# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_rs814_330_55_1_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2340010'
loop_
_audit_author_name
_audit_author_address
'Liqiang Hao'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-05-02 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            'C29 H24 N O4 P'
_chemical_formula_weight         481.46

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.3847(4)
_cell_length_b                   17.7511(5)
_cell_length_c                   18.5322(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.6320(10)
_cell_angle_gamma                90
_cell_volume                     5136.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9148
_cell_measurement_theta_min      5.3772
_cell_measurement_theta_max      75.0377

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.229
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Quest
_diffrn_measurement_method       'phi and omi'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            58205
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.770
_diffrn_reflns_theta_max         68.430
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4667
_reflns_number_gt                4164
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+5.5477P] 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         4667
_refine_ls_number_parameters     354
_refine_ls_number_restraints     187
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1345
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

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
O2 O 0.8706(8) 0.3450(12) 0.3602(13) 0.046(3) Uani 0.56(4) 1 d D U P A 3
O3 O 0.8198(9) 0.3682(10) 0.6369(8) 0.042(2) Uani 0.56(4) 1 d . U P A 3
O4 O 0.6643(9) 0.3386(10) 0.6044(10) 0.0369(19) Uani 0.56(4) 1 d . U P A 3
C28 C 0.9119(10) 0.3710(12) 0.6601(8) 0.055(3) Uani 0.56(4) 1 d . U P A 3
H28A H 0.933413 0.373393 0.714348 0.082 Uiso 0.56(4) 1 calc R U P A 3
H28B H 0.930100 0.414854 0.638823 0.082 Uiso 0.56(4) 1 calc R U P A 3
H28C H 0.933653 0.326646 0.642643 0.082 Uiso 0.56(4) 1 calc R U P A 3
C29 C 0.5791(14) 0.3172(13) 0.5932(14) 0.046(3) Uani 0.56(4) 1 d . U P A 3
H29A H 0.568115 0.314651 0.641135 0.070 Uiso 0.56(4) 1 calc R U P A 3
H29B H 0.569106 0.268755 0.569134 0.070 Uiso 0.56(4) 1 calc R U P A 3
H29C H 0.541522 0.353670 0.561510 0.070 Uiso 0.56(4) 1 calc R U P A 3
O2A O 0.8668(10) 0.3636(12) 0.3581(15) 0.036(2) Uani 0.44(4) 1 d D U P A 4
O3A O 0.8220(12) 0.3899(12) 0.6388(11) 0.044(2) Uani 0.44(4) 1 d . U P A 4
O4A O 0.6580(14) 0.3572(13) 0.6023(14) 0.045(3) Uani 0.44(4) 1 d . U P A 4
C28A C 0.9104(15) 0.3987(16) 0.6595(13) 0.063(4) Uani 0.44(4) 1 d . U P A 4
H28D H 0.931455 0.413183 0.711738 0.094 Uiso 0.44(4) 1 calc R U P A 4
H28E H 0.924468 0.436959 0.628611 0.094 Uiso 0.44(4) 1 calc R U P A 4
H28F H 0.936349 0.351911 0.652268 0.094 Uiso 0.44(4) 1 calc R U P A 4
C29A C 0.5692(19) 0.3343(15) 0.5903(18) 0.048(4) Uani 0.44(4) 1 d . U P A 4
H29D H 0.557875 0.332223 0.638147 0.072 Uiso 0.44(4) 1 calc R U P A 4
H29E H 0.559893 0.285553 0.566892 0.072 Uiso 0.44(4) 1 calc R U P A 4
H29F H 0.531543 0.370263 0.558048 0.072 Uiso 0.44(4) 1 calc R U P A 4
P1 P 0.61471(3) 0.29129(3) 0.15621(3) 0.03394(17) Uani 1 1 d . . . . .
O1 O 0.53689(9) 0.30984(10) 0.17807(9) 0.0452(4) Uani 1 1 d . . . . .
N1 N 0.65142(10) 0.32029(10) 0.33628(9) 0.0371(4) Uani 1 1 d . . . . .
H1 H 0.598543 0.310751 0.312906 0.045 Uiso 1 1 calc R U . . .
C1 C 0.62467(13) 0.34695(12) 0.07769(12) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.67040(16) 0.32414(14) 0.02958(13) 0.0479(5) Uani 1 1 d . . . . .
H2 H 0.690462 0.274914 0.031923 0.058 Uiso 1 1 calc R U . . .
C3 C 0.68640(19) 0.37415(16) -0.02190(15) 0.0615(7) Uani 1 1 d . . . . .
H3 H 0.717445 0.358406 -0.053670 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6567(2) 0.44683(16) -0.02627(17) 0.0672(8) Uani 1 1 d . . . . .
H4 H 0.667969 0.480550 -0.060453 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6102(2) 0.46922(15) 0.02018(19) 0.0701(8) Uani 1 1 d . . . . .
H5 H 0.589323 0.518230 0.016782 0.084 Uiso 1 1 calc R U . . .
C6 C 0.59387(16) 0.42019(14) 0.07199(15) 0.0526(6) Uani 1 1 d . . . . .
H6 H 0.562172 0.436293 0.103088 0.063 Uiso 1 1 calc R U . . .
C7 C 0.61909(13) 0.19361(12) 0.13010(12) 0.0378(5) Uani 1 1 d . . . . .
C8 C 0.65949(16) 0.14044(14) 0.18409(14) 0.0509(6) Uani 1 1 d . . . . .
H8 H 0.689429 0.155650 0.232968 0.061 Uiso 1 1 calc R U . . .
C9 C 0.6552(2) 0.06499(16) 0.16515(19) 0.0692(8) Uani 1 1 d . . . . .
H9 H 0.681980 0.029517 0.201557 0.083 Uiso 1 1 calc R U . . .
C10 C 0.6117(2) 0.04193(16) 0.09308(19) 0.0687(8) Uani 1 1 d . . . . .
H10 H 0.609390 -0.008988 0.080809 0.082 Uiso 1 1 calc R U . . .
C11 C 0.5720(2) 0.09355(15) 0.03934(16) 0.0623(7) Uani 1 1 d . . . . .
H11 H 0.542913 0.077900 -0.009606 0.075 Uiso 1 1 calc R U . . .
C12 C 0.57494(15) 0.16908(14) 0.05783(13) 0.0472(5) Uani 1 1 d . . . . .
H12 H 0.546935 0.203968 0.021260 0.057 Uiso 1 1 calc R U . . .
C13 C 0.71296(13) 0.31136(12) 0.22984(11) 0.0365(4) Uani 1 1 d . . . . .
C14 C 0.71593(12) 0.32362(11) 0.30241(11) 0.0341(4) Uani 1 1 d . . . . .
C15 C 0.79754(12) 0.34438(12) 0.36558(11) 0.0356(4) Uani 1 1 d D . . . .
C16 C 0.77152(12) 0.35005(11) 0.43269(11) 0.0339(4) Uani 1 1 d . . . . .
C17 C 0.68438(12) 0.33461(11) 0.41366(11) 0.0318(4) Uani 1 1 d . . . . .
C18 C 0.79139(8) 0.31681(9) 0.20481(9) 0.0432(5) Uani 1 1 d G U . . .
C19 C 0.83721(10) 0.25216(8) 0.19974(10) 0.0565(6) Uani 1 1 d G U . . .
H19 H 0.819969 0.205693 0.213196 0.068 Uiso 1 1 calc R U . . .
C20 C 0.90878(10) 0.25695(12) 0.17455(11) 0.0763(9) Uani 1 1 d G U . . .
H20 H 0.939431 0.213694 0.171152 0.092 Uiso 1 1 calc R U . . .
C21 C 0.93454(10) 0.32640(14) 0.15443(12) 0.0852(11) Uani 1 1 d G U . . .
H21 H 0.982431 0.329602 0.137578 0.102 Uiso 1 1 calc R U . . .
C22 C 0.88873(13) 0.39105(11) 0.15951(12) 0.0870(11) Uani 1 1 d G U . . .
H22 H 0.905970 0.437510 0.146048 0.104 Uiso 1 1 calc R U . . .
C23 C 0.81716(11) 0.38625(8) 0.18470(11) 0.0640(7) Uani 1 1 d G U . . .
H23 H 0.786508 0.429511 0.188092 0.077 Uiso 1 1 calc R U . . .
C24 C 0.82049(13) 0.36507(12) 0.50737(11) 0.0375(5) Uani 1 1 d . . . . .
H24 H 0.878658 0.375614 0.519159 0.045 Uiso 1 1 calc R U . . .
C25 C 0.78111(13) 0.36393(13) 0.56253(11) 0.0379(5) Uani 1 1 d . . . . .
C26 C 0.69199(13) 0.34733(12) 0.54336(11) 0.0369(5) Uani 1 1 d . . . . .
C27 C 0.64279(13) 0.33329(12) 0.46912(11) 0.0351(4) Uani 1 1 d . . . . .
H27 H 0.584439 0.323419 0.456918 0.042 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
O2 C15 1.232(9) . ?
O3 C25 1.334(15) . ?
O3 C28 1.439(19) . ?
O4 C26 1.348(18) . ?
O4 C29 1.40(3) . ?
O2A C15 1.232(11) . ?
O3A C28A 1.39(3) . ?
O3A C25 1.445(18) . ?
O4A C26 1.38(3) . ?
O4A C29A 1.46(4) . ?
P1 O1 1.4871(15) . ?
P1 C13 1.803(2) . ?
P1 C1 1.807(2) . ?
P1 C7 1.807(2) . ?
N1 C14 1.384(3) . ?
N1 C17 1.394(2) . ?
C1 C6 1.387(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.385(4) . ?
C3 C4 1.373(4) . ?
C4 C5 1.370(4) . ?
C5 C6 1.381(4) . ?
C7 C12 1.385(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.381(4) . ?
C9 C10 1.372(5) . ?
C10 C11 1.365(4) . ?
C11 C12 1.381(4) . ?
C13 C14 1.349(3) . ?
C13 C18 1.496(2) . ?
C14 C15 1.532(3) . ?
C15 C16 1.435(3) . ?
C16 C17 1.390(3) . ?
C16 C24 1.399(3) . ?
C17 C27 1.395(3) . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C24 C25 1.364(3) . ?
C25 C26 1.425(3) . ?
C26 C27 1.390(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
C25 O3 C28 116.0(12) . . ?
C26 O4 C29 118.7(15) . . ?
C28A O3A C25 116.1(16) . . ?
C26 O4A C29A 118(2) . . ?
O1 P1 C13 113.12(9) . . ?
O1 P1 C1 113.11(10) . . ?
C13 P1 C1 102.93(10) . . ?
O1 P1 C7 113.10(10) . . ?
C13 P1 C7 107.07(10) . . ?
C1 P1 C7 106.77(9) . . ?
C14 N1 C17 110.34(16) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 P1 117.03(17) . . ?
C2 C1 P1 123.78(17) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.3(3) . . ?
C5 C4 C3 119.4(2) . . ?
C4 C5 C6 121.1(3) . . ?
C5 C6 C1 120.1(2) . . ?
C12 C7 C8 118.6(2) . . ?
C12 C7 P1 120.58(17) . . ?
C8 C7 P1 120.53(18) . . ?
C9 C8 C7 120.0(2) . . ?
C10 C9 C8 120.5(3) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 C12 119.8(3) . . ?
C11 C12 C7 120.9(2) . . ?
C14 C13 C18 121.60(18) . . ?
C14 C13 P1 122.75(16) . . ?
C18 C13 P1 115.60(13) . . ?
C13 C14 N1 130.04(19) . . ?
C13 C14 C15 124.09(18) . . ?
N1 C14 C15 105.87(16) . . ?
O2 C15 C16 128.4(11) . . ?
O2A C15 C16 127.2(13) . . ?
O2 C15 C14 125.8(11) . . ?
O2A C15 C14 126.9(13) . . ?
C16 C15 C14 105.04(16) . . ?
C17 C16 C24 121.72(18) . . ?
C17 C16 C15 108.54(17) . . ?
C24 C16 C15 129.69(18) . . ?
C16 C17 N1 110.18(17) . . ?
C16 C17 C27 120.64(18) . . ?
N1 C17 C27 129.16(18) . . ?
C19 C18 C23 120.0 . . ?
C19 C18 C13 119.99(13) . . ?
C23 C18 C13 119.98(13) . . ?
C18 C19 C20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C20 C21 C22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C25 C24 C16 118.60(19) . . ?
O3 C25 C24 126.1(6) . . ?
O3 C25 C26 113.6(6) . . ?
C24 C25 C26 119.85(18) . . ?
C24 C25 O3A 123.0(8) . . ?
C26 C25 O3A 116.5(8) . . ?
O4 C26 C27 124.6(6) . . ?
O4A C26 C27 123.7(9) . . ?
O4 C26 C25 113.2(6) . . ?
O4A C26 C25 113.9(9) . . ?
C27 C26 C25 121.80(18) . . ?
C26 C27 C17 117.39(18) . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.068



