# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
# 
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data_1
_audit_block_doi                 10.5517/cc13g8wq
_database_code_depnum_ccdc_archive 'CCDC 1026623'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;
_audit_creation_date             2016-01-21
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.01.04 svn.r3250 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I6 Pb2, C12 H21 N2, C12 H20 N2'
_chemical_formula_sum            'C24 H41 I6 N4 Pb2'
_chemical_formula_weight         1561.39
_chemical_melting_point          ?
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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   20.7859(13)
_cell_length_b                   8.8243(6)
_cell_length_c                   42.787(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7848.0(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.9755
_cell_measurement_theta_min      2.5523
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.309
_exptl_absorpt_correction_T_max  0.295
_exptl_absorpt_correction_T_min  0.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    2.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             5560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            50463
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.426
_diffrn_reflns_theta_min         0.952
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Smart CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6319
_reflns_number_total             9694
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.024
_refine_diff_density_min         -2.237
_refine_diff_density_rms         0.195
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         9694
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+65.0888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1075
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C8, N1, C3, C2, C4, C1, C5, N2, C6, C7, C9, C10, C11, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C24, N3, C15, C14, C16, C13, C17, N4, C18, C19, C20, C21, C22, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Riding coordinates:
 N1(H1A,H1B), N3(H3A,H3B), C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C18(H18A,H18B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B),
 C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.35076(2) -0.03992(4) 0.90148(2) 0.03634(10) Uani 1 1 d . . . . .
Pb2 Pb 0.34799(2) 0.55053(4) 0.84788(2) 0.03698(10) Uani 1 1 d . . . . .
I1 I 0.27949(4) -0.35553(8) 0.92122(2) 0.05031(19) Uani 1 1 d . . . . .
I2 I 0.42605(4) -0.00112(8) 0.96208(2) 0.05003(19) Uani 1 1 d . . . . .
I3 I 0.45761(4) -0.26607(8) 0.87894(2) 0.05229(19) Uani 1 1 d . . . . .
I4 I 0.41661(4) 0.24246(7) 0.86863(2) 0.05167(19) Uani 1 1 d . . . . .
I5 I 0.42400(4) 0.55446(8) 0.78713(2) 0.04948(18) Uani 1 1 d . . . . .
I6 I 0.28643(3) 0.87407(7) 0.82797(2) 0.04187(16) Uani 1 1 d . . . . .
N1 N 1.0244(5) -0.0931(12) 0.9400(2) 0.074(3) Uani 1 1 d . U . . .
H1A H 1.0455 -0.0350 0.9276 0.089 Uiso 1 1 d R . . . .
H1B H 1.0338 -0.1878 0.9412 0.089 Uiso 1 1 d R . . . .
N2 N 0.8769(4) 0.0815(9) 0.99373(19) 0.0412(18) Uani 1 1 d . U . . .
N3 N 0.4711(5) -0.0391(11) 0.8099(2) 0.060(3) Uani 1 1 d . U . . .
H3A H 0.4618 -0.1340 0.8100 0.072 Uiso 1 1 d R . . . .
H3B H 0.4487 0.0233 0.8209 0.072 Uiso 1 1 d R . . . .
N4 N 0.6186(4) 0.1230(9) 0.75615(19) 0.0412(18) Uani 1 1 d . U . . .
C1 C 0.9102(5) 0.1714(12) 0.9743(2) 0.046(2) Uani 1 1 d . U . . .
H1 H 0.8998 0.2738 0.9731 0.056 Uiso 1 1 calc R . . . .
C2 C 0.9589(6) 0.1157(13) 0.9563(3) 0.051(3) Uani 1 1 d . U . . .
H2 H 0.9811 0.1805 0.9430 0.061 Uiso 1 1 calc R . . . .
C3 C 0.9757(6) -0.0364(13) 0.9576(3) 0.052(2) Uani 1 1 d . U . . .
C4 C 0.9412(6) -0.1273(12) 0.9788(3) 0.052(3) Uani 1 1 d . U . . .
H4 H 0.9508 -0.2298 0.9806 0.062 Uiso 1 1 calc R . . . .
C5 C 0.8941(6) -0.0662(12) 0.9965(3) 0.049(2) Uani 1 1 d . U . . .
H5 H 0.8729 -0.1270 1.0109 0.059 Uiso 1 1 calc R . . . .
C6 C 0.8216(5) 0.1390(13) 1.0110(3) 0.051(2) Uani 1 1 d . U . . .
H6A H 0.8227 0.2489 1.0109 0.061 Uiso 1 1 calc R . . . .
H6B H 0.8245 0.1056 1.0325 0.061 Uiso 1 1 calc R . . . .
C7 C 0.7592(6) 0.0875(14) 0.9976(3) 0.060(3) Uani 1 1 d . U . . .
H7A H 0.7248 0.1304 1.0101 0.072 Uiso 1 1 calc R . . . .
H7B H 0.7568 -0.0218 0.9999 0.072 Uiso 1 1 calc R . . . .
C8 C 0.7464(7) 0.1259(16) 0.9640(3) 0.072(4) Uani 1 1 d . U . . .
H8A H 0.7460 0.2354 0.9620 0.087 Uiso 1 1 calc R . . . .
H8B H 0.7821 0.0884 0.9516 0.087 Uiso 1 1 calc R . . . .
C9 C 0.6860(6) 0.0661(14) 0.9505(3) 0.061(3) Uani 1 1 d . U . . .
H9A H 0.6861 -0.0432 0.9529 0.073 Uiso 1 1 calc R . . . .
H9B H 0.6503 0.1052 0.9626 0.073 Uiso 1 1 calc R . . . .
C10 C 0.6741(8) 0.102(2) 0.9172(4) 0.105(6) Uani 1 1 d . U . . .
H10A H 0.7107 0.0674 0.9051 0.126 Uiso 1 1 calc R . . . .
H10B H 0.6713 0.2107 0.9149 0.126 Uiso 1 1 calc R . . . .
C11 C 0.6143(10) 0.032(3) 0.9038(4) 0.134(8) Uani 1 1 d . U . . .
H11A H 0.5771 0.0783 0.9136 0.161 Uiso 1 1 calc R . . . .
H11B H 0.6138 -0.0750 0.9089 0.161 Uiso 1 1 calc R . . . .
C12 C 0.6085(10) 0.050(3) 0.8689(4) 0.146(8) Uani 1 1 d . U . . .
H12A H 0.5935 0.1500 0.8641 0.218 Uiso 1 1 d R . . . .
H12B H 0.5787 -0.0235 0.8607 0.218 Uiso 1 1 d R . . . .
H12C H 0.6500 0.0344 0.8596 0.218 Uiso 1 1 d R . . . .
C13 C 0.5818(5) 0.2171(11) 0.7737(2) 0.044(2) Uani 1 1 d . U . . .
H13 H 0.5899 0.3207 0.7729 0.053 Uiso 1 1 calc R . . . .
C14 C 0.5350(5) 0.1674(11) 0.7919(2) 0.046(2) Uani 1 1 d . U . . .
H14 H 0.5118 0.2355 0.8041 0.055 Uiso 1 1 calc R . . . .
C15 C 0.5201(5) 0.0108(12) 0.7931(2) 0.045(2) Uani 1 1 d . U . . .
C16 C 0.5575(5) -0.0854(12) 0.7748(2) 0.047(2) Uani 1 1 d . U . . .
H16 H 0.5496 -0.1891 0.7748 0.056 Uiso 1 1 calc R . . . .
C17 C 0.6059(5) -0.0272(11) 0.7569(3) 0.046(2) Uani 1 1 d . U . . .
H17 H 0.6307 -0.0927 0.7449 0.055 Uiso 1 1 calc R . . . .
C18 C 0.6754(5) 0.1803(13) 0.7383(3) 0.051(2) Uani 1 1 d . U . . .
H18A H 0.6733 0.1436 0.7170 0.061 Uiso 1 1 calc R . . . .
H18B H 0.6742 0.2902 0.7378 0.061 Uiso 1 1 calc R . . . .
C19 C 0.7371(5) 0.1300(13) 0.7528(3) 0.054(3) Uani 1 1 d . U . . .
H19 H 0.7683 0.0810 0.7410 0.065 Uiso 1 1 calc R . . . .
C20 C 0.7471(7) 0.1595(16) 0.7859(3) 0.071(3) Uani 1 1 d . U . . .
H20A H 0.7121 0.1136 0.7975 0.085 Uiso 1 1 calc R . . . .
H20B H 0.7448 0.2681 0.7893 0.085 Uiso 1 1 calc R . . . .
C21 C 0.8097(7) 0.1028(17) 0.7994(3) 0.080(4) Uani 1 1 d . U . . .
H21A H 0.8448 0.1571 0.7895 0.096 Uiso 1 1 calc R . . . .
H21B H 0.8144 -0.0036 0.7941 0.096 Uiso 1 1 calc R . . . .
C22 C 0.8159(10) 0.120(3) 0.8346(4) 0.142(8) Uani 1 1 d . U . . .
H22A H 0.8169 0.2272 0.8396 0.171 Uiso 1 1 calc R . . . .
H22B H 0.7779 0.0772 0.8444 0.171 Uiso 1 1 calc R . . . .
C23 C 0.8729(11) 0.048(3) 0.8481(5) 0.153(9) Uani 1 1 d . U . . .
H23A H 0.9103 0.1089 0.8431 0.184 Uiso 1 1 calc R . . . .
H23B H 0.8787 -0.0505 0.8384 0.184 Uiso 1 1 calc R . . . .
C24 C 0.8700(12) 0.027(3) 0.8826(5) 0.194(12) Uani 1 1 d . U . . .
H24A H 0.8494 0.1132 0.8920 0.292 Uiso 1 1 d R . . . .
H24B H 0.8458 -0.0628 0.8873 0.292 Uiso 1 1 d R . . . .
H24C H 0.9128 0.0171 0.8908 0.292 Uiso 1 1 d R . . . .


_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 I1 3.2656(8) . ?
Pb1 I1 3.2696(8) 7_665 ?
Pb1 I2 3.0479(8) . ?
Pb1 I3 3.1377(9) . ?
Pb1 I4 3.1715(8) . ?
Pb2 I3 3.0946(9) 1_565 ?
Pb2 I4 3.1957(8) . ?
Pb2 I5 3.0419(8) . ?
Pb2 I6 3.2426(8) . ?
Pb2 I6 3.3101(8) 7_655 ?
I1 Pb1 3.2696(8) 7_655 ?
I3 Pb2 3.0947(8) 1_545 ?
I6 Pb2 3.3101(8) 7_665 ?
N1 H1A 0.8598 . ?
N1 H1B 0.8601 . ?
N1 C3 1.357(14) . ?
N2 C1 1.341(12) . ?
N2 C5 1.357(13) . ?
N2 C6 1.458(13) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8599 . ?
N3 C15 1.324(13) . ?
N4 C13 1.356(12) . ?
N4 C17 1.352(12) . ?
N4 C18 1.493(13) . ?
C1 H1 0.9300 . ?
C1 C2 1.363(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(15) . ?
C3 C4 1.407(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.350(15) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.488(16) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.500(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.480(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.478(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.50(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.51(2) . ?
C12 H12A 0.9601 . ?
C12 H12B 0.9602 . ?
C12 H12C 0.9601 . ?
C13 H13 0.9300 . ?
C13 C14 1.322(14) . ?
C14 H14 0.9300 . ?
C14 C15 1.417(14) . ?
C15 C16 1.392(14) . ?
C16 H16 0.9300 . ?
C16 C17 1.364(15) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.491(15) . ?
C19 H19 0.9300 . ?
C19 C20 1.455(16) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.508(18) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.52(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.46(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.49(3) . ?
C24 H24A 0.9601 . ?
C24 H24B 0.9599 . ?
C24 H24C 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
I1 Pb1 I1 88.969(14) . 7_665 ?
I2 Pb1 I1 98.60(2) . 7_665 ?
I2 Pb1 I1 96.24(2) . . ?
I2 Pb1 I3 88.25(2) . . ?
I2 Pb1 I4 93.85(2) . . ?
I3 Pb1 I1 169.11(2) . 7_665 ?
I3 Pb1 I1 81.85(2) . . ?
I3 Pb1 I4 93.33(2) . . ?
I4 Pb1 I1 94.63(2) . 7_665 ?
I4 Pb1 I1 168.65(2) . . ?
I3 Pb2 I4 89.83(2) 1_565 . ?
I3 Pb2 I6 86.73(2) 1_565 . ?
I3 Pb2 I6 167.96(2) 1_565 7_655 ?
I4 Pb2 I6 176.47(2) . . ?
I4 Pb2 I6 92.75(2) . 7_655 ?
I5 Pb2 I3 88.77(2) . 1_565 ?
I5 Pb2 I4 90.87(2) . . ?
I5 Pb2 I6 88.30(2) . . ?
I5 Pb2 I6 102.94(2) . 7_655 ?
I6 Pb2 I6 90.773(14) . 7_655 ?
Pb1 I1 Pb1 137.16(3) . 7_655 ?
Pb2 I3 Pb1 86.76(2) 1_545 . ?
Pb1 I4 Pb2 126.79(3) . . ?
Pb2 I6 Pb2 132.82(2) . 7_665 ?
H1A N1 H1B 120.0 . . ?
C3 N1 H1A 120.3 . . ?
C3 N1 H1B 119.7 . . ?
C1 N2 C5 119.1(9) . . ?
C1 N2 C6 121.0(9) . . ?
C5 N2 C6 119.9(9) . . ?
H3A N3 H3B 120.0 . . ?
C15 N3 H3A 119.9 . . ?
C15 N3 H3B 120.1 . . ?
C13 N4 C18 121.4(9) . . ?
C17 N4 C13 118.5(9) . . ?
C17 N4 C18 120.0(9) . . ?
N2 C1 H1 119.4 . . ?
N2 C1 C2 121.3(10) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.9(11) . . ?
C3 C2 H2 119.6 . . ?
N1 C3 C2 121.5(11) . . ?
N1 C3 C4 121.8(11) . . ?
C2 C3 C4 116.6(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(10) . . ?
C5 C4 H4 119.9 . . ?
N2 C5 H5 119.1 . . ?
C4 C5 N2 121.7(10) . . ?
C4 C5 H5 119.1 . . ?
N2 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
N2 C6 C7 112.8(9) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 108.1 . . ?
C6 C7 H7B 108.1 . . ?
C6 C7 C8 116.9(10) . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 C7 116.4(11) . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 C8 116.4(12) . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C9 C10 C11 115.0(15) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C10 C11 C12 113.9(17) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 110.0 . . ?
C11 C12 H12C 108.9 . . ?
H12A C12 H12B 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13 118.7 . . ?
C14 C13 N4 122.6(10) . . ?
C14 C13 H13 118.7 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(10) . . ?
C15 C14 H14 119.8 . . ?
N3 C15 C14 120.8(10) . . ?
N3 C15 C16 122.3(10) . . ?
C16 C15 C14 116.9(10) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(10) . . ?
C17 C16 H16 120.1 . . ?
N4 C17 C16 121.8(10) . . ?
N4 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
N4 C18 H18A 109.3 . . ?
N4 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 N4 111.5(9) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.3(10) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
C19 C20 C21 115.9(12) . . ?
H20A C20 H20B 107.4 . . ?
C21 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C20 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
C20 C21 C22 114.7(14) . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 C21 114.6(19) . . ?
C23 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C22 C23 C24 114(2) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C23 C24 H24A 109.6 . . ?
C23 C24 H24B 109.3 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 C3 C4 C5 178.3(11) . . . . ?
N2 C1 C2 C3 -0.1(18) . . . . ?
N2 C6 C7 C8 -57.5(15) . . . . ?
N3 C15 C16 C17 177.4(11) . . . . ?
N4 C13 C14 C15 -1.9(17) . . . . ?
N4 C18 C19 C20 -52.7(15) . . . . ?
C1 N2 C5 C4 -4.2(16) . . . . ?
C1 N2 C6 C7 104.1(12) . . . . ?
C1 C2 C3 N1 -179.5(11) . . . . ?
C1 C2 C3 C4 -1.6(17) . . . . ?
C2 C3 C4 C5 0.4(17) . . . . ?
C3 C4 C5 N2 2.5(18) . . . . ?
C5 N2 C1 C2 2.9(16) . . . . ?
C5 N2 C6 C7 -73.7(13) . . . . ?
C6 N2 C1 C2 -175.0(10) . . . . ?
C6 N2 C5 C4 173.7(10) . . . . ?
C6 C7 C8 C9 176.4(11) . . . . ?
C7 C8 C9 C10 -178.9(14) . . . . ?
C8 C9 C10 C11 176.8(16) . . . . ?
C9 C10 C11 C12 -171.1(18) . . . . ?
C13 N4 C17 C16 -0.2(16) . . . . ?
C13 N4 C18 C19 108.0(11) . . . . ?
C13 C14 C15 N3 -176.3(11) . . . . ?
C13 C14 C15 C16 1.2(17) . . . . ?
C14 C15 C16 C17 -0.1(17) . . . . ?
C15 C16 C17 N4 -0.4(17) . . . . ?
C17 N4 C13 C14 1.4(16) . . . . ?
C17 N4 C18 C19 -66.9(13) . . . . ?
C18 N4 C13 C14 -173.6(10) . . . . ?
C18 N4 C17 C16 174.9(10) . . . . ?
C18 C19 C20 C21 178.6(11) . . . . ?
C19 C20 C21 C22 -173.8(15) . . . . ?
C20 C21 C22 C23 172.6(18) . . . . ?
C21 C22 C23 C24 -164(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/cc13g8xr
_database_code_depnum_ccdc_archive 'CCDC 1026624'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;
_audit_creation_date             2016-01-21
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.01.04 svn.r3250 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I6 Pb2, 2(C12 H21 N2)'
_chemical_formula_sum            'C24 H42 I6 N4 Pb2'
_chemical_formula_weight         1562.39
_chemical_melting_point          ?
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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   21.089(3)
_cell_length_b                   8.9287(11)
_cell_length_c                   42.348(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7974.0(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    393(2)
_cell_measurement_theta_max      23.5418
_cell_measurement_theta_min      2.5217
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.099
_exptl_absorpt_correction_T_max  0.298
_exptl_absorpt_correction_T_min  0.046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    2.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             5568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1788
_diffrn_reflns_av_unetI/netI     0.1243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            79927
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.650
_diffrn_reflns_theta_min         0.962
_diffrn_ambient_temperature      393.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Smart CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4195
_reflns_number_total             9246
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.078
_refine_diff_density_min         -2.262
_refine_diff_density_rms         0.284
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         9246
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.1912
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+9.7067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C6, N1, H1A, H1B, C3, C2, C4, C1, H2, H4, C5, N2, H1, H5, H6A, H6B, C7, H7A,
 H7B, C8, H8A, H8B, C9, H9A, H9B, C10, H10A, H10B, C11, H11A, H11B, C12, H12A,
 H12B, H12C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20, N3, H3A, H3B, C15, C14, C16, C13, H14, H16, C17, N4, H13, H17, C18, H18A,
  H18B, C19, H19A, H19B, H20A, H20B, C21, H21A, H21B, C22, H22A, H22B, C23,
 H23A, H23B, C24, H24A, H24B, H24C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N3(H3A,H3B)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.84624(3) 0.44978(6) 0.84785(2) 0.0559(2) Uani 1 1 d . . . . .
Pb2 Pb 0.84850(3) 0.03956(6) 0.90186(2) 0.0549(2) Uani 1 1 d . . . . .
I1 I 0.78504(5) 0.12987(11) 0.82801(2) 0.0649(3) Uani 1 1 d . . . . .
I2 I 0.92064(6) 0.44626(11) 0.78670(3) 0.0799(4) Uani 1 1 d . . . . .
I3 I 0.91204(7) 0.75821(11) 0.86875(3) 0.0819(4) Uani 1 1 d . . . . .
I4 I 0.95265(7) 0.26623(13) 0.87924(3) 0.0872(4) Uani 1 1 d . . . . .
I5 I 0.92220(6) 0.00150(13) 0.96287(3) 0.0827(4) Uani 1 1 d . . . . .
I6 I 0.77794(6) 0.35269(12) 0.92176(3) 0.0779(4) Uani 1 1 d . . . . .
N1 N 0.4709(7) 0.5387(16) 0.6888(4) 0.105(5) Uani 1 1 d . U . . .
H1A H 0.4481 0.4767 0.6783 0.126 Uiso 1 1 calc R U . . .
H1B H 0.4627 0.6330 0.6881 0.126 Uiso 1 1 calc R U . . .
N2 N 0.6175(6) 0.3821(13) 0.7431(3) 0.067(3) Uani 1 1 d . U . . .
N3 N 0.5252(8) 1.0921(19) 0.9395(4) 0.128(6) Uani 1 1 d . U . . .
H3A H 0.5465 1.0341 0.9272 0.154 Uiso 1 1 calc R U . . .
H3B H 0.5347 1.1856 0.9408 0.154 Uiso 1 1 calc R U . . .
N4 N 0.3783(7) 0.9238(14) 0.9922(3) 0.076(4) Uani 1 1 d . U . . .
C1 C 0.5808(8) 0.2895(17) 0.7257(3) 0.068(4) Uani 1 1 d . U . . .
H1 H 0.5891 0.1872 0.7263 0.081 Uiso 1 1 calc R U . . .
C2 C 0.5340(8) 0.3377(17) 0.7081(4) 0.071(4) Uani 1 1 d . U . . .
H2 H 0.5105 0.2684 0.6967 0.085 Uiso 1 1 calc R U . . .
C3 C 0.5179(9) 0.4899(19) 0.7059(4) 0.078(5) Uani 1 1 d . U . . .
C4 C 0.5564(8) 0.5856(18) 0.7246(4) 0.076(5) Uani 1 1 d . U . . .
H4 H 0.5489 0.6883 0.7244 0.091 Uiso 1 1 calc R U . . .
C5 C 0.6033(8) 0.5308(18) 0.7426(4) 0.077(5) Uani 1 1 d . U . . .
H5 H 0.6268 0.5961 0.7551 0.092 Uiso 1 1 calc R U . . .
C6 C 0.6725(8) 0.3244(19) 0.7602(4) 0.084(4) Uani 1 1 d . U . . .
H6A H 0.6696 0.2160 0.7611 0.101 Uiso 1 1 calc R U . . .
H6B H 0.6714 0.3620 0.7816 0.101 Uiso 1 1 calc R U . . .
C7 C 0.7331(9) 0.366(2) 0.7458(5) 0.102(6) Uani 1 1 d . U . . .
H7A H 0.7395 0.4714 0.7499 0.122 Uiso 1 1 calc R U . . .
H7B H 0.7659 0.3124 0.7573 0.122 Uiso 1 1 calc R U . . .
C8 C 0.7449(11) 0.343(3) 0.7134(5) 0.133(8) Uani 1 1 d . U . . .
H8A H 0.7106 0.3918 0.7021 0.159 Uiso 1 1 calc R U . . .
H8B H 0.7402 0.2363 0.7096 0.159 Uiso 1 1 calc R U . . .
C9 C 0.8029(12) 0.388(3) 0.6981(6) 0.136(8) Uani 1 1 d . U . . .
H9A H 0.8074 0.4943 0.7022 0.163 Uiso 1 1 calc R U . . .
H9B H 0.8369 0.3389 0.7096 0.163 Uiso 1 1 calc R U . . .
C10 C 0.8165(17) 0.369(5) 0.6673(8) 0.244(17) Uani 1 1 d . U . . .
H10A H 0.7827 0.4162 0.6554 0.292 Uiso 1 1 calc R U . . .
H10B H 0.8143 0.2627 0.6630 0.292 Uiso 1 1 calc R U . . .
C11 C 0.873(2) 0.420(5) 0.6554(9) 0.258(19) Uani 1 1 d . U . . .
H11A H 0.9040 0.3417 0.6575 0.310 Uiso 1 1 calc R U . . .
H11B H 0.8866 0.5042 0.6682 0.310 Uiso 1 1 calc R U . . .
C12 C 0.871(2) 0.467(6) 0.6233(10) 0.34(3) Uani 1 1 d . U . . .
H12A H 0.8909 0.3922 0.6104 0.506 Uiso 1 1 calc GR U . . .
H12B H 0.8937 0.5600 0.6212 0.506 Uiso 1 1 calc GR U . . .
H12C H 0.8280 0.4806 0.6168 0.506 Uiso 1 1 calc GR U . . .
C13 C 0.3957(8) 1.0713(17) 0.9956(4) 0.074(4) Uani 1 1 d . U . . .
H13 H 0.3745 1.1307 1.0102 0.089 Uiso 1 1 calc R U . . .
C14 C 0.4419(8) 1.1308(18) 0.9785(4) 0.078(4) Uani 1 1 d . U . . .
H14 H 0.4517 1.2320 0.9804 0.093 Uiso 1 1 calc R U . . .
C15 C 0.4771(9) 1.0367(19) 0.9566(4) 0.085(5) Uani 1 1 d . U . . .
C16 C 0.4598(8) 0.8877(19) 0.9555(4) 0.079(5) Uani 1 1 d . U . . .
H16 H 0.4815 0.8233 0.9420 0.095 Uiso 1 1 calc R U . . .
C17 C 0.4136(8) 0.8352(18) 0.9729(4) 0.081(5) Uani 1 1 d . U . . .
H17 H 0.4045 0.7333 0.9720 0.098 Uiso 1 1 calc R U . . .
C18 C 0.3220(9) 0.865(2) 1.0094(4) 0.090(5) Uani 1 1 d . U . . .
H18A H 0.3243 0.7561 1.0097 0.108 Uiso 1 1 calc R U . . .
H18B H 0.3236 0.8992 1.0311 0.108 Uiso 1 1 calc R U . . .
C19 C 0.2617(10) 0.908(2) 0.9959(5) 0.112(6) Uani 1 1 d . U . . .
H19A H 0.2285 0.8573 1.0075 0.134 Uiso 1 1 calc R U . . .
H19B H 0.2563 1.0149 0.9995 0.134 Uiso 1 1 calc R U . . .
C20 C 0.2518(11) 0.881(3) 0.9633(5) 0.129(7) Uani 1 1 d . U . . .
H20A H 0.2557 0.7739 0.9598 0.155 Uiso 1 1 calc R U . . .
H20B H 0.2859 0.9289 0.9517 0.155 Uiso 1 1 calc R U . . .
C21 C 0.1913(11) 0.930(3) 0.9492(6) 0.129(7) Uani 1 1 d . U . . .
H21A H 0.1577 0.8882 0.9622 0.155 Uiso 1 1 calc R U . . .
H21B H 0.1892 1.0378 0.9517 0.155 Uiso 1 1 calc R U . . .
C22 C 0.1752(16) 0.898(4) 0.9167(7) 0.209(15) Uani 1 1 d . U . . .
H22A H 0.2087 0.9372 0.9034 0.251 Uiso 1 1 calc R U . . .
H22B H 0.1747 0.7901 0.9140 0.251 Uiso 1 1 calc R U . . .
C23 C 0.117(2) 0.955(5) 0.9056(9) 0.28(2) Uani 1 1 d . U . . .
H23A H 0.1146 1.0610 0.9103 0.336 Uiso 1 1 calc R U . . .
H23B H 0.0825 0.9054 0.9166 0.336 Uiso 1 1 calc R U . . .
C24 C 0.110(2) 0.932(6) 0.8713(10) 0.33(3) Uani 1 1 d . U . . .
H24A H 0.0856 1.0124 0.8625 0.490 Uiso 1 1 calc GR U . . .
H24B H 0.0883 0.8386 0.8675 0.490 Uiso 1 1 calc GR U . . .
H24C H 0.1509 0.9288 0.8616 0.490 Uiso 1 1 calc GR 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 I1 3.2451(11) . ?
Pb1 I1 3.3100(12) 7_765 ?
Pb1 I2 3.0280(13) . ?
Pb1 I3 3.2082(12) . ?
Pb1 I4 3.0804(14) . ?
Pb2 I3 3.1738(12) 1_545 ?
Pb2 I4 3.1365(14) . ?
Pb2 I5 3.0342(13) . ?
Pb2 I6 3.2564(13) 7_755 ?
Pb2 I6 3.2773(12) . ?
I1 Pb1 3.3099(12) 7_755 ?
I3 Pb2 3.1738(12) 1_565 ?
I6 Pb2 3.2565(13) 7_765 ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C3 1.30(2) . ?
N2 C1 1.351(18) . ?
N2 C5 1.361(18) . ?
N2 C6 1.460(19) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C15 1.34(2) . ?
N4 C13 1.374(18) . ?
N4 C17 1.361(19) . ?
N4 C18 1.49(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.309(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.40(2) . ?
C3 C4 1.42(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.34(2) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.46(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.41(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.44(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.35(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.37(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.42(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.33(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.45(2) . ?
C15 C16 1.38(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.31(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.45(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.42(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.47(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.45(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.41(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.48(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
I1 Pb1 I1 91.67(2) . 7_765 ?
I2 Pb1 I1 102.79(3) . 7_765 ?
I2 Pb1 I1 88.60(3) . . ?
I2 Pb1 I3 91.19(3) . . ?
I2 Pb1 I4 89.20(4) . . ?
I3 Pb1 I1 177.45(4) . . ?
I3 Pb1 I1 90.85(3) . 7_765 ?
I4 Pb1 I1 167.77(4) . 7_765 ?
I4 Pb1 I1 86.17(3) . . ?
I4 Pb1 I3 91.29(4) . . ?
I3 Pb2 I6 168.69(3) 1_545 . ?
I3 Pb2 I6 93.13(4) 1_545 7_755 ?
I4 Pb2 I3 94.60(4) . 1_545 ?
I4 Pb2 I6 169.44(4) . 7_755 ?
I4 Pb2 I6 81.14(4) . . ?
I5 Pb2 I3 94.08(4) . 1_545 ?
I5 Pb2 I4 88.48(4) . . ?
I5 Pb2 I6 98.15(4) . 7_755 ?
I5 Pb2 I6 96.27(3) . . ?
I6 Pb2 I6 89.93(2) 7_755 . ?
Pb1 I1 Pb1 133.99(4) . 7_755 ?
Pb2 I3 Pb1 128.22(5) 1_565 . ?
Pb1 I4 Pb2 87.99(4) . . ?
Pb2 I6 Pb2 137.93(4) 7_765 . ?
H1A N1 H1B 120.0 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
C1 N2 C5 117.6(14) . . ?
C1 N2 C6 120.6(13) . . ?
C5 N2 C6 121.7(14) . . ?
H3A N3 H3B 120.0 . . ?
C15 N3 H3A 120.0 . . ?
C15 N3 H3B 120.0 . . ?
C13 N4 C18 120.1(14) . . ?
C17 N4 C13 118.3(15) . . ?
C17 N4 C18 121.6(14) . . ?
N2 C1 H1 118.6 . . ?
C2 C1 N2 122.7(15) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 118.7 . . ?
C1 C2 C3 122.6(16) . . ?
C3 C2 H2 118.7 . . ?
N1 C3 C2 123.1(17) . . ?
N1 C3 C4 122.9(16) . . ?
C2 C3 C4 113.9(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(16) . . ?
C5 C4 H4 119.4 . . ?
N2 C5 H5 119.1 . . ?
C4 C5 N2 121.8(17) . . ?
C4 C5 H5 119.1 . . ?
N2 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
N2 C6 C7 113.5(14) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 107.0 . . ?
C6 C7 H7B 107.0 . . ?
H7A C7 H7B 106.7 . . ?
C8 C7 C6 121.5(19) . . ?
C8 C7 H7A 107.0 . . ?
C8 C7 H7B 107.0 . . ?
C7 C8 H8A 106.5 . . ?
C7 C8 H8B 106.5 . . ?
C7 C8 C9 123(2) . . ?
H8A C8 H8B 106.5 . . ?
C9 C8 H8A 106.5 . . ?
C9 C8 H8B 106.5 . . ?
C8 C9 H9A 105.9 . . ?
C8 C9 H9B 105.9 . . ?
H9A C9 H9B 106.3 . . ?
C10 C9 C8 126(3) . . ?
C10 C9 H9A 105.9 . . ?
C10 C9 H9B 105.9 . . ?
C9 C10 H10A 107.3 . . ?
C9 C10 H10B 107.3 . . ?
C9 C10 C11 120(4) . . ?
H10A C10 H10B 106.9 . . ?
C11 C10 H10A 107.3 . . ?
C11 C10 H10B 107.3 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 116(4) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13 119.2 . . ?
C14 C13 N4 121.6(16) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.5(16) . . ?
C15 C14 H14 120.3 . . ?
N3 C15 C14 121.2(17) . . ?
N3 C15 C16 122.4(18) . . ?
C16 C15 C14 116.4(17) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(17) . . ?
C17 C16 H16 119.3 . . ?
N4 C17 H17 118.7 . . ?
C16 C17 N4 122.5(16) . . ?
C16 C17 H17 118.7 . . ?
N4 C18 H18A 108.7 . . ?
N4 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 N4 114.4(15) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 107.8 . . ?
C18 C19 H19B 107.8 . . ?
H19A C19 H19B 107.2 . . ?
C20 C19 C18 117.9(19) . . ?
C20 C19 H19A 107.8 . . ?
C20 C19 H19B 107.8 . . ?
C19 C20 H20A 107.8 . . ?
C19 C20 H20B 107.8 . . ?
C19 C20 C21 118(2) . . ?
H20A C20 H20B 107.1 . . ?
C21 C20 H20A 107.8 . . ?
C21 C20 H20B 107.8 . . ?
C20 C21 H21A 106.8 . . ?
C20 C21 H21B 106.8 . . ?
H21A C21 H21B 106.7 . . ?
C22 C21 C20 122(2) . . ?
C22 C21 H21A 106.8 . . ?
C22 C21 H21B 106.8 . . ?
C21 C22 H22A 108.1 . . ?
C21 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C23 C22 C21 117(3) . . ?
C23 C22 H22A 108.1 . . ?
C23 C22 H22B 108.1 . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C22 C23 C24 112(4) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 C3 C4 C5 178.1(17) . . . . ?
N2 C1 C2 C3 0(3) . . . . ?
N2 C6 C7 C8 -50(3) . . . . ?
N3 C15 C16 C17 178.5(19) . . . . ?
N4 C13 C14 C15 -3(3) . . . . ?
N4 C18 C19 C20 53(3) . . . . ?
C1 N2 C5 C4 -3(2) . . . . ?
C1 N2 C6 C7 106.6(18) . . . . ?
C1 C2 C3 N1 -179.0(18) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C3 C4 C5 N2 2(3) . . . . ?
C5 N2 C1 C2 2(2) . . . . ?
C5 N2 C6 C7 -70(2) . . . . ?
C6 N2 C1 C2 -174.7(15) . . . . ?
C6 N2 C5 C4 173.7(16) . . . . ?
C6 C7 C8 C9 177(2) . . . . ?
C7 C8 C9 C10 -180(3) . . . . ?
C8 C9 C10 C11 178(4) . . . . ?
C9 C10 C11 C12 -149(4) . . . . ?
C13 N4 C17 C16 -6(3) . . . . ?
C13 N4 C18 C19 76(2) . . . . ?
C13 C14 C15 N3 -178.3(18) . . . . ?
C13 C14 C15 C16 -1(3) . . . . ?
C14 C15 C16 C17 1(3) . . . . ?
C15 C16 C17 N4 2(3) . . . . ?
C17 N4 C13 C14 6(2) . . . . ?
C17 N4 C18 C19 -104(2) . . . . ?
C18 N4 C13 C14 -173.6(16) . . . . ?
C18 N4 C17 C16 173.8(17) . . . . ?
C18 C19 C20 C21 -178.0(19) . . . . ?
C19 C20 C21 C22 -176(3) . . . . ?
C20 C21 C22 C23 -178(3) . . . . ?
C21 C22 C23 C24 173(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11
_audit_block_doi                 10.5517/cc13g8ys
_database_code_depnum_ccdc_archive 'CCDC 1026625'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;
_audit_creation_date             2016-01-21
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.01.04 svn.r3250 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I6 Pb2, 2(C12 H21 N2)'
_chemical_formula_sum            'C24 H42 I6 N4 Pb2'
_chemical_formula_weight         1562.39
_chemical_melting_point          ?
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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9573(17)
_cell_length_b                   14.924(3)
_cell_length_c                   15.212(3)
_cell_angle_alpha                84.535(5)
_cell_angle_beta                 86.831(5)
_cell_angle_gamma                89.177(5)
_cell_volume                     2021.1(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3810
_cell_measurement_temperature    413(2)
_cell_measurement_theta_max      21.6094
_cell_measurement_theta_min      2.5825
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.920
_exptl_absorpt_correction_T_max  0.289
_exptl_absorpt_correction_T_min  0.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    2.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.1511
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16200
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.829
_diffrn_ambient_temperature      413.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Smart CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3381
_reflns_number_total             6880
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.770
_refine_diff_density_min         -2.144
_refine_diff_density_rms         0.283
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6880
_refine_ls_number_restraints     1014
_refine_ls_R_factor_all          0.1836
_refine_ls_R_factor_gt           0.0820
_refine_ls_restrained_S_all      0.883
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1178P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1923
_refine_ls_wR_factor_ref         0.2239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-C20' = C19'-C21' = C20'-C22' = C21'-C23' = C22'-C24'
 2.66 with sigma of 0.02
 C18-C19' = C19'-C20' = C20'-C21' = C21'-C22' = C22'-C23'
 1.5 with sigma of 0.02
 C20-C21 = C21-C22 = C22-C23 = C23-C24 = C18-C19 = C19-C20
 1.5 with sigma of 0.02
 C7-C8 = C8-C9 = C9-C10 = C10-C11 = C19-C18 = C11-C12
 1.5 with sigma of 0.02
 C7-C9 = C9-C11 = C20-C22 = C22-C24 = C18-C20 = C19-C21 = C8-C10
 2.66 with sigma of 0.02
 C10-C12 = C10'-C12' = C8'-C10' = C9'-C11' = C7'-C9'
 2.66 with sigma of 0.02
 C6-C7' = C23'-C24'
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C7' \\sim C8
\\sim C8' \\sim C9 \\sim C9' \\sim C10 \\sim C10' \\sim C11 \\sim C11' \\sim
C12 \\sim C12' \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18
\\sim C19 \\sim C19' \\sim C20 \\sim C20' \\sim C21 \\sim C21' \\sim C22 \\sim
C22' \\sim C23 \\sim C23' \\sim C24 \\sim C24': within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C7, C8, C9, C10, C11, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7', C8', C9', C10', C11', C12'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19', C20', C21', C22', C23', C24'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19, C20, C21, C22, C23, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H6BC)=Sof(H6BD)=Sof(C7')=Sof(H7'A)=Sof(H7'B)=Sof(C8')=Sof(H8'A)=Sof(H8'B)=
 Sof(C9')=Sof(H9'A)=Sof(H9'B)=Sof(C10')=Sof(H10C)=Sof(H10D)=Sof(C11')=Sof(H11C)=
 Sof(H11D)=Sof(C12')=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H6AA)=Sof(H6AB)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(C19')=Sof(H19C)=Sof(H19D)=Sof(C20')=Sof(H20C)=
 Sof(H20D)=Sof(C21')=Sof(H21C)=Sof(H21D)=Sof(C22')=Sof(H22C)=Sof(H22D)=
 Sof(C23')=Sof(H23C)=Sof(H23D)=Sof(C24')=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(2)
 Sof(H18C)=Sof(H18D)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=
 Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(2)
6.a Riding coordinates:
 C12(H12A,H12B,H12C), C12'(H12D,H12E,H12F), C24(H24A,H24B,H24C)
6.b Rotating group:
 N2(H2A,H2B), N4(H4A,H4B)
6.c Secondary CH2 refined with riding coordinates:
 C6(H6AA,H6AB), C6(H6BC,H6BD), C7(H7A,H7B), C7'(H7'A,H7'B), C8(H8A,H8B),
 C8'(H8'A,H8'B), C9(H9A,H9B), C9'(H9'A,H9'B), C10(H10A,H10B), C10'(H10C,H10D),
 C11(H11A,H11B), C11'(H11C,H11D), C18(H18C,H18D), C18(H18A,H18B), C19(H19A,
 H19B), C19'(H19C,H19D), C20(H20A,H20B), C20'(H20C,H20D), C21(H21A,H21B),
 C21'(H21C,H21D), C22(H22A,H22B), C22'(H22C,H22D), C23(H23A,H23B), C23'(H23C,
 H23D)
6.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17)
6.e Idealised Me refined as rotating group:
 C24'(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.06091(9) 0.01899(6) 0.14938(6) 0.0615(3) Uani 1 1 d . . . . .
Pb2 Pb 0.56887(10) 0.14498(6) 0.02735(6) 0.0665(3) Uani 1 1 d . . . . .
I1 I -0.23773(17) -0.06862(10) 0.05785(10) 0.0716(5) Uani 1 1 d . . . . .
I2 I 0.2168(2) -0.16537(12) 0.15171(13) 0.0969(6) Uani 1 1 d . . . . .
I3 I -0.0094(2) -0.01178(16) 0.34651(12) 0.1090(8) Uani 1 1 d . . . . .
I4 I -0.1798(2) 0.19140(12) 0.13894(14) 0.0993(7) Uani 1 1 d . . . . .
I5 I 0.3536(2) 0.11068(14) 0.19967(12) 0.0984(6) Uani 1 1 d . . . . .
I6 I 0.4881(2) 0.34190(13) 0.00159(17) 0.1180(8) Uani 1 1 d . . . . .
N1 N 0.535(3) 0.8698(14) 0.3852(13) 0.093(7) Uani 1 1 d . . . . .
N2 N 0.364(3) 0.8923(19) 0.6355(15) 0.126(9) Uani 1 1 d . . . . .
H2A H 0.3771 0.9443 0.6588 0.152 Uiso 1 1 d GR . . . .
H2B H 0.2665 0.8918 0.6311 0.152 Uiso 1 1 d GR . . . .
N3 N 1.077(2) 0.4375(14) 0.1497(14) 0.089(6) Uani 1 1 d . . . . .
N4 N 0.906(3) 0.6841(17) 0.0548(18) 0.133(9) Uani 1 1 d . . . . .
H4A H 0.9835 0.7186 0.0426 0.160 Uiso 1 1 d GR . . . .
H4B H 0.8621 0.6829 0.0052 0.160 Uiso 1 1 d GR . . . .
C1 C 0.631(3) 0.8590(19) 0.450(2) 0.108(3) Uani 1 1 d . U . . .
H1 H 0.7318 0.8458 0.4378 0.130 Uiso 1 1 calc R . . . .
C2 C 0.574(3) 0.8684(19) 0.534(2) 0.103(4) Uani 1 1 d . U . . .
H2 H 0.6382 0.8631 0.5800 0.124 Uiso 1 1 calc R . . . .
C3 C 0.427(3) 0.8852(19) 0.551(2) 0.102(4) Uani 1 1 d . U . . .
C4 C 0.328(3) 0.8958(18) 0.4815(19) 0.104(4) Uani 1 1 d . U . . .
H4 H 0.2262 0.9082 0.4907 0.125 Uiso 1 1 calc R . . . .
C5 C 0.396(4) 0.886(2) 0.398(2) 0.108(3) Uani 1 1 d . U . . .
H5 H 0.3370 0.8912 0.3489 0.129 Uiso 1 1 calc R . . . .
C6 C 0.603(3) 0.8535(19) 0.2941(19) 0.109(3) Uani 1 1 d D U . . .
H6AA H 0.5253 0.8615 0.2520 0.131 Uiso 0.569(18) 1 calc R . P A 1
H6AB H 0.6779 0.8991 0.2769 0.131 Uiso 0.569(18) 1 calc R . P A 1
H6BC H 0.5546 0.8948 0.2512 0.131 Uiso 0.431(18) 1 calc R . P A 2
H6BD H 0.7073 0.8705 0.2923 0.131 Uiso 0.431(18) 1 calc R . P A 2
C7 C 0.670(5) 0.768(2) 0.288(4) 0.112(4) Uani 0.569(18) 1 d D U P A 1
H7A H 0.7473 0.7589 0.3297 0.134 Uiso 0.569(18) 1 calc R . P A 1
H7B H 0.7155 0.7653 0.2287 0.134 Uiso 0.569(18) 1 calc R . P A 1
C7' C 0.597(9) 0.761(2) 0.263(4) 0.112(3) Uani 0.431(18) 1 d D U P A 2
H7'A H 0.4944 0.7525 0.2488 0.135 Uiso 0.431(18) 1 calc R . P A 2
H7'B H 0.6558 0.7643 0.2069 0.135 Uiso 0.431(18) 1 calc R . P A 2
C8 C 0.554(4) 0.696(2) 0.307(3) 0.113(3) Uani 0.569(18) 1 d D U P A 1
H8A H 0.5252 0.6946 0.3690 0.135 Uiso 0.569(18) 1 calc R . P A 1
H8B H 0.4670 0.7172 0.2751 0.135 Uiso 0.569(18) 1 calc R . P A 1
C8' C 0.639(8) 0.687(4) 0.308(5) 0.113(3) Uani 0.431(18) 1 d D U P A 2
H8'A H 0.5707 0.6879 0.3598 0.136 Uiso 0.431(18) 1 calc R . P A 2
H8'B H 0.7336 0.7059 0.3277 0.136 Uiso 0.431(18) 1 calc R . P A 2
C9 C 0.576(6) 0.600(2) 0.288(3) 0.115(3) Uani 0.569(18) 1 d D U P A 1
H9A H 0.6749 0.5963 0.2592 0.138 Uiso 0.569(18) 1 calc R . P A 1
H9B H 0.5055 0.5889 0.2445 0.138 Uiso 0.569(18) 1 calc R . P A 1
C9' C 0.665(7) 0.590(3) 0.307(5) 0.115(3) Uani 0.431(18) 1 d D U P A 2
H9'A H 0.6986 0.5680 0.3644 0.138 Uiso 0.431(18) 1 calc R . P A 2
H9'B H 0.7490 0.5828 0.2646 0.138 Uiso 0.431(18) 1 calc R . P A 2
C10 C 0.565(6) 0.520(2) 0.357(3) 0.116(4) Uani 0.569(18) 1 d D U P A 1
H10A H 0.6111 0.5392 0.4086 0.139 Uiso 0.569(18) 1 calc R . P A 1
H10B H 0.4594 0.5137 0.3737 0.139 Uiso 0.569(18) 1 calc R . P A 1
C10' C 0.540(8) 0.526(3) 0.284(5) 0.115(4) Uani 0.431(18) 1 d D U P A 2
H10C H 0.4484 0.5473 0.3130 0.138 Uiso 0.431(18) 1 calc R . P A 2
H10D H 0.5285 0.5376 0.2214 0.138 Uiso 0.431(18) 1 calc R . P A 2
C11 C 0.623(5) 0.428(2) 0.347(3) 0.119(4) Uani 0.569(18) 1 d D U P A 1
H11A H 0.6192 0.3969 0.4060 0.143 Uiso 0.569(18) 1 calc R . P A 1
H11B H 0.7281 0.4347 0.3290 0.143 Uiso 0.569(18) 1 calc R . P A 1
C11' C 0.537(8) 0.431(4) 0.302(5) 0.117(4) Uani 0.431(18) 1 d D U P A 2
H11C H 0.4502 0.4160 0.2708 0.140 Uiso 0.431(18) 1 calc R . P A 2
H11D H 0.6218 0.4132 0.2651 0.140 Uiso 0.431(18) 1 calc R . P A 2
C12 C 0.563(6) 0.363(3) 0.289(4) 0.119(5) Uani 0.569(18) 1 d D U P A 1
H12A H 0.5691 0.3025 0.3168 0.178 Uiso 0.569(18) 1 d R . P A 1
H12B H 0.4615 0.3772 0.2761 0.178 Uiso 0.569(18) 1 d R . P A 1
H12C H 0.6241 0.3670 0.2344 0.178 Uiso 0.569(18) 1 d R . P A 1
C12' C 0.535(8) 0.363(4) 0.372(5) 0.117(5) Uani 0.431(18) 1 d D U P A 2
H12D H 0.6299 0.3326 0.3708 0.175 Uiso 0.431(18) 1 d R . P A 2
H12E H 0.5177 0.3887 0.4269 0.175 Uiso 0.431(18) 1 d R . P A 2
H12F H 0.4572 0.3214 0.3645 0.175 Uiso 0.431(18) 1 d R . P A 2
C13 C 1.165(4) 0.513(2) 0.136(2) 0.116(4) Uani 1 1 d . U . . .
H13 H 1.2660 0.5097 0.1464 0.139 Uiso 1 1 calc R . . . .
C14 C 1.102(4) 0.592(2) 0.107(2) 0.115(4) Uani 1 1 d . U . . .
H14 H 1.1652 0.6411 0.0989 0.138 Uiso 1 1 calc R . . . .
C15 C 0.957(4) 0.607(2) 0.089(2) 0.113(4) Uani 1 1 d . U . . .
C16 C 0.876(3) 0.528(2) 0.100(2) 0.115(4) Uani 1 1 d . U . . .
H16 H 0.7762 0.5325 0.0856 0.138 Uiso 1 1 calc R . . . .
C17 C 0.927(4) 0.447(2) 0.130(2) 0.115(4) Uani 1 1 d . U . . .
H17 H 0.8634 0.3974 0.1383 0.138 Uiso 1 1 calc R . . . .
C18 C 1.138(3) 0.3514(19) 0.1872(16) 0.119(4) Uani 1 1 d D U . . .
H18C H 1.2303 0.3356 0.1558 0.142 Uiso 0.337(16) 1 calc R . P B 4
H18D H 1.0669 0.3030 0.1873 0.142 Uiso 0.337(16) 1 calc R . P B 4
H18A H 1.2463 0.3528 0.1855 0.142 Uiso 0.663(16) 1 calc R . P B 3
H18B H 1.1072 0.3023 0.1551 0.142 Uiso 0.663(16) 1 calc R . P B 3
C19 C 1.164(8) 0.373(5) 0.279(2) 0.121(4) Uani 0.337(16) 1 d D U P B 4
H19A H 1.2722 0.3721 0.2823 0.145 Uiso 0.337(16) 1 calc R . P B 4
H19B H 1.1346 0.4359 0.2802 0.145 Uiso 0.337(16) 1 calc R . P B 4
C19' C 1.074(5) 0.341(2) 0.2808(19) 0.121(4) Uani 0.663(16) 1 d D U P B 3
H19C H 1.1183 0.3882 0.3107 0.145 Uiso 0.663(16) 1 calc R . P B 3
H19D H 0.9683 0.3559 0.2783 0.145 Uiso 0.663(16) 1 calc R . P B 3
C20 C 1.108(6) 0.330(5) 0.364(2) 0.122(4) Uani 0.337(16) 1 d D U P B 4
H20A H 1.1621 0.3576 0.4078 0.147 Uiso 0.337(16) 1 calc R . P B 4
H20B H 1.1456 0.2683 0.3655 0.147 Uiso 0.337(16) 1 calc R . P B 4
C20' C 1.085(5) 0.256(2) 0.3407(17) 0.124(4) Uani 0.663(16) 1 d D U P B 3
H20C H 1.1907 0.2412 0.3429 0.148 Uiso 0.663(16) 1 calc R . P B 3
H20D H 1.0394 0.2095 0.3116 0.148 Uiso 0.663(16) 1 calc R . P B 3
C21 C 0.953(6) 0.320(6) 0.404(4) 0.122(4) Uani 0.337(16) 1 d D U P B 4
H21A H 0.9275 0.2577 0.4016 0.147 Uiso 0.337(16) 1 calc R . P B 4
H21B H 0.8906 0.3551 0.3636 0.147 Uiso 0.337(16) 1 calc R . P B 4
C21' C 1.022(5) 0.249(2) 0.4344(17) 0.123(4) Uani 0.663(16) 1 d D U P B 3
H21C H 1.0768 0.2004 0.4660 0.148 Uiso 0.663(16) 1 calc R . P B 3
H21D H 0.9199 0.2278 0.4330 0.148 Uiso 0.663(16) 1 calc R . P B 3
C22 C 0.900(7) 0.343(6) 0.495(4) 0.123(4) Uani 0.337(16) 1 d D U P B 4
H22A H 0.9877 0.3758 0.5063 0.148 Uiso 0.337(16) 1 calc R . P B 4
H22B H 0.8301 0.3897 0.4747 0.148 Uiso 0.337(16) 1 calc R . P B 4
C22' C 1.016(5) 0.327(2) 0.491(2) 0.124(4) Uani 0.663(16) 1 d D U P B 3
H22C H 0.9620 0.3759 0.4604 0.148 Uiso 0.663(16) 1 calc R . P B 3
H22D H 1.1178 0.3470 0.4953 0.148 Uiso 0.663(16) 1 calc R . P B 3
C23 C 0.838(6) 0.332(7) 0.589(4) 0.124(4) Uani 0.337(16) 1 d D U P B 4
H23A H 0.8784 0.3818 0.6168 0.149 Uiso 0.337(16) 1 calc R . P B 4
H23B H 0.8834 0.2779 0.6159 0.149 Uiso 0.337(16) 1 calc R . P B 4
C23' C 0.946(5) 0.312(2) 0.585(2) 0.124(4) Uani 0.663(16) 1 d D U P B 3
H23C H 0.8480 0.2870 0.5790 0.149 Uiso 0.663(16) 1 calc R . P B 3
H23D H 1.0041 0.2635 0.6144 0.149 Uiso 0.663(16) 1 calc R . P B 3
C24 C 0.675(7) 0.328(6) 0.618(4) 0.128(6) Uani 0.337(16) 1 d D U P B 4
H24A H 0.6206 0.3044 0.5726 0.191 Uiso 0.337(16) 1 d R . P B 4
H24B H 0.6607 0.2897 0.6720 0.191 Uiso 0.337(16) 1 d R . P B 4
H24C H 0.6389 0.3875 0.6267 0.191 Uiso 0.337(16) 1 d R . P B 4
C24' C 0.923(5) 0.377(3) 0.650(2) 0.129(6) Uani 0.663(16) 1 d D U P B 3
H24D H 0.8848 0.4323 0.6210 0.193 Uiso 0.663(16) 1 calc GR . P B 3
H24E H 1.0160 0.3883 0.6746 0.193 Uiso 0.663(16) 1 calc GR . P B 3
H24F H 0.8521 0.3541 0.6956 0.193 Uiso 0.663(16) 1 calc GR . P B 3


_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 I1 3.4151(17) . ?
Pb1 I2 3.066(2) . ?
Pb1 I3 3.023(2) . ?
Pb1 I4 3.331(2) . ?
Pb1 I5 3.1391(19) . ?
Pb2 I2 3.237(2) 2_655 ?
Pb2 I4 3.0200(19) 1_655 ?
Pb2 I5 3.173(2) . ?
Pb2 I6 3.011(2) . ?
I2 Pb2 3.237(2) 2_655 ?
I4 Pb2 3.0200(19) 1_455 ?
N1 C1 1.34(3) . ?
N1 C5 1.27(3) . ?
N1 C6 1.52(3) . ?
N2 H2A 0.8959 . ?
N2 H2B 0.8796 . ?
N2 C3 1.39(3) . ?
N3 C13 1.38(3) . ?
N3 C17 1.39(3) . ?
N3 C18 1.47(3) . ?
N4 H4A 0.8682 . ?
N4 H4B 0.8738 . ?
N4 C15 1.30(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.37(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.35(4) . ?
C3 C4 1.41(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.41(4) . ?
C5 H5 0.9300 . ?
C6 H6AA 0.9700 . ?
C6 H6AB 0.9700 . ?
C6 H6BC 0.9700 . ?
C6 H6BD 0.9700 . ?
C6 C7 1.41(5) . ?
C6 C7' 1.50(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.51(2) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C7' C8' 1.31(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.492(19) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C8' C9' 1.47(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.507(19) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C9' C10' 1.56(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.486(18) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C10' C11' 1.41(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.50(2) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C11' C12' 1.39(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9601 . ?
C12' H12F 0.9599 . ?
C13 H13 0.9300 . ?
C13 C14 1.34(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.36(4) . ?
C15 C16 1.38(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.35(4) . ?
C17 H17 0.9300 . ?
C18 H18C 0.9700 . ?
C18 H18D 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.497(14) . ?
C18 C19' 1.500(18) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.465(19) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C19' C20' 1.495(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.48(2) . ?
C20' H20C 0.9700 . ?
C20' H20D 0.9700 . ?
C20' C21' 1.499(16) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.50(2) . ?
C21' H21C 0.9700 . ?
C21' H21D 0.9700 . ?
C21' C22' 1.519(18) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.50(2) . ?
C22' H22C 0.9700 . ?
C22' H22D 0.9700 . ?
C22' C23' 1.526(19) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.50(2) . ?
C23' H23C 0.9700 . ?
C23' H23D 0.9700 . ?
C23' C24' 1.451(18) . ?
C24 H24A 0.9602 . ?
C24 H24B 0.9597 . ?
C24 H24C 0.9600 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 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
I2 Pb1 I1 89.23(5) . . ?
I2 Pb1 I4 166.40(6) . . ?
I2 Pb1 I5 91.70(6) . . ?
I3 Pb1 I1 104.41(5) . . ?
I3 Pb1 I2 90.31(6) . . ?
I3 Pb1 I4 89.54(6) . . ?
I3 Pb1 I5 85.46(6) . . ?
I4 Pb1 I1 77.64(5) . . ?
I5 Pb1 I1 170.08(5) . . ?
I5 Pb1 I4 101.84(6) . . ?
I4 Pb2 I2 92.06(6) 1_655 2_655 ?
I4 Pb2 I5 90.28(6) 1_655 . ?
I5 Pb2 I2 175.85(6) . 2_655 ?
I6 Pb2 I2 90.33(6) . 2_655 ?
I6 Pb2 I4 88.98(6) . 1_655 ?
I6 Pb2 I5 93.14(6) . . ?
Pb1 I2 Pb2 102.72(6) . 2_655 ?
Pb2 I4 Pb1 107.93(6) 1_455 . ?
Pb1 I5 Pb2 108.77(6) . . ?
C1 N1 C6 114(3) . . ?
C5 N1 C1 124(3) . . ?
C5 N1 C6 121(3) . . ?
H2A N2 H2B 102.0 . . ?
C3 N2 H2A 116.8 . . ?
C3 N2 H2B 106.3 . . ?
C13 N3 C17 118(2) . . ?
C13 N3 C18 121(2) . . ?
C17 N3 C18 121(2) . . ?
H4A N4 H4B 105.8 . . ?
C15 N4 H4A 106.7 . . ?
C15 N4 H4B 115.6 . . ?
N1 C1 H1 121.8 . . ?
N1 C1 C2 116(3) . . ?
C2 C1 H1 121.8 . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121(3) . . ?
C3 C2 H2 119.3 . . ?
N2 C3 C4 116(3) . . ?
C2 C3 N2 123(3) . . ?
C2 C3 C4 121(3) . . ?
C3 C4 H4 123.2 . . ?
C5 C4 C3 114(3) . . ?
C5 C4 H4 123.2 . . ?
N1 C5 C4 123(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N1 C6 H6AA 108.4 . . ?
N1 C6 H6AB 108.4 . . ?
N1 C6 H6BC 107.4 . . ?
N1 C6 H6BD 107.4 . . ?
H6AA C6 H6AB 107.5 . . ?
H6BC C6 H6BD 106.9 . . ?
C7 C6 N1 115(3) . . ?
C7 C6 H6AA 108.4 . . ?
C7 C6 H6AB 108.4 . . ?
C7' C6 N1 120(4) . . ?
C7' C6 H6BC 107.4 . . ?
C7' C6 H6BD 107.4 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C6 C7 C8 110(3) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7' H7'A 106.2 . . ?
C6 C7' H7'B 106.2 . . ?
H7'A C7' H7'B 106.4 . . ?
C8' C7' C6 125(5) . . ?
C8' C7' H7'A 106.2 . . ?
C8' C7' H7'B 106.2 . . ?
C7 C8 H8A 106.1 . . ?
C7 C8 H8B 106.1 . . ?
H8A C8 H8B 106.3 . . ?
C9 C8 C7 125(2) . . ?
C9 C8 H8A 106.1 . . ?
C9 C8 H8B 106.1 . . ?
C7' C8' H8'A 100.5 . . ?
C7' C8' H8'B 100.5 . . ?
C7' C8' C9' 146(6) . . ?
H8'A C8' H8'B 104.3 . . ?
C9' C8' H8'A 100.5 . . ?
C9' C8' H8'B 100.5 . . ?
C8 C9 H9A 106.1 . . ?
C8 C9 H9B 106.1 . . ?
C8 C9 C10 125(2) . . ?
H9A C9 H9B 106.3 . . ?
C10 C9 H9A 106.1 . . ?
C10 C9 H9B 106.1 . . ?
C8' C9' H9'A 107.0 . . ?
C8' C9' H9'B 107.0 . . ?
C8' C9' C10' 121(5) . . ?
H9'A C9' H9'B 106.7 . . ?
C10' C9' H9'A 107.0 . . ?
C10' C9' H9'B 107.0 . . ?
C9 C10 H10A 105.8 . . ?
C9 C10 H10B 105.8 . . ?
H10A C10 H10B 106.2 . . ?
C11 C10 C9 126(2) . . ?
C11 C10 H10A 105.8 . . ?
C11 C10 H10B 105.8 . . ?
C9' C10' H10C 105.6 . . ?
C9' C10' H10D 105.6 . . ?
H10C C10' H10D 106.1 . . ?
C11' C10' C9' 127(5) . . ?
C11' C10' H10C 105.6 . . ?
C11' C10' H10D 105.6 . . ?
C10 C11 H11A 105.7 . . ?
C10 C11 H11B 105.8 . . ?
C10 C11 C12 126(2) . . ?
H11A C11 H11B 106.2 . . ?
C12 C11 H11A 105.7 . . ?
C12 C11 H11B 105.8 . . ?
C10' C11' H11C 101.6 . . ?
C10' C11' H11D 101.6 . . ?
H11C C11' H11D 104.6 . . ?
C12' C11' C10' 142(7) . . ?
C12' C11' H11C 101.6 . . ?
C12' C11' H11D 101.6 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.6 . . ?
C11 C12 H12C 107.8 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11' C12' H12D 108.8 . . ?
C11' C12' H12E 110.2 . . ?
C11' C12' H12F 109.4 . . ?
H12D C12' H12E 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
N3 C13 H13 120.5 . . ?
C14 C13 N3 119(3) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 116.5 . . ?
C13 C14 C15 127(3) . . ?
C15 C14 H14 116.5 . . ?
N4 C15 C14 123(3) . . ?
N4 C15 C16 125(3) . . ?
C14 C15 C16 112(3) . . ?
C15 C16 H16 117.0 . . ?
C17 C16 C15 126(3) . . ?
C17 C16 H16 117.0 . . ?
N3 C17 H17 120.7 . . ?
C16 C17 N3 119(3) . . ?
C16 C17 H17 120.7 . . ?
N3 C18 H18C 111.7 . . ?
N3 C18 H18D 111.7 . . ?
N3 C18 H18A 110.9 . . ?
N3 C18 H18B 110.9 . . ?
N3 C18 C19 101(4) . . ?
N3 C18 C19' 104(2) . . ?
H18C C18 H18D 109.4 . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 H18C 111.7 . . ?
C19 C18 H18D 111.7 . . ?
C19' C18 H18A 110.9 . . ?
C19' C18 H18B 110.9 . . ?
C18 C19 H19A 104.8 . . ?
C18 C19 H19B 104.8 . . ?
H19A C19 H19B 105.8 . . ?
C20 C19 C18 130(3) . . ?
C20 C19 H19A 104.8 . . ?
C20 C19 H19B 104.8 . . ?
C18 C19' H19C 106.5 . . ?
C18 C19' H19D 106.5 . . ?
H19C C19' H19D 106.5 . . ?
C20' C19' C18 123(2) . . ?
C20' C19' H19C 106.5 . . ?
C20' C19' H19D 106.5 . . ?
C19 C20 H20A 104.5 . . ?
C19 C20 H20B 104.5 . . ?
C19 C20 C21 131(3) . . ?
H20A C20 H20B 105.6 . . ?
C21 C20 H20A 104.5 . . ?
C21 C20 H20B 104.5 . . ?
C19' C20' H20C 106.8 . . ?
C19' C20' H20D 106.8 . . ?
C19' C20' C21' 122.2(19) . . ?
H20C C20' H20D 106.6 . . ?
C21' C20' H20C 106.8 . . ?
C21' C20' H20D 106.8 . . ?
C20 C21 H21A 105.6 . . ?
C20 C21 H21B 105.6 . . ?
C20 C21 C22 127(3) . . ?
H21A C21 H21B 106.1 . . ?
C22 C21 H21A 105.6 . . ?
C22 C21 H21B 105.6 . . ?
C20' C21' H21C 106.6 . . ?
C20' C21' H21D 106.6 . . ?
C20' C21' C22' 122.9(19) . . ?
H21C C21' H21D 106.6 . . ?
C22' C21' H21C 106.6 . . ?
C22' C21' H21D 106.6 . . ?
C21 C22 H22A 95.8 . . ?
C21 C22 H22B 95.8 . . ?
H22A C22 H22B 103.3 . . ?
C23 C22 C21 161(9) . . ?
C23 C22 H22A 95.8 . . ?
C23 C22 H22B 95.8 . . ?
C21' C22' H22C 107.7 . . ?
C21' C22' H22D 107.7 . . ?
C21' C22' C23' 118(2) . . ?
H22C C22' H22D 107.1 . . ?
C23' C22' H22C 107.7 . . ?
C23' C22' H22D 107.7 . . ?
C22 C23 H23A 105.9 . . ?
C22 C23 H23B 106.0 . . ?
C22 C23 C24 125(3) . . ?
H23A C23 H23B 106.3 . . ?
C24 C23 H23A 105.9 . . ?
C24 C23 H23B 106.0 . . ?
C22' C23' H23C 105.3 . . ?
C22' C23' H23D 105.3 . . ?
H23C C23' H23D 106.0 . . ?
C24' C23' C22' 128(2) . . ?
C24' C23' H23C 105.3 . . ?
C24' C23' H23D 105.3 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 110.3 . . ?
C23 C24 H24C 109.1 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23' C24' H24D 109.5 . . ?
C23' C24' H24E 109.5 . . ?
C23' C24' H24F 109.5 . . ?
H24D C24' H24E 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 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
N1 C1 C2 C3 2(5) . . . . ?
N1 C6 C7 C8 63(5) . . . . ?
N1 C6 C7' C8' -50(10) . . . . ?
N2 C3 C4 C5 -178(3) . . . . ?
N3 C13 C14 C15 0(6) . . . . ?
N3 C18 C19 C20 123(6) . . . . ?
N3 C18 C19' C20' 170(4) . . . . ?
N4 C15 C16 C17 176(3) . . . . ?
C1 N1 C5 C4 1(5) . . . . ?
C1 N1 C6 C7 57(4) . . . . ?
C1 N1 C6 C7' 92(4) . . . . ?
C1 C2 C3 N2 178(3) . . . . ?
C1 C2 C3 C4 -2(5) . . . . ?
C2 C3 C4 C5 1(4) . . . . ?
C3 C4 C5 N1 -1(5) . . . . ?
C5 N1 C1 C2 -2(4) . . . . ?
C5 N1 C6 C7 -118(3) . . . . ?
C5 N1 C6 C7' -84(5) . . . . ?
C6 N1 C1 C2 -177(2) . . . . ?
C6 N1 C5 C4 176(3) . . . . ?
C6 C7 C8 C9 167(4) . . . . ?
C6 C7' C8' C9' -173(9) . . . . ?
C7 C8 C9 C10 120(6) . . . . ?
C7' C8' C9' C10' -57(17) . . . . ?
C8 C9 C10 C11 -163(4) . . . . ?
C8' C9' C10' C11' -163(7) . . . . ?
C9 C10 C11 C12 -69(7) . . . . ?
C9' C10' C11' C12' 62(15) . . . . ?
C13 N3 C17 C16 -1(4) . . . . ?
C13 N3 C18 C19 68(4) . . . . ?
C13 N3 C18 C19' 105(3) . . . . ?
C13 C14 C15 N4 -175(3) . . . . ?
C13 C14 C15 C16 -2(5) . . . . ?
C14 C15 C16 C17 4(5) . . . . ?
C15 C16 C17 N3 -2(5) . . . . ?
C17 N3 C13 C14 2(4) . . . . ?
C17 N3 C18 C19 -110(3) . . . . ?
C17 N3 C18 C19' -72(4) . . . . ?
C18 N3 C13 C14 -176(3) . . . . ?
C18 N3 C17 C16 177(3) . . . . ?
C18 C19 C20 C21 -64(10) . . . . ?
C18 C19' C20' C21' 179(4) . . . . ?
C19 C20 C21 C22 -129(9) . . . . ?
C19' C20' C21' C22' -33(7) . . . . ?
C20 C21 C22 C23 -115(15) . . . . ?
C20' C21' C22' C23' 179(4) . . . . ?
C21 C22 C23 C24 -83(21) . . . . ?
C21' C22' C23' C24' -177(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
