# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_zhaoyue_LCM_4_Cl_0m_4_a
_audit_block_doi                 10.5517/ccdc.csd.cc23t9z7
_database_code_depnum_ccdc_archive 'CCDC 1960749'
loop_
_audit_author_name
_audit_author_address
'Jian Li '
;Changzhou University
China
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-24 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            'C18 H11 Br  N2 O3'
_chemical_formula_weight         383.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   7.600
_cell_length_b                   17.754
_cell_length_c                   11.242
_cell_angle_alpha                90
_cell_angle_beta                 91.42
_cell_angle_gamma                90
_cell_volume                     1516.5
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3642
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      32.14

_exptl_crystal_description       block
_exptl_crystal_colour            coloeless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.552
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            2626
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.050
_diffrn_reflns_theta_max         53.047
_diffrn_reflns_theta_full        53.047
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2626
_reflns_number_gt                2433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0998P)²+1.6695P] 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         2626
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_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 0.07372(6) 0.62471(3) -0.05803(4) 0.0420(2) Uani 1 1 d . . . . .
C1 C 0.4590(6) 0.3777(2) 1.1843(4) 0.0397(10) Uani 1 1 d . . . . .
H1A H 0.378823 0.340830 1.213899 0.060 Uiso 1 1 calc R U . . .
H1B H 0.456473 0.421792 1.233718 0.060 Uiso 1 1 calc R U . . .
H1C H 0.575938 0.357289 1.185228 0.060 Uiso 1 1 calc R U . . .
C2 C 0.3818(5) 0.3390(2) 0.9897(3) 0.0322(8) Uani 1 1 d . . . . .
C3 C 0.3240(5) 0.3622(2) 0.8675(4) 0.0334(8) Uani 1 1 d . . . . .
C4 C 0.3433(5) 0.4370(2) 0.8279(4) 0.0362(9) Uani 1 1 d . . . . .
H4 H 0.387667 0.473706 0.879477 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2963(5) 0.4556(2) 0.7123(4) 0.0360(8) Uani 1 1 d . . . . .
H5 H 0.311407 0.504771 0.685901 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2257(5) 0.4011(2) 0.6339(3) 0.0313(8) Uani 1 1 d . . . . .
C7 C 0.2031(5) 0.3274(2) 0.6749(4) 0.0362(8) Uani 1 1 d . . . . .
H7 H 0.154587 0.290998 0.624412 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2528(5) 0.3083(2) 0.7906(3) 0.0353(9) Uani 1 1 d . . . . .
H8 H 0.238370 0.259089 0.816924 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1758(5) 0.4206(2) 0.5131(4) 0.0349(8) Uani 1 1 d . . . . .
C10 C 0.0806(5) 0.3873(2) 0.4218(4) 0.0358(9) Uani 1 1 d . . . . .
H10 H 0.027059 0.340228 0.425249 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1653(5) 0.4936(2) 0.3582(3) 0.0336(8) Uani 1 1 d . . . . .
C12 C 0.1974(5) 0.5623(2) 0.2897(4) 0.0341(8) Uani 1 1 d . . . . .
C13 C 0.2798(6) 0.6272(2) 0.3376(4) 0.0335(9) Uani 1 1 d . . . . .
C14 C 0.2928(5) 0.6916(2) 0.2665(4) 0.0371(9) Uani 1 1 d . . . . .
H14 H 0.344704 0.734892 0.298196 0.045 Uiso 1 1 calc R U . . .
C15 C 0.2297(5) 0.6921(2) 0.1499(4) 0.0370(8) Uani 1 1 d . . . . .
H15 H 0.237362 0.735436 0.103854 0.044 Uiso 1 1 calc R U . . .
C16 C 0.1549(6) 0.6271(2) 0.1026(4) 0.0347(9) Uani 1 1 d . . . . .
C17 C 0.1375(5) 0.5626(2) 0.1705(3) 0.0358(8) Uani 1 1 d . . . . .
H17 H 0.086263 0.519625 0.137296 0.043 Uiso 1 1 calc R U . . .
C18 C 0.3509(6) 0.6321(2) 0.4579(4) 0.0392(10) Uani 1 1 d . . . . .
N1 N 0.0768(4) 0.43462(19) 0.3241(3) 0.0357(7) Uani 1 1 d . . . . .
N2 N 0.4123(6) 0.6399(3) 0.5507(4) 0.0502(10) Uani 1 1 d . . . . .
O1 O 0.4072(4) 0.39784(18) 1.0634(2) 0.0406(7) Uani 1 1 d . . . . .
O2 O 0.4024(4) 0.27444(16) 1.0190(3) 0.0425(7) Uani 1 1 d . . . . .
O3 O 0.2303(3) 0.48949(15) 0.4716(2) 0.0345(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 C16 1.895(4) . ?
C1 O1 1.450(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.201(5) . ?
C2 O1 1.344(5) . ?
C2 C3 1.491(5) . ?
C3 C8 1.391(6) . ?
C3 C4 1.409(6) . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(6) . ?
C6 C9 1.444(5) . ?
C7 C8 1.387(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.375(6) . ?
C9 O3 1.376(5) . ?
C10 N1 1.383(5) . ?
C10 H10 0.9300 . ?
C11 N1 1.297(5) . ?
C11 O3 1.358(5) . ?
C11 C12 1.466(5) . ?
C12 C17 1.405(5) . ?
C12 C13 1.411(6) . ?
C13 C14 1.401(6) . ?
C13 C18 1.447(7) . ?
C14 C15 1.385(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(6) . ?
C17 H17 0.9300 . ?
C18 N2 1.141(6) . ?

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 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.9(4) . . ?
O2 C2 C3 123.4(4) . . ?
O1 C2 C3 112.8(3) . . ?
C8 C3 C4 119.6(4) . . ?
C8 C3 C2 118.9(4) . . ?
C4 C3 C2 121.5(4) . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 C9 120.2(4) . . ?
C5 C6 C9 120.7(4) . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C3 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 O3 106.7(3) . . ?
C10 C9 C6 136.0(4) . . ?
O3 C9 C6 117.3(3) . . ?
C9 C10 N1 109.3(4) . . ?
C9 C10 H10 125.3 . . ?
N1 C10 H10 125.3 . . ?
N1 C11 O3 114.0(3) . . ?
N1 C11 C12 127.5(3) . . ?
O3 C11 C12 118.4(3) . . ?
C17 C12 C13 119.4(4) . . ?
C17 C12 C11 116.7(4) . . ?
C13 C12 C11 123.9(4) . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 C18 117.0(4) . . ?
C12 C13 C18 123.9(4) . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.1(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 121.4(4) . . ?
C17 C16 Br1 118.3(3) . . ?
C15 C16 Br1 120.3(3) . . ?
C16 C17 C12 119.7(4) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
N2 C18 C13 175.8(5) . . ?
C11 N1 C10 104.9(3) . . ?
C2 O1 C1 114.7(3) . . ?
C11 O3 C9 105.1(3) . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.107

