# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_yxl061712_0m
_database_code_depnum_ccdc_archive 'CCDC 2172403'
loop_
_audit_author_name
_audit_author_address
'Xianglin Yu'
;Yunnan University
China
;
_audit_update_record             
;
2022-05-12 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Cl N2 O2'
_chemical_formula_weight         350.79

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.4409(10)
_cell_length_b                   12.1832(16)
_cell_length_c                   19.152(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.399(2)
_cell_angle_gamma                90
_cell_volume                     1735.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4149
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.972
_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      296(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            10535
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         27.659
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4011
_reflns_number_gt                3158
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²] 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         4011
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_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 0.34283(7) 0.05536(3) 0.39048(2) 0.06166(18) Uani 1 1 d . . . . .
O1 O 0.58944(17) 0.39866(11) 0.61707(6) 0.0647(4) Uani 1 1 d . . . . .
O2 O 0.15026(18) 0.46221(9) 0.61168(6) 0.0612(4) Uani 1 1 d . . . . .
N1 N 0.37041(16) 0.26750(9) 0.62084(5) 0.0376(3) Uani 1 1 d . . . . .
N2 N 0.27385(16) 0.56371(9) 0.52574(6) 0.0410(3) Uani 1 1 d . . . . .
H2 H 0.331354 0.559511 0.487423 0.049 Uiso 1 1 calc R U . . .
C1 C 0.0648(4) 0.06602(16) 0.75040(10) 0.0747(7) Uani 1 1 d . . . . .
H1 H -0.003451 0.021628 0.779043 0.090 Uiso 1 1 calc R U . . .
C2 C 0.2483(4) 0.06004(14) 0.75359(9) 0.0698(6) Uani 1 1 d . . . . .
H2A H 0.304646 0.012093 0.784936 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3516(2) 0.12515(13) 0.71027(8) 0.0522(4) Uani 1 1 d . . . . .
H3 H 0.476354 0.119856 0.711811 0.063 Uiso 1 1 calc R U . . .
C4 C 0.26652(19) 0.19768(11) 0.66501(6) 0.0377(3) Uani 1 1 d . . . . .
C5 C 0.32755(17) 0.27065(11) 0.54712(6) 0.0329(3) Uani 1 1 d . . . . .
C6 C 0.26527(17) 0.36657(10) 0.51428(7) 0.0340(3) Uani 1 1 d . . . . .
C7 C 0.22507(19) 0.46821(11) 0.55592(7) 0.0392(3) Uani 1 1 d . . . . .
C8 C 0.23806(18) 0.67058(11) 0.55205(7) 0.0383(3) Uani 1 1 d . . . . .
C9 C 0.1953(2) 0.75246(12) 0.50415(8) 0.0473(4) Uani 1 1 d . . . . .
H9 H 0.190299 0.736512 0.456659 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1601(2) 0.85806(13) 0.52704(10) 0.0572(4) Uani 1 1 d . . . . .
H10 H 0.131917 0.912800 0.494746 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1666(2) 0.88234(14) 0.59688(11) 0.0622(5) Uani 1 1 d . . . . .
H11 H 0.142056 0.953150 0.612090 0.075 Uiso 1 1 calc R U . . .
C12 C 0.4942(2) 0.33582(14) 0.64902(7) 0.0490(4) Uani 1 1 d . . . . .
H12 H 0.508369 0.335026 0.697393 0.059 Uiso 1 1 calc R U . . .
C13 C 0.22976(18) 0.36356(12) 0.44254(7) 0.0386(3) Uani 1 1 d . . . . .
H13 H 0.190266 0.426903 0.419826 0.046 Uiso 1 1 calc R U . . .
C14 C 0.25200(19) 0.26846(12) 0.40444(7) 0.0409(3) Uani 1 1 d . . . . .
H14 H 0.226060 0.267305 0.356700 0.049 Uiso 1 1 calc R U . . .
C15 C 0.31329(18) 0.17519(11) 0.43827(7) 0.0379(3) Uani 1 1 d . . . . .
C16 C 0.35207(18) 0.17475(11) 0.50923(7) 0.0373(3) Uani 1 1 d . . . . .
H16 H 0.393862 0.111343 0.531245 0.045 Uiso 1 1 calc R U . . .
C17 C 0.2095(3) 0.80134(15) 0.64430(10) 0.0642(5) Uani 1 1 d . . . . .
H17 H 0.213963 0.817857 0.691723 0.077 Uiso 1 1 calc R U . . .
C18 C 0.2466(2) 0.69498(13) 0.62249(9) 0.0517(4) Uani 1 1 d . . . . .
H18 H 0.276687 0.640889 0.654980 0.062 Uiso 1 1 calc R U . . .
C19 C 0.0825(2) 0.20438(15) 0.66252(9) 0.0540(4) Uani 1 1 d . . . . .
H19 H 0.025403 0.253796 0.632340 0.065 Uiso 1 1 calc R U . . .
C20 C -0.0181(3) 0.13759(18) 0.70491(11) 0.0697(5) Uani 1 1 d . . . . .
H20 H -0.142910 0.141310 0.702497 0.084 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 C15 1.7399(14) . ?
O1 C12 1.2183(18) . ?
O2 C7 1.2185(17) . ?
N1 C12 1.3445(18) . ?
N1 C4 1.4383(17) . ?
N1 C5 1.4404(16) . ?
N2 C7 1.3527(17) . ?
N2 C8 1.4236(17) . ?
N2 H2 0.8600 . ?
C1 C2 1.368(3) . ?
C1 C20 1.369(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C19 1.372(2) . ?
C5 C16 1.3897(18) . ?
C5 C6 1.4007(18) . ?
C6 C13 1.3933(18) . ?
C6 C7 1.5069(18) . ?
C8 C18 1.381(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C17 1.374(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.3813(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.3825(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9300 . ?
C20 H20 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
C12 N1 C4 120.19(11) . . ?
C12 N1 C5 120.66(11) . . ?
C4 N1 C5 118.88(10) . . ?
C7 N2 C8 125.52(12) . . ?
C7 N2 H2 117.2 . . ?
C8 N2 H2 117.2 . . ?
C2 C1 C20 119.75(17) . . ?
C2 C1 H1 120.1 . . ?
C20 C1 H1 120.1 . . ?
C1 C2 C3 120.54(17) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 119.15(17) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C19 C4 C3 120.15(14) . . ?
C19 C4 N1 119.66(13) . . ?
C3 C4 N1 120.19(14) . . ?
C16 C5 C6 120.87(11) . . ?
C16 C5 N1 117.44(11) . . ?
C6 C5 N1 121.69(11) . . ?
C13 C6 C5 118.27(12) . . ?
C13 C6 C7 120.55(12) . . ?
C5 C6 C7 121.05(12) . . ?
O2 C7 N2 124.00(13) . . ?
O2 C7 C6 121.02(12) . . ?
N2 C7 C6 114.95(11) . . ?
C18 C8 C9 119.70(14) . . ?
C18 C8 N2 122.54(13) . . ?
C9 C8 N2 117.75(13) . . ?
C10 C9 C8 120.03(15) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.45(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C17 119.51(16) . . ?
C10 C11 H11 120.2 . . ?
C17 C11 H11 120.2 . . ?
O1 C12 N1 126.07(13) . . ?
O1 C12 H12 117.0 . . ?
N1 C12 H12 117.0 . . ?
C14 C13 C6 121.38(13) . . ?
C14 C13 H13 119.3 . . ?
C6 C13 H13 119.3 . . ?
C15 C14 C13 119.03(12) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.55(12) . . ?
C14 C15 Cl1 119.24(10) . . ?
C16 C15 Cl1 119.20(11) . . ?
C15 C16 C5 118.90(12) . . ?
C15 C16 H16 120.6 . . ?
C5 C16 H16 120.6 . . ?
C11 C17 C18 121.02(16) . . ?
C11 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C8 C18 C17 119.28(15) . . ?
C8 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C4 C19 C20 119.92(17) . . ?
C4 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C1 C20 C19 120.5(2) . . ?
C1 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?

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
C20 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C19 -0.6(2) . . . . ?
C2 C3 C4 N1 178.65(13) . . . . ?
C12 N1 C4 C19 122.34(16) . . . . ?
C5 N1 C4 C19 -51.69(19) . . . . ?
C12 N1 C4 C3 -56.9(2) . . . . ?
C5 N1 C4 C3 129.04(14) . . . . ?
C12 N1 C5 C16 121.39(15) . . . . ?
C4 N1 C5 C16 -64.60(17) . . . . ?
C12 N1 C5 C6 -57.96(19) . . . . ?
C4 N1 C5 C6 116.05(14) . . . . ?
C16 C5 C6 C13 -0.46(19) . . . . ?
N1 C5 C6 C13 178.87(12) . . . . ?
C16 C5 C6 C7 175.30(12) . . . . ?
N1 C5 C6 C7 -5.37(19) . . . . ?
C8 N2 C7 O2 -3.4(2) . . . . ?
C8 N2 C7 C6 174.97(12) . . . . ?
C13 C6 C7 O2 134.92(16) . . . . ?
C5 C6 C7 O2 -40.7(2) . . . . ?
C13 C6 C7 N2 -43.46(18) . . . . ?
C5 C6 C7 N2 140.88(13) . . . . ?
C7 N2 C8 C18 38.3(2) . . . . ?
C7 N2 C8 C9 -142.47(15) . . . . ?
C18 C8 C9 C10 -0.5(2) . . . . ?
N2 C8 C9 C10 -179.70(14) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C17 0.5(3) . . . . ?
C4 N1 C12 O1 -179.80(17) . . . . ?
C5 N1 C12 O1 -5.9(3) . . . . ?
C5 C6 C13 C14 1.08(19) . . . . ?
C7 C6 C13 C14 -174.70(12) . . . . ?
C6 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C13 C14 C15 Cl1 -179.63(10) . . . . ?
C14 C15 C16 C5 0.3(2) . . . . ?
Cl1 C15 C16 C5 -179.77(10) . . . . ?
C6 C5 C16 C15 -0.23(19) . . . . ?
N1 C5 C16 C15 -179.59(12) . . . . ?
C10 C11 C17 C18 0.0(3) . . . . ?
C9 C8 C18 C17 0.9(2) . . . . ?
N2 C8 C18 C17 -179.91(15) . . . . ?
C11 C17 C18 C8 -0.6(3) . . . . ?
C3 C4 C19 C20 -0.6(2) . . . . ?
N1 C4 C19 C20 -179.92(15) . . . . ?
C2 C1 C20 C19 -0.4(3) . . . . ?
C4 C19 C20 C1 1.2(3) . . . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.036



