# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Complex1
_database_code_depnum_ccdc_archive 'CCDC 1024096'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C24 H14 N4 O4, 2(C12 H7 N2 O2), 2(I6 Pb2), 2(C5 H9 N O), 2(H2 O)'
_chemical_formula_sum            'C58 H50 I12 N10 O12 Pb4'
_chemical_formula_weight         3430.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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  '-P 1'


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

_cell_length_a                   11.361(2)
_cell_length_b                   13.250(3)
_cell_length_c                   15.572(3)
_cell_angle_alpha                66.81(3)
_cell_angle_beta                 78.10(3)
_cell_angle_gamma                74.92(3)
_cell_volume                     2066.4(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528
_exptl_absorpt_coefficient_mu    12.662
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.2688
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19971
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             9307
_reflns_number_gt                7077
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  'SHELXL97 and publCIF (Westrip, 2010)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+7.6737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9307
_refine_ls_number_parameters     445
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.5000 1.0000 0.0000 0.04178(12) Uani 1 2 d S . .
Pb2 Pb 0.48943(3) 0.73353(3) 0.23870(2) 0.04270(9) Uani 1 1 d . . .
Pb3 Pb 0.5000 0.5000 0.5000 0.04854(13) Uani 1 2 d S . .
I1 I 0.69185(5) 0.88141(5) 0.15146(4) 0.05103(16) Uani 1 1 d . . .
I2 I 0.28441(5) 0.96446(5) 0.17549(4) 0.05107(15) Uani 1 1 d . . .
I3 I 0.48295(7) 0.75110(5) 0.02140(5) 0.06050(18) Uani 1 1 d . . .
I4 I 0.33134(6) 0.53650(5) 0.34186(5) 0.05869(17) Uani 1 1 d . . .
I5 I 0.71606(6) 0.52488(6) 0.33003(4) 0.05953(17) Uani 1 1 d . . .
I6 I 0.44400(10) 0.76911(6) 0.43301(4) 0.0826(3) Uani 1 1 d . . .
O1 O 0.8193(7) 1.2358(6) 0.2719(5) 0.0614(17) Uani 1 1 d . . .
O2 O 0.6491(6) 0.9528(7) 0.5001(6) 0.075(2) Uani 1 1 d . . .
O3 O 0.9048(7) 0.9852(5) 0.2785(4) 0.0576(17) Uani 1 1 d . . .
O4 O 1.0634(7) 0.6780(5) 0.2039(4) 0.0601(18) Uani 1 1 d . . .
O5 O 0.7793(7) 1.6626(7) -0.1648(5) 0.078(2) Uani 1 1 d . . .
O6 O 0.9272(9) 0.5576(6) 0.7118(5) 0.0657(19) Uani 1 1 d D . .
H32A H 0.860(6) 0.553(9) 0.701(10) 0.12(6) Uiso 1 1 d D . .
H32B H 0.964(9) 0.491(3) 0.735(8) 0.09(4) Uiso 1 1 d D . .
N1 N 0.4295(8) 1.2097(10) 0.2427(6) 0.078(3) Uani 1 1 d . . .
H1 H 0.3683 1.2337 0.2105 0.093 Uiso 1 1 calc R . .
N2 N 0.7298(6) 1.0999(7) 0.3888(5) 0.0481(17) Uani 1 1 d . . .
N3 N 0.9630(10) 0.6508(7) 0.5243(5) 0.070(3) Uani 1 1 d . . .
H3A H 0.9577 0.6120 0.5836 0.084 Uiso 1 1 calc R . .
N4 N 0.9923(6) 0.8342(5) 0.2393(4) 0.0355(14) Uani 1 1 d . . .
N27 N 0.7721(10) 1.5419(10) -0.0151(9) 0.095(3) Uani 1 1 d . . .
C1 C 0.4620(10) 1.2805(10) 0.2676(8) 0.070(3) Uani 1 1 d . . .
H1A H 0.4175 1.3537 0.2519 0.084 Uiso 1 1 calc R . .
C2 C 0.4858(10) 1.1007(11) 0.2640(8) 0.074(3) Uani 1 1 d . . .
H2 H 0.4575 1.0529 0.2461 0.088 Uiso 1 1 calc R . .
C3 C 0.5873(9) 1.0624(10) 0.3136(8) 0.067(3) Uani 1 1 d . . .
H3 H 0.6294 0.9884 0.3295 0.081 Uiso 1 1 calc R . .
C4 C 0.6234(8) 1.1386(9) 0.3384(7) 0.055(2) Uani 1 1 d . . .
C5 C 0.5607(10) 1.2486(9) 0.3167(7) 0.064(3) Uani 1 1 d . . .
H5 H 0.5847 1.2987 0.3346 0.077 Uiso 1 1 calc R . .
C6 C 0.8287(9) 1.1577(8) 0.3441(6) 0.049(2) Uani 1 1 d . . .
C7 C 0.9417(8) 1.1142(7) 0.3919(6) 0.0444(19) Uani 1 1 d . . .
C8 C 0.9466(7) 1.0204(7) 0.4773(5) 0.0405(18) Uani 1 1 d . . .
C9 C 0.8465(8) 0.9640(8) 0.5179(6) 0.048(2) Uani 1 1 d . . .
C10 C 0.7340(9) 1.0015(8) 0.4715(7) 0.053(2) Uani 1 1 d . . .
C11 C 0.8553(9) 0.8731(8) 0.6015(7) 0.057(2) Uani 1 1 d . . .
H11 H 0.7890 0.8374 0.6280 0.068 Uiso 1 1 calc R . .
C12 C 1.0406(9) 1.1661(8) 0.3533(7) 0.056(2) Uani 1 1 d . . .
H12 H 1.0372 1.2273 0.2971 0.067 Uiso 1 1 calc R . .
C13 C 1.0613(11) 0.6954(9) 0.4843(6) 0.067(3) Uani 1 1 d . . .
H13 H 1.1217 0.6857 0.5206 0.081 Uiso 1 1 calc R . .
C14 C 1.0747(9) 0.7563(8) 0.3891(6) 0.054(2) Uani 1 1 d . . .
H14 H 1.1431 0.7884 0.3601 0.065 Uiso 1 1 calc R . .
C15 C 0.9830(8) 0.7674(6) 0.3389(5) 0.0392(18) Uani 1 1 d . . .
C16 C 0.8814(11) 0.7238(10) 0.3823(7) 0.080(4) Uani 1 1 d . . .
H16 H 0.8182 0.7350 0.3478 0.096 Uiso 1 1 calc R . .
C17 C 0.8722(14) 0.6634(11) 0.4767(7) 0.094(5) Uani 1 1 d . . .
H17 H 0.8038 0.6318 0.5070 0.113 Uiso 1 1 calc R . .
C18 C 1.0363(7) 0.7780(6) 0.1753(5) 0.0365(16) Uani 1 1 d . . .
C19 C 1.0425(7) 0.8508(6) 0.0750(5) 0.0350(16) Uani 1 1 d . . .
C20 C 0.9988(6) 0.9677(5) 0.0482(4) 0.0270(14) Uani 1 1 d . . .
C21 C 0.9496(7) 1.0180(6) 0.1153(5) 0.0315(15) Uani 1 1 d . . .
C22 C 0.9471(7) 0.9483(6) 0.2159(5) 0.0373(17) Uani 1 1 d . . .
C23 C 0.9059(9) 1.1307(7) 0.0881(6) 0.051(2) Uani 1 1 d . . .
H23 H 0.8735 1.1632 0.1333 0.062 Uiso 1 1 calc R . .
C24 C 1.0902(9) 0.8018(7) 0.0080(5) 0.050(2) Uani 1 1 d . . .
H24 H 1.1195 0.7249 0.0265 0.060 Uiso 1 1 calc R . .
C25 C 0.7937(15) 1.5200(15) 0.0771(11) 0.118(6) Uani 1 1 d . . .
H4 H 0.8361 1.4435 0.1064 0.142 Uiso 1 1 calc R . .
H26B H 0.7181 1.5351 0.1163 0.142 Uiso 1 1 calc R . .
C26 C 0.8787(15) 1.6077(15) 0.0560(11) 0.112(5) Uani 1 1 d . . .
H30A H 0.8518 1.6481 0.0991 0.135 Uiso 1 1 calc R . .
H30B H 0.9634 1.5694 0.0633 0.135 Uiso 1 1 calc R . .
C27 C 0.8674(13) 1.6860(13) -0.0422(10) 0.097(4) Uani 1 1 d . . .
H29A H 0.9474 1.6954 -0.0773 0.117 Uiso 1 1 calc R . .
H29B H 0.8188 1.7588 -0.0442 0.117 Uiso 1 1 calc R . .
C28 C 0.8004(11) 1.6258(12) -0.0817(9) 0.082(4) Uani 1 1 d . . .
C29 C 0.6890(13) 1.4781(13) -0.0237(16) 0.152(9) Uani 1 1 d . . .
H31A H 0.6212 1.5292 -0.0556 0.229 Uiso 1 1 calc R . .
H31B H 0.6589 1.4319 0.0379 0.229 Uiso 1 1 calc R . .
H31C H 0.7329 1.4316 -0.0588 0.229 Uiso 1 1 calc 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 3.1940(13) . ?
Pb1 I1 3.1940(13) 2_675 ?
Pb1 I3 3.2352(9) . ?
Pb1 I3 3.2352(9) 2_675 ?
Pb1 I2 3.2428(13) 2_675 ?
Pb1 I2 3.2428(13) . ?
Pb2 I1 3.1519(12) . ?
Pb2 I6 3.1618(10) . ?
Pb2 I4 3.2512(13) . ?
Pb2 I2 3.2591(15) . ?
Pb2 I3 3.3140(10) . ?
Pb2 I5 3.3174(16) . ?
Pb3 I5 3.1929(13) 2_666 ?
Pb3 I5 3.1929(13) . ?
Pb3 I6 3.2206(12) 2_666 ?
Pb3 I6 3.2206(12) . ?
Pb3 I4 3.2396(11) . ?
Pb3 I4 3.2396(11) 2_666 ?
O1 C6 1.193(10) . ?
O2 C10 1.211(11) . ?
O3 C22 1.217(9) . ?
O4 C18 1.195(9) . ?
O5 C28 1.241(14) . ?
N1 C1 1.301(15) . ?
N1 C2 1.355(15) . ?
N2 C10 1.425(12) . ?
N2 C6 1.427(12) . ?
N2 C4 1.447(11) . ?
N3 C13 1.323(14) . ?
N3 C17 1.331(16) . ?
N4 C22 1.387(10) . ?
N4 C18 1.407(10) . ?
N4 C15 1.450(9) . ?
N27 C28 1.247(16) . ?
N27 C25 1.409(18) . ?
N27 C29 1.477(17) . ?
C1 C5 1.368(14) . ?
C2 C3 1.392(14) . ?
C3 C4 1.388(13) . ?
C4 C5 1.385(14) . ?
C6 C7 1.486(12) . ?
C7 C12 1.376(12) . ?
C7 C8 1.417(11) . ?
C8 C8 1.407(16) 2_776 ?
C8 C9 1.422(11) . ?
C9 C11 1.383(13) . ?
C9 C10 1.473(13) . ?
C11 C12 1.378(13) 2_776 ?
C12 C11 1.378(13) 2_776 ?
C13 C14 1.378(12) . ?
C14 C15 1.373(12) . ?
C15 C16 1.356(12) . ?
C16 C17 1.366(13) . ?
C18 C19 1.477(10) . ?
C19 C24 1.384(11) . ?
C19 C20 1.413(9) . ?
C20 C21 1.402(9) . ?
C20 C20 1.402(12) 2_775 ?
C21 C23 1.363(11) . ?
C21 C22 1.471(10) . ?
C23 C24 1.407(11) 2_775 ?
C24 C23 1.407(11) 2_775 ?
C25 C26 1.59(2) . ?
C26 C27 1.481(19) . ?
C27 C28 1.578(19) . ?

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 180.00(2) . 2_675 ?
I1 Pb1 I3 87.00(3) . . ?
I1 Pb1 I3 93.00(3) 2_675 . ?
I1 Pb1 I3 93.00(3) . 2_675 ?
I1 Pb1 I3 87.00(3) 2_675 2_675 ?
I3 Pb1 I3 180.0 . 2_675 ?
I1 Pb1 I2 92.71(3) . 2_675 ?
I1 Pb1 I2 87.29(3) 2_675 2_675 ?
I3 Pb1 I2 96.43(4) . 2_675 ?
I3 Pb1 I2 83.57(4) 2_675 2_675 ?
I1 Pb1 I2 87.29(3) . . ?
I1 Pb1 I2 92.71(3) 2_675 . ?
I3 Pb1 I2 83.57(4) . . ?
I3 Pb1 I2 96.43(4) 2_675 . ?
I2 Pb1 I2 180.00(2) 2_675 . ?
I1 Pb2 I6 93.99(3) . . ?
I1 Pb2 I4 167.53(2) . . ?
I6 Pb2 I4 86.75(3) . . ?
I1 Pb2 I2 87.72(3) . . ?
I6 Pb2 I2 83.95(4) . . ?
I4 Pb2 I2 104.73(3) . . ?
I1 Pb2 I3 86.35(3) . . ?
I6 Pb2 I3 166.02(2) . . ?
I4 Pb2 I3 95.94(3) . . ?
I2 Pb2 I3 82.09(4) . . ?
I1 Pb2 I5 85.83(3) . . ?
I6 Pb2 I5 85.72(4) . . ?
I4 Pb2 I5 81.81(3) . . ?
I2 Pb2 I5 167.41(2) . . ?
I3 Pb2 I5 108.24(4) . . ?
I5 Pb3 I5 180.000(1) 2_666 . ?
I5 Pb3 I6 86.85(4) 2_666 2_666 ?
I5 Pb3 I6 93.15(4) . 2_666 ?
I5 Pb3 I6 93.15(4) 2_666 . ?
I5 Pb3 I6 86.85(4) . . ?
I6 Pb3 I6 180.0 2_666 . ?
I5 Pb3 I4 96.07(2) 2_666 . ?
I5 Pb3 I4 83.93(2) . . ?
I6 Pb3 I4 94.03(4) 2_666 . ?
I6 Pb3 I4 85.97(4) . . ?
I5 Pb3 I4 83.93(2) 2_666 2_666 ?
I5 Pb3 I4 96.07(2) . 2_666 ?
I6 Pb3 I4 85.97(4) 2_666 2_666 ?
I6 Pb3 I4 94.03(4) . 2_666 ?
I4 Pb3 I4 180.0 . 2_666 ?
Pb2 I1 Pb1 78.14(3) . . ?
Pb1 I2 Pb2 75.92(4) . . ?
Pb1 I3 Pb2 75.27(3) . . ?
Pb3 I4 Pb2 76.75(3) . . ?
Pb3 I5 Pb2 76.45(3) . . ?
Pb2 I6 Pb3 78.30(4) . . ?
C1 N1 C2 124.4(9) . . ?
C10 N2 C6 125.3(7) . . ?
C10 N2 C4 118.6(8) . . ?
C6 N2 C4 115.7(8) . . ?
C13 N3 C17 122.8(8) . . ?
C22 N4 C18 125.8(6) . . ?
C22 N4 C15 115.9(6) . . ?
C18 N4 C15 118.1(6) . . ?
C28 N27 C25 120.6(15) . . ?
C28 N27 C29 121.8(16) . . ?
C25 N27 C29 115.9(15) . . ?
N1 C1 C5 120.8(11) . . ?
N1 C2 C3 117.9(10) . . ?
C4 C3 C2 117.6(10) . . ?
C5 C4 C3 122.0(9) . . ?
C5 C4 N2 120.0(9) . . ?
C3 C4 N2 118.0(9) . . ?
C1 C5 C4 117.2(10) . . ?
O1 C6 N2 120.6(9) . . ?
O1 C6 C7 123.0(9) . . ?
N2 C6 C7 116.4(8) . . ?
C12 C7 C8 120.5(8) . . ?
C12 C7 C6 119.7(8) . . ?
C8 C7 C6 119.8(8) . . ?
C8 C8 C7 119.8(9) 2_776 . ?
C8 C8 C9 118.5(9) 2_776 . ?
C7 C8 C9 121.7(8) . . ?
C11 C9 C8 119.6(8) . . ?
C11 C9 C10 119.8(8) . . ?
C8 C9 C10 120.6(8) . . ?
O2 C10 N2 120.7(9) . . ?
O2 C10 C9 123.2(9) . . ?
N2 C10 C9 116.1(8) . . ?
C12 C11 C9 121.9(9) 2_776 . ?
C7 C12 C11 119.7(9) . 2_776 ?
N3 C13 C14 120.5(10) . . ?
C15 C14 C13 117.2(10) . . ?
C16 C15 C14 121.0(8) . . ?
C16 C15 N4 120.2(8) . . ?
C14 C15 N4 118.6(7) . . ?
C15 C16 C17 119.8(11) . . ?
N3 C17 C16 118.6(10) . . ?
O4 C18 N4 119.9(7) . . ?
O4 C18 C19 124.7(7) . . ?
N4 C18 C19 115.4(6) . . ?
C24 C19 C20 120.9(7) . . ?
C24 C19 C18 118.7(7) . . ?
C20 C19 C18 120.4(7) . . ?
C21 C20 C20 120.4(8) . 2_775 ?
C21 C20 C19 121.4(6) . . ?
C20 C20 C19 118.1(8) 2_775 . ?
C23 C21 C20 120.6(7) . . ?
C23 C21 C22 120.0(7) . . ?
C20 C21 C22 119.4(6) . . ?
O3 C22 N4 119.1(7) . . ?
O3 C22 C21 123.5(7) . . ?
N4 C22 C21 117.4(7) . . ?
C21 C23 C24 120.3(8) . 2_775 ?
C19 C24 C23 119.6(8) . 2_775 ?
N27 C25 C26 100.1(12) . . ?
C27 C26 C25 106.6(11) . . ?
C26 C27 C28 102.8(12) . . ?
O5 C28 N27 129.2(16) . . ?
O5 C28 C27 122.9(13) . . ?
N27 C28 C27 107.8(13) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.279
_refine_diff_density_min         -1.469
_refine_diff_density_rms         0.185
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_(H2DPNDI)(2I)
_database_code_depnum_ccdc_archive 'CCDC 1038297'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 N4 O4, 2(I), H2 O'
_chemical_formula_sum            'C24 H16 I2 N4 O5'
_chemical_formula_weight         694.21

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   15.786(3)
_cell_length_b                   8.5029(17)
_cell_length_c                   17.617(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.38(3)
_cell_angle_gamma                90.00
_cell_volume                     2309.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    2.769
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7896
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9225
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2651
_reflns_number_gt                2579
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  'SHELXL97 and publCIF (Westrip, 2010)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0317P)²+8.1014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2651
_refine_ls_number_parameters     162
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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
I1 I 0.086727(13) 0.13768(3) 0.428074(11) 0.02668(9) Uani 1 1 d . . .
O1 O 0.26628(15) 0.2035(3) 0.88249(13) 0.0286(5) Uani 1 1 d . . .
O2 O 0.40956(16) -0.1687(3) 0.77352(14) 0.0309(5) Uani 1 1 d . . .
O3 O 0.5000 0.1737(17) 0.7500 0.201(6) Uani 1 2 d SD . .
H3A H 0.517(12) 0.240(4) 0.788(2) 0.242 Uiso 1 1 d D . .
N1 N 0.1536(2) 0.0411(4) 0.62255(16) 0.0318(6) Uani 1 1 d . . .
H1 H 0.1151 0.0452 0.5799 0.038 Uiso 1 1 calc R . .
N2 N 0.33943(16) 0.0201(3) 0.82780(14) 0.0222(5) Uani 1 1 d . . .
C1 C 0.1290(2) 0.0003(4) 0.6876(2) 0.0311(7) Uani 1 1 d . . .
H1A H 0.0712 -0.0234 0.6863 0.037 Uiso 1 1 calc R . .
C2 C 0.1890(2) -0.0066(4) 0.75669(19) 0.0272(7) Uani 1 1 d . . .
H2 H 0.1725 -0.0340 0.8025 0.033 Uiso 1 1 calc R . .
C3 C 0.2748(2) 0.0281(4) 0.75647(17) 0.0226(6) Uani 1 1 d . . .
C4 C 0.2989(2) 0.0711(4) 0.68828(18) 0.0289(7) Uani 1 1 d . . .
H4 H 0.3561 0.0962 0.6879 0.035 Uiso 1 1 calc R . .
C5 C 0.2356(2) 0.0757(5) 0.62088(19) 0.0313(7) Uani 1 1 d . . .
H5 H 0.2501 0.1031 0.5742 0.038 Uiso 1 1 calc R . .
C6 C 0.3276(2) 0.1147(4) 0.89033(18) 0.0214(6) Uani 1 1 d . . .
C7 C 0.39427(19) 0.1000(4) 0.96316(17) 0.0203(6) Uani 1 1 d . . .
C8 C 0.46757(19) 0.0035(3) 0.96554(16) 0.0202(6) Uani 1 1 d . . .
C9 C 0.47784(19) -0.0865(4) 0.90063(17) 0.0215(6) Uani 1 1 d . . .
C10 C 0.4093(2) -0.0850(4) 0.82873(17) 0.0226(6) Uani 1 1 d . . .
C11 C 0.3853(2) 0.1857(4) 1.02745(17) 0.0228(6) Uani 1 1 d . . .
H11 H 0.3366 0.2485 1.0252 0.027 Uiso 1 1 calc R . .
C12 C 0.5501(2) -0.1783(4) 0.90327(18) 0.0242(6) Uani 1 1 d . . .
H12 H 0.5565 -0.2353 0.8598 0.029 Uiso 1 1 calc 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
O1 C6 1.213(4) . ?
O2 C10 1.206(4) . ?
N1 C1 1.333(5) . ?
N1 C5 1.334(5) . ?
N2 C6 1.408(4) . ?
N2 C10 1.416(4) . ?
N2 C3 1.440(4) . ?
C1 C2 1.374(5) . ?
C2 C3 1.387(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.378(5) . ?
C6 C7 1.480(4) . ?
C7 C11 1.379(4) . ?
C7 C8 1.412(4) . ?
C8 C8 1.412(6) 5_657 ?
C8 C9 1.414(4) . ?
C9 C12 1.375(4) . ?
C9 C10 1.480(4) . ?
C11 C12 1.414(4) 5_657 ?
C12 C11 1.414(4) 5_657 ?

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
C1 N1 C5 122.7(3) . . ?
C6 N2 C10 125.8(3) . . ?
C6 N2 C3 117.9(3) . . ?
C10 N2 C3 116.4(2) . . ?
N1 C1 C2 119.9(3) . . ?
C1 C2 C3 118.5(3) . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 N2 119.7(3) . . ?
C2 C3 N2 119.8(3) . . ?
C5 C4 C3 118.2(3) . . ?
N1 C5 C4 120.1(3) . . ?
O1 C6 N2 120.2(3) . . ?
O1 C6 C7 123.6(3) . . ?
N2 C6 C7 116.2(3) . . ?
C11 C7 C8 120.7(3) . . ?
C11 C7 C6 119.3(3) . . ?
C8 C7 C6 120.0(3) . . ?
C8 C8 C7 119.3(3) 5_657 . ?
C8 C8 C9 119.0(3) 5_657 . ?
C7 C8 C9 121.7(3) . . ?
C12 C9 C8 121.2(3) . . ?
C12 C9 C10 118.9(3) . . ?
C8 C9 C10 119.9(3) . . ?
O2 C10 N2 120.0(3) . . ?
O2 C10 C9 123.8(3) . . ?
N2 C10 C9 116.1(3) . . ?
C7 C11 C12 120.3(3) . 5_657 ?
C9 C12 C11 119.6(3) . 5_657 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.370
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.110
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_(Et2DPNDI)(2I)
_database_code_depnum_ccdc_archive 'CCDC 1038298'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N4 O4, 2(I)'
_chemical_formula_sum            'C28 H22 I2 N4 O4'
_chemical_formula_weight         732.30

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2/c
_symmetry_space_group_name_Hall  '-P 2yc'

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

_cell_length_a                   12.006(2)
_cell_length_b                   7.4721(15)
_cell_length_c                   16.822(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.21(2)
_cell_angle_gamma                90.00
_cell_volume                     1342.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6230
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12197
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3064
_reflns_number_gt                2650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  'SHELXL97 and publCIF (Westrip, 2010)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+5.3023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3064
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.003
_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
O1 O 0.3389(3) 0.1717(6) 0.5112(3) 0.0570(11) Uani 1 1 d . . .
O2 O -0.0172(3) 0.5044(5) 0.3870(3) 0.0478(9) Uani 1 1 d . . .
N1 N 0.3252(4) 0.7219(6) 0.3572(3) 0.0507(11) Uani 1 1 d . . .
N2 N 0.1615(3) 0.3384(5) 0.4496(2) 0.0338(8) Uani 1 1 d . . .
I1 I 0.5000 0.42782(8) 0.2500 0.0587(2) Uani 1 2 d S . .
I2 I 0.0000 0.02483(8) 0.2500 0.0588(2) Uani 1 2 d S . .
C1 C 0.3684(13) 1.0307(17) 0.3383(11) 0.145(5) Uani 1 1 d . . .
H1A H 0.2813 1.0616 0.3137 0.218 Uiso 1 1 calc R . .
H1B H 0.4085 1.1074 0.3133 0.218 Uiso 1 1 calc R . .
H1C H 0.4075 1.0456 0.4021 0.218 Uiso 1 1 calc R . .
C2 C 0.3794(8) 0.8610(11) 0.3187(7) 0.098(3) Uani 1 1 d . . .
H2A H 0.4676 0.8350 0.3399 0.117 Uiso 1 1 calc R . .
H2B H 0.3386 0.8483 0.2542 0.117 Uiso 1 1 calc R . .
C3 C 0.3762(5) 0.6877(8) 0.4448(4) 0.0526(13) Uani 1 1 d . . .
H3 H 0.4470 0.7508 0.4837 0.063 Uiso 1 1 calc R . .
C4 C 0.3263(5) 0.5614(7) 0.4784(4) 0.0440(11) Uani 1 1 d . . .
H4 H 0.3616 0.5396 0.5396 0.053 Uiso 1 1 calc R . .
C5 C 0.2219(4) 0.4672(6) 0.4189(3) 0.0347(9) Uani 1 1 d . . .
C6 C 0.1758(5) 0.4971(8) 0.3294(3) 0.0478(13) Uani 1 1 d . . .
H6 H 0.1097 0.4287 0.2885 0.057 Uiso 1 1 calc R . .
C7 C 0.2283(5) 0.6300(9) 0.3001(4) 0.0558(14) Uani 1 1 d . . .
H7 H 0.1946 0.6547 0.2393 0.067 Uiso 1 1 calc R . .
C8 C 0.2294(4) 0.1871(7) 0.4946(3) 0.0384(10) Uani 1 1 d . . .
C9 C 0.1620(4) 0.0502(7) 0.5190(3) 0.0348(9) Uani 1 1 d . . .
C10 C 0.0325(4) 0.0682(6) 0.4904(3) 0.0303(9) Uani 1 1 d . . .
C11 C -0.0337(4) 0.2209(6) 0.4426(3) 0.0329(9) Uani 1 1 d . . .
C12 C 0.0320(4) 0.3657(7) 0.4228(3) 0.0354(9) Uani 1 1 d . . .
C13 C 0.2248(4) -0.0975(7) 0.5676(4) 0.0420(11) Uani 1 1 d . . .
H13 H 0.3109 -0.1065 0.5881 0.050 Uiso 1 1 calc R . .
C14 C -0.1610(4) 0.2342(7) 0.4137(3) 0.0409(10) Uani 1 1 d . . .
H14 H -0.2044 0.3342 0.3816 0.049 Uiso 1 1 calc 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
O1 C8 1.218(5) . ?
O2 C12 1.209(6) . ?
N1 C7 1.313(7) . ?
N1 C3 1.337(7) . ?
N1 C2 1.519(8) . ?
N2 C8 1.397(6) . ?
N2 C12 1.422(6) . ?
N2 C5 1.435(5) . ?
C1 C2 1.332(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.370(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(7) . ?
C6 C7 1.383(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.475(6) . ?
C9 C13 1.374(6) . ?
C9 C10 1.408(6) . ?
C10 C10 1.408(8) 3_556 ?
C10 C11 1.412(6) . ?
C11 C14 1.379(6) . ?
C11 C12 1.464(6) . ?
C13 C14 1.397(7) 3_556 ?
C13 H13 0.9300 . ?
C14 C13 1.397(7) 3_556 ?
C14 H14 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
C7 N1 C3 120.8(5) . . ?
C7 N1 C2 117.1(6) . . ?
C3 N1 C2 122.1(6) . . ?
C8 N2 C12 124.8(4) . . ?
C8 N2 C5 118.2(4) . . ?
C12 N2 C5 116.7(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 N1 115.9(10) . . ?
C1 C2 H2A 108.3 . . ?
N1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
N1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
N1 C3 C4 121.4(5) . . ?
N1 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.2(5) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 N2 119.3(4) . . ?
C4 C5 N2 121.3(4) . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
N1 C7 C6 120.7(5) . . ?
N1 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O1 C8 N2 120.1(4) . . ?
O1 C8 C9 122.9(4) . . ?
N2 C8 C9 117.0(4) . . ?
C13 C9 C10 120.0(4) . . ?
C13 C9 C8 120.0(4) . . ?
C10 C9 C8 119.9(4) . . ?
C10 C10 C9 119.5(5) 3_556 . ?
C10 C10 C11 119.3(5) 3_556 . ?
C9 C10 C11 121.2(4) . . ?
C14 C11 C10 120.2(4) . . ?
C14 C11 C12 119.4(4) . . ?
C10 C11 C12 120.3(4) . . ?
O2 C12 N2 119.7(4) . . ?
O2 C12 C11 123.7(4) . . ?
N2 C12 C11 116.5(4) . . ?
C9 C13 C14 120.8(4) . 3_556 ?
C9 C13 H13 119.6 . . ?
C14 C13 H13 119.6 3_556 . ?
C11 C14 C13 120.1(4) . 3_556 ?
C11 C14 H14 120.0 . . ?
C13 C14 H14 120.0 3_556 . ?

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
C7 N1 C2 C1 114.0(11) . . . . ?
C3 N1 C2 C1 -68.9(12) . . . . ?
C7 N1 C3 C4 -2.8(9) . . . . ?
C2 N1 C3 C4 -179.9(6) . . . . ?
N1 C3 C4 C5 1.0(9) . . . . ?
C3 C4 C5 C6 2.8(8) . . . . ?
C3 C4 C5 N2 -177.4(5) . . . . ?
C8 N2 C5 C6 116.4(5) . . . . ?
C12 N2 C5 C6 -56.9(6) . . . . ?
C8 N2 C5 C4 -63.4(6) . . . . ?
C12 N2 C5 C4 123.3(5) . . . . ?
C4 C5 C6 C7 -4.8(9) . . . . ?
N2 C5 C6 C7 175.4(5) . . . . ?
C3 N1 C7 C6 0.8(10) . . . . ?
C2 N1 C7 C6 178.0(7) . . . . ?
C5 C6 C7 N1 3.0(10) . . . . ?
C12 N2 C8 O1 176.6(5) . . . . ?
C5 N2 C8 O1 4.0(7) . . . . ?
C12 N2 C8 C9 -2.7(7) . . . . ?
C5 N2 C8 C9 -175.3(4) . . . . ?
O1 C8 C9 C13 4.2(8) . . . . ?
N2 C8 C9 C13 -176.6(5) . . . . ?
O1 C8 C9 C10 -173.9(5) . . . . ?
N2 C8 C9 C10 5.3(7) . . . . ?
C13 C9 C10 C10 -1.8(8) . . . 3_556 ?
C8 C9 C10 C10 176.3(5) . . . 3_556 ?
C13 C9 C10 C11 178.2(5) . . . . ?
C8 C9 C10 C11 -3.7(7) . . . . ?
C10 C10 C11 C14 -1.3(8) 3_556 . . . ?
C9 C10 C11 C14 178.7(5) . . . . ?
C10 C10 C11 C12 179.2(5) 3_556 . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C8 N2 C12 O2 177.3(5) . . . . ?
C5 N2 C12 O2 -10.0(7) . . . . ?
C8 N2 C12 C11 -1.6(7) . . . . ?
C5 N2 C12 C11 171.2(4) . . . . ?
C14 C11 C12 O2 5.1(8) . . . . ?
C10 C11 C12 O2 -175.4(5) . . . . ?
C14 C11 C12 N2 -176.1(4) . . . . ?
C10 C11 C12 N2 3.4(6) . . . . ?
C10 C9 C13 C14 2.3(8) . . . 3_556 ?
C8 C9 C13 C14 -175.8(5) . . . 3_556 ?
C10 C11 C14 C13 0.8(8) . . . 3_556 ?
C12 C11 C14 C13 -179.7(5) . . . 3_556 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         2.395
_refine_diff_density_min         -1.820
_refine_diff_density_rms         0.126
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
