# Supplementary Information (SI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_Ph-cy5-NO2
_database_code_depnum_ccdc_archive 'CCDC 2423384'
loop_
_audit_author_name
_audit_author_address
'Siye Wu'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2025-02-12 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;
_audit_creation_date             2024-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C31 H30 N3 O3'
_chemical_formula_sum            'C31 H30 F6 N3 O3 P'
_chemical_formula_weight         637.55
_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 0.0253 0.0136 '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      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                   8.8295(11)
_cell_length_b                   12.5155(16)
_cell_length_c                   14.1971(18)
_cell_angle_alpha                103.818(4)
_cell_angle_beta                 98.499(4)
_cell_angle_gamma                104.496(4)
_cell_volume                     1438.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      57.01
_cell_measurement_theta_min      4.61
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    0.994
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1521 before and 0.0949 after correction. The Ratio of minimum to maximum transmission is 0.7589. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'bluish black'
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20064
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.006
_diffrn_reflns_theta_min         4.614
_diffrn_ambient_temperature      106.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5148
_reflns_number_total             5782
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 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         0.793
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         5782
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.094
_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)+(0.0926P)²+0.7769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.1632
_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.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C15(H15), C17(H17), C10(H10), C9(H9), C21(H21), C13(H13), C5(H5),
 C20(H20), C2(H2), C12(H12), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C31(H31A,H31B,H31C), C25(H25A,H25B,H25C), C29(H29A,H29B,
 H29C), C28(H28A,H28B,H28C)
;
_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 0.79728(6) 0.54128(4) 0.81680(4) 0.02354(17) Uani 1 1 d . . . . .
F2 F 0.71706(16) 0.56808(12) 0.91080(9) 0.0360(3) Uani 1 1 d . . . . .
F1 F 0.65056(16) 0.56174(12) 0.74921(9) 0.0363(3) Uani 1 1 d . . . . .
F6 F 0.94345(16) 0.52265(13) 0.88567(11) 0.0422(4) Uani 1 1 d . . . . .
O1 O 0.03132(16) 0.39260(11) 0.52917(10) 0.0230(3) Uani 1 1 d . . . . .
F5 F 0.70088(17) 0.40810(11) 0.79031(12) 0.0432(4) Uani 1 1 d . . . . .
F3 F 0.89268(18) 0.67547(12) 0.84416(11) 0.0428(4) Uani 1 1 d . . . . .
F4 F 0.87767(17) 0.51484(15) 0.72400(10) 0.0486(4) Uani 1 1 d . . . . .
O3 O 0.73152(17) 1.07348(12) 1.12583(11) 0.0291(3) Uani 1 1 d . . . . .
O2 O 0.5528(2) 1.02669(13) 1.21091(11) 0.0328(4) Uani 1 1 d . . . . .
N2 N 0.32363(18) 0.58524(12) 0.84071(11) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.15792(19) -0.08280(13) 0.37600(11) 0.0182(3) Uani 1 1 d . . . . .
N3 N 0.6101(2) 1.00838(14) 1.13718(12) 0.0241(4) Uani 1 1 d . . . . .
C23 C 0.2374(2) 0.46146(14) 0.67525(13) 0.0166(4) Uani 1 1 d . . . . .
C24 C 0.2743(2) 0.37132(15) 0.70962(13) 0.0166(4) Uani 1 1 d . . . . .
C18 C 0.6057(2) 0.87243(15) 0.98026(14) 0.0202(4) Uani 1 1 d . . . . .
H18 H 0.705281 0.922285 0.978500 0.024 Uiso 1 1 calc R . . . .
C22 C 0.2650(2) 0.56876(15) 0.74205(13) 0.0170(4) Uani 1 1 d . . . . .
C14 C 0.3260(2) 0.39209(15) 0.81282(13) 0.0180(4) Uani 1 1 d . . . . .
C15 C 0.3486(2) 0.49716(16) 0.87637(14) 0.0193(4) Uani 1 1 d . . . . .
H15 H 0.381775 0.509838 0.945918 0.023 Uiso 1 1 calc R . . . .
C11 C 0.2690(2) 0.25568(15) 0.65921(13) 0.0172(4) Uani 1 1 d . . . . .
C16 C 0.3864(2) 0.69916(15) 0.91141(13) 0.0181(4) Uani 1 1 d . . . . .
C17 C 0.5335(2) 0.76841(15) 0.90681(14) 0.0197(4) Uani 1 1 d . . . . .
H17 H 0.583933 0.744923 0.854166 0.024 Uiso 1 1 calc R . . . .
C10 C 0.2305(2) 0.20376(15) 0.55879(14) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.209141 0.248610 0.515965 0.021 Uiso 1 1 calc R . . . .
C8 C 0.1775(2) 0.03247(15) 0.41455(13) 0.0168(4) Uani 1 1 d . . . . .
C19 C 0.5281(2) 0.90122(15) 1.05607(14) 0.0204(4) Uani 1 1 d . . . . .
C6 C 0.0997(2) -0.02281(15) 0.23911(14) 0.0194(4) Uani 1 1 d . . . . .
C30 C 0.1706(2) 0.44505(15) 0.56672(13) 0.0188(4) Uani 1 1 d . . . . .
C1 C 0.1096(2) -0.11755(15) 0.27196(13) 0.0187(4) Uani 1 1 d . . . . .
C7 C 0.1464(2) 0.08353(15) 0.32811(13) 0.0184(4) Uani 1 1 d . . . . .
C9 C 0.2205(2) 0.08762(15) 0.51488(13) 0.0177(4) Uani 1 1 d . . . . .
H9 H 0.245556 0.044162 0.558180 0.021 Uiso 1 1 calc R . . . .
C21 C 0.3072(2) 0.73012(16) 0.98610(14) 0.0215(4) Uani 1 1 d . . . . .
H21 H 0.205384 0.681954 0.986410 0.026 Uiso 1 1 calc R . . . .
C27 C 0.1754(2) -0.16372(15) 0.43298(14) 0.0204(4) Uani 1 1 d . . . . .
H27A H 0.099422 -0.240603 0.396579 0.025 Uiso 1 1 calc R . . . .
H27B H 0.147042 -0.137995 0.497782 0.025 Uiso 1 1 calc R . . . .
C26 C 0.0087(2) 0.13863(16) 0.32943(14) 0.0223(4) Uani 1 1 d . . . . .
H26A H -0.087620 0.083531 0.335324 0.034 Uiso 1 1 calc GR . . . .
H26B H -0.013835 0.159344 0.267589 0.034 Uiso 1 1 calc GR . . . .
H26C H 0.039869 0.208043 0.386202 0.034 Uiso 1 1 calc GR . . . .
C31 C 0.2295(2) 0.66893(15) 0.71215(14) 0.0224(4) Uani 1 1 d . . . . .
H31A H 0.178879 0.708353 0.760838 0.034 Uiso 1 1 calc GR . . . .
H31B H 0.156882 0.640859 0.646370 0.034 Uiso 1 1 calc GR . . . .
H31C H 0.329747 0.722849 0.709743 0.034 Uiso 1 1 calc GR . . . .
C13 C 0.3626(2) 0.28987(15) 0.83746(14) 0.0220(4) Uani 1 1 d . . . . .
H13 H 0.405252 0.283927 0.900829 0.026 Uiso 1 1 calc R . . . .
C5 C 0.0461(2) -0.03651(17) 0.13909(14) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.039423 0.027672 0.115837 0.029 Uiso 1 1 calc R . . . .
C20 C 0.3807(2) 0.83382(16) 1.06082(14) 0.0224(4) Uani 1 1 d . . . . .
H20 H 0.330724 0.857538 1.113649 0.027 Uiso 1 1 calc R . . . .
C2 C 0.0680(2) -0.22859(16) 0.20761(15) 0.0225(4) Uani 1 1 d . . . . .
H2 H 0.077498 -0.292268 0.230901 0.027 Uiso 1 1 calc R . . . .
C12 C 0.3153(2) 0.19694(15) 0.73653(13) 0.0202(4) Uani 1 1 d . . . . .
H12 H 0.314962 0.118900 0.724850 0.024 Uiso 1 1 calc R . . . .
C4 C 0.0020(2) -0.14760(18) 0.07305(15) 0.0267(4) Uani 1 1 d . . . . .
H4 H -0.035109 -0.158975 0.004049 0.032 Uiso 1 1 calc R . . . .
C25 C 0.3018(2) 0.17158(16) 0.32418(15) 0.0252(4) Uani 1 1 d . . . . .
H25A H 0.336426 0.235879 0.385386 0.038 Uiso 1 1 calc GR . . . .
H25B H 0.281208 0.200699 0.266818 0.038 Uiso 1 1 calc GR . . . .
H25C H 0.386142 0.133903 0.317859 0.038 Uiso 1 1 calc GR . . . .
C3 C 0.0119(2) -0.24146(17) 0.10724(15) 0.0253(4) Uani 1 1 d . . . . .
H3 H -0.020422 -0.316117 0.061104 0.030 Uiso 1 1 calc R . . . .
C29 C 0.2863(3) 0.4928(2) 0.50897(16) 0.0323(5) Uani 1 1 d . . . . .
H29A H 0.367287 0.451720 0.505450 0.049 Uiso 1 1 calc GR . . . .
H29B H 0.338911 0.574951 0.542145 0.049 Uiso 1 1 calc GR . . . .
H29C H 0.228206 0.482818 0.441553 0.049 Uiso 1 1 calc GR . . . .
C28 C 0.3439(3) -0.1739(2) 0.4511(2) 0.0400(6) Uani 1 1 d . . . . .
H28A H 0.372923 -0.199150 0.387232 0.060 Uiso 1 1 calc GR . . . .
H28B H 0.348695 -0.230368 0.488009 0.060 Uiso 1 1 calc GR . . . .
H28C H 0.419228 -0.098791 0.489884 0.060 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
P1 F2 1.6062(13) . ?
P1 F1 1.6064(13) . ?
P1 F6 1.6008(14) . ?
P1 F5 1.5936(14) . ?
P1 F3 1.6015(14) . ?
P1 F4 1.5921(14) . ?
O1 C30 1.209(2) . ?
O3 N3 1.231(2) . ?
O2 N3 1.227(2) . ?
N2 C22 1.366(2) . ?
N2 C15 1.369(2) . ?
N2 C16 1.450(2) . ?
N1 C8 1.371(2) . ?
N1 C1 1.402(2) . ?
N1 C27 1.462(2) . ?
N3 C19 1.476(2) . ?
C23 C24 1.420(2) . ?
C23 C22 1.386(2) . ?
C23 C30 1.511(2) . ?
C24 C14 1.408(2) . ?
C24 C11 1.439(2) . ?
C18 C17 1.389(3) . ?
C18 C19 1.383(3) . ?
C22 C31 1.504(2) . ?
C14 C15 1.353(3) . ?
C14 C13 1.500(2) . ?
C11 C10 1.369(3) . ?
C11 C12 1.522(2) . ?
C16 C17 1.390(3) . ?
C16 C21 1.386(3) . ?
C10 C9 1.413(2) . ?
C8 C7 1.534(2) . ?
C8 C9 1.374(3) . ?
C19 C20 1.384(3) . ?
C6 C1 1.391(3) . ?
C6 C7 1.519(2) . ?
C6 C5 1.384(3) . ?
C30 C29 1.499(3) . ?
C1 C2 1.393(2) . ?
C7 C26 1.541(3) . ?
C7 C25 1.548(3) . ?
C21 C20 1.396(3) . ?
C27 C28 1.514(3) . ?
C13 C12 1.538(2) . ?
C5 C4 1.401(3) . ?
C2 C3 1.394(3) . ?
C4 C3 1.391(3) . ?

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
F2 P1 F1 89.39(7) . . ?
F6 P1 F2 89.85(8) . . ?
F6 P1 F1 179.03(8) . . ?
F6 P1 F3 89.65(8) . . ?
F5 P1 F2 89.83(8) . . ?
F5 P1 F1 90.02(8) . . ?
F5 P1 F6 90.58(8) . . ?
F5 P1 F3 179.33(9) . . ?
F3 P1 F2 89.55(8) . . ?
F3 P1 F1 89.74(8) . . ?
F4 P1 F2 179.70(8) . . ?
F4 P1 F1 90.89(8) . . ?
F4 P1 F6 89.87(8) . . ?
F4 P1 F5 90.28(9) . . ?
F4 P1 F3 90.35(9) . . ?
C22 N2 C15 121.83(15) . . ?
C22 N2 C16 122.18(15) . . ?
C15 N2 C16 115.33(15) . . ?
C8 N1 C1 111.30(15) . . ?
C8 N1 C27 126.17(15) . . ?
C1 N1 C27 122.46(15) . . ?
O3 N3 C19 117.47(16) . . ?
O2 N3 O3 124.51(16) . . ?
O2 N3 C19 118.02(17) . . ?
C24 C23 C30 121.97(15) . . ?
C22 C23 C24 119.77(16) . . ?
C22 C23 C30 118.25(15) . . ?
C23 C24 C11 132.74(17) . . ?
C14 C24 C23 118.00(16) . . ?
C14 C24 C11 109.26(15) . . ?
C19 C18 C17 117.95(17) . . ?
N2 C22 C23 119.27(16) . . ?
N2 C22 C31 117.40(15) . . ?
C23 C22 C31 123.30(16) . . ?
C24 C14 C13 111.81(15) . . ?
C15 C14 C24 120.63(17) . . ?
C15 C14 C13 127.38(17) . . ?
C14 C15 N2 120.20(16) . . ?
C24 C11 C12 108.73(15) . . ?
C10 C11 C24 127.39(16) . . ?
C10 C11 C12 123.87(16) . . ?
C17 C16 N2 117.57(16) . . ?
C21 C16 N2 119.44(16) . . ?
C21 C16 C17 122.66(17) . . ?
C18 C17 C16 119.06(17) . . ?
C11 C10 C9 124.08(17) . . ?
N1 C8 C7 108.49(15) . . ?
N1 C8 C9 122.98(16) . . ?
C9 C8 C7 128.52(16) . . ?
C18 C19 N3 117.70(17) . . ?
C18 C19 C20 123.56(17) . . ?
C20 C19 N3 118.73(17) . . ?
C1 C6 C7 109.21(16) . . ?
C5 C6 C1 120.23(17) . . ?
C5 C6 C7 130.49(17) . . ?
O1 C30 C23 120.47(16) . . ?
O1 C30 C29 122.73(18) . . ?
C29 C30 C23 116.76(16) . . ?
C6 C1 N1 109.43(15) . . ?
C6 C1 C2 122.63(17) . . ?
C2 C1 N1 127.87(17) . . ?
C8 C7 C26 114.31(15) . . ?
C8 C7 C25 110.47(15) . . ?
C6 C7 C8 101.50(14) . . ?
C6 C7 C26 109.63(15) . . ?
C6 C7 C25 110.50(15) . . ?
C26 C7 C25 110.13(15) . . ?
C8 C9 C10 125.25(16) . . ?
C16 C21 C20 118.36(17) . . ?
N1 C27 C28 112.66(16) . . ?
C14 C13 C12 104.08(15) . . ?
C6 C5 C4 118.19(18) . . ?
C19 C20 C21 118.38(18) . . ?
C1 C2 C3 116.54(18) . . ?
C11 C12 C13 105.85(14) . . ?
C3 C4 C5 120.82(18) . . ?
C4 C3 C2 121.57(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
