# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d8v20300
_database_code_depnum_ccdc_archive 'CCDC 2030783'
loop_
_audit_author_name
_audit_author_address
'Ze-jian Xue'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-09-08 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 Cl'
_chemical_formula_weight         342.84

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   10.8825(10)
_cell_length_b                   21.5798(16)
_cell_length_c                   8.2395(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1935.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2736
_cell_measurement_theta_min      5.317
_cell_measurement_theta_max      44.078

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9118
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.658
_diffrn_reflns_theta_max         25.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3743
_reflns_number_gt                2557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.974

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0420P)²+0.0540P] 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     SHELXL
_refine_ls_extinction_coef       0.029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 900 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3743
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_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
Cl1 Cl 0.79740(9) 0.20449(7) 0.4676(2) 0.1267(6) Uani 1 1 d . . . . .
C1 C 0.4456(3) 0.22740(14) 0.3542(5) 0.0650(9) Uani 1 1 d . . . . .
H1 H 0.4003 0.2529 0.2858 0.078 Uiso 1 1 calc R U . . .
C2 C 0.5723(4) 0.23409(17) 0.3606(5) 0.0763(11) Uani 1 1 d . . . . .
H2 H 0.6118 0.2636 0.2970 0.092 Uiso 1 1 calc R U . . .
C3 C 0.6378(3) 0.19676(19) 0.4616(6) 0.0744(10) Uani 1 1 d . . . . .
C4 C 0.5821(3) 0.15304(17) 0.5571(5) 0.0740(10) Uani 1 1 d . . . . .
H4 H 0.6282 0.1285 0.6270 0.089 Uiso 1 1 calc R U . . .
C5 C 0.4557(3) 0.14612(14) 0.5475(4) 0.0610(9) Uani 1 1 d . . . . .
H5 H 0.4174 0.1157 0.6095 0.073 Uiso 1 1 calc R U . . .
C6 C 0.3852(3) 0.18361(12) 0.4473(4) 0.0531(7) Uani 1 1 d . . . . .
C7 C 0.2496(3) 0.17556(13) 0.4357(4) 0.0547(7) Uani 1 1 d . . . . .
C8 C 0.1735(3) 0.22498(13) 0.4435(5) 0.0650(9) Uani 1 1 d . . . . .
H8 H 0.0918 0.2175 0.4168 0.078 Uiso 1 1 calc R U . . .
C9 C 0.2028(3) 0.28741(13) 0.4876(5) 0.0700(10) Uani 1 1 d . . . . .
H9 H 0.2822 0.2951 0.5239 0.084 Uiso 1 1 calc R U . . .
C10 C 0.1259(3) 0.33544(15) 0.4810(5) 0.0775(11) Uani 1 1 d . . . . .
H10 H 0.0478 0.3283 0.4392 0.093 Uiso 1 1 calc R U . . .
C11 C 0.1538(3) 0.39705(15) 0.5331(5) 0.0772(11) Uani 1 1 d . . . . .
H11 H 0.2303 0.4040 0.5800 0.093 Uiso 1 1 calc R U . . .
C12 C 0.0775(4) 0.44523(15) 0.5190(5) 0.0816(12) Uani 1 1 d . . . . .
H12 H 0.0014 0.4374 0.4720 0.098 Uiso 1 1 calc R U . . .
C13 C 0.1011(4) 0.50932(15) 0.5700(5) 0.0731(10) Uani 1 1 d . . . . .
C14 C 0.0197(4) 0.55528(17) 0.5199(6) 0.0916(14) Uani 1 1 d . . . . .
H14 H -0.0481 0.5448 0.4570 0.110 Uiso 1 1 calc R U . . .
C15 C 0.0389(5) 0.61611(19) 0.5630(7) 0.1034(15) Uani 1 1 d . . . . .
H15 H -0.0168 0.6464 0.5307 0.124 Uiso 1 1 calc R U . . .
C16 C 0.1392(5) 0.6322(2) 0.6526(7) 0.1069(16) Uani 1 1 d . . . . .
H16 H 0.1525 0.6735 0.6799 0.128 Uiso 1 1 calc R U . . .
C17 C 0.2197(5) 0.58803(19) 0.7020(7) 0.1052(17) Uani 1 1 d . . . . .
H17 H 0.2880 0.5992 0.7631 0.126 Uiso 1 1 calc R U . . .
C18 C 0.2011(4) 0.52715(18) 0.6626(6) 0.0902(13) Uani 1 1 d . . . . .
H18 H 0.2564 0.4973 0.6986 0.108 Uiso 1 1 calc R U . . .
C19 C 0.2007(3) 0.11261(14) 0.4074(4) 0.0549(8) Uani 1 1 d . . . . .
C20 C 0.2688(3) 0.06867(14) 0.3233(4) 0.0603(9) Uani 1 1 d . . . . .
H20 H 0.3479 0.0784 0.2890 0.072 Uiso 1 1 calc R U . . .
C21 C 0.2214(4) 0.01087(16) 0.2898(5) 0.0764(11) Uani 1 1 d . . . . .
H21 H 0.2681 -0.0176 0.2318 0.092 Uiso 1 1 calc R U . . .
C22 C 0.1064(5) -0.00478(19) 0.3411(6) 0.0855(12) Uani 1 1 d . . . . .
H22 H 0.0749 -0.0439 0.3182 0.103 Uiso 1 1 calc R U . . .
C23 C 0.0375(4) 0.03716(19) 0.4263(5) 0.0816(11) Uani 1 1 d . . . . .
H23 H -0.0409 0.0265 0.4616 0.098 Uiso 1 1 calc R U . . .
C24 C 0.0844(3) 0.09540(16) 0.4600(5) 0.0664(9) Uani 1 1 d . . . . .
H24 H 0.0372 0.1234 0.5189 0.080 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
Cl1 C3 1.746(3) . ?
C1 C6 1.384(4) . ?
C1 C2 1.387(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(5) . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(4) . ?
C7 C8 1.352(4) . ?
C7 C19 1.477(4) . ?
C8 C9 1.431(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.333(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.430(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.336(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.468(5) . ?
C12 H12 0.9300 . ?
C13 C18 1.383(5) . ?
C13 C14 1.392(5) . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.389(4) . ?
C19 C20 1.388(4) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.363(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.384(5) . ?
C23 H23 0.9300 . ?
C24 H24 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
C6 C1 C2 121.5(3) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 Cl1 118.8(3) . . ?
C4 C3 Cl1 119.3(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 C7 121.0(3) . . ?
C5 C6 C7 121.2(3) . . ?
C8 C7 C19 120.8(3) . . ?
C8 C7 C6 120.8(3) . . ?
C19 C7 C6 118.3(3) . . ?
C7 C8 C9 128.2(3) . . ?
C7 C8 H8 115.9 . . ?
C9 C8 H8 115.9 . . ?
C10 C9 C8 125.6(3) . . ?
C10 C9 H9 117.2 . . ?
C8 C9 H9 117.2 . . ?
C9 C10 C11 125.2(4) . . ?
C9 C10 H10 117.4 . . ?
C11 C10 H10 117.4 . . ?
C12 C11 C10 124.4(4) . . ?
C12 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
C11 C12 C13 126.8(4) . . ?
C11 C12 H12 116.6 . . ?
C13 C12 H12 116.6 . . ?
C18 C13 C14 117.8(3) . . ?
C18 C13 C12 123.9(4) . . ?
C14 C13 C12 118.4(4) . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.9(4) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C24 C19 C20 117.4(3) . . ?
C24 C19 C7 121.6(3) . . ?
C20 C19 C7 121.0(3) . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.9(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 121.0(4) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 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(5) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C1 C2 C3 Cl1 179.2(3) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
Cl1 C3 C4 C5 -178.1(3) . . . . ?
C3 C4 C5 C6 -1.9(5) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C1 C6 C7 -178.1(3) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C1 C6 C7 C8 -48.7(5) . . . . ?
C5 C6 C7 C8 133.5(3) . . . . ?
C1 C6 C7 C19 128.2(3) . . . . ?
C5 C6 C7 C19 -49.5(4) . . . . ?
C19 C7 C8 C9 172.4(4) . . . . ?
C6 C7 C8 C9 -10.7(6) . . . . ?
C7 C8 C9 C10 174.4(4) . . . . ?
C8 C9 C10 C11 176.6(4) . . . . ?
C9 C10 C11 C12 176.9(5) . . . . ?
C10 C11 C12 C13 -179.9(4) . . . . ?
C11 C12 C13 C18 -9.8(7) . . . . ?
C11 C12 C13 C14 168.9(4) . . . . ?
C18 C13 C14 C15 -0.4(6) . . . . ?
C12 C13 C14 C15 -179.2(4) . . . . ?
C13 C14 C15 C16 1.2(8) . . . . ?
C14 C15 C16 C17 -1.0(8) . . . . ?
C15 C16 C17 C18 0.0(9) . . . . ?
C16 C17 C18 C13 0.9(8) . . . . ?
C14 C13 C18 C17 -0.7(6) . . . . ?
C12 C13 C18 C17 178.1(5) . . . . ?
C8 C7 C19 C24 -30.3(5) . . . . ?
C6 C7 C19 C24 152.7(3) . . . . ?
C8 C7 C19 C20 148.2(3) . . . . ?
C6 C7 C19 C20 -28.8(4) . . . . ?
C24 C19 C20 C21 1.7(5) . . . . ?
C7 C19 C20 C21 -176.9(3) . . . . ?
C19 C20 C21 C22 -1.0(5) . . . . ?
C20 C21 C22 C23 0.1(6) . . . . ?
C21 C22 C23 C24 0.1(6) . . . . ?
C22 C23 C24 C19 0.6(6) . . . . ?
C20 C19 C24 C23 -1.5(5) . . . . ?
C7 C19 C24 C23 177.1(3) . . . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.024

_shelxl_version_number           2013-4

