# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_20181124pku_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2097260'
loop_
_audit_author_name
_audit_author_address
'Yue Zhao'
;Nanjing university
China
;
_audit_update_record             
;
2021-07-18 deposited with the CCDC.	2022-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Br I N O'
_chemical_formula_weight         392.03

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   19.7902(14)
_cell_length_b                   6.2266(4)
_cell_length_c                   20.7782(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.111(2)
_cell_angle_gamma                90
_cell_volume                     2503.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7085
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    5.729
_shelx_estimated_absorpt_T_min   0.365
_shelx_estimated_absorpt_T_max   0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2580
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            8284
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_full        25.002
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2194
_reflns_number_gt                2084
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0265P)²+5.5770P] 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         2194
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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 0.09058(2) 0.14739(5) 0.21342(2) 0.03405(11) Uani 1 1 d . . . . .
C1 C 0.26952(15) 0.3462(4) 0.34070(13) 0.0197(6) Uani 1 1 d . . . . .
H1 H 0.314394 0.289566 0.357117 0.024 Uiso 1 1 calc R U . . .
C2 C 0.22186(14) 0.2291(4) 0.29518(13) 0.0211(6) Uani 1 1 d . . . . .
H2 H 0.234002 0.093019 0.280302 0.025 Uiso 1 1 calc R U . . .
C3 C 0.15673(15) 0.3133(5) 0.27197(13) 0.0225(6) Uani 1 1 d . . . . .
C4 C 0.13840(15) 0.5151(5) 0.29106(14) 0.0263(6) Uani 1 1 d . . . . .
H4 H 0.093895 0.572948 0.273688 0.032 Uiso 1 1 calc R U . . .
C5 C 0.18654(17) 0.6301(4) 0.33604(14) 0.0256(6) Uani 1 1 d . . . . .
H5 H 0.174864 0.768988 0.349225 0.031 Uiso 1 1 calc R U . . .
C6 C 0.25160(14) 0.5462(4) 0.36223(13) 0.0198(5) Uani 1 1 d . . . . .
C7 C 0.30045(15) 0.6844(4) 0.40932(14) 0.0232(6) Uani 1 1 d . . . . .
C8 C 0.33998(17) 0.3650(4) 0.48398(15) 0.0260(6) Uani 1 1 d . . . . .
H8A H 0.375120 0.277760 0.468284 0.031 Uiso 1 1 calc R U . . .
H8B H 0.293856 0.304984 0.464648 0.031 Uiso 1 1 calc R U . . .
C9 C 0.35240(18) 0.3536(5) 0.55812(15) 0.0311(7) Uani 1 1 d . . . . .
H9A H 0.350128 0.202013 0.571836 0.037 Uiso 1 1 calc R U . . .
H9B H 0.315561 0.433992 0.573418 0.037 Uiso 1 1 calc R U . . .
C10 C 0.42259(16) 0.4473(5) 0.59022(15) 0.0294(6) Uani 1 1 d . . . . .
H10A H 0.425014 0.469524 0.637827 0.035 Uiso 1 1 calc R U . . .
H10B H 0.459745 0.346204 0.585175 0.035 Uiso 1 1 calc R U . . .
C11 C 0.43233(15) 0.6561(4) 0.55829(14) 0.0207(6) Uani 1 1 d . . . . .
C12 C 0.39489(14) 0.7206(4) 0.50096(13) 0.0219(6) Uani 1 1 d . . . . .
H12 H 0.402789 0.859826 0.485377 0.026 Uiso 1 1 calc R U . . .
I1 I 0.50961(2) 0.85965(3) 0.60888(2) 0.02954(10) Uani 1 1 d . . . . .
N1 N 0.34376(12) 0.5900(4) 0.46227(11) 0.0210(5) Uani 1 1 d . . . . .
O1 O 0.30186(14) 0.8787(3) 0.40029(12) 0.0398(6) 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 C3 1.896(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.394(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.495(4) . ?
C7 O1 1.226(3) . ?
C7 N1 1.377(4) . ?
C8 N1 1.478(3) . ?
C8 C9 1.510(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.490(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.326(4) . ?
C11 I1 2.092(3) . ?
C12 N1 1.411(4) . ?
C12 H12 0.9500 . ?

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
C2 C1 C6 120.3(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 Br1 119.0(2) . . ?
C4 C3 Br1 119.3(2) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 117.3(2) . . ?
C1 C6 C7 123.4(3) . . ?
O1 C7 N1 120.9(3) . . ?
O1 C7 C6 120.0(3) . . ?
N1 C7 C6 119.1(2) . . ?
N1 C8 C9 110.3(2) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 111.5(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 109.3(2) . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C10 124.3(3) . . ?
C12 C11 I1 118.7(2) . . ?
C10 C11 I1 117.0(2) . . ?
C11 C12 N1 122.4(2) . . ?
C11 C12 H12 118.8 . . ?
N1 C12 H12 118.8 . . ?
C7 N1 C12 117.5(2) . . ?
C7 N1 C8 125.8(2) . . ?
C12 N1 C8 116.7(2) . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.113



