# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_714
_database_code_depnum_ccdc_archive 'CCDC 1427523'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        azaheptalene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H12 F10 N4'
_chemical_formula_sum            'C38 H12 F10 N4'
_chemical_formula_weight         714.52

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   6.799(3)
_cell_length_b                   8.219(3)
_cell_length_c                   13.376(4)
_cell_angle_alpha                82.308(9)
_cell_angle_beta                 75.542(7)
_cell_angle_gamma                83.754(10)
_cell_volume                     715.1(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13480
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_sigmaI/netI    0.0930
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         28.62
_reflns_number_total             3661
_reflns_number_gt                2230
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3577
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.1119
_refine_ls_wR_factor_ref         0.3393
_refine_ls_wR_factor_gt          0.3271
_refine_ls_goodness_of_fit_ref   1.923
_refine_ls_restrained_S_all      1.923
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F5 F -0.0906(6) 0.5925(4) 0.7727(3) 0.0357(9) Uani 1 1 d . . .
F1 F 0.4982(6) 0.8231(5) 0.7973(3) 0.0407(10) Uani 1 1 d . . .
F4 F -0.2677(6) 0.6402(5) 0.9728(3) 0.0491(11) Uani 1 1 d . . .
N1 N 0.5549(6) 0.2970(5) 0.5776(3) 0.0149(9) Uani 1 1 d . . .
N2 N 0.6876(6) 0.0269(5) 0.5644(3) 0.0179(9) Uani 1 1 d . . .
F3 F -0.0672(8) 0.7856(5) 1.0836(3) 0.0573(13) Uani 1 1 d . . .
F2 F 0.3208(8) 0.8757(6) 0.9956(3) 0.0599(13) Uani 1 1 d . . .
C7 C 0.6523(7) 0.1710(6) 0.5162(4) 0.0150(10) Uani 1 1 d . . .
C4 C 0.4894(7) 0.4620(5) 0.5513(4) 0.0149(10) Uani 1 1 d . . .
C5 C 0.3026(8) 0.6840(6) 0.6669(4) 0.0173(11) Uani 1 1 d . . .
C3 C 0.4042(8) 0.5264(6) 0.6483(4) 0.0178(11) Uani 1 1 d . . .
C2 C 0.4230(8) 0.3983(6) 0.7286(4) 0.0200(11) Uani 1 1 d . . .
H2 H 0.3803 0.4072 0.7995 0.024 Uiso 1 1 calc R . .
C9 C 0.8618(8) -0.2343(6) 0.5005(4) 0.0194(11) Uani 1 1 d . . .
H9 H 0.8386 -0.2923 0.5664 0.023 Uiso 1 1 calc R . .
C1 C 0.5130(8) 0.2615(6) 0.6852(4) 0.0175(11) Uani 1 1 d . . .
H1 H 0.5421 0.1605 0.7212 0.021 Uiso 1 1 calc R . .
C8 C 0.7941(8) -0.0698(6) 0.4858(4) 0.0187(11) Uani 1 1 d . . .
C11 C 0.9989(9) -0.2235(6) 0.3157(5) 0.0239(12) Uani 1 1 d . . .
H11 H 1.0685 -0.2769 0.2586 0.029 Uiso 1 1 calc R . .
C6 C 0.2753(8) 0.8138(6) 0.5966(4) 0.0180(11) Uani 1 1 d . . .
C10 C 0.9654(8) -0.3094(6) 0.4135(4) 0.0225(12) Uani 1 1 d . . .
H10 H 1.0130 -0.4197 0.4212 0.027 Uiso 1 1 calc R . .
C13 C 0.8242(8) 0.0186(6) 0.3866(4) 0.0191(11) Uani 1 1 d . . .
C14 C 0.2092(9) 0.7063(6) 0.7796(4) 0.0233(12) Uani 1 1 d . . .
C19 C 0.0147(9) 0.6605(6) 0.8272(4) 0.0258(13) Uani 1 1 d . . .
C12 C 0.9305(9) -0.0581(6) 0.3009(4) 0.0235(12) Uani 1 1 d . . .
H12 H 0.9558 -0.0005 0.2349 0.028 Uiso 1 1 calc R . .
C15 C 0.3107(10) 0.7760(7) 0.8387(5) 0.0289(13) Uani 1 1 d . . .
C18 C -0.0777(11) 0.6860(7) 0.9286(5) 0.0381(15) Uani 1 1 d . . .
C17 C 0.0261(12) 0.7570(8) 0.9840(4) 0.0380(16) Uani 1 1 d . . .
C16 C 0.2199(11) 0.8048(8) 0.9401(5) 0.0386(16) 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
F5 C19 1.347(6) . ?
F1 C15 1.334(7) . ?
F4 C18 1.351(8) . ?
N1 C1 1.392(7) . ?
N1 C4 1.407(6) . ?
N1 C7 1.412(6) . ?
N2 C7 1.299(6) . ?
N2 C8 1.407(7) . ?
F3 C17 1.365(7) . ?
F2 C16 1.348(7) . ?
C7 C6 1.458(7) 2_666 ?
C4 C4 1.408(10) 2_666 ?
C4 C3 1.429(7) . ?
C5 C6 1.354(7) . ?
C5 C3 1.422(7) . ?
C5 C14 1.510(8) . ?
C3 C2 1.420(7) . ?
C2 C1 1.351(7) . ?
C2 H2 0.9300 . ?
C9 C8 1.385(7) . ?
C9 C10 1.386(8) . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?
C8 C13 1.404(7) . ?
C11 C10 1.378(8) . ?
C11 C12 1.392(7) . ?
C11 H11 0.9300 . ?
C6 C7 1.458(7) 2_666 ?
C6 C13 1.487(7) 2_666 ?
C10 H10 0.9300 . ?
C13 C12 1.383(7) . ?
C13 C6 1.487(7) 2_666 ?
C14 C15 1.382(7) . ?
C14 C19 1.385(8) . ?
C19 C18 1.379(9) . ?
C12 H12 0.9300 . ?
C15 C16 1.382(9) . ?
C18 C17 1.362(9) . ?
C17 C16 1.378(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 109.8(4) . . ?
C1 N1 C7 118.2(4) . . ?
C4 N1 C7 132.0(4) . . ?
C7 N2 C8 105.1(4) . . ?
N2 C7 N1 117.3(4) . . ?
N2 C7 C6 115.8(4) . 2_666 ?
N1 C7 C6 126.8(4) . 2_666 ?
N1 C4 C4 124.4(5) . 2_666 ?
N1 C4 C3 105.1(4) . . ?
C4 C4 C3 130.5(5) 2_666 . ?
C6 C5 C3 128.2(5) . . ?
C6 C5 C14 116.5(4) . . ?
C3 C5 C14 115.3(4) . . ?
C2 C3 C5 123.4(5) . . ?
C2 C3 C4 107.7(4) . . ?
C5 C3 C4 128.7(5) . . ?
C1 C2 C3 108.8(4) . . ?
C1 C2 H2 125.6 . . ?
C3 C2 H2 125.6 . . ?
C8 C9 C10 117.7(5) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C2 C1 N1 108.6(4) . . ?
C2 C1 H1 125.7 . . ?
N1 C1 H1 125.7 . . ?
C9 C8 C13 121.8(5) . . ?
C9 C8 N2 125.8(5) . . ?
C13 C8 N2 112.3(4) . . ?
C10 C11 C12 121.2(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C5 C6 C7 128.9(5) . 2_666 ?
C5 C6 C13 129.6(5) . 2_666 ?
C7 C6 C13 101.4(4) 2_666 2_666 ?
C11 C10 C9 121.1(5) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C13 C8 119.5(5) . . ?
C12 C13 C6 135.1(5) . 2_666 ?
C8 C13 C6 105.4(4) . 2_666 ?
C15 C14 C19 117.3(5) . . ?
C15 C14 C5 121.9(5) . . ?
C19 C14 C5 120.8(5) . . ?
F5 C19 C18 118.4(5) . . ?
F5 C19 C14 119.5(5) . . ?
C18 C19 C14 122.0(5) . . ?
C13 C12 C11 118.6(5) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
F1 C15 C14 120.2(5) . . ?
F1 C15 C16 118.2(5) . . ?
C14 C15 C16 121.6(6) . . ?
F4 C18 C17 120.4(6) . . ?
F4 C18 C19 120.7(6) . . ?
C17 C18 C19 119.0(6) . . ?
C18 C17 F3 119.0(7) . . ?
C18 C17 C16 121.2(6) . . ?
F3 C17 C16 119.8(6) . . ?
F2 C16 C17 120.6(6) . . ?
F2 C16 C15 120.5(6) . . ?
C17 C16 C15 118.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        28.62
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.125
_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# 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_718
_database_code_depnum_ccdc_archive 'CCDC 1427524'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H16 F10 N4 , C3 H6 O'
_chemical_formula_sum            'C41 H22 F10 N4 O'
_chemical_formula_weight         776.63

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.9304(18)
_cell_length_b                   12.231(2)
_cell_length_c                   14.545(3)
_cell_angle_alpha                75.314(4)
_cell_angle_beta                 82.512(4)
_cell_angle_gamma                80.770(4)
_cell_volume                     1679.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28066
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_sigmaI/netI    0.1104
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         28.28
_reflns_number_total             8336
_reflns_number_gt                4445
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0664P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8230
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 0.81298(15) 0.64549(12) -0.43738(11) 0.0276(4) Uani 1 1 d . . .
F8 F -0.00589(17) -0.18416(13) 0.45377(12) 0.0389(5) Uani 1 1 d . . .
F2 F 0.83382(15) 0.65013(11) -0.25368(11) 0.0251(4) Uani 1 1 d . . .
F1 F 0.66885(15) 0.53956(11) -0.11123(10) 0.0215(3) Uani 1 1 d . . .
F10 F 0.42096(15) -0.13831(11) 0.27853(10) 0.0228(4) Uani 1 1 d . . .
F9 F 0.26169(16) -0.26722(11) 0.41218(11) 0.0291(4) Uani 1 1 d . . .
F7 F -0.11215(17) 0.02382(13) 0.35414(13) 0.0441(5) Uani 1 1 d . . .
F6 F 0.04793(16) 0.15357(11) 0.22110(11) 0.0309(4) Uani 1 1 d . . .
F5 F 0.45462(15) 0.42311(12) -0.33490(10) 0.0261(4) Uani 1 1 d . . .
F4 F 0.61931(17) 0.53601(13) -0.47707(10) 0.0323(4) Uani 1 1 d . . .
O1S O 1.0428(2) 0.62666(18) 0.34373(15) 0.0414(6) Uani 1 1 d . . .
N2 N 0.3999(2) 0.16224(15) 0.00605(14) 0.0147(4) Uani 1 1 d . . .
N1 N 0.2695(2) 0.56512(15) -0.17440(14) 0.0182(5) Uani 1 1 d . . .
H1 H 0.3189 0.6173 -0.2040 0.022 Uiso 1 1 calc R . .
N4 N 0.6069(2) 0.22071(15) 0.23587(14) 0.0177(5) Uani 1 1 d . . .
N3 N 0.5625(2) 0.22879(15) 0.07948(14) 0.0151(4) Uani 1 1 d . . .
C4 C 0.7283(3) 0.59359(19) -0.36673(18) 0.0197(6) Uani 1 1 d . . .
C5 C 0.7388(3) 0.59540(19) -0.27388(19) 0.0191(6) Uani 1 1 d . . .
C6 C 0.6527(3) 0.53896(19) -0.20170(17) 0.0175(6) Uani 1 1 d . . .
C1 C 0.5541(2) 0.47955(18) -0.21876(17) 0.0156(5) Uani 1 1 d . . .
C17 C 0.4656(3) 0.41347(18) -0.13979(17) 0.0145(5) Uani 1 1 d . . .
C18 C 0.5272(3) 0.32453(18) -0.07664(17) 0.0149(5) Uani 1 1 d . . .
C19 C 0.4541(3) 0.26332(18) 0.01492(17) 0.0156(5) Uani 1 1 d . . .
H19 H 0.3806 0.3158 0.0387 0.019 Uiso 1 1 calc R . .
C35 C 0.3332(2) 0.09017(18) 0.08176(17) 0.0149(5) Uani 1 1 d . . .
C34 C 0.3339(2) 0.08849(17) 0.18055(17) 0.0149(5) Uani 1 1 d . . .
C7 C 0.2395(3) 0.01249(19) 0.24636(17) 0.0174(6) Uani 1 1 d . . .
C8 C 0.2889(3) -0.09697(19) 0.29600(18) 0.0176(6) Uani 1 1 d . . .
C9 C 0.2083(3) -0.16380(19) 0.36431(18) 0.0222(6) Uani 1 1 d . . .
C10 C 0.0738(3) -0.1224(2) 0.38494(19) 0.0260(7) Uani 1 1 d . . .
C16 C 0.3192(3) 0.45276(18) -0.13530(17) 0.0159(5) Uani 1 1 d . . .
C13 C 0.1313(3) 0.5805(2) -0.15896(19) 0.0224(6) Uani 1 1 d . . .
H13 H 0.0751 0.6492 -0.1775 0.027 Uiso 1 1 calc R . .
C14 C 0.0876(3) 0.47893(19) -0.11178(19) 0.0212(6) Uani 1 1 d . . .
H14 H -0.0028 0.4656 -0.0935 0.025 Uiso 1 1 calc R . .
C15 C 0.2056(3) 0.39828(19) -0.09620(18) 0.0186(6) Uani 1 1 d . . .
H15 H 0.2071 0.3217 -0.0651 0.022 Uiso 1 1 calc R . .
C36 C 0.2776(3) 0.01731(18) 0.04187(18) 0.0175(6) Uani 1 1 d . . .
H36 H 0.2270 -0.0405 0.0753 0.021 Uiso 1 1 calc R . .
C37 C 0.3106(3) 0.04563(18) -0.05620(18) 0.0194(6) Uani 1 1 d . . .
H37 H 0.2865 0.0102 -0.1000 0.023 Uiso 1 1 calc R . .
C38 C 0.3856(3) 0.13562(19) -0.07695(18) 0.0177(6) Uani 1 1 d . . .
H38 H 0.4205 0.1720 -0.1375 0.021 Uiso 1 1 calc R . .
C11 C 0.0198(3) -0.0167(2) 0.3348(2) 0.0277(7) Uani 1 1 d . . .
C12 C 0.1029(3) 0.04882(19) 0.26693(19) 0.0220(6) Uani 1 1 d . . .
C27 C 0.4124(2) 0.14122(18) 0.22194(17) 0.0154(5) Uani 1 1 d . . .
C28 C 0.4182(3) 0.13656(18) 0.32339(18) 0.0168(5) Uani 1 1 d . . .
C33 C 0.3347(3) 0.10376(18) 0.40736(18) 0.0190(6) Uani 1 1 d . . .
H33 H 0.2556 0.0724 0.4068 0.023 Uiso 1 1 calc R . .
C32 C 0.3709(3) 0.1184(2) 0.49186(19) 0.0220(6) Uani 1 1 d . . .
H32 H 0.3151 0.0968 0.5481 0.026 Uiso 1 1 calc R . .
C31 C 0.4890(3) 0.1649(2) 0.49403(18) 0.0227(6) Uani 1 1 d . . .
H31 H 0.5108 0.1741 0.5516 0.027 Uiso 1 1 calc R . .
C30 C 0.5746(3) 0.19762(19) 0.41159(18) 0.0218(6) Uani 1 1 d . . .
H30 H 0.6539 0.2284 0.4130 0.026 Uiso 1 1 calc R . .
C29 C 0.5385(3) 0.18314(18) 0.32733(18) 0.0184(6) Uani 1 1 d . . .
C26 C 0.5314(2) 0.20048(18) 0.17598(17) 0.0148(5) Uani 1 1 d . . .
C25 C 0.6916(3) 0.23503(18) 0.02673(17) 0.0155(5) Uani 1 1 d . . .
C20 C 0.6730(3) 0.28385(18) -0.06947(18) 0.0163(5) Uani 1 1 d . . .
C21 C 0.7884(3) 0.28519(18) -0.13623(19) 0.0188(6) Uani 1 1 d . . .
H21 H 0.7793 0.3150 -0.2010 0.023 Uiso 1 1 calc R . .
C22 C 0.9164(3) 0.24160(19) -0.10458(19) 0.0215(6) Uani 1 1 d . . .
H22 H 0.9931 0.2411 -0.1487 0.026 Uiso 1 1 calc R . .
C23 C 0.9316(3) 0.19884(19) -0.00827(19) 0.0214(6) Uani 1 1 d . . .
H23 H 1.0190 0.1724 0.0112 0.026 Uiso 1 1 calc R . .
C24 C 0.8195(3) 0.19453(18) 0.05987(19) 0.0192(6) Uani 1 1 d . . .
H24 H 0.8297 0.1659 0.1246 0.023 Uiso 1 1 calc R . .
C2 C 0.5459(3) 0.48164(19) -0.31369(18) 0.0187(6) Uani 1 1 d . . .
C3 C 0.6304(3) 0.5371(2) -0.38666(18) 0.0208(6) Uani 1 1 d . . .
C40S C 0.9246(3) 0.6095(2) 0.3490(2) 0.0301(7) Uani 1 1 d . . .
C39S C 0.8106(3) 0.7047(2) 0.3228(2) 0.0325(7) Uani 1 1 d . . .
H39A H 0.8466 0.7762 0.3047 0.049 Uiso 1 1 calc R . .
H39B H 0.7434 0.7046 0.3766 0.049 Uiso 1 1 calc R . .
H39C H 0.7687 0.6943 0.2703 0.049 Uiso 1 1 calc R . .
C41S C 0.8861(3) 0.4907(2) 0.3829(2) 0.0354(8) Uani 1 1 d . . .
H41A H 0.9506 0.4397 0.3532 0.053 Uiso 1 1 calc R . .
H41B H 0.7959 0.4903 0.3661 0.053 Uiso 1 1 calc R . .
H41C H 0.8874 0.4663 0.4510 0.053 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C4 1.335(3) . ?
F8 C10 1.342(3) . ?
F2 C5 1.342(3) . ?
F1 C6 1.348(3) . ?
F10 C8 1.344(3) . ?
F9 C9 1.342(3) . ?
F7 C11 1.344(3) . ?
F6 C12 1.350(3) . ?
F5 C2 1.350(3) . ?
F4 C3 1.337(3) . ?
O1S C40S 1.215(3) . ?
N2 C38 1.357(3) . ?
N2 C35 1.390(3) . ?
N2 C19 1.465(3) . ?
N1 C13 1.351(3) . ?
N1 C16 1.384(3) . ?
N1 H1 0.8600 . ?
N4 C26 1.312(3) . ?
N4 C29 1.413(3) . ?
N3 C26 1.364(3) . ?
N3 C25 1.409(3) . ?
N3 C19 1.461(3) . ?
C4 C3 1.377(4) . ?
C4 C5 1.374(4) . ?
C5 C6 1.377(3) . ?
C6 C1 1.389(3) . ?
C1 C2 1.387(3) . ?
C1 C17 1.496(3) . ?
C17 C18 1.352(3) . ?
C17 C16 1.455(3) . ?
C18 C20 1.462(3) . ?
C18 C19 1.509(3) . ?
C19 H19 0.9800 . ?
C35 C36 1.392(3) . ?
C35 C34 1.433(3) . ?
C34 C27 1.366(3) . ?
C34 C7 1.501(3) . ?
C7 C12 1.377(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.374(3) . ?
C9 C10 1.373(4) . ?
C10 C11 1.376(4) . ?
C16 C15 1.386(3) . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.408(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C36 C37 1.388(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.376(3) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C11 C12 1.377(3) . ?
C27 C28 1.470(4) . ?
C27 C26 1.481(3) . ?
C28 C33 1.391(3) . ?
C28 C29 1.416(4) . ?
C33 C32 1.385(4) . ?
C33 H33 0.9300 . ?
C32 C31 1.390(4) . ?
C32 H32 0.9300 . ?
C31 C30 1.386(3) . ?
C31 H31 0.9300 . ?
C30 C29 1.381(4) . ?
C30 H30 0.9300 . ?
C25 C24 1.389(4) . ?
C25 C20 1.399(4) . ?
C20 C21 1.402(3) . ?
C21 C22 1.386(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C2 C3 1.370(3) . ?
C40S C41S 1.506(4) . ?
C40S C39S 1.499(4) . ?
C39S H39A 0.9600 . ?
C39S H39B 0.9600 . ?
C39S H39C 0.9600 . ?
C41S H41A 0.9600 . ?
C41S H41B 0.9600 . ?
C41S H41C 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
C38 N2 C35 109.53(19) . . ?
C38 N2 C19 125.92(19) . . ?
C35 N2 C19 123.66(19) . . ?
C13 N1 C16 109.66(19) . . ?
C13 N1 H1 125.2 . . ?
C16 N1 H1 125.2 . . ?
C26 N4 C29 105.3(2) . . ?
C26 N3 C25 129.2(2) . . ?
C26 N3 C19 120.8(2) . . ?
C25 N3 C19 110.0(2) . . ?
F3 C4 C3 120.0(2) . . ?
F3 C4 C5 120.4(2) . . ?
C3 C4 C5 119.6(2) . . ?
F2 C5 C6 120.4(2) . . ?
F2 C5 C4 120.1(2) . . ?
C6 C5 C4 119.5(2) . . ?
F1 C6 C5 117.8(2) . . ?
F1 C6 C1 119.6(2) . . ?
C5 C6 C1 122.5(2) . . ?
C2 C1 C6 115.9(2) . . ?
C2 C1 C17 121.7(2) . . ?
C6 C1 C17 122.4(2) . . ?
C18 C17 C16 124.9(2) . . ?
C18 C17 C1 118.1(2) . . ?
C16 C17 C1 116.9(2) . . ?
C17 C18 C20 129.5(2) . . ?
C17 C18 C19 123.5(2) . . ?
C20 C18 C19 105.8(2) . . ?
N2 C19 N3 109.64(18) . . ?
N2 C19 C18 113.42(19) . . ?
N3 C19 C18 102.64(19) . . ?
N2 C19 H19 110.3 . . ?
N3 C19 H19 110.3 . . ?
C18 C19 H19 110.3 . . ?
N2 C35 C36 106.1(2) . . ?
N2 C35 C34 125.2(2) . . ?
C36 C35 C34 128.6(2) . . ?
C27 C34 C35 129.1(2) . . ?
C27 C34 C7 116.9(2) . . ?
C35 C34 C7 113.9(2) . . ?
C12 C7 C8 116.1(2) . . ?
C12 C7 C34 122.5(2) . . ?
C8 C7 C34 121.1(2) . . ?
F10 C8 C9 118.3(2) . . ?
F10 C8 C7 119.3(2) . . ?
C9 C8 C7 122.5(2) . . ?
F9 C9 C10 120.4(2) . . ?
F9 C9 C8 120.2(2) . . ?
C10 C9 C8 119.4(2) . . ?
F8 C10 C9 120.6(2) . . ?
F8 C10 C11 119.5(2) . . ?
C9 C10 C11 119.9(2) . . ?
N1 C16 C15 106.2(2) . . ?
N1 C16 C17 121.1(2) . . ?
C15 C16 C17 132.7(2) . . ?
N1 C13 C14 109.1(2) . . ?
N1 C13 H13 125.4 . . ?
C14 C13 H13 125.4 . . ?
C13 C14 C15 106.8(2) . . ?
C13 C14 H14 126.6 . . ?
C15 C14 H14 126.6 . . ?
C16 C15 C14 108.2(2) . . ?
C16 C15 H15 125.9 . . ?
C14 C15 H15 125.9 . . ?
C35 C36 C37 108.4(2) . . ?
C35 C36 H36 125.8 . . ?
C37 C36 H36 125.8 . . ?
C38 C37 C36 107.7(2) . . ?
C38 C37 H37 126.2 . . ?
C36 C37 H37 126.2 . . ?
N2 C38 C37 108.3(2) . . ?
N2 C38 H38 125.8 . . ?
C37 C38 H38 125.8 . . ?
F7 C11 C10 120.2(2) . . ?
F7 C11 C12 120.3(2) . . ?
C10 C11 C12 119.5(2) . . ?
F6 C12 C7 119.4(2) . . ?
F6 C12 C11 118.1(2) . . ?
C7 C12 C11 122.5(2) . . ?
C34 C27 C28 129.7(2) . . ?
C34 C27 C26 127.3(2) . . ?
C28 C27 C26 102.2(2) . . ?
C33 C28 C29 118.7(2) . . ?
C33 C28 C27 135.7(2) . . ?
C29 C28 C27 105.5(2) . . ?
C28 C33 C32 119.2(2) . . ?
C28 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C33 C32 C31 121.1(2) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C30 C31 C32 121.0(3) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C29 C30 C31 117.9(3) . . ?
C29 C30 H30 121.1 . . ?
C31 C30 H30 121.1 . . ?
C30 C29 C28 122.1(2) . . ?
C30 C29 N4 125.4(2) . . ?
C28 C29 N4 112.3(2) . . ?
N4 C26 N3 122.7(2) . . ?
N4 C26 C27 114.4(2) . . ?
N3 C26 C27 122.9(2) . . ?
C24 C25 C20 123.2(2) . . ?
C24 C25 N3 127.6(2) . . ?
C20 C25 N3 109.1(2) . . ?
C25 C20 C21 118.2(2) . . ?
C25 C20 C18 108.0(2) . . ?
C21 C20 C18 133.8(2) . . ?
C22 C21 C20 119.2(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 121.5(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C23 116.8(2) . . ?
C25 C24 H24 121.6 . . ?
C23 C24 H24 121.6 . . ?
F5 C2 C3 118.5(2) . . ?
F5 C2 C1 118.8(2) . . ?
C3 C2 C1 122.6(2) . . ?
F4 C3 C4 119.8(2) . . ?
F4 C3 C2 120.5(2) . . ?
C4 C3 C2 119.8(2) . . ?
O1S C40S C41S 121.0(3) . . ?
O1S C40S C39S 122.0(3) . . ?
C41S C40S C39S 116.9(3) . . ?
C40S C39S H39A 109.5 . . ?
C40S C39S H39B 109.5 . . ?
H39A C39S H39B 109.5 . . ?
C40S C39S H39C 109.5 . . ?
H39A C39S H39C 109.5 . . ?
H39B C39S H39C 109.5 . . ?
C40S C41S H41A 109.5 . . ?
C40S C41S H41B 109.5 . . ?
H41A C41S H41B 109.5 . . ?
C40S C41S H41C 109.5 . . ?
H41A C41S H41C 109.5 . . ?
H41B C41S H41C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.068
_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# 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_816
_database_code_depnum_ccdc_archive 'CCDC 1427525'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H18 F10 N4'
_chemical_formula_sum            'C46 H18 F10 N4'
_chemical_formula_weight         816.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   10.144(2)
_cell_length_b                   12.998(3)
_cell_length_c                   25.579(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.312(4)
_cell_angle_gamma                90.00
_cell_volume                     3352.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58840
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         28.38
_reflns_number_total             8405
_reflns_number_gt                4439
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0934P)²+0.8918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8355
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1830
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2997(2) 0.14487(16) 0.64261(7) 0.0493(6) Uani 1 1 d . . .
F2 F -0.0303(2) 0.12440(16) 1.19737(7) 0.0492(5) Uani 1 1 d . . .
F3 F 0.1211(2) 0.29361(16) 0.66043(7) 0.0570(6) Uani 1 1 d . . .
F4 F 0.0454(2) 0.31742(15) 0.75689(7) 0.0466(5) Uani 1 1 d . . .
F5 F 0.29558(18) 0.30103(14) 1.11687(7) 0.0387(5) Uani 1 1 d . . .
F6 F 0.2107(2) 0.22013(15) 1.20331(7) 0.0485(5) Uani 1 1 d . . .
F7 F -0.18049(19) 0.10897(15) 1.10436(7) 0.0444(5) Uani 1 1 d . . .
F8 F -0.10424(17) 0.19924(13) 1.01755(6) 0.0330(4) Uani 1 1 d . . .
F9 F 0.3117(2) 0.03649(15) 0.81815(7) 0.0460(5) Uani 1 1 d . . .
F10 F 0.3891(2) 0.01438(17) 0.72050(8) 0.0557(6) Uani 1 1 d . . .
N1 N 0.2466(2) 0.41267(17) 0.93333(9) 0.0250(5) Uani 1 1 d . . .
N2 N 0.2753(3) 0.55620(18) 0.99155(9) 0.0275(6) Uani 1 1 d . . .
N3 N 0.1859(3) 0.06685(19) 0.98626(9) 0.0276(6) Uani 1 1 d . . .
N4 N -0.0917(3) 0.06837(18) 0.92073(10) 0.0284(6) Uani 1 1 d . . .
H4 H -0.1173 0.0439 0.9492 0.034 Uiso 1 1 calc R . .
C1 C 0.2578(3) 0.1545(3) 0.69060(12) 0.0349(8) Uani 1 1 d . . .
C2 C 0.1700(3) 0.2308(3) 0.69964(12) 0.0353(8) Uani 1 1 d . . .
C3 C 0.1319(3) 0.2422(2) 0.74909(11) 0.0303(7) Uani 1 1 d . . .
C4 C 0.1778(3) 0.1788(2) 0.79100(11) 0.0261(7) Uani 1 1 d . . .
C5 C 0.1450(3) 0.2029(2) 0.84529(10) 0.0236(6) Uani 1 1 d . . .
C6 C 0.2150(3) 0.2773(2) 0.87256(11) 0.0247(6) Uani 1 1 d . . .
C7 C 0.1718(3) 0.3166(2) 0.92345(10) 0.0236(6) Uani 1 1 d . . .
H7 H 0.0774 0.3342 0.9171 0.028 Uiso 1 1 calc R . .
C8 C 0.1911(3) 0.2471(2) 0.97222(10) 0.0226(6) Uani 1 1 d . . .
C9 C 0.1385(3) 0.3097(2) 1.01756(10) 0.0236(6) Uani 1 1 d . . .
C10 C 0.0965(3) 0.2549(2) 1.06432(11) 0.0256(6) Uani 1 1 d . . .
C11 C -0.0224(3) 0.2033(2) 1.06304(11) 0.0271(7) Uani 1 1 d . . .
C12 C -0.0636(3) 0.1577(2) 1.10710(12) 0.0309(7) Uani 1 1 d . . .
C13 C 0.0138(4) 0.1655(2) 1.15417(11) 0.0338(8) Uani 1 1 d . . .
C14 C 0.3033(3) 0.0892(2) 0.73014(13) 0.0345(8) Uani 1 1 d . . .
C15 C 0.2627(3) 0.1008(2) 0.77969(12) 0.0320(7) Uani 1 1 d . . .
C16 C 0.2294(3) 0.4659(2) 0.97784(11) 0.0254(6) Uani 1 1 d . . .
C17 C 0.2288(3) 0.5742(2) 1.04157(11) 0.0270(7) Uani 1 1 d . . .
C18 C 0.1518(3) 0.4924(2) 1.05843(11) 0.0257(6) Uani 1 1 d . . .
C19 C 0.0981(3) 0.4984(2) 1.10589(11) 0.0286(7) Uani 1 1 d . . .
H19 H 0.0453 0.4456 1.1166 0.034 Uiso 1 1 calc R . .
C20 C 0.1253(3) 0.5858(2) 1.13734(11) 0.0311(7) Uani 1 1 d . . .
H20 H 0.0910 0.5911 1.1695 0.037 Uiso 1 1 calc R . .
C21 C 0.2037(3) 0.6648(2) 1.12050(12) 0.0315(7) Uani 1 1 d . . .
H21 H 0.2217 0.7219 1.1420 0.038 Uiso 1 1 calc R . .
C22 C 0.2554(3) 0.6603(2) 1.07267(12) 0.0299(7) Uani 1 1 d . . .
H22 H 0.3066 0.7139 1.0617 0.036 Uiso 1 1 calc R . .
C23 C 0.1566(3) 0.4123(2) 1.01819(11) 0.0258(6) Uani 1 1 d . . .
C24 C 0.1246(3) 0.1429(2) 0.96126(11) 0.0245(6) Uani 1 1 d . . .
C25 C 0.3110(3) 0.1087(2) 1.00934(11) 0.0285(7) Uani 1 1 d . . .
C26 C 0.4119(3) 0.0539(2) 1.03725(12) 0.0339(7) Uani 1 1 d . . .
H26 H 0.4010 -0.0149 1.0456 0.041 Uiso 1 1 calc R . .
C27 C 0.5303(3) 0.1052(3) 1.05243(13) 0.0385(8) Uani 1 1 d . . .
H27 H 0.5996 0.0702 1.0716 0.046 Uiso 1 1 calc R . .
C28 C 0.5466(3) 0.2087(2) 1.03931(12) 0.0328(7) Uani 1 1 d . . .
H28 H 0.6272 0.2412 1.0492 0.039 Uiso 1 1 calc R . .
C29 C 0.4442(3) 0.2629(2) 1.01177(11) 0.0284(7) Uani 1 1 d . . .
H29 H 0.4543 0.3320 1.0036 0.034 Uiso 1 1 calc R . .
C30 C 0.3264(3) 0.2119(2) 0.99660(11) 0.0254(6) Uani 1 1 d . . .
C31 C 0.0203(3) 0.1269(2) 0.91766(11) 0.0246(6) Uani 1 1 d . . .
C32 C -0.1567(3) 0.0553(2) 0.87054(11) 0.0264(7) Uani 1 1 d . . .
C33 C -0.2760(3) 0.0055(2) 0.85421(13) 0.0350(8) Uani 1 1 d . . .
H33 H -0.3246 -0.0271 0.8782 0.042 Uiso 1 1 calc R . .
C34 C -0.3192(3) 0.0065(3) 0.80114(13) 0.0388(8) Uani 1 1 d . . .
H34 H -0.3984 -0.0261 0.7892 0.047 Uiso 1 1 calc R . .
C35 C -0.2463(3) 0.0555(2) 0.76488(13) 0.0359(8) Uani 1 1 d . . .
H35 H -0.2782 0.0554 0.7294 0.043 Uiso 1 1 calc R . .
C36 C -0.1291(3) 0.1035(2) 0.78096(11) 0.0310(7) Uani 1 1 d . . .
H36 H -0.0815 0.1359 0.7566 0.037 Uiso 1 1 calc R . .
C37 C -0.0808(3) 0.1036(2) 0.83479(11) 0.0265(7) Uani 1 1 d . . .
C38 C 0.0339(3) 0.1493(2) 0.86533(11) 0.0255(6) Uani 1 1 d . . .
C39 C 0.1750(3) 0.2565(2) 1.11253(12) 0.0305(7) Uani 1 1 d . . .
C40 C 0.1334(4) 0.2141(2) 1.15722(12) 0.0359(8) Uani 1 1 d . . .
C41 C 0.3379(3) 0.4260(2) 0.89632(10) 0.0250(6) Uani 1 1 d . . .
C42 C 0.3234(3) 0.3449(2) 0.85956(11) 0.0262(7) Uani 1 1 d . . .
C43 C 0.4076(3) 0.3420(2) 0.81992(11) 0.0290(7) Uani 1 1 d . . .
H43 H 0.4011 0.2888 0.7954 0.035 Uiso 1 1 calc R . .
C44 C 0.5009(3) 0.4194(2) 0.81751(11) 0.0309(7) Uani 1 1 d . . .
H44 H 0.5566 0.4182 0.7910 0.037 Uiso 1 1 calc R . .
C45 C 0.5123(3) 0.4984(2) 0.85411(12) 0.0312(7) Uani 1 1 d . . .
H45 H 0.5758 0.5493 0.8517 0.037 Uiso 1 1 calc R . .
C46 C 0.4309(3) 0.5034(2) 0.89443(11) 0.0279(7) Uani 1 1 d . . .
H46 H 0.4386 0.5564 0.9190 0.033 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.348(3) . ?
F2 C13 1.347(3) . ?
F3 C2 1.345(4) . ?
F4 C3 1.343(4) . ?
F5 C39 1.347(4) . ?
F6 C40 1.344(3) . ?
F7 C12 1.339(4) . ?
F8 C11 1.354(3) . ?
F9 C15 1.344(3) . ?
F10 C14 1.346(4) . ?
N1 C16 1.359(4) . ?
N1 C41 1.406(4) . ?
N1 C7 1.468(4) . ?
N2 C16 1.297(4) . ?
N2 C17 1.431(4) . ?
N3 C24 1.298(4) . ?
N3 C25 1.446(4) . ?
N4 C31 1.377(4) . ?
N4 C32 1.387(4) . ?
N4 H4 0.8600 . ?
C1 C14 1.361(5) . ?
C1 C2 1.369(5) . ?
C2 C3 1.371(4) . ?
C3 C4 1.391(4) . ?
C4 C15 1.381(4) . ?
C4 C5 1.496(4) . ?
C5 C6 1.348(4) . ?
C5 C38 1.465(4) . ?
C6 C42 1.474(4) . ?
C6 C7 1.508(4) . ?
C7 C8 1.536(4) . ?
C7 H7 0.9800 . ?
C8 C30 1.514(4) . ?
C8 C24 1.525(4) . ?
C8 C9 1.559(4) . ?
C9 C23 1.346(4) . ?
C9 C10 1.494(4) . ?
C10 C11 1.377(4) . ?
C10 C39 1.393(4) . ?
C11 C12 1.378(4) . ?
C12 C13 1.367(4) . ?
C13 C40 1.363(5) . ?
C14 C15 1.383(4) . ?
C16 C23 1.504(4) . ?
C17 C22 1.382(4) . ?
C17 C18 1.414(4) . ?
C18 C19 1.387(4) . ?
C18 C23 1.468(4) . ?
C19 C20 1.402(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.396(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C24 C31 1.465(4) . ?
C25 C26 1.379(4) . ?
C25 C30 1.394(4) . ?
C26 C27 1.391(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.401(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.382(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(4) . ?
C29 H29 0.9300 . ?
C31 C38 1.391(4) . ?
C32 C33 1.396(4) . ?
C32 C37 1.406(4) . ?
C33 C34 1.380(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.402(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.365(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.410(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.455(4) . ?
C39 C40 1.376(4) . ?
C41 C46 1.384(4) . ?
C41 C42 1.410(4) . ?
C42 C43 1.396(4) . ?
C43 C44 1.387(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.386(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.392(4) . ?
C45 H45 0.9300 . ?
C46 H46 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
C16 N1 C41 130.9(2) . . ?
C16 N1 C7 117.7(2) . . ?
C41 N1 C7 110.8(2) . . ?
C16 N2 C17 104.2(2) . . ?
C24 N3 C25 105.4(2) . . ?
C31 N4 C32 109.0(2) . . ?
C31 N4 H4 125.5 . . ?
C32 N4 H4 125.5 . . ?
F1 C1 C14 120.2(3) . . ?
F1 C1 C2 119.8(3) . . ?
C14 C1 C2 120.0(3) . . ?
F3 C2 C1 120.4(3) . . ?
F3 C2 C3 120.3(3) . . ?
C1 C2 C3 119.3(3) . . ?
F4 C3 C2 118.1(3) . . ?
F4 C3 C4 119.1(3) . . ?
C2 C3 C4 122.9(3) . . ?
C15 C4 C3 115.9(3) . . ?
C15 C4 C5 123.8(3) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C38 122.8(3) . . ?
C6 C5 C4 118.2(3) . . ?
C38 C5 C4 118.9(2) . . ?
C5 C6 C42 132.4(3) . . ?
C5 C6 C7 120.2(3) . . ?
C42 C6 C7 106.7(2) . . ?
N1 C7 C6 104.1(2) . . ?
N1 C7 C8 110.1(2) . . ?
C6 C7 C8 118.6(2) . . ?
N1 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C30 C8 C24 99.8(2) . . ?
C30 C8 C7 122.8(2) . . ?
C24 C8 C7 111.1(2) . . ?
C30 C8 C9 102.7(2) . . ?
C24 C8 C9 114.8(2) . . ?
C7 C8 C9 105.8(2) . . ?
C23 C9 C10 120.9(2) . . ?
C23 C9 C8 118.0(2) . . ?
C10 C9 C8 119.8(2) . . ?
C11 C10 C39 116.2(3) . . ?
C11 C10 C9 122.6(3) . . ?
C39 C10 C9 121.1(3) . . ?
F8 C11 C10 119.5(2) . . ?
F8 C11 C12 118.2(3) . . ?
C10 C11 C12 122.3(3) . . ?
F7 C12 C13 120.0(3) . . ?
F7 C12 C11 120.5(3) . . ?
C13 C12 C11 119.5(3) . . ?
F2 C13 C40 120.7(3) . . ?
F2 C13 C12 118.9(3) . . ?
C40 C13 C12 120.4(3) . . ?
F10 C14 C1 119.2(3) . . ?
F10 C14 C15 120.7(3) . . ?
C1 C14 C15 120.2(3) . . ?
F9 C15 C4 119.5(3) . . ?
F9 C15 C14 118.7(3) . . ?
C4 C15 C14 121.8(3) . . ?
N2 C16 N1 127.7(3) . . ?
N2 C16 C23 115.0(2) . . ?
N1 C16 C23 117.2(2) . . ?
C22 C17 C18 120.8(3) . . ?
C22 C17 N2 125.8(3) . . ?
C18 C17 N2 113.4(2) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 C23 134.4(3) . . ?
C17 C18 C23 104.9(2) . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 121.8(3) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C17 C22 C21 118.3(3) . . ?
C17 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C9 C23 C18 134.1(3) . . ?
C9 C23 C16 121.8(3) . . ?
C18 C23 C16 102.1(2) . . ?
N3 C24 C31 122.3(3) . . ?
N3 C24 C8 114.0(3) . . ?
C31 C24 C8 122.2(2) . . ?
C26 C25 C30 121.5(3) . . ?
C26 C25 N3 125.8(3) . . ?
C30 C25 N3 112.5(3) . . ?
C25 C26 C27 117.8(3) . . ?
C25 C26 H26 121.1 . . ?
C27 C26 H26 121.1 . . ?
C26 C27 C28 120.9(3) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 118.4(3) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C29 C30 C25 120.7(3) . . ?
C29 C30 C8 133.4(3) . . ?
C25 C30 C8 105.5(2) . . ?
N4 C31 C38 109.9(2) . . ?
N4 C31 C24 124.5(3) . . ?
C38 C31 C24 124.3(3) . . ?
N4 C32 C33 129.9(3) . . ?
N4 C32 C37 108.0(3) . . ?
C33 C32 C37 122.1(3) . . ?
C34 C33 C32 117.5(3) . . ?
C34 C33 H33 121.3 . . ?
C32 C33 H33 121.3 . . ?
C33 C34 C35 121.4(3) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C36 C35 C34 120.9(3) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C37 119.5(3) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C32 C37 C36 118.6(3) . . ?
C32 C37 C38 107.2(2) . . ?
C36 C37 C38 134.1(3) . . ?
C31 C38 C37 105.9(3) . . ?
C31 C38 C5 126.7(3) . . ?
C37 C38 C5 127.4(3) . . ?
F5 C39 C40 117.5(3) . . ?
F5 C39 C10 120.3(3) . . ?
C40 C39 C10 122.1(3) . . ?
F6 C40 C13 120.5(3) . . ?
F6 C40 C39 120.2(3) . . ?
C13 C40 C39 119.4(3) . . ?
C46 C41 N1 128.0(3) . . ?
C46 C41 C42 122.8(3) . . ?
N1 C41 C42 109.2(2) . . ?
C43 C42 C41 118.5(3) . . ?
C43 C42 C6 132.8(3) . . ?
C41 C42 C6 108.7(2) . . ?
C44 C43 C42 119.2(3) . . ?
C44 C43 H43 120.4 . . ?
C42 C43 H43 120.4 . . ?
C45 C44 C43 120.9(3) . . ?
C45 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C44 C45 C46 121.5(3) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 H45 119.2 . . ?
C41 C46 C45 117.0(3) . . ?
C41 C46 H46 121.5 . . ?
C45 C46 H46 121.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_852
_database_code_depnum_ccdc_archive 'CCDC 1427526'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C57 H36 N6 O3, O'
_chemical_formula_sum            'C57 H36 N6 O4'
_chemical_formula_weight         868.92

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   12.261(6)
_cell_length_b                   13.380(6)
_cell_length_c                   14.218(6)
_cell_angle_alpha                77.740(9)
_cell_angle_beta                 81.518(10)
_cell_angle_gamma                89.721(12)
_cell_volume                     2253.5(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41771
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_av_sigmaI/netI    0.1755
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         28.48
_reflns_number_total             11406
_reflns_number_gt                4205
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11230
_refine_ls_number_parameters     604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2447
_refine_ls_R_factor_gt           0.1061
_refine_ls_wR_factor_ref         0.3764
_refine_ls_wR_factor_gt          0.2889
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1S O 0.4916(8) 0.870(2) 0.2054(11) 0.539(19) Uani 1 1 d . . .
O1 O 1.0144(3) 0.6472(3) 0.0302(2) 0.0560(9) Uani 1 1 d . . .
O2 O 0.9053(3) 0.7142(3) 0.2239(2) 0.0693(11) Uani 1 1 d . . .
O3 O 0.9167(3) 0.8780(3) 0.0288(2) 0.0541(9) Uani 1 1 d . . .
N4 N 0.7876(3) 0.8867(3) 0.2018(2) 0.0467(10) Uani 1 1 d . . .
H4 H 0.8109 0.8372 0.1749 0.056 Uiso 1 1 calc R . .
N3 N 0.8157(3) 1.0176(3) 0.0538(2) 0.0444(9) Uani 1 1 d . . .
N1 N 1.1222(3) 0.6608(3) -0.1178(2) 0.0472(10) Uani 1 1 d . . .
N2 N 1.0211(3) 0.8175(3) -0.1296(2) 0.0434(9) Uani 1 1 d . . .
H2 H 1.0208 0.8224 -0.0702 0.052 Uiso 1 1 calc R . .
N5 N 0.8910(4) 0.5646(3) 0.3408(3) 0.0521(11) Uani 1 1 d . . .
N6 N 1.0204(3) 0.5337(3) 0.2051(3) 0.0472(10) Uani 1 1 d . . .
H6 H 0.9887 0.5717 0.1608 0.057 Uiso 1 1 calc R . .
C45 C 0.7314(6) 0.3938(5) 0.5572(4) 0.085(2) Uani 1 1 d . . .
H45 H 0.7280 0.3279 0.5954 0.102 Uiso 1 1 calc R . .
C46 C 0.8146(5) 0.4217(4) 0.4789(4) 0.0652(15) Uani 1 1 d . . .
H46 H 0.8663 0.3746 0.4630 0.078 Uiso 1 1 calc R . .
C12 C 0.8196(4) 0.5201(4) 0.4252(3) 0.0515(13) Uani 1 1 d . . .
C11 C 0.7426(4) 0.5929(4) 0.4469(3) 0.0535(13) Uani 1 1 d . . .
C10 C 0.7680(4) 0.6878(4) 0.3726(3) 0.0513(13) Uani 1 1 d . . .
C36 C 0.7283(4) 0.7839(4) 0.3736(3) 0.0491(12) Uani 1 1 d . . .
C35 C 0.7462(4) 0.8769(4) 0.2994(3) 0.0500(12) Uani 1 1 d . . .
C32 C 0.7858(4) 0.9873(4) 0.1546(3) 0.0456(11) Uani 1 1 d . . .
C5 C 0.8782(4) 0.9605(4) -0.0056(3) 0.0436(11) Uani 1 1 d . . .
C6 C 0.8830(4) 1.0152(4) -0.1074(3) 0.0436(11) Uani 1 1 d . . .
C21 C 0.9199(4) 0.9783(3) -0.1896(3) 0.0445(11) Uani 1 1 d . . .
C22 C 0.8953(4) 1.0366(4) -0.2861(3) 0.0488(12) Uani 1 1 d . . .
C23 C 0.9729(5) 1.1007(5) -0.3499(4) 0.0688(16) Uani 1 1 d . . .
H23 H 1.0417 1.1111 -0.3329 0.083 Uiso 1 1 calc R . .
C24 C 0.9472(6) 1.1509(5) -0.4422(4) 0.084(2) Uani 1 1 d . . .
H24 H 0.9994 1.1945 -0.4858 0.101 Uiso 1 1 calc R . .
C25 C 0.8472(7) 1.1357(5) -0.4669(4) 0.083(2) Uani 1 1 d . . .
H25 H 0.8316 1.1674 -0.5281 0.099 Uiso 1 1 calc R . .
C55 C 1.4232(5) 0.2480(5) 0.1093(4) 0.0716(17) Uani 1 1 d . . .
H55 H 1.4771 0.1988 0.1110 0.086 Uiso 1 1 calc R . .
C54 C 1.4479(5) 0.3442(5) 0.1185(4) 0.0735(17) Uani 1 1 d . . .
H54 H 1.5192 0.3606 0.1261 0.088 Uiso 1 1 calc R . .
C53 C 1.3677(4) 0.4182(4) 0.1165(4) 0.0587(14) Uani 1 1 d . . .
H53 H 1.3852 0.4835 0.1236 0.070 Uiso 1 1 calc R . .
C52 C 1.2628(4) 0.3945(4) 0.1040(3) 0.0466(12) Uani 1 1 d . . .
C51 C 1.1755(4) 0.4737(3) 0.0962(3) 0.0440(11) Uani 1 1 d . . .
C2 C 1.1657(4) 0.5301(3) 0.0032(3) 0.0425(11) Uani 1 1 d . . .
C1 C 1.0918(4) 0.6156(4) -0.0205(3) 0.0452(11) Uani 1 1 d . . .
C4 C 1.2104(4) 0.6085(4) -0.1604(3) 0.0453(11) Uani 1 1 d . . .
C16 C 1.2677(5) 0.6318(4) -0.2538(4) 0.0616(15) Uani 1 1 d . . .
H16 H 1.2525 0.6902 -0.2980 0.074 Uiso 1 1 calc R . .
C15 C 1.3481(5) 0.5663(5) -0.2797(4) 0.0671(16) Uani 1 1 d . . .
H15 H 1.3859 0.5784 -0.3430 0.080 Uiso 1 1 calc R . .
C14 C 1.3725(5) 0.4825(5) -0.2117(4) 0.0714(17) Uani 1 1 d . . .
H14 H 1.4264 0.4385 -0.2303 0.086 Uiso 1 1 calc R . .
C13 C 1.3198(5) 0.4622(4) -0.1174(4) 0.0632(15) Uani 1 1 d . . .
H13 H 1.3394 0.4062 -0.0726 0.076 Uiso 1 1 calc R . .
C3 C 1.2362(4) 0.5262(4) -0.0888(3) 0.0463(12) Uani 1 1 d . . .
C17 C 1.0664(4) 0.7410(4) -0.1701(3) 0.0449(11) Uani 1 1 d . . .
C18 C 1.0507(4) 0.7587(4) -0.2661(3) 0.0551(14) Uani 1 1 d . . .
H18 H 1.0731 0.7176 -0.3102 0.066 Uiso 1 1 calc R . .
C19 C 0.9957(5) 0.8488(4) -0.2840(3) 0.0569(14) Uani 1 1 d . . .
H19 H 0.9752 0.8797 -0.3436 0.068 Uiso 1 1 calc R . .
C20 C 0.9754(4) 0.8869(4) -0.1996(3) 0.0467(12) Uani 1 1 d . . .
C7 C 0.8260(4) 1.1117(3) -0.1019(3) 0.0435(11) Uani 1 1 d . . .
C8 C 0.7851(4) 1.1103(3) -0.0056(3) 0.0434(11) Uani 1 1 d . . .
C34 C 0.7195(5) 0.9746(4) 0.3115(3) 0.0610(15) Uani 1 1 d . . .
H34 H 0.6895 0.9917 0.3699 0.073 Uiso 1 1 calc R . .
C33 C 0.7448(5) 1.0428(4) 0.2225(4) 0.0619(15) Uani 1 1 d . . .
H33 H 0.7357 1.1132 0.2108 0.074 Uiso 1 1 calc R . .
C37 C 0.6588(5) 0.7996(4) 0.4655(4) 0.0552(13) Uani 1 1 d . . .
C42 C 0.7055(6) 0.7949(5) 0.5474(4) 0.0768(18) Uani 1 1 d . . .
H42 H 0.7807 0.7835 0.5453 0.092 Uiso 1 1 calc R . .
C41 C 0.6436(7) 0.8068(6) 0.6338(5) 0.101(2) Uani 1 1 d . . .
H41 H 0.6763 0.8024 0.6895 0.121 Uiso 1 1 calc R . .
C40 C 0.5333(8) 0.8253(6) 0.6358(5) 0.115(3) Uani 1 1 d . . .
H40 H 0.4917 0.8355 0.6931 0.138 Uiso 1 1 calc R . .
C39 C 0.4831(7) 0.8290(7) 0.5558(5) 0.118(3) Uani 1 1 d . . .
H39 H 0.4078 0.8390 0.5581 0.142 Uiso 1 1 calc R . .
C38 C 0.5490(6) 0.8173(7) 0.4700(4) 0.103(3) Uani 1 1 d . . .
H38 H 0.5167 0.8217 0.4142 0.124 Uiso 1 1 calc R . .
C44 C 0.6534(6) 0.4631(5) 0.5787(4) 0.086(2) Uani 1 1 d . . .
H44 H 0.5963 0.4431 0.6301 0.104 Uiso 1 1 calc R . .
C43 C 0.6593(5) 0.5626(5) 0.5242(4) 0.0744(18) Uani 1 1 d . . .
H43 H 0.6069 0.6091 0.5400 0.089 Uiso 1 1 calc R . .
C47 C 0.9860(4) 0.5186(4) 0.3018(3) 0.0510(13) Uani 1 1 d . . .
C50 C 1.1136(4) 0.4790(4) 0.1884(3) 0.0449(11) Uani 1 1 d . . .
C49 C 1.1361(4) 0.4273(4) 0.2792(3) 0.0552(13) Uani 1 1 d . . .
H49 H 1.1932 0.3825 0.2905 0.066 Uiso 1 1 calc R . .
C48 C 1.0578(5) 0.4547(4) 0.3495(3) 0.0625(15) Uani 1 1 d . . .
H48 H 1.0546 0.4337 0.4166 0.075 Uiso 1 1 calc R . .
C9 C 0.8599(4) 0.6636(4) 0.3004(3) 0.0538(13) Uani 1 1 d . . .
C31 C 0.7200(4) 1.1881(4) 0.0227(4) 0.0554(13) Uani 1 1 d . . .
H31 H 0.6906 1.1845 0.0875 0.066 Uiso 1 1 calc R . .
C30 C 0.7011(5) 1.2704(4) -0.0496(4) 0.0603(14) Uani 1 1 d . . .
H30 H 0.6567 1.3225 -0.0332 0.072 Uiso 1 1 calc R . .
C29 C 0.7466(5) 1.2773(4) -0.1458(4) 0.0607(14) Uani 1 1 d . . .
H29 H 0.7348 1.3348 -0.1925 0.073 Uiso 1 1 calc R . .
C28 C 0.8101(5) 1.1988(4) -0.1735(4) 0.0567(14) Uani 1 1 d . . .
H28 H 0.8413 1.2037 -0.2381 0.068 Uiso 1 1 calc R . .
C27 C 0.7931(5) 1.0246(5) -0.3118(4) 0.0708(16) Uani 1 1 d . . .
H27 H 0.7395 0.9830 -0.2679 0.085 Uiso 1 1 calc R . .
C26 C 0.7688(6) 1.0739(6) -0.4027(5) 0.091(2) Uani 1 1 d . . .
H26 H 0.6996 1.0648 -0.4195 0.109 Uiso 1 1 calc R . .
C57 C 1.2395(5) 0.2971(4) 0.0943(4) 0.0620(14) Uani 1 1 d . . .
H57 H 1.1687 0.2806 0.0852 0.074 Uiso 1 1 calc R . .
C56 C 1.3177(5) 0.2241(4) 0.0976(4) 0.0675(16) Uani 1 1 d . . .
H56 H 1.2998 0.1584 0.0919 0.081 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.235(5) . ?
O2 C9 1.210(6) . ?
O3 C5 1.231(5) . ?
N4 C32 1.373(6) . ?
N4 C35 1.383(5) . ?
N4 H4 0.8600 . ?
N3 C32 1.397(6) . ?
N3 C5 1.401(5) . ?
N3 C8 1.428(6) . ?
N1 C4 1.416(5) . ?
N1 C1 1.383(6) . ?
N1 C17 1.406(6) . ?
N2 C17 1.356(5) . ?
N2 C20 1.391(5) . ?
N2 H2 0.8600 . ?
N5 C12 1.398(6) . ?
N5 C9 1.403(6) . ?
N5 C47 1.410(6) . ?
N6 C47 1.350(6) . ?
N6 C50 1.372(5) . ?
N6 H6 0.8600 . ?
C45 C46 1.383(8) . ?
C45 C44 1.376(8) . ?
C45 H45 0.9300 . ?
C46 C12 1.372(7) . ?
C46 H46 0.9300 . ?
C12 C11 1.402(7) . ?
C11 C43 1.379(7) . ?
C11 C10 1.470(7) . ?
C10 C36 1.375(7) . ?
C10 C9 1.492(6) . ?
C36 C35 1.445(7) . ?
C36 C37 1.504(6) . ?
C35 C34 1.386(7) . ?
C32 C33 1.376(6) . ?
C5 C6 1.469(6) . ?
C6 C21 1.379(6) . ?
C6 C7 1.477(6) . ?
C21 C20 1.421(6) . ?
C21 C22 1.498(6) . ?
C22 C27 1.375(8) . ?
C22 C23 1.374(8) . ?
C23 C24 1.421(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.353(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.368(10) . ?
C25 H25 0.9300 . ?
C55 C56 1.376(8) . ?
C55 C54 1.361(9) . ?
C55 H55 0.9300 . ?
C54 C53 1.392(7) . ?
C54 H54 0.9300 . ?
C53 C52 1.372(7) . ?
C53 H53 0.9300 . ?
C52 C57 1.375(7) . ?
C52 C51 1.501(6) . ?
C51 C2 1.399(6) . ?
C51 C50 1.429(6) . ?
C2 C3 1.468(6) . ?
C2 C1 1.469(6) . ?
C4 C3 1.402(6) . ?
C4 C16 1.380(7) . ?
C16 C15 1.378(7) . ?
C16 H16 0.9300 . ?
C15 C14 1.379(8) . ?
C15 H15 0.9300 . ?
C14 C13 1.372(7) . ?
C14 H14 0.9300 . ?
C13 C3 1.402(6) . ?
C13 H13 0.9300 . ?
C17 C18 1.376(6) . ?
C18 C19 1.373(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(6) . ?
C19 H19 0.9300 . ?
C7 C8 1.383(6) . ?
C7 C28 1.408(7) . ?
C8 C31 1.399(6) . ?
C34 C33 1.389(7) . ?
C34 H34 0.9300 . ?
C33 H33 0.9300 . ?
C37 C38 1.359(8) . ?
C37 C42 1.362(8) . ?
C42 C41 1.385(8) . ?
C42 H42 0.9300 . ?
C41 C40 1.372(11) . ?
C41 H41 0.9300 . ?
C40 C39 1.363(11) . ?
C40 H40 0.9300 . ?
C39 C38 1.398(8) . ?
C39 H39 0.9300 . ?
C38 H38 0.9300 . ?
C44 C43 1.386(8) . ?
C44 H44 0.9300 . ?
C43 H43 0.9300 . ?
C47 C48 1.374(7) . ?
C50 C49 1.395(6) . ?
C49 C48 1.387(7) . ?
C49 H49 0.9300 . ?
C48 H48 0.9300 . ?
C31 C30 1.382(7) . ?
C31 H31 0.9300 . ?
C30 C29 1.383(7) . ?
C30 H30 0.9300 . ?
C29 C28 1.393(7) . ?
C29 H29 0.9300 . ?
C28 H28 0.9300 . ?
C27 C26 1.394(8) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?
C57 C56 1.364(7) . ?
C57 H57 0.9300 . ?
C56 H56 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
C32 N4 C35 109.6(4) . . ?
C32 N4 H4 125.2 . . ?
C35 N4 H4 125.2 . . ?
C32 N3 C5 125.4(4) . . ?
C32 N3 C8 125.6(4) . . ?
C5 N3 C8 109.0(3) . . ?
C4 N1 C1 110.7(4) . . ?
C4 N1 C17 124.2(4) . . ?
C1 N1 C17 124.9(4) . . ?
C17 N2 C20 109.0(3) . . ?
C17 N2 H2 125.5 . . ?
C20 N2 H2 125.5 . . ?
C12 N5 C9 111.9(4) . . ?
C12 N5 C47 124.9(4) . . ?
C9 N5 C47 123.1(4) . . ?
C47 N6 C50 109.5(4) . . ?
C47 N6 H6 125.3 . . ?
C50 N6 H6 125.3 . . ?
C46 C45 C44 120.2(6) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C12 C46 C45 118.8(5) . . ?
C12 C46 H46 120.6 . . ?
C45 C46 H46 120.6 . . ?
C46 C12 N5 129.4(5) . . ?
C46 C12 C11 122.1(5) . . ?
N5 C12 C11 108.4(4) . . ?
C43 C11 C12 118.0(5) . . ?
C43 C11 C10 133.8(5) . . ?
C12 C11 C10 108.1(4) . . ?
C36 C10 C9 125.0(4) . . ?
C36 C10 C11 128.5(4) . . ?
C9 C10 C11 106.0(4) . . ?
C10 C36 C35 129.7(4) . . ?
C10 C36 C37 117.7(4) . . ?
C35 C36 C37 112.6(4) . . ?
C34 C35 N4 106.2(4) . . ?
C34 C35 C36 126.1(4) . . ?
N4 C35 C36 127.6(4) . . ?
N4 C32 N3 121.6(4) . . ?
N4 C32 C33 107.7(4) . . ?
N3 C32 C33 130.6(4) . . ?
O3 C5 N3 121.5(4) . . ?
O3 C5 C6 130.2(4) . . ?
N3 C5 C6 108.2(4) . . ?
C21 C6 C7 127.6(4) . . ?
C21 C6 C5 127.1(4) . . ?
C7 C6 C5 104.8(4) . . ?
C6 C21 C20 130.2(4) . . ?
C6 C21 C22 118.8(4) . . ?
C20 C21 C22 110.8(4) . . ?
C27 C22 C23 119.2(5) . . ?
C27 C22 C21 119.2(5) . . ?
C23 C22 C21 121.6(5) . . ?
C22 C23 C24 119.5(6) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.2(6) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.5(6) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C56 C55 C54 119.4(5) . . ?
C56 C55 H55 120.3 . . ?
C54 C55 H55 120.3 . . ?
C55 C54 C53 120.8(6) . . ?
C55 C54 H54 119.6 . . ?
C53 C54 H54 119.6 . . ?
C52 C53 C54 119.7(5) . . ?
C52 C53 H53 120.1 . . ?
C54 C53 H53 120.1 . . ?
C57 C52 C53 118.7(5) . . ?
C57 C52 C51 119.9(5) . . ?
C53 C52 C51 121.4(4) . . ?
C2 C51 C50 129.7(4) . . ?
C2 C51 C52 117.4(4) . . ?
C50 C51 C52 113.0(4) . . ?
C51 C2 C3 127.5(4) . . ?
C51 C2 C1 126.5(4) . . ?
C3 C2 C1 105.6(4) . . ?
O1 C1 N1 121.6(4) . . ?
O1 C1 C2 131.0(4) . . ?
N1 C1 C2 107.4(4) . . ?
N1 C4 C3 108.0(4) . . ?
N1 C4 C16 128.9(4) . . ?
C3 C4 C16 123.0(4) . . ?
C15 C16 C4 118.2(5) . . ?
C15 C16 H16 120.9 . . ?
C4 C16 H16 120.9 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C13 C14 C15 122.1(5) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C13 C3 119.7(5) . . ?
C14 C13 H13 120.2 . . ?
C3 C13 H13 120.2 . . ?
C4 C3 C13 117.0(4) . . ?
C4 C3 C2 108.1(4) . . ?
C13 C3 C2 134.9(4) . . ?
N2 C17 C18 109.2(4) . . ?
N2 C17 N1 122.2(4) . . ?
C18 C17 N1 128.7(4) . . ?
C17 C18 C19 106.6(4) . . ?
C17 C18 H18 126.7 . . ?
C19 C18 H18 126.7 . . ?
C20 C19 C18 109.7(4) . . ?
C20 C19 H19 125.1 . . ?
C18 C19 H19 125.1 . . ?
C19 C20 N2 105.5(4) . . ?
C19 C20 C21 126.1(4) . . ?
N2 C20 C21 128.4(4) . . ?
C8 C7 C28 118.9(4) . . ?
C8 C7 C6 108.8(4) . . ?
C28 C7 C6 132.3(4) . . ?
C7 C8 C31 122.5(4) . . ?
C7 C8 N3 109.0(4) . . ?
C31 C8 N3 128.4(4) . . ?
C33 C34 C35 108.9(4) . . ?
C33 C34 H34 125.6 . . ?
C35 C34 H34 125.6 . . ?
C34 C33 C32 107.5(5) . . ?
C34 C33 H33 126.2 . . ?
C32 C33 H33 126.2 . . ?
C38 C37 C42 118.3(5) . . ?
C38 C37 C36 121.9(5) . . ?
C42 C37 C36 119.8(5) . . ?
C37 C42 C41 121.4(7) . . ?
C37 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
C40 C41 C42 118.9(7) . . ?
C40 C41 H41 120.6 . . ?
C42 C41 H41 120.6 . . ?
C41 C40 C39 121.5(6) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C40 C39 C38 117.7(7) . . ?
C40 C39 H39 121.2 . . ?
C38 C39 H39 121.2 . . ?
C37 C38 C39 122.3(7) . . ?
C37 C38 H38 118.9 . . ?
C39 C38 H38 118.9 . . ?
C43 C44 C45 120.5(6) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C11 C43 C44 120.4(5) . . ?
C11 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
N6 C47 C48 108.6(4) . . ?
N6 C47 N5 122.1(4) . . ?
C48 C47 N5 129.2(4) . . ?
N6 C50 C49 106.8(4) . . ?
N6 C50 C51 127.3(4) . . ?
C49 C50 C51 126.0(4) . . ?
C48 C49 C50 107.7(4) . . ?
C48 C49 H49 126.2 . . ?
C50 C49 H49 126.2 . . ?
C47 C48 C49 107.4(4) . . ?
C47 C48 H48 126.3 . . ?
C49 C48 H48 126.3 . . ?
O2 C9 N5 123.5(4) . . ?
O2 C9 C10 131.3(5) . . ?
N5 C9 C10 105.2(4) . . ?
C30 C31 C8 117.3(5) . . ?
C30 C31 H31 121.4 . . ?
C8 C31 H31 121.4 . . ?
C31 C30 C29 121.6(5) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C29 C28 120.6(5) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C7 C28 C29 118.8(5) . . ?
C7 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C22 C27 C26 120.9(6) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C25 C26 C27 119.7(6) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C52 C57 C56 121.5(5) . . ?
C52 C57 H57 119.2 . . ?
C56 C57 H57 119.2 . . ?
C55 C56 C57 119.8(5) . . ?
C55 C56 H56 120.1 . . ?
C57 C56 H56 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.48
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.306
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_1122
_database_code_depnum_ccdc_archive 'CCDC 1427527'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C57 H21 F15 N6 O3, 2(C2), C'
_chemical_formula_sum            'C62 H21 F15 N6 O3'
_chemical_formula_weight         1182.85

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   8.6387(19)
_cell_length_b                   14.094(3)
_cell_length_c                   42.764(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.418(5)
_cell_angle_gamma                90.00
_cell_volume                     5205(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2376
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64676
_diffrn_reflns_av_R_equivalents  0.1388
_diffrn_reflns_av_sigmaI/netI    0.1206
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         24.41
_reflns_number_total             8559
_reflns_number_gt                4952
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8490
_refine_ls_number_parameters     775
_refine_ls_number_restraints     247
_refine_ls_R_factor_all          0.1785
_refine_ls_R_factor_gt           0.1046
_refine_ls_wR_factor_ref         0.2842
_refine_ls_wR_factor_gt          0.2612
_refine_ls_goodness_of_fit_ref   1.554
_refine_ls_restrained_S_all      1.536
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F5 F 0.2646(5) 0.3116(3) 1.07181(9) 0.0318(10) Uani 1 1 d U . .
F15 F 1.1936(4) 0.3098(3) 0.87815(9) 0.0307(10) Uani 1 1 d U . .
F11 F 0.8021(5) 0.4762(3) 0.82162(10) 0.0355(11) Uani 1 1 d U . .
F10 F 0.1973(4) -0.1552(3) 0.87018(9) 0.0310(10) Uani 1 1 d U . .
F1 F 0.8131(4) 0.3150(3) 1.08223(9) 0.0304(10) Uani 1 1 d U . .
F14 F 1.4055(5) 0.3749(3) 0.83789(10) 0.0380(11) Uani 1 1 d U . .
F7 F -0.3963(5) -0.0301(3) 0.87256(10) 0.0372(11) Uani 1 1 d U . .
F6 F -0.1706(5) 0.0688(3) 0.90345(9) 0.0342(11) Uani 1 1 d U . .
F4 F 0.2445(5) 0.3721(3) 1.13099(10) 0.0394(11) Uani 1 1 d U . .
F2 F 0.7885(5) 0.3754(3) 1.14156(10) 0.0401(11) Uani 1 1 d U . .
F12 F 1.0160(5) 0.5421(3) 0.78240(10) 0.0445(12) Uani 1 1 d U . .
F9 F -0.0276(5) -0.2516(3) 0.83857(10) 0.0411(12) Uani 1 1 d U . .
F8 F -0.3249(5) -0.1879(3) 0.83986(10) 0.0428(12) Uani 1 1 d U . .
F3 F 0.5052(5) 0.4041(3) 1.16641(10) 0.0441(12) Uani 1 1 d U . .
F13 F 1.3163(5) 0.4893(3) 0.78943(10) 0.0420(12) Uani 1 1 d U . .
O1 O 0.6349(5) 0.2691(3) 0.97185(11) 0.0267(12) Uani 1 1 d U . .
O3 O 0.3723(5) 0.1301(3) 0.94547(11) 0.0266(12) Uani 1 1 d U . .
O2 O 0.5683(6) 0.2665(3) 0.89877(11) 0.0300(12) Uani 1 1 d U . .
N6 N 0.4365(6) 0.1595(4) 1.00575(14) 0.0225(13) Uani 1 1 d U . .
H6 H 0.4459 0.1884 0.9882 0.027 Uiso 1 1 calc R . .
N1 N 0.7363(6) 0.4203(4) 0.98013(13) 0.0206(13) Uani 1 1 d U . .
N3 N 0.5660(7) 0.1837(4) 0.85260(13) 0.0253(14) Uani 1 1 d U . .
N4 N 0.3702(6) 0.1131(4) 0.88383(14) 0.0243(14) Uani 1 1 d U . .
H4 H 0.4193 0.1210 0.9014 0.029 Uiso 1 1 calc R . .
N2 N 0.7743(6) 0.3766(4) 0.92694(13) 0.0228(13) Uani 1 1 d U . .
H2 H 0.7030 0.3340 0.9266 0.027 Uiso 1 1 calc R . .
N5 N 0.2867(6) 0.0296(4) 0.98407(13) 0.0217(13) Uani 1 1 d U . .
C39 C 0.6672(9) 0.1681(5) 0.82739(16) 0.0277(17) Uani 1 1 d U . .
C29 C 0.0211(8) -0.0416(4) 0.88814(16) 0.0208(15) Uani 1 1 d U . .
C4 C 0.7252(8) 0.4915(4) 1.00357(16) 0.0194(15) Uani 1 1 d U . .
C10 C 0.5400(8) 0.3109(4) 1.07483(16) 0.0227(15) Uani 1 1 d U . .
C54 C 0.8675(8) 0.3996(5) 0.90216(17) 0.0246(16) Uani 1 1 d U . .
C44 C 0.7948(8) 0.2274(5) 0.83146(17) 0.0254(16) Uani 1 1 d U . .
C16 C 0.4908(8) 0.1926(5) 1.03428(17) 0.0225(16) Uani 1 1 d U . .
C19 C 0.3652(8) 0.0735(5) 1.00956(16) 0.0217(15) Uani 1 1 d U . .
C1 C 0.6539(8) 0.3387(5) 0.98909(16) 0.0202(15) Uani 1 1 d U . .
C30 C -0.1319(8) -0.0121(5) 0.88843(17) 0.0246(16) Uani 1 1 d U . .
C56 C 0.9330(8) 0.4910(4) 0.94363(17) 0.0236(16) Uani 1 1 d U . .
H56 H 0.9816 0.5354 0.9566 0.028 Uiso 1 1 calc R . .
C20 C 0.1805(8) -0.0476(4) 0.98592(16) 0.0205(15) Uani 1 1 d U . .
C35 C 0.2280(8) 0.0697(5) 0.87994(17) 0.0242(16) Uani 1 1 d U . .
C28 C 0.1490(8) 0.0155(4) 0.90316(16) 0.0206(15) Uani 1 1 d U . .
C27 C 0.2893(8) 0.0629(5) 0.95349(16) 0.0220(15) Uani 1 1 d U . .
C48 C 0.9933(8) 0.3911(5) 0.85121(16) 0.0231(15) Uani 1 1 d U . .
C55 C 0.9667(8) 0.4724(5) 0.91313(17) 0.0266(17) Uani 1 1 d U . .
H55 H 1.0421 0.5027 0.9016 0.032 Uiso 1 1 calc R . .
C50 C 1.0585(9) 0.4838(5) 0.80608(17) 0.0305(18) Uani 1 1 d U . .
C46 C 0.6322(9) 0.2461(5) 0.87385(17) 0.0250(16) Uani 1 1 d U . .
C38 C 0.4201(8) 0.1414(5) 0.85545(17) 0.0251(16) Uani 1 1 d U . .
C57 C 0.8128(8) 0.4312(5) 0.95156(17) 0.0227(16) Uani 1 1 d U . .
C34 C 0.0497(8) -0.1226(5) 0.87131(16) 0.0235(16) Uani 1 1 d U . .
C47 C 0.8705(8) 0.3527(5) 0.87283(16) 0.0230(16) Uani 1 1 d U . .
C52 C 1.2567(8) 0.3996(5) 0.83420(17) 0.0270(17) Uani 1 1 d U . .
C26 C 0.1777(8) 0.0054(5) 0.93448(17) 0.0230(15) Uani 1 1 d U . .
C3 C 0.6471(8) 0.4523(4) 1.02916(16) 0.0203(15) Uani 1 1 d U . .
C25 C 0.1110(8) -0.0627(4) 0.95653(16) 0.0217(15) Uani 1 1 d U . .
C15 C 0.3981(8) 0.3266(5) 1.08885(16) 0.0238(16) Uani 1 1 d U . .
C9 C 0.5510(8) 0.2856(4) 1.04083(16) 0.0211(15) Uani 1 1 d U . .
C45 C 0.7775(8) 0.2815(5) 0.86029(16) 0.0223(15) Uani 1 1 d U . .
C2 C 0.6076(8) 0.3542(4) 1.02185(16) 0.0207(15) Uani 1 1 d U . .
C13 C 0.5164(9) 0.3739(5) 1.13678(17) 0.0304(17) Uani 1 1 d U . .
C18 C 0.3793(8) 0.0471(5) 1.04073(16) 0.0248(17) Uani 1 1 d U . .
H18 H 0.3440 -0.0089 1.0496 0.030 Uiso 1 1 calc R . .
C11 C 0.6717(9) 0.3277(5) 1.09396(17) 0.0246(16) Uani 1 1 d U . .
C17 C 0.4571(8) 0.1214(5) 1.05622(17) 0.0243(16) Uani 1 1 d U . .
H17 H 0.4824 0.1233 1.0775 0.029 Uiso 1 1 calc R . .
C8 C 0.6128(8) 0.5144(4) 1.05377(17) 0.0229(16) Uani 1 1 d U . .
H8 H 0.5565 0.4925 1.0706 0.028 Uiso 1 1 calc R . .
C23 C -0.0347(8) -0.1913(5) 0.97876(17) 0.0271(17) Uani 1 1 d U . .
H23 H -0.1069 -0.2399 0.9765 0.033 Uiso 1 1 calc R . .
C14 C 0.3864(9) 0.3590(5) 1.11831(18) 0.0293(17) Uani 1 1 d U . .
C12 C 0.6585(9) 0.3593(5) 1.12410(18) 0.0295(17) Uani 1 1 d U . .
C36 C 0.1914(9) 0.0742(5) 0.84759(17) 0.0286(17) Uani 1 1 d U . .
H36 H 0.1019 0.0505 0.8379 0.034 Uiso 1 1 calc R . .
C7 C 0.6619(8) 0.6072(5) 1.05315(17) 0.0269(17) Uani 1 1 d U . .
H7 H 0.6421 0.6466 1.0700 0.032 Uiso 1 1 calc R . .
C37 C 0.3115(9) 0.1199(5) 0.83259(18) 0.0319(18) Uani 1 1 d U . .
H37 H 0.3171 0.1333 0.8114 0.038 Uiso 1 1 calc R . .
C33 C -0.0620(9) -0.1731(5) 0.85566(18) 0.0309(18) Uani 1 1 d U . .
C24 C 0.0029(8) -0.1364(4) 0.95265(17) 0.0234(16) Uani 1 1 d U . .
H24 H -0.0429 -0.1486 0.9332 0.028 Uiso 1 1 calc R . .
C6 C 0.7406(8) 0.6431(5) 1.02779(17) 0.0261(17) Uani 1 1 d U . .
H6A H 0.7729 0.7060 1.0278 0.031 Uiso 1 1 calc R . .
C31 C -0.2477(9) -0.0611(5) 0.87212(18) 0.0297(17) Uani 1 1 d U . .
C49 C 0.9517(9) 0.4497(5) 0.82639(17) 0.0269(16) Uani 1 1 d U . .
C5 C 0.7711(8) 0.5849(5) 1.00238(17) 0.0241(17) Uani 1 1 d U . .
H5 H 0.8212 0.6086 0.9850 0.029 Uiso 1 1 calc R . .
C32 C -0.2119(9) -0.1417(5) 0.85576(18) 0.0292(17) Uani 1 1 d U . .
C53 C 1.1472(8) 0.3672(5) 0.85462(17) 0.0247(16) Uani 1 1 d U . .
C51 C 1.2116(9) 0.4564(5) 0.81028(17) 0.0318(17) Uani 1 1 d U . .
C42 C 0.8990(9) 0.1532(5) 0.78527(18) 0.0360(19) Uani 1 1 d U . .
H42 H 0.9759 0.1490 0.7705 0.043 Uiso 1 1 calc R . .
C21 C 0.1438(8) -0.1013(5) 1.01171(17) 0.0246(16) Uani 1 1 d U . .
H21 H 0.1899 -0.0899 1.0312 0.030 Uiso 1 1 calc R . .
C40 C 0.6533(9) 0.1006(5) 0.80405(17) 0.0343(19) Uani 1 1 d U . .
H40 H 0.5684 0.0600 0.8027 0.041 Uiso 1 1 calc R . .
C22 C 0.0328(8) -0.1747(5) 1.00721(18) 0.0299(18) Uani 1 1 d U . .
H22 H 0.0057 -0.2121 1.0241 0.036 Uiso 1 1 calc R . .
C43 C 0.9149(8) 0.2175(5) 0.80975(17) 0.0285(17) Uani 1 1 d U . .
H43 H 1.0042 0.2541 0.8119 0.034 Uiso 1 1 calc R . .
C41 C 0.7707(9) 0.0958(5) 0.78274(19) 0.038(2) Uani 1 1 d U . .
H41 H 0.7627 0.0527 0.7663 0.046 Uiso 1 1 calc R . .
C1S C 0.305(3) 0.2651(9) 0.7634(6) 0.242(10) Uani 1 1 d U . .
C2S C 0.337(2) 0.1834(14) 0.7353(4) 0.165(6) Uani 1 1 d U . .
C3S C 0.550(4) 0.2915(16) 0.7330(6) 0.282(13) Uani 1 1 d U . .
C5S C 0.851(4) 0.370(2) 0.7223(5) 0.325(14) Uani 1 1 d U . .
C6S C 0.594(4) 0.3797(14) 0.7330(6) 0.337(17) 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
F5 C15 1.366(8) . ?
F15 C53 1.345(8) . ?
F11 C49 1.355(8) . ?
F10 C34 1.356(7) . ?
F1 C11 1.344(8) . ?
F14 C52 1.337(8) . ?
F7 C31 1.356(8) . ?
F6 C30 1.355(7) . ?
F4 C14 1.365(8) . ?
F2 C12 1.353(8) . ?
F12 C50 1.348(8) . ?
F9 C33 1.363(8) . ?
F8 C32 1.344(8) . ?
F3 C13 1.342(8) . ?
F13 C51 1.367(8) . ?
O1 C1 1.235(8) . ?
O3 C27 1.242(8) . ?
O2 C46 1.246(8) . ?
N6 C19 1.371(8) . ?
N6 C16 1.378(9) . ?
N1 C1 1.411(8) . ?
N1 C57 1.412(8) . ?
N1 C4 1.423(8) . ?
N3 C46 1.378(9) . ?
N3 C38 1.403(9) . ?
N3 C39 1.421(9) . ?
N4 C38 1.357(8) . ?
N4 C35 1.379(9) . ?
N2 C57 1.339(8) . ?
N2 C54 1.385(8) . ?
N5 C27 1.390(8) . ?
N5 C19 1.412(9) . ?
N5 C20 1.426(8) . ?
C39 C40 1.382(10) . ?
C39 C44 1.391(10) . ?
C29 C34 1.376(9) . ?
C29 C30 1.386(9) . ?
C29 C28 1.498(10) . ?
C4 C5 1.377(9) . ?
C4 C3 1.412(9) . ?
C10 C15 1.395(9) . ?
C10 C11 1.405(10) . ?
C10 C9 1.502(9) . ?
C54 C47 1.419(10) . ?
C54 C55 1.410(9) . ?
C44 C43 1.416(9) . ?
C44 C45 1.460(9) . ?
C16 C17 1.410(9) . ?
C16 C9 1.435(9) . ?
C19 C18 1.387(9) . ?
C1 C2 1.483(10) . ?
C30 C31 1.389(10) . ?
C56 C55 1.369(9) . ?
C56 C57 1.386(9) . ?
C20 C21 1.381(9) . ?
C20 C25 1.395(10) . ?
C35 C36 1.413(10) . ?
C35 C28 1.438(9) . ?
C28 C26 1.364(9) . ?
C27 C26 1.485(10) . ?
C48 C53 1.376(10) . ?
C48 C49 1.386(10) . ?
C48 C47 1.524(10) . ?
C50 C49 1.370(10) . ?
C50 C51 1.385(10) . ?
C46 C45 1.482(10) . ?
C38 C37 1.372(10) . ?
C34 C33 1.361(10) . ?
C47 C45 1.385(9) . ?
C52 C51 1.348(10) . ?
C52 C53 1.381(10) . ?
C26 C25 1.473(9) . ?
C3 C8 1.406(9) . ?
C3 C2 1.457(9) . ?
C25 C24 1.404(9) . ?
C15 C14 1.346(10) . ?
C9 C2 1.361(9) . ?
C13 C14 1.373(11) . ?
C13 C12 1.369(10) . ?
C18 C17 1.402(10) . ?
C11 C12 1.371(10) . ?
C8 C7 1.375(9) . ?
C23 C22 1.356(10) . ?
C23 C24 1.403(10) . ?
C36 C37 1.392(10) . ?
C7 C6 1.389(10) . ?
C33 C32 1.368(10) . ?
C6 C5 1.391(9) . ?
C31 C32 1.374(10) . ?
C42 C41 1.375(11) . ?
C42 C43 1.389(10) . ?
C21 C22 1.420(10) . ?
C40 C41 1.382(10) . ?
C1S C2S 1.69(3) . ?
C2S C3S 2.39(4) . ?
C3S C6S 1.30(3) . ?
C5S C6S 2.28(5) . ?

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
C19 N6 C16 109.8(6) . . ?
C1 N1 C57 125.0(5) . . ?
C1 N1 C4 109.9(5) . . ?
C57 N1 C4 125.1(5) . . ?
C46 N3 C38 124.9(6) . . ?
C46 N3 C39 110.3(6) . . ?
C38 N3 C39 124.8(6) . . ?
C38 N4 C35 108.9(6) . . ?
C57 N2 C54 109.2(6) . . ?
C27 N5 C19 124.0(6) . . ?
C27 N5 C20 109.6(6) . . ?
C19 N5 C20 126.1(6) . . ?
C40 C39 C44 124.0(7) . . ?
C40 C39 N3 127.6(7) . . ?
C44 C39 N3 108.2(6) . . ?
C34 C29 C30 115.9(6) . . ?
C34 C29 C28 122.0(6) . . ?
C30 C29 C28 121.9(6) . . ?
C5 C4 C3 123.1(6) . . ?
C5 C4 N1 128.6(6) . . ?
C3 C4 N1 108.2(5) . . ?
C15 C10 C11 115.5(6) . . ?
C15 C10 C9 122.1(6) . . ?
C11 C10 C9 122.2(6) . . ?
N2 C54 C47 126.2(6) . . ?
N2 C54 C55 106.0(6) . . ?
C47 C54 C55 127.5(7) . . ?
C39 C44 C43 116.7(6) . . ?
C39 C44 C45 108.8(6) . . ?
C43 C44 C45 134.2(7) . . ?
N6 C16 C17 106.1(6) . . ?
N6 C16 C9 126.6(6) . . ?
C17 C16 C9 126.9(7) . . ?
N6 C19 C18 108.8(6) . . ?
N6 C19 N5 120.3(6) . . ?
C18 C19 N5 130.8(6) . . ?
O1 C1 N1 123.1(6) . . ?
O1 C1 C2 130.2(6) . . ?
N1 C1 C2 106.6(6) . . ?
F6 C30 C31 118.2(6) . . ?
F6 C30 C29 120.2(6) . . ?
C31 C30 C29 121.5(6) . . ?
C55 C56 C57 107.2(6) . . ?
C21 C20 C25 122.3(6) . . ?
C21 C20 N5 128.5(7) . . ?
C25 C20 N5 109.2(6) . . ?
N4 C35 C36 106.0(6) . . ?
N4 C35 C28 126.1(7) . . ?
C36 C35 C28 126.9(7) . . ?
C26 C28 C35 130.9(7) . . ?
C26 C28 C29 118.7(6) . . ?
C35 C28 C29 110.3(6) . . ?
O3 C27 N5 122.7(6) . . ?
O3 C27 C26 129.5(6) . . ?
N5 C27 C26 107.8(6) . . ?
C53 C48 C49 117.3(6) . . ?
C53 C48 C47 122.3(6) . . ?
C49 C48 C47 120.3(6) . . ?
C56 C55 C54 108.3(6) . . ?
F12 C50 C49 121.0(7) . . ?
F12 C50 C51 120.6(7) . . ?
C49 C50 C51 118.4(7) . . ?
O2 C46 N3 121.8(6) . . ?
O2 C46 C45 130.8(6) . . ?
N3 C46 C45 107.3(6) . . ?
N4 C38 C37 110.3(6) . . ?
N4 C38 N3 120.6(6) . . ?
C37 C38 N3 129.2(7) . . ?
N2 C57 C56 109.2(6) . . ?
N2 C57 N1 120.4(6) . . ?
C56 C57 N1 130.4(6) . . ?
F10 C34 C33 117.5(6) . . ?
F10 C34 C29 118.7(6) . . ?
C33 C34 C29 123.8(7) . . ?
C45 C47 C54 131.1(7) . . ?
C45 C47 C48 115.3(6) . . ?
C54 C47 C48 113.5(6) . . ?
F14 C52 C51 120.2(7) . . ?
F14 C52 C53 120.7(6) . . ?
C51 C52 C53 119.1(7) . . ?
C28 C26 C25 129.2(6) . . ?
C28 C26 C27 125.5(6) . . ?
C25 C26 C27 105.3(6) . . ?
C4 C3 C8 116.8(6) . . ?
C4 C3 C2 108.6(6) . . ?
C8 C3 C2 134.3(6) . . ?
C20 C25 C24 119.3(6) . . ?
C20 C25 C26 108.1(6) . . ?
C24 C25 C26 132.6(7) . . ?
C14 C15 F5 118.0(7) . . ?
C14 C15 C10 122.9(7) . . ?
F5 C15 C10 119.0(6) . . ?
C2 C9 C16 131.8(7) . . ?
C2 C9 C10 116.2(6) . . ?
C16 C9 C10 112.0(6) . . ?
C47 C45 C44 129.4(7) . . ?
C47 C45 C46 125.5(6) . . ?
C44 C45 C46 105.1(6) . . ?
C9 C2 C3 129.2(6) . . ?
C9 C2 C1 124.6(6) . . ?
C3 C2 C1 106.0(5) . . ?
F3 C13 C14 120.9(7) . . ?
F3 C13 C12 120.5(7) . . ?
C14 C13 C12 118.5(7) . . ?
C19 C18 C17 106.5(6) . . ?
F1 C11 C12 119.4(7) . . ?
F1 C11 C10 119.4(6) . . ?
C12 C11 C10 121.1(7) . . ?
C18 C17 C16 108.8(6) . . ?
C7 C8 C3 120.4(7) . . ?
C22 C23 C24 121.0(7) . . ?
C15 C14 F4 120.4(7) . . ?
C15 C14 C13 120.7(7) . . ?
F4 C14 C13 118.7(7) . . ?
F2 C12 C11 119.1(7) . . ?
F2 C12 C13 119.7(7) . . ?
C11 C12 C13 121.2(7) . . ?
C37 C36 C35 108.7(7) . . ?
C8 C7 C6 121.2(7) . . ?
C38 C37 C36 106.1(7) . . ?
C34 C33 F9 121.7(7) . . ?
C34 C33 C32 119.3(7) . . ?
F9 C33 C32 118.9(6) . . ?
C25 C24 C23 118.7(7) . . ?
C7 C6 C5 120.1(7) . . ?
F7 C31 C32 119.9(7) . . ?
F7 C31 C30 120.2(6) . . ?
C32 C31 C30 119.9(7) . . ?
F11 C49 C50 117.5(7) . . ?
F11 C49 C48 120.5(6) . . ?
C50 C49 C48 121.9(7) . . ?
C4 C5 C6 118.3(7) . . ?
F8 C32 C33 121.2(6) . . ?
F8 C32 C31 119.2(7) . . ?
C33 C32 C31 119.6(7) . . ?
F15 C53 C48 119.7(6) . . ?
F15 C53 C52 118.4(6) . . ?
C48 C53 C52 121.8(7) . . ?
C52 C51 F13 120.8(7) . . ?
C52 C51 C50 121.4(7) . . ?
F13 C51 C50 117.8(7) . . ?
C41 C42 C43 120.5(7) . . ?
C20 C21 C22 117.3(7) . . ?
C39 C40 C41 117.2(7) . . ?
C23 C22 C21 121.4(7) . . ?
C42 C43 C44 119.9(7) . . ?
C42 C41 C40 121.5(7) . . ?
C1S C2S C3S 74.6(15) . . ?
C6S C3S C2S 147(3) . . ?
C3S C6S C5S 103(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.41
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.623
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.209
