# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2054058'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 N3 O4 P'
_chemical_formula_weight         361.33

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/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                   11.592(3)
_cell_length_b                   7.7150(15)
_cell_length_c                   19.848(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.237(7)
_cell_angle_gamma                90
_cell_volume                     1712.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8322
_cell_measurement_theta_min      2.846
_cell_measurement_theta_max      25.361

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8322
_diffrn_reflns_av_unetI/netI     0.1508
_diffrn_reflns_av_R_equivalents  0.1102
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.846
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3108
_reflns_number_gt                1786
_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_data_collection       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 2020.1'
_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)+(0.1069P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0817
_refine_ls_wR_factor_ref         0.2347
_refine_ls_wR_factor_gt          0.1960
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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 0.38876(9) 0.40768(15) 0.59571(6) 0.0413(4) Uani 1 1 d . . . . .
O3 O 0.3994(2) 0.2915(4) 0.53234(16) 0.0478(8) Uani 1 1 d . . . . .
O2 O 0.3022(3) 0.3442(4) 0.63126(16) 0.0530(9) Uani 1 1 d . . . . .
O4 O 0.5217(2) 0.4223(4) 0.64110(17) 0.0532(9) Uani 1 1 d . . . . .
N9 N 0.1558(3) 0.8060(5) 0.59609(19) 0.0438(9) Uani 1 1 d . . . . .
N1 N 0.3052(3) 0.9172(4) 0.69473(19) 0.0458(9) Uani 1 1 d . . . . .
O1 O -0.0402(3) 0.8481(6) 0.5941(2) 0.0839(13) Uani 1 1 d . . . . .
N2 N 0.4253(3) 0.9102(5) 0.7236(2) 0.0564(11) Uani 1 1 d . . . . .
C9A C 0.2737(3) 0.8202(5) 0.6360(2) 0.0380(10) Uani 1 1 d . . . . .
C3A C 0.3734(3) 0.7487(5) 0.6245(2) 0.0390(10) Uani 1 1 d . . . . .
C4A C 0.2412(3) 0.6480(5) 0.5122(2) 0.0407(10) Uani 1 1 d . . . . .
C8A C 0.1430(3) 0.7252(5) 0.5290(2) 0.0434(11) Uani 1 1 d . . . . .
C4 C 0.3650(3) 0.6292(6) 0.5642(2) 0.0424(10) Uani 1 1 d . . . . .
H4 H 0.4267 0.6600 0.5408 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4650(4) 0.8089(7) 0.6809(2) 0.0518(12) Uani 1 1 d . . . . .
H3 H 0.5452 0.7805 0.6875 0.062 Uiso 1 1 calc R U . . .
C5 C 0.2255(4) 0.5822(6) 0.4458(2) 0.0557(13) Uani 1 1 d . . . . .
H5 H 0.2911 0.5334 0.4341 0.067 Uiso 1 1 calc R U . . .
C10 C 0.0642(4) 0.8605(6) 0.6241(3) 0.0560(13) Uani 1 1 d . . . . .
C8 C 0.0329(4) 0.7308(7) 0.4777(3) 0.0595(14) Uani 1 1 d . . . . .
H8 H -0.0326 0.7841 0.4879 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5813(4) 0.2687(7) 0.6781(3) 0.0664(15) Uani 1 1 d . . . . .
H15A H 0.6129 0.1976 0.6468 0.080 Uiso 1 1 calc R U . . .
H15B H 0.5248 0.1999 0.6951 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2216(4) 1.0221(6) 0.7190(3) 0.0561(13) Uani 1 1 d . . . . .
H12A H 0.2155 1.1365 0.6981 0.067 Uiso 1 1 calc R U . . .
H12B H 0.2473 1.0345 0.7693 0.067 Uiso 1 1 calc R U . . .
C6 C 0.1166(5) 0.5852(7) 0.3957(3) 0.0666(15) Uani 1 1 d . . . . .
H6 H 0.1085 0.5388 0.3514 0.080 Uiso 1 1 calc R U . . .
C11 C 0.1032(4) 0.9311(7) 0.6977(3) 0.0631(14) Uani 1 1 d . . . . .
H11A H 0.0423 1.0113 0.7038 0.076 Uiso 1 1 calc R U . . .
H11B H 0.1053 0.8355 0.7297 0.076 Uiso 1 1 calc R U . . .
C7 C 0.0210(5) 0.6595(7) 0.4139(3) 0.0703(16) Uani 1 1 d . . . . .
H7 H -0.0534 0.6608 0.3815 0.084 Uiso 1 1 calc R U . . .
C16 C 0.6804(5) 0.3285(9) 0.7378(3) 0.092(2) Uani 1 1 d . . . . .
H16A H 0.7206 0.2298 0.7628 0.138 Uiso 1 1 calc R U . . .
H16B H 0.7360 0.3960 0.7205 0.138 Uiso 1 1 calc R U . . .
H16C H 0.6482 0.3983 0.7686 0.138 Uiso 1 1 calc R U . . .
C13 C 0.3120(5) 0.1576(7) 0.5051(3) 0.0694(16) Uani 1 1 d . . . . .
H13A H 0.2323 0.2067 0.4949 0.083 Uiso 1 1 calc R U . . .
H13B H 0.3177 0.0676 0.5399 0.083 Uiso 1 1 calc R U . . .
C14 C 0.3321(5) 0.0814(8) 0.4409(3) 0.086(2) Uani 1 1 d . . . . .
H14A H 0.2734 -0.0069 0.4236 0.129 Uiso 1 1 calc R U . . .
H14B H 0.3253 0.1702 0.4062 0.129 Uiso 1 1 calc R U . . .
H14C H 0.4106 0.0313 0.4511 0.129 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 O2 1.455(3) . ?
P1 O4 1.571(3) . ?
P1 O3 1.576(3) . ?
P1 C4 1.816(4) . ?
O3 C13 1.449(5) . ?
O4 C15 1.468(5) . ?
N9 C10 1.387(6) . ?
N9 C9A 1.393(5) . ?
N9 C8A 1.442(5) . ?
N1 C9A 1.352(5) . ?
N1 N2 1.360(5) . ?
N1 C12 1.440(6) . ?
O1 C10 1.205(5) . ?
N2 C3 1.322(6) . ?
C9A C3A 1.353(6) . ?
C3A C3 1.405(6) . ?
C3A C4 1.493(6) . ?
C4A C5 1.379(6) . ?
C4A C8A 1.400(6) . ?
C4A C4 1.539(5) . ?
C8A C8 1.409(6) . ?
C4 H4 0.9800 . ?
C3 H3 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C10 C11 1.512(7) . ?
C8 C7 1.356(7) . ?
C8 H8 0.9300 . ?
C15 C16 1.490(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 C11 1.499(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C7 1.377(7) . ?
C6 H6 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 C14 1.476(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
O2 P1 O4 116.33(19) . . ?
O2 P1 O3 113.86(18) . . ?
O4 P1 O3 103.16(17) . . ?
O2 P1 C4 114.98(19) . . ?
O4 P1 C4 99.62(17) . . ?
O3 P1 C4 107.28(19) . . ?
C13 O3 P1 120.7(3) . . ?
C15 O4 P1 119.4(3) . . ?
C10 N9 C9A 119.2(4) . . ?
C10 N9 C8A 126.7(4) . . ?
C9A N9 C8A 114.0(3) . . ?
C9A N1 N2 110.9(4) . . ?
C9A N1 C12 123.1(4) . . ?
N2 N1 C12 125.9(4) . . ?
C3 N2 N1 104.1(4) . . ?
N1 C9A C3A 108.8(3) . . ?
N1 C9A N9 122.4(4) . . ?
C3A C9A N9 128.7(4) . . ?
C9A C3A C3 103.3(4) . . ?
C9A C3A C4 120.6(3) . . ?
C3 C3A C4 136.0(4) . . ?
C5 C4A C8A 118.3(4) . . ?
C5 C4A C4 118.1(4) . . ?
C8A C4A C4 123.6(4) . . ?
C4A C8A C8 118.7(4) . . ?
C4A C8A N9 120.8(3) . . ?
C8 C8A N9 120.5(4) . . ?
C3A C4 C4A 109.4(3) . . ?
C3A C4 P1 109.5(3) . . ?
C4A C4 P1 110.5(3) . . ?
C3A C4 H4 109.2 . . ?
C4A C4 H4 109.2 . . ?
P1 C4 H4 109.2 . . ?
N2 C3 C3A 112.9(4) . . ?
N2 C3 H3 123.5 . . ?
C3A C3 H3 123.5 . . ?
C4A C5 C6 123.0(5) . . ?
C4A C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
O1 C10 N9 123.6(5) . . ?
O1 C10 C11 120.8(5) . . ?
N9 C10 C11 115.5(4) . . ?
C7 C8 C8A 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
O4 C15 C16 108.1(4) . . ?
O4 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O4 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
N1 C12 C11 106.8(4) . . ?
N1 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
N1 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C7 C6 C5 117.5(5) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C12 C11 C10 117.4(4) . . ?
C12 C11 H11A 107.9 . . ?
C10 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
C10 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C8 C7 C6 121.6(5) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C13 C14 110.7(4) . . ?
O3 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
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 . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.095

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2054059'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 N3 O4 P'
_chemical_formula_weight         361.33

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/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                   7.8318(10)
_cell_length_b                   10.2797(13)
_cell_length_c                   21.689(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.470(6)
_cell_angle_gamma                90
_cell_volume                     1727.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    30838
_cell_measurement_theta_min      2.744
_cell_measurement_theta_max      25.242

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30838
_diffrn_reflns_av_unetI/netI     0.1161
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.744
_diffrn_reflns_theta_max         29.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4838
_reflns_number_gt                3362
_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_data_collection       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 2020.1'
_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)+(0.1213P)²+0.5419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4838
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2458
_refine_ls_wR_factor_gt          0.2171
_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 0.57070(8) 0.40041(7) 0.39382(3) 0.0392(2) Uani 1 1 d . . . . .
O2 O 0.5973(3) 0.3874(2) 0.32881(8) 0.0523(5) Uani 1 1 d . . . . .
O4 O 0.6241(3) 0.2790(2) 0.43623(9) 0.0586(6) Uani 1 1 d . . . . .
O3 O 0.6701(2) 0.5176(2) 0.42939(9) 0.0567(5) Uani 1 1 d . . . . .
N9 N 0.0825(3) 0.4144(2) 0.29229(10) 0.0397(5) Uani 1 1 d . . . . .
O1 O -0.0835(4) 0.4748(3) 0.20098(12) 0.0872(8) Uani 1 1 d . . . . .
N1 N 0.0662(3) 0.1892(2) 0.32221(12) 0.0548(6) Uani 1 1 d . . . . .
C4 C 0.3484(3) 0.4273(2) 0.40629(11) 0.0371(5) Uani 1 1 d . . . . .
H4 H 0.3454 0.4418 0.4508 0.044 Uiso 1 1 calc R U . . .
C3A C 0.2458(3) 0.3092(2) 0.38545(11) 0.0409(5) Uani 1 1 d . . . . .
C9A C 0.1299(3) 0.3100(2) 0.33217(11) 0.0388(5) Uani 1 1 d . . . . .
C4A C 0.2729(3) 0.5457(2) 0.36935(11) 0.0361(5) Uani 1 1 d . . . . .
C8A C 0.1545(3) 0.5384(2) 0.31395(11) 0.0369(5) Uani 1 1 d . . . . .
N2 N 0.1367(4) 0.1061(2) 0.36771(16) 0.0691(8) Uani 1 1 d . . . . .
C8 C 0.1004(4) 0.6536(3) 0.28189(14) 0.0512(7) Uani 1 1 d . . . . .
H8 H 0.0259 0.6491 0.2444 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3239(4) 0.6688(3) 0.39205(14) 0.0492(6) Uani 1 1 d . . . . .
H5 H 0.3980 0.6752 0.4296 0.059 Uiso 1 1 calc R U . . .
C6 C 0.2682(4) 0.7813(3) 0.36079(17) 0.0611(8) Uani 1 1 d . . . . .
H6 H 0.3052 0.8622 0.3767 0.073 Uiso 1 1 calc R U . . .
C7 C 0.1564(4) 0.7718(3) 0.30529(16) 0.0610(8) Uani 1 1 d . . . . .
H7 H 0.1188 0.8471 0.2836 0.073 Uiso 1 1 calc R U . . .
C10 C -0.0430(4) 0.3930(3) 0.24004(14) 0.0548(7) Uani 1 1 d . . . . .
C3 C 0.2436(4) 0.1793(3) 0.40542(16) 0.0577(7) Uani 1 1 d . . . . .
H3 H 0.3104 0.1483 0.4414 0.069 Uiso 1 1 calc R U . . .
C12 C -0.0420(5) 0.1507(4) 0.26541(18) 0.0731(10) Uani 1 1 d . . . . .
H12A H -0.1230 0.0844 0.2743 0.088 Uiso 1 1 calc R U . . .
H12B H 0.0284 0.1150 0.2362 0.088 Uiso 1 1 calc R U . . .
C13 C 0.8325(5) 0.5624(4) 0.4136(2) 0.0739(10) Uani 1 1 d . . . . .
H13A H 0.8258 0.5675 0.3686 0.089 Uiso 1 1 calc R U . . .
H13B H 0.9232 0.5013 0.4291 0.089 Uiso 1 1 calc R U . . .
C11 C -0.1360(5) 0.2662(4) 0.23827(19) 0.0767(11) Uani 1 1 d . . . . .
H11A H -0.2358 0.2780 0.2593 0.092 Uiso 1 1 calc R U . . .
H11B H -0.1789 0.2468 0.1950 0.092 Uiso 1 1 calc R U . . .
C15 C 0.7402(6) 0.1810(4) 0.4196(2) 0.0870(12) Uani 1 1 d . . . . .
H15A H 0.7016 0.1522 0.3772 0.104 Uiso 1 1 calc R U . . .
H15B H 0.8546 0.2181 0.4211 0.104 Uiso 1 1 calc R U . . .
C14 C 0.8724(7) 0.6887(5) 0.4407(2) 0.1134(19) Uani 1 1 d . . . . .
H14A H 0.9806 0.7182 0.4300 0.170 Uiso 1 1 calc R U . . .
H14B H 0.7829 0.7490 0.4248 0.170 Uiso 1 1 calc R U . . .
H14C H 0.8801 0.6830 0.4852 0.170 Uiso 1 1 calc R U . . .
C16 C 0.7484(7) 0.0714(4) 0.4609(2) 0.1028(16) Uani 1 1 d . . . . .
H16A H 0.8267 0.0078 0.4487 0.154 Uiso 1 1 calc R U . . .
H16B H 0.7884 0.0994 0.5028 0.154 Uiso 1 1 calc R U . . .
H16C H 0.6356 0.0336 0.4590 0.154 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 O2 1.4617(18) . ?
P1 O4 1.570(2) . ?
P1 O3 1.574(2) . ?
P1 C4 1.822(2) . ?
O4 C15 1.438(4) . ?
O3 C13 1.440(4) . ?
N9 C9A 1.394(3) . ?
N9 C10 1.404(4) . ?
N9 C8A 1.445(3) . ?
O1 C10 1.202(4) . ?
N1 C9A 1.344(3) . ?
N1 N2 1.359(4) . ?
N1 C12 1.444(4) . ?
C4 C3A 1.489(3) . ?
C4 C4A 1.528(3) . ?
C4 H4 0.9800 . ?
C3A C9A 1.360(4) . ?
C3A C3 1.405(4) . ?
C4A C5 1.394(3) . ?
C4A C8A 1.407(3) . ?
C8A C8 1.406(3) . ?
N2 C3 1.317(4) . ?
C8 C7 1.364(4) . ?
C8 H8 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C10 C11 1.491(5) . ?
C3 H3 0.9300 . ?
C12 C11 1.473(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.440(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 C16 1.436(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
O2 P1 O4 115.39(12) . . ?
O2 P1 O3 114.36(12) . . ?
O4 P1 O3 104.58(13) . . ?
O2 P1 C4 115.62(11) . . ?
O4 P1 C4 102.21(11) . . ?
O3 P1 C4 103.04(11) . . ?
C15 O4 P1 122.2(2) . . ?
C13 O3 P1 121.2(2) . . ?
C9A N9 C10 118.1(2) . . ?
C9A N9 C8A 114.99(19) . . ?
C10 N9 C8A 126.4(2) . . ?
C9A N1 N2 111.3(2) . . ?
C9A N1 C12 123.2(3) . . ?
N2 N1 C12 124.9(3) . . ?
C3A C4 C4A 109.9(2) . . ?
C3A C4 P1 108.41(16) . . ?
C4A C4 P1 110.37(15) . . ?
C3A C4 H4 109.4 . . ?
C4A C4 H4 109.4 . . ?
P1 C4 H4 109.4 . . ?
C9A C3A C3 103.3(2) . . ?
C9A C3A C4 121.0(2) . . ?
C3 C3A C4 135.4(3) . . ?
N1 C9A C3A 108.5(2) . . ?
N1 C9A N9 123.6(2) . . ?
C3A C9A N9 128.0(2) . . ?
C5 C4A C8A 117.9(2) . . ?
C5 C4A C4 118.0(2) . . ?
C8A C4A C4 124.1(2) . . ?
C8 C8A C4A 119.3(2) . . ?
C8 C8A N9 120.5(2) . . ?
C4A C8A N9 120.1(2) . . ?
C3 N2 N1 104.2(2) . . ?
C7 C8 C8A 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C8A C8 H8 119.7 . . ?
C6 C5 C4A 122.3(3) . . ?
C6 C5 H5 118.9 . . ?
C4A C5 H5 118.9 . . ?
C5 C6 C7 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O1 C10 N9 122.7(3) . . ?
O1 C10 C11 121.1(3) . . ?
N9 C10 C11 116.0(3) . . ?
N2 C3 C3A 112.8(3) . . ?
N2 C3 H3 123.6 . . ?
C3A C3 H3 123.6 . . ?
N1 C12 C11 108.4(3) . . ?
N1 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
N1 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
O3 C13 C14 109.7(3) . . ?
O3 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
O3 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11A 107.6 . . ?
C10 C11 H11A 107.6 . . ?
C12 C11 H11B 107.6 . . ?
C10 C11 H11B 107.6 . . ?
H11A C11 H11B 107.1 . . ?
C16 C15 O4 111.4(4) . . ?
C16 C15 H15A 109.3 . . ?
O4 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
O4 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
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 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.089

