# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1946625'
loop_
_audit_author_name
_audit_author_address
'Cheng-kou Liu'
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-08-12 deposited with the CCDC.	2020-11-27 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            'C16 H11 Cl N2 O'
_chemical_formula_weight         282.72

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   18.614(4)
_cell_length_b                   9.1120(18)
_cell_length_c                   16.553(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.01(3)
_cell_angle_gamma                90
_cell_volume                     2684.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       solid
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4934
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         25.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2470
_reflns_number_gt                1787
_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)+(0.1000P)²+0.1500P] 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         2470
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Cl Cl 0.09931(5) 0.45280(9) 0.20350(5) 0.0825(3) Uani 1 1 d . . . . .
O O -0.15438(11) 0.9292(3) -0.04808(13) 0.0832(6) Uani 1 1 d . . . . .
C1 C 0.05465(12) 0.7011(3) -0.00677(14) 0.0492(5) Uani 1 1 d . . . . .
N1 N 0.08311(10) 0.7380(2) -0.07176(13) 0.0577(5) Uani 1 1 d . . . . .
N2 N -0.04643(10) 0.8623(2) -0.07411(12) 0.0534(5) Uani 1 1 d . . . . .
H2A H -0.0199 0.8780 -0.1079 0.064 Uiso 1 1 calc R U . . .
C2 C 0.14627(13) 0.6750(3) -0.07273(18) 0.0684(7) Uani 1 1 d . . . . .
H2B H 0.1657 0.6979 -0.1169 0.082 Uiso 1 1 calc R U . . .
C3 C 0.18583(14) 0.5766(3) -0.0122(2) 0.0730(8) Uani 1 1 d . . . . .
H3A H 0.2307 0.5367 -0.0160 0.088 Uiso 1 1 calc R U . . .
C4 C 0.15875(14) 0.5385(3) 0.05290(18) 0.0653(7) Uani 1 1 d . . . . .
H4A H 0.1845 0.4718 0.0936 0.078 Uiso 1 1 calc R U . . .
C5 C 0.09064(12) 0.6021(3) 0.05753(15) 0.0541(6) Uani 1 1 d . . . . .
C6 C 0.05656(14) 0.5727(3) 0.12217(15) 0.0581(6) Uani 1 1 d . . . . .
C7 C -0.00872(15) 0.6386(3) 0.12206(16) 0.0627(7) Uani 1 1 d . . . . .
H7A H -0.0299 0.6188 0.1653 0.075 Uiso 1 1 calc R U . . .
C8 C -0.04459(15) 0.7361(3) 0.05747(16) 0.0594(6) Uani 1 1 d . . . . .
H8A H -0.0897 0.7794 0.0581 0.071 Uiso 1 1 calc R U . . .
C9 C -0.01450(12) 0.7689(2) -0.00683(14) 0.0489(5) Uani 1 1 d . . . . .
C10 C -0.11377(13) 0.9319(3) -0.09389(16) 0.0542(6) Uani 1 1 d . . . . .
C11 C -0.13531(12) 1.0123(3) -0.17621(15) 0.0520(6) Uani 1 1 d . . . . .
C12 C -0.18406(13) 1.1289(3) -0.18460(17) 0.0599(6) Uani 1 1 d . . . . .
H12A H -0.2022 1.1545 -0.1398 0.072 Uiso 1 1 calc R U . . .
C13 C -0.20621(15) 1.2080(3) -0.2589(2) 0.0723(8) Uani 1 1 d . . . . .
H13A H -0.2376 1.2889 -0.2632 0.087 Uiso 1 1 calc R U . . .
C14 C -0.18195(15) 1.1675(3) -0.32684(19) 0.0724(8) Uani 1 1 d . . . . .
H14A H -0.1971 1.2206 -0.3770 0.087 Uiso 1 1 calc R U . . .
C15 C -0.13544(16) 1.0489(3) -0.32029(18) 0.0701(7) Uani 1 1 d . . . . .
H15A H -0.1199 1.0201 -0.3664 0.084 Uiso 1 1 calc R U . . .
C16 C -0.11161(15) 0.9720(3) -0.24538(17) 0.0604(6) Uani 1 1 d . . . . .
H16A H -0.0794 0.8924 -0.2411 0.073 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
Cl C6 1.735(3) . ?
O C10 1.217(3) . ?
C1 N1 1.373(3) . ?
C1 C5 1.407(3) . ?
C1 C9 1.428(3) . ?
N1 C2 1.313(3) . ?
N2 C10 1.357(3) . ?
N2 C9 1.389(3) . ?
N2 H2A 0.8600 . ?
C2 C3 1.386(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.361(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.416(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.420(3) . ?
C6 C7 1.355(4) . ?
C7 C8 1.400(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.373(3) . ?
C8 H8A 0.9300 . ?
C10 C11 1.495(4) . ?
C11 C12 1.378(3) . ?
C11 C16 1.391(3) . ?
C12 C13 1.381(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.379(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.380(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 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
N1 C1 C5 122.9(2) . . ?
N1 C1 C9 116.6(2) . . ?
C5 C1 C9 120.5(2) . . ?
C2 N1 C1 117.1(2) . . ?
C10 N2 C9 128.93(19) . . ?
C10 N2 H2A 115.5 . . ?
C9 N2 H2A 115.5 . . ?
N1 C2 C3 124.2(2) . . ?
N1 C2 H2B 117.9 . . ?
C3 C2 H2B 117.9 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C1 C5 C4 117.2(2) . . ?
C1 C5 C6 118.2(2) . . ?
C4 C5 C6 124.6(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 Cl 119.18(19) . . ?
C5 C6 Cl 119.92(19) . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C8 C9 N2 125.4(2) . . ?
C8 C9 C1 118.5(2) . . ?
N2 C9 C1 116.10(19) . . ?
O C10 N2 122.6(2) . . ?
O C10 C11 121.9(2) . . ?
N2 C10 C11 115.6(2) . . ?
C12 C11 C16 118.6(2) . . ?
C12 C11 C10 117.6(2) . . ?
C16 C11 C10 123.8(2) . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 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
C5 C1 N1 C2 0.8(3) . . . . ?
C9 C1 N1 C2 -179.3(2) . . . . ?
C1 N1 C2 C3 -1.0(4) . . . . ?
N1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
N1 C1 C5 C4 -0.6(3) . . . . ?
C9 C1 C5 C4 179.6(2) . . . . ?
N1 C1 C5 C6 179.5(2) . . . . ?
C9 C1 C5 C6 -0.4(3) . . . . ?
C3 C4 C5 C1 0.5(4) . . . . ?
C3 C4 C5 C6 -179.6(2) . . . . ?
C1 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C7 179.8(2) . . . . ?
C1 C5 C6 Cl -179.32(17) . . . . ?
C4 C5 C6 Cl 0.8(3) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
Cl C6 C7 C8 179.87(19) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 N2 179.0(2) . . . . ?
C7 C8 C9 C1 0.1(4) . . . . ?
C10 N2 C9 C8 -4.4(4) . . . . ?
C10 N2 C9 C1 174.4(2) . . . . ?
N1 C1 C9 C8 -179.4(2) . . . . ?
C5 C1 C9 C8 0.4(3) . . . . ?
N1 C1 C9 N2 1.6(3) . . . . ?
C5 C1 C9 N2 -178.53(19) . . . . ?
C9 N2 C10 O 6.1(4) . . . . ?
C9 N2 C10 C11 -173.6(2) . . . . ?
O C10 C11 C12 26.0(3) . . . . ?
N2 C10 C11 C12 -154.2(2) . . . . ?
O C10 C11 C16 -151.1(3) . . . . ?
N2 C10 C11 C16 28.7(3) . . . . ?
C16 C11 C12 C13 -2.9(4) . . . . ?
C10 C11 C12 C13 179.9(2) . . . . ?
C11 C12 C13 C14 2.5(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C14 C15 C16 C11 1.0(4) . . . . ?
C12 C11 C16 C15 1.1(4) . . . . ?
C10 C11 C16 C15 178.2(2) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.078

