# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Co_TPA
_database_code_depnum_ccdc_archive 'CCDC 1436795'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Tripticene triacid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H11 Co N3 O4'
_chemical_formula_sum            'C22 H11 Co N3 O4'
_chemical_formula_weight         440.27

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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   13.9619(16)
_cell_length_b                   41.194(5)
_cell_length_c                   17.1363(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.485(7)
_cell_angle_gamma                90
_cell_volume                     9622.8(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       square
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.608
_exptl_crystal_F_000             1784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42934
_diffrn_reflns_av_unetI/netI     0.1172
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11928
_reflns_number_gt                4825
_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_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.2000P)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         11928
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2324
_refine_ls_R_factor_gt           0.1388
_refine_ls_wR_factor_ref         0.4319
_refine_ls_wR_factor_gt          0.3957
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.230
_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
C1 C -0.7500 -0.2467(2) 0.5000 0.060(2) Uani 1 2 d S T P . .
C2 C -0.7500 -0.20861(17) 0.5000 0.055(2) Uani 1 2 d S T P . .
C3 C -0.8293(5) -0.19230(13) 0.4588(4) 0.0673(18) Uani 1 1 d . . . . .
H3 H -0.8830 -0.2037 0.4301 0.081 Uiso 1 1 calc R U . . .
C4 C -0.8301(5) -0.15905(13) 0.4595(4) 0.0585(16) Uani 1 1 d . . . . .
H4 H -0.8853 -0.1479 0.4324 0.070 Uiso 1 1 calc R U . . .
C5 C -0.7500 -0.14211(18) 0.5000 0.0451(18) Uani 1 2 d S T P . .
C6 C -0.7500 -0.10558(14) 0.5000 0.0319(15) Uani 1 2 d S T P . .
C7 C -0.7063(3) -0.05608(10) 0.5288(3) 0.0334(11) Uani 1 1 d . . . . .
C8 C -0.6578(3) -0.02740(10) 0.5598(3) 0.0271(10) Uani 1 1 d . . . . .
H8 H -0.5987 -0.0274 0.5973 0.032 Uiso 1 1 calc R U . . .
C9 C -0.7067(3) 0.00141(9) 0.5290(2) 0.0235(9) Uani 1 1 d . . . . .
C10 C -0.6702(3) 0.03519(10) 0.5538(3) 0.0285(10) Uani 1 1 d . . . . .
H10 H -0.6091 0.0350 0.5948 0.034 Uiso 1 1 calc R U . . .
C11 C -0.6590(3) 0.05200(9) 0.4777(3) 0.0255(10) Uani 1 1 d . . . . .
C12 C -0.7459(3) 0.05220(10) 0.4181(3) 0.0288(11) Uani 1 1 d . . . . .
C13 C -0.7529(3) 0.06504(10) 0.3435(3) 0.0317(10) Uani 1 1 d . . . . .
H13 H -0.8107 0.0646 0.3045 0.038 Uiso 1 1 calc R U . . .
C14 C -0.6652(4) 0.07897(11) 0.3304(3) 0.0333(11) Uani 1 1 d . . . . .
C15 C -0.5788(3) 0.07923(10) 0.3896(3) 0.0312(11) Uani 1 1 d . . . . .
C16 C -0.5745(3) 0.06545(10) 0.4642(3) 0.0262(10) Uani 1 1 d . . . . .
H16 H -0.5167 0.0654 0.5033 0.031 Uiso 1 1 calc R U . . .
C17 C -0.5527(4) 0.10232(12) 0.2815(3) 0.0431(13) Uani 1 1 d . . . . .
C18 C -0.5005(5) 0.11908(13) 0.2264(3) 0.0565(17) Uani 1 1 d . . . . .
C19 C -0.5477(7) 0.1296(2) 0.1557(5) 0.105(3) Uani 1 1 d . . . . .
H19 H -0.6146 0.1255 0.1398 0.126 Uiso 1 1 calc R U . . .
C20 C -0.5009(8) 0.1464(2) 0.1041(5) 0.101(3) Uani 1 1 d . . . . .
H20 H -0.5362 0.1543 0.0555 0.121 Uiso 1 1 calc R U . . .
C21 C -0.4038(7) 0.15100(17) 0.1264(5) 0.077(2) Uani 1 1 d . . . . .
C22 C -0.3544(6) 0.14184(17) 0.1945(5) 0.080(2) Uani 1 1 d . . . . .
H22 H -0.2875 0.1460 0.2098 0.096 Uiso 1 1 calc R U . . .
C23 C -0.4050(5) 0.12493(18) 0.2469(4) 0.074(2) Uani 1 1 d . . . . .
H23 H -0.3699 0.1179 0.2964 0.089 Uiso 1 1 calc R U . . .
C24 C -0.3438(9) 0.16967(19) 0.0726(6) 0.090(3) Uani 1 1 d . . . . .
Co1 Co -0.35881(8) 0.19767(2) -0.08627(7) 0.0831(5) Uani 1 1 d . . . . .
N1 N -0.6791(3) -0.08806(9) 0.5451(2) 0.0364(10) Uani 1 1 d . . . . .
N2 N -0.6447(3) 0.09408(9) 0.2614(2) 0.0403(10) Uani 1 1 d . . . . .
N3 N -0.5085(3) 0.09392(9) 0.3574(2) 0.0354(10) Uani 1 1 d . . . . .
H3A H -0.4483 0.0972 0.3806 0.042 Uiso 1 1 calc R U . . .
O1 O -0.3964(7) 0.17454(16) 0.0015(5) 0.147(3) Uani 1 1 d . . . . .
O2 O -0.2630(6) 0.17661(17) 0.0984(4) 0.129(3) Uani 1 1 d . . . . .
O3 O -0.8214(5) -0.25932(11) 0.4599(3) 0.0866(16) Uani 1 1 d . . . . .
O5 O -0.4620(7) 0.20073(17) -0.1885(5) 0.162(3) 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
C1 O3 1.200(6) . ?
C1 O3 1.200(6) 2_356 ?
C1 C2 1.570(11) . ?
C2 C3 1.355(8) 2_356 ?
C2 C3 1.355(8) . ?
C3 C4 1.370(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(7) . ?
C4 H4 0.9300 . ?
C5 C4 1.373(7) 2_356 ?
C5 C6 1.505(9) . ?
C6 N1 1.330(5) 2_356 ?
C6 N1 1.330(5) . ?
C7 N1 1.383(5) . ?
C7 C7 1.393(10) 2_356 ?
C7 C8 1.407(6) . ?
C8 C9 1.413(6) . ?
C8 H8 0.9300 . ?
C9 C9 1.388(9) 2_356 ?
C9 C10 1.511(6) . ?
C10 C11 1.515(6) . ?
C10 C12 1.530(6) 2_356 ?
C10 H10 0.9800 . ?
C11 C16 1.368(6) . ?
C11 C12 1.407(6) . ?
C12 C13 1.367(6) . ?
C12 C10 1.530(6) 2_356 ?
C13 C14 1.414(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.398(7) . ?
C14 N2 1.419(5) . ?
C15 N3 1.367(5) . ?
C15 C16 1.388(6) . ?
C16 H16 0.9300 . ?
C17 N2 1.301(7) . ?
C17 N3 1.359(7) . ?
C17 C18 1.482(7) . ?
C18 C19 1.320(11) . ?
C18 C23 1.325(9) . ?
C19 C20 1.394(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.340(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.278(10) . ?
C21 C24 1.573(10) . ?
C22 C23 1.437(9) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O2 1.156(12) . ?
C24 O1 1.295(12) . ?
Co1 O1 1.946(6) . ?
Co1 O2 1.960(6) 2_455 ?
Co1 O3 1.964(5) 3_554 ?
Co1 O5 2.017(9) . ?
N3 H3A 0.8600 . ?
O2 Co1 1.960(6) 2_455 ?
O3 Co1 1.964(5) 3_445 ?

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 C1 O3 128.8(9) . 2_356 ?
O3 C1 C2 115.6(5) . . ?
O3 C1 C2 115.6(5) 2_356 . ?
C3 C2 C3 120.6(7) 2_356 . ?
C3 C2 C1 119.7(4) 2_356 . ?
C3 C2 C1 119.7(4) . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C4 118.9(7) . 2_356 ?
C4 C5 C6 120.6(4) . . ?
C4 C5 C6 120.6(4) 2_356 . ?
N1 C6 N1 114.2(5) 2_356 . ?
N1 C6 C5 122.9(3) 2_356 . ?
N1 C6 C5 122.9(3) . . ?
N1 C7 C7 107.7(3) . 2_356 ?
N1 C7 C8 129.4(4) . . ?
C7 C7 C8 122.9(3) 2_356 . ?
C7 C8 C9 114.2(4) . . ?
C7 C8 H8 122.9 . . ?
C9 C8 H8 122.9 . . ?
C9 C9 C8 122.9(3) 2_356 . ?
C9 C9 C10 113.0(2) 2_356 . ?
C8 C9 C10 124.2(4) . . ?
C9 C10 C11 105.6(3) . . ?
C9 C10 C12 106.0(3) . 2_356 ?
C11 C10 C12 106.8(3) . 2_356 ?
C9 C10 H10 112.6 . . ?
C11 C10 H10 112.6 . . ?
C12 C10 H10 112.6 2_356 . ?
C16 C11 C12 121.0(4) . . ?
C16 C11 C10 125.7(4) . . ?
C12 C11 C10 113.3(4) . . ?
C13 C12 C11 123.8(4) . . ?
C13 C12 C10 124.5(4) . 2_356 ?
C11 C12 C10 111.6(4) . 2_356 ?
C12 C13 C14 114.6(4) . . ?
C12 C13 H13 122.7 . . ?
C14 C13 H13 122.7 . . ?
C15 C14 C13 121.9(4) . . ?
C15 C14 N2 107.7(4) . . ?
C13 C14 N2 130.4(5) . . ?
N3 C15 C16 131.3(5) . . ?
N3 C15 C14 107.0(4) . . ?
C16 C15 C14 121.6(4) . . ?
C11 C16 C15 116.9(4) . . ?
C11 C16 H16 121.5 . . ?
C15 C16 H16 121.5 . . ?
N2 C17 N3 113.9(4) . . ?
N2 C17 C18 123.1(5) . . ?
N3 C17 C18 123.0(5) . . ?
C19 C18 C23 117.2(6) . . ?
C19 C18 C17 121.3(6) . . ?
C23 C18 C17 121.4(6) . . ?
C18 C19 C20 122.4(9) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C21 C20 C19 118.2(9) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C22 C21 C20 122.1(7) . . ?
C22 C21 C24 115.4(9) . . ?
C20 C21 C24 122.4(8) . . ?
C21 C22 C23 118.2(7) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C18 C23 C22 121.7(7) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
O2 C24 O1 129.0(9) . . ?
O2 C24 C21 119.8(9) . . ?
O1 C24 C21 111.2(10) . . ?
O1 Co1 O2 104.5(3) . 2_455 ?
O1 Co1 O3 102.9(3) . 3_554 ?
O2 Co1 O3 106.3(3) 2_455 3_554 ?
O1 Co1 O5 116.1(4) . . ?
O2 Co1 O5 114.1(4) 2_455 . ?
O3 Co1 O5 111.8(3) 3_554 . ?
C6 N1 C7 105.2(4) . . ?
C17 N2 C14 105.0(4) . . ?
C17 N3 C15 106.4(4) . . ?
C17 N3 H3A 126.8 . . ?
C15 N3 H3A 126.8 . . ?
C24 O1 Co1 127.6(7) . . ?
C24 O2 Co1 150.1(8) . 2_455 ?
C1 O3 Co1 137.4(6) . 3_445 ?

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
O3 C1 C2 C3 -177.5(4) . . . 2_356 ?
O3 C1 C2 C3 2.5(4) 2_356 . . 2_356 ?
O3 C1 C2 C3 2.5(4) . . . . ?
O3 C1 C2 C3 -177.5(4) 2_356 . . . ?
C3 C2 C3 C4 -0.9(4) 2_356 . . . ?
C1 C2 C3 C4 179.1(4) . . . . ?
C2 C3 C4 C5 1.8(9) . . . . ?
C3 C4 C5 C4 -0.9(4) . . . 2_356 ?
C3 C4 C5 C6 179.1(4) . . . . ?
C4 C5 C6 N1 -7.6(3) . . . 2_356 ?
C4 C5 C6 N1 172.4(3) 2_356 . . 2_356 ?
C4 C5 C6 N1 172.4(3) . . . . ?
C4 C5 C6 N1 -7.6(3) 2_356 . . . ?
N1 C7 C8 C9 179.5(4) . . . . ?
C7 C7 C8 C9 1.5(7) 2_356 . . . ?
C7 C8 C9 C9 -2.2(6) . . . 2_356 ?
C7 C8 C9 C10 179.1(3) . . . . ?
C9 C9 C10 C11 -56.8(5) 2_356 . . . ?
C8 C9 C10 C11 122.1(4) . . . . ?
C9 C9 C10 C12 56.4(5) 2_356 . . 2_356 ?
C8 C9 C10 C12 -124.8(4) . . . 2_356 ?
C9 C10 C11 C16 -122.4(4) . . . . ?
C12 C10 C11 C16 125.0(4) 2_356 . . . ?
C9 C10 C11 C12 56.3(4) . . . . ?
C12 C10 C11 C12 -56.3(4) 2_356 . . . ?
C16 C11 C12 C13 0.9(6) . . . . ?
C10 C11 C12 C13 -177.8(4) . . . . ?
C16 C11 C12 C10 178.8(4) . . . 2_356 ?
C10 C11 C12 C10 0.0(4) . . . 2_356 ?
C11 C12 C13 C14 -1.1(6) . . . . ?
C10 C12 C13 C14 -178.6(4) 2_356 . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
C12 C13 C14 N2 179.4(4) . . . . ?
C13 C14 C15 N3 179.2(4) . . . . ?
N2 C14 C15 N3 -0.2(5) . . . . ?
C13 C14 C15 C16 0.8(7) . . . . ?
N2 C14 C15 C16 -178.6(4) . . . . ?
C12 C11 C16 C15 0.2(6) . . . . ?
C10 C11 C16 C15 178.7(4) . . . . ?
N3 C15 C16 C11 -178.9(4) . . . . ?
C14 C15 C16 C11 -1.0(6) . . . . ?
N2 C17 C18 C19 6.9(9) . . . . ?
N3 C17 C18 C19 -173.6(6) . . . . ?
N2 C17 C18 C23 -174.9(6) . . . . ?
N3 C17 C18 C23 4.6(9) . . . . ?
C23 C18 C19 C20 -0.7(12) . . . . ?
C17 C18 C19 C20 177.6(7) . . . . ?
C18 C19 C20 C21 2.5(14) . . . . ?
C19 C20 C21 C22 -3.5(14) . . . . ?
C19 C20 C21 C24 179.9(7) . . . . ?
C20 C21 C22 C23 2.6(12) . . . . ?
C24 C21 C22 C23 179.4(6) . . . . ?
C19 C18 C23 C22 -0.3(11) . . . . ?
C17 C18 C23 C22 -178.5(6) . . . . ?
C21 C22 C23 C18 -0.7(11) . . . . ?
C22 C21 C24 O2 -6.6(12) . . . . ?
C20 C21 C24 O2 170.1(9) . . . . ?
C22 C21 C24 O1 172.2(7) . . . . ?
C20 C21 C24 O1 -11.0(11) . . . . ?
N1 C6 N1 C7 0.6(2) 2_356 . . . ?
C5 C6 N1 C7 -179.4(2) . . . . ?
C7 C7 N1 C6 -1.5(5) 2_356 . . . ?
C8 C7 N1 C6 -179.8(4) . . . . ?
N3 C17 N2 C14 0.6(6) . . . . ?
C18 C17 N2 C14 -179.9(4) . . . . ?
C15 C14 N2 C17 -0.3(5) . . . . ?
C13 C14 N2 C17 -179.5(5) . . . . ?
N2 C17 N3 C15 -0.7(6) . . . . ?
C18 C17 N3 C15 179.8(4) . . . . ?
C16 C15 N3 C17 178.7(5) . . . . ?
C14 C15 N3 C17 0.5(5) . . . . ?
O2 C24 O1 Co1 -3.6(14) . . . . ?
C21 C24 O1 Co1 177.7(5) . . . . ?
O1 C24 O2 Co1 4(2) . . . 2_455 ?
C21 C24 O2 Co1 -177.6(9) . . . 2_455 ?
O3 C1 O3 Co1 -16.9(4) 2_356 . . 3_445 ?
C2 C1 O3 Co1 163.1(4) . . . 3_445 ?

_refine_diff_density_max         2.500
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.115


# SQUEEZE RESULTS (Version =  70515)
# 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 -0.015 -0.004 0.000 6735 1581 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
####################################################################### 
# 
# 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_Mn_TPA
_database_code_depnum_ccdc_archive 'CCDC 1436796'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Tripticene triacid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H11 Mn N3 O6'
_chemical_formula_sum            'C22 H11 Mn N3 O6'
_chemical_formula_weight         468.28

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'
Mn Mn 0.3368 0.7283 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   13.7763(11)
_cell_length_b                   40.730(6)
_cell_length_c                   17.9835(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.209(2)
_cell_angle_gamma                90
_cell_volume                     9898.2(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       square
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.628
_exptl_crystal_F_000             1896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75845
_diffrn_reflns_av_unetI/netI     0.2101
_diffrn_reflns_av_R_equivalents  0.1160
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.126
_diffrn_reflns_theta_max         28.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12462
_reflns_number_gt                3207
_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_cell_refinement       'Bruker SAINT'

_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.2000P)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         12462
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3694
_refine_ls_R_factor_gt           0.1177
_refine_ls_wR_factor_ref         0.4213
_refine_ls_wR_factor_gt          0.3329
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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 0.12119(8) 0.30667(3) -0.07862(6) 0.1139(6) Uani 1 1 d . . . . .
C1 C -0.1718(11) -0.1640(2) 0.4140(7) 0.153(4) Uani 1 1 d . . . . .
O1 O -0.2610(7) -0.17322(19) 0.3855(4) 0.185(3) Uani 1 1 d . . . . .
N1 N 0.3181(4) 0.08916(11) 0.0419(3) 0.0775(13) Uani 1 1 d . . . . .
N3 N 0.0037(3) -0.09462(11) 0.1374(3) 0.0791(14) Uani 1 1 d . . . . .
H3 H -0.0570 -0.0982 0.1162 0.095 Uiso 1 1 calc R U . . .
O3 O 0.1742(6) 0.26174(15) -0.0369(5) 0.177(3) Uani 1 1 d . . . . .
C3 C -0.1616(6) -0.13992(17) 0.2897(4) 0.118(2) Uani 1 1 d . . . . .
H3A H -0.2282 -0.1449 0.2730 0.141 Uiso 1 1 calc R U . . .
O4 O 0.0852(7) 0.2795(2) -0.2023(6) 0.265(4) Uani 1 1 d . . . . .
O2 O -0.1274(7) -0.1691(2) 0.4772(4) 0.213(4) Uani 1 1 d . . . . .
C2 C -0.1162(8) -0.14774(18) 0.3588(5) 0.114(2) Uani 1 1 d . . . . .
N2 N 0.1425(4) -0.09468(12) 0.2279(3) 0.0896(15) Uani 1 1 d . . . . .
C4 C -0.1077(6) -0.12399(18) 0.2416(4) 0.110(2) Uani 1 1 d . . . . .
H4 H -0.1407 -0.1169 0.1943 0.132 Uiso 1 1 calc R U . . .
O5 O -0.0284(6) 0.2934(3) -0.0618(7) 0.346(7) Uani 1 1 d . . . . .
C5 C -0.0132(6) -0.11883(15) 0.2611(4) 0.0921(19) Uani 1 1 d . . . . .
C8 C 0.0472(6) -0.10275(14) 0.2082(4) 0.0886(19) Uani 1 1 d . . . . .
C7 C -0.0159(8) -0.1429(2) 0.3804(4) 0.139(3) Uani 1 1 d . . . . .
H7 H 0.0165 -0.1496 0.4282 0.167 Uiso 1 1 calc R U . . .
C6 C 0.0360(6) -0.12851(19) 0.3332(4) 0.131(3) Uani 1 1 d . . . . .
H6 H 0.1037 -0.1251 0.3483 0.158 Uiso 1 1 calc R U . . .
C9 C 0.0731(4) -0.07979(13) 0.1058(3) 0.0722(15) Uani 1 1 d . . . . .
C11 C 0.2488(4) -0.06612(13) 0.1467(3) 0.0698(14) Uani 1 1 d . . . . .
H11 H 0.3067 -0.0668 0.1832 0.084 Uiso 1 1 calc R U . . .
C10 C 0.1608(5) -0.07975(13) 0.1601(3) 0.0760(16) Uani 1 1 d . . . . .
C12 C 0.2463(4) -0.05217(13) 0.0799(3) 0.0668(14) Uani 1 1 d . . . . .
C14 C 0.3432(4) -0.05216(12) -0.0222(3) 0.0639(14) Uani 1 1 d . . . . .
C13 C 0.3308(4) -0.03498(12) 0.0509(3) 0.0649(14) Uani 1 1 d . . . . .
H13 H 0.3923 -0.0346 0.0889 0.078 Uiso 1 1 calc R U . . .
C15 C 0.4276(4) -0.06619(13) -0.0363(3) 0.0715(15) Uani 1 1 d . . . . .
H15 H 0.4849 -0.0665 0.0009 0.086 Uiso 1 1 calc R U . . .
C16 C 0.2932(3) -0.00014(14) 0.0267(2) 0.0592(14) Uani 1 1 d . . . . .
C17 C 0.3398(4) 0.02826(14) 0.0553(3) 0.0659(14) Uani 1 1 d . . . . .
H17 H 0.3983 0.0282 0.0912 0.079 Uiso 1 1 calc R U . . .
C18 C 0.2918(3) 0.05768(15) 0.0257(2) 0.0618(14) Uani 1 1 d . . . . .
C19 C 0.2500 0.10711(19) 0.0000 0.076(3) Uani 1 2 d S T P . .
C20 C 0.2500 0.1409(3) 0.0000 0.085(3) Uani 1 2 d S T P . .
C21 C 0.1697(6) 0.15979(18) -0.0396(4) 0.110(2) Uani 1 1 d . . . . .
H21 H 0.1136 0.1488 -0.0647 0.132 Uiso 1 1 calc R U . . .
C22 C 0.2500 0.2104(3) 0.0000 0.137(5) Uani 1 2 d S T P . .
C23 C 0.2500 0.2478(7) 0.0000 0.190(9) Uani 1 2 d S T P . .
C24 C 0.1707(6) 0.1928(2) -0.0426(5) 0.134(3) Uani 1 1 d . . . . .
H24 H 0.1188 0.2039 -0.0730 0.161 Uiso 1 1 calc R U . . .
O7 O 0.0526(11) 0.3544(3) -0.1340(10) 0.406(9) 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 O1 2.032(8) 3_554 ?
Mn1 O3 2.057(7) . ?
Mn1 O2 2.062(7) 4_455 ?
Mn1 O5 2.207(9) . ?
Mn1 O7 2.301(11) . ?
Mn1 O4 2.447(10) . ?
C1 O2 1.199(13) . ?
C1 O1 1.291(13) . ?
C1 C2 1.519(11) . ?
O1 Mn1 2.032(8) 3_445 ?
N1 C19 1.306(5) . ?
N1 C18 1.348(7) . ?
N3 C8 1.339(7) . ?
N3 C9 1.348(6) . ?
N3 H3 0.8600 . ?
O3 C23 1.259(11) . ?
C3 C2 1.316(10) . ?
C3 C4 1.403(8) . ?
C3 H3A 0.9300 . ?
O2 Mn1 2.062(7) 4_445 ?
C2 C7 1.376(10) . ?
N2 C8 1.333(7) . ?
N2 C10 1.428(6) . ?
C4 C5 1.297(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(9) . ?
C5 C8 1.528(8) . ?
C7 C6 1.344(10) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C9 C15 1.365(7) 2 ?
C9 C10 1.398(7) . ?
C11 C12 1.323(6) . ?
C11 C10 1.397(7) . ?
C11 H11 0.9300 . ?
C12 C14 1.448(7) 2 ?
C12 C13 1.534(7) . ?
C14 C15 1.364(6) . ?
C14 C12 1.448(7) 2 ?
C14 C13 1.528(6) . ?
C13 C16 1.544(7) . ?
C13 H13 0.9800 . ?
C15 C9 1.365(7) 2 ?
C15 H15 0.9300 . ?
C16 C17 1.373(6) . ?
C16 C16 1.376(9) 2 ?
C17 C18 1.421(7) . ?
C17 H17 0.9300 . ?
C18 C18 1.330(9) 2 ?
C19 N1 1.306(5) 2 ?
C19 C20 1.376(12) . ?
C20 C21 1.420(9) 2 ?
C20 C21 1.420(9) . ?
C21 C24 1.344(10) . ?
C21 H21 0.9300 . ?
C22 C24 1.404(9) . ?
C22 C24 1.404(9) 2 ?
C22 C23 1.52(3) . ?
C23 O3 1.259(11) 2 ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O3 103.0(3) 3_554 . ?
O1 Mn1 O2 100.9(3) 3_554 4_455 ?
O3 Mn1 O2 98.8(3) . 4_455 ?
O1 Mn1 O5 165.2(5) 3_554 . ?
O3 Mn1 O5 90.4(4) . . ?
O2 Mn1 O5 82.8(4) 4_455 . ?
O1 Mn1 O7 79.0(5) 3_554 . ?
O3 Mn1 O7 174.8(5) . . ?
O2 Mn1 O7 85.4(5) 4_455 . ?
O5 Mn1 O7 87.1(6) . . ?
O1 Mn1 O4 85.8(3) 3_554 . ?
O3 Mn1 O4 85.6(3) . . ?
O2 Mn1 O4 170.8(3) 4_455 . ?
O5 Mn1 O4 89.1(4) . . ?
O7 Mn1 O4 89.7(5) . . ?
O2 C1 O1 126.6(10) . . ?
O2 C1 C2 117.7(13) . . ?
O1 C1 C2 115.4(12) . . ?
C1 O1 Mn1 138.5(7) . 3_445 ?
C19 N1 C18 106.0(5) . . ?
C8 N3 C9 106.7(5) . . ?
C8 N3 H3 126.6 . . ?
C9 N3 H3 126.6 . . ?
C23 O3 Mn1 142.6(13) . . ?
C2 C3 C4 118.8(8) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C1 O2 Mn1 147.8(9) . 4_445 ?
C3 C2 C7 119.9(7) . . ?
C3 C2 C1 121.0(10) . . ?
C7 C2 C1 119.0(10) . . ?
C8 N2 C10 101.8(5) . . ?
C5 C4 C3 122.2(7) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 118.9(6) . . ?
C4 C5 C8 122.8(6) . . ?
C6 C5 C8 118.3(7) . . ?
N2 C8 N3 115.4(5) . . ?
N2 C8 C5 124.6(6) . . ?
N3 C8 C5 120.0(7) . . ?
C6 C7 C2 120.8(8) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C7 C6 C5 119.1(8) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N3 C9 C15 133.5(6) . 2 ?
N3 C9 C10 107.0(5) . . ?
C15 C9 C10 119.5(5) 2 . ?
C12 C11 C10 117.2(5) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 H11 121.4 . . ?
C11 C10 C9 122.7(5) . . ?
C11 C10 N2 128.3(6) . . ?
C9 C10 N2 109.0(5) . . ?
C11 C12 C14 121.2(5) . 2 ?
C11 C12 C13 128.1(5) . . ?
C14 C12 C13 110.7(4) 2 . ?
C15 C14 C12 120.4(4) . 2 ?
C15 C14 C13 126.4(5) . . ?
C12 C14 C13 113.2(4) 2 . ?
C14 C13 C12 107.6(4) . . ?
C14 C13 C16 105.4(4) . . ?
C12 C13 C16 106.3(4) . . ?
C14 C13 H13 112.4 . . ?
C12 C13 H13 112.4 . . ?
C16 C13 H13 112.4 . . ?
C14 C15 C9 119.0(5) . 2 ?
C14 C15 H15 120.5 . . ?
C9 C15 H15 120.5 2 . ?
C17 C16 C16 122.6(3) . 2 ?
C17 C16 C13 124.2(5) . . ?
C16 C16 C13 113.2(3) 2 . ?
C16 C17 C18 114.9(5) . . ?
C16 C17 H17 122.6 . . ?
C18 C17 H17 122.6 . . ?
C18 C18 N1 108.0(3) 2 . ?
C18 C18 C17 122.5(3) 2 . ?
N1 C18 C17 129.5(5) . . ?
N1 C19 N1 111.9(6) . 2 ?
N1 C19 C20 124.0(3) . . ?
N1 C19 C20 124.0(3) 2 . ?
C19 C20 C21 122.8(5) . 2 ?
C19 C20 C21 122.8(5) . . ?
C21 C20 C21 114.4(9) 2 . ?
C24 C21 C20 123.2(8) . . ?
C24 C21 H21 118.4 . . ?
C20 C21 H21 118.4 . . ?
C24 C22 C24 118.5(10) . 2 ?
C24 C22 C23 120.7(5) . . ?
C24 C22 C23 120.7(5) 2 . ?
O3 C23 O3 126(2) 2 . ?
O3 C23 C22 116.9(12) 2 . ?
O3 C23 C22 116.9(12) . . ?
C21 C24 C22 120.1(8) . . ?
C21 C24 H24 119.9 . . ?
C22 C24 H24 119.9 . . ?

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
O2 C1 O1 Mn1 10(2) . . . 3_445 ?
C2 C1 O1 Mn1 -175.9(6) . . . 3_445 ?
O1 C1 O2 Mn1 10(2) . . . 4_445 ?
C2 C1 O2 Mn1 -164.6(9) . . . 4_445 ?
C4 C3 C2 C7 -5.7(12) . . . . ?
C4 C3 C2 C1 178.0(7) . . . . ?
O2 C1 C2 C3 -176.5(9) . . . . ?
O1 C1 C2 C3 8.7(13) . . . . ?
O2 C1 C2 C7 7.1(13) . . . . ?
O1 C1 C2 C7 -167.7(9) . . . . ?
C2 C3 C4 C5 5.0(12) . . . . ?
C3 C4 C5 C6 -2.1(11) . . . . ?
C3 C4 C5 C8 177.5(6) . . . . ?
C10 N2 C8 N3 -0.5(7) . . . . ?
C10 N2 C8 C5 -177.9(5) . . . . ?
C9 N3 C8 N2 -0.2(7) . . . . ?
C9 N3 C8 C5 177.3(5) . . . . ?
C4 C5 C8 N2 174.4(7) . . . . ?
C6 C5 C8 N2 -6.0(9) . . . . ?
C4 C5 C8 N3 -2.9(10) . . . . ?
C6 C5 C8 N3 176.7(6) . . . . ?
C3 C2 C7 C6 3.7(14) . . . . ?
C1 C2 C7 C6 -179.8(8) . . . . ?
C2 C7 C6 C5 -0.8(13) . . . . ?
C4 C5 C6 C7 0.0(12) . . . . ?
C8 C5 C6 C7 -179.6(7) . . . . ?
C8 N3 C9 C15 -179.3(6) . . . 2 ?
C8 N3 C9 C10 0.8(6) . . . . ?
C12 C11 C10 C9 1.6(8) . . . . ?
C12 C11 C10 N2 -176.8(5) . . . . ?
N3 C9 C10 C11 -179.8(5) . . . . ?
C15 C9 C10 C11 0.3(8) 2 . . . ?
N3 C9 C10 N2 -1.2(6) . . . . ?
C15 C9 C10 N2 179.0(5) 2 . . . ?
C8 N2 C10 C11 179.5(6) . . . . ?
C8 N2 C10 C9 1.0(6) . . . . ?
C10 C11 C12 C14 -2.2(7) . . . 2 ?
C10 C11 C12 C13 178.9(5) . . . . ?
C15 C14 C13 C12 -123.5(5) . . . . ?
C12 C14 C13 C12 57.4(5) 2 . . . ?
C15 C14 C13 C16 123.4(5) . . . . ?
C12 C14 C13 C16 -55.8(5) 2 . . . ?
C11 C12 C13 C14 123.2(6) . . . . ?
C14 C12 C13 C14 -55.9(5) 2 . . . ?
C11 C12 C13 C16 -124.3(5) . . . . ?
C14 C12 C13 C16 56.7(5) 2 . . . ?
C12 C14 C15 C9 0.9(7) 2 . . 2 ?
C13 C14 C15 C9 -178.1(5) . . . 2 ?
C14 C13 C16 C17 -123.1(5) . . . . ?
C12 C13 C16 C17 122.8(5) . . . . ?
C14 C13 C16 C16 57.3(5) . . . 2 ?
C12 C13 C16 C16 -56.8(6) . . . 2 ?
C16 C16 C17 C18 0.2(7) 2 . . . ?
C13 C16 C17 C18 -179.3(4) . . . . ?
C19 N1 C18 C18 0.0(6) . . . 2 ?
C19 N1 C18 C17 -180.0(4) . . . . ?
C16 C17 C18 C18 0.0(7) . . . 2 ?
C16 C17 C18 N1 179.9(4) . . . . ?
C18 N1 C19 N1 0.0(2) . . . 2 ?
C18 N1 C19 C20 180.0(2) . . . . ?
N1 C19 C20 C21 7.2(4) . . . 2 ?
N1 C19 C20 C21 -172.8(4) 2 . . 2 ?
N1 C19 C20 C21 -172.8(4) . . . . ?
N1 C19 C20 C21 7.2(4) 2 . . . ?
C19 C20 C21 C24 -177.1(6) . . . . ?
C21 C20 C21 C24 2.9(6) 2 . . . ?
Mn1 O3 C23 O3 12.0(7) . . . 2 ?
Mn1 O3 C23 C22 -168.0(7) . . . . ?
C24 C22 C23 O3 -176.9(6) . . . 2 ?
C24 C22 C23 O3 3.1(6) 2 . . 2 ?
C24 C22 C23 O3 3.1(6) . . . . ?
C24 C22 C23 O3 -176.9(6) 2 . . . ?
C20 C21 C24 C22 -5.7(11) . . . . ?
C24 C22 C24 C21 2.8(5) 2 . . . ?
C23 C22 C24 C21 -177.2(5) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.069


# SQUEEZE RESULTS (Version =  70515)
# 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 -0.042 0.031 0.326 6697 1360 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
####################################################################### 
# 
# 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_TPA
_database_code_depnum_ccdc_archive 'CCDC 1506278'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Tripticene triacid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44  H26 N6  O6, 4(C2 F3 O2)'
_chemical_formula_sum            'C52 H26 F12 N6 O14'
_chemical_formula_weight         1186.79

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.425(3)
_cell_length_b                   13.460(4)
_cell_length_c                   24.125(8)
_cell_angle_alpha                92.963(7)
_cell_angle_beta                 91.438(8)
_cell_angle_gamma                106.991(8)
_cell_volume                     2920.6(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    120
_cell_measurement_theta_min      5
_cell_measurement_theta_max      20

_exptl_crystal_description       square
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28908
_diffrn_reflns_av_unetI/netI     0.2531
_diffrn_reflns_av_R_equivalents  0.1228
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.022
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             10126
_reflns_number_gt                3787
_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_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1991P)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         10126
_refine_ls_number_parameters     737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2597
_refine_ls_R_factor_gt           0.1317
_refine_ls_wR_factor_ref         0.3729
_refine_ls_wR_factor_gt          0.3206
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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
F1 F 0.1653(10) 0.6697(7) 0.1991(3) 0.137(4) Uani 1 1 d . . . . .
O1 O 1.1421(6) 1.3281(4) 0.3339(2) 0.0330(15) Uani 1 1 d . . . . .
N1 N 0.9748(7) 0.7742(5) 0.2941(3) 0.0298(17) Uani 1 1 d . . . . .
H1 H 1.0702 0.7922 0.2960 0.036 Uiso 1 1 calc R U . . .
C1 C 1.1173(8) 1.2783(6) 0.2845(4) 0.025(2) Uani 1 1 d . . . . .
F2 F 0.1930(8) 0.8311(8) 0.2004(3) 0.133(3) Uani 1 1 d . . . . .
O2 O 1.1367(6) 1.3229(5) 0.2414(2) 0.0387(16) Uani 1 1 d . . . . .
N2 N 0.7515(7) 0.7849(5) 0.2893(2) 0.0258(17) Uani 1 1 d . . . . .
H2 H 0.6795 0.8120 0.2879 0.031 Uiso 1 1 calc R U . . .
C2 C 1.0634(8) 1.1656(6) 0.2857(3) 0.023(2) Uani 1 1 d . . . . .
F3 F 0.3599(9) 0.7689(7) 0.1645(3) 0.126(3) Uani 1 1 d . . . . .
O3 O 0.3360(7) -0.0088(5) -0.1780(2) 0.0501(18) Uani 1 1 d . . . . .
N3 N 0.4573(7) 0.2232(6) 0.0940(3) 0.0353(19) Uani 1 1 d . . . . .
H3 H 0.3669 0.2151 0.0831 0.042 Uiso 1 1 calc R U . . .
C3 C 1.0165(10) 1.1032(7) 0.2377(3) 0.040(2) Uani 1 1 d . . . . .
H3A H 1.0243 1.1335 0.2037 0.048 Uiso 1 1 calc R U . . .
F4 F 0.2691(15) 0.5869(6) 0.4795(3) 0.144(5) Uani 1 1 d . . . . .
O4 O 0.5604(8) -0.0312(5) -0.1742(2) 0.0512(18) Uani 1 1 d . . . . .
N4 N 0.6858(7) 0.2179(6) 0.0950(3) 0.039(2) Uani 1 1 d . . . . .
H4 H 0.7658 0.2056 0.0845 0.047 Uiso 1 1 calc R U . . .
C4 C 0.9588(11) 0.9978(8) 0.2391(4) 0.050(3) Uani 1 1 d . . . . .
H4A H 0.9225 0.9569 0.2066 0.060 Uiso 1 1 calc R U . . .
F5 F 0.2748(10) 0.4514(5) 0.4360(2) 0.110(3) Uani 1 1 d . . . . .
O5 O 0.3497(6) -0.0505(5) 0.7146(2) 0.0392(16) Uani 1 1 d . . . . .
N5 N 0.4666(6) 0.1958(5) 0.4642(2) 0.0180(15) Uani 1 1 d . . . . .
H5 H 0.3770 0.1870 0.4741 0.022 Uiso 1 1 calc R U . . .
C5 C 0.9551(9) 0.9522(6) 0.2898(3) 0.028(2) Uani 1 1 d . . . . .
F6 F 0.4575(16) 0.5718(10) 0.4500(6) 0.222(7) Uani 1 1 d . . . . .
O6 O 0.5865(6) -0.0482(4) 0.7183(2) 0.0376(15) Uani 1 1 d . . . . .
N6 N 0.6902(7) 0.1892(5) 0.4641(2) 0.0206(15) Uani 1 1 d . . . . .
H6 H 0.7702 0.1752 0.4739 0.025 Uiso 1 1 calc R U . . .
C6 C 1.0051(9) 1.0119(7) 0.3372(3) 0.032(2) Uani 1 1 d . . . . .
H6A H 1.0051 0.9806 0.3707 0.038 Uiso 1 1 calc R U . . .
F7 F 1.0064(9) 0.2968(7) 0.5386(4) 0.135(4) Uani 1 1 d . . . . .
O7 O 0.2595(7) 0.7648(5) 0.3022(3) 0.0470(17) Uani 1 1 d . . . . .
C7 C 1.0548(9) 1.1168(6) 0.3363(3) 0.030(2) Uani 1 1 d . . . . .
H7 H 1.0837 1.1571 0.3694 0.036 Uiso 1 1 calc R U . . .
F8 F 1.0863(11) 0.1955(5) 0.5824(2) 0.132(4) Uani 1 1 d . . . . .
O8 O 0.4809(7) 0.7975(6) 0.2650(4) 0.093(3) Uani 1 1 d . . . . .
C8 C 0.8938(10) 0.8358(7) 0.2903(3) 0.032(2) Uani 1 1 d . . . . .
F9 F 1.2239(7) 0.3059(6) 0.5382(3) 0.100(3) Uani 1 1 d . . . . .
O9 O 0.3235(9) 0.6920(5) 0.3875(3) 0.073(2) Uani 1 1 d . . . . .
C9 C 0.8803(9) 0.6736(6) 0.2948(3) 0.0234(19) Uani 1 1 d . . . . .
F10 F 1.113(2) 0.3674(8) 0.1157(5) 0.308(12) Uani 1 1 d . . . . .
O10 O 0.2495(7) 0.5386(5) 0.3419(3) 0.0442(17) Uani 1 1 d . . . . .
C10 C 0.9122(8) 0.5781(7) 0.2948(3) 0.024(2) Uani 1 1 d . . . . .
H10 H 1.0086 0.5731 0.2960 0.029 Uiso 1 1 calc R U . . .
F11 F 1.0184(13) 0.3457(9) 0.0419(6) 0.206(6) Uani 1 1 d . . . . .
O11 O 0.9345(6) 0.1282(5) 0.4704(2) 0.0393(16) Uani 1 1 d . . . . .
C11 C 0.7900(9) 0.4934(6) 0.2927(3) 0.0207(19) Uani 1 1 d . . . . .
F12 F 1.2315(11) 0.3500(8) 0.0526(6) 0.196(6) Uani 1 1 d . . . . .
O12 O 1.1733(6) 0.1413(5) 0.4688(2) 0.0382(16) Uani 1 1 d . . . . .
C12 C 0.6467(8) 0.4992(6) 0.2918(3) 0.0199(18) Uani 1 1 d . . . . .
O13 O 0.9270(7) 0.1597(7) 0.0809(3) 0.080(3) Uani 1 1 d . . . . .
C13 C 0.6160(9) 0.5947(7) 0.2901(3) 0.029(2) Uani 1 1 d . . . . .
H13 H 0.5198 0.5999 0.2884 0.035 Uiso 1 1 calc R U . . .
O14 O 1.1609(8) 0.1598(7) 0.0830(3) 0.093(3) Uani 1 1 d . . . . .
C14 C 0.7379(9) 0.6794(6) 0.2910(3) 0.024(2) Uani 1 1 d . . . . .
C15 C 0.4618(11) -0.0002(8) -0.1544(4) 0.047(3) Uani 1 1 d . . . . .
C16 C 0.4840(9) 0.0542(7) -0.0962(3) 0.033(2) Uani 1 1 d . . . . .
C17 C 0.6191(11) 0.0721(8) -0.0701(4) 0.055(3) Uani 1 1 d . . . . .
H17 H 0.6938 0.0525 -0.0880 0.066 Uiso 1 1 calc R U . . .
C18 C 0.6469(11) 0.1194(7) -0.0169(4) 0.043(2) Uiso 1 1 d . . . . .
H18 H 0.7385 0.1308 0.0016 0.052 Uiso 1 1 calc R U . . .
C19 C 0.5354(10) 0.1484(8) 0.0071(4) 0.045(3) Uani 1 1 d . . . . .
C20 C 0.3985(10) 0.1315(8) -0.0199(4) 0.054(3) Uani 1 1 d . . . . .
H20 H 0.3240 0.1527 -0.0028 0.065 Uiso 1 1 calc R U . . .
C21 C 0.3732(11) 0.0828(8) -0.0727(4) 0.050(3) Uani 1 1 d . . . . .
H21 H 0.2816 0.0701 -0.0914 0.060 Uiso 1 1 calc R U . . .
C22 C 0.5592(9) 0.1982(7) 0.0646(4) 0.039(2) Uani 1 1 d . . . . .
C23 C 0.6659(9) 0.2612(6) 0.1458(3) 0.029(2) Uani 1 1 d . . . . .
C24 C 0.5212(8) 0.2651(6) 0.1461(3) 0.026(2) Uani 1 1 d . . . . .
C25 C 0.4676(9) 0.3037(6) 0.1911(3) 0.027(2) Uani 1 1 d . . . . .
H25 H 0.3704 0.3069 0.1913 0.032 Uiso 1 1 calc R U . . .
C26 C 0.5615(8) 0.3372(5) 0.2356(3) 0.0187(18) Uani 1 1 d . . . . .
C27 C 0.7101(8) 0.3331(5) 0.2360(3) 0.0193(18) Uani 1 1 d . . . . .
C28 C 0.7666(9) 0.2942(6) 0.1911(3) 0.026(2) Uani 1 1 d . . . . .
H28 H 0.8634 0.2901 0.1907 0.031 Uiso 1 1 calc R U . . .
C29 C 0.4693(9) -0.0351(6) 0.6951(3) 0.026(2) Uani 1 1 d . . . . .
C30 C 0.4933(9) 0.0057(6) 0.6381(3) 0.0236(19) Uani 1 1 d . . . . .
C31 C 0.3775(9) 0.0311(6) 0.6119(3) 0.032(2) Uani 1 1 d . . . . .
H31 H 0.2839 0.0144 0.6266 0.038 Uiso 1 1 calc R U . . .
C32 C 0.4040(9) 0.0813(6) 0.5638(3) 0.026(2) Uiso 1 1 d . . . . .
H32 H 0.3271 0.0993 0.5461 0.032 Uiso 1 1 calc R U . . .
C33 C 0.5391(8) 0.1056(6) 0.5409(3) 0.0229(19) Uani 1 1 d . . . . .
C34 C 0.6492(9) 0.0749(6) 0.5664(3) 0.031(2) Uani 1 1 d . . . . .
H34 H 0.7408 0.0881 0.5501 0.037 Uiso 1 1 calc R U . . .
C35 C 0.6295(9) 0.0255(6) 0.6149(3) 0.025(2) Uani 1 1 d . . . . .
H35 H 0.7061 0.0057 0.6317 0.030 Uiso 1 1 calc R U . . .
C36 C 0.5661(8) 0.1643(6) 0.4897(3) 0.0184(18) Uani 1 1 d . . . . .
C37 C 0.5296(8) 0.2467(6) 0.4177(3) 0.0219(19) Uani 1 1 d . . . . .
C38 C 0.4695(8) 0.2959(6) 0.3772(3) 0.024(2) Uani 1 1 d . . . . .
H38 H 0.3734 0.3013 0.3777 0.029 Uiso 1 1 calc R U . . .
C39 C 0.5676(9) 0.3359(6) 0.3360(3) 0.025(2) Uani 1 1 d . . . . .
C40 C 0.7137(8) 0.3305(6) 0.3368(3) 0.0181(18) Uani 1 1 d . . . . .
C41 C 0.7678(8) 0.2808(6) 0.3771(3) 0.0209(19) Uiso 1 1 d . . . . .
H41 H 0.8630 0.2738 0.3766 0.025 Uiso 1 1 calc R U . . .
C42 C 0.6712(7) 0.2419(5) 0.4186(3) 0.0104(16) Uani 1 1 d . . . . .
C43 C 0.7975(8) 0.3818(6) 0.2888(3) 0.0218(19) Uani 1 1 d . . . . .
H43 H 0.8998 0.3780 0.2890 0.026 Uiso 1 1 calc R U . . .
C44 C 0.5307(8) 0.3937(6) 0.2885(3) 0.0210(19) Uani 1 1 d . . . . .
H44 H 0.4289 0.3985 0.2888 0.025 Uiso 1 1 calc R U . . .
C45 C 0.3453(11) 0.7795(8) 0.2634(5) 0.046(3) Uani 1 1 d . . . . .
C46 C 0.2694(14) 0.7553(13) 0.2049(7) 0.088(4) Uani 1 1 d . . . . .
C47 C 0.2925(10) 0.5957(8) 0.3830(4) 0.047(3) Uani 1 1 d . . . . .
C48 C 0.298(2) 0.5445(11) 0.4378(6) 0.097(5) Uani 1 1 d . . . . .
C49 C 1.0646(9) 0.1601(7) 0.4857(3) 0.034(2) Uani 1 1 d . . . . .
C50 C 1.0987(11) 0.2441(8) 0.5365(4) 0.045(3) Uani 1 1 d . . . . .
C51 C 1.0592(13) 0.1973(9) 0.0791(4) 0.050(3) Uiso 1 1 d . . . . .
C52 C 1.1034(17) 0.3141(13) 0.0728(6) 0.091(5) 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
F1 C46 1.275(14) . ?
O1 C1 1.319(9) . ?
N1 C8 1.285(10) . ?
N1 C9 1.387(9) . ?
N1 H1 0.8600 . ?
C1 O2 1.218(9) . ?
C1 C2 1.454(11) . ?
F2 C46 1.417(15) . ?
N2 C8 1.314(10) . ?
N2 C14 1.391(10) . ?
N2 H2 0.8600 . ?
C2 C3 1.379(11) . ?
C2 C7 1.409(11) . ?
F3 C46 1.297(14) . ?
O3 C15 1.274(10) . ?
N3 C22 1.319(10) . ?
N3 C24 1.396(9) . ?
N3 H3 0.8600 . ?
C3 C4 1.366(12) . ?
C3 H3A 0.9300 . ?
F4 C48 1.206(15) . ?
O4 C15 1.223(10) . ?
N4 C22 1.335(9) . ?
N4 C23 1.370(9) . ?
N4 H4 0.8600 . ?
C4 C5 1.393(11) . ?
C4 H4A 0.9300 . ?
F5 C48 1.205(13) . ?
O5 C29 1.198(8) . ?
N5 C36 1.291(9) . ?
N5 C37 1.398(9) . ?
N5 H5 0.8600 . ?
C5 C6 1.354(11) . ?
C5 C8 1.505(12) . ?
F6 C48 1.460(19) . ?
O6 C29 1.287(9) . ?
N6 C36 1.300(9) . ?
N6 C42 1.372(8) . ?
N6 H6 0.8600 . ?
C6 C7 1.353(11) . ?
C6 H6A 0.9300 . ?
F7 C50 1.274(11) . ?
O7 C45 1.239(10) . ?
C7 H7 0.9300 . ?
F8 C50 1.304(11) . ?
O8 C45 1.229(10) . ?
F9 C50 1.227(10) . ?
O9 C47 1.240(11) . ?
C9 C14 1.368(10) . ?
C9 C10 1.404(11) . ?
F10 C52 1.215(15) . ?
O10 C47 1.207(10) . ?
C10 C11 1.361(10) . ?
C10 H10 0.9300 . ?
F11 C52 1.256(14) . ?
O11 C49 1.216(9) . ?
C11 C12 1.376(10) . ?
C11 C43 1.522(10) . ?
F12 C52 1.281(14) . ?
O12 C49 1.201(9) . ?
C12 C13 1.400(11) . ?
C12 C44 1.515(10) . ?
O13 C51 1.203(11) . ?
C13 C14 1.360(10) . ?
C13 H13 0.9300 . ?
O14 C51 1.210(11) . ?
C15 C16 1.530(13) . ?
C16 C21 1.343(11) . ?
C16 C17 1.357(11) . ?
C17 C18 1.386(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.356(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(11) . ?
C19 C22 1.490(12) . ?
C20 C21 1.384(12) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C23 C24 1.381(10) . ?
C23 C28 1.394(10) . ?
C24 C25 1.351(10) . ?
C25 C26 1.344(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.417(10) . ?
C26 C44 1.530(10) . ?
C27 C28 1.367(10) . ?
C27 C43 1.510(10) . ?
C28 H28 0.9300 . ?
C29 C30 1.504(11) . ?
C30 C35 1.373(10) . ?
C30 C31 1.384(11) . ?
C31 C32 1.364(11) . ?
C31 H31 0.9300 . ?
C32 C33 1.357(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.369(10) . ?
C33 C36 1.488(11) . ?
C34 C35 1.365(10) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C37 C42 1.355(9) . ?
C37 C38 1.406(10) . ?
C38 C39 1.393(10) . ?
C38 H38 0.9300 . ?
C39 C40 1.400(10) . ?
C39 C44 1.507(10) . ?
C40 C41 1.376(10) . ?
C40 C43 1.501(10) . ?
C41 C42 1.387(9) . ?
C41 H41 0.9300 . ?
C43 H43 0.9800 . ?
C44 H44 0.9800 . ?
C45 C46 1.541(17) . ?
C47 C48 1.529(16) . ?
C49 C50 1.584(13) . ?
C51 C52 1.522(17) . ?

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
C8 N1 C9 107.6(7) . . ?
C8 N1 H1 126.2 . . ?
C9 N1 H1 126.2 . . ?
O2 C1 O1 122.8(7) . . ?
O2 C1 C2 122.9(8) . . ?
O1 C1 C2 114.3(7) . . ?
C8 N2 C14 107.9(7) . . ?
C8 N2 H2 126.0 . . ?
C14 N2 H2 126.0 . . ?
C3 C2 C7 117.8(8) . . ?
C3 C2 C1 121.2(8) . . ?
C7 C2 C1 121.0(7) . . ?
C22 N3 C24 108.4(7) . . ?
C22 N3 H3 125.8 . . ?
C24 N3 H3 125.8 . . ?
C4 C3 C2 121.3(8) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C22 N4 C23 108.2(7) . . ?
C22 N4 H4 125.9 . . ?
C23 N4 H4 125.9 . . ?
C3 C4 C5 119.1(8) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C36 N5 C37 108.3(6) . . ?
C36 N5 H5 125.9 . . ?
C37 N5 H5 125.9 . . ?
C6 C5 C4 120.4(8) . . ?
C6 C5 C8 121.3(7) . . ?
C4 C5 C8 118.3(8) . . ?
C36 N6 C42 108.1(6) . . ?
C36 N6 H6 126.0 . . ?
C42 N6 H6 126.0 . . ?
C7 C6 C5 120.5(8) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C2 120.7(8) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N1 C8 N2 111.7(8) . . ?
N1 C8 C5 123.8(8) . . ?
N2 C8 C5 124.4(8) . . ?
C14 C9 N1 107.5(7) . . ?
C14 C9 C10 122.1(7) . . ?
N1 C9 C10 130.3(7) . . ?
C11 C10 C9 114.2(7) . . ?
C11 C10 H10 122.9 . . ?
C9 C10 H10 122.9 . . ?
C10 C11 C12 123.7(8) . . ?
C10 C11 C43 123.4(7) . . ?
C12 C11 C43 112.8(7) . . ?
C11 C12 C13 121.5(7) . . ?
C11 C12 C44 113.4(7) . . ?
C13 C12 C44 124.9(7) . . ?
C14 C13 C12 114.8(7) . . ?
C14 C13 H13 122.6 . . ?
C12 C13 H13 122.6 . . ?
C13 C14 C9 123.5(8) . . ?
C13 C14 N2 131.2(8) . . ?
C9 C14 N2 105.3(7) . . ?
O4 C15 O3 125.9(10) . . ?
O4 C15 C16 120.0(9) . . ?
O3 C15 C16 114.1(9) . . ?
C21 C16 C17 122.1(8) . . ?
C21 C16 C15 120.6(8) . . ?
C17 C16 C15 117.3(8) . . ?
C16 C17 C18 120.7(9) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 117.5(9) . . ?
C19 C18 H18 121.3 . . ?
C17 C18 H18 121.3 . . ?
C18 C19 C20 121.8(9) . . ?
C18 C19 C22 119.5(8) . . ?
C20 C19 C22 118.7(8) . . ?
C19 C20 C21 119.5(9) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 118.4(9) . . ?
C16 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
N3 C22 N4 110.0(7) . . ?
N3 C22 C19 125.5(7) . . ?
N4 C22 C19 124.3(8) . . ?
N4 C23 C24 107.5(7) . . ?
N4 C23 C28 128.8(7) . . ?
C24 C23 C28 123.7(7) . . ?
C25 C24 C23 121.4(7) . . ?
C25 C24 N3 132.6(7) . . ?
C23 C24 N3 105.9(7) . . ?
C26 C25 C24 116.8(7) . . ?
C26 C25 H25 121.6 . . ?
C24 C25 H25 121.6 . . ?
C25 C26 C27 122.4(7) . . ?
C25 C26 C44 125.9(7) . . ?
C27 C26 C44 111.5(6) . . ?
C28 C27 C26 121.8(7) . . ?
C28 C27 C43 125.1(7) . . ?
C26 C27 C43 113.0(7) . . ?
C27 C28 C23 113.8(7) . . ?
C27 C28 H28 123.1 . . ?
C23 C28 H28 123.1 . . ?
O5 C29 O6 126.8(8) . . ?
O5 C29 C30 119.6(7) . . ?
O6 C29 C30 113.6(7) . . ?
C35 C30 C31 120.8(7) . . ?
C35 C30 C29 121.1(7) . . ?
C31 C30 C29 117.9(7) . . ?
C32 C31 C30 118.4(8) . . ?
C32 C31 H31 120.8 . . ?
C30 C31 H31 120.8 . . ?
C33 C32 C31 122.1(8) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C32 C33 C34 118.0(7) . . ?
C32 C33 C36 120.8(7) . . ?
C34 C33 C36 121.2(7) . . ?
C35 C34 C33 122.3(8) . . ?
C35 C34 H34 118.8 . . ?
C33 C34 H34 118.8 . . ?
C34 C35 C30 118.1(7) . . ?
C34 C35 H35 120.9 . . ?
C30 C35 H35 120.9 . . ?
N5 C36 N6 110.9(7) . . ?
N5 C36 C33 123.7(7) . . ?
N6 C36 C33 125.3(7) . . ?
C42 C37 N5 105.4(6) . . ?
C42 C37 C38 123.8(7) . . ?
N5 C37 C38 130.8(7) . . ?
C39 C38 C37 113.6(7) . . ?
C39 C38 H38 123.2 . . ?
C37 C38 H38 123.2 . . ?
C38 C39 C40 122.5(7) . . ?
C38 C39 C44 123.8(7) . . ?
C40 C39 C44 113.6(6) . . ?
C41 C40 C39 122.0(7) . . ?
C41 C40 C43 126.0(7) . . ?
C39 C40 C43 112.0(6) . . ?
C40 C41 C42 115.7(7) . . ?
C40 C41 H41 122.1 . . ?
C42 C41 H41 122.1 . . ?
C37 C42 N6 107.4(6) . . ?
C37 C42 C41 122.2(7) . . ?
N6 C42 C41 130.3(6) . . ?
C40 C43 C27 107.9(6) . . ?
C40 C43 C11 105.8(6) . . ?
C27 C43 C11 105.0(6) . . ?
C40 C43 H43 112.5 . . ?
C27 C43 H43 112.5 . . ?
C11 C43 H43 112.5 . . ?
C39 C44 C12 106.3(6) . . ?
C39 C44 C26 105.9(6) . . ?
C12 C44 C26 105.3(6) . . ?
C39 C44 H44 112.9 . . ?
C12 C44 H44 112.9 . . ?
C26 C44 H44 112.9 . . ?
O8 C45 O7 128.9(11) . . ?
O8 C45 C46 115.3(11) . . ?
O7 C45 C46 115.0(9) . . ?
F1 C46 F3 113.1(15) . . ?
F1 C46 F2 103.1(11) . . ?
F3 C46 F2 105.8(12) . . ?
F1 C46 C45 114.5(12) . . ?
F3 C46 C45 114.8(11) . . ?
F2 C46 C45 103.9(12) . . ?
O10 C47 O9 128.1(10) . . ?
O10 C47 C48 117.0(10) . . ?
O9 C47 C48 114.6(9) . . ?
F5 C48 F4 118.5(15) . . ?
F5 C48 F6 96.6(13) . . ?
F4 C48 F6 96.1(12) . . ?
F5 C48 C47 117.8(11) . . ?
F4 C48 C47 117.9(12) . . ?
F6 C48 C47 101.4(13) . . ?
O12 C49 O11 131.9(9) . . ?
O12 C49 C50 113.6(8) . . ?
O11 C49 C50 114.5(8) . . ?
F9 C50 F7 107.6(10) . . ?
F9 C50 F8 106.8(9) . . ?
F7 C50 F8 106.2(10) . . ?
F9 C50 C49 114.6(8) . . ?
F7 C50 C49 112.9(8) . . ?
F8 C50 C49 108.3(8) . . ?
O13 C51 O14 131.8(12) . . ?
O13 C51 C52 112.4(11) . . ?
O14 C51 C52 115.7(11) . . ?
F10 C52 F11 103.4(18) . . ?
F10 C52 F12 103.1(15) . . ?
F11 C52 F12 104.3(13) . . ?
F10 C52 C51 115.3(12) . . ?
F11 C52 C51 115.8(13) . . ?
F12 C52 C51 113.4(14) . . ?

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
O2 C1 C2 C3 -6.8(12) . . . . ?
O1 C1 C2 C3 172.6(7) . . . . ?
O2 C1 C2 C7 174.4(7) . . . . ?
O1 C1 C2 C7 -6.2(10) . . . . ?
C7 C2 C3 C4 2.2(13) . . . . ?
C1 C2 C3 C4 -176.6(8) . . . . ?
C2 C3 C4 C5 -3.6(14) . . . . ?
C3 C4 C5 C6 1.4(14) . . . . ?
C3 C4 C5 C8 -178.9(8) . . . . ?
C4 C5 C6 C7 2.1(13) . . . . ?
C8 C5 C6 C7 -177.6(7) . . . . ?
C5 C6 C7 C2 -3.5(12) . . . . ?
C3 C2 C7 C6 1.4(12) . . . . ?
C1 C2 C7 C6 -179.8(7) . . . . ?
C9 N1 C8 N2 1.2(9) . . . . ?
C9 N1 C8 C5 178.4(7) . . . . ?
C14 N2 C8 N1 -1.9(9) . . . . ?
C14 N2 C8 C5 -179.2(7) . . . . ?
C6 C5 C8 N1 -77.9(11) . . . . ?
C4 C5 C8 N1 102.4(10) . . . . ?
C6 C5 C8 N2 99.0(10) . . . . ?
C4 C5 C8 N2 -80.7(10) . . . . ?
C8 N1 C9 C14 0.1(9) . . . . ?
C8 N1 C9 C10 175.3(8) . . . . ?
C14 C9 C10 C11 -2.3(11) . . . . ?
N1 C9 C10 C11 -176.8(7) . . . . ?
C9 C10 C11 C12 -1.1(10) . . . . ?
C9 C10 C11 C43 176.2(7) . . . . ?
C10 C11 C12 C13 3.3(11) . . . . ?
C43 C11 C12 C13 -174.3(7) . . . . ?
C10 C11 C12 C44 179.0(6) . . . . ?
C43 C11 C12 C44 1.4(9) . . . . ?
C11 C12 C13 C14 -1.8(11) . . . . ?
C44 C12 C13 C14 -177.0(7) . . . . ?
C12 C13 C14 C9 -1.5(11) . . . . ?
C12 C13 C14 N2 179.2(7) . . . . ?
N1 C9 C14 C13 179.4(7) . . . . ?
C10 C9 C14 C13 3.7(12) . . . . ?
N1 C9 C14 N2 -1.2(8) . . . . ?
C10 C9 C14 N2 -176.9(7) . . . . ?
C8 N2 C14 C13 -178.8(8) . . . . ?
C8 N2 C14 C9 1.9(8) . . . . ?
O4 C15 C16 C21 -175.8(9) . . . . ?
O3 C15 C16 C21 4.0(13) . . . . ?
O4 C15 C16 C17 4.3(13) . . . . ?
O3 C15 C16 C17 -175.8(8) . . . . ?
C21 C16 C17 C18 1.3(15) . . . . ?
C15 C16 C17 C18 -178.9(9) . . . . ?
C16 C17 C18 C19 -1.2(14) . . . . ?
C17 C18 C19 C20 0.2(14) . . . . ?
C17 C18 C19 C22 179.2(9) . . . . ?
C18 C19 C20 C21 0.7(15) . . . . ?
C22 C19 C20 C21 -178.3(9) . . . . ?
C17 C16 C21 C20 -0.3(15) . . . . ?
C15 C16 C21 C20 179.8(9) . . . . ?
C19 C20 C21 C16 -0.7(15) . . . . ?
C24 N3 C22 N4 2.2(10) . . . . ?
C24 N3 C22 C19 178.2(9) . . . . ?
C23 N4 C22 N3 -2.3(10) . . . . ?
C23 N4 C22 C19 -178.3(9) . . . . ?
C18 C19 C22 N3 -174.9(9) . . . . ?
C20 C19 C22 N3 4.1(15) . . . . ?
C18 C19 C22 N4 0.5(14) . . . . ?
C20 C19 C22 N4 179.5(9) . . . . ?
C22 N4 C23 C24 1.4(10) . . . . ?
C22 N4 C23 C28 179.9(9) . . . . ?
N4 C23 C24 C25 179.6(8) . . . . ?
C28 C23 C24 C25 1.1(13) . . . . ?
N4 C23 C24 N3 -0.1(9) . . . . ?
C28 C23 C24 N3 -178.7(7) . . . . ?
C22 N3 C24 C25 179.0(9) . . . . ?
C22 N3 C24 C23 -1.2(9) . . . . ?
C23 C24 C25 C26 -0.5(12) . . . . ?
N3 C24 C25 C26 179.2(8) . . . . ?
C24 C25 C26 C27 0.1(11) . . . . ?
C24 C25 C26 C44 173.3(7) . . . . ?
C25 C26 C27 C28 -0.3(11) . . . . ?
C44 C26 C27 C28 -174.4(7) . . . . ?
C25 C26 C27 C43 176.0(7) . . . . ?
C44 C26 C27 C43 1.9(8) . . . . ?
C26 C27 C28 C23 0.8(10) . . . . ?
C43 C27 C28 C23 -175.0(7) . . . . ?
N4 C23 C28 C27 -179.4(8) . . . . ?
C24 C23 C28 C27 -1.2(12) . . . . ?
O5 C29 C30 C35 179.1(7) . . . . ?
O6 C29 C30 C35 0.3(11) . . . . ?
O5 C29 C30 C31 4.5(11) . . . . ?
O6 C29 C30 C31 -174.4(7) . . . . ?
C35 C30 C31 C32 -3.4(12) . . . . ?
C29 C30 C31 C32 171.2(7) . . . . ?
C30 C31 C32 C33 0.7(12) . . . . ?
C31 C32 C33 C34 2.5(12) . . . . ?
C31 C32 C33 C36 -177.4(7) . . . . ?
C32 C33 C34 C35 -3.1(12) . . . . ?
C36 C33 C34 C35 176.7(7) . . . . ?
C33 C34 C35 C30 0.5(12) . . . . ?
C31 C30 C35 C34 2.8(12) . . . . ?
C29 C30 C35 C34 -171.7(7) . . . . ?
C37 N5 C36 N6 -0.3(8) . . . . ?
C37 N5 C36 C33 -179.3(7) . . . . ?
C42 N6 C36 N5 0.5(8) . . . . ?
C42 N6 C36 C33 179.5(7) . . . . ?
C32 C33 C36 N5 0.4(11) . . . . ?
C34 C33 C36 N5 -179.5(7) . . . . ?
C32 C33 C36 N6 -178.4(7) . . . . ?
C34 C33 C36 N6 1.7(12) . . . . ?
C36 N5 C37 C42 0.0(8) . . . . ?
C36 N5 C37 C38 -179.0(8) . . . . ?
C42 C37 C38 C39 2.7(11) . . . . ?
N5 C37 C38 C39 -178.4(7) . . . . ?
C37 C38 C39 C40 -2.4(11) . . . . ?
C37 C38 C39 C44 -178.9(7) . . . . ?
C38 C39 C40 C41 3.1(12) . . . . ?
C44 C39 C40 C41 180.0(7) . . . . ?
C38 C39 C40 C43 -178.3(7) . . . . ?
C44 C39 C40 C43 -1.5(9) . . . . ?
C39 C40 C41 C42 -3.6(11) . . . . ?
C43 C40 C41 C42 178.0(7) . . . . ?
N5 C37 C42 N6 0.3(8) . . . . ?
C38 C37 C42 N6 179.4(7) . . . . ?
N5 C37 C42 C41 177.2(6) . . . . ?
C38 C37 C42 C41 -3.7(12) . . . . ?
C36 N6 C42 C37 -0.5(8) . . . . ?
C36 N6 C42 C41 -177.1(7) . . . . ?
C40 C41 C42 C37 3.9(11) . . . . ?
C40 C41 C42 N6 180.0(7) . . . . ?
C41 C40 C43 C27 123.5(8) . . . . ?
C39 C40 C43 C27 -55.0(8) . . . . ?
C41 C40 C43 C11 -124.4(8) . . . . ?
C39 C40 C43 C11 57.1(8) . . . . ?
C28 C27 C43 C40 -129.2(8) . . . . ?
C26 C27 C43 C40 54.7(8) . . . . ?
C28 C27 C43 C11 118.2(8) . . . . ?
C26 C27 C43 C11 -57.9(8) . . . . ?
C10 C11 C43 C40 124.8(7) . . . . ?
C12 C11 C43 C40 -57.5(8) . . . . ?
C10 C11 C43 C27 -121.1(7) . . . . ?
C12 C11 C43 C27 56.5(8) . . . . ?
C38 C39 C44 C12 122.6(8) . . . . ?
C40 C39 C44 C12 -54.2(8) . . . . ?
C38 C39 C44 C26 -125.8(7) . . . . ?
C40 C39 C44 C26 57.4(8) . . . . ?
C11 C12 C44 C39 54.1(8) . . . . ?
C13 C12 C44 C39 -130.4(8) . . . . ?
C11 C12 C44 C26 -57.9(8) . . . . ?
C13 C12 C44 C26 117.6(8) . . . . ?
C25 C26 C44 C39 129.2(8) . . . . ?
C27 C26 C44 C39 -56.9(8) . . . . ?
C25 C26 C44 C12 -118.4(8) . . . . ?
C27 C26 C44 C12 55.5(7) . . . . ?
O8 C45 C46 F1 125.6(12) . . . . ?
O7 C45 C46 F1 -45.4(16) . . . . ?
O8 C45 C46 F3 -7.7(17) . . . . ?
O7 C45 C46 F3 -178.7(11) . . . . ?
O8 C45 C46 F2 -122.7(10) . . . . ?
O7 C45 C46 F2 66.3(12) . . . . ?
O10 C47 C48 F5 8(2) . . . . ?
O9 C47 C48 F5 -176.9(14) . . . . ?
O10 C47 C48 F4 -144.9(15) . . . . ?
O9 C47 C48 F4 30(2) . . . . ?
O10 C47 C48 F6 111.8(12) . . . . ?
O9 C47 C48 F6 -73.1(14) . . . . ?
O12 C49 C50 F9 26.9(12) . . . . ?
O11 C49 C50 F9 -151.7(9) . . . . ?
O12 C49 C50 F7 150.5(9) . . . . ?
O11 C49 C50 F7 -28.0(12) . . . . ?
O12 C49 C50 F8 -92.2(10) . . . . ?
O11 C49 C50 F8 89.2(10) . . . . ?
O13 C51 C52 F10 83.3(19) . . . . ?
O14 C51 C52 F10 -94.5(19) . . . . ?
O13 C51 C52 F11 -37.6(18) . . . . ?
O14 C51 C52 F11 144.5(14) . . . . ?
O13 C51 C52 F12 -158.1(12) . . . . ?
O14 C51 C52 F12 24.0(17) . . . . ?

_refine_diff_density_max         0.715
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_Cd_TPA_DMSO
_database_code_depnum_ccdc_archive 'CCDC 1506926'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Tripticene triacid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 Cd N3 O6 S'
_chemical_formula_weight         587.86

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'
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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   14.0040(14)
_cell_length_b                   41.869(5)
_cell_length_c                   17.1369(17)
_cell_angle_alpha                90
_cell_angle_beta                 104.489(3)
_cell_angle_gamma                90
_cell_volume                     9728.4(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    150
_cell_measurement_theta_min      5
_cell_measurement_theta_max      20

_exptl_crystal_description       square
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.803
_exptl_crystal_F_000             2352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.514
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30948
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.094
_diffrn_reflns_theta_max         18.485
_diffrn_reflns_theta_full        18.485
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3617
_reflns_number_gt                2958
_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    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0012(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3617
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1801
_refine_ls_R_factor_gt           0.1699
_refine_ls_wR_factor_ref         0.4914
_refine_ls_wR_factor_gt          0.4741
_refine_ls_goodness_of_fit_ref   2.383
_refine_ls_restrained_S_all      2.383
_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
O1 O 0.7132(14) 0.3259(4) 0.0846(11) 0.198(8) Uani 1 1 d . . . . .
S1 S 0.1296(8) 0.5477(3) 0.7156(10) 0.384(8) Uani 1 1 d . . . . .
N1 N 0.4873(6) 0.40660(19) 0.3580(6) 0.057(2) Uani 1 1 d . . . . .
H1 H 0.5480 0.4031 0.3821 0.069 Uiso 1 1 calc R U . . .
C1 C 0.6406(18) 0.3330(4) 0.0739(14) 0.115(6) Uani 1 1 d . . . . .
O2 O 0.5844(16) 0.3280(4) -0.0024(12) 0.220(8) Uani 1 1 d . . . . .
N2 N 0.3469(7) 0.4063(2) 0.2637(5) 0.060(3) Uani 1 1 d . . . . .
C2 C 0.582(2) 0.3507(3) 0.1268(13) 0.113(5) Uani 1 1 d . . . . .
O3 O 0.3192(12) 0.7543(3) 0.5358(9) 0.170(6) Uani 1 1 d . . . . .
N3 N 0.3229(5) 0.5865(2) 0.5452(4) 0.051(2) Uani 1 1 d . . . . .
C3 C 0.4856(14) 0.3559(5) 0.1025(11) 0.138(7) Uani 1 1 d . . . . .
H3 H 0.4504 0.3489 0.0520 0.166 Uiso 1 1 calc R U . . .
C4 C 0.4380(12) 0.3717(4) 0.1521(10) 0.124(6) Uani 1 1 d . . . . .
H4 H 0.3708 0.3759 0.1345 0.149 Uiso 1 1 calc R U . . .
C5 C 0.4904(10) 0.3817(3) 0.2291(8) 0.072(3) Uani 1 1 d . . . . .
C6 C 0.5834(14) 0.3755(4) 0.2495(9) 0.113(5) Uani 1 1 d . . . . .
H6 H 0.6203 0.3820 0.2999 0.135 Uiso 1 1 calc R U . . .
C7 C 0.6325(11) 0.3586(4) 0.1971(13) 0.107(5) Uani 1 1 d . . . . .
H7 H 0.6992 0.3536 0.2140 0.129 Uiso 1 1 calc R U . . .
C8 C 0.4408(9) 0.3985(2) 0.2822(8) 0.057(3) Uani 1 1 d . . . . .
C9 C 0.3286(8) 0.4222(2) 0.3308(6) 0.051(3) Uani 1 1 d . . . . .
C10 C 0.4178(7) 0.4218(2) 0.3895(7) 0.046(3) Uani 1 1 d . . . . .
C11 C 0.4243(7) 0.4359(2) 0.4638(7) 0.049(3) Uani 1 1 d . . . . .
H11 H 0.4837 0.4367 0.5029 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3405(7) 0.44853(19) 0.4772(5) 0.039(3) Uani 1 1 d . . . . .
C13 C 0.2499(6) 0.44888(19) 0.4176(6) 0.040(3) Uani 1 1 d . . . . .
C14 C 0.2420(7) 0.4351(2) 0.3438(6) 0.050(3) Uani 1 1 d . . . . .
H14 H 0.1826 0.4344 0.3047 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3325(6) 0.4657(2) 0.5568(6) 0.044(3) Uani 1 1 d . . . . .
H15 H 0.3947 0.4661 0.5986 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2941(6) 0.4982(2) 0.5293(5) 0.038(3) Uani 1 1 d . . . . .
C17 C 0.3418(6) 0.5271(2) 0.5579(5) 0.042(3) Uani 1 1 d . . . . .
H17 H 0.4028 0.5273 0.5951 0.051 Uiso 1 1 calc R U . . .
C18 C 0.2945(6) 0.5547(3) 0.5284(4) 0.039(3) Uani 1 1 d . . . . .
C19 C 0.2500 0.6044(4) 0.5000 0.045(4) Uani 1 2 d S T P . .
C20 C 0.2500 0.6372(5) 0.5000 0.059(4) Uani 1 2 d S T P . .
C21 C 0.3324(10) 0.6556(3) 0.5360(8) 0.094(4) Uani 1 1 d . . . . .
H21 H 0.3906 0.6451 0.5611 0.112 Uiso 1 1 calc R U . . .
C22 C 0.3318(11) 0.6884(5) 0.5362(9) 0.106(4) Uani 1 1 d . . . . .
H22 H 0.3887 0.6995 0.5617 0.128 Uiso 1 1 calc R U . . .
C23 C 0.2500 0.7048(5) 0.5000 0.093(7) Uani 1 2 d S T P . .
C24 C 0.2500 0.7394(11) 0.5000 0.139(13) Uani 1 2 d S T P . .
O4 O 0.2295(16) 0.5542(6) 0.741(2) 0.384(8) Uani 1 1 d . . . . .
C26 C 0.016(2) 0.5574(9) 0.725(3) 0.384(8) Uani 1 1 d . . . . .
H26A H 0.0168 0.5791 0.7430 0.575 Uiso 1 1 calc R U . . .
H26B H -0.0020 0.5434 0.7625 0.575 Uiso 1 1 calc R U . . .
H26C H -0.0300 0.5554 0.6730 0.575 Uiso 1 1 calc R U . . .
Cd1 Cd 0.8658(3) 0.30378(9) 0.1021(3) 0.091(2) Uani 0.353(11) 1 d . . P A 1
O5A O 0.8551(16) 0.2742(5) 0.2158(11) 0.091(2) Uani 0.353(11) 1 d . . P A 1
O6A O 1.0233(17) 0.2889(6) 0.1375(12) 0.091(2) Uani 0.353(11) 1 d . . P A 1
Cd2 Cd 0.8114(9) 0.30244(8) 0.0488(7) 0.246(6) Uani 0.647(11) 1 d . . P A 2
O5B O 0.755(2) 0.2595(5) 0.2023(15) 0.246(6) Uani 0.647(11) 1 d . . P A 2
O6B O 0.970(3) 0.3030(4) 0.1789(19) 0.246(6) Uani 0.647(11) 1 d . . P A 2
C25 C 0.140(2) 0.5149(9) 0.670(3) 0.384(8) Uani 1 1 d . . . . .
H25A H 0.0757 0.5062 0.6472 0.575 Uiso 1 1 calc R U . . .
H25B H 0.1726 0.5189 0.6279 0.575 Uiso 1 1 calc R U . . .
H25C H 0.1781 0.4999 0.7077 0.575 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.03(2) . ?
O1 Cd2 1.911(16) . ?
O1 Cd1 2.279(18) . ?
O1 Cd2 2.43(2) 2_655 ?
S1 O4 1.39(2) . ?
S1 C25 1.60(3) . ?
S1 C26 1.68(3) . ?
N1 C8 1.342(12) . ?
N1 C10 1.380(12) . ?
N1 H1 0.8600 . ?
C1 O2 1.36(2) . ?
C1 C2 1.56(2) . ?
C1 Cd2 2.687(17) 2_655 ?
O2 Cd2 2.119(17) 2_655 ?
O2 Cd1 2.242(15) 2_655 ?
N2 C8 1.315(12) . ?
N2 C9 1.407(12) . ?
C2 C7 1.280(18) . ?
C2 C3 1.32(2) . ?
O3 C24 1.186(19) . ?
O3 Cd2 2.034(15) 3_455 ?
O3 Cd1 2.374(15) 3_455 ?
N3 C19 1.345(10) . ?
N3 C18 1.398(12) . ?
C3 C4 1.37(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.289(17) . ?
C5 C8 1.457(16) . ?
C6 C7 1.44(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.394(12) . ?
C9 C14 1.395(13) . ?
C10 C11 1.386(13) . ?
C11 C12 1.359(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.416(11) . ?
C12 C15 1.570(13) . ?
C13 C14 1.369(12) . ?
C13 C15 1.507(12) 2_556 ?
C14 H14 0.9300 . ?
C15 C16 1.493(12) . ?
C15 C13 1.507(12) 2_556 ?
C15 H15 0.9800 . ?
C16 C16 1.382(16) 2_556 ?
C16 C17 1.411(12) . ?
C17 C18 1.366(12) . ?
C17 H17 0.9300 . ?
C18 C18 1.377(15) 2_556 ?
C19 N3 1.344(10) 2_556 ?
C19 C20 1.37(2) . ?
C20 C21 1.396(15) 2_556 ?
C20 C21 1.396(15) . ?
C21 C22 1.37(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.346(16) . ?
C22 H22 0.9300 . ?
C23 C22 1.346(16) 2_556 ?
C23 C24 1.45(4) . ?
C24 O3 1.186(19) 2_556 ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
Cd1 O6A 2.22(2) . ?
Cd1 O2 2.242(15) 2_655 ?
Cd1 O5A 2.35(2) . ?
Cd1 O3 2.374(15) 3_544 ?
Cd2 O3 2.034(15) 3_544 ?
Cd2 Cd2 2.08(3) 2_655 ?
Cd2 O2 2.119(17) 2_655 ?
Cd2 O1 2.43(2) 2_655 ?
Cd2 C1 2.687(17) 2_655 ?
Cd2 O6B 2.73(4) . ?
Cd2 O5B 3.44(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 Cd2 148(2) . . ?
C1 O1 Cd1 172.4(19) . . ?
C1 O1 Cd2 92.8(17) . 2_655 ?
Cd2 O1 Cd2 55.6(8) . 2_655 ?
O4 S1 C25 96.6(15) . . ?
O4 S1 C26 145.5(17) . . ?
C25 S1 C26 117.1(18) . . ?
C8 N1 C10 106.0(8) . . ?
C8 N1 H1 127.0 . . ?
C10 N1 H1 127.0 . . ?
O1 C1 O2 115.7(18) . . ?
O1 C1 C2 133(3) . . ?
O2 C1 C2 112(2) . . ?
O1 C1 Cd2 64.7(13) . 2_655 ?
O2 C1 Cd2 51.2(9) . 2_655 ?
C2 C1 Cd2 163(2) . 2_655 ?
C1 O2 Cd2 98.7(14) . 2_655 ?
C1 O2 Cd1 125.8(14) . 2_655 ?
C8 N2 C9 107.2(8) . . ?
C7 C2 C3 122.3(17) . . ?
C7 C2 C1 115(2) . . ?
C3 C2 C1 123(2) . . ?
C24 O3 Cd2 121(3) . 3_455 ?
C24 O3 Cd1 143(2) . 3_455 ?
C19 N3 C18 106.0(8) . . ?
C2 C3 C4 119.8(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.3(15) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 116.8(14) . . ?
C6 C5 C8 122.3(12) . . ?
C4 C5 C8 120.8(13) . . ?
C5 C6 C7 122.4(15) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C2 C7 C6 118.3(14) . . ?
C2 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
N2 C8 N1 112.6(9) . . ?
N2 C8 C5 125.0(12) . . ?
N1 C8 C5 122.4(11) . . ?
C10 C9 C14 123.2(9) . . ?
C10 C9 N2 105.6(9) . . ?
C14 C9 N2 131.1(10) . . ?
N1 C10 C11 131.7(10) . . ?
N1 C10 C9 108.5(9) . . ?
C11 C10 C9 119.9(9) . . ?
C12 C11 C10 117.5(8) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C11 C12 C13 122.5(8) . . ?
C11 C12 C15 125.3(9) . . ?
C13 C12 C15 112.1(8) . . ?
C14 C13 C12 120.8(8) . . ?
C14 C13 C15 125.1(9) . 2_556 ?
C12 C13 C15 114.1(9) . 2_556 ?
C13 C14 C9 116.0(9) . . ?
C13 C14 H14 122.0 . . ?
C9 C14 H14 122.0 . . ?
C16 C15 C13 106.0(6) . 2_556 ?
C16 C15 C12 104.0(7) . . ?
C13 C15 C12 105.3(7) 2_556 . ?
C16 C15 H15 113.6 . . ?
C13 C15 H15 113.6 2_556 . ?
C12 C15 H15 113.6 . . ?
C16 C16 C17 120.8(5) 2_556 . ?
C16 C16 C15 114.5(5) 2_556 . ?
C17 C16 C15 124.7(7) . . ?
C18 C17 C16 117.1(8) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C17 C18 C18 122.1(5) . 2_556 ?
C17 C18 N3 130.1(8) . . ?
C18 C18 N3 107.8(4) 2_556 . ?
N3 C19 N3 112.3(13) 2_556 . ?
N3 C19 C20 123.9(6) 2_556 . ?
N3 C19 C20 123.9(6) . . ?
C19 C20 C21 123.4(8) . 2_556 ?
C19 C20 C21 123.4(8) . . ?
C21 C20 C21 113.2(17) 2_556 . ?
C22 C21 C20 123.2(14) . . ?
C22 C21 H21 118.4 . . ?
C20 C21 H21 118.4 . . ?
C23 C22 C21 120.8(15) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C22 119(2) 2_556 . ?
C22 C23 C24 120.6(10) 2_556 . ?
C22 C23 C24 120.6(10) . . ?
O3 C24 O3 117(4) 2_556 . ?
O3 C24 C23 122(2) 2_556 . ?
O3 C24 C23 122(2) . . ?
S1 C26 H26A 109.5 . . ?
S1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
S1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O6A Cd1 O2 81.9(8) . 2_655 ?
O6A Cd1 O1 169.3(8) . . ?
O2 Cd1 O1 100.2(7) 2_655 . ?
O6A Cd1 O5A 83.7(8) . . ?
O2 Cd1 O5A 165.6(9) 2_655 . ?
O1 Cd1 O5A 94.1(7) . . ?
O6A Cd1 O3 91.2(7) . 3_544 ?
O2 Cd1 O3 97.5(6) 2_655 3_544 ?
O1 Cd1 O3 98.9(7) . 3_544 ?
O5A Cd1 O3 82.5(6) . 3_544 ?
O1 Cd2 O3 127.4(8) . 3_544 ?
O1 Cd2 Cd2 75.0(8) . 2_655 ?
O3 Cd2 Cd2 88.2(7) 3_544 2_655 ?
O1 Cd2 O2 118.7(8) . 2_655 ?
O3 Cd2 O2 113.4(7) 3_544 2_655 ?
Cd2 Cd2 O2 101.9(7) 2_655 2_655 ?
O1 Cd2 O1 98.6(8) . 2_655 ?
O3 Cd2 O1 107.2(7) 3_544 2_655 ?
Cd2 Cd2 O1 49.4(5) 2_655 2_655 ?
O2 Cd2 O1 52.6(6) 2_655 2_655 ?
O1 Cd2 C1 110.3(7) . 2_655 ?
O3 Cd2 C1 110.8(6) 3_544 2_655 ?
Cd2 Cd2 C1 71.8(7) 2_655 2_655 ?
O2 Cd2 C1 30.1(7) 2_655 2_655 ?
O1 Cd2 C1 22.5(5) 2_655 2_655 ?
O1 Cd2 O6B 103.8(9) . . ?
O3 Cd2 O6B 92.4(7) 3_544 . ?
Cd2 Cd2 O6B 178.9(5) 2_655 . ?
O2 Cd2 O6B 78.7(9) 2_655 . ?
O1 Cd2 O6B 131.2(7) 2_655 . ?
C1 Cd2 O6B 108.8(8) 2_655 . ?
O1 Cd2 O5B 72.6(6) . . ?
O3 Cd2 O5B 66.1(5) 3_544 . ?
Cd2 Cd2 O5B 108.3(6) 2_655 . ?
O2 Cd2 O5B 149.7(10) 2_655 . ?
O1 Cd2 O5B 157.6(8) 2_655 . ?
C1 Cd2 O5B 176.8(5) 2_655 . ?
O6B Cd2 O5B 71.1(8) . . ?
S1 C25 H25A 109.5 . . ?
S1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         1.092
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.152

####################################################################### 
# 
# 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_Cd_TPA
_database_code_depnum_ccdc_archive 'CCDC 1432465'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Tripticene triacid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H13 Br Cd N3 O7'
_chemical_formula_sum            'C25 H13 Br Cd N3 O7'
_chemical_formula_weight         659.69

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'
Br Br -0.2901 2.4595 '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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   13.9438(15)
_cell_length_b                   42.307(6)
_cell_length_c                   16.9583(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.249(7)
_cell_angle_gamma                90
_cell_volume                     9696(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    150
_cell_measurement_theta_min      5
_cell_measurement_theta_max      20

_exptl_crystal_description       square
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.904
_exptl_crystal_F_000             2584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.300
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            78947
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.087
_diffrn_reflns_theta_max         25.172
_diffrn_reflns_theta_full        25.172
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8696
_reflns_number_gt                5070
_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_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.2000P)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         8696
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2267
_refine_ls_R_factor_gt           0.1802
_refine_ls_wR_factor_ref         0.5026
_refine_ls_wR_factor_gt          0.4784
_refine_ls_goodness_of_fit_ref   1.840
_refine_ls_restrained_S_all      1.840
_refine_ls_shift/su_max          0.014
_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
C1 C -0.6399(14) 0.1701(3) 0.4267(10) 0.115(5) Uani 1 1 d . . . . .
C2 C -0.5851(9) 0.1514(2) 0.3738(7) 0.086(3) Uani 1 1 d . . . . .
C3 C -0.6379(8) 0.1395(3) 0.2987(9) 0.109(4) Uani 1 1 d . . . . .
H3 H -0.7062 0.1420 0.2824 0.131 Uiso 1 1 calc R U . . .
C4 C -0.5909(7) 0.1248(3) 0.2511(6) 0.089(3) Uani 1 1 d . . . . .
H4 H -0.6273 0.1178 0.2006 0.107 Uiso 1 1 calc R U . . .
C5 C -0.4900(6) 0.1191(2) 0.2724(5) 0.059(2) Uani 1 1 d . . . . .
C6 C -0.4424(9) 0.1313(3) 0.3394(8) 0.107(4) Uani 1 1 d . . . . .
H6 H -0.3736 0.1303 0.3534 0.128 Uiso 1 1 calc R U . . .
C7 C -0.4923(10) 0.1467(3) 0.3943(7) 0.109(4) Uani 1 1 d . . . . .
H7 H -0.4559 0.1533 0.4452 0.131 Uiso 1 1 calc R U . . .
C8 C -0.4415(5) 0.10228(18) 0.2179(5) 0.053(2) Uani 1 1 d . . . . .
C9 C -0.4172(5) 0.07755(16) 0.1116(4) 0.0428(16) Uani 1 1 d . . . . .
C10 C -0.4248(4) 0.06369(14) 0.0355(4) 0.0377(15) Uani 1 1 d . . . . .
H10 H -0.4841 0.0637 -0.0044 0.045 Uiso 1 1 calc R U . . .
C11 C -0.3417(4) 0.05013(15) 0.0224(4) 0.0359(15) Uani 1 1 d . . . . .
C12 C -0.2508(4) 0.05104(16) 0.0831(4) 0.0377(15) Uani 1 1 d . . . . .
C13 C -0.2412(5) 0.06470(16) 0.1573(4) 0.0428(17) Uani 1 1 d . . . . .
H13 H -0.1813 0.0649 0.1965 0.051 Uiso 1 1 calc R U . . .
C14 C -0.3268(4) 0.07845(16) 0.1712(4) 0.0399(16) Uani 1 1 d . . . . .
C15 C -0.3315(4) 0.03376(15) -0.0551(4) 0.0351(15) Uani 1 1 d . . . . .
H15 H -0.3939 0.0338 -0.0972 0.042 Uiso 1 1 calc R U . . .
C16 C -0.2958(4) 0.00027(15) -0.0307(4) 0.0334(15) Uani 1 1 d . . . . .
C17 C -0.3427(4) -0.02661(16) -0.0597(4) 0.0371(16) Uani 1 1 d . . . . .
H17 H -0.4032 -0.0266 -0.0980 0.045 Uiso 1 1 calc R U . . .
C18 C -0.2947(4) -0.05446(16) -0.0287(4) 0.0380(16) Uani 1 1 d . . . . .
C19 C -0.2500 -0.1033(2) 0.0000 0.042(2) Uani 1 2 d S T P . .
C20 C -0.2500 -0.1385(2) 0.0000 0.055(3) Uani 1 2 d S T P . .
C21 C -0.1678(9) -0.1545(2) 0.0335(7) 0.098(4) Uani 1 1 d . . . . .
H21 H -0.1097 -0.1435 0.0552 0.118 Uiso 1 1 calc R U . . .
C22 C -0.1665(10) -0.1879(3) 0.0370(7) 0.105(4) Uani 1 1 d . . . . .
H22 H -0.1098 -0.1987 0.0640 0.126 Uiso 1 1 calc R U . . .
C23 C -0.2500 -0.2038(3) 0.0000 0.098(6) Uani 1 2 d S T P . .
C24 C -0.2500 -0.2378(4) 0.0000 0.110(6) Uani 1 2 d S T P . .
C25 C 0.0933(10) 0.0611(4) 0.1883(9) 0.095(3) Uani 0.5 1 d G . P . .
C26 C 0.1267(10) 0.0334(4) 0.1647(9) 0.095(3) Uani 0.5 1 d G . P . .
H26 H 0.1663 0.0334 0.1279 0.114 Uiso 0.5 1 calc R U P . .
C27 C 0.1022(10) 0.0056(4) 0.1949(9) 0.095(3) Uani 0.5 1 d G . P . .
H27 H 0.1251 -0.0134 0.1788 0.114 Uiso 0.5 1 calc R U P . .
C28 C 0.0444(10) 0.0056(4) 0.2488(9) 0.095(3) Uani 0.5 1 d G . P . .
C29 C 0.0110(9) 0.0333(4) 0.2723(9) 0.095(3) Uani 0.5 1 d G . P . .
H29 H -0.0286 0.0333 0.3092 0.114 Uiso 0.5 1 calc R U P . .
C30 C 0.0355(10) 0.0611(4) 0.2421(9) 0.095(3) Uani 0.5 1 d G . P . .
H30 H 0.0126 0.0801 0.2583 0.114 Uiso 0.5 1 calc R U P . .
Br1 Br 0.0060(3) -0.03195(8) 0.29087(19) 0.1379(12) Uani 0.5 1 d . . P . .
Br2 Br 0.1263(2) 0.10160(8) 0.1505(2) 0.1319(12) Uani 0.5 1 d . . P . .
N1 N -0.3438(4) 0.09355(15) 0.2376(3) 0.0513(16) Uani 1 1 d . . . . .
N2 N -0.4857(4) 0.09313(14) 0.1436(4) 0.0455(15) Uani 1 1 d . . . . .
H2 H -0.5468 0.0963 0.1193 0.055 Uiso 1 1 calc R U . . .
N3 N -0.3218(4) -0.08577(13) -0.0459(3) 0.0427(14) Uani 1 1 d . . . . .
O1 O -0.5881(8) 0.1774(3) 0.4971(7) 0.149(4) Uani 1 1 d . . . . .
O2 O -0.7261(10) 0.1750(3) 0.4012(6) 0.181(6) Uani 1 1 d . . . . .
O4 O -0.1936(12) 0.0990(4) 0.3783(9) 0.241(8) Uani 1 1 d . . . . .
Cd2 Cd -0.86126(15) 0.20073(4) 0.40409(15) 0.1106(9) Uani 0.662(4) 1 d . . P A
1
O6A O -0.9622(9) 0.1861(3) 0.3190(7) 0.1106(9) Uani 0.662(4) 1 d . . P A 1
O7A O -0.8297(10) 0.2183(3) 0.2828(8) 0.1106(9) Uani 0.662(4) 1 d . . P A 1
Cd1 Cd -0.7852(4) 0.20119(6) 0.4698(3) 0.116(3) Uani 0.338(4) 1 d . . P A 2
O6B O -0.994(2) 0.2104(6) 0.3409(14) 0.116(3) Uani 0.338(4) 1 d . . P A 2
O7B O -0.919(2) 0.2123(5) 0.2349(14) 0.116(3) Uani 0.338(4) 1 d . . P A 2
O5 O -0.3682(11) 0.1719(3) 0.1479(11) 0.224(7) Uani 1 1 d . . . . .
O3 O -0.3171(12) -0.25243(19) -0.0315(10) 0.203(7) 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
C1 O2 1.191(18) . ?
C1 O1 1.271(18) . ?
C1 C2 1.535(15) . ?
C1 Cd1 2.607(11) 2_356 ?
C1 Cd1 2.664(13) . ?
C2 C7 1.270(15) . ?
C2 C3 1.399(16) . ?
C3 C4 1.314(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.276(13) . ?
C5 C8 1.458(10) . ?
C6 C7 1.446(15) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.317(9) . ?
C8 N1 1.370(9) . ?
C9 N2 1.378(8) . ?
C9 C10 1.398(9) . ?
C9 C14 1.408(9) . ?
C10 C11 1.360(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.423(9) . ?
C11 C15 1.523(9) . ?
C12 C13 1.362(9) . ?
C12 C15 1.531(8) 2_455 ?
C13 C14 1.398(9) . ?
C13 H13 0.9300 . ?
C14 N1 1.366(8) . ?
C15 C16 1.525(9) . ?
C15 C12 1.531(8) 2_455 ?
C15 H15 0.9800 . ?
C16 C17 1.343(9) . ?
C16 C16 1.435(12) 2_455 ?
C17 C18 1.393(10) . ?
C17 H17 0.9300 . ?
C18 C18 1.378(12) 2_455 ?
C18 N3 1.389(9) . ?
C19 N3 1.331(8) 2_455 ?
C19 N3 1.331(8) . ?
C19 C20 1.489(14) . ?
C20 C21 1.333(11) 2_455 ?
C20 C21 1.333(11) . ?
C21 C22 1.412(16) . ?
C21 H21 0.9300 . ?
C22 C23 1.356(14) . ?
C22 H22 0.9300 . ?
C23 C22 1.356(14) 2_455 ?
C23 C24 1.44(2) . ?
C24 O3 1.138(13) . ?
C24 O3 1.138(13) 2_455 ?
C24 Cd1 2.652(15) 3_544 ?
C24 Cd1 2.652(15) 4_345 ?
C25 C30 1.358(9) . ?
C25 C26 1.358(9) . ?
C25 Br2 1.925(15) . ?
C26 C27 1.358(9) . ?
C26 H26 0.9300 . ?
C27 C28 1.358(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.358(9) . ?
C28 Br1 1.873(16) . ?
C29 C30 1.358(9) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
N2 H2 0.8600 . ?
O1 Cd2 2.206(8) 2_356 ?
O1 Cd1 2.221(9) 2_356 ?
O2 Cd1 1.932(9) . ?
O2 Cd2 2.187(10) . ?
O2 Cd1 2.422(11) 2_356 ?
Cd2 O6A 1.856(13) . ?
Cd2 O1 2.206(8) 2_356 ?
Cd2 O3 2.273(11) 3_455 ?
Cd2 O7A 2.328(11) . ?
Cd1 Cd1 1.232(12) 2_356 ?
Cd1 O3 2.011(9) 3_455 ?
Cd1 O1 2.222(9) 2_356 ?
Cd1 O2 2.422(11) 2_356 ?
Cd1 O3 2.499(13) 4_355 ?
Cd1 C1 2.607(11) 2_356 ?
Cd1 C24 2.652(15) 3_455 ?
Cd1 O6B 3.20(3) . ?
Cd1 O7B 3.99(3) . ?
O3 Cd1 2.011(9) 3_544 ?
O3 Cd2 2.273(11) 3_544 ?
O3 Cd1 2.499(13) 4_345 ?

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 C1 O1 126.1(12) . . ?
O2 C1 C2 118.7(16) . . ?
O1 C1 C2 115.1(15) . . ?
O2 C1 Cd1 67.8(7) . 2_356 ?
O1 C1 Cd1 58.4(6) . 2_356 ?
C2 C1 Cd1 173.4(13) . 2_356 ?
O2 C1 Cd1 41.1(7) . . ?
O1 C1 Cd1 85.3(7) . . ?
C2 C1 Cd1 159.5(13) . . ?
Cd1 C1 Cd1 27.0(3) 2_356 . ?
C7 C2 C3 117.7(10) . . ?
C7 C2 C1 122.8(14) . . ?
C3 C2 C1 119.5(12) . . ?
C4 C3 C2 119.9(10) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 123.4(10) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C6 C5 C4 115.7(8) . . ?
C6 C5 C8 122.8(8) . . ?
C4 C5 C8 121.3(7) . . ?
C5 C6 C7 121.9(11) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C2 C7 C6 120.9(11) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N2 C8 N1 110.9(6) . . ?
N2 C8 C5 124.6(6) . . ?
N1 C8 C5 124.4(7) . . ?
N2 C9 C10 131.5(6) . . ?
N2 C9 C14 106.8(6) . . ?
C10 C9 C14 121.7(6) . . ?
C11 C10 C9 117.0(6) . . ?
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C10 C11 C12 120.9(6) . . ?
C10 C11 C15 126.6(6) . . ?
C12 C11 C15 112.4(5) . . ?
C13 C12 C11 123.2(6) . . ?
C13 C12 C15 125.3(6) . 2_455 ?
C11 C12 C15 111.4(5) . 2_455 ?
C12 C13 C14 116.0(6) . . ?
C12 C13 H13 122.0 . . ?
C14 C13 H13 122.0 . . ?
N1 C14 C13 131.4(6) . . ?
N1 C14 C9 107.3(5) . . ?
C13 C14 C9 121.2(6) . . ?
C11 C15 C16 106.4(5) . . ?
C11 C15 C12 106.6(5) . 2_455 ?
C16 C15 C12 107.9(5) . 2_455 ?
C11 C15 H15 111.9 . . ?
C16 C15 H15 111.9 . . ?
C12 C15 H15 111.9 2_455 . ?
C17 C16 C16 122.1(4) . 2_455 ?
C17 C16 C15 126.2(5) . . ?
C16 C16 C15 111.7(3) 2_455 . ?
C16 C17 C18 115.6(5) . . ?
C16 C17 H17 122.2 . . ?
C18 C17 H17 122.2 . . ?
C18 C18 N3 107.5(3) 2_455 . ?
C18 C18 C17 122.2(4) 2_455 . ?
N3 C18 C17 130.3(6) . . ?
N3 C19 N3 112.4(9) 2_455 . ?
N3 C19 C20 123.8(4) 2_455 . ?
N3 C19 C20 123.8(4) . . ?
C21 C20 C21 118.7(12) 2_455 . ?
C21 C20 C19 120.7(6) 2_455 . ?
C21 C20 C19 120.7(6) . . ?
C20 C21 C22 121.9(11) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 118.3(12) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C22 C23 C22 120.7(15) 2_455 . ?
C22 C23 C24 119.7(7) 2_455 . ?
C22 C23 C24 119.7(7) . . ?
O3 C24 O3 114.3(18) . 2_455 ?
O3 C24 C23 122.8(9) . . ?
O3 C24 C23 122.8(9) 2_455 . ?
O3 C24 Cd1 44.8(9) . 3_544 ?
O3 C24 Cd1 69.8(10) 2_455 3_544 ?
C23 C24 Cd1 166.57(15) . 3_544 ?
O3 C24 Cd1 69.8(10) . 4_345 ?
O3 C24 Cd1 44.8(9) 2_455 4_345 ?
C23 C24 Cd1 166.57(15) . 4_345 ?
Cd1 C24 Cd1 26.9(3) 3_544 4_345 ?
C30 C25 C26 120.0 . . ?
C30 C25 Br2 117.1(8) . . ?
C26 C25 Br2 122.9(8) . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 120.0 . . ?
C27 C28 Br1 122.0(8) . . ?
C29 C28 Br1 118.0(8) . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C25 120.0 . . ?
C29 C30 H30 120.0 . . ?
C25 C30 H30 120.0 . . ?
C14 N1 C8 106.8(6) . . ?
C8 N2 C9 108.1(5) . . ?
C8 N2 H2 126.0 . . ?
C9 N2 H2 126.0 . . ?
C19 N3 C18 106.3(6) . . ?
C1 O1 Cd2 127.4(9) . 2_356 ?
C1 O1 Cd1 92.5(9) . 2_356 ?
C1 O2 Cd1 115.0(11) . . ?
C1 O2 Cd2 151.2(12) . . ?
C1 O2 Cd1 85.1(9) . 2_356 ?
Cd1 O2 Cd1 30.3(3) . 2_356 ?
O6A Cd2 O2 108.0(6) . . ?
O6A Cd2 O1 96.8(5) . 2_356 ?
O2 Cd2 O1 103.4(4) . 2_356 ?
O6A Cd2 O3 136.7(6) . 3_455 ?
O2 Cd2 O3 108.1(6) . 3_455 ?
O1 Cd2 O3 97.2(5) 2_356 3_455 ?
O6A Cd2 O7A 72.0(5) . . ?
O2 Cd2 O7A 77.8(4) . . ?
O1 Cd2 O7A 168.4(5) 2_356 . ?
O3 Cd2 O7A 93.3(5) 3_455 . ?
Cd1 Cd1 O2 97.4(5) 2_356 . ?
Cd1 Cd1 O3 98.0(5) 2_356 3_455 ?
O2 Cd1 O3 132.7(6) . 3_455 ?
Cd1 Cd1 O1 108.1(4) 2_356 2_356 ?
O2 Cd1 O1 112.1(6) . 2_356 ?
O3 Cd1 O1 105.0(5) 3_455 2_356 ?
Cd1 Cd1 O2 52.3(3) 2_356 2_356 ?
O2 Cd1 O2 109.8(7) . 2_356 ?
O3 Cd1 O2 115.0(6) 3_455 2_356 ?
O1 Cd1 O2 56.2(4) 2_356 2_356 ?
Cd1 Cd1 O3 52.8(3) 2_356 4_355 ?
O2 Cd1 O3 114.7(6) . 4_355 ?
O3 Cd1 O3 48.7(8) 3_455 4_355 ?
O1 Cd1 O3 131.1(5) 2_356 4_355 ?
O2 Cd1 O3 94.4(5) 2_356 4_355 ?
Cd1 Cd1 C1 79.1(5) 2_356 2_356 ?
O2 Cd1 C1 114.7(5) . 2_356 ?
O3 Cd1 C1 112.1(5) 3_455 2_356 ?
O1 Cd1 C1 29.1(5) 2_356 2_356 ?
O2 Cd1 C1 27.1(4) 2_356 2_356 ?
O3 Cd1 C1 113.3(5) 4_355 2_356 ?
Cd1 Cd1 C24 76.58(15) 2_356 3_455 ?
O2 Cd1 C24 126.0(5) . 3_455 ?
O3 Cd1 C24 23.5(5) 3_455 3_455 ?
O1 Cd1 C24 120.9(3) 2_356 3_455 ?
O2 Cd1 C24 107.6(3) 2_356 3_455 ?
O3 Cd1 C24 25.3(3) 4_355 3_455 ?
C1 Cd1 C24 116.5(3) 2_356 3_455 ?
Cd1 Cd1 C1 73.9(5) 2_356 . ?
O2 Cd1 C1 23.9(5) . . ?
O3 Cd1 C1 131.2(5) 3_455 . ?
O1 Cd1 C1 123.4(4) 2_356 . ?
O2 Cd1 C1 97.9(5) 2_356 . ?
O3 Cd1 C1 96.2(5) 4_355 . ?
C1 Cd1 C1 113.2(5) 2_356 . ?
C24 Cd1 C1 114.5(3) 3_455 . ?
Cd1 Cd1 O6B 166.3(5) 2_356 . ?
O2 Cd1 O6B 96.3(6) . . ?
O3 Cd1 O6B 73.3(6) 3_455 . ?
O1 Cd1 O6B 65.4(5) 2_356 . ?
O2 Cd1 O6B 121.2(5) 2_356 . ?
O3 Cd1 O6B 121.3(5) 4_355 . ?
C1 Cd1 O6B 94.3(6) 2_356 . ?
C24 Cd1 O6B 96.2(4) 3_455 . ?
C1 Cd1 O6B 119.8(6) . . ?
Cd1 Cd1 O7B 155.7(5) 2_356 . ?
O2 Cd1 O7B 68.4(5) . . ?
O3 Cd1 O7B 79.9(6) 3_455 . ?
O1 Cd1 O7B 95.7(5) 2_356 . ?
O2 Cd1 O7B 150.0(5) 2_356 . ?
O3 Cd1 O7B 113.9(5) 4_355 . ?
C1 Cd1 O7B 124.3(6) 2_356 . ?
C24 Cd1 O7B 95.6(3) 3_455 . ?
C1 Cd1 O7B 89.2(5) . . ?
O6B Cd1 O7B 34.9(5) . . ?
C24 O3 Cd1 111.7(13) . 3_544 ?
C24 O3 Cd2 142.4(12) . 3_544 ?
C24 O3 Cd1 84.9(12) . 4_345 ?
Cd1 O3 Cd1 29.2(3) 3_544 4_345 ?

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
O2 C1 C2 C7 175.9(14) . . . . ?
O1 C1 C2 C7 -8.1(17) . . . . ?
Cd1 C1 C2 C7 168.2(17) . . . . ?
O2 C1 C2 C3 -2.6(17) . . . . ?
O1 C1 C2 C3 173.4(12) . . . . ?
Cd1 C1 C2 C3 -10(3) . . . . ?
C7 C2 C3 C4 -2(2) . . . . ?
C1 C2 C3 C4 176.7(11) . . . . ?
C2 C3 C4 C5 3(2) . . . . ?
C3 C4 C5 C6 -5.4(19) . . . . ?
C3 C4 C5 C8 179.1(12) . . . . ?
C4 C5 C6 C7 7.4(18) . . . . ?
C8 C5 C6 C7 -177.2(11) . . . . ?
C3 C2 C7 C6 4(2) . . . . ?
C1 C2 C7 C6 -174.6(11) . . . . ?
C5 C6 C7 C2 -7(2) . . . . ?
C6 C5 C8 N2 -170.2(10) . . . . ?
C4 C5 C8 N2 4.9(14) . . . . ?
C6 C5 C8 N1 10.5(15) . . . . ?
C4 C5 C8 N1 -174.3(9) . . . . ?
N2 C9 C10 C11 179.5(7) . . . . ?
C14 C9 C10 C11 2.2(9) . . . . ?
C9 C10 C11 C12 -1.8(9) . . . . ?
C9 C10 C11 C15 -179.8(6) . . . . ?
C10 C11 C12 C13 1.2(10) . . . . ?
C15 C11 C12 C13 179.4(6) . . . . ?
C10 C11 C12 C15 178.9(6) . . . 2_455 ?
C15 C11 C12 C15 -2.8(7) . . . 2_455 ?
C11 C12 C13 C14 -0.7(10) . . . . ?
C15 C12 C13 C14 -178.1(6) 2_455 . . . ?
C12 C13 C14 N1 179.2(7) . . . . ?
C12 C13 C14 C9 1.0(10) . . . . ?
N2 C9 C14 N1 1.8(7) . . . . ?
C10 C9 C14 N1 179.6(6) . . . . ?
N2 C9 C14 C13 -179.7(6) . . . . ?
C10 C9 C14 C13 -1.8(10) . . . . ?
C10 C11 C15 C16 -122.5(6) . . . . ?
C12 C11 C15 C16 59.4(6) . . . . ?
C10 C11 C15 C12 122.5(6) . . . 2_455 ?
C12 C11 C15 C12 -55.6(6) . . . 2_455 ?
C11 C15 C16 C17 120.6(6) . . . . ?
C12 C15 C16 C17 -125.3(6) 2_455 . . . ?
C11 C15 C16 C16 -57.7(7) . . . 2_455 ?
C12 C15 C16 C16 56.4(7) 2_455 . . 2_455 ?
C16 C16 C17 C18 -2.5(10) 2_455 . . . ?
C15 C16 C17 C18 179.3(5) . . . . ?
C16 C17 C18 C18 0.6(10) . . . 2_455 ?
C16 C17 C18 N3 -179.3(6) . . . . ?
N3 C19 C20 C21 165.7(7) 2_455 . . 2_455 ?
N3 C19 C20 C21 -14.3(7) . . . 2_455 ?
N3 C19 C20 C21 -14.3(7) 2_455 . . . ?
N3 C19 C20 C21 165.7(7) . . . . ?
C21 C20 C21 C22 -2.3(9) 2_455 . . . ?
C19 C20 C21 C22 177.7(9) . . . . ?
C20 C21 C22 C23 4.6(19) . . . . ?
C21 C22 C23 C22 -2.2(9) . . . 2_455 ?
C21 C22 C23 C24 177.8(9) . . . . ?
C22 C23 C24 O3 1.8(12) 2_455 . . . ?
C22 C23 C24 O3 -178.2(12) . . . . ?
C22 C23 C24 O3 -178.2(12) 2_455 . . 2_455 ?
C22 C23 C24 O3 1.8(12) . . . 2_455 ?
C22 C23 C24 Cd1 22.6(7) 2_455 . . 3_544 ?
C22 C23 C24 Cd1 -157.4(7) . . . 3_544 ?
C22 C23 C24 Cd1 -157.4(7) 2_455 . . 4_345 ?
C22 C23 C24 Cd1 22.6(7) . . . 4_345 ?
C30 C25 C26 C27 0.0 . . . . ?
Br2 C25 C26 C27 178.7(11) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C26 C27 C28 Br1 178.7(11) . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
Br1 C28 C29 C30 -178.7(10) . . . . ?
C28 C29 C30 C25 0.0 . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
Br2 C25 C30 C29 -178.8(10) . . . . ?
C13 C14 N1 C8 -179.9(7) . . . . ?
C9 C14 N1 C8 -1.5(8) . . . . ?
N2 C8 N1 C14 0.7(9) . . . . ?
C5 C8 N1 C14 -180.0(8) . . . . ?
N1 C8 N2 C9 0.4(9) . . . . ?
C5 C8 N2 C9 -178.9(8) . . . . ?
C10 C9 N2 C8 -179.0(7) . . . . ?
C14 C9 N2 C8 -1.3(8) . . . . ?
N3 C19 N3 C18 0.1(3) 2_455 . . . ?
C20 C19 N3 C18 -179.9(3) . . . . ?
C18 C18 N3 C19 -0.2(7) 2_455 . . . ?
C17 C18 N3 C19 179.7(5) . . . . ?
O2 C1 O1 Cd2 1(2) . . . 2_356 ?
C2 C1 O1 Cd2 -175.0(7) . . . 2_356 ?
O2 C1 O1 Cd1 -3.5(16) . . . 2_356 ?
C2 C1 O1 Cd1 -179.1(8) . . . 2_356 ?
Cd1 C1 O1 Cd1 2.1(4) . . . 2_356 ?
O1 C1 O2 Cd1 9(2) . . . . ?
C2 C1 O2 Cd1 -176.0(8) . . . . ?
Cd1 C1 O2 Cd1 5.3(6) 2_356 . . . ?
O1 C1 O2 Cd2 21(3) . . . . ?
C2 C1 O2 Cd2 -163.3(17) . . . . ?
O1 C1 O2 Cd1 3.2(15) . . . 2_356 ?
C2 C1 O2 Cd1 178.7(9) . . . 2_356 ?
Cd1 C1 O2 Cd1 -5.3(6) . . . 2_356 ?
O3 C24 O3 Cd1 -6.7(3) 2_455 . . 3_544 ?
C23 C24 O3 Cd1 173.3(3) . . . 3_544 ?
Cd1 C24 O3 Cd1 -11.8(5) 4_345 . . 3_544 ?
O3 C24 O3 Cd2 -30.4(13) 2_455 . . 3_544 ?
C23 C24 O3 Cd2 149.6(13) . . . 3_544 ?
O3 C24 O3 Cd1 5.0(2) 2_455 . . 4_345 ?
C23 C24 O3 Cd1 -175.0(2) . . . 4_345 ?
Cd1 C24 O3 Cd1 11.8(5) 3_544 . . 4_345 ?

_refine_diff_density_max         1.726
_refine_diff_density_min         -1.664
_refine_diff_density_rms         0.186

