# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20181219dzr_0m
_database_code_depnum_ccdc_archive 'CCDC 1978530'
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2018-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 O2'
_chemical_formula_sum            'C21 H24 O2'
_chemical_formula_weight         308.40
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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'
O O 0.0412 0.0250 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.5540(3)
_cell_length_b                   16.2084(7)
_cell_length_c                   16.8478(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1789.74(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6775
_cell_measurement_temperature    280(2)
_cell_measurement_theta_max      47.012
_cell_measurement_theta_min      3.293
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1706 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.8479. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22461
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.952
_diffrn_reflns_theta_min         3.292
_diffrn_ambient_temperature      280.63
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2470
_reflns_number_total             3392
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 840 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.128
_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)+(0.0546P)²+0.0437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1141
_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 Ternary CH refined with riding coordinates:
 C1(H1), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
;
_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
O1 O 0.2771(2) 0.42510(11) 0.62332(11) 0.0536(5) Uani 1 1 d . . . . .
O2 O 0.0372(3) 0.34151(14) 0.57469(13) 0.0740(6) Uani 1 1 d . . . . .
C1 C 0.5999(4) 0.42015(16) 0.69588(16) 0.0537(7) Uani 1 1 d . . . . .
H1 H 0.747138 0.416322 0.686473 0.064 Uiso 1 1 calc R . . . .
C2 C 0.4978(4) 0.43705(16) 0.61433(16) 0.0497(6) Uani 1 1 d . . . . .
C3 C 0.5522(4) 0.37093(16) 0.55617(17) 0.0549(7) Uani 1 1 d . . . . .
H3 H 0.683532 0.360728 0.537757 0.066 Uiso 1 1 calc R . . . .
C4 C 0.3895(5) 0.32916(17) 0.53455(17) 0.0582(7) Uani 1 1 d . . . . .
H4 H 0.387214 0.285805 0.498402 0.070 Uiso 1 1 calc R . . . .
C5 C 0.2148(5) 0.36190(17) 0.57638(17) 0.0563(7) Uani 1 1 d . . . . .
C6 C 0.5340(4) 0.52439(16) 0.58221(16) 0.0549(7) Uani 1 1 d . . . . .
H6 H 0.485994 0.563215 0.622695 0.066 Uiso 1 1 calc R . . . .
C7 C 0.4118(5) 0.54140(19) 0.50623(19) 0.0749(9) Uani 1 1 d . . . . .
H7A H 0.454307 0.503149 0.465146 0.090 Uiso 1 1 calc R . . . .
H7B H 0.267984 0.532186 0.516517 0.090 Uiso 1 1 calc R . . . .
C8 C 0.4425(7) 0.6294(2) 0.4770(2) 0.0980(13) Uani 1 1 d . . . . .
H8A H 0.366839 0.637403 0.428162 0.118 Uiso 1 1 calc R . . . .
H8B H 0.389484 0.667662 0.516214 0.118 Uiso 1 1 calc R . . . .
C9 C 0.6635(7) 0.6474(2) 0.4627(2) 0.0989(14) Uani 1 1 d . . . . .
H9A H 0.679323 0.704693 0.447210 0.119 Uiso 1 1 calc R . . . .
H9B H 0.713110 0.613178 0.419618 0.119 Uiso 1 1 calc R . . . .
C10 C 0.7892(6) 0.6307(2) 0.5373(2) 0.0925(12) Uani 1 1 d . . . . .
H10A H 0.932512 0.639437 0.525702 0.111 Uiso 1 1 calc R . . . .
H10B H 0.749672 0.669310 0.578522 0.111 Uiso 1 1 calc R . . . .
C11 C 0.7586(5) 0.54335(19) 0.5670(2) 0.0722(9) Uani 1 1 d . . . . .
H11A H 0.834907 0.535810 0.615825 0.087 Uiso 1 1 calc R . . . .
H11B H 0.811664 0.504869 0.528058 0.087 Uiso 1 1 calc R . . . .
C12 C 0.5335(5) 0.33908(18) 0.73040(18) 0.0693(8) Uani 1 1 d . . . . .
H12 H 0.393622 0.330377 0.734411 0.083 Uiso 1 1 calc R . . . .
C13 C 0.6533(6) 0.27841(19) 0.75586(19) 0.0753(9) Uani 1 1 d . . . . .
H13 H 0.587489 0.232477 0.776811 0.090 Uiso 1 1 calc R . . . .
C14 C 0.8699(6) 0.2754(2) 0.7549(2) 0.0839(10) Uani 1 1 d . . . . .
H14 H 0.940283 0.319383 0.732327 0.101 Uiso 1 1 calc R . . . .
C15 C 0.9769(7) 0.2133(3) 0.7844(2) 0.1150(15) Uani 1 1 d . . . . .
H15A H 0.910211 0.168538 0.807235 0.138 Uiso 1 1 calc R . . . .
H15B H 1.118624 0.214341 0.782210 0.138 Uiso 1 1 calc R . . . .
C16 C 0.5675(4) 0.48810(17) 0.75668(16) 0.0546(7) Uani 1 1 d . . . . .
C17 C 0.7316(5) 0.5309(2) 0.78672(19) 0.0709(8) Uani 1 1 d . . . . .
H17 H 0.862240 0.518824 0.768584 0.085 Uiso 1 1 calc R . . . .
C18 C 0.7050(7) 0.5917(2) 0.8436(2) 0.0862(11) Uani 1 1 d . . . . .
H18 H 0.817591 0.619916 0.863457 0.103 Uiso 1 1 calc R . . . .
C19 C 0.5153(7) 0.6103(2) 0.87050(19) 0.0857(11) Uani 1 1 d . . . . .
H19 H 0.497822 0.651238 0.908580 0.103 Uiso 1 1 calc R . . . .
C20 C 0.3507(6) 0.5688(2) 0.84154(19) 0.0858(10) Uani 1 1 d . . . . .
H20 H 0.220754 0.581594 0.859960 0.103 Uiso 1 1 calc R . . . .
C21 C 0.3753(5) 0.5079(2) 0.78501(19) 0.0729(9) Uani 1 1 d . . . . .
H21 H 0.261697 0.479935 0.765790 0.087 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.467(3) . ?
O1 C5 1.357(3) . ?
O2 C5 1.210(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.553(4) . ?
C1 C12 1.501(4) . ?
C1 C16 1.519(4) . ?
C2 C3 1.495(4) . ?
C2 C6 1.534(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.314(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.445(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.535(4) . ?
C6 C11 1.525(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.522(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.497(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.527(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.330(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.421(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.324(5) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 C17 1.376(4) . ?
C16 C21 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(4) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C2 109.7(2) . . ?
C2 C1 H1 107.0 . . ?
C12 C1 H1 107.0 . . ?
C12 C1 C2 111.9(2) . . ?
C12 C1 C16 109.4(2) . . ?
C16 C1 H1 107.0 . . ?
C16 C1 C2 114.1(2) . . ?
O1 C2 C1 108.1(2) . . ?
O1 C2 C3 102.0(2) . . ?
O1 C2 C6 108.1(2) . . ?
C3 C2 C1 110.5(2) . . ?
C3 C2 C6 113.2(2) . . ?
C6 C2 C1 114.1(2) . . ?
C2 C3 H3 124.5 . . ?
C4 C3 C2 110.9(2) . . ?
C4 C3 H3 124.5 . . ?
C3 C4 H4 125.7 . . ?
C3 C4 C5 108.6(2) . . ?
C5 C4 H4 125.7 . . ?
O1 C5 C4 108.8(2) . . ?
O2 C5 O1 120.6(3) . . ?
O2 C5 C4 130.6(3) . . ?
C2 C6 H6 107.3 . . ?
C2 C6 C7 112.3(2) . . ?
C7 C6 H6 107.3 . . ?
C11 C6 C2 113.2(2) . . ?
C11 C6 H6 107.3 . . ?
C11 C6 C7 109.1(3) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.6(3) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.3(3) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 C10 110.8(3) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.5(3) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C6 C11 H11A 109.3 . . ?
C6 C11 H11B 109.3 . . ?
C10 C11 C6 111.8(3) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C1 C12 H12 116.5 . . ?
C13 C12 C1 127.0(3) . . ?
C13 C12 H12 116.5 . . ?
C12 C13 H13 116.1 . . ?
C12 C13 C14 127.7(3) . . ?
C14 C13 H13 116.1 . . ?
C13 C14 H14 118.3 . . ?
C15 C14 C13 123.4(4) . . ?
C15 C14 H14 118.3 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C17 C16 C1 120.3(3) . . ?
C17 C16 C21 117.9(3) . . ?
C21 C16 C1 121.8(2) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.6(3) . . ?
C20 C21 H21 119.7 . . ?

_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_20190115dzy
_database_code_depnum_ccdc_archive 'CCDC 1978531'
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C49 H34 F12 N3 O6 P'
_chemical_formula_sum            'C49 H34 F12 N3 O6 P'
_chemical_formula_weight         1019.76
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2596 0.3354 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.5180(7)
_cell_length_b                   8.3701(4)
_cell_length_c                   19.8041(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.284(3)
_cell_angle_gamma                90
_cell_volume                     2197.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.95
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1399 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.7826. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23560
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.906
_diffrn_reflns_theta_min         2.900
_diffrn_ambient_temperature      169.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.765
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                5579
_reflns_number_total             7351
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.364
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         7351
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.160
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1775
_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:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B), C16(H16A,H16B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
 C30(H30), C31(H31), C34(H34), C36(H36), C38(H38), C43(H43), C45(H45), C47(H47)
;
_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
P1 P 0.27186(11) 0.2685(2) 0.73340(7) 0.0303(4) Uani 1 1 d . . . . .
F1 F 0.1650(4) -0.1206(6) 0.8969(3) 0.0773(16) Uani 1 1 d . . . . .
F2 F 0.0152(3) -0.0312(6) 0.8711(2) 0.0632(12) Uani 1 1 d . . . . .
F3 F 0.0866(3) -0.0551(5) 0.9762(2) 0.0608(12) Uani 1 1 d . . . . .
F4 F 0.0926(3) 0.6109(5) 1.0100(2) 0.0537(11) Uani 1 1 d . . . . .
F5 F 0.1806(4) 0.4531(6) 1.08201(18) 0.0673(14) Uani 1 1 d . . . . .
F6 F 0.2517(3) 0.6318(7) 1.0296(2) 0.0809(17) Uani 1 1 d . . . . .
F7 F 0.3897(3) 1.0806(6) 0.9259(3) 0.0744(15) Uani 1 1 d . . . . .
F8 F 0.5397(3) 1.0419(6) 0.9790(2) 0.0768(16) Uani 1 1 d . . . . .
F9 F 0.5098(5) 1.1208(7) 0.8744(3) 0.099(2) Uani 1 1 d . . . . .
F10 F 0.6771(6) 0.4644(12) 0.9574(3) 0.163(4) Uani 1 1 d . . . . .
F11 F 0.7283(4) 0.5896(8) 0.8848(6) 0.164(4) Uani 1 1 d . . . . .
F12 F 0.6475(3) 0.3813(6) 0.8564(2) 0.0670(13) Uani 1 1 d . . . . .
O1 O 0.1724(3) 0.2947(5) 0.67357(18) 0.0300(10) Uani 1 1 d . . . . .
O2 O 0.3567(3) 0.3665(6) 0.70225(18) 0.0331(10) Uani 1 1 d . . . . .
O3 O 0.0016(4) 0.0676(7) 0.7034(3) 0.0516(13) Uani 1 1 d . . . . .
O4 O -0.0366(3) 0.2342(7) 0.6175(2) 0.0477(13) Uani 1 1 d . . . . .
O5 O 0.5715(4) 0.4633(8) 0.6937(3) 0.0632(15) Uani 1 1 d . . . . .
O6 O 0.7226(4) 0.3761(10) 0.6963(4) 0.100(3) Uani 1 1 d . . . . .
N1 N 0.2627(4) 0.4023(6) 0.7961(2) 0.0302(12) Uani 1 1 d . . . . .
N2 N -0.0168(4) 0.2039(8) 0.6794(3) 0.0414(15) Uani 1 1 d . . . . .
N3 N 0.6331(5) 0.3570(9) 0.6990(3) 0.0558(18) Uani 1 1 d . . . . .
C1 C 0.1500(4) 0.4449(8) 0.6432(3) 0.0279(13) Uani 1 1 d . . . . .
C2 C 0.0703(5) 0.5323(8) 0.6599(3) 0.0325(15) Uani 1 1 d . . . . .
C3 C 0.0521(5) 0.6838(9) 0.6279(3) 0.0393(16) Uani 1 1 d . . . . .
H3 H -0.003627 0.744973 0.635952 0.047 Uiso 1 1 calc R . . . .
C4 C 0.1130(5) 0.7464(8) 0.5852(3) 0.0350(15) Uani 1 1 d . . . . .
C5 C 0.0874(6) 0.9073(9) 0.5538(4) 0.0498(19) Uani 1 1 d . . . . .
H5A H 0.058113 0.973629 0.586341 0.060 Uiso 1 1 calc R . . . .
H5B H 0.035395 0.894581 0.511388 0.060 Uiso 1 1 calc R . . . .
C6 C 0.1774(6) 0.9940(11) 0.5361(4) 0.060(2) Uani 1 1 d . . . . .
H6A H 0.153877 1.088949 0.507562 0.072 Uiso 1 1 calc R . . . .
H6B H 0.222027 1.031153 0.578886 0.072 Uiso 1 1 calc R . . . .
C7 C 0.2358(6) 0.8851(10) 0.4971(4) 0.054(2) Uani 1 1 d . . . . .
H7A H 0.191374 0.849474 0.453928 0.064 Uiso 1 1 calc R . . . .
H7B H 0.293002 0.944698 0.484792 0.064 Uiso 1 1 calc R . . . .
C8 C 0.2752(5) 0.7413(9) 0.5400(3) 0.0402(16) Uani 1 1 d . . . . .
H8A H 0.332482 0.774834 0.576418 0.048 Uiso 1 1 calc R . . . .
H8B H 0.301046 0.662653 0.510334 0.048 Uiso 1 1 calc R . . . .
C9 C 0.1951(5) 0.6602(8) 0.5738(3) 0.0330(15) Uani 1 1 d . . . . .
C10 C 0.2109(5) 0.5035(8) 0.5995(3) 0.0329(15) Uani 1 1 d . . . . .
C11 C 0.2917(4) 0.3979(8) 0.5817(3) 0.0274(14) Uani 1 1 d . . . . .
C12 C 0.2935(4) 0.3587(8) 0.5123(3) 0.0326(15) Uani 1 1 d . . . . .
C13 C 0.2072(5) 0.4057(9) 0.4543(3) 0.0381(16) Uani 1 1 d . . . . .
H13A H 0.148709 0.335569 0.455801 0.046 Uiso 1 1 calc R . . . .
H13B H 0.186809 0.516819 0.461919 0.046 Uiso 1 1 calc R . . . .
C14 C 0.2336(6) 0.3942(10) 0.3839(3) 0.0452(18) Uani 1 1 d . . . . .
H14A H 0.171659 0.407326 0.348214 0.054 Uiso 1 1 calc R . . . .
H14B H 0.280740 0.481322 0.378133 0.054 Uiso 1 1 calc R . . . .
C15 C 0.2816(6) 0.2353(10) 0.3743(3) 0.0482(19) Uani 1 1 d . . . . .
H15A H 0.292591 0.225990 0.326457 0.058 Uiso 1 1 calc R . . . .
H15B H 0.236383 0.147475 0.382575 0.058 Uiso 1 1 calc R . . . .
C16 C 0.3822(5) 0.2228(9) 0.4248(3) 0.0430(18) Uani 1 1 d . . . . .
H16A H 0.431440 0.295918 0.409992 0.052 Uiso 1 1 calc R . . . .
H16B H 0.408410 0.112508 0.423816 0.052 Uiso 1 1 calc R . . . .
C17 C 0.3726(4) 0.2645(8) 0.4986(3) 0.0306(14) Uani 1 1 d . . . . .
C18 C 0.4432(5) 0.2022(8) 0.5522(3) 0.0337(15) Uani 1 1 d . . . . .
H18 H 0.496138 0.137536 0.542017 0.040 Uiso 1 1 calc R . . . .
C19 C 0.4388(4) 0.2320(8) 0.6209(3) 0.0307(15) Uani 1 1 d . . . . .
C20 C 0.3622(4) 0.3296(8) 0.6330(3) 0.0313(15) Uani 1 1 d . . . . .
C21 C 0.5083(5) 0.1419(9) 0.6766(3) 0.0374(16) Uani 1 1 d . . . . .
C22 C 0.4811(5) -0.0179(10) 0.6909(3) 0.0430(17) Uani 1 1 d . . . . .
H22 H 0.417019 -0.059116 0.669756 0.052 Uiso 1 1 calc R . . . .
C23 C 0.5477(6) -0.1119(11) 0.7355(4) 0.054(2) Uani 1 1 d . . . . .
H23 H 0.530070 -0.219097 0.743512 0.065 Uiso 1 1 calc R . . . .
C24 C 0.6399(5) -0.0523(11) 0.7686(3) 0.0479(19) Uani 1 1 d . . . . .
H24 H 0.683783 -0.118565 0.800058 0.058 Uiso 1 1 calc R . . . .
C25 C 0.6693(5) 0.0994(10) 0.7572(3) 0.0448(18) Uani 1 1 d . . . . .
H25 H 0.733050 0.139545 0.779553 0.054 Uiso 1 1 calc R . . . .
C26 C 0.6017(5) 0.1944(9) 0.7110(4) 0.0450(18) Uani 1 1 d . . . . .
C27 C 0.0157(5) 0.4875(9) 0.7145(3) 0.0357(16) Uani 1 1 d . . . . .
C28 C 0.0022(5) 0.6057(10) 0.7630(3) 0.0426(17) Uani 1 1 d . . . . .
H28 H 0.023247 0.712143 0.756893 0.051 Uiso 1 1 calc R . . . .
C29 C -0.0406(5) 0.5704(11) 0.8192(4) 0.053(2) Uani 1 1 d . . . . .
H29 H -0.049813 0.653580 0.850013 0.063 Uiso 1 1 calc R . . . .
C30 C -0.0703(5) 0.4181(11) 0.8313(4) 0.052(2) Uani 1 1 d . . . . .
H30 H -0.098192 0.394947 0.870690 0.062 Uiso 1 1 calc R . . . .
C31 C -0.0586(4) 0.2987(10) 0.7850(3) 0.0446(18) Uani 1 1 d . . . . .
H31 H -0.078033 0.192277 0.792747 0.054 Uiso 1 1 calc R . . . .
C32 C -0.0189(4) 0.3338(9) 0.7278(3) 0.0371(16) Uani 1 1 d . . . . .
C33 C 0.2215(4) 0.3544(8) 0.8541(3) 0.0304(14) Uani 1 1 d . . . . .
C34 C 0.1802(5) 0.2023(9) 0.8567(3) 0.0359(16) Uani 1 1 d . . . . .
H34 H 0.178009 0.131481 0.818946 0.043 Uiso 1 1 calc R . . . .
C35 C 0.1423(4) 0.1528(8) 0.9134(3) 0.0360(15) Uani 1 1 d . . . . .
C36 C 0.1407(4) 0.2577(9) 0.9681(3) 0.0362(15) Uani 1 1 d . . . . .
H36 H 0.112259 0.226135 1.006246 0.043 Uiso 1 1 calc R . . . .
C37 C 0.1817(4) 0.4091(8) 0.9653(3) 0.0340(15) Uani 1 1 d . . . . .
C38 C 0.2222(4) 0.4575(9) 0.9086(3) 0.0343(15) Uani 1 1 d . . . . .
H38 H 0.250237 0.561352 0.907743 0.041 Uiso 1 1 calc R . . . .
C39 C 0.1770(5) 0.5241(10) 1.0206(3) 0.0427(18) Uani 1 1 d . . . . .
C40 C 0.1031(5) -0.0104(9) 0.9151(4) 0.0413(17) Uani 1 1 d . . . . .
C41 C 0.2820(4) 0.5754(8) 0.7879(3) 0.0311(14) Uani 1 1 d . . . . .
H41A H 0.225109 0.636812 0.799606 0.037 Uiso 1 1 calc R . . . .
H41B H 0.283532 0.596664 0.738911 0.037 Uiso 1 1 calc R . . . .
C42 C 0.3799(4) 0.6358(9) 0.8320(3) 0.0321(15) Uani 1 1 d . . . . .
C43 C 0.3838(4) 0.7907(8) 0.8563(3) 0.0326(14) Uani 1 1 d . . . . .
H43 H 0.324493 0.854484 0.847320 0.039 Uiso 1 1 calc R . . . .
C44 C 0.4729(5) 0.8556(8) 0.8936(3) 0.0328(14) Uani 1 1 d . . . . .
C45 C 0.5601(5) 0.7609(9) 0.9072(3) 0.0375(15) Uani 1 1 d . . . . .
H45 H 0.621133 0.801072 0.933780 0.045 Uiso 1 1 calc R . . . .
C46 C 0.5549(5) 0.6073(9) 0.8808(3) 0.0361(15) Uani 1 1 d . . . . .
C47 C 0.4664(5) 0.5421(8) 0.8434(3) 0.0352(15) Uani 1 1 d . . . . .
H47 H 0.465087 0.436194 0.826042 0.042 Uiso 1 1 calc R . . . .
C48 C 0.6492(5) 0.5089(11) 0.8934(4) 0.056(2) Uani 1 1 d . . . . .
C49 C 0.4785(5) 1.0208(10) 0.9185(4) 0.0454(18) 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
P1 O1 1.624(4) . ?
P1 O2 1.626(4) . ?
P1 N1 1.694(5) . ?
F1 C40 1.341(8) . ?
F2 C40 1.341(8) . ?
F3 C40 1.327(8) . ?
F4 C39 1.335(8) . ?
F5 C39 1.346(8) . ?
F6 C39 1.339(8) . ?
F7 C49 1.335(8) . ?
F8 C49 1.327(8) . ?
F9 C49 1.337(9) . ?
F10 C48 1.305(10) . ?
F11 C48 1.304(11) . ?
F12 C48 1.292(9) . ?
O1 C1 1.401(7) . ?
O2 C20 1.421(6) . ?
O3 N2 1.242(8) . ?
O4 N2 1.227(7) . ?
O5 N3 1.208(8) . ?
O6 N3 1.232(8) . ?
N1 C33 1.429(7) . ?
N1 C41 1.486(8) . ?
N2 C32 1.454(9) . ?
N3 C26 1.459(10) . ?
C1 C2 1.394(9) . ?
C1 C10 1.395(8) . ?
C2 C3 1.417(10) . ?
C2 C27 1.472(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(9) . ?
C4 C5 1.496(10) . ?
C4 C9 1.378(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.515(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.509(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.538(9) . ?
C9 C10 1.408(10) . ?
C10 C11 1.499(9) . ?
C11 C12 1.418(8) . ?
C11 C20 1.374(8) . ?
C12 C13 1.520(8) . ?
C12 C17 1.397(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.509(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.507(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.526(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.533(8) . ?
C17 C18 1.384(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(8) . ?
C19 C20 1.376(8) . ?
C19 C21 1.504(9) . ?
C21 C22 1.431(11) . ?
C21 C26 1.383(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(10) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.362(11) . ?
C25 H25 0.9500 . ?
C25 C26 1.406(10) . ?
C27 C28 1.417(10) . ?
C27 C32 1.411(10) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(10) . ?
C29 H29 0.9500 . ?
C29 C30 1.372(12) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(11) . ?
C31 H31 0.9500 . ?
C31 C32 1.375(9) . ?
C33 C34 1.395(9) . ?
C33 C38 1.381(9) . ?
C34 H34 0.9500 . ?
C34 C35 1.385(9) . ?
C35 C36 1.398(9) . ?
C35 C40 1.468(10) . ?
C36 H36 0.9500 . ?
C36 C37 1.389(10) . ?
C37 C38 1.402(8) . ?
C37 C39 1.468(10) . ?
C38 H38 0.9500 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C42 1.523(8) . ?
C42 C43 1.380(10) . ?
C42 C47 1.389(9) . ?
C43 H43 0.9500 . ?
C43 C44 1.394(9) . ?
C44 C45 1.403(9) . ?
C44 C49 1.465(10) . ?
C45 H45 0.9500 . ?
C45 C46 1.383(10) . ?
C46 C47 1.390(9) . ?
C46 C48 1.498(10) . ?
C47 H47 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 101.5(2) . . ?
O1 P1 N1 106.0(2) . . ?
O2 P1 N1 95.9(2) . . ?
C1 O1 P1 120.9(4) . . ?
C20 O2 P1 115.5(4) . . ?
C33 N1 P1 119.9(4) . . ?
C33 N1 C41 117.7(5) . . ?
C41 N1 P1 121.7(4) . . ?
O3 N2 C32 117.5(6) . . ?
O4 N2 O3 124.1(6) . . ?
O4 N2 C32 118.4(6) . . ?
O5 N3 O6 124.5(8) . . ?
O5 N3 C26 119.0(6) . . ?
O6 N3 C26 116.5(7) . . ?
C2 C1 O1 118.8(5) . . ?
C2 C1 C10 122.7(6) . . ?
C10 C1 O1 118.5(5) . . ?
C1 C2 C3 116.0(6) . . ?
C1 C2 C27 124.2(6) . . ?
C3 C2 C27 119.2(6) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.4(6) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 118.3(6) . . ?
C9 C4 C3 119.6(6) . . ?
C9 C4 C5 122.1(6) . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.4(6) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 C5 110.6(7) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.9(6) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.3(6) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C4 C9 C8 119.9(6) . . ?
C4 C9 C10 119.9(6) . . ?
C10 C9 C8 119.9(6) . . ?
C1 C10 C9 119.0(6) . . ?
C1 C10 C11 118.9(6) . . ?
C9 C10 C11 122.0(6) . . ?
C12 C11 C10 121.0(5) . . ?
C20 C11 C10 120.2(5) . . ?
C20 C11 C12 118.6(5) . . ?
C11 C12 C13 121.1(5) . . ?
C17 C12 C11 118.6(5) . . ?
C17 C12 C13 120.1(5) . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.4(5) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.0(6) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C14 C15 C16 109.2(6) . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C15 C16 C17 112.2(5) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C12 C17 C16 121.7(5) . . ?
C18 C17 C12 120.2(5) . . ?
C18 C17 C16 118.1(6) . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.7(6) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C21 119.0(5) . . ?
C20 C19 C18 117.0(5) . . ?
C20 C19 C21 123.6(5) . . ?
C11 C20 O2 117.5(5) . . ?
C11 C20 C19 123.7(5) . . ?
C19 C20 O2 118.7(5) . . ?
C22 C21 C19 117.8(6) . . ?
C26 C21 C19 125.5(7) . . ?
C26 C21 C22 116.4(6) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(7) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.9(8) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.5(7) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 121.2 . . ?
C24 C25 C26 117.5(7) . . ?
C26 C25 H25 121.2 . . ?
C21 C26 N3 118.8(6) . . ?
C21 C26 C25 123.7(7) . . ?
C25 C26 N3 117.4(7) . . ?
C28 C27 C2 118.0(7) . . ?
C32 C27 C2 127.0(6) . . ?
C32 C27 C28 114.7(6) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 C27 121.8(8) . . ?
C29 C28 H28 119.1 . . ?
C28 C29 H29 119.2 . . ?
C30 C29 C28 121.5(7) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 120.7 . . ?
C29 C30 C31 118.6(7) . . ?
C31 C30 H30 120.7 . . ?
C30 C31 H31 119.9 . . ?
C32 C31 C30 120.3(7) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 N2 120.5(6) . . ?
C31 C32 N2 116.4(6) . . ?
C31 C32 C27 123.1(6) . . ?
C34 C33 N1 120.5(5) . . ?
C38 C33 N1 120.6(6) . . ?
C38 C33 C34 118.8(5) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.1(6) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 C36 120.3(7) . . ?
C34 C35 C40 119.3(6) . . ?
C36 C35 C40 120.4(6) . . ?
C35 C36 H36 120.8 . . ?
C37 C36 C35 118.4(6) . . ?
C37 C36 H36 120.8 . . ?
C36 C37 C38 121.1(6) . . ?
C36 C37 C39 119.5(6) . . ?
C38 C37 C39 119.3(6) . . ?
C33 C38 C37 120.2(7) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
F4 C39 F5 105.2(5) . . ?
F4 C39 F6 104.7(6) . . ?
F4 C39 C37 113.6(5) . . ?
F5 C39 C37 112.7(6) . . ?
F6 C39 F5 106.4(5) . . ?
F6 C39 C37 113.5(5) . . ?
F1 C40 C35 112.8(5) . . ?
F2 C40 F1 104.9(6) . . ?
F2 C40 C35 112.6(6) . . ?
F3 C40 F1 106.0(6) . . ?
F3 C40 F2 105.7(5) . . ?
F3 C40 C35 114.2(6) . . ?
N1 C41 H41A 108.7 . . ?
N1 C41 H41B 108.7 . . ?
N1 C41 C42 114.4(5) . . ?
H41A C41 H41B 107.6 . . ?
C42 C41 H41A 108.7 . . ?
C42 C41 H41B 108.7 . . ?
C43 C42 C41 118.8(6) . . ?
C43 C42 C47 120.0(6) . . ?
C47 C42 C41 121.0(6) . . ?
C42 C43 H43 119.3 . . ?
C42 C43 C44 121.4(6) . . ?
C44 C43 H43 119.3 . . ?
C43 C44 C45 119.2(6) . . ?
C43 C44 C49 121.9(6) . . ?
C45 C44 C49 118.9(6) . . ?
C44 C45 H45 120.8 . . ?
C46 C45 C44 118.3(6) . . ?
C46 C45 H45 120.8 . . ?
C45 C46 C47 122.7(6) . . ?
C45 C46 C48 118.1(6) . . ?
C47 C46 C48 119.2(7) . . ?
C42 C47 C46 118.3(6) . . ?
C42 C47 H47 120.8 . . ?
C46 C47 H47 120.8 . . ?
F10 C48 C46 113.1(7) . . ?
F11 C48 F10 100.7(8) . . ?
F11 C48 C46 112.7(8) . . ?
F12 C48 F10 106.5(8) . . ?
F12 C48 F11 106.2(7) . . ?
F12 C48 C46 116.1(6) . . ?
F7 C49 F9 104.1(7) . . ?
F7 C49 C44 113.7(6) . . ?
F8 C49 F7 105.5(5) . . ?
F8 C49 F9 106.5(6) . . ?
F8 C49 C44 114.3(6) . . ?
F9 C49 C44 111.8(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
