# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2081144'
loop_
_audit_author_name
_audit_author_address
'Fang Wang'
;Taizhou University
China
;
_audit_update_record             
;
2021-04-30 deposited with the CCDC.	2021-06-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl2 N O'
_chemical_formula_weight         322.21
_chemical_absolute_configuration ?
_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 0.0033 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'
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'

_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      trigonal
_space_group_IT_number           159
_space_group_name_H-M_alt        'P 3 1 c'
_space_group_name_Hall           'P 3 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   17.8125(12)
_cell_length_b                   17.8125(12)
_cell_length_c                   8.4655(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2326.1(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.19
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11584
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2439
_reflns_number_total             2728
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.3584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.58217(7) 0.88066(7) 0.62219(13) 0.0536(3) Uani 1 1 d . . . . .
Cl2 Cl 0.67725(6) 0.83752(7) 0.40258(14) 0.0542(3) Uani 1 1 d . . . . .
O1 O 0.44012(19) 0.6966(2) 0.5792(4) 0.0532(8) Uani 1 1 d . . . . .
H1 H 0.4226 0.7312 0.5828 0.080 Uiso 1 1 calc R U . . .
N1 N 0.5202(2) 0.6562(2) 0.4150(4) 0.0433(8) Uani 1 1 d . . . . .
C6 C 0.3821(3) 0.4787(3) 0.1367(6) 0.0596(13) Uani 1 1 d . . . . .
H6 H 0.3524 0.4185 0.1326 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4717(2) 0.6107(3) 0.2816(5) 0.0405(9) Uani 1 1 d . . . . .
C10 C 0.5957(3) 0.7932(2) 0.5513(5) 0.0373(8) Uani 1 1 d . . . . .
C12 C 0.7003(2) 0.8167(2) 0.7787(5) 0.0382(8) Uani 1 1 d . . . . .
C5 C 0.4259(3) 0.5203(3) 0.2739(6) 0.0469(10) Uani 1 1 d . . . . .
H5 H 0.4247 0.4878 0.3608 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6200(2) 0.7528(2) 0.6886(4) 0.0373(8) Uani 1 1 d . . . . .
H9 H 0.5717 0.7308 0.7639 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5110(2) 0.7271(2) 0.4705(5) 0.0411(9) Uani 1 1 d . . . . .
H11 H 0.4999 0.7547 0.3804 0.049 Uiso 1 1 calc R U . . .
C13 C 0.7831(3) 0.8403(3) 0.7269(5) 0.0466(9) Uani 1 1 d . . . . .
H13 H 0.7902 0.8142 0.6375 0.056 Uiso 1 1 calc R U . . .
C1 C 0.3817(3) 0.5243(4) 0.0087(7) 0.0681(14) Uani 1 1 d . . . . .
H1A H 0.3515 0.4956 -0.0820 0.082 Uiso 1 1 calc R U . . .
C3 C 0.4709(3) 0.6558(3) 0.1476(5) 0.0568(11) Uani 1 1 d . . . . .
H3 H 0.5011 0.7161 0.1488 0.068 Uiso 1 1 calc R U . . .
C14 C 0.8556(3) 0.9029(3) 0.8078(6) 0.0582(12) Uani 1 1 d . . . . .
H14 H 0.9109 0.9183 0.7723 0.070 Uiso 1 1 calc R U . . .
C7 C 0.5388(3) 0.6107(3) 0.5404(5) 0.0473(10) Uani 1 1 d . . . . .
H7A H 0.5443 0.5637 0.4948 0.057 Uiso 1 1 calc R U . . .
H7B H 0.4913 0.5861 0.6156 0.057 Uiso 1 1 calc R U . . .
C16 C 0.7645(3) 0.9178(3) 0.9954(6) 0.0585(12) Uani 1 1 d . . . . .
H16 H 0.7578 0.9434 1.0861 0.070 Uiso 1 1 calc R U . . .
C8 C 0.6221(3) 0.6733(3) 0.6240(5) 0.0458(10) Uani 1 1 d . . . . .
H8A H 0.6702 0.6924 0.5509 0.055 Uiso 1 1 calc R U . . .
H8B H 0.6319 0.6436 0.7107 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6923(3) 0.8550(3) 0.9156(6) 0.0505(10) Uani 1 1 d . . . . .
H17 H 0.6373 0.8383 0.9546 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8458(3) 0.9419(3) 0.9398(6) 0.0586(12) Uani 1 1 d . . . . .
H15 H 0.8944 0.9848 0.9917 0.070 Uiso 1 1 calc R U . . .
C2 C 0.4265(3) 0.6133(4) 0.0143(6) 0.0667(13) Uani 1 1 d . . . . .
H2 H 0.4267 0.6449 -0.0732 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 C10 1.794(4) . ?
Cl2 C10 1.781(4) . ?
O1 H1 0.8200 . ?
O1 C11 1.432(5) . ?
N1 C4 1.407(5) . ?
N1 C11 1.430(5) . ?
N1 C7 1.470(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(6) . ?
C6 C1 1.356(8) . ?
C4 C5 1.397(6) . ?
C4 C3 1.394(6) . ?
C10 C9 1.539(5) . ?
C10 C11 1.534(5) . ?
C12 C9 1.515(5) . ?
C12 C13 1.386(6) . ?
C12 C17 1.389(6) . ?
C5 H5 0.9300 . ?
C9 H9 0.9800 . ?
C9 C8 1.537(6) . ?
C11 H11 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.393(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.373(8) . ?
C3 H3 0.9300 . ?
C3 C2 1.369(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.515(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(6) . ?
C16 C15 1.371(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C2 H2 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
C11 O1 H1 109.5 . . ?
C4 N1 C11 117.7(3) . . ?
C4 N1 C7 120.3(3) . . ?
C11 N1 C7 114.0(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C1 C6 C5 121.3(4) . . ?
C5 C4 N1 122.6(4) . . ?
C3 C4 N1 120.1(3) . . ?
C3 C4 C5 117.3(4) . . ?
Cl2 C10 Cl1 106.6(2) . . ?
C9 C10 Cl1 110.1(3) . . ?
C9 C10 Cl2 112.6(3) . . ?
C9 C10 C11 112.1(3) . . ?
C11 C10 Cl1 108.0(3) . . ?
C11 C10 Cl2 107.2(3) . . ?
C13 C12 C9 122.1(4) . . ?
C13 C12 C17 118.1(4) . . ?
C17 C12 C9 119.8(4) . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C10 C9 H9 106.5 . . ?
C12 C9 C10 114.2(3) . . ?
C12 C9 H9 106.5 . . ?
C12 C9 C8 114.9(3) . . ?
C8 C9 C10 107.7(3) . . ?
C8 C9 H9 106.5 . . ?
O1 C11 N1 110.1(3) . . ?
O1 C11 C10 110.3(3) . . ?
O1 C11 H11 109.2 . . ?
N1 C11 C10 108.8(3) . . ?
N1 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C6 C1 H1A 120.4 . . ?
C6 C1 C2 119.3(5) . . ?
C2 C1 H1A 120.4 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
N1 C7 C8 109.8(3) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(4) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 C9 112.2(3) . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?

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
Cl1 C10 C9 C12 -56.4(4) . . . . ?
Cl1 C10 C9 C8 174.7(3) . . . . ?
Cl1 C10 C11 O1 -58.3(3) . . . . ?
Cl1 C10 C11 N1 -179.2(3) . . . . ?
Cl2 C10 C9 C12 62.5(4) . . . . ?
Cl2 C10 C9 C8 -66.5(4) . . . . ?
Cl2 C10 C11 O1 -172.9(2) . . . . ?
Cl2 C10 C11 N1 66.3(3) . . . . ?
N1 C4 C5 C6 -177.3(4) . . . . ?
N1 C4 C3 C2 177.9(4) . . . . ?
N1 C7 C8 C9 55.2(5) . . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
C4 N1 C11 O1 87.7(4) . . . . ?
C4 N1 C11 C10 -151.3(3) . . . . ?
C4 N1 C7 C8 152.7(4) . . . . ?
C4 C3 C2 C1 -0.4(8) . . . . ?
C10 C9 C8 C7 -53.5(4) . . . . ?
C12 C9 C8 C7 178.0(3) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C5 C6 C1 C2 0.8(7) . . . . ?
C5 C4 C3 C2 0.4(7) . . . . ?
C9 C10 C11 O1 63.2(4) . . . . ?
C9 C10 C11 N1 -57.7(4) . . . . ?
C9 C12 C13 C14 176.4(4) . . . . ?
C9 C12 C17 C16 -175.9(4) . . . . ?
C11 N1 C4 C5 -134.7(4) . . . . ?
C11 N1 C4 C3 47.9(5) . . . . ?
C11 N1 C7 C8 -59.2(5) . . . . ?
C11 C10 C9 C12 -176.6(3) . . . . ?
C11 C10 C9 C8 54.4(4) . . . . ?
C13 C12 C9 C10 -83.0(4) . . . . ?
C13 C12 C9 C8 42.2(5) . . . . ?
C13 C12 C17 C16 2.6(6) . . . . ?
C13 C14 C15 C16 1.8(7) . . . . ?
C1 C6 C5 C4 -0.8(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C7 N1 C4 C5 12.2(6) . . . . ?
C7 N1 C4 C3 -165.1(4) . . . . ?
C7 N1 C11 O1 -61.2(4) . . . . ?
C7 N1 C11 C10 59.8(4) . . . . ?
C17 C12 C9 C10 95.4(4) . . . . ?
C17 C12 C9 C8 -139.4(4) . . . . ?
C17 C12 C13 C14 -2.1(6) . . . . ?
C17 C16 C15 C14 -1.3(7) . . . . ?
C15 C16 C17 C12 -0.9(7) . . . . ?

