# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_l212-5h2o
_database_code_depnum_ccdc_archive 'CCDC 2286895'
loop_
_audit_author_name
_audit_author_address
'Yu-Ru Xu'
;Fuzhou University
China
;
_audit_update_record             
;
2023-08-05 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'F6 P, C19 H17 N4 O3, 5(H2 O)'
_chemical_formula_sum            'C19 H27 F6 N4 O8 P'
_chemical_formula_weight         584.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'

_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                   8.6215(5)
_cell_length_b                   26.4188(14)
_cell_length_c                   11.3368(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.383(2)
_cell_angle_gamma                90
_cell_volume                     2531.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8756
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.409
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            32369
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         1.988
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3412
_reflns_number_total             4484
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.344
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.038
_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)+(0.0363P)²+1.9462P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O4W(H4WA,H4WB), O2W(H2WA,H2WB), O5W(H5WA,H5WB), O3W(H3WA,H3WB)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C13(H13), C19(H19), C14(H14), C16(H16), C17(H17), C3(H3),
 C10(H10), C4(H4), C6(H6), C18(H18), C11(H11), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.23866(9) 0.40988(2) 0.43065(6) 0.03789(19) Uani 1 1 d . . . . .
O3 O 0.66455(18) 0.21453(6) 0.65001(14) 0.0309(4) Uani 1 1 d . . . . .
O2 O 0.32656(19) 0.18847(5) 0.46290(14) 0.0324(4) Uani 1 1 d . . . . .
O1 O 0.59886(19) 0.05782(6) 0.51025(13) 0.0315(4) Uani 1 1 d . . . . .
H1 H 0.6600 0.0347 0.5036 0.047 Uiso 1 1 calc GR . . . .
O1W O 0.3218(2) 0.28462(6) 0.55855(14) 0.0347(4) Uani 1 1 d . . . . .
H1WA H 0.3156 0.2541 0.5347 0.052 Uiso 1 1 d G . . . .
H1WB H 0.3075 0.3043 0.4981 0.052 Uiso 1 1 d G . . . .
F3 F -0.15117(19) 0.45901(6) 0.39382(14) 0.0557(4) Uani 1 1 d . . . . .
O4W O 0.2552(2) 0.15213(6) 0.85173(16) 0.0362(4) Uani 1 1 d . . . . .
H4WA H 0.2355 0.1208 0.8578 0.054 Uiso 1 1 d G . . . .
H4WB H 0.1714 0.1674 0.8178 0.054 Uiso 1 1 d G . . . .
F4 F -0.2914(2) 0.44238(6) 0.53402(14) 0.0571(5) Uani 1 1 d . . . . .
F6 F -0.0803(2) 0.39488(6) 0.52390(15) 0.0613(5) Uani 1 1 d . . . . .
F1 F -0.3955(2) 0.42531(6) 0.34058(16) 0.0670(5) Uani 1 1 d . . . . .
N1 N 0.4641(2) 0.13456(6) 0.59861(16) 0.0244(4) Uani 1 1 d . . . . .
H1A H 0.5067 0.1052 0.6129 0.029 Uiso 1 1 calc R . . . .
N3 N 0.6645(2) 0.27961(6) 0.83396(16) 0.0227(4) Uani 1 1 d . . . . .
N2 N 0.4613(2) 0.16810(6) 0.69159(16) 0.0241(4) Uani 1 1 d . . . . .
H2 H 0.3934 0.1644 0.7373 0.029 Uiso 1 1 calc R . . . .
O2W O 0.0273(2) 0.29386(7) 0.62130(18) 0.0450(5) Uani 1 1 d . . . . .
H2WA H 0.1174 0.2901 0.6025 0.068 Uiso 1 1 d G . . . .
H2WB H -0.0127 0.3219 0.5935 0.068 Uiso 1 1 d G . . . .
N4 N 1.1902(2) 0.48308(6) 0.97502(16) 0.0246(4) Uani 1 1 d . . . . .
F5 F -0.3228(2) 0.36127(6) 0.47145(17) 0.0767(6) Uani 1 1 d . . . . .
O5W O 0.1824(2) 0.04758(7) 0.86913(17) 0.0479(5) Uani 1 1 d . . . . .
H5WA H 0.2305 0.0223 0.9055 0.072 Uiso 1 1 d G . . . .
H5WB H 0.0938 0.0482 0.8913 0.072 Uiso 1 1 d G . . . .
O3W O 0.0017(2) 0.20792(8) 0.7548(2) 0.0551(5) Uani 1 1 d . . . . .
H3WA H 0.0184 0.2366 0.7260 0.083 Uiso 1 1 d G . . . .
H3WB H -0.0967 0.2014 0.7382 0.083 Uiso 1 1 d G . . . .
F2 F -0.1851(3) 0.37781(8) 0.32975(18) 0.0947(8) Uani 1 1 d . . . . .
C7 C 0.3993(2) 0.14839(8) 0.4851(2) 0.0240(5) Uani 1 1 d . . . . .
C13 C 0.7566(2) 0.35798(8) 0.77679(19) 0.0229(5) Uani 1 1 d . . . . .
H13 H 0.7463 0.3851 0.7234 0.028 Uiso 1 1 calc R . . . .
C12 C 0.8792(2) 0.35756(8) 0.87722(18) 0.0213(5) Uani 1 1 d . . . . .
C8 C 0.5647(2) 0.20620(8) 0.70995(19) 0.0228(5) Uani 1 1 d . . . . .
C1 C 0.5107(3) 0.06900(8) 0.40075(19) 0.0243(5) Uani 1 1 d . . . . .
C19 C 1.0159(3) 0.43591(8) 0.82425(19) 0.0239(5) Uani 1 1 d . . . . .
H19 H 0.9679 0.4323 0.7437 0.029 Uiso 1 1 calc R . . . .
C2 C 0.4147(2) 0.11245(8) 0.38720(19) 0.0223(5) Uani 1 1 d . . . . .
C15 C 0.9854(2) 0.40159(8) 0.90983(19) 0.0218(5) Uani 1 1 d . . . . .
C14 C 0.6512(3) 0.31882(8) 0.7562(2) 0.0243(5) Uani 1 1 d . . . . .
H14 H 0.5703 0.3192 0.6885 0.029 Uiso 1 1 calc R . . . .
C16 C 1.0573(3) 0.41001(8) 1.0290(2) 0.0250(5) Uani 1 1 d . . . . .
H16 H 1.0380 0.3884 1.0891 0.030 Uiso 1 1 calc R . . . .
C17 C 1.1575(3) 0.45066(8) 1.0573(2) 0.0256(5) Uani 1 1 d . . . . .
H17 H 1.2048 0.4558 1.1375 0.031 Uiso 1 1 calc R . . . .
C3 C 0.3265(3) 0.12362(8) 0.27320(19) 0.0261(5) Uani 1 1 d . . . . .
H3 H 0.2624 0.1522 0.2633 0.031 Uiso 1 1 calc R . . . .
C10 C 0.7870(3) 0.27619(8) 0.92617(19) 0.0272(5) Uani 1 1 d . . . . .
H10 H 0.7983 0.2477 0.9752 0.033 Uiso 1 1 calc R . . . .
C4 C 0.3317(3) 0.09351(9) 0.1749(2) 0.0304(5) Uani 1 1 d . . . . .
H4 H 0.2729 0.1019 0.0996 0.036 Uiso 1 1 calc R . . . .
C6 C 0.5131(3) 0.03844(8) 0.3012(2) 0.0287(5) Uani 1 1 d . . . . .
H6 H 0.5749 0.0093 0.3100 0.034 Uiso 1 1 calc R . . . .
C18 C 1.1187(3) 0.47544(8) 0.8609(2) 0.0254(5) Uani 1 1 d . . . . .
H18 H 1.1392 0.4980 0.8029 0.030 Uiso 1 1 calc R . . . .
C11 C 0.8962(3) 0.31439(8) 0.9490(2) 0.0276(5) Uani 1 1 d . . . . .
H11 H 0.9820 0.3115 1.0128 0.033 Uiso 1 1 calc R . . . .
C9 C 0.5429(3) 0.23991(8) 0.8146(2) 0.0272(5) Uani 1 1 d . . . . .
H9A H 0.4387 0.2553 0.7971 0.033 Uiso 1 1 calc R . . . .
H9B H 0.5509 0.2197 0.8869 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4256(3) 0.05064(9) 0.1899(2) 0.0299(5) Uani 1 1 d . . . . .
H5 H 0.4295 0.0299 0.1242 0.036 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 F3 1.5975(17) . ?
P1 F4 1.5899(17) . ?
P1 F6 1.6030(16) . ?
P1 F1 1.5788(17) . ?
P1 F5 1.5881(18) . ?
P1 F2 1.5648(19) . ?
O3 C8 1.217(3) . ?
O2 C7 1.231(3) . ?
O1 C1 1.354(3) . ?
N1 N2 1.381(2) . ?
N1 C7 1.348(3) . ?
N3 C14 1.350(3) . ?
N3 C10 1.335(3) . ?
N3 C9 1.468(3) . ?
N2 C8 1.334(3) . ?
N4 C17 1.336(3) . ?
N4 C18 1.334(3) . ?
C7 C2 1.487(3) . ?
C13 C12 1.392(3) . ?
C13 C14 1.366(3) . ?
C12 C15 1.481(3) . ?
C12 C11 1.392(3) . ?
C8 C9 1.524(3) . ?
C1 C2 1.406(3) . ?
C1 C6 1.392(3) . ?
C19 C15 1.390(3) . ?
C19 C18 1.380(3) . ?
C2 C3 1.396(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.376(3) . ?
C3 C4 1.377(3) . ?
C10 C11 1.369(3) . ?
C4 C5 1.383(3) . ?
C6 C5 1.375(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
F3 P1 F6 89.35(9) . . ?
F4 P1 F3 88.42(9) . . ?
F4 P1 F6 88.74(10) . . ?
F1 P1 F3 90.55(9) . . ?
F1 P1 F4 90.23(10) . . ?
F1 P1 F6 178.97(11) . . ?
F1 P1 F5 90.86(10) . . ?
F5 P1 F3 178.22(10) . . ?
F5 P1 F4 90.48(10) . . ?
F5 P1 F6 89.23(9) . . ?
F2 P1 F3 91.50(12) . . ?
F2 P1 F4 179.43(12) . . ?
F2 P1 F6 90.70(11) . . ?
F2 P1 F1 90.33(11) . . ?
F2 P1 F5 89.59(13) . . ?
C7 N1 N2 119.22(17) . . ?
C14 N3 C9 118.97(18) . . ?
C10 N3 C14 121.00(18) . . ?
C10 N3 C9 120.02(18) . . ?
C8 N2 N1 119.43(18) . . ?
C18 N4 C17 117.31(18) . . ?
O2 C7 N1 121.8(2) . . ?
O2 C7 C2 120.9(2) . . ?
N1 C7 C2 117.27(18) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C12 C15 122.01(19) . . ?
C11 C12 C13 117.37(19) . . ?
C11 C12 C15 120.60(19) . . ?
O3 C8 N2 125.0(2) . . ?
O3 C8 C9 122.56(19) . . ?
N2 C8 C9 112.40(19) . . ?
O1 C1 C2 119.35(19) . . ?
O1 C1 C6 121.45(19) . . ?
C6 C1 C2 119.2(2) . . ?
C18 C19 C15 118.8(2) . . ?
C1 C2 C7 125.28(19) . . ?
C3 C2 C7 116.33(19) . . ?
C3 C2 C1 118.4(2) . . ?
C19 C15 C12 122.05(19) . . ?
C16 C15 C12 120.27(19) . . ?
C16 C15 C19 117.68(19) . . ?
N3 C14 C13 120.1(2) . . ?
C17 C16 C15 119.4(2) . . ?
N4 C17 C16 123.1(2) . . ?
C4 C3 C2 121.9(2) . . ?
N3 C10 C11 120.4(2) . . ?
C3 C4 C5 119.1(2) . . ?
C5 C6 C1 121.0(2) . . ?
N4 C18 C19 123.6(2) . . ?
C10 C11 C12 120.3(2) . . ?
N3 C9 C8 109.87(18) . . ?
C6 C5 C4 120.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 2286896'
loop_
_audit_author_name
_audit_author_address
'Yu-Ru Xu'
;Fuzhou University
China
;
_audit_update_record             
;
2023-08-05 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'F6 P, C19 H17 N4 O3, H2 O'
_chemical_formula_sum            'C19 H19 F6 N4 O4 P'
_chemical_formula_weight         512.35
_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'
O O 0.0106 0.0060 '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'

_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                   5.7747(4)
_cell_length_b                   12.6277(10)
_cell_length_c                   28.442(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.394(2)
_cell_angle_gamma                90
_cell_volume                     2064.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.98
_cell_measurement_theta_min      2.694
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32821
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_min         2.161
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2553
_reflns_number_total             3645
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.236
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.027
_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)+(0.0567P)²+1.6832P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C3(H3), C17(H17), C4(H4), C16(H16), C10(H10), C13(H13),
 C19(H19), C6(H6), C11(H11), C5(H5), C18(H18), C14(H14)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.34774(13) 0.52548(6) 0.84353(3) 0.0299(2) Uani 1 1 d . . . . .
F2 F 0.3845(3) 0.59474(15) 0.79733(6) 0.0427(5) Uani 1 1 d . . . . .
F6 F 0.3848(3) 0.41942(14) 0.81513(7) 0.0472(5) Uani 1 1 d . . . . .
O2 O 0.8338(3) 0.60905(16) 0.47955(7) 0.0301(5) Uani 1 1 d . . . . .
O1 O 0.2627(3) 0.66753(16) 0.55383(7) 0.0303(5) Uani 1 1 d . . . . .
H1 H 0.1516 0.6898 0.5668 0.045 Uiso 1 1 calc GR . . . .
F1 F 0.3051(4) 0.63374(15) 0.87058(7) 0.0527(6) Uani 1 1 d . . . . .
F5 F 0.6157(3) 0.53240(16) 0.85906(7) 0.0517(5) Uani 1 1 d . . . . .
F3 F 0.0775(3) 0.51999(15) 0.82680(9) 0.0640(7) Uani 1 1 d . . . . .
O3 O 0.5991(4) 0.46265(18) 0.61976(7) 0.0460(6) Uani 1 1 d . . . . .
N1 N 0.6414(4) 0.56682(18) 0.54192(8) 0.0233(5) Uani 1 1 d . . . . .
H1A H 0.5234 0.5790 0.5575 0.028 Uiso 1 1 calc R . . . .
F4 F 0.3081(4) 0.45885(17) 0.88902(8) 0.0670(7) Uani 1 1 d . . . . .
N2 N 0.7914(4) 0.48516(18) 0.55607(8) 0.0233(5) Uani 1 1 d . . . . .
H2 H 0.9017 0.4663 0.5396 0.028 Uiso 1 1 calc R . . . .
N3 N 0.8828(4) 0.31264(18) 0.65859(8) 0.0263(6) Uani 1 1 d . . . . .
N4 N 0.5450(4) 0.20822(19) 0.88538(8) 0.0272(6) Uani 1 1 d . . . . .
C1 C 0.3163(5) 0.7375(2) 0.52032(9) 0.0228(6) Uani 1 1 d . . . . .
C7 C 0.6755(5) 0.6272(2) 0.50471(9) 0.0211(6) Uani 1 1 d . . . . .
C12 C 0.7732(4) 0.2619(2) 0.74842(9) 0.0216(6) Uani 1 1 d . . . . .
C15 C 0.7064(4) 0.2377(2) 0.79631(10) 0.0215(6) Uani 1 1 d . . . . .
C2 C 0.5143(4) 0.7193(2) 0.49613(9) 0.0212(6) Uani 1 1 d . . . . .
C3 C 0.5680(5) 0.7930(2) 0.46245(9) 0.0241(6) Uani 1 1 d . . . . .
H3 H 0.6996 0.7825 0.4465 0.029 Uiso 1 1 calc R . . . .
O1W O 0.4369(5) 0.4985(3) 0.70791(10) 0.0677(8) Uani 1 1 d . . . . .
H1WA H 0.4938 0.5111 0.7360 0.102 Uiso 1 1 d G . . . .
H1WB H 0.5455 0.4963 0.6898 0.102 Uiso 1 1 d G . . . .
C17 C 0.7279(5) 0.2692(2) 0.87957(10) 0.0276(7) Uani 1 1 d . . . . .
H17 H 0.8016 0.3027 0.9060 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4323(5) 0.8811(2) 0.45200(10) 0.0287(7) Uani 1 1 d . . . . .
H4 H 0.4719 0.9292 0.4293 0.034 Uiso 1 1 calc R . . . .
C16 C 0.8146(5) 0.2856(2) 0.83649(9) 0.0253(7) Uani 1 1 d . . . . .
H16 H 0.9444 0.3284 0.8344 0.030 Uiso 1 1 calc R . . . .
C10 C 1.0200(5) 0.3464(2) 0.69620(10) 0.0299(7) Uani 1 1 d . . . . .
H10 H 1.1507 0.3869 0.6918 0.036 Uiso 1 1 calc R . . . .
C13 C 0.6383(5) 0.2283(2) 0.70838(10) 0.0277(7) Uani 1 1 d . . . . .
H13 H 0.5058 0.1882 0.7117 0.033 Uiso 1 1 calc R . . . .
C19 C 0.5195(5) 0.1705(2) 0.80253(10) 0.0294(7) Uani 1 1 d . . . . .
H19 H 0.4457 0.1339 0.7770 0.035 Uiso 1 1 calc R . . . .
C6 C 0.1792(5) 0.8263(2) 0.50966(10) 0.0274(7) Uani 1 1 d . . . . .
H6 H 0.0481 0.8379 0.5256 0.033 Uiso 1 1 calc R . . . .
C11 C 0.9702(5) 0.3220(2) 0.74114(10) 0.0296(7) Uani 1 1 d . . . . .
H11 H 1.0678 0.3456 0.7669 0.035 Uiso 1 1 calc R . . . .
C5 C 0.2358(5) 0.8973(2) 0.47568(10) 0.0298(7) Uani 1 1 d . . . . .
H5 H 0.1420 0.9561 0.4686 0.036 Uiso 1 1 calc R . . . .
C8 C 0.7571(5) 0.4375(2) 0.59618(10) 0.0286(7) Uani 1 1 d . . . . .
C9 C 0.9252(5) 0.3475(2) 0.61068(10) 0.0298(7) Uani 1 1 d . . . . .
H9A H 0.9006 0.2890 0.5887 0.036 Uiso 1 1 calc R . . . .
H9B H 1.0844 0.3717 0.6104 0.036 Uiso 1 1 calc R . . . .
C18 C 0.4459(5) 0.1590(2) 0.84701(11) 0.0326(7) Uani 1 1 d . . . . .
H18 H 0.3202 0.1146 0.8505 0.039 Uiso 1 1 calc R . . . .
C14 C 0.6956(5) 0.2527(2) 0.66419(10) 0.0304(7) Uani 1 1 d . . . . .
H14 H 0.6043 0.2277 0.6378 0.037 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 F2 1.6093(19) . ?
P1 F6 1.5890(19) . ?
P1 F1 1.5990(19) . ?
P1 F5 1.5711(19) . ?
P1 F3 1.590(2) . ?
P1 F4 1.578(2) . ?
O2 C7 1.234(3) . ?
O1 H1 0.8200 . ?
O1 C1 1.357(3) . ?
O3 C8 1.224(3) . ?
N1 H1A 0.8600 . ?
N1 N2 1.382(3) . ?
N1 C7 1.334(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.321(3) . ?
N3 C10 1.340(4) . ?
N3 C9 1.474(3) . ?
N3 C14 1.342(4) . ?
N4 C17 1.330(4) . ?
N4 C18 1.337(4) . ?
C1 C2 1.408(4) . ?
C1 C6 1.389(4) . ?
C7 C2 1.495(4) . ?
C12 C15 1.482(4) . ?
C12 C13 1.385(4) . ?
C12 C11 1.399(4) . ?
C15 C16 1.389(4) . ?
C15 C19 1.396(4) . ?
C2 C3 1.392(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8496 . ?
C17 H17 0.9300 . ?
C17 C16 1.382(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C16 H16 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.380(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(4) . ?
C11 H11 0.9300 . ?
C5 H5 0.9300 . ?
C8 C9 1.527(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C18 H18 0.9300 . ?
C14 H14 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
F6 P1 F2 90.48(11) . . ?
F6 P1 F1 178.03(12) . . ?
F6 P1 F3 89.21(11) . . ?
F1 P1 F2 88.07(10) . . ?
F5 P1 F2 89.84(11) . . ?
F5 P1 F6 90.79(10) . . ?
F5 P1 F1 90.53(12) . . ?
F5 P1 F3 178.72(14) . . ?
F5 P1 F4 90.81(13) . . ?
F3 P1 F2 88.88(12) . . ?
F3 P1 F1 89.44(11) . . ?
F4 P1 F2 179.02(12) . . ?
F4 P1 F6 90.25(12) . . ?
F4 P1 F1 91.19(11) . . ?
F4 P1 F3 90.46(13) . . ?
C1 O1 H1 109.5 . . ?
N2 N1 H1A 119.2 . . ?
C7 N1 H1A 119.2 . . ?
C7 N1 N2 121.5(2) . . ?
N1 N2 H2 121.6 . . ?
C8 N2 N1 116.8(2) . . ?
C8 N2 H2 121.6 . . ?
C10 N3 C9 120.4(2) . . ?
C10 N3 C14 120.5(2) . . ?
C14 N3 C9 118.9(3) . . ?
C17 N4 C18 116.9(2) . . ?
O1 C1 C2 119.1(2) . . ?
O1 C1 C6 121.1(2) . . ?
C6 C1 C2 119.9(3) . . ?
O2 C7 N1 121.7(2) . . ?
O2 C7 C2 122.3(2) . . ?
N1 C7 C2 116.0(2) . . ?
C13 C12 C15 121.2(2) . . ?
C13 C12 C11 116.5(3) . . ?
C11 C12 C15 122.3(3) . . ?
C16 C15 C12 122.0(2) . . ?
C16 C15 C19 117.0(3) . . ?
C19 C15 C12 120.9(3) . . ?
C1 C2 C7 124.7(2) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 C7 117.2(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
H1WA O1W H1WB 109.5 . . ?
N4 C17 H17 118.1 . . ?
N4 C17 C16 123.7(3) . . ?
C16 C17 H17 118.1 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
N3 C10 H10 119.6 . . ?
N3 C10 C11 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.3 . . ?
C15 C19 H19 120.4 . . ?
C18 C19 C15 119.2(3) . . ?
C18 C19 H19 120.4 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
O3 C8 N2 122.4(3) . . ?
O3 C8 C9 122.2(3) . . ?
N2 C8 C9 115.4(2) . . ?
N3 C9 C8 108.4(2) . . ?
N3 C9 H9A 110.0 . . ?
N3 C9 H9B 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N4 C18 C19 123.7(3) . . ?
N4 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
N3 C14 C13 120.3(3) . . ?
N3 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N4 0.82 1.87 2.644(3) 158.0 2_556
N1 H1A O1 0.86 1.87 2.580(3) 138.7 .
N2 H2 O2 0.86 1.92 2.746(3) 160.3 3_766
O1W H1WA F2 0.85 2.18 2.860(3) 136.6 .
O1W H1WB O3 0.85 2.09 2.795(3) 140.4 .

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 2286897'
loop_
_audit_author_name
_audit_author_address
'Yu-Ru Xu'
;Fuzhou University
China
;
_audit_update_record             
;
2023-08-05 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2022-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'F6 P, C19 H17 N4 O3, C3 H7 N O'
_chemical_formula_sum            'C22 H24 F6 N5 O4 P'
_chemical_formula_weight         567.43
_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'
O O 0.0106 0.0060 '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'

_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                   22.036(11)
_cell_length_b                   10.119(5)
_cell_length_c                   22.787(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5081(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7720
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7410
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1159 before and 0.0702 after correction. The Ratio of minimum to maximum transmission is 0.9568. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            123745
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.126
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2347
_reflns_number_total             4516
_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         0.305
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.015
_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)+(0.0656P)²+4.2225P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1675
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1A), C10(H10), C11(H11), C13(H13), C14(H14), C6(H6), C5(H5),
 C16(H16), C4(H4), C17(H17), C1S(H1S), C19(H19), C18(H18), C3(H3)
2.c Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C2S(H2SA,H2SB,H2SC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.34490(5) 1.07134(11) 1.04893(5) 0.0638(4) Uani 1 1 d . . . . .
F5 F 0.37670(11) 1.1553(3) 1.09908(10) 0.0875(8) Uani 1 1 d . . . . .
O3 O 0.25388(12) 0.2615(3) 0.68962(11) 0.0644(7) Uani 1 1 d . . . . .
N3 N 0.17128(12) 0.4529(3) 0.65203(12) 0.0461(7) Uani 1 1 d . . . . .
N2 N 0.30796(14) 0.4247(3) 0.73179(12) 0.0553(8) Uani 1 1 d . . . . .
H2 H 0.3096 0.5072 0.7407 0.066 Uiso 1 1 calc R . . . .
F6 F 0.28565(12) 1.1573(3) 1.05875(12) 0.1045(9) Uani 1 1 d . . . . .
O1 O 0.43981(13) 0.1794(4) 0.70224(11) 0.0859(10) Uani 1 1 d . . . . .
H1 H 0.4671 0.1537 0.6806 0.129 Uiso 1 1 calc GR . . . .
F2 F 0.36651(15) 1.1753(3) 1.00207(11) 0.1097(10) Uani 1 1 d . . . . .
N1 N 0.35705(13) 0.3429(3) 0.74184(13) 0.0615(9) Uani 1 1 d . . . . .
H1A H 0.3831 0.3287 0.7145 0.074 Uiso 1 1 calc R . . . .
O2 O 0.32974(14) 0.3151(3) 0.83497(12) 0.0856(10) Uani 1 1 d . . . . .
N4 N 0.01463(14) 0.3821(4) 0.38539(14) 0.0650(9) Uani 1 1 d . . . . .
O1S O 0.33735(17) 0.6655(3) 0.78529(15) 0.0953(11) Uani 1 1 d . . . . .
F1 F 0.40482(14) 0.9891(3) 1.03979(13) 0.1221(11) Uani 1 1 d . . . . .
F4 F 0.32276(16) 0.9705(3) 1.09727(13) 0.1223(11) Uani 1 1 d . . . . .
N1S N 0.31113(16) 0.7414(4) 0.87578(16) 0.0690(10) Uani 1 1 d . . . . .
F3 F 0.31181(17) 0.9904(3) 1.00072(14) 0.1408(13) Uani 1 1 d . . . . .
C8 C 0.25810(17) 0.3735(4) 0.70807(14) 0.0470(9) Uani 1 1 d . . . . .
C10 C 0.17752(17) 0.5444(3) 0.61018(16) 0.0520(9) Uani 1 1 d . . . . .
H10 H 0.2020 0.6179 0.6167 0.062 Uiso 1 1 calc R . . . .
C12 C 0.11144(15) 0.4223(3) 0.54721(15) 0.0470(9) Uani 1 1 d . . . . .
C15 C 0.07841(15) 0.4075(3) 0.49071(16) 0.0482(9) Uani 1 1 d . . . . .
C9 C 0.20432(16) 0.4673(4) 0.70720(14) 0.0501(9) Uani 1 1 d . . . . .
H9A H 0.1776 0.4477 0.7399 0.060 Uiso 1 1 calc R . . . .
H9B H 0.2184 0.5576 0.7113 0.060 Uiso 1 1 calc R . . . .
C1 C 0.41582(16) 0.1948(4) 0.80275(15) 0.0490(9) Uani 1 1 d . . . . .
C7 C 0.36373(17) 0.2857(4) 0.79476(17) 0.0542(10) Uani 1 1 d . . . . .
C11 C 0.14807(17) 0.5304(4) 0.55787(16) 0.0547(10) Uani 1 1 d . . . . .
H11 H 0.1527 0.5945 0.5290 0.066 Uiso 1 1 calc R . . . .
C2 C 0.45349(18) 0.1483(4) 0.75866(17) 0.0627(11) Uani 1 1 d . . . . .
C13 C 0.10715(19) 0.3288(4) 0.59117(18) 0.0691(12) Uani 1 1 d . . . . .
H13 H 0.0836 0.2536 0.5854 0.083 Uiso 1 1 calc R . . . .
C14 C 0.13705(19) 0.3459(4) 0.64282(18) 0.0686(12) Uani 1 1 d . . . . .
H14 H 0.1336 0.2823 0.6721 0.082 Uiso 1 1 calc R . . . .
C6 C 0.42863(18) 0.1565(4) 0.85995(17) 0.0596(10) Uani 1 1 d . . . . .
H6 H 0.4031 0.1845 0.8900 0.071 Uiso 1 1 calc R . . . .
C5 C 0.4778(2) 0.0787(4) 0.87364(19) 0.0741(13) Uani 1 1 d . . . . .
H5 H 0.4853 0.0540 0.9123 0.089 Uiso 1 1 calc R . . . .
C16 C 0.0833(2) 0.4970(5) 0.44682(18) 0.0839(15) Uani 1 1 d . . . . .
H16 H 0.1084 0.5703 0.4514 0.101 Uiso 1 1 calc R . . . .
C4 C 0.5152(2) 0.0383(5) 0.8294(2) 0.0889(15) Uani 1 1 d . . . . .
H4 H 0.5493 -0.0125 0.8381 0.107 Uiso 1 1 calc R . . . .
C17 C 0.0513(2) 0.4799(5) 0.39550(19) 0.0901(16) Uani 1 1 d . . . . .
H17 H 0.0563 0.5426 0.3661 0.108 Uiso 1 1 calc R . . . .
C1S C 0.3101(3) 0.6559(5) 0.8337(3) 0.0936(16) Uani 1 1 d . . . . .
H1S H 0.2871 0.5800 0.8397 0.112 Uiso 1 1 calc R . . . .
C19 C 0.0395(2) 0.3046(4) 0.48046(19) 0.0819(14) Uani 1 1 d . . . . .
H19 H 0.0336 0.2403 0.5090 0.098 Uiso 1 1 calc R . . . .
C18 C 0.0094(2) 0.2966(5) 0.4283(2) 0.0861(15) Uani 1 1 d . . . . .
H18 H -0.0168 0.2255 0.4228 0.103 Uiso 1 1 calc R . . . .
C3 C 0.5033(2) 0.0717(5) 0.7725(2) 0.0915(16) Uani 1 1 d . . . . .
H3 H 0.5289 0.0425 0.7428 0.110 Uiso 1 1 calc R . . . .
C3S C 0.2755(2) 0.7271(6) 0.9291(2) 0.1053(18) Uani 1 1 d . . . . .
H3SA H 0.2454 0.7958 0.9307 0.158 Uiso 1 1 calc GR . . . .
H3SB H 0.3017 0.7337 0.9626 0.158 Uiso 1 1 calc GR . . . .
H3SC H 0.2558 0.6425 0.9291 0.158 Uiso 1 1 calc GR . . . .
C2S C 0.3429(3) 0.8641(5) 0.8689(2) 0.118(2) Uani 1 1 d . . . . .
H2SA H 0.3713 0.8568 0.8371 0.177 Uiso 1 1 calc GR . . . .
H2SB H 0.3643 0.8846 0.9044 0.177 Uiso 1 1 calc GR . . . .
H2SC H 0.3143 0.9333 0.8605 0.177 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 F5 1.587(3) . ?
P1 F6 1.584(3) . ?
P1 F2 1.573(3) . ?
P1 F1 1.574(3) . ?
P1 F4 1.579(3) . ?
P1 F3 1.552(3) . ?
O3 C8 1.213(4) . ?
N3 C10 1.337(4) . ?
N3 C9 1.460(4) . ?
N3 C14 1.336(5) . ?
N2 N1 1.381(4) . ?
N2 C8 1.330(4) . ?
O1 C2 1.357(4) . ?
N1 C7 1.346(5) . ?
O2 C7 1.220(4) . ?
N4 C17 1.298(5) . ?
N4 C18 1.310(5) . ?
O1S C1S 1.259(6) . ?
N1S C1S 1.292(6) . ?
N1S C3S 1.454(5) . ?
N1S C2S 1.434(6) . ?
C8 C9 1.518(5) . ?
C10 C11 1.365(5) . ?
C12 C15 1.487(5) . ?
C12 C11 1.380(5) . ?
C12 C13 1.381(5) . ?
C15 C16 1.354(5) . ?
C15 C19 1.369(5) . ?
C1 C7 1.482(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.389(5) . ?
C2 C3 1.381(5) . ?
C13 C14 1.360(5) . ?
C6 C5 1.375(5) . ?
C5 C4 1.367(6) . ?
C16 C17 1.377(5) . ?
C4 C3 1.364(6) . ?
C19 C18 1.364(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
F6 P1 F5 88.19(15) . . ?
F2 P1 F5 89.85(16) . . ?
F2 P1 F6 88.76(17) . . ?
F2 P1 F1 90.54(17) . . ?
F2 P1 F4 178.29(17) . . ?
F1 P1 F5 90.44(17) . . ?
F1 P1 F6 178.47(18) . . ?
F1 P1 F4 90.58(18) . . ?
F4 P1 F5 88.85(16) . . ?
F4 P1 F6 90.08(18) . . ?
F3 P1 F5 178.18(19) . . ?
F3 P1 F6 90.13(18) . . ?
F3 P1 F2 90.82(19) . . ?
F3 P1 F1 91.25(19) . . ?
F3 P1 F4 90.4(2) . . ?
C10 N3 C9 119.6(3) . . ?
C14 N3 C10 120.5(3) . . ?
C14 N3 C9 119.8(3) . . ?
C8 N2 N1 118.8(3) . . ?
C7 N1 N2 119.5(3) . . ?
C17 N4 C18 115.2(4) . . ?
C1S N1S C3S 123.0(5) . . ?
C1S N1S C2S 120.5(5) . . ?
C2S N1S C3S 116.2(4) . . ?
O3 C8 N2 124.6(3) . . ?
O3 C8 C9 121.3(3) . . ?
N2 C8 C9 114.0(3) . . ?
N3 C10 C11 120.1(3) . . ?
C11 C12 C15 121.2(3) . . ?
C11 C12 C13 117.1(3) . . ?
C13 C12 C15 121.7(3) . . ?
C16 C15 C12 122.2(3) . . ?
C16 C15 C19 115.6(4) . . ?
C19 C15 C12 122.1(4) . . ?
N3 C9 C8 109.8(3) . . ?
C2 C1 C7 125.8(3) . . ?
C2 C1 C6 117.7(3) . . ?
C6 C1 C7 116.5(3) . . ?
N1 C7 C1 117.5(3) . . ?
O2 C7 N1 120.1(4) . . ?
O2 C7 C1 122.3(4) . . ?
C10 C11 C12 121.0(3) . . ?
O1 C2 C1 118.4(3) . . ?
O1 C2 C3 121.5(4) . . ?
C3 C2 C1 120.1(4) . . ?
C14 C13 C12 120.5(4) . . ?
N3 C14 C13 120.8(4) . . ?
C5 C6 C1 122.2(4) . . ?
C4 C5 C6 118.7(4) . . ?
C15 C16 C17 120.2(4) . . ?
C3 C4 C5 120.7(4) . . ?
N4 C17 C16 124.4(4) . . ?
O1S C1S N1S 126.2(5) . . ?
C18 C19 C15 119.9(4) . . ?
N4 C18 C19 124.6(4) . . ?
C4 C3 C2 120.6(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1S 0.86 1.99 2.800(5) 156.0 .
O1 H1 N4 0.82 1.87 2.663(4) 163.1 4_556
N1 H1A O1 0.86 1.98 2.623(4) 130.7 .

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
O3 C8 C9 N3 -41.1(5) . . . . ?
N3 C10 C11 C12 0.1(6) . . . . ?
N2 N1 C7 O2 -6.4(6) . . . . ?
N2 N1 C7 C1 177.7(3) . . . . ?
N2 C8 C9 N3 140.5(3) . . . . ?
O1 C2 C3 C4 -178.0(5) . . . . ?
N1 N2 C8 O3 -6.7(5) . . . . ?
N1 N2 C8 C9 171.6(3) . . . . ?
C8 N2 N1 C7 -93.8(4) . . . . ?
C10 N3 C9 C8 -103.8(4) . . . . ?
C10 N3 C14 C13 -1.0(6) . . . . ?
C12 C15 C16 C17 -179.3(4) . . . . ?
C12 C15 C19 C18 178.8(4) . . . . ?
C12 C13 C14 N3 -0.3(7) . . . . ?
C15 C12 C11 C10 179.0(3) . . . . ?
C15 C12 C13 C14 -178.9(4) . . . . ?
C15 C16 C17 N4 1.0(8) . . . . ?
C15 C19 C18 N4 0.0(8) . . . . ?
C9 N3 C10 C11 178.3(3) . . . . ?
C9 N3 C14 C13 -178.3(4) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C1 C6 C5 C4 0.3(6) . . . . ?
C7 C1 C2 O1 -5.3(6) . . . . ?
C7 C1 C2 C3 175.2(4) . . . . ?
C7 C1 C6 C5 -176.2(4) . . . . ?
C11 C12 C15 C16 1.2(6) . . . . ?
C11 C12 C15 C19 -176.6(4) . . . . ?
C11 C12 C13 C14 1.4(6) . . . . ?
C2 C1 C7 N1 -9.7(6) . . . . ?
C2 C1 C7 O2 174.6(4) . . . . ?
C2 C1 C6 C5 1.9(6) . . . . ?
C13 C12 C15 C16 -178.5(4) . . . . ?
C13 C12 C15 C19 3.7(6) . . . . ?
C13 C12 C11 C10 -1.3(5) . . . . ?
C14 N3 C10 C11 1.1(5) . . . . ?
C14 N3 C9 C8 73.5(4) . . . . ?
C6 C1 C7 N1 168.2(3) . . . . ?
C6 C1 C7 O2 -7.5(6) . . . . ?
C6 C1 C2 O1 176.8(4) . . . . ?
C6 C1 C2 C3 -2.8(6) . . . . ?
C6 C5 C4 C3 -1.7(7) . . . . ?
C5 C4 C3 C2 0.8(8) . . . . ?
C16 C15 C19 C18 0.9(7) . . . . ?
C17 N4 C18 C19 -0.4(7) . . . . ?
C19 C15 C16 C17 -1.4(7) . . . . ?
C18 N4 C17 C16 -0.1(7) . . . . ?
C3S N1S C1S O1S 176.1(5) . . . . ?
C2S N1S C1S O1S 3.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
