# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_q258-cl
_database_code_depnum_ccdc_archive 'CCDC 2364270'
loop_
_audit_author_name
_audit_author_address
Yang
;luoyang normal university
China
;
_audit_update_record             
;
2024-06-21 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cd Cl2 N'
_chemical_formula_sum            'C13 H9 Cd Cl2 N'
_chemical_formula_weight         362.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1Cd1Cl1
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'
Cd Cd -0.8075 1.2024 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.095(2)
_cell_length_b                   10.0218(10)
_cell_length_c                   7.0974(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.333(10)
_cell_angle_gamma                90
_cell_volume                     1199.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2065
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0740
_cell_measurement_theta_min      3.8840
_shelx_estimated_absorpt_T_max   0.651
_shelx_estimated_absorpt_T_min   0.583
_exptl_absorpt_coefficient_mu    2.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.007
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.825
_diffrn_reflns_Laue_measured_fraction_max 0.714
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4343
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.714
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.254
_diffrn_reflns_theta_min         3.549
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.714
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  71.00   1.00   10.00    --   15.05 178.00 150.00   34
  2  ω    -11.00  21.00   1.00   10.00    --   15.05  77.00   0.00   32
  3  ω     24.00  79.00   1.00   10.00    --   15.05  77.00   0.00   55
  4  ω    -53.00  42.00   1.00   10.00    --   15.05 -77.00-120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0142335000
_diffrn_orient_matrix_UB_12      -0.0006279000
_diffrn_orient_matrix_UB_13      -0.0884824000
_diffrn_orient_matrix_UB_21      -0.0116378000
_diffrn_orient_matrix_UB_22      0.0675917000
_diffrn_orient_matrix_UB_23      -0.0153917000
_diffrn_orient_matrix_UB_31      0.0377872000
_diffrn_orient_matrix_UB_32      0.0210454000
_diffrn_orient_matrix_UB_33      0.0467942000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1704
_reflns_number_total             2123
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.687
_refine_diff_density_min         -2.470
_refine_diff_density_rms         0.295
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.391
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0994
_refine_ls_restrained_S_all      1.392
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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
Cd1 Cd 0.25280(4) 0.67679(6) 0.60142(10) 0.0152(3) Uani 1 1 d . . . . .
Cl1 Cl 0.3470(2) 0.8118(3) 0.8311(5) 0.0309(7) Uani 1 1 d . . . . .
Cl2 Cl 0.1617(2) 0.8219(3) 0.3796(5) 0.0312(8) Uani 1 1 d . . . . .
N007 N 0.2513(4) 0.4469(9) 0.5925(9) 0.0150(19) Uani 1 1 d . . . . .
C1 C 0.3187(6) 0.3774(10) 0.6654(15) 0.020(2) Uani 1 1 d . . . . .
C2 C 0.3891(7) 0.4459(11) 0.7431(18) 0.030(3) Uani 1 1 d . . . . .
H2 H 0.3898 0.5386 0.7451 0.036 Uiso 1 1 calc R . . . .
C3 C 0.4549(8) 0.3775(13) 0.8137(17) 0.035(3) Uani 1 1 d . . . . .
H3 H 0.5010 0.4237 0.8615 0.042 Uiso 1 1 calc R . . . .
C4 C 0.4553(7) 0.2350(13) 0.8168(18) 0.034(3) Uani 1 1 d . . . . .
H4 H 0.5012 0.1883 0.8654 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3870(7) 0.1688(10) 0.7469(19) 0.024(3) Uani 1 1 d . . . . .
H5 H 0.3862 0.0761 0.7525 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3183(6) 0.2366(11) 0.6675(15) 0.023(2) Uani 1 1 d . U . . .
C7 C 0.2503(6) 0.1695(10) 0.5956(13) 0.020(3) Uani 1 1 d . . . . .
H7 H 0.2491 0.0768 0.5997 0.024 Uiso 1 1 calc R . . . .
C8 C 0.1832(6) 0.2403(10) 0.5167(15) 0.022(2) Uani 1 1 d . . . . .
C9 C 0.1083(8) 0.1767(11) 0.441(2) 0.031(3) Uani 1 1 d . . . . .
H9 H 0.1043 0.0842 0.4462 0.038 Uiso 1 1 calc R . . . .
C10 C 0.0451(7) 0.2480(15) 0.3634(17) 0.038(3) Uani 1 1 d . . . . .
H10 H -0.0013 0.2045 0.3100 0.045 Uiso 1 1 calc R . . . .
C11 C 0.0484(7) 0.3910(12) 0.3621(18) 0.037(3) Uani 1 1 d . . . . .
H11 H 0.0041 0.4403 0.3095 0.045 Uiso 1 1 calc R . . . .
C12 C 0.1162(7) 0.4534(10) 0.4378(17) 0.028(3) Uani 1 1 d . . . . .
H12 H 0.1170 0.5461 0.4392 0.034 Uiso 1 1 calc R . . . .
C13 C 0.1854(7) 0.3846(9) 0.5144(16) 0.022(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
Cd1 Cl1 2.496(3) . ?
Cd1 Cl1 2.700(3) 4_575 ?
Cd1 Cl2 2.495(3) . ?
Cd1 Cl2 2.705(3) 4_576 ?
Cd1 N007 2.305(9) . ?
Cl1 Cd1 2.700(3) 4_576 ?
Cl2 Cd1 2.705(3) 4_575 ?
N007 C1 1.373(13) . ?
N007 C13 1.328(13) . ?
C1 C2 1.418(15) . ?
C1 C6 1.411(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.342(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.428(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(15) . ?
C6 C7 1.367(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(14) . ?
C8 C9 1.452(16) . ?
C8 C13 1.447(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.337(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.43(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.349(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.401(15) . ?

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
Cl1 Cd1 Cl1 92.58(10) . 4_575 ?
Cl1 Cd1 Cl2 84.70(10) . 4_576 ?
Cl1 Cd1 Cl2 176.92(9) 4_575 4_576 ?
Cl2 Cd1 Cl1 111.51(11) . . ?
Cl2 Cd1 Cl1 84.84(10) . 4_575 ?
Cl2 Cd1 Cl2 94.80(11) . 4_576 ?
N007 Cd1 Cl1 124.25(19) . . ?
N007 Cd1 Cl1 91.60(19) . 4_575 ?
N007 Cd1 Cl2 91.13(18) . 4_576 ?
N007 Cd1 Cl2 124.23(18) . . ?
Cd1 Cl1 Cd1 95.22(10) . 4_576 ?
Cd1 Cl2 Cd1 95.12(10) . 4_575 ?
C1 N007 Cd1 119.5(6) . . ?
C13 N007 Cd1 119.1(6) . . ?
C13 N007 C1 121.4(10) . . ?
N007 C1 C2 120.6(9) . . ?
N007 C1 C6 120.4(9) . . ?
C6 C1 C2 119.0(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(10) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(11) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(10) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(10) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.1(10) . . ?
C7 C6 C1 119.5(9) . . ?
C7 C6 C5 121.3(10) . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(11) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 123.1(10) . . ?
C7 C8 C13 119.6(9) . . ?
C13 C8 C9 117.3(9) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.5(11) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(10) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.5(10) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 118.5 . . ?
C11 C12 C13 122.9(10) . . ?
C13 C12 H12 118.5 . . ?
N007 C13 C8 119.2(9) . . ?
N007 C13 C12 122.5(9) . . ?
C12 C13 C8 118.3(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.639
