# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_LCS16034
_database_code_depnum_ccdc_archive 'CCDC 1588230'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

# ========================================================================= #

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '29 November 2017'

# ========================================================================= #


_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H15 F15 N4 O2, 0.5(C6), C6 H14'
_chemical_formula_sum            'C54 H36 F15 N4 O2'
_chemical_formula_weight         1057.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.7872(9)
_cell_length_b                   24.9663(13)
_cell_length_c                   26.3075(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.737(2)
_cell_angle_gamma                90
_cell_volume                     11020.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6583
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      24.25

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             4312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71076
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.691
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_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             9700
_reflns_number_gt                7884
_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       'APEX2 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


_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)+(0.2000P)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         9700
_refine_ls_number_parameters     701
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.2696
_refine_ls_wR_factor_gt          0.2499
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      3.290
_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
F6 F 0.71983(10) 0.77388(7) 0.25863(6) 0.0461(5) Uani 1 1 d . . . . .
F10 F 0.85888(11) 0.71829(8) 0.40736(7) 0.0570(5) Uani 1 1 d . . . . .
F5 F 0.35390(12) 0.74590(8) 0.33720(6) 0.0606(6) Uani 1 1 d . . . . .
F1 F 0.43219(12) 0.72073(9) 0.50824(6) 0.0608(6) Uani 1 1 d . . . . .
F7 F 0.83181(12) 0.84870(7) 0.24325(7) 0.0576(5) Uani 1 1 d . . . . .
N1 N 0.48581(12) 0.59436(7) 0.39880(7) 0.0234(4) Uani 1 1 d . . . . .
F11 F 0.72493(12) 0.48565(9) 0.21951(7) 0.0657(6) Uani 1 1 d . . . . .
F9 F 0.97001(12) 0.79337(9) 0.39195(8) 0.0690(6) Uani 1 1 d . . . . .
O1 O 0.33282(14) 0.29037(9) 0.51905(8) 0.0516(6) Uani 1 1 d D . . . .
O2 O 0.23851(13) 0.29940(9) 0.45882(8) 0.0534(6) Uani 1 1 d . . . . .
N2 N 0.59099(12) 0.68231(8) 0.37166(7) 0.0246(5) Uani 1 1 d D . . . .
N4 N 0.60164(12) 0.51572(8) 0.36984(7) 0.0263(5) Uani 1 1 d D . . . .
F8 F 0.95831(13) 0.85748(8) 0.30902(9) 0.0680(6) Uani 1 1 d . . . . .
F13 F 0.91767(12) 0.35160(9) 0.23053(10) 0.0758(7) Uani 1 1 d . . . . .
F15 F 0.83975(14) 0.43891(10) 0.37776(8) 0.0748(7) Uani 1 1 d . . . . .
N3 N 0.70428(12) 0.60256(8) 0.33928(8) 0.0286(5) Uani 1 1 d . . . . .
F4 F 0.25003(14) 0.82068(10) 0.36401(9) 0.0836(8) Uani 1 1 d . . . . .
F3 F 0.23427(15) 0.84576(9) 0.46329(10) 0.0861(8) Uani 1 1 d . . . . .
F14 F 0.92925(14) 0.36518(10) 0.33300(10) 0.0850(8) Uani 1 1 d . . . . .
F12 F 0.81317(14) 0.41055(11) 0.17529(9) 0.0881(9) Uani 1 1 d . . . . .
F2 F 0.32562(15) 0.79571(10) 0.53530(8) 0.0804(7) Uani 1 1 d . . . . .
C2 C 0.44457(15) 0.54951(9) 0.41162(9) 0.0258(5) Uani 1 1 d . . . . .
C5 C 0.43674(15) 0.63602(10) 0.40977(9) 0.0265(5) Uani 1 1 d . . . . .
C1 C 0.47360(15) 0.49656(9) 0.40899(8) 0.0264(5) Uani 1 1 d . . . . .
C6 C 0.45643(15) 0.69061(9) 0.40554(9) 0.0264(5) Uani 1 1 d . . . . .
C10 C 0.65229(15) 0.71570(9) 0.35971(9) 0.0263(5) Uani 1 1 d . . . . .
C7 C 0.52833(15) 0.71140(9) 0.38864(8) 0.0251(5) Uani 1 1 d . . . . .
C20 C 0.54669(15) 0.48160(9) 0.38963(9) 0.0266(5) Uani 1 1 d . . . . .
C21 C 0.42454(15) 0.45186(9) 0.42890(9) 0.0278(5) Uani 1 1 d . . . . .
C34 C 0.78568(15) 0.74288(10) 0.33300(10) 0.0313(6) Uani 1 1 d . . . . .
C8 C 0.55086(16) 0.76651(10) 0.38684(9) 0.0293(6) Uani 1 1 d . . . . .
H8 H 0.5190 0.7961 0.3962 0.035 Uiso 1 1 calc R U . . .
C9 C 0.62587(15) 0.76894(10) 0.36941(9) 0.0285(5) Uani 1 1 d . . . . .
H9 H 0.6558 0.8007 0.3645 0.034 Uiso 1 1 calc R U . . .
C27 C 0.29974(17) 0.31504(11) 0.48078(10) 0.0353(6) Uani 1 1 d . . . . .
C28 C 0.39666(16) 0.73115(10) 0.42133(10) 0.0309(6) Uani 1 1 d . . . . .
C24 C 0.34173(16) 0.36358(10) 0.46380(9) 0.0322(6) Uani 1 1 d . . . . .
C15 C 0.74854(16) 0.56087(11) 0.32131(10) 0.0322(6) Uani 1 1 d . . . . .
C12 C 0.74834(15) 0.64702(10) 0.33060(10) 0.0308(6) Uani 1 1 d . . . . .
C11 C 0.72567(15) 0.69995(10) 0.34151(9) 0.0277(5) Uani 1 1 d . . . . .
C3 C 0.36711(16) 0.56323(11) 0.43065(10) 0.0341(6) Uani 1 1 d . . . . .
H3 H 0.3277 0.5391 0.4421 0.041 Uiso 1 1 calc R U . . .
C35 C 0.78072(16) 0.77754(10) 0.29177(10) 0.0329(6) Uani 1 1 d . . . . .
C19 C 0.57372(16) 0.42851(10) 0.38181(10) 0.0329(6) Uani 1 1 d . . . . .
H19 H 0.5479 0.3968 0.3925 0.040 Uiso 1 1 calc R U . . .
C17 C 0.66153(15) 0.48595(10) 0.34859(9) 0.0288(5) Uani 1 1 d . . . . .
C16 C 0.72847(15) 0.50673(10) 0.32477(9) 0.0300(6) Uani 1 1 d . . . . .
C4 C 0.36211(16) 0.61690(11) 0.42887(11) 0.0350(6) Uani 1 1 d . . . . .
H4 H 0.3180 0.6382 0.4383 0.042 Uiso 1 1 calc DR U . . .
C26 C 0.45060(17) 0.42514(11) 0.47223(10) 0.0351(6) Uani 1 1 d . . . . .
H26 H 0.4971 0.4372 0.4902 0.042 Uiso 1 1 calc R U . . .
C39 C 0.85121(17) 0.74953(11) 0.36647(10) 0.0378(6) Uani 1 1 d . . . . .
C25 C 0.41001(17) 0.38105(11) 0.48991(10) 0.0364(6) Uani 1 1 d . . . . .
H25 H 0.4287 0.3629 0.5197 0.044 Uiso 1 1 calc R U . . .
C40 C 0.78095(15) 0.46626(10) 0.30077(11) 0.0357(6) Uani 1 1 d . . . . .
C22 C 0.35526(16) 0.43474(11) 0.40366(10) 0.0336(6) Uani 1 1 d . . . . .
H22 H 0.3361 0.4532 0.3742 0.040 Uiso 1 1 calc R U . . .
C23 C 0.31434(17) 0.39112(11) 0.42119(10) 0.0373(6) Uani 1 1 d . . . . .
H23 H 0.2668 0.3798 0.4039 0.045 Uiso 1 1 calc R U . . .
C18 C 0.64326(16) 0.43083(10) 0.35635(10) 0.0337(6) Uani 1 1 d . . . . .
H18 H 0.6739 0.4011 0.3457 0.040 Uiso 1 1 calc R U . . .
C14 C 0.82261(17) 0.57976(12) 0.30104(11) 0.0407(7) Uani 1 1 d . . . . .
H14 H 0.8629 0.5586 0.2863 0.049 Uiso 1 1 calc R U . . .
C13 C 0.82327(17) 0.63304(11) 0.30710(11) 0.0393(7) Uani 1 1 d . . . . .
H13 H 0.8644 0.6570 0.2979 0.047 Uiso 1 1 calc R U . . .
C33 C 0.34811(18) 0.75706(12) 0.38625(11) 0.0400(7) Uani 1 1 d . . . . .
C36 C 0.83830(19) 0.81613(11) 0.28378(11) 0.0426(7) Uani 1 1 d . . . . .
C37 C 0.90228(18) 0.82082(12) 0.31696(12) 0.0453(7) Uani 1 1 d . . . . .
C29 C 0.38753(18) 0.74486(11) 0.47196(11) 0.0397(7) Uani 1 1 d . . . . .
C41 C 0.77576(17) 0.45741(12) 0.24827(11) 0.0418(7) Uani 1 1 d . . . . .
C38 C 0.90849(18) 0.78771(13) 0.35890(12) 0.0443(7) Uani 1 1 d . . . . .
C45 C 0.83362(19) 0.43420(13) 0.32769(12) 0.0478(8) Uani 1 1 d . . . . .
C44 C 0.8800(2) 0.39535(13) 0.30537(15) 0.0553(9) Uani 1 1 d . . . . .
C30 C 0.3341(2) 0.78327(13) 0.48656(12) 0.0520(8) Uani 1 1 d . . . . .
C43 C 0.87339(18) 0.38823(13) 0.25346(14) 0.0519(8) Uani 1 1 d . . . . .
C31 C 0.2871(2) 0.80874(13) 0.44976(14) 0.0550(9) Uani 1 1 d . . . . .
C42 C 0.82068(18) 0.41915(15) 0.22493(13) 0.0536(9) Uani 1 1 d . . . . .
C32 C 0.2947(2) 0.79623(13) 0.39996(14) 0.0539(9) Uani 1 1 d . . . . .
C57 C 0.5000 0.72870(19) 0.2500 0.0590(13) Uani 1 2 d S T P . .
C55 C 0.5000 0.6281(2) 0.2500 0.082(2) Uani 1 2 d S T P . .
C52 C 0.5000 0.4733(2) 0.2500 0.0737(17) Uani 1 2 d S T P . .
C54 C 0.5000 0.5730(2) 0.2500 0.087(2) Uani 1 2 d S T P . .
C49 C 0.8923(4) 0.6335(3) 0.1613(2) 0.1106(19) Uani 1 1 d . . . . .
H49A H 0.8440 0.6272 0.1812 0.133 Uiso 1 1 calc R U . . .
H49B H 0.8754 0.6355 0.1250 0.133 Uiso 1 1 calc R U . . .
C47 C 0.9143(4) 0.5359(3) 0.1541(3) 0.130(2) Uani 1 1 d . . . . .
H47A H 0.8965 0.5370 0.1178 0.156 Uiso 1 1 calc R U . . .
H47B H 0.8669 0.5284 0.1745 0.156 Uiso 1 1 calc R U . . .
C48 C 0.9460(4) 0.5880(3) 0.1685(3) 0.120(2) Uani 1 1 d . . . . .
H48A H 0.9941 0.5946 0.1486 0.144 Uiso 1 1 calc R U . . .
H48B H 0.9630 0.5865 0.2048 0.144 Uiso 1 1 calc R U . . .
C50 C 0.9300(4) 0.6893(4) 0.1778(3) 0.148(3) Uani 1 1 d . . . . .
H50A H 0.9467 0.6877 0.2142 0.178 Uiso 1 1 calc R U . . .
H50B H 0.9780 0.6961 0.1579 0.178 Uiso 1 1 calc R U . . .
C56 C 0.4581(4) 0.6728(2) 0.2595(2) 0.0411(13) Uani 0.5 1 d . . P . .
C53 C 0.5386(4) 0.5298(3) 0.2373(2) 0.0525(16) Uani 0.5 1 d . . P . .
C51 C 0.8731(5) 0.7338(4) 0.1699(3) 0.172(4) Uani 1 1 d . . . . .
H51A H 0.8589 0.7368 0.1336 0.258 Uiso 1 1 calc R U . . .
H51B H 0.8976 0.7673 0.1818 0.258 Uiso 1 1 calc R U . . .
H51C H 0.8250 0.7268 0.1890 0.258 Uiso 1 1 calc R U . . .
C46 C 0.9729(5) 0.4908(4) 0.1613(4) 0.188(4) Uani 1 1 d . . . . .
H46A H 1.0225 0.4997 0.1445 0.281 Uiso 1 1 calc R U . . .
H46B H 0.9504 0.4579 0.1465 0.281 Uiso 1 1 calc R U . . .
H46C H 0.9840 0.4853 0.1978 0.281 Uiso 1 1 calc R U . . .
H2 H 0.5953(19) 0.6487(7) 0.3726(12) 0.046(9) Uiso 1 1 d D . . . .
H5 H 0.6046(17) 0.5548(13) 0.3703(10) 0.037(8) Uiso 1 1 d . . . . .
H1 H 0.324(3) 0.2568(11) 0.530(2) 0.13(2) Uiso 1 1 d 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
F6 C35 1.326(3) . ?
F10 C39 1.332(3) . ?
F5 C33 1.327(3) . ?
F1 C29 1.339(3) . ?
F7 C36 1.343(3) . ?
N1 C5 1.363(3) . ?
N1 C2 1.364(3) . ?
F11 C41 1.326(4) . ?
F9 C38 1.337(3) . ?
O1 C27 1.291(3) . ?
O1 H1 0.91(2) . ?
O2 C27 1.228(3) . ?
N2 C7 1.365(3) . ?
N2 C10 1.368(3) . ?
N2 H2 0.844(18) . ?
N4 C20 1.370(3) . ?
N4 C17 1.382(3) . ?
N4 H5 0.98(3) . ?
F8 C37 1.333(3) . ?
F13 C43 1.334(3) . ?
F15 C45 1.323(4) . ?
N3 C12 1.357(3) . ?
N3 C15 1.371(3) . ?
F4 C32 1.337(4) . ?
F3 C31 1.337(3) . ?
F14 C44 1.320(4) . ?
F12 C42 1.326(4) . ?
F2 C30 1.331(4) . ?
C2 C1 1.411(3) . ?
C2 C3 1.449(3) . ?
C5 C6 1.408(3) . ?
C5 C4 1.445(3) . ?
C1 C20 1.393(3) . ?
C1 C21 1.491(3) . ?
C6 C7 1.399(3) . ?
C6 C28 1.493(3) . ?
C10 C11 1.392(4) . ?
C10 C9 1.427(3) . ?
C7 C8 1.428(3) . ?
C20 C19 1.418(4) . ?
C21 C26 1.380(4) . ?
C21 C22 1.389(4) . ?
C34 C35 1.388(4) . ?
C34 C39 1.398(4) . ?
C34 C11 1.492(3) . ?
C8 C9 1.355(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C27 C24 1.478(3) . ?
C28 C33 1.374(4) . ?
C28 C29 1.388(4) . ?
C24 C23 1.382(4) . ?
C24 C25 1.389(4) . ?
C15 C16 1.397(4) . ?
C15 C14 1.447(4) . ?
C12 C11 1.407(4) . ?
C12 C13 1.461(4) . ?
C3 C4 1.343(4) . ?
C3 H3 0.9500 . ?
C35 C36 1.385(4) . ?
C19 C18 1.365(4) . ?
C19 H19 0.9500 . ?
C17 C16 1.403(4) . ?
C17 C18 1.426(4) . ?
C16 C40 1.493(3) . ?
C4 H4 0.9500 . ?
C26 C25 1.383(4) . ?
C26 H26 0.9500 . ?
C39 C38 1.373(4) . ?
C25 H25 0.9500 . ?
C40 C45 1.373(4) . ?
C40 C41 1.399(4) . ?
C22 C23 1.375(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C18 H18 0.9500 . ?
C14 C13 1.340(4) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?
C33 C32 1.382(4) . ?
C36 C37 1.368(4) . ?
C37 C38 1.380(4) . ?
C29 C30 1.376(4) . ?
C41 C42 1.373(4) . ?
C45 C44 1.386(4) . ?
C44 C43 1.378(5) . ?
C30 C31 1.384(5) . ?
C43 C42 1.379(5) . ?
C31 C32 1.357(5) . ?
C57 C56 1.586(7) . ?
C57 C56 1.586(7) 2_655 ?
C55 C56 1.345(7) 2_655 ?
C55 C56 1.345(7) . ?
C55 C54 1.376(7) . ?
C52 C53 1.590(8) 2_655 ?
C52 C53 1.590(8) . ?
C54 C53 1.308(7) . ?
C54 C53 1.308(7) 2_655 ?
C49 C48 1.459(8) . ?
C49 C50 1.586(10) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C47 C48 1.451(9) . ?
C47 C46 1.504(9) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C50 C51 1.477(10) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C56 C56 1.507(12) 2_655 ?
C53 C53 1.476(15) 2_655 ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?

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
C5 N1 C2 105.0(2) . . ?
C27 O1 H1 129(4) . . ?
C7 N2 C10 110.1(2) . . ?
C7 N2 H2 126(2) . . ?
C10 N2 H2 123(2) . . ?
C20 N4 C17 109.0(2) . . ?
C20 N4 H5 130.6(17) . . ?
C17 N4 H5 120.3(17) . . ?
C12 N3 C15 105.0(2) . . ?
N1 C2 C1 125.3(2) . . ?
N1 C2 C3 111.0(2) . . ?
C1 C2 C3 123.6(2) . . ?
N1 C5 C6 125.3(2) . . ?
N1 C5 C4 110.9(2) . . ?
C6 C5 C4 123.7(2) . . ?
C20 C1 C2 125.3(2) . . ?
C20 C1 C21 115.4(2) . . ?
C2 C1 C21 119.2(2) . . ?
C7 C6 C5 126.3(2) . . ?
C7 C6 C28 115.5(2) . . ?
C5 C6 C28 118.2(2) . . ?
N2 C10 C11 125.9(2) . . ?
N2 C10 C9 106.6(2) . . ?
C11 C10 C9 127.4(2) . . ?
N2 C7 C6 126.0(2) . . ?
N2 C7 C8 107.1(2) . . ?
C6 C7 C8 126.9(2) . . ?
N4 C20 C1 125.7(2) . . ?
N4 C20 C19 107.7(2) . . ?
C1 C20 C19 126.3(2) . . ?
C26 C21 C22 119.1(2) . . ?
C26 C21 C1 119.1(2) . . ?
C22 C21 C1 121.7(2) . . ?
C35 C34 C39 116.5(2) . . ?
C35 C34 C11 122.7(2) . . ?
C39 C34 C11 120.8(2) . . ?
C9 C8 C7 107.7(2) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
C8 C9 C10 108.4(2) . . ?
C8 C9 H9 125.8 . . ?
C10 C9 H9 125.8 . . ?
O2 C27 O1 123.3(2) . . ?
O2 C27 C24 121.3(2) . . ?
O1 C27 C24 115.4(2) . . ?
C33 C28 C29 116.6(2) . . ?
C33 C28 C6 121.5(2) . . ?
C29 C28 C6 121.9(2) . . ?
C23 C24 C25 119.6(2) . . ?
C23 C24 C27 120.2(2) . . ?
C25 C24 C27 120.1(2) . . ?
N3 C15 C16 125.3(2) . . ?
N3 C15 C14 111.1(2) . . ?
C16 C15 C14 123.4(2) . . ?
N3 C12 C11 125.6(2) . . ?
N3 C12 C13 110.9(2) . . ?
C11 C12 C13 123.5(2) . . ?
C10 C11 C12 125.7(2) . . ?
C10 C11 C34 117.2(2) . . ?
C12 C11 C34 117.1(2) . . ?
C4 C3 C2 106.2(2) . . ?
C4 C3 H3 126.9 . . ?
C2 C3 H3 126.9 . . ?
F6 C35 C36 118.4(2) . . ?
F6 C35 C34 119.8(2) . . ?
C36 C35 C34 121.8(3) . . ?
C18 C19 C20 108.3(2) . . ?
C18 C19 H19 125.9 . . ?
C20 C19 H19 125.9 . . ?
N4 C17 C16 125.8(2) . . ?
N4 C17 C18 107.4(2) . . ?
C16 C17 C18 126.8(2) . . ?
C15 C16 C17 125.8(2) . . ?
C15 C16 C40 118.7(2) . . ?
C17 C16 C40 115.4(2) . . ?
C3 C4 C5 106.7(2) . . ?
C3 C4 H4 126.6 . . ?
C5 C4 H4 126.6 . . ?
C21 C26 C25 121.0(2) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
F10 C39 C38 118.2(2) . . ?
F10 C39 C34 119.6(2) . . ?
C38 C39 C34 122.2(3) . . ?
C26 C25 C24 119.4(2) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C45 C40 C41 115.9(3) . . ?
C45 C40 C16 123.7(3) . . ?
C41 C40 C16 120.3(2) . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C18 C17 107.6(2) . . ?
C19 C18 H18 126.2 . . ?
C17 C18 H18 126.2 . . ?
C13 C14 C15 106.5(2) . . ?
C13 C14 H14 126.8 . . ?
C15 C14 H14 126.8 . . ?
C14 C13 C12 106.5(2) . . ?
C14 C13 H13 126.8 . . ?
C12 C13 H13 126.8 . . ?
F5 C33 C28 119.7(2) . . ?
F5 C33 C32 118.0(3) . . ?
C28 C33 C32 122.3(3) . . ?
F7 C36 C37 119.9(3) . . ?
F7 C36 C35 120.1(3) . . ?
C37 C36 C35 120.0(3) . . ?
F8 C37 C36 120.2(3) . . ?
F8 C37 C38 120.0(3) . . ?
C36 C37 C38 119.8(3) . . ?
F1 C29 C30 118.1(3) . . ?
F1 C29 C28 119.8(2) . . ?
C30 C29 C28 122.1(3) . . ?
F11 C41 C42 117.9(3) . . ?
F11 C41 C40 119.9(2) . . ?
C42 C41 C40 122.2(3) . . ?
F9 C38 C39 120.6(3) . . ?
F9 C38 C37 119.7(3) . . ?
C39 C38 C37 119.7(3) . . ?
F15 C45 C40 119.4(3) . . ?
F15 C45 C44 117.1(3) . . ?
C40 C45 C44 123.4(3) . . ?
F14 C44 C43 120.2(3) . . ?
F14 C44 C45 121.1(3) . . ?
C43 C44 C45 118.7(3) . . ?
F2 C30 C29 121.4(3) . . ?
F2 C30 C31 119.5(3) . . ?
C29 C30 C31 119.2(3) . . ?
F13 C43 C44 120.5(3) . . ?
F13 C43 C42 119.7(3) . . ?
C44 C43 C42 119.9(3) . . ?
F3 C31 C32 119.9(3) . . ?
F3 C31 C30 120.0(3) . . ?
C32 C31 C30 120.1(3) . . ?
F12 C42 C41 121.1(3) . . ?
F12 C42 C43 119.1(3) . . ?
C41 C42 C43 119.9(3) . . ?
F4 C32 C31 120.7(3) . . ?
F4 C32 C33 119.6(3) . . ?
C31 C32 C33 119.7(3) . . ?
C56 C57 C56 56.7(4) . 2_655 ?
C56 C55 C56 68.1(6) 2_655 . ?
C56 C55 C54 145.9(3) 2_655 . ?
C56 C55 C54 145.9(3) . . ?
C53 C52 C53 55.3(5) 2_655 . ?
C53 C54 C53 68.7(7) . 2_655 ?
C53 C54 C55 145.7(4) . . ?
C53 C54 C55 145.7(4) 2_655 . ?
C48 C49 C50 114.1(6) . . ?
C48 C49 H49A 108.7 . . ?
C50 C49 H49A 108.7 . . ?
C48 C49 H49B 108.7 . . ?
C50 C49 H49B 108.7 . . ?
H49A C49 H49B 107.6 . . ?
C48 C47 C46 113.9(6) . . ?
C48 C47 H47A 108.8 . . ?
C46 C47 H47A 108.8 . . ?
C48 C47 H47B 108.8 . . ?
C46 C47 H47B 108.8 . . ?
H47A C47 H47B 107.7 . . ?
C47 C48 C49 116.4(6) . . ?
C47 C48 H48A 108.2 . . ?
C49 C48 H48A 108.2 . . ?
C47 C48 H48B 108.2 . . ?
C49 C48 H48B 108.2 . . ?
H48A C48 H48B 107.3 . . ?
C51 C50 C49 111.8(7) . . ?
C51 C50 H50A 109.3 . . ?
C49 C50 H50A 109.3 . . ?
C51 C50 H50B 109.3 . . ?
C49 C50 H50B 109.3 . . ?
H50A C50 H50B 107.9 . . ?
C55 C56 C56 55.9(3) . 2_655 ?
C55 C56 C57 117.6(4) . . ?
C56 C56 C57 61.6(2) 2_655 . ?
C54 C53 C53 55.7(4) . 2_655 ?
C54 C53 C52 118.0(5) . . ?
C53 C53 C52 62.4(3) 2_655 . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C47 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C47 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C1 -176.9(2) . . . . ?
C5 N1 C2 C3 0.6(3) . . . . ?
C2 N1 C5 C6 175.9(2) . . . . ?
C2 N1 C5 C4 -1.3(3) . . . . ?
N1 C2 C1 C20 -4.7(4) . . . . ?
C3 C2 C1 C20 178.1(2) . . . . ?
N1 C2 C1 C21 174.3(2) . . . . ?
C3 C2 C1 C21 -3.0(3) . . . . ?
N1 C5 C6 C7 1.3(4) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
N1 C5 C6 C28 -177.4(2) . . . . ?
C4 C5 C6 C28 -0.5(4) . . . . ?
C7 N2 C10 C11 179.6(2) . . . . ?
C7 N2 C10 C9 -0.6(2) . . . . ?
C10 N2 C7 C6 -178.2(2) . . . . ?
C10 N2 C7 C8 0.6(2) . . . . ?
C5 C6 C7 N2 2.4(4) . . . . ?
C28 C6 C7 N2 -179.0(2) . . . . ?
C5 C6 C7 C8 -176.2(2) . . . . ?
C28 C6 C7 C8 2.5(3) . . . . ?
C17 N4 C20 C1 -172.3(2) . . . . ?
C17 N4 C20 C19 1.5(3) . . . . ?
C2 C1 C20 N4 -0.4(4) . . . . ?
C21 C1 C20 N4 -179.4(2) . . . . ?
C2 C1 C20 C19 -173.1(2) . . . . ?
C21 C1 C20 C19 7.9(3) . . . . ?
C20 C1 C21 C26 67.8(3) . . . . ?
C2 C1 C21 C26 -111.2(3) . . . . ?
C20 C1 C21 C22 -109.0(3) . . . . ?
C2 C1 C21 C22 71.9(3) . . . . ?
N2 C7 C8 C9 -0.5(3) . . . . ?
C6 C7 C8 C9 178.3(2) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
N2 C10 C9 C8 0.2(3) . . . . ?
C11 C10 C9 C8 -179.9(2) . . . . ?
C7 C6 C28 C33 81.5(3) . . . . ?
C5 C6 C28 C33 -99.7(3) . . . . ?
C7 C6 C28 C29 -98.0(3) . . . . ?
C5 C6 C28 C29 80.8(3) . . . . ?
O2 C27 C24 C23 -2.8(4) . . . . ?
O1 C27 C24 C23 175.9(3) . . . . ?
O2 C27 C24 C25 178.7(3) . . . . ?
O1 C27 C24 C25 -2.6(4) . . . . ?
C12 N3 C15 C16 176.3(3) . . . . ?
C12 N3 C15 C14 0.3(3) . . . . ?
C15 N3 C12 C11 178.0(2) . . . . ?
C15 N3 C12 C13 -0.8(3) . . . . ?
N2 C10 C11 C12 2.4(4) . . . . ?
C9 C10 C11 C12 -177.4(2) . . . . ?
N2 C10 C11 C34 -177.4(2) . . . . ?
C9 C10 C11 C34 2.8(4) . . . . ?
N3 C12 C11 C10 -4.7(4) . . . . ?
C13 C12 C11 C10 174.1(3) . . . . ?
N3 C12 C11 C34 175.1(2) . . . . ?
C13 C12 C11 C34 -6.2(4) . . . . ?
C35 C34 C11 C10 -75.5(3) . . . . ?
C39 C34 C11 C10 105.4(3) . . . . ?
C35 C34 C11 C12 104.7(3) . . . . ?
C39 C34 C11 C12 -74.3(3) . . . . ?
N1 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 177.9(2) . . . . ?
C39 C34 C35 F6 -179.5(2) . . . . ?
C11 C34 C35 F6 1.4(4) . . . . ?
C39 C34 C35 C36 1.0(4) . . . . ?
C11 C34 C35 C36 -178.1(2) . . . . ?
N4 C20 C19 C18 -1.6(3) . . . . ?
C1 C20 C19 C18 172.2(2) . . . . ?
C20 N4 C17 C16 -179.8(2) . . . . ?
C20 N4 C17 C18 -0.9(3) . . . . ?
N3 C15 C16 C17 -2.3(4) . . . . ?
C14 C15 C16 C17 173.2(3) . . . . ?
N3 C15 C16 C40 176.7(2) . . . . ?
C14 C15 C16 C40 -7.7(4) . . . . ?
N4 C17 C16 C15 4.3(4) . . . . ?
C18 C17 C16 C15 -174.3(3) . . . . ?
N4 C17 C16 C40 -174.8(2) . . . . ?
C18 C17 C16 C40 6.6(4) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
N1 C5 C4 C3 1.6(3) . . . . ?
C6 C5 C4 C3 -175.8(2) . . . . ?
C22 C21 C26 C25 1.7(4) . . . . ?
C1 C21 C26 C25 -175.3(3) . . . . ?
C35 C34 C39 F10 178.7(2) . . . . ?
C11 C34 C39 F10 -2.2(4) . . . . ?
C35 C34 C39 C38 -0.9(4) . . . . ?
C11 C34 C39 C38 178.2(3) . . . . ?
C21 C26 C25 C24 -0.4(4) . . . . ?
C23 C24 C25 C26 -1.4(4) . . . . ?
C27 C24 C25 C26 177.2(3) . . . . ?
C15 C16 C40 C45 104.1(3) . . . . ?
C17 C16 C40 C45 -76.7(4) . . . . ?
C15 C16 C40 C41 -78.9(3) . . . . ?
C17 C16 C40 C41 100.3(3) . . . . ?
C26 C21 C22 C23 -1.3(4) . . . . ?
C1 C21 C22 C23 175.6(2) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C25 C24 C23 C22 1.8(4) . . . . ?
C27 C24 C23 C22 -176.7(3) . . . . ?
C20 C19 C18 C17 1.0(3) . . . . ?
N4 C17 C18 C19 -0.1(3) . . . . ?
C16 C17 C18 C19 178.8(2) . . . . ?
N3 C15 C14 C13 0.4(3) . . . . ?
C16 C15 C14 C13 -175.7(3) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?
N3 C12 C13 C14 1.1(3) . . . . ?
C11 C12 C13 C14 -177.8(3) . . . . ?
C29 C28 C33 F5 179.9(3) . . . . ?
C6 C28 C33 F5 0.3(4) . . . . ?
C29 C28 C33 C32 2.3(4) . . . . ?
C6 C28 C33 C32 -177.3(3) . . . . ?
F6 C35 C36 F7 -0.1(4) . . . . ?
C34 C35 C36 F7 179.5(2) . . . . ?
F6 C35 C36 C37 -179.5(3) . . . . ?
C34 C35 C36 C37 0.1(4) . . . . ?
F7 C36 C37 F8 -0.3(4) . . . . ?
C35 C36 C37 F8 179.2(3) . . . . ?
F7 C36 C37 C38 179.3(3) . . . . ?
C35 C36 C37 C38 -1.2(5) . . . . ?
C33 C28 C29 F1 179.2(3) . . . . ?
C6 C28 C29 F1 -1.2(4) . . . . ?
C33 C28 C29 C30 -1.4(4) . . . . ?
C6 C28 C29 C30 178.2(3) . . . . ?
C45 C40 C41 F11 178.3(3) . . . . ?
C16 C40 C41 F11 1.1(4) . . . . ?
C45 C40 C41 C42 -0.2(4) . . . . ?
C16 C40 C41 C42 -177.4(3) . . . . ?
F10 C39 C38 F9 -0.3(4) . . . . ?
C34 C39 C38 F9 179.3(3) . . . . ?
F10 C39 C38 C37 -179.9(3) . . . . ?
C34 C39 C38 C37 -0.3(5) . . . . ?
F8 C37 C38 F9 1.4(5) . . . . ?
C36 C37 C38 F9 -178.2(3) . . . . ?
F8 C37 C38 C39 -179.1(3) . . . . ?
C36 C37 C38 C39 1.3(5) . . . . ?
C41 C40 C45 F15 -177.6(3) . . . . ?
C16 C40 C45 F15 -0.5(5) . . . . ?
C41 C40 C45 C44 0.4(5) . . . . ?
C16 C40 C45 C44 177.5(3) . . . . ?
F15 C45 C44 F14 -1.3(5) . . . . ?
C40 C45 C44 F14 -179.3(3) . . . . ?
F15 C45 C44 C43 178.1(3) . . . . ?
C40 C45 C44 C43 0.0(5) . . . . ?
F1 C29 C30 F2 -1.1(5) . . . . ?
C28 C29 C30 F2 179.5(3) . . . . ?
F1 C29 C30 C31 -179.9(3) . . . . ?
C28 C29 C30 C31 0.7(5) . . . . ?
F14 C44 C43 F13 -1.3(5) . . . . ?
C45 C44 C43 F13 179.3(3) . . . . ?
F14 C44 C43 C42 178.7(3) . . . . ?
C45 C44 C43 C42 -0.7(5) . . . . ?
F2 C30 C31 F3 0.4(5) . . . . ?
C29 C30 C31 F3 179.3(3) . . . . ?
F2 C30 C31 C32 -179.6(3) . . . . ?
C29 C30 C31 C32 -0.7(5) . . . . ?
F11 C41 C42 F12 -0.3(5) . . . . ?
C40 C41 C42 F12 178.2(3) . . . . ?
F11 C41 C42 C43 -179.0(3) . . . . ?
C40 C41 C42 C43 -0.4(5) . . . . ?
F13 C43 C42 F12 2.2(5) . . . . ?
C44 C43 C42 F12 -177.8(3) . . . . ?
F13 C43 C42 C41 -179.1(3) . . . . ?
C44 C43 C42 C41 0.9(5) . . . . ?
F3 C31 C32 F4 0.3(5) . . . . ?
C30 C31 C32 F4 -179.7(3) . . . . ?
F3 C31 C32 C33 -178.5(3) . . . . ?
C30 C31 C32 C33 1.5(5) . . . . ?
F5 C33 C32 F4 1.2(5) . . . . ?
C28 C33 C32 F4 178.9(3) . . . . ?
F5 C33 C32 C31 180.0(3) . . . . ?
C28 C33 C32 C31 -2.4(5) . . . . ?
C56 C55 C54 C53 -7.5(6) 2_655 . . . ?
C56 C55 C54 C53 172.5(6) . . . . ?
C56 C55 C54 C53 172.6(6) 2_655 . . 2_655 ?
C56 C55 C54 C53 -7.5(6) . . . 2_655 ?
C46 C47 C48 C49 178.9(6) . . . . ?
C50 C49 C48 C47 179.8(6) . . . . ?
C48 C49 C50 C51 -179.9(6) . . . . ?
C54 C55 C56 C56 180.002(2) . . . 2_655 ?
C56 C55 C56 C57 -0.002(1) 2_655 . . . ?
C54 C55 C56 C57 180.000(1) . . . . ?
C56 C57 C56 C55 0.002(1) 2_655 . . . ?
C55 C54 C53 C53 180.002(2) . . . 2_655 ?
C53 C54 C53 C52 -0.002(1) 2_655 . . . ?
C55 C54 C53 C52 180.000(1) . . . . ?
C53 C52 C53 C54 0.001(1) 2_655 . . . ?

_refine_diff_density_max         0.462
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.059




#=============================================================================#
#    Luis Cunha-Silva @ REQUIMTE-LAQV & DQB FCUP   *   29/11/2017  *   END    #
#=============================================================================#
