# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1856754'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5,6-dioxophenanthriporphyrin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H26 N2 O2'
_chemical_formula_weight         602.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.516(3)
_cell_length_b                   11.551(6)
_cell_length_c                   13.616(7)
_cell_angle_alpha                91.24(4)
_cell_angle_beta                 106.05(4)
_cell_angle_gamma                99.94(3)
_cell_volume                     1412.9(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    415
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      78.49

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.685
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.982
_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     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.20
_diffrn_reflns_number            8357
_diffrn_reflns_av_unetI/netI     0.4114
_diffrn_reflns_av_R_equivalents  0.2960
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.387
_diffrn_reflns_theta_max         74.468
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             4981
_reflns_number_gt                1131
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0086P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4981
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3027
_refine_ls_R_factor_gt           0.1221
_refine_ls_wR_factor_ref         0.3452
_refine_ls_wR_factor_gt          0.2214
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.895
_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 -0.0844(10) -0.0623(10) 0.7556(9) 0.032(3) Uani 1 1 d . . . . .
C2 C 0.0168(11) -0.0035(10) 0.8469(10) 0.042(3) Uani 1 1 d . . . . .
H2A H 0.0095 -0.0285 0.9116 0.051 Uiso 1 1 calc R U . . .
C3 C 0.1276(12) 0.0914(11) 0.8420(9) 0.045(3) Uani 1 1 d . . . . .
H3A H 0.2036 0.1229 0.9026 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1278(11) 0.1400(10) 0.7495(9) 0.036(3) Uani 1 1 d . . . . .
O5 O 0.3556(8) 0.2779(8) 0.8170(7) 0.053(3) Uani 1 1 d . . . . .
C5 C 0.2468(12) 0.2394(10) 0.7430(10) 0.040(3) Uani 1 1 d . . . . .
O6 O 0.3253(8) 0.3845(7) 0.6407(7) 0.048(2) Uani 1 1 d . . . . .
C6 C 0.2344(10) 0.3007(11) 0.6428(9) 0.036(3) Uani 1 1 d . . . . .
C7 C 0.1099(11) 0.2481(10) 0.5553(9) 0.036(3) Uani 1 1 d . . . . .
C8 C 0.0904(11) 0.2968(10) 0.4605(9) 0.037(3) Uani 1 1 d . . . . .
H8A H 0.1654 0.3577 0.4509 0.045 Uiso 1 1 calc R U . . .
C9 C -0.0396(10) 0.2567(10) 0.3784(10) 0.040(3) Uani 1 1 d . . . . .
H9A H -0.0511 0.2908 0.3144 0.048 Uiso 1 1 calc R U . . .
C10 C -0.1498(11) 0.1679(10) 0.3911(9) 0.037(3) Uani 1 1 d . . . . .
C11 C -0.2935(10) 0.1252(11) 0.3117(9) 0.036(3) Uani 1 1 d . . . . .
C12 C -0.4011(11) 0.0331(11) 0.3152(10) 0.045(3) Uani 1 1 d . . . . .
C13 C -0.5451(11) 0.0004(10) 0.2390(9) 0.039(3) Uani 1 1 d . . . . .
H13A H -0.5800 0.0406 0.1795 0.047 Uiso 1 1 calc R U . . .
C14 C -0.6198(11) -0.0959(11) 0.2670(9) 0.043(3) Uani 1 1 d . . . . .
H14A H -0.7155 -0.1385 0.2306 0.051 Uiso 1 1 calc R U . . .
C15 C -0.5229(11) -0.1230(13) 0.3666(9) 0.044(3) Uani 1 1 d . . . . .
C16 C -0.5597(10) -0.2284(10) 0.4178(9) 0.035(3) Uani 1 1 d . . . . .
C17 C -0.4816(10) -0.2456(11) 0.5163(9) 0.036(3) Uani 1 1 d . . . . .
C18 C -0.4956(11) -0.3507(10) 0.5702(8) 0.041(3) Uani 1 1 d . . . . .
H18A H -0.5662 -0.4208 0.5439 0.049 Uiso 1 1 calc R U . . .
C19 C -0.3953(11) -0.3358(11) 0.6629(10) 0.042(3) Uani 1 1 d . . . . .
H19A H -0.3816 -0.3928 0.7123 0.050 Uiso 1 1 calc R U . . .
C20 C -0.3109(11) -0.2157(11) 0.6736(10) 0.040(3) Uani 1 1 d . . . . .
C21 C -0.1907(11) -0.1677(10) 0.7535(9) 0.033(3) Uani 1 1 d . . . . .
C22 C -0.0768(9) -0.0094(9) 0.6645(8) 0.029(3) Uani 1 1 d . . . . .
H22A H -0.1419 -0.0469 0.6016 0.035 Uiso 1 1 calc R U . . .
C23 C 0.0195(10) 0.0935(10) 0.6612(8) 0.032(3) Uani 1 1 d . . . . .
C24 C 0.0057(10) 0.1487(11) 0.5645(9) 0.039(3) Uani 1 1 d . . . . .
C25 C -0.1248(10) 0.1123(11) 0.4836(9) 0.041(3) Uani 1 1 d . . . . .
H25A H -0.1978 0.0487 0.4916 0.049 Uiso 1 1 calc R U . . .
N26 N -0.3940(9) -0.0458(9) 0.3924(7) 0.038(3) Uani 1 1 d . . . . .
N27 N -0.3657(9) -0.1670(9) 0.5829(7) 0.040(3) Uani 1 1 d . . . . .
H27 H -0.3479 -0.1102 0.5413 0.048 Uiso 1 1 d R U . . .
C27 C -0.0244(10) -0.2571(11) 0.9005(9) 0.036(3) Uani 1 1 d . . . . .
H27A H 0.0567 -0.2298 0.8739 0.043 Uiso 1 1 calc R U . . .
C28 C -0.3198(11) 0.2002(10) 0.2198(10) 0.041(3) Uani 1 1 d . . . . .
C29 C -0.3142(10) 0.3189(11) 0.2311(10) 0.043(3) Uani 1 1 d . . . . .
H29A H -0.2938 0.3573 0.2973 0.051 Uiso 1 1 calc R U . . .
C30 C -0.3391(10) 0.3837(12) 0.1431(11) 0.052(4) Uani 1 1 d . . . . .
H30A H -0.3351 0.4662 0.1512 0.063 Uiso 1 1 calc R U . . .
C31 C -0.3690(11) 0.3311(11) 0.0463(10) 0.045(3) Uani 1 1 d . . . . .
H31A H -0.3825 0.3772 -0.0114 0.054 Uiso 1 1 calc R U . . .
C32 C -0.3793(11) 0.2109(14) 0.0335(11) 0.056(4) Uani 1 1 d . . . . .
H32A H -0.4043 0.1731 -0.0334 0.067 Uiso 1 1 calc R U . . .
C33 C -0.3525(10) 0.1440(12) 0.1203(9) 0.043(3) Uani 1 1 d . . . . .
H33A H -0.3563 0.0615 0.1120 0.052 Uiso 1 1 calc R U . . .
C34 C -0.6866(11) -0.3189(12) 0.3601(9) 0.039(3) Uani 1 1 d . . . . .
C35 C -0.6904(11) -0.3698(11) 0.2636(10) 0.046(3) Uani 1 1 d . . . . .
H35A H -0.6088 -0.3477 0.2363 0.055 Uiso 1 1 calc R U . . .
C36 C -0.8097(11) -0.4497(11) 0.2105(10) 0.042(3) Uani 1 1 d . . . . .
H36A H -0.8123 -0.4827 0.1454 0.051 Uiso 1 1 calc R U . . .
C37 C -0.9304(11) -0.4844(10) 0.2508(10) 0.040(3) Uani 1 1 d . . . . .
H37A H -1.0149 -0.5395 0.2122 0.048 Uiso 1 1 calc R U . . .
C38 C -0.9263(11) -0.4399(11) 0.3433(10) 0.039(3) Uani 1 1 d . . . . .
H38A H -1.0082 -0.4640 0.3699 0.047 Uiso 1 1 calc R U . . .
C39 C -0.8028(11) -0.3580(12) 0.4017(10) 0.046(3) Uani 1 1 d . . . . .
H39A H -0.7987 -0.3299 0.4687 0.056 Uiso 1 1 calc R U . . .
C40 C -0.1646(10) -0.2347(10) 0.8504(8) 0.036(3) Uani 1 1 d . . . . .
C41 C -0.2827(10) -0.2746(9) 0.8923(9) 0.033(3) Uani 1 1 d . . . . .
H41A H -0.3793 -0.2592 0.8607 0.040 Uiso 1 1 calc R U . . .
C42 C -0.2579(12) -0.3357(11) 0.9788(9) 0.043(3) Uani 1 1 d . . . . .
H42A H -0.3381 -0.3621 1.0065 0.052 Uiso 1 1 calc R U . . .
C43 C -0.1183(11) -0.3600(11) 1.0268(10) 0.043(3) Uani 1 1 d . . . . .
H43A H -0.1028 -0.4047 1.0853 0.052 Uiso 1 1 calc R U . . .
C44 C -0.0007(11) -0.3165(10) 0.9862(9) 0.036(3) Uani 1 1 d . . . . .
H44A H 0.0968 -0.3290 1.0194 0.043 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
C1 C22 1.409(13) . ?
C1 C2 1.418(16) . ?
C1 C21 1.437(14) . ?
C2 C3 1.400(15) . ?
C2 H2A 0.9500 . ?
C3 C4 1.390(16) . ?
C3 H3A 0.9500 . ?
C4 C23 1.376(15) . ?
C4 C5 1.490(14) . ?
O5 C5 1.237(14) . ?
C5 C6 1.536(15) . ?
O6 C6 1.188(12) . ?
C6 C7 1.460(15) . ?
C7 C8 1.398(15) . ?
C7 C24 1.414(14) . ?
C8 C9 1.417(16) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(14) . ?
C9 H9A 0.9500 . ?
C10 C25 1.406(15) . ?
C10 C11 1.487(15) . ?
C11 C12 1.354(15) . ?
C11 C28 1.526(15) . ?
C12 N26 1.402(14) . ?
C12 C13 1.455(15) . ?
C13 C14 1.336(15) . ?
C13 H13A 0.9500 . ?
C14 C15 1.488(15) . ?
C14 H14A 0.9500 . ?
C15 N26 1.339(14) . ?
C15 C16 1.455(16) . ?
C16 C17 1.379(14) . ?
C16 C34 1.473(16) . ?
C17 N27 1.388(14) . ?
C17 C18 1.438(15) . ?
C18 C19 1.343(15) . ?
C18 H18A 0.9500 . ?
C19 C20 1.460(16) . ?
C19 H19A 0.9500 . ?
C20 C21 1.366(16) . ?
C20 N27 1.375(14) . ?
C21 C40 1.527(15) . ?
C22 C23 1.379(13) . ?
C22 H22A 0.9500 . ?
C23 C24 1.458(15) . ?
C24 C25 1.406(15) . ?
C25 H25A 0.9500 . ?
N27 H27 0.9002 . ?
C27 C44 1.351(15) . ?
C27 C40 1.391(14) . ?
C27 H27A 0.9500 . ?
C28 C29 1.366(18) . ?
C28 C33 1.418(17) . ?
C29 C30 1.412(16) . ?
C29 H29A 0.9500 . ?
C30 C31 1.374(18) . ?
C30 H30A 0.9500 . ?
C31 C32 1.379(19) . ?
C31 H31A 0.9500 . ?
C32 C33 1.414(17) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C34 C39 1.390(15) . ?
C34 C35 1.417(17) . ?
C35 C36 1.349(16) . ?
C35 H35A 0.9500 . ?
C36 C37 1.406(14) . ?
C36 H36A 0.9500 . ?
C37 C38 1.338(17) . ?
C37 H37A 0.9500 . ?
C38 C39 1.405(16) . ?
C38 H38A 0.9500 . ?
C39 H39A 0.9500 . ?
C40 C41 1.410(14) . ?
C41 C42 1.371(15) . ?
C41 H41A 0.9500 . ?
C42 C43 1.388(16) . ?
C42 H42A 0.9500 . ?
C43 C44 1.404(14) . ?
C43 H43A 0.9500 . ?
C44 H44A 0.9500 . ?

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
C22 C1 C2 115.6(9) . . ?
C22 C1 C21 120.9(10) . . ?
C2 C1 C21 123.6(10) . . ?
C3 C2 C1 120.1(10) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 120.9(11) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C23 C4 C3 119.9(10) . . ?
C23 C4 C5 118.8(10) . . ?
C3 C4 C5 121.3(10) . . ?
O5 C5 C4 122.4(11) . . ?
O5 C5 C6 117.6(10) . . ?
C4 C5 C6 120.0(10) . . ?
O6 C6 C7 124.8(11) . . ?
O6 C6 C5 119.2(10) . . ?
C7 C6 C5 116.0(9) . . ?
C8 C7 C24 118.6(10) . . ?
C8 C7 C6 120.2(10) . . ?
C24 C7 C6 121.2(10) . . ?
C7 C8 C9 120.9(10) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C10 C9 C8 120.2(11) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C25 118.8(10) . . ?
C9 C10 C11 124.0(10) . . ?
C25 C10 C11 117.2(9) . . ?
C12 C11 C10 127.4(11) . . ?
C12 C11 C28 118.9(9) . . ?
C10 C11 C28 113.6(9) . . ?
C11 C12 N26 126.3(10) . . ?
C11 C12 C13 125.3(11) . . ?
N26 C12 C13 108.4(9) . . ?
C14 C13 C12 108.2(10) . . ?
C14 C13 H13A 125.9 . . ?
C12 C13 H13A 125.9 . . ?
C13 C14 C15 106.2(9) . . ?
C13 C14 H14A 126.9 . . ?
C15 C14 H14A 126.9 . . ?
N26 C15 C16 126.7(10) . . ?
N26 C15 C14 110.0(10) . . ?
C16 C15 C14 122.8(9) . . ?
C17 C16 C15 122.7(9) . . ?
C17 C16 C34 120.0(10) . . ?
C15 C16 C34 117.3(10) . . ?
C16 C17 N27 127.3(10) . . ?
C16 C17 C18 127.7(10) . . ?
N27 C17 C18 104.9(9) . . ?
C19 C18 C17 110.6(10) . . ?
C19 C18 H18A 124.7 . . ?
C17 C18 H18A 124.7 . . ?
C18 C19 C20 107.2(10) . . ?
C18 C19 H19A 126.4 . . ?
C20 C19 H19A 126.4 . . ?
C21 C20 N27 127.4(10) . . ?
C21 C20 C19 126.0(11) . . ?
N27 C20 C19 106.2(10) . . ?
C20 C21 C1 127.1(10) . . ?
C20 C21 C40 116.4(10) . . ?
C1 C21 C40 116.4(9) . . ?
C23 C22 C1 123.9(10) . . ?
C23 C22 H22A 118.1 . . ?
C1 C22 H22A 118.1 . . ?
C4 C23 C22 118.7(10) . . ?
C4 C23 C24 121.9(9) . . ?
C22 C23 C24 119.5(9) . . ?
C25 C24 C7 119.3(10) . . ?
C25 C24 C23 118.6(9) . . ?
C7 C24 C23 121.4(10) . . ?
C24 C25 C10 121.5(10) . . ?
C24 C25 H25A 119.3 . . ?
C10 C25 H25A 119.3 . . ?
C15 N26 C12 107.2(9) . . ?
C20 N27 C17 111.2(9) . . ?
C20 N27 H27 145.8 . . ?
C17 N27 H27 101.4 . . ?
C44 C27 C40 121.7(10) . . ?
C44 C27 H27A 119.2 . . ?
C40 C27 H27A 119.2 . . ?
C29 C28 C33 119.7(11) . . ?
C29 C28 C11 121.7(13) . . ?
C33 C28 C11 118.6(11) . . ?
C28 C29 C30 119.1(13) . . ?
C28 C29 H29A 120.4 . . ?
C30 C29 H29A 120.4 . . ?
C31 C30 C29 122.0(14) . . ?
C31 C30 H30A 119.0 . . ?
C29 C30 H30A 119.0 . . ?
C30 C31 C32 119.4(13) . . ?
C30 C31 H31A 120.3 . . ?
C32 C31 H31A 120.3 . . ?
C31 C32 C33 119.7(14) . . ?
C31 C32 H32A 120.1 . . ?
C33 C32 H32A 120.1 . . ?
C32 C33 C28 119.9(13) . . ?
C32 C33 H33A 120.0 . . ?
C28 C33 H33A 120.0 . . ?
C39 C34 C35 119.0(10) . . ?
C39 C34 C16 120.0(12) . . ?
C35 C34 C16 121.0(10) . . ?
C36 C35 C34 120.1(11) . . ?
C36 C35 H35A 120.0 . . ?
C34 C35 H35A 120.0 . . ?
C35 C36 C37 120.5(13) . . ?
C35 C36 H36A 119.7 . . ?
C37 C36 H36A 119.7 . . ?
C38 C37 C36 120.1(10) . . ?
C38 C37 H37A 120.0 . . ?
C36 C37 H37A 120.0 . . ?
C37 C38 C39 121.1(11) . . ?
C37 C38 H38A 119.5 . . ?
C39 C38 H38A 119.5 . . ?
C34 C39 C38 119.1(13) . . ?
C34 C39 H39A 120.5 . . ?
C38 C39 H39A 120.5 . . ?
C27 C40 C41 118.1(10) . . ?
C27 C40 C21 121.4(9) . . ?
C41 C40 C21 120.5(9) . . ?
C42 C41 C40 119.8(10) . . ?
C42 C41 H41A 120.1 . . ?
C40 C41 H41A 120.1 . . ?
C41 C42 C43 121.6(10) . . ?
C41 C42 H42A 119.2 . . ?
C43 C42 H42A 119.2 . . ?
C42 C43 C44 118.0(11) . . ?
C42 C43 H43A 121.0 . . ?
C44 C43 H43A 121.0 . . ?
C27 C44 C43 120.8(10) . . ?
C27 C44 H44A 119.6 . . ?
C43 C44 H44A 119.6 . . ?

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
C22 C1 C2 C3 -7.9(17) . . . . ?
C21 C1 C2 C3 173.1(12) . . . . ?
C1 C2 C3 C4 9(2) . . . . ?
C2 C3 C4 C23 -1(2) . . . . ?
C2 C3 C4 C5 -178.8(12) . . . . ?
C23 C4 C5 O5 -172.6(13) . . . . ?
C3 C4 C5 O5 5(2) . . . . ?
C23 C4 C5 C6 9.3(18) . . . . ?
C3 C4 C5 C6 -172.9(12) . . . . ?
O5 C5 C6 O6 -3(2) . . . . ?
C4 C5 C6 O6 175.3(12) . . . . ?
O5 C5 C6 C7 176.1(12) . . . . ?
C4 C5 C6 C7 -5.8(18) . . . . ?
O6 C6 C7 C8 0(2) . . . . ?
C5 C6 C7 C8 -179.3(11) . . . . ?
O6 C6 C7 C24 -179.4(13) . . . . ?
C5 C6 C7 C24 1.7(18) . . . . ?
C24 C7 C8 C9 7(2) . . . . ?
C6 C7 C8 C9 -171.9(12) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
C8 C9 C10 C25 -5(2) . . . . ?
C8 C9 C10 C11 176.2(13) . . . . ?
C9 C10 C11 C12 174.3(14) . . . . ?
C25 C10 C11 C12 -4(2) . . . . ?
C9 C10 C11 C28 -9(2) . . . . ?
C25 C10 C11 C28 172.7(11) . . . . ?
C10 C11 C12 N26 -5(2) . . . . ?
C28 C11 C12 N26 178.5(13) . . . . ?
C10 C11 C12 C13 174.9(14) . . . . ?
C28 C11 C12 C13 -2(2) . . . . ?
C11 C12 C13 C14 178.7(14) . . . . ?
N26 C12 C13 C14 -1.8(17) . . . . ?
C12 C13 C14 C15 2.3(16) . . . . ?
C13 C14 C15 N26 -2.1(16) . . . . ?
C13 C14 C15 C16 -174.3(13) . . . . ?
N26 C15 C16 C17 19(2) . . . . ?
C14 C15 C16 C17 -170.6(12) . . . . ?
N26 C15 C16 C34 -161.6(13) . . . . ?
C14 C15 C16 C34 9(2) . . . . ?
C15 C16 C17 N27 4(2) . . . . ?
C34 C16 C17 N27 -176.0(12) . . . . ?
C15 C16 C17 C18 -172.0(13) . . . . ?
C34 C16 C17 C18 8(2) . . . . ?
C16 C17 C18 C19 176.8(12) . . . . ?
N27 C17 C18 C19 0.2(15) . . . . ?
C17 C18 C19 C20 0.9(16) . . . . ?
C18 C19 C20 C21 -174.8(13) . . . . ?
C18 C19 C20 N27 -1.7(15) . . . . ?
N27 C20 C21 C1 -8(2) . . . . ?
C19 C20 C21 C1 163.6(13) . . . . ?
N27 C20 C21 C40 173.3(12) . . . . ?
C19 C20 C21 C40 -15.0(19) . . . . ?
C22 C1 C21 C20 -14(2) . . . . ?
C2 C1 C21 C20 165.2(13) . . . . ?
C22 C1 C21 C40 164.9(11) . . . . ?
C2 C1 C21 C40 -16.1(18) . . . . ?
C2 C1 C22 C23 -0.9(17) . . . . ?
C21 C1 C22 C23 178.1(11) . . . . ?
C3 C4 C23 C22 -7.6(18) . . . . ?
C5 C4 C23 C22 170.2(11) . . . . ?
C3 C4 C23 C24 173.5(12) . . . . ?
C5 C4 C23 C24 -8.7(18) . . . . ?
C1 C22 C23 C4 8.7(18) . . . . ?
C1 C22 C23 C24 -172.3(11) . . . . ?
C8 C7 C24 C25 -9.1(19) . . . . ?
C6 C7 C24 C25 170.0(13) . . . . ?
C8 C7 C24 C23 179.9(12) . . . . ?
C6 C7 C24 C23 -1(2) . . . . ?
C4 C23 C24 C25 -166.4(12) . . . . ?
C22 C23 C24 C25 14.7(19) . . . . ?
C4 C23 C24 C7 5(2) . . . . ?
C22 C23 C24 C7 -174.3(12) . . . . ?
C7 C24 C25 C10 4(2) . . . . ?
C23 C24 C25 C10 175.3(12) . . . . ?
C9 C10 C25 C24 3(2) . . . . ?
C11 C10 C25 C24 -178.1(12) . . . . ?
C16 C15 N26 C12 172.8(13) . . . . ?
C14 C15 N26 C12 1.0(16) . . . . ?
C11 C12 N26 C15 180.0(14) . . . . ?
C13 C12 N26 C15 0.4(17) . . . . ?
C21 C20 N27 C17 174.8(13) . . . . ?
C19 C20 N27 C17 1.8(14) . . . . ?
C16 C17 N27 C20 -177.9(12) . . . . ?
C18 C17 N27 C20 -1.3(15) . . . . ?
C12 C11 C28 C29 122.3(13) . . . . ?
C10 C11 C28 C29 -55.0(15) . . . . ?
C12 C11 C28 C33 -56.9(16) . . . . ?
C10 C11 C28 C33 125.8(12) . . . . ?
C33 C28 C29 C30 -0.9(15) . . . . ?
C11 C28 C29 C30 179.9(9) . . . . ?
C28 C29 C30 C31 0.1(16) . . . . ?
C29 C30 C31 C32 1.8(16) . . . . ?
C30 C31 C32 C33 -2.8(16) . . . . ?
C31 C32 C33 C28 2.0(15) . . . . ?
C29 C28 C33 C32 -0.1(15) . . . . ?
C11 C28 C33 C32 179.2(9) . . . . ?
C17 C16 C34 C39 54.6(18) . . . . ?
C15 C16 C34 C39 -125.3(14) . . . . ?
C17 C16 C34 C35 -123.5(14) . . . . ?
C15 C16 C34 C35 56.6(18) . . . . ?
C39 C34 C35 C36 4(2) . . . . ?
C16 C34 C35 C36 -177.8(11) . . . . ?
C34 C35 C36 C37 -0.9(19) . . . . ?
C35 C36 C37 C38 -1.3(18) . . . . ?
C36 C37 C38 C39 0.2(19) . . . . ?
C35 C34 C39 C38 -5(2) . . . . ?
C16 C34 C39 C38 176.8(11) . . . . ?
C37 C38 C39 C34 3(2) . . . . ?
C44 C27 C40 C41 0.9(19) . . . . ?
C44 C27 C40 C21 -179.9(12) . . . . ?
C20 C21 C40 C27 132.9(13) . . . . ?
C1 C21 C40 C27 -45.9(17) . . . . ?
C20 C21 C40 C41 -47.8(17) . . . . ?
C1 C21 C40 C41 133.3(12) . . . . ?
C27 C40 C41 C42 -1.4(18) . . . . ?
C21 C40 C41 C42 179.4(12) . . . . ?
C40 C41 C42 C43 0(2) . . . . ?
C41 C42 C43 C44 2(2) . . . . ?
C40 C27 C44 C43 1(2) . . . . ?
C42 C43 C44 C27 -2.7(19) . . . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.089


####################################################################### 
# 
# 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_2H+
_database_code_depnum_ccdc_archive 'CCDC 1856755'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'monocation of 5,6-dioxophenanthriporphyrin'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C43 H27 N2 O2, 3(C6 H6), B F4'
_chemical_formula_sum            'C61 H45 B F4 N2 O2'
_chemical_formula_weight         924.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.154(3)
_cell_length_b                   17.553(3)
_cell_length_c                   19.832(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.78(3)
_cell_angle_gamma                90
_cell_volume                     4717.4(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9442
_cell_measurement_theta_min      2.3250
_cell_measurement_theta_max      67.9931

_exptl_crystal_description       plate
_exptl_crystal_colour            blueish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.721
_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     1.54175
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_reflns_number            18917
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.416
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_full        67.676
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             8435
_reflns_number_gt                6112
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1159P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8435
_refine_ls_number_parameters     639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2389(2) 1.24161(15) -0.08151(13) 0.0383(5) Uani 1 1 d . . . . .
F1 F 0.28546(13) 1.20107(10) -0.12084(9) 0.0666(5) Uani 1 1 d . . . . .
F2 F 0.25254(11) 1.20686(9) -0.01571(7) 0.0564(4) Uani 1 1 d . . . . .
F3 F 0.27855(12) 1.31363(9) -0.06877(9) 0.0636(4) Uani 1 1 d . . . . .
F4 F 0.13894(11) 1.24479(9) -0.11423(9) 0.0632(4) Uani 1 1 d . . . . .
C1 C 0.26899(15) 1.43362(10) 0.04813(10) 0.0282(4) Uani 1 1 d . . . . .
C2 C 0.23750(15) 1.49392(11) -0.00017(11) 0.0317(4) Uani 1 1 d . . . . .
H2A H 0.2817 1.5319 -0.0037 0.038 Uiso 1 1 calc R U . . .
C3 C 0.14117(16) 1.49655(11) -0.04215(10) 0.0318(4) Uani 1 1 d . . . . .
H3A H 0.1207 1.5371 -0.0731 0.038 Uiso 1 1 calc R U . . .
C4 C 0.07335(15) 1.43924(11) -0.03906(10) 0.0291(4) Uani 1 1 d . . . . .
O5 O -0.05595(12) 1.49088(9) -0.13143(8) 0.0427(4) Uani 1 1 d . . . . .
C5 C -0.02666(15) 1.44119(11) -0.08835(10) 0.0316(4) Uani 1 1 d . . . . .
O6 O -0.18146(11) 1.37846(9) -0.12242(8) 0.0426(4) Uani 1 1 d . . . . .
C6 C -0.09704(15) 1.37507(11) -0.08515(10) 0.0315(4) Uani 1 1 d . . . . .
C7 C -0.05773(14) 1.31064(11) -0.03798(10) 0.0292(4) Uani 1 1 d . . . . .
C8 C -0.11435(14) 1.24470(12) -0.04036(10) 0.0320(4) Uani 1 1 d . . . . .
H8A H -0.1779 1.2427 -0.0710 0.038 Uiso 1 1 calc R U . . .
C9 C -0.07785(14) 1.18268(11) 0.00173(10) 0.0307(4) Uani 1 1 d . . . . .
H9A H -0.1165 1.1393 -0.0011 0.037 Uiso 1 1 calc R U . . .
C10 C 0.01827(14) 1.18494(11) 0.04924(10) 0.0285(4) Uani 1 1 d . . . . .
C11 C 0.06117(14) 1.11926(11) 0.09221(10) 0.0289(4) Uani 1 1 d . . . . .
C12 C 0.16134(14) 1.10713(11) 0.12118(10) 0.0284(4) Uani 1 1 d . . . . .
C13 C 0.20768(15) 1.05378(11) 0.17508(11) 0.0328(4) Uani 1 1 d . . . . .
H13A H 0.1749 1.0185 0.1952 0.039 Uiso 1 1 calc R U . . .
C14 C 0.30621(15) 1.06255(11) 0.19215(11) 0.0322(4) Uani 1 1 d . . . . .
H14A H 0.3527 1.0342 0.2254 0.039 Uiso 1 1 calc R U . . .
C15 C 0.32728(14) 1.12371(11) 0.14990(10) 0.0282(4) Uani 1 1 d . . . . .
C16 C 0.42153(14) 1.15637(11) 0.16126(10) 0.0287(4) Uani 1 1 d . . . . .
C17 C 0.44065(14) 1.23342(11) 0.14808(10) 0.0292(4) Uani 1 1 d . . . . .
C18 C 0.52728(14) 1.27562(12) 0.18492(11) 0.0340(5) Uani 1 1 d . . . . .
H18A H 0.5843 1.2551 0.2154 0.041 Uiso 1 1 calc R U . . .
C19 C 0.51221(15) 1.34954(12) 0.16799(11) 0.0341(4) Uani 1 1 d . . . . .
H19A H 0.5566 1.3887 0.1859 0.041 Uiso 1 1 calc R U . . .
C20 C 0.41656(14) 1.35860(11) 0.11775(10) 0.0297(4) Uani 1 1 d . . . . .
C21 C 0.37226(15) 1.42601(11) 0.08993(10) 0.0306(4) Uani 1 1 d . . . . .
C22 C 0.19915(14) 1.37976(11) 0.05380(10) 0.0272(4) Uani 1 1 d . . . . .
H22A H 0.2176 1.3424 0.0884 0.033 Uiso 1 1 calc R U . . .
C23 C 0.10296(14) 1.37986(11) 0.00957(10) 0.0268(4) Uani 1 1 d . . . . .
C24 C 0.03745(14) 1.31437(11) 0.00996(10) 0.0272(4) Uani 1 1 d . . . . .
C25 C 0.07125(14) 1.25293(11) 0.05370(10) 0.0283(4) Uani 1 1 d . . . . .
H25A H 0.1320 1.2569 0.0877 0.034 Uiso 1 1 calc R U . . .
N26 N 0.23854(12) 1.14864(9) 0.10778(9) 0.0278(3) Uani 1 1 d . . . . .
N27 N 0.37665(12) 1.28475(9) 0.10726(9) 0.0284(4) Uani 1 1 d . . . . .
C28 C -0.00586(14) 1.06131(11) 0.10862(10) 0.0305(4) Uani 1 1 d . . . . .
C29 C 0.00133(16) 0.98476(12) 0.09228(12) 0.0359(5) Uani 1 1 d . . . . .
H29A H 0.0472 0.9695 0.0695 0.043 Uiso 1 1 calc R U . . .
C30 C -0.05987(17) 0.93097(13) 0.10992(12) 0.0410(5) Uani 1 1 d . . . . .
H30A H -0.0553 0.8800 0.0984 0.049 Uiso 1 1 calc R U . . .
C31 C -0.12685(17) 0.95281(14) 0.14425(13) 0.0447(6) Uani 1 1 d . . . . .
H31A H -0.1668 0.9166 0.1566 0.054 Uiso 1 1 calc R U . . .
C32 C -0.13495(17) 1.02882(14) 0.16056(13) 0.0436(5) Uani 1 1 d . . . . .
H32A H -0.1804 1.0435 0.1838 0.052 Uiso 1 1 calc R U . . .
C33 C -0.07520(16) 1.08323(12) 0.14220(12) 0.0372(5) Uani 1 1 d . . . . .
H33A H -0.0817 1.1343 0.1524 0.045 Uiso 1 1 calc R U . . .
C34 C 0.50613(14) 1.10709(11) 0.19941(11) 0.0301(4) Uani 1 1 d . . . . .
C35 C 0.52632(15) 1.04128(11) 0.16656(11) 0.0328(4) Uani 1 1 d . . . . .
H35A H 0.4859 1.0283 0.1221 0.039 Uiso 1 1 calc R U . . .
C36 C 0.60564(16) 0.99509(12) 0.19919(13) 0.0401(5) Uani 1 1 d . . . . .
H36A H 0.6179 0.9512 0.1769 0.048 Uiso 1 1 calc R U . . .
C37 C 0.66663(16) 1.01430(14) 0.26506(13) 0.0431(5) Uani 1 1 d . . . . .
H37A H 0.7213 0.9843 0.2864 0.052 Uiso 1 1 calc R U . . .
C38 C 0.64591(16) 1.07845(14) 0.29906(12) 0.0406(5) Uani 1 1 d . . . . .
H38A H 0.6862 1.0910 0.3437 0.049 Uiso 1 1 calc R U . . .
C39 C 0.56578(15) 1.12386(12) 0.26716(11) 0.0343(4) Uani 1 1 d . . . . .
H39A H 0.5514 1.1659 0.2910 0.041 Uiso 1 1 calc R U . . .
C40 C 0.43356(15) 1.49610(11) 0.10377(11) 0.0313(4) Uani 1 1 d . . . . .
C41 C 0.52293(15) 1.50010(12) 0.08800(11) 0.0335(4) Uani 1 1 d . . . . .
H41A H 0.5465 1.4574 0.0702 0.040 Uiso 1 1 calc R U . . .
C42 C 0.57731(16) 1.56698(13) 0.09844(12) 0.0387(5) Uani 1 1 d . . . . .
H42A H 0.6365 1.5693 0.0870 0.046 Uiso 1 1 calc R U . . .
C43 C 0.54336(18) 1.63037(13) 0.12597(13) 0.0452(6) Uani 1 1 d . . . . .
H43A H 0.5798 1.6753 0.1333 0.054 Uiso 1 1 calc R U . . .
C44 C 0.45540(19) 1.62661(13) 0.14242(14) 0.0469(6) Uani 1 1 d . . . . .
H44A H 0.4330 1.6690 0.1614 0.056 Uiso 1 1 calc R U . . .
C45 C 0.39980(17) 1.56034(12) 0.13109(12) 0.0390(5) Uani 1 1 d . . . . .
H45A H 0.3400 1.5587 0.1417 0.047 Uiso 1 1 calc R U . . .
C61 C 0.72688(18) 0.20199(14) 0.14864(14) 0.0465(6) Uani 1 1 d . . . . .
H61A H 0.6849 0.1602 0.1424 0.056 Uiso 1 1 calc R U . . .
C62 C 0.73688(19) 0.24128(15) 0.09082(14) 0.0498(6) Uani 1 1 d . . . . .
H62A H 0.7017 0.2262 0.0456 0.060 Uiso 1 1 calc R U . . .
C63 C 0.7995(2) 0.30314(14) 0.10075(15) 0.0536(7) Uani 1 1 d . . . . .
H63A H 0.8063 0.3299 0.0619 0.064 Uiso 1 1 calc R U . . .
C64 C 0.8519(2) 0.32561(14) 0.16738(15) 0.0521(6) Uani 1 1 d . . . . .
H64A H 0.8943 0.3672 0.1736 0.063 Uiso 1 1 calc R U . . .
C65 C 0.84144(19) 0.28625(15) 0.22527(14) 0.0483(6) Uani 1 1 d . . . . .
H65A H 0.8765 0.3015 0.2705 0.058 Uiso 1 1 calc R U . . .
C66 C 0.77916(17) 0.22468(14) 0.21574(13) 0.0455(5) Uani 1 1 d . . . . .
H66A H 0.7721 0.1981 0.2546 0.055 Uiso 1 1 calc R U . . .
C71 C 0.2211(3) 0.24090(17) 0.26090(14) 0.0631(8) Uani 1 1 d . . . . .
H71A H 0.2192 0.1899 0.2733 0.076 Uiso 1 1 calc R U . . .
C72 C 0.1355(2) 0.27953(15) 0.23084(12) 0.0548(7) Uani 1 1 d . . . . .
H72A H 0.0751 0.2550 0.2232 0.066 Uiso 1 1 calc R U . . .
C73 C 0.1383(2) 0.35503(14) 0.21170(12) 0.0475(6) Uani 1 1 d . . . . .
H73A H 0.0797 0.3808 0.1912 0.057 Uiso 1 1 calc R U . . .
C74 C 0.22706(19) 0.39255(14) 0.22258(12) 0.0447(6) Uani 1 1 d . . . . .
H74A H 0.2282 0.4431 0.2089 0.054 Uiso 1 1 calc R U . . .
C75 C 0.3141(2) 0.35473(17) 0.25378(13) 0.0549(7) Uani 1 1 d . . . . .
H75A H 0.3742 0.3798 0.2621 0.066 Uiso 1 1 calc R U . . .
C76 C 0.3110(3) 0.27820(19) 0.27282(13) 0.0666(9) Uani 1 1 d . . . . .
H76A H 0.3695 0.2522 0.2935 0.080 Uiso 1 1 calc R U . . .
C81 C 0.4647(2) 0.85360(16) 0.06482(14) 0.0542(6) Uani 1 1 d . . . . .
H81A H 0.5197 0.8220 0.0762 0.065 Uiso 1 1 calc R U . . .
C82 C 0.4007(2) 0.85280(15) 0.10510(14) 0.0543(7) Uani 1 1 d . . . . .
H82A H 0.4124 0.8203 0.1437 0.065 Uiso 1 1 calc R U . . .
C83 C 0.3195(2) 0.89948(15) 0.08914(13) 0.0508(6) Uani 1 1 d . . . . .
H83A H 0.2766 0.8986 0.1168 0.061 Uiso 1 1 calc R U . . .
C84 C 0.30172(19) 0.94786(16) 0.03182(14) 0.0525(6) Uani 1 1 d . . . . .
H84A H 0.2468 0.9796 0.0208 0.063 Uiso 1 1 calc R U . . .
C85 C 0.3665(2) 0.94874(16) -0.00915(14) 0.0528(7) Uani 1 1 d . . . . .
H85A H 0.3552 0.9813 -0.0477 0.063 Uiso 1 1 calc R U . . .
C86 C 0.4473(2) 0.90131(16) 0.00741(14) 0.0535(6) Uani 1 1 d . . . . .
H86A H 0.4904 0.9015 -0.0202 0.064 Uiso 1 1 calc R U . . .
H26 H 0.2320(15) 1.1720(13) 0.0688(12) 0.026(5) Uiso 1 1 d . . . . .
H27 H 0.3319(18) 1.2718(14) 0.0687(13) 0.037(6) Uiso 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
B1 F1 1.359(3) . ?
B1 F3 1.377(3) . ?
B1 F4 1.377(3) . ?
B1 F2 1.402(3) . ?
C1 C22 1.396(3) . ?
C1 C2 1.411(3) . ?
C1 C21 1.463(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.404(3) . ?
C4 C23 1.399(3) . ?
C4 C5 1.470(3) . ?
O5 C5 1.208(3) . ?
C5 C6 1.543(3) . ?
O6 C6 1.211(3) . ?
C6 C7 1.471(3) . ?
C7 C8 1.401(3) . ?
C7 C24 1.408(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.414(3) . ?
C10 C25 1.399(3) . ?
C10 C11 1.458(3) . ?
C11 C12 1.384(3) . ?
C11 C28 1.490(3) . ?
C12 N26 1.401(2) . ?
C12 C13 1.430(3) . ?
C13 C14 1.346(3) . ?
C14 C15 1.445(3) . ?
C15 N26 1.364(3) . ?
C15 C16 1.409(3) . ?
C16 C17 1.418(3) . ?
C16 C34 1.494(3) . ?
C17 N27 1.365(3) . ?
C17 C18 1.438(3) . ?
C18 C19 1.342(3) . ?
C19 C20 1.439(3) . ?
C20 C21 1.378(3) . ?
C20 N27 1.405(3) . ?
C21 C40 1.485(3) . ?
C22 C23 1.390(3) . ?
C23 C24 1.478(3) . ?
C24 C25 1.380(3) . ?
C28 C33 1.390(3) . ?
C28 C29 1.393(3) . ?
C29 C30 1.393(3) . ?
C30 C31 1.372(4) . ?
C31 C32 1.385(4) . ?
C32 C33 1.392(3) . ?
C34 C35 1.396(3) . ?
C34 C39 1.396(3) . ?
C35 C36 1.385(3) . ?
C36 C37 1.384(4) . ?
C37 C38 1.387(4) . ?
C38 C39 1.381(3) . ?
C40 C41 1.390(3) . ?
C40 C45 1.394(3) . ?
C41 C42 1.386(3) . ?
C42 C43 1.385(3) . ?
C43 C44 1.377(4) . ?
C44 C45 1.386(3) . ?
C61 C62 1.380(4) . ?
C61 C66 1.382(4) . ?
C62 C63 1.379(4) . ?
C63 C64 1.373(4) . ?
C64 C65 1.384(4) . ?
C65 C66 1.373(4) . ?
C71 C72 1.367(4) . ?
C71 C76 1.390(5) . ?
C72 C73 1.382(4) . ?
C73 C74 1.379(4) . ?
C74 C75 1.378(4) . ?
C75 C76 1.399(5) . ?
C81 C82 1.369(4) . ?
C81 C86 1.377(4) . ?
C82 C83 1.372(4) . ?
C83 C84 1.383(4) . ?
C84 C85 1.390(4) . ?
C85 C86 1.376(4) . ?

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
F1 B1 F3 110.3(2) . . ?
F1 B1 F4 110.7(2) . . ?
F3 B1 F4 111.0(2) . . ?
F1 B1 F2 110.3(2) . . ?
F3 B1 F2 106.82(19) . . ?
F4 B1 F2 107.6(2) . . ?
C22 C1 C2 118.08(18) . . ?
C22 C1 C21 120.48(17) . . ?
C2 C1 C21 121.42(18) . . ?
C3 C2 C1 119.94(19) . . ?
C2 C3 C4 121.28(18) . . ?
C23 C4 C3 119.42(18) . . ?
C23 C4 C5 120.99(19) . . ?
C3 C4 C5 119.56(18) . . ?
O5 C5 C4 123.7(2) . . ?
O5 C5 C6 118.59(18) . . ?
C4 C5 C6 117.67(17) . . ?
O6 C6 C7 123.4(2) . . ?
O6 C6 C5 118.23(19) . . ?
C7 C6 C5 118.32(17) . . ?
C8 C7 C24 119.18(18) . . ?
C8 C7 C6 120.41(18) . . ?
C24 C7 C6 120.41(18) . . ?
C9 C8 C7 121.42(18) . . ?
C8 C9 C10 120.11(19) . . ?
C25 C10 C9 117.46(18) . . ?
C25 C10 C11 120.84(17) . . ?
C9 C10 C11 121.70(18) . . ?
C12 C11 C10 124.63(18) . . ?
C12 C11 C28 116.42(17) . . ?
C10 C11 C28 118.92(17) . . ?
C11 C12 N26 127.07(18) . . ?
C11 C12 C13 127.23(19) . . ?
N26 C12 C13 105.53(16) . . ?
C14 C13 C12 109.36(18) . . ?
C13 C14 C15 108.15(17) . . ?
N26 C15 C16 128.99(18) . . ?
N26 C15 C14 106.60(17) . . ?
C16 C15 C14 123.64(18) . . ?
C15 C16 C17 125.50(18) . . ?
C15 C16 C34 115.39(17) . . ?
C17 C16 C34 118.55(17) . . ?
N27 C17 C16 127.54(18) . . ?
N27 C17 C18 106.48(17) . . ?
C16 C17 C18 125.27(18) . . ?
C19 C18 C17 108.68(18) . . ?
C18 C19 C20 109.26(19) . . ?
C21 C20 N27 128.02(18) . . ?
C21 C20 C19 126.91(19) . . ?
N27 C20 C19 104.96(17) . . ?
C20 C21 C1 124.74(18) . . ?
C20 C21 C40 117.61(17) . . ?
C1 C21 C40 117.64(17) . . ?
C23 C22 C1 122.38(18) . . ?
C22 C23 C4 118.65(18) . . ?
C22 C23 C24 119.81(18) . . ?
C4 C23 C24 121.28(17) . . ?
C25 C24 C7 118.58(18) . . ?
C25 C24 C23 120.45(17) . . ?
C7 C24 C23 120.78(18) . . ?
C24 C25 C10 123.02(17) . . ?
C15 N26 C12 110.35(16) . . ?
C17 N27 C20 110.57(16) . . ?
C33 C28 C29 119.18(19) . . ?
C33 C28 C11 119.87(19) . . ?
C29 C28 C11 120.93(19) . . ?
C30 C29 C28 120.2(2) . . ?
C31 C30 C29 120.3(2) . . ?
C30 C31 C32 120.0(2) . . ?
C31 C32 C33 120.2(2) . . ?
C28 C33 C32 120.1(2) . . ?
C35 C34 C39 118.38(19) . . ?
C35 C34 C16 119.01(18) . . ?
C39 C34 C16 122.61(19) . . ?
C36 C35 C34 120.9(2) . . ?
C37 C36 C35 120.0(2) . . ?
C36 C37 C38 119.7(2) . . ?
C39 C38 C37 120.5(2) . . ?
C38 C39 C34 120.5(2) . . ?
C41 C40 C45 118.88(19) . . ?
C41 C40 C21 121.44(19) . . ?
C45 C40 C21 119.64(19) . . ?
C42 C41 C40 120.8(2) . . ?
C43 C42 C41 119.9(2) . . ?
C44 C43 C42 119.7(2) . . ?
C43 C44 C45 120.8(2) . . ?
C44 C45 C40 120.0(2) . . ?
C62 C61 C66 120.1(2) . . ?
C63 C62 C61 119.4(2) . . ?
C64 C63 C62 120.6(3) . . ?
C63 C64 C65 119.8(2) . . ?
C66 C65 C64 119.8(2) . . ?
C65 C66 C61 120.2(2) . . ?
C72 C71 C76 119.6(3) . . ?
C71 C72 C73 120.2(3) . . ?
C74 C73 C72 120.8(3) . . ?
C75 C74 C73 119.7(3) . . ?
C74 C75 C76 119.4(3) . . ?
C71 C76 C75 120.3(3) . . ?
C82 C81 C86 119.9(3) . . ?
C81 C82 C83 120.7(3) . . ?
C82 C83 C84 119.9(3) . . ?
C83 C84 C85 119.5(3) . . ?
C86 C85 C84 119.8(3) . . ?
C85 C86 C81 120.2(3) . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.059


####################################################################### 
# 
# 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_2BF2
_database_code_depnum_ccdc_archive 'CCDC 1856756'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C43 H27 B F2 N2 O2), 3(B2 F6 O) [+ solvent]'
_chemical_formula_sum            'C86 H54 B8 F22 N4 O7'
_chemical_formula_weight         1759.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   8.090(2)
_cell_length_b                   12.074(3)
_cell_length_c                   24.254(3)
_cell_angle_alpha                82.58(2)
_cell_angle_beta                 89.11(2)
_cell_angle_gamma                70.85(3)
_cell_volume                     2218.3(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1241
_cell_measurement_theta_min      1.8361
_cell_measurement_theta_max      80.2418

_exptl_crystal_description       needle
_exptl_crystal_colour            maroon
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.986
_shelx_estimated_absorpt_T_min   0.565
_shelx_estimated_absorpt_T_max   0.966
_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     1.54175
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.20
_diffrn_reflns_number            22839
_diffrn_reflns_av_unetI/netI     0.2807
_diffrn_reflns_av_R_equivalents  0.1544
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.838
_diffrn_reflns_theta_max         80.508
_diffrn_reflns_theta_full        67.676
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9238
_reflns_number_gt                2150
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9238
_refine_ls_number_parameters     632
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.2001
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.2196
_refine_ls_wR_factor_gt          0.1883
_refine_ls_goodness_of_fit_ref   0.664
_refine_ls_restrained_S_all      0.687
_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 0.1376(8) 0.5726(5) 0.1502(2) 0.0435(15) Uani 1 1 d . . . . .
B1 B -0.2891(10) 1.0836(6) 0.2169(4) 0.054(2) Uani 1 1 d . . . . .
F1A F -0.2204(5) 1.1602(3) 0.24190(16) 0.0548(10) Uani 1 1 d . . . . .
F2A F -0.4314(5) 1.1477(3) 0.18658(17) 0.0640(11) Uani 1 1 d . . . . .
O5 O -0.1498(5) 1.0034(3) 0.18636(18) 0.0473(11) Uani 1 1 d . . . . .
O6 O -0.3298(6) 1.0020(3) 0.26409(18) 0.0530(12) Uani 1 1 d . . . . .
C2 C 0.1631(8) 0.6763(5) 0.1235(3) 0.0447(15) Uani 1 1 d . . . . .
H2A H 0.2349 0.6723 0.0920 0.054 Uiso 1 1 calc R U . . .
C3 C 0.0842(8) 0.7840(5) 0.1428(2) 0.0421(15) Uani 1 1 d . . . . .
H3A H 0.0964 0.8546 0.1237 0.051 Uiso 1 1 calc R U . . .
C4 C -0.0143(7) 0.7870(5) 0.1912(2) 0.0395(14) Uani 1 1 d . . . . .
C5 C -0.1233(8) 0.8935(5) 0.2102(3) 0.0450(15) Uani 1 1 d . . . . .
C6 C -0.2348(8) 0.8932(5) 0.2569(3) 0.0420(15) Uani 1 1 d . . . . .
C7 C -0.2320(8) 0.7905(5) 0.2906(2) 0.0445(16) Uani 1 1 d . . . . .
C8 C -0.3322(8) 0.7838(6) 0.3380(3) 0.0507(16) Uani 1 1 d . . . . .
H8A H -0.4180 0.8534 0.3474 0.061 Uiso 1 1 calc R U . . .
C9 C -0.3075(8) 0.6777(5) 0.3708(3) 0.0486(16) Uani 1 1 d . . . . .
H9A H -0.3776 0.6754 0.4024 0.058 Uiso 1 1 calc R U . . .
C10 C -0.1800(8) 0.5714(5) 0.3587(3) 0.0456(15) Uani 1 1 d . . . . .
C11 C -0.1405(8) 0.4614(5) 0.3933(3) 0.0479(16) Uani 1 1 d . . . . .
C12 C -0.0339(8) 0.3522(5) 0.3763(3) 0.0482(16) Uani 1 1 d . . . . .
C13 C 0.0736(8) 0.2532(5) 0.4109(3) 0.0527(17) Uani 1 1 d . . . . .
H13A H 0.0875 0.2477 0.4501 0.063 Uiso 1 1 calc R U . . .
C14 C 0.1569(8) 0.1642(5) 0.3786(3) 0.0520(17) Uani 1 1 d . . . . .
H14A H 0.2337 0.0869 0.3912 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1023(8) 0.2139(5) 0.3226(3) 0.0466(16) Uani 1 1 d . . . . .
C16 C 0.1477(8) 0.1528(5) 0.2742(3) 0.0436(15) Uani 1 1 d . . . . .
C17 C 0.1502(8) 0.2135(5) 0.2212(3) 0.0428(15) Uani 1 1 d . . . . .
C18 C 0.1240(8) 0.1820(5) 0.1684(3) 0.0441(15) Uani 1 1 d . . . . .
H18A H 0.0963 0.1139 0.1622 0.053 Uiso 1 1 calc R U . . .
C19 C 0.1449(7) 0.2648(5) 0.1285(3) 0.0406(14) Uani 1 1 d . . . . .
H19A H 0.1379 0.2635 0.0896 0.049 Uiso 1 1 calc R U . . .
C20 C 0.1798(8) 0.3555(5) 0.1550(3) 0.0400(14) Uani 1 1 d . . . . .
C21 C 0.1921(8) 0.4608(4) 0.1265(3) 0.0402(14) Uani 1 1 d . . . . .
C22 C 0.0443(8) 0.5813(5) 0.1993(3) 0.0454(16) Uani 1 1 d . . . . .
H22A H 0.0254 0.5121 0.2175 0.054 Uiso 1 1 calc R U . . .
C23 C -0.0218(8) 0.6843(5) 0.2229(3) 0.0470(16) Uani 1 1 d . . . . .
C24 C -0.1130(9) 0.6811(5) 0.2749(3) 0.0480(16) Uani 1 1 d . . . . .
C25 C -0.0822(9) 0.5809(5) 0.3102(3) 0.0505(17) Uani 1 1 d . . . . .
H25A H 0.0099 0.5127 0.3023 0.061 Uiso 1 1 calc R U . . .
N26 N -0.0110(7) 0.3265(4) 0.3223(2) 0.0440(13) Uani 1 1 d . . . . .
H26 H -0.0914 0.3650 0.2970 0.066 Uiso 1 1 d R U . . .
N27 N 0.1765(6) 0.3216(4) 0.2113(2) 0.0400(12) Uani 1 1 d . . . . .
H27 H 0.1996 0.3553 0.2384 0.060 Uiso 1 1 d R U . . .
C28 C -0.2034(9) 0.4543(6) 0.4509(3) 0.0516(17) Uani 1 1 d . . . . .
C29 C -0.2546(9) 0.3597(6) 0.4720(3) 0.0589(19) Uani 1 1 d . . . . .
H29A H -0.2520 0.3010 0.4492 0.071 Uiso 1 1 calc R U . . .
C30 C -0.3099(10) 0.3490(7) 0.5260(3) 0.065(2) Uani 1 1 d . . . . .
H30A H -0.3456 0.2834 0.5399 0.078 Uiso 1 1 calc R U . . .
C31 C -0.3133(9) 0.4344(7) 0.5601(3) 0.068(2) Uani 1 1 d . . . . .
H31A H -0.3499 0.4269 0.5974 0.082 Uiso 1 1 calc R U . . .
C32 C -0.2633(9) 0.5289(7) 0.5392(3) 0.064(2) Uani 1 1 d . . . . .
H32A H -0.2680 0.5877 0.5623 0.077 Uiso 1 1 calc R U . . .
C33 C -0.2062(9) 0.5413(6) 0.4858(3) 0.0560(18) Uani 1 1 d . . . . .
H33A H -0.1694 0.6067 0.4724 0.067 Uiso 1 1 calc R U . . .
C34 C 0.1848(9) 0.0246(5) 0.2808(3) 0.0517(17) Uani 1 1 d . . . . .
C35 C 0.1045(9) -0.0296(5) 0.3230(3) 0.0576(19) Uani 1 1 d . . . . .
H35A H 0.0229 0.0167 0.3465 0.069 Uiso 1 1 calc R U . . .
C36 C 0.1461(11) -0.1513(6) 0.3295(3) 0.073(2) Uani 1 1 d . . . . .
H36A H 0.0936 -0.1885 0.3582 0.087 Uiso 1 1 calc R U . . .
C37 C 0.2622(12) -0.2193(6) 0.2953(3) 0.078(3) Uani 1 1 d . . . . .
H37A H 0.2916 -0.3030 0.3011 0.093 Uiso 1 1 calc R U . . .
C38 C 0.3350(10) -0.1667(6) 0.2530(3) 0.069(2) Uani 1 1 d . . . . .
H38A H 0.4090 -0.2135 0.2279 0.083 Uiso 1 1 calc R U . . .
C39 C 0.3015(9) -0.0456(6) 0.2464(3) 0.0584(19) Uani 1 1 d . . . . .
H39A H 0.3584 -0.0102 0.2183 0.070 Uiso 1 1 calc R U . . .
C40 C 0.2529(8) 0.4561(5) 0.0695(3) 0.0410(14) Uani 1 1 d . . . . .
C41 C 0.3979(8) 0.3586(5) 0.0584(3) 0.0435(15) Uani 1 1 d . . . . .
H41A H 0.4559 0.2988 0.0877 0.052 Uiso 1 1 calc R U . . .
C42 C 0.4545(8) 0.3511(6) 0.0043(3) 0.0506(16) Uani 1 1 d . . . . .
H42A H 0.5523 0.2860 -0.0033 0.061 Uiso 1 1 calc R U . . .
C43 C 0.3715(8) 0.4359(5) -0.0382(3) 0.0475(16) Uani 1 1 d . . . . .
H43A H 0.4113 0.4291 -0.0750 0.057 Uiso 1 1 calc R U . . .
C44 C 0.2294(8) 0.5322(5) -0.0279(3) 0.0478(16) Uani 1 1 d . . . . .
H44A H 0.1738 0.5922 -0.0574 0.057 Uiso 1 1 calc R U . . .
C45 C 0.1699(8) 0.5403(5) 0.0249(2) 0.0409(14) Uani 1 1 d . . . . .
H45A H 0.0697 0.6048 0.0314 0.049 Uiso 1 1 calc R U . . .
F1 F -0.2198(5) 0.4448(4) 0.22821(17) 0.0743(13) Uani 1 1 d . U . . .
F2 F -0.3906(9) 0.4318(5) 0.1630(2) 0.135(2) Uani 1 1 d . U . . .
F3 F -0.4934(8) 0.5673(4) 0.2192(3) 0.146(2) Uani 1 1 d . U . . .
F4 F -0.6968(8) 0.4115(7) 0.3007(3) 0.0807(19) Uani 0.711(6) 1 d . U P A 1
F5 F -0.4734(11) 0.4515(8) 0.3354(3) 0.110(2) Uani 0.711(6) 1 d . U P A 1
F6 F -0.4674(14) 0.2640(9) 0.3377(4) 0.139(3) Uani 0.711(6) 1 d . U P A 1
F41 F -0.613(3) 0.317(2) 0.3102(9) 0.100(4) Uani 0.289(6) 1 d . U P A 2
F51 F -0.392(3) 0.354(2) 0.3402(10) 0.120(4) Uani 0.289(6) 1 d . U P A 2
F61 F -0.635(3) 0.5072(19) 0.3015(8) 0.115(4) Uani 0.289(6) 1 d . U P A 2
B10 B -0.3893(12) 0.4636(7) 0.2141(4) 0.066(3) Uani 1 1 d . . . . .
B20 B -0.5200(16) 0.3795(8) 0.3073(5) 0.084(3) Uani 1 1 d . . . . .
O10 O -0.4408(6) 0.3704(4) 0.2512(2) 0.0704(15) Uani 1 1 d . . . . .
B30 B 1.0147(15) 0.9004(7) -0.0253(6) 0.085(4) Uani 1 1 d . . . . .
O20 O 1.0911(10) 0.9931(7) -0.0190(4) 0.055(2) Uani 0.5 1 d . . P B -1
F8 F 1.1551(11) 0.8286(7) -0.0632(4) 0.075(2) Uani 0.5 1 d . U P B -1
F9 F 0.8804(12) 0.9589(7) -0.0719(4) 0.062(2) Uani 0.5 1 d . U P B -1
F10 F 1.0000(16) 1.0599(10) 0.0705(5) 0.078(3) Uani 0.5 1 d . U P C -1
F12 F 0.8340(10) 1.1452(7) -0.0056(4) 0.070(2) Uani 0.5 1 d . U P D -1
F11 F 1.0632(8) 1.1638(5) -0.0027(2) 0.126(2) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C22 1.397(8) . ?
C1 C2 1.409(8) . ?
C1 C21 1.466(8) . ?
B1 F2A 1.327(8) . ?
B1 F1A 1.423(9) . ?
B1 O5 1.484(8) . ?
B1 O6 1.517(9) . ?
O5 C5 1.326(6) . ?
O6 C6 1.319(7) . ?
C2 C3 1.387(8) . ?
C3 C4 1.407(7) . ?
C4 C23 1.390(8) . ?
C4 C5 1.428(8) . ?
C5 C6 1.437(8) . ?
C6 C7 1.387(8) . ?
C7 C8 1.406(8) . ?
C7 C24 1.449(8) . ?
C8 C9 1.374(8) . ?
C9 C10 1.420(8) . ?
C10 C11 1.420(8) . ?
C10 C25 1.420(8) . ?
C11 C12 1.427(8) . ?
C11 C28 1.480(8) . ?
C12 N26 1.379(8) . ?
C12 C13 1.404(8) . ?
C13 C14 1.396(9) . ?
C14 C15 1.427(9) . ?
C15 N26 1.367(7) . ?
C15 C16 1.446(8) . ?
C16 C17 1.399(8) . ?
C16 C34 1.464(8) . ?
C17 N27 1.381(7) . ?
C17 C18 1.418(8) . ?
C18 C19 1.349(8) . ?
C19 C20 1.443(8) . ?
C20 N27 1.376(7) . ?
C20 C21 1.399(7) . ?
C21 C40 1.464(8) . ?
C22 C23 1.377(8) . ?
C23 C24 1.453(8) . ?
C24 C25 1.342(8) . ?
C28 C29 1.375(9) . ?
C28 C33 1.427(9) . ?
C29 C30 1.380(9) . ?
C30 C31 1.396(11) . ?
C31 C32 1.367(10) . ?
C32 C33 1.376(9) . ?
C34 C39 1.393(9) . ?
C34 C35 1.407(9) . ?
C35 C36 1.383(9) . ?
C36 C37 1.376(11) . ?
C37 C38 1.363(10) . ?
C38 C39 1.386(9) . ?
C40 C45 1.394(8) . ?
C40 C41 1.415(7) . ?
C41 C42 1.387(8) . ?
C42 C43 1.363(8) . ?
C43 C44 1.387(8) . ?
C44 C45 1.364(8) . ?
F1 B10 1.356(10) . ?
F2 B10 1.346(10) . ?
F3 B10 1.279(9) . ?
F4 B20 1.359(14) . ?
F5 B20 1.319(14) . ?
F6 B20 1.423(13) . ?
F41 B20 1.23(2) . ?
F51 B20 1.25(2) . ?
F61 B20 1.51(2) . ?
B10 O10 1.512(10) . ?
B20 O10 1.496(12) . ?
B30 F11 1.277(12) 2_775 ?
B30 O20 1.470(12) . ?
B30 F9 1.511(15) . ?
B30 F8 1.554(14) . ?
F11 B30 1.277(12) 2_775 ?

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
C22 C1 C2 117.3(5) . . ?
C22 C1 C21 119.6(5) . . ?
C2 C1 C21 122.9(5) . . ?
F2A B1 F1A 109.2(5) . . ?
F2A B1 O5 115.0(7) . . ?
F1A B1 O5 109.8(6) . . ?
F2A B1 O6 111.7(6) . . ?
F1A B1 O6 106.6(6) . . ?
O5 B1 O6 104.1(5) . . ?
C5 O5 B1 107.8(5) . . ?
C6 O6 B1 106.8(5) . . ?
C3 C2 C1 120.6(5) . . ?
C2 C3 C4 118.8(5) . . ?
C23 C4 C3 121.9(5) . . ?
C23 C4 C5 114.2(5) . . ?
C3 C4 C5 123.8(5) . . ?
O5 C5 C4 127.2(5) . . ?
O5 C5 C6 110.3(5) . . ?
C4 C5 C6 122.3(5) . . ?
O6 C6 C7 126.2(5) . . ?
O6 C6 C5 110.8(5) . . ?
C7 C6 C5 122.9(5) . . ?
C6 C7 C8 126.0(6) . . ?
C6 C7 C24 116.0(5) . . ?
C8 C7 C24 118.0(5) . . ?
C9 C8 C7 120.7(6) . . ?
C8 C9 C10 121.8(6) . . ?
C9 C10 C11 124.0(6) . . ?
C9 C10 C25 116.1(5) . . ?
C11 C10 C25 119.8(6) . . ?
C10 C11 C12 123.0(6) . . ?
C10 C11 C28 121.2(6) . . ?
C12 C11 C28 115.8(5) . . ?
N26 C12 C13 107.3(5) . . ?
N26 C12 C11 126.2(6) . . ?
C13 C12 C11 126.5(6) . . ?
C14 C13 C12 109.2(6) . . ?
C13 C14 C15 105.4(6) . . ?
N26 C15 C14 108.9(6) . . ?
N26 C15 C16 125.1(6) . . ?
C14 C15 C16 125.9(5) . . ?
C17 C16 C15 121.7(5) . . ?
C17 C16 C34 119.5(6) . . ?
C15 C16 C34 118.8(6) . . ?
N27 C17 C16 124.2(6) . . ?
N27 C17 C18 106.6(5) . . ?
C16 C17 C18 129.2(5) . . ?
C19 C18 C17 108.7(5) . . ?
C18 C19 C20 108.5(5) . . ?
N27 C20 C21 129.7(5) . . ?
N27 C20 C19 105.7(5) . . ?
C21 C20 C19 124.2(6) . . ?
C20 C21 C40 116.3(5) . . ?
C20 C21 C1 122.9(5) . . ?
C40 C21 C1 120.6(5) . . ?
C23 C22 C1 123.9(5) . . ?
C22 C23 C4 116.4(6) . . ?
C22 C23 C24 118.5(5) . . ?
C4 C23 C24 124.5(5) . . ?
C25 C24 C7 119.1(6) . . ?
C25 C24 C23 121.7(6) . . ?
C7 C24 C23 119.1(5) . . ?
C24 C25 C10 123.5(6) . . ?
C15 N26 C12 109.2(5) . . ?
C20 N27 C17 110.3(5) . . ?
C29 C28 C33 119.0(6) . . ?
C29 C28 C11 119.5(6) . . ?
C33 C28 C11 121.5(6) . . ?
C28 C29 C30 121.0(7) . . ?
C29 C30 C31 120.0(7) . . ?
C32 C31 C30 119.3(7) . . ?
C31 C32 C33 121.9(8) . . ?
C32 C33 C28 118.8(7) . . ?
C39 C34 C35 119.1(6) . . ?
C39 C34 C16 120.8(6) . . ?
C35 C34 C16 120.1(6) . . ?
C36 C35 C34 118.9(7) . . ?
C37 C36 C35 121.2(7) . . ?
C38 C37 C36 120.0(7) . . ?
C37 C38 C39 120.4(8) . . ?
C38 C39 C34 120.2(7) . . ?
C45 C40 C41 118.2(6) . . ?
C45 C40 C21 123.2(5) . . ?
C41 C40 C21 118.5(5) . . ?
C42 C41 C40 119.3(6) . . ?
C43 C42 C41 120.9(6) . . ?
C42 C43 C44 120.4(6) . . ?
C45 C44 C43 119.7(6) . . ?
C44 C45 C40 121.5(6) . . ?
F3 B10 F2 114.6(8) . . ?
F3 B10 F1 114.6(9) . . ?
F2 B10 F1 106.9(7) . . ?
F3 B10 O10 110.9(7) . . ?
F2 B10 O10 103.6(7) . . ?
F1 B10 O10 105.3(6) . . ?
F41 B20 F51 120.1(18) . . ?
F5 B20 F4 112.0(8) . . ?
F5 B20 F6 109.6(12) . . ?
F4 B20 F6 105.2(10) . . ?
F41 B20 O10 105.2(14) . . ?
F51 B20 O10 104.3(14) . . ?
F5 B20 O10 113.2(9) . . ?
F4 B20 O10 108.6(10) . . ?
F6 B20 O10 107.9(7) . . ?
F41 B20 F61 108.9(17) . . ?
F51 B20 F61 114.2(18) . . ?
O10 B20 F61 102.0(10) . . ?
B20 O10 B10 127.8(6) . . ?
F11 B30 O20 140.8(13) 2_775 . ?
F11 B30 F9 99.7(9) 2_775 . ?
O20 B30 F9 102.4(8) . . ?
F11 B30 F8 111.9(7) 2_775 . ?
O20 B30 F8 98.2(8) . . ?
F9 B30 F8 94.8(10) . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.085




# start Validation Reply Form
_vrf_RINTA01_2                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: poor data according to small organic crystal weekly diffracting
;
_vrf_PLAT020_2                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.296 Report
RESPONSE: poor data according to small organic crystal weakly diffracting
;
_vrf_PLAT026_2                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        23% Check 
RESPONSE: poor data according to small organic crystal weekly diffracting
;
_vrf_PLAT029_2                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.916 Why?  
RESPONSE: data was collected for the whole required theta range (0.991) but
ratio observed / unique reflections for the whole required range  
is very low (15%)
;
_vrf_PLAT026_2BF2                
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        23% Check 
RESPONSE: data collected for low quality crystal 
;
# end Validation Reply Form


#====== end of cif
