# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_a
_audit_block_doi                 10.5517/ccdc.csd.cc2gwyr2
_database_code_depnum_ccdc_archive 'CCDC 2290985'
loop_
_audit_author_name
_audit_author_address
'Zhi-Llin Ren'
;Hubei University of Arts and Science
China
;
_audit_update_record             
;
2023-08-27 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Cl N2 O'
_chemical_formula_weight         338.82

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'
O O 0.0106 0.0060 '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      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                   9.876(5)
_cell_length_b                   17.391(9)
_cell_length_c                   10.776(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.377(10)
_cell_angle_gamma                90
_cell_volume                     1814.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5790
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      22.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27362
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.408
_diffrn_reflns_theta_max         25.160
_diffrn_reflns_theta_full        25.160
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3220
_reflns_number_gt                1910
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0656P)²+1.1425P] 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         3220
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 -0.1845(3) 0.6315(2) 0.3084(3) 0.0599(9) Uani 1 1 d . . . . .
C2 C -0.1399(3) 0.5918(2) 0.4176(3) 0.0622(9) Uani 1 1 d . . . . .
H2 H -0.2000 0.5597 0.4496 0.075 Uiso 1 1 calc R U . . .
C3 C -0.0048(3) 0.59959(18) 0.4804(3) 0.0575(8) Uani 1 1 d . . . . .
H3 H 0.0251 0.5731 0.5558 0.069 Uiso 1 1 calc R U . . .
C4 C 0.0874(3) 0.64620(17) 0.4333(3) 0.0476(7) Uani 1 1 d . . . . .
C5 C 0.0381(4) 0.6853(2) 0.3225(3) 0.0785(12) Uani 1 1 d . . . . .
H5 H 0.0978 0.7166 0.2885 0.094 Uiso 1 1 calc R U . . .
C6 C -0.0975(4) 0.6789(3) 0.2607(3) 0.0888(13) Uani 1 1 d . . . . .
H6 H -0.1294 0.7068 0.1871 0.107 Uiso 1 1 calc R U . . .
C7 C 0.2351(3) 0.64732(18) 0.5001(3) 0.0502(8) Uani 1 1 d . . . . .
C8 C 0.3324(3) 0.69904(17) 0.4604(3) 0.0497(8) Uani 1 1 d . . . . .
H8 H 0.3004 0.7345 0.3968 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4692(3) 0.69765(17) 0.5130(3) 0.0464(7) Uani 1 1 d . . . . .
C10 C 0.5814(3) 0.74802(17) 0.4903(3) 0.0468(7) Uani 1 1 d . . . . .
C11 C 0.7013(3) 0.72648(17) 0.5744(3) 0.0469(7) Uani 1 1 d . . . . .
C12 C 0.8244(3) 0.76554(19) 0.5766(3) 0.0584(9) Uani 1 1 d . . . . .
H12 H 0.9048 0.7518 0.6329 0.070 Uiso 1 1 calc R U . . .
C13 C 0.8233(3) 0.8252(2) 0.4926(3) 0.0686(10) Uani 1 1 d . . . . .
H13 H 0.9041 0.8529 0.4935 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7049(4) 0.8453(2) 0.4066(3) 0.0672(9) Uani 1 1 d . . . . .
H14 H 0.7086 0.8848 0.3493 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5819(3) 0.80752(19) 0.4046(3) 0.0578(8) Uani 1 1 d . . . . .
H15 H 0.5021 0.8214 0.3478 0.069 Uiso 1 1 calc R U . . .
C16 C 0.6708(3) 0.65925(17) 0.6482(3) 0.0456(7) Uani 1 1 d . . . . .
C17 C 0.7247(3) 0.5537(2) 0.7961(3) 0.0634(9) Uani 1 1 d . . . . .
C18 C 0.6200(6) 0.5709(3) 0.8786(4) 0.1209(18) Uani 1 1 d . . . . .
H18A H 0.5320 0.5821 0.8257 0.181 Uiso 1 1 calc R U . . .
H18B H 0.6503 0.6145 0.9315 0.181 Uiso 1 1 calc R U . . .
H18C H 0.6114 0.5271 0.9306 0.181 Uiso 1 1 calc R U . . .
C19 C 0.6669(5) 0.4903(2) 0.7031(4) 0.0986(14) Uani 1 1 d . . . . .
H19A H 0.6613 0.4433 0.7485 0.148 Uiso 1 1 calc R U . . .
H19B H 0.7265 0.4832 0.6437 0.148 Uiso 1 1 calc R U . . .
H19C H 0.5764 0.5046 0.6586 0.148 Uiso 1 1 calc R U . . .
C20 C 0.8601(5) 0.5256(3) 0.8731(6) 0.173(3) Uani 1 1 d . . . . .
H20A H 0.8966 0.5634 0.9357 0.259 Uiso 1 1 calc R U . . .
H20B H 0.9245 0.5173 0.8183 0.259 Uiso 1 1 calc R U . . .
H20C H 0.8454 0.4782 0.9142 0.259 Uiso 1 1 calc R U . . .
Cl1 Cl -0.35571(9) 0.62261(7) 0.23026(10) 0.0927(4) Uani 1 1 d . . . . .
N1 N 0.5288(2) 0.64660(14) 0.6051(2) 0.0519(7) Uani 1 1 d . . . . .
H1 H 0.4837 0.6105 0.6334 0.062 Uiso 1 1 calc R U . . .
N2 N 0.7584(2) 0.62365(14) 0.7297(2) 0.0533(7) Uani 1 1 d . . . . .
O1 O 0.2714(2) 0.60133(13) 0.5893(2) 0.0673(7) 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 1.360(4) . ?
C1 C6 1.362(5) . ?
C1 Cl1 1.740(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 C7 1.494(4) . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.247(4) . ?
C7 C8 1.441(4) . ?
C8 C9 1.358(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.374(4) . ?
C9 C10 1.471(4) . ?
C10 C15 1.387(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.389(4) . ?
C11 C16 1.479(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N2 1.267(3) . ?
C16 N1 1.404(4) . ?
C17 N2 1.482(4) . ?
C17 C20 1.510(5) . ?
C17 C18 1.521(6) . ?
C17 C19 1.523(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 H1 0.8600 . ?

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 120.8(3) . . ?
C2 C1 Cl1 119.4(3) . . ?
C6 C1 Cl1 119.8(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 C7 123.8(3) . . ?
C3 C4 C7 118.7(3) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O1 C7 C8 121.5(3) . . ?
O1 C7 C4 117.9(3) . . ?
C8 C7 C4 120.6(3) . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 N1 124.2(3) . . ?
C8 C9 C10 129.8(3) . . ?
N1 C9 C10 106.0(2) . . ?
C15 C10 C11 121.2(3) . . ?
C15 C10 C9 131.1(3) . . ?
C11 C10 C9 107.7(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 C16 130.4(3) . . ?
C10 C11 C16 109.0(2) . . ?
C13 C12 C11 117.6(3) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 117.7(3) . . ?
C14 C15 H15 121.2 . . ?
C10 C15 H15 121.2 . . ?
N2 C16 N1 130.9(3) . . ?
N2 C16 C11 125.1(3) . . ?
N1 C16 C11 104.0(2) . . ?
N2 C17 C20 105.8(3) . . ?
N2 C17 C18 111.4(3) . . ?
C20 C17 C18 111.9(4) . . ?
N2 C17 C19 111.5(3) . . ?
C20 C17 C19 107.7(4) . . ?
C18 C17 C19 108.5(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 N1 C16 113.3(2) . . ?
C9 N1 H1 123.3 . . ?
C16 N1 H1 123.3 . . ?
C16 N2 C17 123.2(3) . . ?

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 -0.2(5) . . . . ?
Cl1 C1 C2 C3 -179.2(3) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 C7 -175.1(3) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C7 C4 C5 C6 176.3(4) . . . . ?
C2 C1 C6 C5 1.5(6) . . . . ?
Cl1 C1 C6 C5 -179.5(3) . . . . ?
C4 C5 C6 C1 -1.6(7) . . . . ?
C5 C4 C7 O1 -170.0(3) . . . . ?
C3 C4 C7 O1 5.9(4) . . . . ?
C5 C4 C7 C8 8.9(5) . . . . ?
C3 C4 C7 C8 -175.3(3) . . . . ?
O1 C7 C8 C9 3.6(5) . . . . ?
C4 C7 C8 C9 -175.1(3) . . . . ?
C7 C8 C9 N1 1.8(5) . . . . ?
C7 C8 C9 C10 -176.2(3) . . . . ?
C8 C9 C10 C15 -4.5(5) . . . . ?
N1 C9 C10 C15 177.2(3) . . . . ?
C8 C9 C10 C11 175.7(3) . . . . ?
N1 C9 C10 C11 -2.7(3) . . . . ?
C15 C10 C11 C12 1.6(4) . . . . ?
C9 C10 C11 C12 -178.5(3) . . . . ?
C15 C10 C11 C16 -176.9(3) . . . . ?
C9 C10 C11 C16 3.0(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C16 C11 C12 C13 177.6(3) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C12 C13 C14 C15 2.1(6) . . . . ?
C13 C14 C15 C10 -1.0(5) . . . . ?
C11 C10 C15 C14 -0.8(4) . . . . ?
C9 C10 C15 C14 179.4(3) . . . . ?
C12 C11 C16 N2 -1.0(5) . . . . ?
C10 C11 C16 N2 177.3(3) . . . . ?
C12 C11 C16 N1 179.6(3) . . . . ?
C10 C11 C16 N1 -2.2(3) . . . . ?
C8 C9 N1 C16 -177.1(3) . . . . ?
C10 C9 N1 C16 1.3(3) . . . . ?
N2 C16 N1 C9 -179.0(3) . . . . ?
C11 C16 N1 C9 0.5(3) . . . . ?
N1 C16 N2 C17 3.0(5) . . . . ?
C11 C16 N2 C17 -176.3(3) . . . . ?
C20 C17 N2 C16 174.1(4) . . . . ?
C18 C17 N2 C16 -64.0(4) . . . . ?
C19 C17 N2 C16 57.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.06 2.635(3) 123.3 .

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.042



