# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_tk212_brteg
_database_code_depnum_ccdc_archive 'CCDC 1538521'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_formula_moiety         '2(C6 H14 O4), C H6 N, Br3 Pb'
_chemical_formula_sum            'C13 H34 Br3 N O8 Pb'
_chemical_formula_weight         779.33
_chemical_melting_point          314.75

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'
O O 0.0106 0.0060 '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'
Pb Pb -3.3944 10.1111 '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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P c a b'
_space_group_name_Hall           '-P 2bc 2ac'

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.7705(5)
_cell_length_b                   21.1114(15)
_cell_length_c                   29.069(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4768.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20078
_cell_measurement_temperature    100(2)
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      27.25



_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.171
_exptl_crystal_F_000             2960
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    12.138
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.0768
_exptl_absorpt_correction_T_max  0.2889
_exptl_absorpt_process_details   STOE-XRED32


_exptl_special_details           
;
 ?
;

_diffrn_reflns_av_R_equivalents  0.1272
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            22499
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.779
_diffrn_reflns_theta_min         1.701
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   '12 x 0.4 mm long-fine focus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3824
_reflns_number_total             4977
_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_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_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    'ShelXS (Sheldrick, 2008)'

_refine_diff_density_max         1.852
_refine_diff_density_min         -2.578
_refine_diff_density_rms         0.339
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1340
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.7042(7) 0.3701(2) 0.3243(2) 0.0266(13) Uani 1 1 d . . . . .
H1 H 0.6419 0.4013 0.3219 0.040 Uiso 1 1 calc GR . . . .
O2 O 0.3908(7) 0.3212(2) 0.2827(2) 0.0220(11) Uani 1 1 d . . . . .
O3 O 0.2029(6) 0.4318(2) 0.2843(2) 0.0223(12) Uani 1 1 d . . . . .
O4 O 0.2377(9) 0.5555(3) 0.3146(3) 0.0416(17) Uani 1 1 d . . . . .
H4 H 0.2957 0.5363 0.2956 0.062 Uiso 1 1 calc GR . . . .
C2 C 0.7042(10) 0.3367(4) 0.2829(3) 0.0277(18) Uani 1 1 d . . . . .
H2A H 0.8112 0.3133 0.2802 0.033 Uiso 1 1 calc R . . . .
H2B H 0.6990 0.3665 0.2575 0.033 Uiso 1 1 calc R . . . .
C3 C 0.5553(9) 0.2911(3) 0.2791(3) 0.0253(17) Uani 1 1 d . . . . .
H3A H 0.5621 0.2694 0.2497 0.030 Uiso 1 1 calc R . . . .
H3B H 0.5654 0.2595 0.3031 0.030 Uiso 1 1 calc R . . . .
C4 C 0.3440(10) 0.3526(4) 0.2412(3) 0.0277(17) Uani 1 1 d . . . . .
H4A H 0.3323 0.3220 0.2166 0.033 Uiso 1 1 calc R . . . .
H4B H 0.4326 0.3827 0.2327 0.033 Uiso 1 1 calc R . . . .
C5 C 0.1761(10) 0.3865(3) 0.2486(3) 0.0251(17) Uani 1 1 d . . . . .
H5A H 0.1405 0.4076 0.2205 0.030 Uiso 1 1 calc R . . . .
H5B H 0.0872 0.3566 0.2574 0.030 Uiso 1 1 calc R . . . .
C6 C 0.0556(10) 0.4730(4) 0.2887(3) 0.0287(18) Uani 1 1 d . . . . .
H6A H -0.0466 0.4484 0.2957 0.034 Uiso 1 1 calc R . . . .
H6B H 0.0363 0.4957 0.2602 0.034 Uiso 1 1 calc R . . . .
C7 C 0.0921(12) 0.5183(4) 0.3268(4) 0.035(2) Uani 1 1 d . . . . .
H7A H -0.0067 0.5455 0.3318 0.042 Uiso 1 1 calc R . . . .
H7B H 0.1150 0.4953 0.3550 0.042 Uiso 1 1 calc R . . . .
O5 O -0.0489(7) 0.3421(3) 0.3868(2) 0.0278(12) Uani 1 1 d . . . . .
H5 H -0.1199 0.3442 0.3660 0.042 Uiso 1 1 calc GR . . . .
O6 O 0.0846(7) 0.4257(2) 0.4519(2) 0.0280(13) Uani 1 1 d . . . . .
O7 O 0.4107(7) 0.4852(2) 0.4313(2) 0.0231(11) Uani 1 1 d . . . . .
O8 O 0.5272(7) 0.4815(2) 0.3376(2) 0.0268(12) Uani 1 1 d . . . . .
H8 H 0.4754 0.4516 0.3491 0.040 Uiso 1 1 calc GR . . . .
C8 C -0.1326(10) 0.3526(4) 0.4300(3) 0.0283(17) Uani 1 1 d . . . . .
H8A H -0.1952 0.3148 0.4389 0.034 Uiso 1 1 calc R . . . .
H8B H -0.2144 0.3870 0.4270 0.034 Uiso 1 1 calc R . . . .
C9 C -0.0031(10) 0.3686(4) 0.4661(3) 0.0274(17) Uani 1 1 d . . . . .
H9A H -0.0598 0.3753 0.4954 0.033 Uiso 1 1 calc R . . . .
H9B H 0.0788 0.3342 0.4695 0.033 Uiso 1 1 calc R . . . .
C10 C 0.2015(9) 0.4481(3) 0.4852(3) 0.0251(17) Uani 1 1 d . . . . .
H10A H 0.2835 0.4152 0.4929 0.030 Uiso 1 1 calc R . . . .
H10B H 0.1401 0.4598 0.5130 0.030 Uiso 1 1 calc R . . . .
C11 C 0.2939(11) 0.5045(3) 0.4663(3) 0.0275(18) Uani 1 1 d . . . . .
H11A H 0.2113 0.5342 0.4536 0.033 Uiso 1 1 calc R . . . .
H11B H 0.3564 0.5257 0.4907 0.033 Uiso 1 1 calc R . . . .
C12 C 0.4922(11) 0.5389(4) 0.4109(3) 0.0280(18) Uani 1 1 d . . . . .
H12A H 0.5562 0.5621 0.4340 0.034 Uiso 1 1 calc R . . . .
H12B H 0.4058 0.5670 0.3980 0.034 Uiso 1 1 calc R . . . .
C13 C 0.6132(10) 0.5168(3) 0.3732(3) 0.0277(18) Uani 1 1 d . . . . .
H13A H 0.6686 0.5535 0.3595 0.033 Uiso 1 1 calc R . . . .
H13B H 0.7022 0.4906 0.3867 0.033 Uiso 1 1 calc R . . . .
N1 N 0.2980(8) 0.3743(3) 0.3747(3) 0.0238(14) Uani 1 1 d . . . . .
H1A H 0.3214 0.3742 0.3448 0.029 Uiso 1 1 calc GR . . . .
H1B H 0.3347 0.4104 0.3871 0.029 Uiso 1 1 calc GR . . . .
H1C H 0.1849 0.3708 0.3789 0.029 Uiso 1 1 calc GR . . . .
C1 C 0.3865(12) 0.3202(4) 0.3971(4) 0.033(2) Uani 1 1 d . . . . .
H1D H 0.5039 0.3185 0.3869 0.050 Uiso 1 1 calc GR . . . .
H1E H 0.3291 0.2815 0.3890 0.050 Uiso 1 1 calc GR . . . .
H1F H 0.3837 0.3256 0.4299 0.050 Uiso 1 1 calc GR . . . .
Pb1 Pb 0.19649(3) 0.25175(2) 0.09204(2) 0.01892(12) Uani 1 1 d . . . . .
Br1 Br 0.43034(9) 0.19414(3) 0.16213(3) 0.02297(18) Uani 1 1 d . . . . .
Br2 Br 0.43663(9) 0.19773(3) 0.02226(3) 0.02446(19) Uani 1 1 d . . . . .
Br3 Br -0.02956(10) 0.14045(3) 0.09774(3) 0.02466(19) 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
O1 C2 1.395(11) . ?
O2 C3 1.432(8) . ?
O2 C4 1.423(10) . ?
O3 C5 1.427(9) . ?
O3 C6 1.444(8) . ?
O4 C7 1.421(12) . ?
C2 C3 1.509(10) . ?
C4 C5 1.503(10) . ?
C6 C7 1.490(13) . ?
O5 C8 1.430(11) . ?
O6 C9 1.445(9) . ?
O6 C10 1.410(10) . ?
O7 C11 1.422(10) . ?
O7 C12 1.429(9) . ?
O8 C13 1.440(10) . ?
C8 C9 1.493(12) . ?
C10 C11 1.496(11) . ?
C12 C13 1.517(13) . ?
N1 C1 1.483(10) . ?
Pb1 Br1 3.1200(8) 8_565 ?
Pb1 Br1 2.9888(8) . ?
Pb1 Br2 3.0543(8) 8_565 ?
Pb1 Br2 2.9827(8) . ?
Pb1 Br3 2.9384(8) . ?
Pb1 Br3 3.1207(8) 8_665 ?
Br1 Pb1 3.1199(8) 8_665 ?
Br2 Pb1 3.0544(8) 8_665 ?
Br3 Pb1 3.1207(8) 8_565 ?

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
C4 O2 C3 111.8(7) . . ?
C5 O3 C6 110.7(6) . . ?
O1 C2 C3 112.7(7) . . ?
O2 C3 C2 113.3(6) . . ?
O2 C4 C5 108.8(7) . . ?
O3 C5 C4 107.2(6) . . ?
O3 C6 C7 107.6(7) . . ?
O4 C7 C6 108.8(8) . . ?
C10 O6 C9 112.8(6) . . ?
C11 O7 C12 110.6(6) . . ?
O5 C8 C9 110.2(7) . . ?
O6 C9 C8 107.8(7) . . ?
O6 C10 C11 108.9(7) . . ?
O7 C11 C10 109.9(6) . . ?
O7 C12 C13 109.3(6) . . ?
O8 C13 C12 113.0(7) . . ?
Br1 Pb1 Br1 96.13(3) . 8_565 ?
Br1 Pb1 Br2 175.39(2) . 8_565 ?
Br1 Pb1 Br3 81.13(2) . 8_665 ?
Br1 Pb1 Br3 98.65(2) 8_565 8_665 ?
Br2 Pb1 Br1 85.85(2) . . ?
Br2 Pb1 Br1 177.21(2) . 8_565 ?
Br2 Pb1 Br1 82.39(2) 8_565 8_565 ?
Br2 Pb1 Br2 95.48(3) . 8_565 ?
Br2 Pb1 Br3 103.39(2) 8_565 8_665 ?
Br2 Pb1 Br3 83.58(2) . 8_665 ?
Br3 Pb1 Br1 89.97(2) . . ?
Br3 Pb1 Br1 81.93(2) . 8_565 ?
Br3 Pb1 Br2 96.12(2) . . ?
Br3 Pb1 Br2 85.50(2) . 8_565 ?
Br3 Pb1 Br3 171.10(3) . 8_665 ?
Pb1 Br1 Pb1 78.98(2) . 8_665 ?
Pb1 Br2 Pb1 80.12(2) . 8_665 ?
Pb1 Br3 Pb1 79.722(17) . 8_565 ?

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
O1 C2 C3 O2 58.5(10) . . . . ?
O2 C4 C5 O3 61.0(8) . . . . ?
O3 C6 C7 O4 62.4(9) . . . . ?
C3 O2 C4 C5 -176.4(6) . . . . ?
C4 O2 C3 C2 77.4(9) . . . . ?
C5 O3 C6 C7 179.5(7) . . . . ?
C6 O3 C5 C4 171.2(7) . . . . ?
O5 C8 C9 O6 60.4(8) . . . . ?
O6 C10 C11 O7 -71.2(8) . . . . ?
O7 C12 C13 O8 59.0(9) . . . . ?
C9 O6 C10 C11 176.3(6) . . . . ?
C10 O6 C9 C8 175.5(7) . . . . ?
C11 O7 C12 C13 -178.9(7) . . . . ?
C12 O7 C11 C10 176.4(7) . . . . ?


# start Validation Reply Form
_vrf_PLAT974_tk212_brteg         
;
PROBLEM: Check Calcd Negative Residual Density on     Pb1      -2.70 eA-3  
RESPONSE: Issue is related to not optimal absorption correction.
;
_vrf_PLAT417_tk212_brteg         
;
PROBLEM: Short Inter D-H..H-D       H1     ..  H8      ..       1.85 Ang.  
RESPONSE: H1 and H8 were treated in a riding model using AFIX 147, thus bonding geometries reflected by H-bonds have not been considered.
;
_vrf_PLAT919_tk212_brteg         
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check 
RESPONSE: ...
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'From the Melt'
