# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1920326'
_audit_update_record             
;
2019-06-01 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 Cl4 N O'
_chemical_formula_sum            'C24 H15 Cl4 N O'
_chemical_formula_weight         475.17

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'
N N 0.0061 0.0033 '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/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                   10.0953(5)
_cell_length_b                   26.4194(9)
_cell_length_c                   8.7916(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.895(6)
_cell_angle_gamma                90
_cell_volume                     2126.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7811
_cell_measurement_theta_min      3.8020
_cell_measurement_theta_max      27.7060

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.573
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26358
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.447
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3733
_reflns_number_gt                3302
_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       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0396P)²+1.6848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3733
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
Cl1 Cl 0.83544(8) 0.66432(3) 0.43143(9) 0.05119(19) Uani 1 1 d . . . . .
Cl2 Cl 1.09478(7) 0.65112(3) 0.73655(10) 0.0568(2) Uani 1 1 d . . . . .
Cl4 Cl 0.51699(8) 0.53989(3) 0.24983(8) 0.0534(2) Uani 1 1 d . . . . .
Cl3 Cl 0.88061(8) 0.72488(2) 0.72019(10) 0.0567(2) Uani 1 1 d . . . . .
O1 O 0.79101(17) 0.49827(6) 0.5229(2) 0.0385(4) Uani 1 1 d . . . . .
N1 N 0.67106(19) 0.63240(7) 0.6505(2) 0.0316(4) Uani 1 1 d . . . . .
C19 C 0.9723(2) 0.53309(8) 0.7565(3) 0.0330(5) Uani 1 1 d . . . . .
C8 C 0.6084(2) 0.63609(9) 0.7696(3) 0.0330(5) Uani 1 1 d . . . . .
C7 C 0.5757(2) 0.61136(8) 0.4928(3) 0.0313(5) Uani 1 1 d . . . . .
C16 C 0.7535(2) 0.54662(8) 0.5453(3) 0.0332(5) Uani 1 1 d . . . . .
C14 C 0.8290(2) 0.62292(8) 0.7176(3) 0.0313(5) Uani 1 1 d . . . . .
C17 C 0.6157(2) 0.56834(9) 0.4413(3) 0.0340(5) Uani 1 1 d . . . . .
C15 C 0.8572(2) 0.56988(8) 0.6793(3) 0.0316(5) Uani 1 1 d . . . . .
C1 C 0.4427(2) 0.64168(9) 0.3978(3) 0.0351(5) Uani 1 1 d . . . . .
C20 C 0.9271(3) 0.49061(9) 0.6532(3) 0.0356(5) Uani 1 1 d . . . . .
C24 C 1.1049(3) 0.53120(10) 0.8979(3) 0.0411(6) Uani 1 1 d . . . . .
H24 H 1.138689 0.558849 0.969470 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5008(3) 0.60222(10) 0.7620(3) 0.0408(6) Uani 1 1 d . . . . .
H9 H 0.471311 0.576688 0.681744 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6530(3) 0.67348(10) 0.8926(3) 0.0431(6) Uani 1 1 d . . . . .
H13 H 0.725929 0.696227 0.900346 0.052 Uiso 1 1 calc R U . . .
C21 C 1.0067(3) 0.44683(10) 0.6790(4) 0.0456(6) Uani 1 1 d . . . . .
H21 H 0.974215 0.419503 0.605858 0.055 Uiso 1 1 calc R U . . .
C2 C 0.3060(3) 0.61981(11) 0.3143(3) 0.0456(6) Uani 1 1 d . . . . .
H2 H 0.294563 0.585086 0.321238 0.055 Uiso 1 1 calc R U . . .
C23 C 1.1849(3) 0.48660(10) 0.9286(4) 0.0502(7) Uani 1 1 d . . . . .
H23 H 1.272166 0.484154 1.024296 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9051(3) 0.66363(9) 0.6535(3) 0.0381(6) Uani 1 1 d . . . . .
C10 C 0.4377(3) 0.60626(12) 0.8726(4) 0.0528(7) Uani 1 1 d . . . . .
H10 H 0.365221 0.583494 0.866112 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5883(3) 0.67658(11) 1.0031(3) 0.0517(7) Uani 1 1 d . . . . .
H12 H 0.618543 0.701434 1.085656 0.062 Uiso 1 1 calc R U . . .
C22 C 1.1381(3) 0.44569(10) 0.8204(4) 0.0525(7) Uani 1 1 d . . . . .
H22 H 1.196181 0.416862 0.843105 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4560(3) 0.69360(10) 0.3873(4) 0.0516(7) Uani 1 1 d . . . . .
H6 H 0.546165 0.709002 0.445731 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4802(3) 0.64352(12) 0.9925(4) 0.0545(8) Uani 1 1 d . . . . .
H11 H 0.435940 0.646307 1.066027 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1869(3) 0.64960(12) 0.2207(4) 0.0569(8) Uani 1 1 d . . . . .
H3 H 0.095397 0.634742 0.166048 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2020(3) 0.70075(13) 0.2074(4) 0.0669(9) Uani 1 1 d . . . . .
H4 H 0.121645 0.720436 0.142288 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3365(3) 0.72260(11) 0.2909(4) 0.0704(10) Uani 1 1 d . . . . .
H5 H 0.347269 0.757309 0.282430 0.084 Uiso 1 1 calc R U . . .
H14 H 0.871(3) 0.6284(9) 0.837(3) 0.036(6) Uiso 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
Cl1 C18 1.775(3) . ?
Cl2 C18 1.769(2) . ?
Cl4 C17 1.726(2) . ?
Cl3 C18 1.774(2) . ?
O1 C16 1.370(3) . ?
O1 C20 1.385(3) . ?
N1 C7 1.426(3) . ?
N1 C8 1.436(3) . ?
N1 C14 1.470(3) . ?
C19 C24 1.393(3) . ?
C19 C20 1.394(3) . ?
C19 C15 1.446(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.392(3) . ?
C7 C17 1.347(3) . ?
C7 C1 1.483(3) . ?
C16 C15 1.350(3) . ?
C16 C17 1.425(3) . ?
C14 C15 1.496(3) . ?
C14 C18 1.558(3) . ?
C14 H14 0.96(2) . ?
C1 C6 1.385(4) . ?
C1 C2 1.387(3) . ?
C20 C21 1.371(3) . ?
C24 C23 1.389(4) . ?
C24 H24 0.9300 . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C13 C12 1.383(4) . ?
C13 H13 0.9300 . ?
C21 C22 1.385(4) . ?
C21 H21 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C23 C22 1.385(4) . ?
C23 H23 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C12 C11 1.370(4) . ?
C12 H12 0.9300 . ?
C22 H22 0.9300 . ?
C6 C5 1.378(4) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4 0.9300 . ?
C5 H5 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
C16 O1 C20 104.80(17) . . ?
C7 N1 C8 114.28(17) . . ?
C7 N1 C14 119.83(18) . . ?
C8 N1 C14 117.09(18) . . ?
C24 C19 C20 118.7(2) . . ?
C24 C19 C15 136.3(2) . . ?
C20 C19 C15 105.0(2) . . ?
C9 C8 C13 119.1(2) . . ?
C9 C8 N1 119.8(2) . . ?
C13 C8 N1 121.1(2) . . ?
C17 C7 N1 118.8(2) . . ?
C17 C7 C1 126.5(2) . . ?
N1 C7 C1 114.69(19) . . ?
C15 C16 O1 112.9(2) . . ?
C15 C16 C17 124.5(2) . . ?
O1 C16 C17 122.5(2) . . ?
N1 C14 C15 110.27(18) . . ?
N1 C14 C18 110.74(18) . . ?
C15 C14 C18 113.31(19) . . ?
N1 C14 H14 108.6(14) . . ?
C15 C14 H14 110.3(14) . . ?
C18 C14 H14 103.3(14) . . ?
C7 C17 C16 118.3(2) . . ?
C7 C17 Cl4 124.34(18) . . ?
C16 C17 Cl4 117.23(17) . . ?
C16 C15 C19 106.2(2) . . ?
C16 C15 C14 118.1(2) . . ?
C19 C15 C14 135.7(2) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 C7 118.8(2) . . ?
C2 C1 C7 122.4(2) . . ?
C21 C20 O1 124.6(2) . . ?
C21 C20 C19 124.3(2) . . ?
O1 C20 C19 111.08(19) . . ?
C23 C24 C19 117.7(2) . . ?
C23 C24 H24 121.1 . . ?
C19 C24 H24 121.1 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C20 C21 C22 116.1(2) . . ?
C20 C21 H21 121.9 . . ?
C22 C21 H21 121.9 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C22 C23 C24 121.8(2) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C14 C18 Cl2 109.54(16) . . ?
C14 C18 Cl3 110.59(17) . . ?
Cl2 C18 Cl3 108.15(13) . . ?
C14 C18 Cl1 112.15(16) . . ?
Cl2 C18 Cl1 108.34(14) . . ?
Cl3 C18 Cl1 107.95(13) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C23 C22 C21 121.3(2) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.043

