# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_C:\CRYSTA~1\15c29\prr29
_database_code_depnum_ccdc_archive 'CCDC 1416616'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2015-08-21 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         'C14 H13 N O5 Pb'
_chemical_formula_sum            'C14 H13 N O5 Pb'
_chemical_formula_weight         482.44

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'
Pb Pb -3.3944 10.1111 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

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

_cell_length_a                   19.0391(2)
_cell_length_b                   19.0391(2)
_cell_length_c                   8.0073(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2902.55(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6022
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.8510
_cell_measurement_theta_min      3.4700

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.208
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_coefficient_mu    11.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1468
_diffrn_detector_type            EosS2
_diffrn_reflns_number            16891
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.325
_diffrn_reflns_theta_max         29.484
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3585
_reflns_number_gt                3182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    1.000

_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'POV-Ray, version 3.6, 2004'
_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)+(0.0136P)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_abs_structure_details 
;
 Flack x determined using 1224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3585
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0430
_refine_ls_wR_factor_gt          0.0409
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.83598(2) 0.35869(2) -0.01692(3) 0.01447(7) Uani 1 1 d . . . . .
O1 O 0.7166(2) 0.3027(2) 0.0183(6) 0.0272(11) Uani 1 1 d . . . . .
O2 O 0.7639(3) 0.3555(3) 0.2358(5) 0.0210(12) Uani 1 1 d . . . . .
O3 O 0.4652(3) 0.2285(3) 0.0598(5) 0.0290(13) Uani 1 1 d . . . . .
O4 O 0.4095(3) 0.2299(3) 0.3018(6) 0.0237(12) Uani 1 1 d . . . . .
O5 O 0.8889(3) 0.4505(3) 0.2058(7) 0.0356(15) Uani 1 1 d . . . . .
C2 C 0.6473(4) 0.3137(4) 0.2650(8) 0.0184(16) Uani 1 1 d . . . . .
C8 C 0.6445(4) 0.3372(4) 0.4305(7) 0.0230(16) Uani 1 1 d . . . . .
H8 H 0.6857 0.3561 0.4801 0.028 Uiso 1 1 calc R U . . .
C1 C 0.7127(4) 0.3233(4) 0.1657(8) 0.0175(16) Uani 1 1 d . . . . .
C12 C 0.8507(5) 0.5019(5) 0.2261(9) 0.031(2) Uani 1 1 d . . . . .
H12 H 0.8019 0.4929 0.2390 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4618(4) 0.2436(4) 0.2125(9) 0.0181(17) Uani 1 1 d . . . . .
C3 C 0.5868(4) 0.2856(4) 0.1943(9) 0.0200(17) Uani 1 1 d . . . . .
H3 H 0.5873 0.2711 0.0808 0.024 Uiso 1 1 calc R U . . .
N1 N 0.8707(4) 0.5683(4) 0.2317(10) 0.044(2) Uani 1 1 d . . . . .
C4 C 0.5249(4) 0.2784(4) 0.2888(8) 0.0211(17) Uani 1 1 d . . . . .
C14 C 0.8215(6) 0.6256(5) 0.2505(10) 0.047(3) Uani 1 1 d . . . . .
H14A H 0.7735 0.6077 0.2397 0.071 Uiso 1 1 calc R U . . .
H14B H 0.8302 0.6609 0.1639 0.071 Uiso 1 1 calc R U . . .
H14C H 0.8275 0.6470 0.3609 0.071 Uiso 1 1 calc R U . . .
C13 C 0.9437(6) 0.5875(6) 0.209(2) 0.110(6) Uani 1 1 d . . . . .
H13A H 0.9674 0.5514 0.1423 0.165 Uiso 1 1 calc R U . . .
H13B H 0.9666 0.5913 0.3182 0.165 Uiso 1 1 calc R U . . .
H13C H 0.9465 0.6327 0.1511 0.165 Uiso 1 1 calc R U . . .
C7 C 0.5832(4) 0.3334(4) 0.5240(8) 0.0264(16) Uani 1 1 d . . . . .
C6 C 0.5238(4) 0.3029(4) 0.4532(8) 0.0214(17) Uani 1 1 d . . . . .
H6 H 0.4821 0.2987 0.5174 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5832(5) 0.3617(5) 0.6972(9) 0.034(2) Uani 1 1 d . . . . .
H9 H 0.6275 0.3696 0.7486 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5278(5) 0.3764(5) 0.7830(9) 0.032(2) Uani 1 1 d . . . . .
C11 C 0.4728(5) 0.3914(6) 0.8684(11) 0.044(2) Uani 1 1 d D . . . .
H11A H 0.454(5) 0.437(2) 0.847(10) 0.052 Uiso 1 1 d D U . . .
H11B H 0.451(4) 0.361(3) 0.944(8) 0.052 Uiso 1 1 d D 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 O3 2.396(5) 4_655 ?
Pb1 O2 2.446(4) . ?
Pb1 O1 2.527(4) . ?
Pb1 O5 2.693(5) . ?
Pb1 O2 2.705(5) 8_544 ?
Pb1 C1 2.847(7) . ?
O1 C1 1.246(8) . ?
O2 C1 1.281(8) . ?
O2 Pb1 2.705(5) 8_545 ?
O3 C5 1.257(8) . ?
O3 Pb1 2.396(5) 2_565 ?
O4 C5 1.254(8) . ?
O5 C12 1.229(10) . ?
C2 C3 1.390(10) . ?
C2 C8 1.399(9) . ?
C2 C1 1.489(10) . ?
C8 C7 1.389(9) . ?
C8 H8 0.9500 . ?
C12 N1 1.322(10) . ?
C12 H12 0.9500 . ?
C5 C4 1.503(10) . ?
C3 C4 1.406(10) . ?
C3 H3 0.9500 . ?
N1 C14 1.446(12) . ?
N1 C13 1.448(12) . ?
C4 C6 1.397(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C7 C6 1.392(9) . ?
C7 C9 1.488(10) . ?
C6 H6 0.9500 . ?
C9 C10 1.291(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.282(12) . ?
C11 H11A 0.96(3) . ?
C11 H11B 0.94(3) . ?

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 81.49(17) 4_655 . ?
O3 Pb1 O1 84.96(17) 4_655 . ?
O2 Pb1 O1 52.57(15) . . ?
O3 Pb1 O5 74.75(18) 4_655 . ?
O2 Pb1 O5 71.22(17) . . ?
O1 Pb1 O5 122.44(17) . . ?
O3 Pb1 O2 122.04(15) 4_655 8_544 ?
O2 Pb1 O2 131.8(2) . 8_544 ?
O1 Pb1 O2 85.64(15) . 8_544 ?
O5 Pb1 O2 150.06(18) . 8_544 ?
O3 Pb1 C1 81.47(19) 4_655 . ?
O2 Pb1 C1 26.66(17) . . ?
O1 Pb1 C1 25.95(18) . . ?
O5 Pb1 C1 97.00(19) . . ?
O2 Pb1 C1 109.36(18) 8_544 . ?
C1 O1 Pb1 91.5(4) . . ?
C1 O2 Pb1 94.4(4) . . ?
C1 O2 Pb1 139.7(4) . 8_545 ?
Pb1 O2 Pb1 103.55(18) . 8_545 ?
C5 O3 Pb1 102.3(4) . 2_565 ?
C12 O5 Pb1 112.5(5) . . ?
C3 C2 C8 118.5(7) . . ?
C3 C2 C1 121.5(6) . . ?
C8 C2 C1 119.8(7) . . ?
C7 C8 C2 121.7(7) . . ?
C7 C8 H8 119.2 . . ?
C2 C8 H8 119.2 . . ?
O1 C1 O2 121.3(6) . . ?
O1 C1 C2 121.1(6) . . ?
O2 C1 C2 117.5(6) . . ?
O1 C1 Pb1 62.5(4) . . ?
O2 C1 Pb1 59.0(4) . . ?
C2 C1 Pb1 173.3(5) . . ?
O5 C12 N1 126.5(9) . . ?
O5 C12 H12 116.7 . . ?
N1 C12 H12 116.7 . . ?
O4 C5 O3 123.2(7) . . ?
O4 C5 C4 119.7(6) . . ?
O3 C5 C4 117.0(6) . . ?
C2 C3 C4 120.8(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C12 N1 C14 122.6(9) . . ?
C12 N1 C13 120.9(9) . . ?
C14 N1 C13 116.4(8) . . ?
C6 C4 C3 119.2(7) . . ?
C6 C4 C5 121.2(7) . . ?
C3 C4 C5 119.6(6) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C7 C6 119.0(6) . . ?
C8 C7 C9 118.9(6) . . ?
C6 C7 C9 122.0(6) . . ?
C7 C6 C4 120.7(7) . . ?
C7 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
C10 C9 C7 125.1(8) . . ?
C10 C9 H9 117.4 . . ?
C7 C9 H9 117.4 . . ?
C11 C10 C9 179.7(11) . . ?
C10 C11 H11A 114(6) . . ?
C10 C11 H11B 124(5) . . ?
H11A C11 H11B 121(8) . . ?

_refine_diff_density_max         0.873
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.164


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_chemical_properties_physical    Hygroscopic
