# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2131046'
loop_
_audit_author_name
_audit_author_address
'Ding Guanyu'
;Changchun University of Science and Technology
China
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C27 H22 N3'
_chemical_formula_sum            'C27 H22 F6 N3 P'
_chemical_formula_weight         533.44
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.9009(4)
_cell_length_b                   29.1051(18)
_cell_length_c                   14.6172(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.585(4)
_cell_angle_gamma                90
_cell_volume                     2502.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      63.463
_cell_measurement_theta_min      3.037
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.571
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32290
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        63.915
_diffrn_reflns_theta_max         63.915
_diffrn_reflns_theta_min         3.037
_diffrn_ambient_temperature      273.58
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3198
_reflns_number_total             4114
_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       ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0846
_refine_ls_restrained_S_all      1.041
_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)+(0.0993P)²+5.6970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2160
_refine_ls_wR_factor_ref         0.2288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C19(H19), C11(H11), C15(H15), C9(H9), C12(H12), C5(H5), C21(H21),
 C17(H17), C3(H3), C18(H18), C14(H14), C20(H20), C6(H6), C27(H27), C23(H23),
 C26(H26), C25(H25), C24(H24)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 1.0524(2) 0.28682(4) 0.55158(8) 0.0488(4) Uani 1 1 d . . . . .
F1 F 1.0247(8) 0.31261(16) 0.4571(3) 0.1240(16) Uani 1 1 d . . . . .
F2 F 1.0876(8) 0.25927(19) 0.6438(3) 0.1311(18) Uani 1 1 d . . . . .
F3 F 1.3056(7) 0.27912(19) 0.5370(4) 0.1341(18) Uani 1 1 d . . . . .
F4 F 0.7974(7) 0.2893(3) 0.5600(4) 0.181(3) Uani 1 1 d . . . . .
F5 F 0.9987(11) 0.24113(17) 0.4953(4) 0.150(2) Uani 1 1 d . . . . .
F6 F 1.1129(14) 0.33008(17) 0.6037(5) 0.201(3) Uani 1 1 d . . . . .
N1 N 0.8825(7) 0.25664(12) 0.8301(2) 0.0464(9) Uani 1 1 d . . . . .
N3 N -0.2255(6) 0.54842(12) 0.7440(3) 0.0482(9) Uani 1 1 d . . . . .
N2 N 0.6882(8) 0.43497(17) 0.9762(3) 0.0760(14) Uani 1 1 d . . . . .
C4 C 0.6443(7) 0.33872(14) 0.8396(3) 0.0408(10) Uani 1 1 d . . . . .
C16 C -0.1698(7) 0.58965(14) 0.7961(3) 0.0430(10) Uani 1 1 d . . . . .
C7 C 0.5167(8) 0.38133(14) 0.8492(3) 0.0424(10) Uani 1 1 d . . . . .
C13 C -0.1067(8) 0.50858(14) 0.7633(3) 0.0442(10) Uani 1 1 d . . . . .
C22 C -0.3898(8) 0.55448(14) 0.6673(3) 0.0462(11) Uani 1 1 d . . . . .
C2 C 0.9674(9) 0.29052(17) 0.8838(3) 0.0547(12) Uani 1 1 d . . . . .
H2 H 1.105644 0.286395 0.918046 0.066 Uiso 1 1 calc R . . . .
C19 C -0.0839(9) 0.67096(16) 0.8879(3) 0.0562(13) Uani 1 1 d . . . . .
H19 H -0.056375 0.698896 0.917648 0.067 Uiso 1 1 calc R . . . .
C11 C 0.1820(8) 0.46714(15) 0.8564(3) 0.0501(11) Uani 1 1 d . . . . .
H11 H 0.282499 0.465935 0.908705 0.060 Uiso 1 1 calc R . . . .
C15 C 0.0069(9) 0.43267(15) 0.7202(3) 0.0581(13) Uani 1 1 d . . . . .
H15 H -0.012209 0.407605 0.680865 0.070 Uiso 1 1 calc R . . . .
C9 C 0.3221(8) 0.39102(14) 0.7965(3) 0.0499(11) Uani 1 1 d . . . . .
H9 H 0.277283 0.368062 0.754598 0.060 Uiso 1 1 calc R . . . .
C10 C 0.1727(8) 0.43017(14) 0.7934(3) 0.0494(11) Uani 1 1 d . . . . .
C12 C 0.0447(8) 0.50458(15) 0.8412(3) 0.0486(11) Uani 1 1 d . . . . .
H12 H 0.052365 0.528196 0.884159 0.058 Uiso 1 1 calc R . . . .
C5 C 0.5680(9) 0.30275(16) 0.7814(3) 0.0540(12) Uani 1 1 d . . . . .
H5 H 0.434321 0.306096 0.743732 0.065 Uiso 1 1 calc R . . . .
C21 C -0.3244(8) 0.60626(16) 0.8532(3) 0.0511(11) Uani 1 1 d . . . . .
H21 H -0.456980 0.589970 0.861094 0.061 Uiso 1 1 calc R . . . .
C8 C 0.6090(8) 0.41187(15) 0.9196(3) 0.0486(11) Uani 1 1 d . . . . .
C17 C 0.0297(8) 0.61256(16) 0.7865(3) 0.0528(11) Uani 1 1 d . . . . .
H17 H 0.135387 0.600753 0.748787 0.063 Uiso 1 1 calc R . . . .
C3 C 0.8531(8) 0.33156(16) 0.8892(3) 0.0512(11) Uani 1 1 d . . . . .
H3 H 0.916116 0.354873 0.926614 0.061 Uiso 1 1 calc R . . . .
C18 C 0.0732(9) 0.65348(16) 0.8333(4) 0.0596(13) Uani 1 1 d . . . . .
H18 H 0.209095 0.669019 0.827650 0.072 Uiso 1 1 calc R . . . .
C14 C -0.1292(9) 0.47028(15) 0.7035(3) 0.0551(13) Uani 1 1 d . . . . .
H14 H -0.235881 0.470694 0.653101 0.066 Uiso 1 1 calc R . . . .
C20 C -0.2815(10) 0.64763(18) 0.8991(3) 0.0618(14) Uani 1 1 d . . . . .
H20 H -0.386314 0.659360 0.937240 0.074 Uiso 1 1 calc R . . . .
C6 C 0.6885(9) 0.26295(16) 0.7796(3) 0.0565(12) Uani 1 1 d . . . . .
H6 H 0.632440 0.239266 0.741528 0.068 Uiso 1 1 calc R . . . .
C27 C -0.5829(9) 0.52746(18) 0.6560(3) 0.0580(13) Uani 1 1 d . . . . .
H27 H -0.603609 0.503309 0.696124 0.070 Uiso 1 1 calc R . . . .
C23 C -0.3593(11) 0.58985(17) 0.6055(4) 0.0671(15) Uani 1 1 d . . . . .
H23 H -0.227431 0.607459 0.611304 0.081 Uiso 1 1 calc R . . . .
C26 C -0.7452(10) 0.5366(2) 0.5844(4) 0.0714(16) Uani 1 1 d . . . . .
H26 H -0.873528 0.518044 0.575919 0.086 Uiso 1 1 calc R . . . .
C1 C 1.0004(10) 0.21196(17) 0.8310(4) 0.0657(15) Uani 1 1 d . . . . .
H1A H 1.160064 0.216872 0.826537 0.099 Uiso 1 1 calc GR . . . .
H1B H 0.940236 0.193818 0.779820 0.099 Uiso 1 1 calc GR . . . .
H1C H 0.977823 0.196117 0.887111 0.099 Uiso 1 1 calc GR . . . .
C25 C -0.7183(12) 0.5727(2) 0.5261(4) 0.083(2) Uani 1 1 d . . . . .
H25 H -0.831378 0.579399 0.480017 0.099 Uiso 1 1 calc R . . . .
C24 C -0.5251(14) 0.5989(2) 0.5355(4) 0.088(2) Uani 1 1 d . . . . .
H24 H -0.505299 0.622783 0.494695 0.105 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
P1 F1 1.569(4) . ?
P1 F2 1.568(4) . ?
P1 F3 1.542(4) . ?
P1 F4 1.521(4) . ?
P1 F5 1.582(4) . ?
P1 F6 1.499(4) . ?
N1 C2 1.333(6) . ?
N1 C6 1.324(6) . ?
N1 C1 1.475(6) . ?
N3 C16 1.444(5) . ?
N3 C13 1.372(5) . ?
N3 C22 1.434(5) . ?
N2 C8 1.138(6) . ?
C4 C7 1.463(6) . ?
C4 C5 1.401(6) . ?
C4 C3 1.395(6) . ?
C16 C21 1.373(6) . ?
C16 C17 1.370(6) . ?
C7 C9 1.360(6) . ?
C7 C8 1.434(6) . ?
C13 C12 1.394(6) . ?
C13 C14 1.416(6) . ?
C22 C27 1.383(7) . ?
C22 C23 1.390(7) . ?
C2 C3 1.377(6) . ?
C19 C18 1.369(7) . ?
C19 C20 1.370(7) . ?
C11 C10 1.415(6) . ?
C11 C12 1.365(6) . ?
C15 C10 1.393(6) . ?
C15 C14 1.368(6) . ?
C9 C10 1.439(6) . ?
C5 C6 1.361(6) . ?
C21 C20 1.392(7) . ?
C17 C18 1.388(7) . ?
C27 C26 1.387(7) . ?
C23 C24 1.384(8) . ?
C26 C25 1.370(9) . ?
C25 C24 1.369(9) . ?

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
F1 P1 F5 86.7(3) . . ?
F2 P1 F1 177.2(3) . . ?
F2 P1 F5 91.4(3) . . ?
F3 P1 F1 89.0(3) . . ?
F3 P1 F2 88.9(3) . . ?
F3 P1 F5 87.8(3) . . ?
F4 P1 F1 90.8(3) . . ?
F4 P1 F2 91.0(3) . . ?
F4 P1 F3 173.4(4) . . ?
F4 P1 F5 85.6(4) . . ?
F6 P1 F1 92.8(3) . . ?
F6 P1 F2 89.0(3) . . ?
F6 P1 F3 89.9(4) . . ?
F6 P1 F4 96.7(4) . . ?
F6 P1 F5 177.7(4) . . ?
C2 N1 C1 119.5(4) . . ?
C6 N1 C2 119.6(4) . . ?
C6 N1 C1 120.9(4) . . ?
C13 N3 C16 120.2(3) . . ?
C13 N3 C22 124.5(3) . . ?
C22 N3 C16 114.9(3) . . ?
C5 C4 C7 123.3(4) . . ?
C3 C4 C7 121.1(4) . . ?
C3 C4 C5 115.6(4) . . ?
C21 C16 N3 118.6(4) . . ?
C17 C16 N3 120.8(4) . . ?
C17 C16 C21 120.6(4) . . ?
C9 C7 C4 122.6(4) . . ?
C9 C7 C8 122.2(4) . . ?
C8 C7 C4 115.2(4) . . ?
N3 C13 C12 121.4(4) . . ?
N3 C13 C14 121.2(4) . . ?
C12 C13 C14 117.4(4) . . ?
C27 C22 N3 121.5(4) . . ?
C27 C22 C23 119.4(4) . . ?
C23 C22 N3 119.0(4) . . ?
N1 C2 C3 120.8(4) . . ?
C18 C19 C20 120.5(4) . . ?
C12 C11 C10 120.6(4) . . ?
C14 C15 C10 123.0(4) . . ?
C7 C9 C10 132.0(4) . . ?
C11 C10 C9 126.2(4) . . ?
C15 C10 C11 116.7(4) . . ?
C15 C10 C9 117.2(4) . . ?
C11 C12 C13 122.2(4) . . ?
C6 C5 C4 120.3(4) . . ?
C16 C21 C20 119.6(5) . . ?
N2 C8 C7 177.5(5) . . ?
C16 C17 C18 119.6(5) . . ?
C2 C3 C4 121.1(4) . . ?
C19 C18 C17 120.0(5) . . ?
C15 C14 C13 119.7(4) . . ?
C19 C20 C21 119.7(5) . . ?
N1 C6 C5 122.5(4) . . ?
C22 C27 C26 119.6(5) . . ?
C24 C23 C22 120.0(6) . . ?
C25 C26 C27 120.6(6) . . ?
C24 C25 C26 120.1(5) . . ?
C25 C24 C23 120.2(6) . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2131047'
loop_
_audit_author_name
_audit_author_address
'Ding Guanyu'
;Changchun University of Science and Technology
China
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H24 N3 S, F6 P'
_chemical_formula_sum            'C31 H24 F6 N3 P S'
_chemical_formula_weight         615.56
_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   19.1907(5)
_cell_length_b                   8.6600(2)
_cell_length_c                   33.8602(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5627.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6722
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.790
_cell_measurement_theta_min      3.482
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.155
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            29550
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        63.570
_diffrn_reflns_theta_max         63.570
_diffrn_reflns_theta_min         3.481
_diffrn_ambient_temperature      173.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3071
_reflns_number_total             4565
_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       ?
_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         0.614
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.016
_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)+(0.0635P)²+9.7639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C15(H15), C5(H5), C19(H19), C3(H3), C11(H11), C25(H25),
 C31(H31), C2(H2), C16(H16), C12(H12), C6(H6), C21(H21), C27(H27), C30(H30),
 C29(H29), C23(H23), C28(H28), C22(H22), C24(H24)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
S001 S 0.24266(5) 0.45389(12) 0.34037(3) 0.0313(3) Uani 1 1 d . . . . .
P1 P 0.39457(6) -0.39469(14) 0.17810(4) 0.0424(3) Uani 1 1 d . . . . .
F1 F 0.46197(14) -0.2950(4) 0.18546(9) 0.0733(9) Uani 1 1 d . . . . .
F5 F 0.43882(14) -0.5406(4) 0.16674(10) 0.0811(10) Uani 1 1 d . . . . .
N1 N 0.42371(17) 0.0710(4) 0.16827(9) 0.0356(9) Uani 1 1 d . . . . .
N3 N 0.13405(18) 0.9150(4) 0.48634(10) 0.0380(9) Uani 1 1 d . . . . .
F3 F 0.34811(16) -0.2478(4) 0.18638(13) 0.1033(14) Uani 1 1 d . . . . .
F4 F 0.32679(15) -0.4926(4) 0.16868(13) 0.0969(13) Uani 1 1 d . . . . .
N2 N 0.40095(18) 0.4112(5) 0.31608(11) 0.0441(9) Uani 1 1 d . . . . .
F6 F 0.39759(19) -0.3437(4) 0.13284(9) 0.0960(12) Uani 1 1 d . . . . .
C14 C 0.15249(18) 0.6108(4) 0.38906(11) 0.0280(9) Uani 1 1 d . . . . .
C26 C 0.11293(19) 1.0691(5) 0.48230(12) 0.0325(10) Uani 1 1 d . . . . .
C7 C 0.32136(18) 0.2670(5) 0.26697(11) 0.0285(9) Uani 1 1 d . . . . .
F2 F 0.3889(3) -0.4412(4) 0.22195(10) 0.1227(17) Uani 1 1 d . . . . .
C8 C 0.3662(2) 0.3456(5) 0.29423(12) 0.0318(10) Uani 1 1 d . . . . .
C4 C 0.35651(19) 0.1920(5) 0.23362(11) 0.0294(9) Uani 1 1 d . . . . .
C17 C 0.1394(2) 0.8131(5) 0.45362(12) 0.0329(10) Uani 1 1 d . . . . .
C18 C 0.0835(2) 0.7874(5) 0.42827(12) 0.0337(10) Uani 1 1 d . . . . .
H18 H 0.040367 0.837795 0.433021 0.040 Uiso 1 1 calc R . . . .
C9 C 0.2512(2) 0.2755(5) 0.27101(11) 0.0308(9) Uani 1 1 d . . . . .
H9 H 0.225181 0.221074 0.251624 0.037 Uiso 1 1 calc R . . . .
C15 C 0.2071(2) 0.6348(5) 0.41543(12) 0.0379(11) Uani 1 1 d . . . . .
H15 H 0.249732 0.581386 0.411377 0.045 Uiso 1 1 calc R . . . .
C10 C 0.21053(19) 0.3540(5) 0.30008(11) 0.0296(9) Uani 1 1 d . . . . .
C5 C 0.3194(2) 0.1350(5) 0.20126(12) 0.0382(11) Uani 1 1 d . . . . .
H5 H 0.269919 0.137302 0.201380 0.046 Uiso 1 1 calc R . . . .
C19 C 0.09002(19) 0.6897(5) 0.39635(12) 0.0324(10) Uani 1 1 d . . . . .
H19 H 0.051586 0.675615 0.379040 0.039 Uiso 1 1 calc R . . . .
C20 C 0.1583(2) 0.8568(5) 0.52359(12) 0.0340(10) Uani 1 1 d . . . . .
C3 C 0.4286(2) 0.1763(5) 0.23204(12) 0.0389(11) Uani 1 1 d . . . . .
H3 H 0.455925 0.206887 0.254077 0.047 Uiso 1 1 calc R . . . .
C13 C 0.16038(19) 0.5118(4) 0.35470(11) 0.0283(9) Uani 1 1 d . . . . .
C11 C 0.1390(2) 0.3655(5) 0.29877(12) 0.0361(10) Uani 1 1 d . . . . .
H11 H 0.111270 0.317154 0.279094 0.043 Uiso 1 1 calc R . . . .
C25 C 0.1186(2) 0.7474(5) 0.54241(13) 0.0419(11) Uani 1 1 d . . . . .
H25 H 0.075259 0.715139 0.531659 0.050 Uiso 1 1 calc R . . . .
C31 C 0.1058(2) 1.1394(5) 0.44530(13) 0.0364(10) Uani 1 1 d . . . . .
H31 H 0.114275 1.081308 0.421990 0.044 Uiso 1 1 calc R . . . .
C2 C 0.4603(2) 0.1183(5) 0.19963(13) 0.0427(11) Uani 1 1 d . . . . .
H2 H 0.509674 0.111000 0.199120 0.051 Uiso 1 1 calc R . . . .
C16 C 0.2014(2) 0.7329(5) 0.44701(13) 0.0394(11) Uani 1 1 d . . . . .
H16 H 0.239753 0.746401 0.464433 0.047 Uiso 1 1 calc R . . . .
C12 C 0.1113(2) 0.4549(5) 0.32910(12) 0.0385(11) Uani 1 1 d . . . . .
H12 H 0.062829 0.474722 0.331825 0.046 Uiso 1 1 calc R . . . .
C6 C 0.3540(2) 0.0763(5) 0.16956(13) 0.0413(11) Uani 1 1 d . . . . .
H6 H 0.327978 0.037996 0.147775 0.050 Uiso 1 1 calc R . . . .
C21 C 0.2213(2) 0.9034(5) 0.53886(13) 0.0438(11) Uani 1 1 d . . . . .
H21 H 0.248142 0.979708 0.525650 0.053 Uiso 1 1 calc R . . . .
C27 C 0.1001(2) 1.1585(5) 0.51593(13) 0.0409(11) Uani 1 1 d . . . . .
H27 H 0.104096 1.113371 0.541405 0.049 Uiso 1 1 calc R . . . .
C30 C 0.0865(2) 1.2922(5) 0.44250(14) 0.0447(12) Uani 1 1 d . . . . .
H30 H 0.081565 1.338292 0.417187 0.054 Uiso 1 1 calc R . . . .
C29 C 0.0744(2) 1.3794(5) 0.47589(15) 0.0508(12) Uani 1 1 d . . . . .
H29 H 0.061243 1.484842 0.473636 0.061 Uiso 1 1 calc R . . . .
C1 C 0.4591(2) 0.0170(6) 0.13204(13) 0.0492(13) Uani 1 1 d . . . . .
H1A H 0.458995 0.099840 0.112322 0.074 Uiso 1 1 calc GR . . . .
H1B H 0.434439 -0.073096 0.121477 0.074 Uiso 1 1 calc GR . . . .
H1C H 0.507243 -0.011512 0.138302 0.074 Uiso 1 1 calc GR . . . .
C23 C 0.2069(3) 0.7288(6) 0.59275(14) 0.0523(13) Uani 1 1 d . . . . .
H23 H 0.223992 0.683290 0.616376 0.063 Uiso 1 1 calc R . . . .
C28 C 0.0814(2) 1.3127(5) 0.51229(15) 0.0494(12) Uani 1 1 d . . . . .
H28 H 0.073480 1.372625 0.535354 0.059 Uiso 1 1 calc R . . . .
C22 C 0.2453(3) 0.8382(6) 0.57365(14) 0.0512(12) Uani 1 1 d . . . . .
H22 H 0.288805 0.870000 0.584280 0.061 Uiso 1 1 calc R . . . .
C24 C 0.1434(3) 0.6843(5) 0.57777(14) 0.0527(13) Uani 1 1 d . . . . .
H24 H 0.116148 0.610206 0.591538 0.063 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
S001 C10 1.729(4) . ?
S001 C13 1.726(4) . ?
P1 F1 1.575(3) . ?
P1 F5 1.570(3) . ?
P1 F3 1.578(3) . ?
P1 F4 1.585(3) . ?
P1 F6 1.596(3) . ?
P1 F2 1.542(3) . ?
N1 C2 1.337(5) . ?
N1 C6 1.340(5) . ?
N1 C1 1.478(5) . ?
N3 C26 1.402(5) . ?
N3 C17 1.420(5) . ?
N3 C20 1.436(5) . ?
N2 C8 1.147(5) . ?
C14 C15 1.392(5) . ?
C14 C19 1.402(5) . ?
C14 C13 1.454(5) . ?
C26 C31 1.399(6) . ?
C26 C27 1.399(6) . ?
C7 C8 1.433(6) . ?
C7 C4 1.467(5) . ?
C7 C9 1.356(5) . ?
C4 C5 1.397(5) . ?
C4 C3 1.391(5) . ?
C17 C18 1.391(5) . ?
C17 C16 1.396(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.428(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(6) . ?
C10 C11 1.377(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.360(6) . ?
C19 H19 0.9500 . ?
C20 C25 1.373(6) . ?
C20 C21 1.375(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.352(6) . ?
C13 C12 1.372(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(6) . ?
C25 H25 0.9500 . ?
C25 C24 1.400(6) . ?
C31 H31 0.9500 . ?
C31 C30 1.378(6) . ?
C2 H2 0.9500 . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
C6 H6 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.385(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(6) . ?
C30 H30 0.9500 . ?
C30 C29 1.380(6) . ?
C29 H29 0.9500 . ?
C29 C28 1.368(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C22 1.364(7) . ?
C23 C24 1.375(7) . ?
C28 H28 0.9500 . ?
C22 H22 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S001 C10 92.34(18) . . ?
F1 P1 F3 89.67(18) . . ?
F1 P1 F4 177.4(2) . . ?
F1 P1 F6 88.30(18) . . ?
F5 P1 F1 92.03(17) . . ?
F5 P1 F3 175.9(2) . . ?
F5 P1 F4 87.93(17) . . ?
F5 P1 F6 88.2(2) . . ?
F3 P1 F4 90.20(18) . . ?
F3 P1 F6 88.2(2) . . ?
F4 P1 F6 89.1(2) . . ?
F2 P1 F1 92.8(2) . . ?
F2 P1 F5 93.7(2) . . ?
F2 P1 F3 90.0(2) . . ?
F2 P1 F4 89.8(2) . . ?
F2 P1 F6 177.8(3) . . ?
C2 N1 C6 119.2(4) . . ?
C2 N1 C1 121.0(4) . . ?
C6 N1 C1 119.8(4) . . ?
C26 N3 C17 122.5(3) . . ?
C26 N3 C20 120.9(3) . . ?
C17 N3 C20 116.4(3) . . ?
C15 C14 C19 117.3(4) . . ?
C15 C14 C13 121.5(3) . . ?
C19 C14 C13 121.2(3) . . ?
C31 C26 N3 122.0(4) . . ?
C27 C26 N3 119.9(4) . . ?
C27 C26 C31 118.1(4) . . ?
C8 C7 C4 115.5(3) . . ?
C9 C7 C8 120.3(4) . . ?
C9 C7 C4 123.9(3) . . ?
N2 C8 C7 178.4(4) . . ?
C5 C4 C7 121.7(3) . . ?
C3 C4 C7 122.0(4) . . ?
C3 C4 C5 116.2(4) . . ?
C18 C17 N3 121.7(4) . . ?
C18 C17 C16 118.6(4) . . ?
C16 C17 N3 119.7(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C7 C9 H9 115.2 . . ?
C7 C9 C10 129.7(4) . . ?
C10 C9 H9 115.2 . . ?
C14 C15 H15 118.9 . . ?
C16 C15 C14 122.2(4) . . ?
C16 C15 H15 118.9 . . ?
C9 C10 S001 125.9(3) . . ?
C11 C10 S001 110.2(3) . . ?
C11 C10 C9 123.9(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C25 C20 N3 118.0(4) . . ?
C25 C20 C21 121.0(4) . . ?
C21 C20 N3 120.8(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C14 C13 S001 119.4(3) . . ?
C12 C13 S001 110.3(3) . . ?
C12 C13 C14 130.2(3) . . ?
C10 C11 H11 123.3 . . ?
C10 C11 C12 113.4(4) . . ?
C12 C11 H11 123.3 . . ?
C20 C25 H25 120.7 . . ?
C20 C25 C24 118.5(4) . . ?
C24 C25 H25 120.7 . . ?
C26 C31 H31 119.8 . . ?
C30 C31 C26 120.4(4) . . ?
C30 C31 H31 119.8 . . ?
N1 C2 C3 121.5(4) . . ?
N1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 120.0 . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12 123.1 . . ?
C11 C12 H12 123.1 . . ?
N1 C6 C5 121.7(4) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.5(5) . . ?
C22 C21 H21 120.2 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.4(4) . . ?
C28 C27 H27 119.8 . . ?
C31 C30 H30 119.5 . . ?
C31 C30 C29 121.0(4) . . ?
C29 C30 H30 119.5 . . ?
C30 C29 H29 120.3 . . ?
C28 C29 C30 119.4(4) . . ?
C28 C29 H29 120.3 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.9(5) . . ?
C24 C23 H23 120.0 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(5) . . ?
C29 C28 H28 119.6 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.5(5) . . ?
C23 C22 H22 119.8 . . ?
C25 C24 H24 119.7 . . ?
C23 C24 C25 120.5(5) . . ?
C23 C24 H24 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
