# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2013305'
loop_
_audit_author_name
_audit_author_address
'Yasushi Yoshida'
;Chiba University
Japan
;
_audit_update_record             
;
2020-07-01 deposited with the CCDC.	2021-01-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Br Cl O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         303.58

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.8208(16)
_cell_length_b                   7.0277(7)
_cell_length_c                   19.5682(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2450.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8887
_cell_measurement_theta_min      4.5192
_cell_measurement_theta_max      68.3206
_cell_measurement_temperature    173

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216

_exptl_absorpt_coefficient_mu    6.442
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10596
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_theta_min         4.519
_diffrn_reflns_theta_max         68.315
_diffrn_reflns_theta_full        68.315
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             2216
_reflns_number_gt                2164
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0748
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         2216
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.7747P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.455
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

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 Br01 0.61531(2) 0.57886(2) 0.79165(2) 0.02605(12) Uani d . . . 1 . .
Cl Cl02 0.54441(2) 0.52664(8) 0.65063(2) 0.03818(14) Uani d . . . 1 . .
C C005 0.73779(10) 0.6126(2) 0.87665(9) 0.0269(4) Uani d . . . 1 . .
C C006 0.77752(10) 0.6362(3) 0.93780(9) 0.0309(4) Uani d . . . 1 . .
H H006 0.8308 0.6398 0.9376 0.037 Uiso calc U . R 1 . .
C C007 0.71661(10) 0.5777(2) 0.75594(10) 0.0269(4) Uani d . . . 1 . .
C C008 0.66030(10) 0.6103(2) 0.88114(8) 0.0277(3) Uani d . . . 1 . .
C C009 0.61914(10) 0.6281(3) 0.94031(10) 0.0339(4) Uani d . . . 1 . .
H H009 0.5658 0.6254 0.9404 0.041 Uiso calc U . R 1 . .
C C00A 0.76862(10) 0.5932(2) 0.80825(10) 0.0272(4) Uani d . . . 1 . .
C C00B 0.73830(11) 0.6544(3) 0.99841(9) 0.0354(4) Uani d . . . 1 . .
H H00B 0.7653 0.6702 1.0399 0.042 Uiso calc U . R 1 . .
C C00C 0.84456(12) 0.5887(2) 0.78971(9) 0.0308(4) Uani d . . . 1 . .
H H00C 0.8826 0.5968 0.8236 0.037 Uiso calc U . R 1 . .
C C00D 0.73306(11) 0.5608(3) 0.68759(10) 0.0317(4) Uani d . . . 1 . .
H H00D 0.695 0.5513 0.6538 0.038 Uiso calc U . R 1 . .
C C00E 0.86338(13) 0.5723(3) 0.72119(12) 0.0349(4) Uani d . . . 1 . .
H H00E 0.9148 0.5703 0.7084 0.042 Uiso calc U . R 1 . .
C C00F 0.66071(11) 0.6503(3) 1.00010(9) 0.0371(4) Uani d . . . 1 . .
H H00F 0.6354 0.6628 1.0426 0.044 Uiso calc U . R 1 . .
C C00G 0.80877(12) 0.5586(3) 0.67098(10) 0.0359(4) Uani d . . . 1 . .
H H00G 0.8234 0.5476 0.6245 0.043 Uiso calc U . R 1 . .
O O100 0.57648(10) 0.8736(3) 0.55280(10) 0.0507(4) Uani d . . . 1 . .
O O101 0.52535(10) 0.8418(3) 0.41855(9) 0.0517(4) Uani d . . . 1 . .
H H2 0.5063(14) 0.751(4) 0.4031(13) 0.035(6) Uiso d . . . 1 . .
H H1 0.5703(15) 0.785(4) 0.5776(15) 0.049(7) Uiso d . . . 1 . .
H H3 0.5633(16) 0.839(4) 0.5207(15) 0.046(8) Uiso d . . . 1 . .
H H4 0.492(2) 0.903(5) 0.4221(19) 0.079(13) Uiso 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
Br01 C007 . 1.9358(18) ?
Br01 C008 . 1.9385(17) ?
C005 C008 . 1.384(3) ?
C005 C006 . 1.400(2) ?
C005 C00A . 1.453(3) ?
C006 C00B . 1.382(3) ?
C006 H006 . 0.95 ?
C007 C00D . 1.374(3) ?
C007 C00A . 1.385(3) ?
C008 C009 . 1.376(3) ?
C009 C00F . 1.394(3) ?
C009 H009 . 0.95 ?
C00A C00C . 1.401(3) ?
C00B C00F . 1.383(3) ?
C00B H00B . 0.95 ?
C00C C00E . 1.387(3) ?
C00C H00C . 0.95 ?
C00D C00G . 1.388(3) ?
C00D H00D . 0.95 ?
C00E C00G . 1.386(3) ?
C00E H00E . 0.95 ?
C00F H00F . 0.95 ?
C00G H00G . 0.95 ?
O100 H1 . 0.80(3) ?
O100 H3 . 0.71(3) ?
O101 H2 . 0.78(3) ?
O101 H4 . 0.74(4) ?

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
C007 Br01 C008 . . 86.61(8) ?
C008 C005 C006 . . 116.85(16) ?
C008 C005 C00A . . 115.76(16) ?
C006 C005 C00A . . 127.38(17) ?
C00B C006 C005 . . 119.24(17) ?
C00B C006 H006 . . 120.4 ?
C005 C006 H006 . . 120.4 ?
C00D C007 C00A . . 125.67(17) ?
C00D C007 Br01 . . 123.41(14) ?
C00A C007 Br01 . . 110.92(14) ?
C009 C008 C005 . . 125.74(16) ?
C009 C008 Br01 . . 123.36(14) ?
C005 C008 Br01 . . 110.90(13) ?
C008 C009 C00F . . 115.67(16) ?
C008 C009 H009 . . 122.2 ?
C00F C009 H009 . . 122.2 ?
C007 C00A C00C . . 116.95(17) ?
C007 C00A C005 . . 115.78(16) ?
C00C C00A C005 . . 127.27(17) ?
C006 C00B C00F . . 121.59(17) ?
C006 C00B H00B . . 119.2 ?
C00F C00B H00B . . 119.2 ?
C00E C00C C00A . . 119.05(19) ?
C00E C00C H00C . . 120.5 ?
C00A C00C H00C . . 120.5 ?
C007 C00D C00G . . 115.87(18) ?
C007 C00D H00D . . 122.1 ?
C00G C00D H00D . . 122.1 ?
C00G C00E C00C . . 121.4(2) ?
C00G C00E H00E . . 119.3 ?
C00C C00E H00E . . 119.3 ?
C00B C00F C009 . . 120.90(17) ?
C00B C00F H00F . . 119.5 ?
C009 C00F H00F . . 119.5 ?
C00E C00G C00D . . 121.03(19) ?
C00E C00G H00G . . 119.5 ?
C00D C00G H00G . . 119.5 ?
H1 O100 H3 . . 103.(3) ?
H2 O101 H4 . . 99.(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C008 C005 C006 C00B . . . . 0.5(2) ?
C00A C005 C006 C00B . . . . 179.28(17) ?
C006 C005 C008 C009 . . . . -0.4(3) ?
C00A C005 C008 C009 . . . . -179.39(18) ?
C006 C005 C008 Br01 . . . . 179.44(13) ?
C00A C005 C008 Br01 . . . . 0.48(18) ?
C005 C008 C009 C00F . . . . 0.1(3) ?
Br01 C008 C009 C00F . . . . -179.78(14) ?
C00D C007 C00A C00C . . . . -0.9(2) ?
Br01 C007 C00A C00C . . . . 178.23(12) ?
C00D C007 C00A C005 . . . . 179.07(15) ?
Br01 C007 C00A C005 . . . . -1.81(17) ?
C008 C005 C00A C007 . . . . 0.9(2) ?
C006 C005 C00A C007 . . . . -177.92(16) ?
C008 C005 C00A C00C . . . . -179.15(16) ?
C006 C005 C00A C00C . . . . 2.0(3) ?
C005 C006 C00B C00F . . . . -0.2(3) ?
C007 C00A C00C C00E . . . . 1.0(2) ?
C005 C00A C00C C00E . . . . -178.98(16) ?
C00A C007 C00D C00G . . . . 0.3(3) ?
Br01 C007 C00D C00G . . . . -178.70(13) ?
C00A C00C C00E C00G . . . . -0.6(3) ?
C006 C00B C00F C009 . . . . -0.2(3) ?
C008 C009 C00F C00B . . . . 0.2(3) ?
C00C C00E C00G C00D . . . . 0.0(3) ?
C007 C00D C00G C00E . . . . 0.2(3) ?

