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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_HA111

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N6 O3 Pb S, 1.5(C H4 O)'
_chemical_formula_sum            'C14.50 H16 N6 O4.50 Pb S'
_chemical_formula_weight         585.58

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   31.684(4)
_cell_length_b                   10.0017(12)
_cell_length_c                   13.3763(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.607(3)
_cell_angle_gamma                90.00
_cell_volume                     4062.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3094
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.73

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2232
_exptl_absorpt_coefficient_mu    8.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.161
_exptl_absorpt_correction_T_max  0.365
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24504
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         29.83
_reflns_number_total             5776
_reflns_number_gt                4613
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5776
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.246458(6) 0.173727(18) 0.145186(14) 0.01135(6) Uani 1 1 d . . .
O1 O 0.25334(11) 0.3851(4) 0.2849(3) 0.0153(7) Uani 1 1 d . . .
O2 O 0.31156(14) 0.4457(4) 0.4065(3) 0.0237(9) Uani 1 1 d . . .
O3 O 0.31327(13) 0.2684(4) 0.3115(3) 0.0227(9) Uani 1 1 d . . .
S1 S 0.28856(7) 0.62536(16) 0.14398(14) 0.0409(5) Uani 1 1 d . . .
N1 N 0.27171(15) 0.3704(4) 0.0582(3) 0.0148(9) Uani 1 1 d . . .
N2 N 0.32135(14) 0.0794(4) 0.1275(3) 0.0153(9) Uani 1 1 d . . .
N3 N 0.47606(14) -0.0265(5) 0.1227(4) 0.0198(10) Uani 1 1 d . . .
N4 N 0.51267(14) -0.1056(5) 0.1194(4) 0.0189(10) Uani 1 1 d . . .
N5 N 0.66835(15) -0.2045(5) 0.1146(4) 0.0171(9) Uani 1 1 d . . .
N6 N 0.29283(15) 0.3666(5) 0.3344(4) 0.0164(9) Uani 1 1 d . . .
C1 C 0.27902(17) 0.4779(5) 0.0950(4) 0.0158(10) Uani 1 1 d . . .
C2 C 0.32388(17) -0.0517(5) 0.1069(4) 0.0146(10) Uani 1 1 d . . .
H2A H 0.2978 -0.1041 0.0917 0.017 Uiso 1 1 calc R . .
C3 C 0.36313(18) -0.1126(5) 0.1070(4) 0.0176(11) Uani 1 1 d . . .
H3A H 0.3641 -0.2061 0.0955 0.021 Uiso 1 1 calc R . .
C4 C 0.40126(17) -0.0352(6) 0.1243(4) 0.0175(11) Uani 1 1 d . . .
C5 C 0.39838(17) 0.1002(5) 0.1446(4) 0.0158(10) Uani 1 1 d . . .
H5A H 0.4238 0.1554 0.1579 0.019 Uiso 1 1 calc R . .
C6 C 0.35808(17) 0.1540(5) 0.1452(4) 0.0165(11) Uani 1 1 d . . .
H6A H 0.3564 0.2469 0.1585 0.020 Uiso 1 1 calc R . .
C7 C 0.44266(18) -0.0993(6) 0.1204(4) 0.0181(11) Uani 1 1 d . . .
H7A H 0.4445 -0.1938 0.1161 0.022 Uiso 1 1 calc R . .
C8 C 0.54528(17) -0.0310(6) 0.1190(4) 0.0191(11) Uani 1 1 d . . .
H8A H 0.5426 0.0635 0.1203 0.023 Uiso 1 1 calc R . .
C9 C 0.58750(17) -0.0935(6) 0.1165(4) 0.0167(11) Uani 1 1 d . . .
C10 C 0.59274(18) -0.2305(6) 0.1114(5) 0.0205(12) Uani 1 1 d . . .
H10A H 0.5688 -0.2891 0.1087 0.025 Uiso 1 1 calc R . .
C11 C 0.63281(19) -0.2804(6) 0.1104(5) 0.0234(12) Uani 1 1 d . . .
H11A H 0.6358 -0.3747 0.1065 0.028 Uiso 1 1 calc R . .
C12 C 0.66365(17) -0.0707(5) 0.1223(4) 0.0157(10) Uani 1 1 d . . .
H12A H 0.6885 -0.0151 0.1278 0.019 Uiso 1 1 calc R . .
C13 C 0.62403(16) -0.0110(6) 0.1226(4) 0.0167(11) Uani 1 1 d . . .
H13A H 0.6217 0.0834 0.1269 0.020 Uiso 1 1 calc R . .
O4 O 0.3978(3) 0.3997(8) 0.5173(7) 0.061(2) Uani 0.75 1 d P . .
H4O H 0.4182 0.4041 0.4889 0.091 Uiso 0.75 1 calc PR . .
O5 O 0.5654(4) 0.3174(9) 0.1366(10) 0.087(3) Uani 0.75 1 d P . .
H5O H 0.5812 0.3849 0.1573 0.131 Uiso 0.75 1 calc PR . .
C14 C 0.4091(4) 0.4839(10) 0.6130(9) 0.055(3) Uani 0.75 1 d P . .
H14A H 0.3993 0.4390 0.6677 0.083 Uiso 0.75 1 calc PR . .
H14B H 0.3943 0.5707 0.5972 0.083 Uiso 0.75 1 calc PR . .
H14C H 0.4410 0.4975 0.6372 0.083 Uiso 0.75 1 calc PR . .
C15 C 0.5210(4) 0.3538(16) 0.1134(12) 0.081(5) Uani 0.75 1 d P . .
H15A H 0.5114 0.3484 0.1769 0.122 Uiso 0.75 1 calc PR . .
H15B H 0.5032 0.2929 0.0606 0.122 Uiso 0.75 1 calc PR . .
H15C H 0.5172 0.4455 0.0866 0.122 Uiso 0.75 1 calc PR . .


_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 N1 2.529(4) . ?
Pb1 N2 2.627(4) . ?
Pb1 N1 2.652(4) 7 ?
Pb1 N5 2.683(4) 3_455 ?
Pb1 O3 2.763(4) . ?
Pb1 O1 2.789(4) . ?
Pb1 O2 2.886(4) 4_545 ?
Pb1 O1 3.034(4) 4_545 ?
Pb1 S1 3.348(2) 4_545 ?
O1 N6 1.251(6) . ?
O2 N6 1.258(6) . ?
O3 N6 1.261(6) . ?
S1 C1 1.607(6) . ?
N1 C1 1.178(7) . ?
N1 Pb1 2.652(4) 7 ?
N2 C6 1.345(7) . ?
N2 C2 1.346(7) . ?
N3 C7 1.277(7) . ?
N3 N4 1.415(6) . ?
N4 C8 1.276(7) . ?
N5 C11 1.346(7) . ?
N5 C12 1.353(7) . ?
N5 Pb1 2.683(4) 3_545 ?
C2 C3 1.384(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.397(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(8) . ?
C4 C7 1.474(7) . ?
C5 C6 1.388(7) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.486(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.384(8) . ?
C9 C13 1.404(7) . ?
C10 C11 1.368(8) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.391(7) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
O4 C14 1.488(13) . ?
O4 H4O 0.8400 . ?
O5 C15 1.399(16) . ?
O5 H5O 0.8400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
N1 Pb1 N2 79.93(14) . . ?
N1 Pb1 N1 70.23(16) . 7 ?
N2 Pb1 N1 77.56(14) . 7 ?
N1 Pb1 N5 88.62(14) . 3_455 ?
N2 Pb1 N5 165.28(14) . 3_455 ?
N1 Pb1 N5 89.92(14) 7 3_455 ?
C1 N1 Pb1 124.6(4) . . ?
C1 N1 Pb1 122.7(4) . 7 ?
Pb1 N1 Pb1 109.77(16) . 7 ?
C6 N2 C2 118.5(5) . . ?
C6 N2 Pb1 122.9(3) . . ?
C2 N2 Pb1 118.4(3) . . ?
C7 N3 N4 111.2(5) . . ?
C8 N4 N3 110.2(5) . . ?
C11 N5 C12 116.9(5) . . ?
C11 N5 Pb1 118.3(4) . 3_545 ?
C12 N5 Pb1 123.7(3) . 3_545 ?
O1 N6 O2 119.6(4) . . ?
O1 N6 O3 119.5(4) . . ?
O2 N6 O3 120.9(4) . . ?
N1 C1 S1 179.3(6) . . ?
N2 C2 C3 122.3(5) . . ?
N2 C2 H2A 118.8 . . ?
C3 C2 H2A 118.8 . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 C7 122.6(5) . . ?
C3 C4 C7 119.3(5) . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
N2 C6 C5 122.3(5) . . ?
N2 C6 H6A 118.8 . . ?
C5 C6 H6A 118.8 . . ?
N3 C7 C4 119.4(5) . . ?
N3 C7 H7A 120.3 . . ?
C4 C7 H7A 120.3 . . ?
N4 C8 C9 119.3(5) . . ?
N4 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C13 118.4(5) . . ?
C10 C9 C8 122.6(5) . . ?
C13 C9 C8 118.9(5) . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
N5 C11 C10 124.2(5) . . ?
N5 C11 H11A 117.9 . . ?
C10 C11 H11A 117.9 . . ?
N5 C12 C13 122.9(5) . . ?
N5 C12 H12A 118.5 . . ?
C13 C12 H12A 118.5 . . ?
C12 C13 C9 118.5(5) . . ?
C12 C13 H13A 120.8 . . ?
C9 C13 H13A 120.8 . . ?
C14 O4 H4O 109.5 . . ?
C15 O5 H5O 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
N2 Pb1 N1 C1 -118.8(5) . . . . ?
N1 Pb1 N1 C1 160.9(6) 7 . . . ?
N5 Pb1 N1 C1 70.5(5) 3_455 . . . ?
N2 Pb1 N1 Pb1 80.29(17) . . . 7 ?
N1 Pb1 N1 Pb1 0.0 7 . . 7 ?
N5 Pb1 N1 Pb1 -90.41(17) 3_455 . . 7 ?
N1 Pb1 N2 C6 40.6(4) . . . . ?
N1 Pb1 N2 C6 112.4(4) 7 . . . ?
N5 Pb1 N2 C6 80.1(7) 3_455 . . . ?
N1 Pb1 N2 C2 -144.1(4) . . . . ?
N1 Pb1 N2 C2 -72.3(4) 7 . . . ?
N5 Pb1 N2 C2 -104.6(6) 3_455 . . . ?
C7 N3 N4 C8 178.3(5) . . . . ?
Pb1 N1 C1 S1 -128(42) . . . . ?
Pb1 N1 C1 S1 31(43) 7 . . . ?
C6 N2 C2 C3 2.4(8) . . . . ?
Pb1 N2 C2 C3 -173.1(4) . . . . ?
N2 C2 C3 C4 -3.0(8) . . . . ?
C2 C3 C4 C5 2.3(8) . . . . ?
C2 C3 C4 C7 -177.6(5) . . . . ?
C3 C4 C5 C6 -1.1(8) . . . . ?
C7 C4 C5 C6 178.8(5) . . . . ?
C2 N2 C6 C5 -1.1(8) . . . . ?
Pb1 N2 C6 C5 174.2(4) . . . . ?
C4 C5 C6 N2 0.5(8) . . . . ?
N4 N3 C7 C4 179.3(4) . . . . ?
C5 C4 C7 N3 -8.9(8) . . . . ?
C3 C4 C7 N3 171.0(5) . . . . ?
N3 N4 C8 C9 179.6(4) . . . . ?
N4 C8 C9 C10 1.9(8) . . . . ?
N4 C8 C9 C13 -176.1(5) . . . . ?
C13 C9 C10 C11 -1.3(8) . . . . ?
C8 C9 C10 C11 -179.4(5) . . . . ?
C12 N5 C11 C10 1.4(9) . . . . ?
Pb1 N5 C11 C10 169.5(5) 3_545 . . . ?
C9 C10 C11 N5 0.3(10) . . . . ?
C11 N5 C12 C13 -2.1(8) . . . . ?
Pb1 N5 C12 C13 -169.5(4) 3_545 . . . ?
N5 C12 C13 C9 1.2(8) . . . . ?
C10 C9 C13 C12 0.6(7) . . . . ?
C8 C9 C13 C12 178.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4O O5 0.84 2.08 2.77(2) 138 2_655 yes

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        29.83
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.683
_refine_diff_density_min         -2.000
_refine_diff_density_rms         0.188

_vrf_PLAT420_HA111               
;
PROBLEM: D-H Without Acceptor      >O5     -  >H5O    ...          ? 
RESPONSE: This hydrogen atom belongs to the water molecule with the partly
occupied position.
;
_database_code_depnum_ccdc_archive 'CCDC 983874'
