# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_liujie201719_0m_5
_database_code_depnum_ccdc_archive 'CCDC 1562483'
_audit_update_record             
;
2017-08-01 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 Br3 N O Pb'
_chemical_formula_weight         543.03

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   4.3093(8)
_cell_length_b                   10.586(2)
_cell_length_c                   12.335(2)
_cell_angle_alpha                103.012(2)
_cell_angle_beta                 97.348(2)
_cell_angle_gamma                94.651(2)
_cell_volume                     540.23(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5888
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.338
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    26.660
_shelx_estimated_absorpt_T_min   0.071
_shelx_estimated_absorpt_T_max   0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.016785
_exptl_absorpt_correction_T_max  0.094913
_exptl_absorpt_process_details   'Bruker TWINABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2481
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2481
_reflns_number_gt                2112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²+0.3663P] 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         2481
_refine_ls_number_parameters     102
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_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
Pb1 Pb 0.28773(7) 0.68451(3) 0.60486(2) 0.03945(13) Uani 1 1 d . . . . .
N1 N 0.910(3) 0.8508(8) 0.2676(7) 0.0704(5) Uani 1 1 d . U . . .
H6 H 0.9096 0.8978 0.3342 0.084 Uiso 1 1 calc R U . . .
Br1 Br 0.7658(2) 0.50092(8) 0.65295(7) 0.0462(2) Uani 1 1 d . . . . .
O1 O 0.901(2) 0.6337(7) -0.0471(5) 0.0705(5) Uani 1 1 d . U . . .
H3 H 1.0376 0.6649 -0.0770 0.106 Uiso 1 1 calc R U . . .
C1 C 0.775(3) 0.7248(10) 0.2394(8) 0.0704(5) Uani 1 1 d . U . . .
H1 H 0.6873 0.6890 0.2925 0.084 Uiso 1 1 calc R U . . .
C2 C 0.767(3) 0.6517(11) 0.1329(8) 0.0704(5) Uani 1 1 d . U . . .
H2 H 0.6739 0.5658 0.1119 0.085 Uiso 1 1 calc R U . . .
Br2 Br 0.3979(2) 0.82372(10) 0.83017(8) 0.0585(3) Uani 1 1 d . . . . .
C3 C 0.903(3) 0.7083(10) 0.0562(8) 0.0704(5) Uani 1 1 d . U . . .
Br3 Br -0.2123(2) 0.85437(8) 0.54003(7) 0.0460(2) Uani 1 1 d . . . . .
C4 C 1.033(3) 0.8351(10) 0.0861(8) 0.0704(5) Uani 1 1 d . U . . .
H4 H 1.1121 0.8751 0.0340 0.085 Uiso 1 1 calc R U . . .
C5 C 1.042(3) 0.9012(11) 0.1950(8) 0.0704(5) Uani 1 1 d . U . . .
H5 H 1.1453 0.9854 0.2185 0.084 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pb1 0.03588(19) 0.04037(19) 0.0427(2) 0.00893(13) 0.01087(13) 0.00274(13)
N1 0.1117(10) 0.0556(9) 0.0456(9) 0.0105(9) 0.0188(9) 0.0127(9)
Br1 0.0477(5) 0.0440(4) 0.0491(5) 0.0159(4) 0.0087(4) 0.0016(4)
O1 0.1117(10) 0.0557(9) 0.0457(9) 0.0105(9) 0.0188(9) 0.0128(9)
C1 0.1117(10) 0.0556(9) 0.0457(9) 0.0105(9) 0.0188(9) 0.0127(9)
C2 0.1117(10) 0.0556(9) 0.0457(9) 0.0105(9) 0.0188(9) 0.0127(9)
Br2 0.0618(6) 0.0675(6) 0.0434(5) 0.0055(4) 0.0129(4) 0.0062(5)
C3 0.1117(10) 0.0556(9) 0.0457(9) 0.0105(9) 0.0188(9) 0.0127(9)
Br3 0.0538(5) 0.0431(4) 0.0432(5) 0.0133(4) 0.0134(4) 0.0006(4)
C4 0.1117(10) 0.0556(9) 0.0457(9) 0.0105(9) 0.0188(9) 0.0127(9)
C5 0.1117(10) 0.0556(9) 0.0457(9) 0.0105(9) 0.0188(9) 0.0127(9)

_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 Br2 2.7974(11) . ?
Pb1 Br3 2.9959(9) 1_655 ?
Pb1 Br1 3.0380(10) . ?
Pb1 Br1 3.0560(9) 1_455 ?
Pb1 Br3 3.0578(10) . ?
N1 C5 1.305(14) . ?
N1 C1 1.362(13) . ?
N1 H6 0.8600 . ?
Br1 Pb1 3.0560(9) 1_655 ?
O1 C3 1.338(11) . ?
O1 H3 0.8200 . ?
C1 C2 1.361(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(15) . ?
Br3 Pb1 2.9959(9) 1_455 ?
C4 C5 1.362(13) . ?
C4 H4 0.9300 . ?
C5 H5 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
Br2 Pb1 Br3 93.10(3) . 1_655 ?
Br2 Pb1 Br1 91.06(3) . . ?
Br3 Pb1 Br1 90.21(3) 1_655 . ?
Br2 Pb1 Br1 91.06(3) . 1_455 ?
Br3 Pb1 Br1 175.84(2) 1_655 1_455 ?
Br1 Pb1 Br1 90.00(3) . 1_455 ?
Br2 Pb1 Br3 93.04(3) . . ?
Br3 Pb1 Br3 90.76(3) 1_655 . ?
Br1 Pb1 Br3 175.73(2) . . ?
Br1 Pb1 Br3 88.72(3) 1_455 . ?
C5 N1 C1 120.9(9) . . ?
C5 N1 H6 119.5 . . ?
C1 N1 H6 119.5 . . ?
Pb1 Br1 Pb1 90.01(3) . 1_655 ?
C3 O1 H3 109.5 . . ?
C2 C1 N1 119.5(10) . . ?
C2 C1 H1 120.3 . . ?
N1 C1 H1 120.3 . . ?
C1 C2 C3 118.6(11) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
O1 C3 C4 121.7(10) . . ?
O1 C3 C2 117.6(10) . . ?
C4 C3 C2 120.7(10) . . ?
Pb1 Br3 Pb1 90.76(3) 1_455 . ?
C3 C4 C5 117.6(10) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
N1 C5 C4 122.5(11) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?

_refine_diff_density_max         1.191
_refine_diff_density_min         -2.118
_refine_diff_density_rms         0.255

_shelx_res_file                  
;

    liujie201719_0m_5.res created by SHELXL-2014/7


TITL liujie201719_0m_4_a.res in P-1
CELL  0.71073   4.3093  10.5864  12.3348  103.012   97.348   94.651
ZERR    2.000   0.0008   0.0020   0.0023    0.002    0.002    0.002
LATT 1
SFAC C  H  Br N  O  Pb
UNIT 10  12  6  2  2  2
LIST 4
MERG  0
L.S. 10
ACTA
OMIT 3 4 3
OMIT 0 -2 1
OMIT 4 4 3
OMIT -5 5 3
OMIT -4 5 3
OMIT -3 5 3
OMIT -2 5 3
BOND $H
DELU 0.000001 O1 N1 C1 C2 C3 C4 C5
SIMU 0.0000001 O1 N1 C1 C2 C3 C4 C5
FMAP 2
PLAN 20
SIZE 0.101 0.11 0.21
TEMP 23
WGHT    0.060500    0.366300
BASF   0.50703
FVAR       0.37424
PB1   6    0.287732    0.684512    0.604860    11.00000    0.03588    0.04037 =
         0.04270    0.00893    0.01087    0.00274
N1    4    0.910348    0.850798    0.267597    11.00000    0.11166    0.05561 =
         0.04565    0.01053    0.01885    0.01273
AFIX  43
H6    2    0.909569    0.897819    0.334204    11.00000   -1.20000
AFIX   0
BR1   3    0.765805    0.500924    0.652945    11.00000    0.04766    0.04398 =
         0.04911    0.01587    0.00869    0.00158
O1    5    0.900593    0.633683   -0.047074    11.00000    0.11170    0.05565 =
         0.04568    0.01050    0.01882    0.01275
AFIX 147
H3    2    1.037625    0.664856   -0.076962    11.00000   -1.50000
AFIX   0
C1    1    0.774542    0.724820    0.239398    11.00000    0.11166    0.05561 =
         0.04565    0.01053    0.01884    0.01273
AFIX  43
H1    2    0.687336    0.689020    0.292467    11.00000   -1.20000
AFIX   0
C2    1    0.767439    0.651718    0.132939    11.00000    0.11167    0.05562 =
         0.04566    0.01052    0.01883    0.01274
AFIX  43
H2    2    0.673936    0.565779    0.111915    11.00000   -1.20000
AFIX   0
BR2   3    0.397949    0.823718    0.830167    11.00000    0.06179    0.06755 =
         0.04342    0.00546    0.01291    0.00618
C3    1    0.903071    0.708328    0.056250    11.00000    0.11168    0.05563 =
         0.04566    0.01052    0.01883    0.01275
BR3   3   -0.212258    0.854368    0.540029    11.00000    0.05380    0.04311 =
         0.04322    0.01330    0.01338    0.00061
C4    1    1.032633    0.835074    0.086088    11.00000    0.11167    0.05562 =
         0.04566    0.01053    0.01884    0.01274
AFIX  43
H4    2    1.112142    0.875109    0.034016    11.00000   -1.20000
AFIX   0
C5    1    1.041632    0.901160    0.194975    11.00000    0.11166    0.05561 =
         0.04565    0.01053    0.01885    0.01273
AFIX  43
H5    2    1.145306    0.985407    0.218480    11.00000   -1.20000
REM #####
REM #####
AFIX   0
HKLF 5

REM  liujie201719_0m_4_a.res in P-1
REM R1 =  0.0368 for    2112 Fo > 4sig(Fo)  and  0.0450 for all    2481 data
REM    102 parameters refined using     42 restraints

END

WGHT      0.0630      0.6025

REM Highest difference peak  1.191,  deepest hole -2.118,  1-sigma level  0.255
Q1    1   0.2596  0.6999  0.6817  11.00000  0.05    1.19
Q2    1   0.3277  0.6492  0.5180  11.00000  0.05    1.18
Q3    1   0.4970  0.6804  0.6062  11.00000  0.05    1.17
Q4    1   0.4178  0.7462  0.5528  11.00000  0.05    0.94
Q5    1   1.0079  0.9265  0.1782  11.00000  0.05    0.88
Q6    1  -0.0084  0.6128  0.5605  11.00000  0.05    0.83
Q7    1   0.6954  0.5965 -0.0433  11.00000  0.05    0.76
Q8    1   0.0635  0.6888  0.6005  11.00000  0.05    0.75
Q9    1   0.1918  0.6427  0.6604  11.00000  0.05    0.74
Q10   1   1.4495  0.6405 -0.0587  11.00000  0.05    0.74
Q11   1   1.1733  0.7381  0.4208  11.00000  0.05    0.73
Q12   1   0.5145  0.7650  0.6604  11.00000  0.05    0.73
Q13   1   1.0932  0.8659  0.1272  11.00000  0.05    0.69
Q14   1   0.0438  0.6987  0.7043  11.00000  0.05    0.68
Q15   1  -0.3483  0.7466  0.5725  11.00000  0.05    0.66
Q16   1   0.9032  0.6496  0.6536  11.00000  0.05    0.66
Q17   1   0.6040  0.7381 -0.0448  11.00000  0.05    0.65
Q18   1   0.6691  0.8078  0.7459  11.00000  0.05    0.65
Q19   1   0.6376  0.8184  0.8396  11.00000  0.05    0.65
Q20   1   0.2744  0.8012  0.6559  11.00000  0.05    0.65
;
_shelx_res_checksum              82468
