# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_1
_audit_block_doi                 10.5517/ccdc.csd.cc27x4z9
_database_code_depnum_ccdc_archive 'CCDC 2082641'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acscatal.1c01671 2021
loop_
_audit_author_name
_audit_author_address
'Haolan Zhang'
;xianjiaotong University
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        8b
_chemical_formula_moiety         'C20 H18 Cl N O2'
_chemical_formula_sum            'C20 H18 Cl N O2'
_chemical_formula_weight         339.80
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
N N 0.0311 0.0180 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2846(5)
_cell_length_b                   11.5452(7)
_cell_length_c                   17.4901(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1672.88(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6320
_cell_measurement_temperature    150
_cell_measurement_theta_max      58.842
_cell_measurement_theta_min      4.589
_shelx_estimated_absorpt_T_max   0.631
_shelx_estimated_absorpt_T_min   0.589
_exptl_absorpt_coefficient_mu    2.112
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1176 before and 0.0544 after correction.
The Ratio of minimum to maximum transmission is 0.8163.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9171
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        58.861
_diffrn_reflns_theta_max         58.861
_diffrn_reflns_theta_min         4.589
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.65
_diffrn_source_power             0.029133
_diffrn_source_voltage           44.82
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2305
_reflns_number_total             2378
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.032(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0216
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0249P)²+0.1807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0535
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.968(15)
 0.032(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C007(H007)
3.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M)
3.c Idealised Me refined as rotating group:
 C00N(H00E,H00L,H00N), C00O(H00O,H00P,H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl01 Cl 0.61434(7) 0.68423(5) 0.72361(3) 0.03126(16) Uani 1 1 d . . . . .
O002 O 0.86884(19) 0.13394(13) 0.60424(8) 0.0291(4) Uani 1 1 d . . . . .
O003 O 0.6673(2) 0.59388(15) 0.39423(8) 0.0338(4) Uani 1 1 d . . . . .
N004 N 0.2273(2) 0.52146(17) 0.60312(11) 0.0283(4) Uani 1 1 d . . . . .
C005 C 0.5727(2) 0.55458(18) 0.59492(12) 0.0207(5) Uani 1 1 d . . . . .
C006 C 0.3196(2) 0.48600(18) 0.66130(12) 0.0213(5) Uani 1 1 d . . . . .
C007 C 0.4969(3) 0.46180(19) 0.64522(11) 0.0205(5) Uani 1 1 d . . . . .
H007 H 0.553231 0.466807 0.695674 0.025 Uiso 1 1 calc R U . . .
C008 C 0.5275(2) 0.33936(18) 0.61544(11) 0.0205(5) Uani 1 1 d . . . . .
C009 C 0.7196(2) 0.1840(2) 0.59895(11) 0.0234(5) Uani 1 1 d . . . . .
C00A C 0.6837(3) 0.29526(19) 0.62344(11) 0.0230(5) Uani 1 1 d . . . . .
H00A H 0.765748 0.341757 0.645769 0.028 Uiso 1 1 calc R U . . .
C00B C 0.4094(3) 0.27188(19) 0.58210(11) 0.0256(5) Uani 1 1 d . . . . .
H00B H 0.303556 0.301790 0.575343 0.031 Uiso 1 1 calc R U . . .
C00C C 0.2584(3) 0.4679(2) 0.73396(12) 0.0270(5) Uani 1 1 d . . . . .
H00C H 0.327648 0.444120 0.774300 0.032 Uiso 1 1 calc R U . . .
C00D C 0.7262(3) 0.7213(2) 0.50230(13) 0.0282(5) Uani 1 1 d . . . . .
H00D H 0.779816 0.776766 0.471213 0.034 Uiso 1 1 calc R U . . .
C00E C 0.6625(3) 0.62087(19) 0.47047(12) 0.0242(5) Uani 1 1 d . . . . .
C00F C 0.0697(3) 0.5390(2) 0.61717(14) 0.0327(6) Uani 1 1 d . . . . .
H00F H 0.003208 0.564950 0.576393 0.039 Uiso 1 1 calc R U . . .
C00G C 0.5868(3) 0.53895(19) 0.51648(11) 0.0237(5) Uani 1 1 d . . . . .
H00G H 0.543874 0.470856 0.493753 0.028 Uiso 1 1 calc R U . . .
C00H C 0.5991(3) 0.11534(19) 0.56679(12) 0.0274(5) Uani 1 1 d . . . . .
H00H H 0.622663 0.038522 0.550827 0.033 Uiso 1 1 calc R U . . .
C00I C -0.0003(3) 0.5212(2) 0.68751(13) 0.0329(6) Uani 1 1 d . . . . .
H00I H -0.112592 0.533916 0.694744 0.039 Uiso 1 1 calc R U . . .
C00J C 0.7100(3) 0.7389(2) 0.58035(12) 0.0285(5) Uani 1 1 d . . . . .
H00J H 0.751620 0.807458 0.603006 0.034 Uiso 1 1 calc R U . . .
C00K C 0.0954(3) 0.4846(2) 0.74736(12) 0.0317(6) Uani 1 1 d . . . . .
H00K H 0.050589 0.471127 0.796556 0.038 Uiso 1 1 calc R U . . .
C00L C 0.6336(3) 0.65711(18) 0.62540(11) 0.0241(5) Uani 1 1 d . . . . .
C00M C 0.4462(3) 0.1593(2) 0.55828(13) 0.0294(5) Uani 1 1 d . . . . .
H00M H 0.364372 0.112618 0.535941 0.035 Uiso 1 1 calc R U . . .
C00N C 0.9960(3) 0.2023(2) 0.63530(14) 0.0345(6) Uani 1 1 d . . . . .
H00E H 1.009389 0.272635 0.604533 0.052 Uiso 1 1 calc R U . . .
H00L H 1.096628 0.157699 0.634673 0.052 Uiso 1 1 calc R U . . .
H00N H 0.969560 0.223745 0.688048 0.052 Uiso 1 1 calc R U . . .
C00O C 0.7695(4) 0.6628(2) 0.34684(14) 0.0441(7) Uani 1 1 d . . . . .
H00O H 0.769764 0.631208 0.294833 0.066 Uiso 1 1 calc R U . . .
H00P H 0.879553 0.661868 0.367345 0.066 Uiso 1 1 calc R U . . .
H00Q H 0.729248 0.742591 0.345804 0.066 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
Cl01 C00L 1.753(2) . ?
O002 C009 1.368(3) . ?
O002 C00N 1.424(3) . ?
O003 C00E 1.370(3) . ?
O003 C00O 1.427(3) . ?
N004 C006 1.337(3) . ?
N004 C00F 1.344(3) . ?
C005 C007 1.522(3) . ?
C005 C00G 1.389(3) . ?
C005 C00L 1.393(3) . ?
C006 C007 1.521(3) . ?
C006 C00C 1.384(3) . ?
C007 H007 1.0000 . ?
C007 C008 1.528(3) . ?
C008 C00A 1.398(3) . ?
C008 C00B 1.380(3) . ?
C009 C00A 1.386(3) . ?
C009 C00H 1.393(3) . ?
C00A H00A 0.9500 . ?
C00B H00B 0.9500 . ?
C00B C00M 1.399(3) . ?
C00C H00C 0.9500 . ?
C00C C00K 1.383(3) . ?
C00D H00D 0.9500 . ?
C00D C00E 1.391(3) . ?
C00D C00J 1.387(3) . ?
C00E C00G 1.391(3) . ?
C00F H00F 0.9500 . ?
C00F C00I 1.376(3) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00M 1.372(3) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.380(3) . ?
C00J H00J 0.9500 . ?
C00J C00L 1.383(3) . ?
C00K H00K 0.9500 . ?
C00M H00M 0.9500 . ?
C00N H00E 0.9800 . ?
C00N H00L 0.9800 . ?
C00N H00N 0.9800 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 0.9800 . ?

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
C009 O002 C00N 117.40(17) . . ?
C00E O003 C00O 117.13(18) . . ?
C006 N004 C00F 117.6(2) . . ?
C00G C005 C007 120.96(19) . . ?
C00G C005 C00L 117.26(19) . . ?
C00L C005 C007 121.78(18) . . ?
N004 C006 C007 117.89(19) . . ?
N004 C006 C00C 122.3(2) . . ?
C00C C006 C007 119.74(19) . . ?
C005 C007 H007 106.1 . . ?
C005 C007 C008 112.69(17) . . ?
C006 C007 C005 112.09(18) . . ?
C006 C007 H007 106.1 . . ?
C006 C007 C008 113.16(18) . . ?
C008 C007 H007 106.1 . . ?
C00A C008 C007 117.18(19) . . ?
C00B C008 C007 123.28(19) . . ?
C00B C008 C00A 119.5(2) . . ?
O002 C009 C00A 124.3(2) . . ?
O002 C009 C00H 115.7(2) . . ?
C00A C009 C00H 119.9(2) . . ?
C008 C00A H00A 119.8 . . ?
C009 C00A C008 120.3(2) . . ?
C009 C00A H00A 119.8 . . ?
C008 C00B H00B 120.1 . . ?
C008 C00B C00M 119.7(2) . . ?
C00M C00B H00B 120.1 . . ?
C006 C00C H00C 120.3 . . ?
C00K C00C C006 119.5(2) . . ?
C00K C00C H00C 120.3 . . ?
C00E C00D H00D 120.7 . . ?
C00J C00D H00D 120.7 . . ?
C00J C00D C00E 118.6(2) . . ?
O003 C00E C00D 124.63(19) . . ?
O003 C00E C00G 114.94(19) . . ?
C00D C00E C00G 120.4(2) . . ?
N004 C00F H00F 118.3 . . ?
N004 C00F C00I 123.4(2) . . ?
C00I C00F H00F 118.3 . . ?
C005 C00G C00E 121.4(2) . . ?
C005 C00G H00G 119.3 . . ?
C00E C00G H00G 119.3 . . ?
C009 C00H H00H 120.2 . . ?
C00M C00H C009 119.6(2) . . ?
C00M C00H H00H 120.2 . . ?
C00F C00I H00I 120.6 . . ?
C00F C00I C00K 118.8(2) . . ?
C00K C00I H00I 120.6 . . ?
C00D C00J H00J 119.8 . . ?
C00L C00J C00D 120.3(2) . . ?
C00L C00J H00J 119.8 . . ?
C00C C00K H00K 120.8 . . ?
C00I C00K C00C 118.4(2) . . ?
C00I C00K H00K 120.8 . . ?
C005 C00L Cl01 119.58(16) . . ?
C00J C00L Cl01 118.54(16) . . ?
C00J C00L C005 121.88(18) . . ?
C00B C00M H00M 119.6 . . ?
C00H C00M C00B 120.8(2) . . ?
C00H C00M H00M 119.6 . . ?
O002 C00N H00E 109.5 . . ?
O002 C00N H00L 109.5 . . ?
O002 C00N H00N 109.5 . . ?
H00E C00N H00L 109.5 . . ?
H00E C00N H00N 109.5 . . ?
H00L C00N H00N 109.5 . . ?
O003 C00O H00O 109.5 . . ?
O003 C00O H00P 109.5 . . ?
O003 C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?

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
O002 C009 C00A C008 179.76(18) . . . . ?
O002 C009 C00H C00M -179.08(19) . . . . ?
O003 C00E C00G C005 -179.95(19) . . . . ?
N004 C006 C007 C005 43.4(3) . . . . ?
N004 C006 C007 C008 -85.4(2) . . . . ?
N004 C006 C00C C00K 1.3(4) . . . . ?
N004 C00F C00I C00K 0.6(4) . . . . ?
C005 C007 C008 C00A 72.7(2) . . . . ?
C005 C007 C008 C00B -107.7(2) . . . . ?
C006 N004 C00F C00I -0.7(4) . . . . ?
C006 C007 C008 C00A -158.82(18) . . . . ?
C006 C007 C008 C00B 20.8(3) . . . . ?
C006 C00C C00K C00I -1.2(3) . . . . ?
C007 C005 C00G C00E -177.0(2) . . . . ?
C007 C005 C00L Cl01 -3.2(3) . . . . ?
C007 C005 C00L C00J 176.6(2) . . . . ?
C007 C006 C00C C00K -176.8(2) . . . . ?
C007 C008 C00A C009 178.85(18) . . . . ?
C007 C008 C00B C00M -178.16(19) . . . . ?
C008 C00B C00M C00H -0.8(3) . . . . ?
C009 C00H C00M C00B -0.5(3) . . . . ?
C00A C008 C00B C00M 1.5(3) . . . . ?
C00A C009 C00H C00M 1.2(3) . . . . ?
C00B C008 C00A C009 -0.8(3) . . . . ?
C00C C006 C007 C005 -138.4(2) . . . . ?
C00C C006 C007 C008 92.8(2) . . . . ?
C00D C00E C00G C005 0.0(3) . . . . ?
C00D C00J C00L Cl01 -179.32(18) . . . . ?
C00D C00J C00L C005 0.9(3) . . . . ?
C00E C00D C00J C00L 0.8(3) . . . . ?
C00F N004 C006 C007 177.8(2) . . . . ?
C00F N004 C006 C00C -0.3(3) . . . . ?
C00F C00I C00K C00C 0.3(4) . . . . ?
C00G C005 C007 C006 -96.8(2) . . . . ?
C00G C005 C007 C008 32.2(3) . . . . ?
C00G C005 C00L Cl01 178.12(16) . . . . ?
C00G C005 C00L C00J -2.1(3) . . . . ?
C00H C009 C00A C008 -0.5(3) . . . . ?
C00J C00D C00E O003 178.7(2) . . . . ?
C00J C00D C00E C00G -1.2(3) . . . . ?
C00L C005 C007 C006 84.5(2) . . . . ?
C00L C005 C007 C008 -146.4(2) . . . . ?
C00L C005 C00G C00E 1.7(3) . . . . ?
C00N O002 C009 C00A -1.6(3) . . . . ?
C00N O002 C009 C00H 178.67(19) . . . . ?
C00O O003 C00E C00D 11.8(3) . . . . ?
C00O O003 C00E C00G -168.3(2) . . . . ?

# (APPEND TO CIF)

_THETM01_1                       
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
         Calculated sin(theta_max)/wavelength =    0.5551
RESPONSE: This is because diffracted intensity of the single crystal is
weaker. 
;

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.968(15)
2 0.032(15)

