# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2234240'
loop_
_audit_author_name
_audit_author_address
'Zhang Chihong'
;Nanchang University
China
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_audit_creation_date             2023-01-04
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68
_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'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5545(14)
_cell_length_b                   4.7731(7)
_cell_length_c                   12.5151(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.509(2)
_cell_angle_gamma                90
_cell_volume                     554.96(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1466
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9253.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             248
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3399
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.703
_diffrn_reflns_theta_min         3.054
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.578
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.721
_reflns_number_gt                1989
_reflns_number_total             2250
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.064
_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)+(0.0448P)²+0.0326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl01 Cl 0.09563(7) -0.2902(2) 0.60747(6) 0.0522(2) Uani 1 1 d . . . . .
N002 N 0.5525(2) 0.5619(4) 0.69329(15) 0.0290(4) Uani 1 1 d . . . . .
N003 N 0.4189(2) 0.4033(5) 0.86239(16) 0.0380(5) Uani 1 1 d . . . . .
C004 C 0.4464(2) 0.3651(5) 0.67594(18) 0.0279(5) Uani 1 1 d . . . . .
C005 C 0.3782(2) 0.2837(5) 0.76006(19) 0.0292(6) Uani 1 1 d . . . . .
C006 C 0.5910(2) 0.6759(6) 0.79187(17) 0.0290(6) Uani 1 1 d . . . . .
C007 C 0.2693(3) 0.0780(6) 0.7388(2) 0.0354(6) Uani 1 1 d . . . . .
H007 H 0.224740 0.022231 0.793882 0.042 Uiso 1 1 calc R U . . .
C008 C 0.7066(3) 0.8883(5) 0.8119(2) 0.0309(5) Uani 1 1 d . . . . .
C009 C 0.2302(3) -0.0379(5) 0.6371(2) 0.0351(6) Uani 1 1 d . . . . .
C00A C 0.2971(3) 0.0397(6) 0.5525(2) 0.0384(6) Uani 1 1 d . . . . .
H00A H 0.269188 -0.043813 0.483672 0.046 Uiso 1 1 calc R U . . .
C00B C 0.4026(2) 0.2374(7) 0.57188(19) 0.0345(6) Uani 1 1 d . . . . .
H00B H 0.446414 0.288928 0.515800 0.041 Uiso 1 1 calc R U . . .
C00C C 0.7756(3) 0.9565(6) 0.7283(2) 0.0396(6) Uani 1 1 d . . . . .
H00C H 0.748191 0.866737 0.660684 0.048 Uiso 1 1 calc R U . . .
C00D C 0.5206(3) 0.5903(6) 0.87610(19) 0.0369(6) Uani 1 1 d . . . . .
H00D H 0.549606 0.673872 0.944855 0.044 Uiso 1 1 calc R U . . .
C00E C 0.7521(3) 1.0262(6) 0.9127(2) 0.0399(6) Uani 1 1 d . . . . .
H00E H 0.708817 0.984142 0.970037 0.048 Uiso 1 1 calc R U . . .
C00F C 0.8833(3) 1.1545(6) 0.7446(2) 0.0459(7) Uani 1 1 d . . . . .
H00F H 0.927247 1.197928 0.687720 0.055 Uiso 1 1 calc R U . . .
C00G C 0.8606(3) 1.2245(8) 0.9281(2) 0.0474(7) Uani 1 1 d . . . . .
H00G H 0.889075 1.315119 0.995434 0.057 Uiso 1 1 calc R U . . .
C00H C 0.9267(3) 1.2890(6) 0.8445(3) 0.0471(8) Uani 1 1 d . . . . .
H00H H 0.999825 1.421894 0.855322 0.056 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
Cl01 C009 1.737(3) . ?
N002 C004 1.361(3) . ?
N002 C006 1.320(3) . ?
N003 C005 1.373(3) . ?
N003 C00D 1.301(3) . ?
C004 C005 1.416(3) . ?
C004 C00B 1.410(3) . ?
C005 C007 1.410(3) . ?
C006 C008 1.477(4) . ?
C006 C00D 1.436(3) . ?
C007 H007 0.9300 . ?
C007 C009 1.357(3) . ?
C008 C00C 1.399(3) . ?
C008 C00E 1.399(4) . ?
C009 C00A 1.408(4) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.361(4) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00F 1.377(4) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00G 1.384(4) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.381(4) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.376(4) . ?
C00H H00H 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
C006 N002 C004 117.9(2) . . ?
C00D N003 C005 116.6(2) . . ?
N002 C004 C005 121.7(2) . . ?
N002 C004 C00B 119.7(2) . . ?
C00B C004 C005 118.6(2) . . ?
N003 C005 C004 120.0(2) . . ?
N003 C005 C007 120.1(2) . . ?
C007 C005 C004 119.9(2) . . ?
N002 C006 C008 118.42(19) . . ?
N002 C006 C00D 119.5(2) . . ?
C00D C006 C008 122.1(2) . . ?
C005 C007 H007 120.3 . . ?
C009 C007 C005 119.4(2) . . ?
C009 C007 H007 120.3 . . ?
C00C C008 C006 119.8(2) . . ?
C00C C008 C00E 117.6(2) . . ?
C00E C008 C006 122.6(2) . . ?
C007 C009 Cl01 120.7(2) . . ?
C007 C009 C00A 121.6(2) . . ?
C00A C009 Cl01 117.7(2) . . ?
C009 C00A H00A 120.1 . . ?
C00B C00A C009 119.7(2) . . ?
C00B C00A H00A 120.1 . . ?
C004 C00B H00B 119.6 . . ?
C00A C00B C004 120.8(2) . . ?
C00A C00B H00B 119.6 . . ?
C008 C00C H00C 119.5 . . ?
C00F C00C C008 121.0(3) . . ?
C00F C00C H00C 119.5 . . ?
N003 C00D C006 124.2(2) . . ?
N003 C00D H00D 117.9 . . ?
C006 C00D H00D 117.9 . . ?
C008 C00E H00E 119.6 . . ?
C00G C00E C008 120.8(2) . . ?
C00G C00E H00E 119.6 . . ?
C00C C00F H00F 119.7 . . ?
C00C C00F C00H 120.6(3) . . ?
C00H C00F H00F 119.7 . . ?
C00E C00G H00G 119.7 . . ?
C00H C00G C00E 120.6(3) . . ?
C00H C00G H00G 119.7 . . ?
C00F C00H H00H 120.3 . . ?
C00G C00H C00F 119.4(3) . . ?
C00G C00H H00H 120.3 . . ?

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
Cl01 C009 C00A C00B 179.7(2) . . . . ?
N002 C004 C005 N003 -0.2(3) . . . . ?
N002 C004 C005 C007 -179.7(2) . . . . ?
N002 C004 C00B C00A 179.9(2) . . . . ?
N002 C006 C008 C00C -2.2(4) . . . . ?
N002 C006 C008 C00E 178.2(2) . . . . ?
N002 C006 C00D N003 0.1(4) . . . . ?
N003 C005 C007 C009 179.9(2) . . . . ?
C004 N002 C006 C008 179.6(2) . . . . ?
C004 N002 C006 C00D -0.1(3) . . . . ?
C004 C005 C007 C009 -0.6(3) . . . . ?
C005 N003 C00D C006 -0.1(4) . . . . ?
C005 C004 C00B C00A -0.1(4) . . . . ?
C005 C007 C009 Cl01 -179.55(17) . . . . ?
C005 C007 C009 C00A 0.8(4) . . . . ?
C006 N002 C004 C005 0.2(3) . . . . ?
C006 N002 C004 C00B -179.7(3) . . . . ?
C006 C008 C00C C00F 179.7(2) . . . . ?
C006 C008 C00E C00G -179.8(3) . . . . ?
C007 C009 C00A C00B -0.6(4) . . . . ?
C008 C006 C00D N003 -179.6(3) . . . . ?
C008 C00C C00F C00H 0.5(4) . . . . ?
C008 C00E C00G C00H -0.4(5) . . . . ?
C009 C00A C00B C004 0.2(4) . . . . ?
C00B C004 C005 N003 179.7(2) . . . . ?
C00B C004 C005 C007 0.3(3) . . . . ?
C00C C008 C00E C00G 0.5(4) . . . . ?
C00C C00F C00H C00G -0.3(4) . . . . ?
C00D N003 C005 C004 0.1(3) . . . . ?
C00D N003 C005 C007 179.6(2) . . . . ?
C00D C006 C008 C00C 177.5(2) . . . . ?
C00D C006 C008 C00E -2.1(4) . . . . ?
C00E C008 C00C C00F -0.6(4) . . . . ?
C00E C00G C00H C00F 0.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
