 
data_k306 
# Single crystal after exposed to 1 min UV light. Photoproduct  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H17 I2 N3 O Pb' 
_chemical_formula_weight          716.30 
  
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' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_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+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    8.3498(4) 
_cell_length_b                    20.1849(11) 
_cell_length_c                    12.2245(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  105.776(2) 
_cell_angle_gamma                 90 
_cell_volume                      1982.71(17) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     9879 
_cell_measurement_theta_min       2.66 
_cell_measurement_theta_max       29.52 
  
_exptl_crystal_description        Rod 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_density_diffrn     2.400 
_exptl_crystal_F_000              1296 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.559 
_exptl_crystal_size_mid           0.367 
_exptl_crystal_size_min           0.130 
_exptl_absorpt_coefficient_mu     11.627 
_shelx_estimated_absorpt_T_min    0.059 
_shelx_estimated_absorpt_T_max    0.313 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.013 
_exptl_absorpt_correction_T_max   0.235 
_exptl_absorpt_process_details    'SADABS (Sheldrick, 2015)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       298(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker D8 Venture' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             39541 
_diffrn_reflns_av_unetI/netI      0.0362 
_diffrn_reflns_av_R_equivalents   0.0558 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -28 
_diffrn_reflns_limit_k_max        28 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          2.659 
_diffrn_reflns_theta_max          29.666 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.994 
_diffrn_measured_fraction_theta_full  0.998 
_diffrn_reflns_Laue_measured_fraction_max    0.994 
_diffrn_reflns_Laue_measured_fraction_full   0.998 
_diffrn_reflns_point_group_measured_fraction_max   0.994 
_diffrn_reflns_point_group_measured_fraction_full  0.998 
_reflns_number_total              5575 
_reflns_number_gt                 4444 
_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-2014/7 (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)+(0.0450P)²+16.6831P] 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          5575 
_refine_ls_number_parameters      328 
_refine_ls_number_restraints      80 
_refine_ls_R_factor_all           0.0636 
_refine_ls_R_factor_gt            0.0460 
_refine_ls_wR_factor_ref          0.1219 
_refine_ls_wR_factor_gt           0.1105 
_refine_ls_goodness_of_fit_ref    1.061 
_refine_ls_restrained_S_all       1.055 
_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 0.72914(4) 0.53151(2) 0.93153(3) 0.04288(10) Uani 1 1 d . . . . . 
I1 I 0.56853(8) 0.39781(3) 0.98587(6) 0.05692(17) Uani 1 1 d . . . . . 
I2 I 0.97853(8) 0.44364(4) 0.83216(5) 0.06126(19) Uani 1 1 d . . . . . 
N1 N 0.545(3) 0.5360(13) 0.7286(18) 0.040(6) Uani 0.519(17) 1 d D . P A 1 
C1 C 0.588(3) 0.5721(12) 0.648(2) 0.062(8) Uani 0.519(17) 1 d D . P A 1 
H1 H 0.6923 0.5916 0.6673 0.075 Uiso 0.519(17) 1 calc R U P A 1 
N2 N 0.491(3) 0.5821(11) 0.542(2) 0.053(6) Uani 0.519(17) 1 d D . P A 1 
C2 C 0.339(3) 0.5523(14) 0.5190(17) 0.047(7) Uani 0.519(17) 1 d D . P A 1 
H2 H 0.2658 0.5592 0.4476 0.056 Uiso 0.519(17) 1 calc R U P A 1 
C3 C 0.2878(19) 0.5126(11) 0.5938(14) 0.039(4) Uani 0.519(17) 1 d D . P A 1 
C4 C 0.399(3) 0.5032(14) 0.6965(17) 0.040(6) Uani 0.519(17) 1 d D . P A 1 
H4 H 0.3729 0.4730 0.7468 0.048 Uiso 0.519(17) 1 calc R U P A 1 
C5 C 0.1138(19) 0.4851(9) 0.5671(13) 0.045(4) Uani 0.519(17) 1 d . . P A 1 
H5 H 0.1057 0.4512 0.6228 0.054 Uiso 0.519(17) 1 calc R U P A 1 
C6 C 0.0322(19) 0.4606(11) 0.4460(13) 0.048(5) Uani 0.519(17) 1 d . . P A 1 
H6 H 0.1017 0.4697 0.3948 0.058 Uiso 0.519(17) 1 calc R U P A 1 
C7 C -0.036(2) 0.3911(12) 0.4315(19) 0.058(6) Uani 0.519(17) 1 d D . P A 1 
C8 C -0.126(3) 0.3728(15) 0.321(2) 0.083(12) Uani 0.519(17) 1 d D . P A 1 
H8 H -0.1390 0.4029 0.2620 0.099 Uiso 0.519(17) 1 calc R U P A 1 
C9 C -0.196(4) 0.3102(14) 0.301(2) 0.095(13) Uani 0.519(17) 1 d D . P A 1 
H9 H -0.2523 0.2984 0.2266 0.114 Uiso 0.519(17) 1 calc R U P A 1 
C10 C -0.183(5) 0.2650(13) 0.387(2) 0.101(12) Uani 0.519(17) 1 d D . P A 1 
H10 H -0.2351 0.2240 0.3724 0.122 Uiso 0.519(17) 1 calc R U P A 1 
C11 C -0.092(6) 0.2820(14) 0.494(3) 0.095(17) Uani 0.519(17) 1 d D . P A 1 
H11 H -0.0808 0.2518 0.5532 0.114 Uiso 0.519(17) 1 calc R U P A 1 
C12 C -0.015(4) 0.3433(15) 0.517(2) 0.080(9) Uani 0.519(17) 1 d D . P A 1 
H12 H 0.0512 0.3527 0.5897 0.096 Uiso 0.519(17) 1 calc R U P A 1 
N1A N 0.518(4) 0.5279(15) 0.718(2) 0.048(8) Uani 0.481(17) 1 d D . P A 2 
C1A C 0.526(3) 0.5757(12) 0.6428(19) 0.047(6) Uani 0.481(17) 1 d D . P A 2 
H1A H 0.6084 0.6077 0.6658 0.057 Uiso 0.481(17) 1 calc R U P A 2 
N2A N 0.424(3) 0.5809(11) 0.5368(16) 0.043(5) Uani 0.481(17) 1 d D . P A 2 
C2A C 0.309(4) 0.5321(12) 0.507(2) 0.054(9) Uani 0.481(17) 1 d D . P A 2 
H2A H 0.2386 0.5324 0.4335 0.065 Uiso 0.481(17) 1 calc R U P A 2 
C3A C 0.289(2) 0.4825(11) 0.5787(15) 0.036(4) Uani 0.481(17) 1 d D . P A 2 
C4A C 0.395(4) 0.4826(15) 0.6845(19) 0.046(8) Uani 0.481(17) 1 d D . P A 2 
H4A H 0.3821 0.4505 0.7360 0.055 Uiso 0.481(17) 1 calc R U P A 2 
C5A C 0.164(2) 0.4274(10) 0.5500(16) 0.048(5) Uani 0.481(17) 1 d . . P A 2 
H5A H 0.1515 0.4013 0.6099 0.058 Uiso 0.481(17) 1 calc R U P A 2 
C6A C 0.070(3) 0.4127(11) 0.4468(15) 0.050(5) Uani 0.481(17) 1 d . . P A 2 
H6A H 0.0822 0.4390 0.3871 0.060 Uiso 0.481(17) 1 calc R U P A 2 
C7A C -0.048(2) 0.3610(10) 0.4189(14) 0.036(4) Uani 0.481(17) 1 d D . P A 2 
C8A C -0.158(3) 0.3577(12) 0.3098(17) 0.052(7) Uani 0.481(17) 1 d D . P A 2 
H8A H -0.1488 0.3885 0.2553 0.062 Uiso 0.481(17) 1 calc R U P A 2 
C9A C -0.280(3) 0.3093(11) 0.282(2) 0.065(7) Uani 0.481(17) 1 d D . P A 2 
H9A H -0.3575 0.3104 0.2107 0.079 Uiso 0.481(17) 1 calc R U P A 2 
C10A C -0.288(3) 0.2597(10) 0.357(2) 0.067(7) Uani 0.481(17) 1 d D . P A 2 
H10A H -0.3655 0.2257 0.3368 0.081 Uiso 0.481(17) 1 calc R U P A 2 
C11A C -0.179(3) 0.2615(14) 0.464(3) 0.074(11) Uani 0.481(17) 1 d D . P A 2 
H11A H -0.1837 0.2282 0.5160 0.089 Uiso 0.481(17) 1 calc R U P A 2 
C12A C -0.062(4) 0.3118(15) 0.497(2) 0.068(11) Uani 0.481(17) 1 d D . P A 2 
H12A H 0.0077 0.3128 0.5707 0.082 Uiso 0.481(17) 1 calc R U P A 2 
O1 O 0.8115(11) 0.6404(4) 0.8512(7) 0.079(2) Uani 1 1 d . . . . . 
C13 C 0.9272(15) 0.6788(6) 0.8931(10) 0.066(3) Uani 1 1 d . . . . . 
H13 H 1.0110 0.6638 0.9549 0.079 Uiso 1 1 calc R U . . . 
N3 N 0.9402(13) 0.7379(4) 0.8575(9) 0.073(3) Uani 1 1 d . . . . . 
C14 C 1.084(2) 0.7809(8) 0.9092(17) 0.128(7) Uani 1 1 d . . . . . 
H14A H 1.1276 0.7991 0.8505 0.192 Uiso 1 1 calc R U . . . 
H14B H 1.1691 0.7553 0.9606 0.192 Uiso 1 1 calc R U . . . 
H14C H 1.0495 0.8163 0.9501 0.192 Uiso 1 1 calc R U . . . 
C15 C 0.819(3) 0.7665(9) 0.7667(18) 0.146(8) Uani 1 1 d . . . . . 
H15A H 0.8649 0.7724 0.7032 0.219 Uiso 1 1 calc R U . . . 
H15B H 0.7867 0.8087 0.7897 0.219 Uiso 1 1 calc R U . . . 
H15C H 0.7242 0.7379 0.7451 0.219 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 N1 2.54(2) . ? 
Pb1 O1 2.575(7) . ? 
Pb1 N1A 2.72(2) . ? 
Pb1 I1 3.1633(7) . ? 
Pb1 I2 3.2145(7) . ? 
Pb1 I1 3.2554(7) 3_667 ? 
Pb1 I2 3.2742(7) 3_767 ? 
I1 Pb1 3.2554(7) 3_667 ? 
I2 Pb1 3.2742(7) 3_767 ? 
N1 C1 1.348(16) . ? 
N1 C4 1.352(16) . ? 
C1 N2 1.342(16) . ? 
N2 C2 1.359(16) . ? 
C2 C3 1.370(16) . ? 
C3 C4 1.355(15) . ? 
C3 C5 1.51(2) . ? 
C5 C6 1.53(2) . ? 
C5 C6 1.61(2) 3_566 ? 
C6 C7 1.51(3) . ? 
C6 C5 1.62(2) 3_566 ? 
C7 C12 1.40(2) . ? 
C7 C8 1.40(2) . ? 
C8 C9 1.39(2) . ? 
C9 C10 1.37(2) . ? 
C10 C11 1.37(2) . ? 
C11 C12 1.39(3) . ? 
N1A C1A 1.348(16) . ? 
N1A C4A 1.355(16) . ? 
C1A N2A 1.346(16) . ? 
N2A C2A 1.357(16) . ? 
C2A C3A 1.369(16) . ? 
C3A C4A 1.352(16) . ? 
C3A C5A 1.50(3) . ? 
C5A C6A 1.33(3) . ? 
C6A C7A 1.41(3) . ? 
C7A C8A 1.399(19) . ? 
C7A C12A 1.40(2) . ? 
C8A C9A 1.39(2) . ? 
C9A C10A 1.38(2) . ? 
C10A C11A 1.37(2) . ? 
C11A C12A 1.39(3) . ? 
O1 C13 1.237(13) . ? 
C13 N3 1.284(14) . ? 
N3 C15 1.405(19) . ? 
N3 C14 1.479(16) . ? 
  
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 O1 75.6(6) . . ? 
O1 Pb1 N1A 80.1(6) . . ? 
N1 Pb1 I1 93.3(6) . . ? 
O1 Pb1 I1 168.61(18) . . ? 
N1A Pb1 I1 88.7(5) . . ? 
N1 Pb1 I2 86.1(6) . . ? 
O1 Pb1 I2 93.4(2) . . ? 
N1A Pb1 I2 86.5(7) . . ? 
I1 Pb1 I2 87.93(2) . . ? 
N1 Pb1 I1 88.7(6) . 3_667 ? 
O1 Pb1 I1 92.9(2) . 3_667 ? 
N1A Pb1 I1 87.7(7) . 3_667 ? 
I1 Pb1 I1 84.591(18) . 3_667 ? 
I2 Pb1 I1 170.64(2) . 3_667 ? 
N1 Pb1 I2 164.6(6) . 3_767 ? 
O1 Pb1 I2 89.62(18) . 3_767 ? 
N1A Pb1 I2 169.2(5) . 3_767 ? 
I1 Pb1 I2 101.68(2) . 3_767 ? 
I2 Pb1 I2 90.793(18) . 3_767 ? 
I1 Pb1 I2 96.205(19) 3_667 3_767 ? 
Pb1 I1 Pb1 95.409(18) . 3_667 ? 
Pb1 I2 Pb1 89.209(18) . 3_767 ? 
C1 N1 C4 116.8(17) . . ? 
C1 N1 Pb1 121.5(16) . . ? 
C4 N1 Pb1 121.7(13) . . ? 
N2 C1 N1 125.2(17) . . ? 
C1 N2 C2 114.7(16) . . ? 
N2 C2 C3 124.2(17) . . ? 
C4 C3 C2 116.3(15) . . ? 
C4 C3 C5 121.7(17) . . ? 
C2 C3 C5 121.9(16) . . ? 
N1 C4 C3 122.4(16) . . ? 
C3 C5 C6 118.5(14) . . ? 
C3 C5 C6 115.4(15) . 3_566 ? 
C6 C5 C6 89.9(13) . 3_566 ? 
C7 C6 C5 118.0(16) . . ? 
C7 C6 C5 111.6(11) . 3_566 ? 
C5 C6 C5 90.1(13) . 3_566 ? 
C12 C7 C8 118(2) . . ? 
C12 C7 C6 126(2) . . ? 
C8 C7 C6 116(2) . . ? 
C9 C8 C7 120(2) . . ? 
C10 C9 C8 121(2) . . ? 
C11 C10 C9 118(3) . . ? 
C10 C11 C12 121(2) . . ? 
C11 C12 C7 121(2) . . ? 
C1A N1A C4A 116.6(18) . . ? 
C1A N1A Pb1 119.9(14) . . ? 
C4A N1A Pb1 123.4(14) . . ? 
N2A C1A N1A 125.4(17) . . ? 
C1A N2A C2A 114.7(17) . . ? 
N2A C2A C3A 123.9(19) . . ? 
C4A C3A C2A 116.9(17) . . ? 
C4A C3A C5A 117.1(17) . . ? 
C2A C3A C5A 126.0(17) . . ? 
C3A C4A N1A 122.4(17) . . ? 
C6A C5A C3A 125.7(18) . . ? 
C5A C6A C7A 126.1(18) . . ? 
C8A C7A C12A 118(2) . . ? 
C8A C7A C6A 119.8(18) . . ? 
C12A C7A C6A 122.6(17) . . ? 
C9A C8A C7A 121.1(18) . . ? 
C10A C9A C8A 121(2) . . ? 
C11A C10A C9A 119(2) . . ? 
C10A C11A C12A 122(2) . . ? 
C11A C12A C7A 120(2) . . ? 
C13 O1 Pb1 129.6(7) . . ? 
O1 C13 N3 124.8(11) . . ? 
C13 N3 C15 122.7(13) . . ? 
C13 N3 C14 122.3(13) . . ? 
C15 N3 C14 115.0(13) . . ? 
  
_refine_diff_density_max    1.311 
_refine_diff_density_min   -2.827 
_refine_diff_density_rms    0.204 
  
  
  
