# 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_exp_9506
_database_code_depnum_ccdc_archive 'CCDC 2084551'
loop_
_audit_author_name
_audit_author_address
'Taoyuan Liang'
;School of Chemistry and Chemical Engineering, Guangxi University
China
;
_audit_update_record             
;
2021-05-19 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl N2'
_chemical_formula_sum            'C18 H15 Cl N2'
_chemical_formula_weight         294.77

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'

_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                   13.1846(10)
_cell_length_b                   7.7958(7)
_cell_length_c                   15.6184(12)
_cell_angle_alpha                90
_cell_angle_beta                 113.389(9)
_cell_angle_gamma                90
_cell_volume                     1473.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3375
_cell_measurement_theta_min      3.686
_cell_measurement_theta_max      29.178

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'ω scans'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6775
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.686
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3375
_reflns_number_gt                2409
_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-2013 (Sheldrick, 2013)'
_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)+(0.0614P)²+0.2656P]
 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         3375
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
N2 N 0.92167(15) 0.1892(3) 0.26417(14) 0.0436(5) Uani 1 1 d . . . . .
C10 C 0.73947(17) 0.1647(3) 0.22984(14) 0.0354(5) Uani 1 1 d . . . . .
N1 N 0.62210(15) 0.1240(3) 0.31996(12) 0.0400(5) Uani 1 1 d . . . . .
C9 C 0.63414(17) 0.1771(3) 0.23942(14) 0.0347(5) Uani 1 1 d . . . . .
C2 C 0.51611(19) 0.1609(3) 0.31080(16) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.45791(18) 0.2361(3) 0.22325(16) 0.0396(5) Uani 1 1 d . . . . .
C18 C 0.76059(18) 0.1081(3) 0.15034(15) 0.0357(5) Uani 1 1 d . . . . .
C8 C 0.53441(18) 0.2421(3) 0.17974(15) 0.0372(5) Uani 1 1 d . . . . .
C13 C 0.87501(18) 0.1250(3) 0.17528(16) 0.0394(5) Uani 1 1 d . . . . .
C11 C 0.84018(18) 0.2123(3) 0.29591(16) 0.0413(6) Uani 1 1 d . . . . .
H11 H 0.8514 0.2547 0.3546 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6947(2) 0.0454(3) 0.06200(15) 0.0444(6) Uani 1 1 d . . . . .
H17 H 0.6190 0.0318 0.0442 0.053 Uiso 1 1 calc R U . . .
C3 C 0.4663(2) 0.1355(4) 0.3736(2) 0.0603(8) Uani 1 1 d . . . . .
H3 H 0.5043 0.0840 0.4313 0.072 Uiso 1 1 calc R U . . .
C1 C 0.7046(2) 0.0434(4) 0.40122(15) 0.0496(6) Uani 1 1 d . . . . .
H1A H 0.7594 -0.0104 0.3842 0.074 Uiso 1 1 calc R U . . .
H1B H 0.6700 -0.0415 0.4251 0.074 Uiso 1 1 calc R U . . .
H1C H 0.7391 0.1286 0.4482 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7438(2) 0.0039(4) 0.00152(17) 0.0574(7) Uani 1 1 d . . . . .
H16 H 0.7005 -0.0364 -0.0579 0.069 Uiso 1 1 calc R U . . .
C12 C 1.0366(2) 0.2357(4) 0.3152(2) 0.0617(8) Uani 1 1 d . . . . .
H12A H 1.0831 0.1420 0.3134 0.093 Uiso 1 1 calc R U . . .
H12B H 1.0493 0.2607 0.3788 0.093 Uiso 1 1 calc R U . . .
H12C H 1.0537 0.3350 0.2871 0.093 Uiso 1 1 calc R U . . .
C14 C 0.9245(2) 0.0810(4) 0.11398(19) 0.0558(7) Uani 1 1 d . . . . .
H14 H 1.0003 0.0920 0.1312 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3583(3) 0.1898(5) 0.3468(2) 0.0731(10) Uani 1 1 d . . . . .
H4 H 0.3232 0.1741 0.3874 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3488(2) 0.2901(4) 0.1985(2) 0.0555(7) Uani 1 1 d . . . . .
H6 H 0.3097 0.3407 0.1408 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3007(2) 0.2671(5) 0.2610(2) 0.0710(9) Uani 1 1 d . . . . .
H5 H 0.2284 0.3037 0.2457 0.085 Uiso 1 1 calc R U . . .
C15 C 0.8574(3) 0.0215(4) 0.02814(19) 0.0633(8) Uani 1 1 d . . . . .
H15 H 0.8882 -0.0083 -0.0140 0.076 Uiso 1 1 calc R U . . .
Cl1 Cl 0.50718(5) 0.33689(9) 0.07327(4) 0.0499(2) 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
N2 C11 1.362(3) . ?
N2 C13 1.370(3) . ?
N2 C12 1.451(3) . ?
C10 C11 1.370(3) . ?
C10 C18 1.445(3) . ?
C10 C9 1.458(3) . ?
N1 C2 1.377(3) . ?
N1 C9 1.392(3) . ?
N1 C1 1.446(3) . ?
C9 C8 1.372(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.403(3) . ?
C7 C6 1.398(3) . ?
C7 C8 1.423(3) . ?
C18 C17 1.395(3) . ?
C18 C13 1.407(3) . ?
C8 Cl1 1.722(2) . ?
C13 C14 1.399(3) . ?
C11 H11 0.9300 . ?
C17 C16 1.379(3) . ?
C17 H17 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C16 C15 1.392(4) . ?
C16 H16 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9300 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9300 . ?
C6 C5 1.372(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C15 H15 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 N2 C13 108.36(18) . . ?
C11 N2 C12 124.8(2) . . ?
C13 N2 C12 126.7(2) . . ?
C11 C10 C18 105.66(18) . . ?
C11 C10 C9 125.6(2) . . ?
C18 C10 C9 128.66(19) . . ?
C2 N1 C9 108.60(18) . . ?
C2 N1 C1 124.06(19) . . ?
C9 N1 C1 127.34(18) . . ?
C8 C9 N1 107.55(18) . . ?
C8 C9 C10 130.5(2) . . ?
N1 C9 C10 121.87(19) . . ?
N1 C2 C3 129.7(2) . . ?
N1 C2 C7 109.16(19) . . ?
C3 C2 C7 121.1(2) . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 C8 134.8(2) . . ?
C2 C7 C8 105.2(2) . . ?
C17 C18 C13 119.0(2) . . ?
C17 C18 C10 134.4(2) . . ?
C13 C18 C10 106.54(19) . . ?
C9 C8 C7 109.5(2) . . ?
C9 C8 Cl1 126.21(16) . . ?
C7 C8 Cl1 124.02(18) . . ?
N2 C13 C14 129.7(2) . . ?
N2 C13 C18 108.40(18) . . ?
C14 C13 C18 121.9(2) . . ?
N2 C11 C10 111.0(2) . . ?
N2 C11 H11 124.5 . . ?
C10 C11 H11 124.5 . . ?
C16 C17 C18 118.8(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C14 C13 117.4(2) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C5 C6 C7 118.7(3) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C14 C15 C16 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?

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
C2 N1 C9 C8 -1.7(3) . . . . ?
C1 N1 C9 C8 178.3(2) . . . . ?
C2 N1 C9 C10 176.4(2) . . . . ?
C1 N1 C9 C10 -3.6(4) . . . . ?
C11 C10 C9 C8 132.1(3) . . . . ?
C18 C10 C9 C8 -45.3(4) . . . . ?
C11 C10 C9 N1 -45.5(3) . . . . ?
C18 C10 C9 N1 137.1(2) . . . . ?
C9 N1 C2 C3 -178.4(3) . . . . ?
C1 N1 C2 C3 1.6(4) . . . . ?
C9 N1 C2 C7 0.9(3) . . . . ?
C1 N1 C2 C7 -179.1(2) . . . . ?
N1 C2 C7 C6 -178.0(2) . . . . ?
C3 C2 C7 C6 1.3(4) . . . . ?
N1 C2 C7 C8 0.2(3) . . . . ?
C3 C2 C7 C8 179.6(2) . . . . ?
C11 C10 C18 C17 -179.8(3) . . . . ?
C9 C10 C18 C17 -2.0(4) . . . . ?
C11 C10 C18 C13 0.4(3) . . . . ?
C9 C10 C18 C13 178.2(2) . . . . ?
N1 C9 C8 C7 1.9(3) . . . . ?
C10 C9 C8 C7 -176.0(2) . . . . ?
N1 C9 C8 Cl1 175.76(17) . . . . ?
C10 C9 C8 Cl1 -2.1(4) . . . . ?
C6 C7 C8 C9 176.6(3) . . . . ?
C2 C7 C8 C9 -1.3(3) . . . . ?
C6 C7 C8 Cl1 2.5(4) . . . . ?
C2 C7 C8 Cl1 -175.36(18) . . . . ?
C11 N2 C13 C14 179.9(3) . . . . ?
C12 N2 C13 C14 3.4(4) . . . . ?
C11 N2 C13 C18 0.3(3) . . . . ?
C12 N2 C13 C18 -176.2(2) . . . . ?
C17 C18 C13 N2 179.7(2) . . . . ?
C10 C18 C13 N2 -0.4(3) . . . . ?
C17 C18 C13 C14 0.1(4) . . . . ?
C10 C18 C13 C14 180.0(2) . . . . ?
C13 N2 C11 C10 0.0(3) . . . . ?
C12 N2 C11 C10 176.6(2) . . . . ?
C18 C10 C11 N2 -0.3(3) . . . . ?
C9 C10 C11 N2 -178.1(2) . . . . ?
C13 C18 C17 C16 -0.8(4) . . . . ?
C10 C18 C17 C16 179.4(3) . . . . ?
N1 C2 C3 C4 178.1(3) . . . . ?
C7 C2 C3 C4 -1.0(4) . . . . ?
C18 C17 C16 C15 0.9(4) . . . . ?
N2 C13 C14 C15 -179.1(3) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C7 C6 C5 -0.4(4) . . . . ?
C8 C7 C6 C5 -178.0(3) . . . . ?
C7 C6 C5 C4 -0.8(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C17 C16 C15 C14 -0.5(5) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-2

