# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20160719e
_database_code_depnum_ccdc_archive 'CCDC 1862717'
loop_
_audit_author_name
_audit_author_address
'Xiao-Gang Yang'
;Beijing Normal university
China
;
_audit_update_record             
;
2018-08-19 deposited with the CCDC.	2019-03-08 downloaded from the CCDC.
;
_audit_creation_date             2018-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        OIP-AD
_chemical_formula_moiety         'Cl2 Pb, 0.5(Cl), C6 H5 N'
_chemical_formula_sum            'C6 H5 Cl2.5 N Pb'
_chemical_formula_weight         386.96
_chemical_oxdiff_formula         'C1 H1 N1 Cl1 Pb1'
_chemical_oxdiff_usercomment     Y567
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Pb -3.20855 10.15388 31.06170 13.06370 18.44200 5.96960 0.69020 2.35760 8.61800
47.25790 13.4118003845
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   4.0291(3)
_cell_length_b                   8.8371(6)
_cell_length_c                   12.3963(10)
_cell_angle_alpha                100.672(6)
_cell_angle_beta                 91.860(6)
_cell_angle_gamma                102.273(6)
_cell_volume                     422.64(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1530
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.7420
_cell_measurement_theta_min      4.7600
_exptl_absorpt_coefficient_mu    20.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    3.0404
_exptl_crystal_description       block
_exptl_crystal_F_000             339.9181
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.1073
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3273
_diffrn_reflns_theta_full        25.4984
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.35
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  82.00   1.00    2.06    --   12.45  57.00  60.00   98
  2  ω    -20.00  15.00   1.00    2.06    --   12.45  77.00 -60.00   35
  3  ω    -55.00  33.00   1.00    2.06    --   12.45 -57.00 -90.00   88
  4  ω    -18.00  47.00   1.00    2.06    --   12.45 -99.00-180.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0797290000
_diffrn_orient_matrix_UB_12      -0.0682044000
_diffrn_orient_matrix_UB_13      -0.0393578000
_diffrn_orient_matrix_UB_21      -0.0526119000
_diffrn_orient_matrix_UB_22      -0.0402638000
_diffrn_orient_matrix_UB_23      0.0431277000
_diffrn_orient_matrix_UB_31      -0.1533509000
_diffrn_orient_matrix_UB_32      0.0273082000
_diffrn_orient_matrix_UB_33      0.0005211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.0
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1357
_reflns_number_total             1560
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.5972
_refine_diff_density_min         -2.4223
_refine_diff_density_rms         0.4122
_refine_ls_d_res_high            0.8255
_refine_ls_d_res_low             6.0739
_refine_ls_goodness_of_fit_ref   0.9427
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1560
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      0.9408
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1053
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 C5
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1a), C2(H2), C5(H5), C6(H6)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Pb1 Pb 0.37351(10) 0.24492(5) 0.05760(4) 0.0290(2) Uani 1.000000 1 . . .
Cl1 Cl -0.0989(8) 0.2727(4) 0.2244(3) 0.0365(8) Uani 1.000000 1 . . .
Cl2 Cl 0.2249(7) -0.0733(3) 0.0963(3) 0.0297(7) Uani 1.000000 1 . . .
Cl3 Cl 0.0 0.5 0.0 0.0456(13) Uani 1.000000 2 S T P
N1 N 0.080(3) 0.0379(15) 0.4000(11) 0.053(3) Uani 1.000000 1 . . .
H1 H 0.129(3) 0.0619(15) 0.3374(11) 0.064(4) Uiso 1.000000 1 R . .
C1 C 0.645(4) 0.3704(17) 0.5886(16) 0.050(4) Uani 1.000000 1 . . .
H1a H 0.805(4) 0.4626(17) 0.5868(16) 0.060(5) Uiso 1.000000 1 R . .
C2 C 0.490(4) 0.2765(16) 0.4916(12) 0.042(4) Uani 1.000000 1 . . .
H2 H 0.546(4) 0.3040(16) 0.4245(12) 0.050(4) Uiso 1.000000 1 R . .
C3 C 0.243(4) 0.1367(16) 0.4953(12) 0.042(4) Uani 1.000000 1 . . .
C4 C -0.160(3) -0.0999(14) 0.4033(10) 0.030(3) Uani 1.000000 1 . . .
C5 C -0.324(4) -0.1952(17) 0.3046(13) 0.046(4) Uani 1.000000 1 . U .
H5 H -0.271(4) -0.1681(17) 0.2373(13) 0.056(4) Uiso 1.000000 1 R . .
C6 C -0.565(4) -0.329(2) 0.3093(15) 0.056(4) Uani 1.000000 1 . . .
H6 H -0.676(4) -0.393(2) 0.2446(15) 0.067(5) Uiso 1.000000 1 R . .


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
Pb1 Cl1 2.856(4) 1_655 ?
Pb1 Cl1 2.868(3) . ?
Pb1 Cl2 2.881(3) . ?
Pb1 Cl2 2.955(3) 2_655 ?
Pb1 Cl2 2.971(3) 2 ?
N1 H1 0.8600 . ?
N1 C3 1.38(2) . ?
N1 C4 1.394(17) . ?
C1 H1a 0.9300 . ?
C1 C2 1.37(2) . ?
C1 C6 1.41(2) 2_556 ?
C2 H2 0.9300 . ?
C2 C3 1.422(19) . ?
C3 C4 1.389(18) 2_556 ?
C4 C5 1.404(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.37(2) . ?
C6 H6 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
Cl2 Pb1 Cl1 86.66(9) 2 . ?
Cl2 Pb1 Cl1 87.18(9) 2_655 1_655 ?
Cl2 Pb1 Cl1 154.66(9) 2 1_655 ?
Cl2 Pb1 Cl1 154.60(9) 2_655 . ?
Cl2 Pb1 Cl1 79.83(9) . . ?
Cl2 Pb1 Cl1 80.27(9) . 1_655 ?
C3 N1 H1 119.3(8) . . ?
C4 N1 H1 119.3(8) . . ?
C4 N1 C3 121.4(12) . . ?
C2 C1 H1a 119.5(9) . . ?
C6 C1 H1a 119.5(10) 2_556 . ?
C6 C1 C2 121.0(14) 2_556 . ?
H2 C2 C1 120.5(9) . . ?
C3 C2 C1 119.0(14) . . ?
C3 C2 H2 120.5(9) . . ?
C2 C3 N1 121.2(13) . . ?
C4 C3 N1 119.5(13) 2_556 . ?
C4 C3 C2 119.3(14) 2_556 . ?
C3 C4 N1 119.1(12) 2_556 . ?
C5 C4 N1 119.6(12) . . ?
C5 C4 C3 121.3(13) . 2_556 ?
H5 C5 C4 120.6(8) . . ?
C6 C5 C4 118.9(15) . . ?
C6 C5 H5 120.6(10) . . ?
C5 C6 C1 120.5(17) . 2_556 ?
H6 C6 C1 119.8(10) . 2_556 ?
H6 C6 C5 119.8(10) . . ?

_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 2.854
_oxdiff_exptl_absorpt_empirical_full_min 0.589
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C5 0.0050

