# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_M263
_database_code_depnum_ccdc_archive 'CCDC 2243302'
loop_
_audit_author_name
_audit_author_address
'Sun Yuli'
;The National university of Singapore Crystallographic Date Centre
Singapore
;
_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H30 F N2 O5 P'
_chemical_formula_weight         596.57

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0878(4)
_cell_length_b                   14.2865(8)
_cell_length_c                   11.2346(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.771(2)
_cell_angle_gamma                90
_cell_volume                     1451.23(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      29.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_T_max  0.7405
_exptl_absorpt_process_details   
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0918 before and 0.0654 after correction.            
The Ratio of minimum to maximum transmission is 0.9587.        
The λ/2 correction factor is Not present. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus Sealed Tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47818
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         30.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8831
_reflns_number_gt                7917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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_bruker_data_scaling   'SADABS V2016/2 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX4 v2021.10-1 (Bruker AXS)'
_computing_data_collection       'APEX4 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0366P)²+0.3887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
; 
 Flack x determined using 3421 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8831
_refine_ls_number_parameters     390
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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 0.96217(6) 0.40546(4) 0.78407(5) 0.01567(11) Uani 1 1 d . . . . .
F1 F 0.26417(19) 0.75025(13) 0.83573(15) 0.0361(4) Uani 1 1 d . . . . .
O1 O 0.87015(19) 0.46428(13) 0.85680(16) 0.0220(4) Uani 1 1 d . . . . .
O2 O 0.8708(2) 0.68230(12) 0.54253(16) 0.0233(4) Uani 1 1 d . . . . .
O3 O 0.68758(19) 0.38795(11) 0.58252(16) 0.0221(4) Uani 1 1 d . . . . .
N1 N 0.7504(2) 0.54240(14) 0.56039(17) 0.0174(4) Uani 1 1 d . . . . .
N2 N 0.6088(2) 0.57613(14) 0.53598(17) 0.0182(4) Uani 1 1 d . . . . .
C1 C 1.1577(2) 0.41288(17) 0.8292(2) 0.0179(4) Uani 1 1 d . . . . .
C2 C 1.2016(3) 0.43010(18) 0.9496(2) 0.0241(5) Uani 1 1 d . . . . .
H2 H 1.129580 0.441262 1.003637 0.029 Uiso 1 1 calc R U . . .
C3 C 1.3516(3) 0.4309(2) 0.9907(3) 0.0297(6) Uani 1 1 d . . . . .
H3 H 1.381513 0.441538 1.073043 0.036 Uiso 1 1 calc R U . . .
C4 C 1.4567(3) 0.41639(19) 0.9121(3) 0.0277(5) Uani 1 1 d . . . . .
H4 H 1.558756 0.416845 0.940528 0.033 Uiso 1 1 calc R U . . .
C5 C 1.4135(3) 0.4011(2) 0.7919(3) 0.0261(5) Uani 1 1 d . . . . .
H5 H 1.486107 0.392522 0.737648 0.031 Uiso 1 1 calc R U . . .
C6 C 1.2646(3) 0.39837(18) 0.7505(2) 0.0220(4) Uani 1 1 d . . . . .
H6 H 1.235392 0.386570 0.668253 0.026 Uiso 1 1 calc R U . . .
C7 C 0.9133(2) 0.28348(16) 0.7851(2) 0.0166(4) Uani 1 1 d . . . . .
C8 C 0.9804(3) 0.21772(17) 0.7162(2) 0.0188(4) Uani 1 1 d . . . . .
H8 H 1.051417 0.237164 0.664793 0.023 Uiso 1 1 calc R U . . .
C9 C 0.9431(3) 0.12397(17) 0.7232(2) 0.0223(5) Uani 1 1 d . . . . .
H9 H 0.988789 0.079038 0.676545 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8394(3) 0.09563(18) 0.7981(2) 0.0235(5) Uani 1 1 d . . . . .
H10 H 0.814172 0.031280 0.802634 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7723(3) 0.16061(19) 0.8663(2) 0.0255(5) Uani 1 1 d . . . . .
H11 H 0.701189 0.140753 0.917474 0.031 Uiso 1 1 calc R U . . .
C12 C 0.8086(3) 0.25487(18) 0.8601(2) 0.0217(5) Uani 1 1 d . . . . .
H12 H 0.762370 0.299544 0.906766 0.026 Uiso 1 1 calc R U . . .
C13 C 0.9436(2) 0.44172(16) 0.6273(2) 0.0168(4) Uani 1 1 d . . . . .
H13 H 0.991270 0.394933 0.577140 0.020 Uiso 1 1 calc R U . . .
C14 C 1.0062(3) 0.54023(17) 0.6091(2) 0.0195(4) Uani 1 1 d . . . . .
H14A H 1.056479 0.564530 0.685081 0.023 Uiso 1 1 calc R U . . .
H14B H 1.078057 0.538846 0.548480 0.023 Uiso 1 1 calc R U . . .
C15 C 0.8752(3) 0.60067(17) 0.5670(2) 0.0177(4) Uani 1 1 d . . . . .
C16 C 0.7791(2) 0.44879(16) 0.5880(2) 0.0166(4) Uani 1 1 d . . . . .
C17 C 0.5339(3) 0.61520(16) 0.6259(2) 0.0179(4) Uani 1 1 d . . . . .
C18 C 0.5621(3) 0.60598(17) 0.7491(2) 0.0201(4) Uani 1 1 d . . . . .
H18 H 0.641999 0.569116 0.784271 0.024 Uiso 1 1 calc R U . . .
C19 C 0.4687(3) 0.65290(18) 0.8179(2) 0.0232(5) Uani 1 1 d . . . . .
H19 H 0.483332 0.649285 0.902692 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3529(3) 0.70556(19) 0.7622(2) 0.0248(5) Uani 1 1 d . . . . .
C21 C 0.3226(3) 0.71553(18) 0.6410(2) 0.0234(5) Uani 1 1 d . . . . .
H21 H 0.241277 0.751742 0.607057 0.028 Uiso 1 1 calc R U . . .
C22 C 0.4181(2) 0.66938(17) 0.5697(2) 0.0190(4) Uani 1 1 d . . . . .
C23 C 0.4309(3) 0.66610(17) 0.4435(2) 0.0201(4) Uani 1 1 d . . . . .
H23 H 0.367668 0.696803 0.383247 0.024 Uiso 1 1 calc R U . . .
C24 C 0.5492(3) 0.61141(16) 0.4249(2) 0.0179(4) Uani 1 1 d . . . . .
C25 C 0.6130(3) 0.58915(16) 0.3136(2) 0.0185(4) Uani 1 1 d . . . . .
C26 C 0.6133(3) 0.65937(18) 0.2271(2) 0.0224(5) Uani 1 1 d . . . . .
H26 H 0.571827 0.718808 0.241694 0.027 Uiso 1 1 calc R U . . .
C27 C 0.6733(3) 0.6435(2) 0.1204(2) 0.0270(5) Uani 1 1 d . . . . .
H27 H 0.673476 0.692062 0.062725 0.032 Uiso 1 1 calc R U . . .
C28 C 0.7329(3) 0.5570(2) 0.0977(2) 0.0287(6) Uani 1 1 d . . . . .
H28 H 0.774989 0.546239 0.024934 0.034 Uiso 1 1 calc R U . . .
C29 C 0.7308(3) 0.4863(2) 0.1816(2) 0.0262(5) Uani 1 1 d . . . . .
H29 H 0.769455 0.426425 0.165197 0.031 Uiso 1 1 calc R U . . .
C30 C 0.6727(3) 0.50189(18) 0.2897(2) 0.0219(5) Uani 1 1 d . . . . .
H30 H 0.673613 0.453176 0.347335 0.026 Uiso 1 1 calc R U . . .
O1S O 0.0971(2) 0.40419(15) 0.40086(18) 0.0306(4) Uani 1 1 d . . . . .
O2S O 0.2052(2) 0.32062(14) 0.26462(18) 0.0284(4) Uani 1 1 d . . . . .
C1S C 0.3592(3) 0.3841(2) 0.4245(3) 0.0373(7) Uani 1 1 d . . . . .
H1SA H 0.430209 0.383273 0.364412 0.056 Uiso 1 1 calc R U . . .
H1SB H 0.381630 0.333021 0.481617 0.056 Uiso 1 1 calc R U . . .
H1SC H 0.366033 0.444113 0.467071 0.056 Uiso 1 1 calc R U . . .
C2S C 0.2073(3) 0.37209(19) 0.3646(2) 0.0261(5) Uani 1 1 d . . . . .
C3S C 0.0608(3) 0.2959(2) 0.2088(3) 0.0293(6) Uani 1 1 d . . . . .
H3SA H 0.012650 0.351023 0.168250 0.035 Uiso 1 1 calc R U . . .
H3SB H -0.002354 0.273154 0.269563 0.035 Uiso 1 1 calc R U . . .
C4S C 0.0818(4) 0.2198(2) 0.1191(3) 0.0366(7) Uani 1 1 d . . . . .
H4SA H -0.014348 0.202600 0.077528 0.055 Uiso 1 1 calc R U . . .
H4SB H 0.126578 0.164925 0.160628 0.055 Uiso 1 1 calc R U . . .
H4SC H 0.146822 0.242539 0.060862 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
P1 O1 1.4868(18) . ?
P1 C7 1.799(2) . ?
P1 C1 1.801(2) . ?
P1 C13 1.828(2) . ?
F1 C20 1.369(3) . ?
O2 C15 1.198(3) . ?
O3 C16 1.200(3) . ?
N1 N2 1.376(3) . ?
N1 C16 1.392(3) . ?
N1 C15 1.402(3) . ?
N2 C17 1.390(3) . ?
N2 C24 1.403(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.394(3) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.395(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C16 1.519(3) . ?
C13 C14 1.539(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.508(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 C18 1.388(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.369(4) . ?
C21 C22 1.404(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.435(3) . ?
C23 C24 1.362(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.465(3) . ?
C25 C30 1.396(3) . ?
C25 C26 1.397(3) . ?
C26 C27 1.384(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.383(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
O1S C2S 1.208(3) . ?
O2S C2S 1.341(3) . ?
O2S C3S 1.440(3) . ?
C1S C2S 1.484(4) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C3S C4S 1.506(4) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 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 C7 113.03(11) . . ?
O1 P1 C1 113.91(11) . . ?
C7 P1 C1 107.00(11) . . ?
O1 P1 C13 111.54(11) . . ?
C7 P1 C13 106.38(11) . . ?
C1 P1 C13 104.33(11) . . ?
N2 N1 C16 122.10(19) . . ?
N2 N1 C15 122.53(19) . . ?
C16 N1 C15 115.23(19) . . ?
N1 N2 C17 120.81(19) . . ?
N1 N2 C24 124.9(2) . . ?
C17 N2 C24 109.18(19) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 P1 117.55(18) . . ?
C6 C1 P1 122.89(18) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 120.0(2) . . ?
C12 C7 P1 118.15(18) . . ?
C8 C7 P1 121.78(18) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C16 C13 C14 105.45(18) . . ?
C16 C13 P1 106.93(15) . . ?
C14 C13 P1 112.80(16) . . ?
C16 C13 H13 110.5 . . ?
C14 C13 H13 110.5 . . ?
P1 C13 H13 110.5 . . ?
C15 C14 C13 105.95(19) . . ?
C15 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
O2 C15 N1 123.9(2) . . ?
O2 C15 C14 129.5(2) . . ?
N1 C15 C14 106.59(19) . . ?
O3 C16 N1 124.8(2) . . ?
O3 C16 C13 128.6(2) . . ?
N1 C16 C13 106.58(19) . . ?
C18 C17 N2 129.1(2) . . ?
C18 C17 C22 123.8(2) . . ?
N2 C17 C22 107.1(2) . . ?
C19 C18 C17 116.8(2) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C18 C19 C20 119.5(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
F1 C20 C21 118.7(2) . . ?
F1 C20 C19 116.5(2) . . ?
C21 C20 C19 124.8(2) . . ?
C20 C21 C22 116.4(2) . . ?
C20 C21 H21 121.8 . . ?
C22 C21 H21 121.8 . . ?
C21 C22 C17 118.7(2) . . ?
C21 C22 C23 134.1(2) . . ?
C17 C22 C23 107.2(2) . . ?
C24 C23 C22 108.3(2) . . ?
C24 C23 H23 125.9 . . ?
C22 C23 H23 125.9 . . ?
C23 C24 N2 108.1(2) . . ?
C23 C24 C25 129.9(2) . . ?
N2 C24 C25 122.1(2) . . ?
C30 C25 C26 118.6(2) . . ?
C30 C25 C24 123.5(2) . . ?
C26 C25 C24 117.8(2) . . ?
C27 C26 C25 120.9(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C26 120.1(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C29 C30 120.7(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C25 120.0(2) . . ?
C29 C30 H30 120.0 . . ?
C25 C30 H30 120.0 . . ?
C2S O2S C3S 115.8(2) . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O1S C2S O2S 123.2(3) . . ?
O1S C2S C1S 124.6(3) . . ?
O2S C2S C1S 112.2(2) . . ?
O2S C3S C4S 107.3(2) . . ?
O2S C3S H3SA 110.3 . . ?
C4S C3S H3SA 110.3 . . ?
O2S C3S H3SB 110.3 . . ?
C4S C3S H3SB 110.3 . . ?
H3SA C3S H3SB 108.5 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 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
C16 N1 N2 C17 93.6(3) . . . . ?
C15 N1 N2 C17 -82.0(3) . . . . ?
C16 N1 N2 C24 -114.3(3) . . . . ?
C15 N1 N2 C24 70.0(3) . . . . ?
O1 P1 C1 C2 30.5(2) . . . . ?
C7 P1 C1 C2 -95.2(2) . . . . ?
C13 P1 C1 C2 152.3(2) . . . . ?
O1 P1 C1 C6 -152.2(2) . . . . ?
C7 P1 C1 C6 82.1(2) . . . . ?
C13 P1 C1 C6 -30.4(2) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
P1 C1 C2 C3 176.1(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
P1 C1 C6 C5 -177.2(2) . . . . ?
O1 P1 C7 C12 -6.1(2) . . . . ?
C1 P1 C7 C12 120.10(19) . . . . ?
C13 P1 C7 C12 -128.82(18) . . . . ?
O1 P1 C7 C8 175.89(18) . . . . ?
C1 P1 C7 C8 -57.9(2) . . . . ?
C13 P1 C7 C8 53.2(2) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
P1 C7 C8 C9 177.66(18) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
P1 C7 C12 C11 -177.70(19) . . . . ?
O1 P1 C13 C16 -49.62(18) . . . . ?
C7 P1 C13 C16 74.05(17) . . . . ?
C1 P1 C13 C16 -173.02(15) . . . . ?
O1 P1 C13 C14 65.86(18) . . . . ?
C7 P1 C13 C14 -170.47(15) . . . . ?
C1 P1 C13 C14 -57.54(18) . . . . ?
C16 C13 C14 C15 3.0(2) . . . . ?
P1 C13 C14 C15 -113.33(18) . . . . ?
N2 N1 C15 O2 -6.5(3) . . . . ?
C16 N1 C15 O2 177.5(2) . . . . ?
N2 N1 C15 C14 173.58(19) . . . . ?
C16 N1 C15 C14 -2.4(3) . . . . ?
C13 C14 C15 O2 179.5(2) . . . . ?
C13 C14 C15 N1 -0.6(2) . . . . ?
N2 N1 C16 O3 7.2(4) . . . . ?
C15 N1 C16 O3 -176.8(2) . . . . ?
N2 N1 C16 C13 -171.62(19) . . . . ?
C15 N1 C16 C13 4.3(3) . . . . ?
C14 C13 C16 O3 176.8(2) . . . . ?
P1 C13 C16 O3 -62.9(3) . . . . ?
C14 C13 C16 N1 -4.4(2) . . . . ?
P1 C13 C16 N1 115.94(17) . . . . ?
N1 N2 C17 C18 -18.8(4) . . . . ?
C24 N2 C17 C18 -174.8(2) . . . . ?
N1 N2 C17 C22 160.9(2) . . . . ?
C24 N2 C17 C22 4.9(3) . . . . ?
N2 C17 C18 C19 -179.8(2) . . . . ?
C22 C17 C18 C19 0.5(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 F1 179.9(2) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
F1 C20 C21 C22 179.1(2) . . . . ?
C19 C20 C21 C22 -0.8(4) . . . . ?
C20 C21 C22 C17 1.5(4) . . . . ?
C20 C21 C22 C23 -175.7(3) . . . . ?
C18 C17 C22 C21 -1.5(4) . . . . ?
N2 C17 C22 C21 178.8(2) . . . . ?
C18 C17 C22 C23 176.4(2) . . . . ?
N2 C17 C22 C23 -3.3(3) . . . . ?
C21 C22 C23 C24 177.9(3) . . . . ?
C17 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 N2 2.6(3) . . . . ?
C22 C23 C24 C25 -177.0(2) . . . . ?
N1 N2 C24 C23 -159.5(2) . . . . ?
C17 N2 C24 C23 -4.7(3) . . . . ?
N1 N2 C24 C25 20.1(3) . . . . ?
C17 N2 C24 C25 174.9(2) . . . . ?
C23 C24 C25 C30 -143.7(3) . . . . ?
N2 C24 C25 C30 36.8(3) . . . . ?
C23 C24 C25 C26 36.2(4) . . . . ?
N2 C24 C25 C26 -143.4(2) . . . . ?
C30 C25 C26 C27 -0.9(4) . . . . ?
C24 C25 C26 C27 179.3(2) . . . . ?
C25 C26 C27 C28 0.5(4) . . . . ?
C26 C27 C28 C29 0.7(4) . . . . ?
C27 C28 C29 C30 -1.6(4) . . . . ?
C28 C29 C30 C25 1.2(4) . . . . ?
C26 C25 C30 C29 0.0(4) . . . . ?
C24 C25 C30 C29 179.8(2) . . . . ?
C3S O2S C2S O1S -7.0(4) . . . . ?
C3S O2S C2S C1S 172.7(2) . . . . ?
C2S O2S C3S C4S -165.9(2) . . . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_N343
_database_code_depnum_ccdc_archive 'CCDC 2295537'
loop_
_audit_author_name
_audit_author_address
'sun yuli'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N3 O6'
_chemical_formula_weight         439.46

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.6376(2)
_cell_length_b                   12.5870(3)
_cell_length_c                   25.9116(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2164.85(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9709
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      72.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.818
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
; 
SADABS-2016 (Bruker,2016). wR2(int)= 0.1322 before correction 
and =0.0358 after correction. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microfocus Sealed Tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            87952
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.411
_diffrn_reflns_theta_max         72.134
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4262
_reflns_number_gt                4256
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.991

_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_bruker_data_scaling   'SADABS V2016/2 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX4 v2021.10-1 (Bruker AXS)'
_computing_data_collection       'APEX4 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(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)+(0.0324P)²+0.4297P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual Space'
_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_abs_structure_details 
; 
 Flack x determined using 1784 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.015(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4262
_refine_ls_number_parameters     374
_refine_ls_number_restraints     295
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0604
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.048
_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
O1 O -0.09897(16) 0.32023(9) 0.25385(4) 0.0231(2) Uani 1 1 d . . . . .
O2 O -0.05620(17) 0.32217(8) 0.34008(4) 0.0229(2) Uani 1 1 d . . . . .
O3 O 0.14202(17) 0.57815(8) 0.39717(4) 0.0236(2) Uani 1 1 d . . . . .
O4 O 0.38456(17) 0.24322(8) 0.37223(4) 0.0216(2) Uani 1 1 d . . . . .
C16 C 0.2211(2) 0.48934(11) 0.57377(5) 0.0177(3) Uani 0.863(3) 1 d D U P A 1
C17 C 0.2227(4) 0.59984(18) 0.58036(9) 0.0174(5) Uani 0.863(3) 1 d D U P A 1
C18 C 0.3867(4) 0.64861(19) 0.60417(8) 0.0227(5) Uani 0.863(3) 1 d D U P A 1
H18 H 0.389122 0.723545 0.608506 0.027 Uiso 0.863(3) 1 calc R U P A 1
C19 C 0.5466(4) 0.5870(3) 0.62153(10) 0.0260(6) Uani 0.863(3) 1 d D U P A 1
H19 H 0.658654 0.620510 0.637535 0.031 Uiso 0.863(3) 1 calc R U P A 1
C20 C 0.5455(5) 0.4778(3) 0.61591(14) 0.0256(8) Uani 0.863(3) 1 d D U P A 1
H20 H 0.655520 0.436390 0.627894 0.031 Uiso 0.863(3) 1 calc R U P A 1
C21 C 0.3809(7) 0.4296(3) 0.5925(3) 0.0226(10) Uani 0.863(3) 1 d D U P A 1
H21 H 0.377756 0.354470 0.589209 0.027 Uiso 0.863(3) 1 calc R U P A 1
O5 O 0.0567(2) 0.65109(10) 0.56127(5) 0.0223(3) Uani 0.863(3) 1 d D U P A 1
C22 C 0.0337(3) 0.76274(13) 0.57164(7) 0.0263(4) Uani 0.863(3) 1 d D U P A 1
H22A H 0.082397 0.778064 0.606982 0.032 Uiso 0.863(3) 1 calc R U P A 1
H22B H -0.110952 0.781546 0.570098 0.032 Uiso 0.863(3) 1 calc R U P A 1
C23 C 0.1482(5) 0.8303(3) 0.53377(12) 0.0327(7) Uani 0.863(3) 1 d D U P A 1
H23A H 0.128399 0.905471 0.542152 0.049 Uiso 0.863(3) 1 calc R U P A 1
H23B H 0.098835 0.816317 0.498776 0.049 Uiso 0.863(3) 1 calc R U P A 1
H23C H 0.291996 0.813026 0.535702 0.049 Uiso 0.863(3) 1 calc R U P A 1
C16A C 0.2211(2) 0.48934(11) 0.57377(5) 0.0177(3) Uani 0.137(3) 1 d D U P A 2
C17A C 0.297(2) 0.6007(11) 0.5756(6) 0.019(2) Uani 0.137(3) 1 d D U P A 2
C18A C 0.472(3) 0.6281(12) 0.6016(6) 0.020(2) Uani 0.137(3) 1 d D U P A 2
H18A H 0.513533 0.700133 0.604598 0.023 Uiso 0.137(3) 1 calc R U P A 2
C19A C 0.584(3) 0.5475(16) 0.6228(7) 0.022(3) Uani 0.137(3) 1 d D U P A 2
H19A H 0.706364 0.564464 0.640027 0.026 Uiso 0.137(3) 1 calc R U P A 2
C20A C 0.527(4) 0.4456(16) 0.6199(10) 0.022(3) Uani 0.137(3) 1 d D U P A 2
H20A H 0.606904 0.392508 0.636068 0.026 Uiso 0.137(3) 1 calc R U P A 2
C21A C 0.354(5) 0.416(2) 0.5940(18) 0.016(3) Uani 0.137(3) 1 d D U P A 2
H21A H 0.325435 0.342814 0.589923 0.019 Uiso 0.137(3) 1 calc R U P A 2
O5A O 0.1758(16) 0.6703(6) 0.5508(3) 0.0250(19) Uani 0.137(3) 1 d D U P A 2
C22A C 0.232(2) 0.7816(9) 0.5557(5) 0.027(2) Uani 0.137(3) 1 d D U P A 2
H22C H 0.370794 0.792749 0.543134 0.033 Uiso 0.137(3) 1 calc R U P A 2
H22D H 0.225139 0.803864 0.592361 0.033 Uiso 0.137(3) 1 calc R U P A 2
C23A C 0.086(3) 0.8454(17) 0.5241(9) 0.031(3) Uani 0.137(3) 1 d D U P A 2
H23D H 0.124329 0.920580 0.525247 0.047 Uiso 0.137(3) 1 calc R U P A 2
H23E H -0.050131 0.836900 0.538088 0.047 Uiso 0.137(3) 1 calc R U P A 2
H23F H 0.089001 0.820437 0.488286 0.047 Uiso 0.137(3) 1 calc R U P A 2
N1 N 0.31492(19) 0.43894(9) 0.32359(4) 0.0166(2) Uani 1 1 d . . . . .
N2 N 0.29458(18) 0.41943(9) 0.37545(4) 0.0157(2) Uani 1 1 d . . . . .
N3 N 0.03238(19) 0.46705(11) 0.49040(5) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.1810(2) 0.40751(11) 0.28502(5) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.2543(2) 0.44228(11) 0.23871(5) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.193681 0.431670 0.205900 0.021 Uiso 1 1 calc R U . . .
H3 H 0.015(3) 0.5356(17) 0.4887(7) 0.027 Uiso 1 1 d . U . . .
C3 C 0.4386(2) 0.49747(11) 0.24852(5) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.5768(2) 0.55195(12) 0.21709(5) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.556495 0.556415 0.180859 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7419(2) 0.59868(12) 0.23972(6) 0.0229(3) Uani 1 1 d . . . . .
H5 H 0.835336 0.636232 0.218771 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7757(2) 0.59204(11) 0.29348(6) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.892168 0.624387 0.307877 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6425(2) 0.53937(11) 0.32549(6) 0.0191(3) Uani 1 1 d . . . . .
H7 H 0.664437 0.534516 0.361642 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4743(2) 0.49371(10) 0.30212(5) 0.0157(3) Uani 1 1 d . . . . .
C9 C -0.0020(2) 0.34692(11) 0.29697(6) 0.0175(3) Uani 1 1 d . . . . .
C10 C -0.2739(2) 0.25265(13) 0.26121(7) 0.0278(3) Uani 1 1 d . . . . .
H10A H -0.338376 0.239333 0.227808 0.042 Uiso 1 1 calc R U . . .
H10B H -0.369754 0.287993 0.284298 0.042 Uiso 1 1 calc R U . . .
H10C H -0.231686 0.185006 0.276502 0.042 Uiso 1 1 calc R U . . .
C11 C 0.2073(2) 0.49232(11) 0.40899(5) 0.0165(3) Uani 1 1 d . . . . .
C12 C 0.2169(2) 0.44215(11) 0.46220(5) 0.0159(3) Uani 1 1 d . . . . .
H12 H 0.335657 0.470949 0.481410 0.019 Uiso 1 1 calc R U . . .
C13 C 0.2486(2) 0.32330(11) 0.45161(5) 0.0180(3) Uani 1 1 d . . . . .
H13A H 0.350106 0.293252 0.475498 0.022 Uiso 1 1 calc R U . . .
H13B H 0.120781 0.283702 0.455798 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3217(2) 0.31724(11) 0.39648(5) 0.0162(3) Uani 1 1 d . . . . .
C15 C 0.0457(2) 0.43895(12) 0.54591(5) 0.0219(3) Uani 1 1 d . . . . .
H15A H 0.056772 0.360784 0.549042 0.026 Uiso 1 1 calc R U . A 1
H15B H -0.080751 0.460862 0.563157 0.026 Uiso 1 1 calc R U . A 1
O1W O 0.70730(18) 0.36400(11) 0.43750(5) 0.0290(3) Uani 1 1 d . . . . .
H1W H 0.804(4) 0.4007(19) 0.4541(9) 0.043 Uiso 1 1 d . U . . .
H2W H 0.758(4) 0.3469(19) 0.4082(9) 0.043 Uiso 1 1 d . 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
O1 C9 1.3323(18) . ?
O1 C10 1.4520(18) . ?
O2 C9 1.2141(18) . ?
O3 C11 1.2037(18) . ?
O4 C14 1.1987(18) . ?
C16 C21 1.387(4) . ?
C16 C17 1.401(3) . ?
C16 C15 1.510(2) . ?
C17 O5 1.369(3) . ?
C17 C18 1.394(3) . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O5 C22 1.439(2) . ?
C22 C23 1.504(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C16A C21A 1.38(2) . ?
C16A C17A 1.491(14) . ?
C16A C15 1.510(2) . ?
C17A O5A 1.352(14) . ?
C17A C18A 1.388(17) . ?
C18A C19A 1.372(17) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.340(17) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.38(2) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?
O5A C22A 1.455(13) . ?
C22A C23A 1.500(16) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
N1 N2 1.3725(16) . ?
N1 C8 1.3798(19) . ?
N1 C1 1.3949(18) . ?
N2 C11 1.3901(18) . ?
N2 C14 1.4085(17) . ?
N3 C12 1.4604(18) . ?
N3 C15 1.4838(18) . ?
N3 H3 0.87(2) . ?
C1 C2 1.3669(19) . ?
C1 C9 1.467(2) . ?
C2 C3 1.430(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(2) . ?
C3 C8 1.4095(19) . ?
C4 C5 1.375(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.413(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(2) . ?
C7 H7 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5179(19) . ?
C12 C13 1.5354(19) . ?
C12 H12 1.0000 . ?
C13 C14 1.5106(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O1W H1W 0.90(3) . ?
O1W H2W 0.86(3) . ?

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
C9 O1 C10 115.08(12) . . ?
C21 C16 C17 119.3(2) . . ?
C21 C16 C15 121.9(2) . . ?
C17 C16 C15 118.74(16) . . ?
O5 C17 C18 125.5(2) . . ?
O5 C17 C16 114.69(19) . . ?
C18 C17 C16 119.8(2) . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C20 121.1(4) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C17 O5 C22 118.54(16) . . ?
O5 C22 C23 112.12(18) . . ?
O5 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
O5 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21A C16A C17A 113.5(13) . . ?
C21A C16A C15 113.3(12) . . ?
C17A C16A C15 132.2(5) . . ?
O5A C17A C18A 124.6(13) . . ?
O5A C17A C16A 113.1(10) . . ?
C18A C17A C16A 122.2(11) . . ?
C19A C18A C17A 117.6(14) . . ?
C19A C18A H18A 121.2 . . ?
C17A C18A H18A 121.2 . . ?
C20A C19A C18A 122.2(18) . . ?
C20A C19A H19A 118.9 . . ?
C18A C19A H19A 118.9 . . ?
C19A C20A C21A 121(2) . . ?
C19A C20A H20A 119.4 . . ?
C21A C20A H20A 119.4 . . ?
C16A C21A C20A 123(2) . . ?
C16A C21A H21A 118.7 . . ?
C20A C21A H21A 118.7 . . ?
C17A O5A C22A 115.5(10) . . ?
O5A C22A C23A 107.7(13) . . ?
O5A C22A H22C 110.2 . . ?
C23A C22A H22C 110.2 . . ?
O5A C22A H22D 110.2 . . ?
C23A C22A H22D 110.2 . . ?
H22C C22A H22D 108.5 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
N2 N1 C8 124.03(12) . . ?
N2 N1 C1 126.01(12) . . ?
C8 N1 C1 109.96(11) . . ?
N1 N2 C11 122.34(11) . . ?
N1 N2 C14 121.97(11) . . ?
C11 N2 C14 114.46(11) . . ?
C12 N3 C15 112.57(12) . . ?
C12 N3 H3 107.5(14) . . ?
C15 N3 H3 107.1(13) . . ?
C2 C1 N1 108.14(12) . . ?
C2 C1 C9 130.27(13) . . ?
N1 C1 C9 121.59(12) . . ?
C1 C2 C3 107.70(12) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
C4 C3 C8 118.54(13) . . ?
C4 C3 C2 133.83(13) . . ?
C8 C3 C2 107.62(12) . . ?
C5 C4 C3 118.79(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.43(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.23(14) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 116.71(13) . . ?
C6 C7 H7 121.6 . . ?
C8 C7 H7 121.6 . . ?
N1 C8 C7 130.14(13) . . ?
N1 C8 C3 106.58(12) . . ?
C7 C8 C3 123.28(13) . . ?
O2 C9 O1 124.31(13) . . ?
O2 C9 C1 124.94(13) . . ?
O1 C9 C1 110.74(12) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N2 125.68(13) . . ?
O3 C11 C12 128.29(13) . . ?
N2 C11 C12 106.02(11) . . ?
N3 C12 C11 109.26(12) . . ?
N3 C12 C13 114.42(12) . . ?
C11 C12 C13 104.40(11) . . ?
N3 C12 H12 109.5 . . ?
C11 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
C14 C13 C12 105.20(11) . . ?
C14 C13 H13A 110.7 . . ?
C12 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
O4 C14 N2 123.47(13) . . ?
O4 C14 C13 130.29(13) . . ?
N2 C14 C13 106.18(11) . . ?
N3 C15 C16 114.16(12) . . ?
N3 C15 C16A 114.16(12) . . ?
N3 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
N3 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
H1W O1W H2W 106(2) . . ?

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
C21 C16 C17 O5 -179.0(4) . . . . ?
C15 C16 C17 O5 1.6(2) . . . . ?
C21 C16 C17 C18 1.9(5) . . . . ?
C15 C16 C17 C18 -177.52(16) . . . . ?
O5 C17 C18 C19 -179.5(2) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C18 C19 C20 C21 0.0(5) . . . . ?
C17 C16 C21 C20 -2.4(8) . . . . ?
C15 C16 C21 C20 177.0(4) . . . . ?
C19 C20 C21 C16 1.4(8) . . . . ?
C18 C17 O5 C22 -8.2(3) . . . . ?
C16 C17 O5 C22 172.75(17) . . . . ?
C17 O5 C22 C23 84.0(2) . . . . ?
C21A C16A C17A O5A 173(2) . . . . ?
C15 C16A C17A O5A 6.2(16) . . . . ?
C21A C16A C17A C18A -8(3) . . . . ?
C15 C16A C17A C18A -175.6(10) . . . . ?
O5A C17A C18A C19A -177.1(15) . . . . ?
C16A C17A C18A C19A 5(2) . . . . ?
C17A C18A C19A C20A -1(3) . . . . ?
C18A C19A C20A C21A 2(4) . . . . ?
C17A C16A C21A C20A 9(5) . . . . ?
C15 C16A C21A C20A 179(3) . . . . ?
C19A C20A C21A C16A -6(6) . . . . ?
C18A C17A O5A C22A -4(2) . . . . ?
C16A C17A O5A C22A 174.0(10) . . . . ?
C17A O5A C22A C23A 177.5(14) . . . . ?
C8 N1 N2 C11 85.29(17) . . . . ?
C1 N1 N2 C11 -94.63(17) . . . . ?
C8 N1 N2 C14 -108.06(16) . . . . ?
C1 N1 N2 C14 72.03(18) . . . . ?
N2 N1 C1 C2 179.84(13) . . . . ?
C8 N1 C1 C2 -0.09(16) . . . . ?
N2 N1 C1 C9 -0.6(2) . . . . ?
C8 N1 C1 C9 179.51(12) . . . . ?
N1 C1 C2 C3 -0.31(16) . . . . ?
C9 C1 C2 C3 -179.85(14) . . . . ?
C1 C2 C3 C4 -178.05(16) . . . . ?
C1 C2 C3 C8 0.58(15) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C5 179.01(15) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
N2 N1 C8 C7 0.2(2) . . . . ?
C1 N1 C8 C7 -179.84(14) . . . . ?
N2 N1 C8 C3 -179.48(12) . . . . ?
C1 N1 C8 C3 0.45(15) . . . . ?
C6 C7 C8 N1 -178.40(14) . . . . ?
C6 C7 C8 C3 1.3(2) . . . . ?
C4 C3 C8 N1 178.26(13) . . . . ?
C2 C3 C8 N1 -0.62(15) . . . . ?
C4 C3 C8 C7 -1.5(2) . . . . ?
C2 C3 C8 C7 179.64(13) . . . . ?
C10 O1 C9 O2 -3.2(2) . . . . ?
C10 O1 C9 C1 175.28(12) . . . . ?
C2 C1 C9 O2 -178.03(15) . . . . ?
N1 C1 C9 O2 2.5(2) . . . . ?
C2 C1 C9 O1 3.5(2) . . . . ?
N1 C1 C9 O1 -176.00(12) . . . . ?
N1 N2 C11 O3 -0.2(2) . . . . ?
C14 N2 C11 O3 -167.76(14) . . . . ?
N1 N2 C11 C12 -178.98(12) . . . . ?
C14 N2 C11 C12 13.44(16) . . . . ?
C15 N3 C12 C11 -168.96(12) . . . . ?
C15 N3 C12 C13 74.43(15) . . . . ?
O3 C11 C12 N3 39.5(2) . . . . ?
N2 C11 C12 N3 -141.77(12) . . . . ?
O3 C11 C12 C13 162.28(15) . . . . ?
N2 C11 C12 C13 -18.96(14) . . . . ?
N3 C12 C13 C14 137.22(12) . . . . ?
C11 C12 C13 C14 17.83(14) . . . . ?
N1 N2 C14 O4 8.2(2) . . . . ?
C11 N2 C14 O4 175.86(14) . . . . ?
N1 N2 C14 C13 -169.38(12) . . . . ?
C11 N2 C14 C13 -1.76(16) . . . . ?
C12 C13 C14 O4 172.10(15) . . . . ?
C12 C13 C14 N2 -10.52(14) . . . . ?
C12 N3 C15 C16 55.70(17) . . . . ?
C12 N3 C15 C16A 55.70(17) . . . . ?
C21 C16 C15 N3 -112.5(4) . . . . ?
C17 C16 C15 N3 66.82(19) . . . . ?
C21A C16A C15 N3 -119(2) . . . . ?
C17A C16A C15 N3 48.5(9) . . . . ?

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
C22^a H22B^a O3 0.99 2.55 3.380(2) 140.8 4_466 yes
N3 H3 O5^a 0.87(2) 2.39(2) 2.9605(18) 123.0(16) . yes
N3 H3 O5A^b 0.87(2) 2.57(2) 3.148(9) 124.3(16) . yes
O1W H1W N3 0.90(3) 1.97(3) 2.8665(18) 174(2) 1_655 yes
O1W H2W O2 0.86(3) 2.18(3) 3.0189(16) 167(2) 1_655 yes

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037

