# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_cdyb001
_database_code_depnum_ccdc_archive 'CCDC 1023395'
_audit_update_record             
;
2014-09-08 deposited with the CCDC.
2014-12-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_DIFMN02_cdyb001             
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: The features on the final difference map 
are most likely absorption artifacts.
The compound strongly absorbs X-rays and 
consistently deposits as thin plates. We have explored 
several absorption corrections and the data presented 
have been treated to give the best resulting Rint values. 
;
_vrf_PLAT098_cdyb001             
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -9.57 eA-3  
RESPONSE: See response to DIFMN02.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H34 O4 Pb'
_chemical_formula_weight         521.64

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'

_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                   54.872(6)
_cell_length_b                   4.9603(5)
_cell_length_c                   7.1628(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.368(2)
_cell_angle_gamma                90
_cell_volume                     1949.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3708
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.52

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    8.670
_shelx_estimated_absorpt_T_min   0.220
_shelx_estimated_absorpt_T_max   0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4056
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'

_exptl_special_details           
; 
Data collection is performed with four batch runs at 
φ = 0.00 ° (600 frames), at φ = 90.00 ° 
(600 frames), at φ = 180 ° (600 frames) and 
at φ = 270 ° (600 frames). 
Frame width = 0.30 \& in ω. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            25918
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_limit_h_min       -71
_diffrn_reflns_limit_h_max       71
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.113
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4459
_reflns_number_gt                3837
_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       'Bruker APEX2'
_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          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+69.3239P] 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         4459
_refine_ls_number_parameters     198
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_restrained_S_all      1.276
_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 0.24763(2) 0.27160(9) 0.96741(7) 0.01878(16) Uani 1 1 d . U . . .
O1 O 0.23156(18) 0.119(2) 0.6327(15) 0.0319(16) Uani 1 1 d D U . . .
O2 O 0.2112(2) 0.487(2) 0.6962(15) 0.0333(17) Uani 1 1 d D U . . .
O3 O 0.28569(19) 0.044(2) 0.9160(15) 0.0319(16) Uani 1 1 d D U . . .
O4 O 0.26839(18) -0.317(2) 0.7906(15) 0.0333(17) Uani 1 1 d D U . . .
C1 C 0.2120(2) 0.256(2) 0.6252(18) 0.020(2) Uani 1 1 d D U . . .
C2 C 0.1900(2) 0.142(3) 0.5283(18) 0.019(2) Uani 1 1 d . U . . .
H2A H 0.1882 -0.0493 0.5652 0.023 Uiso 1 1 calc R U . . .
H2B H 0.1928 0.1469 0.3918 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1664(2) 0.292(3) 0.5721(18) 0.021(3) Uani 1 1 d . U . . .
H3A H 0.1682 0.4841 0.5362 0.025 Uiso 1 1 calc R U . . .
H3B H 0.1635 0.2857 0.7084 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1440(2) 0.173(3) 0.4694(19) 0.024(3) Uani 1 1 d . U . . .
H4A H 0.1463 0.1955 0.3332 0.028 Uiso 1 1 calc R U . . .
H4B H 0.1431 -0.0222 0.4960 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1201(2) 0.306(3) 0.526(2) 0.025(3) Uani 1 1 d . U . . .
H5A H 0.1181 0.2883 0.6629 0.030 Uiso 1 1 calc R U . . .
H5B H 0.1209 0.5013 0.4969 0.030 Uiso 1 1 calc R U . . .
C6 C 0.0978(3) 0.187(3) 0.430(2) 0.026(3) Uani 1 1 d . U . . .
H6A H 0.0992 0.2168 0.2933 0.031 Uiso 1 1 calc R U . . .
H6B H 0.0976 -0.0099 0.4514 0.031 Uiso 1 1 calc R U . . .
C7 C 0.0740(3) 0.306(3) 0.496(2) 0.031(3) Uani 1 1 d . U . . .
H7A H 0.0742 0.5028 0.4725 0.037 Uiso 1 1 calc R U . . .
H7B H 0.0728 0.2786 0.6323 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0514(3) 0.185(3) 0.401(2) 0.034(3) Uani 1 1 d . U . . .
H8A H 0.0522 0.2205 0.2655 0.041 Uiso 1 1 calc R U . . .
H8B H 0.0515 -0.0124 0.4197 0.041 Uiso 1 1 calc R U . . .
C9 C 0.0277(3) 0.297(4) 0.475(3) 0.052(5) Uani 1 1 d . U . . .
H9A H 0.0269 0.2681 0.6103 0.078 Uiso 1 1 calc R U . . .
H9B H 0.0140 0.2049 0.4143 0.078 Uiso 1 1 calc R U . . .
H9C H 0.0268 0.4907 0.4486 0.078 Uiso 1 1 calc R U . . .
C10 C 0.2868(2) -0.182(2) 0.8395(17) 0.019(2) Uani 1 1 d D U . . .
C11 C 0.3110(2) -0.312(3) 0.8017(17) 0.019(2) Uani 1 1 d . U . . .
H11A H 0.3139 -0.3074 0.6655 0.023 Uiso 1 1 calc R U . . .
H11B H 0.3100 -0.5035 0.8395 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3329(2) -0.184(3) 0.9001(18) 0.021(3) Uani 1 1 d . U . . .
H12A H 0.3313 -0.2082 1.0367 0.025 Uiso 1 1 calc R U . . .
H12B H 0.3331 0.0117 0.8738 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3571(2) -0.310(3) 0.8359(19) 0.023(3) Uani 1 1 d . U . . .
H13A H 0.3568 -0.5062 0.8621 0.028 Uiso 1 1 calc R U . . .
H13B H 0.3586 -0.2870 0.6992 0.028 Uiso 1 1 calc R U . . .
C14 C 0.3795(2) -0.188(3) 0.9306(19) 0.023(3) Uani 1 1 d . U . . .
H14A H 0.3785 -0.2178 1.0670 0.027 Uiso 1 1 calc R U . . .
H14B H 0.3797 0.0091 0.9084 0.027 Uiso 1 1 calc R U . . .
C15 C 0.4032(2) -0.310(3) 0.858(2) 0.026(3) Uani 1 1 d . U . . .
H15A H 0.4029 -0.5071 0.8812 0.031 Uiso 1 1 calc R U . . .
H15B H 0.4040 -0.2825 0.7214 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4260(3) -0.193(3) 0.947(2) 0.029(3) Uani 1 1 d . U . . .
H16A H 0.4254 -0.2218 1.0837 0.035 Uiso 1 1 calc R U . . .
H16B H 0.4263 0.0044 0.9247 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4495(3) -0.316(3) 0.872(2) 0.034(3) Uani 1 1 d . U . . .
H17A H 0.4501 -0.2856 0.7353 0.041 Uiso 1 1 calc R U . . .
H17B H 0.4491 -0.5132 0.8930 0.041 Uiso 1 1 calc R U . . .
C18 C 0.4728(3) -0.203(4) 0.960(3) 0.048(5) Uani 1 1 d . U . . .
H18A H 0.4734 -0.0072 0.9406 0.072 Uiso 1 1 calc R U . . .
H18B H 0.4870 -0.2870 0.9026 0.072 Uiso 1 1 calc R U . . .
H18C H 0.4728 -0.2408 1.0946 0.072 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 O3 2.403(10) . ?
Pb1 O1 2.437(10) 4_556 ?
Pb1 O4 2.583(10) 4_556 ?
Pb1 O4 2.661(10) 1_565 ?
Pb1 O1 2.660(10) . ?
O1 C1 1.270(12) . ?
O1 Pb1 2.437(10) 4 ?
O2 C1 1.257(12) . ?
O3 C10 1.249(12) . ?
O4 C10 1.262(12) . ?
O4 Pb1 2.583(10) 4 ?
O4 Pb1 2.661(10) 1_545 ?
C1 C2 1.499(17) . ?
C2 C3 1.533(18) . ?
C3 C4 1.542(18) . ?
C4 C5 1.529(19) . ?
C5 C6 1.522(19) . ?
C6 C7 1.51(2) . ?
C7 C8 1.53(2) . ?
C8 C9 1.51(2) . ?
C10 C11 1.502(18) . ?
C11 C12 1.526(18) . ?
C12 C13 1.543(18) . ?
C13 C14 1.525(18) . ?
C14 C15 1.529(18) . ?
C15 C16 1.519(19) . ?
C16 C17 1.53(2) . ?
C17 C18 1.53(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
O3 Pb1 O1 91.1(4) . 4_556 ?
O3 Pb1 O4 78.5(3) . 4_556 ?
O1 Pb1 O4 78.1(3) 4_556 4_556 ?
O3 Pb1 O4 84.9(3) . 1_565 ?
O1 Pb1 O4 175.8(3) 4_556 1_565 ?
O4 Pb1 O4 99.9(3) 4_556 1_565 ?
O3 Pb1 O1 90.7(3) . . ?
O1 Pb1 O1 95.3(2) 4_556 . ?
O4 Pb1 O1 167.0(3) 4_556 . ?
O4 Pb1 O1 86.0(3) 1_565 . ?
C1 O1 Pb1 135.5(8) . 4 ?
C1 O1 Pb1 99.2(8) . . ?
Pb1 O1 Pb1 123.1(4) 4 . ?
C10 O3 Pb1 122.2(9) . . ?
C10 O4 Pb1 123.3(9) . 4 ?
C10 O4 Pb1 128.4(9) . 1_545 ?
Pb1 O4 Pb1 107.8(3) 4 1_545 ?
O2 C1 O1 120.5(12) . . ?
O2 C1 C2 119.9(11) . . ?
O1 C1 C2 119.6(10) . . ?
C1 C2 C3 113.8(10) . . ?
C2 C3 C4 112.8(11) . . ?
C5 C4 C3 112.9(11) . . ?
C6 C5 C4 113.6(12) . . ?
C7 C6 C5 113.5(12) . . ?
C6 C7 C8 114.1(13) . . ?
C9 C8 C7 113.6(14) . . ?
O3 C10 O4 124.0(13) . . ?
O3 C10 C11 120.7(11) . . ?
O4 C10 C11 115.3(11) . . ?
C10 C11 C12 115.6(10) . . ?
C11 C12 C13 111.8(11) . . ?
C14 C13 C12 113.5(11) . . ?
C13 C14 C15 112.0(11) . . ?
C16 C15 C14 113.9(12) . . ?
C15 C16 C17 113.1(13) . . ?
C16 C17 C18 114.2(14) . . ?

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
Pb1 O1 C1 O2 -162.2(10) 4 . . . ?
Pb1 O1 C1 O2 35.4(14) . . . . ?
Pb1 O1 C1 C2 17(2) 4 . . . ?
Pb1 O1 C1 C2 -145.5(10) . . . . ?
O2 C1 C2 C3 -15.7(18) . . . . ?
O1 C1 C2 C3 165.2(12) . . . . ?
C1 C2 C3 C4 179.4(11) . . . . ?
C2 C3 C4 C5 174.8(11) . . . . ?
C3 C4 C5 C6 -178.7(12) . . . . ?
C4 C5 C6 C7 176.0(12) . . . . ?
C5 C6 C7 C8 -179.3(13) . . . . ?
C6 C7 C8 C9 177.4(14) . . . . ?
Pb1 O3 C10 O4 -3.6(19) . . . . ?
Pb1 O3 C10 C11 177.2(9) . . . . ?
Pb1 O4 C10 O3 88.7(15) 4 . . . ?
Pb1 O4 C10 O3 -99.7(15) 1_545 . . . ?
Pb1 O4 C10 C11 -92.0(12) 4 . . . ?
Pb1 O4 C10 C11 79.6(14) 1_545 . . . ?
O3 C10 C11 C12 13.3(18) . . . . ?
O4 C10 C11 C12 -166.1(12) . . . . ?
C10 C11 C12 C13 -173.5(11) . . . . ?
C11 C12 C13 C14 179.9(11) . . . . ?
C12 C13 C14 C15 -177.8(12) . . . . ?
C13 C14 C15 C16 179.4(12) . . . . ?
C14 C15 C16 C17 -179.6(13) . . . . ?
C15 C16 C17 C18 -179.5(14) . . . . ?

_refine_diff_density_max         4.344
_refine_diff_density_min         -9.570
_refine_diff_density_rms         0.286

_shelxl_version_number           2014-3



