# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ejwddc230223
_database_code_depnum_ccdc_archive 'CCDC 2322393'
loop_
_audit_author_name
_audit_author_address
'Corinne Bailly '
;University of Strasbourg
France
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-04-01 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         'C12 H7 Br2 I'
_chemical_formula_sum            'C12 H7 Br2 I'
_chemical_formula_weight         437.90

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.5376(9)
_cell_length_b                   7.9320(9)
_cell_length_c                   11.5935(12)
_cell_angle_alpha                82.325(4)
_cell_angle_beta                 74.766(4)
_cell_angle_gamma                65.240(3)
_cell_volume                     607.10(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2558
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.395
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    9.182
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4594
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6603
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.829
_diffrn_reflns_theta_max         27.898
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2883
_reflns_number_gt                2351
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0319P)²+0.1902P] 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         2883
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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
C1 C 0.4066(6) 0.2920(5) 0.4675(3) 0.0271(9) Uani 1 1 d . . . . .
H1 H 0.495832 0.173033 0.489463 0.032 Uiso 1 1 calc R U . . .
C2 C 0.3067(6) 0.4307(6) 0.5513(3) 0.0306(9) Uani 1 1 d . . . . .
H2 H 0.328229 0.405736 0.630124 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1755(6) 0.6058(6) 0.5208(3) 0.0277(9) Uani 1 1 d . . . . .
H3 H 0.106917 0.700586 0.578168 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1463(6) 0.6398(5) 0.4051(3) 0.0249(8) Uani 1 1 d . . . . .
C5 C 0.2448(6) 0.5020(5) 0.3208(3) 0.0235(8) Uani 1 1 d . . . . .
C6 C 0.3772(6) 0.3257(5) 0.3521(3) 0.0229(8) Uani 1 1 d . . . . .
Br1 Br -0.03570(6) 0.88268(5) 0.36680(4) 0.03273(12) Uani 1 1 d . . . . .
I1 I 0.19834(4) 0.55210(4) 0.14620(2) 0.03405(10) Uani 1 1 d . . . . .
C7 C 0.4770(6) 0.1698(5) 0.2655(3) 0.0230(8) Uani 1 1 d . . . . .
C8 C 0.6484(6) 0.1495(5) 0.1757(3) 0.0258(8) Uani 1 1 d . . . . .
C9 C 0.7292(6) 0.0096(6) 0.0927(4) 0.0329(10) Uani 1 1 d . . . . .
H9 H 0.843140 0.000434 0.030237 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6424(7) -0.1156(6) 0.1020(4) 0.0370(11) Uani 1 1 d . . . . .
H10 H 0.697063 -0.211895 0.046047 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4770(7) -0.1013(6) 0.1921(4) 0.0365(10) Uani 1 1 d . . . . .
H11 H 0.418694 -0.188599 0.198620 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3946(7) 0.0397(6) 0.2736(4) 0.0335(10) Uani 1 1 d . . . . .
H12 H 0.280576 0.047633 0.335649 0.040 Uiso 1 1 calc R U . . .
Br2 Br 0.78125(7) 0.31123(6) 0.16661(3) 0.03263(12) 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
C1 C6 1.387(5) . ?
C1 C2 1.388(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C4 Br1 1.915(4) . ?
C5 C6 1.403(5) . ?
C5 I1 2.103(4) . ?
C6 C7 1.502(5) . ?
C7 C12 1.393(6) . ?
C7 C8 1.394(5) . ?
C8 C9 1.392(5) . ?
C8 Br2 1.909(4) . ?
C9 C10 1.381(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9500 . ?
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
C6 C1 C2 120.6(4) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 Br1 121.4(3) . . ?
C3 C4 Br1 117.6(3) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 I1 121.1(3) . . ?
C6 C5 I1 119.1(3) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C7 119.5(3) . . ?
C5 C6 C7 121.3(3) . . ?
C12 C7 C8 117.8(3) . . ?
C12 C7 C6 119.1(3) . . ?
C8 C7 C6 123.1(3) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 Br2 118.5(3) . . ?
C7 C8 Br2 120.2(3) . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(6) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C2 C3 C4 Br1 180.0(3) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
Br1 C4 C5 C6 180.0(3) . . . . ?
C3 C4 C5 I1 179.3(3) . . . . ?
Br1 C4 C5 I1 -0.3(5) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
C2 C1 C6 C7 -176.2(4) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
I1 C5 C6 C1 -179.4(3) . . . . ?
C4 C5 C6 C7 176.3(4) . . . . ?
I1 C5 C6 C7 -3.4(5) . . . . ?
C1 C6 C7 C12 78.3(5) . . . . ?
C5 C6 C7 C12 -97.7(5) . . . . ?
C1 C6 C7 C8 -102.4(5) . . . . ?
C5 C6 C7 C8 81.6(5) . . . . ?
C12 C7 C8 C9 3.2(6) . . . . ?
C6 C7 C8 C9 -176.0(4) . . . . ?
C12 C7 C8 Br2 -175.3(3) . . . . ?
C6 C7 C8 Br2 5.4(5) . . . . ?
C7 C8 C9 C10 -2.4(6) . . . . ?
Br2 C8 C9 C10 176.2(3) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C10 C11 C12 0.7(7) . . . . ?
C10 C11 C12 C7 0.3(7) . . . . ?
C8 C7 C12 C11 -2.2(6) . . . . ?
C6 C7 C12 C11 177.1(4) . . . . ?

_refine_diff_density_max         0.781
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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_jwddcm230706
_database_code_depnum_ccdc_archive 'CCDC 2322394'
loop_
_audit_author_name
_audit_author_address
'Dr. Corinne Bailly '
;University of Strasbourg
France
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Br Cl I'
_chemical_formula_sum            'C12 H7 Br Cl I'
_chemical_formula_weight         393.44

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.5445(3)
_cell_length_b                   7.7965(3)
_cell_length_c                   11.5759(4)
_cell_angle_alpha                81.1650(10)
_cell_angle_beta                 73.5190(10)
_cell_angle_gamma                64.5410(10)
_cell_volume                     589.13(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      28.01

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.218
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    6.298
_shelx_estimated_absorpt_T_min   0.519
_shelx_estimated_absorpt_T_max   0.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19446
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.896
_diffrn_reflns_theta_max         28.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2812
_reflns_number_gt                2605
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_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)+(0.0116P)²+1.1296P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2812
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0439
_refine_ls_wR_factor_gt          0.0425
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_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
C1 C 0.4060(4) 0.2889(4) 0.4717(2) 0.0210(5) Uani 1 1 d . . . . .
H1 H 0.495773 0.166572 0.493958 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3058(4) 0.4315(4) 0.5552(2) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.328242 0.406179 0.633974 0.028 Uiso 1 1 calc R U . . .
C3 C 0.1743(4) 0.6094(4) 0.5244(2) 0.0224(5) Uani 1 1 d . . . . .
H3 H 0.106262 0.706213 0.581808 0.027 Uiso 1 1 calc R U . . .
C4 C 0.1414(4) 0.6469(4) 0.4091(2) 0.0191(5) Uani 1 1 d . . . . .
C5 C 0.2413(4) 0.5049(4) 0.3240(2) 0.0183(5) Uani 1 1 d . . . . .
C6 C 0.3751(4) 0.3245(4) 0.3550(2) 0.0183(5) Uani 1 1 d . . . . .
C7 C 0.4747(4) 0.1673(4) 0.2684(2) 0.0187(5) Uani 1 1 d . . . . .
C8 C 0.6484(4) 0.1442(4) 0.1766(2) 0.0190(5) Uani 1 1 d . . . . .
C9 C 0.7291(4) 0.0048(4) 0.0924(2) 0.0240(5) Uani 1 1 d . . . . .
H9 H 0.845160 -0.005212 0.029291 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6387(4) -0.1197(4) 0.1014(3) 0.0253(6) Uani 1 1 d . . . . .
H10 H 0.693051 -0.215895 0.044271 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4694(4) -0.1047(4) 0.1934(3) 0.0252(6) Uani 1 1 d . . . . .
H11 H 0.409160 -0.191780 0.200165 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3874(4) 0.0386(4) 0.2761(2) 0.0235(5) Uani 1 1 d . . . . .
H12 H 0.270574 0.048913 0.338640 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl -0.02856(10) 0.87684(9) 0.37294(6) 0.02339(13) Uani 1 1 d . . . . .
Br1 Br 0.78481(4) 0.30614(4) 0.16637(2) 0.02316(7) Uani 1 1 d . . . . .
I1 I 0.19007(3) 0.55989(3) 0.15056(2) 0.02469(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
C1 C2 1.391(4) . ?
C1 C6 1.402(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(3) . ?
C4 Cl1 1.769(3) . ?
C5 C6 1.398(4) . ?
C5 I1 2.097(2) . ?
C6 C7 1.494(3) . ?
C7 C8 1.394(4) . ?
C7 C12 1.398(3) . ?
C8 C9 1.386(4) . ?
C8 Br1 1.915(2) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
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 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 Cl1 118.6(2) . . ?
C5 C4 Cl1 121.1(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 I1 119.67(18) . . ?
C4 C5 I1 120.5(2) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 121.0(2) . . ?
C1 C6 C7 119.8(2) . . ?
C8 C7 C12 117.5(2) . . ?
C8 C7 C6 123.5(2) . . ?
C12 C7 C6 119.0(2) . . ?
C9 C8 C7 122.1(2) . . ?
C9 C8 Br1 118.19(19) . . ?
C7 C8 Br1 119.69(18) . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 Cl1 179.95(19) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
Cl1 C4 C5 C6 179.92(18) . . . . ?
C3 C4 C5 I1 179.38(18) . . . . ?
Cl1 C4 C5 I1 -0.6(3) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
I1 C5 C6 C1 -179.17(18) . . . . ?
C4 C5 C6 C7 176.5(2) . . . . ?
I1 C5 C6 C7 -3.0(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 C7 -176.7(2) . . . . ?
C5 C6 C7 C8 82.6(3) . . . . ?
C1 C6 C7 C8 -101.3(3) . . . . ?
C5 C6 C7 C12 -95.4(3) . . . . ?
C1 C6 C7 C12 80.8(3) . . . . ?
C12 C7 C8 C9 2.6(4) . . . . ?
C6 C7 C8 C9 -175.4(3) . . . . ?
C12 C7 C8 Br1 -176.4(2) . . . . ?
C6 C7 C8 Br1 5.6(4) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
Br1 C8 C9 C10 177.0(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C7 -0.5(4) . . . . ?
C8 C7 C12 C11 -1.3(4) . . . . ?
C6 C7 C12 C11 176.8(3) . . . . ?

_refine_diff_density_max         0.696
_refine_diff_density_min         -0.833
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_ejwddc230704
_database_code_depnum_ccdc_archive 'CCDC 2322396'
loop_
_audit_author_name
_audit_author_address
'Corinne BAILLY'
;University of Strasbourg
France
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-04-01 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         'C13 H7 Cl O'
_chemical_formula_sum            'C13 H7 Cl O'
_chemical_formula_weight         214.64

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'
Cl Cl 0.1484 0.1585 '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           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                   7.3449(2)
_cell_length_b                   15.5390(3)
_cell_length_c                   8.8357(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.8270(10)
_cell_angle_gamma                90
_cell_volume                     974.86(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.90

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.355
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19777
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         27.898
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2335
_reflns_number_gt                2202
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_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)+(0.0433P)²+0.4810P] 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         2335
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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
C1 C 0.19431(17) 0.64827(8) 0.53919(14) 0.0218(2) Uani 1 1 d . . . . .
H1 H 0.070918 0.626414 0.528782 0.026 Uiso 1 1 calc R U . . .
C2 C 0.26531(18) 0.71504(8) 0.64382(14) 0.0242(3) Uani 1 1 d . . . . .
H2 H 0.189643 0.737668 0.706964 0.029 Uiso 1 1 calc R U . . .
C3 C 0.44361(18) 0.74908(8) 0.65770(14) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.488197 0.795082 0.728265 0.029 Uiso 1 1 calc R U . . .
C4 C 0.55694(16) 0.71519(8) 0.56719(14) 0.0207(2) Uani 1 1 d . . . . .
C5 C 0.49213(16) 0.64735(7) 0.46628(13) 0.0183(2) Uani 1 1 d . . . . .
C6 C 0.30891(16) 0.61495(7) 0.45127(13) 0.0182(2) Uani 1 1 d . . . . .
C7 C 0.27431(16) 0.54473(7) 0.33379(13) 0.0191(2) Uani 1 1 d . . . . .
C8 C 0.43784(17) 0.53240(7) 0.28261(13) 0.0191(2) Uani 1 1 d . . . . .
C9 C 0.58312(17) 0.59619(7) 0.36129(13) 0.0189(2) Uani 1 1 d . . . . .
C10 C 0.44900(19) 0.47018(8) 0.17331(14) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.561552 0.461709 0.141047 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2887(2) 0.42019(9) 0.11200(16) 0.0298(3) Uani 1 1 d . . . . .
H11 H 0.291720 0.377039 0.036517 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1251(2) 0.43308(9) 0.16050(17) 0.0297(3) Uani 1 1 d . . . . .
H12 H 0.017592 0.398658 0.116782 0.036 Uiso 1 1 calc R U . . .
C13 C 0.11481(18) 0.49560(8) 0.27231(15) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.002470 0.504049 0.304899 0.029 Uiso 1 1 calc R U . . .
Cl1 Cl 0.77701(4) 0.76038(2) 0.58212(4) 0.02894(11) Uani 1 1 d . . . . .
O1 O 0.74048(13) 0.60468(6) 0.34225(11) 0.0257(2) 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
C1 C6 1.3837(16) . ?
C1 C2 1.3987(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3883(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3966(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3840(16) . ?
C4 Cl1 1.7360(12) . ?
C5 C6 1.4109(16) . ?
C5 C9 1.5022(16) . ?
C6 C7 1.4824(16) . ?
C7 C13 1.3874(17) . ?
C7 C8 1.4007(16) . ?
C8 C10 1.3838(17) . ?
C8 C9 1.4915(16) . ?
C9 O1 1.2170(15) . ?
C10 C11 1.3987(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4014(19) . ?
C12 H12 0.9500 . ?
C13 H13 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
C6 C1 C2 118.11(11) . . ?
C6 C1 H1 120.9 . . ?
C2 C1 H1 120.9 . . ?
C3 C2 C1 121.65(11) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 119.52(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.92(11) . . ?
C5 C4 Cl1 121.14(9) . . ?
C3 C4 Cl1 118.94(10) . . ?
C4 C5 C6 119.67(11) . . ?
C4 C5 C9 131.83(11) . . ?
C6 C5 C9 108.51(10) . . ?
C1 C6 C5 121.08(11) . . ?
C1 C6 C7 130.43(11) . . ?
C5 C6 C7 108.48(10) . . ?
C13 C7 C8 120.41(11) . . ?
C13 C7 C6 130.96(11) . . ?
C8 C7 C6 108.62(10) . . ?
C10 C8 C7 121.99(11) . . ?
C10 C8 C9 128.80(11) . . ?
C7 C8 C9 109.20(10) . . ?
O1 C9 C8 126.80(11) . . ?
O1 C9 C5 128.05(11) . . ?
C8 C9 C5 105.15(10) . . ?
C8 C10 C11 117.64(12) . . ?
C8 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C12 C11 C10 120.61(12) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.60(12) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C7 C13 C12 117.72(12) . . ?
C7 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.56(18) . . . . ?
C1 C2 C3 C4 -1.07(19) . . . . ?
C2 C3 C4 C5 -0.93(18) . . . . ?
C2 C3 C4 Cl1 178.30(9) . . . . ?
C3 C4 C5 C6 2.35(17) . . . . ?
Cl1 C4 C5 C6 -176.86(9) . . . . ?
C3 C4 C5 C9 -177.17(11) . . . . ?
Cl1 C4 C5 C9 3.62(18) . . . . ?
C2 C1 C6 C5 -0.10(17) . . . . ?
C2 C1 C6 C7 179.39(11) . . . . ?
C4 C5 C6 C1 -1.85(17) . . . . ?
C9 C5 C6 C1 177.77(10) . . . . ?
C4 C5 C6 C7 178.56(10) . . . . ?
C9 C5 C6 C7 -1.82(12) . . . . ?
C1 C6 C7 C13 3.9(2) . . . . ?
C5 C6 C7 C13 -176.53(12) . . . . ?
C1 C6 C7 C8 -177.25(12) . . . . ?
C5 C6 C7 C8 2.29(13) . . . . ?
C13 C7 C8 C10 -1.70(18) . . . . ?
C6 C7 C8 C10 179.33(10) . . . . ?
C13 C7 C8 C9 177.16(10) . . . . ?
C6 C7 C8 C9 -1.81(13) . . . . ?
C10 C8 C9 O1 0.0(2) . . . . ?
C7 C8 C9 O1 -178.72(11) . . . . ?
C10 C8 C9 C5 179.46(11) . . . . ?
C7 C8 C9 C5 0.70(12) . . . . ?
C4 C5 C9 O1 -0.3(2) . . . . ?
C6 C5 C9 O1 -179.86(12) . . . . ?
C4 C5 C9 C8 -179.71(12) . . . . ?
C6 C5 C9 C8 0.73(12) . . . . ?
C7 C8 C10 C11 1.23(18) . . . . ?
C9 C8 C10 C11 -177.39(11) . . . . ?
C8 C10 C11 C12 -0.18(19) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C8 C7 C13 C12 1.04(18) . . . . ?
C6 C7 C13 C12 179.75(12) . . . . ?
C11 C12 C13 C7 0.0(2) . . . . ?

_refine_diff_density_max         0.603
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_ejwddc230712
_database_code_depnum_ccdc_archive 'CCDC 2322395'
loop_
_audit_author_name
_audit_author_address
'Dr. Corinne Bailly '
;University of Strasbourg
France
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-04-01 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         'C12 H7 Br3'
_chemical_formula_sum            'C12 H7 Br3'
_chemical_formula_weight         390.91

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.4022(3)
_cell_length_b                   7.8572(3)
_cell_length_c                   11.3380(4)
_cell_angle_alpha                83.9920(10)
_cell_angle_beta                 76.4460(10)
_cell_angle_gamma                65.0730(10)
_cell_volume                     581.33(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.233
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    10.370
_shelx_estimated_absorpt_T_min   0.288
_shelx_estimated_absorpt_T_max   0.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4154
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24581
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         27.928
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2772
_reflns_number_gt                2485
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_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)+(0.0244P)²+0.8713P] 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         2772
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0550
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3555(4) 0.8515(4) 0.8335(2) 0.0191(5) Uani 1 1 d . . . . .
C2 C 0.5234(4) 0.8326(4) 0.7415(2) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.6002(5) 0.9700(4) 0.7322(3) 0.0239(6) Uani 1 1 d . . . . .
H3 H 0.714097 0.961609 0.669477 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5121(5) 1.1185(4) 0.8133(3) 0.0262(6) Uani 1 1 d . . . . .
H4 H 0.564746 1.211460 0.805255 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3481(5) 1.1306(4) 0.9056(3) 0.0266(6) Uani 1 1 d . . . . .
H5 H 0.289459 1.230913 0.961820 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2684(4) 0.9971(4) 0.9167(3) 0.0243(6) Uani 1 1 d . . . . .
H6 H 0.155822 1.004975 0.980246 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6262(4) 0.6747(3) 0.6527(2) 0.0173(5) Uani 1 1 d . . . . .
C8 C 0.5974(4) 0.7083(4) 0.5335(2) 0.0194(5) Uani 1 1 d . . . . .
H8 H 0.507981 0.828923 0.510870 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6992(4) 0.5658(4) 0.4476(2) 0.0212(5) Uani 1 1 d . . . . .
H9 H 0.678888 0.590081 0.366832 0.025 Uiso 1 1 calc R U . . .
C10 C 0.8298(4) 0.3889(4) 0.4792(2) 0.0207(5) Uani 1 1 d . . . . .
H10 H 0.898455 0.291833 0.420604 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8593(4) 0.3550(4) 0.5974(2) 0.0185(5) Uani 1 1 d . . . . .
C12 C 0.7585(4) 0.4964(4) 0.6842(2) 0.0172(5) Uani 1 1 d . . . . .
Br1 Br 0.23068(4) 0.68006(4) 0.84436(2) 0.02382(8) Uani 1 1 d . . . . .
Br2 Br 0.80376(5) 0.45059(4) 0.84427(2) 0.02681(8) Uani 1 1 d . . . . .
Br3 Br 1.04204(4) 0.11323(4) 0.63784(3) 0.02385(8) 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
C1 C2 1.387(4) . ?
C1 C6 1.390(4) . ?
C1 Br1 1.909(3) . ?
C2 C3 1.402(4) . ?
C2 C7 1.496(3) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.397(4) . ?
C7 C8 1.398(4) . ?
C8 C9 1.394(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(3) . ?
C11 Br3 1.895(3) . ?
C12 Br2 1.893(3) . ?

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 122.0(3) . . ?
C2 C1 Br1 119.84(19) . . ?
C6 C1 Br1 118.1(2) . . ?
C1 C2 C3 117.6(2) . . ?
C1 C2 C7 123.8(2) . . ?
C3 C2 C7 118.6(2) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C12 C7 C8 119.0(2) . . ?
C12 C7 C2 121.6(2) . . ?
C8 C7 C2 119.3(2) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 Br3 118.57(19) . . ?
C12 C11 Br3 120.7(2) . . ?
C11 C12 C7 120.1(2) . . ?
C11 C12 Br2 120.5(2) . . ?
C7 C12 Br2 119.43(19) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.0(4) . . . . ?
Br1 C1 C2 C3 175.4(2) . . . . ?
C6 C1 C2 C7 177.9(3) . . . . ?
Br1 C1 C2 C7 -4.7(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C7 C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
Br1 C1 C6 C5 -175.7(2) . . . . ?
C1 C2 C7 C12 -77.5(4) . . . . ?
C3 C2 C7 C12 102.4(3) . . . . ?
C1 C2 C7 C8 105.7(3) . . . . ?
C3 C2 C7 C8 -74.5(3) . . . . ?
C12 C7 C8 C9 0.0(4) . . . . ?
C2 C7 C8 C9 176.9(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C9 C10 C11 Br3 -179.0(2) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
Br3 C11 C12 C7 179.1(2) . . . . ?
C10 C11 C12 Br2 -178.7(2) . . . . ?
Br3 C11 C12 Br2 0.5(3) . . . . ?
C8 C7 C12 C11 -0.1(4) . . . . ?
C2 C7 C12 C11 -176.9(2) . . . . ?
C8 C7 C12 Br2 178.55(19) . . . . ?
C2 C7 C12 Br2 1.7(3) . . . . ?

_refine_diff_density_max         0.853
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.098

