# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cx1132
_database_code_depnum_ccdc_archive 'CCDC 1955702'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H28 N4 S2, C12 H14 N2, 3(F6 P)'
_chemical_formula_sum            'C44 H42 F18 N6 P3 S2'
_chemical_formula_weight         1153.86
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.8195(8)
_cell_length_b                   20.8662(12)
_cell_length_c                   9.5394(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2949.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4318
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.810
_cell_measurement_theta_min      3.659
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.573
_exptl_absorpt_coefficient_mu    2.411
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1137 before and 0.0766 after correction. The Ratio of minimum to maximum transmission is 0.7206. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1174
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.915
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9385
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         63.824
_diffrn_reflns_theta_min         3.658
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2309
_reflns_number_total             2597
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2597
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.1123
_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)+(0.1249P)²+17.7906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2975
_refine_ls_wR_factor_ref         0.3018
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H9C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
S1 S 0.26563(17) 0.63987(11) 0.0000 0.0652(9) Uani 1 2 d S T P A 1
N1 N 0.2118(4) 0.5766(3) 0.3166(6) 0.0619(16) Uani 1 1 d . . . . .
C1 C 0.2060(5) 0.5114(3) 0.3262(7) 0.064(2) Uani 1 1 d . . . . .
H1 H 0.2598 0.4867 0.3285 0.077 Uiso 1 1 calc R . . . .
C2 C 0.1250(5) 0.4810(3) 0.3326(6) 0.0541(18) Uani 1 1 d . . . . .
H2 H 0.1236 0.4355 0.3379 0.065 Uiso 1 1 calc R . . . .
C3 C 0.0421(4) 0.5157(3) 0.3314(6) 0.0511(16) Uani 1 1 d . . . . .
C4 C 0.0518(5) 0.5832(3) 0.3277(7) 0.0564(18) Uani 1 1 d . . . . .
H4 H -0.0006 0.6093 0.3321 0.068 Uiso 1 1 calc R . . . .
C5 C 0.1342(5) 0.6116(3) 0.3180(7) 0.0579(18) Uani 1 1 d . . . . .
H5 H 0.1377 0.6569 0.3121 0.070 Uiso 1 1 calc R . . . .
C6 C 0.2968(6) 0.6078(4) 0.2842(11) 0.085(3) Uani 1 1 d . . . . .
H6A H 0.3454 0.5896 0.3433 0.102 Uiso 1 1 calc R . . . .
H6B H 0.2923 0.6542 0.3051 0.102 Uiso 1 1 calc R . . . .
C7 C 0.3201(5) 0.5982(3) 0.1287(11) 0.072(2) Uani 1 1 d . . . . .
C8 C 0.3786(5) 0.5546(4) 0.0732(11) 0.086(3) Uani 1 1 d . . . B 1
H8 H 0.4155 0.5271 0.1283 0.103 Uiso 1 1 calc R . . B 1
N2 N 0.1471(6) 0.3681(4) 0.0000 0.056(2) Uani 1 2 d S T P . .
C9 C 0.2091(8) 0.3109(5) 0.0000 0.076(3) Uani 1 2 d S T P . .
H9A H 0.2193 0.2967 0.0967 0.114 Uiso 0.5 1 calc GR . . C -1
H9B H 0.2669 0.3227 -0.0429 0.114 Uiso 0.5 1 calc GR . . C -1
H9C H 0.1815 0.2760 -0.0538 0.114 Uiso 0.5 1 calc GR . . C -1
C10 C 0.1803(7) 0.4284(5) 0.0000 0.054(2) Uani 1 2 d S T P . .
H10 H 0.2438 0.4346 0.0000 0.065 Uiso 1 2 calc RS T P . .
C11 C 0.1258(7) 0.4795(5) 0.0000 0.050(2) Uani 1 2 d S T P . .
H11 H 0.1516 0.5212 0.0000 0.061 Uiso 1 2 calc RS T P . .
C12 C 0.0291(6) 0.4728(4) 0.0000 0.042(2) Uani 1 2 d S T P . .
C13 C -0.0018(6) 0.4096(4) 0.0000 0.046(2) Uani 1 2 d S T P . .
H13 H -0.0649 0.4013 0.0000 0.055 Uiso 1 2 calc RS T P . .
C14 C 0.0594(8) 0.3581(5) 0.0000 0.059(3) Uani 1 2 d S T P . .
H14 H 0.0371 0.3154 0.0000 0.071 Uiso 1 2 calc RS T P . .
P2 P 0.31319(17) 0.78681(11) 0.5000 0.0569(8) Uani 1 2 d S T P . .
F4 F 0.3784(5) 0.8129(3) 0.3894(12) 0.199(5) Uani 1 1 d . . . . .
F5 F 0.3658(4) 0.7203(2) 0.5000 0.0621(15) Uani 1 2 d S T P . .
F6 F 0.2484(5) 0.7611(3) 0.6113(10) 0.185(4) Uani 1 1 d . . . . .
F7 F 0.2592(5) 0.8526(3) 0.5000 0.106(3) Uani 1 2 d S T P . .
P1 P 0.5000 0.5000 0.5000 0.0375(7) Uani 1 4 d S T P . .
F1 F 0.5272(4) 0.4264(3) 0.5000 0.0677(17) Uani 1 2 d S T P . .
F2 F 0.5000 0.5000 0.3383(8) 0.146(4) Uani 1 2 d S T P . .
F3 F 0.3986(4) 0.4809(3) 0.5000 0.119(4) Uani 1 2 d S T P . .


_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
S1 C7 1.706(9) 6 ?
S1 C7 1.706(9) . ?
N1 C1 1.367(9) . ?
N1 C5 1.362(9) . ?
N1 C6 1.452(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.359(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.426(9) . ?
C3 C3 1.409(14) 2_565 ?
C3 C4 1.416(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.360(10) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.537(14) . ?
C7 C8 1.365(11) . ?
C8 C8 1.40(2) 6 ?
C8 H8 0.9500 . ?
N2 C9 1.506(12) . ?
N2 C10 1.351(12) . ?
N2 C14 1.316(14) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.337(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.441(13) . ?
C12 C12 1.424(16) 5_565 ?
C12 C13 1.396(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.407(13) . ?
C14 H14 0.9500 . ?
P2 F4 1.531(7) . ?
P2 F4 1.531(7) 6_556 ?
P2 F5 1.591(6) . ?
P2 F6 1.529(7) 6_556 ?
P2 F6 1.529(7) . ?
P2 F7 1.589(7) . ?
P1 F1 1.589(5) 5_666 ?
P1 F1 1.589(5) . ?
P1 F2 1.543(7) . ?
P1 F2 1.543(7) 5_666 ?
P1 F3 1.555(6) 5_666 ?
P1 F3 1.555(6) . ?

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
C7 S1 C7 92.0(6) 6 . ?
C1 N1 C6 121.1(6) . . ?
C5 N1 C1 118.6(7) . . ?
C5 N1 C6 119.7(6) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 N1 121.6(7) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.5(6) . . ?
C3 C2 H2 119.2 . . ?
C3 C3 C2 121.8(7) 2_565 . ?
C3 C3 C4 123.5(7) 2_565 . ?
C4 C3 C2 114.7(6) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.7(6) . . ?
C5 C4 H4 119.1 . . ?
N1 C5 H5 119.2 . . ?
C4 C5 N1 121.7(6) . . ?
C4 C5 H5 119.2 . . ?
N1 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
N1 C6 C7 109.9(6) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 S1 121.5(6) . . ?
C8 C7 S1 111.2(8) . . ?
C8 C7 C6 127.1(8) . . ?
C7 C8 C8 112.8(6) . 6 ?
C7 C8 H8 123.6 . . ?
C8 C8 H8 123.6 6 . ?
C10 N2 C9 121.1(9) . . ?
C14 N2 C9 118.5(9) . . ?
C14 N2 C10 120.4(8) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10 119.2 . . ?
C11 C10 N2 121.5(10) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(9) . . ?
C12 C11 H11 119.2 . . ?
C12 C12 C11 121.7(11) 5_565 . ?
C13 C12 C11 114.7(8) . . ?
C13 C12 C12 123.6(11) . 5_565 ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(9) . . ?
C14 C13 H13 119.7 . . ?
N2 C14 C13 121.1(9) . . ?
N2 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
F4 P2 F4 87.2(9) 6_556 . ?
F4 P2 F5 90.0(3) . . ?
F4 P2 F5 90.0(3) 6_556 . ?
F4 P2 F7 90.6(3) . . ?
F4 P2 F7 90.6(3) 6_556 . ?
F6 P2 F4 179.6(6) 6_556 6_556 ?
F6 P2 F4 92.4(6) . 6_556 ?
F6 P2 F4 179.6(6) . . ?
F6 P2 F4 92.4(6) 6_556 . ?
F6 P2 F5 90.1(3) 6_556 . ?
F6 P2 F5 90.1(3) . . ?
F6 P2 F6 88.0(8) . 6_556 ?
F6 P2 F7 89.3(3) . . ?
F6 P2 F7 89.3(3) 6_556 . ?
F7 P2 F5 179.1(4) . . ?
F1 P1 F1 180.0 5_666 . ?
F2 P1 F1 90.0 5_666 . ?
F2 P1 F1 90.0 . . ?
F2 P1 F1 90.0 5_666 5_666 ?
F2 P1 F1 90.0 . 5_666 ?
F2 P1 F2 180.0 . 5_666 ?
F2 P1 F3 90.000(2) . . ?
F2 P1 F3 90.000(2) 5_666 . ?
F2 P1 F3 90.000(2) . 5_666 ?
F2 P1 F3 90.000(2) 5_666 5_666 ?
F3 P1 F1 90.2(3) 5_666 . ?
F3 P1 F1 89.8(3) . . ?
F3 P1 F1 89.8(3) 5_666 5_666 ?
F3 P1 F1 90.2(3) . 5_666 ?
F3 P1 F3 180.0 . 5_666 ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 812.6 Ang³ [27.5%]
Total electron count / cell = 206.4
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.063 0.185 -0.625 203.2 51.6 ?
2 0.063 0.815 -0.518 203.2 51.6 ?
3 0.437 0.315 -0.642 203.2 51.6 ?
4 0.563 0.685 -0.929 203.2 51.6 ?

_olex2_date_sample_data_collection 2017-12-11
_olex2_date_sample_submission    2017-12-06
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1132
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cx1163
_database_code_depnum_ccdc_archive 'CCDC 1955704'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2018-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C36 H32 N4), 5(F6 P), 3(C2 H3 N)'
_chemical_formula_sum            'C78 H73 F30 N11 P5'
_chemical_formula_weight         1889.32
_chemical_absolute_configuration .
_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'
P P 0.2955 0.4335 '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      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   19.886(4)
_cell_length_b                   20.698(4)
_cell_length_c                   20.515(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8444(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.064
_cell_measurement_theta_min      3.083
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    2.051
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0827 before and 0.0513 after correction. The Ratio of minimum to maximum transmission is 0.8959. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3852
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.083
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31740
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.528
_diffrn_reflns_theta_max         66.528
_diffrn_reflns_theta_min         3.082
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                5011
_reflns_number_total             7349
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.40(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     714
_refine_ls_number_reflns         7349
_refine_ls_number_restraints     325
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²+2.9460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1579
_refine_special_details          
'The enhanced rigid-bond restraint (SHELX keyword RIGU) was applied on the disordered PF6 anions. (Acta Cryst. A68 (2012) 448-451). Distance restraints were also imposed on the disordered anions.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.60(4)
 0.40(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 F6-F10 \\sim F6-F9 \\sim F6-F8 \\sim F6-F7 \\sim F5-F10 \\sim F5-F9 \\sim
F5-F8 \\sim F5-F7 \\sim F10-F9 ~
 F10-F7 \\sim F9-F8
 with sigma of 0.02
 P2-F6 \\sim P2-F5 \\sim P2-F10 \\sim P2-F9 \\sim P2-F8 \\sim P2-F7
 with sigma of 0.01
 F16-F12 \\sim F16-F15 \\sim F16-F11 \\sim F16-F13 \\sim F12-F15 \\sim F12-F13
\\sim F12-F14 \\sim F15-F11
 \\sim F15-F14
 with sigma of 0.02
 P3-F16 \\sim P3-F12 \\sim P3-F15 \\sim P3-F11 \\sim P3-F13 \\sim P3-F14
 with sigma of 0.01
 F5-F7 \\sim F5-F8 \\sim F5-F9 \\sim F5-F10 \\sim F6-F7 \\sim F6-F8 \\sim F6-F9
\\sim F6-F10 \\sim F7-F8 \\sim F7-
 F10 \\sim F8-F9 \\sim F9-F10
 with sigma of 0.02
 P2-F5 \\sim P2-F6 \\sim P2-F7 \\sim P2-F8 \\sim P2-F9 \\sim P2-F10
 with sigma of 0.01
 F5A-F7A \\sim F5A-F8A \\sim F5A-F9A \\sim F5A-F10A \\sim F6A-F7A \\sim F6A-F8A
\\sim F6A-F9A \\sim F6A-
 F10A \\sim F7A-F8A \\sim F7A-F10A \\sim F8A-F9A \\sim F9A-F10A
 with sigma of 0.02
 P2A-F5A \\sim P2A-F6A \\sim P2A-F7A \\sim P2A-F8A \\sim P2A-F9A \\sim P2A-F10A
 with sigma of 0.01
 F11-F13 \\sim F11-F14 \\sim F11-F15 \\sim F11-F16 \\sim F12-F13 \\sim F12-F14
\\sim F12-F15 \\sim F12-F16
 \\sim F13-F14 \\sim F13-F16 \\sim F14-F15 \\sim F15-F16
 with sigma of 0.02
 P3-F11 \\sim P3-F12 \\sim P3-F13 \\sim P3-F14 \\sim P3-F15 \\sim P3-F16
 with sigma of 0.01
 F11A-F13A \\sim F11A-F14A \\sim F11A-F15A \\sim F11A-F16A \\sim F12A-F13A
\\sim F12A-F14A \\sim F12A-
 F15A \\sim F12A-F16A \\sim F13A-F14A \\sim F13A-F16A \\sim F14A-F15A \\sim
F15A-F16A
 with sigma of 0.02
 P3A-F11A \\sim P3A-F12A \\sim P3A-F13A \\sim P3A-F14A \\sim P3A-F15A \\sim
P3A-F16A
 with sigma of 0.01
4. Rigid body (RIGU) restrains
 F5A, F6A, F7A, F8A, F9A, F10A, F5, F6, F7, F8, F9, F10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F13A, F16A, F11A, F12A, F14A, F15A, F11, F12, F13, F14, F15, F16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(P2A)=Sof(F5A)=Sof(F6A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=1-FVAR(1)
 Sof(P2)=Sof(F5)=Sof(F6)=Sof(F7)=Sof(F8)=Sof(F9)=Sof(F10)=FVAR(1)
 Sof(P3A)=Sof(F11A)=Sof(F12A)=Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(F16A)=1-FVAR(2)
 Sof(P3)=Sof(F11)=Sof(F12)=Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=FVAR(2)
 Fixed Sof: H21A(0.5) H21B(0.5) H21C(0.5) H23A(0.5) H23B(0.5) H23C(0.5)
 H25A(0.5) H25B(0.5) H25C(0.5)
6.a Everything fixed:
 H23A, H23B, H23C
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C15(H15A,H15B), C4A(H4AA,H4AB), C15A(H15C,H15D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C1A(H1A), C3A(H3A), C5A(H5A), C6A(H6A),
  C8A(H8A), C9A(H9A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A),
 C17A(H17A), C18A(H18A), C19A(H19A)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.6633(3) 0.9669(3) 0.3802(5) 0.071(2) Uani 1 1 d . . . . .
N2 N 0.6403(3) 0.7496(3) 0.1200(3) 0.0519(15) Uani 1 1 d . . . . .
C1 C 0.5343(4) 0.9575(3) 0.4628(4) 0.0535(19) Uani 1 1 d . . . . .
H1 H 0.557903 0.920075 0.476892 0.064 Uiso 1 1 calc R . . . .
C2 C 0.5700(3) 1.0116(3) 0.4425(3) 0.0465(16) Uani 1 1 d . . . . .
C3 C 0.5349(3) 1.0662(3) 0.4240(3) 0.0516(18) Uani 1 1 d . . . . .
H3 H 0.558606 1.103943 0.411206 0.062 Uiso 1 1 calc R . . . .
C4 C 0.6452(4) 1.0087(4) 0.4369(5) 0.069(2) Uani 1 1 d . . . . .
H4A H 0.663456 1.052762 0.430393 0.083 Uiso 1 1 calc R . . . .
H4B H 0.664703 0.990757 0.477364 0.083 Uiso 1 1 calc R . . . .
C5 C 0.6792(4) 0.9042(4) 0.3897(5) 0.071(3) Uani 1 1 d . . . . .
H5 H 0.688507 0.888998 0.432439 0.085 Uiso 1 1 calc R . . . .
C6 C 0.6820(4) 0.8625(4) 0.3381(5) 0.073(3) Uani 1 1 d . . . . .
H6 H 0.692967 0.818488 0.345785 0.087 Uiso 1 1 calc R . . . .
C7 C 0.6693(3) 0.8828(3) 0.2744(5) 0.057(2) Uani 1 1 d . . . . .
C8 C 0.6587(4) 0.9505(4) 0.2672(5) 0.074(3) Uani 1 1 d . . . . .
H8 H 0.653937 0.968225 0.224691 0.089 Uiso 1 1 calc R . . . .
C9 C 0.6553(4) 0.9901(4) 0.3196(6) 0.077(3) Uani 1 1 d . . . . .
H9 H 0.647073 1.034848 0.313422 0.092 Uiso 1 1 calc R . . . .
C10 C 0.6628(3) 0.8374(4) 0.2207(5) 0.057(2) Uani 1 1 d . . . . .
C11 C 0.6552(5) 0.7710(4) 0.2328(5) 0.078(3) Uani 1 1 d . . . . .
H11 H 0.656904 0.755310 0.276315 0.093 Uiso 1 1 calc R . . . .
C12 C 0.6453(5) 0.7289(4) 0.1824(5) 0.079(3) Uani 1 1 d . . . . .
H12 H 0.641899 0.683977 0.191444 0.094 Uiso 1 1 calc R . . . .
C13 C 0.6486(4) 0.8119(4) 0.1063(5) 0.068(2) Uani 1 1 d . . . . .
H13 H 0.646174 0.825980 0.062279 0.082 Uiso 1 1 calc R . . . .
C14 C 0.6607(4) 0.8563(4) 0.1547(5) 0.072(3) Uani 1 1 d . . . . .
H14 H 0.667754 0.900344 0.143553 0.087 Uiso 1 1 calc R . . . .
C15 C 0.6267(4) 0.7028(4) 0.0663(4) 0.066(2) Uani 1 1 d . . . . .
H15A H 0.626660 0.658465 0.084467 0.080 Uiso 1 1 calc R . . . .
H15B H 0.663529 0.705463 0.033980 0.080 Uiso 1 1 calc R . . . .
C16 C 0.5609(4) 0.7143(3) 0.0321(3) 0.0482(17) Uani 1 1 d . . . . .
C17 C 0.5605(5) 0.7308(4) -0.0327(4) 0.073(3) Uani 1 1 d . . . . .
H17 H 0.601798 0.736410 -0.055252 0.087 Uiso 1 1 calc R . . . .
C18 C 0.500000 0.7395(5) -0.0656(6) 0.093(5) Uani 1 2 d S T P . .
H18 H 0.500001 0.751261 -0.110395 0.112 Uiso 1 2 calc RS T P . .
C19 C 0.500000 0.7054(4) 0.0643(5) 0.048(2) Uani 1 2 d S T P . .
H19 H 0.499999 0.692936 0.108857 0.057 Uiso 1 2 calc RS T P . .
N1A N 0.8356(4) 0.7868(3) 0.1070(3) 0.071(2) Uani 1 1 d . . . . .
N2A N 0.8592(3) 0.9860(3) 0.3838(3) 0.0569(17) Uani 1 1 d . . . . .
C1A C 0.9660(4) 0.6946(3) 0.0706(4) 0.0517(18) Uani 1 1 d . . . . .
H1A H 0.942484 0.659213 0.089315 0.062 Uiso 1 1 calc R . . . .
C2A C 0.9298(4) 0.7457(3) 0.0434(3) 0.0517(19) Uani 1 1 d . . . . .
C3A C 0.9656(4) 0.7956(3) 0.0157(4) 0.071(3) Uani 1 1 d . . . . .
H3A H 0.942183 0.830638 -0.003723 0.086 Uiso 1 1 calc R . . . .
C4A C 0.8544(4) 0.7482(4) 0.0492(4) 0.066(2) Uani 1 1 d . . . . .
H4AA H 0.834969 0.768042 0.009469 0.079 Uiso 1 1 calc R . . . .
H4AB H 0.836192 0.703914 0.053379 0.079 Uiso 1 1 calc R . . . .
C5A C 0.8383(4) 0.7592(4) 0.1677(4) 0.059(2) Uani 1 1 d . . . . .
H5A H 0.842037 0.713622 0.171517 0.071 Uiso 1 1 calc R . . . .
C6A C 0.8358(4) 0.7960(4) 0.2227(4) 0.0529(19) Uani 1 1 d . . . . .
H6A H 0.837862 0.775422 0.264005 0.063 Uiso 1 1 calc R . . . .
C7A C 0.8301(4) 0.8638(3) 0.2200(4) 0.055(2) Uani 1 1 d . . . . .
C8A C 0.8230(5) 0.8895(4) 0.1558(4) 0.076(3) Uani 1 1 d . . . . .
H8A H 0.816471 0.934640 0.150357 0.091 Uiso 1 1 calc R . . . .
C9A C 0.8254(5) 0.8514(4) 0.1033(4) 0.082(3) Uani 1 1 d . . . . .
H9A H 0.819623 0.870448 0.061564 0.098 Uiso 1 1 calc R . . . .
C10A C 0.8371(4) 0.9042(3) 0.2756(4) 0.055(2) Uani 1 1 d . . . . .
C11A C 0.8479(5) 0.8803(3) 0.3395(4) 0.059(2) Uani 1 1 d . . . . .
H11A H 0.846746 0.835003 0.346756 0.070 Uiso 1 1 calc R . . . .
C12A C 0.8598(4) 0.9203(3) 0.3904(4) 0.060(2) Uani 1 1 d . . . . .
H12A H 0.868823 0.902066 0.431990 0.072 Uiso 1 1 calc R . . . .
C13A C 0.8465(4) 1.0106(4) 0.3234(4) 0.068(2) Uani 1 1 d . . . . .
H13A H 0.845697 1.056220 0.317994 0.081 Uiso 1 1 calc R . . . .
C14A C 0.8353(4) 0.9732(3) 0.2719(4) 0.061(2) Uani 1 1 d . . . . .
H14A H 0.825632 0.993021 0.231132 0.073 Uiso 1 1 calc R . . . .
C15A C 0.8730(5) 1.0274(3) 0.4409(4) 0.070(3) Uani 1 1 d . . . . .
H15C H 0.836075 1.022097 0.472864 0.084 Uiso 1 1 calc R . . . .
H15D H 0.873202 1.073143 0.426779 0.084 Uiso 1 1 calc R . . . .
C16A C 0.9390(5) 1.0127(3) 0.4743(4) 0.062(2) Uani 1 1 d . . . . .
C17A C 0.9394(7) 0.9855(4) 0.5358(4) 0.104(4) Uani 1 1 d . . . . .
H17A H 0.898246 0.974610 0.556563 0.124 Uiso 1 1 calc R . . . .
C18A C 1.000000 0.9742(7) 0.5669(7) 0.144(11) Uani 1 2 d S T P . .
H18A H 1.000000 0.958423 0.610429 0.173 Uiso 1 2 calc RS T P . .
C19A C 1.000000 1.0264(4) 0.4433(5) 0.051(3) Uani 1 2 d S T P . .
H19A H 1.000001 1.045148 0.401024 0.062 Uiso 1 2 calc RS T P . .
P1 P 0.500000 0.61894(12) 0.25929(13) 0.0460(6) Uani 1 2 d S T P . .
F1 F 0.500000 0.5462(2) 0.2855(3) 0.0623(17) Uani 1 2 d S T P . .
F2 F 0.5567(2) 0.60046(18) 0.2078(2) 0.0547(10) Uani 1 1 d . . . . .
F3 F 0.500000 0.6923(2) 0.2326(3) 0.0504(14) Uani 1 2 d S T P . .
F4 F 0.4436(3) 0.6382(2) 0.3113(2) 0.0833(16) Uani 1 1 d . . . . .
P2 P 0.7328(3) 1.0799(4) 0.1097(3) 0.0440(17) Uani 0.524(14) 1 d D . . A 1
F5 F 0.8058(5) 1.0662(6) 0.1389(5) 0.051(3) Uani 0.524(14) 1 d D U . A 1
F6 F 0.6601(5) 1.0934(6) 0.0783(7) 0.068(4) Uani 0.524(14) 1 d D U . A 1
F7 F 0.7187(4) 1.0036(4) 0.1054(6) 0.068(4) Uani 0.524(14) 1 d D U . A 1
F8 F 0.7018(5) 1.0821(6) 0.1808(4) 0.095(5) Uani 0.524(14) 1 d D U . A 1
F9 F 0.7460(6) 1.1560(5) 0.1129(7) 0.056(3) Uani 0.524(14) 1 d D U . A 1
F10 F 0.7651(7) 1.0778(7) 0.0378(6) 0.045(4) Uani 0.524(14) 1 d D U . A 1
P3 P 0.7623(3) 0.6810(3) 0.4105(3) 0.039(2) Uani 0.507(11) 1 d D . . B 1
F11 F 0.7597(8) 0.6169(5) 0.3668(5) 0.042(3) Uani 0.507(11) 1 d D U . B 1
F12 F 0.7648(5) 0.7451(5) 0.4527(6) 0.065(3) Uani 0.507(11) 1 d D U . B 1
F13 F 0.8397(3) 0.6679(4) 0.4258(5) 0.056(3) Uani 0.507(11) 1 d D U . B 1
F14 F 0.7824(5) 0.7216(4) 0.3475(5) 0.071(4) Uani 0.507(11) 1 d D U . B 1
F15 F 0.6851(5) 0.6940(7) 0.3944(7) 0.045(4) Uani 0.507(11) 1 d D U . B 1
F16 F 0.7423(6) 0.6410(5) 0.4737(5) 0.063(3) Uani 0.507(11) 1 d D U . B 1
P2A P 0.7351(4) 1.0565(4) 0.0921(4) 0.0440(17) Uani 0.476(14) 1 d D . . A 2
F5A F 0.8108(5) 1.0460(6) 0.1134(6) 0.051(3) Uani 0.476(14) 1 d D U . A 2
F6A F 0.6599(6) 1.0681(7) 0.0695(9) 0.083(6) Uani 0.476(14) 1 d D U . A 2
F7A F 0.7341(5) 0.9862(4) 0.0606(6) 0.060(3) Uani 0.476(14) 1 d D U . A 2
F8A F 0.7110(6) 1.0285(6) 0.1596(4) 0.089(5) Uani 0.476(14) 1 d D U . A 2
F9A F 0.7384(7) 1.1274(6) 0.1229(6) 0.053(4) Uani 0.476(14) 1 d D U . A 2
F10A F 0.7598(9) 1.0861(8) 0.0245(6) 0.059(5) Uani 0.476(14) 1 d D U . A 2
P3A P 0.7567(4) 0.6838(4) 0.3856(3) 0.0409(18) Uani 0.493(11) 1 d D . . B 2
F11A F 0.7491(10) 0.6103(6) 0.3645(9) 0.086(7) Uani 0.493(11) 1 d D U . B 2
F12A F 0.7638(5) 0.7567(4) 0.4096(6) 0.063(3) Uani 0.493(11) 1 d D U . B 2
F13A F 0.8346(3) 0.6810(4) 0.3703(5) 0.057(3) Uani 0.493(11) 1 d D U . B 2
F14A F 0.7411(5) 0.7084(5) 0.3133(4) 0.081(4) Uani 0.493(11) 1 d D U . B 2
F15A F 0.6784(6) 0.6863(8) 0.4024(8) 0.072(6) Uani 0.493(11) 1 d D U . B 2
F16A F 0.7732(6) 0.6611(6) 0.4590(5) 0.066(4) Uani 0.493(11) 1 d D U . B 2
N3 N 0.500000 0.8845(9) 0.2824(7) 0.132(6) Uani 1 2 d S T P . .
C20 C 0.500000 0.8408(7) 0.3174(7) 0.083(4) Uani 1 2 d S T P . .
C21 C 0.500000 0.7900(6) 0.3633(6) 0.111(6) Uani 1 2 d S T P . .
H21A H 0.546435 0.777189 0.372763 0.166 Uiso 0.5 1 calc GR . . C -1
H21B H 0.475389 0.752962 0.345466 0.166 Uiso 0.5 1 calc GR . . C -1
H21C H 0.478176 0.804510 0.403547 0.166 Uiso 0.5 1 calc GR . . C -1
N4 N 0.500000 0.8774(9) 0.0852(12) 0.206(11) Uani 1 2 d S T P . .
C22 C 0.500000 0.9286(9) 0.1080(8) 0.096(5) Uani 1 2 d S T P . .
C23 C 0.500000 0.9891(8) 0.1389(9) 0.122(6) Uani 1 2 d S T P . .
H23A H 0.527880 1.019480 0.113630 0.183 Uiso 0.5 1 d . . . D -1
H23B H 0.518240 0.984620 0.182630 0.183 Uiso 0.5 1 d . . . E -1
H23C H 0.453870 1.005690 0.140920 0.183 Uiso 0.5 1 d . . . F -1
N5 N 1.000000 0.8104(6) 0.2694(6) 0.088(3) Uani 1 2 d S T P . .
C25 C 1.000000 0.9115(7) 0.1945(7) 0.089(4) Uani 1 2 d S T P . .
H25A H 0.976129 0.901539 0.153924 0.133 Uiso 0.5 1 calc GR . . G -1
H25B H 1.046457 0.923766 0.184504 0.133 Uiso 0.5 1 calc GR . . G -1
H25C H 0.977413 0.947257 0.216823 0.133 Uiso 0.5 1 calc GR . . G -1
C24 C 1.000000 0.8541(7) 0.2369(7) 0.067(3) Uani 1 2 d S T P . .


_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
N1 C4 1.493(11) . ?
N1 C5 1.350(10) . ?
N1 C9 1.342(12) . ?
N2 C12 1.355(10) . ?
N2 C13 1.331(9) . ?
N2 C15 1.492(10) . ?
C1 C1 1.364(14) 4_655 ?
C1 H1 0.9500 . ?
C1 C2 1.390(9) . ?
C2 C3 1.383(9) . ?
C2 C4 1.499(9) . ?
C3 C3 1.386(14) 4_655 ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C6 1.368(12) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(12) . ?
C7 C8 1.426(10) . ?
C7 C10 1.453(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.354(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(10) . ?
C10 C14 1.411(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(12) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.374(12) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.502(11) . ?
C16 C17 1.374(10) . ?
C16 C19 1.392(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1A C4A 1.478(9) . ?
N1A C5A 1.371(10) . ?
N1A C9A 1.354(10) . ?
N2A C12A 1.368(8) . ?
N2A C13A 1.363(10) . ?
N2A C15A 1.478(9) . ?
C1A C1A 1.353(14) 4_755 ?
C1A H1A 0.9500 . ?
C1A C2A 1.396(9) . ?
C2A C3A 1.378(10) . ?
C2A C4A 1.505(11) . ?
C3A C3A 1.367(18) 4_755 ?
C3A H3A 0.9500 . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.362(10) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.408(9) . ?
C7A C8A 1.426(10) . ?
C7A C10A 1.421(10) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.336(11) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.416(10) . ?
C10A C14A 1.432(9) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.353(10) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C13A C14A 1.330(11) . ?
C14A H14A 0.9500 . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.512(12) . ?
C16A C17A 1.380(11) . ?
C16A C19A 1.398(9) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.384(13) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
P1 F1 1.598(6) . ?
P1 F2 1.591(4) . ?
P1 F2 1.591(4) 4_655 ?
P1 F3 1.614(5) . ?
P1 F4 1.599(4) 4_655 ?
P1 F4 1.599(4) . ?
P2 F5 1.594(8) . ?
P2 F6 1.608(9) . ?
P2 F7 1.606(8) . ?
P2 F8 1.584(8) . ?
P2 F9 1.598(8) . ?
P2 F10 1.609(9) . ?
P3 F11 1.602(9) . ?
P3 F12 1.586(8) . ?
P3 F13 1.595(8) . ?
P3 F14 1.591(8) . ?
P3 F15 1.594(8) . ?
P3 F16 1.589(8) . ?
P2A F5A 1.584(9) . ?
P2A F6A 1.583(10) . ?
P2A F7A 1.592(8) . ?
P2A F8A 1.577(9) . ?
P2A F9A 1.600(9) . ?
P2A F10A 1.592(10) . ?
P3A F11A 1.590(10) . ?
P3A F12A 1.593(9) . ?
P3A F13A 1.580(9) . ?
P3A F14A 1.599(9) . ?
P3A F15A 1.596(10) . ?
P3A F16A 1.611(9) . ?
N3 C20 1.154(16) . ?
C20 C21 1.412(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N4 C22 1.16(2) . ?
C22 C23 1.40(2) . ?
C23 H23A 0.9856 . ?
C23 H23B 0.9718 . ?
C23 H23C 0.9802 . ?
N5 C24 1.123(15) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 C24 1.472(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 120.1(8) . . ?
C9 N1 C4 119.1(7) . . ?
C9 N1 C5 120.3(8) . . ?
C12 N2 C15 120.4(7) . . ?
C13 N2 C12 119.8(7) . . ?
C13 N2 C15 119.8(7) . . ?
C1 C1 H1 119.6 4_655 . ?
C1 C1 C2 120.8(4) 4_655 . ?
C2 C1 H1 119.6 . . ?
C1 C2 C4 120.1(6) . . ?
C3 C2 C1 118.8(6) . . ?
C3 C2 C4 121.0(6) . . ?
C2 C3 C3 120.4(4) . 4_655 ?
C2 C3 H3 119.8 . . ?
C3 C3 H3 119.8 4_655 . ?
N1 C4 C2 108.9(6) . . ?
N1 C4 H4A 109.9 . . ?
N1 C4 H4B 109.9 . . ?
C2 C4 H4A 109.9 . . ?
C2 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 H5 119.8 . . ?
N1 C5 C6 120.3(9) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.9(8) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 114.8(8) . . ?
C6 C7 C10 122.1(7) . . ?
C8 C7 C10 123.0(8) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(9) . . ?
C9 C8 H8 119.4 . . ?
N1 C9 C8 121.0(7) . . ?
N1 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C7 120.6(8) . . ?
C11 C10 C14 116.0(8) . . ?
C14 C10 C7 123.4(7) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(9) . . ?
C12 C11 H11 119.8 . . ?
N2 C12 C11 121.6(7) . . ?
N2 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
N2 C13 H13 119.4 . . ?
N2 C13 C14 121.2(8) . . ?
C14 C13 H13 119.4 . . ?
C10 C14 H14 119.6 . . ?
C13 C14 C10 120.9(7) . . ?
C13 C14 H14 119.6 . . ?
N2 C15 H15A 108.9 . . ?
N2 C15 H15B 108.9 . . ?
N2 C15 C16 113.5(6) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C17 C16 C15 119.8(7) . . ?
C17 C16 C19 119.1(8) . . ?
C19 C16 C15 121.0(7) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(9) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C17 119.7(11) 4_655 . ?
C17 C18 H18 120.2 . . ?
C17 C18 H18 120.2 4_655 . ?
C16 C19 C16 121.0(9) . 4_655 ?
C16 C19 H19 119.5 4_655 . ?
C16 C19 H19 119.5 . . ?
C5A N1A C4A 119.6(7) . . ?
C9A N1A C4A 121.8(7) . . ?
C9A N1A C5A 117.9(7) . . ?
C12A N2A C15A 119.8(7) . . ?
C13A N2A C12A 117.6(7) . . ?
C13A N2A C15A 122.6(6) . . ?
C1A C1A H1A 119.5 4_755 . ?
C1A C1A C2A 121.1(5) 4_755 . ?
C2A C1A H1A 119.5 . . ?
C1A C2A C4A 120.6(7) . . ?
C3A C2A C1A 117.7(8) . . ?
C3A C2A C4A 121.5(7) . . ?
C2A C3A H3A 119.4 . . ?
C3A C3A C2A 121.2(5) 4_755 . ?
C3A C3A H3A 119.4 4_755 . ?
N1A C4A C2A 109.4(7) . . ?
N1A C4A H4AA 109.8 . . ?
N1A C4A H4AB 109.8 . . ?
C2A C4A H4AA 109.8 . . ?
C2A C4A H4AB 109.8 . . ?
H4AA C4A H4AB 108.2 . . ?
N1A C5A H5A 119.4 . . ?
C6A C5A N1A 121.2(7) . . ?
C6A C5A H5A 119.4 . . ?
C5A C6A H6A 119.1 . . ?
C5A C6A C7A 121.9(7) . . ?
C7A C6A H6A 119.1 . . ?
C6A C7A C8A 114.5(7) . . ?
C6A C7A C10A 123.1(7) . . ?
C10A C7A C8A 122.1(7) . . ?
C7A C8A H8A 119.3 . . ?
C9A C8A C7A 121.4(7) . . ?
C9A C8A H8A 119.3 . . ?
N1A C9A H9A 118.6 . . ?
C8A C9A N1A 122.9(7) . . ?
C8A C9A H9A 118.6 . . ?
C7A C10A C14A 122.7(7) . . ?
C11A C10A C7A 123.6(6) . . ?
C11A C10A C14A 113.7(7) . . ?
C10A C11A H11A 119.1 . . ?
C12A C11A C10A 121.9(7) . . ?
C12A C11A H11A 119.1 . . ?
N2A C12A H12A 119.0 . . ?
C11A C12A N2A 122.0(7) . . ?
C11A C12A H12A 119.0 . . ?
N2A C13A H13A 118.8 . . ?
C14A C13A N2A 122.4(7) . . ?
C14A C13A H13A 118.8 . . ?
C10A C14A H14A 118.9 . . ?
C13A C14A C10A 122.3(8) . . ?
C13A C14A H14A 118.9 . . ?
N2A C15A H15C 108.8 . . ?
N2A C15A H15D 108.8 . . ?
N2A C15A C16A 113.8(6) . . ?
H15C C15A H15D 107.7 . . ?
C16A C15A H15C 108.8 . . ?
C16A C15A H15D 108.8 . . ?
C17A C16A C15A 120.0(9) . . ?
C17A C16A C19A 119.6(10) . . ?
C19A C16A C15A 120.4(7) . . ?
C16A C17A H17A 120.2 . . ?
C16A C17A C18A 119.7(12) . . ?
C18A C17A H17A 120.2 . . ?
C17A C18A C17A 121.1(13) . 4_755 ?
C17A C18A H18A 119.5 4_755 . ?
C17A C18A H18A 119.5 . . ?
C16A C19A C16A 120.2(10) 4_755 . ?
C16A C19A H19A 119.9 4_755 . ?
C16A C19A H19A 119.9 . . ?
F1 P1 F3 179.8(3) . . ?
F1 P1 F4 90.6(2) . . ?
F1 P1 F4 90.6(2) . 4_655 ?
F2 P1 F1 89.8(2) 4_655 . ?
F2 P1 F1 89.8(2) . . ?
F2 P1 F2 90.2(3) 4_655 . ?
F2 P1 F3 90.0(2) 4_655 . ?
F2 P1 F3 90.0(2) . . ?
F2 P1 F4 90.3(2) 4_655 . ?
F2 P1 F4 90.3(2) . 4_655 ?
F2 P1 F4 179.3(3) . . ?
F2 P1 F4 179.3(3) 4_655 4_655 ?
F4 P1 F3 89.5(2) 4_655 . ?
F4 P1 F3 89.5(2) . . ?
F4 P1 F4 89.1(4) 4_655 . ?
F5 P2 F6 178.4(7) . . ?
F5 P2 F7 90.3(5) . . ?
F5 P2 F9 90.7(6) . . ?
F5 P2 F10 88.7(6) . . ?
F6 P2 F10 89.8(6) . . ?
F7 P2 F6 89.5(5) . . ?
F7 P2 F10 89.6(7) . . ?
F8 P2 F5 90.8(6) . . ?
F8 P2 F6 90.7(6) . . ?
F8 P2 F7 90.6(6) . . ?
F8 P2 F9 89.9(6) . . ?
F8 P2 F10 179.5(7) . . ?
F9 P2 F6 89.6(6) . . ?
F9 P2 F7 178.9(7) . . ?
F9 P2 F10 90.0(6) . . ?
F12 P3 F11 179.1(7) . . ?
F12 P3 F13 90.2(5) . . ?
F12 P3 F14 89.6(6) . . ?
F12 P3 F15 90.0(6) . . ?
F12 P3 F16 89.8(6) . . ?
F13 P3 F11 90.1(6) . . ?
F14 P3 F11 89.5(6) . . ?
F14 P3 F13 90.4(6) . . ?
F14 P3 F15 89.1(7) . . ?
F15 P3 F11 89.7(6) . . ?
F15 P3 F13 179.5(7) . . ?
F16 P3 F11 91.0(6) . . ?
F16 P3 F13 89.5(6) . . ?
F16 P3 F14 179.4(7) . . ?
F16 P3 F15 90.9(6) . . ?
F5A P2A F7A 89.9(5) . . ?
F5A P2A F9A 88.8(6) . . ?
F5A P2A F10A 90.0(7) . . ?
F6A P2A F5A 178.7(9) . . ?
F6A P2A F7A 90.4(6) . . ?
F6A P2A F9A 90.9(6) . . ?
F6A P2A F10A 88.7(8) . . ?
F7A P2A F9A 178.3(7) . . ?
F8A P2A F5A 89.8(6) . . ?
F8A P2A F6A 91.5(7) . . ?
F8A P2A F7A 90.9(6) . . ?
F8A P2A F9A 90.2(7) . . ?
F8A P2A F10A 178.9(9) . . ?
F10A P2A F7A 90.1(7) . . ?
F10A P2A F9A 88.8(7) . . ?
F11A P3A F12A 177.8(8) . . ?
F11A P3A F14A 91.9(7) . . ?
F11A P3A F15A 89.8(7) . . ?
F11A P3A F16A 89.7(7) . . ?
F12A P3A F14A 90.2(6) . . ?
F12A P3A F15A 89.4(7) . . ?
F12A P3A F16A 88.3(6) . . ?
F13A P3A F11A 90.3(7) . . ?
F13A P3A F12A 90.5(6) . . ?
F13A P3A F14A 91.1(6) . . ?
F13A P3A F15A 178.9(8) . . ?
F13A P3A F16A 88.6(6) . . ?
F14A P3A F16A 178.4(8) . . ?
F15A P3A F14A 90.0(7) . . ?
F15A P3A F16A 90.3(7) . . ?
N3 C20 C21 176.6(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 C23 177(2) . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.4 . . ?
C22 C23 H23C 109.3 . . ?
H23A C23 H23B 109.7 . . ?
H23A C23 H23C 109.0 . . ?
H23B C23 H23C 110.1 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
N5 C24 C25 179.9(14) . . ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.


Total solvent accessible volume / cell = 366.3 Ang³ [4.3%]
Total electron count / cell = 107.8
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.374 0.753 91.6 26.9 ?
2 0.000 0.626 0.253 91.6 27.0 ?
3 0.500 0.126 0.253 91.6 27.0 ?
4 0.500 0.874 0.753 91.6 26.9 ?

_olex2_date_sample_data_collection 2018-01-11
_olex2_date_sample_submission    2018-01-08
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1163
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.60(4)
2 0.40(4)

####################################################################### 
# 
# 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_cx1022
_database_code_depnum_ccdc_archive 'CCDC 1955707'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H32 N4, 0.5(C24 H28 N4), 3(F6 P)'
_chemical_formula_sum            'C48 H46 F18 N6 P3'
_chemical_formula_weight         1141.82
_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'
P P 0.2955 0.4335 '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      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.1423(6)
_cell_length_b                   21.9108(7)
_cell_length_c                   9.5937(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2972.79(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.353
_cell_measurement_theta_min      3.720
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.791
_exptl_absorpt_coefficient_mu    1.748
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0860 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.8754. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1166
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14176
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        65.061
_diffrn_reflns_theta_max         65.061
_diffrn_reflns_theta_min         3.720
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_special_details          ?
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1433
_reflns_number_total             2679
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2679
_refine_ls_number_restraints     342
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.1009
_refine_ls_restrained_S_all      1.392
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3140
_refine_ls_wR_factor_ref         0.3523
_refine_special_details          
'Distance restraints were imposed on the disordered atoms as well as a "FLAT" command on the disordered rings and the enhanced rigid-bond restraint (SHELX keyword RIGU) was applied globally. (Acta Cryst. A68 (2012) 448-451).'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9_$1-C8_$1 \\sim C7_$1-C8 \\sim C12-C7 \\sim C11-C10
 with sigma of 0.01
 C9_$1-C7_$1 \\sim C9-C9_$1 \\sim C9-C7 \\sim C8-C7 \\sim C8-C8_$1 \\sim
C8_$1-C7_$1 \\sim C7_$1-C10 ~
 C7-C10 \\sim C11-C7 \\sim C12-C11 \\sim C12-C11_$1 \\sim C11_$1-C7_$1
 with sigma of 0.01
 C12-C7 \\sim C10-C11
 with sigma of 0.01
 F1A-F1A_$3 \\sim F1A-F1A_$4 \\sim F1A_$3-F1A_$2 \\sim F1A_$2-F1A_$4
 with sigma of 0.04
 P1-F3 \\sim P1-F3_$3 \\sim P1-F1A \\sim P1-F1A_$3 \\sim P1-F1A_$2 \\sim
P1-F1A_$4
 with sigma of 0.02
3. Restrained planarity
 C7, C7_$1, C8_$1, C8, C9, C9_$1
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F7A)=1-FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(F8A)=Sof(P2A)=0.5*(1-FVAR(2))
 Sof(F4)=Sof(F5)=Sof(F6)=Sof(F8)=Sof(P2)=0.5*FVAR(2)
 Sof(F7)=FVAR(1)
 Fixed Sof: C8(0.5) H8(0.5) C9(0.5) H9(0.5) C10(0.25) H10(0.25) C11(0.5)
 H11(0.5) C12(0.25) H12(0.25) H18B(0.5) H18C(0.5) F1(0.25) F1A(0.5) F2(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.b Me refined with riding coordinates:
 C18(H18A,H18B,H18C)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17)
;
_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 0.2877(6) 0.4760(4) 0.6835(7) 0.132(2) Uani 1 1 d . U . . .
H1 H 0.227869 0.495430 0.691889 0.158 Uiso 1 1 calc R . . . .
C2 C 0.3657(5) 0.5101(3) 0.6722(5) 0.1097(19) Uani 1 1 d . U . . .
H2 H 0.359847 0.553214 0.665714 0.132 Uiso 1 1 calc R . . . .
C3 C 0.4578(4) 0.4831(3) 0.6697(5) 0.1015(18) Uani 1 1 d . U . . .
C4 C 0.4585(5) 0.4190(3) 0.6678(5) 0.1039(18) Uani 1 1 d . U . . .
H4 H 0.517354 0.398209 0.661069 0.125 Uiso 1 1 calc R . . . .
C5 C 0.3789(5) 0.3864(3) 0.6753(6) 0.114(2) Uani 1 1 d . U . . .
H5 H 0.382482 0.343079 0.675206 0.136 Uiso 1 1 calc R . . . .
C6 C 0.2059(6) 0.3786(4) 0.7137(9) 0.150(3) Uani 1 1 d . U . . .
H6A H 0.215580 0.335427 0.686572 0.180 Uiso 1 1 calc R . . . .
H6B H 0.152730 0.394964 0.658022 0.180 Uiso 1 1 calc R . . . .
C7 C 0.1818(5) 0.3817(3) 0.8637(7) 0.140(3) Uani 1 1 d D U . . .
C8 C 0.2311(8) 0.3359(4) 0.9279(5) 0.123(4) Uani 0.5 1 d D U . A 1
H8 H 0.263737 0.305591 0.875963 0.147 Uiso 0.5 1 calc R . . A 1
C9 C 0.1480(9) 0.4312(4) 0.9291(5) 0.116(4) Uani 0.5 1 d D U . A 1
H9 H 0.124763 0.465206 0.877988 0.139 Uiso 0.5 1 calc R . . A 1
C10 C 0.2098(10) 0.3649(7) 1.000000 0.122(6) Uani 0.5 2 d DS TU P A 2
H10 H 0.258975 0.335320 1.000000 0.146 Uiso 0.5 2 calc RS T P A 2
C11 C 0.0910(8) 0.4086(6) 0.8672(9) 0.141(4) Uani 0.5 1 d D U . A 2
H11 H 0.057141 0.419141 0.785070 0.169 Uiso 0.5 1 calc R . . A 2
C12 C 0.0550(14) 0.4184(14) 1.000000 0.190(10) Uani 0.5 2 d DS TU P A 2
H12 H -0.006814 0.435341 1.000000 0.229 Uiso 0.5 2 calc RS T P A 2
N1 N 0.2926(4) 0.4139(3) 0.6831(6) 0.133(2) Uani 1 1 d . U . . .
C13 C 0.4873(7) 0.3604(4) 1.000000 0.102(2) Uani 1 2 d S TU P . .
H13 H 0.443374 0.327615 1.000000 0.123 Uiso 1 2 calc RS T P . .
C14 C 0.4553(6) 0.4185(4) 1.000000 0.093(2) Uani 1 2 d S TU P . .
H14 H 0.389061 0.425638 1.000000 0.112 Uiso 1 2 calc RS T P . .
C15 C 0.5191(5) 0.4699(3) 1.000000 0.0820(18) Uani 1 2 d S TU P . .
C16 C 0.6147(6) 0.4540(4) 1.000000 0.094(2) Uani 1 2 d S TU P . .
H16 H 0.660701 0.485616 1.000000 0.113 Uiso 1 2 calc RS T P . .
C17 C 0.6440(7) 0.3955(4) 1.000000 0.102(2) Uani 1 2 d S TU P . .
H17 H 0.709698 0.386550 1.000000 0.122 Uiso 1 2 calc RS T P . .
C18 C 0.6141(8) 0.2846(4) 1.000000 0.134(4) Uani 1 2 d S TU P . .
H18A H 0.683409 0.284658 1.000000 0.202 Uiso 1 2 calc RS T P . .
H18B H 0.591038 0.263531 1.083405 0.202 Uiso 0.5 1 calc R . . . .
H18C H 0.591038 0.263530 0.916595 0.202 Uiso 0.5 1 calc R . . . .
N2 N 0.5790(6) 0.3486(3) 1.000000 0.1019(19) Uani 1 2 d S TU P . .
F1 F 0.000000 0.500000 0.6621(14) 0.147(7) Uani 0.5 2 d S TU P B 1
F1A F 0.0735(7) 0.5160(6) 0.6145(10) 0.250(12) Uani 0.5 1 d D U . B 2
F2 F 0.0984(9) 0.5229(7) 0.500000 0.122(4) Uani 0.5 2 d S TU P B 1
F3 F 0.0370(4) 0.43229(19) 0.500000 0.1279(18) Uani 1 2 d DS TU P B .
P1 P 0.000000 0.500000 0.500000 0.0933(10) Uani 1 4 d DS TU P . .
F4 F 0.0976(11) 0.2864(9) 0.500000 0.148(7) Uani 0.55(3) 2 d S TU P C 1
F5 F 0.1536(11) 0.1559(8) 0.500000 0.147(6) Uani 0.55(3) 2 d S TU P C 1
F6 F 0.2271(10) 0.2423(11) 0.500000 0.192(11) Uani 0.55(3) 2 d S TU P C 1
F7 F 0.1106(19) 0.2110(11) 0.6506(18) 0.224(7) Uani 0.55(3) 1 d . U . C 1
F8 F 0.0217(12) 0.2056(8) 0.500000 0.200(8) Uani 0.55(3) 2 d S TU P C 1
P2 P 0.1258(5) 0.2237(4) 0.500000 0.088(3) Uani 0.55(3) 2 d S TU P C 1
F4A F 0.1051(18) 0.2926(10) 0.500000 0.140(7) Uani 0.45(3) 2 d S TU P C 2
F5A F 0.184(4) 0.1494(12) 0.500000 0.229(13) Uani 0.45(3) 2 d S TU P C 2
F6A F 0.256(3) 0.2478(15) 0.500000 0.235(12) Uani 0.45(3) 2 d S TU P C 2
F7A F 0.158(3) 0.2320(8) 0.655(2) 0.222(9) Uani 0.45(3) 1 d . U . C 2
F8A F 0.045(4) 0.1880(18) 0.500000 0.275(15) Uani 0.45(3) 2 d S TU P C 2
P2A P 0.152(2) 0.2169(6) 0.500000 0.175(6) Uani 0.45(3) 2 d S TU P C 2


_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 1.336(10) . ?
C1 N1 1.364(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.430(8) . ?
C3 C3 1.405(12) 2_665 ?
C3 C4 1.406(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.335(9) . ?
C5 H5 0.9500 . ?
C5 N1 1.363(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.480(10) . ?
C6 N1 1.479(10) . ?
C7 C8 1.369(7) . ?
C7 C9 1.340(7) . ?
C7 C10 1.416(7) . ?
C7 C11 1.413(8) . ?
C8 C8 1.383(9) 6_557 ?
C8 H8 0.9500 . ?
C9 C9 1.361(9) 6_557 ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.389(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.350(12) . ?
C13 N2 1.322(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.443(11) . ?
C15 C15 1.426(14) 5_667 ?
C15 C16 1.396(10) . ?
C16 H16 0.9500 . ?
C16 C17 1.348(11) . ?
C17 H17 0.9500 . ?
C17 N2 1.379(11) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 N2 1.486(11) . ?
F1 P1 1.555(14) . ?
F1A P1 1.552(9) . ?
F2 P1 1.480(12) . ?
F3 P1 1.573(4) . ?
F4 P2 1.43(2) . ?
F5 P2 1.537(18) . ?
F6 P2 1.490(15) . ?
F7 P2 1.487(14) . ?
F8 P2 1.53(2) . ?
F4A P2A 1.79(3) . ?
F5A P2A 1.54(3) . ?
F6A P2A 1.61(3) . ?
F7A P2A 1.521(18) . ?
F8A P2A 1.64(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.5 . . ?
C2 C1 N1 121.0(7) . . ?
N1 C1 H1 119.5 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.5(7) . . ?
C3 C2 H2 119.3 . . ?
C3 C3 C2 123.8(8) 2_665 . ?
C3 C3 C4 121.3(7) 2_665 . ?
C4 C3 C2 114.9(6) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(6) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 N1 121.4(7) . . ?
N1 C5 H5 119.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N1 C6 C7 111.1(6) . . ?
C8 C7 C6 106.6(5) . . ?
C9 C7 C6 125.1(5) . . ?
C9 C7 C8 124.4(5) . . ?
C10 C7 C6 145.2(7) . . ?
C11 C7 C6 104.6(5) . . ?
C11 C7 C10 110.0(5) . . ?
C7 C8 C8 116.7(3) . 6_557 ?
C7 C8 H8 121.6 . . ?
C8 C8 H8 121.6 6_557 . ?
C7 C9 C9 117.9(3) . 6_557 ?
C7 C9 H9 121.1 . . ?
C9 C9 H9 121.1 6_557 . ?
C7 C10 C7 135.0(10) 6_557 . ?
C7 C10 H10 112.5 . . ?
C7 C10 H10 112.5 6_557 . ?
C7 C11 H11 122.6 . . ?
C12 C11 C7 114.8(7) . . ?
C12 C11 H11 122.6 . . ?
C11 C12 C11 133.2(11) 6_557 . ?
C11 C12 H12 113.4 . . ?
C11 C12 H12 113.4 6_557 . ?
C1 N1 C6 118.7(6) . . ?
C5 N1 C1 119.2(7) . . ?
C5 N1 C6 121.5(7) . . ?
C14 C13 H13 119.5 . . ?
N2 C13 H13 119.5 . . ?
N2 C13 C14 120.9(10) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.7(8) . . ?
C15 C14 H14 119.1 . . ?
C15 C15 C14 119.1(9) 5_667 . ?
C16 C15 C14 114.3(7) . . ?
C16 C15 C15 126.6(9) . 5_667 ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.3(8) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 N2 120.3(8) . . ?
N2 C17 H17 119.8 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
C13 N2 C17 120.4(8) . . ?
C13 N2 C18 120.8(9) . . ?
C17 N2 C18 118.7(8) . . ?
F1 P1 F1 180.0 . 5_566 ?
F1 P1 F3 90.0 . 2_565 ?
F1 P1 F3 90.0 5_566 . ?
F1 P1 F3 90.0 . . ?
F1 P1 F3 90.0 5_566 2_565 ?
F1A P1 F1A 180.0(9) 5_566 . ?
F1A P1 F3 89.4(5) 6_556 . ?
F1A P1 F3 90.6(5) 2_565 . ?
F1A P1 F3 90.6(5) 5_566 . ?
F1A P1 F3 89.4(5) . . ?
F2 P1 F1 90.000(3) 5_566 5_566 ?
F2 P1 F1 90.000(3) . 5_566 ?
F2 P1 F1 90.000(3) 5_566 . ?
F2 P1 F1 90.000(3) . . ?
F2 P1 F1A 45.1(4) 5_566 5_566 ?
F2 P1 F1A 134.9(4) . 2_565 ?
F2 P1 F1A 45.1(4) 5_566 2_565 ?
F2 P1 F1A 45.1(4) . 6_556 ?
F2 P1 F1A 134.9(4) . 5_566 ?
F2 P1 F1A 134.9(4) 5_566 6_556 ?
F2 P1 F2 180.0 5_566 . ?
F2 P1 F3 89.6(6) . 2_565 ?
F2 P1 F3 89.6(6) 5_566 . ?
F2 P1 F3 90.4(6) . . ?
F2 P1 F3 90.4(6) 5_566 2_565 ?
F3 P1 F3 180.0 . 2_565 ?
F4 P2 F5 178.7(11) . . ?
F4 P2 F6 90.3(11) . . ?
F4 P2 F7 98.0(10) . 6_556 ?
F4 P2 F7 98.0(10) . . ?
F4 P2 F8 88.9(10) . . ?
F6 P2 F5 91.1(10) . . ?
F6 P2 F8 179.2(12) . . ?
F7 P2 F5 81.7(10) . . ?
F7 P2 F5 81.7(10) 6_556 . ?
F7 P2 F6 101.0(11) . . ?
F7 P2 F6 101.0(11) 6_556 . ?
F7 P2 F7 153(2) 6_556 . ?
F7 P2 F8 79.1(11) . . ?
F7 P2 F8 79.1(11) 6_556 . ?
F8 P2 F5 89.7(9) . . ?
F5A P2A F4A 175(2) . . ?
F5A P2A F6A 98(2) . . ?
F5A P2A F8A 84.0(18) . . ?
F6A P2A F4A 87.1(15) . . ?
F6A P2A F8A 178(2) . . ?
F7A P2A F4A 79.6(10) 6_556 . ?
F7A P2A F4A 79.6(10) . . ?
F7A P2A F5A 101.0(10) 6_556 . ?
F7A P2A F5A 101.0(10) . . ?
F7A P2A F6A 81.8(12) . . ?
F7A P2A F6A 81.8(12) 6_556 . ?
F7A P2A F7A 154.1(18) 6_556 . ?
F7A P2A F8A 97.8(13) . . ?
F7A P2A F8A 97.8(13) 6_556 . ?
F8A P2A F4A 90.9(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C3 -174.5(4) . . . 2_665 ?
C1 C2 C3 C4 5.2(7) . . . . ?
C2 C1 N1 C5 2.0(10) . . . . ?
C2 C1 N1 C6 172.3(6) . . . . ?
C2 C3 C4 C5 -3.3(7) . . . . ?
C3 C3 C4 C5 176.4(4) 2_665 . . . ?
C3 C4 C5 N1 1.0(9) . . . . ?
C4 C5 N1 C1 -0.1(9) . . . . ?
C4 C5 N1 C6 -170.2(6) . . . . ?
C6 C7 C8 C8 170.2(4) . . . 6_557 ?
C6 C7 C9 C9 -166.4(5) . . . 6_557 ?
C6 C7 C10 C7 167.6(10) . . . 6_557 ?
C6 C7 C11 C12 -177.6(18) . . . . ?
C7 C6 N1 C1 -73.4(8) . . . . ?
C7 C6 N1 C5 96.7(7) . . . . ?
C7 C11 C12 C11 2(4) . . . 6_557 ?
C8 C7 C9 C9 -11.9(9) . . . 6_557 ?
C9 C7 C8 C8 11.8(9) . . . 6_557 ?
C10 C7 C11 C12 7(2) . . . . ?
C11 C7 C10 C7 -20(2) . . . 6_557 ?
N1 C1 C2 C3 -4.7(9) . . . . ?
N1 C6 C7 C8 -86.7(8) . . . . ?
N1 C6 C7 C9 71.6(10) . . . . ?
N1 C6 C7 C10 -67.1(17) . . . . ?
N1 C6 C7 C11 119.9(9) . . . . ?
C13 C14 C15 C15 180.0 . . . 5_667 ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C13 N2 C17 0.0 . . . . ?
C14 C13 N2 C18 180.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C15 C16 C17 180.0 5_667 . . . ?
C15 C16 C17 N2 0.0 . . . . ?
C16 C17 N2 C13 0.0 . . . . ?
C16 C17 N2 C18 180.0 . . . . ?
N2 C13 C14 C15 0.0 . . . . ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 626.7 Ang³ [21.0%]
Total electron count / cell = 171.6
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.115 0.333 -0.054 156.7 42.9 ?
2 0.115 0.667 -0.216 156.7 42.9 ?
3 0.385 0.167 -0.675 156.7 42.9 ?
4 0.615 0.833 -0.950 156.7 42.9 ?

_olex2_date_sample_data_collection 2017-07-17
_olex2_date_sample_submission    2017-07-07
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a glass fibre in Paratone oil'
_olex2_submission_original_sample_id cx1022
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cx1072
_database_code_depnum_ccdc_archive 'CCDC 1955703'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H32 N4, 4(F6 P)'
_chemical_formula_sum            'C36 H32 F24 N4 P4'
_chemical_formula_weight         1100.53
_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'
P P 0.2955 0.4335 '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                   7.4563(11)
_cell_length_b                   20.125(3)
_cell_length_c                   13.948(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.831(8)
_cell_angle_gamma                90
_cell_volume                     2092.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6342
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.030
_cell_measurement_theta_min      4.394
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.331
_exptl_absorpt_coefficient_mu    3.004
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1298 before and 0.0465 after correction. The Ratio of minimum to maximum transmission is 0.8065. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.473
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12508
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        65.074
_diffrn_reflns_theta_max         65.074
_diffrn_reflns_theta_min         3.857
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2993
_reflns_number_total             3544
_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 V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.068
_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)+(0.0447P)²+2.8834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1248
_refine_special_details          
'Rigid bond restraints were imposed on the displacement parameters as well as restraints on similar amplitudes separated by less than 1.7 Ang. on the disordered C13, C19 and the disordered Fluorine atoms.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Rigid bond restraints
 C13, C19, F3, F3A, F4, F4A, F5, F5A, F6, F6A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C13 \\sim C19 \\sim F3 \\sim F3A \\sim F4 \\sim F4A \\sim F5 \\sim F5A \\sim F6
\\sim F6A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Fixed Sof: H1BC(0.5) H1BD(0.5) H1AA(0.5) H1AB(0.5) H12C(0.5) H12D(0.5)
 H12A(0.5) H12B(0.5) C13(0.5) C14(0.5) H14(0.5) C15(0.5) H15(0.5) C16(0.5)
 H16(0.5) C17(0.5) C18(0.5) H18(0.5) C19(0.5) C20(0.5) H20(0.5) C21(0.5)
 H21(0.5) C22(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1BC,H1BD), C1(H1AA,H1AB), C12(H12C,H12D), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C18(H18), C20(H20), C21(H21), 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
N1 N 0.5856(4) 0.72524(15) 0.4719(2) 0.0518(8) Uani 1 1 d . . . . .
N2 N 0.4741(4) 0.47596(15) 0.8141(2) 0.0491(7) Uani 1 1 d . . . . .
C1 C 0.6033(6) 0.7714(2) 0.3872(4) 0.0761(14) Uani 1 1 d . . . . .
H1BC H 0.700880 0.803753 0.400455 0.091 Uiso 0.5 1 calc R . P A 2
H1BD H 0.490076 0.796279 0.375891 0.091 Uiso 0.5 1 calc R . P A 2
H1AA H 0.498896 0.801782 0.383920 0.091 Uiso 0.5 1 calc R . P B 1
H1AB H 0.712805 0.798680 0.396776 0.091 Uiso 0.5 1 calc R . P B 1
C2 C 0.4299(5) 0.72084(16) 0.5178(3) 0.0483(9) Uani 1 1 d . . . . .
H2 H 0.334058 0.750042 0.500672 0.058 Uiso 1 1 calc R . . . .
C3 C 0.4077(4) 0.67492(16) 0.5888(2) 0.0412(8) Uani 1 1 d . . . . .
H3 H 0.297251 0.672622 0.620757 0.049 Uiso 1 1 calc R . . . .
C4 C 0.5471(4) 0.63143(15) 0.6145(2) 0.0337(7) Uani 1 1 d . . . . .
C5 C 0.7090(4) 0.63887(17) 0.5682(2) 0.0412(8) Uani 1 1 d . . . . .
H5 H 0.808367 0.611344 0.585535 0.049 Uiso 1 1 calc R . . . .
C6 C 0.7253(5) 0.68579(19) 0.4977(3) 0.0529(9) Uani 1 1 d . . . . .
H6 H 0.836092 0.690564 0.466644 0.063 Uiso 1 1 calc R . . . .
C7 C 0.5214(4) 0.57817(15) 0.6861(2) 0.0340(7) Uani 1 1 d . . . . .
C8 C 0.3625(4) 0.54090(16) 0.6849(2) 0.0405(8) Uani 1 1 d . . . . .
H8 H 0.268735 0.550664 0.639329 0.049 Uiso 1 1 calc R . . . .
C9 C 0.3429(4) 0.49079(18) 0.7489(3) 0.0502(9) Uani 1 1 d . . . . .
H9 H 0.234880 0.465749 0.747707 0.060 Uiso 1 1 calc R . . . .
C10 C 0.6282(4) 0.51142(17) 0.8178(2) 0.0401(8) Uani 1 1 d . . . . .
H10 H 0.719105 0.500962 0.864615 0.048 Uiso 1 1 calc R . . . .
C11 C 0.6541(4) 0.56219(16) 0.7547(2) 0.0356(7) Uani 1 1 d . . . . .
H11 H 0.763111 0.586651 0.757587 0.043 Uiso 1 1 calc R . . . .
C12 C 0.4485(6) 0.4187(2) 0.8824(3) 0.0681(12) Uani 1 1 d . . . . .
H12C H 0.360795 0.431660 0.930869 0.082 Uiso 0.5 1 calc R . P C 2
H12D H 0.563942 0.408922 0.916521 0.082 Uiso 0.5 1 calc R . P C 2
H12A H 0.558411 0.412447 0.923108 0.082 Uiso 0.5 1 calc R . P D 1
H12B H 0.347666 0.428403 0.924760 0.082 Uiso 0.5 1 calc R . P D 1
C13 C 0.376(3) 0.3509(13) 0.826(2) 0.040(3) Uani 0.5 1 d . U P E 2
C14 C 0.2023(13) 0.3406(6) 0.8542(8) 0.056(3) Uani 0.5 1 d . . P E 2
H14 H 0.149019 0.368565 0.900214 0.067 Uiso 0.5 1 calc R . P E 2
C15 C 0.1111(10) 0.2891(5) 0.8137(7) 0.071(3) Uani 0.5 1 d . . P E 2
H15 H -0.001399 0.276405 0.838074 0.085 Uiso 0.5 1 calc R . P E 2
C16 C 0.1797(14) 0.2546(5) 0.7371(9) 0.063(3) Uani 0.5 1 d . . P E 2
H16 H 0.115118 0.220124 0.704908 0.075 Uiso 0.5 1 calc R . P E 2
C17 C 0.350(3) 0.2743(8) 0.7109(14) 0.038(4) Uani 0.5 1 d . . P E 2
C18 C 0.4436(8) 0.3234(3) 0.7475(4) 0.0348(14) Uani 0.5 1 d . . P E 2
H18 H 0.551611 0.338627 0.720589 0.042 Uiso 0.5 1 calc R . P E 2
C19 C 0.415(3) 0.3657(11) 0.834(2) 0.034(3) Uani 0.5 1 d . U P E 1
C20 C 0.2569(14) 0.3313(5) 0.8138(7) 0.044(2) Uani 0.5 1 d . . P E 1
H20 H 0.154320 0.341839 0.849501 0.052 Uiso 0.5 1 calc R . P E 1
C21 C 0.2411(14) 0.2821(5) 0.7441(7) 0.043(2) Uani 0.5 1 d . . P E 1
H21 H 0.126817 0.262593 0.731311 0.052 Uiso 0.5 1 calc R . P E 1
C22 C 0.388(2) 0.2600(7) 0.6915(13) 0.029(3) Uani 0.5 1 d . . P E 1
C23 C 0.5629(8) 0.2852(3) 0.7278(5) 0.0416(16) Uani 0.5 1 d . . P E 1
H23 H 0.669739 0.267852 0.702294 0.050 Uiso 0.5 1 calc R . P E 1
C24 C 0.5753(7) 0.3331(3) 0.7976(4) 0.0399(15) Uani 0.5 1 d . . P E 1
H24 H 0.690240 0.345532 0.822932 0.048 Uiso 0.5 1 calc R . P E 1
P1 P 0.10173(11) 0.60753(4) 0.92571(6) 0.0426(3) Uani 1 1 d . . . . .
F1 F -0.1105(2) 0.60388(10) 0.93753(15) 0.0515(5) Uani 1 1 d . . . . .
F2 F 0.3139(3) 0.61183(14) 0.91311(18) 0.0740(7) Uani 1 1 d . . . . .
F3 F 0.0745(3) 0.62085(16) 0.81325(18) 0.0590(7) Uani 0.908(4) 1 d . U P F 1
F3A F 0.071(3) 0.5550(15) 0.842(2) 0.064(6) Uani 0.092(4) 1 d . U P F 2
F4 F 0.0935(4) 0.68570(13) 0.9458(2) 0.0728(9) Uani 0.908(4) 1 d . U P F 1
F4A F 0.052(4) 0.6601(16) 0.849(2) 0.069(6) Uani 0.092(4) 1 d . U P F 2
F5 F 0.1283(3) 0.5944(2) 1.03769(19) 0.0739(10) Uani 0.908(4) 1 d . U P F 1
F5A F 0.157(3) 0.6525(14) 1.009(2) 0.064(6) Uani 0.092(4) 1 d . U P F 2
F6 F 0.1065(4) 0.53062(13) 0.9051(3) 0.0746(9) Uani 0.908(4) 1 d . U P F 1
F6A F 0.151(3) 0.5497(15) 0.992(3) 0.064(6) Uani 0.092(4) 1 d . U P F 2
P2 P 0.88323(10) 0.41577(4) 0.61172(5) 0.0340(2) Uani 1 1 d . . . . .
F7 F 0.6694(2) 0.41773(10) 0.60483(14) 0.0504(5) Uani 1 1 d . . . . .
F8 F 1.0986(2) 0.41343(10) 0.61808(15) 0.0533(5) Uani 1 1 d . . . . .
F9 F 0.8910(2) 0.41061(10) 0.49735(12) 0.0431(5) Uani 1 1 d . . . . .
F10 F 0.8927(3) 0.49421(10) 0.60879(16) 0.0574(6) Uani 1 1 d . . . . .
F11 F 0.8793(3) 0.41853(11) 0.72653(14) 0.0620(6) Uani 1 1 d . . . . .
F12 F 0.8776(3) 0.33623(10) 0.61640(14) 0.0520(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.512(5) . ?
N1 C2 1.346(5) . ?
N1 C6 1.349(4) . ?
N2 C9 1.348(4) . ?
N2 C10 1.352(4) . ?
N2 C12 1.511(5) . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 C17 1.694(14) 3_666 ?
C1 C22 1.269(15) 3_666 ?
C2 H2 0.9500 . ?
C2 C3 1.368(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(4) . ?
C4 C5 1.395(4) . ?
C4 C7 1.482(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.371(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(4) . ?
C7 C11 1.392(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.358(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.366(5) . ?
C11 H11 0.9500 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.66(2) . ?
C12 C19 1.28(2) . ?
C13 C14 1.38(2) . ?
C13 C18 1.34(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.354(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.39(2) . ?
C17 C18 1.30(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(15) . ?
C19 C24 1.47(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.410(14) . ?
C22 C23 1.47(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.370(10) . ?
C24 H24 0.9500 . ?
P1 F1 1.598(2) . ?
P1 F2 1.600(2) . ?
P1 F3 1.598(2) . ?
P1 F3A 1.59(3) . ?
P1 F4 1.599(3) . ?
P1 F4A 1.54(3) . ?
P1 F5 1.590(3) . ?
P1 F5A 1.52(2) . ?
P1 F6 1.575(3) . ?
P1 F6A 1.52(2) . ?
P2 F7 1.5944(19) . ?
P2 F8 1.6060(19) . ?
P2 F9 1.6014(19) . ?
P2 F10 1.581(2) . ?
P2 F11 1.604(2) . ?
P2 F12 1.603(2) . ?

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 N1 C1 120.7(3) . . ?
C2 N1 C6 120.3(3) . . ?
C6 N1 C1 118.9(3) . . ?
C9 N2 C10 120.4(3) . . ?
C9 N2 C12 119.4(3) . . ?
C10 N2 C12 120.2(3) . . ?
N1 C1 H1BC 109.9 . . ?
N1 C1 H1BD 109.9 . . ?
N1 C1 H1AA 109.1 . . ?
N1 C1 H1AB 109.1 . . ?
N1 C1 C17 108.9(7) . 3_666 ?
H1BC C1 H1BD 108.3 . . ?
H1AA C1 H1AB 107.9 . . ?
C17 C1 H1BC 109.9 3_666 . ?
C17 C1 H1BD 109.9 3_666 . ?
C22 C1 N1 112.3(9) 3_666 . ?
C22 C1 H1AA 109.1 3_666 . ?
C22 C1 H1AB 109.1 3_666 . ?
C22 C1 C17 9.7(14) 3_666 3_666 ?
N1 C2 H2 119.5 . . ?
N1 C2 C3 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 C7 121.5(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C5 120.7(3) . . ?
N1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C4 120.4(2) . . ?
C11 C7 C4 121.7(3) . . ?
C11 C7 C8 117.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
N2 C9 C8 121.2(3) . . ?
N2 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
N2 C10 H10 119.7 . . ?
N2 C10 C11 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C7 C11 H11 119.9 . . ?
C10 C11 C7 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
N2 C12 H12C 109.2 . . ?
N2 C12 H12D 109.2 . . ?
N2 C12 H12A 109.9 . . ?
N2 C12 H12B 109.9 . . ?
N2 C12 C13 111.9(10) . . ?
H12C C12 H12D 107.9 . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12C 109.2 . . ?
C13 C12 H12D 109.2 . . ?
C19 C12 N2 109.1(12) . . ?
C19 C12 H12A 109.9 . . ?
C19 C12 H12B 109.9 . . ?
C14 C13 C12 106(2) . . ?
C18 C13 C12 127.1(14) . . ?
C18 C13 C14 123.6(16) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 C13 117.3(16) . . ?
C15 C14 H14 121.4 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(8) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 122.5 . . ?
C15 C16 C17 115.0(12) . . ?
C17 C16 H16 122.5 . . ?
C18 C17 C16 126.4(13) . . ?
C13 C18 H18 122.5 . . ?
C17 C18 C13 115.1(11) . . ?
C17 C18 H18 122.5 . . ?
C12 C19 C20 132(3) . . ?
C12 C19 C24 114.0(14) . . ?
C20 C19 C24 113.8(18) . . ?
C19 C20 H20 118.4 . . ?
C19 C20 C21 123.3(15) . . ?
C21 C20 H20 118.4 . . ?
C20 C21 H21 118.7 . . ?
C20 C21 C22 122.6(11) . . ?
C22 C21 H21 118.7 . . ?
C1 C22 C21 131.9(16) 3_666 . ?
C1 C22 C23 113.6(11) 3_666 . ?
C21 C22 C23 113.9(11) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.8(7) . . ?
C24 C23 H23 119.1 . . ?
C19 C24 H24 119.3 . . ?
C23 C24 C19 121.5(9) . . ?
C23 C24 H24 119.3 . . ?
F1 P1 F2 179.40(14) . . ?
F1 P1 F4 89.06(13) . . ?
F3 P1 F1 90.79(12) . . ?
F3 P1 F2 88.75(13) . . ?
F3 P1 F4 90.14(16) . . ?
F3A P1 F1 85.7(8) . . ?
F3A P1 F2 94.3(8) . . ?
F4 P1 F2 90.55(14) . . ?
F4A P1 F1 83.4(10) . . ?
F4A P1 F2 96.0(10) . . ?
F4A P1 F3A 85.5(18) . . ?
F5 P1 F1 89.06(13) . . ?
F5 P1 F2 91.40(13) . . ?
F5 P1 F3 179.83(19) . . ?
F5 P1 F4 89.80(18) . . ?
F5A P1 F1 101.3(9) . . ?
F5A P1 F2 78.7(9) . . ?
F5A P1 F3A 171.6(14) . . ?
F5A P1 F4A 99.9(19) . . ?
F5A P1 F6A 86.6(18) . . ?
F6 P1 F1 90.10(13) . . ?
F6 P1 F2 90.28(15) . . ?
F6 P1 F3 89.33(18) . . ?
F6 P1 F4 179.00(17) . . ?
F6 P1 F5 90.73(19) . . ?
F6A P1 F1 97.1(9) . . ?
F6A P1 F2 83.5(9) . . ?
F6A P1 F3A 87.9(19) . . ?
F6A P1 F4A 173(2) . . ?
F7 P2 F8 179.61(13) . . ?
F7 P2 F9 90.54(10) . . ?
F7 P2 F11 90.51(12) . . ?
F7 P2 F12 90.00(11) . . ?
F9 P2 F8 89.16(10) . . ?
F9 P2 F11 178.00(12) . . ?
F9 P2 F12 88.72(11) . . ?
F10 P2 F7 91.11(11) . . ?
F10 P2 F8 89.14(11) . . ?
F10 P2 F9 92.07(11) . . ?
F10 P2 F11 89.62(12) . . ?
F10 P2 F12 178.64(12) . . ?
F11 P2 F8 89.78(12) . . ?
F12 P2 F8 89.76(11) . . ?
F12 P2 F11 89.57(12) . . ?

_olex2_date_sample_data_collection 2017-09-18
_olex2_date_sample_submission    2017-09-18
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1072
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cx1161
_database_code_depnum_ccdc_archive 'CCDC 1955705'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2018-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H28 N4 S2, 2(F6 P)'
_chemical_formula_sum            'C32 H28 F12 N4 P2 S2'
_chemical_formula_weight         822.64
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.3821(5)
_cell_length_b                   21.5348(9)
_cell_length_c                   9.6558(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2158.81(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.934
_cell_measurement_theta_min      4.106
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.522
_exptl_absorpt_coefficient_mu    2.526
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1001 before and 0.0456 after correction. The Ratio of minimum to maximum transmission is 0.9038. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             836
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.021
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12125
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.964
_diffrn_reflns_theta_min         4.106
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1746
_reflns_number_total             1999
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.080
_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)+(0.0968P)²+1.8458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1561
_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:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8)
;
_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
S1 S 0.82219(9) 0.30198(5) 1.0000 0.0320(3) Uani 1 2 d S T P . .
N1 N 0.8193(2) 0.36179(9) 0.6839(2) 0.0251(5) Uani 1 1 d . . . . .
C1 C 0.7586(3) 0.41788(12) 0.6768(2) 0.0258(6) Uani 1 1 d . . . . .
H1 H 0.6672 0.4194 0.6804 0.031 Uiso 1 1 calc R . . . .
C2 C 0.8262(2) 0.47154(11) 0.6648(2) 0.0253(6) Uani 1 1 d . . . . .
H2 H 0.7809 0.5098 0.6593 0.030 Uiso 1 1 calc R . . . .
C3 C 0.9634(2) 0.47209(10) 0.6601(2) 0.0221(5) Uani 1 1 d . . . . .
C4 C 1.0220(2) 0.41202(11) 0.6631(2) 0.0242(6) Uani 1 1 d . . . . .
H4 H 1.1130 0.4088 0.6573 0.029 Uiso 1 1 calc R . . . .
C5 C 0.9501(2) 0.35941(11) 0.6741(2) 0.0251(6) Uani 1 1 d . . . . .
H5 H 0.9920 0.3202 0.6750 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7436(3) 0.30600(11) 0.7211(3) 0.0288(6) Uani 1 1 d . . . . .
H6A H 0.7948 0.2683 0.7008 0.035 Uiso 1 1 calc R . . . .
H6B H 0.6644 0.3045 0.6641 0.035 Uiso 1 1 calc R . . . .
C7 C 0.7077(2) 0.30659(11) 0.8713(3) 0.0241(6) Uani 1 1 d . . . . .
C8 C 0.5875(3) 0.31263(13) 0.9265(3) 0.0343(7) Uani 1 1 d . . . . .
H8 H 0.5116 0.3165 0.8722 0.041 Uiso 1 1 calc R . . . .
P1 P 0.88021(8) 0.15612(4) 0.5000 0.0239(3) Uani 1 2 d S T P . .
F1 F 0.8792(2) 0.15668(10) 0.66473(19) 0.0613(6) Uani 1 1 d . . . . .
F2 F 0.7391(2) 0.18564(10) 0.5000 0.0353(6) Uani 1 2 d S T P . .
F3 F 0.8200(2) 0.08831(11) 0.5000 0.0478(7) Uani 1 2 d S T P . .
F4 F 1.0215(2) 0.12791(11) 0.5000 0.0517(7) Uani 1 2 d S T P . .
F5 F 0.9391(2) 0.22441(11) 0.5000 0.0495(7) Uani 1 2 d S T P . .


_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
S1 C7 1.722(3) 6_557 ?
S1 C7 1.722(3) . ?
N1 C1 1.364(3) . ?
N1 C5 1.362(3) . ?
N1 C6 1.480(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.357(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.425(4) . ?
C3 C3 1.422(5) 2_765 ?
C3 C4 1.429(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(3) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.497(3) . ?
C7 C8 1.363(4) . ?
C8 C8 1.420(5) 6_557 ?
C8 H8 0.9500 . ?
P1 F1 1.5907(19) 6_556 ?
P1 F1 1.5907(19) . ?
P1 F2 1.597(2) . ?
P1 F3 1.589(2) . ?
P1 F4 1.588(2) . ?
P1 F5 1.593(2) . ?

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
C7 S1 C7 92.36(18) 6_557 . ?
C1 N1 C6 119.0(2) . . ?
C5 N1 C1 119.4(2) . . ?
C5 N1 C6 121.0(2) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 N1 121.3(2) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 114.6(2) . . ?
C3 C3 C2 122.7(3) 2_765 . ?
C3 C3 C4 122.6(3) 2_765 . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.3 . . ?
N1 C5 H5 119.3 . . ?
C4 C5 N1 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N1 C6 C7 111.11(19) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 S1 121.8(2) . . ?
C8 C7 S1 110.80(19) . . ?
C8 C7 C6 127.4(2) . . ?
C7 C8 C8 113.01(16) . 6_557 ?
C7 C8 H8 123.5 . . ?
C8 C8 H8 123.5 6_557 . ?
F1 P1 F1 178.85(17) . 6_556 ?
F1 P1 F2 89.49(8) 6_556 . ?
F1 P1 F2 89.48(8) . . ?
F1 P1 F5 89.74(9) 6_556 . ?
F1 P1 F5 89.74(9) . . ?
F3 P1 F1 90.25(9) . 6_556 ?
F3 P1 F1 90.25(9) . . ?
F3 P1 F2 90.28(12) . . ?
F3 P1 F5 179.40(14) . . ?
F4 P1 F1 90.51(8) . . ?
F4 P1 F1 90.51(8) . 6_556 ?
F4 P1 F2 179.03(13) . . ?
F4 P1 F3 90.70(13) . . ?
F4 P1 F5 89.90(14) . . ?
F5 P1 F2 89.12(13) . . ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 646.5 Ang³ [29.9%]
Total electron count / cell = 149.4
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.183 0.000 -0.142 323.3 74.7 ?
2 0.633 0.500 -0.593 323.3 74.7 ?

_olex2_date_sample_data_collection 2018-01-10
_olex2_date_sample_submission    2018-01-08
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1161
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cx1045
_database_code_depnum_ccdc_archive 'CCDC 1955706'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H31 N5, 4(F6 P)'
_chemical_formula_sum            'C35 H31 F24 N5 P4'
_chemical_formula_weight         1101.53
_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'
P P 0.2955 0.4335 '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                   11.2904(11)
_cell_length_b                   16.9439(18)
_cell_length_c                   24.966(3)
_cell_angle_alpha                75.157(10)
_cell_angle_beta                 86.061(11)
_cell_angle_gamma                86.580(9)
_cell_volume                     4601.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4665
_cell_measurement_temperature    99.98
_cell_measurement_theta_max      64.6830
_cell_measurement_theta_min      2.7680
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.489
_exptl_absorpt_coefficient_mu    2.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2208
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1817
_diffrn_reflns_av_unetI/netI     0.1636
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34289
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        60.000
_diffrn_reflns_theta_max         60.000
_diffrn_reflns_theta_min         1.833
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -360.00   9.50   0.50   30.00 -55.02 -97.50  33.00    --   739
  2  φ   -328.39   9.11   0.50   30.00-152.20 -97.50-164.56    --   675
  3  φ     20.88 270.38   0.50   29.99 163.25  90.00 105.51    --   499
  4  φ    114.12 287.62   0.50   10.00  13.41 -35.00  58.00    --   347
  5  φ    182.41 312.91   0.50   29.99-113.97 -87.50-107.00    --   261
  6  φ    155.10 295.60   0.50   29.99-150.75 -97.50-119.51    --   281
  7  ω    -73.97  -4.47   0.50   10.00    --  -52.50  78.01-127.50  139
  8  φ      7.42 129.92   0.50   10.00  52.90  27.50-129.52    --   245
  9  ω   -126.86 -18.36   0.50   30.00    --  -90.00 143.03  64.98  217
 10  ω    180.33 272.83   0.50   30.00    --  -95.00-109.52  80.02  185
 11  ω     70.50 105.50   0.50   10.00    --   20.00 133.01 169.99   70
 12  ω    246.92 280.92   0.50   10.00    --  -52.50-104.50-172.50   68
 13  ω   -123.60 -20.10   0.50   30.00    --  -97.50 140.52-157.52  207
 14  ω   -108.99  -7.49   0.50   30.00    --  -92.50 100.50 120.00  203
 15  ω    109.76 145.76   0.50   30.00    --   87.50-169.60 107.58   72
 16  ω    224.43 265.43   0.50   30.00    -- -100.00 -52.01  15.00   82
 17  ω    247.00 285.50   0.50   30.00    --  -92.50-119.51  10.01   77
 18  ω    236.01 345.51   0.50   30.00    -- -100.00  25.50 -90.01  219
 19  φ     18.91 117.91   0.50   10.00  43.34 -40.00-174.63    --   198
 20  ω    218.63 258.63   0.50   30.00    --  -92.50 -52.01 122.50   80
 21  ω     55.88  97.38   0.50   30.00    --   90.00 -32.00  87.50   83
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0273204000
_diffrn_orient_matrix_UB_12      -0.0011751000
_diffrn_orient_matrix_UB_13      -0.0611086000
_diffrn_orient_matrix_UB_21      0.0841168000
_diffrn_orient_matrix_UB_22      -0.0757481000
_diffrn_orient_matrix_UB_23      0.0184631000
_diffrn_orient_matrix_UB_31      -0.1045001000
_diffrn_orient_matrix_UB_32      -0.0559018000
_diffrn_orient_matrix_UB_33      0.0035222000
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4387
_reflns_number_total             13418
_reflns_odcompleteness_completeness 91.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.36
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.947
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.535
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1276
_refine_ls_number_reflns         13418
_refine_ls_number_restraints     1402
_refine_ls_R_factor_all          0.3412
_refine_ls_R_factor_gt           0.2375
_refine_ls_restrained_S_all      1.476
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5158
_refine_ls_wR_factor_ref         0.6050
_refine_special_details          
'The enhanced rigid-bond restraint (SHELX keyword RIGU) was applied globally. (Acta Cryst. A68 (2012) 448-451). Distance restraints were imposed on the PF6 anions.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F33-F32 \\sim F33-F34 \\sim F33-F36 \\sim F32-F35 \\sim F32-F34 \\sim F32-F36
\\sim F35-F34 \\sim F35-F36
 with sigma of 0.04
 P6-F33 \\sim P6-F32 \\sim P6-F35 \\sim P6-F31 \\sim P6-F34 \\sim P6-F36
 with sigma of 0.02
 F30-F26 \\sim F30-F25 \\sim F30-F29 \\sim F28-F26 \\sim F28-F25 \\sim F28-F29
\\sim F27-F26 \\sim F27-F25
 \\sim F25-F29
 with sigma of 0.02
 P5-F30 \\sim P5-F28 \\sim P5-F27 \\sim P5-F26 \\sim P5-F25 \\sim P5-F29
 with sigma of 0.01
 F22-F23 \\sim F22-F20 \\sim F22-F19 \\sim F22-F21 \\sim F24-F23 \\sim F24-F20
\\sim F24-F19 \\sim F24-F21
 \\sim F23-F20 \\sim F23-F19 \\sim F20-F21 \\sim F19-F21
 with sigma of 0.02
 P4-F22 \\sim P4-F24 \\sim P4-F23 \\sim P4-F20 \\sim P4-F19 \\sim P4-F21
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: P4(0.5) F19(0.5) F20(0.5) F21(0.5) F22(0.5) F23(0.5) F24(0.5)
 P6(0.5) F31(0.5) F32(0.5) F33(0.5) F34(0.5) F35(0.5) F36(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C18(H18A,H18B), C29(H29A,H29B), C1A(H1AA,H1AB),
 C12A(H12C,H12D), C18A(H18C,H18D), C29A(H29C,H29D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
  C27(H27), C28(H28), C34(H34), C35(H35), C31(H31), C32(H32), C2A(H2A),
 C3A(H3A), C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C14A(H14A), C15A(H15A), C16A(H16A), C19A(H19A), C20A(H20A), C22A(H22A),
 C23A(H23A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C31A(H31A),
 C32A(H32A), C34A(H34A), C35A(H35A)
5.c Fitted hexagon refined as free rotating group:
 C33(C34,C35,C30,C31,C32)
;
_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
N1 N 0.9564(13) 0.9959(12) 0.3969(9) 0.119(6) Uani 1 1 d . U . . .
N2 N 1.3579(12) 1.0733(11) 0.1698(10) 0.112(5) Uani 1 1 d . U . . .
N3 N 1.3766(11) 0.9880(10) 0.0772(8) 0.104(6) Uani 1 1 d . U . . .
N4 N 1.1946(13) 0.8708(10) 0.0783(8) 0.103(5) Uani 1 1 d . U . . .
N5 N 0.7709(15) 0.7462(12) 0.2940(11) 0.124(6) Uani 1 1 d . U . . .
C1 C 0.8619(19) 0.9679(17) 0.4412(12) 0.149(9) Uani 1 1 d . U . . .
H1A H 0.807915 1.014590 0.445009 0.179 Uiso 1 1 calc R . . . .
H1B H 0.897965 0.944110 0.477166 0.179 Uiso 1 1 calc R . . . .
C2 C 1.053(2) 0.9445(14) 0.3991(13) 0.135(9) Uani 1 1 d . U . . .
H2 H 1.064413 0.898627 0.429774 0.162 Uiso 1 1 calc R . . . .
C3 C 1.1391(19) 0.9631(16) 0.3519(14) 0.149(10) Uani 1 1 d . U . . .
H3 H 1.209330 0.929397 0.351784 0.179 Uiso 1 1 calc R . . . .
C4 C 1.1206(17) 1.0267(14) 0.3091(12) 0.113(6) Uani 1 1 d . U . . .
C5 C 1.0182(16) 1.0792(13) 0.3077(10) 0.101(6) Uani 1 1 d . U . . .
H5 H 1.004361 1.125237 0.277394 0.121 Uiso 1 1 calc R . . . .
C6 C 0.9384(18) 1.0585(15) 0.3541(12) 0.131(8) Uani 1 1 d . U . . .
H6 H 0.867470 1.091470 0.354743 0.157 Uiso 1 1 calc R . . . .
C7 C 1.2078(14) 1.0438(11) 0.2589(11) 0.102(5) Uani 1 1 d . U . . .
C8 C 1.3263(15) 1.0301(12) 0.2628(12) 0.112(6) Uani 1 1 d . U . . .
H8 H 1.356838 1.007082 0.298243 0.135 Uiso 1 1 calc R . . . .
C9 C 1.4060(16) 1.0488(14) 0.2159(12) 0.125(7) Uani 1 1 d . U . . .
H9 H 1.489766 1.043540 0.218581 0.150 Uiso 1 1 calc R . . . .
C10 C 1.2381(13) 1.0849(9) 0.1616(10) 0.091(5) Uani 1 1 d . U . . .
H10 H 1.208649 1.104867 0.125674 0.109 Uiso 1 1 calc R . . . .
C11 C 1.1627(15) 1.0657(13) 0.2093(11) 0.113(6) Uani 1 1 d . U . . .
H11 H 1.079121 1.068152 0.206226 0.135 Uiso 1 1 calc R . . . .
C12 C 1.4426(15) 1.0913(12) 0.1182(10) 0.114(6) Uani 1 1 d . U . . .
H12A H 1.408329 1.137123 0.089604 0.136 Uiso 1 1 calc R . . . .
H12B H 1.519066 1.108379 0.127817 0.136 Uiso 1 1 calc R . . . .
C13 C 1.4648(16) 1.0187(11) 0.0951(11) 0.108(6) Uani 1 1 d . U . . .
C14 C 1.5789(17) 0.9829(11) 0.0929(9) 0.098(6) Uani 1 1 d . U . . .
H14 H 1.643061 1.004871 0.106211 0.118 Uiso 1 1 calc R . . . .
C15 C 1.5992(17) 0.9138(12) 0.0710(12) 0.125(8) Uani 1 1 d . U . . .
H15 H 1.675729 0.887701 0.069623 0.150 Uiso 1 1 calc R . . . .
C16 C 1.5006(17) 0.8861(12) 0.0515(11) 0.117(8) Uani 1 1 d . U . . .
H16 H 1.509923 0.839555 0.036710 0.140 Uiso 1 1 calc R . . . .
C17 C 1.3940(16) 0.9234(13) 0.0531(10) 0.109(7) Uani 1 1 d . U . . .
C18 C 1.2805(16) 0.9017(13) 0.0288(10) 0.109(6) Uani 1 1 d . U . . .
H18A H 1.245675 0.950582 0.002898 0.130 Uiso 1 1 calc R . . . .
H18B H 1.299640 0.858914 0.008615 0.130 Uiso 1 1 calc R . . . .
C19 C 1.1951(17) 0.7891(14) 0.1050(11) 0.120(7) Uani 1 1 d . U . . .
H19 H 1.249656 0.751159 0.093320 0.144 Uiso 1 1 calc R . . . .
C20 C 1.1153(18) 0.7640(15) 0.1486(11) 0.121(7) Uani 1 1 d . U . . .
H20 H 1.119510 0.708414 0.169163 0.145 Uiso 1 1 calc R . . . .
C21 C 1.0227(17) 0.8193(14) 0.1652(12) 0.117(6) Uani 1 1 d . U . . .
C22 C 1.0260(16) 0.8966(15) 0.1325(12) 0.127(8) Uani 1 1 d . U . . .
H22 H 0.965149 0.934258 0.139723 0.152 Uiso 1 1 calc R . . . .
C23 C 1.1082(17) 0.9263(13) 0.0898(11) 0.114(7) Uani 1 1 d . U . . .
H23 H 1.105737 0.981983 0.069412 0.137 Uiso 1 1 calc R . . . .
C24 C 0.9400(16) 0.7911(10) 0.2074(11) 0.099(5) Uani 1 1 d . U . . .
C25 C 0.9710(18) 0.7476(14) 0.2595(12) 0.121(7) Uani 1 1 d . U . . .
H25 H 1.052299 0.731863 0.265136 0.145 Uiso 1 1 calc R . . . .
C26 C 0.8881(17) 0.7257(12) 0.3044(11) 0.116(6) Uani 1 1 d . U . . .
H26 H 0.911723 0.697947 0.340366 0.139 Uiso 1 1 calc R . . . .
C27 C 0.7422(19) 0.7833(13) 0.2446(13) 0.121(7) Uani 1 1 d . U . . .
H27 H 0.660179 0.791941 0.237610 0.146 Uiso 1 1 calc R . . . .
C28 C 0.8201(17) 0.8097(13) 0.2035(12) 0.125(7) Uani 1 1 d . U . . .
H28 H 0.792683 0.843148 0.169609 0.150 Uiso 1 1 calc R . . . .
C29 C 0.695(2) 0.7195(17) 0.3435(13) 0.153(9) Uani 1 1 d . U . . .
H29A H 0.719039 0.663303 0.363789 0.184 Uiso 1 1 calc R . . . .
H29B H 0.611238 0.720110 0.333758 0.184 Uiso 1 1 calc R . . . .
C33 C 0.7919(14) 0.9026(9) 0.4246(7) 0.139(8) Uani 1 1 d . U . . .
C34 C 0.8311(12) 0.8217(10) 0.4443(6) 0.134(8) Uani 1 1 d G U . . .
H34 H 0.886190 0.807428 0.472654 0.161 Uiso 1 1 calc R . . . .
C35 C 0.7897(12) 0.7615(7) 0.4224(8) 0.137(8) Uani 1 1 d G U . . .
H35 H 0.816422 0.706132 0.435906 0.165 Uiso 1 1 calc R . . . .
C30 C 0.7091(13) 0.7823(10) 0.3809(7) 0.133(7) Uani 1 1 d G U . . .
C31 C 0.6699(11) 0.8633(11) 0.3612(6) 0.154(9) Uani 1 1 d G U . . .
H31 H 0.614796 0.877499 0.332798 0.185 Uiso 1 1 calc R . . . .
C32 C 0.7113(12) 0.9234(8) 0.3830(8) 0.135(8) Uani 1 1 d G U . . .
H32 H 0.684563 0.978797 0.369547 0.162 Uiso 1 1 calc R . . . .
N1A N 0.5353(14) 0.7655(12) 0.6006(9) 0.116(6) Uani 1 1 d . U . . .
N2A N 0.1362(13) 0.6973(11) 0.8333(9) 0.109(5) Uani 1 1 d . U . . .
N3A N 0.1258(13) 0.5487(11) 0.9216(9) 0.116(6) Uani 1 1 d . U . . .
N4A N 0.3221(13) 0.4251(9) 0.9198(9) 0.108(6) Uani 1 1 d . U . . .
N5A N 0.7791(14) 0.4529(10) 0.7125(10) 0.119(5) Uani 1 1 d . U . . .
C1A C 0.633(2) 0.7697(18) 0.5554(12) 0.149(8) Uani 1 1 d . U . . .
H1AA H 0.673653 0.821719 0.548256 0.179 Uiso 1 1 calc R . . . .
H1AB H 0.599284 0.765872 0.520541 0.179 Uiso 1 1 calc R . . . .
C2A C 0.4571(19) 0.7067(15) 0.6055(12) 0.127(7) Uani 1 1 d . U . . .
H2A H 0.457229 0.677552 0.577612 0.153 Uiso 1 1 calc R . . . .
C3A C 0.3783(15) 0.6888(12) 0.6498(10) 0.102(6) Uani 1 1 d . U . . .
H3A H 0.326927 0.644886 0.654341 0.122 Uiso 1 1 calc R . . . .
C4A C 0.3726(15) 0.7365(11) 0.6900(10) 0.098(5) Uani 1 1 d . U . . .
C5A C 0.4570(18) 0.7988(13) 0.6825(11) 0.113(7) Uani 1 1 d . U . . .
H5A H 0.458809 0.832391 0.707565 0.136 Uiso 1 1 calc R . . . .
C6A C 0.5351(19) 0.8072(17) 0.6369(13) 0.128(8) Uani 1 1 d . U . . .
H6A H 0.593555 0.846927 0.631842 0.154 Uiso 1 1 calc R . . . .
C7A C 0.2868(16) 0.7252(14) 0.7397(12) 0.116(7) Uani 1 1 d . U . . .
C8A C 0.1686(16) 0.7091(12) 0.7381(11) 0.106(6) Uani 1 1 d . U . . .
H8A H 0.136789 0.708310 0.704025 0.127 Uiso 1 1 calc R . . . .
C9A C 0.0998(16) 0.6947(12) 0.7847(11) 0.110(7) Uani 1 1 d . U . . .
H9A H 0.019761 0.681711 0.782841 0.132 Uiso 1 1 calc R . . . .
C10A C 0.2469(16) 0.7076(14) 0.8362(11) 0.124(7) Uani 1 1 d . U . . .
H10A H 0.275067 0.708960 0.870971 0.148 Uiso 1 1 calc R . . . .
C11A C 0.3260(16) 0.7168(11) 0.7913(11) 0.099(5) Uani 1 1 d . U . . .
H11A H 0.408631 0.717355 0.796081 0.119 Uiso 1 1 calc R . . . .
C12A C 0.0480(16) 0.6811(12) 0.8809(10) 0.108(6) Uani 1 1 d . U . . .
H12C H -0.029337 0.707897 0.868728 0.129 Uiso 1 1 calc R . . . .
H12D H 0.073910 0.705115 0.910116 0.129 Uiso 1 1 calc R . . . .
C13A C 0.0319(15) 0.5876(12) 0.9056(10) 0.095(6) Uani 1 1 d . U . . .
C14A C -0.0791(15) 0.5611(13) 0.9077(10) 0.109(8) Uani 1 1 d . U . . .
H14A H -0.144151 0.597597 0.894756 0.131 Uiso 1 1 calc R . . . .
C15A C -0.0945(17) 0.4752(13) 0.9302(11) 0.114(8) Uani 1 1 d . U . . .
H15A H -0.168417 0.450278 0.932163 0.137 Uiso 1 1 calc R . . . .
C16A C 0.0039(18) 0.4345(14) 0.9479(11) 0.124(9) Uani 1 1 d . U . . .
H16A H -0.000199 0.377729 0.965018 0.149 Uiso 1 1 calc R . . . .
C17A C 0.1115(16) 0.4687(13) 0.9433(10) 0.105(7) Uani 1 1 d . U . . .
C18A C 0.2241(16) 0.4185(13) 0.9654(12) 0.130(7) Uani 1 1 d . U . . .
H18C H 0.252273 0.438546 0.996015 0.156 Uiso 1 1 calc R . . . .
H18D H 0.204908 0.360444 0.980396 0.156 Uiso 1 1 calc R . . . .
C19A C 0.3405(15) 0.3695(11) 0.8933(11) 0.109(7) Uani 1 1 d . U . . .
H19A H 0.291571 0.323714 0.901740 0.130 Uiso 1 1 calc R . . . .
C20A C 0.4263(15) 0.3756(11) 0.8547(10) 0.102(6) Uani 1 1 d . U . . .
H20A H 0.432916 0.334618 0.834683 0.122 Uiso 1 1 calc R . . . .
C21A C 0.5029(15) 0.4321(12) 0.8412(10) 0.104(6) Uani 1 1 d . U . . .
C22A C 0.4815(15) 0.4944(10) 0.8691(11) 0.110(7) Uani 1 1 d . U . . .
H22A H 0.528433 0.541232 0.859760 0.133 Uiso 1 1 calc R . . . .
C23A C 0.3947(17) 0.4869(12) 0.9086(11) 0.115(7) Uani 1 1 d . U . . .
H23A H 0.384284 0.526825 0.929395 0.138 Uiso 1 1 calc R . . . .
C24A C 0.6011(15) 0.4403(12) 0.7946(12) 0.108(6) Uani 1 1 d . U . . .
C25A C 0.5846(17) 0.4233(11) 0.7460(11) 0.109(6) Uani 1 1 d . U . . .
H25A H 0.509406 0.405976 0.739800 0.131 Uiso 1 1 calc R . . . .
C26A C 0.6741(17) 0.4304(11) 0.7048(11) 0.110(6) Uani 1 1 d . U . . .
H26A H 0.659381 0.418973 0.670649 0.133 Uiso 1 1 calc R . . . .
C27A C 0.7983(17) 0.4744(12) 0.7603(12) 0.117(6) Uani 1 1 d . U . . .
H27A H 0.873017 0.494159 0.764879 0.140 Uiso 1 1 calc R . . . .
C28A C 0.7110(16) 0.4677(12) 0.8013(12) 0.119(7) Uani 1 1 d . U . . .
H28A H 0.725385 0.481759 0.834714 0.143 Uiso 1 1 calc R . . . .
C29A C 0.8694(16) 0.4729(13) 0.6678(11) 0.113(6) Uani 1 1 d . U . . .
H29C H 0.877010 0.429766 0.647308 0.135 Uiso 1 1 calc R . . . .
H29D H 0.947105 0.476673 0.682858 0.135 Uiso 1 1 calc R . . . .
C30A C 0.8317(18) 0.5575(15) 0.6275(13) 0.125(7) Uani 1 1 d . U . . .
C31A C 0.852(2) 0.6212(16) 0.6462(12) 0.132(8) Uani 1 1 d . U . . .
H31A H 0.903204 0.617362 0.675506 0.159 Uiso 1 1 calc R . . . .
C32A C 0.794(2) 0.6948(17) 0.6201(13) 0.141(8) Uani 1 1 d . U . . .
H32A H 0.804289 0.743315 0.631286 0.169 Uiso 1 1 calc R . . . .
C33A C 0.7201(18) 0.6957(18) 0.5771(14) 0.139(8) Uani 1 1 d . U . . .
C34A C 0.714(2) 0.624(2) 0.5585(15) 0.156(9) Uani 1 1 d . U . . .
H34A H 0.668721 0.624874 0.527668 0.187 Uiso 1 1 calc R . . . .
C35A C 0.774(2) 0.5534(18) 0.5850(13) 0.136(8) Uani 1 1 d . U . . .
H35A H 0.773482 0.504503 0.573027 0.163 Uiso 1 1 calc R . . . .
P1 P 0.6353(5) 0.1910(4) 0.7599(4) 0.135(3) Uani 1 1 d . U . . .
F1 F 0.5298(10) 0.1309(7) 0.7714(8) 0.154(6) Uani 1 1 d . U . . .
F2 F 0.7379(8) 0.2523(7) 0.7494(7) 0.150(6) Uani 1 1 d . U . . .
F3 F 0.5877(15) 0.2238(8) 0.8145(9) 0.169(5) Uani 1 1 d . U . . .
F4 F 0.7166(11) 0.1208(8) 0.7987(8) 0.156(5) Uani 1 1 d . U . . .
F5 F 0.6798(15) 0.1588(8) 0.7084(9) 0.167(5) Uani 1 1 d . U . . .
F6 F 0.5526(11) 0.2592(7) 0.7210(8) 0.151(5) Uani 1 1 d . U . . .
P2 P 0.0946(4) 0.1750(3) 1.0053(3) 0.116(2) Uani 1 1 d . U . . .
F7 F 0.1084(12) 0.0923(8) 0.9797(7) 0.150(5) Uani 1 1 d . U . . .
F8 F 0.0873(10) 0.2565(7) 1.0303(7) 0.133(4) Uani 1 1 d . U . . .
F9 F -0.0403(10) 0.1904(7) 0.9916(7) 0.139(5) Uani 1 1 d . U . . .
F10 F 0.0599(9) 0.1217(6) 1.0658(6) 0.116(4) Uani 1 1 d . U . . .
F11 F 0.2305(9) 0.1615(8) 1.0189(7) 0.128(4) Uani 1 1 d . U . . .
F12 F 0.1307(10) 0.2328(7) 0.9446(7) 0.130(4) Uani 1 1 d . U . . .
P3 P 0.1771(5) 0.4660(4) 0.7540(4) 0.134(3) Uani 1 1 d . U . . .
F13 F 0.0734(12) 0.4086(7) 0.7747(8) 0.153(6) Uani 1 1 d . U . . .
F14 F 0.2803(13) 0.5223(9) 0.7288(10) 0.203(8) Uani 1 1 d . U . . .
F15 F 0.0771(11) 0.5419(8) 0.7421(8) 0.156(6) Uani 1 1 d . U . . .
F16 F 0.1949(15) 0.4844(10) 0.8093(9) 0.174(5) Uani 1 1 d . U . . .
F17 F 0.2728(11) 0.3916(9) 0.7620(8) 0.158(6) Uani 1 1 d . U . . .
F18 F 0.1612(14) 0.4446(9) 0.6946(8) 0.160(5) Uani 1 1 d . U . . .
P4 P 0.5066(15) 0.5353(10) 0.4727(9) 0.221(12) Uani 0.5 1 d D U P . .
F19 F 0.539(2) 0.4587(19) 0.4472(17) 0.26(2) Uani 0.5 1 d D U P . .
F20 F 0.476(3) 0.6119(19) 0.4980(18) 0.26(2) Uani 0.5 1 d D U P . .
F21 F 0.386(2) 0.495(2) 0.5008(16) 0.245(18) Uani 0.5 1 d D U P . .
F22 F 0.575(3) 0.490(2) 0.5269(13) 0.218(17) Uani 0.5 1 d D U P . .
F23 F 0.627(2) 0.5751(18) 0.4443(13) 0.240(16) Uani 0.5 1 d D U P . .
F24 F 0.439(3) 0.5803(19) 0.4182(13) 0.30(2) Uani 0.5 1 d D U P . .
P5 P 0.1199(8) 0.7874(5) 0.5547(5) 0.206(5) Uani 1 1 d D U . . .
F25 F 0.0260(15) 0.7443(10) 0.5305(8) 0.264(11) Uani 1 1 d D U . . .
F26 F 0.2128(12) 0.8311(8) 0.5791(8) 0.206(8) Uani 1 1 d D U . . .
F27 F 0.0429(14) 0.8688(8) 0.5395(11) 0.232(10) Uani 1 1 d D U . . .
F28 F 0.066(2) 0.7512(16) 0.6143(7) 0.314(13) Uani 1 1 d D U . . .
F29 F 0.2064(18) 0.7107(12) 0.5607(13) 0.408(18) Uani 1 1 d D U . . .
F30 F 0.176(2) 0.8223(18) 0.4952(7) 0.396(17) Uani 1 1 d D U . . .
P6 P 0.5859(9) 1.0342(8) 0.5413(7) 0.132(5) Uani 0.5 1 d D U P . .
F31 F 0.4644(19) 0.997(2) 0.5419(14) 0.151(10) Uani 0.5 1 d D U P . .
F32 F 0.7071(17) 1.0750(14) 0.5361(11) 0.158(10) Uani 0.5 1 d D U P . .
F33 F 0.529(2) 1.1196(12) 0.5398(11) 0.144(8) Uani 0.5 1 d D U P . .
F34 F 0.591(2) 1.0123(13) 0.6042(9) 0.141(8) Uani 0.5 1 d D U P . .
F35 F 0.663(2) 0.9558(13) 0.5420(13) 0.190(12) Uani 0.5 1 d D U P . .
F36 F 0.589(2) 1.0547(18) 0.4778(9) 0.157(9) Uani 0.5 1 d D U P . .
P7 P 0.7135(4) 0.7096(4) 0.7846(4) 0.125(2) Uani 1 1 d . U . . .
F37 F 0.6321(10) 0.6677(7) 0.7518(7) 0.141(5) Uani 1 1 d . U . . .
F38 F 0.7978(8) 0.7479(6) 0.8185(6) 0.122(4) Uani 1 1 d . U . . .
F39 F 0.6071(8) 0.7668(7) 0.7955(6) 0.131(5) Uani 1 1 d . U . . .
F40 F 0.6747(9) 0.6447(6) 0.8405(7) 0.126(4) Uani 1 1 d . U . . .
F41 F 0.8230(8) 0.6489(7) 0.7738(6) 0.125(4) Uani 1 1 d . U . . .
F42 F 0.7549(10) 0.7721(7) 0.7303(7) 0.141(4) Uani 1 1 d . U . . .
P8 P 0.2220(4) 0.9490(3) 0.7867(4) 0.120(2) Uani 1 1 d . U . . .
F43 F 0.1260(7) 0.8794(6) 0.8026(6) 0.117(4) Uani 1 1 d . U . . .
F44 F 0.3208(9) 1.0175(7) 0.7704(7) 0.143(5) Uani 1 1 d . U . . .
F45 F 0.1905(9) 0.9752(6) 0.8450(7) 0.127(4) Uani 1 1 d . U . . .
F46 F 0.3215(7) 0.8883(6) 0.8158(6) 0.124(4) Uani 1 1 d . U . . .
F47 F 0.2564(9) 0.9245(7) 0.7277(7) 0.129(4) Uani 1 1 d . U . . .
F48 F 0.1216(8) 1.0151(7) 0.7559(6) 0.124(4) Uani 1 1 d . U . . .
P9 P 0.4125(5) 0.6780(4) 0.9844(4) 0.131(3) Uani 1 1 d . U . . .
F49 F 0.2761(12) 0.6762(10) 0.9784(7) 0.168(6) Uani 1 1 d . U . . .
F50 F 0.5473(11) 0.6817(12) 0.9921(7) 0.169(6) Uani 1 1 d . U . . .
F51 F 0.3829(10) 0.6883(7) 1.0473(7) 0.131(4) Uani 1 1 d . U . . .
F52 F 0.422(2) 0.5803(9) 1.0119(9) 0.205(8) Uani 1 1 d . U . . .
F53 F 0.4400(12) 0.6680(9) 0.9213(8) 0.153(5) Uani 1 1 d . U . . .
F54 F 0.4000(13) 0.7746(7) 0.9627(7) 0.146(5) 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
N1 C1 1.49(3) . ?
N1 C2 1.35(3) . ?
N1 C6 1.32(3) . ?
N2 C9 1.27(3) . ?
N2 C10 1.38(2) . ?
N2 C12 1.53(3) . ?
N3 C13 1.30(2) . ?
N3 C17 1.38(3) . ?
N4 C18 1.52(3) . ?
N4 C19 1.37(3) . ?
N4 C23 1.38(3) . ?
N5 C26 1.37(3) . ?
N5 C27 1.29(3) . ?
N5 C29 1.44(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C33 1.55(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.46(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.33(3) . ?
C4 C5 1.41(3) . ?
C4 C7 1.52(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.40(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.35(2) . ?
C7 C11 1.33(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.41(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.39(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.49(3) . ?
C13 C14 1.39(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.41(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.40(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.33(3) . ?
C17 C18 1.56(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19 0.9500 . ?
C19 C20 1.36(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.47(3) . ?
C21 C22 1.36(3) . ?
C21 C24 1.37(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.38(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.38(3) . ?
C24 C28 1.38(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.40(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.31(3) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.61(3) . ?
C33 C34 1.3900 . ?
C33 C32 1.3900 . ?
C34 H34 0.9500 . ?
C34 C35 1.3900 . ?
C35 H35 0.9500 . ?
C35 C30 1.3900 . ?
C30 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C32 1.3900 . ?
C32 H32 0.9500 . ?
N1A C1A 1.51(3) . ?
N1A C2A 1.35(3) . ?
N1A C6A 1.28(3) . ?
N2A C9A 1.32(3) . ?
N2A C10A 1.28(2) . ?
N2A C12A 1.48(3) . ?
N3A C13A 1.25(3) . ?
N3A C17A 1.34(3) . ?
N4A C18A 1.52(3) . ?
N4A C19A 1.28(3) . ?
N4A C23A 1.33(2) . ?
N5A C26A 1.31(2) . ?
N5A C27A 1.37(3) . ?
N5A C29A 1.45(3) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C33A 1.56(3) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.35(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.44(3) . ?
C4A C5A 1.43(2) . ?
C4A C7A 1.50(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.37(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.38(2) . ?
C7A C11A 1.36(3) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.33(3) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
C10A C11A 1.37(3) . ?
C11A H11A 0.9500 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C12A C13A 1.56(3) . ?
C13A C14A 1.35(2) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.44(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.31(3) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.36(2) . ?
C17A C18A 1.54(3) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A H19A 0.9500 . ?
C19A C20A 1.31(3) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.29(2) . ?
C21A C22A 1.41(3) . ?
C21A C24A 1.53(3) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.33(3) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.35(3) . ?
C24A C28A 1.39(2) . ?
C25A H25A 0.9500 . ?
C25A C26A 1.38(3) . ?
C26A H26A 0.9500 . ?
C27A H27A 0.9500 . ?
C27A C28A 1.36(3) . ?
C28A H28A 0.9500 . ?
C29A H29C 0.9900 . ?
C29A H29D 0.9900 . ?
C29A C30A 1.58(3) . ?
C30A C31A 1.32(3) . ?
C30A C35A 1.30(4) . ?
C31A H31A 0.9500 . ?
C31A C32A 1.40(3) . ?
C32A H32A 0.9500 . ?
C32A C33A 1.40(4) . ?
C33A C34A 1.41(4) . ?
C34A H34A 0.9500 . ?
C34A C35A 1.38(4) . ?
C35A H35A 0.9500 . ?
P1 F1 1.577(11) . ?
P1 F2 1.566(10) . ?
P1 F3 1.65(2) . ?
P1 F4 1.611(16) . ?
P1 F5 1.56(2) . ?
P1 F6 1.605(15) . ?
P2 F7 1.677(15) . ?
P2 F8 1.651(15) . ?
P2 F9 1.576(12) . ?
P2 F10 1.585(15) . ?
P2 F11 1.584(12) . ?
P2 F12 1.620(16) . ?
P3 F13 1.543(12) . ?
P3 F14 1.545(14) . ?
P3 F15 1.641(14) . ?
P3 F16 1.52(2) . ?
P3 F17 1.591(15) . ?
P3 F18 1.64(2) . ?
P4 P4 1.57(4) 2_666 ?
P4 F19 1.597(15) . ?
P4 F19 2.06(5) 2_666 ?
P4 F20 1.595(15) . ?
P4 F21 1.594(15) . ?
P4 F21 1.43(4) 2_666 ?
P4 F22 1.598(15) . ?
P4 F22 1.03(4) 2_666 ?
P4 F23 1.596(15) . ?
P4 F24 1.597(15) . ?
F19 F20 1.58(4) 2_666 ?
F19 F22 1.69(6) 2_666 ?
F21 F22 0.79(5) 2_666 ?
F21 F23 1.58(4) 2_666 ?
F22 F24 1.57(4) 2_666 ?
P5 F25 1.558(10) . ?
P5 F26 1.559(10) . ?
P5 F27 1.561(10) . ?
P5 F28 1.555(11) . ?
P5 F29 1.560(10) . ?
P5 F30 1.559(11) . ?
P6 F31 1.544(16) . ?
P6 F32 1.551(15) . ?
P6 F33 1.539(16) . ?
P6 F34 1.522(16) . ?
P6 F35 1.539(16) . ?
P6 F36 1.533(17) . ?
F31 F36 1.30(3) 2_676 ?
P7 F37 1.580(13) . ?
P7 F38 1.585(13) . ?
P7 F39 1.552(14) . ?
P7 F40 1.591(16) . ?
P7 F41 1.613(13) . ?
P7 F42 1.555(16) . ?
P8 F43 1.605(9) . ?
P8 F44 1.614(9) . ?
P8 F45 1.639(17) . ?
P8 F46 1.561(12) . ?
P8 F47 1.645(17) . ?
P8 F48 1.630(12) . ?
P9 F49 1.561(14) . ?
P9 F50 1.554(14) . ?
P9 F51 1.635(18) . ?
P9 F52 1.622(17) . ?
P9 F53 1.63(2) . ?
P9 F54 1.587(15) . ?

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 N1 C1 115(2) . . ?
C6 N1 C1 122(2) . . ?
C6 N1 C2 122(2) . . ?
C9 N2 C10 127(2) . . ?
C9 N2 C12 116.0(17) . . ?
C10 N2 C12 117(2) . . ?
C13 N3 C17 121.6(17) . . ?
C19 N4 C18 120.2(19) . . ?
C19 N4 C23 122.5(19) . . ?
C23 N4 C18 116.7(19) . . ?
C26 N5 C29 111(2) . . ?
C27 N5 C26 120(2) . . ?
C27 N5 C29 129(2) . . ?
N1 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
N1 C1 C33 108(2) . . ?
H1A C1 H1B 108.4 . . ?
C33 C1 H1A 110.1 . . ?
C33 C1 H1B 110.1 . . ?
N1 C2 H2 121.8 . . ?
N1 C2 C3 116(2) . . ?
C3 C2 H2 121.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 121(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 122(2) . . ?
C3 C4 C7 121(2) . . ?
C5 C4 C7 118(2) . . ?
C4 C5 H5 122.4 . . ?
C6 C5 C4 115(2) . . ?
C6 C5 H5 122.4 . . ?
N1 C6 C5 124(2) . . ?
N1 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
C8 C7 C4 123(2) . . ?
C11 C7 C4 117.3(17) . . ?
C11 C7 C8 120(2) . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 122(2) . . ?
C9 C8 H8 119.0 . . ?
N2 C9 C8 115.1(18) . . ?
N2 C9 H9 122.4 . . ?
C8 C9 H9 122.4 . . ?
N2 C10 H10 122.1 . . ?
N2 C10 C11 116(2) . . ?
C11 C10 H10 122.1 . . ?
C7 C11 C10 120.0(17) . . ?
C7 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
N2 C12 H12A 109.3 . . ?
N2 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 N2 111.8(15) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
N3 C13 C12 119.7(18) . . ?
N3 C13 C14 119.9(19) . . ?
C14 C13 C12 120.4(15) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(17) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 121.8 . . ?
C16 C15 C14 116(2) . . ?
C16 C15 H15 121.8 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121(2) . . ?
C17 C16 H16 119.3 . . ?
N3 C17 C18 113.9(18) . . ?
C16 C17 N3 120.4(16) . . ?
C16 C17 C18 126(2) . . ?
N4 C18 C17 105.8(17) . . ?
N4 C18 H18A 110.6 . . ?
N4 C18 H18B 110.6 . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
N4 C19 H19 120.9 . . ?
C20 C19 N4 118(2) . . ?
C20 C19 H19 120.9 . . ?
C19 C20 H20 118.6 . . ?
C19 C20 C21 123(2) . . ?
C21 C20 H20 118.6 . . ?
C22 C21 C20 113(2) . . ?
C22 C21 C24 126(2) . . ?
C24 C21 C20 121(2) . . ?
C21 C22 H22 116.5 . . ?
C21 C22 C23 127(2) . . ?
C23 C22 H22 116.5 . . ?
N4 C23 H23 121.8 . . ?
C22 C23 N4 116(2) . . ?
C22 C23 H23 121.8 . . ?
C21 C24 C25 122(2) . . ?
C21 C24 C28 124(3) . . ?
C28 C24 C25 114(2) . . ?
C24 C25 H25 118.6 . . ?
C24 C25 C26 123(2) . . ?
C26 C25 H25 118.6 . . ?
N5 C26 C25 117(2) . . ?
N5 C26 H26 121.5 . . ?
C25 C26 H26 121.5 . . ?
N5 C27 H27 118.3 . . ?
N5 C27 C28 123(2) . . ?
C28 C27 H27 118.3 . . ?
C24 C28 H28 118.6 . . ?
C27 C28 C24 123(3) . . ?
C27 C28 H28 118.6 . . ?
N5 C29 H29A 110.4 . . ?
N5 C29 H29B 110.4 . . ?
N5 C29 C30 106.6(16) . . ?
H29A C29 H29B 108.6 . . ?
C30 C29 H29A 110.4 . . ?
C30 C29 H29B 110.4 . . ?
C34 C33 C1 116.6(16) . . ?
C34 C33 C32 120.0 . . ?
C32 C33 C1 122.0(16) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C30 120.0 . . ?
C30 C35 H35 120.0 . . ?
C35 C30 C29 118.4(16) . . ?
C31 C30 C29 118.8(17) . . ?
C31 C30 C35 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C2A N1A C1A 116(2) . . ?
C6A N1A C1A 123(2) . . ?
C6A N1A C2A 121(2) . . ?
C9A N2A C12A 117.2(15) . . ?
C10A N2A C9A 117(2) . . ?
C10A N2A C12A 125(2) . . ?
C13A N3A C17A 113.5(14) . . ?
C19A N4A C18A 121.1(14) . . ?
C19A N4A C23A 118.5(19) . . ?
C23A N4A C18A 120.3(18) . . ?
C26A N5A C27A 120(2) . . ?
C26A N5A C29A 122(2) . . ?
C27A N5A C29A 116.9(15) . . ?
N1A C1A H1AA 110.6 . . ?
N1A C1A H1AB 110.6 . . ?
N1A C1A C33A 106(2) . . ?
H1AA C1A H1AB 108.7 . . ?
C33A C1A H1AA 110.6 . . ?
C33A C1A H1AB 110.6 . . ?
N1A C2A H2A 119.8 . . ?
N1A C2A C3A 120(3) . . ?
C3A C2A H2A 119.8 . . ?
C2A C3A H3A 120.1 . . ?
C2A C3A C4A 119.8(18) . . ?
C4A C3A H3A 120.1 . . ?
C3A C4A C7A 125.2(15) . . ?
C5A C4A C3A 117(2) . . ?
C5A C4A C7A 117(2) . . ?
C4A C5A H5A 121.9 . . ?
C6A C5A C4A 116(2) . . ?
C6A C5A H5A 121.9 . . ?
N1A C6A C5A 125(2) . . ?
N1A C6A H6A 117.5 . . ?
C5A C6A H6A 117.5 . . ?
C8A C7A C4A 123(2) . . ?
C11A C7A C4A 120.8(17) . . ?
C11A C7A C8A 115(2) . . ?
C7A C8A H8A 120.2 . . ?
C9A C8A C7A 120(2) . . ?
C9A C8A H8A 120.2 . . ?
N2A C9A C8A 123.9(16) . . ?
N2A C9A H9A 118.0 . . ?
C8A C9A H9A 118.0 . . ?
N2A C10A H10A 118.7 . . ?
N2A C10A C11A 123(2) . . ?
C11A C10A H10A 118.7 . . ?
C7A C11A C10A 120.3(19) . . ?
C7A C11A H11A 119.8 . . ?
C10A C11A H11A 119.8 . . ?
N2A C12A H12C 109.2 . . ?
N2A C12A H12D 109.2 . . ?
N2A C12A C13A 112.0(18) . . ?
H12C C12A H12D 107.9 . . ?
C13A C12A H12C 109.2 . . ?
C13A C12A H12D 109.2 . . ?
N3A C13A C12A 113.6(13) . . ?
N3A C13A C14A 130(2) . . ?
C14A C13A C12A 117(2) . . ?
C13A C14A H14A 121.5 . . ?
C13A C14A C15A 117(2) . . ?
C15A C14A H14A 121.5 . . ?
C14A C15A H15A 123.4 . . ?
C16A C15A C14A 113.2(15) . . ?
C16A C15A H15A 123.4 . . ?
C15A C16A H16A 117.9 . . ?
C15A C16A C17A 124(2) . . ?
C17A C16A H16A 117.9 . . ?
N3A C17A C16A 122(2) . . ?
N3A C17A C18A 115.4(14) . . ?
C16A C17A C18A 122(2) . . ?
N4A C18A C17A 111(2) . . ?
N4A C18A H18C 109.4 . . ?
N4A C18A H18D 109.4 . . ?
C17A C18A H18C 109.4 . . ?
C17A C18A H18D 109.4 . . ?
H18C C18A H18D 108.0 . . ?
N4A C19A H19A 119.8 . . ?
N4A C19A C20A 120.3(14) . . ?
C20A C19A H19A 119.8 . . ?
C19A C20A H20A 116.9 . . ?
C21A C20A C19A 126(2) . . ?
C21A C20A H20A 116.9 . . ?
C20A C21A C22A 114(2) . . ?
C20A C21A C24A 126(2) . . ?
C22A C21A C24A 119.9(14) . . ?
C21A C22A H22A 120.4 . . ?
C23A C22A C21A 119.1(14) . . ?
C23A C22A H22A 120.4 . . ?
N4A C23A C22A 122(2) . . ?
N4A C23A H23A 119.1 . . ?
C22A C23A H23A 119.1 . . ?
C25A C24A C21A 122.5(16) . . ?
C25A C24A C28A 117(2) . . ?
C28A C24A C21A 120(2) . . ?
C24A C25A H25A 119.2 . . ?
C24A C25A C26A 121.7(19) . . ?
C26A C25A H25A 119.2 . . ?
N5A C26A C25A 120(2) . . ?
N5A C26A H26A 119.8 . . ?
C25A C26A H26A 119.8 . . ?
N5A C27A H27A 119.9 . . ?
C28A C27A N5A 120.3(18) . . ?
C28A C27A H27A 119.9 . . ?
C24A C28A H28A 119.9 . . ?
C27A C28A C24A 120(3) . . ?
C27A C28A H28A 119.9 . . ?
N5A C29A H29C 110.0 . . ?
N5A C29A H29D 110.0 . . ?
N5A C29A C30A 108.3(18) . . ?
H29C C29A H29D 108.4 . . ?
C30A C29A H29C 110.0 . . ?
C30A C29A H29D 110.0 . . ?
C31A C30A C29A 114(3) . . ?
C35A C30A C29A 116(2) . . ?
C35A C30A C31A 130(3) . . ?
C30A C31A H31A 122.1 . . ?
C30A C31A C32A 116(3) . . ?
C32A C31A H31A 122.1 . . ?
C31A C32A H32A 120.6 . . ?
C33A C32A C31A 119(3) . . ?
C33A C32A H32A 120.6 . . ?
C32A C33A C1A 121(3) . . ?
C32A C33A C34A 119(3) . . ?
C34A C33A C1A 119(3) . . ?
C33A C34A H34A 120.1 . . ?
C35A C34A C33A 120(3) . . ?
C35A C34A H34A 120.1 . . ?
C30A C35A C34A 116(3) . . ?
C30A C35A H35A 122.1 . . ?
C34A C35A H35A 122.1 . . ?
F1 P1 F3 89.5(9) . . ?
F1 P1 F4 89.5(7) . . ?
F1 P1 F6 89.3(7) . . ?
F2 P1 F1 178.4(11) . . ?
F2 P1 F3 89.0(9) . . ?
F2 P1 F4 91.2(7) . . ?
F2 P1 F6 90.0(7) . . ?
F4 P1 F3 89.9(10) . . ?
F5 P1 F1 89.8(9) . . ?
F5 P1 F2 91.7(9) . . ?
F5 P1 F3 179.3(9) . . ?
F5 P1 F4 89.8(10) . . ?
F5 P1 F6 89.6(10) . . ?
F6 P1 F3 90.7(10) . . ?
F6 P1 F4 178.6(8) . . ?
F8 P2 F7 177.5(7) . . ?
F9 P2 F7 92.4(8) . . ?
F9 P2 F8 89.9(8) . . ?
F9 P2 F10 91.1(7) . . ?
F9 P2 F11 178.8(7) . . ?
F9 P2 F12 89.3(7) . . ?
F10 P2 F7 92.1(7) . . ?
F10 P2 F8 88.6(8) . . ?
F10 P2 F12 177.5(8) . . ?
F11 P2 F7 88.6(7) . . ?
F11 P2 F8 89.0(7) . . ?
F11 P2 F10 89.5(8) . . ?
F11 P2 F12 90.1(7) . . ?
F12 P2 F7 90.4(8) . . ?
F12 P2 F8 88.9(7) . . ?
F13 P3 F14 175.7(14) . . ?
F13 P3 F15 87.3(7) . . ?
F13 P3 F17 92.4(8) . . ?
F13 P3 F18 84.0(9) . . ?
F14 P3 F15 93.0(8) . . ?
F14 P3 F17 87.1(8) . . ?
F14 P3 F18 91.7(12) . . ?
F16 P3 F13 96.5(12) . . ?
F16 P3 F14 87.9(11) . . ?
F16 P3 F15 88.2(9) . . ?
F16 P3 F17 95.2(10) . . ?
F16 P3 F18 178.5(10) . . ?
F17 P3 F15 176.6(12) . . ?
F17 P3 F18 83.3(9) . . ?
F18 P3 F15 93.3(9) . . ?
P4 P4 F19 81(2) 2_666 . ?
P4 P4 F19 50.1(15) 2_666 2_666 ?
P4 P4 F20 99(2) 2_666 . ?
P4 P4 F21 53.7(15) 2_666 . ?
P4 P4 F22 38.0(14) 2_666 . ?
P4 P4 F23 126.5(15) 2_666 . ?
P4 P4 F24 142.1(15) 2_666 . ?
F19 P4 F19 131.0(13) . 2_666 ?
F19 P4 F22 89.6(7) . . ?
F19 P4 F24 90.0(7) . . ?
F20 P4 F19 179.5(9) . . ?
F20 P4 F19 49.2(13) . 2_666 ?
F20 P4 F22 90.2(7) . . ?
F20 P4 F23 90.2(7) . . ?
F20 P4 F24 90.2(7) . . ?
F21 P4 P4 64.0(18) 2_666 2_666 ?
F21 P4 F19 80(2) 2_666 . ?
F21 P4 F19 79(2) 2_666 2_666 ?
F21 P4 F19 90.4(7) . . ?
F21 P4 F19 62.7(11) . 2_666 ?
F21 P4 F20 100(2) 2_666 . ?
F21 P4 F20 90.0(7) . . ?
F21 P4 F21 117.6(16) 2_666 . ?
F21 P4 F22 29.5(19) 2_666 . ?
F21 P4 F22 90.2(7) . . ?
F21 P4 F23 179.7(9) . . ?
F21 P4 F23 62.5(17) 2_666 . ?
F21 P4 F24 90.0(7) . . ?
F21 P4 F24 150(2) 2_666 . ?
F22 P4 P4 72(2) 2_666 2_666 ?
F22 P4 F19 77(3) 2_666 . ?
F22 P4 F19 87(3) 2_666 2_666 ?
F22 P4 F19 53.3(13) . 2_666 ?
F22 P4 F20 104(3) 2_666 . ?
F22 P4 F21 133(4) 2_666 2_666 ?
F22 P4 F21 25(3) 2_666 . ?
F22 P4 F22 110(2) 2_666 . ?
F22 P4 F23 155(3) 2_666 . ?
F22 P4 F24 70(3) 2_666 . ?
F23 P4 F19 89.4(7) . . ?
F23 P4 F19 117.6(11) . 2_666 ?
F23 P4 F22 90.0(7) . . ?
F23 P4 F24 89.8(7) . . ?
F24 P4 F19 127.1(13) . 2_666 ?
F24 P4 F22 179.5(9) . . ?
P4 F19 P4 49.0(13) . 2_666 ?
P4 F19 F22 36.5(13) . 2_666 ?
F20 F19 P4 50.0(15) 2_666 2_666 ?
F20 F19 P4 99(2) 2_666 . ?
F20 F19 F22 88(2) 2_666 2_666 ?
F22 F19 P4 49.3(15) 2_666 2_666 ?
F19 F20 P4 81(2) 2_666 . ?
P4 F21 P4 62.4(16) 2_666 . ?
P4 F21 F23 63.9(19) 2_666 2_666 ?
F22 F21 P4 87(3) 2_666 2_666 ?
F22 F21 P4 33(3) 2_666 . ?
F22 F21 F23 143(5) 2_666 2_666 ?
F23 F21 P4 126.3(17) 2_666 . ?
P4 F22 P4 70(2) 2_666 . ?
P4 F22 F19 77.4(16) . 2_666 ?
P4 F22 F19 67(3) 2_666 2_666 ?
P4 F22 F24 72(2) 2_666 2_666 ?
F21 F22 P4 122(5) 2_666 2_666 ?
F21 F22 P4 63(3) 2_666 . ?
F21 F22 F19 128(5) 2_666 2_666 ?
F21 F22 F24 144(5) 2_666 2_666 ?
F24 F22 P4 141.9(16) 2_666 . ?
F24 F22 F19 87(3) 2_666 2_666 ?
F21 F23 P4 53.6(15) 2_666 . ?
F22 F24 P4 38.0(14) 2_666 . ?
F25 P5 F26 179.3(9) . . ?
F25 P5 F27 89.6(6) . . ?
F25 P5 F29 90.4(7) . . ?
F26 P5 F27 89.9(6) . . ?
F26 P5 F29 90.2(9) . . ?
F28 P5 F25 90.1(7) . . ?
F28 P5 F26 89.7(6) . . ?
F28 P5 F27 99.1(16) . . ?
F28 P5 F29 89.7(8) . . ?
F28 P5 F30 178.8(12) . . ?
F29 P5 F27 171.2(16) . . ?
F30 P5 F25 90.2(7) . . ?
F30 P5 F26 90.1(7) . . ?
F30 P5 F27 82.1(15) . . ?
F30 P5 F29 89.1(8) . . ?
F31 P6 F32 175.8(19) . . ?
F33 P6 F31 93.0(16) . . ?
F33 P6 F32 86.0(12) . . ?
F34 P6 F31 94.7(17) . . ?
F34 P6 F32 89.4(12) . . ?
F34 P6 F33 92.4(12) . . ?
F34 P6 F35 87.5(12) . . ?
F34 P6 F36 176.5(14) . . ?
F35 P6 F31 96.6(17) . . ?
F35 P6 F32 84.5(12) . . ?
F35 P6 F33 170.4(15) . . ?
F36 P6 F31 87.9(17) . . ?
F36 P6 F32 88.1(12) . . ?
F36 P6 F33 89.8(12) . . ?
F36 P6 F35 89.9(12) . . ?
F36 F31 P6 143(2) 2_676 . ?
F31 F36 P6 114(2) 2_676 . ?
F37 P7 F38 177.6(7) . . ?
F37 P7 F40 89.3(7) . . ?
F37 P7 F41 89.3(7) . . ?
F38 P7 F40 89.3(8) . . ?
F38 P7 F41 88.7(6) . . ?
F39 P7 F37 90.3(7) . . ?
F39 P7 F38 91.7(7) . . ?
F39 P7 F40 89.0(7) . . ?
F39 P7 F41 179.2(8) . . ?
F39 P7 F42 92.3(8) . . ?
F40 P7 F41 90.2(7) . . ?
F42 P7 F37 91.5(9) . . ?
F42 P7 F38 89.9(7) . . ?
F42 P7 F40 178.5(8) . . ?
F42 P7 F41 88.5(8) . . ?
F43 P8 F44 178.7(8) . . ?
F43 P8 F45 91.6(7) . . ?
F43 P8 F47 89.9(7) . . ?
F43 P8 F48 90.4(5) . . ?
F44 P8 F45 89.2(7) . . ?
F44 P8 F47 89.3(8) . . ?
F44 P8 F48 90.6(6) . . ?
F45 P8 F47 178.5(6) . . ?
F46 P8 F43 91.7(6) . . ?
F46 P8 F44 87.2(6) . . ?
F46 P8 F45 88.9(8) . . ?
F46 P8 F47 91.0(8) . . ?
F46 P8 F48 177.9(5) . . ?
F48 P8 F45 90.8(7) . . ?
F48 P8 F47 89.3(8) . . ?
F49 P9 F51 88.3(9) . . ?
F49 P9 F52 91.8(10) . . ?
F49 P9 F53 90.9(9) . . ?
F49 P9 F54 87.7(9) . . ?
F50 P9 F49 177.9(12) . . ?
F50 P9 F51 89.8(9) . . ?
F50 P9 F52 89.0(11) . . ?
F50 P9 F53 91.1(9) . . ?
F50 P9 F54 91.3(9) . . ?
F52 P9 F51 86.8(10) . . ?
F52 P9 F53 93.4(10) . . ?
F53 P9 F51 179.1(8) . . ?
F54 P9 F51 88.2(9) . . ?
F54 P9 F52 175.0(13) . . ?
F54 P9 F53 91.6(9) . . ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 319.1 Ang³ [6.9%]
Total electron count / cell = 117.5
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 290.1 115.7 ?
2 0.150 0.123 0.392 7.2 0.6 ?
3 0.183 0.815 0.912 7.2 0.2 ?
4 0.817 0.185 0.088 7.2 0.3 ?
5 0.850 0.877 0.608 7.2 0.7 ?

_olex2_date_sample_data_collection 2017-09-22
_olex2_date_sample_submission    2017-08-07
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a glass fibre in Paratone oil'
_olex2_submission_original_sample_id cx1045
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.277
_oxdiff_exptl_absorpt_empirical_full_min 0.377
_vrf_PLAT082_cx1045              
;
PROBLEM: High R1 Value .................................. 0.24 Report
RESPONSE: Despite the high R factor we are confident in the structure and it's packing.
;
_vrf_PLAT084_cx1045              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.61 Report
RESPONSE: Despite the high R factor we are confident in the structure and it's packing.
;
_vrf_PLAT434_cx1045              
;
PROBLEM: Short Inter HL..HL Contact F30 .. F32 .. 2.19 Ang.
RESPONSE: These are between disordered PF6 anions and are not there at the same time
;
####################################################################### 
# 
# 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_cx1162
_database_code_depnum_ccdc_archive 'CCDC 1955710'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2018-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C34 H30 N4 S, 2(F6 P)'
_chemical_formula_sum            'C34 H30 F12 N4 P2 S'
_chemical_formula_weight         816.62
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.2660(6)
_cell_length_b                   21.7433(14)
_cell_length_c                   9.8244(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2193.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.763
_cell_measurement_theta_min      4.066
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.563
_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.6297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0975 before and 0.0540 after correction. The Ratio of minimum to maximum transmission is 0.8368. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.026
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11620
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.382
_diffrn_reflns_theta_min         4.066
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1633
_reflns_number_total             1953
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.073
_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)+(0.0909P)²+1.4114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1601
_refine_special_details          
'The enhanced rigid-bond restraint (SHELX keyword RIGU) was applied on the disordered sulfur atom. (Acta Cryst. A68 (2012) 448-451)'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 S1, S1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(S1A)=0.25*(1-FVAR(2))
 Sof(S1)=0.25*FVAR(2)
 Fixed Sof: C3(0.5) H3(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9)
;
_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
S1 S 0.1709(2) 0.30054(12) 0.0000 0.0374(8) Uani 0.443(4) 2 d S TU P A 4
S1A S 0.302(2) 0.3483(10) 0.0000 0.056(8) Uani 0.057(4) 2 d S TU P A 3
N1 N 0.1842(2) 0.36324(10) 0.3223(2) 0.0397(6) Uani 1 1 d . . . . .
C1 C 0.3902(3) 0.32334(18) 0.0716(3) 0.0587(9) Uani 1 1 d . . . B 1
H1 H 0.4646 0.3358 0.1220 0.070 Uiso 1 1 calc R . . B 1
C2 C 0.2801(3) 0.30488(12) 0.1342(3) 0.0383(6) Uani 1 1 d . . . . .
C3 C 0.1756(7) 0.2755(4) 0.0725(7) 0.0601(19) Uani 0.5 1 d . . . A 2
H3 H 0.1082 0.2565 0.1238 0.072 Uiso 0.5 1 calc R . . A 2
C4 C 0.2605(3) 0.30767(12) 0.2851(3) 0.0447(7) Uani 1 1 d . . . . .
H4A H 0.2138 0.2704 0.3160 0.054 Uiso 1 1 calc R . . . .
H4B H 0.3462 0.3088 0.3312 0.054 Uiso 1 1 calc R . . . .
C5 C 0.2450(3) 0.41929(12) 0.3273(3) 0.0398(7) Uani 1 1 d . . . . .
H5 H 0.3374 0.4211 0.3231 0.048 Uiso 1 1 calc R . . . .
C6 C 0.1760(3) 0.47214(12) 0.3380(2) 0.0363(6) Uani 1 1 d . . . . .
H6 H 0.2213 0.5102 0.3431 0.044 Uiso 1 1 calc R . . . .
C7 C 0.0374(3) 0.47225(11) 0.3419(2) 0.0324(6) Uani 1 1 d . . . . .
C8 C -0.0209(3) 0.41286(12) 0.3407(2) 0.0363(6) Uani 1 1 d . . . . .
H8 H -0.1129 0.4095 0.3470 0.044 Uiso 1 1 calc R . . . .
C9 C 0.0520(3) 0.36095(12) 0.3308(3) 0.0404(7) Uani 1 1 d . . . . .
H9 H 0.0097 0.3221 0.3297 0.048 Uiso 1 1 calc R . . . .
P1 P 0.12174(9) 0.15659(4) 0.5000 0.0364(3) Uani 1 2 d S T P . .
F1 F 0.1229(2) 0.15657(11) 0.3390(2) 0.0757(7) Uani 1 1 d . . . . .
F2 F 0.0629(2) 0.22422(11) 0.5000 0.0625(8) Uani 1 2 d S T P . .
F3 F -0.0213(2) 0.12843(11) 0.5000 0.0659(8) Uani 1 2 d S T P . .
F4 F 0.1814(2) 0.08927(11) 0.5000 0.0664(8) Uani 1 2 d S T P . .
F5 F 0.2638(2) 0.18530(10) 0.5000 0.0481(6) Uani 1 2 d S T P . .


_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
S1 C2 1.733(3) . ?
S1 C2 1.733(3) 6 ?
S1A C2 1.637(13) 6 ?
S1A C2 1.637(13) . ?
N1 C4 1.486(3) . ?
N1 C5 1.370(3) . ?
N1 C9 1.361(4) . ?
C1 C1 1.407(6) 6 ?
C1 H1 0.9500 . ?
C1 C2 1.348(4) . ?
C2 C3 1.388(7) . ?
C2 C4 1.497(4) . ?
C3 C3 1.424(14) 6 ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C6 1.354(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.424(4) . ?
C7 C7 1.430(5) 2_565 ?
C7 C8 1.423(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.357(4) . ?
C9 H9 0.9500 . ?
P1 F1 1.582(2) . ?
P1 F1 1.582(2) 6_556 ?
P1 F2 1.590(2) . ?
P1 F3 1.591(2) . ?
P1 F4 1.587(2) . ?
P1 F5 1.586(2) . ?

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 S1 C2 99.1(2) . 6 ?
C2 S1A C2 107.3(12) . 6 ?
C5 N1 C4 119.5(2) . . ?
C9 N1 C4 120.8(2) . . ?
C9 N1 C5 119.0(2) . . ?
C1 C1 H1 121.4 6 . ?
C2 C1 C1 117.14(17) . 6 ?
C2 C1 H1 121.4 . . ?
C1 C2 C4 123.5(3) . . ?
C3 C2 C4 110.4(4) . . ?
C4 C2 S1 132.0(2) . . ?
C4 C2 S1A 142.4(6) . . ?
C2 C3 C3 115.9(3) . 6 ?
C2 C3 H3 122.0 . . ?
C3 C3 H3 122.0 6 . ?
N1 C4 C2 110.3(2) . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C2 C4 H4A 109.6 . . ?
C2 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 H5 119.4 . . ?
C6 C5 N1 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C7 122.5(3) . 2_565 ?
C8 C7 C6 114.7(2) . . ?
C8 C7 C7 122.7(3) . 2_565 ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
N1 C9 H9 119.2 . . ?
C8 C9 N1 121.6(3) . . ?
C8 C9 H9 119.2 . . ?
F1 P1 F1 179.15(18) 6_556 . ?
F1 P1 F2 90.18(9) 6_556 . ?
F1 P1 F2 90.18(9) . . ?
F1 P1 F3 90.39(8) . . ?
F1 P1 F3 90.39(8) 6_556 . ?
F1 P1 F4 89.82(9) 6_556 . ?
F1 P1 F4 89.82(9) . . ?
F1 P1 F5 89.62(8) . . ?
F1 P1 F5 89.62(8) 6_556 . ?
F2 P1 F3 90.31(13) . . ?
F4 P1 F2 179.63(13) . . ?
F4 P1 F3 90.05(14) . . ?
F5 P1 F2 89.16(12) . . ?
F5 P1 F3 179.48(14) . . ?
F5 P1 F4 90.47(13) . . ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.


Total solvent accessible volume / cell = 625.1 Ang³ [28.5%]
Total electron count / cell = 157.8
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.377 0.000 -0.130 312.6 78.9 ?
2 -0.011 0.500 -0.562 312.6 78.9 ?

_olex2_date_sample_data_collection 2018-01-09
_olex2_date_sample_submission    2018-01-08
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1162
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cx1122
_database_code_depnum_ccdc_archive 'CCDC 1955709'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H28 N4 S, C12 H14 N2, 3(F6 P)'
_chemical_formula_sum            'C44 H42 F18 N6 P3 S'
_chemical_formula_weight         1121.80
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.8597(15)
_cell_length_b                   21.003(2)
_cell_length_c                   9.5902(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2993.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5573
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.666
_cell_measurement_theta_min      3.643
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.319
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.4849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1363 before and 0.0812 after correction. The Ratio of minimum to maximum transmission is 0.6443. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1142
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12833
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.662
_diffrn_reflns_theta_min         3.644
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2137
_reflns_number_total             2655
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.170
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     325
_refine_ls_R_factor_all          0.1497
_refine_ls_R_factor_gt           0.1358
_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)+(0.1469P)²+25.6386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3484
_refine_ls_wR_factor_ref         0.3577
_refine_special_details          
'Rigid bond restraints were imposed on the displacement parameters as well as restraints on similar amplitudes separated by less than 1.7 Ang globally. Distance restraints were imposed on the disordered PF6 anion. C9 was restrained esd (0.01) that its Uij components approximate to isotropic.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F9A-F7A \\sim F9A-F5A \\sim F7A-F8A \\sim F5A-F8A
 with sigma of 0.02
 P2-F9A \\sim P2-F7A \\sim P2-F5A \\sim P2-F6 \\sim P2-F4 \\sim P2-F8A
 with sigma of 0.01
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C9)=Sof(H9)=1-FVAR(1)
 Sof(S1A)=0.25*(1-FVAR(2))
 Sof(S1)=0.25*FVAR(2)
 Sof(C8)=Sof(H8)=FVAR(1)
 Sof(F5A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=0.5*(1-FVAR(3))
 Sof(F5)=Sof(F7)=FVAR(2)
 Fixed Sof: H15A(0.5) H15B(0.5) H15C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14)
6.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
S1 S 0.7683(4) 0.3587(4) 0.0000 0.0335(18) Uani 0.374(8) 2 d S TU P A 1
S1A S 0.860(2) 0.4414(13) 0.0000 0.060(4) Uani 0.126(8) 2 d S TU P A 2
N1 N 0.7142(4) 0.4244(3) 0.3235(7) 0.0544(15) Uani 1 1 d . U . . .
C1 C 0.6355(5) 0.3899(4) 0.3258(9) 0.0549(18) Uani 1 1 d . U . . .
H1 H 0.6385 0.3448 0.3250 0.066 Uiso 1 1 calc R . . . .
C2 C 0.5539(5) 0.4184(4) 0.3291(8) 0.0518(17) Uani 1 1 d . U . . .
H2 H 0.5016 0.3923 0.3292 0.062 Uiso 1 1 calc R . . . .
C3 C 0.5431(5) 0.4848(4) 0.3326(8) 0.0502(17) Uani 1 1 d . U . . .
C4 C 0.6249(5) 0.5191(4) 0.3330(9) 0.0549(18) Uani 1 1 d . U . . .
H4 H 0.6227 0.5643 0.3360 0.066 Uiso 1 1 calc R . . . .
C5 C 0.7065(6) 0.4902(4) 0.3291(9) 0.0583(19) Uani 1 1 d . U . . .
H5 H 0.7594 0.5155 0.3303 0.070 Uiso 1 1 calc R . . . .
C6 C 0.7994(5) 0.3940(4) 0.2919(10) 0.0593(18) Uani 1 1 d . U . . .
H6A H 0.7981 0.3493 0.3243 0.071 Uiso 1 1 calc R . . . .
H6B H 0.8486 0.4163 0.3418 0.071 Uiso 1 1 calc R . . . .
C7 C 0.8169(5) 0.3958(4) 0.1396(9) 0.0526(17) Uani 1 1 d . U . . .
C8 C 0.8709(8) 0.4389(5) 0.0840(13) 0.055(3) Uani 0.748(17) 1 d . U . A 1
H8 H 0.9065 0.4672 0.1381 0.066 Uiso 0.748(17) 1 calc R . . A 1
C9 C 0.763(2) 0.3487(15) 0.063(4) 0.034(4) Uani 0.252(17) 1 d . U . A 2
H9 H 0.7280 0.3184 0.1129 0.041 Uiso 0.252(17) 1 calc R . . A 2
N2 N 0.6495(6) 0.6282(5) 0.0000 0.056(2) Uani 1 2 d S TU P . .
C10 C 0.5621(7) 0.6383(6) 0.0000 0.053(2) Uani 1 2 d S TU P . .
H10 H 0.5418 0.6812 0.0000 0.063 Uiso 1 2 calc RS T P . .
C11 C 0.4991(7) 0.5916(5) 0.0000 0.051(2) Uani 1 2 d S TU P . .
H11 H 0.4365 0.6010 0.0000 0.061 Uiso 1 2 calc RS T P . .
C12 C 0.5316(6) 0.5268(5) 0.0000 0.042(2) Uani 1 2 d S TU P . .
C13 C 0.6267(7) 0.5179(5) 0.0000 0.047(2) Uani 1 2 d S TU P . .
H13 H 0.6508 0.4760 0.0000 0.056 Uiso 1 2 calc RS T P . .
C14 C 0.6832(7) 0.5686(6) 0.0000 0.052(2) Uani 1 2 d S TU P . .
H14 H 0.7465 0.5622 0.0000 0.062 Uiso 1 2 calc RS T P . .
C15 C 0.7175(9) 0.6848(7) 0.0000 0.075(4) Uani 1 2 d S TU P . .
H15A H 0.7771 0.6694 0.0282 0.113 Uiso 0.5 1 calc GR . . B -1
H15B H 0.6971 0.7175 0.0657 0.113 Uiso 0.5 1 calc GR . . B -1
H15C H 0.7211 0.7030 -0.0939 0.113 Uiso 0.5 1 calc GR . . B -1
P2 P 0.81022(18) 0.21181(13) 0.5000 0.0532(9) Uani 1 2 d DS TU P . .
F4 F 0.8659(4) 0.2767(3) 0.5000 0.0584(17) Uani 1 2 d DS TU P C .
F5 F 0.7459(5) 0.2408(4) 0.3826(9) 0.082(3) Uani 0.754(10) 1 d . U . C 1
F5A F 0.7206(12) 0.2530(12) 0.5000 0.067(5) Uani 0.246(10) 2 d DS TU P C 2
F6 F 0.7531(5) 0.1479(3) 0.5000 0.084(2) Uani 1 2 d DS TU P C .
F7 F 0.8734(5) 0.1846(4) 0.6169(11) 0.098(3) Uani 0.754(10) 1 d . U . C 1
F7A F 0.8975(13) 0.1683(12) 0.5000 0.071(5) Uani 0.246(10) 2 d DS TU P C 2
F8A F 0.8237(17) 0.2263(17) 0.3388(14) 0.066(4) Uani 0.123(5) 1 d D U . C 2
F9A F 0.8000(18) 0.2009(17) 0.6631(13) 0.070(4) Uani 0.123(5) 1 d D U . C 2
P1 P 1.0000 0.5000 0.5000 0.0443(10) Uani 1 4 d S TU P . .
F1 F 1.0210(4) 0.5740(3) 0.5000 0.078(2) Uani 1 2 d S TU P . .
F2 F 0.8940(4) 0.5148(4) 0.5000 0.068(2) Uani 1 2 d S TU P . .
F3 F 1.0000 0.5000 0.3331(9) 0.086(2) Uani 1 2 d S TU P . .


_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
S1 C7 1.709(9) 6 ?
S1 C7 1.709(9) . ?
S1A C7 1.77(2) 6 ?
S1A C7 1.77(2) . ?
N1 C1 1.377(10) . ?
N1 C5 1.386(11) . ?
N1 C6 1.450(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.352(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.405(12) . ?
C3 C3 1.430(16) 2_665 ?
C3 C4 1.414(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.357(11) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.484(13) . ?
C7 C8 1.322(14) . ?
C7 C9 1.47(3) . ?
C8 C8 1.61(3) 6 ?
C8 H8 0.9500 . ?
C9 C9 1.21(8) 6 ?
C9 H9 0.9500 . ?
N2 C10 1.317(14) . ?
N2 C14 1.346(15) . ?
N2 C15 1.560(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.357(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.444(15) . ?
C12 C12 1.466(19) 5_665 ?
C12 C13 1.426(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.356(15) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
P2 F4 1.595(6) . ?
P2 F5 1.597(7) . ?
P2 F5 1.597(7) 6_556 ?
P2 F5A 1.589(9) . ?
P2 F6 1.589(6) . ?
P2 F7 1.570(8) . ?
P2 F7 1.570(8) 6_556 ?
P2 F7A 1.586(9) . ?
P2 F8A 1.588(9) 6_556 ?
P2 F8A 1.588(9) . ?
P2 F9A 1.589(9) 6_556 ?
P2 F9A 1.589(9) . ?
F8A F9A 0.64(5) 6_556 ?
F9A F8A 0.64(5) 6_556 ?
P1 F1 1.585(7) 5_766 ?
P1 F1 1.585(7) . ?
P1 F2 1.605(6) 5_766 ?
P1 F2 1.605(6) . ?
P1 F3 1.601(8) . ?
P1 F3 1.601(8) 5_766 ?

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
C7 S1 C7 103.1(7) 6 . ?
C7 S1A C7 98.3(15) . 6 ?
C1 N1 C5 116.9(7) . . ?
C1 N1 C6 120.9(7) . . ?
C5 N1 C6 121.3(7) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 N1 122.0(8) . . ?
C2 C1 H1 119.0 . . ?
C1 C2 H2 118.6 . . ?
C1 C2 C3 122.8(8) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C3 123.1(9) . 2_665 ?
C2 C3 C4 114.1(7) . . ?
C4 C3 C3 122.9(9) . 2_665 ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.7(8) . . ?
C5 C4 H4 118.7 . . ?
N1 C5 H5 119.3 . . ?
C4 C5 N1 121.4(8) . . ?
C4 C5 H5 119.3 . . ?
N1 C6 H6A 109.6 . . ?
N1 C6 H6B 109.6 . . ?
N1 C6 C7 110.3(7) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 S1 133.3(7) . . ?
C6 C7 S1A 145.3(10) . . ?
C8 C7 S1 104.6(8) . . ?
C8 C7 C6 121.3(9) . . ?
C9 C7 S1A 100.8(17) . . ?
C9 C7 C6 112.2(17) . . ?
C7 C8 C8 113.8(7) . 6 ?
C7 C8 H8 123.1 . . ?
C8 C8 H8 123.1 6 . ?
C7 C9 H9 120.1 . . ?
C9 C9 C7 119.9(16) 6 . ?
C9 C9 H9 120.1 6 . ?
C10 N2 C14 121.1(10) . . ?
C10 N2 C15 121.0(11) . . ?
C14 N2 C15 117.8(9) . . ?
N2 C10 H10 117.8 . . ?
N2 C10 C11 124.3(12) . . ?
C11 C10 H10 117.8 . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.8(10) . . ?
C12 C11 H11 121.6 . . ?
C11 C12 C12 120.7(11) . 5_665 ?
C13 C12 C11 117.1(9) . . ?
C13 C12 C12 122.3(12) . 5_665 ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(11) . . ?
C14 C13 H13 119.6 . . ?
N2 C14 C13 120.0(10) . . ?
N2 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F4 P2 F5 89.1(3) . 6_556 ?
F4 P2 F5 89.1(3) . . ?
F5 P2 F5 89.7(7) . 6_556 ?
F5A P2 F4 88.3(11) . . ?
F5A P2 F6 90.7(11) . . ?
F6 P2 F4 179.0(4) . . ?
F6 P2 F5 90.1(3) . 6_556 ?
F6 P2 F5 90.1(3) . . ?
F7 P2 F4 90.0(3) 6_556 . ?
F7 P2 F4 90.0(3) . . ?
F7 P2 F5 89.6(5) 6_556 . ?
F7 P2 F5 89.6(5) . 6_556 ?
F7 P2 F5 178.9(5) 6_556 6_556 ?
F7 P2 F5 178.9(5) . . ?
F7 P2 F6 90.7(4) . . ?
F7 P2 F6 90.7(4) 6_556 . ?
F7 P2 F7 91.1(8) 6_556 . ?
F7A P2 F4 93.9(12) . . ?
F7A P2 F5A 177.8(15) . . ?
F7A P2 F6 87.1(12) . . ?
F7A P2 F8A 90.4(6) . 6_556 ?
F7A P2 F8A 90.4(6) . . ?
F7A P2 F9A 89.7(6) . 6_556 ?
F7A P2 F9A 89.7(6) . . ?
F8A P2 F4 76.8(15) 6_556 . ?
F8A P2 F4 76.8(15) . . ?
F8A P2 F5A 90.1(6) 6_556 . ?
F8A P2 F5A 90.1(6) . . ?
F8A P2 F6 103.2(15) 6_556 . ?
F8A P2 F6 103.2(15) . . ?
F8A P2 F8A 154(3) 6_556 . ?
F8A P2 F9A 23.2(17) . 6_556 ?
F8A P2 F9A 177(3) . . ?
F8A P2 F9A 177(3) 6_556 6_556 ?
F8A P2 F9A 23.2(17) 6_556 . ?
F9A P2 F4 100.0(16) 6_556 . ?
F9A P2 F4 100.0(16) . . ?
F9A P2 F5A 89.9(6) 6_556 . ?
F9A P2 F5A 89.9(6) . . ?
F9A P2 F6 80.0(16) 6_556 . ?
F9A P2 F6 80.0(16) . . ?
F9A P2 F9A 160(3) 6_556 . ?
F9A F8A P2 78.4(12) 6_556 . ?
F8A F9A P2 78.4(12) 6_556 . ?
F1 P1 F1 180.0 . 5_766 ?
F1 P1 F2 89.8(3) 5_766 . ?
F1 P1 F2 90.2(3) . . ?
F1 P1 F2 90.2(3) 5_766 5_766 ?
F1 P1 F2 89.8(3) . 5_766 ?
F1 P1 F3 90.000(1) . . ?
F1 P1 F3 90.000(1) 5_766 5_766 ?
F1 P1 F3 90.000(1) . 5_766 ?
F1 P1 F3 90.000(1) 5_766 . ?
F2 P1 F2 180.0 5_766 . ?
F3 P1 F2 90.000(2) . . ?
F3 P1 F2 90.000(2) 5_766 . ?
F3 P1 F2 90.000(2) . 5_766 ?
F3 P1 F2 90.000(2) 5_766 5_766 ?
F3 P1 F3 180.0 . 5_766 ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 754.1 Ang³ [25.6%]
Total electron count / cell = 197.6
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.058 0.318 -0.072 188.5 49.2 ?
2 -0.058 0.682 -0.638 188.5 49.6 ?
3 0.442 0.818 -0.008 188.5 49.5 ?
4 0.558 0.182 -0.848 188.5 49.3 ?

_olex2_date_sample_data_collection 2017-12-06
_olex2_date_sample_submission    2017-11-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1122
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cx1121
_database_code_depnum_ccdc_archive 'CCDC 1955708'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C34 H30 N4 S), 2(F6 P), 0.5(C2 H3 N)'
_chemical_formula_sum            'C18 H16.50 F12 N2.50 P2 S0.50'
_chemical_formula_weight         573.81
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.6030(13)
_cell_length_b                   13.8062(13)
_cell_length_c                   16.0216(16)
_cell_angle_alpha                101.314(6)
_cell_angle_beta                 111.832(6)
_cell_angle_gamma                107.987(6)
_cell_volume                     2486.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.024
_cell_measurement_theta_min      2.529
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0999 before and 0.0748 after correction. The Ratio of minimum to maximum transmission is 0.7513. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.015
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.521
_diffrn_reflns_theta_min         1.463
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'QuazarTM optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4014
_reflns_number_total             10194
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.945
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         10194
_refine_ls_number_restraints     411
_refine_ls_R_factor_all          0.2373
_refine_ls_R_factor_gt           0.1355
_refine_ls_restrained_S_all      1.300
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3849
_refine_ls_wR_factor_ref         0.4408
_refine_special_details          
'Distance restraints were imposed on the disordered PF6 anions and disordered rings. Rigid bond restraints were imposed on the displacement parameters as well as restraints on similar amplitudes separated by less than 1.7 Ang. on the disordered atoms.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S2-C34 \\sim S2-C31 \\sim S1_$1-C12_$1 \\sim S1_$1-C15_$1
 with sigma of 0.01
 C17-C16 \\sim C17-C12 \\sim C13-C12 \\sim C14-C13 \\sim C15-C14 \\sim C16-C15
\\sim C33_$2-C32_$2 ~
 C34_$2-C33_$2 \\sim C35_$2-C34_$2 \\sim C36_$2-C35_$2 \\sim C36_$2-C31_$2
\\sim C32_$2-C31_$2
 with sigma of 0.01
 S1-C12 \\sim S1-C15 \\sim S2_$2-C31_$2 \\sim S2_$2-C34_$2
 with sigma of 0.01
 S2-C35 \\sim S1_$3-C14_$3 \\sim S1_$3-C13_$3 \\sim S2-C36
 with sigma of 0.001
 F18-F16 \\sim F18-F21 \\sim F18-F19 \\sim F18-F17 \\sim F16-F20 \\sim F16-F21
\\sim F16-F19 \\sim F20-F21
 \\sim F20-F19 \\sim F20-F17 \\sim F21-F17 \\sim F19-F17
 with sigma of 0.04
 P4-F18 \\sim P4-F16 \\sim P4-F20 \\sim P4-F21 \\sim P4-F19 \\sim P4-F17
 with sigma of 0.02
 F18A-F16A \\sim F18A-F21A \\sim F18A-F19A \\sim F18A-F17A \\sim F16A-F20A
\\sim F16A-F21A \\sim F16A-
 F19A \\sim F20A-F21A \\sim F20A-F19A \\sim F20A-F17A \\sim F21A-F17A \\sim
F19A-F17A
 with sigma of 0.04
 P4A-F18A \\sim P4A-F16A \\sim P4A-F20A \\sim P4A-F21A \\sim P4A-F19A \\sim
P4A-F17A
 with sigma of 0.02
3. Rigid bond restraints
 C31, C32, C33, C34A, C35A, C36A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S2, C31, C34, C35, C36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1, C12, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C33 \\sim C34A \\sim C35A \\sim C36A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
S2 \\sim C31 \\sim C34 \\sim C35 \\sim C36: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
S1 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(P4A)=Sof(F16A)=Sof(F17A)=Sof(F18A)=Sof(F19A)=Sof(F20A)=Sof(F21A)=1-FVAR(1)
 Sof(P4)=Sof(F16)=Sof(F17)=Sof(F18)=Sof(F19)=Sof(F20)=Sof(F21)=FVAR(1)
 Fixed Sof: S1(0.5) C16(0.5) H16(0.5) C17(0.5) H17(0.5) S2(0.5) H19C(0.5)
 H19D(0.5) H19A(0.5) H19B(0.5) C32(0.5) H32(0.5) C33(0.5) H33(0.5) C34A(0.5)
 C35A(0.5) H35A(0.5) C36A(0.5) H36A(0.5) C34(0.5) C35(0.5) H35(0.5) C36(0.5)
 H36(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C19(H19C,H19D), C19(H19A,H19B), C30(H30A,H30B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C32(H32), C33(H33), C35A(H35A), C36A(H36A),
 C35(H35), C36(H36)
6.c Fitted hexagon refined as free rotating group:
 C31(C32,C33,C34A,C35A,C36A)
6.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C)
;
_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
S1 S 0.6550(5) 0.7568(5) 0.3396(4) 0.0804(16) Uani 0.5 1 d D U . A 1
N1 N 0.5962(8) 0.2648(7) -0.1563(6) 0.065(2) Uani 1 1 d . . . . .
N2 N 0.7393(7) 0.5487(7) 0.3129(6) 0.067(2) Uani 1 1 d . . . . .
C1 C 0.5265(12) 0.2273(8) -0.1150(8) 0.087(4) Uani 1 1 d . . . . .
H1 H 0.4562 0.1629 -0.1518 0.105 Uiso 1 1 calc R . . . .
C2 C 0.5561(11) 0.2794(9) -0.0259(8) 0.091(4) Uani 1 1 d . . . . .
H2 H 0.5067 0.2507 0.0006 0.109 Uiso 1 1 calc R . . . .
C3 C 0.6558(7) 0.3741(7) 0.0314(6) 0.051(2) Uani 1 1 d . . . . .
C4 C 0.7196(9) 0.4152(11) -0.0139(7) 0.085(4) Uani 1 1 d . . . . .
H4 H 0.7846 0.4841 0.0185 0.102 Uiso 1 1 calc R . . . .
C5 C 0.6866(9) 0.3534(11) -0.1084(7) 0.077(3) Uani 1 1 d . . . . .
H5 H 0.7340 0.3792 -0.1373 0.092 Uiso 1 1 calc R . . . .
C6 C 0.6838(8) 0.4314(8) 0.1280(7) 0.055(2) Uani 1 1 d . . . . .
C7 C 0.6409(9) 0.3848(8) 0.1812(8) 0.068(3) Uani 1 1 d . . . . .
H7 H 0.5920 0.3091 0.1552 0.082 Uiso 1 1 calc R . . . .
C8 C 0.6666(9) 0.4449(8) 0.2728(7) 0.063(3) Uani 1 1 d . . . . .
H8 H 0.6315 0.4109 0.3069 0.076 Uiso 1 1 calc R . . . .
C9 C 0.7884(9) 0.5987(9) 0.2659(8) 0.077(3) Uani 1 1 d . . . . .
H9 H 0.8415 0.6733 0.2970 0.092 Uiso 1 1 calc R . . . .
C10 C 0.7650(8) 0.5466(8) 0.1759(8) 0.073(3) Uani 1 1 d . . . . .
H10 H 0.8007 0.5841 0.1438 0.087 Uiso 1 1 calc R . . . .
C11 C 0.7562(9) 0.6134(9) 0.4094(7) 0.074(3) Uani 1 1 d . . . . .
H11A H 0.7410 0.5651 0.4456 0.089 Uiso 1 1 calc R . . . .
H11B H 0.8369 0.6706 0.4482 0.089 Uiso 1 1 calc R . . . .
C12 C 0.6718(8) 0.6624(7) 0.3875(7) 0.076(2) Uani 1 1 d D U . . .
C13 C 0.5582(7) 0.6095(7) 0.3732(7) 0.083(3) Uani 1 1 d D U . . .
H13 H 0.5350 0.5457 0.3883 0.100 Uiso 1 1 calc R . . . .
C14 C 0.4795(6) 0.6547(7) 0.3357(7) 0.082(3) Uani 1 1 d D U . . .
H14 H 0.4010 0.6227 0.3244 0.098 Uiso 1 1 calc R . . . .
C15 C 0.5211(7) 0.7478(8) 0.3158(7) 0.071(2) Uani 1 1 d D U . . .
C16 C 0.6386(10) 0.8139(15) 0.3466(15) 0.072(3) Uani 0.5 1 d D U . A 2
H16 H 0.6639 0.8844 0.3428 0.086 Uiso 0.5 1 calc R . . A 2
C17 C 0.7160(17) 0.7671(11) 0.3837(16) 0.072(4) Uani 0.5 1 d D U . A 2
H17 H 0.7973 0.8059 0.4059 0.087 Uiso 0.5 1 calc R . . A 2
C18 C 0.4442(10) 0.7866(9) 0.2612(7) 0.073(3) Uani 1 1 d . . . . .
H18A H 0.4844 0.8666 0.2808 0.088 Uiso 1 1 calc R . . . .
H18B H 0.3760 0.7700 0.2737 0.088 Uiso 1 1 calc R . . . .
S2 S 0.1064(5) 0.2016(5) 0.3330(5) 0.0908(19) Uani 0.5 1 d D U . B 1
N3 N -0.2820(7) -0.0883(7) -0.3044(6) 0.065(2) Uani 1 1 d . . . . .
N4 N -0.0613(7) 0.2740(7) 0.1557(6) 0.067(2) Uani 1 1 d . . . . .
C19 C -0.3136(9) -0.1676(8) -0.3984(7) 0.069(3) Uani 1 1 d . . . . .
H19C H -0.3980 -0.2153 -0.4290 0.082 Uiso 0.5 1 calc R . . C 2
H19D H -0.3013 -0.1262 -0.4403 0.082 Uiso 0.5 1 calc R . . C 2
H19A H -0.3982 -0.2155 -0.4328 0.082 Uiso 0.5 1 calc R . . D 1
H19B H -0.2929 -0.1292 -0.4397 0.082 Uiso 0.5 1 calc R . . D 1
C20 C -0.3151(8) -0.1172(9) -0.2433(8) 0.069(3) Uani 1 1 d . . . . .
H20 H -0.3682 -0.1905 -0.2625 0.083 Uiso 1 1 calc R . . . .
C21 C -0.2791(9) -0.0503(9) -0.1560(10) 0.085(3) Uani 1 1 d . . . . .
H21 H -0.3063 -0.0760 -0.1144 0.102 Uiso 1 1 calc R . . . .
C22 C -0.2005(8) 0.0588(8) -0.1252(7) 0.060(2) Uani 1 1 d . . . . .
C23 C -0.1633(13) 0.0913(9) -0.1900(8) 0.096(4) Uani 1 1 d . . . . .
H23 H -0.1059 0.1625 -0.1715 0.116 Uiso 1 1 calc R . . . .
C24 C -0.2134(13) 0.0156(10) -0.2826(8) 0.096(4) Uani 1 1 d . . . . .
H24 H -0.1984 0.0384 -0.3306 0.115 Uiso 1 1 calc R . . . .
C25 C -0.1548(7) 0.1348(8) -0.0291(7) 0.062(3) Uani 1 1 d . . . . .
C26 C -0.2168(10) 0.1260(10) 0.0248(8) 0.088(4) Uani 1 1 d . . . . .
H26 H -0.2951 0.0737 -0.0023 0.105 Uiso 1 1 calc R . . . .
C27 C -0.1595(12) 0.1959(11) 0.1173(10) 0.107(5) Uani 1 1 d . . . . .
H27 H -0.1973 0.1843 0.1561 0.129 Uiso 1 1 calc R . . . .
C28 C -0.0004(10) 0.2912(8) 0.1067(7) 0.070(3) Uani 1 1 d . . . . .
H28 H 0.0744 0.3503 0.1360 0.084 Uiso 1 1 calc R . . . .
C29 C -0.0466(9) 0.2233(9) 0.0143(7) 0.071(3) Uani 1 1 d . . . . .
H29 H -0.0041 0.2366 -0.0209 0.085 Uiso 1 1 calc R . . . .
C30 C -0.0031(9) 0.3399(9) 0.2620(7) 0.071(3) Uani 1 1 d . . . . .
H30A H 0.0292 0.4185 0.2722 0.086 Uiso 1 1 calc R . . . .
H30B H -0.0612 0.3249 0.2863 0.086 Uiso 1 1 calc R . . . .
C31 C 0.0889(7) 0.3117(7) 0.3135(6) 0.080(2) Uani 1 1 d D U . . .
C32 C 0.0543(8) 0.2133(7) 0.3280(10) 0.092(5) Uani 0.5 1 d DG U . B 2
H32 H -0.0255 0.1724 0.3095 0.111 Uiso 0.5 1 calc R . . B 2
C33 C 0.1366(10) 0.1747(10) 0.3695(12) 0.094(5) Uani 0.5 1 d DG U . B 2
H33 H 0.1129 0.1074 0.3794 0.113 Uiso 0.5 1 calc R . . B 2
C34A C 0.2534(9) 0.2345(11) 0.3966(13) 0.086(6) Uani 0.5 1 d G U . B 2
C35A C 0.2880(6) 0.3329(9) 0.3821(16) 0.079(5) Uani 0.5 1 d G U . B 2
H35A H 0.3678 0.3738 0.4006 0.095 Uiso 0.5 1 calc R . . B 2
C36A C 0.2058(8) 0.3715(8) 0.3405(13) 0.085(5) Uani 0.5 1 d G U . B 2
H36A H 0.2294 0.4388 0.3306 0.102 Uiso 0.5 1 calc R . . B 2
C34 C 0.2464(8) 0.2289(13) 0.3730(16) 0.066(4) Uani 0.5 1 d D U . B 1
C35 C 0.2856(8) 0.3310(11) 0.3632(19) 0.078(5) Uani 0.5 1 d D U . B 1
H35 H 0.3635 0.3680 0.3745 0.093 Uiso 0.5 1 calc R . . B 1
C36 C 0.2038(9) 0.3754(9) 0.3358(17) 0.081(5) Uani 0.5 1 d D U . B 1
H36 H 0.2258 0.4464 0.3327 0.098 Uiso 0.5 1 calc R . . B 1
P1 P 0.6016(2) 0.0871(2) 0.2011(2) 0.0698(8) Uani 1 1 d . . . . .
F1 F 0.5915(8) 0.1325(6) 0.1177(5) 0.125(3) Uani 1 1 d . . . . .
F2 F 0.6185(6) 0.0409(5) 0.2838(5) 0.0938(19) Uani 1 1 d . . . . .
F3 F 0.6511(5) 0.0096(4) 0.1576(5) 0.0871(19) Uani 1 1 d . . . . .
F4 F 0.4759(5) -0.0081(5) 0.1422(5) 0.107(2) Uani 1 1 d . . . . .
F5 F 0.5555(5) 0.1636(5) 0.2463(4) 0.0863(18) Uani 1 1 d . . . . .
F6 F 0.7353(6) 0.1796(5) 0.2661(5) 0.105(2) Uani 1 1 d . . . . .
P2 P 0.3157(3) 0.3443(3) 0.1052(2) 0.0845(10) Uani 1 1 d . . . . .
F7 F 0.4124(6) 0.4411(7) 0.1056(5) 0.113(2) Uani 1 1 d . . . . .
F8 F 0.2173(5) 0.2457(5) 0.1066(4) 0.0831(18) Uani 1 1 d . . . . .
F9 F 0.2251(7) 0.3272(7) 0.0016(5) 0.119(3) Uani 1 1 d . . . . .
F10 F 0.3526(6) 0.2559(7) 0.0597(5) 0.109(2) Uani 1 1 d . . . . .
F11 F 0.4008(5) 0.3551(5) 0.2103(4) 0.0899(19) Uani 1 1 d . . . . .
F12 F 0.2744(6) 0.4267(5) 0.1523(5) 0.0946(19) Uani 1 1 d . . . . .
P3 P 0.5000 1.0000 0.5000 0.0530(9) Uani 1 2 d S T P . .
F13 F 0.5347(5) 0.9898(5) 0.6037(4) 0.0762(16) Uani 1 1 d . . . . .
F14 F 0.3744(5) 0.9831(4) 0.4904(4) 0.0704(15) Uani 1 1 d . . . . .
F15 F 0.4573(5) 0.8711(4) 0.4545(4) 0.0739(16) Uani 1 1 d . . . . .
P4 P 0.9207(6) 0.3673(7) 0.7802(6) 0.061(2) Uani 0.654(13) 1 d D . . E 1
F16 F 0.8860(10) 0.3428(9) 0.8616(7) 0.079(3) Uani 0.654(13) 1 d D . . E 1
F17 F 0.9506(9) 0.3867(9) 0.6980(7) 0.073(3) Uani 0.654(13) 1 d D . . E 1
F18 F 1.0053(7) 0.3060(8) 0.8035(9) 0.073(3) Uani 0.654(13) 1 d D . . E 1
F19 F 1.0275(9) 0.4798(9) 0.8550(8) 0.077(4) Uani 0.654(13) 1 d D . . E 1
F20 F 0.8336(14) 0.4235(15) 0.7590(14) 0.115(8) Uani 0.654(13) 1 d D . . E 1
F21 F 0.8136(7) 0.2532(7) 0.7065(7) 0.082(4) Uani 0.654(13) 1 d D . . E 1
P4A P 0.9300(13) 0.3963(12) 0.8060(11) 0.087(7) Uani 0.346(13) 1 d D . . E 2
F16A F 0.8240(13) 0.2950(11) 0.7907(16) 0.077(7) Uani 0.346(13) 1 d D . . E 2
F17A F 1.0329(19) 0.4959(18) 0.8181(18) 0.105(12) Uani 0.346(13) 1 d D . . E 2
F18A F 1.0180(11) 0.3557(15) 0.8691(15) 0.074(6) Uani 0.346(13) 1 d D . . E 2
F19A F 0.9281(19) 0.4619(18) 0.8962(15) 0.143(11) Uani 0.346(13) 1 d D . . E 2
F20A F 0.8412(19) 0.4332(19) 0.7417(18) 0.091(12) Uani 0.346(13) 1 d D . . E 2
F21A F 0.928(2) 0.329(2) 0.7142(15) 0.131(11) Uani 0.346(13) 1 d D . . E 2
P5 P 1.0000 0.5000 0.5000 0.0501(9) Uani 1 2 d S T P . .
F22 F 0.9934(5) 0.3856(4) 0.5143(5) 0.0795(17) Uani 1 1 d . . . . .
F23 F 0.8947(5) 0.4363(5) 0.3939(4) 0.0831(18) Uani 1 1 d . . . . .
F24 F 1.0927(4) 0.5001(4) 0.4611(4) 0.0664(14) Uani 1 1 d . . . . .
N5 N 0.5849(9) 0.3778(9) 0.4507(7) 0.095(3) Uani 1 1 d . . . . .
C37 C 0.6428(9) 0.3323(9) 0.4666(8) 0.072(3) Uani 1 1 d . . . . .
C38 C 0.7097(9) 0.2685(9) 0.4773(8) 0.076(3) Uani 1 1 d . . . . .
H38A H 0.6568 0.1911 0.4515 0.114 Uiso 1 1 calc GR . . . .
H38B H 0.7627 0.2893 0.5455 0.114 Uiso 1 1 calc GR . . . .
H38C H 0.7551 0.2816 0.4422 0.114 Uiso 1 1 calc GR . . . .


_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
S1 C12 1.669(8) . ?
S1 C15 1.674(7) . ?
N1 C1 1.379(13) . ?
N1 C5 1.264(12) . ?
N1 C18 1.494(11) 2_665 ?
N2 C8 1.318(12) . ?
N2 C9 1.336(13) . ?
N2 C11 1.519(12) . ?
C1 H1 0.9500 . ?
C1 C2 1.307(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(13) . ?
C3 C4 1.389(13) . ?
C3 C6 1.435(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.404(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.354(12) . ?
C6 C10 1.465(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(13) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.344(13) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.473(12) . ?
C12 C13 1.397(7) . ?
C12 C17 1.407(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.406(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(7) . ?
C15 C16 1.402(8) . ?
C15 C18 1.413(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.408(8) . ?
C17 H17 0.9500 . ?
C18 N1 1.494(11) 2_665 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
S2 C31 1.679(8) . ?
S2 C34 1.655(8) . ?
N3 C19 1.494(12) . ?
N3 C20 1.300(13) . ?
N3 C24 1.336(13) . ?
N4 C27 1.251(13) . ?
N4 C28 1.340(12) . ?
N4 C30 1.517(12) . ?
C19 H19C 0.9900 . ?
C19 H19D 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C34A 1.41(8) 2 ?
C19 C34 1.433(16) 2 ?
C20 H20 0.9500 . ?
C20 C21 1.324(14) . ?
C21 H21 0.9500 . ?
C21 C22 1.406(14) . ?
C22 C23 1.403(14) . ?
C22 C25 1.452(13) . ?
C23 H23 0.9500 . ?
C23 C24 1.400(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.412(14) . ?
C25 C29 1.392(13) . ?
C26 H26 0.9500 . ?
C26 C27 1.360(15) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.365(13) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.434(12) . ?
C31 C32 1.3900 . ?
C31 C36A 1.3900 . ?
C31 C36 1.398(8) . ?
C32 H32 0.9500 . ?
C32 C33 1.3900 . ?
C33 H33 0.9500 . ?
C33 C34A 1.3900 . ?
C34A C19 1.409(14) 2 ?
C34A C35A 1.3900 . ?
C35A H35A 0.9500 . ?
C35A C36A 1.3900 . ?
C36A H36A 0.9500 . ?
C34 C19 1.433(16) 2 ?
C34 C35 1.407(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.403(8) . ?
C36 H36 0.9500 . ?
P1 F1 1.563(8) . ?
P1 F2 1.552(7) . ?
P1 F3 1.609(6) . ?
P1 F4 1.571(6) . ?
P1 F5 1.574(7) . ?
P1 F6 1.630(7) . ?
P2 F7 1.555(8) . ?
P2 F8 1.599(7) . ?
P2 F9 1.572(7) . ?
P2 F10 1.604(8) . ?
P2 F11 1.596(7) . ?
P2 F12 1.598(7) . ?
P3 F13 1.598(5) . ?
P3 F13 1.598(5) 2_676 ?
P3 F14 1.594(5) . ?
P3 F14 1.594(5) 2_676 ?
P3 F15 1.604(5) . ?
P3 F15 1.604(5) 2_676 ?
P4 F16 1.604(10) . ?
P4 F17 1.563(10) . ?
P4 F18 1.608(9) . ?
P4 F19 1.594(10) . ?
P4 F20 1.579(11) . ?
P4 F21 1.603(10) . ?
P4A F16A 1.566(15) . ?
P4A F17A 1.546(15) . ?
P4A F18A 1.582(15) . ?
P4A F19A 1.563(16) . ?
P4A F20A 1.562(15) . ?
P4A F21A 1.566(16) . ?
P5 F22 1.620(6) 2_766 ?
P5 F22 1.620(6) . ?
P5 F23 1.593(5) . ?
P5 F23 1.593(5) 2_766 ?
P5 F24 1.601(5) . ?
P5 F24 1.601(5) 2_766 ?
N5 C37 1.139(13) . ?
C37 C38 1.440(15) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C15 106.6(5) . . ?
C1 N1 C18 120.7(9) . 2_665 ?
C5 N1 C1 119.1(8) . . ?
C5 N1 C18 119.2(9) . 2_665 ?
C8 N2 C9 120.9(9) . . ?
C8 N2 C11 118.5(9) . . ?
C9 N2 C11 120.3(9) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 N1 120.7(10) . . ?
C2 C1 H1 119.6 . . ?
C1 C2 H2 118.5 . . ?
C1 C2 C3 123.0(10) . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C4 115.3(9) . . ?
C2 C3 C6 121.7(8) . . ?
C4 C3 C6 122.8(8) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(10) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.4(9) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C3 C6 C10 120.4(8) . . ?
C7 C6 C3 123.9(9) . . ?
C7 C6 C10 115.8(9) . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.6(9) . . ?
C8 C7 H7 119.2 . . ?
N2 C8 C7 120.5(9) . . ?
N2 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
N2 C9 H9 119.0 . . ?
N2 C9 C10 122.0(10) . . ?
C10 C9 H9 119.0 . . ?
C6 C10 H10 120.4 . . ?
C9 C10 C6 119.1(9) . . ?
C9 C10 H10 120.4 . . ?
N2 C11 H11A 110.6 . . ?
N2 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C12 C11 N2 105.9(8) . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
C11 C12 S1 135.6(8) . . ?
C13 C12 S1 98.9(5) . . ?
C13 C12 C11 122.5(8) . . ?
C13 C12 C17 123.0(10) . . ?
C17 C12 C11 114.4(11) . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C14 117.2(4) . . ?
C14 C13 H13 121.4 . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.4(4) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 S1 99.2(5) . . ?
C14 C15 C16 126.0(10) . . ?
C14 C15 C18 121.1(8) . . ?
C16 C15 C18 112.8(11) . . ?
C18 C15 S1 136.3(8) . . ?
C15 C16 H16 122.7 . . ?
C15 C16 C17 114.5(15) . . ?
C17 C16 H16 122.7 . . ?
C12 C17 C16 119.4(15) . . ?
C12 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N1 C18 H18A 109.5 2_665 . ?
N1 C18 H18B 109.5 2_665 . ?
C15 C18 N1 110.8(8) . 2_665 ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C34 S2 C31 107.5(6) . . ?
C20 N3 C19 122.8(9) . . ?
C20 N3 C24 119.9(9) . . ?
C24 N3 C19 117.3(9) . . ?
C27 N4 C28 120.3(9) . . ?
C27 N4 C30 120.1(9) . . ?
C28 N4 C30 119.1(8) . . ?
N3 C19 H19C 108.0 . . ?
N3 C19 H19D 108.0 . . ?
N3 C19 H19A 110.9 . . ?
N3 C19 H19B 110.9 . . ?
H19C C19 H19D 107.2 . . ?
H19A C19 H19B 108.9 . . ?
C34A C19 N3 117.3(12) 2 . ?
C34A C19 H19C 108.0 2 . ?
C34A C19 H19D 108.0 2 . ?
C34 C19 N3 104.3(11) 2 . ?
C34 C19 H19A 110.9 2 . ?
C34 C19 H19B 110.9 2 . ?
N3 C20 H20 118.1 . . ?
N3 C20 C21 123.8(11) . . ?
C21 C20 H20 118.1 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.7(11) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C25 122.2(10) . . ?
C23 C22 C21 117.3(10) . . ?
C23 C22 C25 120.5(9) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 C22 117.9(11) . . ?
C24 C23 H23 121.1 . . ?
N3 C24 C23 120.8(10) . . ?
N3 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C22 123.0(9) . . ?
C29 C25 C22 121.0(9) . . ?
C29 C25 C26 116.0(9) . . ?
C25 C26 H26 121.5 . . ?
C27 C26 C25 117.0(10) . . ?
C27 C26 H26 121.5 . . ?
N4 C27 C26 125.6(11) . . ?
N4 C27 H27 117.2 . . ?
C26 C27 H27 117.2 . . ?
N4 C28 H28 120.3 . . ?
N4 C28 C29 119.5(10) . . ?
C29 C28 H28 120.3 . . ?
C25 C29 H29 119.4 . . ?
C28 C29 C25 121.1(10) . . ?
C28 C29 H29 119.4 . . ?
N4 C30 H30A 109.7 . . ?
N4 C30 H30B 109.7 . . ?
H30A C30 H30B 108.2 . . ?
C31 C30 N4 109.7(8) . . ?
C31 C30 H30A 109.7 . . ?
C31 C30 H30B 109.7 . . ?
C30 C31 S2 138.9(8) . . ?
C32 C31 C30 116.0(7) . . ?
C32 C31 C36A 120.0 . . ?
C36A C31 C30 123.7(7) . . ?
C36 C31 S2 98.5(5) . . ?
C36 C31 C30 119.8(9) . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34A 120.0 . . ?
C34A C33 H33 120.0 . . ?
C33 C34A C19 111.6(7) . 2 ?
C33 C34A C35A 120.0 . . ?
C35A C34A C19 123.1(7) . 2 ?
C34A C35A H35A 120.0 . . ?
C34A C35A C36A 120.0 . . ?
C36A C35A H35A 120.0 . . ?
C31 C36A H36A 120.0 . . ?
C35A C36A C31 120.0 . . ?
C35A C36A H36A 120.0 . . ?
C19 C34 S2 133.9(10) 2 . ?
C35 C34 S2 99.2(6) . . ?
C35 C34 C19 126.4(9) . 2 ?
C34 C35 H35 121.7 . . ?
C36 C35 C34 116.7(4) . . ?
C36 C35 H35 121.7 . . ?
C31 C36 C35 117.8(4) . . ?
C31 C36 H36 121.1 . . ?
C35 C36 H36 121.1 . . ?
F1 P1 F3 87.8(4) . . ?
F1 P1 F4 94.2(5) . . ?
F1 P1 F5 93.3(4) . . ?
F1 P1 F6 89.4(4) . . ?
F2 P1 F1 176.3(5) . . ?
F2 P1 F3 89.1(4) . . ?
F2 P1 F4 87.7(4) . . ?
F2 P1 F5 89.9(4) . . ?
F2 P1 F6 88.5(4) . . ?
F3 P1 F6 88.4(3) . . ?
F4 P1 F3 89.1(3) . . ?
F4 P1 F5 91.7(3) . . ?
F4 P1 F6 175.6(4) . . ?
F5 P1 F3 178.6(4) . . ?
F5 P1 F6 90.6(3) . . ?
F7 P2 F8 179.1(4) . . ?
F7 P2 F9 92.2(5) . . ?
F7 P2 F10 93.2(4) . . ?
F7 P2 F11 91.7(4) . . ?
F7 P2 F12 90.3(4) . . ?
F8 P2 F10 87.2(4) . . ?
F9 P2 F8 88.6(4) . . ?
F9 P2 F10 90.1(4) . . ?
F9 P2 F11 176.1(5) . . ?
F9 P2 F12 90.8(4) . . ?
F11 P2 F8 87.4(4) . . ?
F11 P2 F10 89.7(4) . . ?
F11 P2 F12 89.1(4) . . ?
F12 P2 F8 89.3(3) . . ?
F12 P2 F10 176.4(4) . . ?
F13 P3 F13 180.0(4) 2_676 . ?
F13 P3 F15 91.0(3) 2_676 . ?
F13 P3 F15 89.0(3) 2_676 2_676 ?
F13 P3 F15 91.0(3) . 2_676 ?
F13 P3 F15 89.0(3) . . ?
F14 P3 F13 88.1(3) . . ?
F14 P3 F13 88.1(3) 2_676 2_676 ?
F14 P3 F13 91.9(3) . 2_676 ?
F14 P3 F13 91.9(3) 2_676 . ?
F14 P3 F14 180.0 . 2_676 ?
F14 P3 F15 91.0(3) . . ?
F14 P3 F15 89.0(3) . 2_676 ?
F14 P3 F15 91.0(3) 2_676 2_676 ?
F14 P3 F15 89.0(3) 2_676 . ?
F15 P3 F15 180.0(5) . 2_676 ?
F16 P4 F18 90.6(6) . . ?
F16 P4 F21 87.3(6) . . ?
F17 P4 F16 177.7(9) . . ?
F17 P4 F18 89.3(6) . . ?
F17 P4 F19 90.4(7) . . ?
F17 P4 F20 93.1(8) . . ?
F17 P4 F21 90.5(7) . . ?
F19 P4 F16 91.9(9) . . ?
F19 P4 F18 90.0(6) . . ?
F19 P4 F21 179.0(8) . . ?
F20 P4 F16 86.9(8) . . ?
F20 P4 F18 177.1(8) . . ?
F20 P4 F19 91.6(8) . . ?
F20 P4 F21 88.9(8) . . ?
F21 P4 F18 89.6(6) . . ?
F16A P4A F18A 90.5(10) . . ?
F17A P4A F16A 178.4(14) . . ?
F17A P4A F18A 90.7(10) . . ?
F17A P4A F19A 91.6(11) . . ?
F17A P4A F20A 90.3(12) . . ?
F17A P4A F21A 89.7(12) . . ?
F19A P4A F16A 89.4(11) . . ?
F19A P4A F18A 91.6(12) . . ?
F19A P4A F21A 178.4(13) . . ?
F20A P4A F16A 88.5(11) . . ?
F20A P4A F18A 178.5(14) . . ?
F20A P4A F19A 89.4(12) . . ?
F20A P4A F21A 89.6(12) . . ?
F21A P4A F16A 89.2(12) . . ?
F21A P4A F18A 89.3(11) . . ?
F22 P5 F22 180.0 . 2_766 ?
F23 P5 F22 90.4(3) 2_766 2_766 ?
F23 P5 F22 90.4(3) . . ?
F23 P5 F22 89.6(3) 2_766 . ?
F23 P5 F22 89.6(3) . 2_766 ?
F23 P5 F23 180.0(5) 2_766 . ?
F23 P5 F24 88.9(3) 2_766 . ?
F23 P5 F24 91.1(3) 2_766 2_766 ?
F23 P5 F24 88.9(3) . 2_766 ?
F23 P5 F24 91.1(3) . . ?
F24 P5 F22 90.8(3) . 2_766 ?
F24 P5 F22 89.2(3) 2_766 2_766 ?
F24 P5 F22 89.2(3) . . ?
F24 P5 F22 90.8(3) 2_766 . ?
F24 P5 F24 180.0 . 2_766 ?
N5 C37 C38 174.7(12) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 348.6 Ang³ [14.5%]
Total electron count / cell = 80.0
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.415 348.6 80.0 ?

_olex2_date_sample_data_collection 2017-11-27
_olex2_date_sample_submission    2017-11-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1121
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cx1123
_database_code_depnum_ccdc_archive 'CCDC 1955711'
loop_
_audit_author_name
_audit_author_address
'Charlotte L Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C35 H31 N5, (C12 H14 N2), 3(F6 P)'
_chemical_formula_sum            'C47 H45 F18 N7 P3'
_chemical_formula_weight         1142.81
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.1183(9)
_cell_length_b                   21.8905(11)
_cell_length_c                   9.5412(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2948.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.266
_cell_measurement_theta_min      3.725
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.676
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0733 before and 0.0457 after correction. The Ratio of minimum to maximum transmission is 0.8748. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1166
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.102
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10929
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.062
_diffrn_reflns_theta_min         3.725
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2067
_reflns_number_total             2676
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.116
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.821
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.1250
_refine_ls_restrained_S_all      1.821
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3812
_refine_ls_wR_factor_ref         0.4081
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: N2(0.25) H6AA(0.5) H6AB(0.5) H6BC(0.5) H6BD(0.5) C7(0.5) C8(0.5)
 H8(0.5) C9(0.25) H9(0.25) C10(0.5) C11(0.5) H11(0.5) C12(0.5) H12(0.5)
 H18A(0.5) H18B(0.5) H18C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6AA,H6AB), C6(H6BC,H6BD)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
N1 N 0.2916(3) 0.5875(3) 0.1893(6) 0.114(2) Uani 1 1 d . . . . .
N2 N 0.2007(9) 0.6271(5) 0.5000 0.084(3) Uani 0.5 2 d S T P A 2
C1 C 0.2870(4) 0.5249(3) 0.1842(7) 0.111(2) Uani 1 1 d . . . . .
H1 H 0.2269 0.5056 0.1890 0.133 Uiso 1 1 calc R . . . .
C2 C 0.3657(4) 0.4899(3) 0.1724(5) 0.0862(16) Uani 1 1 d . . . . .
H2 H 0.3594 0.4468 0.1661 0.103 Uiso 1 1 calc R . . . .
C3 C 0.4590(3) 0.5171(2) 0.1692(4) 0.0777(14) Uani 1 1 d . . . . .
C4 C 0.4600(4) 0.5813(3) 0.1673(4) 0.0812(15) Uani 1 1 d . . . . .
H4 H 0.5187 0.6022 0.1597 0.097 Uiso 1 1 calc R . . . .
C5 C 0.3784(4) 0.6138(3) 0.1761(6) 0.0934(18) Uani 1 1 d . . . . .
H5 H 0.3821 0.6572 0.1730 0.112 Uiso 1 1 calc R . . . .
C6 C 0.2065(5) 0.6215(4) 0.2156(10) 0.134(3) Uani 1 1 d . . . . .
H6AA H 0.2124 0.6640 0.1813 0.161 Uiso 0.5 1 calc R . . B 1
H6AB H 0.1512 0.6020 0.1698 0.161 Uiso 0.5 1 calc R . . B 1
H6BC H 0.1588 0.6092 0.1449 0.161 Uiso 0.5 1 calc R . . C 2
H6BD H 0.2205 0.6653 0.1999 0.161 Uiso 0.5 1 calc R . . C 2
C7 C 0.1565(11) 0.6144(6) 0.376(2) 0.089(5) Uani 0.5 1 d . . . A 2
C8 C 0.0699(10) 0.5901(6) 0.3783(17) 0.105(3) Uani 0.5 1 d . . . A 2
H8 H 0.0410 0.5807 0.2910 0.126 Uiso 0.5 1 calc R . . A 2
C9 C 0.0191(13) 0.5778(10) 0.5000 0.133(9) Uani 0.5 2 d S T P A 2
H9 H -0.0439 0.5625 0.5000 0.160 Uiso 0.5 2 calc RS T P A 2
C10 C 0.1978(9) 0.6200(8) 0.360(2) 0.084(4) Uani 0.5 1 d . . . A 1
C11 C 0.2381(6) 0.6659(4) 0.4275(12) 0.083(3) Uani 0.5 1 d . . . A 1
H11 H 0.2667 0.6985 0.3771 0.099 Uiso 0.5 1 calc R . . A 1
C12 C 0.1545(8) 0.5699(6) 0.4270(13) 0.093(3) Uani 0.5 1 d . . . A 1
H12 H 0.1266 0.5376 0.3751 0.112 Uiso 0.5 1 calc R . . A 1
N3 N 0.5739(6) 0.6531(4) 0.5000 0.100(2) Uani 1 2 d S T P . .
C13 C 0.4803(7) 0.6390(5) 0.5000 0.094(2) Uani 1 2 d S T P . .
H13 H 0.4349 0.6710 0.5000 0.113 Uiso 1 2 calc RS T P . .
C14 C 0.4505(5) 0.5800(4) 0.5000 0.0819(19) Uani 1 2 d S T P . .
H14 H 0.3845 0.5716 0.5000 0.098 Uiso 1 2 calc RS T P . .
C15 C 0.5163(5) 0.5305(4) 0.5000 0.081(2) Uani 1 2 d S T P . .
C16 C 0.6132(5) 0.5481(5) 0.5000 0.089(2) Uani 1 2 d S T P . .
H16 H 0.6604 0.5172 0.5000 0.107 Uiso 1 2 calc RS T P . .
C17 C 0.6407(7) 0.6072(6) 0.5000 0.103(3) Uani 1 2 d S T P . .
H17 H 0.7062 0.6171 0.5000 0.124 Uiso 1 2 calc RS T P . .
C18 C 0.6065(10) 0.7180(5) 0.5000 0.128(4) Uani 1 2 d S T P . .
H18A H 0.6670 0.7211 0.4502 0.192 Uiso 0.5 1 calc GR . . D -1
H18B H 0.6147 0.7320 0.5968 0.192 Uiso 0.5 1 calc GR . . D -1
H18C H 0.5592 0.7436 0.4530 0.192 Uiso 0.5 1 calc GR . . D -1
P1 P 0.0000 0.5000 0.0000 0.0718(8) Uani 1 4 d S T P . .
F1 F 0.1006(4) 0.4763(3) 0.0000 0.214(5) Uani 1 2 d S T P . .
F2 F 0.0000 0.5000 0.1616(7) 0.211(5) Uani 1 2 d S T P . .
F3 F 0.0341(4) 0.5695(2) 0.0000 0.1129(18) Uani 1 2 d S T P . .
P2 P 0.12286(15) 0.77434(7) 0.0000 0.0853(8) Uani 1 2 d S T P . .
F4 F 0.0920(4) 0.7054(2) 0.0000 0.1074(16) Uani 1 2 d S T P . .
F5 F 0.2292(5) 0.7535(3) 0.0000 0.185(4) Uani 1 2 d S T P . .
F6 F 0.1215(8) 0.7749(4) 0.1579(6) 0.241(5) Uani 1 1 d . . . . .
F7 F 0.1535(5) 0.8433(2) 0.0000 0.137(2) Uani 1 2 d S T P . .
F8 F 0.0159(6) 0.7949(3) 0.0000 0.190(4) Uani 1 2 d S T P . .


_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
N1 C1 1.371(9) . ?
N1 C5 1.360(7) . ?
N1 C6 1.436(10) . ?
N2 C7 1.36(2) . ?
N2 C7 1.36(2) 6_556 ?
C1 H1 0.9500 . ?
C1 C2 1.354(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.446(6) . ?
C3 C3 1.380(11) 2_665 ?
C3 C4 1.405(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.357(9) . ?
C5 H5 0.9500 . ?
C6 H6AA 0.9900 . ?
C6 H6AB 0.9900 . ?
C6 H6BC 0.9900 . ?
C6 H6BD 0.9900 . ?
C6 C7 1.70(2) . ?
C6 C10 1.38(2) . ?
C7 C8 1.33(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(17) . ?
C9 C8 1.391(17) 6_556 ?
C9 H9 0.9500 . ?
C10 C11 1.32(2) . ?
C10 C12 1.409(19) . ?
C11 C11 1.38(2) 6_556 ?
C11 H11 0.9500 . ?
C12 C12 1.39(3) 6_556 ?
C12 H12 0.9500 . ?
N3 C13 1.356(12) . ?
N3 C17 1.379(14) . ?
N3 C18 1.495(13) . ?
C13 H13 0.9500 . ?
C13 C14 1.358(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.428(12) . ?
C15 C15 1.410(17) 5_666 ?
C15 C16 1.422(10) . ?
C16 H16 0.9500 . ?
C16 C17 1.350(13) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
P1 F1 1.512(6) 5_565 ?
P1 F1 1.512(6) . ?
P1 F2 1.541(7) . ?
P1 F2 1.541(7) 5_565 ?
P1 F3 1.597(4) . ?
P1 F3 1.597(4) 5_565 ?
P2 F4 1.571(5) . ?
P2 F5 1.569(7) . ?
P2 F6 1.507(6) . ?
P2 F6 1.507(6) 6 ?
P2 F7 1.570(5) . ?
P2 F8 1.575(7) . ?

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 C6 119.0(5) . . ?
C5 N1 C1 117.6(6) . . ?
C5 N1 C6 123.4(6) . . ?
C7 N2 C7 120(2) . 6_556 ?
N1 C1 H1 119.0 . . ?
C2 C1 N1 122.0(5) . . ?
C2 C1 H1 119.0 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C3 C3 C2 122.7(6) 2_665 . ?
C3 C3 C4 122.3(5) 2_665 . ?
C4 C3 C2 114.9(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(5) . . ?
C5 C4 H4 119.5 . . ?
N1 C5 H5 118.4 . . ?
C4 C5 N1 123.2(5) . . ?
C4 C5 H5 118.4 . . ?
N1 C6 H6AA 111.0 . . ?
N1 C6 H6AB 111.0 . . ?
N1 C6 H6BC 108.0 . . ?
N1 C6 H6BD 108.0 . . ?
N1 C6 C7 117.3(7) . . ?
H6AA C6 H6AB 109.0 . . ?
H6BC C6 H6BD 107.2 . . ?
C7 C6 H6BC 108.0 . . ?
C7 C6 H6BD 108.0 . . ?
C10 C6 N1 103.7(8) . . ?
C10 C6 H6AA 111.0 . . ?
C10 C6 H6AB 111.0 . . ?
N2 C7 C6 125.0(12) . . ?
C8 C7 N2 119.3(19) . . ?
C8 C7 C6 115.5(15) . . ?
C7 C8 H8 117.9 . . ?
C7 C8 C9 124.1(17) . . ?
C9 C8 H8 117.9 . . ?
C8 C9 C8 113.2(17) 6_556 . ?
C8 C9 H9 123.4 . . ?
C8 C9 H9 123.4 6_556 . ?
C6 C10 C12 120.7(15) . . ?
C11 C10 C6 115.5(13) . . ?
C11 C10 C12 123.6(18) . . ?
C10 C11 C11 119.2(10) . 6_556 ?
C10 C11 H11 120.4 . . ?
C11 C11 H11 120.4 6_556 . ?
C10 C12 H12 121.4 . . ?
C12 C12 C10 117.1(10) 6_556 . ?
C12 C12 H12 121.4 6_556 . ?
C13 N3 C17 120.1(9) . . ?
C13 N3 C18 121.1(10) . . ?
C17 N3 C18 118.8(9) . . ?
N3 C13 H13 119.4 . . ?
N3 C13 C14 121.2(9) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(8) . . ?
C15 C14 H14 119.3 . . ?
C15 C15 C14 120.5(8) 5_666 . ?
C15 C15 C16 124.8(9) 5_666 . ?
C16 C15 C14 114.8(8) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.5(9) . . ?
C17 C16 H16 118.8 . . ?
N3 C17 H17 120.0 . . ?
C16 C17 N3 120.1(8) . . ?
C16 C17 H17 120.0 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 P1 F1 180.0 5_565 . ?
F1 P1 F2 90.000(1) 5_565 5_565 ?
F1 P1 F2 90.000(1) 5_565 . ?
F1 P1 F2 90.000(1) . . ?
F1 P1 F2 90.000(1) . 5_565 ?
F1 P1 F3 87.5(3) 5_565 . ?
F1 P1 F3 92.5(3) 5_565 5_565 ?
F1 P1 F3 87.5(3) . 5_565 ?
F1 P1 F3 92.5(3) . . ?
F2 P1 F2 180.0 . 5_565 ?
F2 P1 F3 90.0 5_565 5_565 ?
F2 P1 F3 90.0 . . ?
F2 P1 F3 90.0 5_565 . ?
F2 P1 F3 90.0 . 5_565 ?
F3 P1 F3 180.0 . 5_565 ?
F4 P2 F8 90.5(3) . . ?
F5 P2 F4 89.2(3) . . ?
F5 P2 F7 90.9(3) . . ?
F5 P2 F8 179.7(4) . . ?
F6 P2 F4 90.3(3) . . ?
F6 P2 F4 90.3(3) 6 . ?
F6 P2 F5 90.8(4) . . ?
F6 P2 F5 90.8(4) 6 . ?
F6 P2 F6 178.3(9) . 6 ?
F6 P2 F7 89.7(3) 6 . ?
F6 P2 F7 89.7(3) . . ?
F6 P2 F8 89.2(4) 6 . ?
F6 P2 F8 89.2(4) . . ?
F7 P2 F4 179.9(3) . . ?
F7 P2 F8 89.4(4) . . ?

_smtbx_masks_special_details     
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 690.2 Ang³ [23.4%]
Total electron count / cell = 155.2
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.134 0.333 0.340 172.6 38.8 ?
2 -0.134 0.667 -0.786 172.6 38.8 ?
3 0.366 0.833 -0.203 172.6 38.8 ?
4 0.634 0.167 -0.817 172.6 38.8 ?

_olex2_date_sample_data_collection 2017-12-06
_olex2_date_sample_submission    2017-11-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1123
_olex2_submission_special_instructions 'No special instructions were received'
