# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_1-Mn
_database_code_depnum_ccdc_archive 'CCDC 1504617'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 Mn N2 O8'
_chemical_formula_sum            'C24 H20 Mn N2 O8'
_chemical_formula_weight         519.36

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.048(3)
_cell_length_b                   20.458(5)
_cell_length_c                   10.462(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.797(5)
_cell_angle_gamma                90
_cell_volume                     2148.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3976
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.672
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18306
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_max         23.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.799
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.799
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.799
_reflns_number_total             3105
_reflns_number_gt                2308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+8.0749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0021(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3105
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_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
Mn1 Mn 0.26166(8) 0.28620(4) 0.13279(8) 0.0319(3) Uani 1 1 d . . . . .
C1 C 0.6347(6) 0.2747(3) 0.2380(5) 0.0401(14) Uani 1 1 d . . . . .
H1 H 0.6359 0.2446 0.1714 0.048 Uiso 1 1 calc R U . . .
C2 C 0.7457(6) 0.3101(3) 0.2709(6) 0.0428(14) Uani 1 1 d . . . . .
H2 H 0.8235 0.3033 0.2282 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7434(6) 0.3557(3) 0.3673(6) 0.0421(14) Uani 1 1 d . . . . .
H3A H 0.8195 0.3798 0.3897 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6275(5) 0.3657(3) 0.4306(5) 0.0348(13) Uani 1 1 d . . . . .
C5 C 0.5173(6) 0.3268(3) 0.3972(5) 0.0348(13) Uani 1 1 d . . . . .
H5 H 0.4395 0.3310 0.4412 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6208(5) 0.4170(3) 0.5315(5) 0.0356(13) Uani 1 1 d . . . . .
C7 C 0.4457(6) 0.5906(3) 0.3574(5) 0.0405(14) Uani 1 1 d . . . . .
H7 H 0.4913 0.6294 0.3436 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4463(6) 0.5415(3) 0.2652(5) 0.0390(14) Uani 1 1 d . . . . .
H8 H 0.4913 0.5476 0.1906 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3789(5) 0.4829(3) 0.2855(5) 0.0332(13) Uani 1 1 d . . . . .
C10 C 0.3139(5) 0.4754(3) 0.3975(5) 0.0392(14) Uani 1 1 d . . . . .
H10 H 0.2685 0.4367 0.4119 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3149(5) 0.5242(3) 0.4889(5) 0.0364(13) Uani 1 1 d . . . . .
H11 H 0.2721 0.5175 0.5647 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3760(5) 0.4291(3) 0.1879(5) 0.0336(13) Uani 1 1 d . . . . .
C13 C -0.1052(7) 0.3326(3) -0.0735(6) 0.0590(19) Uani 1 1 d . . . . .
H13 H -0.1017 0.2966 -0.1276 0.071 Uiso 1 1 calc R U . . .
C14 C -0.2219(7) 0.3657(4) -0.0632(7) 0.069(2) Uani 1 1 d . . . . .
H14 H -0.2979 0.3520 -0.1100 0.083 Uiso 1 1 calc R U . . .
C15 C -0.2282(7) 0.4195(3) 0.0164(6) 0.0557(18) Uani 1 1 d . . . . .
H15 H -0.3081 0.4418 0.0239 0.067 Uiso 1 1 calc R U . . .
C16 C -0.1132(6) 0.4401(3) 0.0855(5) 0.0382(14) Uani 1 1 d . . . . .
C17 C 0.0022(6) 0.4044(3) 0.0725(5) 0.0397(14) Uani 1 1 d . . . . .
H17 H 0.0796 0.4168 0.1185 0.048 Uiso 1 1 calc R U . . .
C18 C -0.1145(5) 0.4957(3) 0.1754(5) 0.0341(13) Uani 1 1 d . . . . .
C19 C 0.0209(6) 0.0006(3) 0.2221(6) 0.0463(16) Uani 1 1 d . . . . .
H19 H -0.0457 -0.0307 0.2108 0.056 Uiso 1 1 calc R U . . .
C20 C 0.0276(6) 0.0524(3) 0.1372(6) 0.0415(14) Uani 1 1 d . . . . .
H20 H -0.0359 0.0556 0.0698 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1256(5) 0.0993(3) 0.1499(5) 0.0355(13) Uani 1 1 d . . . . .
C22 C 0.2163(5) 0.0950(3) 0.2530(5) 0.0380(14) Uani 1 1 d . . . . .
H22 H 0.2821 0.1267 0.2642 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2108(5) 0.0443(3) 0.3399(5) 0.0392(14) Uani 1 1 d . . . . .
H23 H 0.2721 0.0426 0.4093 0.047 Uiso 1 1 calc R U . . .
C24 C 0.1387(5) 0.1507(3) 0.0497(5) 0.0333(13) Uani 1 1 d . . . . .
N1 N 0.5236(4) 0.2834(2) 0.3015(4) 0.0326(11) Uani 1 1 d . . . . .
N2 N 0.0052(5) 0.3518(2) -0.0054(4) 0.0392(12) Uani 1 1 d . . . . .
O1 O 0.4165(4) 0.24565(17) 0.2717(3) 0.0381(9) Uani 1 1 d . . . . .
O4 O 0.1171(4) 0.31963(19) -0.0186(4) 0.0457(10) Uani 1 1 d . . . . .
O1W O 0.1090(4) 0.26917(18) 0.2687(4) 0.0438(10) Uani 1 1 d . . . . .
H1WB H 0.1258 0.2339 0.3094 0.066 Uiso 1 1 d R U . . .
H1WA H 0.1076 0.3010 0.3207 0.066 Uiso 1 1 d R U . . .
O2W O 0.4225(4) 0.30989(18) 0.0073(3) 0.0398(9) Uani 1 1 d . . . . .
H2WB H 0.3951 0.3055 -0.0704 0.060 Uiso 1 1 d R U . . .
H2WA H 0.4475 0.3491 0.0208 0.060 Uiso 1 1 d R U . . .
O5 O 0.0579(4) 0.1497(2) -0.0453(4) 0.0505(11) Uani 1 1 d . . . . .
O6 O 0.2359(3) 0.19036(17) 0.0630(3) 0.0367(9) Uani 1 1 d . . . . .
O2 O 0.2959(4) 0.38221(17) 0.2091(4) 0.0418(10) Uani 1 1 d . . . . .
O3 O 0.4486(4) 0.43205(19) 0.0958(4) 0.0506(11) Uani 1 1 d . . . . .


_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
Mn1 O6 2.104(4) . ?
Mn1 O2 2.142(4) . ?
Mn1 O1W 2.170(4) . ?
Mn1 O2W 2.186(4) . ?
Mn1 O4 2.205(4) . ?
Mn1 O1 2.236(4) . ?
C1 N1 1.338(7) . ?
C1 C2 1.360(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.394(7) . ?
C4 C6 1.492(7) . ?
C5 N1 1.343(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(8) 3_666 ?
C6 C11 1.387(7) 3_666 ?
C7 C6 1.378(8) 3_666 ?
C7 C8 1.393(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(7) . ?
C9 C12 1.500(7) . ?
C10 C11 1.382(7) . ?
C10 H10 0.9300 . ?
C11 C6 1.387(7) 3_666 ?
C11 H11 0.9300 . ?
C12 O3 1.238(6) . ?
C12 O2 1.279(6) . ?
C13 N2 1.348(8) . ?
C13 C14 1.364(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(8) . ?
C16 C18 1.478(7) . ?
C17 N2 1.350(7) . ?
C17 H17 0.9300 . ?
C18 C23 1.390(7) 2 ?
C18 C19 1.395(8) 2 ?
C19 C20 1.386(8) . ?
C19 C18 1.395(8) 2_545 ?
C19 H19 0.9300 . ?
C20 C21 1.376(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(7) . ?
C21 C24 1.496(7) . ?
C22 C23 1.382(8) . ?
C22 H22 0.9300 . ?
C23 C18 1.390(7) 2_545 ?
C23 H23 0.9300 . ?
C24 O5 1.253(6) . ?
C24 O6 1.271(6) . ?
N1 O1 1.348(5) . ?
N2 O4 1.316(6) . ?
O1W H1WB 0.8500 . ?
O1W H1WA 0.8500 . ?
O2W H2WB 0.8499 . ?
O2W H2WA 0.8499 . ?

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
O6 Mn1 O2 177.30(15) . . ?
O6 Mn1 O1W 89.92(14) . . ?
O2 Mn1 O1W 90.52(14) . . ?
O6 Mn1 O2W 94.60(14) . . ?
O2 Mn1 O2W 84.87(14) . . ?
O1W Mn1 O2W 175.02(14) . . ?
O6 Mn1 O4 88.53(14) . . ?
O2 Mn1 O4 94.11(15) . . ?
O1W Mn1 O4 93.34(15) . . ?
O2W Mn1 O4 88.87(14) . . ?
O6 Mn1 O1 87.11(14) . . ?
O2 Mn1 O1 90.22(14) . . ?
O1W Mn1 O1 90.38(15) . . ?
O2W Mn1 O1 87.77(14) . . ?
O4 Mn1 O1 174.26(14) . . ?
N1 C1 C2 119.9(5) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 120.3(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.7(5) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 118.3(5) . . ?
C3 C4 C6 120.7(5) . . ?
C5 C4 C6 121.0(5) . . ?
N1 C5 C4 119.9(5) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C11 118.4(5) 3_666 3_666 ?
C7 C6 C4 123.9(5) 3_666 . ?
C11 C6 C4 117.6(5) 3_666 . ?
C6 C7 C8 121.4(5) 3_666 . ?
C6 C7 H7 119.3 3_666 . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 118.5(5) . . ?
C10 C9 C12 120.2(5) . . ?
C8 C9 C12 121.3(5) . . ?
C9 C10 C11 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 120.5(5) . 3_666 ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 3_666 . ?
O3 C12 O2 124.8(5) . . ?
O3 C12 C9 120.1(5) . . ?
O2 C12 C9 115.0(5) . . ?
N2 C13 C14 120.1(6) . . ?
N2 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.5(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.3(6) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 117.8(5) . . ?
C17 C16 C18 120.2(5) . . ?
C15 C16 C18 121.9(5) . . ?
N2 C17 C16 121.5(5) . . ?
N2 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C23 C18 C19 118.5(5) 2 2 ?
C23 C18 C16 120.3(5) 2 . ?
C19 C18 C16 121.2(5) 2 . ?
C20 C19 C18 119.7(5) . 2_545 ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 2_545 . ?
C21 C20 C19 121.8(5) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 118.2(5) . . ?
C20 C21 C24 120.6(5) . . ?
C22 C21 C24 121.0(5) . . ?
C21 C22 C23 121.0(5) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 120.7(5) . 2_545 ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 2_545 . ?
O5 C24 O6 124.2(5) . . ?
O5 C24 C21 117.9(5) . . ?
O6 C24 C21 117.7(5) . . ?
C1 N1 C5 121.9(5) . . ?
C1 N1 O1 119.0(4) . . ?
C5 N1 O1 119.0(4) . . ?
O4 N2 C13 118.9(5) . . ?
O4 N2 C17 120.4(5) . . ?
C13 N2 C17 120.7(5) . . ?
N1 O1 Mn1 117.4(3) . . ?
N2 O4 Mn1 128.0(3) . . ?
Mn1 O1W H1WB 109.6 . . ?
Mn1 O1W H1WA 109.3 . . ?
H1WB O1W H1WA 109.8 . . ?
Mn1 O2W H2WB 109.7 . . ?
Mn1 O2W H2WA 109.3 . . ?
H2WB O2W H2WA 109.8 . . ?
C24 O6 Mn1 135.5(3) . . ?
C12 O2 Mn1 135.6(4) . . ?

_refine_diff_density_max         0.767
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.082

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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-Zn
_database_code_depnum_ccdc_archive 'CCDC 1504618'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N O4 Zn'
_chemical_formula_sum            'C12 H9 N O4 Zn'
_chemical_formula_weight         296.57

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.380(5)
_cell_length_b                   6.836(3)
_cell_length_c                   13.578(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.624(7)
_cell_angle_gamma                90
_cell_volume                     1044.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3976
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.356
_shelx_estimated_absorpt_T_min   0.650
_shelx_estimated_absorpt_T_max   0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4890
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.809
_diffrn_reflns_theta_max         24.646
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             1750
_reflns_number_gt                1001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1750
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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_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
Zn1 Zn 0.49514(8) 1.12578(14) 0.26105(7) 0.0360(4) Uani 1 1 d . . . . .
C1 C 0.3908(7) 0.7632(13) 0.4144(6) 0.040(2) Uani 1 1 d . . . . .
H1A H 0.4640 0.7845 0.4721 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3407(7) 0.5786(11) 0.3955(6) 0.038(2) Uani 1 1 d . . . . .
H2A H 0.3814 0.4747 0.4395 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2321(7) 0.5479(12) 0.3127(6) 0.037(2) Uani 1 1 d . . . . .
H3A H 0.1988 0.4234 0.3007 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1713(6) 0.7013(11) 0.2464(5) 0.0257(18) Uani 1 1 d . . . . .
C5 C 0.2269(6) 0.8788(11) 0.2681(6) 0.0327(18) Uani 1 1 d . . . . .
H5A H 0.1885 0.9839 0.2239 0.039 Uiso 1 1 calc R U . . .
C6 C 0.0492(6) 0.6768(11) 0.1587(6) 0.0292(19) Uani 1 1 d . . . . .
C7 C -0.0064(7) 0.4980(11) 0.1302(6) 0.034(2) Uani 1 1 d . . . . .
H7A H 0.0343 0.3869 0.1662 0.041 Uiso 1 1 calc R U . . .
C8 C -0.1194(6) 0.4770(10) 0.0508(5) 0.0263(18) Uani 1 1 d . . . . .
H8A H -0.1536 0.3532 0.0348 0.032 Uiso 1 1 calc R U . . .
C9 C -0.1831(6) 0.6382(11) -0.0060(5) 0.0277(17) Uani 1 1 d . . . . .
C10 C -0.1275(6) 0.8204(11) 0.0215(5) 0.031(2) Uani 1 1 d . . . . .
H10A H -0.1678 0.9309 -0.0157 0.037 Uiso 1 1 calc R U . . .
C11 C -0.0151(7) 0.8407(11) 0.1018(6) 0.037(2) Uani 1 1 d . . . . .
H11A H 0.0190 0.9644 0.1187 0.044 Uiso 1 1 calc R U . . .
C12 C -0.3073(6) 0.6254(12) -0.0945(5) 0.0272(17) Uani 1 1 d . . . . .
N1 N 0.3335(5) 0.9104(10) 0.3494(5) 0.0338(16) Uani 1 1 d . . . . .
O1 O 0.3812(5) 1.0842(8) 0.3640(4) 0.0462(15) Uani 1 1 d . . . . .
O2 O -0.3552(5) 0.7850(8) -0.1330(4) 0.0468(16) Uani 1 1 d . . . . .
O3 O -0.3504(4) 0.4577(7) -0.1214(4) 0.0331(13) Uani 1 1 d . . . . .
O4 O -0.5408(4) 0.6177(7) -0.3114(4) 0.0372(13) Uani 1 1 d . . . . .


_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
Zn1 O4 1.882(5) 3_575 ?
Zn1 O4 1.890(5) 4_676 ?
Zn1 O2 1.972(5) 3_575 ?
Zn1 O3 1.996(5) 4_676 ?
Zn1 O1 2.381(5) . ?
C1 N1 1.331(9) . ?
C1 C2 1.382(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.363(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.366(9) . ?
C4 C6 1.494(9) . ?
C5 N1 1.339(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.376(10) . ?
C6 C11 1.405(9) . ?
C7 C8 1.372(10) . ?
C7 H7A 0.9300 . ?
C8 C9 1.388(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.396(9) . ?
C9 C12 1.509(9) . ?
C10 C11 1.372(10) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O2 1.248(8) . ?
C12 O3 1.253(8) . ?
N1 O1 1.305(7) . ?
O2 Zn1 1.972(5) 3_575 ?
O3 Zn1 1.996(5) 4_475 ?
O4 Zn1 1.882(5) 3_575 ?
O4 Zn1 1.890(5) 4_475 ?

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
O4 Zn1 O4 168.51(9) 3_575 4_676 ?
O4 Zn1 O2 93.0(2) 3_575 3_575 ?
O4 Zn1 O2 83.3(2) 4_676 3_575 ?
O4 Zn1 O3 86.2(2) 3_575 4_676 ?
O4 Zn1 O3 96.0(2) 4_676 4_676 ?
O2 Zn1 O3 172.1(2) 3_575 4_676 ?
O4 Zn1 O1 93.4(2) 3_575 . ?
O4 Zn1 O1 97.6(2) 4_676 . ?
O2 Zn1 O1 92.1(2) 3_575 . ?
O3 Zn1 O1 95.8(2) 4_676 . ?
N1 C1 C2 119.5(7) . . ?
N1 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C3 C2 C1 120.4(7) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 120.2(8) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 116.4(7) . . ?
C5 C4 C6 121.5(7) . . ?
C3 C4 C6 122.0(7) . . ?
N1 C5 C4 123.8(7) . . ?
N1 C5 H5A 118.1 . . ?
C4 C5 H5A 118.1 . . ?
C7 C6 C11 116.8(7) . . ?
C7 C6 C4 123.0(7) . . ?
C11 C6 C4 120.2(6) . . ?
C8 C7 C6 122.7(7) . . ?
C8 C7 H7A 118.6 . . ?
C6 C7 H7A 118.6 . . ?
C7 C8 C9 120.7(7) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C8 C9 C10 117.2(7) . . ?
C8 C9 C12 123.5(7) . . ?
C10 C9 C12 119.3(7) . . ?
C11 C10 C9 121.8(7) . . ?
C11 C10 H10A 119.1 . . ?
C9 C10 H10A 119.1 . . ?
C10 C11 C6 120.7(7) . . ?
C10 C11 H11A 119.6 . . ?
C6 C11 H11A 119.6 . . ?
O2 C12 O3 127.4(6) . . ?
O2 C12 C9 115.6(7) . . ?
O3 C12 C9 117.0(7) . . ?
O1 N1 C1 120.3(7) . . ?
O1 N1 C5 120.0(6) . . ?
C1 N1 C5 119.6(7) . . ?
N1 O1 Zn1 111.1(4) . . ?
C12 O2 Zn1 136.9(5) . 3_575 ?
C12 O3 Zn1 130.1(5) . 4_475 ?
Zn1 O4 Zn1 131.4(2) 3_575 4_475 ?

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.123

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_3-Pb
_database_code_depnum_ccdc_archive 'CCDC 1504619'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2 O7 Pb'
_chemical_formula_sum            'C12 H10 N2 O7 Pb'
_chemical_formula_weight         501.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.864(2)
_cell_length_b                   10.2331(14)
_cell_length_c                   8.4530(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.405(2)
_cell_angle_gamma                90
_cell_volume                     1369.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3976
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.431
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    12.355
_shelx_estimated_absorpt_T_min   0.191
_shelx_estimated_absorpt_T_max   0.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
The largest residual density peaks in
3 appear adjacent to the Pb atom, typical of strong
absorption of this kind of heavy metal atom.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13630
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         25.196
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2454
_reflns_number_gt                2094
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1079P)²+14.8061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2454
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_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 0.37089(3) 0.27797(4) 0.26734(5) 0.0334(3) Uani 1 1 d . . . . .
C1 C 0.3458(8) 0.5957(14) 0.0123(17) 0.049(3) Uani 1 1 d . . . . .
H1 H 0.4038 0.5935 0.0354 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3015(11) 0.7110(13) 0.009(2) 0.059(4) Uani 1 1 d . . . . .
H2 H 0.3302 0.7879 0.0351 0.071 Uiso 1 1 calc R U . . .
C3 C 0.2177(10) 0.7171(12) -0.032(2) 0.056(4) Uani 1 1 d . . . . .
H3 H 0.1897 0.7969 -0.0341 0.067 Uiso 1 1 calc R U . . .
C4 C 0.1742(8) 0.6026(11) -0.0701(14) 0.036(3) Uani 1 1 d . . . . .
C5 C 0.2202(7) 0.4865(11) -0.0619(13) 0.031(2) Uani 1 1 d . . . . .
H5 H 0.1929 0.4083 -0.0873 0.037 Uiso 1 1 calc R U . . .
C6 C 0.0555(8) 0.3119(12) 0.1119(15) 0.039(3) Uani 1 1 d . . . . .
H6 H 0.0929 0.2568 0.0636 0.047 Uiso 1 1 calc R U . . .
C7 C -0.0278(8) 0.3141(12) 0.0577(15) 0.039(3) Uani 1 1 d . . . . .
H7 H -0.0462 0.2600 -0.0258 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0840(7) 0.6046(11) -0.1255(14) 0.034(2) Uani 1 1 d . . . . .
C9 C -0.0559(7) 0.4778(13) 0.2494(14) 0.039(3) Uani 1 1 d . . . . .
H9 H -0.0932 0.5347 0.2949 0.047 Uiso 1 1 calc R U . . .
C10 C 0.0269(8) 0.4739(12) 0.3031(15) 0.041(3) Uani 1 1 d . . . . .
H10 H 0.0453 0.5286 0.3860 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0851(7) 0.3901(11) 0.2372(13) 0.031(2) Uani 1 1 d . . . . .
C12 C 0.1742(8) 0.3814(12) 0.3058(15) 0.038(3) Uani 1 1 d . . . . .
N1 N 0.3006(6) 0.4846(9) -0.0196(11) 0.035(2) Uani 1 1 d . . . . .
N2 N 0.5279(7) 0.1009(11) 0.1436(13) 0.045(3) Uani 1 1 d . . . . .
O1 O 0.3431(5) 0.3712(8) -0.0089(9) 0.0385(19) Uani 1 1 d . . . . .
O2 O 0.2212(7) 0.3026(11) 0.2395(13) 0.056(3) Uani 1 1 d . . . . .
O3 O 0.1936(6) 0.4507(11) 0.4230(13) 0.062(3) Uani 1 1 d . . . . .
O4 O 0.4871(7) 0.0617(15) 0.2555(12) 0.072(3) Uani 1 1 d . . . . .
O5 O 0.5002(8) 0.1969(11) 0.0654(16) 0.065(3) Uani 1 1 d . . . . .
O6 O 0.5936(6) 0.0443(10) 0.1106(13) 0.058(3) Uani 1 1 d . . . . .
O1W O 0.3197(6) 0.0890(9) 0.1251(10) 0.046(2) Uani 1 1 d . . . . .
H1WB H 0.3070 0.0300 0.1903 0.055 Uiso 1 1 d R U . . .
H1WA H 0.2764 0.1095 0.0664 0.069 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pb1 O2 2.386(10) . ?
Pb1 O1W 2.394(9) . ?
Pb1 O1 2.490(8) 4_566 ?
Pb1 O1 2.537(8) . ?
C1 N1 1.362(17) . ?
C1 C2 1.37(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.35(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(16) . ?
C4 C8 1.479(16) . ?
C5 N1 1.304(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(19) . ?
C6 C11 1.386(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(17) 3_565 ?
C7 H7 0.9300 . ?
C8 C7 1.370(17) 3_565 ?
C8 C9 1.397(17) 3_565 ?
C9 C10 1.365(18) . ?
C9 C8 1.397(17) 3_565 ?
C9 H9 0.9300 . ?
C10 C11 1.400(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.498(17) . ?
C12 O3 1.242(16) . ?
C12 O2 1.253(16) . ?
N1 O1 1.342(12) . ?
N2 O6 1.239(14) . ?
N2 O4 1.244(15) . ?
N2 O5 1.249(16) . ?
O1 Pb1 2.490(8) 4_565 ?
O1W H1WB 0.8500 . ?
O1W H1WA 0.8500 . ?

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
O2 Pb1 O1W 74.3(3) . . ?
O2 Pb1 O1 85.4(3) . 4_566 ?
O1W Pb1 O1 79.4(3) . 4_566 ?
O2 Pb1 O1 75.6(3) . . ?
O1W Pb1 O1 78.8(3) . . ?
O1 Pb1 O1 154.3(3) 4_566 . ?
N1 C1 C2 116.8(11) . . ?
N1 C1 H1 121.6 . . ?
C2 C1 H1 121.6 . . ?
C3 C2 C1 122.6(13) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 119.2(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 117.1(11) . . ?
C3 C4 C8 121.3(11) . . ?
C5 C4 C8 121.5(10) . . ?
N1 C5 C4 121.9(11) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C7 C6 C11 121.5(12) . . ?
C7 C6 H6 119.3 . . ?
C11 C6 H6 119.3 . . ?
C8 C7 C6 120.5(12) 3_565 . ?
C8 C7 H7 119.8 3_565 . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.6(11) 3_565 3_565 ?
C7 C8 C4 121.2(11) 3_565 . ?
C9 C8 C4 119.3(10) 3_565 . ?
C10 C9 C8 119.3(11) . 3_565 ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 3_565 . ?
C9 C10 C11 122.0(11) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C6 C11 C10 117.1(11) . . ?
C6 C11 C12 122.1(11) . . ?
C10 C11 C12 120.7(10) . . ?
O3 C12 O2 126.7(12) . . ?
O3 C12 C11 117.3(11) . . ?
O2 C12 C11 115.9(11) . . ?
C5 N1 O1 120.7(10) . . ?
C5 N1 C1 122.4(10) . . ?
O1 N1 C1 116.9(9) . . ?
O6 N2 O4 120.2(12) . . ?
O6 N2 O5 121.5(12) . . ?
O4 N2 O5 118.3(12) . . ?
N1 O1 Pb1 126.1(6) . 4_565 ?
N1 O1 Pb1 116.5(6) . . ?
Pb1 O1 Pb1 116.1(3) 4_565 . ?
C12 O2 Pb1 129.7(9) . . ?
Pb1 O1W H1WB 109.6 . . ?
Pb1 O1W H1WA 109.4 . . ?
H1WB O1W H1WA 109.8 . . ?

_refine_diff_density_max         3.388
_refine_diff_density_min         -1.959
_refine_diff_density_rms         0.277

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_4-Mn
_database_code_depnum_ccdc_archive 'CCDC 1504620'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H54 Mn3 N4 O26'
_chemical_formula_sum            'C50 H54 Mn3 N4 O26'
_chemical_formula_weight         1291.79

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.412(3)
_cell_length_b                   15.726(3)
_cell_length_c                   12.078(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.315(4)
_cell_angle_gamma                90
_cell_volume                     2545.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3976
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_F_000             1330
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.832
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10790
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.997
_diffrn_reflns_theta_max         23.232
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.784
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.784
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.784
_reflns_number_total             3618
_reflns_number_gt                2212
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2200P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3618
_refine_ls_number_parameters     356
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0911
_refine_ls_wR_factor_ref         0.3230
_refine_ls_wR_factor_gt          0.2806
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Mn1 Mn 1.0000 0.0000 0.0000 0.0469(7) Uani 1 2 d S . P . .
Mn2 Mn 1.01232(9) 0.16071(10) 0.24450(11) 0.0511(6) Uani 1 1 d . . . . .
C1 C 1.2389(6) 0.0367(6) 0.1962(7) 0.047(2) Uani 1 1 d . . . . .
H1A H 1.2037 0.0069 0.2485 0.056 Uiso 1 1 calc R U . . .
C2 C 1.3414(6) 0.0336(6) 0.2007(7) 0.048(2) Uani 1 1 d . . . . .
H2A H 1.3746 0.0024 0.2563 0.057 Uiso 1 1 calc R U . . .
C3 C 1.3958(6) 0.0770(5) 0.1223(7) 0.041(2) Uani 1 1 d . . . . .
C4 C 1.3395(6) 0.1220(6) 0.0426(8) 0.053(2) Uani 1 1 d . . . . .
H4A H 1.3718 0.1506 -0.0131 0.064 Uiso 1 1 calc R U . . .
C5 C 1.2370(6) 0.1251(7) 0.0446(9) 0.062(3) Uani 1 1 d . . . . .
H5A H 1.2011 0.1583 -0.0067 0.075 Uiso 1 1 calc R U . . .
C6 C 1.5069(5) 0.0753(5) 0.1218(7) 0.038(2) Uani 1 1 d . . . . .
C7 C 1.5637(6) 0.0473(6) 0.2161(7) 0.047(2) Uani 1 1 d . . . . .
H7A H 1.5317 0.0279 0.2781 0.057 Uiso 1 1 calc R U . . .
C8 C 1.6678(6) 0.0489(6) 0.2161(7) 0.048(2) Uani 1 1 d . . . . .
H8A H 1.7047 0.0322 0.2792 0.058 Uiso 1 1 calc R U . . .
C9 C 1.7163(6) 0.0746(5) 0.1242(7) 0.039(2) Uani 1 1 d . . . . .
C10 C 1.6602(6) 0.1000(6) 0.0314(8) 0.049(2) Uani 1 1 d . . . . .
H10A H 1.6923 0.1168 -0.0318 0.059 Uiso 1 1 calc R U . . .
C11 C 1.5578(6) 0.1007(5) 0.0315(7) 0.046(2) Uani 1 1 d . . . . .
H11A H 1.5220 0.1190 -0.0316 0.055 Uiso 1 1 calc R U . . .
C12 C 1.8279(6) 0.0806(6) 0.1234(9) 0.048(2) Uani 1 1 d . . . . .
C13 C 0.7768(7) 0.2067(6) 0.4065(8) 0.055(2) Uani 1 1 d . . . . .
H13A H 0.8056 0.1732 0.4626 0.066 Uiso 1 1 calc R U . . .
C14 C 0.6753(7) 0.2080(7) 0.3905(9) 0.061(3) Uani 1 1 d . . . . .
H14A H 0.6360 0.1756 0.4362 0.074 Uiso 1 1 calc R U . . .
C15 C 0.6292(6) 0.2579(6) 0.3057(8) 0.049(2) Uani 1 1 d . . . . .
C16 C 0.6925(6) 0.3042(6) 0.2403(9) 0.057(3) Uani 1 1 d . . . . .
H16A H 0.6664 0.3377 0.1827 0.068 Uiso 1 1 calc R U . . .
C17 C 0.7955(7) 0.3003(7) 0.2616(9) 0.060(3) Uani 1 1 d . . . . .
H17A H 0.8373 0.3320 0.2178 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5171(6) 0.2620(6) 0.2910(8) 0.050(2) Uani 1 1 d . . . . .
C19 C 0.4560(6) 0.2129(6) 0.3530(8) 0.051(2) Uani 1 1 d . . . . .
H19A H 0.4834 0.1757 0.4058 0.061 Uiso 1 1 calc R U . . .
C20 C 0.3519(6) 0.2187(6) 0.3369(8) 0.054(3) Uani 1 1 d . . . . .
H20A H 0.3113 0.1841 0.3784 0.064 Uiso 1 1 calc R U . . .
C21 C 0.3083(6) 0.2739(6) 0.2614(9) 0.055(3) Uani 1 1 d . . . . .
C22 C 0.3699(7) 0.3237(7) 0.1997(10) 0.068(3) Uani 1 1 d . . . . .
H22A H 0.3421 0.3614 0.1478 0.081 Uiso 1 1 calc R U . . .
C23 C 0.4735(7) 0.3182(7) 0.2141(9) 0.064(3) Uani 1 1 d . . . . .
H23A H 0.5139 0.3524 0.1719 0.076 Uiso 1 1 calc R U . . .
C24 C 0.1973(8) 0.2791(8) 0.2455(10) 0.069(3) Uani 1 1 d . . . . .
C25 C 1.018(3) -0.025(2) 0.383(4) 0.348(17) Uiso 1 1 d D U . . .
H25A H 0.9503 -0.0385 0.3741 0.418 Uiso 1 1 calc R U . . .
N1 N 1.1893(4) 0.0810(4) 0.1191(6) 0.0439(18) Uani 1 1 d . . . . .
N2 N 0.8354(5) 0.2529(5) 0.3424(6) 0.0477(19) Uani 1 1 d . . . . .
O1 O 1.0873(4) 0.0826(4) 0.1168(5) 0.0570(17) Uani 1 1 d . . . . .
O1W O 0.9770(5) -0.0905(4) 0.1355(6) 0.070(2) Uani 1 1 d . . . . .
H1WB H 0.9153 -0.1023 0.1375 0.083 Uiso 1 1 d R U . . .
H1WA H 1.0102 -0.1355 0.1242 0.104 Uiso 1 1 d R U . . .
O2 O 1.8745(4) 0.0963(4) 0.2136(6) 0.0599(18) Uani 1 1 d . . . . .
O2W O 0.9856(5) 0.2546(5) 0.1041(6) 0.070(2) Uani 1 1 d . . . . .
H2WB H 0.9394 0.2363 0.0600 0.084 Uiso 1 1 d R U . . .
H2WA H 0.9688 0.3024 0.1306 0.105 Uiso 1 1 d R U . . .
O3 O 1.8674(4) 0.0704(4) 0.0309(5) 0.0543(17) Uani 1 1 d . . . . .
O3W O 0.3874(5) 0.9699(4) 0.4692(4) 0.0486(16) Uani 1 1 d . . . . .
O4 O 0.9351(4) 0.2485(4) 0.3586(5) 0.0555(17) Uani 1 1 d . . . . .
O4W O 0.2233(19) 1.0742(16) 0.513(2) 0.275(11) Uiso 1 1 d . . . . .
O5 O 0.1487(4) 0.2222(5) 0.2874(6) 0.0644(19) Uani 1 1 d . . . . .
O5W O 1.1521(17) 0.0245(15) 0.5446(19) 0.255(9) Uiso 1 1 d . . . . .
O6 O 0.1610(6) 0.3409(7) 0.1977(12) 0.145(5) Uani 1 1 d . . . . .
O7 O 1.0390(8) 0.0657(6) 0.3699(7) 0.110(3) Uani 1 1 d . . . . .
O8 O 1.073(2) -0.0880(16) 0.405(3) 0.309(11) Uiso 1 1 d D 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
Mn1 O3 2.140(6) 3_855 ?
Mn1 O3 2.140(6) 1_455 ?
Mn1 O1 2.218(6) . ?
Mn1 O1 2.218(6) 3_755 ?
Mn1 O1W 2.199(7) . ?
Mn1 O1W 2.199(7) 3_755 ?
Mn2 O5 2.115(6) 1_655 ?
Mn2 O7 2.147(9) . ?
Mn2 O2 2.128(6) 1_455 ?
Mn2 O4 2.235(6) . ?
Mn2 O1 2.241(6) . ?
Mn2 O2W 2.267(7) . ?
C1 N1 1.321(11) . ?
C1 C2 1.374(11) . ?
C1 H1A 0.9300 . ?
C2 C3 1.398(12) . ?
C2 H2A 0.9300 . ?
C3 C4 1.393(12) . ?
C3 C6 1.490(10) . ?
C4 C5 1.378(12) . ?
C4 H4A 0.9300 . ?
C5 N1 1.322(12) . ?
C5 H5A 0.9300 . ?
C6 C11 1.369(11) . ?
C6 C7 1.414(12) . ?
C7 C8 1.396(11) . ?
C7 H7A 0.9300 . ?
C8 C9 1.370(12) . ?
C8 H8A 0.9300 . ?
C9 C10 1.383(12) . ?
C9 C12 1.500(11) . ?
C10 C11 1.374(11) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O2 1.257(11) . ?
C12 O3 1.267(11) . ?
C13 N2 1.340(12) . ?
C13 C14 1.368(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.414(13) . ?
C14 H14A 0.9300 . ?
C15 C16 1.389(13) . ?
C15 C18 1.507(11) . ?
C16 C17 1.397(12) . ?
C16 H16A 0.9300 . ?
C17 N2 1.324(12) . ?
C17 H17A 0.9300 . ?
C18 C23 1.394(14) . ?
C18 C19 1.371(12) . ?
C19 C20 1.405(11) . ?
C19 H19A 0.9300 . ?
C20 C21 1.372(13) . ?
C20 H20A 0.9300 . ?
C21 C22 1.378(14) . ?
C21 C24 1.496(13) . ?
C22 C23 1.396(12) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 O6 1.221(13) . ?
C24 O5 1.229(12) . ?
C25 O7 1.46(4) . ?
C25 O8 1.260(19) . ?
C25 H25A 0.9300 . ?
N1 O1 1.367(8) . ?
N2 O4 1.345(8) . ?
O1W H1WB 0.8500 . ?
O1W H1WA 0.8501 . ?
O2 Mn2 2.128(6) 1_655 ?
O2W H2WB 0.8500 . ?
O2W H2WA 0.8500 . ?
O3 Mn1 2.140(6) 1_655 ?
O4W O5W 1.30(3) 1_465 ?
O5 Mn2 2.115(6) 1_455 ?
O5W O4W 1.30(3) 1_645 ?

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
O3 Mn1 O3 180.0(5) 3_855 1_455 ?
O3 Mn1 O1 89.6(2) 3_855 . ?
O3 Mn1 O1 90.4(2) 1_455 . ?
O3 Mn1 O1 90.4(2) 3_855 3_755 ?
O3 Mn1 O1 89.6(2) 1_455 3_755 ?
O1 Mn1 O1 180.0 . 3_755 ?
O3 Mn1 O1W 86.4(3) 3_855 . ?
O3 Mn1 O1W 93.6(3) 1_455 . ?
O1 Mn1 O1W 89.5(3) . . ?
O1 Mn1 O1W 90.5(3) 3_755 . ?
O3 Mn1 O1W 93.6(3) 3_855 3_755 ?
O3 Mn1 O1W 86.4(3) 1_455 3_755 ?
O1 Mn1 O1W 90.5(3) . 3_755 ?
O1 Mn1 O1W 89.5(3) 3_755 3_755 ?
O1W Mn1 O1W 180.0 . 3_755 ?
O5 Mn2 O7 91.6(3) 1_655 . ?
O5 Mn2 O2 175.9(3) 1_655 1_455 ?
O7 Mn2 O2 84.9(3) . 1_455 ?
O5 Mn2 O4 89.1(2) 1_655 . ?
O7 Mn2 O4 93.7(3) . . ?
O2 Mn2 O4 88.9(2) 1_455 . ?
O5 Mn2 O1 90.6(2) 1_655 . ?
O7 Mn2 O1 92.1(3) . . ?
O2 Mn2 O1 91.7(2) 1_455 . ?
O4 Mn2 O1 174.2(3) . . ?
O5 Mn2 O2W 89.7(3) 1_655 . ?
O7 Mn2 O2W 176.4(3) . . ?
O2 Mn2 O2W 94.0(3) 1_455 . ?
O4 Mn2 O2W 89.7(3) . . ?
O1 Mn2 O2W 84.5(3) . . ?
N1 C1 C2 121.5(8) . . ?
N1 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C1 C2 C3 120.3(8) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 C4 115.7(8) . . ?
C2 C3 C6 122.9(8) . . ?
C4 C3 C6 121.4(8) . . ?
C5 C4 C3 121.2(9) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
N1 C5 C4 120.3(9) . . ?
N1 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C11 C6 C7 117.5(7) . . ?
C11 C6 C3 121.9(7) . . ?
C7 C6 C3 120.6(7) . . ?
C8 C7 C6 120.1(8) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C9 C8 C7 120.8(8) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 C10 118.8(7) . . ?
C8 C9 C12 122.0(8) . . ?
C10 C9 C12 119.1(8) . . ?
C11 C10 C9 120.8(8) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C6 C11 C10 121.9(8) . . ?
C6 C11 H11A 119.0 . . ?
C10 C11 H11A 119.0 . . ?
O2 C12 O3 125.3(8) . . ?
O2 C12 C9 117.9(8) . . ?
O3 C12 C9 116.8(8) . . ?
N2 C13 C14 120.9(9) . . ?
N2 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
C13 C14 C15 121.0(9) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 116.3(8) . . ?
C16 C15 C18 122.7(9) . . ?
C14 C15 C18 120.9(9) . . ?
C17 C16 C15 119.7(10) . . ?
C17 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
N2 C17 C16 121.8(9) . . ?
N2 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C23 C18 C19 118.5(8) . . ?
C23 C18 C15 119.6(8) . . ?
C19 C18 C15 121.8(9) . . ?
C18 C19 C20 120.0(9) . . ?
C18 C19 H19A 120.0 . . ?
C20 C19 H19A 120.0 . . ?
C21 C20 C19 121.8(9) . . ?
C21 C20 H20A 119.1 . . ?
C19 C20 H20A 119.1 . . ?
C20 C21 C22 118.1(8) . . ?
C20 C21 C24 121.0(9) . . ?
C22 C21 C24 120.9(10) . . ?
C23 C22 C21 120.8(10) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C18 C23 C22 120.8(9) . . ?
C18 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
O6 C24 O5 124.5(10) . . ?
O6 C24 C21 118.7(10) . . ?
O5 C24 C21 116.7(10) . . ?
O7 C25 O8 132(4) . . ?
O7 C25 H25A 113.9 . . ?
O8 C25 H25A 113.9 . . ?
C1 N1 C5 120.8(7) . . ?
C1 N1 O1 120.0(7) . . ?
C5 N1 O1 119.1(7) . . ?
C17 N2 C13 120.2(8) . . ?
C17 N2 O4 120.4(8) . . ?
C13 N2 O4 119.4(8) . . ?
N1 O1 Mn1 120.2(5) . . ?
N1 O1 Mn2 118.2(5) . . ?
Mn1 O1 Mn2 121.2(3) . . ?
Mn1 O1W H1WB 109.2 . . ?
Mn1 O1W H1WA 109.3 . . ?
H1WB O1W H1WA 109.8 . . ?
C12 O2 Mn2 130.0(6) . 1_655 ?
Mn2 O2W H2WB 109.7 . . ?
Mn2 O2W H2WA 109.3 . . ?
H2WB O2W H2WA 109.8 . . ?
C12 O3 Mn1 126.9(6) . 1_655 ?
N2 O4 Mn2 115.1(4) . . ?
C24 O5 Mn2 134.4(7) . 1_455 ?
C25 O7 Mn2 137(2) . . ?

_refine_diff_density_max         1.017
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.144

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_5-Zn
_database_code_depnum_ccdc_archive 'CCDC 1504621'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N2 O8 Zn'
_chemical_formula_sum            'C24 H20 N2 O8 Zn'
_chemical_formula_weight         529.79

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.133(8)
_cell_length_b                   7.397(3)
_cell_length_c                   15.679(6)
_cell_angle_alpha                90
_cell_angle_beta                 118.019(7)
_cell_angle_gamma                90
_cell_volume                     2163.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3976
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.192
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5084
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.471
_diffrn_reflns_theta_max         24.140
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.879
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.817
_reflns_number_total             3207
_reflns_number_gt                2373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.743

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1204P)²+34.3258P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0007(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 780 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.52(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3207
_refine_ls_number_parameters     324
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0906
_refine_ls_wR_factor_ref         0.2743
_refine_ls_wR_factor_gt          0.2572
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003

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
Zn1 Zn 1.0000 0.6890(4) 1.0000 0.0443(10) Uani 1 2 d S T P . .
Zn2 Zn 1.0000 0.4279(4) 0.5000 0.0466(11) Uani 1 2 d S T P . .
C1 C 0.6898(13) 0.731(3) 0.2513(14) 0.053(6) Uani 1 1 d . . . . .
H1A H 0.7076 0.7593 0.2089 0.064 Uiso 1 1 calc R U . . .
C2 C 0.7344(11) 0.728(3) 0.3510(15) 0.050(6) Uani 1 1 d . . . . .
H2A H 0.7827 0.7569 0.3759 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7068(11) 0.683(4) 0.4140(13) 0.042(5) Uani 1 1 d . . . . .
C4 C 0.6357(12) 0.641(4) 0.3758(16) 0.062(7) Uani 1 1 d . . . . .
H4A H 0.6159 0.6100 0.4156 0.074 Uiso 1 1 calc R U . . .
C5 C 0.5933(13) 0.647(4) 0.2752(18) 0.068(8) Uani 1 1 d . . . . .
H5A H 0.5448 0.6198 0.2493 0.082 Uiso 1 1 calc R U . . .
C6 C 0.7715(10) 0.723(3) 0.6832(13) 0.043(5) Uani 1 1 d . . . . .
H6A H 0.7520 0.7471 0.7243 0.051 Uiso 1 1 calc R U . . .
C7 C 0.7278(10) 0.723(3) 0.5843(14) 0.044(5) Uani 1 1 d . . . . .
H7A H 0.6796 0.7507 0.5604 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7529(12) 0.683(5) 0.5194(14) 0.040(5) Uani 1 1 d . . . . .
C9 C 0.8292(10) 0.646(3) 0.5586(14) 0.043(6) Uani 1 1 d . . . . .
H9A H 0.8490 0.6223 0.5179 0.051 Uiso 1 1 calc R U . . .
C10 C 0.8716(9) 0.648(3) 0.6582(14) 0.041(5) Uani 1 1 d . . . . .
H10A H 0.9200 0.6207 0.6831 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8458(9) 0.688(4) 0.7222(13) 0.038(5) Uani 1 1 d . . . . .
C12 C 0.8921(10) 0.688(3) 0.8300(13) 0.040(4) Uani 1 1 d . . . . .
C13 C 0.6516(11) 0.494(3) -0.2510(15) 0.045(5) Uani 1 1 d . . . . .
H13A H 0.6579 0.5383 -0.3021 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7071(10) 0.496(3) -0.1613(13) 0.038(4) Uani 1 1 d . . . . .
H14A H 0.7509 0.5399 -0.1529 0.045 Uiso 1 1 calc R U . . .
C15 C 0.7025(10) 0.436(4) -0.0808(13) 0.036(5) Uani 1 1 d . . . . .
C16 C 0.6336(10) 0.372(3) -0.0998(14) 0.043(5) Uani 1 1 d . . . . .
H16A H 0.6255 0.3335 -0.0493 0.051 Uiso 1 1 calc R U . . .
C17 C 0.5794(10) 0.368(3) -0.1927(13) 0.042(5) Uani 1 1 d . . . . .
H17A H 0.5353 0.3212 -0.2037 0.050 Uiso 1 1 calc R U . . .
C18 C 0.8037(10) 0.478(3) 0.1881(14) 0.041(5) Uani 1 1 d . . . . .
H18A H 0.7943 0.5080 0.2387 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7483(11) 0.478(3) 0.0962(13) 0.042(5) Uani 1 1 d . . . . .
H19A H 0.7020 0.5046 0.0850 0.051 Uiso 1 1 calc R U . . .
C20 C 0.7617(10) 0.438(3) 0.0180(14) 0.031(4) Uani 1 1 d . . . . .
C21 C 0.8320(11) 0.407(4) 0.0366(14) 0.051(6) Uani 1 1 d . . . . .
H21A H 0.8418 0.3876 -0.0146 0.061 Uiso 1 1 calc R U . . .
C22 C 0.8871(10) 0.403(3) 0.1300(13) 0.045(5) Uani 1 1 d . . . . .
H22A H 0.9336 0.3799 0.1411 0.054 Uiso 1 1 calc R U . . .
C23 C 0.8740(10) 0.434(3) 0.2095(13) 0.038(5) Uani 1 1 d . . . . .
C24 C 0.9327(10) 0.421(3) 0.3114(14) 0.037(4) Uani 1 1 d . . . . .
N1 N 0.6181(11) 0.689(3) 0.2175(14) 0.067(6) Uani 1 1 d . . . . .
N2 N 0.5860(8) 0.428(3) -0.2688(10) 0.038(4) Uani 1 1 d . . . . .
O1 O 0.5759(12) 0.688(3) 0.1236(10) 0.093(7) Uani 1 1 d . . . . .
O1W O 1.0000 0.425(5) 1.0000 0.112(12) Uani 1 2 d S T P . .
O2 O 0.9599(7) 0.692(3) 0.8611(9) 0.046(3) Uani 1 1 d . . . . .
O2W O 1.0000 0.944(4) 1.0000 0.128(16) Uani 1 2 d S T P . .
O3 O 0.8634(7) 0.691(3) 0.8812(9) 0.061(4) Uani 1 1 d . . . . .
O3W O 1.0000 0.157(5) 0.5000 0.096(10) Uani 1 2 d S TU P . .
O4 O 0.5318(8) 0.422(3) -0.3570(9) 0.051(4) Uani 1 1 d . . . . .
O4W O 1.0209(12) 0.682(4) 0.5004(19) 0.041(6) Uani 0.5 1 d . U P . .
O5 O 0.9949(7) 0.406(3) 0.3289(10) 0.065(5) Uani 1 1 d . . . . .
O6 O 0.9140(7) 0.435(3) 0.3781(9) 0.055(4) Uani 1 1 d . . . . .


_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
Zn1 O2W 1.89(3) . ?
Zn1 O2 1.931(12) . ?
Zn1 O2 1.931(12) 2_757 ?
Zn1 O1W 1.95(4) . ?
Zn1 C12 2.568(19) 2_757 ?
Zn2 O6 1.923(13) 2_756 ?
Zn2 O6 1.923(13) . ?
Zn2 O4W 1.93(3) 2_756 ?
Zn2 O4W 1.93(3) . ?
Zn2 O3W 2.00(3) . ?
C1 N1 1.39(3) . ?
C1 C2 1.40(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.40(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.36(3) . ?
C3 C8 1.47(3) . ?
C4 C5 1.40(3) . ?
C4 H4A 0.9300 . ?
C5 N1 1.28(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.38(3) . ?
C6 C11 1.42(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.38(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.45(3) . ?
C9 C10 1.39(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.38(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.50(3) . ?
C12 O3 1.22(2) . ?
C12 O2 1.28(2) . ?
C13 C14 1.34(3) . ?
C13 N2 1.37(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.38(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.42(3) . ?
C15 C20 1.46(3) . ?
C16 C17 1.37(3) . ?
C16 H16A 0.9300 . ?
C17 N2 1.34(2) . ?
C17 H17A 0.9300 . ?
C18 C19 1.36(3) . ?
C18 C23 1.40(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.41(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.39(3) . ?
C21 C22 1.38(3) . ?
C21 H21A 0.9300 . ?
C22 C23 1.42(3) . ?
C22 H22A 0.9300 . ?
C23 C24 1.50(2) . ?
C24 O5 1.22(2) . ?
C24 O6 1.28(2) . ?
N1 O1 1.31(2) . ?
N2 O4 1.319(18) . ?
O4W O4W 0.88(4) 2_756 ?

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
O2W Zn1 O2 89.4(6) . . ?
O2W Zn1 O2 89.4(6) . 2_757 ?
O2 Zn1 O2 178.9(11) . 2_757 ?
O2W Zn1 O1W 180.00(3) . . ?
O2 Zn1 O1W 90.6(6) . . ?
O2 Zn1 O1W 90.6(6) 2_757 . ?
O2W Zn1 C12 90.2(6) . 2_757 ?
O2 Zn1 C12 151.2(6) . 2_757 ?
O2 Zn1 C12 28.8(6) 2_757 2_757 ?
O1W Zn1 C12 89.8(6) . 2_757 ?
O6 Zn2 O6 176.7(14) 2_756 . ?
O6 Zn2 O4W 94.8(10) 2_756 2_756 ?
O6 Zn2 O4W 82.0(10) . 2_756 ?
O6 Zn2 O4W 82.0(10) 2_756 . ?
O6 Zn2 O4W 94.8(10) . . ?
O4W Zn2 O4W 26.3(13) 2_756 . ?
O6 Zn2 O3W 91.6(7) 2_756 . ?
O6 Zn2 O3W 91.6(7) . . ?
O4W Zn2 O3W 166.9(6) 2_756 . ?
O4W Zn2 O3W 166.9(6) . . ?
N1 C1 C2 118(2) . . ?
N1 C1 H1A 121.0 . . ?
C2 C1 H1A 121.0 . . ?
C1 C2 C3 120(2) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 118.7(19) . . ?
C4 C3 C8 120(2) . . ?
C2 C3 C8 121(2) . . ?
C3 C4 C5 119(2) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
N1 C5 C4 123(2) . . ?
N1 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
C7 C6 C11 120.2(17) . . ?
C7 C6 H6A 119.9 . . ?
C11 C6 H6A 119.9 . . ?
C8 C7 C6 122.8(18) . . ?
C8 C7 H7A 118.6 . . ?
C6 C7 H7A 118.6 . . ?
C7 C8 C9 117.4(18) . . ?
C7 C8 C3 123(2) . . ?
C9 C8 C3 119.5(17) . . ?
C10 C9 C8 118.4(18) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
C11 C10 C9 123.6(17) . . ?
C11 C10 H10A 118.2 . . ?
C9 C10 H10A 118.2 . . ?
C10 C11 C6 117.5(16) . . ?
C10 C11 C12 123.1(16) . . ?
C6 C11 C12 119.3(16) . . ?
O3 C12 O2 124.5(18) . . ?
O3 C12 C11 118.7(16) . . ?
O2 C12 C11 116.8(16) . . ?
C14 C13 N2 121.3(19) . . ?
C14 C13 H13A 119.4 . . ?
N2 C13 H13A 119.3 . . ?
C13 C14 C15 123.5(19) . . ?
C13 C14 H14A 118.3 . . ?
C15 C14 H14A 118.3 . . ?
C14 C15 C16 114.8(17) . . ?
C14 C15 C20 125(2) . . ?
C16 C15 C20 120(2) . . ?
C17 C16 C15 119.6(19) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
N2 C17 C16 123.8(19) . . ?
N2 C17 H17A 118.1 . . ?
C16 C17 H17A 118.1 . . ?
C19 C18 C23 122.7(19) . . ?
C19 C18 H18A 118.6 . . ?
C23 C18 H18A 118.6 . . ?
C18 C19 C20 119.6(19) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C21 C20 C19 118.9(18) . . ?
C21 C20 C15 121(2) . . ?
C19 C20 C15 120.0(18) . . ?
C22 C21 C20 121(2) . . ?
C22 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C21 C22 C23 120.9(19) . . ?
C21 C22 H22A 119.5 . . ?
C23 C22 H22A 119.5 . . ?
C18 C23 C22 116.9(17) . . ?
C18 C23 C24 121.7(19) . . ?
C22 C23 C24 121.4(19) . . ?
O5 C24 O6 122.5(19) . . ?
O5 C24 C23 120.9(19) . . ?
O6 C24 C23 116.4(18) . . ?
C5 N1 O1 120(2) . . ?
C5 N1 C1 121(2) . . ?
O1 N1 C1 118(2) . . ?
O4 N2 C17 121.3(16) . . ?
O4 N2 C13 121.5(18) . . ?
C17 N2 C13 117.1(16) . . ?
C12 O2 Zn1 104.5(12) . . ?
O4W O4W Zn2 76.9(6) 2_756 . ?
C24 O6 Zn2 107.3(13) . . ?

_refine_diff_density_max         1.588
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.131

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_6-Pb
_database_code_depnum_ccdc_archive 'CCDC 1504622'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 N2 O6 Pb'
_chemical_formula_sum            'C24 H16 N2 O6 Pb'
_chemical_formula_weight         635.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.213(5)
_cell_length_b                   17.232(5)
_cell_length_c                   7.666(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.997(5)
_cell_angle_gamma                90
_cell_volume                     2655.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3976
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    6.390
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 In complex 6, free solvent molecules were disordered, therefore, the diffused electron densities resulting from these residual solvent molecules were removed from the data set using the SQUEEZE routing of PLATON and refined further using the data generated. The number of electrons in the voids is 388, which may be assigned to 3DMF and 7 water guest solvents molecules.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11933
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.013
_diffrn_reflns_theta_max         23.846
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.851
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.851
_reflns_number_total             4094
_reflns_number_gt                2922
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00013(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4094
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_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 0.28098(2) 0.31377(2) 0.19677(4) 0.04138(15) Uani 1 1 d . . . . .
C1 C 0.5400(6) 0.7013(6) -0.7420(13) 0.064(3) Uani 1 1 d . . . . .
H1A H 0.5649 0.7280 -0.8179 0.077 Uiso 1 1 calc R U . . .
C2 C 0.4748(6) 0.6828(6) -0.7931(13) 0.071(3) Uani 1 1 d . . . . .
H2A H 0.4557 0.6986 -0.9031 0.085 Uiso 1 1 calc R U . . .
C3 C 0.4366(6) 0.6414(6) -0.6861(14) 0.073(3) Uani 1 1 d . . . . .
H3A H 0.3920 0.6308 -0.7212 0.088 Uiso 1 1 calc R U . . .
C4 C 0.4667(5) 0.6156(5) -0.5228(12) 0.047(2) Uani 1 1 d . . . . .
C5 C 0.5320(5) 0.6354(5) -0.4765(13) 0.051(3) Uani 1 1 d . . . . .
H5A H 0.5529 0.6175 -0.3702 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4302(4) 0.5684(5) -0.3993(12) 0.047(2) Uani 1 1 d . . . . .
C7 C 0.3767(5) 0.5205(6) -0.4572(13) 0.056(3) Uani 1 1 d . . . . .
H7A H 0.3604 0.5209 -0.5751 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3471(5) 0.4716(5) -0.3401(12) 0.055(3) Uani 1 1 d . . . . .
H8A H 0.3117 0.4396 -0.3805 0.066 Uiso 1 1 calc R U . . .
C9 C 0.3713(4) 0.4716(5) -0.1639(12) 0.046(2) Uani 1 1 d . . . . .
C10 C 0.4221(5) 0.5221(6) -0.1035(12) 0.062(3) Uani 1 1 d . . . . .
H10A H 0.4363 0.5241 0.0158 0.074 Uiso 1 1 calc R U . . .
C11 C 0.4521(5) 0.5698(6) -0.2192(13) 0.067(3) Uani 1 1 d . . . . .
H11A H 0.4867 0.6026 -0.1771 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3449(5) 0.4152(6) -0.0355(12) 0.049(3) Uani 1 1 d . . . . .
C13 C 0.1804(5) 0.4303(6) 0.2230(14) 0.055(3) Uani 1 1 d . . . . .
C14 C 0.1225(5) 0.4832(6) 0.2567(12) 0.049(3) Uani 1 1 d . . . . .
C15 C 0.0593(5) 0.4593(6) 0.1990(12) 0.061(3) Uani 1 1 d . . . . .
H15A H 0.0526 0.4132 0.1368 0.073 Uiso 1 1 calc R U . . .
C16 C 0.0048(5) 0.5053(6) 0.2347(12) 0.060(3) Uani 1 1 d . . . . .
H16A H -0.0379 0.4892 0.1941 0.072 Uiso 1 1 calc R U . . .
C17 C 0.0129(4) 0.5732(5) 0.3275(12) 0.045(2) Uani 1 1 d . . . . .
C18 C 0.0772(5) 0.5976(6) 0.3830(16) 0.081(4) Uani 1 1 d . . . . .
H18A H 0.0843 0.6445 0.4421 0.097 Uiso 1 1 calc R U . . .
C19 C 0.1309(5) 0.5513(6) 0.3493(15) 0.075(3) Uani 1 1 d . . . . .
H19A H 0.1736 0.5670 0.3909 0.090 Uiso 1 1 calc R U . . .
C20 C -0.1658(4) 0.6395(6) 0.3445(13) 0.053(3) Uani 1 1 d . . . . .
H20A H -0.2080 0.6267 0.2922 0.063 Uiso 1 1 calc R U . . .
C21 C -0.1100(5) 0.6015(6) 0.2934(12) 0.054(3) Uani 1 1 d . . . . .
H21A H -0.1157 0.5639 0.2061 0.065 Uiso 1 1 calc R U . . .
C22 C -0.0456(5) 0.6184(5) 0.3703(12) 0.045(2) Uani 1 1 d . . . . .
C23 C -0.0424(5) 0.6782(6) 0.4966(13) 0.058(3) Uani 1 1 d . . . . .
H23A H -0.0011 0.6932 0.5510 0.069 Uiso 1 1 calc R U . . .
C24 C -0.0967(5) 0.7139(5) 0.5402(13) 0.056(3) Uani 1 1 d . . . . .
H24A H -0.0921 0.7536 0.6227 0.067 Uiso 1 1 calc R U . . .
N1 N 0.5678(4) 0.6805(5) -0.5815(10) 0.056(2) Uani 1 1 d . . . . .
N2 N -0.1588(4) 0.6943(4) 0.4685(9) 0.0456(19) Uani 1 1 d . . . . .
O1 O 0.6290(3) 0.7013(4) -0.5276(8) 0.067(2) Uani 1 1 d . . . . .
O2 O 0.3743(3) 0.4118(4) 0.1162(9) 0.070(2) Uani 1 1 d . . . . .
O3 O 0.2939(3) 0.3755(4) -0.0855(8) 0.0585(19) Uani 1 1 d . . . . .
O4 O 0.1693(3) 0.3712(4) 0.1366(8) 0.0589(19) Uani 1 1 d . . . . .
O5 O 0.2379(3) 0.4497(4) 0.2958(9) 0.072(2) Uani 1 1 d . . . . .
O6 O -0.2130(3) 0.7275(4) 0.5230(8) 0.0524(17) Uani 1 1 d . . . . .


_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 O3 2.450(6) . ?
Pb1 O4 2.464(6) . ?
Pb1 O6 2.541(6) 2_545 ?
Pb1 O5 2.638(7) . ?
Pb1 O2 2.653(6) . ?
C1 N1 1.346(12) . ?
C1 C2 1.373(13) . ?
C1 H1A 0.9300 . ?
C2 C3 1.383(13) . ?
C2 H2A 0.9300 . ?
C3 C4 1.406(13) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(12) . ?
C4 C6 1.501(11) . ?
C5 N1 1.378(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(12) . ?
C6 C11 1.406(12) . ?
C7 C8 1.410(12) . ?
C7 H7A 0.9300 . ?
C8 C9 1.387(12) . ?
C8 H8A 0.9300 . ?
C9 C10 1.388(12) . ?
C9 C12 1.519(12) . ?
C10 C11 1.394(12) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O2 1.251(10) . ?
C12 O3 1.262(10) . ?
C13 O4 1.222(11) . ?
C13 O5 1.280(11) . ?
C13 C14 1.527(12) . ?
C14 C19 1.373(13) . ?
C14 C15 1.370(12) . ?
C15 C16 1.408(12) . ?
C15 H15A 0.9300 . ?
C16 C17 1.369(12) . ?
C16 H16A 0.9300 . ?
C17 C18 1.390(12) . ?
C17 C22 1.481(11) . ?
C18 C19 1.392(12) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 N2 1.337(11) . ?
C20 C21 1.395(11) . ?
C20 H20A 0.9300 . ?
C21 C22 1.403(12) . ?
C21 H21A 0.9300 . ?
C22 C23 1.411(12) . ?
C23 C24 1.332(12) . ?
C23 H23A 0.9300 . ?
C24 N2 1.358(11) . ?
C24 H24A 0.9300 . ?
N1 O1 1.313(9) . ?
N2 O6 1.340(8) . ?
O6 Pb1 2.541(6) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Pb1 O4 80.8(2) . . ?
O3 Pb1 O6 76.6(2) . 2_545 ?
O4 Pb1 O6 71.9(2) . 2_545 ?
O3 Pb1 O5 86.4(2) . . ?
O4 Pb1 O5 51.2(2) . . ?
O6 Pb1 O5 122.6(2) 2_545 . ?
O3 Pb1 O2 51.22(19) . . ?
O4 Pb1 O2 111.1(2) . . ?
O6 Pb1 O2 124.55(19) 2_545 . ?
O5 Pb1 O2 76.4(2) . . ?
N1 C1 C2 119.8(9) . . ?
N1 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C1 C2 C3 122.0(10) . . ?
C1 C2 H2A 119.0 . . ?
C3 C2 H2A 119.0 . . ?
C2 C3 C4 118.3(10) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 117.9(9) . . ?
C5 C4 C6 119.6(9) . . ?
C3 C4 C6 122.4(9) . . ?
C4 C5 N1 122.5(9) . . ?
C4 C5 H5A 118.7 . . ?
N1 C5 H5A 118.7 . . ?
C7 C6 C11 118.5(8) . . ?
C7 C6 C4 122.4(8) . . ?
C11 C6 C4 119.0(8) . . ?
C6 C7 C8 121.2(9) . . ?
C6 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C9 C8 C7 119.3(9) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C8 C9 C10 119.9(8) . . ?
C8 C9 C12 121.3(8) . . ?
C10 C9 C12 118.8(8) . . ?
C9 C10 C11 120.9(9) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C6 C11 C10 120.1(9) . . ?
C6 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
O2 C12 O3 123.4(9) . . ?
O2 C12 C9 117.8(9) . . ?
O3 C12 C9 118.8(8) . . ?
O4 C13 O5 124.2(9) . . ?
O4 C13 C14 119.2(9) . . ?
O5 C13 C14 116.5(10) . . ?
C19 C14 C15 118.9(9) . . ?
C19 C14 C13 122.9(9) . . ?
C15 C14 C13 118.1(9) . . ?
C14 C15 C16 119.3(10) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C17 C16 C15 121.9(9) . . ?
C17 C16 H16A 119.0 . . ?
C15 C16 H16A 119.0 . . ?
C16 C17 C18 118.3(9) . . ?
C16 C17 C22 120.7(9) . . ?
C18 C17 C22 121.0(9) . . ?
C19 C18 C17 119.5(10) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C14 C19 C18 122.0(9) . . ?
C14 C19 H19A 119.0 . . ?
C18 C19 H19A 119.0 . . ?
N2 C20 C21 120.2(9) . . ?
N2 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C20 C21 C22 121.7(9) . . ?
C20 C21 H21A 119.1 . . ?
C22 C21 H21A 119.1 . . ?
C21 C22 C23 114.5(9) . . ?
C21 C22 C17 121.7(9) . . ?
C23 C22 C17 123.8(9) . . ?
C24 C23 C22 121.9(9) . . ?
C24 C23 H23A 119.0 . . ?
C22 C23 H23A 119.0 . . ?
C23 C24 N2 122.4(9) . . ?
C23 C24 H24A 118.8 . . ?
N2 C24 H24A 118.8 . . ?
O1 N1 C1 120.3(8) . . ?
O1 N1 C5 120.4(8) . . ?
C1 N1 C5 119.3(9) . . ?
O6 N2 C20 119.5(8) . . ?
O6 N2 C24 121.2(8) . . ?
C20 N2 C24 119.2(8) . . ?
C12 O2 Pb1 88.0(6) . . ?
C12 O3 Pb1 97.3(5) . . ?
C13 O4 Pb1 96.9(6) . . ?
C13 O5 Pb1 87.4(6) . . ?
N2 O6 Pb1 116.5(4) . 2 ?

_refine_diff_density_max         1.877
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.121

_shelxl_version_number           2014-3


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.789 0.250 -0.045 387 97 ' '
2 0.211 0.750 -0.059 388 97 ' '
_platon_squeeze_details          ?
