# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 2097483'
loop_
_audit_author_name
_audit_author_address
'Haruhiko Fukaya'
;Tokyo University of Pharmacy and Life Science
Japan
;

_audit_update_record             
;
2021-07-17 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;
_publcif_datablock.id            {6a67144f-ef50-4748-b6d1-20533f7cf274}
_audit_creation_date             2019-10-18
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2016/6
_audit_contact_letter            
;
 ?
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N O4 P'
_chemical_formula_sum            'C19 H20 N O4 P'
_chemical_formula_weight         357.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.872(2)
_cell_length_b                   10.452(3)
_cell_length_c                   10.957(3)
_cell_angle_alpha                102.427(3)
_cell_angle_beta                 90.106(3)
_cell_angle_gamma                113.697(3)
_cell_volume                     904.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3876
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0684 before and 0.0344 after correction.
The Ratio of minimum to maximum transmission is 0.8678.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.221
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9044
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         1.913
_diffrn_ambient_temperature      90
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'Bruker SMART APEX II CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Bruker SMART APEX II Ultra'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm  '
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3310
_reflns_number_total             4093
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.6442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C11(H11), C15(H15), C5(H5), C12(H12), C7(H7), C13(H13),
 C6(H6), C14(H14)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 1.08390(6) 0.71252(5) 0.75841(4) 0.01879(12) Uani 1 1 d . U . . .
O2 O 1.13454(15) 0.64661(13) 0.85958(11) 0.0216(2) Uani 1 1 d . U . . .
O4 O 1.13850(16) 0.87432(13) 0.82954(11) 0.0238(3) Uani 1 1 d . U . . .
O3 O 1.14278(16) 0.68762(14) 0.63419(11) 0.0234(3) Uani 1 1 d . U . . .
O1 O 0.33630(16) 0.18864(13) 0.33967(11) 0.0243(3) Uani 1 1 d . U . . .
N1 N 0.7468(2) 0.72794(17) 0.95060(14) 0.0260(3) Uani 1 1 d . U . . .
C1 C 0.8627(2) 0.62942(18) 0.75324(15) 0.0189(3) Uani 1 1 d . U . . .
C2 C 0.7759(2) 0.52514(18) 0.65106(15) 0.0191(3) Uani 1 1 d . U . . .
H2 H 0.841409 0.505133 0.587548 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5983(2) 0.43826(18) 0.62224(15) 0.0199(3) Uani 1 1 d . U . . .
C9 C 0.5465(2) 0.34816(18) 0.50062(15) 0.0199(3) Uani 1 1 d . U . . .
H9 H 0.625907 0.343884 0.443652 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2556(2) -0.03664(19) 0.40578(16) 0.0223(3) Uani 1 1 d . U . . .
H11 H 0.306254 0.012395 0.488676 0.027 Uiso 1 1 calc R U . . .
C15 C 0.1858(2) -0.03039(19) 0.19407(16) 0.0214(3) Uani 1 1 d . U . . .
H15 H 0.188438 0.022686 0.133163 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4791(2) 0.43992(19) 0.70562(16) 0.0227(3) Uani 1 1 d . U . . .
H5 H 0.512078 0.498598 0.788555 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2579(2) 0.04027(18) 0.31615(15) 0.0208(3) Uani 1 1 d . U . . .
C8 C 0.3809(2) 0.26644(18) 0.46459(16) 0.0217(3) Uani 1 1 d . U . . .
C12 C 0.1785(2) -0.1859(2) 0.37271(17) 0.0242(3) Uani 1 1 d . U . . .
H12 H 0.175858 -0.239123 0.433500 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7927(2) 0.68065(18) 0.86141(15) 0.0204(3) Uani 1 1 d . U . . .
C7 C 0.2617(2) 0.26919(19) 0.54540(16) 0.0244(3) Uani 1 1 d . U . . .
H7 H 0.147513 0.213370 0.518809 0.029 Uiso 1 1 calc R U . . .
C16 C 1.2012(2) 0.99282(19) 0.76602(17) 0.0244(3) Uani 1 1 d . U . . .
H16A H 1.172857 1.072203 0.810089 0.029 Uiso 1 1 calc R U . . .
H16B H 1.148150 0.959390 0.678753 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1052(2) -0.2579(2) 0.25128(17) 0.0251(3) Uani 1 1 d . U . . .
H13 H 0.052313 -0.359898 0.229025 0.030 Uiso 1 1 calc R U . . .
C18 C 1.3095(2) 0.6976(2) 0.90427(17) 0.0245(3) Uani 1 1 d . U . . .
H18A H 1.352697 0.798813 0.952695 0.029 Uiso 1 1 calc R U . . .
H18B H 1.375570 0.691876 0.832198 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3136(2) 0.35601(19) 0.66687(17) 0.0252(3) Uani 1 1 d . U . . .
H6 H 0.233565 0.357408 0.723989 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1100(2) -0.1794(2) 0.16258(17) 0.0241(3) Uani 1 1 d . U . . .
H14 H 0.060643 -0.228486 0.079390 0.029 Uiso 1 1 calc R U . . .
C19 C 1.3210(2) 0.6029(2) 0.98643(17) 0.0263(4) Uani 1 1 d . U . . .
H19A H 1.276912 0.502873 0.937779 0.039 Uiso 1 1 calc R U . . .
H19B H 1.256629 0.610517 1.058079 0.039 Uiso 1 1 calc R U . . .
H19C H 1.436970 0.633571 1.016925 0.039 Uiso 1 1 calc R U . . .
C17 C 1.3844(3) 1.0461(2) 0.7647(2) 0.0347(4) Uani 1 1 d . U . . .
H17A H 1.411353 0.971078 0.712204 0.052 Uiso 1 1 calc R U . . .
H17B H 1.435831 1.070199 0.850573 0.052 Uiso 1 1 calc R U . . .
H17C H 1.426215 1.131950 0.730597 0.052 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 1.5751(13) . ?
P1 O4 1.5732(13) . ?
P1 O3 1.4673(13) . ?
P1 C1 1.7941(19) . ?
O2 C18 1.468(2) . ?
O4 C16 1.465(2) . ?
O1 C10 1.384(2) . ?
O1 C8 1.397(2) . ?
N1 C3 1.149(2) . ?
C1 C2 1.353(2) . ?
C1 C3 1.440(2) . ?
C2 H2 0.9500 . ?
C2 C4 1.460(2) . ?
C4 C9 1.408(2) . ?
C4 C5 1.402(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.374(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(2) . ?
C11 C12 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C10 1.391(2) . ?
C15 C14 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(3) . ?
C8 C7 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.396(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.493(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.505(3) . ?
C6 H6 0.9500 . ?
C14 H14 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O2 P1 C1 100.81(8) . . ?
O4 P1 O2 102.69(7) . . ?
O4 P1 C1 106.29(7) . . ?
O3 P1 O2 116.82(7) . . ?
O3 P1 O4 116.03(7) . . ?
O3 P1 C1 112.51(8) . . ?
C18 O2 P1 119.81(11) . . ?
C16 O4 P1 122.78(11) . . ?
C10 O1 C8 118.12(13) . . ?
C2 C1 P1 118.70(13) . . ?
C2 C1 C3 125.50(16) . . ?
C3 C1 P1 115.80(12) . . ?
C1 C2 H2 114.6 . . ?
C1 C2 C4 130.70(16) . . ?
C4 C2 H2 114.6 . . ?
C9 C4 C2 116.17(15) . . ?
C5 C4 C2 124.83(15) . . ?
C5 C4 C9 119.00(16) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 C4 119.82(16) . . ?
C8 C9 H9 120.1 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C10 119.30(16) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C10 119.04(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.82(16) . . ?
C6 C5 H5 120.1 . . ?
O1 C10 C11 123.19(15) . . ?
O1 C10 C15 115.87(15) . . ?
C15 C10 C11 120.88(16) . . ?
C9 C8 O1 117.14(16) . . ?
C9 C8 C7 121.70(16) . . ?
C7 C8 O1 120.97(16) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.43(17) . . ?
C13 C12 H12 119.8 . . ?
N1 C3 C1 175.63(19) . . ?
C8 C7 H7 120.8 . . ?
C8 C7 C6 118.35(17) . . ?
C6 C7 H7 120.8 . . ?
O4 C16 H16A 109.6 . . ?
O4 C16 H16B 109.6 . . ?
O4 C16 C17 110.30(15) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.52(17) . . ?
C14 C13 H13 120.2 . . ?
O2 C18 H18A 110.2 . . ?
O2 C18 H18B 110.2 . . ?
O2 C18 C19 107.56(15) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
C5 C6 C7 121.28(17) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C15 C14 C13 120.83(16) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
P1 O2 C18 C19 -172.86(11) . . . . ?
P1 O4 C16 C17 -89.17(17) . . . . ?
P1 C1 C2 C4 178.78(14) . . . . ?
O2 P1 O4 C16 146.02(13) . . . . ?
O2 P1 C1 C2 -107.88(14) . . . . ?
O2 P1 C1 C3 71.67(14) . . . . ?
O4 P1 O2 C18 -63.98(13) . . . . ?
O4 P1 C1 C2 145.34(14) . . . . ?
O4 P1 C1 C3 -35.11(14) . . . . ?
O3 P1 O2 C18 64.17(14) . . . . ?
O3 P1 O4 C16 17.37(16) . . . . ?
O3 P1 C1 C2 17.32(17) . . . . ?
O3 P1 C1 C3 -163.13(12) . . . . ?
O1 C8 C7 C6 -176.03(16) . . . . ?
C1 P1 O2 C18 -173.60(12) . . . . ?
C1 P1 O4 C16 -108.55(14) . . . . ?
C1 C2 C4 C9 173.70(17) . . . . ?
C1 C2 C4 C5 -5.7(3) . . . . ?
C2 C4 C9 C8 -177.85(16) . . . . ?
C2 C4 C5 C6 178.13(17) . . . . ?
C4 C9 C8 O1 174.72(15) . . . . ?
C4 C9 C8 C7 -0.4(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C9 C4 C5 C6 -1.3(3) . . . . ?
C9 C8 C7 C6 -1.1(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C5 C4 C9 C8 1.6(2) . . . . ?
C10 O1 C8 C9 118.17(18) . . . . ?
C10 O1 C8 C7 -66.6(2) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C10 C15 C14 C13 0.1(3) . . . . ?
C8 O1 C10 C11 -15.5(3) . . . . ?
C8 O1 C10 C15 167.19(16) . . . . ?
C8 C7 C6 C5 1.4(3) . . . . ?
C12 C11 C10 O1 -177.87(16) . . . . ?
C12 C11 C10 C15 -0.7(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C3 C1 C2 C4 -0.7(3) . . . . ?
C14 C15 C10 O1 177.81(16) . . . . ?
C14 C15 C10 C11 0.5(3) . . . . ?



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