# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_p2
_database_code_depnum_ccdc_archive 'CCDC 1844709'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H8 F4 N2 O4 Pb'
_chemical_formula_weight         599.45

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.962(3)
_cell_length_b                   12.927(3)
_cell_length_c                   13.826(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.856(4)
_cell_angle_gamma                90
_cell_volume                     1728.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3134
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.303
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    9.831
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.096
_exptl_absorpt_correction_T_max  0.134
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMARTAPEX II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14622
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3939
_reflns_number_gt                3566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0270P)²]
 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         3939
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_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 0.69888(2) 0.46918(2) 0.04404(2) 0.02608(7) Uani 1 1 d . . . . .
F3 F 0.2600(4) -0.1011(3) 0.0908(2) 0.0620(10) Uani 1 1 d . . . . .
F1 F 0.3686(3) 0.1477(2) -0.1214(2) 0.0500(9) Uani 1 1 d . . . . .
F2 F 0.2454(4) -0.0311(3) -0.0943(3) 0.0644(11) Uani 1 1 d . . . . .
F4 F 0.5199(3) 0.1898(2) 0.2254(2) 0.0393(7) Uani 1 1 d . . . . .
O1 O 0.4283(4) 0.3410(3) -0.0189(3) 0.0426(9) Uani 1 1 d . . . . .
O2 O 0.6304(4) 0.2957(3) 0.0812(3) 0.0421(9) Uani 1 1 d . . . . .
O3 O 0.5097(4) -0.0107(3) 0.3266(3) 0.0438(10) Uani 1 1 d . . . . .
O4 O 0.2803(4) 0.0001(3) 0.2883(3) 0.0441(10) Uani 1 1 d . . . . .
N1 N 0.9223(4) 0.5817(3) 0.0979(3) 0.0289(9) Uani 1 1 d . . . . .
N2 N 0.9304(4) 0.3737(3) 0.1051(3) 0.0300(9) Uani 1 1 d . . . . .
C11 C 1.1723(6) 0.2650(5) 0.1798(4) 0.0469(15) Uani 1 1 d . . . . .
H11A H 1.2525 0.2286 0.2084 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3763(5) 0.1161(4) -0.0276(3) 0.0314(11) Uani 1 1 d . . . . .
C16 C 1.1497(6) 0.7060(5) 0.1728(4) 0.0469(15) Uani 1 1 d . . . . .
H16A H 1.2261 0.7473 0.1994 0.056 Uiso 1 1 calc R U . . .
C3 C 0.3143(6) 0.0245(4) -0.0143(4) 0.0370(13) Uani 1 1 d . . . . .
C8 C 0.5064(5) 0.2800(4) 0.0359(4) 0.0283(10) Uani 1 1 d . . . . .
C9 C 0.9330(5) 0.2697(4) 0.1061(4) 0.0383(12) Uani 1 1 d . . . . .
H9A H 0.8506 0.2345 0.0812 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3235(6) -0.0119(4) 0.0808(4) 0.0357(12) Uani 1 1 d . . . . .
C7 C 0.3981(6) 0.0066(4) 0.2688(4) 0.0318(11) Uani 1 1 d . . . . .
C1 C 0.4473(4) 0.1742(3) 0.0520(3) 0.0247(10) Uani 1 1 d . . . . .
C12 C 1.1743(5) 0.3702(5) 0.1752(4) 0.0399(13) Uani 1 1 d . . . . .
H12A H 1.2572 0.4059 0.1960 0.048 Uiso 1 1 calc R U . . .
C15 C 1.1620(5) 0.5987(5) 0.1737(4) 0.0404(13) Uani 1 1 d . . . . .
H15A H 1.2476 0.5678 0.1987 0.049 Uiso 1 1 calc R U . . .
C5 C 0.3942(5) 0.0420(3) 0.1634(4) 0.0279(10) Uani 1 1 d . . . . .
C6 C 0.4558(4) 0.1332(3) 0.1456(3) 0.0245(10) Uani 1 1 d . . . . .
C18 C 0.9124(5) 0.6850(4) 0.0958(4) 0.0378(12) Uani 1 1 d . . . . .
H18A H 0.8263 0.7142 0.0687 0.045 Uiso 1 1 calc R U . . .
C13 C 1.0518(5) 0.4239(4) 0.1393(3) 0.0283(10) Uani 1 1 d . . . . .
C14 C 1.0459(5) 0.5382(4) 0.1371(3) 0.0297(11) Uani 1 1 d . . . . .
C17 C 1.0221(6) 0.7506(4) 0.1315(4) 0.0445(14) Uani 1 1 d . . . . .
H17A H 1.0110 0.8220 0.1281 0.053 Uiso 1 1 calc R U . . .
C10 C 1.0502(6) 0.2127(5) 0.1417(4) 0.0448(14) Uani 1 1 d . . . . .
H10A H 1.0476 0.1408 0.1402 0.054 Uiso 1 1 calc R U . . .


_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 O4 2.312(4) 2_655 ?
Pb1 O2 2.435(3) . ?
Pb1 N2 2.573(4) . ?
Pb1 N1 2.613(4) . ?
Pb1 O1 2.745(4) 3_665 ?
F3 C4 1.338(5) . ?
F1 C2 1.344(5) . ?
F2 C3 1.360(6) . ?
F4 C6 1.350(5) . ?
O1 C8 1.234(6) . ?
O1 Pb1 2.745(4) 3_665 ?
O2 C8 1.260(6) . ?
O3 C7 1.224(6) . ?
O4 C7 1.269(6) . ?
O4 Pb1 2.312(4) 2_645 ?
N1 C18 1.339(6) . ?
N1 C14 1.345(6) . ?
N2 C9 1.345(6) . ?
N2 C13 1.354(6) . ?
C11 C12 1.362(7) . ?
C11 C10 1.381(8) . ?
C11 H11A 0.9300 . ?
C2 C3 1.367(7) . ?
C2 C1 1.379(6) . ?
C16 C17 1.388(8) . ?
C16 C15 1.392(8) . ?
C16 H16A 0.9300 . ?
C3 C4 1.379(7) . ?
C8 C1 1.526(6) . ?
C9 C10 1.368(7) . ?
C9 H9A 0.9300 . ?
C4 C5 1.378(7) . ?
C7 C5 1.520(7) . ?
C1 C6 1.383(6) . ?
C12 C13 1.388(6) . ?
C12 H12A 0.9300 . ?
C15 C14 1.388(7) . ?
C15 H15A 0.9300 . ?
C5 C6 1.378(6) . ?
C18 C17 1.377(7) . ?
C18 H18A 0.9300 . ?
C13 C14 1.478(7) . ?
C17 H17A 0.9300 . ?
C10 H10A 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
O4 Pb1 O2 84.83(13) 2_655 . ?
O4 Pb1 N2 84.00(13) 2_655 . ?
O2 Pb1 N2 76.31(12) . . ?
O4 Pb1 N1 75.67(12) 2_655 . ?
O2 Pb1 N1 135.65(12) . . ?
N2 Pb1 N1 62.49(13) . . ?
O4 Pb1 O1 84.27(13) 2_655 3_665 ?
O2 Pb1 O1 134.91(12) . 3_665 ?
N2 Pb1 O1 145.12(12) . 3_665 ?
N1 Pb1 O1 82.78(12) . 3_665 ?
C8 O1 Pb1 148.6(3) . 3_665 ?
C8 O2 Pb1 109.5(3) . . ?
C7 O4 Pb1 111.0(3) . 2_645 ?
C18 N1 C14 118.8(4) . . ?
C18 N1 Pb1 119.7(3) . . ?
C14 N1 Pb1 121.2(3) . . ?
C9 N2 C13 117.5(4) . . ?
C9 N2 Pb1 119.8(3) . . ?
C13 N2 Pb1 122.7(3) . . ?
C12 C11 C10 119.4(5) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
F1 C2 C3 118.0(4) . . ?
F1 C2 C1 120.3(4) . . ?
C3 C2 C1 121.7(4) . . ?
C17 C16 C15 119.2(5) . . ?
C17 C16 H16A 120.4 . . ?
C15 C16 H16A 120.4 . . ?
F2 C3 C2 120.3(5) . . ?
F2 C3 C4 120.0(5) . . ?
C2 C3 C4 119.7(5) . . ?
O1 C8 O2 127.0(4) . . ?
O1 C8 C1 117.0(4) . . ?
O2 C8 C1 116.0(4) . . ?
N2 C9 C10 123.7(5) . . ?
N2 C9 H9A 118.1 . . ?
C10 C9 H9A 118.1 . . ?
F3 C4 C5 120.7(5) . . ?
F3 C4 C3 117.9(5) . . ?
C5 C4 C3 121.4(5) . . ?
O3 C7 O4 126.3(5) . . ?
O3 C7 C5 119.4(5) . . ?
O4 C7 C5 114.2(4) . . ?
C2 C1 C6 116.3(4) . . ?
C2 C1 C8 120.9(4) . . ?
C6 C1 C8 122.7(4) . . ?
C11 C12 C13 119.7(5) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C14 C15 C16 119.7(5) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C6 C5 C4 116.5(4) . . ?
C6 C5 C7 121.2(4) . . ?
C4 C5 C7 122.2(4) . . ?
F4 C6 C5 117.5(4) . . ?
F4 C6 C1 117.9(4) . . ?
C5 C6 C1 124.4(4) . . ?
N1 C18 C17 123.9(5) . . ?
N1 C18 H18A 118.0 . . ?
C17 C18 H18A 118.0 . . ?
N2 C13 C12 121.3(5) . . ?
N2 C13 C14 116.4(4) . . ?
C12 C13 C14 122.3(4) . . ?
N1 C14 C15 120.9(5) . . ?
N1 C14 C13 117.0(4) . . ?
C15 C14 C13 122.1(4) . . ?
C18 C17 C16 117.5(5) . . ?
C18 C17 H17A 121.3 . . ?
C16 C17 H17A 121.3 . . ?
C9 C10 C11 118.2(5) . . ?
C9 C10 H10A 120.9 . . ?
C11 C10 H10A 120.9 . . ?

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
F1 C2 C3 F2 -1.0(8) . . . . ?
C1 C2 C3 F2 -179.8(5) . . . . ?
F1 C2 C3 C4 178.1(5) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
Pb1 O1 C8 O2 -56.9(9) 3_665 . . . ?
Pb1 O1 C8 C1 122.5(5) 3_665 . . . ?
Pb1 O2 C8 O1 -0.3(7) . . . . ?
Pb1 O2 C8 C1 -179.7(3) . . . . ?
C13 N2 C9 C10 1.6(8) . . . . ?
Pb1 N2 C9 C10 -176.8(4) . . . . ?
F2 C3 C4 F3 -1.7(8) . . . . ?
C2 C3 C4 F3 179.2(5) . . . . ?
F2 C3 C4 C5 179.1(5) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
Pb1 O4 C7 O3 6.7(7) 2_645 . . . ?
Pb1 O4 C7 C5 -171.7(3) 2_645 . . . ?
F1 C2 C1 C6 -176.8(4) . . . . ?
C3 C2 C1 C6 1.9(7) . . . . ?
F1 C2 C1 C8 5.9(7) . . . . ?
C3 C2 C1 C8 -175.3(5) . . . . ?
O1 C8 C1 C2 48.8(6) . . . . ?
O2 C8 C1 C2 -131.7(5) . . . . ?
O1 C8 C1 C6 -128.2(5) . . . . ?
O2 C8 C1 C6 51.2(6) . . . . ?
C10 C11 C12 C13 4.9(8) . . . . ?
C17 C16 C15 C14 -2.5(8) . . . . ?
F3 C4 C5 C6 -179.8(5) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
F3 C4 C5 C7 -3.0(8) . . . . ?
C3 C4 C5 C7 176.2(5) . . . . ?
O3 C7 C5 C6 -61.4(7) . . . . ?
O4 C7 C5 C6 117.1(5) . . . . ?
O3 C7 C5 C4 122.0(6) . . . . ?
O4 C7 C5 C4 -59.5(7) . . . . ?
C4 C5 C6 F4 176.9(4) . . . . ?
C7 C5 C6 F4 0.1(6) . . . . ?
C4 C5 C6 C1 2.0(7) . . . . ?
C7 C5 C6 C1 -174.8(4) . . . . ?
C2 C1 C6 F4 -177.5(4) . . . . ?
C8 C1 C6 F4 -0.3(6) . . . . ?
C2 C1 C6 C5 -2.7(7) . . . . ?
C8 C1 C6 C5 174.5(4) . . . . ?
C14 N1 C18 C17 0.2(8) . . . . ?
Pb1 N1 C18 C17 173.6(4) . . . . ?
C9 N2 C13 C12 -0.8(7) . . . . ?
Pb1 N2 C13 C12 177.6(3) . . . . ?
C9 N2 C13 C14 179.8(4) . . . . ?
Pb1 N2 C13 C14 -1.8(5) . . . . ?
C11 C12 C13 N2 -2.5(8) . . . . ?
C11 C12 C13 C14 176.9(5) . . . . ?
C18 N1 C14 C15 -0.9(7) . . . . ?
Pb1 N1 C14 C15 -174.2(3) . . . . ?
C18 N1 C14 C13 179.1(4) . . . . ?
Pb1 N1 C14 C13 5.8(5) . . . . ?
C16 C15 C14 N1 2.1(8) . . . . ?
C16 C15 C14 C13 -177.9(5) . . . . ?
N2 C13 C14 N1 -2.7(6) . . . . ?
C12 C13 C14 N1 178.0(4) . . . . ?
N2 C13 C14 C15 177.4(4) . . . . ?
C12 C13 C14 C15 -2.0(7) . . . . ?
N1 C18 C17 C16 -0.7(8) . . . . ?
C15 C16 C17 C18 1.8(8) . . . . ?
N2 C9 C10 C11 0.8(8) . . . . ?
C12 C11 C10 C9 -4.1(8) . . . . ?

_refine_diff_density_max         0.615
_refine_diff_density_min         -1.411
_refine_diff_density_rms         0.171

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_p222
_database_code_depnum_ccdc_archive 'CCDC 1844712'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 F4 N2 O4 Pb'
_chemical_formula_weight         641.54

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'
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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.211(2)
_cell_length_b                   15.947(4)
_cell_length_c                   27.262(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4004.5(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3631
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_F_000             4520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    8.496
_shelx_estimated_absorpt_T_min   0.158
_shelx_estimated_absorpt_T_max   0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.093
_exptl_absorpt_correction_T_max  0.168
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMARTAPEX II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29421
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.959
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4484
_reflns_number_gt                3823
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0409P)²+6.7477P]
 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         4484
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_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 0.84437(2) 0.18645(2) 0.74381(2) 0.03174(8) Uani 1 1 d . . . . .
C1 C 0.8743(6) 0.1405(4) 0.8664(2) 0.0433(13) Uani 1 1 d . . . . .
H1 H 0.9633 0.1649 0.8589 0.052 Uiso 1 1 calc R U . . .
C2 C 0.8384(6) 0.1303(4) 0.9149(2) 0.0454(14) Uani 1 1 d . . . . .
H2 H 0.9032 0.1464 0.9393 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7051(6) 0.0959(3) 0.9274(2) 0.0389(12) Uani 1 1 d . . . . .
C4 C 0.6167(7) 0.0714(4) 0.8887(2) 0.0432(13) Uani 1 1 d . . . . .
H4 H 0.5263 0.0480 0.8952 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6605(6) 0.0814(4) 0.8410(2) 0.0409(13) Uani 1 1 d . . . . .
H5 H 0.6001 0.0628 0.8159 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6545(7) 0.0918(4) 0.9799(2) 0.0541(16) Uani 1 1 d . . . . .
H6A H 0.7361 0.1015 1.0016 0.065 Uiso 1 1 calc R U . . .
H6B H 0.6164 0.0362 0.9867 0.065 Uiso 1 1 calc R U . . .
C7 C 0.5370(8) 0.1571(5) 0.9896(2) 0.0638(19) Uani 1 1 d . . . . .
H7A H 0.5763 0.2121 0.9823 0.077 Uiso 1 1 calc R U . . .
H7B H 0.4571 0.1472 0.9672 0.077 Uiso 1 1 calc R U . . .
C8 C 0.4780(8) 0.1580(5) 1.0411(3) 0.068(2) Uani 1 1 d . . . . .
H8A H 0.4408 0.1025 1.0484 0.081 Uiso 1 1 calc R U . . .
H8B H 0.3964 0.1964 1.0420 0.081 Uiso 1 1 calc R U . . .
C9 C 0.5818(7) 0.1825(4) 1.0818(2) 0.0477(15) Uani 1 1 d . . . . .
C10 C 0.6853(8) 0.2451(4) 1.0771(2) 0.0569(17) Uani 1 1 d . . . . .
H10 H 0.7013 0.2704 1.0468 0.068 Uiso 1 1 calc R U . . .
C11 C 0.7650(7) 0.2699(4) 1.1178(2) 0.0503(15) Uani 1 1 d . . . . .
H11 H 0.8338 0.3121 1.1141 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6512(8) 0.1742(4) 1.1653(3) 0.0522(16) Uani 1 1 d . . . . .
H12 H 0.6395 0.1481 1.1956 0.063 Uiso 1 1 calc R U . . .
C13 C 0.5685(8) 0.1469(4) 1.1268(2) 0.0571(18) Uani 1 1 d . . . . .
H13 H 0.5026 0.1034 1.1314 0.069 Uiso 1 1 calc R U . . .
C14 C 0.5884(6) 0.3763(3) 0.8281(2) 0.0341(12) Uani 1 1 d . . . . .
C15 C 0.5794(7) 0.3669(4) 0.8777(2) 0.0444(14) Uani 1 1 d . . . . .
C16 C 0.4869(7) 0.4153(4) 0.9062(2) 0.0485(15) Uani 1 1 d . . . . .
C17 C 0.4012(6) 0.4739(4) 0.8836(2) 0.0406(13) Uani 1 1 d . . . . .
C18 C 0.4047(6) 0.4875(3) 0.83350(19) 0.0342(11) Uani 1 1 d . . . . .
C19 C 0.5011(5) 0.4381(3) 0.80735(18) 0.0329(11) Uani 1 1 d . . . . .
C20 C 0.6864(6) 0.3199(3) 0.7975(2) 0.0375(12) Uani 1 1 d . . . . .
C21 C 0.3091(6) 0.5527(3) 0.80923(19) 0.0351(11) Uani 1 1 d . . . . .
N1 N 0.7885(5) 0.1172(3) 0.82937(16) 0.0397(10) Uani 1 1 d . . . . .
N2 N 0.7473(5) 0.2360(3) 1.16183(18) 0.0440(11) Uani 1 1 d . . . . .
O1A O 0.821(3) 0.3241(15) 0.8059(9) 0.062(6) Uani 0.5 1 d . . P A 2
O1B O 0.810(3) 0.3442(14) 0.7888(8) 0.054(5) Uani 0.5 1 d . . P A 1
O2 O 0.6287(4) 0.2596(3) 0.77593(17) 0.0457(10) Uani 1 1 d . . . . .
O3 O 0.3680(4) 0.6017(2) 0.77858(15) 0.0412(9) Uani 1 1 d . . . . .
O4 O 0.1800(4) 0.5548(3) 0.82113(17) 0.0511(11) Uani 1 1 d . . . . .
F1 F 0.3128(4) 0.5205(2) 0.91263(13) 0.0628(10) Uani 1 1 d . . . . .
F2 F 0.6595(5) 0.3076(3) 0.90046(17) 0.0688(12) Uani 1 1 d . . . . .
F3 F 0.5143(4) 0.4496(2) 0.75880(11) 0.0518(9) Uani 1 1 d . . . . .
F4 F 0.4843(5) 0.4052(3) 0.95565(14) 0.0805(13) 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
Pb1 O3 2.455(4) 3_646 ?
Pb1 O2 2.464(4) . ?
Pb1 N1 2.632(4) . ?
Pb1 N2 2.706(5) 7_565 ?
Pb1 O4 2.756(4) 3_646 ?
C1 N1 1.334(7) . ?
C1 C2 1.372(8) . ?
C2 C3 1.387(8) . ?
C3 C4 1.389(8) . ?
C3 C6 1.506(8) . ?
C4 C5 1.370(8) . ?
C5 N1 1.348(7) . ?
C6 C7 1.525(9) . ?
C7 C8 1.506(9) . ?
C8 C9 1.514(9) . ?
C9 C13 1.357(9) . ?
C9 C10 1.387(9) . ?
C10 C11 1.389(9) . ?
C11 N2 1.325(7) . ?
C12 N2 1.328(8) . ?
C12 C13 1.370(9) . ?
C14 C15 1.365(8) . ?
C14 C19 1.392(7) . ?
C14 C20 1.522(7) . ?
C15 F2 1.349(7) . ?
C15 C16 1.388(9) . ?
C16 F4 1.357(7) . ?
C16 C17 1.370(8) . ?
C17 F1 1.358(6) . ?
C17 C18 1.383(8) . ?
C18 C19 1.384(7) . ?
C18 C21 1.515(7) . ?
C19 F3 1.342(6) . ?
C20 O1B 1.23(3) . ?
C20 O2 1.246(7) . ?
C20 O1A 1.27(3) . ?
C21 O4 1.233(7) . ?
C21 O3 1.266(6) . ?
N2 Pb1 2.706(5) 7_566 ?
O3 Pb1 2.455(4) 3_656 ?
O4 Pb1 2.756(4) 3_656 ?

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
O3 Pb1 O2 72.94(13) 3_646 . ?
O3 Pb1 N1 80.41(14) 3_646 . ?
O2 Pb1 N1 74.10(15) . . ?
O3 Pb1 N2 77.45(14) 3_646 7_565 ?
O2 Pb1 N2 79.10(15) . 7_565 ?
N1 Pb1 N2 149.21(15) . 7_565 ?
O3 Pb1 O4 49.90(12) 3_646 3_646 ?
O2 Pb1 O4 121.56(13) . 3_646 ?
N1 Pb1 O4 103.51(14) . 3_646 ?
N2 Pb1 O4 77.91(14) 7_565 3_646 ?
N1 C1 C2 123.5(5) . . ?
C1 C2 C3 119.8(5) . . ?
C2 C3 C4 116.3(5) . . ?
C2 C3 C6 121.7(5) . . ?
C4 C3 C6 121.8(5) . . ?
C5 C4 C3 121.0(5) . . ?
N1 C5 C4 122.0(5) . . ?
C3 C6 C7 110.8(5) . . ?
C8 C7 C6 115.2(6) . . ?
C7 C8 C9 117.2(6) . . ?
C13 C9 C10 116.5(6) . . ?
C13 C9 C8 119.8(6) . . ?
C10 C9 C8 123.5(6) . . ?
C9 C10 C11 119.7(6) . . ?
N2 C11 C10 122.8(6) . . ?
N2 C12 C13 123.5(6) . . ?
C9 C13 C12 120.7(6) . . ?
C15 C14 C19 116.4(5) . . ?
C15 C14 C20 120.9(5) . . ?
C19 C14 C20 122.6(5) . . ?
F2 C15 C14 119.9(5) . . ?
F2 C15 C16 117.9(5) . . ?
C14 C15 C16 122.1(5) . . ?
F4 C16 C17 121.3(6) . . ?
F4 C16 C15 120.0(5) . . ?
C17 C16 C15 118.7(5) . . ?
F1 C17 C16 117.1(5) . . ?
F1 C17 C18 120.2(5) . . ?
C16 C17 C18 122.6(5) . . ?
C17 C18 C19 115.7(5) . . ?
C17 C18 C21 121.7(5) . . ?
C19 C18 C21 122.6(5) . . ?
F3 C19 C18 119.3(4) . . ?
F3 C19 C14 116.4(4) . . ?
C18 C19 C14 124.4(5) . . ?
O1B C20 O2 123.3(14) . . ?
O2 C20 O1A 123.0(14) . . ?
O1B C20 C14 118.0(13) . . ?
O2 C20 C14 117.5(5) . . ?
O1A C20 C14 116.9(14) . . ?
O4 C21 O3 124.8(5) . . ?
O4 C21 C18 117.6(5) . . ?
O3 C21 C18 117.6(5) . . ?
C1 N1 C5 117.2(5) . . ?
C1 N1 Pb1 115.9(4) . . ?
C5 N1 Pb1 123.9(4) . . ?
C11 N2 C12 116.7(6) . . ?
C11 N2 Pb1 121.4(4) . 7_566 ?
C12 N2 Pb1 120.0(4) . 7_566 ?
C20 O2 Pb1 100.9(3) . . ?
C21 O3 Pb1 99.3(3) . 3_656 ?
C21 O4 Pb1 86.0(3) . 3_656 ?

_refine_diff_density_max         1.989
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.115

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_pc
_database_code_depnum_ccdc_archive 'CCDC 1844710'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H8 F4 N2 O4 Pb'
_chemical_formula_weight         623.47

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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   8.3379(13)
_cell_length_b                   12.8358(12)
_cell_length_c                   8.7757(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.116(10)
_cell_angle_gamma                90
_cell_volume                     914.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3097
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.264
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    9.295
_shelx_estimated_absorpt_T_min   0.214
_shelx_estimated_absorpt_T_max   0.318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.117
_exptl_absorpt_correction_T_max  0.236
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMARTAPEX II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6965
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.174
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2097
_reflns_number_gt                1974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0187P)²+1.0949P]
 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         2097
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0525
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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 1.0000 0.01339(2) 0.2500 0.03631(9) Uani 1 2 d S T P . .
C1 C 0.5000 0.1218(4) 0.2500 0.0387(13) Uani 1 2 d S T P . .
C2 C 0.6135(5) 0.1717(3) 0.3676(5) 0.0346(9) Uani 1 1 d . . . . .
C3 C 0.6076(5) 0.2789(3) 0.3644(6) 0.0485(11) Uani 1 1 d . . . . .
C4 C 0.5000 0.3328(5) 0.2500 0.059(2) Uani 1 2 d S T P . .
C5 C 0.7339(5) 0.1131(4) 0.4939(5) 0.0437(10) Uani 1 1 d . . . . .
C6 C 0.7653(6) 0.1867(4) -0.0178(5) 0.0519(12) Uani 1 1 d . . . . .
H6 H 0.7230 0.1237 -0.0614 0.062 Uiso 1 1 calc R U . . .
C7 C 0.7078(7) 0.2793(4) -0.0963(6) 0.0689(16) Uani 1 1 d . . . . .
H7 H 0.6332 0.2768 -0.1927 0.083 Uiso 1 1 calc R U . . .
C8 C 0.7608(7) 0.3715(4) -0.0318(7) 0.0696(16) Uani 1 1 d . . . . .
H8 H 0.7189 0.4331 -0.0809 0.083 Uiso 1 1 calc R U . . .
C9 C 0.8796(6) 0.3747(4) 0.1098(6) 0.0532(12) Uani 1 1 d . . . . .
C10 C 0.9369(5) 0.2784(3) 0.1781(5) 0.0407(9) Uani 1 1 d . . . . .
C11 C 0.9426(8) 0.4699(4) 0.1833(8) 0.0725(16) Uani 1 1 d . . . . .
H11 H 0.9031 0.5329 0.1376 0.087 Uiso 1 1 calc R U . . .
F1 F 0.5000 0.0177(3) 0.2500 0.0730(14) Uani 1 2 d S T P . .
F2 F 0.7133(4) 0.3342(2) 0.4731(4) 0.0809(10) Uani 1 1 d . . . . .
F3A F 0.493(6) 0.428(5) 0.283(3) 0.069(8) Uani 0.25 1 d . . P A 2
F3B F 0.510(6) 0.449(5) 0.222(3) 0.069(8) Uani 0.25 1 d . . P A 1
N1 N 0.8775(4) 0.1856(3) 0.1159(4) 0.0408(8) Uani 1 1 d . . . . .
O1 O 0.7284(6) 0.1289(4) 0.6303(4) 0.0993(16) Uani 1 1 d . . . . .
O3 O 0.8333(4) 0.0529(3) 0.4507(3) 0.0490(7) 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
Pb1 O3 2.530(3) 2_755 ?
Pb1 O3 2.530(3) . ?
Pb1 N1 2.601(3) 2_755 ?
Pb1 N1 2.601(3) . ?
C1 F1 1.337(6) . ?
C1 C2 1.388(4) . ?
C1 C2 1.388(4) 2_655 ?
C2 C3 1.377(6) . ?
C2 C5 1.515(5) . ?
C3 F2 1.345(5) . ?
C3 C4 1.372(5) . ?
C4 F3A 1.26(6) 2_655 ?
C4 F3A 1.26(6) . ?
C4 C3 1.372(5) 2_655 ?
C4 F3B 1.52(6) . ?
C4 F3B 1.52(6) 2_655 ?
C5 O1 1.226(5) . ?
C5 O3 1.253(5) . ?
C6 N1 1.324(5) . ?
C6 C7 1.402(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.343(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(6) . ?
C9 C11 1.425(7) . ?
C10 N1 1.357(5) . ?
C10 C10 1.448(8) 2_755 ?
C11 C11 1.333(12) 2_755 ?
C11 H11 0.9300 . ?
F3A F3A 0.62(6) 2_655 ?
F3B F3B 0.56(6) 2_655 ?

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
O3 Pb1 O3 156.85(15) 2_755 . ?
O3 Pb1 N1 85.60(10) 2_755 2_755 ?
O3 Pb1 N1 74.68(11) . 2_755 ?
O3 Pb1 N1 74.68(11) 2_755 . ?
O3 Pb1 N1 85.60(10) . . ?
N1 Pb1 N1 63.66(15) 2_755 . ?
F1 C1 C2 117.5(2) . . ?
F1 C1 C2 117.5(2) . 2_655 ?
C2 C1 C2 125.1(5) . 2_655 ?
C3 C2 C1 115.5(4) . . ?
C3 C2 C5 121.7(4) . . ?
C1 C2 C5 122.8(4) . . ?
F2 C3 C4 117.8(4) . . ?
F2 C3 C2 119.9(4) . . ?
C4 C3 C2 122.2(4) . . ?
F3A C4 F3A 28(3) 2_655 . ?
F3A C4 C3 112.3(15) 2_655 2_655 ?
F3A C4 C3 126.7(17) . 2_655 ?
F3A C4 C3 126.8(17) 2_655 . ?
F3A C4 C3 112.3(15) . . ?
C3 C4 C3 119.5(6) 2_655 . ?
C3 C4 F3B 115.3(14) 2_655 . ?
C3 C4 F3B 124.3(16) . . ?
C3 C4 F3B 124.3(16) 2_655 2_655 ?
C3 C4 F3B 115.3(14) . 2_655 ?
F3B C4 F3B 21(2) . 2_655 ?
O1 C5 O3 124.8(4) . . ?
O1 C5 C2 117.8(4) . . ?
O3 C5 C2 117.3(4) . . ?
N1 C6 C7 122.6(5) . . ?
N1 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 119.9(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 117.0(5) . . ?
C8 C9 C11 122.7(5) . . ?
C10 C9 C11 120.3(4) . . ?
N1 C10 C9 122.8(4) . . ?
N1 C10 C10 118.5(2) . 2_755 ?
C9 C10 C10 118.7(3) . 2_755 ?
C11 C11 C9 121.0(3) 2_755 . ?
C11 C11 H11 119.5 2_755 . ?
C9 C11 H11 119.5 . . ?
F3A F3A C4 75.8(13) 2_655 . ?
F3B F3B C4 79.4(12) 2_655 . ?
C6 N1 C10 117.8(4) . . ?
C6 N1 Pb1 122.4(3) . . ?
C10 N1 Pb1 119.6(3) . . ?
C5 O3 Pb1 147.1(3) . . ?

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
F1 C1 C2 C3 -179.1(3) . . . . ?
C2 C1 C2 C3 0.9(3) 2_655 . . . ?
F1 C1 C2 C5 -0.5(4) . . . . ?
C2 C1 C2 C5 179.5(4) 2_655 . . . ?
C1 C2 C3 F2 -179.7(4) . . . . ?
C5 C2 C3 F2 1.6(7) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C5 C2 C3 C4 179.5(4) . . . . ?
F2 C3 C4 F3A 14(2) . . . 2_655 ?
C2 C3 C4 F3A -164(2) . . . 2_655 ?
F2 C3 C4 F3A -14(2) . . . . ?
C2 C3 C4 F3A 168(2) . . . . ?
F2 C3 C4 C3 178.9(5) . . . 2_655 ?
C2 C3 C4 C3 1.0(3) . . . 2_655 ?
F2 C3 C4 F3B 10.5(18) . . . . ?
C2 C3 C4 F3B -167.4(18) . . . . ?
F2 C3 C4 F3B -11.7(19) . . . 2_655 ?
C2 C3 C4 F3B 170.4(18) . . . 2_655 ?
C3 C2 C5 O1 57.9(7) . . . . ?
C1 C2 C5 O1 -120.7(5) . . . . ?
C3 C2 C5 O3 -121.2(5) . . . . ?
C1 C2 C5 O3 60.2(5) . . . . ?
N1 C6 C7 C8 -3.4(9) . . . . ?
C6 C7 C8 C9 3.2(9) . . . . ?
C7 C8 C9 C10 -0.4(9) . . . . ?
C7 C8 C9 C11 179.1(6) . . . . ?
C8 C9 C10 N1 -2.6(7) . . . . ?
C11 C9 C10 N1 177.8(5) . . . . ?
C8 C9 C10 C10 178.2(5) . . . 2_755 ?
C11 C9 C10 C10 -1.3(8) . . . 2_755 ?
C8 C9 C11 C11 -178.9(8) . . . 2_755 ?
C10 C9 C11 C11 0.6(12) . . . 2_755 ?
C3 C4 F3A F3A -67(9) 2_655 . . 2_655 ?
C3 C4 F3A F3A 127(7) . . . 2_655 ?
F3B C4 F3A F3A 2(5) . . . 2_655 ?
F3B C4 F3A F3A -16(31) 2_655 . . 2_655 ?
F3A C4 F3B F3B 158(41) 2_655 . . 2_655 ?
F3A C4 F3B F3B -3(6) . . . 2_655 ?
C3 C4 F3B F3B 120(9) 2_655 . . 2_655 ?
C3 C4 F3B F3B -71(10) . . . 2_655 ?
C7 C6 N1 C10 0.4(7) . . . . ?
C7 C6 N1 Pb1 -175.2(4) . . . . ?
C9 C10 N1 C6 2.6(7) . . . . ?
C10 C10 N1 C6 -178.3(5) 2_755 . . . ?
C9 C10 N1 Pb1 178.4(3) . . . . ?
C10 C10 N1 Pb1 -2.5(6) 2_755 . . . ?
O1 C5 O3 Pb1 -149.0(5) . . . . ?
C2 C5 O3 Pb1 30.1(7) . . . . ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.116

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_p1
_database_code_depnum_ccdc_archive 'CCDC 1844711'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H F4 N O5 Pb'
_chemical_formula_weight         534.34

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'
F F 0.0171 0.0103 '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                   7.722(2)
_cell_length_b                   8.4029(19)
_cell_length_c                   12.016(3)
_cell_angle_alpha                93.629(3)
_cell_angle_beta                 103.750(9)
_cell_angle_gamma                106.323(11)
_cell_volume                     719.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3576
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      27.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.466
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    11.793
_shelx_estimated_absorpt_T_min   0.164
_shelx_estimated_absorpt_T_max   0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.093
_exptl_absorpt_correction_T_max  0.177
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMARTAPEX II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8198
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3274
_reflns_number_gt                2830
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0381P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3274
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.41749(4) 1.21757(3) 0.96129(3) 0.02988(12) Uani 1 1 d . . . . .
C1 C 0.1918(11) 0.8430(9) 1.1972(7) 0.0281(17) Uani 1 1 d . . . . .
C2 C 0.0517(10) 0.7049(9) 1.1374(7) 0.0259(16) Uani 1 1 d . . . . .
C3 C -0.0515(11) 0.5772(9) 1.1876(7) 0.0294(17) Uani 1 1 d . . . . .
C4 C 0.0062(13) 0.5945(10) 1.3062(8) 0.039(2) Uani 1 1 d . . . . .
C5 C 0.1475(14) 0.7303(11) 1.3711(8) 0.042(2) Uani 1 1 d . . . . .
C6 C 0.2368(13) 0.8522(10) 1.3169(7) 0.037(2) Uani 1 1 d . . . . .
C7 C 0.2829(11) 0.9811(9) 1.1355(7) 0.0277(17) Uani 1 1 d . . . . .
C8 C -0.2241(10) 0.4423(10) 1.1171(7) 0.0302(18) Uani 1 1 d . . . . .
C9 C 0.5770(15) 1.4855(11) 0.7616(8) 0.045(2) Uani 1 1 d . . . . .
H9 H 0.6507 1.5472 0.8324 0.054 Uiso 1 1 calc R U . . .
C10 C 0.5976(14) 1.5533(10) 0.6626(8) 0.043(2) Uani 1 1 d . . . . .
H10 H 0.6833 1.6583 0.6679 0.052 Uiso 1 1 calc R U . . .
C11 C 0.4924(12) 1.4669(9) 0.5559(7) 0.0310(18) Uani 1 1 d . . . . .
C12 C 0.3649(14) 1.3117(11) 0.5557(8) 0.049(2) Uani 1 1 d . . . . .
H12 H 0.2889 1.2484 0.4860 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3511(14) 1.2521(11) 0.6583(8) 0.047(2) Uani 1 1 d . . . . .
H13 H 0.2642 1.1488 0.6559 0.056 Uiso 1 1 calc R U . . .
O1 O 0.4046(8) 0.9610(6) 1.0890(5) 0.0381(14) Uani 1 1 d . . . . .
O2 O 0.2269(9) 1.1078(7) 1.1356(6) 0.0469(17) Uani 1 1 d . . . . .
O3 O -0.3168(8) 0.4823(7) 1.0274(5) 0.0402(15) Uani 1 1 d . . . . .
O4 O -0.2676(8) 0.3027(7) 1.1431(5) 0.0397(14) Uani 1 1 d . . . . .
O5 O 0.1306(10) 0.9632(9) 0.8088(8) 0.056(2) Uani 1 1 d D . . . .
F1 F 0.0041(7) 0.6980(6) 1.0212(4) 0.0432(12) Uani 1 1 d . . . . .
F2 F -0.0812(9) 0.4804(7) 1.3641(5) 0.0632(17) Uani 1 1 d . . . . .
F3 F 0.1963(10) 0.7444(8) 1.4884(5) 0.077(2) Uani 1 1 d . . . . .
F4 F 0.3749(8) 0.9886(6) 1.3810(5) 0.0589(16) Uani 1 1 d . . . . .
H5A H 0.028(17) 0.940(15) 0.819(11) 0.071 Uiso 1 1 d . U . . .
H5B H 0.054(14) 0.931(14) 0.745(5) 0.071 Uiso 1 1 d D U . . .
N1 N 0.4579(11) 1.3370(9) 0.7618(6) 0.0401(18) 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
Pb1 O1 2.437(6) 2_677 ?
Pb1 O3 2.495(5) 1_665 ?
Pb1 N1 2.708(7) . ?
Pb1 O1 2.717(5) . ?
Pb1 O4 2.738(6) 1_665 ?
C1 C2 1.362(11) . ?
C1 C6 1.388(11) . ?
C1 C7 1.514(10) . ?
C2 F1 1.350(8) . ?
C2 C3 1.408(10) . ?
C3 C4 1.373(12) . ?
C3 C8 1.507(11) . ?
C4 F2 1.343(9) . ?
C4 C5 1.372(13) . ?
C5 F3 1.357(10) . ?
C5 C6 1.360(12) . ?
C6 F4 1.363(9) . ?
C7 O1 1.246(9) . ?
C7 O2 1.256(9) . ?
C8 O4 1.209(9) . ?
C8 O3 1.265(10) . ?
C9 N1 1.327(11) . ?
C9 C10 1.374(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(12) . ?
C11 C11 1.504(15) 2_686 ?
C12 C13 1.375(12) . ?
C12 H12 0.9300 . ?
C13 N1 1.344(11) . ?
C13 H13 0.9300 . ?
O1 Pb1 2.437(6) 2_677 ?
O3 Pb1 2.495(5) 1_445 ?
O4 Pb1 2.738(6) 1_445 ?
O5 H5A 0.80(11) . ?
O5 H5B 0.82(2) . ?

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 O3 97.54(19) 2_677 1_665 ?
O1 Pb1 N1 83.5(2) 2_677 . ?
O3 Pb1 N1 76.4(2) 1_665 . ?
O1 Pb1 O1 67.7(2) 2_677 . ?
O3 Pb1 O1 119.25(19) 1_665 . ?
N1 Pb1 O1 148.13(19) . . ?
O1 Pb1 O4 76.41(19) 2_677 1_665 ?
O3 Pb1 O4 48.62(18) 1_665 1_665 ?
N1 Pb1 O4 116.6(2) . 1_665 ?
O1 Pb1 O4 70.74(17) . 1_665 ?
C2 C1 C6 115.9(7) . . ?
C2 C1 C7 121.1(7) . . ?
C6 C1 C7 123.0(7) . . ?
F1 C2 C1 115.9(6) . . ?
F1 C2 C3 118.8(7) . . ?
C1 C2 C3 125.1(7) . . ?
C4 C3 C2 114.9(7) . . ?
C4 C3 C8 122.8(7) . . ?
C2 C3 C8 122.1(7) . . ?
F2 C4 C5 117.0(8) . . ?
F2 C4 C3 120.4(8) . . ?
C5 C4 C3 122.6(8) . . ?
F3 C5 C6 120.2(8) . . ?
F3 C5 C4 120.5(8) . . ?
C6 C5 C4 119.3(8) . . ?
C5 C6 F4 119.5(8) . . ?
C5 C6 C1 122.2(8) . . ?
F4 C6 C1 118.3(7) . . ?
O1 C7 O2 125.5(7) . . ?
O1 C7 C1 118.5(6) . . ?
O2 C7 C1 116.0(7) . . ?
O4 C8 O3 122.2(7) . . ?
O4 C8 C3 121.7(8) . . ?
O3 C8 C3 116.1(7) . . ?
N1 C9 C10 123.7(9) . . ?
N1 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C11 C10 C9 120.4(8) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 116.1(7) . . ?
C10 C11 C11 123.3(9) . 2_686 ?
C12 C11 C11 120.5(9) . 2_686 ?
C13 C12 C11 120.3(8) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N1 C13 C12 122.7(8) . . ?
N1 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C7 O1 Pb1 149.0(5) . 2_677 ?
C7 O1 Pb1 97.4(5) . . ?
Pb1 O1 Pb1 112.3(2) 2_677 . ?
C8 O3 Pb1 99.6(5) . 1_445 ?
C8 O4 Pb1 89.3(5) . 1_445 ?
H5A O5 H5B 72(10) . . ?
C9 N1 C13 116.7(8) . . ?
C9 N1 Pb1 121.8(6) . . ?
C13 N1 Pb1 121.4(6) . . ?

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
C6 C1 C2 F1 178.2(7) . . . . ?
C7 C1 C2 F1 1.6(11) . . . . ?
C6 C1 C2 C3 2.1(12) . . . . ?
C7 C1 C2 C3 -174.5(7) . . . . ?
F1 C2 C3 C4 -179.8(7) . . . . ?
C1 C2 C3 C4 -3.8(12) . . . . ?
F1 C2 C3 C8 -5.9(11) . . . . ?
C1 C2 C3 C8 170.1(7) . . . . ?
C2 C3 C4 F2 -179.9(8) . . . . ?
C8 C3 C4 F2 6.2(13) . . . . ?
C2 C3 C4 C5 3.1(13) . . . . ?
C8 C3 C4 C5 -170.8(8) . . . . ?
F2 C4 C5 F3 1.1(14) . . . . ?
C3 C4 C5 F3 178.1(9) . . . . ?
F2 C4 C5 C6 -178.0(8) . . . . ?
C3 C4 C5 C6 -0.9(14) . . . . ?
F3 C5 C6 F4 -0.2(14) . . . . ?
C4 C5 C6 F4 178.9(8) . . . . ?
F3 C5 C6 C1 179.9(8) . . . . ?
C4 C5 C6 C1 -1.0(14) . . . . ?
C2 C1 C6 C5 0.5(13) . . . . ?
C7 C1 C6 C5 177.0(8) . . . . ?
C2 C1 C6 F4 -179.4(7) . . . . ?
C7 C1 C6 F4 -2.9(12) . . . . ?
C2 C1 C7 O1 -80.0(10) . . . . ?
C6 C1 C7 O1 103.7(9) . . . . ?
C2 C1 C7 O2 99.8(9) . . . . ?
C6 C1 C7 O2 -76.6(11) . . . . ?
C4 C3 C8 O4 -37.7(12) . . . . ?
C2 C3 C8 O4 148.9(8) . . . . ?
C4 C3 C8 O3 144.5(8) . . . . ?
C2 C3 C8 O3 -29.0(11) . . . . ?
N1 C9 C10 C11 -0.2(15) . . . . ?
C9 C10 C11 C12 1.1(14) . . . . ?
C9 C10 C11 C11 -180.0(10) . . . 2_686 ?
C10 C11 C12 C13 -0.8(14) . . . . ?
C11 C11 C12 C13 -179.7(10) 2_686 . . . ?
C11 C12 C13 N1 -0.6(16) . . . . ?
O2 C7 O1 Pb1 -176.6(7) . . . 2_677 ?
C1 C7 O1 Pb1 3.2(15) . . . 2_677 ?
O2 C7 O1 Pb1 -13.1(9) . . . . ?
C1 C7 O1 Pb1 166.6(6) . . . . ?
O4 C8 O3 Pb1 5.3(9) . . . 1_445 ?
C3 C8 O3 Pb1 -176.9(6) . . . 1_445 ?
O3 C8 O4 Pb1 -4.7(8) . . . 1_445 ?
C3 C8 O4 Pb1 177.6(7) . . . 1_445 ?
C10 C9 N1 C13 -1.1(14) . . . . ?
C10 C9 N1 Pb1 -177.8(7) . . . . ?
C12 C13 N1 C9 1.5(14) . . . . ?
C12 C13 N1 Pb1 178.2(8) . . . . ?

_refine_diff_density_max         1.740
_refine_diff_density_min         -1.478
_refine_diff_density_rms         0.211

_shelxl_version_number           2013-2

