# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20210322wuxx_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2249069'
loop_
_audit_author_name
_audit_author_address
'Xin-Xing Wu'
;lzu
China
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-19 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            'C19 H20 Cl N O'
_chemical_formula_weight         313.81

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.564(9)
_cell_length_b                   10.371(12)
_cell_length_c                   11.366(14)
_cell_angle_alpha                109.224(14)
_cell_angle_beta                 91.783(15)
_cell_angle_gamma                96.951(14)
_cell_volume                     833.3(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3483
_cell_measurement_theta_min      2.7205
_cell_measurement_theta_max      27.5975

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.231
_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      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16878
_diffrn_reflns_av_unetI/netI     0.1226
_diffrn_reflns_av_R_equivalents  0.1891
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2920
_reflns_number_gt                1895
_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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.2950P] 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         2920
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2439
_refine_ls_R_factor_gt           0.1879
_refine_ls_wR_factor_ref         0.2955
_refine_ls_wR_factor_gt          0.2712
_refine_ls_goodness_of_fit_ref   1.355
_refine_ls_restrained_S_all      1.355
_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 1.0927(8) 0.7864(6) 0.8952(5) 0.0334(15) Uani 1 1 d . . . . .
C2 C 0.9346(9) 0.8291(6) 0.8664(6) 0.0394(17) Uani 1 1 d . . . . .
H2 H 0.9351 0.9163 0.8601 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7759(8) 0.7396(6) 0.8473(6) 0.0387(17) Uani 1 1 d . . . . .
H3 H 0.6694 0.7690 0.8307 0.046 Uiso 1 1 calc R U . . .
C4 C 0.7723(7) 0.6064(5) 0.8523(5) 0.0246(14) Uani 1 1 d . . . . .
C5 C 0.9335(8) 0.5667(6) 0.8806(5) 0.0355(16) Uani 1 1 d . . . . .
H5 H 0.9342 0.4786 0.8845 0.043 Uiso 1 1 calc R U . . .
C6 C 1.0936(8) 0.6559(6) 0.9032(6) 0.0376(17) Uani 1 1 d . . . . .
H6 H 1.1996 0.6284 0.9234 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5956(8) 0.5114(6) 0.8313(5) 0.0314(15) Uani 1 1 d . . . . .
H7 H 0.5083 0.5631 0.8819 0.038 Uiso 1 1 calc R U . . .
C8 C 0.5184(8) 0.4527(6) 0.6931(5) 0.0336(15) Uani 1 1 d . . . . .
H8 H 0.5094 0.5303 0.6630 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3267(8) 0.3758(7) 0.6878(6) 0.0455(18) Uani 1 1 d . . . . .
H9A H 0.2991 0.3034 0.6074 0.055 Uiso 1 1 calc R U . . .
H9B H 0.2404 0.4398 0.6971 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3144(9) 0.3121(7) 0.7944(6) 0.0471(18) Uani 1 1 d . . . . .
H10 H 0.2891 0.3841 0.8704 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5018(8) 0.2745(6) 0.8174(6) 0.0359(16) Uani 1 1 d . . . . .
H11 H 0.4901 0.2272 0.8791 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1675(10) 0.1921(8) 0.7678(8) 0.066(2) Uani 1 1 d . . . . .
H12A H 0.0554 0.2207 0.7527 0.099 Uiso 1 1 calc R U . . .
H12B H 0.1621 0.1607 0.8383 0.099 Uiso 1 1 calc R U . . .
H12C H 0.1915 0.1185 0.6954 0.099 Uiso 1 1 calc R U . . .
C13 C 0.6033(12) 0.0448(7) 0.7123(8) 0.066(2) Uani 1 1 d . . . . .
H13A H 0.5743 -0.0238 0.6312 0.099 Uiso 1 1 calc R U . . .
H13B H 0.5298 0.0213 0.7716 0.099 Uiso 1 1 calc R U . . .
H13C H 0.7268 0.0487 0.7373 0.099 Uiso 1 1 calc R U . . .
C14 C 0.6645(8) 0.2304(6) 0.6207(5) 0.0366(16) Uani 1 1 d . . . . .
C15 C 0.7779(10) 0.1516(7) 0.5399(6) 0.052(2) Uani 1 1 d . . . . .
H15 H 0.7920 0.0650 0.5434 0.062 Uiso 1 1 calc R U . . .
C16 C 0.8702(10) 0.1996(8) 0.4544(7) 0.060(2) Uani 1 1 d . . . . .
H16 H 0.9436 0.1447 0.4017 0.072 Uiso 1 1 calc R U . . .
C17 C 0.8527(10) 0.3285(8) 0.4480(6) 0.053(2) Uani 1 1 d . . . . .
H17 H 0.9149 0.3616 0.3922 0.064 Uiso 1 1 calc R U . . .
C18 C 0.7402(9) 0.4070(7) 0.5267(6) 0.0416(17) Uani 1 1 d . . . . .
H18 H 0.7286 0.4938 0.5228 0.050 Uiso 1 1 calc R U . . .
C19 C 0.6428(8) 0.3611(6) 0.6122(5) 0.0325(15) Uani 1 1 d . . . . .
Cl1 Cl 1.2961(2) 0.89812(19) 0.92212(18) 0.0581(7) Uani 1 1 d . . . . .
N1 N 0.5713(8) 0.1795(5) 0.7072(5) 0.0449(15) Uani 1 1 d . . . . .
O1 O 0.6228(5) 0.3978(4) 0.8742(3) 0.0366(11) 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 C6 1.386(8) . ?
C1 C2 1.390(9) . ?
C1 Cl1 1.763(7) . ?
C2 C3 1.390(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(8) . ?
C4 C7 1.522(9) . ?
C5 C6 1.394(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.449(7) . ?
C7 C8 1.552(8) . ?
C7 H7 0.9800 . ?
C8 C19 1.526(9) . ?
C8 C9 1.557(9) . ?
C8 H8 0.9800 . ?
C9 C10 1.560(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.507(10) . ?
C10 C11 1.552(9) . ?
C10 H10 0.9800 . ?
C11 O1 1.423(7) . ?
C11 N1 1.473(8) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N1 1.465(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.404(9) . ?
C14 C19 1.419(9) . ?
C14 N1 1.427(8) . ?
C15 C16 1.399(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.406(9) . ?
C18 H18 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 120.9(6) . . ?
C6 C1 Cl1 118.9(5) . . ?
C2 C1 Cl1 120.2(5) . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.8(6) . . ?
C5 C4 C7 122.1(5) . . ?
C3 C4 C7 120.1(5) . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O1 C7 C4 108.3(4) . . ?
O1 C7 C8 108.9(5) . . ?
C4 C7 C8 114.0(5) . . ?
O1 C7 H7 108.5 . . ?
C4 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C19 C8 C7 110.5(5) . . ?
C19 C8 C9 113.0(5) . . ?
C7 C8 C9 108.5(5) . . ?
C19 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C8 C9 C10 109.8(5) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C12 C10 C11 113.1(6) . . ?
C12 C10 C9 113.3(6) . . ?
C11 C10 C9 107.1(5) . . ?
C12 C10 H10 107.7 . . ?
C11 C10 H10 107.7 . . ?
C9 C10 H10 107.7 . . ?
O1 C11 N1 112.4(5) . . ?
O1 C11 C10 109.2(5) . . ?
N1 C11 C10 115.1(5) . . ?
O1 C11 H11 106.5 . . ?
N1 C11 H11 106.5 . . ?
C10 C11 H11 106.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.0(6) . . ?
C15 C14 N1 121.0(6) . . ?
C19 C14 N1 121.0(5) . . ?
C16 C15 C14 121.8(7) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C17 C16 C15 120.3(7) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 118.4(7) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C19 122.8(6) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C18 C19 C14 118.6(6) . . ?
C18 C19 C8 119.4(6) . . ?
C14 C19 C8 122.0(5) . . ?
C14 N1 C13 117.8(6) . . ?
C14 N1 C11 120.7(5) . . ?
C13 N1 C11 117.6(5) . . ?
C11 O1 C7 115.2(4) . . ?

_refine_diff_density_max         0.597
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.085

# start Validation Reply Form
_vrf_RINTA01_20210322wuxx_0m_a   
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.189
RESPONSE: We made several attempts to obtain better quality data for
this structure, however, due to twinning, disorder, poor crystal
quality etc. the Rint value is high. We are confidant the structural
characterization is valid.
;

_vrf_PLAT020_20210322wuxx_0m_a   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.189 Report
RESPONSE: We made several attempts to obtain better quality data for
this structure, however, due to twinning, disorder, poor crystal
quality etc. the Rint value is high. We are confidant the structural
characterization is valid.
;

_vrf_PLAT082_20210322wuxx_0m_a   
;
PROBLEM: High R1 Value ..................................       0.19 Report
RESPONSE: We made several attempts to obtain better quality data for
this structure, however, due to twinning, disorder, poor crystal
quality etc. the R1 value is high. We are confidant the structural
characterization is valid.
;


# end Validation Reply Form
