# Electronic Supplementary Material (ESI) for ChemComm.
# 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_191115a_a
_audit_block_doi                 10.5517/ccdc.csd.cc25kc7c
_database_code_depnum_ccdc_archive 'CCDC 2012682'
loop_
_audit_author_name
_audit_author_address
'Honghan Fei'
;Tongji University
China
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_audit_creation_date             2020-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C6 H2 Br O4 Pb S, C2 H8 N'
_chemical_formula_sum            'C8 H10 Br N O4 Pb S'
_chemical_formula_weight         503.36
_chemical_absolute_configuration unk
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
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'
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'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'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'
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'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'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'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           ' P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+5/6
3 y,-x+y,z+1/6
4 -y,x-y,z+2/3
5 -x+y,-x,z+1/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      170
_cell_length_a                   10.1079(9)
_cell_length_b                   10.1079(9)
_cell_length_c                   21.838(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1932.2(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9538
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.98
_exptl_absorpt_coefficient_mu    16.361
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1521 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.5688.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.5953
_exptl_crystal_description       block
_exptl_crystal_F_000             1362.0334
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27306
_diffrn_reflns_theta_full        27.9868
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.51
_diffrn_ambient_temperature      299.0
_diffrn_measured_fraction_theta_full 0.9716
_diffrn_measured_fraction_theta_max 0.9716
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.954
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              28
_reflns_limit_l_min              -28
_reflns_number_gt                2926
_reflns_number_total             3015
_reflns_threshold_expression     I>=2u(I)
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.5309
_refine_diff_density_min         -1.2797
_refine_diff_density_rms         0.1557
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.010(8)
_refine_ls_d_res_high            0.7573
_refine_ls_d_res_low             8.1252
_refine_ls_goodness_of_fit_ref   1.0330
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0210
_refine_ls_restrained_S_all      1.0265
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+1.0478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0539
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C7 \\sim N1-C8 \\sim N1'-C7' \\sim N1'-C8'
 with sigma of 0.01
 C7-C8 \\sim C7'-C8'
 with sigma of 0.02
3. Rigid bond restraints
 N1, C7, C8, N1', C7', C8'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim C7 \\sim C8 \\sim N1' \\sim C7' \\sim C8': within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(N1')=Sof(H1'a)=Sof(H1'b)=Sof(C7')=Sof(H7'a)=Sof(H7'b)=Sof(H7'c)=Sof(C8')=
 Sof(H8'a)=Sof(H8'b)=Sof(H8'c)=1-FVAR(1)
 Sof(N1)=Sof(H1a)=Sof(H1b)=Sof(C7)=Sof(H7a)=Sof(H7b)=Sof(H7c)=Sof(C8)=Sof(H8a)=
 Sof(H8b)=Sof(H8c)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 N1(H1a,H1b), N1'(H1'a,H1'b)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
6.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C7'(H7'a,H7'b,H7'c), C8'(H8'a,H8'b,H8'c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Pb1 Pb 1.163879(19) 1.05721(2) 0.578550(5) 0.02405(6) Uani 1.000000 . . .
S1 S 0.57694(15) 0.48846(14) 0.58222(6) 0.0343(3) Uani 1.000000 . . .
Br1 Br 1.20155(8) 1.23555(7) 0.69464(2) 0.04194(14) Uani 1.000000 . . .
C1 C 0.8167(7) 0.7355(7) 0.6424(3) 0.0331(12) Uani 1.000000 . . .
O1 O 0.9304(5) 0.8704(5) 0.6378(2) 0.0441(11) Uani 1.000000 . . .
C2 C 0.7139(6) 0.6785(6) 0.5886(3) 0.0295(11) Uani 1.000000 . . .
O2 O 0.7896(6) 0.6563(6) 0.6890(2) 0.0568(14) Uani 1.000000 . . .
C3 C 0.7140(7) 0.7601(7) 0.5386(3) 0.0408(14) Uani 1.000000 . . .
H3 H 0.7824(7) 0.8638(7) 0.5332(3) 0.0490(17) Uiso 1.000000 R . .
O3 O 0.3416(6) 0.4284(5) 0.4313(2) 0.0474(12) Uani 1.000000 . . .
O4 O 0.3382(5) 0.2580(5) 0.49717(19) 0.0354(9) Uani 1.000000 . . .
C4 C 0.5990(8) 0.6696(7) 0.4966(3) 0.0442(16) Uani 1.000000 . . .
H4 H 0.5806(8) 0.7081(7) 0.4609(3) 0.0530(19) Uiso 1.000000 R . .
C6 C 0.3905(6) 0.3937(6) 0.4783(3) 0.0303(11) Uani 1.000000 . . .
C5 C 0.5176(6) 0.5207(6) 0.5130(2) 0.0306(11) Uani 1.000000 . . .
N1 N 1.1253(18) 1.6024(16) 0.6340(5) 0.104(5) Uani 0.668(13) D U 1
H1a H 1.1424(18) 1.6537(16) 0.6695(5) 0.124(5) Uiso 0.668(13) R . 1
H1b H 1.1139(18) 1.6594(16) 0.6051(5) 0.124(5) Uiso 0.668(13) R . 1
C7 C 1.262(2) 1.603(3) 0.6198(7) 0.101(5) Uani 0.668(13) D U 1
H7a H 1.298(12) 1.65(2) 0.580(4) 0.151(8) Uiso 0.668(13) GR . 1
H7b H 1.338(7) 1.661(19) 0.650(5) 0.151(8) Uiso 0.668(13) GR . 1
H7c H 1.243(6) 1.500(3) 0.619(9) 0.151(8) Uiso 0.668(13) GR . 1
C8 C 0.983(2) 1.469(2) 0.6400(7) 0.107(6) Uani 0.668(13) D U 1
H8a H 0.925(9) 1.483(8) 0.672(6) 0.160(8) Uiso 0.668(13) GR . 1
H8b H 0.929(8) 1.448(11) 0.602(3) 0.160(8) Uiso 0.668(13) GR . 1
H8c H 0.998(2) 1.385(5) 0.651(8) 0.160(8) Uiso 0.668(13) GR . 1
N1' N 1.1175(15) 1.5500(16) 0.5868(5) 0.037(4) Uani 0.332(13) D U 2
H1'a H 1.1226(15) 1.6229(16) 0.5616(5) 0.045(4) Uiso 0.332(13) R . 2
H1'b H 1.0864(15) 1.4662(16) 0.5634(5) 0.045(4) Uiso 0.332(13) R . 2
C7' C 1.2687(19) 1.597(3) 0.6019(7) 0.037(4) Uani 0.332(13) D U 2
H7'a H 1.326(5) 1.706(3) 0.605(8) 0.056(6) Uiso 0.332(13) GR . 2
H7'b H 1.272(2) 1.552(17) 0.640(4) 0.056(6) Uiso 0.332(13) GR . 2
H7'c H 1.313(7) 1.565(18) 0.570(4) 0.056(6) Uiso 0.332(13) GR . 2
C8' C 0.995(2) 1.515(3) 0.6261(7) 0.048(5) Uani 0.332(13) D U 2
H8'a H 0.901(3) 1.46(2) 0.604(2) 0.072(7) Uiso 0.332(13) GR . 2
H8'b H 0.996(14) 1.45(2) 0.659(5) 0.072(7) Uiso 0.332(13) GR . 2
H8'c H 1.004(13) 1.608(3) 0.642(8) 0.072(7) Uiso 0.332(13) GR . 2


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 Br1 3.0224(6) . ?
Pb1 O1 2.521(5) . ?
Pb1 O3 2.573(4) 3_665 ?
Pb1 O4 2.609(4) 1_665 ?
S1 C2 1.722(5) . ?
S1 C5 1.717(6) . ?
C1 O1 1.274(8) . ?
C1 C2 1.482(7) . ?
C1 O2 1.237(8) . ?
C2 C3 1.367(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(8) . ?
O3 C6 1.263(7) . ?
O4 C6 1.268(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.353(8) . ?
C6 C5 1.491(7) . ?
N1 H1a 0.9000 . ?
N1 H1b 0.9000 . ?
N1 C7 1.413(12) . ?
N1 C8 1.400(12) . ?
C7 H7a 0.9600 . ?
C7 H7b 0.9600 . ?
C7 H7c 0.9600 . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
N1' H1'a 0.9000 . ?
N1' H1'b 0.9000 . ?
N1' C7' 1.395(12) . ?
N1' C8' 1.399(12) . ?
C7' H7'a 0.9600 . ?
C7' H7'b 0.9600 . ?
C7' H7'c 0.9600 . ?
C8' H8'a 0.9600 . ?
C8' H8'b 0.9600 . ?
C8' H8'c 0.9600 . ?

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
O1 Pb1 Br1 78.90(11) . . ?
O3 Pb1 Br1 88.79(12) 3_665 . ?
O3 Pb1 O1 122.14(15) 3_665 . ?
O4 Pb1 Br1 105.83(9) 1_665 . ?
O4 Pb1 O1 161.41(14) 1_665 . ?
O4 Pb1 O3 76.29(14) 1_665 3_665 ?
C5 S1 C2 91.2(3) . . ?
C2 C1 O1 115.9(5) . . ?
O2 C1 O1 123.1(5) . . ?
O2 C1 C2 121.0(5) . . ?
C1 O1 Pb1 147.9(4) . . ?
C1 C2 S1 120.9(4) . . ?
C3 C2 S1 111.5(4) . . ?
C3 C2 C1 127.5(5) . . ?
H3 C3 C2 123.9(3) . . ?
C4 C3 C2 112.2(5) . . ?
C4 C3 H3 123.9(3) . . ?
C6 O3 Pb1 97.5(3) . 2_544 ?
C6 O4 Pb1 144.9(4) . 1_445 ?
H4 C4 C3 123.3(3) . . ?
C5 C4 C3 113.4(6) . . ?
C5 C4 H4 123.3(4) . . ?
O4 C6 O3 123.8(5) . . ?
C5 C6 O3 117.5(5) . . ?
C5 C6 O4 118.7(5) . . ?
C4 C5 S1 111.6(4) . . ?
C6 C5 S1 121.1(4) . . ?
C6 C5 C4 127.3(5) . . ?
H1b N1 H1a 106.5 . . ?
C7 N1 H1a 106.4(9) . . ?
C7 N1 H1b 106.4(10) . . ?
C8 N1 H1a 106.4(8) . . ?
C8 N1 H1b 106.4(11) . . ?
C8 N1 C7 123.7(16) . . ?
H7a C7 N1 109.5 . . ?
H7b C7 N1 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 N1 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8a C8 N1 109.5 . . ?
H8b C8 N1 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 N1 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
H1'b N1' H1'a 105.9 . . ?
C7' N1' H1'a 105.2(11) . . ?
C7' N1' H1'b 105.2(10) . . ?
C8' N1' H1'a 105.2(11) . . ?
C8' N1' H1'b 105.2(11) . . ?
C8' N1' C7' 128.4(14) . . ?
H7'a C7' N1' 109.5 . . ?
H7'b C7' N1' 109.5 . . ?
H7'b C7' H7'a 109.5 . . ?
H7'c C7' N1' 109.5 . . ?
H7'c C7' H7'a 109.5 . . ?
H7'c C7' H7'b 109.5 . . ?
H8'a C8' N1' 109.5 . . ?
H8'b C8' N1' 109.5 . . ?
H8'b C8' H8'a 109.5 . . ?
H8'c C8' N1' 109.5 . . ?
H8'c C8' H8'a 109.5 . . ?
H8'c C8' H8'b 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
N1 C7 1 1
N1 C8 1 1
C7 C8 1 2
N1' C7' 1 1
N1' C8' 1 1
C7' C8' 1 2

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0100 1.4016 0.0068 0.0112
2 0.0200 2.4979 0.0178 0.0178

loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
N1 C7 0.0100 0.1175 -0.0002
N1 C8 0.0100 0.1213 -0.0067
C7 C8 0.0100 0.1405 -0.0040
N1' C7' 0.0100 0.0480 0.0006
N1' C8' 0.0100 0.0472 0.0013
C7' C8' 0.0100 0.0516 -0.0053

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
N1 C7 0.0100
N1 C8 0.0100
N1' C7' 0.0100
N1' C8' 0.0100

####################################################################### 
# 
# 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_90507a_a
_database_code_depnum_ccdc_archive 'CCDC 2012683'
loop_
_audit_author_name
_audit_author_address
'Honghan Fei'
;Tongji University
China
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_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         'C6 H2 Cl O4 Pb S, C2 H8 N'
_chemical_formula_sum            'C8 H10 Cl N O4 Pb S'
_chemical_formula_weight         458.87
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   10.0345(9)
_cell_length_b                   10.0345(9)
_cell_length_c                   21.669(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1889.6(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    4970
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.768
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1272
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13945
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.568
_diffrn_reflns_theta_min         2.525
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                2513
_reflns_number_total             2806
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      0.998
_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)+(0.0097P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0444
_refine_ls_wR_factor_ref         0.0458
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C7 = N1-C8
 1.45 with sigma of 0.01
 N1-C7 \\sim N1-C8 \\sim N1'-C7' \\sim N1'-C8'
 with sigma of 0.01
 C7-C8 \\sim C7'-C8'
 with sigma of 0.02
3. Rigid bond restraints
 N1, C7, C8, N1', C7', C8'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim C7 \\sim C8 \\sim N1' \\sim C7' \\sim C8': within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(N1')=Sof(H1'A)=Sof(H1'B)=Sof(C7')=Sof(H7'A)=Sof(H7'B)=Sof(H7'C)=Sof(C8')=
 Sof(H8'A)=Sof(H8'B)=Sof(H8'C)=1-FVAR(1)
 Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=
 Sof(H8B)=Sof(H8C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N1'(H1'A,H1'B)
6.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
6.d Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C8'(H8'A,H8'B,H8'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Pb1 Pb 1.06593(3) 0.16577(3) 0.59994(3) 0.02950(9) Uani 1 1 d . . . . .
S1 S 0.5777(3) 0.0844(3) 0.43433(13) 0.0413(5) Uani 1 1 d . . . . .
Cl1 Cl 1.2277(3) 0.2014(3) 0.71522(12) 0.0482(6) Uani 1 1 d . . . . .
O1 O 0.7911(10) 0.1312(10) 0.5422(4) 0.069(2) Uani 1 1 d . . . . .
C1 C 0.8208(11) 0.0787(10) 0.4969(4) 0.036(2) Uani 1 1 d . . . . .
O2 O 0.9339(7) 0.0599(8) 0.4930(3) 0.0497(18) Uani 1 1 d . . . . .
C2 C 0.7153(9) 0.0309(10) 0.4422(4) 0.035(2) Uani 1 1 d . . . . .
O3 O 0.3376(7) 0.0719(8) 0.3478(3) 0.0382(15) Uani 1 1 d . . . . .
C3 C 0.7164(12) -0.0504(12) 0.3922(5) 0.046(3) Uani 1 1 d . . . . .
H3 H 0.7852 -0.0863 0.3876 0.055 Uiso 1 1 calc R . . . .
C4 C 0.6037(10) -0.0748(13) 0.3480(5) 0.048(3) Uani 1 1 d . . . . .
H4 H 0.5867 -0.1329 0.3124 0.058 Uiso 1 1 calc R . . . .
O4 O 0.3429(8) -0.0934(8) 0.2819(3) 0.053(2) Uani 1 1 d . . . . .
C5 C 0.5216(10) -0.0040(10) 0.3631(4) 0.036(2) Uani 1 1 d . . . . .
C6 C 0.3909(10) -0.0084(10) 0.3293(4) 0.034(2) Uani 1 1 d . . . . .
N1 N 0.6044(18) 0.1241(16) 0.6502(8) 0.070(4) Uani 0.618(17) 1 d D U P A 1
H1A H 0.6351 0.1332 0.6893 0.084 Uiso 0.618(17) 1 calc R . P A 1
H1B H 0.6816 0.1333 0.6269 0.084 Uiso 0.618(17) 1 calc R . P A 1
C7 C 0.585(3) 0.253(2) 0.6367(11) 0.063(5) Uani 0.618(17) 1 d D U P A 1
H7A H 0.6796 0.3470 0.6444 0.094 Uiso 0.618(17) 1 calc R . P A 1
H7B H 0.5564 0.2497 0.5942 0.094 Uiso 0.618(17) 1 calc R . P A 1
H7C H 0.5054 0.2497 0.6626 0.094 Uiso 0.618(17) 1 calc R . P A 1
C8 C 0.479(3) -0.030(2) 0.6424(13) 0.077(7) Uani 0.618(17) 1 d D U P A 1
H8A H 0.5112 -0.1020 0.6533 0.115 Uiso 0.618(17) 1 calc R . P A 1
H8B H 0.3946 -0.0456 0.6685 0.115 Uiso 0.618(17) 1 calc R . P A 1
H8C H 0.4456 -0.0456 0.6001 0.115 Uiso 0.618(17) 1 calc R . P A 1
N1' N 0.540(3) 0.111(3) 0.6074(12) 0.067(5) Uani 0.382(17) 1 d D U P A 2
H1'A H 0.6098 0.0924 0.5902 0.081 Uiso 0.382(17) 1 calc R . P A 2
H1'B H 0.4640 0.0824 0.5803 0.081 Uiso 0.382(17) 1 calc R . P A 2
C7' C 0.610(6) 0.274(3) 0.616(2) 0.076(9) Uani 0.382(17) 1 d D U P A 2
H7'A H 0.7037 0.3253 0.5924 0.114 Uiso 0.382(17) 1 calc GR . P A 2
H7'B H 0.6331 0.2984 0.6589 0.114 Uiso 0.382(17) 1 calc GR . P A 2
H7'C H 0.5409 0.3077 0.6023 0.114 Uiso 0.382(17) 1 calc GR . P A 2
C8' C 0.479(6) 0.013(4) 0.6605(16) 0.083(11) Uani 0.382(17) 1 d D U P A 2
H8'A H 0.3697 -0.0529 0.6557 0.124 Uiso 0.382(17) 1 calc GR . P A 2
H8'B H 0.4991 0.0746 0.6969 0.124 Uiso 0.382(17) 1 calc GR . P A 2
H8'C H 0.5267 -0.0492 0.6645 0.124 Uiso 0.382(17) 1 calc GR . P A 2


_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
Pb1 Cl1 3.070(3) 5_664 ?
Pb1 Cl1 2.902(3) . ?
Pb1 O2 2.617(7) . ?
Pb1 O2 2.513(7) 6_545 ?
Pb1 O3 2.721(6) 2_655 ?
Pb1 O3 2.639(6) 6_655 ?
Pb1 O4 2.609(6) 2_655 ?
S1 C2 1.722(8) . ?
S1 C5 1.728(10) . ?
Cl1 Pb1 3.070(3) 6_545 ?
O1 C1 1.220(12) . ?
C1 O2 1.243(11) . ?
C1 C2 1.499(13) . ?
O2 Pb1 2.513(7) 5_664 ?
C2 C3 1.360(13) . ?
O3 Pb1 2.639(6) 5_564 ?
O3 Pb1 2.721(6) 3_664 ?
O3 C6 1.235(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.406(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(13) . ?
O4 Pb1 2.609(6) 3_664 ?
O4 C6 1.266(10) . ?
C5 C6 1.483(12) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C7 1.436(10) . ?
N1 C8 1.436(10) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N1' H1'A 0.8900 . ?
N1' H1'B 0.8900 . ?
N1' C7' 1.435(14) . ?
N1' C8' 1.438(14) . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?

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 Pb1 Cl1 89.63(5) . 5_664 ?
O2 Pb1 Cl1 161.96(16) . . ?
O2 Pb1 Cl1 78.09(17) 6_545 . ?
O2 Pb1 Cl1 73.57(15) . 5_664 ?
O2 Pb1 Cl1 88.87(18) 6_545 5_664 ?
O2 Pb1 O2 94.69(18) 6_545 . ?
O2 Pb1 O3 161.1(2) 6_545 6_655 ?
O2 Pb1 O3 73.1(2) . 6_655 ?
O2 Pb1 O3 73.3(2) 6_545 2_655 ?
O2 Pb1 O3 118.4(2) . 2_655 ?
O2 Pb1 O4 122.1(2) 6_545 2_655 ?
O3 Pb1 Cl1 75.75(15) 2_655 . ?
O3 Pb1 Cl1 74.07(15) 6_655 5_664 ?
O3 Pb1 Cl1 158.81(14) 2_655 5_664 ?
O3 Pb1 Cl1 109.14(16) 6_655 . ?
O3 Pb1 O3 124.96(15) 6_655 2_655 ?
O4 Pb1 Cl1 148.19(15) 2_655 5_664 ?
O4 Pb1 Cl1 90.06(18) 2_655 . ?
O4 Pb1 O2 107.7(2) 2_655 . ?
O4 Pb1 O3 76.0(2) 2_655 6_655 ?
O4 Pb1 O3 48.9(2) 2_655 2_655 ?
C2 S1 C5 92.0(4) . . ?
Pb1 Cl1 Pb1 81.29(6) . 6_545 ?
O1 C1 O2 124.0(9) . . ?
O1 C1 C2 119.3(9) . . ?
O2 C1 C2 116.7(8) . . ?
Pb1 O2 Pb1 98.7(2) 5_664 . ?
C1 O2 Pb1 148.6(6) . 5_664 ?
C1 O2 Pb1 101.2(6) . . ?
C1 C2 S1 121.7(7) . . ?
C3 C2 S1 110.9(7) . . ?
C3 C2 C1 127.3(8) . . ?
Pb1 O3 Pb1 93.11(18) 5_564 3_664 ?
C6 O3 Pb1 144.7(6) . 5_564 ?
C6 O3 Pb1 90.8(5) . 3_664 ?
C2 C3 H3 123.2 . . ?
C2 C3 C4 113.6(8) . . ?
C4 C3 H3 123.2 . . ?
C3 C4 H4 123.6 . . ?
C5 C4 C3 112.8(9) . . ?
C5 C4 H4 123.6 . . ?
C6 O4 Pb1 95.3(5) . 3_664 ?
C4 C5 S1 110.7(7) . . ?
C4 C5 C6 128.2(9) . . ?
C6 C5 S1 120.9(7) . . ?
O3 C6 O4 124.1(8) . . ?
O3 C6 C5 118.9(8) . . ?
O4 C6 C5 116.9(8) . . ?
H1A N1 H1B 106.9 . . ?
C7 N1 H1A 107.2 . . ?
C7 N1 H1B 107.2 . . ?
C7 N1 C8 120.3(19) . . ?
C8 N1 H1A 107.2 . . ?
C8 N1 H1B 107.2 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H1'A N1' H1'B 107.1 . . ?
C7' N1' H1'A 107.7 . . ?
C7' N1' H1'B 107.7 . . ?
C7' N1' C8' 118(2) . . ?
C8' N1' H1'A 107.7 . . ?
C8' N1' H1'B 107.7 . . ?
N1' C7' H7'A 109.5 . . ?
N1' C7' H7'B 109.5 . . ?
N1' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
N1' C8' H8'A 109.5 . . ?
N1' C8' H8'B 109.5 . . ?
N1' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
