# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_s1
_database_code_depnum_ccdc_archive 'CCDC 2087155'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H8 Cl4 O2'
_chemical_formula_weight         470.10

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'
O O 0.0492 0.0322 '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                   3.8349(4)
_cell_length_b                   8.8365(7)
_cell_length_c                   13.2606(9)
_cell_angle_alpha                88.717(5)
_cell_angle_beta                 89.773(6)
_cell_angle_gamma                78.865(6)
_cell_volume                     440.79(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1613
_cell_measurement_theta_min      3.334
_cell_measurement_theta_max      72.447

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   0.4965
_exptl_transmission_factor_max   0.7536
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.291
_shelx_estimated_absorpt_T_min   0.188
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4965
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12693
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.334
_diffrn_reflns_theta_max         72.447
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1722
_reflns_number_gt                1613
_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-2017/1 (Sheldrick, 2017)'
_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)+(0.0692P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         1722
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.9265(4) 0.48541(17) 0.04576(11) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.7175(4) 0.61071(18) 0.11240(12) 0.0299(4) Uani 1 1 d . . . . .
C3 C 0.6145(4) 0.53376(18) 0.20381(12) 0.0269(3) Uani 1 1 d . . . . .
C4 C 0.7400(4) 0.37472(17) 0.19588(11) 0.0242(3) Uani 1 1 d . . . . .
C5 C 0.9268(4) 0.33870(17) 0.10277(11) 0.0245(3) Uani 1 1 d . . . . .
C6 C 1.0582(5) 0.18421(19) 0.08766(13) 0.0338(4) Uani 1 1 d . . . . .
H6 H 1.180259 0.153148 0.028609 0.041 Uiso 1 1 calc R U . . .
C7 C 1.0079(5) 0.07397(19) 0.16118(14) 0.0352(4) Uani 1 1 d . . . . .
H7 H 1.099430 -0.029354 0.149069 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8308(4) 0.11057(19) 0.24999(12) 0.0307(4) Uani 1 1 d . . . . .
C9 C 0.6846(4) 0.26745(18) 0.27182(11) 0.0265(3) Uani 1 1 d . . . . .
C10 C 0.4907(4) 0.3347(2) 0.35760(12) 0.0297(3) Uani 1 1 d . . . . .
C11 C 0.3709(4) 0.4917(2) 0.36418(12) 0.0332(4) Uani 1 1 d . . . . .
H11 H 0.246851 0.530489 0.421386 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4310(4) 0.5940(2) 0.28713(13) 0.0325(4) Uani 1 1 d . . . . .
H12 H 0.349015 0.699683 0.292269 0.039 Uiso 1 1 calc R U . . .
Cl1 Cl 0.38834(13) 0.22513(5) 0.45934(3) 0.04481(19) Uani 1 1 d . . . . .
Cl2 Cl 0.79668(13) -0.04139(5) 0.33117(4) 0.0496(2) Uani 1 1 d . . . . .
O1 O 0.6396(5) 0.74782(15) 0.09571(11) 0.0568(4) 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 C1 1.376(3) 2_765 ?
C1 C5 1.486(2) . ?
C1 C2 1.531(2) . ?
C2 O1 1.206(2) . ?
C2 C3 1.467(2) . ?
C3 C12 1.369(2) . ?
C3 C4 1.401(2) . ?
C4 C9 1.411(2) . ?
C4 C5 1.436(2) . ?
C5 C6 1.380(2) . ?
C6 C7 1.402(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(2) . ?
C8 Cl2 1.7266(17) . ?
C9 C10 1.433(2) . ?
C10 C11 1.379(2) . ?
C10 Cl1 1.7309(17) . ?
C11 C12 1.397(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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
C1 C1 C5 131.34(18) 2_765 . ?
C1 C1 C2 123.97(17) 2_765 . ?
C5 C1 C2 104.69(12) . . ?
O1 C2 C3 124.12(15) . . ?
O1 C2 C1 128.59(15) . . ?
C3 C2 C1 107.28(13) . . ?
C12 C3 C4 121.29(15) . . ?
C12 C3 C2 130.33(15) . . ?
C4 C3 C2 108.38(13) . . ?
C3 C4 C9 122.63(14) . . ?
C3 C4 C5 111.43(14) . . ?
C9 C4 C5 125.94(14) . . ?
C6 C5 C4 115.70(14) . . ?
C6 C5 C1 136.10(14) . . ?
C4 C5 C1 108.21(13) . . ?
C5 C6 C7 120.11(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 123.39(16) . . ?
C8 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
C7 C8 C9 120.36(15) . . ?
C7 C8 Cl2 116.59(13) . . ?
C9 C8 Cl2 123.06(12) . . ?
C4 C9 C8 114.50(14) . . ?
C4 C9 C10 114.46(14) . . ?
C8 C9 C10 131.04(15) . . ?
C11 C10 C9 122.01(15) . . ?
C11 C10 Cl1 115.49(12) . . ?
C9 C10 Cl1 122.50(13) . . ?
C10 C11 C12 121.70(15) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C3 C12 C11 117.90(15) . . ?
C3 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.052




####################################################################### 
# 
# 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_s1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2101214'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
(E)-2H,2'H-[1,1'-biacenaphthylenylidene]-2,2'-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H12 O2'
_chemical_formula_weight         332.34

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'
O O 0.0492 0.0322 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   3.8029(3)
_cell_length_b                   13.8237(10)
_cell_length_c                   14.1694(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.395(5)
_cell_angle_gamma                90
_cell_volume                     742.70(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1071
_cell_measurement_theta_min      4.475
_cell_measurement_theta_max      72.488

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.5865
_exptl_transmission_factor_max   0.7536
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10769
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.475
_diffrn_reflns_theta_max         72.488
_diffrn_reflns_theta_full        67.679
_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             1475
_reflns_number_gt                1071
_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-2017/1 (Sheldrick, 2017)'
_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)+(0.0413P)²+0.6197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         1475
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1407
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.5129(5) 0.54536(15) 0.48149(15) 0.0309(5) Uani 1 1 d . . . . .
C2 C 0.3991(6) 0.63701(15) 0.53124(16) 0.0350(5) Uani 1 1 d . . . . .
C3 C 0.4864(6) 0.72078(15) 0.47286(16) 0.0347(5) Uani 1 1 d . . . . .
C4 C 0.4463(6) 0.81813(16) 0.48465(17) 0.0409(6) Uani 1 1 d . . . . .
H4 H 0.356089 0.843577 0.540201 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5433(6) 0.87946(17) 0.41173(18) 0.0440(6) Uani 1 1 d . . . . .
H5 H 0.518461 0.947395 0.418898 0.053 Uiso 1 1 calc R U . . .
C6 C 0.6728(6) 0.84430(17) 0.33036(17) 0.0418(6) Uani 1 1 d . . . . .
H6 H 0.733869 0.888072 0.282583 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7160(6) 0.74390(16) 0.31716(16) 0.0348(5) Uani 1 1 d . . . . .
C8 C 0.6210(5) 0.68336(15) 0.39046(15) 0.0306(5) Uani 1 1 d . . . . .
C9 C 0.8429(6) 0.69760(17) 0.23711(16) 0.0384(5) Uani 1 1 d . . . . .
H9 H 0.911314 0.734611 0.185067 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7706(6) 0.53936(16) 0.31159(15) 0.0357(5) Uani 1 1 d . . . . .
H10 H 0.794537 0.471111 0.307533 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8652(6) 0.59902(17) 0.23601(16) 0.0389(6) Uani 1 1 d . . . . .
H11 H 0.948526 0.568752 0.181809 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6439(5) 0.58049(15) 0.39086(14) 0.0296(5) Uani 1 1 d . . . . .
O1 O 0.2503(5) 0.64329(12) 0.60410(12) 0.0525(5) 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 C1 1.366(4) 3_666 ?
C1 C12 1.494(3) . ?
C1 C2 1.528(3) . ?
C2 O1 1.218(3) . ?
C2 C3 1.476(3) . ?
C3 C4 1.366(3) . ?
C3 C8 1.409(3) . ?
C4 C5 1.407(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(3) . ?
C7 C9 1.419(3) . ?
C8 C12 1.425(3) . ?
C9 C11 1.366(3) . ?
C9 H9 0.9500 . ?
C10 C12 1.378(3) . ?
C10 C11 1.420(3) . ?
C10 H10 0.9500 . ?
C11 H11 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
C1 C1 C12 131.8(2) 3_666 . ?
C1 C1 C2 123.6(2) 3_666 . ?
C12 C1 C2 104.59(17) . . ?
O1 C2 C3 123.9(2) . . ?
O1 C2 C1 128.1(2) . . ?
C3 C2 C1 107.95(18) . . ?
C4 C3 C8 120.9(2) . . ?
C4 C3 C2 132.3(2) . . ?
C8 C3 C2 106.75(18) . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 116.7(2) . . ?
C8 C7 C9 116.5(2) . . ?
C6 C7 C9 126.8(2) . . ?
C7 C8 C3 121.7(2) . . ?
C7 C8 C12 125.4(2) . . ?
C3 C8 C12 112.91(18) . . ?
C11 C9 C7 119.0(2) . . ?
C11 C9 H9 120.5 . . ?
C7 C9 H9 120.5 . . ?
C12 C10 C11 120.0(2) . . ?
C12 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C11 C10 123.5(2) . . ?
C9 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C10 C12 C8 115.70(19) . . ?
C10 C12 C1 136.6(2) . . ?
C8 C12 C1 107.67(17) . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.050




####################################################################### 
# 
# 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_YH2
_database_code_depnum_ccdc_archive 'CCDC 2087157'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_YH2                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.021 Ang.  
RESPONSE: Relatively poor diffraction data from a challenging
sample. Multiple attempts were made to grow better diffracting 
crystals, met with limited success. 
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H8 Br4 O2'
_chemical_formula_weight         647.94

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   31.7745(16)
_cell_length_b                   3.8742(2)
_cell_length_c                   15.4074(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1896.66(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2878
_cell_measurement_theta_min      2.781
_cell_measurement_theta_max      72.450

_exptl_crystal_description       needles
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.269
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   0.5977
_exptl_transmission_factor_max   0.7536
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    10.539
_shelx_estimated_absorpt_T_min   0.144
_shelx_estimated_absorpt_T_max   0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25266
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.1123
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.781
_diffrn_reflns_theta_max         72.450
_diffrn_reflns_theta_full        67.679
_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             3746
_reflns_number_gt                2878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0753P)²+6.8040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3746
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Br1A Br 0.37106(5) 0.9863(5) 0.36799(13) 0.0588(5) Uani 1 1 d . . . . .
Br2A Br 0.35537(5) 1.2266(5) 0.57052(15) 0.0605(5) Uani 1 1 d . . . . .
Br2B Br 0.77180(6) -0.1662(6) 0.42792(18) 0.0764(7) Uani 1 1 d . . . . .
Br1B Br 0.75358(6) -0.0430(6) 0.63534(16) 0.0742(7) Uani 1 1 d . . . . .
O1A O 0.5612(4) 0.748(4) 0.6710(7) 0.063(3) Uani 1 1 d . . . . .
O1B O 0.5720(4) 0.452(4) 0.3323(7) 0.072(4) Uani 1 1 d . . . . .
C9A C 0.4352(5) 0.925(4) 0.5068(10) 0.040(3) Uani 1 1 d . . . . .
C4A C 0.4761(5) 0.832(4) 0.5268(10) 0.040(3) Uani 1 1 d . . . . .
C3A C 0.4946(4) 0.887(4) 0.6096(10) 0.041(3) Uani 1 1 d . . . . .
C1B C 0.5824(4) 0.459(4) 0.4892(9) 0.038(3) Uani 1 1 d . . . . .
C9B C 0.6926(4) 0.104(4) 0.4973(10) 0.040(3) Uani 1 1 d . . . . .
C4B C 0.6515(5) 0.237(4) 0.4773(10) 0.042(3) Uani 1 1 d . . . . .
C5B C 0.6216(5) 0.361(4) 0.5380(10) 0.043(3) Uani 1 1 d . . . . .
C2A C 0.5370(5) 0.739(4) 0.6083(9) 0.042(3) Uani 1 1 d . . . . .
C10A C 0.4129(5) 1.084(4) 0.5771(11) 0.046(3) Uani 1 1 d . . . . .
C5A C 0.5051(5) 0.661(4) 0.4699(10) 0.041(3) Uani 1 1 d . . . . .
C1A C 0.5453(4) 0.598(4) 0.5175(9) 0.039(3) Uani 1 1 d . . . . .
C12A C 0.4725(5) 1.045(4) 0.6732(9) 0.043(3) Uani 1 1 d . . . . .
H12A H 0.484742 1.090180 0.726859 0.052 Uiso 1 1 calc R U . . .
C2B C 0.5933(5) 0.391(5) 0.3965(10) 0.048(4) Uani 1 1 d . . . . .
C3B C 0.6359(5) 0.245(4) 0.3919(11) 0.049(4) Uani 1 1 d . . . . .
C6A C 0.4901(5) 0.567(4) 0.3898(9) 0.046(4) Uani 1 1 d . . . . .
H6A H 0.506437 0.435100 0.352262 0.055 Uiso 1 1 calc R U . . .
C7A C 0.4499(5) 0.673(4) 0.3656(10) 0.043(3) Uani 1 1 d . . . . .
H7A H 0.440786 0.622354 0.309709 0.052 Uiso 1 1 calc R U . . .
C11A C 0.4308(5) 1.140(4) 0.6565(10) 0.048(4) Uani 1 1 d . . . . .
H11A H 0.415020 1.242677 0.700250 0.057 Uiso 1 1 calc R U . . .
C8B C 0.7013(5) 0.118(5) 0.5876(11) 0.050(4) Uani 1 1 d . . . . .
C10B C 0.7159(5) 0.001(4) 0.4219(14) 0.059(5) Uani 1 1 d . . . . .
C8A C 0.4226(4) 0.850(4) 0.4196(10) 0.040(3) Uani 1 1 d . . . . .
C6B C 0.6330(5) 0.358(5) 0.6244(12) 0.058(4) Uani 1 1 d . . . . .
H6B H 0.614763 0.435758 0.667383 0.070 Uiso 1 1 calc R U . . .
C12B C 0.6587(6) 0.144(5) 0.3219(13) 0.061(5) Uani 1 1 d . . . . .
H12B H 0.647720 0.156351 0.266036 0.073 Uiso 1 1 calc R U . . .
C11B C 0.6995(6) 0.020(5) 0.3369(13) 0.064(5) Uani 1 1 d . . . . .
H11B H 0.716024 -0.050554 0.290312 0.077 Uiso 1 1 calc R U . . .
C7B C 0.6739(5) 0.229(5) 0.6450(12) 0.058(4) Uani 1 1 d . . . . .
H7B H 0.681733 0.223086 0.703176 0.069 Uiso 1 1 calc R U . . .


_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
Br1A C8A 1.895(14) . ?
Br2A C10A 1.912(16) . ?
Br2B C10B 1.893(17) . ?
Br1B C8B 1.922(15) . ?
O1A C2A 1.236(19) . ?
O1B C2B 1.22(2) . ?
C9A C4A 1.38(2) . ?
C9A C10A 1.43(2) . ?
C9A C8A 1.43(2) . ?
C4A C3A 1.42(2) . ?
C4A C5A 1.43(2) . ?
C3A C12A 1.35(2) . ?
C3A C2A 1.46(2) . ?
C1B C1A 1.369(18) . ?
C1B C2B 1.49(2) . ?
C1B C5B 1.50(2) . ?
C9B C8B 1.42(2) . ?
C9B C4B 1.44(2) . ?
C9B C10B 1.43(3) . ?
C4B C3B 1.41(2) . ?
C4B C5B 1.42(2) . ?
C5B C6B 1.38(2) . ?
C2A C1A 1.53(2) . ?
C10A C11A 1.37(2) . ?
C5A C6A 1.37(2) . ?
C5A C1A 1.49(2) . ?
C12A C11A 1.40(2) . ?
C12A H12A 0.9300 . ?
C2B C3B 1.47(2) . ?
C3B C12B 1.36(2) . ?
C6A C7A 1.39(2) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.38(2) . ?
C7A H7A 0.9300 . ?
C11A H11A 0.9300 . ?
C8B C7B 1.31(2) . ?
C10B C11B 1.41(3) . ?
C6B C7B 1.43(2) . ?
C6B H6B 0.9300 . ?
C12B C11B 1.40(3) . ?
C12B H12B 0.9300 . ?
C11B H11B 0.9300 . ?
C7B H7B 0.9300 . ?

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
C4A C9A C10A 114.1(14) . . ?
C4A C9A C8A 114.8(14) . . ?
C10A C9A C8A 131.1(15) . . ?
C9A C4A C3A 123.3(14) . . ?
C9A C4A C5A 126.1(14) . . ?
C3A C4A C5A 110.6(13) . . ?
C12A C3A C4A 120.2(14) . . ?
C12A C3A C2A 131.7(15) . . ?
C4A C3A C2A 108.1(13) . . ?
C1A C1B C2B 125.0(13) . . ?
C1A C1B C5B 130.8(13) . . ?
C2B C1B C5B 104.1(12) . . ?
C8B C9B C4B 111.9(14) . . ?
C8B C9B C10B 134.8(15) . . ?
C4B C9B C10B 113.2(14) . . ?
C3B C4B C5B 111.9(14) . . ?
C3B C4B C9B 122.0(14) . . ?
C5B C4B C9B 126.1(15) . . ?
C6B C5B C4B 117.2(15) . . ?
C6B C5B C1B 134.6(15) . . ?
C4B C5B C1B 108.1(13) . . ?
O1A C2A C3A 123.5(14) . . ?
O1A C2A C1A 128.2(14) . . ?
C3A C2A C1A 108.2(12) . . ?
C11A C10A C9A 122.5(15) . . ?
C11A C10A Br2A 113.6(12) . . ?
C9A C10A Br2A 123.9(12) . . ?
C6A C5A C4A 116.6(14) . . ?
C6A C5A C1A 134.2(15) . . ?
C4A C5A C1A 109.0(13) . . ?
C1B C1A C5A 130.2(13) . . ?
C1B C1A C2A 125.7(12) . . ?
C5A C1A C2A 104.1(12) . . ?
C3A C12A C11A 118.5(14) . . ?
C3A C12A H12A 120.7 . . ?
C11A C12A H12A 120.7 . . ?
O1B C2B C3B 123.1(14) . . ?
O1B C2B C1B 127.8(15) . . ?
C3B C2B C1B 109.1(14) . . ?
C12B C3B C4B 123.3(16) . . ?
C12B C3B C2B 129.9(17) . . ?
C4B C3B C2B 106.8(13) . . ?
C5A C6A C7A 118.7(14) . . ?
C5A C6A H6A 120.6 . . ?
C7A C6A H6A 120.6 . . ?
C8A C7A C6A 124.2(14) . . ?
C8A C7A H7A 117.9 . . ?
C6A C7A H7A 117.9 . . ?
C10A C11A C12A 121.2(15) . . ?
C10A C11A H11A 119.4 . . ?
C12A C11A H11A 119.4 . . ?
C7B C8B C9B 123.0(15) . . ?
C7B C8B Br1B 114.8(13) . . ?
C9B C8B Br1B 122.1(12) . . ?
C11B C10B C9B 123.2(16) . . ?
C11B C10B Br2B 114.1(14) . . ?
C9B C10B Br2B 122.7(15) . . ?
C7A C8A C9A 119.2(13) . . ?
C7A C8A Br1A 115.3(11) . . ?
C9A C8A Br1A 125.4(11) . . ?
C5B C6B C7B 117.2(16) . . ?
C5B C6B H6B 121.4 . . ?
C7B C6B H6B 121.4 . . ?
C3B C12B C11B 117.5(18) . . ?
C3B C12B H12B 121.3 . . ?
C11B C12B H12B 121.3 . . ?
C12B C11B C10B 120.8(17) . . ?
C12B C11B H11B 119.6 . . ?
C10B C11B H11B 119.6 . . ?
C8B C7B C6B 124.5(16) . . ?
C8B C7B H7B 117.7 . . ?
C6B C7B H7B 117.7 . . ?

_refine_diff_density_max         0.707
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.135





