# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

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

data_cas2057a_0m
_database_code_depnum_ccdc_archive 'CCDC 1521360'
_audit_update_record             
;
2016-12-07 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
_audit_creation_date             2016-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N4 O'
_chemical_formula_sum            'C24 H16 N4 O'
_chemical_formula_weight         376.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.4429(4)
_cell_length_b                   8.4127(2)
_cell_length_c                   15.5871(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.5300(10)
_cell_angle_gamma                90
_cell_volume                     1862.00(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1929
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.978
_cell_measurement_theta_min      27.890
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.805781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1408 before and 0.0840 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1449 before and 0.0879 after correction.
 The Ratio of minimum to maximum transmission is 0.81.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 34378 reflections, Rint = 0.0913
 (20167 with I > 3sig(I), Rint = 0.0714)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.088
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3385
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_min         3.112
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2910
_reflns_number_total             3385
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+2.8489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1291
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7232(18) 0.2768(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C5(H5), C3(H3), C25(H25), C2(H2), C1(H1), C27(H27), C29(H29),
 C28(H28), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O13 O 0.61018(14) 0.3851(3) 0.45980(13) 0.0167(5) Uani 1 1 d . . . . .
N23 N 0.82538(18) 0.1767(3) 0.70076(16) 0.0191(6) Uani 1 1 d . . . . .
N17 N 0.98571(19) 0.4198(3) 0.59797(18) 0.0242(6) Uani 1 1 d . . . . .
N21 N 0.64168(19) 0.5722(3) 0.65814(17) 0.0218(6) Uani 1 1 d . . . . .
N19 N 0.7812(2) 0.7647(3) 0.52563(18) 0.0248(6) Uani 1 1 d . . . . .
C22 C 0.7885(2) 0.2625(3) 0.64875(19) 0.0139(6) Uani 1 1 d . . . . .
C8 C 0.7200(2) 0.1543(4) 0.46946(18) 0.0148(6) Uani 1 1 d . . . . .
H8 H 0.7074 0.0434 0.4681 0.018 Uiso 1 1 calc R . . . .
C16 C 0.9074(2) 0.4326(3) 0.57069(19) 0.0161(6) Uani 1 1 d . . . . .
C6 C 0.5953(2) 0.1801(4) 0.56396(18) 0.0144(6) Uani 1 1 d . . . . .
C24 C 0.8479(2) 0.1098(4) 0.38567(19) 0.0156(6) Uani 1 1 d . . . . .
C4 C 0.5593(2) -0.0413(4) 0.65124(19) 0.0180(7) Uani 1 1 d . . . . .
H4 H 0.5750 -0.1425 0.6769 0.022 Uiso 1 1 calc R . . . .
C12 C 0.7368(2) 0.3690(3) 0.58069(18) 0.0133(6) Uani 1 1 d . . . . .
C9 C 0.7890(2) 0.2116(4) 0.43193(19) 0.0149(6) Uani 1 1 d . . . . .
C10 C 0.8004(2) 0.3909(4) 0.43070(18) 0.0144(6) Uani 1 1 d . . . . .
H10 H 0.8607 0.4155 0.4106 0.017 Uiso 1 1 calc R . . . .
C5 C 0.6189(2) 0.0314(4) 0.60319(19) 0.0157(6) Uani 1 1 d . . . . .
H5 H 0.6760 -0.0192 0.5967 0.019 Uiso 1 1 calc R . . . .
C3 C 0.4765(2) 0.0331(4) 0.6621(2) 0.0173(6) Uani 1 1 d . . . . .
H3 H 0.4363 -0.0158 0.6963 0.021 Uiso 1 1 calc R . . . .
C20 C 0.6839(2) 0.4851(4) 0.62421(19) 0.0160(6) Uani 1 1 d . . . . .
C25 C 0.8081(2) -0.0211(4) 0.3382(2) 0.0174(6) Uani 1 1 d . . . . .
H25 H 0.7434 -0.0447 0.3361 0.021 Uiso 1 1 calc R . . . .
C7 C 0.6619(2) 0.2654(3) 0.51410(19) 0.0142(6) Uani 1 1 d . . . . .
C2 C 0.4525(2) 0.1784(4) 0.6232(2) 0.0192(7) Uani 1 1 d . . . . .
H2 H 0.3955 0.2287 0.6305 0.023 Uiso 1 1 calc R . . . .
C11 C 0.8079(2) 0.4563(3) 0.52756(19) 0.0135(6) Uani 1 1 d . . . . .
C1 C 0.5108(2) 0.2519(4) 0.57343(19) 0.0180(7) Uani 1 1 d . . . . .
H1 H 0.4931 0.3509 0.5459 0.022 Uiso 1 1 calc R . . . .
C18 C 0.7920(2) 0.6311(4) 0.5264(2) 0.0186(7) Uani 1 1 d . . . . .
C15 C 0.7190(2) 0.4651(4) 0.36533(19) 0.0182(7) Uani 1 1 d . . . . .
H15A H 0.7176 0.5810 0.3761 0.022 Uiso 1 1 calc R . . . .
H15B H 0.7312 0.4494 0.3054 0.022 Uiso 1 1 calc R . . . .
C14 C 0.6235(2) 0.3953(4) 0.37104(19) 0.0188(7) Uani 1 1 d . . . . .
H14A H 0.5734 0.4627 0.3374 0.023 Uiso 1 1 calc R . . . .
H14B H 0.6181 0.2879 0.3447 0.023 Uiso 1 1 calc R . . . .
C27 C 0.9566(2) -0.0848(4) 0.2972(2) 0.0213(7) Uani 1 1 d . . . . .
H27 H 0.9936 -0.1499 0.2668 0.026 Uiso 1 1 calc R . . . .
C29 C 0.9437(2) 0.1423(4) 0.3889(2) 0.0209(7) Uani 1 1 d . . . . .
H29 H 0.9719 0.2313 0.4210 0.025 Uiso 1 1 calc R . . . .
C28 C 0.9975(2) 0.0454(4) 0.3457(2) 0.0214(7) Uani 1 1 d . . . . .
H28 H 1.0625 0.0673 0.3490 0.026 Uiso 1 1 calc R . . . .
C26 C 0.8619(2) -0.1184(4) 0.2935(2) 0.0218(7) Uani 1 1 d . . . . .
H26 H 0.8337 -0.2069 0.2609 0.026 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
O13 C7 1.434(3) . ?
O13 C14 1.434(3) . ?
N23 C22 1.142(4) . ?
N17 C16 1.138(4) . ?
N21 C20 1.143(4) . ?
N19 C18 1.134(4) . ?
C22 C12 1.482(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.335(4) . ?
C8 C7 1.509(4) . ?
C16 C11 1.485(4) . ?
C6 C5 1.406(4) . ?
C6 C7 1.522(4) . ?
C6 C1 1.394(4) . ?
C24 C9 1.484(4) . ?
C24 C25 1.391(4) . ?
C24 C29 1.403(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C4 C3 1.388(4) . ?
C12 C20 1.479(4) . ?
C12 C7 1.612(4) . ?
C12 C11 1.610(4) . ?
C9 C10 1.518(4) . ?
C10 H10 1.0000 . ?
C10 C11 1.592(4) . ?
C10 C15 1.540(4) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.381(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.399(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.390(4) . ?
C11 C18 1.488(4) . ?
C1 H1 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.517(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C27 H27 0.9500 . ?
C27 C28 1.398(5) . ?
C27 C26 1.388(5) . ?
C29 H29 0.9500 . ?
C29 C28 1.383(4) . ?
C28 H28 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O13 C7 117.7(2) . . ?
N23 C22 C12 177.4(3) . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
N17 C16 C11 174.5(3) . . ?
C5 C6 C7 121.1(3) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C7 119.8(3) . . ?
C25 C24 C9 119.8(3) . . ?
C25 C24 C29 118.9(3) . . ?
C29 C24 C9 121.3(3) . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C22 C12 C7 109.0(2) . . ?
C22 C12 C11 111.0(2) . . ?
C20 C12 C22 107.8(2) . . ?
C20 C12 C7 108.1(2) . . ?
C20 C12 C11 111.5(2) . . ?
C11 C12 C7 109.4(2) . . ?
C8 C9 C24 123.0(3) . . ?
C8 C9 C10 117.2(3) . . ?
C24 C9 C10 119.6(3) . . ?
C9 C10 H10 108.2 . . ?
C9 C10 C11 108.7(2) . . ?
C9 C10 C15 109.8(3) . . ?
C11 C10 H10 108.2 . . ?
C15 C10 H10 108.2 . . ?
C15 C10 C11 113.5(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
N21 C20 C12 178.5(3) . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
O13 C7 C8 115.9(2) . . ?
O13 C7 C6 108.9(2) . . ?
O13 C7 C12 102.5(2) . . ?
C8 C7 C6 113.5(2) . . ?
C8 C7 C12 105.5(2) . . ?
C6 C7 C12 109.8(2) . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.7(3) . . ?
C1 C2 H2 119.7 . . ?
C16 C11 C12 111.2(2) . . ?
C16 C11 C10 106.0(2) . . ?
C16 C11 C18 105.8(3) . . ?
C10 C11 C12 113.0(2) . . ?
C18 C11 C12 110.2(2) . . ?
C18 C11 C10 110.2(2) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 H1 120.1 . . ?
N19 C18 C11 179.1(4) . . ?
C10 C15 H15A 108.9 . . ?
C10 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C14 C15 C10 113.4(2) . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
O13 C14 C15 111.3(2) . . ?
O13 C14 H14A 109.4 . . ?
O13 C14 H14B 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.8(3) . . ?
C24 C29 H29 119.8 . . ?
C28 C29 C24 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.6(3) . . ?
C27 C26 H26 120.2 . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7232(18)
2 0.2768(18)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, Dichloromethane, Hexanes'
####################################################################### 
# 
# 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_cas_1284c_0m
_database_code_depnum_ccdc_archive 'CCDC 1521359'
_audit_update_record             
;
2016-12-07 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
_audit_creation_date             2016-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Fe O'
_chemical_formula_sum            'C22 H20 Fe O'
_chemical_formula_weight         356.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2823(2)
_cell_length_b                   10.5512(3)
_cell_length_c                   11.3059(3)
_cell_angle_alpha                92.6290(10)
_cell_angle_beta                 100.8210(10)
_cell_angle_gamma                101.1970(10)
_cell_volume                     833.96(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      4.00
_shelx_estimated_absorpt_T_max   0.713
_shelx_estimated_absorpt_T_min   0.324
_exptl_absorpt_coefficient_mu    7.265
_exptl_absorpt_correction_T_max  0.4813
_exptl_absorpt_correction_T_min  0.3191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1060 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.6630.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9825
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.522
_diffrn_reflns_theta_max         66.522
_diffrn_reflns_theta_min         3.995
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2713
_reflns_number_total             2911
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²+0.7810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4945(3) 0.6376(2) 0.5968(2) 0.0164(4) Uani 1 1 d . . . . .
H1 H 0.5021 0.5486 0.5934 0.020 Uiso 1 1 calc R . . . .
C2 C 0.3482(3) 0.6772(2) 0.5196(2) 0.0195(5) Uani 1 1 d . . . . .
H2 H 0.2584 0.6158 0.4625 0.023 Uiso 1 1 calc R . . . .
C3 C 0.3327(3) 0.8061(2) 0.5256(2) 0.0182(5) Uani 1 1 d . . . . .
H3 H 0.2317 0.8331 0.4736 0.022 Uiso 1 1 calc R . . . .
C4 C 0.4657(3) 0.8953(2) 0.6081(2) 0.0176(5) Uani 1 1 d . . . . .
H4 H 0.4549 0.9836 0.6130 0.021 Uiso 1 1 calc R . . . .
C5 C 0.6153(3) 0.8565(2) 0.68406(19) 0.0146(4) Uani 1 1 d . . . . .
H5 H 0.7070 0.9187 0.7393 0.018 Uiso 1 1 calc R . . . .
C6 C 0.6305(3) 0.7268(2) 0.67921(19) 0.0129(4) Uani 1 1 d . . . . .
C7 C 0.7960(3) 0.6829(2) 0.75815(19) 0.0129(4) Uani 1 1 d . . . . .
O8 O 0.8778(2) 0.77804(15) 0.85869(14) 0.0177(3) Uani 1 1 d . . . . .
C9 C 1.0752(4) 0.7750(3) 0.8981(2) 0.0334(6) Uani 1 1 d . . . A 2
H9A H 1.0946 0.7354 0.9760 0.040 Uiso 1 1 calc R . . A 2
H9B H 1.1535 0.8641 0.9097 0.040 Uiso 1 1 calc R . . A 2
C10 C 1.1343(3) 0.6947(2) 0.8013(2) 0.0217(5) Uani 1 1 d . . . . .
H10A H 1.1529 0.6096 0.8289 0.026 Uiso 1 1 calc R . . A 2
H10B H 1.2535 0.7410 0.7795 0.026 Uiso 1 1 calc R . . A 2
C11 C 0.9646(3) 0.6789(2) 0.6948(2) 0.0161(4) Uani 1 1 d . . . . .
H11A H 0.9460 0.5952 0.6462 0.019 Uiso 1 1 calc R . . . .
H11B H 0.9821 0.7506 0.6419 0.019 Uiso 1 1 calc R . . . .
C12 C 0.7278(3) 0.5546(2) 0.80094(19) 0.0144(4) Uani 1 1 d . . . . .
C13 C 0.6601(3) 0.4504(2) 0.82857(19) 0.0139(4) Uani 1 1 d . . . . .
C14 C 0.5784(3) 0.3270(2) 0.86464(19) 0.0136(4) Uani 1 1 d . . . . .
C15 C 0.4706(3) 0.3054(2) 0.9581(2) 0.0169(4) Uani 1 1 d . . . . .
H15 H 0.4400 0.3705 1.0072 0.020 Uiso 1 1 calc R . . . .
C16 C 0.4174(3) 0.1693(2) 0.96435(19) 0.0159(4) Uani 1 1 d . . . . .
H16 H 0.3459 0.1277 1.0190 0.019 Uiso 1 1 calc R . . . .
C17 C 0.4898(3) 0.1059(2) 0.8746(2) 0.0150(4) Uani 1 1 d . . . . .
H17 H 0.4752 0.0149 0.8594 0.018 Uiso 1 1 calc R . . . .
C18 C 0.5874(3) 0.2020(2) 0.81196(19) 0.0129(4) Uani 1 1 d . . . . .
H18 H 0.6481 0.1867 0.7468 0.016 Uiso 1 1 calc R . . . .
Fe19 Fe 0.31024(4) 0.21816(3) 0.79625(3) 0.01129(11) Uani 1 1 d . . . . .
C20 C 0.0647(3) 0.2890(2) 0.7646(2) 0.0219(5) Uani 1 1 d . . . . .
H20 H 0.0305 0.3507 0.8158 0.026 Uiso 1 1 calc R . . . .
C21 C 0.1676(3) 0.3173(2) 0.6710(2) 0.0241(5) Uani 1 1 d . . . . .
H21 H 0.2146 0.4014 0.6487 0.029 Uiso 1 1 calc R . . . .
C22 C 0.1885(3) 0.1979(3) 0.6159(2) 0.0233(5) Uani 1 1 d . . . . .
H22 H 0.2516 0.1883 0.5508 0.028 Uiso 1 1 calc R . . . .
C23 C 0.0978(3) 0.0958(2) 0.6764(2) 0.0207(5) Uani 1 1 d . . . . .
H23 H 0.0896 0.0058 0.6585 0.025 Uiso 1 1 calc R . . . .
C24 C 0.0216(3) 0.1518(2) 0.7684(2) 0.0205(5) Uani 1 1 d . . . . .
H24 H -0.0460 0.1058 0.8227 0.025 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
C1 H1 0.9500 . ?
C1 C2 1.389(3) . ?
C1 C6 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 C7 1.522(3) . ?
C7 O8 1.437(3) . ?
C7 C11 1.539(3) . ?
C7 C12 1.484(3) . ?
O8 C9 1.430(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.533(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.195(3) . ?
C13 C14 1.433(3) . ?
C14 C15 1.431(3) . ?
C14 C18 1.440(3) . ?
C14 Fe19 2.052(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.421(3) . ?
C15 Fe19 2.045(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.424(3) . ?
C16 Fe19 2.044(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.418(3) . ?
C17 Fe19 2.040(2) . ?
C18 H18 0.9500 . ?
C18 Fe19 2.034(2) . ?
Fe19 C20 2.047(2) . ?
Fe19 C21 2.046(2) . ?
Fe19 C22 2.048(2) . ?
Fe19 C23 2.043(2) . ?
Fe19 C24 2.041(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.418(4) . ?
C20 C24 1.425(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.427(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.423(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.423(3) . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.8(2) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.20(19) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 120.01(18) . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 121.19(18) . . ?
C6 C7 C11 113.22(17) . . ?
O8 C7 C6 109.00(16) . . ?
O8 C7 C11 103.24(16) . . ?
O8 C7 C12 110.64(17) . . ?
C12 C7 C6 109.98(17) . . ?
C12 C7 C11 110.57(17) . . ?
C9 O8 C7 109.28(17) . . ?
O8 C9 H9A 110.1 . . ?
O8 C9 H9B 110.1 . . ?
O8 C9 C10 107.95(19) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C9 C10 C11 103.00(18) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C7 C11 H11A 111.2 . . ?
C7 C11 H11B 111.2 . . ?
C10 C11 C7 102.58(17) . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.2 . . ?
C13 C12 C7 174.9(2) . . ?
C12 C13 C14 178.5(2) . . ?
C13 C14 C18 126.09(19) . . ?
C13 C14 Fe19 126.60(15) . . ?
C15 C14 C13 126.34(19) . . ?
C15 C14 C18 107.56(18) . . ?
C15 C14 Fe19 69.31(12) . . ?
C18 C14 Fe19 68.70(11) . . ?
C14 C15 H15 126.0 . . ?
C14 C15 Fe19 69.81(12) . . ?
C16 C15 C14 108.00(19) . . ?
C16 C15 H15 126.0 . . ?
C16 C15 Fe19 69.60(12) . . ?
Fe19 C15 H15 126.2 . . ?
C15 C16 H16 125.9 . . ?
C15 C16 C17 108.26(19) . . ?
C15 C16 Fe19 69.72(13) . . ?
C17 C16 H16 125.9 . . ?
C17 C16 Fe19 69.43(12) . . ?
Fe19 C16 H16 126.6 . . ?
C16 C17 H17 125.8 . . ?
C16 C17 Fe19 69.74(12) . . ?
C18 C17 C16 108.33(18) . . ?
C18 C17 H17 125.8 . . ?
C18 C17 Fe19 69.41(12) . . ?
Fe19 C17 H17 126.6 . . ?
C14 C18 H18 126.1 . . ?
C14 C18 Fe19 70.03(11) . . ?
C17 C18 C14 107.84(18) . . ?
C17 C18 H18 126.1 . . ?
C17 C18 Fe19 69.84(12) . . ?
Fe19 C18 H18 125.6 . . ?
C15 Fe19 C14 40.88(9) . . ?
C15 Fe19 C20 107.52(10) . . ?
C15 Fe19 C21 122.60(10) . . ?
C15 Fe19 C22 158.56(10) . . ?
C16 Fe19 C14 68.58(9) . . ?
C16 Fe19 C15 40.68(9) . . ?
C16 Fe19 C20 120.72(10) . . ?
C16 Fe19 C21 157.10(10) . . ?
C16 Fe19 C22 159.74(10) . . ?
C17 Fe19 C14 68.74(8) . . ?
C17 Fe19 C15 68.74(9) . . ?
C17 Fe19 C16 40.83(9) . . ?
C17 Fe19 C20 155.77(9) . . ?
C17 Fe19 C21 161.45(10) . . ?
C17 Fe19 C22 123.67(10) . . ?
C17 Fe19 C23 106.08(9) . . ?
C17 Fe19 C24 119.74(9) . . ?
C18 Fe19 C14 41.26(8) . . ?
C18 Fe19 C15 69.18(9) . . ?
C18 Fe19 C16 68.83(9) . . ?
C18 Fe19 C17 40.75(9) . . ?
C18 Fe19 C20 162.33(9) . . ?
C18 Fe19 C21 125.54(9) . . ?
C18 Fe19 C22 107.78(9) . . ?
C18 Fe19 C23 120.74(9) . . ?
C18 Fe19 C24 155.62(9) . . ?
C20 Fe19 C14 125.05(9) . . ?
C20 Fe19 C22 68.57(10) . . ?
C21 Fe19 C14 109.19(9) . . ?
C21 Fe19 C20 40.55(10) . . ?
C21 Fe19 C22 40.81(10) . . ?
C22 Fe19 C14 122.91(9) . . ?
C23 Fe19 C14 157.70(9) . . ?
C23 Fe19 C15 159.38(9) . . ?
C23 Fe19 C16 122.54(9) . . ?
C23 Fe19 C20 68.55(9) . . ?
C23 Fe19 C21 68.45(10) . . ?
C23 Fe19 C22 40.70(10) . . ?
C24 Fe19 C14 160.82(9) . . ?
C24 Fe19 C15 123.07(9) . . ?
C24 Fe19 C16 105.76(9) . . ?
C24 Fe19 C20 40.82(9) . . ?
C24 Fe19 C21 68.48(9) . . ?
C24 Fe19 C22 68.65(10) . . ?
C24 Fe19 C23 40.79(10) . . ?
Fe19 C20 H20 126.5 . . ?
C21 C20 Fe19 69.70(13) . . ?
C21 C20 H20 126.0 . . ?
C21 C20 C24 107.9(2) . . ?
C24 C20 Fe19 69.39(13) . . ?
C24 C20 H20 126.0 . . ?
Fe19 C21 H21 126.3 . . ?
C20 C21 Fe19 69.75(13) . . ?
C20 C21 H21 125.8 . . ?
C20 C21 C22 108.3(2) . . ?
C22 C21 Fe19 69.68(13) . . ?
C22 C21 H21 125.8 . . ?
Fe19 C22 H22 126.4 . . ?
C21 C22 Fe19 69.51(14) . . ?
C21 C22 H22 126.2 . . ?
C23 C22 Fe19 69.44(13) . . ?
C23 C22 C21 107.6(2) . . ?
C23 C22 H22 126.2 . . ?
Fe19 C23 H23 126.3 . . ?
C22 C23 Fe19 69.86(13) . . ?
C22 C23 H23 125.9 . . ?
C22 C23 C24 108.3(2) . . ?
C24 C23 Fe19 69.56(13) . . ?
C24 C23 H23 125.9 . . ?
Fe19 C24 H24 126.1 . . ?
C20 C24 Fe19 69.79(12) . . ?
C20 C24 H24 126.1 . . ?
C23 C24 Fe19 69.66(12) . . ?
C23 C24 C20 107.9(2) . . ?
C23 C24 H24 126.1 . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, Hexanes'
####################################################################### 
# 
# 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_cas_2057d_0m
_database_code_depnum_ccdc_archive 'CCDC 1521361'
_audit_update_record             
;
2016-12-07 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
_audit_creation_date             2016-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H15 F3 N4 O'
_chemical_formula_sum            'C25 H15 F3 N4 O'
_chemical_formula_weight         444.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3921(3)
_cell_length_b                   11.9914(3)
_cell_length_c                   17.5331(4)
_cell_angle_alpha                80.3565(12)
_cell_angle_beta                 89.9964(14)
_cell_angle_gamma                76.6551(13)
_cell_volume                     2094.17(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5391
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.45
_cell_measurement_theta_min      3.85
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.9238.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30098
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.194
_diffrn_reflns_theta_min         2.558
_diffrn_ambient_temperature      100.04
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6375
_reflns_number_total             8427
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00301(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         8427
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+1.5991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F72-C70A = F71-C70A = F73-C70A
 1.32 with sigma of 0.02
 F74-C70B = F76-C70B = F75-C70B
 1.32 with sigma of 0.01
 F75-F76 = F74-F75 = F76-F74
 2.12 with sigma of 0.02
 F73-F72 = F72-F71 = F71-F73
 2.12 with sigma of 0.04
 F75-C67 = F74-C67 = F76-C67
 2.35 with sigma of 0.04
 C70B-C67 \\sim C70A-C67
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C70B) = Uanis(C70A)
4. Rigid body (RIGU) restrains
 F73, F72, C70A, F71
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C70B)=Sof(F74)=Sof(F75)=Sof(F76)=1-FVAR(1)
 Sof(F71)=Sof(F72)=Sof(F73)=Sof(C70A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C10(H10), C50(H50)
6.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C61(H61A,H61B), C62(H62A,H62B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C25(H25), C26(H26), C28(H28),
 C29(H29), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C48(H48), C65(H65),
  C66(H66), C68(H68), C69(H69)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.84973(19) 0.47467(16) 0.64433(11) 0.0191(4) Uani 1 1 d . . . . .
H1 H 0.9153 0.4984 0.6713 0.023 Uiso 1 1 calc R . . . .
C2 C 0.8096(2) 0.37374(17) 0.67483(12) 0.0221(4) Uani 1 1 d . . . . .
H2 H 0.8476 0.3290 0.7228 0.026 Uiso 1 1 calc R . . . .
C3 C 0.7149(2) 0.33828(17) 0.63564(12) 0.0245(5) Uani 1 1 d . . . . .
H3 H 0.6891 0.2686 0.6563 0.029 Uiso 1 1 calc R . . . .
C4 C 0.6574(2) 0.40432(17) 0.56623(12) 0.0219(4) Uani 1 1 d . . . . .
H4 H 0.5917 0.3803 0.5396 0.026 Uiso 1 1 calc R . . . .
C5 C 0.69592(19) 0.50569(16) 0.53558(11) 0.0179(4) Uani 1 1 d . . . . .
H5 H 0.6557 0.5511 0.4883 0.021 Uiso 1 1 calc R . . . .
C6 C 0.79311(18) 0.54117(15) 0.57379(11) 0.0160(4) Uani 1 1 d . . . . .
C7 C 0.83691(18) 0.65115(15) 0.53985(11) 0.0152(4) Uani 1 1 d . . . . .
C8 C 0.83401(17) 0.67535(15) 0.45235(10) 0.0147(4) Uani 1 1 d . . . . .
H8 H 0.8186 0.6185 0.4239 0.018 Uiso 1 1 calc R . . . .
C9 C 0.85313(17) 0.77658(16) 0.41484(11) 0.0147(4) Uani 1 1 d . . . . .
C10 C 0.87374(18) 0.86436(16) 0.46418(10) 0.0153(4) Uani 1 1 d . . . . .
H10 H 0.8708 0.9400 0.4292 0.018 Uiso 1 1 calc R . . . .
C11 C 0.75181(18) 0.88149(15) 0.51746(10) 0.0153(4) Uani 1 1 d . . . . .
C12 C 0.74054(18) 0.76114(16) 0.56949(10) 0.0152(4) Uani 1 1 d . . . . .
C13 C 1.00724(19) 0.82658(16) 0.50996(11) 0.0187(4) Uani 1 1 d . . . . .
H13A H 1.0739 0.8588 0.4789 0.022 Uiso 1 1 calc R . . . .
H13B H 0.9981 0.8599 0.5582 0.022 Uiso 1 1 calc R . . . .
C14 C 1.05648(18) 0.69588(16) 0.53049(11) 0.0185(4) Uani 1 1 d . . . . .
H14A H 1.0732 0.6631 0.4822 0.022 Uiso 1 1 calc R . . . .
H14B H 1.1415 0.6775 0.5607 0.022 Uiso 1 1 calc R . . . .
O15 O 0.96393(12) 0.64162(11) 0.57477(7) 0.0185(3) Uani 1 1 d . . . . .
C16 C 0.76007(19) 0.96921(16) 0.56608(11) 0.0177(4) Uani 1 1 d . . . . .
N17 N 0.77334(19) 1.03575(15) 0.60337(10) 0.0263(4) Uani 1 1 d . . . . .
C18 C 0.63553(18) 0.92869(16) 0.46277(11) 0.0165(4) Uani 1 1 d . . . . .
N19 N 0.55168(17) 0.96623(15) 0.41702(10) 0.0245(4) Uani 1 1 d . . . . .
C20 C 0.7789(2) 0.75618(16) 0.65158(11) 0.0186(4) Uani 1 1 d . . . . .
N21 N 0.8049(2) 0.74933(16) 0.71572(10) 0.0307(4) Uani 1 1 d . . . . .
C22 C 0.60088(19) 0.75172(15) 0.56845(11) 0.0167(4) Uani 1 1 d . . . . .
N23 N 0.49281(17) 0.74541(15) 0.56919(10) 0.0239(4) Uani 1 1 d . . . . .
C24 C 0.85521(18) 0.80771(15) 0.32961(11) 0.0155(4) Uani 1 1 d . . . . .
C25 C 0.7790(2) 0.76450(17) 0.28167(11) 0.0210(4) Uani 1 1 d . . . . .
H25 H 0.7252 0.7143 0.3039 0.025 Uiso 1 1 calc R . . . .
C26 C 0.7808(2) 0.79396(18) 0.20191(12) 0.0259(5) Uani 1 1 d . . . . .
H26 H 0.7282 0.7643 0.1696 0.031 Uiso 1 1 calc R . . . .
C27 C 0.8595(2) 0.86696(17) 0.16924(11) 0.0238(5) Uani 1 1 d . . . . .
C28 C 0.9366(2) 0.91041(17) 0.21618(11) 0.0220(4) Uani 1 1 d . . . . .
H28 H 0.9910 0.9598 0.1937 0.026 Uiso 1 1 calc R . . . .
C29 C 0.9339(2) 0.88141(16) 0.29579(11) 0.0193(4) Uani 1 1 d . . . . .
H29 H 0.9860 0.9118 0.3279 0.023 Uiso 1 1 calc R . . . .
C30 C 0.8621(3) 0.90124(19) 0.08339(13) 0.0326(5) Uani 1 1 d . . . . .
F31 F 0.98445(16) 0.88488(15) 0.05773(8) 0.0585(5) Uani 1 1 d . . . . .
F32 F 0.80446(15) 1.01367(11) 0.05911(7) 0.0402(4) Uani 1 1 d . . . . .
F33 F 0.7975(2) 0.84200(13) 0.04469(8) 0.0575(5) Uani 1 1 d . . . . .
C41 C 0.73642(19) 0.57636(17) 0.02300(11) 0.0191(4) Uani 1 1 d . . . . .
H41 H 0.6878 0.6283 0.0538 0.023 Uiso 1 1 calc R . . . .
C42 C 0.7980(2) 0.61940(18) -0.04186(12) 0.0227(4) Uani 1 1 d . . . . .
H42 H 0.7910 0.7007 -0.0554 0.027 Uiso 1 1 calc R . . . .
C43 C 0.8694(2) 0.54444(18) -0.08674(12) 0.0233(4) Uani 1 1 d . . . . .
H43 H 0.9098 0.5744 -0.1317 0.028 Uiso 1 1 calc R . . . .
C44 C 0.8821(2) 0.42527(18) -0.06610(12) 0.0228(4) Uani 1 1 d . . . . .
H44 H 0.9330 0.3736 -0.0963 0.027 Uiso 1 1 calc R . . . .
C45 C 0.82052(19) 0.38149(17) -0.00122(11) 0.0194(4) Uani 1 1 d . . . . .
H45 H 0.8295 0.3000 0.0128 0.023 Uiso 1 1 calc R . . . .
C46 C 0.74555(18) 0.45686(16) 0.04327(11) 0.0165(4) Uani 1 1 d . . . . .
C47 C 0.67362(18) 0.41209(15) 0.11354(11) 0.0155(4) Uani 1 1 d . . . . .
C48 C 0.61849(18) 0.30844(15) 0.10366(11) 0.0152(4) Uani 1 1 d . . . . .
H48 H 0.6224 0.2825 0.0552 0.018 Uiso 1 1 calc R . . . .
C49 C 0.56440(18) 0.25399(15) 0.16350(10) 0.0147(4) Uani 1 1 d . . . . .
C50 C 0.54732(18) 0.31023(16) 0.23501(10) 0.0155(4) Uani 1 1 d . . . . .
H50 H 0.5218 0.2540 0.2778 0.019 Uiso 1 1 calc R . . . .
C51 C 0.68394(19) 0.33353(16) 0.26024(10) 0.0163(4) Uani 1 1 d . . . . .
C52 C 0.77168(19) 0.36596(16) 0.18806(11) 0.0164(4) Uani 1 1 d . . . . .
C53 C 0.84086(19) 0.45570(16) 0.20272(11) 0.0177(4) Uani 1 1 d . . . . .
N54 N 0.89848(17) 0.52192(15) 0.21453(10) 0.0242(4) Uani 1 1 d . . . . .
C55 C 0.87474(19) 0.26373(16) 0.17493(11) 0.0183(4) Uani 1 1 d . . . . .
N56 N 0.95621(18) 0.18731(15) 0.16316(10) 0.0269(4) Uani 1 1 d . . . . .
C57 C 0.66161(19) 0.42710(16) 0.30765(11) 0.0176(4) Uani 1 1 d . . . . .
N58 N 0.64662(17) 0.49968(15) 0.34394(10) 0.0236(4) Uani 1 1 d . . . . .
C59 C 0.75697(19) 0.22543(17) 0.31076(11) 0.0182(4) Uani 1 1 d . . . . .
N60 N 0.80845(18) 0.13940(15) 0.34867(10) 0.0251(4) Uani 1 1 d . . . . .
C61 C 0.43307(19) 0.42001(16) 0.21991(11) 0.0178(4) Uani 1 1 d . . . . .
H61A H 0.3479 0.3966 0.2183 0.021 Uiso 1 1 calc R . . . .
H61B H 0.4317 0.4637 0.2632 0.021 Uiso 1 1 calc R . . . .
C62 C 0.44651(18) 0.49860(16) 0.14444(11) 0.0170(4) Uani 1 1 d . . . . .
H62A H 0.4185 0.4663 0.1005 0.020 Uiso 1 1 calc R . . . .
H62B H 0.3880 0.5767 0.1437 0.020 Uiso 1 1 calc R . . . .
O63 O 0.58172(12) 0.50846(11) 0.13588(7) 0.0166(3) Uani 1 1 d . . . . .
C64 C 0.51385(18) 0.14834(15) 0.16159(11) 0.0157(4) Uani 1 1 d . . . . .
C65 C 0.46930(19) 0.12521(16) 0.09210(11) 0.0190(4) Uani 1 1 d . . . . .
H65 H 0.4688 0.1790 0.0456 0.023 Uiso 1 1 calc R . . . .
C66 C 0.4259(2) 0.02511(17) 0.09006(12) 0.0215(4) Uani 1 1 d . . . . .
H66 H 0.3955 0.0104 0.0425 0.026 Uiso 1 1 calc R . . . .
C67 C 0.4269(2) -0.05428(17) 0.15806(12) 0.0217(4) Uani 1 1 d D . . . .
C68 C 0.4691(2) -0.03198(17) 0.22773(12) 0.0232(4) Uani 1 1 d . . . . .
H68 H 0.4684 -0.0855 0.2742 0.028 Uiso 1 1 calc R . . . .
C69 C 0.5125(2) 0.06854(17) 0.22940(11) 0.0205(4) Uani 1 1 d . . . . .
H69 H 0.5416 0.0834 0.2772 0.025 Uiso 1 1 calc R . . . .
F71 F 0.4535(3) -0.25454(13) 0.20621(9) 0.0388(6) Uani 0.907(6) 1 d D U P A 1
F72 F 0.25715(17) -0.15591(15) 0.17773(16) 0.0548(8) Uani 0.907(6) 1 d D U P A
1
F73 F 0.3876(4) -0.1945(2) 0.08659(10) 0.0582(9) Uani 0.907(6) 1 d D U P A 1
C70B C 0.3752(17) -0.1563(11) 0.1456(10) 0.0302(5) Uani 0.093(6) 1 d D . P A 2
F74 F 0.2503(15) -0.1316(17) 0.1209(14) 0.063(7) Uiso 0.093(6) 1 d D . P A 2
F75 F 0.384(2) -0.2316(16) 0.2106(9) 0.049(6) Uiso 0.093(6) 1 d D . P A 2
F76 F 0.4483(16) -0.2132(17) 0.0965(11) 0.035(6) Uiso 0.093(6) 1 d D . P A 2
C70A C 0.3813(3) -0.1633(2) 0.15700(16) 0.0302(5) Uani 0.907(6) 1 d D U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.393(3) . ?
C1 C6 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 C7 1.521(2) . ?
C7 C8 1.512(3) . ?
C7 C12 1.622(3) . ?
C7 O15 1.427(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.338(3) . ?
C9 C10 1.520(3) . ?
C9 C24 1.480(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.570(3) . ?
C10 C13 1.537(3) . ?
C11 C12 1.602(2) . ?
C11 C16 1.477(3) . ?
C11 C18 1.484(3) . ?
C12 C20 1.481(3) . ?
C12 C22 1.482(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.513(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 O15 1.439(2) . ?
C16 N17 1.144(3) . ?
C18 N19 1.142(2) . ?
C20 N21 1.141(3) . ?
C22 N23 1.143(3) . ?
C24 C25 1.392(3) . ?
C24 C29 1.400(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(3) . ?
C27 C28 1.388(3) . ?
C27 C30 1.494(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.383(3) . ?
C29 H29 0.9500 . ?
C30 F31 1.331(3) . ?
C30 F32 1.339(2) . ?
C30 F33 1.340(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.387(3) . ?
C41 C46 1.398(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.381(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.389(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.391(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.394(3) . ?
C46 C47 1.526(3) . ?
C47 C48 1.518(3) . ?
C47 C52 1.597(3) . ?
C47 O63 1.429(2) . ?
C48 H48 0.9500 . ?
C48 C49 1.335(3) . ?
C49 C50 1.512(2) . ?
C49 C64 1.484(2) . ?
C50 H50 1.0000 . ?
C50 C51 1.586(3) . ?
C50 C61 1.541(3) . ?
C51 C52 1.607(3) . ?
C51 C57 1.482(3) . ?
C51 C59 1.484(3) . ?
C52 C53 1.480(3) . ?
C52 C55 1.480(3) . ?
C53 N54 1.143(3) . ?
C55 N56 1.142(3) . ?
C57 N58 1.144(3) . ?
C59 N60 1.144(2) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61 C62 1.517(3) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C62 O63 1.443(2) . ?
C64 C65 1.396(3) . ?
C64 C69 1.398(3) . ?
C65 H65 0.9500 . ?
C65 C66 1.382(3) . ?
C66 H66 0.9500 . ?
C66 C67 1.394(3) . ?
C67 C68 1.386(3) . ?
C67 C70B 1.492(9) . ?
C67 C70A 1.493(3) . ?
C68 H68 0.9500 . ?
C68 C69 1.385(3) . ?
C69 H69 0.9500 . ?
F71 C70A 1.345(3) . ?
F72 C70A 1.327(3) . ?
F73 C70A 1.346(3) . ?
C70B F74 1.319(10) . ?
C70B F75 1.320(10) . ?
C70B F76 1.320(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
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.83(19) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.39(18) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.08(18) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.00(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.45(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 120.17(17) . . ?
C5 C6 C1 119.23(17) . . ?
C5 C6 C7 120.60(16) . . ?
C6 C7 C12 108.70(14) . . ?
C8 C7 C6 113.99(15) . . ?
C8 C7 C12 108.40(14) . . ?
O15 C7 C6 106.65(14) . . ?
O15 C7 C8 113.61(15) . . ?
O15 C7 C12 105.04(14) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.16(17) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 116.89(16) . . ?
C8 C9 C24 124.40(17) . . ?
C24 C9 C10 118.71(15) . . ?
C9 C10 H10 108.3 . . ?
C9 C10 C11 105.80(14) . . ?
C9 C10 C13 112.80(15) . . ?
C11 C10 H10 108.3 . . ?
C13 C10 H10 108.3 . . ?
C13 C10 C11 113.08(15) . . ?
C10 C11 C12 111.61(14) . . ?
C16 C11 C10 110.02(15) . . ?
C16 C11 C12 111.12(15) . . ?
C16 C11 C18 108.51(15) . . ?
C18 C11 C10 104.53(15) . . ?
C18 C11 C12 110.81(15) . . ?
C11 C12 C7 111.16(14) . . ?
C20 C12 C7 107.39(15) . . ?
C20 C12 C11 111.35(15) . . ?
C20 C12 C22 106.29(15) . . ?
C22 C12 C7 111.10(15) . . ?
C22 C12 C11 109.44(15) . . ?
C10 C13 H13A 108.9 . . ?
C10 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C10 113.18(16) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
O15 C14 C13 112.56(15) . . ?
O15 C14 H14A 109.1 . . ?
O15 C14 H14B 109.1 . . ?
C7 O15 C14 118.31(14) . . ?
N17 C16 C11 176.5(2) . . ?
N19 C18 C11 175.6(2) . . ?
N21 C20 C12 177.1(2) . . ?
N23 C22 C12 178.4(2) . . ?
C25 C24 C9 120.71(17) . . ?
C25 C24 C29 118.82(17) . . ?
C29 C24 C9 120.47(17) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.65(19) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.8(2) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.28(18) . . ?
C26 C27 C30 121.0(2) . . ?
C28 C27 C30 118.8(2) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.71(19) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 H29 119.6 . . ?
C28 C29 C24 120.70(19) . . ?
C28 C29 H29 119.6 . . ?
F31 C30 C27 112.74(19) . . ?
F31 C30 F32 106.27(19) . . ?
F31 C30 F33 106.63(19) . . ?
F32 C30 C27 112.36(18) . . ?
F32 C30 F33 105.53(19) . . ?
F33 C30 C27 112.77(19) . . ?
C42 C41 H41 119.8 . . ?
C42 C41 C46 120.34(19) . . ?
C46 C41 H41 119.8 . . ?
C41 C42 H42 119.9 . . ?
C43 C42 C41 120.22(19) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 120.0 . . ?
C42 C43 C44 120.02(18) . . ?
C44 C43 H43 120.0 . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 120.07(19) . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 119.9 . . ?
C44 C45 C46 120.23(18) . . ?
C46 C45 H45 119.9 . . ?
C41 C46 C47 119.30(17) . . ?
C45 C46 C41 119.09(17) . . ?
C45 C46 C47 121.62(16) . . ?
C46 C47 C52 111.24(15) . . ?
C48 C47 C46 113.58(15) . . ?
C48 C47 C52 104.28(14) . . ?
O63 C47 C46 108.67(14) . . ?
O63 C47 C48 116.00(15) . . ?
O63 C47 C52 102.40(14) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 C47 119.57(17) . . ?
C49 C48 H48 120.2 . . ?
C48 C49 C50 116.32(16) . . ?
C48 C49 C64 124.12(17) . . ?
C64 C49 C50 119.44(16) . . ?
C49 C50 H50 107.8 . . ?
C49 C50 C51 109.73(15) . . ?
C49 C50 C61 109.41(15) . . ?
C51 C50 H50 107.8 . . ?
C61 C50 H50 107.8 . . ?
C61 C50 C51 114.03(15) . . ?
C50 C51 C52 113.08(14) . . ?
C57 C51 C50 110.60(15) . . ?
C57 C51 C52 109.52(15) . . ?
C57 C51 C59 106.98(15) . . ?
C59 C51 C50 106.72(15) . . ?
C59 C51 C52 109.73(15) . . ?
C47 C52 C51 107.28(14) . . ?
C53 C52 C47 110.98(15) . . ?
C53 C52 C51 110.37(15) . . ?
C53 C52 C55 106.98(16) . . ?
C55 C52 C47 109.70(15) . . ?
C55 C52 C51 111.56(15) . . ?
N54 C53 C52 177.5(2) . . ?
N56 C55 C52 177.7(2) . . ?
N58 C57 C51 178.7(2) . . ?
N60 C59 C51 176.5(2) . . ?
C50 C61 H61A 109.2 . . ?
C50 C61 H61B 109.2 . . ?
H61A C61 H61B 107.9 . . ?
C62 C61 C50 112.00(15) . . ?
C62 C61 H61A 109.2 . . ?
C62 C61 H61B 109.2 . . ?
C61 C62 H62A 109.6 . . ?
C61 C62 H62B 109.6 . . ?
H62A C62 H62B 108.1 . . ?
O63 C62 C61 110.48(15) . . ?
O63 C62 H62A 109.6 . . ?
O63 C62 H62B 109.6 . . ?
C47 O63 C62 117.01(14) . . ?
C65 C64 C49 120.92(16) . . ?
C65 C64 C69 118.57(17) . . ?
C69 C64 C49 120.49(17) . . ?
C64 C65 H65 119.6 . . ?
C66 C65 C64 120.85(18) . . ?
C66 C65 H65 119.6 . . ?
C65 C66 H66 120.1 . . ?
C65 C66 C67 119.81(18) . . ?
C67 C66 H66 120.1 . . ?
C66 C67 C70B 112.8(7) . . ?
C66 C67 C70A 120.6(2) . . ?
C68 C67 C66 120.12(18) . . ?
C68 C67 C70B 127.1(7) . . ?
C68 C67 C70A 119.24(19) . . ?
C67 C68 H68 120.1 . . ?
C69 C68 C67 119.79(18) . . ?
C69 C68 H68 120.1 . . ?
C64 C69 H69 119.6 . . ?
C68 C69 C64 120.85(18) . . ?
C68 C69 H69 119.6 . . ?
F74 C70B C67 115.2(13) . . ?
F74 C70B F75 105.9(12) . . ?
F74 C70B F76 108.5(12) . . ?
F75 C70B C67 110.7(13) . . ?
F76 C70B C67 110.4(14) . . ?
F76 C70B F75 105.7(13) . . ?
F71 C70A C67 112.4(2) . . ?
F71 C70A F73 106.6(2) . . ?
F72 C70A C67 113.4(2) . . ?
F72 C70A F71 105.1(2) . . ?
F72 C70A F73 106.1(3) . . ?
F73 C70A C67 112.6(2) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
