3) ?
C25 C20 S1 . . 119.8(3) ?
C22 C21 C20 . . 119.9(4) ?
C21 C22 C23 . . 121.4(5) ?
C22 C23 C24 . . 118.2(4) ?
C22 C23 C26 . . 120.3(5) ?
C24 C23 C26 . . 121.5(5) ?
C25 C24 C23 . . 121.7(4) ?
C24 C25 C20 . . 119.1(4) ?
O3 N1 O4 . . 123.4(4) ?
O3 N1 C3 . . 118.7(4) ?
O4 N1 C3 . . 117.9(5) ?
C8 N2 C19 . . 112.6(4) ?
C8 N2 S1 . . 114.2(3) ?
C19 N2 S1 . . 116.2(3) ?
O1 S1 O2 . . 119.2(2) ?
O1 S1 N2 . . 107.01(19) ?
O2 S1 N2 . . 106.2(2) ?
O1 S1 C20 . . 108.3(2) ?
O2 S1 C20 . . 109.2(2) ?
N2 S1 C20 . . 106.20(19) ?

