# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ck3major
_database_code_depnum_ccdc_archive 'CCDC 1413928'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_audit_creation_date             2013-03-22T11:18:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H38 F3 N2 O5 P1'
_chemical_formula_sum            'C23 H38 F3 N2 O5 P1'
_chemical_formula_weight         510.52
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7802(3)
_cell_length_b                   23.3448(7)
_cell_length_c                   13.2357(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.722(2)
_cell_angle_gamma                90
_cell_volume                     2807.35(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22356
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.37
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.15
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.072
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_number            22356
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.949
_reflns_number_total             5453
_reflns_number_gt                2695
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1105P)²+0.9055P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5453
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.2218
_refine_ls_wR_factor_gt          0.1623
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6764(4) 0.71115(13) 0.2470(2) 0.0543(8) Uani 1 1 d . . .
H1 H 0.7636 0.6902 0.2941 0.065 Uiso 1 1 calc R . .
C2 C 0.6849(4) 0.71907(15) 0.1343(3) 0.0633(9) Uani 1 1 d . . .
H2A H 0.6966 0.6819 0.1059 0.076 Uiso 1 1 calc R . .
H2B H 0.593 0.7353 0.0855 0.076 Uiso 1 1 calc R . .
C3 C 0.9437(5) 0.7404(2) 0.1825(3) 0.0821(11) Uani 1 1 d . . .
C4 C 1.0582(6) 0.7824(3) 0.1762(5) 0.1033(16) Uani 1 1 d . . .
C5 C 0.6686(4) 0.76767(14) 0.2978(3) 0.0618(9) Uani 1 1 d . . .
C6 C 0.5390(5) 0.79822(17) 0.2678(3) 0.0820(11) Uani 1 1 d . . .
H6 H 0.4532 0.7825 0.2178 0.098 Uiso 1 1 calc R . .
C7 C 0.5345(8) 0.8518(2) 0.3108(5) 0.1112(18) Uani 1 1 d . . .
H7 H 0.446 0.8717 0.2903 0.133 Uiso 1 1 calc R . .
C8 C 0.6581(11) 0.8753(2) 0.3824(6) 0.129(2) Uani 1 1 d . . .
H8 H 0.6551 0.9117 0.4097 0.154 Uiso 1 1 calc R . .
C9 C 0.7885(9) 0.8457(3) 0.4153(4) 0.1182(19) Uani 1 1 d . . .
H9 H 0.8732 0.8619 0.4656 0.142 Uiso 1 1 calc R . .
C10 C 0.7941(5) 0.79121(18) 0.3733(3) 0.0836(11) Uani 1 1 d . . .
H10 H 0.8822 0.7709 0.3962 0.1 Uiso 1 1 calc R . .
C11 C 0.6099(4) 0.58232(14) 0.2933(3) 0.0595(8) Uani 1 1 d . . .
H11 H 0.5385 0.5509 0.2759 0.071 Uiso 1 1 calc R . .
C12 C 0.7606(4) 0.55211(15) 0.3051(3) 0.0705(10) Uani 1 1 d . . .
C13 C 0.8963(4) 0.57878(18) 0.3930(3) 0.0873(12) Uani 1 1 d . . .
H13A H 0.9838 0.561 0.3911 0.131 Uiso 1 1 calc R . .
H13B H 0.8908 0.573 0.4632 0.131 Uiso 1 1 calc R . .
H13C H 0.8991 0.6191 0.3796 0.131 Uiso 1 1 calc R . .
C14 C 0.7887(5) 0.5553(2) 0.1991(4) 0.1004(14) Uani 1 1 d . . .
H14A H 0.8813 0.5375 0.2091 0.151 Uiso 1 1 calc R . .
H14B H 0.7913 0.5947 0.179 0.151 Uiso 1 1 calc R . .
H14C H 0.7112 0.5358 0.1426 0.151 Uiso 1 1 calc R . .
C15 C 0.7530(5) 0.48924(18) 0.3332(4) 0.1052(15) Uani 1 1 d . . .
H15A H 0.8466 0.4714 0.3465 0.158 Uiso 1 1 calc R . .
H15B H 0.6785 0.4703 0.2737 0.158 Uiso 1 1 calc R . .
H15C H 0.7292 0.4863 0.3972 0.158 Uiso 1 1 calc R . .
C16 C 0.4000(4) 0.60887(16) 0.1165(3) 0.0723(10) Uani 1 1 d . . .
C17 C 0.2768(5) 0.6086(2) 0.1619(4) 0.0958(13) Uani 1 1 d . . .
H17A H 0.2942 0.5784 0.2144 0.144 Uiso 1 1 calc R . .
H17B H 0.1839 0.6024 0.1036 0.144 Uiso 1 1 calc R . .
H17C H 0.2751 0.6447 0.196 0.144 Uiso 1 1 calc R . .
C18 C 0.3620(5) 0.6540(2) 0.0278(3) 0.0988(14) Uani 1 1 d . . .
H18A H 0.3604 0.6911 0.0588 0.148 Uiso 1 1 calc R . .
H18B H 0.2669 0.6459 -0.0264 0.148 Uiso 1 1 calc R . .
H18C H 0.4345 0.6537 -0.0051 0.148 Uiso 1 1 calc R . .
C19 C 0.4067(6) 0.5509(2) 0.0659(4) 0.1134(17) Uani 1 1 d . . .
H19A H 0.4797 0.552 0.0334 0.17 Uiso 1 1 calc R . .
H19B H 0.3124 0.5422 0.0112 0.17 Uiso 1 1 calc R . .
H19C H 0.4324 0.5219 0.1212 0.17 Uiso 1 1 calc R . .
C20 C 0.6550(7) 0.5589(3) 0.6045(4) 0.1225(18) Uani 1 1 d . . .
H20A H 0.6604 0.5986 0.6269 0.147 Uiso 1 1 calc R . .
H20B H 0.5676 0.5423 0.6109 0.147 Uiso 1 1 calc R . .
C21 C 0.7770(9) 0.5303(3) 0.6730(5) 0.178(3) Uani 1 1 d . . .
H21A H 0.7787 0.4923 0.646 0.267 Uiso 1 1 calc R . .
H21B H 0.7732 0.5283 0.7444 0.267 Uiso 1 1 calc R . .
H21C H 0.8643 0.5504 0.6766 0.267 Uiso 1 1 calc R . .
C22 C 0.3798(5) 0.6754(2) 0.4180(5) 0.1077(16) Uani 1 1 d . . .
H22A H 0.3344 0.6954 0.3494 0.129 Uiso 1 1 calc R . .
H22B H 0.4581 0.6994 0.4658 0.129 Uiso 1 1 calc R . .
C23 C 0.2720(6) 0.6658(3) 0.4660(5) 0.144(2) Uani 1 1 d . . .
H23A H 0.201 0.6384 0.4232 0.215 Uiso 1 1 calc R . .
H23B H 0.2233 0.7012 0.4684 0.215 Uiso 1 1 calc R . .
H23C H 0.3197 0.6513 0.5386 0.215 Uiso 1 1 calc R . .
N1 N 0.5515(3) 0.62168(11) 0.1982(2) 0.0586(7) Uani 1 1 d . . .
N2 N 0.8055(3) 0.75592(12) 0.1360(2) 0.0650(7) Uani 1 1 d . . .
H2 H 0.7856 0.789 0.1055 0.078 Uiso 1 1 calc R . .
O1 O 0.5454(2) 0.67942(9) 0.23837(17) 0.0581(6) Uani 1 1 d . . .
O2 O 0.9883(3) 0.69548(16) 0.2315(3) 0.1239(13) Uani 1 1 d . . .
O3 O 0.7007(3) 0.66098(10) 0.47162(18) 0.0698(7) Uani 1 1 d . . .
O4 O 0.6413(3) 0.55638(11) 0.4907(2) 0.0838(8) Uani 1 1 d . . .
O5 O 0.4398(3) 0.62242(10) 0.4002(2) 0.0762(7) Uani 1 1 d . . .
F1 F 1.132(4) 0.8049(15) 0.2745(14) 0.231(13) Uani 0.50(3) 1 d P . .
F2 F 1.1532(17) 0.7553(7) 0.143(2) 0.161(9) Uani 0.50(3) 1 d P . .
F3 F 1.0120(14) 0.8253(8) 0.1077(16) 0.125(5) Uani 0.50(3) 1 d P . .
F4 F 1.0123(18) 0.8338(8) 0.169(3) 0.185(10) Uani 0.50(3) 1 d P . .
F5 F 1.087(5) 0.7745(18) 0.092(3) 0.272(15) Uani 0.50(3) 1 d P . .
F6 F 1.1720(14) 0.7841(8) 0.2543(18) 0.157(8) Uani 0.50(3) 1 d P . .
P1 P 0.60542(11) 0.61244(4) 0.42001(7) 0.0632(3) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.447(4) . ?
C1 C5 1.496(4) . ?
C1 C2 1.535(4) . ?
C1 H1 0.98 . ?
C2 N2 1.453(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 O2 1.225(5) . ?
C3 N2 1.312(5) . ?
C3 C4 1.513(6) . ?
C4 F6 1.207(15) . ?
C4 F5 1.254(16) . ?
C4 F4 1.27(2) . ?
C4 F3 1.315(16) . ?
C4 F2 1.328(15) . ?
C4 F1 1.340(18) . ?
C5 C10 1.378(5) . ?
C5 C6 1.378(5) . ?
C6 C7 1.382(6) . ?
C6 H6 0.93 . ?
C7 C8 1.346(9) . ?
C7 H7 0.93 . ?
C8 C9 1.371(9) . ?
C8 H8 0.93 . ?
C9 C10 1.397(7) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C11 N1 1.492(4) . ?
C11 C12 1.588(5) . ?
C11 P1 1.833(3) . ?
C11 H11 0.98 . ?
C12 C15 1.523(6) . ?
C12 C14 1.528(5) . ?
C12 C13 1.536(5) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 N1 1.506(4) . ?
C16 C18 1.518(6) . ?
C16 C19 1.523(5) . ?
C16 C17 1.533(5) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 C21 1.375(7) . ?
C20 O4 1.463(5) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C22 O5 1.426(5) . ?
C22 C23 1.435(7) . ?
C22 H22A 0.97 . ?
C23 H22B 0.97 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
N1 O1 1.458(3) . ?
N2 H2 0.86 . ?
O3 P1 1.466(2) . ?
O4 P1 1.571(3) . ?
O5 P1 1.560(3) . ?
F1 F6 0.73(3) . ?
F1 F4 1.61(3) . ?
F2 F5 0.86(5) . ?
F2 F6 1.57(3) . ?
F3 F4 0.83(3) . ?
F3 F5 1.45(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 107.2(2) . . ?
O1 C1 C2 110.5(3) . . ?
C5 C1 C2 111.2(3) . . ?
O1 C1 H1 109.3 . . ?
C5 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
N2 C2 C1 113.1(3) . . ?
N2 C2 H2A 109 . . ?
C1 C2 H2A 109 . . ?
N2 C2 H2B 109 . . ?
C1 C2 H2B 109 . . ?
H2A C2 H2B 107.8 . . ?
O2 C3 N2 126.0(4) . . ?
O2 C3 C4 117.3(4) . . ?
N2 C3 C4 116.8(4) . . ?
F6 C4 F5 108.9(19) . . ?
F6 C4 F4 102.8(15) . . ?
F5 C4 F4 104.9(15) . . ?
F6 C4 F3 122.5(11) . . ?
F5 C4 F3 69(2) . . ?
F4 C4 F3 37.4(15) . . ?
F6 C4 F2 76.4(12) . . ?
F5 C4 F2 39(2) . . ?
F4 C4 F2 133.9(15) . . ?
F3 C4 F2 103.8(11) . . ?
F6 C4 F1 32.8(15) . . ?
F5 C4 F1 134.2(14) . . ?
F4 C4 F1 75.8(14) . . ?
F3 C4 F1 107.1(15) . . ?
F2 C4 F1 108.4(16) . . ?
F6 C4 C3 116.2(10) . . ?
F5 C4 C3 111.5(10) . . ?
F4 C4 C3 111.6(9) . . ?
F3 C4 C3 117.3(7) . . ?
F2 C4 C3 109.4(9) . . ?
F1 C4 C3 110.3(10) . . ?
C10 C5 C6 118.7(4) . . ?
C10 C5 C1 119.8(3) . . ?
C6 C5 C1 121.4(3) . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.1(6) . . ?
C8 C7 H7 120 . . ?
C6 C7 H7 120 . . ?
C7 C8 C9 120.4(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 120.0(6) . . ?
C8 C9 H9 120 . . ?
C10 C9 H9 120 . . ?
C5 C10 C9 119.7(5) . . ?
C5 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C12 114.1(3) . . ?
N1 C11 P1 113.8(2) . . ?
C12 C11 P1 114.6(2) . . ?
N1 C11 H11 104.2 . . ?
C12 C11 H11 104.2 . . ?
P1 C11 H11 104.2 . . ?
C15 C12 C14 108.3(3) . . ?
C15 C12 C13 108.2(3) . . ?
C14 C12 C13 106.1(3) . . ?
C15 C12 C11 108.9(3) . . ?
C14 C12 C11 111.3(3) . . ?
C13 C12 C11 113.9(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C18 108.2(3) . . ?
N1 C16 C19 107.6(3) . . ?
C18 C16 C19 108.4(3) . . ?
N1 C16 C17 115.2(3) . . ?
C18 C16 C17 107.6(4) . . ?
C19 C16 C17 109.7(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 O4 112.7(5) . . ?
C21 C20 H20A 109 . . ?
O4 C20 H20A 109 . . ?
C21 C20 H20B 109 . . ?
O4 C20 H20B 109 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 C23 110.5(5) . . ?
O5 C22 H22A 109.5 . . ?
C24 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 N1 C11 108.4(2) . . ?
O1 N1 C16 106.5(2) . . ?
C11 N1 C16 116.9(3) . . ?
C3 N2 C2 122.2(3) . . ?
C3 N2 H2 118.9 . . ?
C2 N2 H2 118.9 . . ?
C1 O1 N1 110.4(2) . . ?
C20 O4 P1 119.7(3) . . ?
C22 O5 P1 124.6(3) . . ?
F6 F1 C4 64(2) . . ?
F6 F1 F4 106(3) . . ?
C4 F1 F4 50.2(10) . . ?
F5 F2 C4 65.9(17) . . ?
F5 F2 F6 107(3) . . ?
C4 F2 F6 48.3(8) . . ?
F4 F3 C4 68.5(18) . . ?
F4 F3 F5 121(3) . . ?
C4 F3 F5 53.7(12) . . ?
F3 F4 C4 74(3) . . ?
F3 F4 F1 119(3) . . ?
C4 F4 F1 54.0(11) . . ?
F2 F5 C4 75(2) . . ?
F2 F5 F3 126(3) . . ?
C4 F5 F3 57.7(12) . . ?
F1 F6 C4 84(2) . . ?
F1 F6 F2 137(3) . . ?
C4 F6 F2 55.3(10) . . ?
O3 P1 O5 113.84(14) . . ?
O3 P1 O4 113.79(15) . . ?
O5 P1 O4 102.32(15) . . ?
O3 P1 C11 119.77(15) . . ?
O5 P1 C11 106.20(15) . . ?
O4 P1 C11 98.58(14) . . ?

# END of CIF
####################################################################### 
# 
# 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_ck3minor
_database_code_depnum_ccdc_archive 'CCDC 1413931'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_audit_creation_date             2013-03-25T10:40:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H38 F3 N2 O5 P1'
_chemical_formula_sum            'C23 H38 F3 N2 O5 P1'
_chemical_formula_weight         510.52
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6414(2)
_cell_length_b                   17.8695(3)
_cell_length_c                   16.8961(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.21
_cell_angle_gamma                90
_cell_volume                     2731.72(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    26568
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.52
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_number            26568
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_reflns_number_total             6706
_reflns_number_gt                3905
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1501P)²+1.0120P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6706
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0813
_refine_ls_wR_factor_ref         0.272
_refine_ls_wR_factor_gt          0.2216
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.151

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5081(3) 0.26122(17) 0.57236(17) 0.0500(6) Uani 1 1 d . . .
H1 H 0.4582 0.2154 0.58 0.06 Uiso 1 1 calc R . .
C2 C 0.6520(3) 0.26784(19) 0.64670(19) 0.0579(7) Uani 1 1 d . . .
H2A H 0.6297 0.2652 0.6984 0.069 Uiso 1 1 calc R . .
H2B H 0.7136 0.2251 0.646 0.069 Uiso 1 1 calc R . .
C3 C 0.7535(4) 0.3865(2) 0.7083(2) 0.0610(8) Uani 1 1 d . . .
C4 C 0.8532(5) 0.4510(3) 0.7057(3) 0.0824(11) Uani 1 1 d . . .
C5 C 0.4051(3) 0.32549(17) 0.56634(18) 0.0532(7) Uani 1 1 d . . .
C6 C 0.2957(4) 0.3195(2) 0.6018(2) 0.0706(9) Uani 1 1 d . . .
H6 H 0.2847 0.275 0.6277 0.085 Uiso 1 1 calc R . .
C7 C 0.2025(4) 0.3793(3) 0.5990(3) 0.0901(13) Uani 1 1 d . . .
H7 H 0.1294 0.3749 0.623 0.108 Uiso 1 1 calc R . .
C8 C 0.2179(5) 0.4448(3) 0.5609(3) 0.0938(14) Uani 1 1 d . . .
H8 H 0.1544 0.4846 0.5583 0.113 Uiso 1 1 calc R . .
C9 C 0.3258(5) 0.4518(2) 0.5268(3) 0.0802(11) Uani 1 1 d . . .
H9 H 0.3369 0.4967 0.5018 0.096 Uiso 1 1 calc R . .
C10 C 0.4188(4) 0.39282(19) 0.5291(2) 0.0658(8) Uani 1 1 d . . .
H10 H 0.492 0.3982 0.5054 0.079 Uiso 1 1 calc R . .
C11 C 0.7143(3) 0.18938(16) 0.45579(18) 0.0502(6) Uani 1 1 d . . .
H11 H 0.6919 0.1619 0.4026 0.06 Uiso 1 1 calc R . .
C12 C 0.8558(4) 0.14827(19) 0.5192(2) 0.0630(8) Uani 1 1 d . . .
C13 C 0.9381(5) 0.1093(3) 0.4676(3) 0.0876(12) Uani 1 1 d . . .
H13A H 0.9737 0.1462 0.438 0.131 Uiso 1 1 calc R . .
H13B H 0.8721 0.0758 0.4278 0.131 Uiso 1 1 calc R . .
H13C H 1.0201 0.0816 0.5048 0.131 Uiso 1 1 calc R . .
C14 C 0.9643(4) 0.2011(2) 0.5821(3) 0.0799(11) Uani 1 1 d . . .
H14A H 1.0444 0.1726 0.6198 0.12 Uiso 1 1 calc R . .
H14B H 0.9141 0.2273 0.6138 0.12 Uiso 1 1 calc R . .
H14C H 1.0024 0.2364 0.552 0.12 Uiso 1 1 calc R . .
C15 C 0.8115(5) 0.0874(2) 0.5703(3) 0.0842(11) Uani 1 1 d . . .
H15A H 0.7499 0.0511 0.5325 0.126 Uiso 1 1 calc R . .
H15B H 0.7582 0.1099 0.6028 0.126 Uiso 1 1 calc R . .
H15C H 0.8987 0.0634 0.6075 0.126 Uiso 1 1 calc R . .
C16 C 0.4491(4) 0.14371(18) 0.4132(2) 0.0588(7) Uani 1 1 d . . .
C17 C 0.3286(4) 0.1339(2) 0.4517(2) 0.0713(9) Uani 1 1 d . . .
H17A H 0.3676 0.1068 0.5037 0.107 Uiso 1 1 calc R . .
H17B H 0.2474 0.1066 0.4132 0.107 Uiso 1 1 calc R . .
H17C H 0.295 0.1822 0.4623 0.107 Uiso 1 1 calc R . .
C18 C 0.4960(5) 0.0654(2) 0.3959(3) 0.0826(11) Uani 1 1 d . . .
H18A H 0.5775 0.0692 0.3758 0.124 Uiso 1 1 calc R . .
H18B H 0.4146 0.0411 0.3541 0.124 Uiso 1 1 calc R . .
H18C H 0.5255 0.0366 0.4471 0.124 Uiso 1 1 calc R . .
C19 C 0.3884(4) 0.1859(2) 0.3304(2) 0.0802(11) Uani 1 1 d . . .
H19A H 0.3598 0.2354 0.3408 0.12 Uiso 1 1 calc R . .
H19B H 0.3039 0.1599 0.2932 0.12 Uiso 1 1 calc R . .
H19C H 0.4631 0.1891 0.3049 0.12 Uiso 1 1 calc R . .
C20 C 0.5332(5) 0.3752(2) 0.3352(3) 0.0876(12) Uani 1 1 d . . .
H20A H 0.4453 0.3675 0.3497 0.105 Uiso 1 1 calc R . .
H20B H 0.5924 0.4136 0.3721 0.105 Uiso 1 1 calc R . .
C21 C 0.4913(10) 0.3996(4) 0.2501(4) 0.179(4) Uani 1 1 d . . .
H21A H 0.5753 0.4212 0.2405 0.268 Uiso 1 1 calc R . .
H21B H 0.4145 0.4365 0.2394 0.268 Uiso 1 1 calc R . .
H21C H 0.4557 0.3578 0.213 0.268 Uiso 1 1 calc R . .
C22 C 0.9500(6) 0.3310(3) 0.3682(4) 0.1142(19) Uani 1 1 d . . .
H22A H 0.8755 0.3622 0.3287 0.137 Uiso 1 1 calc R . .
H22B H 1.0014 0.3614 0.4171 0.137 Uiso 1 1 calc R . .
C23 C 1.0484(7) 0.3092(4) 0.3314(4) 0.134(2) Uani 1 1 d . . .
H23A H 1.1407 0.2966 0.3743 0.201 Uiso 1 1 calc R . .
H23B H 1.0635 0.3493 0.2974 0.201 Uiso 1 1 calc R . .
H23C H 1.0105 0.2662 0.2964 0.201 Uiso 1 1 calc R . .
N1 N 0.5786(3) 0.18117(13) 0.47869(15) 0.0492(5) Uani 1 1 d . . .
N2 N 0.7355(3) 0.33508(15) 0.64850(16) 0.0574(6) Uani 1 1 d . . .
H2 H 0.7743 0.3421 0.6103 0.069 Uiso 1 1 calc R . .
O1 O 0.5295(2) 0.25603(10) 0.49199(12) 0.0491(5) Uani 1 1 d . . .
O2 O 0.6993(3) 0.38515(19) 0.76319(17) 0.0915(9) Uani 1 1 d . . .
O3 O 0.7846(3) 0.34405(12) 0.49526(14) 0.0649(6) Uani 1 1 d . . .
O4 O 0.6162(3) 0.30695(12) 0.34808(14) 0.0642(6) Uani 1 1 d . . .
O5 O 0.8774(3) 0.27089(14) 0.39433(16) 0.0718(7) Uani 1 1 d . . .
F1 F 0.8975(3) 0.45438(16) 0.64201(17) 0.1044(8) Uani 1 1 d . . .
F2 F 0.9748(6) 0.4481(4) 0.7699(2) 0.219(3) Uani 1 1 d . . .
F3 F 0.7973(7) 0.5128(2) 0.7112(5) 0.246(4) Uani 1 1 d . . .
P1 P 0.74889(9) 0.28590(4) 0.42985(5) 0.0546(3) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.445(3) . ?
C1 C5 1.498(4) . ?
C1 C2 1.521(4) . ?
C1 H1 0.98 . ?
C2 N2 1.440(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 O2 1.212(4) . ?
C3 N2 1.332(4) . ?
C3 C4 1.511(5) . ?
C4 F3 1.246(6) . ?
C4 F1 1.289(4) . ?
C4 F2 1.294(6) . ?
C5 C10 1.385(5) . ?
C5 C6 1.385(4) . ?
C6 C7 1.387(5) . ?
C6 H6 0.93 . ?
C7 C8 1.369(7) . ?
C7 H7 0.93 . ?
C8 C9 1.357(6) . ?
C8 H8 0.93 . ?
C9 C10 1.376(5) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C11 N1 1.495(3) . ?
C11 C12 1.593(4) . ?
C11 P1 1.838(3) . ?
C11 H11 0.98 . ?
C12 C14 1.531(5) . ?
C12 C13 1.534(5) . ?
C12 C15 1.537(5) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 N1 1.509(4) . ?
C16 C19 1.517(5) . ?
C16 C17 1.525(4) . ?
C16 C18 1.530(5) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 C21 1.421(7) . ?
C20 O4 1.433(4) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C22 C23 1.359(6) . ?
C22 O5 1.432(4) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
N1 O1 1.462(3) . ?
N2 H2 0.86 . ?
O3 P1 1.469(2) . ?
O4 P1 1.570(2) . ?
O5 P1 1.575(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 107.0(2) . . ?
O1 C1 C2 113.3(2) . . ?
C5 C1 C2 113.0(3) . . ?
O1 C1 H1 107.8 . . ?
C5 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
N2 C2 C1 115.2(3) . . ?
N2 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
N2 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O2 C3 N2 126.1(3) . . ?
O2 C3 C4 119.0(3) . . ?
N2 C3 C4 115.0(3) . . ?
F3 C4 F1 107.3(5) . . ?
F3 C4 F2 105.2(5) . . ?
F1 C4 F2 103.6(4) . . ?
F3 C4 C3 112.2(4) . . ?
F1 C4 C3 117.2(3) . . ?
F2 C4 C3 110.3(4) . . ?
C10 C5 C6 118.0(3) . . ?
C10 C5 C1 122.1(3) . . ?
C6 C5 C1 119.8(3) . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120 . . ?
C6 C7 H7 120 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
N1 C11 C12 113.8(2) . . ?
N1 C11 P1 113.63(19) . . ?
C12 C11 P1 114.2(2) . . ?
N1 C11 H11 104.6 . . ?
C12 C11 H11 104.6 . . ?
P1 C11 H11 104.6 . . ?
C14 C12 C13 108.1(3) . . ?
C14 C12 C15 107.6(3) . . ?
C13 C12 C15 107.3(3) . . ?
C14 C12 C11 113.8(3) . . ?
C13 C12 C11 108.5(3) . . ?
C15 C12 C11 111.4(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C19 114.4(3) . . ?
N1 C16 C17 107.3(2) . . ?
C19 C16 C17 110.0(3) . . ?
N1 C16 C18 108.8(3) . . ?
C19 C16 C18 108.9(3) . . ?
C17 C16 C18 107.2(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 O4 111.3(4) . . ?
C21 C20 H20A 109.4 . . ?
O4 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
O4 C20 H20B 109.4 . . ?
H20A C20 H20B 108 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 O5 114.8(5) . . ?
C23 C22 H22A 108.6 . . ?
O5 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
O5 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 N1 C11 107.99(19) . . ?
O1 N1 C16 106.8(2) . . ?
C11 N1 C16 115.5(2) . . ?
C3 N2 C2 121.2(3) . . ?
C3 N2 H2 119.4 . . ?
C2 N2 H2 119.4 . . ?
C1 O1 N1 111.22(19) . . ?
C20 O4 P1 125.4(2) . . ?
C22 O5 P1 121.5(3) . . ?
O3 P1 O4 113.61(14) . . ?
O3 P1 O5 113.37(14) . . ?
O4 P1 O5 102.38(14) . . ?
O3 P1 C11 119.94(13) . . ?
O4 P1 C11 105.95(13) . . ?
O5 P1 C11 99.35(13) . . ?

# END of CIF
