# 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_hddx1205
_database_code_depnum_ccdc_archive 'CCDC 1981157'
loop_
_audit_author_name
_audit_author_address
Penglifen
;Hunan University
China
;
_audit_update_record             
;
2021-12-07 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_audit_creation_date             2018-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H20 N O3 P'
_chemical_formula_sum            'C29 H20 N O3 P'
_chemical_formula_weight         461.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5429(11)
_cell_length_b                   10.9205(10)
_cell_length_c                   11.7539(12)
_cell_angle_alpha                65.707(10)
_cell_angle_beta                 75.725(9)
_cell_angle_gamma                64.564(10)
_cell_volume                     1109.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.0810
_cell_measurement_theta_min      2.4480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10135
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.147
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  40.00   1.00    1.00    --   11.74 -57.00 -60.00  100
  2  ω    -21.00  88.00   1.00    1.00    --   11.74  77.00-150.00  109
  3  ω    -16.00  85.00   1.00    1.00    --   11.74  57.00  90.00  101
  4  ω     34.00  99.00   1.00    1.00    --   11.74-178.00 -60.00   65
  5  ω    -16.00   9.00   1.00    1.00    --   11.74  57.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0482762000
_diffrn_orient_matrix_UB_12      -0.0259444000
_diffrn_orient_matrix_UB_13      -0.0061076000
_diffrn_orient_matrix_UB_21      0.0112907000
_diffrn_orient_matrix_UB_22      0.0287571000
_diffrn_orient_matrix_UB_23      -0.0661651000
_diffrn_orient_matrix_UB_31      0.0559678000
_diffrn_orient_matrix_UB_32      -0.0662619000
_diffrn_orient_matrix_UB_33      0.0005431000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3375
_reflns_number_total             3901
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.4707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C28(H28), C19(H19), C6(H6), C25(H25), C27(H27), C26(H26), C2(H2A),
 C17(H17), C4(H4), C14(H14), C5(H5), C16(H16), C23(H23), C15(H15), C20(H20),
 C3(H3), C21(H21), C22(H22)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.17823(5) 0.23297(5) 0.28763(4) 0.01840(14) Uani 1 1 d . . . . .
O1 O 0.51668(12) 0.47694(13) 0.21385(12) 0.0208(3) Uani 1 1 d . . . . .
O2 O 0.39453(13) 0.10569(14) 0.09947(13) 0.0276(3) Uani 1 1 d . . . . .
H2 H 0.317538 0.102816 0.133761 0.041 Uiso 1 1 calc GR . . . .
O3 O 0.15516(13) 0.14472(13) 0.23102(12) 0.0247(3) Uani 1 1 d . . . . .
N1 N 0.32558(14) 0.42771(15) 0.32188(14) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.40537(17) 0.49920(18) 0.30247(17) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.55227(18) 0.21958(19) 0.06824(16) 0.0206(4) Uani 1 1 d . . . . .
C13 C 0.34037(17) 0.25911(18) 0.21765(16) 0.0176(4) Uani 1 1 d . . . . .
C24 C 0.18555(17) 0.14895(18) 0.45417(17) 0.0181(4) Uani 1 1 d . . . . .
C12 C 0.42460(18) 0.19532(18) 0.13115(17) 0.0201(4) Uani 1 1 d . . . . .
C9 C 0.50306(18) 0.38009(18) 0.17571(17) 0.0186(4) Uani 1 1 d . . . . .
C18 C 0.03703(17) 0.40791(19) 0.25920(17) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.59237(18) 0.31723(18) 0.08863(17) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.38604(17) 0.35206(18) 0.24013(17) 0.0183(4) Uani 1 1 d . . . . .
C29 C 0.30030(18) 0.11082(18) 0.51611(17) 0.0207(4) Uani 1 1 d . . . . .
H29 H 0.377286 0.135386 0.471935 0.025 Uiso 1 1 calc R . . . .
C1 C 0.39011(18) 0.59535(18) 0.36487(17) 0.0207(4) Uani 1 1 d . . . . .
C28 C 0.29996(19) 0.03610(19) 0.64384(18) 0.0235(4) Uani 1 1 d . . . . .
H28 H 0.377241 0.009904 0.685357 0.028 Uiso 1 1 calc R . . . .
C19 C 0.00963(18) 0.4935(2) 0.32894(18) 0.0243(4) Uani 1 1 d . . . . .
H19 H 0.062375 0.459573 0.395910 0.029 Uiso 1 1 calc R . . . .
C6 C 0.30343(18) 0.5900(2) 0.47554(18) 0.0241(4) Uani 1 1 d . . . . .
H6 H 0.254045 0.528199 0.506409 0.029 Uiso 1 1 calc R . . . .
C25 C 0.07043(18) 0.11204(19) 0.52180(18) 0.0239(4) Uani 1 1 d . . . . .
H25 H -0.006912 0.137928 0.480488 0.029 Uiso 1 1 calc R . . . .
C27 C 0.18515(19) -0.00004(19) 0.71044(18) 0.0253(4) Uani 1 1 d . . . . .
H27 H 0.185418 -0.049669 0.796440 0.030 Uiso 1 1 calc R . . . .
C26 C 0.07015(19) 0.0376(2) 0.64923(18) 0.0267(4) Uani 1 1 d . . . . .
H26 H -0.006678 0.012876 0.693656 0.032 Uiso 1 1 calc R . . . .
C2 C 0.4613(2) 0.6902(2) 0.31850(19) 0.0264(4) Uani 1 1 d . . . . .
H2A H 0.519609 0.694505 0.244454 0.032 Uiso 1 1 calc R . . . .
C17 C 0.71602(19) 0.3417(2) 0.02398(17) 0.0254(4) Uani 1 1 d . . . . .
H17 H 0.741463 0.407233 0.035447 0.030 Uiso 1 1 calc R . . . .
C4 C 0.3611(2) 0.7702(2) 0.4930(2) 0.0300(5) Uani 1 1 d . . . . .
H4 H 0.351752 0.828643 0.536362 0.036 Uiso 1 1 calc R . . . .
C14 C 0.6404(2) 0.1466(2) -0.01343(18) 0.0270(4) Uani 1 1 d . . . . .
H14 H 0.616539 0.081200 -0.026878 0.032 Uiso 1 1 calc R . . . .
C5 C 0.29073(19) 0.6760(2) 0.53937(19) 0.0278(5) Uani 1 1 d . . . . .
H5 H 0.234227 0.670745 0.614425 0.033 Uiso 1 1 calc R . . . .
C16 C 0.7984(2) 0.2694(2) -0.05531(19) 0.0312(5) Uani 1 1 d . . . . .
H16 H 0.879840 0.285833 -0.097534 0.037 Uiso 1 1 calc R . . . .
C23 C -0.0441(2) 0.4584(2) 0.16086(19) 0.0300(5) Uani 1 1 d . . . . .
H23 H -0.027326 0.400934 0.114255 0.036 Uiso 1 1 calc R . . . .
C15 C 0.7609(2) 0.1707(2) -0.07344(19) 0.0319(5) Uani 1 1 d . . . . .
H15 H 0.818458 0.121020 -0.126765 0.038 Uiso 1 1 calc R . . . .
C20 C -0.09629(19) 0.6299(2) 0.2993(2) 0.0306(5) Uani 1 1 d . . . . .
H20 H -0.114255 0.687330 0.346203 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4452(2) 0.7774(2) 0.3824(2) 0.0326(5) Uani 1 1 d . . . . .
H3 H 0.491615 0.841881 0.350545 0.039 Uiso 1 1 calc R . . . .
C21 C -0.1749(2) 0.6804(2) 0.2005(2) 0.0367(5) Uani 1 1 d . . . . .
H21 H -0.244788 0.772520 0.179805 0.044 Uiso 1 1 calc R . . . .
C22 C -0.1500(2) 0.5945(2) 0.1324(2) 0.0394(6) Uani 1 1 d . . . . .
H22 H -0.204705 0.628063 0.066880 0.047 Uiso 1 1 calc R . . . .


_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 O3 1.4965(13) . ?
P1 C13 1.7924(17) . ?
P1 C24 1.7932(18) . ?
P1 C18 1.8040(18) . ?
O1 C7 1.372(2) . ?
O1 C9 1.376(2) . ?
O2 C12 1.350(2) . ?
N1 C7 1.301(2) . ?
N1 C8 1.382(2) . ?
C7 C1 1.448(3) . ?
C11 C12 1.443(3) . ?
C11 C10 1.421(3) . ?
C11 C14 1.405(3) . ?
C13 C12 1.383(3) . ?
C13 C8 1.427(2) . ?
C24 C29 1.385(2) . ?
C24 C25 1.396(2) . ?
C9 C10 1.398(3) . ?
C9 C8 1.365(2) . ?
C18 C19 1.383(3) . ?
C18 C23 1.389(3) . ?
C10 C17 1.411(3) . ?
C29 C28 1.383(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.390(2) . ?
C28 C27 1.387(3) . ?
C19 C20 1.387(3) . ?
C6 C5 1.374(3) . ?
C25 C26 1.379(3) . ?
C27 C26 1.384(3) . ?
C2 C3 1.374(3) . ?
C17 C16 1.365(3) . ?
C4 C5 1.378(3) . ?
C4 C3 1.375(3) . ?
C14 C15 1.369(3) . ?
C16 C15 1.400(3) . ?
C23 C22 1.385(3) . ?
C20 C21 1.376(3) . ?
C21 C22 1.375(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
O3 P1 C13 108.80(8) . . ?
O3 P1 C24 112.53(8) . . ?
O3 P1 C18 110.97(8) . . ?
C13 P1 C18 108.56(8) . . ?
C24 P1 C13 109.16(8) . . ?
C24 P1 C18 106.75(9) . . ?
C7 O1 C9 103.57(13) . . ?
C7 N1 C8 104.19(15) . . ?
O1 C7 C1 117.98(15) . . ?
N1 C7 O1 114.74(16) . . ?
N1 C7 C1 127.27(17) . . ?
C10 C11 C12 120.56(17) . . ?
C14 C11 C12 120.98(17) . . ?
C14 C11 C10 118.46(17) . . ?
C12 C13 P1 120.55(13) . . ?
C12 C13 C8 116.10(16) . . ?
C8 C13 P1 123.22(14) . . ?
C29 C24 P1 124.23(14) . . ?
C29 C24 C25 119.49(17) . . ?
C25 C24 P1 116.12(13) . . ?
O2 C12 C11 114.93(16) . . ?
O2 C12 C13 122.91(16) . . ?
C13 C12 C11 122.16(16) . . ?
O1 C9 C10 127.43(15) . . ?
C8 C9 O1 107.91(16) . . ?
C8 C9 C10 124.65(17) . . ?
C19 C18 P1 122.66(13) . . ?
C19 C18 C23 119.51(17) . . ?
C23 C18 P1 117.81(15) . . ?
C9 C10 C11 115.03(16) . . ?
C9 C10 C17 125.39(17) . . ?
C17 C10 C11 119.57(18) . . ?
N1 C8 C13 129.04(16) . . ?
C9 C8 N1 109.58(15) . . ?
C9 C8 C13 121.37(17) . . ?
C28 C29 C24 119.75(17) . . ?
C6 C1 C7 118.48(16) . . ?
C6 C1 C2 119.48(18) . . ?
C2 C1 C7 122.03(17) . . ?
C29 C28 C27 120.44(16) . . ?
C18 C19 C20 120.15(18) . . ?
C5 C6 C1 119.89(18) . . ?
C26 C25 C24 120.71(16) . . ?
C26 C27 C28 120.15(17) . . ?
C25 C26 C27 119.45(17) . . ?
C3 C2 C1 119.78(19) . . ?
C16 C17 C10 120.21(19) . . ?
C3 C4 C5 119.68(19) . . ?
C15 C14 C11 120.73(19) . . ?
C6 C5 C4 120.50(19) . . ?
C17 C16 C15 120.36(19) . . ?
C22 C23 C18 119.8(2) . . ?
C14 C15 C16 120.6(2) . . ?
C21 C20 C19 120.1(2) . . ?
C4 C3 C2 120.64(19) . . ?
C22 C21 C20 119.98(18) . . ?
C21 C22 C23 120.38(19) . . ?

_olex2_date_sample_data_collection 2018-12-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.632
