Supplementary material (ESI) for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Zhi Rong Chen'
_publ_contact_author_address     
;
College of Chemistry and Chemical Engineering
Fuzhou University
Fuzhou
350108
CHINA
;

_publ_contact_author_email       ZRCHEN@FZU.EDU.CN

_publ_section_title              
;
A Series of Lead(II)/Iodine Hybrid Materials Based on
1- and 2-D Metal-Organic Motifs Linked by Different Organic Conjugated
Ligands
;
loop_
_publ_author_name
'Zhi Rong Chen'
'Miao Feng'
'Chang-Cang Huang'
'Xi He Huang'
;
HaoHong Li
;
'Yun Lin'
'YunJie Wang'

data_y08f
_database_code_depnum_ccdc_archive 'CCDC 634298'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 I2 N O Pb'
_chemical_formula_sum            'C5 H4 I2 N O Pb'
_chemical_formula_weight         555.09

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5644(9)
_cell_length_b                   8.9738(18)
_cell_length_c                   11.778(2)
_cell_angle_alpha                78.05(3)
_cell_angle_beta                 83.67(3)
_cell_angle_gamma                84.67(3)
_cell_volume                     467.88(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18
_cell_measurement_theta_min      12
_cell_measurement_theta_max      15

_exptl_crystal_description       Block
_exptl_crystal_colour            Blown
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.940
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             474.0
_exptl_absorpt_coefficient_mu    24.567
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.013
_exptl_absorpt_correction_T_max  0.052
_exptl_absorpt_process_details   
'TEXRAY software (Molecular Structure Corporation, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotor target'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Weissenberg IP'
_diffrn_measurement_method       'scintillation counter'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            4670
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_sigmaI/netI    0.1128
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2140
_reflns_number_gt                1510
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'TEXRAY software (Molecular Structure Corporation, 1999)'
_computing_cell_refinement       'TEXRAY software'
_computing_data_reduction        
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  "SHELXL-97/2 (Sheldrick,1997)')"

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.30452(8) 0.91374(5) 0.35680(4) 0.04399(19) Uani 1 1 d . . .
I1 I 0.22646(16) 1.24247(10) 0.45986(7) 0.0513(3) Uani 1 1 d . . .
I2 I -0.17756(15) 1.03626(10) 0.17402(7) 0.0499(3) Uani 1 1 d . . .
N1 N 0.5211(19) 0.6420(11) 0.2119(9) 0.043(3) Uani 1 1 d . . .
O1 O 0.331(2) 0.6819(12) 0.2918(9) 0.066(3) Uani 1 1 d . . .
C1 C 0.505(3) 0.7035(14) 0.0998(11) 0.048(3) Uani 1 1 d . . .
H1 H 0.3678 0.7848 0.0782 0.057 Uiso 1 1 calc R . .
C2 C 0.686(3) 0.6496(14) 0.0173(11) 0.047(3) Uani 1 1 d . . .
H2 H 0.6663 0.6929 -0.0606 0.057 Uiso 1 1 calc R . .
C3 C 0.902(2) 0.5315(12) 0.0442(11) 0.038(3) Uani 1 1 d . . .
C4 C 0.915(3) 0.4791(14) 0.1635(12) 0.049(3) Uani 1 1 d . . .
H4 H 1.0594 0.4030 0.1882 0.059 Uiso 1 1 calc R . .
C5 C 0.731(3) 0.5319(16) 0.2438(12) 0.054(4) Uani 1 1 d . . .
H5 H 0.7486 0.4922 0.3225 0.065 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pb1 0.0350(3) 0.0522(3) 0.0421(3) -0.0016(2) -0.0046(2) -0.00580(18)
I1 0.0433(4) 0.0562(6) 0.0468(5) 0.0093(4) -0.0072(4) -0.0048(3)
I2 0.0379(4) 0.0618(6) 0.0423(5) 0.0089(4) -0.0050(3) -0.0053(3)
N1 0.037(5) 0.047(6) 0.046(6) -0.011(5) -0.004(5) -0.010(4)
O1 0.069(6) 0.060(7) 0.071(7) -0.030(5) 0.015(5) -0.009(5)
C1 0.049(7) 0.045(8) 0.042(8) 0.003(6) -0.006(6) 0.006(5)
C2 0.058(7) 0.045(8) 0.037(7) 0.007(6) -0.015(6) -0.010(6)
C3 0.043(6) 0.017(5) 0.057(8) -0.005(5) -0.016(5) -0.005(4)
C4 0.056(7) 0.040(7) 0.050(8) 0.000(6) -0.013(7) -0.003(5)
C5 0.044(7) 0.068(9) 0.045(8) 0.014(7) -0.016(6) -0.015(6)

_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 2.350(11) . ?
Pb1 I2 3.1324(14) 1_655 ?
Pb1 I2 3.2094(12) . ?
Pb1 I1 3.2279(13) 2_676 ?
Pb1 I1 3.2749(14) 2_576 ?
Pb1 I1 3.3905(14) . ?
I1 Pb1 3.2279(13) 2_676 ?
I1 Pb1 3.2749(14) 2_576 ?
I2 Pb1 3.1324(14) 1_455 ?
N1 O1 1.291(15) . ?
N1 C1 1.329(14) . ?
N1 C5 1.336(16) . ?
C1 C2 1.34(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(17) . ?
C3 C3 1.47(3) 2_765 ?
C4 C5 1.33(2) . ?
C4 H4 0.9300 . ?
C5 H5 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
O1 Pb1 I2 92.1(3) . 1_655 ?
O1 Pb1 I2 86.6(2) . . ?
I2 Pb1 I2 92.06(3) 1_655 . ?
O1 Pb1 I1 88.3(2) . 2_676 ?
I2 Pb1 I1 90.27(3) 1_655 2_676 ?
I2 Pb1 I1 174.45(3) . 2_676 ?
O1 Pb1 I1 82.9(2) . 2_576 ?
I2 Pb1 I1 175.03(3) 1_655 2_576 ?
I2 Pb1 I1 88.09(3) . 2_576 ?
I1 Pb1 I1 89.16(3) 2_676 2_576 ?
O1 Pb1 I1 176.5(2) . . ?
I2 Pb1 I1 91.29(4) 1_655 . ?
I2 Pb1 I1 92.50(3) . . ?
I1 Pb1 I1 92.48(3) 2_676 . ?
I1 Pb1 I1 93.67(3) 2_576 . ?
Pb1 I1 Pb1 89.16(3) 2_676 2_576 ?
Pb1 I1 Pb1 87.52(3) 2_676 . ?
Pb1 I1 Pb1 86.33(3) 2_576 . ?
Pb1 I2 Pb1 92.06(3) 1_455 . ?
O1 N1 C1 121.7(11) . . ?
O1 N1 C5 118.5(11) . . ?
C1 N1 C5 119.8(12) . . ?
N1 O1 Pb1 125.7(7) . . ?
N1 C1 C2 120.8(11) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 122.2(11) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C2 C3 C4 113.4(12) . . ?
C2 C3 C3 123.3(13) . 2_765 ?
C4 C3 C3 123.3(12) . 2_765 ?
C5 C4 C3 123.5(12) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C4 C5 N1 120.1(11) . . ?
C4 C5 H5 120.0 . . ?
N1 C5 H5 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.447
_refine_diff_density_min         -1.900
_refine_diff_density_rms         0.299


data_1
_database_code_depnum_ccdc_archive 'CCDC 656622'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 I2 N2 O2 Pb'
_chemical_formula_sum            'C10 H8 I2 N2 O2 Pb'
_chemical_formula_weight         649.18

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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                   18.866(4)
_cell_length_b                   8.6033(17)
_cell_length_c                   9.6102(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.43(3)
_cell_angle_gamma                90.00
_cell_volume                     1408.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18
_cell_measurement_theta_min      12
_cell_measurement_theta_max      15

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.061
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    16.351
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.054
_exptl_absorpt_correction_T_max  0.141
_exptl_absorpt_process_details   
'TEXRAY software (Molecular Structure Corporation, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotor target'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Weissenberg IP'
_diffrn_measurement_method       'scintillation counter'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            6759
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1629
_reflns_number_gt                1495
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'TEXRAY software (Molecular Structure Corporation, 1999)'
_computing_cell_refinement       'TEXRAY software'
_computing_data_reduction        
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  "SHELXL-97/2 (Sheldrick,1997)')"

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0369P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1629
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0655
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.0000 0.42769(4) 0.2500 0.03335(13) Uani 1 2 d S . .
I1 I -0.12045(3) 0.60635(5) 0.39394(4) 0.04324(15) Uani 1 1 d . . .
O1 O 0.0583(3) 0.2083(5) 0.1924(4) 0.0382(10) Uani 1 1 d . . .
N1 N 0.0892(3) 0.0966(5) 0.2943(5) 0.0309(10) Uani 1 1 d . . .
C1 C 0.1665(4) 0.0939(7) 0.3799(7) 0.0403(14) Uani 1 1 d . . .
H1 H 0.1976 0.1730 0.3699 0.048 Uiso 1 1 calc R . .
C2 C 0.2011(4) -0.0259(9) 0.4840(7) 0.0453(16) Uani 1 1 d . . .
H2 H 0.2550 -0.0272 0.5441 0.054 Uiso 1 1 calc R . .
C3 C 0.1549(4) -0.1416(8) 0.4969(7) 0.0416(15) Uani 1 1 d . . .
H3 H 0.1773 -0.2220 0.5669 0.050 Uiso 1 1 calc R . .
C4 C 0.0751(4) -0.1395(7) 0.4063(6) 0.0368(14) Uani 1 1 d . . .
H4 H 0.0438 -0.2186 0.4156 0.044 Uiso 1 1 calc R . .
C5 C 0.0414(3) -0.0210(7) 0.3021(6) 0.0309(12) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pb1 0.0303(2) 0.03680(19) 0.03370(18) 0.000 0.01449(14) 0.000
I1 0.0290(3) 0.0603(3) 0.0367(2) -0.00470(17) 0.01062(18) 0.00032(17)
O1 0.043(3) 0.043(2) 0.035(2) 0.0092(17) 0.0224(19) 0.0109(19)
N1 0.024(3) 0.042(3) 0.029(2) 0.0034(19) 0.013(2) 0.0013(19)
C1 0.029(4) 0.048(3) 0.045(3) -0.004(3) 0.017(3) -0.006(3)
C2 0.030(4) 0.067(4) 0.038(3) 0.001(3) 0.013(3) 0.008(3)
C3 0.038(4) 0.052(4) 0.033(3) 0.009(3) 0.014(3) 0.013(3)
C4 0.047(4) 0.036(3) 0.030(3) 0.002(2) 0.019(3) 0.001(3)
C5 0.026(3) 0.039(3) 0.027(2) 0.000(2) 0.011(2) 0.002(2)

_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 2.366(4) . ?
Pb1 O1 2.366(4) 2 ?
Pb1 I1 3.2063(13) 6_565 ?
Pb1 I1 3.2063(13) 5_566 ?
Pb1 I1 3.4841(8) 2 ?
Pb1 I1 3.4841(8) . ?
I1 Pb1 3.2063(13) 5_566 ?
O1 N1 1.317(6) . ?
N1 C1 1.332(8) . ?
N1 C5 1.379(7) . ?
C1 C2 1.389(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(8) . ?
C4 H4 0.9300 . ?
C5 C5 1.448(11) 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 O1 74.2(2) . 2 ?
O1 Pb1 I1 82.23(10) . 6_565 ?
O1 Pb1 I1 89.40(10) 2 6_565 ?
O1 Pb1 I1 89.40(10) . 5_566 ?
O1 Pb1 I1 82.23(10) 2 5_566 ?
I1 Pb1 I1 169.52(2) 6_565 5_566 ?
O1 Pb1 I1 79.12(10) . 2 ?
O1 Pb1 I1 153.18(10) 2 2 ?
I1 Pb1 I1 84.30(2) 6_565 2 ?
I1 Pb1 I1 100.36(2) 5_566 2 ?
O1 Pb1 I1 153.18(10) . . ?
O1 Pb1 I1 79.12(10) 2 . ?
I1 Pb1 I1 100.36(2) 6_565 . ?
I1 Pb1 I1 84.30(2) 5_566 . ?
I1 Pb1 I1 127.64(2) 2 . ?
Pb1 I1 Pb1 95.70(2) 5_566 . ?
N1 O1 Pb1 120.7(3) . . ?
O1 N1 C1 119.3(5) . . ?
O1 N1 C5 119.0(5) . . ?
C1 N1 C5 121.5(5) . . ?
N1 C1 C2 120.6(6) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.1(7) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.1(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.4(6) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 N1 118.3(5) . . ?
C4 C5 C5 121.8(5) . 2 ?
N1 C5 C5 119.9(4) . 2 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.881
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.170


data_1
_database_code_depnum_ccdc_archive 'CCDC 659647'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 I N O Pb, C3 H7 N O'
_chemical_formula_sum            'C12 H13 I N2 O2 Pb'
_chemical_formula_weight         551.34

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'
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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   16.872(5)
_cell_length_b                   7.2993(17)
_cell_length_c                   12.074(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.850(4)
_cell_angle_gamma                90.00
_cell_volume                     1415.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12
_cell_measurement_theta_max      18

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000.0
_exptl_absorpt_coefficient_mu    14.096
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.14
_exptl_absorpt_correction_T_max  0.250
_exptl_absorpt_process_details   
'TEXRAY software (Molecular Structure Corporation, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      -120.00
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotor target'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Weissenberg IP'
_diffrn_measurement_method       'scintillation counter'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            10536
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3253
_reflns_number_gt                2863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'TEXRAY software (Molecular Structure Corporation, 1999)'
_computing_cell_refinement       'TEXRAY software'
_computing_data_reduction        
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  "SHELXL-97/2 (Sheldrick,1997)')"

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0369P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3253
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.008897(13) 0.70046(3) 0.613069(18) 0.02558(9) Uani 1 1 d . . .
I1 I -0.09276(2) 1.07724(5) 0.58435(3) 0.03137(11) Uani 1 1 d . . .
O1 O -0.0787(2) 0.5859(5) 0.4424(3) 0.0281(9) Uani 1 1 d . . .
N1 N -0.1217(3) 0.5871(6) 0.6418(4) 0.0234(10) Uani 1 1 d . . .
N2 N -0.4173(4) 0.8660(9) 0.4382(6) 0.0509(16) Uani 1 1 d . . .
O2 O -0.5382(4) 0.7179(11) 0.4088(8) 0.107(3) Uani 1 1 d . . .
C1 C -0.1408(4) 0.5810(8) 0.7395(5) 0.0327(14) Uani 1 1 d . . .
H1 H -0.1014 0.6198 0.8078 0.039 Uiso 1 1 calc R . .
C2 C -0.2183(4) 0.5181(10) 0.7447(6) 0.0414(16) Uani 1 1 d . . .
H2 H -0.2294 0.5127 0.8154 0.050 Uiso 1 1 calc R . .
C3 C -0.2767(4) 0.4653(9) 0.6451(6) 0.0364(15) Uani 1 1 d . . .
H3 H -0.3282 0.4233 0.6475 0.044 Uiso 1 1 calc R . .
C4 C -0.2596(4) 0.4740(8) 0.5381(5) 0.0302(13) Uani 1 1 d . . .
C5 C -0.3173(4) 0.4253(9) 0.4303(6) 0.0380(15) Uani 1 1 d . . .
H5 H -0.3706 0.3870 0.4269 0.046 Uiso 1 1 calc R . .
C6 C -0.2953(4) 0.4343(9) 0.3322(6) 0.0389(16) Uani 1 1 d . . .
H6 H -0.3341 0.4030 0.2616 0.047 Uiso 1 1 calc R . .
C7 C -0.2152(4) 0.4899(8) 0.3337(5) 0.0330(14) Uani 1 1 d . . .
H7 H -0.2016 0.4932 0.2647 0.040 Uiso 1 1 calc R . .
C8 C -0.1564(3) 0.5395(7) 0.4367(5) 0.0264(12) Uani 1 1 d . . .
C9 C -0.1794(3) 0.5354(7) 0.5414(5) 0.0254(12) Uani 1 1 d . . .
C10 C -0.4705(6) 0.7677(14) 0.4698(9) 0.072(3) Uani 1 1 d . . .
H10 H -0.4551 0.7317 0.5474 0.086 Uiso 1 1 calc R . .
C11 C -0.3363(5) 0.9185(12) 0.5133(9) 0.076(3) Uani 1 1 d . . .
H11A H -0.3079 0.9887 0.4698 0.114 Uiso 1 1 calc R . .
H11B H -0.3045 0.8106 0.5437 0.114 Uiso 1 1 calc R . .
H11C H -0.3425 0.9911 0.5764 0.114 Uiso 1 1 calc R . .
C12 C -0.4367(7) 0.921(2) 0.3164(9) 0.111(5) Uani 1 1 d . . .
H12A H -0.3911 0.9899 0.3060 0.167 Uiso 1 1 calc R . .
H12B H -0.4862 0.9946 0.2949 0.167 Uiso 1 1 calc R . .
H12C H -0.4457 0.8133 0.2681 0.167 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pb1 0.02948(13) 0.01923(12) 0.02726(15) -0.00102(8) 0.00757(10) -0.00095(8)
I1 0.0372(2) 0.0233(2) 0.0354(2) 0.00263(16) 0.01378(17) 0.00501(16)
O1 0.033(2) 0.025(2) 0.027(2) -0.0003(17) 0.0093(17) 0.0012(17)
N1 0.028(2) 0.020(2) 0.024(3) -0.0036(19) 0.010(2) 0.0013(19)
N2 0.043(3) 0.049(4) 0.055(4) 0.001(3) 0.008(3) -0.007(3)
O2 0.048(4) 0.129(7) 0.139(8) 0.003(5) 0.023(4) -0.034(4)
C1 0.034(3) 0.031(3) 0.031(3) 0.003(3) 0.007(3) 0.003(3)
C2 0.046(4) 0.046(4) 0.040(4) 0.001(3) 0.023(3) -0.001(3)
C3 0.033(3) 0.033(3) 0.046(4) 0.002(3) 0.016(3) -0.005(3)
C4 0.032(3) 0.021(3) 0.038(4) 0.000(3) 0.010(3) 0.001(2)
C5 0.031(3) 0.032(3) 0.046(4) -0.006(3) 0.005(3) -0.007(3)
C6 0.036(3) 0.043(4) 0.034(4) -0.013(3) 0.004(3) -0.005(3)
C7 0.039(3) 0.031(3) 0.029(3) -0.002(3) 0.010(3) 0.002(3)
C8 0.029(3) 0.017(3) 0.031(3) 0.002(2) 0.004(2) 0.005(2)
C9 0.030(3) 0.015(3) 0.029(3) -0.005(2) 0.006(2) 0.004(2)
C10 0.065(6) 0.075(6) 0.080(7) 0.002(5) 0.030(5) -0.002(5)
C11 0.058(5) 0.052(5) 0.101(7) -0.002(5) -0.002(5) -0.011(4)
C12 0.107(9) 0.158(13) 0.067(7) 0.020(8) 0.023(6) -0.028(9)

_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 2.294(4) . ?
Pb1 N1 2.475(5) . ?
Pb1 O1 2.586(4) 3_566 ?
Pb1 I1 3.2033(7) . ?
O1 C8 1.336(7) . ?
O1 Pb1 2.586(4) 3_566 ?
N1 C1 1.316(8) . ?
N1 C9 1.355(7) . ?
N2 C10 1.294(11) . ?
N2 C11 1.441(9) . ?
N2 C12 1.461(12) . ?
O2 C10 1.210(10) . ?
C1 C2 1.406(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.355(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.411(8) . ?
C4 C9 1.415(8) . ?
C5 C6 1.347(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.432(8) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 N1 69.40(14) . . ?
O1 Pb1 O1 72.04(14) . 3_566 ?
N1 Pb1 O1 105.16(13) . 3_566 ?
O1 Pb1 I1 92.27(10) . . ?
N1 Pb1 I1 80.33(10) . . ?
O1 Pb1 I1 159.58(9) 3_566 . ?
C8 O1 Pb1 119.3(4) . . ?
C8 O1 Pb1 107.4(3) . 3_566 ?
Pb1 O1 Pb1 107.96(14) . 3_566 ?
C1 N1 C9 119.1(5) . . ?
C1 N1 Pb1 127.6(4) . . ?
C9 N1 Pb1 113.2(4) . . ?
C10 N2 C11 124.8(8) . . ?
C10 N2 C12 119.1(8) . . ?
C11 N2 C12 116.0(8) . . ?
N1 C1 C2 122.5(6) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.1(6) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.3(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 123.9(6) . . ?
C3 C4 C9 116.8(5) . . ?
C5 C4 C9 119.2(6) . . ?
C6 C5 C4 120.1(6) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.7(6) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 120.7(6) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
O1 C8 C7 122.4(6) . . ?
O1 C8 C9 119.2(5) . . ?
C7 C8 C9 118.4(5) . . ?
N1 C9 C4 122.2(5) . . ?
N1 C9 C8 118.0(5) . . ?
C4 C9 C8 119.9(5) . . ?
O2 C10 N2 126.7(10) . . ?
O2 C10 H10 116.7 . . ?
N2 C10 H10 116.7 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.335
_refine_diff_density_min         -2.525
_refine_diff_density_rms         0.221


