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

data_6a
_database_code_depnum_ccdc_archive 'CCDC 2172329'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2022-05-12 deposited with the CCDC.	2022-07-01 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         ?
_chemical_formula_sum            'C21 H30 N O4 P'
_chemical_formula_weight         391.43

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                   8.5489(2)
_cell_length_b                   9.9570(2)
_cell_length_c                   12.8587(3)
_cell_angle_alpha                71.144(2)
_cell_angle_beta                 81.512(2)
_cell_angle_gamma                81.501(2)
_cell_volume                     1018.59(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    16002
_cell_measurement_theta_min      3.6340
_cell_measurement_theta_max      76.0550

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.409
_shelx_estimated_absorpt_T_min   0.603
_shelx_estimated_absorpt_T_max   0.766
_exptl_absorpt_correction_T_min  0.78569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            19681
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.653
_diffrn_reflns_theta_max         76.282
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4211
_reflns_number_gt                4170
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_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)+(0.0396P)²+0.4097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_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         4211
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.31751(3) 0.67462(3) 0.00669(2) 0.02043(9) Uani 1 1 d . . . . .
O1 O 0.48880(10) 0.66053(9) 0.01688(7) 0.02714(19) Uani 1 1 d . . . . .
O2 O 0.29171(10) 0.69322(9) -0.11620(7) 0.02632(19) Uani 1 1 d . . . . .
C3 C 0.13139(15) 0.71513(14) -0.14975(10) 0.0281(3) Uani 1 1 d . . . . .
H3A H 0.052041 0.734552 -0.090594 0.034 Uiso 1 1 calc R U . . .
H3B H 0.107121 0.628686 -0.163741 0.034 Uiso 1 1 calc R U . . .
C4 C 0.12526(18) 0.83961(17) -0.25284(13) 0.0414(3) Uani 1 1 d . . . . .
H4A H 0.201814 0.818057 -0.311480 0.062 Uiso 1 1 calc R U . . .
H4B H 0.152031 0.923958 -0.238553 0.062 Uiso 1 1 calc R U . . .
H4C H 0.017903 0.858418 -0.276057 0.062 Uiso 1 1 calc R U . . .
O5 O 0.22173(10) 0.80741(9) 0.03832(7) 0.02692(19) Uani 1 1 d . . . . .
C6 C 0.30117(17) 0.93404(14) 0.02062(13) 0.0349(3) Uani 1 1 d . . . . .
H6A H 0.321925 0.983719 -0.059502 0.042 Uiso 1 1 calc R U . . .
H6B H 0.404149 0.906674 0.052437 0.042 Uiso 1 1 calc R U . . .
C7 C 0.19458(18) 1.03019(14) 0.07588(12) 0.0366(3) Uani 1 1 d . . . . .
H7A H 0.094528 1.059418 0.042010 0.055 Uiso 1 1 calc R U . . .
H7B H 0.247041 1.114892 0.067085 0.055 Uiso 1 1 calc R U . . .
H7C H 0.172409 0.979184 0.154716 0.055 Uiso 1 1 calc R U . . .
C8 C 0.20769(13) 0.52969(12) 0.09852(9) 0.0213(2) Uani 1 1 d . . . . .
H8 H 0.093704 0.569079 0.107541 0.026 Uiso 1 1 calc R U . . .
O9 O 0.21372(11) 0.41624(9) 0.05362(7) 0.02529(19) Uani 1 1 d . . . . .
H9 H 0.310(2) 0.389(2) 0.0391(15) 0.044(5) Uiso 1 1 d . . . . .
C10 C 0.26890(15) 0.48246(13) 0.21224(10) 0.0254(2) Uani 1 1 d . . . . .
H19A H 0.270140 0.567336 0.236120 0.030 Uiso 1 1 calc R U . . .
H10B H 0.379423 0.436511 0.206871 0.030 Uiso 1 1 calc R U . . .
C11 C 0.16471(14) 0.37732(12) 0.29895(9) 0.0227(2) Uani 1 1 d . . . . .
H11A H 0.055013 0.425149 0.303835 0.027 Uiso 1 1 calc R U . . .
H11B H 0.161040 0.295078 0.272371 0.027 Uiso 1 1 calc R U . . .
N12 N 0.21571(12) 0.32230(10) 0.41102(8) 0.0212(2) Uani 1 1 d . . . . .
C13 C 0.36468(14) 0.22712(12) 0.41695(10) 0.0232(2) Uani 1 1 d . . . . .
H13A H 0.400128 0.204156 0.491220 0.028 Uiso 1 1 calc R U . . .
H13B H 0.447662 0.277296 0.362056 0.028 Uiso 1 1 calc R U . . .
C14 C 0.34780(14) 0.08981(12) 0.39515(9) 0.0220(2) Uani 1 1 d . . . . .
C15 C 0.45215(15) 0.04373(14) 0.31680(11) 0.0288(3) Uani 1 1 d . . . . .
H15 H 0.531691 0.101704 0.273453 0.035 Uiso 1 1 calc R U . . .
C16 C 0.44129(18) -0.08639(15) 0.30121(12) 0.0350(3) Uani 1 1 d . . . . .
H16 H 0.514296 -0.117520 0.248292 0.042 Uiso 1 1 calc R U . . .
C17 C 0.32434(18) -0.17035(14) 0.36270(12) 0.0353(3) Uani 1 1 d . . . . .
H17 H 0.316643 -0.259039 0.351897 0.042 Uiso 1 1 calc R U . . .
C18 C 0.21845(18) -0.12502(14) 0.44003(11) 0.0337(3) Uani 1 1 d . . . . .
H18 H 0.137528 -0.182301 0.481983 0.040 Uiso 1 1 calc R U . . .
C19 C 0.23046(16) 0.00432(13) 0.45633(10) 0.0278(3) Uani 1 1 d . . . . .
H19 H 0.157793 0.034652 0.509802 0.033 Uiso 1 1 calc R U . . .
C20 C 0.22625(14) 0.43848(12) 0.45506(9) 0.0233(2) Uani 1 1 d . . . . .
H20A H 0.135253 0.512006 0.434028 0.028 Uiso 1 1 calc R U . . .
H20B H 0.324938 0.483075 0.420230 0.028 Uiso 1 1 calc R U . . .
C21 C 0.22635(14) 0.39241(12) 0.57939(10) 0.0219(2) Uani 1 1 d . . . . .
C22 C 0.13604(15) 0.28659(13) 0.64954(10) 0.0258(2) Uani 1 1 d . . . . .
H22 H 0.077505 0.236898 0.619232 0.031 Uiso 1 1 calc R U . . .
C23 C 0.13094(16) 0.25319(14) 0.76351(11) 0.0301(3) Uani 1 1 d . . . . .
H23 H 0.068041 0.181577 0.810628 0.036 Uiso 1 1 calc R U . . .
C24 C 0.21722(16) 0.32387(14) 0.80888(10) 0.0305(3) Uani 1 1 d . . . . .
H24 H 0.213740 0.300592 0.886837 0.037 Uiso 1 1 calc R U . . .
C25 C 0.30835(15) 0.42841(14) 0.74005(11) 0.0305(3) Uani 1 1 d . . . . .
H25 H 0.368126 0.476736 0.770693 0.037 Uiso 1 1 calc R U . . .
C26 C 0.31238(14) 0.46266(13) 0.62610(10) 0.0262(2) Uani 1 1 d . . . . .
H26 H 0.374630 0.534993 0.579323 0.031 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 1.4714(9) . ?
P1 O2 1.5753(9) . ?
P1 O5 1.5854(9) . ?
P1 C8 1.8248(11) . ?
O2 C3 1.4620(14) . ?
C3 C4 1.4952(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O5 C6 1.4576(14) . ?
C6 C7 1.4976(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O9 1.4168(13) . ?
C8 C10 1.5303(15) . ?
C8 H8 1.0000 . ?
O9 H9 0.844(19) . ?
C10 C11 1.5364(16) . ?
C10 H19A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.4736(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C20 1.4616(14) . ?
N12 C13 1.4667(15) . ?
C13 C14 1.5121(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3906(18) . ?
C14 C19 1.3915(17) . ?
C15 C16 1.3915(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3903(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.5141(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.3930(16) . ?
C21 C26 1.3947(16) . ?
C22 C23 1.3895(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.3877(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3892(18) . ?
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 O2 109.61(5) . . ?
O1 P1 O5 113.18(5) . . ?
O2 P1 O5 107.62(5) . . ?
O1 P1 C8 116.26(5) . . ?
O2 P1 C8 108.59(5) . . ?
O5 P1 C8 101.00(5) . . ?
C3 O2 P1 120.71(8) . . ?
O2 C3 C4 107.75(10) . . ?
O2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
O2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 O5 P1 119.42(8) . . ?
O5 C6 C7 107.98(11) . . ?
O5 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
O5 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O9 C8 C10 113.27(9) . . ?
O9 C8 P1 112.10(8) . . ?
C10 C8 P1 108.69(8) . . ?
O9 C8 H8 107.5 . . ?
C10 C8 H8 107.5 . . ?
P1 C8 H8 107.5 . . ?
C8 O9 H9 107.7(12) . . ?
C8 C10 C11 111.65(9) . . ?
C8 C10 H19A 109.3 . . ?
C11 C10 H19A 109.3 . . ?
C8 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H19A C10 H10B 108.0 . . ?
N12 C11 C10 116.04(9) . . ?
N12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
N12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C20 N12 C13 111.08(9) . . ?
C20 N12 C11 111.32(9) . . ?
C13 N12 C11 112.90(9) . . ?
N12 C13 C14 112.58(9) . . ?
N12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C19 118.65(11) . . ?
C15 C14 C13 120.96(11) . . ?
C19 C14 C13 120.35(11) . . ?
C14 C15 C16 120.70(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.03(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.89(12) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.03(13) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.69(12) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
N12 C20 C21 114.10(9) . . ?
N12 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
N12 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C26 118.55(11) . . ?
C22 C21 C20 121.97(10) . . ?
C26 C21 C20 119.39(10) . . ?
C23 C22 C21 120.49(11) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.35(12) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.69(12) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 119.95(11) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.96(11) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?

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
O9 H9 O1 0.844(19) 1.82(2) 2.6583(12) 170.1(18) 2_665 yes

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 2172331'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2022-05-12 deposited with the CCDC.	2022-07-01 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         ?
_chemical_formula_sum            'C27 H34 N O4 P'
_chemical_formula_weight         467.52

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                   10.0312(6)
_cell_length_b                   10.9576(9)
_cell_length_c                   13.1760(13)
_cell_angle_alpha                72.616(8)
_cell_angle_beta                 81.716(7)
_cell_angle_gamma                67.437(7)
_cell_volume                     1275.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5339
_cell_measurement_theta_min      3.3890
_cell_measurement_theta_max      26.6270

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.67647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            14455
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.242
_diffrn_reflns_theta_max         26.943
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4957
_reflns_number_gt                4117
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_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)+(0.0531P)²+1.3269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4957
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.64629(6) 0.29522(6) 0.12668(4) 0.02706(17) Uani 1 1 d . . . . .
O1 O 0.68350(17) 0.37095(18) 0.02120(13) 0.0385(4) Uani 1 1 d . . . . .
O2 O 0.68825(18) 0.13802(17) 0.13768(13) 0.0380(4) Uani 1 1 d . . . . .
C3 C 0.7029(5) 0.0809(4) 0.0500(3) 0.0750(11) Uani 1 1 d . . . . .
H3A1 H 0.637016 0.149439 -0.003866 0.090 Uiso 0.507(9) 1 d R U P A 1
H3B1 H 0.670427 0.003889 0.074945 0.090 Uiso 0.507(9) 1 d R U P A 1
H3A2 H 0.791526 0.001130 0.058395 0.090 Uiso 0.493(9) 1 d R U P A 2
H3B2 H 0.715127 0.147660 -0.014545 0.090 Uiso 0.493(9) 1 d R U P A 2
C4A C 0.5967(11) 0.0432(8) 0.0351(9) 0.115(5) Uani 0.493(9) 1 d . . P A 2
H4A1 H 0.511244 0.125013 0.010545 0.172 Uiso 0.493(9) 1 calc R U P A 2
H4A2 H 0.572689 -0.014279 0.102291 0.172 Uiso 0.493(9) 1 calc R U P A 2
H4A3 H 0.628487 -0.008782 -0.018481 0.172 Uiso 0.493(9) 1 calc R U P A 2
C4B C 0.8347(10) 0.0373(9) 0.0022(7) 0.100(4) Uani 0.507(9) 1 d . . P A 1
H4B1 H 0.829048 -0.001658 -0.054305 0.150 Uiso 0.507(9) 1 calc R U P A 1
H4B2 H 0.903515 -0.032993 0.054824 0.150 Uiso 0.507(9) 1 calc R U P A 1
H4B3 H 0.867197 0.114791 -0.028529 0.150 Uiso 0.507(9) 1 calc R U P A 1
O5 O 0.72424(16) 0.29642(17) 0.22205(13) 0.0326(4) Uani 1 1 d . . . . .
C6 C 0.8639(2) 0.3136(3) 0.2059(2) 0.0362(6) Uani 1 1 d . . . . .
H6A H 0.871738 0.359469 0.257933 0.043 Uiso 1 1 calc R U . . .
H6B H 0.870037 0.373183 0.133640 0.043 Uiso 1 1 calc R U . . .
C7 C 0.9871(3) 0.1787(3) 0.2187(2) 0.0385(6) Uani 1 1 d . . . . .
H7A H 0.980901 0.119142 0.290048 0.058 Uiso 1 1 calc R U . . .
H7B H 1.078747 0.193927 0.209361 0.058 Uiso 1 1 calc R U . . .
H7C H 0.982224 0.134934 0.165210 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4564(2) 0.3599(2) 0.16663(16) 0.0226(4) Uani 1 1 d . . . . .
H8 H 0.429974 0.455314 0.172699 0.027 Uiso 1 1 calc R U . . .
O9 O 0.37369(17) 0.36312(17) 0.08633(12) 0.0328(4) Uani 1 1 d . . . . .
H9 H 0.347546 0.441527 0.043483 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4223(2) 0.2717(2) 0.27205(16) 0.0220(4) Uani 1 1 d . . . . .
H10A H 0.496013 0.251255 0.323381 0.026 Uiso 1 1 calc R U . . .
H10B H 0.428985 0.183583 0.261905 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2716(2) 0.3390(2) 0.31966(16) 0.0193(4) Uani 1 1 d . . . . .
H11 H 0.199962 0.348050 0.269800 0.023 Uiso 1 1 calc R U . . .
N12 N 0.24767(17) 0.48044(17) 0.32284(13) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.0966(2) 0.5554(2) 0.34900(16) 0.0212(4) Uani 1 1 d . . . . .
H13A H 0.090527 0.641576 0.362524 0.025 Uiso 1 1 calc R U . . .
H13B H 0.066968 0.499667 0.415884 0.025 Uiso 1 1 calc R U . . .
C14 C -0.0098(2) 0.5907(2) 0.26498(16) 0.0212(4) Uani 1 1 d . . . . .
C15 C -0.1549(2) 0.6184(2) 0.2961(2) 0.0311(5) Uani 1 1 d . . . . .
H15 H -0.183010 0.608629 0.369186 0.037 Uiso 1 1 calc R U . . .
C16 C -0.2591(3) 0.6602(3) 0.2210(2) 0.0429(7) Uani 1 1 d . . . . .
H16 H -0.357844 0.680012 0.243127 0.052 Uiso 1 1 calc R U . . .
C17 C -0.2197(3) 0.6728(3) 0.1155(2) 0.0453(7) Uani 1 1 d . . . . .
H17 H -0.290566 0.700034 0.064346 0.054 Uiso 1 1 calc R U . . .
C18 C -0.0758(3) 0.6454(3) 0.0841(2) 0.0423(6) Uani 1 1 d . . . . .
H18 H -0.048221 0.654004 0.010938 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0293(2) 0.6053(2) 0.15813(18) 0.0302(5) Uani 1 1 d . . . . .
H19 H 0.127519 0.588011 0.135346 0.036 Uiso 1 1 calc R U . . .
C20 C 0.3458(2) 0.4835(2) 0.39419(17) 0.0231(4) Uani 1 1 d . . . . .
H20A H 0.446630 0.433188 0.374049 0.028 Uiso 1 1 calc R U . . .
H20B H 0.326077 0.435472 0.468010 0.028 Uiso 1 1 calc R U . . .
C21 C 0.3301(2) 0.6274(2) 0.39053(18) 0.0251(5) Uani 1 1 d . . . . .
C22 C 0.3332(2) 0.7235(2) 0.2945(2) 0.0333(5) Uani 1 1 d . . . . .
H22 H 0.344806 0.699592 0.229340 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3193(3) 0.8558(3) 0.2942(2) 0.0418(6) Uani 1 1 d . . . . .
H23 H 0.321754 0.921528 0.228594 0.050 Uiso 1 1 calc R U . . .
C24 C 0.3019(2) 0.8912(3) 0.3890(3) 0.0425(7) Uani 1 1 d . . . . .
H24 H 0.292707 0.981020 0.388373 0.051 Uiso 1 1 calc R U . . .
C25 C 0.2979(2) 0.7964(3) 0.4840(2) 0.0380(6) Uani 1 1 d . . . . .
H25 H 0.285087 0.820904 0.549066 0.046 Uiso 1 1 calc R U . . .
C26 C 0.3126(2) 0.6654(2) 0.4848(2) 0.0303(5) Uani 1 1 d . . . . .
H26 H 0.310664 0.600132 0.550857 0.036 Uiso 1 1 calc R U . . .
C27 C 0.2444(2) 0.2463(2) 0.42593(16) 0.0193(4) Uani 1 1 d . . . . .
C28 C 0.3501(2) 0.1736(2) 0.50223(16) 0.0218(4) Uani 1 1 d . . . . .
H28 H 0.443292 0.179399 0.487054 0.026 Uiso 1 1 calc R U . . .
C29 C 0.3216(2) 0.0931(2) 0.59952(17) 0.0250(5) Uani 1 1 d . . . . .
H29 H 0.394564 0.045855 0.650771 0.030 Uiso 1 1 calc R U . . .
C30 C 0.1872(2) 0.0812(2) 0.62262(18) 0.0261(5) Uani 1 1 d . . . . .
H30 H 0.168043 0.025502 0.689333 0.031 Uiso 1 1 calc R U . . .
C31 C 0.0807(2) 0.1511(2) 0.54762(18) 0.0256(5) Uani 1 1 d . . . . .
H31 H -0.011424 0.142684 0.562579 0.031 Uiso 1 1 calc R U . . .
C32 C 0.1091(2) 0.2331(2) 0.45089(17) 0.0236(4) Uani 1 1 d . . . . .
H32 H 0.035198 0.281452 0.400393 0.028 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 1.4692(17) . ?
P1 O2 1.5740(18) . ?
P1 O5 1.5785(17) . ?
P1 C8 1.818(2) . ?
O2 C3 1.435(3) . ?
C3 C4A 1.338(9) . ?
C3 C4B 1.352(8) . ?
C3 H3A1 0.9700 . ?
C3 H3B1 0.9701 . ?
C3 H3A2 0.9700 . ?
C3 H3B2 0.9699 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?
C4B H4B3 0.9800 . ?
O5 C6 1.462(3) . ?
C6 C7 1.500(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O9 1.421(2) . ?
C8 C10 1.515(3) . ?
C8 H8 1.0000 . ?
O9 H9 0.8400 . ?
C10 C11 1.540(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.487(2) . ?
C11 C27 1.523(3) . ?
C11 H11 1.0000 . ?
N12 C13 1.468(2) . ?
N12 C20 1.471(2) . ?
C13 C14 1.511(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.384(3) . ?
C14 C15 1.394(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.511(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.388(3) . ?
C21 C26 1.391(3) . ?
C22 C23 1.401(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.396(3) . ?
C27 C32 1.402(3) . ?
C28 C29 1.384(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(3) . ?
C31 H31 0.9500 . ?
C32 H32 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 O2 113.22(10) . . ?
O1 P1 O5 114.88(10) . . ?
O2 P1 O5 103.50(9) . . ?
O1 P1 C8 114.63(9) . . ?
O2 P1 C8 106.69(10) . . ?
O5 P1 C8 102.73(9) . . ?
C3 O2 P1 124.4(2) . . ?
C4A C3 O2 118.4(6) . . ?
C4B C3 O2 118.5(5) . . ?
C4B C3 H3A1 107.7 . . ?
O2 C3 H3A1 107.7 . . ?
C4B C3 H3B1 107.7 . . ?
O2 C3 H3B1 107.7 . . ?
H3A1 C3 H3B1 107.1 . . ?
C4A C3 H3A2 107.7 . . ?
O2 C3 H3A2 107.7 . . ?
C4A C3 H3B2 107.7 . . ?
O2 C3 H3B2 107.7 . . ?
H3A2 C3 H3B2 107.1 . . ?
C3 C4A H4A1 109.5 . . ?
C3 C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3 C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C3 C4B H4B1 109.5 . . ?
C3 C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C3 C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
C6 O5 P1 121.17(15) . . ?
O5 C6 C7 111.8(2) . . ?
O5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
O5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O9 C8 C10 109.26(17) . . ?
O9 C8 P1 108.18(13) . . ?
C10 C8 P1 112.31(13) . . ?
O9 C8 H8 109.0 . . ?
C10 C8 H8 109.0 . . ?
P1 C8 H8 109.0 . . ?
C8 O9 H9 109.5 . . ?
C8 C10 C11 113.52(16) . . ?
C8 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C8 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N12 C11 C27 114.33(15) . . ?
N12 C11 C10 111.35(16) . . ?
C27 C11 C10 111.03(15) . . ?
N12 C11 H11 106.5 . . ?
C27 C11 H11 106.5 . . ?
C10 C11 H11 106.5 . . ?
C13 N12 C20 110.94(15) . . ?
C13 N12 C11 112.15(15) . . ?
C20 N12 C11 112.75(15) . . ?
N12 C13 C14 115.33(16) . . ?
N12 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N12 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C19 C14 C15 118.9(2) . . ?
C19 C14 C13 122.82(18) . . ?
C15 C14 C13 118.14(19) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 119.8(2) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
N12 C20 C21 112.77(16) . . ?
N12 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N12 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C26 118.9(2) . . ?
C22 C21 C20 121.3(2) . . ?
C26 C21 C20 119.8(2) . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 121.1(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C28 C27 C32 117.52(19) . . ?
C28 C27 C11 122.26(18) . . ?
C32 C27 C11 120.21(17) . . ?
C29 C28 C27 121.24(19) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.36(19) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C31 119.6(2) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 119.83(19) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C27 121.45(19) . . ?
C31 C32 H32 119.3 . . ?
C27 C32 H32 119.3 . . ?

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
O9 H9 O1 0.84 1.89 2.704(2) 161.8 2_665 yes

_refine_diff_density_max         0.920
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 2172330'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2022-05-12 deposited with the CCDC.	2022-07-01 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         ?
_chemical_formula_sum            'C22 H32 N O4 P'
_chemical_formula_weight         405.45

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      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                   10.7214(4)
_cell_length_b                   11.9743(6)
_cell_length_c                   18.1464(8)
_cell_angle_alpha                88.453(4)
_cell_angle_beta                 77.487(4)
_cell_angle_gamma                74.219(4)
_cell_volume                     2187.33(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9175
_cell_measurement_theta_min      3.4530
_cell_measurement_theta_max      27.1080

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            15919
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.413
_diffrn_reflns_theta_max         26.973
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8706
_reflns_number_gt                7298
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'


_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)+(0.0907P)²+2.5317P] 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         8706
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1818
_refine_ls_wR_factor_gt          0.1714
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
P1A P 0.53844(6) 0.31921(5) 0.42478(3) 0.02035(16) Uani 1 1 d . . . . .
O1A O 0.53681(18) 0.43996(14) 0.40627(9) 0.0257(4) Uani 1 1 d . . . . .
O2A O 0.66067(19) 0.22171(15) 0.37945(10) 0.0311(4) Uani 1 1 d . . . . .
C3A C 0.7265(3) 0.2337(3) 0.30159(15) 0.0381(7) Uani 1 1 d . . . . .
H3A1 H 0.8095 0.1700 0.2883 0.046 Uiso 1 1 calc R U . . .
H3A2 H 0.7510 0.3080 0.2978 0.046 Uiso 1 1 calc R U . . .
C4A C 0.6448(4) 0.2313(3) 0.24715(18) 0.0512(8) Uani 1 1 d . . . . .
H4A1 H 0.6953 0.2374 0.1960 0.077 Uiso 1 1 calc R U . . .
H4A2 H 0.5645 0.2967 0.2582 0.077 Uiso 1 1 calc R U . . .
H4A3 H 0.6196 0.1582 0.2507 0.077 Uiso 1 1 calc R U . . .
O5A O 0.41565(18) 0.28484(15) 0.40875(10) 0.0292(4) Uani 1 1 d . . . . .
C6A C 0.2876(3) 0.3707(3) 0.41442(17) 0.0383(7) Uani 1 1 d . . . . .
H6A1 H 0.2788 0.4329 0.4515 0.046 Uiso 1 1 calc R U . . .
H6A2 H 0.2154 0.3332 0.4329 0.046 Uiso 1 1 calc R U . . .
C7A C 0.2735(3) 0.4225(3) 0.34003(18) 0.0417(7) Uani 1 1 d . . . . .
H7A1 H 0.2945 0.3604 0.3016 0.063 Uiso 1 1 calc R U . . .
H7A2 H 0.3346 0.4711 0.3259 0.063 Uiso 1 1 calc R U . . .
H7A3 H 0.1820 0.4702 0.3438 0.063 Uiso 1 1 calc R U . . .
C8A C 0.5444(2) 0.28443(18) 0.52192(12) 0.0172(4) Uani 1 1 d . . . . .
H8A H 0.6211 0.3056 0.5352 0.021 Uiso 1 1 calc R U . . .
O9A O 0.42311(16) 0.35308(14) 0.56715(9) 0.0220(4) Uani 1 1 d . . . . .
H9A H 0.4311 0.4190 0.5759 0.033 Uiso 1 1 calc R U . . .
C10A C 0.5556(2) 0.15634(18) 0.53669(12) 0.0190(4) Uani 1 1 d . . . . .
H10A H 0.6326 0.1089 0.4997 0.023 Uiso 1 1 calc R U . . .
H10B H 0.4750 0.1386 0.5278 0.023 Uiso 1 1 calc R U . . .
C11A C 0.5720(2) 0.12014(19) 0.61626(12) 0.0186(4) Uani 1 1 d . . . . .
H11A H 0.4904 0.1652 0.6524 0.022 Uiso 1 1 calc R U . . .
N12A N 0.68660(18) 0.15018(16) 0.63549(10) 0.0178(4) Uani 1 1 d . . . . .
C13A C 0.8151(2) 0.0770(2) 0.59436(14) 0.0243(5) Uani 1 1 d . . . . .
H13A H 0.8118 0.0691 0.5407 0.029 Uiso 1 1 calc R U . . .
H13B H 0.8307 -0.0014 0.6155 0.029 Uiso 1 1 calc R U . . .
C14A C 0.9299(2) 0.1253(2) 0.59862(13) 0.0252(5) Uani 1 1 d . . . . .
C15A C 1.0513(3) 0.0494(2) 0.60524(16) 0.0340(6) Uani 1 1 d . . . . .
H15A H 1.0598 -0.0315 0.6090 0.041 Uiso 1 1 calc R U . . .
C16A C 1.1596(3) 0.0915(3) 0.60628(17) 0.0415(7) Uani 1 1 d . . . . .
H16A H 1.2417 0.0395 0.6110 0.050 Uiso 1 1 calc R U . . .
C17A C 1.1476(3) 0.2099(3) 0.60034(17) 0.0428(7) Uani 1 1 d . . . . .
H17A H 1.2218 0.2389 0.6002 0.051 Uiso 1 1 calc R U . . .
C18A C 1.0272(3) 0.2849(3) 0.59473(17) 0.0403(7) Uani 1 1 d . . . . .
H18A H 1.0188 0.3658 0.5911 0.048 Uiso 1 1 calc R U . . .
C19A C 0.9183(3) 0.2438(2) 0.59426(15) 0.0325(6) Uani 1 1 d . . . . .
H19A H 0.8358 0.2965 0.5910 0.039 Uiso 1 1 calc R U . . .
C20A C 0.6810(2) 0.1476(2) 0.71687(12) 0.0212(5) Uani 1 1 d . . . . .
H20A H 0.7682 0.1503 0.7254 0.025 Uiso 1 1 calc R U . . .
H20B H 0.6662 0.0728 0.7355 0.025 Uiso 1 1 calc R U . . .
C21A C 0.5745(2) 0.24505(19) 0.76311(12) 0.0180(4) Uani 1 1 d . . . . .
C22A C 0.5335(2) 0.2323(2) 0.84046(13) 0.0241(5) Uani 1 1 d . . . . .
H22A H 0.5703 0.1616 0.8626 0.029 Uiso 1 1 calc R U . . .
C23A C 0.4399(3) 0.3214(2) 0.88572(14) 0.0303(6) Uani 1 1 d . . . . .
H23A H 0.4137 0.3118 0.9384 0.036 Uiso 1 1 calc R U . . .
C24A C 0.3842(2) 0.4252(2) 0.85354(15) 0.0313(6) Uani 1 1 d . . . . .
H24A H 0.3195 0.4862 0.8841 0.038 Uiso 1 1 calc R U . . .
C25A C 0.4241(2) 0.4384(2) 0.77696(15) 0.0279(5) Uani 1 1 d . . . . .
H25A H 0.3863 0.5089 0.7549 0.033 Uiso 1 1 calc R U . . .
C26A C 0.5191(2) 0.34957(19) 0.73177(13) 0.0211(5) Uani 1 1 d . . . . .
H26A H 0.5464 0.3602 0.6793 0.025 Uiso 1 1 calc R U . . .
C27A C 0.5762(2) -0.0095(2) 0.62386(14) 0.0257(5) Uani 1 1 d . . . . .
H27A H 0.6492 -0.0557 0.5851 0.039 Uiso 1 1 calc R U . . .
H27B H 0.4920 -0.0206 0.6172 0.039 Uiso 1 1 calc R U . . .
H27C H 0.5901 -0.0345 0.6740 0.039 Uiso 1 1 calc R U . . .
P1B P 0.02844(6) 0.31720(5) -0.07097(3) 0.02076(16) Uani 1 1 d . . . . .
O1B O 0.02446(17) 0.43616(14) -0.09450(9) 0.0245(4) Uani 1 1 d . . . . .
O2B O -0.08820(18) 0.27470(15) -0.08953(10) 0.0298(4) Uani 1 1 d . . . . .
C3B C -0.2027(3) 0.3544(3) -0.10949(17) 0.0385(7) Uani 1 1 d . . . . .
H3B1 H -0.2212 0.4303 -0.0830 0.046 Uiso 1 1 calc R U . . .
H3B2 H -0.2811 0.3241 -0.0926 0.046 Uiso 1 1 calc R U . . .
C4B C -0.1816(4) 0.3711(4) -0.1925(2) 0.0590(11) Uani 1 1 d . . . . .
H4B1 H -0.2643 0.4183 -0.2048 0.088 Uiso 1 1 calc R U . . .
H4B2 H -0.1549 0.2954 -0.2191 0.088 Uiso 1 1 calc R U . . .
H4B3 H -0.1118 0.4107 -0.2083 0.088 Uiso 1 1 calc R U . . .
O5B O 0.15768(18) 0.22008(16) -0.10819(10) 0.0324(4) Uani 1 1 d . . . . .
C6B C 0.2059(3) 0.2103(2) -0.18971(14) 0.0338(6) Uani 1 1 d . . . . .
H6B1 H 0.2574 0.2671 -0.2065 0.041 Uiso 1 1 calc R U . . .
H6B2 H 0.1304 0.2261 -0.2152 0.041 Uiso 1 1 calc R U . . .
C7B C 0.2925(3) 0.0891(3) -0.20884(18) 0.0437(7) Uani 1 1 d . . . . .
H7B1 H 0.3665 0.0744 -0.1830 0.065 Uiso 1 1 calc R U . . .
H7B2 H 0.3274 0.0798 -0.2636 0.065 Uiso 1 1 calc R U . . .
H7B3 H 0.2403 0.0337 -0.1924 0.065 Uiso 1 1 calc R U . . .
C8B C 0.0241(2) 0.29560(19) 0.02848(13) 0.0201(5) Uani 1 1 d . . . . .
H8B H 0.1009 0.3168 0.0415 0.024 Uiso 1 1 calc R U . . .
O9B O -0.09636(15) 0.37157(14) 0.06922(9) 0.0228(4) Uani 1 1 d . . . . .
H9B H -0.0839 0.4360 0.0773 0.034 Uiso 1 1 calc R U . . .
C10B C 0.0286(2) 0.1712(2) 0.05145(14) 0.0233(5) Uani 1 1 d . . . . .
H10C H 0.1015 0.1171 0.0156 0.028 Uiso 1 1 calc R U . . .
H10D H -0.0557 0.1555 0.0474 0.028 Uiso 1 1 calc R U . . .
C11B C 0.0495(2) 0.1467(2) 0.13213(14) 0.0249(5) Uani 1 1 d . . . . .
H11B H -0.0308 0.1955 0.1674 0.030 Uiso 1 1 calc R U . . .
N12B N 0.16501(19) 0.18188(16) 0.14492(11) 0.0216(4) Uani 1 1 d . . . . .
C13B C 0.2919(2) 0.1142(2) 0.09967(15) 0.0281(5) Uani 1 1 d . . . . .
H13C H 0.2792 0.0969 0.0492 0.034 Uiso 1 1 calc R U . . .
H13D H 0.3205 0.0393 0.1240 0.034 Uiso 1 1 calc R U . . .
C14B C 0.4009(2) 0.1753(2) 0.08998(13) 0.0278(5) Uani 1 1 d . . . . .
C15B C 0.5316(3) 0.1109(3) 0.06478(16) 0.0392(7) Uani 1 1 d . . . . .
H15B H 0.5516 0.0292 0.0574 0.047 Uiso 1 1 calc R U . . .
C16B C 0.6335(3) 0.1642(3) 0.05021(19) 0.0503(9) Uani 1 1 d . . . . .
H16B H 0.7222 0.1191 0.0313 0.060 Uiso 1 1 calc R U . . .
C17B C 0.6075(3) 0.2828(3) 0.06295(18) 0.0458(8) Uani 1 1 d . . . . .
H17B H 0.6779 0.3188 0.0542 0.055 Uiso 1 1 calc R U . . .
C18B C 0.4784(3) 0.3476(3) 0.08843(16) 0.0375(6) Uani 1 1 d . . . . .
H18B H 0.4595 0.4289 0.0972 0.045 Uiso 1 1 calc R U . . .
C19B C 0.3753(3) 0.2949(2) 0.10144(15) 0.0307(6) Uani 1 1 d . . . . .
H19B H 0.2864 0.3409 0.1183 0.037 Uiso 1 1 calc R U . . .
C20B C 0.1697(2) 0.1854(2) 0.22505(14) 0.0252(5) Uani 1 1 d . . . . .
H20C H 0.2571 0.1945 0.2289 0.030 Uiso 1 1 calc R U . . .
H20D H 0.1625 0.1101 0.2468 0.030 Uiso 1 1 calc R U . . .
C21B C 0.0620(2) 0.2816(2) 0.27156(13) 0.0205(5) Uani 1 1 d . . . . .
C22B C 0.0222(2) 0.2708(2) 0.34960(14) 0.0277(5) Uani 1 1 d . . . . .
H22B H 0.0605 0.2013 0.3724 0.033 Uiso 1 1 calc R U . . .
C23B C -0.0724(3) 0.3601(3) 0.39399(15) 0.0332(6) Uani 1 1 d . . . . .
H23B H -0.0972 0.3518 0.4469 0.040 Uiso 1 1 calc R U . . .
C24B C -0.1308(2) 0.4617(2) 0.36146(15) 0.0306(6) Uani 1 1 d . . . . .
H24B H -0.1964 0.5225 0.3918 0.037 Uiso 1 1 calc R U . . .
C25B C -0.0927(2) 0.4733(2) 0.28449(14) 0.0255(5) Uani 1 1 d . . . . .
H25B H -0.1322 0.5426 0.2619 0.031 Uiso 1 1 calc R U . . .
C26B C 0.0033(2) 0.3843(2) 0.23979(13) 0.0212(5) Uani 1 1 d . . . . .
H26B H 0.0290 0.3937 0.1870 0.025 Uiso 1 1 calc R U . . .
C27B C 0.0539(3) 0.0190(2) 0.14830(17) 0.0365(6) Uani 1 1 d . . . . .
H27D H 0.1327 -0.0318 0.1155 0.055 Uiso 1 1 calc R U . . .
H27E H -0.0261 0.0031 0.1385 0.055 Uiso 1 1 calc R U . . .
H27F H 0.0579 0.0044 0.2013 0.055 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
P1A O1A 1.4718(16) . ?
P1A O5A 1.5666(18) . ?
P1A O2A 1.5841(18) . ?
P1A C8A 1.811(2) . ?
O2A C3A 1.459(3) . ?
C3A C4A 1.461(4) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
O5A C6A 1.459(3) . ?
C6A C7A 1.491(4) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A O9A 1.426(3) . ?
C8A C10A 1.527(3) . ?
C8A H8A 1.0000 . ?
O9A H9A 0.8400 . ?
C10A C11A 1.529(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A N12A 1.481(3) . ?
C11A C27A 1.544(3) . ?
C11A H11A 1.0000 . ?
N12A C20A 1.465(3) . ?
N12A C13A 1.469(3) . ?
C13A C14A 1.511(3) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C19A 1.392(4) . ?
C14A C15A 1.397(4) . ?
C15A C16A 1.390(4) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.392(4) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.380(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.387(4) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
C20A C21A 1.511(3) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C21A C22A 1.394(3) . ?
C21A C26A 1.395(3) . ?
C22A C23A 1.389(4) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.396(4) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.381(4) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.392(3) . ?
C25A H25A 0.9500 . ?
C26A H26A 0.9500 . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
P1B O1B 1.4681(17) . ?
P1B O2B 1.5729(18) . ?
P1B O5B 1.5776(18) . ?
P1B C8B 1.809(2) . ?
O2B C3B 1.445(3) . ?
C3B C4B 1.491(4) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?
C4B H4B3 0.9800 . ?
O5B C6B 1.454(3) . ?
C6B C7B 1.498(4) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B O9B 1.423(3) . ?
C8B C10B 1.527(3) . ?
C8B H8B 1.0000 . ?
O9B H9B 0.8400 . ?
C10B C11B 1.537(3) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B N12B 1.476(3) . ?
C11B C27B 1.538(3) . ?
C11B H11B 1.0000 . ?
N12B C13B 1.461(3) . ?
N12B C20B 1.468(3) . ?
C13B C14B 1.517(3) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.386(4) . ?
C14B C19B 1.396(4) . ?
C15B C16B 1.384(4) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.386(5) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.374(4) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.391(4) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
C20B C21B 1.510(3) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C21B C26B 1.392(3) . ?
C21B C22B 1.401(3) . ?
C22B C23B 1.387(4) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.388(4) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.382(4) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.394(3) . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 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
O1A P1A O5A 113.00(10) . . ?
O1A P1A O2A 116.16(10) . . ?
O5A P1A O2A 103.13(10) . . ?
O1A P1A C8A 114.53(10) . . ?
O5A P1A C8A 106.53(10) . . ?
O2A P1A C8A 102.19(10) . . ?
C3A O2A P1A 123.06(17) . . ?
O2A C3A C4A 113.4(3) . . ?
O2A C3A H3A1 108.9 . . ?
C4A C3A H3A1 108.9 . . ?
O2A C3A H3A2 108.9 . . ?
C4A C3A H3A2 108.9 . . ?
H3A1 C3A H3A2 107.7 . . ?
C3A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C6A O5A P1A 121.34(16) . . ?
O5A C6A C7A 111.4(2) . . ?
O5A C6A H6A1 109.3 . . ?
C7A C6A H6A1 109.3 . . ?
O5A C6A H6A2 109.3 . . ?
C7A C6A H6A2 109.3 . . ?
H6A1 C6A H6A2 108.0 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
O9A C8A C10A 109.03(17) . . ?
O9A C8A P1A 106.35(14) . . ?
C10A C8A P1A 112.37(15) . . ?
O9A C8A H8A 109.7 . . ?
C10A C8A H8A 109.7 . . ?
P1A C8A H8A 109.7 . . ?
C8A O9A H9A 109.5 . . ?
C8A C10A C11A 114.56(18) . . ?
C8A C10A H10A 108.6 . . ?
C11A C10A H10A 108.6 . . ?
C8A C10A H10B 108.6 . . ?
C11A C10A H10B 108.6 . . ?
H10A C10A H10B 107.6 . . ?
N12A C11A C10A 111.86(17) . . ?
N12A C11A C27A 114.33(18) . . ?
C10A C11A C27A 108.72(18) . . ?
N12A C11A H11A 107.2 . . ?
C10A C11A H11A 107.2 . . ?
C27A C11A H11A 107.2 . . ?
C20A N12A C13A 110.09(18) . . ?
C20A N12A C11A 112.11(17) . . ?
C13A N12A C11A 113.01(17) . . ?
N12A C13A C14A 112.96(19) . . ?
N12A C13A H13A 109.0 . . ?
C14A C13A H13A 109.0 . . ?
N12A C13A H13B 109.0 . . ?
C14A C13A H13B 109.0 . . ?
H13A C13A H13B 107.8 . . ?
C19A C14A C15A 119.1(2) . . ?
C19A C14A C13A 121.4(2) . . ?
C15A C14A C13A 119.5(2) . . ?
C16A C15A C14A 120.5(3) . . ?
C16A C15A H15A 119.8 . . ?
C14A C15A H15A 119.8 . . ?
C15A C16A C17A 119.9(3) . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C18A C17A C16A 119.6(3) . . ?
C18A C17A H17A 120.2 . . ?
C16A C17A H17A 120.2 . . ?
C17A C18A C19A 120.9(3) . . ?
C17A C18A H18A 119.6 . . ?
C19A C18A H18A 119.6 . . ?
C18A C19A C14A 120.1(3) . . ?
C18A C19A H19A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
N12A C20A C21A 114.91(18) . . ?
N12A C20A H20A 108.5 . . ?
C21A C20A H20A 108.5 . . ?
N12A C20A H20B 108.5 . . ?
C21A C20A H20B 108.5 . . ?
H20A C20A H20B 107.5 . . ?
C22A C21A C26A 118.6(2) . . ?
C22A C21A C20A 119.1(2) . . ?
C26A C21A C20A 122.3(2) . . ?
C23A C22A C21A 121.1(2) . . ?
C23A C22A H22A 119.5 . . ?
C21A C22A H22A 119.5 . . ?
C22A C23A C24A 119.8(2) . . ?
C22A C23A H23A 120.1 . . ?
C24A C23A H23A 120.1 . . ?
C25A C24A C23A 119.5(2) . . ?
C25A C24A H24A 120.3 . . ?
C23A C24A H24A 120.3 . . ?
C24A C25A C26A 120.6(2) . . ?
C24A C25A H25A 119.7 . . ?
C26A C25A H25A 119.7 . . ?
C25A C26A C21A 120.4(2) . . ?
C25A C26A H26A 119.8 . . ?
C21A C26A H26A 119.8 . . ?
C11A C27A H27A 109.5 . . ?
C11A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
C11A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
O1B P1B O2B 112.80(10) . . ?
O1B P1B O5B 115.90(10) . . ?
O2B P1B O5B 104.19(10) . . ?
O1B P1B C8B 114.28(10) . . ?
O2B P1B C8B 107.00(10) . . ?
O5B P1B C8B 101.49(10) . . ?
C3B O2B P1B 121.91(16) . . ?
O2B C3B C4B 111.6(3) . . ?
O2B C3B H3B1 109.3 . . ?
C4B C3B H3B1 109.3 . . ?
O2B C3B H3B2 109.3 . . ?
C4B C3B H3B2 109.3 . . ?
H3B1 C3B H3B2 108.0 . . ?
C3B C4B H4B1 109.5 . . ?
C3B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C3B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
C6B O5B P1B 120.74(17) . . ?
O5B C6B C7B 107.4(2) . . ?
O5B C6B H6B1 110.2 . . ?
C7B C6B H6B1 110.2 . . ?
O5B C6B H6B2 110.2 . . ?
C7B C6B H6B2 110.2 . . ?
H6B1 C6B H6B2 108.5 . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
O9B C8B C10B 108.85(18) . . ?
O9B C8B P1B 107.28(15) . . ?
C10B C8B P1B 113.24(16) . . ?
O9B C8B H8B 109.1 . . ?
C10B C8B H8B 109.1 . . ?
P1B C8B H8B 109.1 . . ?
C8B O9B H9B 109.5 . . ?
C8B C10B C11B 113.54(19) . . ?
C8B C10B H10C 108.9 . . ?
C11B C10B H10C 108.9 . . ?
C8B C10B H10D 108.9 . . ?
C11B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
N12B C11B C10B 111.70(19) . . ?
N12B C11B C27B 114.8(2) . . ?
C10B C11B C27B 108.7(2) . . ?
N12B C11B H11B 107.1 . . ?
C10B C11B H11B 107.1 . . ?
C27B C11B H11B 107.1 . . ?
C13B N12B C20B 111.01(19) . . ?
C13B N12B C11B 113.76(19) . . ?
C20B N12B C11B 112.98(18) . . ?
N12B C13B C14B 113.5(2) . . ?
N12B C13B H13C 108.9 . . ?
C14B C13B H13C 108.9 . . ?
N12B C13B H13D 108.9 . . ?
C14B C13B H13D 108.9 . . ?
H13C C13B H13D 107.7 . . ?
C15B C14B C19B 118.1(2) . . ?
C15B C14B C13B 118.9(2) . . ?
C19B C14B C13B 123.0(2) . . ?
C16B C15B C14B 120.9(3) . . ?
C16B C15B H15B 119.6 . . ?
C14B C15B H15B 119.6 . . ?
C15B C16B C17B 120.7(3) . . ?
C15B C16B H16B 119.7 . . ?
C17B C16B H16B 119.7 . . ?
C18B C17B C16B 119.1(3) . . ?
C18B C17B H17B 120.5 . . ?
C16B C17B H17B 120.5 . . ?
C17B C18B C19B 120.5(3) . . ?
C17B C18B H18B 119.8 . . ?
C19B C18B H18B 119.8 . . ?
C18B C19B C14B 120.8(3) . . ?
C18B C19B H19B 119.6 . . ?
C14B C19B H19B 119.6 . . ?
N12B C20B C21B 114.30(19) . . ?
N12B C20B H20C 108.7 . . ?
C21B C20B H20C 108.7 . . ?
N12B C20B H20D 108.7 . . ?
C21B C20B H20D 108.7 . . ?
H20C C20B H20D 107.6 . . ?
C26B C21B C22B 118.1(2) . . ?
C26B C21B C20B 122.0(2) . . ?
C22B C21B C20B 119.9(2) . . ?
C23B C22B C21B 121.0(2) . . ?
C23B C22B H22B 119.5 . . ?
C21B C22B H22B 119.5 . . ?
C22B C23B C24B 120.3(2) . . ?
C22B C23B H23B 119.8 . . ?
C24B C23B H23B 119.8 . . ?
C25B C24B C23B 119.3(2) . . ?
C25B C24B H24B 120.4 . . ?
C23B C24B H24B 120.4 . . ?
C24B C25B C26B 120.6(2) . . ?
C24B C25B H25B 119.7 . . ?
C26B C25B H25B 119.7 . . ?
C21B C26B C25B 120.8(2) . . ?
C21B C26B H26B 119.6 . . ?
C25B C26B H26B 119.6 . . ?
C11B C27B H27D 109.5 . . ?
C11B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C11B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 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
O1A P1A O2A C3A -32.6(2) . . . . ?
O5A P1A O2A C3A 91.6(2) . . . . ?
C8A P1A O2A C3A -158.0(2) . . . . ?
P1A O2A C3A C4A -69.3(3) . . . . ?
O1A P1A O5A C6A -30.1(2) . . . . ?
O2A P1A O5A C6A -156.31(18) . . . . ?
C8A P1A O5A C6A 96.52(19) . . . . ?
P1A O5A C6A C7A 92.8(3) . . . . ?
O1A P1A C8A O9A 64.74(17) . . . . ?
O5A P1A C8A O9A -60.95(16) . . . . ?
O2A P1A C8A O9A -168.80(14) . . . . ?
O1A P1A C8A C10A -176.04(15) . . . . ?
O5A P1A C8A C10A 58.27(17) . . . . ?
O2A P1A C8A C10A -49.58(17) . . . . ?
O9A C8A C10A C11A -66.9(2) . . . . ?
P1A C8A C10A C11A 175.46(15) . . . . ?
C8A C10A C11A N12A -55.1(2) . . . . ?
C8A C10A C11A C27A 177.73(18) . . . . ?
C10A C11A N12A C20A 163.42(18) . . . . ?
C27A C11A N12A C20A -72.5(2) . . . . ?
C10A C11A N12A C13A -71.5(2) . . . . ?
C27A C11A N12A C13A 52.6(2) . . . . ?
C20A N12A C13A C14A -68.1(2) . . . . ?
C11A N12A C13A C14A 165.72(19) . . . . ?
N12A C13A C14A C19A -39.6(3) . . . . ?
N12A C13A C14A C15A 142.0(2) . . . . ?
C19A C14A C15A C16A -1.0(4) . . . . ?
C13A C14A C15A C16A 177.5(2) . . . . ?
C14A C15A C16A C17A -0.3(4) . . . . ?
C15A C16A C17A C18A 1.1(4) . . . . ?
C16A C17A C18A C19A -0.6(4) . . . . ?
C17A C18A C19A C14A -0.7(4) . . . . ?
C15A C14A C19A C18A 1.5(4) . . . . ?
C13A C14A C19A C18A -176.9(2) . . . . ?
C13A N12A C20A C21A 162.23(19) . . . . ?
C11A N12A C20A C21A -71.1(2) . . . . ?
N12A C20A C21A C22A 160.5(2) . . . . ?
N12A C20A C21A C26A -22.1(3) . . . . ?
C26A C21A C22A C23A -0.1(3) . . . . ?
C20A C21A C22A C23A 177.4(2) . . . . ?
C21A C22A C23A C24A 0.7(4) . . . . ?
C22A C23A C24A C25A -0.6(4) . . . . ?
C23A C24A C25A C26A -0.1(4) . . . . ?
C24A C25A C26A C21A 0.7(3) . . . . ?
C22A C21A C26A C25A -0.6(3) . . . . ?
C20A C21A C26A C25A -178.0(2) . . . . ?
O1B P1B O2B C3B -14.5(2) . . . . ?
O5B P1B O2B C3B -141.1(2) . . . . ?
C8B P1B O2B C3B 112.0(2) . . . . ?
P1B O2B C3B C4B 89.3(3) . . . . ?
O1B P1B O5B C6B -51.3(2) . . . . ?
O2B P1B O5B C6B 73.2(2) . . . . ?
C8B P1B O5B C6B -175.71(19) . . . . ?
P1B O5B C6B C7B -158.5(2) . . . . ?
O1B P1B C8B O9B 59.97(18) . . . . ?
O2B P1B C8B O9B -65.65(16) . . . . ?
O5B P1B C8B O9B -174.53(14) . . . . ?
O1B P1B C8B C10B -179.91(15) . . . . ?
O2B P1B C8B C10B 54.47(18) . . . . ?
O5B P1B C8B C10B -54.42(18) . . . . ?
O9B C8B C10B C11B -70.9(2) . . . . ?
P1B C8B C10B C11B 169.92(16) . . . . ?
C8B C10B C11B N12B -51.6(3) . . . . ?
C8B C10B C11B C27B -179.3(2) . . . . ?
C10B C11B N12B C13B -65.7(2) . . . . ?
C27B C11B N12B C13B 58.7(3) . . . . ?
C10B C11B N12B C20B 166.54(19) . . . . ?
C27B C11B N12B C20B -69.1(3) . . . . ?
C20B N12B C13B C14B -72.6(3) . . . . ?
C11B N12B C13B C14B 158.6(2) . . . . ?
N12B C13B C14B C15B 164.3(2) . . . . ?
N12B C13B C14B C19B -19.2(4) . . . . ?
C19B C14B C15B C16B -1.1(4) . . . . ?
C13B C14B C15B C16B 175.6(3) . . . . ?
C14B C15B C16B C17B 2.2(5) . . . . ?
C15B C16B C17B C18B -1.7(5) . . . . ?
C16B C17B C18B C19B 0.1(5) . . . . ?
C17B C18B C19B C14B 0.9(4) . . . . ?
C15B C14B C19B C18B -0.5(4) . . . . ?
C13B C14B C19B C18B -177.0(2) . . . . ?
C13B N12B C20B C21B 161.63(19) . . . . ?
C11B N12B C20B C21B -69.2(2) . . . . ?
N12B C20B C21B C26B -26.7(3) . . . . ?
N12B C20B C21B C22B 155.7(2) . . . . ?
C26B C21B C22B C23B -0.4(4) . . . . ?
C20B C21B C22B C23B 177.2(2) . . . . ?
C21B C22B C23B C24B 1.0(4) . . . . ?
C22B C23B C24B C25B -0.8(4) . . . . ?
C23B C24B C25B C26B 0.1(4) . . . . ?
C22B C21B C26B C25B -0.3(3) . . . . ?
C20B C21B C26B C25B -177.8(2) . . . . ?
C24B C25B C26B C21B 0.4(4) . . . . ?

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
O9A H9A O1A 0.84 1.86 2.700(2) 175.5 2_666
O9B H9B O1B 0.84 1.87 2.698(2) 169.7 2_565

_refine_diff_density_max         1.142
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.072

