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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Structure-2c
_database_code_depnum_ccdc_archive 'CCDC 2083632'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H25 N2 O4 P'
_chemical_formula_sum            'C18 H25 N2 O4 P'
_chemical_formula_weight         364.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   14.4732(3)
_cell_length_b                   8.9061(2)
_cell_length_c                   15.9214(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.314(2)
_cell_angle_gamma                90
_cell_volume                     1936.76(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4054
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.6260
_cell_measurement_theta_min      3.5510

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.462
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.759
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            7323
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.582
_diffrn_reflns_theta_max         70.035
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3670
_reflns_number_gt                3295
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0886P)²+0.6388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3670
_refine_ls_number_parameters     234
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.64302(3) 0.32750(5) 0.39745(3) 0.02121(17) Uani 1 1 d . . . . .
O1 O 0.62809(10) 0.31054(15) 0.30227(8) 0.0288(3) Uani 1 1 d . . . . .
O2 O 0.71019(9) 0.67945(14) 0.29553(8) 0.0268(3) Uani 1 1 d . . . . .
O3 O 0.72491(9) 0.22361(15) 0.46011(8) 0.0290(3) Uani 1 1 d . . . . .
O4 O 0.55089(9) 0.29365(14) 0.42633(9) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.92787(11) 0.4822(2) 0.56472(11) 0.0355(4) Uani 1 1 d . . . . .
N2 N 0.87093(11) 0.64823(19) 0.34751(11) 0.0286(4) Uani 1 1 d D . . . .
H2A H 0.8676(18) 0.699(2) 0.2972(12) 0.034 Uiso 1 1 d D U . . .
H2B H 0.9263(13) 0.609(3) 0.3808(14) 0.034 Uiso 1 1 d D U . . .
C1 C 0.67362(11) 0.51795(19) 0.43748(11) 0.0211(4) Uani 1 1 d . . . . .
H1 H 0.672796 0.525979 0.499880 0.025 Uiso 1 1 calc R U . . .
C2 C 0.77489(12) 0.5556(2) 0.43555(11) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.78730(12) 0.6242(2) 0.36283(11) 0.0229(4) Uani 1 1 d . . . . .
C4 C 0.62149(12) 0.6994(2) 0.31065(12) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.60016(12) 0.62616(19) 0.37858(11) 0.0225(4) Uani 1 1 d . . . . .
C6 C 0.55606(13) 0.7960(2) 0.25244(13) 0.0300(4) Uani 1 1 d . . . . .
H6 H 0.572860 0.845407 0.206598 0.036 Uiso 1 1 calc R U . . .
C7 C 0.46552(14) 0.8194(2) 0.26234(15) 0.0335(5) Uani 1 1 d . . . . .
H7 H 0.419270 0.884068 0.222436 0.040 Uiso 1 1 calc R U . . .
C8 C 0.44221(13) 0.7485(2) 0.33031(14) 0.0339(4) Uani 1 1 d . . . . .
H8 H 0.380437 0.765955 0.337381 0.041 Uiso 1 1 calc R U . . .
C9 C 0.50879(13) 0.6526(2) 0.38782(13) 0.0283(4) Uani 1 1 d . . . . .
H9 H 0.492246 0.604122 0.434069 0.034 Uiso 1 1 calc R U . . .
C10 C 0.85902(12) 0.5142(2) 0.50656(12) 0.0245(4) Uani 1 1 d . . . . .
C11 C 0.79865(15) 0.1487(3) 0.43041(15) 0.0370(5) Uani 1 1 d . . . . .
H11A H 0.863250 0.197087 0.457838 0.044 Uiso 1 1 calc R U . . .
H11B H 0.780651 0.156490 0.364921 0.044 Uiso 1 1 calc R U . . .
C12 C 0.80365(16) -0.0152(2) 0.45804(18) 0.0479(6) Uani 1 1 d . . . . .
H12A H 0.738117 -0.060640 0.430575 0.057 Uiso 1 1 calc R U . . .
H12B H 0.849485 -0.068071 0.433791 0.057 Uiso 1 1 calc R U . . .
C13 C 0.83599(18) -0.0419(3) 0.5574(2) 0.0529(7) Uani 1 1 d . . . . .
H13A H 0.831260 -0.150542 0.568361 0.064 Uiso 1 1 calc R U . . .
H13B H 0.790555 0.011274 0.581982 0.064 Uiso 1 1 calc R U . . .
C14 C 0.9397(2) 0.0103(4) 0.6066(2) 0.0676(8) Uani 1 1 d . . . . .
H14A H 0.985570 -0.044230 0.584162 0.101 Uiso 1 1 calc R U . . .
H14B H 0.955651 -0.009378 0.670374 0.101 Uiso 1 1 calc R U . . .
H14C H 0.944917 0.118239 0.596987 0.101 Uiso 1 1 calc R U . . .
C15 C 0.50277(14) 0.1479(2) 0.40246(16) 0.0350(5) Uani 1 1 d . . . . .
H15A H 0.533625 0.073325 0.449502 0.042 Uiso 1 1 calc R U . . .
H15B H 0.509505 0.111905 0.345942 0.042 Uiso 1 1 calc R U . . .
C16 C 0.39580(15) 0.1658(3) 0.39226(16) 0.0401(5) Uani 1 1 d . . . . .
H16A H 0.390747 0.204258 0.448922 0.048 Uiso 1 1 calc R U . . .
H16B H 0.364260 0.065748 0.381345 0.048 Uiso 1 1 calc R U . . .
C17 C 0.34011(16) 0.2702(3) 0.3178(2) 0.0558(7) Uani 1 1 d . . . . .
H17A H 0.373648 0.368738 0.326287 0.067 Uiso 1 1 calc R U . . .
H17B H 0.273507 0.286279 0.320606 0.067 Uiso 1 1 calc R U . . .
C18 C 0.3321(2) 0.2080(5) 0.2254(2) 0.0739(9) Uani 1 1 d . . . . .
H18A H 0.294335 0.278120 0.179321 0.111 Uiso 1 1 calc R U . . .
H18B H 0.298928 0.110462 0.216649 0.111 Uiso 1 1 calc R U . . .
H18C H 0.397763 0.195989 0.221360 0.111 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4661(13) . ?
P1 O3 1.5729(13) . ?
P1 O4 1.5766(12) . ?
P1 C1 1.8145(17) . ?
O2 C3 1.358(2) . ?
O2 C4 1.394(2) . ?
O3 C11 1.463(2) . ?
O4 C15 1.463(2) . ?
N1 C10 1.149(2) . ?
N2 C3 1.329(2) . ?
N2 H2A 0.908(16) . ?
N2 H2B 0.875(16) . ?
C1 C5 1.510(2) . ?
C1 C2 1.514(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.372(2) . ?
C2 C10 1.409(2) . ?
C4 C5 1.383(3) . ?
C4 C6 1.384(3) . ?
C5 C9 1.398(2) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.512(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.519(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.511(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.513(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.540(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O3 114.68(7) . . ?
O1 P1 O4 115.60(7) . . ?
O3 P1 O4 103.60(7) . . ?
O1 P1 C1 113.25(8) . . ?
O3 P1 C1 106.37(8) . . ?
O4 P1 C1 102.00(7) . . ?
C3 O2 C4 118.26(14) . . ?
C11 O3 P1 122.70(12) . . ?
C15 O4 P1 118.02(12) . . ?
C3 N2 H2A 117.2(16) . . ?
C3 N2 H2B 122.1(16) . . ?
H2A N2 H2B 120(2) . . ?
C5 C1 C2 109.48(14) . . ?
C5 C1 P1 109.79(11) . . ?
C2 C1 P1 109.00(12) . . ?
C5 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
P1 C1 H1 109.5 . . ?
C3 C2 C10 118.30(15) . . ?
C3 C2 C1 120.90(14) . . ?
C10 C2 C1 120.72(15) . . ?
N2 C3 O2 110.94(15) . . ?
N2 C3 C2 127.44(16) . . ?
O2 C3 C2 121.61(15) . . ?
C5 C4 C6 122.48(16) . . ?
C5 C4 O2 122.12(15) . . ?
C6 C4 O2 115.40(16) . . ?
C4 C5 C9 117.81(16) . . ?
C4 C5 C1 119.58(15) . . ?
C9 C5 C1 122.58(16) . . ?
C4 C6 C7 118.69(18) . . ?
C4 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C8 120.24(18) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.09(17) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C5 120.70(18) . . ?
C8 C9 H9 119.7 . . ?
C5 C9 H9 119.7 . . ?
N1 C10 C2 179.1(2) . . ?
O3 C11 C12 108.31(18) . . ?
O3 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O3 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C13 C12 C11 114.96(19) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 113.7(2) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C16 108.50(16) . . ?
O4 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
O4 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C15 C16 C17 114.24(19) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 112.3(2) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O1 P1 O3 C11 16.63(18) . . . . ?
O4 P1 O3 C11 143.53(15) . . . . ?
C1 P1 O3 C11 -109.37(16) . . . . ?
O1 P1 O4 C15 54.90(16) . . . . ?
O3 P1 O4 C15 -71.41(15) . . . . ?
C1 P1 O4 C15 178.23(14) . . . . ?
O1 P1 C1 C5 51.11(14) . . . . ?
O3 P1 C1 C5 177.97(11) . . . . ?
O4 P1 C1 C5 -73.79(13) . . . . ?
O1 P1 C1 C2 -68.81(13) . . . . ?
O3 P1 C1 C2 58.05(13) . . . . ?
O4 P1 C1 C2 166.29(11) . . . . ?
C5 C1 C2 C3 -27.5(2) . . . . ?
P1 C1 C2 C3 92.62(18) . . . . ?
C5 C1 C2 C10 155.81(16) . . . . ?
P1 C1 C2 C10 -84.07(18) . . . . ?
C4 O2 C3 N2 -163.56(15) . . . . ?
C4 O2 C3 C2 15.7(2) . . . . ?
C10 C2 C3 N2 5.1(3) . . . . ?
C1 C2 C3 N2 -171.66(17) . . . . ?
C10 C2 C3 O2 -173.98(16) . . . . ?
C1 C2 C3 O2 9.2(3) . . . . ?
C3 O2 C4 C5 -19.8(2) . . . . ?
C3 O2 C4 C6 160.96(16) . . . . ?
C6 C4 C5 C9 -0.2(3) . . . . ?
O2 C4 C5 C9 -179.41(16) . . . . ?
C6 C4 C5 C1 177.76(16) . . . . ?
O2 C4 C5 C1 -1.5(2) . . . . ?
C2 C1 C5 C4 23.3(2) . . . . ?
P1 C1 C5 C4 -96.38(16) . . . . ?
C2 C1 C5 C9 -158.90(16) . . . . ?
P1 C1 C5 C9 81.47(18) . . . . ?
C5 C4 C6 C7 -0.4(3) . . . . ?
O2 C4 C6 C7 178.84(16) . . . . ?
C4 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C5 0.3(3) . . . . ?
C4 C5 C9 C8 0.3(3) . . . . ?
C1 C5 C9 C8 -177.60(17) . . . . ?
P1 O3 C11 C12 -131.82(16) . . . . ?
O3 C11 C12 C13 -62.9(2) . . . . ?
C11 C12 C13 C14 -63.5(3) . . . . ?
P1 O4 C15 C16 -151.38(15) . . . . ?
O4 C15 C16 C17 63.4(3) . . . . ?
C15 C16 C17 C18 66.2(3) . . . . ?

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
_geom_hbond_publ_flag
N2 H2A O1 0.908(16) 1.887(16) 2.793(2) 175(2) 2_655 yes
N2 H2B N1 0.875(16) 2.157(17) 3.015(2) 167(2) 3_766 yes

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_Structure-14a
_database_code_depnum_ccdc_archive 'CCDC 2083634'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N2 O2 P, C2 H3 N'
_chemical_formula_sum            'C24 H20 N3 O2 P'
_chemical_formula_weight         413.40

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.3634(7)
_cell_length_b                   10.7573(6)
_cell_length_c                   15.9936(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.939(5)
_cell_angle_gamma                90
_cell_volume                     2081.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4516
_cell_measurement_theta_max      30.1200
_cell_measurement_theta_min      3.1840

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            10972
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4755
_reflns_number_gt                3899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+1.1508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4755
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.22153(3) 0.30863(4) 0.74340(2) 0.01778(12) Uani 1 1 d . . . . .
O1 O 0.12363(9) 0.31502(11) 0.78451(7) 0.0223(3) Uani 1 1 d . . . . .
O2 O 0.11313(9) 0.62068(12) 0.77838(7) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.15525(13) 0.51495(17) 0.49917(9) 0.0338(4) Uani 1 1 d . . . . .
N2 N 0.00225(12) 0.63429(16) 0.65015(9) 0.0266(3) Uani 1 1 d . . . . .
H2A H -0.0373(17) 0.689(2) 0.6746(13) 0.032 Uiso 1 1 d . U . . .
H2B H -0.0253(16) 0.607(2) 0.5987(13) 0.032 Uiso 1 1 d . U . . .
C1 C 0.27109(12) 0.46490(16) 0.72316(9) 0.0183(3) Uani 1 1 d . . . . .
H1 H 0.336931 0.457686 0.696189 0.022 Uiso 1 1 calc R U . . .
C2 C 0.17779(12) 0.52989(16) 0.66201(10) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.09877(13) 0.59233(16) 0.69373(9) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.22011(12) 0.61443(16) 0.82771(9) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.30095(12) 0.54062(16) 0.80407(9) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.24001(14) 0.68649(18) 0.90114(11) 0.0268(4) Uani 1 1 d . . . . .
H6 H 0.182876 0.735708 0.915782 0.032 Uiso 1 1 calc R U . . .
C7 C 0.34485(15) 0.68533(19) 0.95276(11) 0.0310(4) Uani 1 1 d . . . . .
H7 H 0.359873 0.732873 1.003908 0.037 Uiso 1 1 calc R U . . .
C8 C 0.42789(14) 0.61469(19) 0.92969(11) 0.0302(4) Uani 1 1 d . . . . .
H8 H 0.500112 0.615551 0.964564 0.036 Uiso 1 1 calc R U . . .
C9 C 0.40631(13) 0.54277(17) 0.85607(11) 0.0250(4) Uani 1 1 d . . . . .
H9 H 0.463830 0.494641 0.841028 0.030 Uiso 1 1 calc R U . . .
C10 C 0.16537(13) 0.51991(17) 0.57241(10) 0.0229(3) Uani 1 1 d . . . . .
C11 C 0.18685(13) 0.23569(16) 0.63993(10) 0.0206(3) Uani 1 1 d . . . . .
C12 C 0.26536(14) 0.18928(19) 0.59693(11) 0.0305(4) Uani 1 1 d . . . . .
H12 H 0.341801 0.195614 0.622112 0.037 Uiso 1 1 calc R U . . .
C13 C 0.23229(16) 0.1340(2) 0.51762(11) 0.0352(5) Uani 1 1 d . . . . .
H13 H 0.286227 0.103538 0.488220 0.042 Uiso 1 1 calc R U . . .
C14 C 0.12161(16) 0.12276(19) 0.48108(11) 0.0314(4) Uani 1 1 d . . . . .
H14 H 0.099314 0.083226 0.427145 0.038 Uiso 1 1 calc R U . . .
C15 C 0.04294(15) 0.1692(2) 0.52302(11) 0.0319(4) Uani 1 1 d . . . . .
H15 H -0.033357 0.162071 0.497556 0.038 Uiso 1 1 calc R U . . .
C16 C 0.07505(13) 0.22600(18) 0.60204(10) 0.0263(4) Uani 1 1 d . . . . .
H16 H 0.020803 0.258355 0.630399 0.032 Uiso 1 1 calc R U . . .
C17 C 0.33346(13) 0.21953(16) 0.80476(10) 0.0207(3) Uani 1 1 d . . . . .
C18 C 0.30650(14) 0.12956(18) 0.85983(10) 0.0273(4) Uani 1 1 d . . . . .
H18 H 0.233415 0.125336 0.869704 0.033 Uiso 1 1 calc R U . . .
C19 C 0.38580(16) 0.0464(2) 0.90015(11) 0.0339(4) Uani 1 1 d . . . . .
H19 H 0.366446 -0.017055 0.935671 0.041 Uiso 1 1 calc R U . . .
C20 C 0.49347(16) 0.0560(2) 0.88857(11) 0.0336(4) Uani 1 1 d . . . . .
H20 H 0.547751 -0.001407 0.915953 0.040 Uiso 1 1 calc R U . . .
C21 C 0.52244(14) 0.14852(18) 0.83753(11) 0.0279(4) Uani 1 1 d . . . . .
H21 H 0.597095 0.156707 0.831857 0.033 Uiso 1 1 calc R U . . .
C22 C 0.44251(13) 0.22966(17) 0.79443(10) 0.0241(4) Uani 1 1 d . . . . .
H22 H 0.462033 0.291847 0.758048 0.029 Uiso 1 1 calc R U . . .
N3 N 0.6759(3) 0.3853(3) 0.8094(2) 0.0991(10) Uani 1 1 d . . . . .
C23 C 0.7622(2) 0.4024(2) 0.79670(17) 0.0552(6) Uani 1 1 d . . . . .
C24 C 0.86868(18) 0.4283(2) 0.77637(19) 0.0568(7) Uani 1 1 d . . . . .
H24A H 0.863148 0.420557 0.714572 0.085 Uiso 1 1 calc R U . . .
H24B H 0.923374 0.368866 0.806232 0.085 Uiso 1 1 calc R U . . .
H24C H 0.891656 0.512958 0.794529 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4937(11) . ?
P1 C17 1.7986(17) . ?
P1 C11 1.8011(16) . ?
P1 C1 1.8407(17) . ?
O2 C3 1.3631(18) . ?
O2 C4 1.3945(18) . ?
N1 C10 1.153(2) . ?
N2 C3 1.330(2) . ?
N2 H2A 0.91(2) . ?
N2 H2B 0.87(2) . ?
C1 C5 1.509(2) . ?
C1 C2 1.520(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.367(2) . ?
C2 C10 1.413(2) . ?
C4 C6 1.386(2) . ?
C4 C5 1.389(2) . ?
C5 C9 1.393(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.393(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.395(2) . ?
C17 C22 1.396(2) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N3 C23 1.141(3) . ?
C23 C24 1.447(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C17 112.73(7) . . ?
O1 P1 C11 111.34(7) . . ?
C17 P1 C11 106.21(8) . . ?
O1 P1 C1 111.40(7) . . ?
C17 P1 C1 109.64(7) . . ?
C11 P1 C1 105.12(7) . . ?
C3 O2 C4 117.68(11) . . ?
C3 N2 H2A 120.1(13) . . ?
C3 N2 H2B 120.8(14) . . ?
H2A N2 H2B 119.0(18) . . ?
C5 C1 C2 108.79(13) . . ?
C5 C1 P1 111.93(11) . . ?
C2 C1 P1 107.30(10) . . ?
C5 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
P1 C1 H1 109.6 . . ?
C3 C2 C10 118.53(14) . . ?
C3 C2 C1 119.53(13) . . ?
C10 C2 C1 121.76(14) . . ?
N2 C3 O2 111.28(14) . . ?
N2 C3 C2 127.22(14) . . ?
O2 C3 C2 121.50(14) . . ?
C6 C4 C5 122.61(15) . . ?
C6 C4 O2 115.70(14) . . ?
C5 C4 O2 121.69(14) . . ?
C4 C5 C9 117.69(15) . . ?
C4 C5 C1 118.68(13) . . ?
C9 C5 C1 123.62(15) . . ?
C7 C6 C4 118.69(16) . . ?
C7 C6 H6 120.7 . . ?
C4 C6 H6 120.7 . . ?
C6 C7 C8 119.95(17) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.54(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C5 120.51(16) . . ?
C8 C9 H9 119.7 . . ?
C5 C9 H9 119.7 . . ?
N1 C10 C2 178.3(2) . . ?
C12 C11 C16 119.22(15) . . ?
C12 C11 P1 123.50(13) . . ?
C16 C11 P1 117.28(12) . . ?
C13 C12 C11 120.18(16) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.37(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.93(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.24(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.05(16) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C18 C17 C22 119.45(16) . . ?
C18 C17 P1 117.19(12) . . ?
C22 C17 P1 123.14(13) . . ?
C19 C18 C17 120.26(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.81(17) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.46(17) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.07(16) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 119.82(16) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 120.1 . . ?
N3 C23 C24 176.7(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
O1 P1 C1 C5 57.67(12) . . . . ?
C17 P1 C1 C5 -67.81(12) . . . . ?
C11 P1 C1 C5 178.39(11) . . . . ?
O1 P1 C1 C2 -61.61(11) . . . . ?
C17 P1 C1 C2 172.91(10) . . . . ?
C11 P1 C1 C2 59.11(11) . . . . ?
C5 C1 C2 C3 -34.9(2) . . . . ?
P1 C1 C2 C3 86.38(17) . . . . ?
C5 C1 C2 C10 149.98(15) . . . . ?
P1 C1 C2 C10 -88.74(16) . . . . ?
C4 O2 C3 N2 -162.57(15) . . . . ?
C4 O2 C3 C2 16.6(2) . . . . ?
C10 C2 C3 N2 8.5(3) . . . . ?
C1 C2 C3 N2 -166.77(17) . . . . ?
C10 C2 C3 O2 -170.57(15) . . . . ?
C1 C2 C3 O2 14.2(2) . . . . ?
C3 O2 C4 C6 156.02(15) . . . . ?
C3 O2 C4 C5 -23.9(2) . . . . ?
C6 C4 C5 C9 -1.6(3) . . . . ?
O2 C4 C5 C9 178.31(15) . . . . ?
C6 C4 C5 C1 179.67(15) . . . . ?
O2 C4 C5 C1 -0.5(2) . . . . ?
C2 C1 C5 C4 27.66(19) . . . . ?
P1 C1 C5 C4 -90.74(16) . . . . ?
C2 C1 C5 C9 -151.04(15) . . . . ?
P1 C1 C5 C9 90.56(17) . . . . ?
C5 C4 C6 C7 0.3(3) . . . . ?
O2 C4 C6 C7 -179.52(16) . . . . ?
C4 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C5 0.1(3) . . . . ?
C4 C5 C9 C8 1.3(3) . . . . ?
C1 C5 C9 C8 180.00(16) . . . . ?
O1 P1 C11 C12 -163.25(15) . . . . ?
C17 P1 C11 C12 -40.18(18) . . . . ?
C1 P1 C11 C12 76.00(17) . . . . ?
O1 P1 C11 C16 16.68(17) . . . . ?
C17 P1 C11 C16 139.75(14) . . . . ?
C1 P1 C11 C16 -104.07(15) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
P1 C11 C12 C13 179.75(16) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
P1 C11 C16 C15 -179.05(15) . . . . ?
O1 P1 C17 C18 24.94(16) . . . . ?
C11 P1 C17 C18 -97.25(14) . . . . ?
C1 P1 C17 C18 149.65(13) . . . . ?
O1 P1 C17 C22 -160.39(13) . . . . ?
C11 P1 C17 C22 77.42(15) . . . . ?
C1 P1 C17 C22 -35.68(16) . . . . ?
C22 C17 C18 C19 -3.7(3) . . . . ?
P1 C17 C18 C19 171.21(14) . . . . ?
C17 C18 C19 C20 2.8(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C22 -2.7(3) . . . . ?
C20 C21 C22 C17 1.8(3) . . . . ?
C18 C17 C22 C21 1.4(3) . . . . ?
P1 C17 C22 C21 -173.15(13) . . . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_Structure-13
_database_code_depnum_ccdc_archive 'CCDC 2083633'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N2 O5 P'
_chemical_formula_sum            'C26 H25 N2 O5 P'
_chemical_formula_weight         476.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9066(4)
_cell_length_b                   9.9454(4)
_cell_length_c                   12.3415(6)
_cell_angle_alpha                102.791(4)
_cell_angle_beta                 101.823(4)
_cell_angle_gamma                90.163(3)
_cell_volume                     1159.14(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4996
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.4510
_cell_measurement_theta_min      3.7230

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.398
_shelx_estimated_absorpt_T_min   0.542
_shelx_estimated_absorpt_T_max   0.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            7877
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.757
_diffrn_reflns_theta_max         70.074
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4385
_reflns_number_gt                4086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.2759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4385
_refine_ls_number_parameters     314
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.75173(4) 0.69643(3) 0.54377(3) 0.01844(13) Uani 1 1 d . . . . .
O1 O 0.59991(11) 0.68399(11) 0.50983(9) 0.0245(2) Uani 1 1 d . . . . .
O2 O 0.62263(10) 1.07324(10) 0.65334(8) 0.0200(2) Uani 1 1 d . . . . .
O3 O 0.82664(11) 0.65302(11) 0.44076(9) 0.0236(2) Uani 1 1 d . . . . .
O4 O 0.81805(12) 0.60866(11) 0.63066(9) 0.0250(3) Uani 1 1 d . . . . .
O5 O 0.55267(12) 1.15970(11) 0.84676(9) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.86729(16) 0.96053(15) 0.35665(12) 0.0314(3) Uani 1 1 d . . . . .
N2 N 0.62558(14) 1.14501(14) 0.49555(11) 0.0228(3) Uani 1 1 d D . . . .
H2A H 0.5571(17) 1.1936(19) 0.5120(16) 0.027 Uiso 1 1 d D U . . .
H2B H 0.647(2) 1.135(2) 0.4298(14) 0.027 Uiso 1 1 d D U . . .
C1 C 0.82621(15) 0.86839(14) 0.61421(12) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.929011 0.866277 0.625697 0.023 Uiso 1 1 calc R U . . .
C2 C 0.77624(15) 0.96591(14) 0.53778(12) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.67755(15) 1.05771(15) 0.55941(12) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.68976(15) 1.01569(15) 0.74126(12) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.78855(15) 0.91902(15) 0.72886(12) 0.0199(3) Uani 1 1 d . . . . .
C6 C 0.65255(15) 1.06625(15) 0.84615(13) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.71864(17) 1.01823(17) 0.93963(13) 0.0262(3) Uani 1 1 d . . . . .
H7 H 0.695296 1.051272 1.011442 0.031 Uiso 1 1 calc R U . . .
C8 C 0.81921(18) 0.92161(17) 0.92823(14) 0.0281(3) Uani 1 1 d . . . . .
H8 H 0.864553 0.889496 0.992638 0.034 Uiso 1 1 calc R U . . .
C9 C 0.85372(16) 0.87198(16) 0.82424(13) 0.0248(3) Uani 1 1 d . . . . .
H9 H 0.922040 0.805575 0.817485 0.030 Uiso 1 1 calc R U . . .
C10 C 0.82806(16) 0.96199(15) 0.43866(13) 0.0226(3) Uani 1 1 d . . . . .
C11 C 0.52091(19) 1.21798(18) 0.95559(13) 0.0304(4) Uani 1 1 d . . . . .
H11A H 0.602650 1.270773 1.007754 0.036 Uiso 1 1 calc R U . . .
H11B H 0.493435 1.143868 0.989853 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4041(2) 1.3117(3) 0.93608(17) 0.0513(6) Uani 1 1 d . . . . .
H12A H 0.324373 1.258552 0.883461 0.077 Uiso 1 1 calc R U . . .
H12B H 0.433130 1.385502 0.903470 0.077 Uiso 1 1 calc R U . . .
H12C H 0.378592 1.352200 1.008587 0.077 Uiso 1 1 calc R U . . .
C13 C 0.74868(17) 0.61574(16) 0.32324(13) 0.0249(3) Uani 1 1 d . . . . .
H13A H 0.805074 0.640256 0.272183 0.030 Uiso 1 1 calc R U . . .
H13B H 0.663765 0.668182 0.315747 0.030 Uiso 1 1 calc R U . . .
C14 C 0.71076(16) 0.46361(16) 0.28911(12) 0.0221(3) Uani 1 1 d . . . . .
C15 C 0.81114(17) 0.36893(18) 0.26841(14) 0.0281(3) Uani 1 1 d . . . . .
H15 H 0.903025 0.400776 0.272777 0.034 Uiso 1 1 calc R U . . .
C16 C 0.77719(17) 0.22830(17) 0.24143(14) 0.0288(4) Uani 1 1 d . . . . .
H16 H 0.846302 0.164063 0.229033 0.035 Uiso 1 1 calc R U . . .
C17 C 0.64254(18) 0.18136(17) 0.23255(13) 0.0272(3) Uani 1 1 d . . . . .
H17 H 0.619398 0.085035 0.213355 0.033 Uiso 1 1 calc R U . . .
C18 C 0.54187(17) 0.27449(18) 0.25158(14) 0.0287(4) Uani 1 1 d . . . . .
H18 H 0.449419 0.242387 0.244689 0.034 Uiso 1 1 calc R U . . .
C19 C 0.57664(17) 0.41543(17) 0.28085(13) 0.0265(3) Uani 1 1 d . . . . .
H19 H 0.507825 0.479321 0.295334 0.032 Uiso 1 1 calc R U . . .
C20 C 0.78177(18) 0.46095(15) 0.60732(14) 0.0274(4) Uani 1 1 d . . . . .
H20A H 0.826693 0.410008 0.546934 0.033 Uiso 1 1 calc R U . . .
H20B H 0.680559 0.444072 0.581197 0.033 Uiso 1 1 calc R U . . .
C21 C 0.83027(16) 0.41254(15) 0.71514(13) 0.0232(3) Uani 1 1 d . . . . .
C22 C 0.91153(16) 0.29905(15) 0.71576(14) 0.0242(3) Uani 1 1 d . . . . .
H22 H 0.938722 0.253432 0.648011 0.029 Uiso 1 1 calc R U . . .
C23 C 0.95342(17) 0.25163(16) 0.81458(15) 0.0283(4) Uani 1 1 d . . . . .
H23 H 1.008676 0.173666 0.814022 0.034 Uiso 1 1 calc R U . . .
C24 C 0.91487(18) 0.31767(18) 0.91371(15) 0.0308(4) Uani 1 1 d . . . . .
H24 H 0.943368 0.285270 0.981304 0.037 Uiso 1 1 calc R U . . .
C25 C 0.83410(18) 0.43182(19) 0.91385(15) 0.0319(4) Uani 1 1 d . . . . .
H25 H 0.807391 0.477545 0.981785 0.038 Uiso 1 1 calc R U . . .
C26 C 0.79251(17) 0.47905(17) 0.81547(15) 0.0288(4) Uani 1 1 d . . . . .
H26 H 0.737791 0.557418 0.816347 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4733(11) . ?
P1 O4 1.5724(11) . ?
P1 O3 1.5807(11) . ?
P1 C1 1.8157(14) . ?
O2 C3 1.3577(18) . ?
O2 C4 1.3888(17) . ?
O3 C13 1.4625(18) . ?
O4 C20 1.4619(18) . ?
O5 C6 1.3594(18) . ?
O5 C11 1.4383(18) . ?
N1 C10 1.153(2) . ?
N2 C3 1.3338(19) . ?
N2 H2A 0.866(15) . ?
N2 H2B 0.865(15) . ?
C1 C2 1.5139(19) . ?
C1 C5 1.515(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.366(2) . ?
C2 C10 1.413(2) . ?
C4 C5 1.381(2) . ?
C4 C6 1.405(2) . ?
C5 C9 1.398(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.503(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.503(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.387(2) . ?
C14 C15 1.394(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.502(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.389(2) . ?
C21 C26 1.393(2) . ?
C22 C23 1.389(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O4 115.51(6) . . ?
O1 P1 O3 113.66(6) . . ?
O4 P1 O3 104.71(6) . . ?
O1 P1 C1 115.80(6) . . ?
O4 P1 C1 102.02(6) . . ?
O3 P1 C1 103.59(6) . . ?
C3 O2 C4 117.80(11) . . ?
C13 O3 P1 121.47(10) . . ?
C20 O4 P1 120.02(9) . . ?
C6 O5 C11 116.03(12) . . ?
C3 N2 H2A 119.5(13) . . ?
C3 N2 H2B 117.3(13) . . ?
H2A N2 H2B 121.3(18) . . ?
C2 C1 C5 110.07(12) . . ?
C2 C1 P1 108.56(10) . . ?
C5 C1 P1 112.13(10) . . ?
C2 C1 H1 108.7 . . ?
C5 C1 H1 108.7 . . ?
P1 C1 H1 108.7 . . ?
C3 C2 C10 117.42(13) . . ?
C3 C2 C1 121.92(13) . . ?
C10 C2 C1 120.63(13) . . ?
N2 C3 O2 111.35(12) . . ?
N2 C3 C2 125.89(14) . . ?
O2 C3 C2 122.74(13) . . ?
C5 C4 O2 123.31(13) . . ?
C5 C4 C6 121.84(13) . . ?
O2 C4 C6 114.82(13) . . ?
C4 C5 C9 118.56(14) . . ?
C4 C5 C1 119.97(13) . . ?
C9 C5 C1 121.46(13) . . ?
O5 C6 C7 125.31(14) . . ?
O5 C6 C4 116.10(13) . . ?
C7 C6 C4 118.59(14) . . ?
C6 C7 C8 120.02(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.67(14) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C5 120.31(14) . . ?
C8 C9 H9 119.8 . . ?
C5 C9 H9 119.8 . . ?
N1 C10 C2 178.18(16) . . ?
O5 C11 C12 107.24(13) . . ?
O5 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O5 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 110.22(12) . . ?
O3 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O3 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C19 C14 C15 119.19(15) . . ?
C19 C14 C13 120.55(14) . . ?
C15 C14 C13 120.24(14) . . ?
C16 C15 C14 120.17(15) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.11(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.14(15) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.69(15) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.67(15) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O4 C20 C21 108.07(12) . . ?
O4 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
O4 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C22 C21 C26 118.96(14) . . ?
C22 C21 C20 120.42(15) . . ?
C26 C21 C20 120.61(14) . . ?
C21 C22 C23 120.59(15) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.14(15) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.58(15) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.26(16) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 120.47(15) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?

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
O1 P1 O3 C13 4.78(13) . . . . ?
O4 P1 O3 C13 131.73(11) . . . . ?
C1 P1 O3 C13 -121.71(11) . . . . ?
O1 P1 O4 C20 51.98(13) . . . . ?
O3 P1 O4 C20 -73.83(12) . . . . ?
C1 P1 O4 C20 178.46(12) . . . . ?
O1 P1 C1 C2 -56.04(12) . . . . ?
O4 P1 C1 C2 177.67(10) . . . . ?
O3 P1 C1 C2 69.10(11) . . . . ?
O1 P1 C1 C5 65.79(12) . . . . ?
O4 P1 C1 C5 -60.50(11) . . . . ?
O3 P1 C1 C5 -169.08(10) . . . . ?
C5 C1 C2 C3 -18.13(19) . . . . ?
P1 C1 C2 C3 104.95(14) . . . . ?
C5 C1 C2 C10 163.75(13) . . . . ?
P1 C1 C2 C10 -73.17(15) . . . . ?
C4 O2 C3 N2 -164.26(12) . . . . ?
C4 O2 C3 C2 14.00(19) . . . . ?
C10 C2 C3 N2 -0.3(2) . . . . ?
C1 C2 C3 N2 -178.49(14) . . . . ?
C10 C2 C3 O2 -178.31(13) . . . . ?
C1 C2 C3 O2 3.5(2) . . . . ?
C3 O2 C4 C5 -15.14(19) . . . . ?
C3 O2 C4 C6 163.11(12) . . . . ?
O2 C4 C5 C9 177.44(13) . . . . ?
C6 C4 C5 C9 -0.7(2) . . . . ?
O2 C4 C5 C1 -1.3(2) . . . . ?
C6 C4 C5 C1 -179.47(13) . . . . ?
C2 C1 C5 C4 16.74(18) . . . . ?
P1 C1 C5 C4 -104.22(13) . . . . ?
C2 C1 C5 C9 -162.01(13) . . . . ?
P1 C1 C5 C9 77.03(16) . . . . ?
C11 O5 C6 C7 3.9(2) . . . . ?
C11 O5 C6 C4 -176.17(14) . . . . ?
C5 C4 C6 O5 -179.15(13) . . . . ?
O2 C4 C6 O5 2.57(19) . . . . ?
C5 C4 C6 C7 0.8(2) . . . . ?
O2 C4 C6 C7 -177.52(13) . . . . ?
O5 C6 C7 C8 179.69(15) . . . . ?
C4 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C5 0.5(3) . . . . ?
C4 C5 C9 C8 0.1(2) . . . . ?
C1 C5 C9 C8 178.84(14) . . . . ?
C6 O5 C11 C12 -177.07(16) . . . . ?
P1 O3 C13 C14 -89.52(14) . . . . ?
O3 C13 C14 C19 104.83(16) . . . . ?
O3 C13 C14 C15 -73.39(18) . . . . ?
C19 C14 C15 C16 -0.9(2) . . . . ?
C13 C14 C15 C16 177.36(14) . . . . ?
C14 C15 C16 C17 1.4(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C15 C14 C19 C18 -0.4(2) . . . . ?
C13 C14 C19 C18 -178.65(14) . . . . ?
C17 C18 C19 C14 1.2(2) . . . . ?
P1 O4 C20 C21 -165.83(10) . . . . ?
O4 C20 C21 C22 -128.16(15) . . . . ?
O4 C20 C21 C26 53.0(2) . . . . ?
C26 C21 C22 C23 0.6(2) . . . . ?
C20 C21 C22 C23 -178.22(14) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C24 C25 C26 C21 0.4(3) . . . . ?
C22 C21 C26 C25 -0.7(2) . . . . ?
C20 C21 C26 C25 178.17(15) . . . . ?

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
_geom_hbond_publ_flag
N2 H2A O1 0.866(15) 1.989(16) 2.8102(17) 157.7(18) 2_676 yes
C1 H1 N1 1.00 2.59 3.391(2) 136.7 2_776 yes

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_Structure-14c
_database_code_depnum_ccdc_archive 'CCDC 2083636'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N2 O2 P'
_chemical_formula_sum            'C26 H25 N2 O2 P'
_chemical_formula_weight         428.45

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.9952(5)
_cell_length_b                   11.0767(5)
_cell_length_c                   15.1578(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.224(4)
_cell_angle_gamma                90
_cell_volume                     2178.42(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4046
_cell_measurement_theta_max      30.1230
_cell_measurement_theta_min      3.1640

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80050
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11113
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4993
_reflns_number_gt                4000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+1.0008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4993
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.24953(3) 0.78683(4) 0.29845(3) 0.01789(11) Uani 1 1 d . . . . .
O1 O 0.27838(9) 0.90174(10) 0.25480(7) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.30260(8) 0.72309(10) 0.55913(7) 0.0229(3) Uani 1 1 d . . . . .
N1 N -0.01017(12) 0.59769(15) 0.41388(11) 0.0360(4) Uani 1 1 d . . . . .
N2 N 0.20007(11) 0.56524(13) 0.57304(10) 0.0228(3) Uani 1 1 d . . . . .
H2A H 0.2263(15) 0.5674(18) 0.6281(14) 0.027 Uiso 1 1 d . U . . .
H2B H 0.1415(15) 0.5271(18) 0.5636(13) 0.027 Uiso 1 1 d . U . . .
C1 C 0.19175(12) 0.81875(14) 0.40483(10) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.129033 0.869280 0.391474 0.022 Uiso 1 1 calc R U . . .
C2 C 0.15827(11) 0.70958(14) 0.45583(10) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.21535(11) 0.66655(14) 0.52699(10) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.31832(12) 0.84227(14) 0.53446(10) 0.0200(3) Uani 1 1 d . . . . .
C5 C 0.26607(12) 0.89367(14) 0.46169(10) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.38887(13) 0.90646(16) 0.58760(11) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.423882 0.868826 0.636974 0.032 Uiso 1 1 calc R U . . .
C7 C 0.40778(14) 1.02551(17) 0.56815(12) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.456290 1.070472 0.604027 0.037 Uiso 1 1 calc R U . . .
C8 C 0.35610(14) 1.07968(16) 0.49630(13) 0.0314(4) Uani 1 1 d . . . . .
H8 H 0.368603 1.162138 0.483403 0.038 Uiso 1 1 calc R U . . .
C9 C 0.28647(13) 1.01445(15) 0.44329(12) 0.0250(4) Uani 1 1 d . . . . .
H9 H 0.252036 1.052234 0.393708 0.030 Uiso 1 1 calc R U . . .
C10 C 0.06504(13) 0.64857(15) 0.43147(11) 0.0235(3) Uani 1 1 d . . . . .
C11 C 0.35799(12) 0.68920(14) 0.32180(10) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.45533(12) 0.73101(15) 0.30105(11) 0.0220(3) Uani 1 1 d . . . . .
H12 H 0.462033 0.809010 0.275952 0.026 Uiso 1 1 calc R U . . .
C13 C 0.54232(13) 0.65946(17) 0.31681(11) 0.0270(4) Uani 1 1 d . . . . .
C14 C 0.53024(13) 0.54523(17) 0.35294(12) 0.0293(4) Uani 1 1 d . . . . .
H14 H 0.589110 0.495068 0.362480 0.035 Uiso 1 1 calc R U . . .
C15 C 0.43482(13) 0.50220(16) 0.37551(11) 0.0259(4) Uani 1 1 d . . . . .
C16 C 0.34865(12) 0.57509(15) 0.35951(11) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.282796 0.546917 0.374401 0.027 Uiso 1 1 calc R U . . .
C17 C 0.64834(14) 0.7025(2) 0.29541(15) 0.0391(5) Uani 1 1 d . . . . .
H17A H 0.673896 0.653173 0.247653 0.059 Uiso 1 1 calc R U . . .
H17B H 0.695330 0.695242 0.348010 0.059 Uiso 1 1 calc R U . . .
H17C H 0.644585 0.787189 0.276676 0.059 Uiso 1 1 calc R U . . .
C18 C 0.42441(16) 0.37974(17) 0.41720(13) 0.0347(4) Uani 1 1 d . . . . .
H18A H 0.363305 0.378649 0.452258 0.052 Uiso 1 1 calc R U . . .
H18B H 0.485861 0.362724 0.455641 0.052 Uiso 1 1 calc R U . . .
H18C H 0.417279 0.318142 0.370853 0.052 Uiso 1 1 calc R U . . .
C19 C 0.15134(12) 0.70619(15) 0.23375(10) 0.0205(3) Uani 1 1 d . . . . .
C20 C 0.06225(12) 0.77113(15) 0.20827(11) 0.0233(3) Uani 1 1 d . . . . .
H20 H 0.054943 0.851866 0.228119 0.028 Uiso 1 1 calc R U . . .
C21 C -0.01543(12) 0.71950(16) 0.15456(12) 0.0259(4) Uani 1 1 d . . . . .
C22 C -0.00240(13) 0.60073(16) 0.12656(11) 0.0264(4) Uani 1 1 d . . . . .
H22 H -0.055610 0.564239 0.090198 0.032 Uiso 1 1 calc R U . . .
C23 C 0.08518(13) 0.53398(16) 0.14974(11) 0.0241(4) Uani 1 1 d . . . . .
C24 C 0.16239(12) 0.58840(15) 0.20415(11) 0.0219(3) Uani 1 1 d . . . . .
H24 H 0.223060 0.544344 0.221045 0.026 Uiso 1 1 calc R U . . .
C25 C -0.11113(14) 0.79030(18) 0.12721(14) 0.0358(4) Uani 1 1 d . . . . .
H25A H -0.168530 0.762772 0.161340 0.054 Uiso 1 1 calc R U . . .
H25B H -0.128282 0.777767 0.064085 0.054 Uiso 1 1 calc R U . . .
H25C H -0.098764 0.876362 0.138428 0.054 Uiso 1 1 calc R U . . .
C26 C 0.10013(14) 0.40720(17) 0.11753(13) 0.0310(4) Uani 1 1 d . . . . .
H26A H 0.168397 0.399893 0.093674 0.047 Uiso 1 1 calc R U . . .
H26B H 0.047004 0.388375 0.071122 0.047 Uiso 1 1 calc R U . . .
H26C H 0.094744 0.350676 0.166794 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4921(12) . ?
P1 C11 1.7958(16) . ?
P1 C19 1.8020(16) . ?
P1 C1 1.8508(15) . ?
O2 C3 1.3612(18) . ?
O2 C4 1.3903(19) . ?
N1 C10 1.147(2) . ?
N2 C3 1.342(2) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.88(2) . ?
C1 C5 1.507(2) . ?
C1 C2 1.512(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.360(2) . ?
C2 C10 1.418(2) . ?
C4 C6 1.383(2) . ?
C4 C5 1.385(2) . ?
C5 C9 1.395(2) . ?
C6 C7 1.376(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C16 1.395(2) . ?
C11 C12 1.399(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 C17 1.511(2) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 C18 1.506(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.390(2) . ?
C19 C20 1.399(2) . ?
C20 C21 1.384(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(2) . ?
C21 C25 1.509(2) . ?
C22 C23 1.386(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.399(2) . ?
C23 C26 1.503(2) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C11 112.77(7) . . ?
O1 P1 C19 111.68(7) . . ?
C11 P1 C19 109.43(8) . . ?
O1 P1 C1 110.35(7) . . ?
C11 P1 C1 107.19(7) . . ?
C19 P1 C1 105.03(7) . . ?
C3 O2 C4 118.21(12) . . ?
C3 N2 H2A 114.1(13) . . ?
C3 N2 H2B 118.1(13) . . ?
H2A N2 H2B 116.9(18) . . ?
C5 C1 C2 109.98(13) . . ?
C5 C1 P1 108.97(10) . . ?
C2 C1 P1 115.79(11) . . ?
C5 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
P1 C1 H1 107.2 . . ?
C3 C2 C10 117.34(14) . . ?
C3 C2 C1 121.71(14) . . ?
C10 C2 C1 120.94(14) . . ?
N2 C3 C2 127.97(15) . . ?
N2 C3 O2 110.06(14) . . ?
C2 C3 O2 121.91(14) . . ?
C6 C4 C5 122.14(15) . . ?
C6 C4 O2 115.74(15) . . ?
C5 C4 O2 122.12(14) . . ?
C4 C5 C9 117.60(15) . . ?
C4 C5 C1 119.93(14) . . ?
C9 C5 C1 122.46(15) . . ?
C7 C6 C4 119.23(17) . . ?
C7 C6 H6 120.4 . . ?
C4 C6 H6 120.4 . . ?
C6 C7 C8 119.96(17) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.30(17) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C5 120.76(17) . . ?
C8 C9 H9 119.6 . . ?
C5 C9 H9 119.6 . . ?
N1 C10 C2 178.19(19) . . ?
C16 C11 C12 119.49(15) . . ?
C16 C11 P1 122.75(12) . . ?
C12 C11 P1 117.76(12) . . ?
C13 C12 C11 120.62(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 118.52(15) . . ?
C12 C13 C17 121.71(17) . . ?
C14 C13 C17 119.76(16) . . ?
C15 C14 C13 122.08(16) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 118.62(16) . . ?
C14 C15 C18 121.00(16) . . ?
C16 C15 C18 120.38(16) . . ?
C15 C16 C11 120.64(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 119.51(15) . . ?
C24 C19 P1 123.93(12) . . ?
C20 C19 P1 116.43(12) . . ?
C21 C20 C19 120.98(16) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 118.12(16) . . ?
C20 C21 C25 120.63(16) . . ?
C22 C21 C25 121.25(16) . . ?
C23 C22 C21 122.54(16) . . ?
C23 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C22 C23 C24 118.11(16) . . ?
C22 C23 C26 122.38(16) . . ?
C24 C23 C26 119.51(16) . . ?
C19 C24 C23 120.73(15) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
O1 P1 C1 C5 -55.81(12) . . . . ?
C11 P1 C1 C5 67.35(12) . . . . ?
C19 P1 C1 C5 -176.31(11) . . . . ?
O1 P1 C1 C2 179.62(11) . . . . ?
C11 P1 C1 C2 -57.22(13) . . . . ?
C19 P1 C1 C2 59.12(13) . . . . ?
C5 C1 C2 C3 -21.6(2) . . . . ?
P1 C1 C2 C3 102.47(16) . . . . ?
C5 C1 C2 C10 157.84(14) . . . . ?
P1 C1 C2 C10 -78.11(17) . . . . ?
C10 C2 C3 N2 7.2(2) . . . . ?
C1 C2 C3 N2 -173.39(15) . . . . ?
C10 C2 C3 O2 -175.77(14) . . . . ?
C1 C2 C3 O2 3.7(2) . . . . ?
C4 O2 C3 N2 -165.08(13) . . . . ?
C4 O2 C3 C2 17.4(2) . . . . ?
C3 O2 C4 C6 161.20(14) . . . . ?
C3 O2 C4 C5 -18.3(2) . . . . ?
C6 C4 C5 C9 -0.3(2) . . . . ?
O2 C4 C5 C9 179.17(14) . . . . ?
C6 C4 C5 C1 178.63(14) . . . . ?
O2 C4 C5 C1 -1.9(2) . . . . ?
C2 C1 C5 C4 20.27(19) . . . . ?
P1 C1 C5 C4 -107.65(14) . . . . ?
C2 C1 C5 C9 -160.83(14) . . . . ?
P1 C1 C5 C9 71.26(17) . . . . ?
C5 C4 C6 C7 0.3(2) . . . . ?
O2 C4 C6 C7 -179.22(14) . . . . ?
C4 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C5 0.8(3) . . . . ?
C4 C5 C9 C8 -0.2(2) . . . . ?
C1 C5 C9 C8 -179.14(15) . . . . ?
O1 P1 C11 C16 -177.61(12) . . . . ?
C19 P1 C11 C16 -52.64(15) . . . . ?
C1 P1 C11 C16 60.75(15) . . . . ?
O1 P1 C11 C12 2.55(15) . . . . ?
C19 P1 C11 C12 127.51(13) . . . . ?
C1 P1 C11 C12 -119.10(13) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
P1 C11 C12 C13 -179.47(12) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C11 C12 C13 C17 -179.73(16) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C17 C13 C14 C15 178.65(17) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C13 C14 C15 C18 -178.03(17) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
C18 C15 C16 C11 179.28(16) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
P1 C11 C16 C15 179.31(13) . . . . ?
O1 P1 C19 C24 122.86(14) . . . . ?
C11 P1 C19 C24 -2.73(16) . . . . ?
C1 P1 C19 C24 -117.52(14) . . . . ?
O1 P1 C19 C20 -53.00(14) . . . . ?
C11 P1 C19 C20 -178.59(12) . . . . ?
C1 P1 C19 C20 66.62(14) . . . . ?
C24 C19 C20 C21 0.5(2) . . . . ?
P1 C19 C20 C21 176.55(13) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C19 C20 C21 C25 -179.84(16) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
C25 C21 C22 C23 179.21(16) . . . . ?
C21 C22 C23 C24 0.7(2) . . . . ?
C21 C22 C23 C26 -178.37(16) . . . . ?
C20 C19 C24 C23 -0.4(2) . . . . ?
P1 C19 C24 C23 -176.18(12) . . . . ?
C22 C23 C24 C19 -0.2(2) . . . . ?
C26 C23 C24 C19 178.97(15) . . . . ?

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
_geom_hbond_publ_flag
N2 H2A O1 0.88(2) 2.03(2) 2.9060(19) 171.4(18) 4_576 yes
N2 H2B N1 0.88(2) 2.24(2) 3.073(2) 159.5(18) 3_566 yes

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_Structure-14b
_database_code_depnum_ccdc_archive 'CCDC 2083635'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N2 O2 P'
_chemical_formula_sum            'C24 H21 N2 O2 P'
_chemical_formula_weight         400.40

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0000(5)
_cell_length_b                   11.1653(8)
_cell_length_c                   12.3858(7)
_cell_angle_alpha                115.027(7)
_cell_angle_beta                 91.058(5)
_cell_angle_gamma                113.010(6)
_cell_volume                     1012.50(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2713
_cell_measurement_theta_max      29.2170
_cell_measurement_theta_min      3.2980

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81350
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            8457
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.521
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4649
_reflns_number_gt                3712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.4120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4649
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.79848(5) 0.33470(5) 0.69995(4) 0.02001(12) Uani 1 1 d . . . . .
O1 O 0.96948(15) 0.43682(13) 0.70721(11) 0.0265(3) Uani 1 1 d . . . . .
O2 O 0.89208(15) 0.31868(13) 0.40524(11) 0.0242(3) Uani 1 1 d . . . . .
N1 N 0.3870(2) 0.33259(18) 0.49603(16) 0.0317(4) Uani 1 1 d . . . . .
N2 N 0.7693(2) 0.45458(18) 0.39766(14) 0.0264(3) Uani 1 1 d . . . . .
H2B H 0.713(3) 0.502(2) 0.4270(19) 0.032 Uiso 1 1 d . U . . .
H2A H 0.857(3) 0.489(2) 0.3649(18) 0.032 Uiso 1 1 d . U . . .
C1 C 0.6814(2) 0.20370(18) 0.54088(15) 0.0199(3) Uani 1 1 d . . . . .
H1 H 0.573940 0.128961 0.540849 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6474(2) 0.28866(18) 0.48279(15) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.7641(2) 0.35505(18) 0.43102(15) 0.0209(3) Uani 1 1 d . . . . .
C4 C 0.8778(2) 0.18841(18) 0.40246(15) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.7771(2) 0.12646(18) 0.46639(15) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.9707(2) 0.1250(2) 0.33318(16) 0.0282(4) Uani 1 1 d . . . . .
H6 H 1.041962 0.171296 0.292679 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9584(2) -0.0068(2) 0.32357(17) 0.0304(4) Uani 1 1 d . . . . .
H7 H 1.020314 -0.052136 0.275133 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8566(2) -0.0727(2) 0.38408(16) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.847142 -0.163933 0.376180 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7683(2) -0.00551(18) 0.45630(16) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.700829 -0.049912 0.499536 0.028 Uiso 1 1 calc R U . . .
C10 C 0.5046(2) 0.31422(18) 0.49173(16) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.6755(2) 0.43029(18) 0.76411(15) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.7157(2) 0.56359(19) 0.76304(17) 0.0276(4) Uani 1 1 d . . . . .
H12 H 0.809460 0.603784 0.733402 0.033 Uiso 1 1 calc R U . . .
C13 C 0.6191(2) 0.6378(2) 0.80524(17) 0.0315(4) Uani 1 1 d . . . . .
H13 H 0.647231 0.728386 0.803722 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4822(2) 0.5818(2) 0.84954(16) 0.0289(4) Uani 1 1 d . . . . .
C15 C 0.4416(2) 0.4480(2) 0.84910(17) 0.0295(4) Uani 1 1 d . . . . .
H15 H 0.347528 0.407737 0.878380 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5368(2) 0.3722(2) 0.80643(16) 0.0264(4) Uani 1 1 d . . . . .
H16 H 0.506924 0.280474 0.806189 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3793(3) 0.6638(2) 0.89898(19) 0.0389(5) Uani 1 1 d . . . . .
H17A H 0.414839 0.748036 0.882287 0.058 Uiso 1 1 calc R U . . .
H17B H 0.393897 0.698942 0.987347 0.058 Uiso 1 1 calc R U . . .
H17C H 0.262324 0.597799 0.859359 0.058 Uiso 1 1 calc R U . . .
C18 C 0.7966(2) 0.23459(18) 0.78267(15) 0.0217(4) Uani 1 1 d . . . . .
C19 C 0.9313(2) 0.3033(2) 0.88031(16) 0.0266(4) Uani 1 1 d . . . . .
H19 H 1.022613 0.392039 0.893921 0.032 Uiso 1 1 calc R U . . .
C20 C 0.9321(2) 0.2426(2) 0.95731(16) 0.0315(4) Uani 1 1 d . . . . .
H20 H 1.024093 0.290907 1.023641 0.038 Uiso 1 1 calc R U . . .
C21 C 0.8011(3) 0.1127(2) 0.93944(16) 0.0300(4) Uani 1 1 d . . . . .
C22 C 0.6700(2) 0.0425(2) 0.84002(17) 0.0284(4) Uani 1 1 d . . . . .
H22 H 0.581225 -0.048534 0.824557 0.034 Uiso 1 1 calc R U . . .
C23 C 0.6662(2) 0.10265(19) 0.76277(16) 0.0250(4) Uani 1 1 d . . . . .
H23 H 0.574305 0.053678 0.696177 0.030 Uiso 1 1 calc R U . . .
C24 C 0.8002(3) 0.0536(3) 1.0294(2) 0.0461(6) Uani 1 1 d . . . . .
H24A H 0.873187 0.004855 1.013739 0.069 Uiso 1 1 calc R U . . .
H24B H 0.687316 -0.017373 1.019728 0.069 Uiso 1 1 calc R U . . .
H24C H 0.839481 0.135096 1.112800 0.069 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4876(13) . ?
P1 C11 1.7983(17) . ?
P1 C18 1.8040(17) . ?
P1 C1 1.8472(17) . ?
O2 C3 1.3650(19) . ?
O2 C4 1.395(2) . ?
N1 C10 1.152(2) . ?
N2 C3 1.325(2) . ?
N2 H2B 0.85(2) . ?
N2 H2A 0.92(2) . ?
C1 C5 1.508(2) . ?
C1 C2 1.519(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.372(2) . ?
C2 C10 1.418(2) . ?
C4 C6 1.382(2) . ?
C4 C5 1.388(2) . ?
C5 C9 1.395(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C16 1.390(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 C17 1.511(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.392(2) . ?
C18 C19 1.398(2) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 C24 1.514(3) . ?
C22 C23 1.389(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C11 112.15(8) . . ?
O1 P1 C18 112.09(8) . . ?
C11 P1 C18 106.14(8) . . ?
O1 P1 C1 112.55(7) . . ?
C11 P1 C1 103.88(8) . . ?
C18 P1 C1 109.54(8) . . ?
C3 O2 C4 117.74(13) . . ?
C3 N2 H2B 119.0(14) . . ?
C3 N2 H2A 117.1(13) . . ?
H2B N2 H2A 120.9(19) . . ?
C5 C1 C2 108.48(13) . . ?
C5 C1 P1 111.73(11) . . ?
C2 C1 P1 108.46(11) . . ?
C5 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
P1 C1 H1 109.4 . . ?
C3 C2 C10 118.51(15) . . ?
C3 C2 C1 119.82(14) . . ?
C10 C2 C1 121.35(14) . . ?
N2 C3 O2 111.73(15) . . ?
N2 C3 C2 127.55(15) . . ?
O2 C3 C2 120.70(14) . . ?
C6 C4 C5 121.86(16) . . ?
C6 C4 O2 116.22(15) . . ?
C5 C4 O2 121.92(14) . . ?
C4 C5 C9 117.87(15) . . ?
C4 C5 C1 118.44(14) . . ?
C9 C5 C1 123.69(15) . . ?
C4 C6 C7 119.15(17) . . ?
C4 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.30(17) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.91(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C5 120.87(17) . . ?
C8 C9 H9 119.6 . . ?
C5 C9 H9 119.6 . . ?
N1 C10 C2 178.3(2) . . ?
C16 C11 C12 119.17(15) . . ?
C16 C11 P1 122.85(13) . . ?
C12 C11 P1 117.83(13) . . ?
C13 C12 C11 120.15(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 121.00(17) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.57(16) . . ?
C13 C14 C17 121.38(17) . . ?
C15 C14 C17 120.04(18) . . ?
C14 C15 C16 120.98(17) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 120.12(16) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.75(16) . . ?
C23 C18 P1 124.85(13) . . ?
C19 C18 P1 116.16(13) . . ?
C20 C19 C18 120.28(17) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.28(17) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 118.16(17) . . ?
C20 C21 C24 120.22(18) . . ?
C22 C21 C24 121.58(19) . . ?
C21 C22 C23 121.31(17) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 120.17(17) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
O1 P1 C1 C5 50.81(13) . . . . ?
C11 P1 C1 C5 172.35(11) . . . . ?
C18 P1 C1 C5 -74.60(13) . . . . ?
O1 P1 C1 C2 -68.71(13) . . . . ?
C11 P1 C1 C2 52.82(13) . . . . ?
C18 P1 C1 C2 165.88(11) . . . . ?
C5 C1 C2 C3 -36.3(2) . . . . ?
P1 C1 C2 C3 85.21(17) . . . . ?
C5 C1 C2 C10 150.28(16) . . . . ?
P1 C1 C2 C10 -88.17(17) . . . . ?
C4 O2 C3 N2 -162.14(14) . . . . ?
C4 O2 C3 C2 16.5(2) . . . . ?
C10 C2 C3 N2 7.3(3) . . . . ?
C1 C2 C3 N2 -166.23(16) . . . . ?
C10 C2 C3 O2 -171.09(15) . . . . ?
C1 C2 C3 O2 15.3(2) . . . . ?
C3 O2 C4 C6 155.89(15) . . . . ?
C3 O2 C4 C5 -24.6(2) . . . . ?
C6 C4 C5 C9 -1.7(3) . . . . ?
O2 C4 C5 C9 178.82(15) . . . . ?
C6 C4 C5 C1 179.35(15) . . . . ?
O2 C4 C5 C1 -0.1(2) . . . . ?
C2 C1 C5 C4 28.2(2) . . . . ?
P1 C1 C5 C4 -91.32(16) . . . . ?
C2 C1 C5 C9 -150.69(16) . . . . ?
P1 C1 C5 C9 89.79(17) . . . . ?
C5 C4 C6 C7 2.4(3) . . . . ?
O2 C4 C6 C7 -178.08(16) . . . . ?
C4 C6 C7 C8 -1.0(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C5 1.7(3) . . . . ?
C4 C5 C9 C8 -0.4(2) . . . . ?
C1 C5 C9 C8 178.50(15) . . . . ?
O1 P1 C11 C16 -157.36(14) . . . . ?
C18 P1 C11 C16 -34.65(17) . . . . ?
C1 P1 C11 C16 80.83(16) . . . . ?
O1 P1 C11 C12 27.16(16) . . . . ?
C18 P1 C11 C12 149.88(14) . . . . ?
C1 P1 C11 C12 -94.64(15) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
P1 C11 C12 C13 176.42(14) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C12 C13 C14 C17 178.21(17) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C17 C14 C15 C16 -178.62(17) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
P1 C11 C16 C15 -176.57(14) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
O1 P1 C18 C23 -158.94(14) . . . . ?
C11 P1 C18 C23 78.31(16) . . . . ?
C1 P1 C18 C23 -33.26(17) . . . . ?
O1 P1 C18 C19 26.82(15) . . . . ?
C11 P1 C18 C19 -95.93(14) . . . . ?
C1 P1 C18 C19 152.50(13) . . . . ?
C23 C18 C19 C20 -1.7(2) . . . . ?
P1 C18 C19 C20 172.95(13) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C22 1.6(3) . . . . ?
C19 C20 C21 C24 -176.23(17) . . . . ?
C20 C21 C22 C23 -2.4(3) . . . . ?
C24 C21 C22 C23 175.39(17) . . . . ?
C21 C22 C23 C18 1.2(3) . . . . ?
C19 C18 C23 C22 0.9(2) . . . . ?
P1 C18 C23 C22 -173.23(13) . . . . ?

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
_geom_hbond_publ_flag
N2 H2B N1 0.85(2) 2.23(2) 3.065(2) 167.6(19) 2_666 yes
N2 H2A O1 0.92(2) 1.89(2) 2.811(2) 177.2(19) 2_766 yes

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.052

