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

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

data_x-ray-1
_database_code_depnum_ccdc_archive 'CCDC 2236285'
loop_
_audit_author_name
_audit_author_address
'Fukaya H.'
;Tokyo University of Pharmacy and Life Sciences
Japan
;
_audit_update_record             
;
2023-01-15 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2022-12-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
fukayah@toyaku.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 Cl N O3 P'
_chemical_formula_sum            'C20 H25 Cl N O3 P'
_chemical_formula_weight         393.83
_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'
Cl Cl 0.1484 0.1585 '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                   8.6173(2)
_cell_length_b                   9.9762(2)
_cell_length_c                   13.0120(3)
_cell_angle_alpha                75.0040(10)
_cell_angle_beta                 89.6230(10)
_cell_angle_gamma                65.8280(10)
_cell_volume                     979.49(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9096
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9627.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.091
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44212
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_min         1.631
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX II ULTRA'
_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_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5582
_reflns_number_total             5995
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5995
_refine_ls_number_restraints     185
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.3660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0829
_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. Rigid body (RIGU) restrains
 P1, C7, C14, O2, C5, O1, C12, Cl1, C9, O3, C10, N1, C19, C3, C13, C4, C1, C16,
  C20, C2, C6, C11, C17, C15, C18, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.55089(3) 0.81231(3) 0.49155(2) 0.02164(6) Uani 1 1 d . . . . .
P1 P 0.76827(3) 0.12398(2) 0.15490(2) 0.01263(6) Uani 1 1 d . . . . .
O1 O 0.86656(8) 0.17599(8) 0.07335(5) 0.01632(13) Uani 1 1 d . . . . .
O2 O 0.88884(9) 0.03741(8) 0.26455(5) 0.01840(13) Uani 1 1 d . . . . .
O3 O 0.69607(8) 0.01187(7) 0.13205(6) 0.01665(13) Uani 1 1 d . . . . .
N1 N 0.23388(11) 0.87546(9) 0.13767(7) 0.01742(15) Uani 1 1 d . . . . .
C1 C 0.38792(11) 0.54817(9) 0.16035(7) 0.01229(14) Uani 1 1 d . . . . .
H1 H 0.347384 0.627949 0.089621 0.015 Uiso 1 1 calc R U . . .
C2 C 0.54650(11) 0.41642(10) 0.14504(7) 0.01354(15) Uani 1 1 d . . . . .
H2 H 0.631551 0.441404 0.109129 0.016 Uiso 1 1 calc R U . . .
C3 C 0.57772(11) 0.26873(10) 0.17729(7) 0.01507(16) Uani 1 1 d . . . . .
H3 H 0.495054 0.240174 0.213463 0.018 Uiso 1 1 calc R U . . .
C4 C 0.24159(11) 0.50260(9) 0.19194(7) 0.01283(15) Uani 1 1 d . . . . .
C5 C 0.17473(12) 0.44902(11) 0.12199(8) 0.01722(16) Uani 1 1 d . . . . .
H5 H 0.216665 0.447296 0.054420 0.021 Uiso 1 1 calc R U . . .
C6 C 0.04802(12) 0.39829(11) 0.14966(9) 0.02068(18) Uani 1 1 d . . . . .
H6 H 0.006616 0.359121 0.102239 0.025 Uiso 1 1 calc R U . . .
C7 C -0.01788(13) 0.40500(12) 0.24675(9) 0.02250(19) Uani 1 1 d . . . . .
H7 H -0.104663 0.370634 0.265981 0.027 Uiso 1 1 calc R U . . .
C8 C 0.04348(13) 0.46204(12) 0.31553(8) 0.02243(19) Uani 1 1 d . . . . .
H8 H -0.003451 0.469193 0.381217 0.027 Uiso 1 1 calc R U . . .
C9 C 0.17400(12) 0.50902(11) 0.28865(7) 0.01704(16) Uani 1 1 d . . . . .
H9 H 0.217042 0.545783 0.337042 0.020 Uiso 1 1 calc R U . . .
C10 C 0.43411(11) 0.61976(9) 0.23856(7) 0.01217(14) Uani 1 1 d . . . . .
C11 C 0.35006(11) 0.77872(10) 0.22560(7) 0.01257(14) Uani 1 1 d . . . . .
C12 C 0.38836(11) 0.84267(10) 0.30227(7) 0.01429(15) Uani 1 1 d . . . . .
C13 C 0.50577(12) 0.74240(10) 0.39058(7) 0.01495(15) Uani 1 1 d . . . . .
C14 C 0.58969(12) 0.58591(11) 0.40511(7) 0.01639(16) Uani 1 1 d . . . . .
H14 H 0.670352 0.521166 0.465979 0.020 Uiso 1 1 calc R U . . .
C15 C 0.55238(12) 0.52677(10) 0.32816(7) 0.01506(15) Uani 1 1 d . . . . .
H15 H 0.609057 0.419770 0.336753 0.018 Uiso 1 1 calc R U . . .
C16 C 0.30368(13) 1.01316(11) 0.28351(8) 0.02069(18) Uani 1 1 d . . . . .
H16A H 0.326165 1.063451 0.213476 0.031 Uiso 1 1 calc R U . . .
H16B H 0.349688 1.040466 0.339661 0.031 Uiso 1 1 calc R U . . .
H16C H 0.179945 1.046807 0.285164 0.031 Uiso 1 1 calc R U . . .
C17 C 0.83021(15) -0.03259(15) 0.35967(9) 0.0294(2) Uani 1 1 d . . . . .
H17A H 0.760147 -0.081858 0.340157 0.035 Uiso 1 1 calc R U . . .
H17B H 0.758852 0.046289 0.394067 0.035 Uiso 1 1 calc R U . . .
C18 C 0.98391(19) -0.14956(16) 0.43513(10) 0.0384(3) Uani 1 1 d . . . . .
H18A H 1.049554 -0.230837 0.402299 0.058 Uiso 1 1 calc R U . . .
H18B H 0.946991 -0.193560 0.501812 0.058 Uiso 1 1 calc R U . . .
H18C H 1.055867 -0.100892 0.450709 0.058 Uiso 1 1 calc R U . . .
C19 C 0.81157(12) -0.13197(10) 0.11143(8) 0.01832(17) Uani 1 1 d . . . . .
H19A H 0.882826 -0.205361 0.178336 0.022 Uiso 1 1 calc R U . . .
H19B H 0.888286 -0.113172 0.058205 0.022 Uiso 1 1 calc R U . . .
C20 C 0.70324(14) -0.19530(13) 0.06946(11) 0.0275(2) Uani 1 1 d . . . . .
H20A H 0.638541 -0.124564 0.001048 0.041 Uiso 1 1 calc R U . . .
H20B H 0.623488 -0.208062 0.121035 0.041 Uiso 1 1 calc R U . . .
H20C H 0.776728 -0.294757 0.058783 0.041 Uiso 1 1 calc R U . . .
H1A H 0.2032(19) 0.8388(17) 0.0921(12) 0.025(3) Uiso 1 1 d . . . . .
H1B H 0.162(2) 0.9642(19) 0.1397(13) 0.031(4) Uiso 1 1 d . . . . .


_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
Cl1 C13 1.7512(9) . ?
P1 O1 1.4751(7) . ?
P1 O2 1.5836(7) . ?
P1 O3 1.5719(7) . ?
P1 C3 1.7708(9) . ?
O2 C17 1.4520(12) . ?
O3 C19 1.4656(11) . ?
N1 C11 1.3767(11) . ?
N1 H1A 0.865(15) . ?
N1 H1B 0.855(16) . ?
C1 H1 1.0000 . ?
C1 C2 1.5151(12) . ?
C1 C4 1.5270(12) . ?
C1 C10 1.5227(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.3328(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.3989(12) . ?
C4 C9 1.3887(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.3897(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.3879(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.3858(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3959(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.4108(11) . ?
C10 C15 1.3929(12) . ?
C11 C12 1.4203(12) . ?
C12 C13 1.3916(13) . ?
C12 C16 1.5020(12) . ?
C13 C14 1.3858(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.3854(12) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.4962(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.4957(14) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 O2 108.25(4) . . ?
O1 P1 O3 116.71(4) . . ?
O1 P1 C3 115.95(4) . . ?
O2 P1 C3 108.46(4) . . ?
O3 P1 O2 106.69(4) . . ?
O3 P1 C3 100.12(4) . . ?
C17 O2 P1 121.31(7) . . ?
C19 O3 P1 120.30(6) . . ?
C11 N1 H1A 120.3(10) . . ?
C11 N1 H1B 119.9(11) . . ?
H1A N1 H1B 115.1(14) . . ?
C2 C1 H1 107.0 . . ?
C2 C1 C4 112.74(7) . . ?
C2 C1 C10 109.93(7) . . ?
C4 C1 H1 107.0 . . ?
C10 C1 H1 107.0 . . ?
C10 C1 C4 112.84(7) . . ?
C1 C2 H2 117.0 . . ?
C3 C2 C1 126.04(8) . . ?
C3 C2 H2 117.0 . . ?
P1 C3 H3 118.9 . . ?
C2 C3 P1 122.14(7) . . ?
C2 C3 H3 118.9 . . ?
C5 C4 C1 118.97(8) . . ?
C9 C4 C1 122.67(8) . . ?
C9 C4 C5 118.34(8) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.13(9) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.82(9) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.71(9) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.24(9) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.71(9) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C1 120.82(7) . . ?
C15 C10 C1 119.91(7) . . ?
C15 C10 C11 119.14(8) . . ?
N1 C11 C10 121.24(8) . . ?
N1 C11 C12 118.60(8) . . ?
C10 C11 C12 120.13(8) . . ?
C11 C12 C16 118.98(8) . . ?
C13 C12 C11 117.48(8) . . ?
C13 C12 C16 123.54(8) . . ?
C12 C13 Cl1 119.89(7) . . ?
C14 C13 Cl1 116.72(7) . . ?
C14 C13 C12 123.38(8) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 117.98(8) . . ?
C15 C14 H14 121.0 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.86(8) . . ?
C14 C15 H15 119.1 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 110.0 . . ?
O2 C17 H17B 110.0 . . ?
O2 C17 C18 108.24(10) . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 110.2 . . ?
O3 C19 H19B 110.2 . . ?
O3 C19 C20 107.52(8) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Cl1 C13 C14 C15 177.99(7) . . . . ?
P1 O2 C17 C18 159.73(9) . . . . ?
P1 O3 C19 C20 -167.79(7) . . . . ?
O1 P1 O2 C17 -177.62(8) . . . . ?
O1 P1 O3 C19 55.81(8) . . . . ?
O1 P1 C3 C2 -16.90(10) . . . . ?
O2 P1 O3 C19 -65.30(8) . . . . ?
O2 P1 C3 C2 105.07(8) . . . . ?
O3 P1 O2 C17 -51.26(9) . . . . ?
O3 P1 C3 C2 -143.39(8) . . . . ?
N1 C11 C12 C13 179.79(8) . . . . ?
N1 C11 C12 C16 -1.22(12) . . . . ?
C1 C2 C3 P1 179.97(7) . . . . ?
C1 C4 C5 C6 176.44(8) . . . . ?
C1 C4 C9 C8 -178.14(9) . . . . ?
C1 C10 C11 N1 -5.20(12) . . . . ?
C1 C10 C11 C12 176.77(7) . . . . ?
C1 C10 C15 C14 -175.61(8) . . . . ?
C2 C1 C4 C5 -60.81(10) . . . . ?
C2 C1 C4 C9 117.79(9) . . . . ?
C2 C1 C10 C11 145.08(8) . . . . ?
C2 C1 C10 C15 -39.28(10) . . . . ?
C3 P1 O2 C17 55.80(9) . . . . ?
C3 P1 O3 C19 -178.21(7) . . . . ?
C4 C1 C2 C3 -14.74(13) . . . . ?
C4 C1 C10 C11 -88.14(9) . . . . ?
C4 C1 C10 C15 87.50(9) . . . . ?
C4 C5 C6 C7 2.06(14) . . . . ?
C5 C4 C9 C8 0.47(13) . . . . ?
C5 C6 C7 C8 -0.12(15) . . . . ?
C6 C7 C8 C9 -1.61(15) . . . . ?
C7 C8 C9 C4 1.43(15) . . . . ?
C9 C4 C5 C6 -2.22(13) . . . . ?
C10 C1 C2 C3 112.10(10) . . . . ?
C10 C1 C4 C5 173.91(8) . . . . ?
C10 C1 C4 C9 -7.48(11) . . . . ?
C10 C11 C12 C13 -2.12(12) . . . . ?
C10 C11 C12 C16 176.87(8) . . . . ?
C11 C10 C15 C14 0.11(13) . . . . ?
C11 C12 C13 Cl1 -176.81(6) . . . . ?
C11 C12 C13 C14 2.08(13) . . . . ?
C12 C13 C14 C15 -0.93(14) . . . . ?
C13 C14 C15 C10 -0.21(14) . . . . ?
C15 C10 C11 N1 179.13(8) . . . . ?
C15 C10 C11 C12 1.09(12) . . . . ?
C16 C12 C13 Cl1 4.26(12) . . . . ?
C16 C12 C13 C14 -176.86(9) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MiTeGEN MicroMounts in  perfluoropolyether oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_x-ray-2
_database_code_depnum_ccdc_archive 'CCDC 2236286'
loop_
_audit_author_name
_audit_author_address
'Fukaya H.'
;Tokyo University of Pharmacy and Life Sciences
Japan
;
_audit_update_record             
;
2023-01-15 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2022-12-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
fukayah@toyaku.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H28 N O4 P'
_chemical_formula_sum            'C21 H28 N O4 P'
_chemical_formula_weight         389.41
_chemical_absolute_configuration unk
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.8383(3)
_cell_length_b                   9.6582(3)
_cell_length_c                   10.9876(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.2870(10)
_cell_angle_gamma                90
_cell_volume                     1020.13(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9042
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1604 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.9042.
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    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.147
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27544
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.549
_diffrn_reflns_theta_min         1.897
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX II ULTRA'
_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_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5955
_reflns_number_total             6233
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         6233
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.029
_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)+(0.0472P)²+0.2222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0867
_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. Restrained distances
 N1-H1A \\sim N1-H1B
 with sigma of 0.001
 C12-H1A \\sim C12-H1B
 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16)
3.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.81534(4) 0.50452(5) 0.86391(4) 0.01500(10) Uani 1 1 d . . . . .
O1 O 0.19175(14) 0.60090(15) 0.63628(14) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.78712(14) 0.65367(14) 0.87035(13) 0.0207(3) Uani 1 1 d . . . . .
O3 O 0.75632(13) 0.41417(14) 0.96168(13) 0.0192(3) Uani 1 1 d . . . . .
O4 O 0.97321(13) 0.46202(15) 0.89520(13) 0.0198(3) Uani 1 1 d . . . . .
N1 N 0.43111(16) 0.32726(16) 0.28777(15) 0.0175(3) Uani 1 1 d D . . . .
C1 C 0.60935(17) 0.45276(18) 0.49736(16) 0.0135(3) Uani 1 1 d . . . . .
H1 H 0.630059 0.351757 0.492757 0.016 Uiso 1 1 calc R U . . .
C2 C 0.68043(15) 0.5022(2) 0.62533(14) 0.0134(3) Uani 1 1 d . . . . .
H2 H 0.674462 0.598265 0.642068 0.016 Uiso 1 1 calc R U . . .
C3 C 0.75116(17) 0.42317(18) 0.71749(17) 0.0157(3) Uani 1 1 d . . . . .
C4 C 0.7759(2) 0.2701(2) 0.7112(2) 0.0282(4) Uani 1 1 d . . . . .
H4A H 0.873954 0.253232 0.710314 0.042 Uiso 1 1 calc R U . . .
H4B H 0.717138 0.232306 0.635132 0.042 Uiso 1 1 calc R U . . .
H4C H 0.752885 0.224808 0.784042 0.042 Uiso 1 1 calc R U . . .
C5 C 0.67355(16) 0.52596(17) 0.39993(15) 0.0145(3) Uani 1 1 d . . . . .
C6 C 0.76292(18) 0.4528(2) 0.34092(17) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.781596 0.357862 0.360314 0.022 Uiso 1 1 calc R U . . .
C7 C 0.82527(18) 0.5179(2) 0.25344(17) 0.0224(4) Uani 1 1 d . . . . .
H7 H 0.885502 0.467041 0.212942 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7994(2) 0.6568(2) 0.22551(19) 0.0236(4) Uani 1 1 d . . . . .
H8 H 0.842500 0.701577 0.166601 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7102(2) 0.7298(2) 0.28419(19) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.692202 0.824918 0.265159 0.027 Uiso 1 1 calc R U . . .
C10 C 0.64706(19) 0.66504(18) 0.37058(18) 0.0190(3) Uani 1 1 d . . . . .
H10 H 0.585575 0.715760 0.409791 0.023 Uiso 1 1 calc R U . . .
C11 C 0.45137(16) 0.46794(17) 0.47552(16) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.36890(17) 0.40184(17) 0.37053(16) 0.0153(3) Uani 1 1 d D . . . .
C13 C 0.22511(18) 0.40097(18) 0.35773(18) 0.0178(3) Uani 1 1 d . . . . .
H13 H 0.169004 0.355721 0.288007 0.021 Uiso 1 1 calc R U . . .
C14 C 0.16152(18) 0.4648(2) 0.44463(18) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.063301 0.461561 0.435036 0.023 Uiso 1 1 calc R U . . .
C15 C 0.24262(18) 0.53303(17) 0.54515(18) 0.0172(3) Uani 1 1 d . . . . .
C16 C 0.38695(17) 0.53469(16) 0.55967(17) 0.0155(3) Uani 1 1 d . . . . .
H16 H 0.442051 0.582393 0.628423 0.019 Uiso 1 1 calc R U . . .
C17 C 0.0448(2) 0.5995(2) 0.6244(2) 0.0292(4) Uani 1 1 d . . . . .
H17A H -0.000022 0.642517 0.545241 0.044 Uiso 1 1 calc R U . . .
H17B H 0.020588 0.651320 0.693490 0.044 Uiso 1 1 calc R U . . .
H17C H 0.012608 0.503630 0.626308 0.044 Uiso 1 1 calc R U . . .
C18 C 0.61096(19) 0.4304(2) 0.96781(19) 0.0221(4) Uani 1 1 d . . . . .
H18A H 0.554864 0.455441 0.884847 0.027 Uiso 1 1 calc R U . . .
H18B H 0.601052 0.504728 1.027323 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5618(2) 0.2946(2) 1.0101(2) 0.0293(4) Uani 1 1 d . . . . .
H19A H 0.567953 0.222693 0.948623 0.044 Uiso 1 1 calc R U . . .
H19B H 0.464991 0.303786 1.018547 0.044 Uiso 1 1 calc R U . . .
H19C H 0.620309 0.269003 1.090729 0.044 Uiso 1 1 calc R U . . .
C20 C 1.0683(2) 0.5292(3) 0.9990(2) 0.0341(5) Uani 1 1 d . . . . .
H20A H 1.043234 0.504539 1.078856 0.041 Uiso 1 1 calc R U . . .
H20B H 1.062982 0.631044 0.989204 0.041 Uiso 1 1 calc R U . . .
C21 C 1.2110(2) 0.4799(2) 0.9977(2) 0.0282(4) Uani 1 1 d . . . . .
H21A H 1.236423 0.509048 0.920066 0.042 Uiso 1 1 calc R U . . .
H21B H 1.213818 0.378649 1.003420 0.042 Uiso 1 1 calc R U . . .
H21C H 1.276811 0.519513 1.068760 0.042 Uiso 1 1 calc R U . . .
H1A H 0.3764(18) 0.289(2) 0.2247(19) 0.029(7) Uiso 1 1 d D . . . .
H1B H 0.5045(19) 0.363(2) 0.269(2) 0.024(6) Uiso 1 1 d D . . . .


_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 1.4716(14) . ?
P1 O3 1.5869(14) . ?
P1 O4 1.5722(13) . ?
P1 C3 1.7810(18) . ?
O1 C15 1.377(2) . ?
O1 C17 1.424(2) . ?
O3 C18 1.454(2) . ?
O4 C20 1.463(2) . ?
N1 C12 1.399(2) . ?
N1 H1A 0.865(17) . ?
N1 H1B 0.865(17) . ?
C1 H1 1.0000 . ?
C1 C2 1.509(2) . ?
C1 C5 1.527(2) . ?
C1 C11 1.528(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.339(2) . ?
C3 C4 1.503(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.391(2) . ?
C5 C10 1.393(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.414(2) . ?
C11 C16 1.386(2) . ?
C12 C13 1.392(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 C16 1.395(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.505(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.485(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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 O3 113.94(8) . . ?
O2 P1 O4 115.65(8) . . ?
O2 P1 C3 116.17(8) . . ?
O3 P1 C3 104.98(8) . . ?
O4 P1 O3 101.25(7) . . ?
O4 P1 C3 103.07(8) . . ?
C15 O1 C17 116.61(16) . . ?
C18 O3 P1 118.51(12) . . ?
C20 O4 P1 119.52(13) . . ?
C12 N1 H1A 117.2(12) . . ?
C12 N1 H1B 117.2(12) . . ?
H1A N1 H1B 113(2) . . ?
C2 C1 H1 107.3 . . ?
C2 C1 C5 109.14(14) . . ?
C2 C1 C11 111.73(14) . . ?
C5 C1 H1 107.3 . . ?
C5 C1 C11 113.82(13) . . ?
C11 C1 H1 107.3 . . ?
C1 C2 H2 117.0 . . ?
C3 C2 C1 125.99(18) . . ?
C3 C2 H2 117.0 . . ?
C2 C3 P1 117.32(14) . . ?
C2 C3 C4 126.13(17) . . ?
C4 C3 P1 116.48(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 119.21(16) . . ?
C6 C5 C10 119.19(17) . . ?
C10 C5 C1 121.59(16) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.40(18) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.09(18) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.55(18) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.50(18) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.25(18) . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C1 118.21(15) . . ?
C16 C11 C1 122.27(15) . . ?
C16 C11 C12 119.33(15) . . ?
N1 C12 C11 120.56(15) . . ?
C13 C12 N1 120.47(16) . . ?
C13 C12 C11 118.67(16) . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.57(16) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.43(16) . . ?
C15 C14 H14 120.3 . . ?
O1 C15 C14 124.74(16) . . ?
O1 C15 C16 115.47(15) . . ?
C14 C15 C16 119.79(16) . . ?
C11 C16 C15 121.14(16) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 110.2 . . ?
O3 C18 H18B 110.2 . . ?
O3 C18 C19 107.74(15) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
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 . . ?
O4 C20 H20A 110.2 . . ?
O4 C20 H20B 110.2 . . ?
O4 C20 C21 107.43(18) . . ?
H20A C20 H20B 108.5 . . ?
C21 C20 H20A 110.2 . . ?
C21 C20 H20B 110.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 O3 C18 C19 150.83(14) . . . . ?
P1 O4 C20 C21 -174.07(15) . . . . ?
O1 C15 C16 C11 178.80(15) . . . . ?
O2 P1 O3 C18 51.62(16) . . . . ?
O2 P1 O4 C20 41.38(18) . . . . ?
O2 P1 C3 C2 -1.14(17) . . . . ?
O2 P1 C3 C4 -178.28(15) . . . . ?
O3 P1 O4 C20 -82.29(17) . . . . ?
O3 P1 C3 C2 125.70(14) . . . . ?
O3 P1 C3 C4 -51.45(16) . . . . ?
O4 P1 O3 C18 176.45(13) . . . . ?
O4 P1 C3 C2 -128.67(14) . . . . ?
O4 P1 C3 C4 54.19(17) . . . . ?
N1 C12 C13 C14 174.64(17) . . . . ?
C1 C2 C3 P1 -175.71(13) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C1 C5 C6 C7 -178.67(15) . . . . ?
C1 C5 C10 C9 178.10(16) . . . . ?
C1 C11 C12 N1 -1.4(2) . . . . ?
C1 C11 C12 C13 172.43(15) . . . . ?
C1 C11 C16 C15 -172.32(15) . . . . ?
C2 C1 C5 C6 105.59(17) . . . . ?
C2 C1 C5 C10 -73.06(19) . . . . ?
C2 C1 C11 C12 -167.87(15) . . . . ?
C2 C1 C11 C16 7.1(2) . . . . ?
C3 P1 O3 C18 -76.57(15) . . . . ?
C3 P1 O4 C20 169.25(16) . . . . ?
C5 C1 C2 C3 -119.42(18) . . . . ?
C5 C1 C11 C12 67.9(2) . . . . ?
C5 C1 C11 C16 -117.11(17) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C10 C5 C6 C7 0.0(3) . . . . ?
C11 C1 C2 C3 113.81(18) . . . . ?
C11 C1 C5 C6 -128.84(16) . . . . ?
C11 C1 C5 C10 52.5(2) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C11 C16 C15 2.6(2) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 O1 179.38(17) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C16 C11 C12 N1 -176.47(15) . . . . ?
C16 C11 C12 C13 -2.7(2) . . . . ?
C17 O1 C15 C14 0.0(3) . . . . ?
C17 O1 C15 C16 -179.34(17) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MiTeGEN MicroMounts in  perfluoropolyether oil'
_olex2_submission_special_instructions 'No special instructions were received'
