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

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

data_221109huanhy1_0m
_database_code_depnum_ccdc_archive 'CCDC 2300782'
loop_
_audit_author_name
_audit_author_address
'haiyang huang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_audit_creation_date             2023-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H23 O3 P'
_chemical_formula_sum            'C28 H23 O3 P'
_chemical_formula_weight         438.43
_chemical_absolute_configuration ?
_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'
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   22.937(4)
_cell_length_b                   8.7952(15)
_cell_length_c                   11.1318(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2245.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4657
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.666
_cell_measurement_theta_min      2.550
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.8722.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13137
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.695
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Smart APEX-II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                4171
_reflns_number_total             5008
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1630 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5008
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.044
_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)+(0.0539P)²+0.1740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C14(H14), C11(H11), C17(H17), C13(H13), C7(H7), C4(H4),
 C26(H26), C20(H20), C5(H5), C22(H22), C6(H6), C19(H19), C24(H24), C23(H23),
 C25(H25)
2.b Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c), C28(H28a,H28b,H28c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.63741(3) 0.57591(8) 0.54622(8) 0.03631(18) Uani 1 1 d . . . . .
O1 O 0.60667(10) 0.6863(2) 0.4682(2) 0.0484(5) Uani 1 1 d . . . . .
O2 O 0.53058(11) 0.0054(3) 0.2136(3) 0.0604(7) Uani 1 1 d . . . . .
O3 O 0.88468(11) -0.0533(3) 0.3583(2) 0.0600(7) Uani 1 1 d . . . . .
C9 C 0.63679(12) 0.3037(3) 0.4048(3) 0.0357(6) Uani 1 1 d . . . . .
C16 C 0.78145(14) 0.2568(3) 0.3553(3) 0.0405(7) Uani 1 1 d . . . . .
H16 H 0.7631 0.3170 0.2979 0.049 Uiso 1 1 calc R U . . .
C12 C 0.56375(13) 0.1095(3) 0.2740(3) 0.0415(7) Uani 1 1 d . . . . .
C1 C 0.67167(12) 0.4111(3) 0.4772(3) 0.0360(6) Uani 1 1 d . . . . .
C3 C 0.74780(14) 0.5287(3) 0.5917(3) 0.0368(6) Uani 1 1 d . . . . .
C10 C 0.59496(13) 0.3594(3) 0.3265(3) 0.0417(7) Uani 1 1 d . . . . .
H10 H 0.5908 0.4640 0.3181 0.050 Uiso 1 1 calc R U . . .
C14 C 0.64046(13) 0.1454(3) 0.4175(3) 0.0401(7) Uani 1 1 d . . . . .
H14 H 0.6676 0.1040 0.4703 0.048 Uiso 1 1 calc R U . . .
C21 C 0.59069(13) 0.4941(3) 0.6591(3) 0.0410(7) Uani 1 1 d . . . . .
C8 C 0.70365(13) 0.6350(3) 0.6176(3) 0.0397(7) Uani 1 1 d . . . . .
C11 C 0.55899(14) 0.2641(3) 0.2603(3) 0.0451(7) Uani 1 1 d . . . . .
H11 H 0.5319 0.3048 0.2072 0.054 Uiso 1 1 calc R U . . .
C15 C 0.76967(12) 0.2811(3) 0.4759(3) 0.0350(6) Uani 1 1 d . . . . .
C17 C 0.81973(15) 0.1455(4) 0.3186(3) 0.0472(8) Uani 1 1 d . . . . .
H17 H 0.8274 0.1320 0.2372 0.057 Uiso 1 1 calc R U . . .
C13 C 0.60454(14) 0.0502(3) 0.3530(3) 0.0439(7) Uani 1 1 d . . . . .
H13 H 0.6077 -0.0546 0.3625 0.053 Uiso 1 1 calc R U . . .
C18 C 0.84687(14) 0.0537(3) 0.4030(3) 0.0431(7) Uani 1 1 d . . . . .
C2 C 0.72817(12) 0.4018(3) 0.5129(2) 0.0350(6) Uani 1 1 d . . . . .
C7 C 0.71440(15) 0.7603(4) 0.6883(4) 0.0516(9) Uani 1 1 d . . . . .
H7 H 0.6849 0.8300 0.7045 0.062 Uiso 1 1 calc R U . . .
C4 C 0.80287(14) 0.5525(4) 0.6379(3) 0.0468(8) Uani 1 1 d . . . . .
H4 H 0.8329 0.4850 0.6204 0.056 Uiso 1 1 calc R U . . .
C26 C 0.60537(16) 0.4866(4) 0.7788(4) 0.0574(9) Uani 1 1 d . . . . .
H26 H 0.6400 0.5303 0.8050 0.069 Uiso 1 1 calc R U . . .
C20 C 0.79803(16) 0.1892(4) 0.5587(3) 0.0518(8) Uani 1 1 d . . . . .
H20 H 0.7914 0.2047 0.6402 0.062 Uiso 1 1 calc R U . . .
C5 C 0.81310(16) 0.6782(4) 0.7110(4) 0.0565(9) Uani 1 1 d . . . . .
H5 H 0.8499 0.6926 0.7440 0.068 Uiso 1 1 calc R U . . .
C22 C 0.53839(15) 0.4277(4) 0.6215(4) 0.0560(9) Uani 1 1 d . . . . .
H22 H 0.5274 0.4317 0.5411 0.067 Uiso 1 1 calc R U . . .
C6 C 0.76964(17) 0.7812(4) 0.7350(4) 0.0605(10) Uani 1 1 d . . . . .
H6 H 0.7774 0.8653 0.7830 0.073 Uiso 1 1 calc R U . . .
C19 C 0.83598(16) 0.0751(4) 0.5232(3) 0.0521(9) Uani 1 1 d . . . . .
H19 H 0.8539 0.0135 0.5802 0.062 Uiso 1 1 calc R U . . .
C24 C 0.51822(19) 0.3482(4) 0.8231(5) 0.0701(12) Uani 1 1 d . . . . .
H24 H 0.4942 0.2982 0.8775 0.084 Uiso 1 1 calc R U . . .
C27 C 0.48545(19) 0.0611(5) 0.1362(4) 0.0741(12) Uani 1 1 d . . . . .
H27A H 0.5026 0.1149 0.0700 0.111 Uiso 1 1 calc R U . . .
H27B H 0.4605 0.1286 0.1805 0.111 Uiso 1 1 calc R U . . .
H27C H 0.4630 -0.0228 0.1063 0.111 Uiso 1 1 calc R U . . .
C23 C 0.50323(17) 0.3561(4) 0.7050(5) 0.0691(11) Uani 1 1 d . . . . .
H23 H 0.4684 0.3122 0.6799 0.083 Uiso 1 1 calc R U . . .
C25 C 0.5692(2) 0.4146(5) 0.8612(4) 0.0743(13) Uani 1 1 d . . . . .
H25 H 0.5794 0.4113 0.9419 0.089 Uiso 1 1 calc R U . . .
C28 C 0.9103(2) -0.1559(6) 0.4407(5) 0.0903(16) Uani 1 1 d . . . . .
H28A H 0.9371 -0.2212 0.3990 0.135 Uiso 1 1 calc R U . . .
H28B H 0.8804 -0.2163 0.4776 0.135 Uiso 1 1 calc R U . . .
H28C H 0.9308 -0.0999 0.5015 0.135 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 1.481(2) . ?
P1 C1 1.818(3) . ?
P1 C21 1.802(3) . ?
P1 C8 1.792(3) . ?
O2 C12 1.368(4) . ?
O2 C27 1.433(5) . ?
O3 C18 1.373(4) . ?
O3 C28 1.414(5) . ?
C9 C1 1.478(4) . ?
C9 C10 1.385(4) . ?
C9 C14 1.402(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.386(4) . ?
C16 C17 1.376(4) . ?
C12 C11 1.373(4) . ?
C12 C13 1.386(5) . ?
C1 C2 1.358(4) . ?
C3 C8 1.408(4) . ?
C3 C2 1.489(4) . ?
C3 C4 1.380(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.377(4) . ?
C21 C26 1.376(5) . ?
C21 C22 1.399(5) . ?
C8 C7 1.377(4) . ?
C11 H11 0.9300 . ?
C15 C2 1.484(4) . ?
C15 C20 1.388(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(5) . ?
C13 H13 0.9300 . ?
C18 C19 1.375(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(5) . ?
C26 H26 0.9300 . ?
C26 C25 1.390(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(5) . ?
C6 H6 0.9300 . ?
C19 H19 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.360(7) . ?
C24 C25 1.374(7) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C23 H23 0.9300 . ?
C25 H25 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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 C1 118.70(15) . . ?
O1 P1 C21 112.80(14) . . ?
O1 P1 C8 118.25(14) . . ?
C21 P1 C1 103.48(13) . . ?
C8 P1 C1 93.01(13) . . ?
C8 P1 C21 108.15(16) . . ?
C12 O2 C27 117.9(3) . . ?
C18 O3 C28 117.7(3) . . ?
C10 C9 C1 119.5(2) . . ?
C10 C9 C14 117.1(3) . . ?
C14 C9 C1 123.2(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C17 C16 C15 121.4(3) . . ?
O2 C12 C11 124.4(3) . . ?
O2 C12 C13 115.8(3) . . ?
C11 C12 C13 119.8(3) . . ?
C9 C1 P1 120.4(2) . . ?
C2 C1 P1 109.6(2) . . ?
C2 C1 C9 129.7(3) . . ?
C8 C3 C2 113.6(3) . . ?
C4 C3 C8 118.8(3) . . ?
C4 C3 C2 127.6(3) . . ?
C9 C10 H10 118.9 . . ?
C9 C10 C11 122.2(3) . . ?
C11 C10 H10 118.9 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
C26 C21 P1 123.3(3) . . ?
C26 C21 C22 118.7(3) . . ?
C22 C21 P1 117.9(3) . . ?
C3 C8 P1 109.0(2) . . ?
C7 C8 P1 129.7(2) . . ?
C7 C8 C3 121.3(3) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C16 C15 C2 120.3(3) . . ?
C16 C15 C20 117.6(3) . . ?
C20 C15 C2 122.1(3) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
O3 C18 C17 115.9(3) . . ?
O3 C18 C19 124.2(3) . . ?
C19 C18 C17 119.9(3) . . ?
C1 C2 C3 114.6(3) . . ?
C1 C2 C15 125.0(3) . . ?
C15 C2 C3 120.4(2) . . ?
C8 C7 H7 120.5 . . ?
C8 C7 C6 119.1(3) . . ?
C6 C7 H7 120.5 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C21 C26 H26 119.5 . . ?
C21 C26 C25 120.9(4) . . ?
C25 C26 H26 119.5 . . ?
C15 C20 H20 119.1 . . ?
C19 C20 C15 121.7(3) . . ?
C19 C20 H20 119.1 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.3(4) . . ?
C23 C22 H22 120.3 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.5(4) . . ?
C25 C24 H24 120.3 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.7(4) . . ?
C24 C23 H23 119.2 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.0 . . ?
O3 C28 H28A 109.5 . . ?
O3 C28 H28B 109.5 . . ?
O3 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -2.9(3) . . . . ?
P1 C1 C2 C15 179.3(2) . . . . ?
P1 C21 C26 C25 -176.3(3) . . . . ?
P1 C21 C22 C23 176.2(3) . . . . ?
P1 C8 C7 C6 179.2(3) . . . . ?
O1 P1 C1 C9 -57.9(3) . . . . ?
O1 P1 C1 C2 127.6(2) . . . . ?
O1 P1 C21 C26 -130.8(3) . . . . ?
O1 P1 C21 C22 52.9(3) . . . . ?
O1 P1 C8 C3 -127.2(2) . . . . ?
O1 P1 C8 C7 53.3(4) . . . . ?
O2 C12 C11 C10 179.9(3) . . . . ?
O2 C12 C13 C14 179.5(3) . . . . ?
O3 C18 C19 C20 178.4(3) . . . . ?
C9 C1 C2 C3 -176.7(3) . . . . ?
C9 C1 C2 C15 5.5(5) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C9 C14 C13 C12 -0.1(5) . . . . ?
C16 C15 C2 C1 57.8(4) . . . . ?
C16 C15 C2 C3 -119.9(3) . . . . ?
C16 C15 C20 C19 -1.2(5) . . . . ?
C16 C17 C18 O3 -179.5(3) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C1 P1 C21 C26 99.7(3) . . . . ?
C1 P1 C21 C22 -76.7(3) . . . . ?
C1 P1 C8 C3 -2.1(2) . . . . ?
C1 P1 C8 C7 178.3(3) . . . . ?
C1 C9 C10 C11 -176.9(3) . . . . ?
C1 C9 C14 C13 176.1(3) . . . . ?
C3 C8 C7 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 -1.8(6) . . . . ?
C10 C9 C1 P1 41.3(4) . . . . ?
C10 C9 C1 C2 -145.5(3) . . . . ?
C10 C9 C14 C13 1.1(5) . . . . ?
C14 C9 C1 P1 -133.6(3) . . . . ?
C14 C9 C1 C2 39.7(5) . . . . ?
C14 C9 C10 C11 -1.8(5) . . . . ?
C21 P1 C1 C9 67.9(3) . . . . ?
C21 P1 C1 C2 -106.6(2) . . . . ?
C21 P1 C8 C3 103.1(2) . . . . ?
C21 P1 C8 C7 -76.5(4) . . . . ?
C21 C26 C25 C24 0.7(6) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C8 P1 C1 C9 177.4(2) . . . . ?
C8 P1 C1 C2 2.9(2) . . . . ?
C8 P1 C21 C26 1.9(3) . . . . ?
C8 P1 C21 C22 -174.4(2) . . . . ?
C8 C3 C2 C1 1.3(4) . . . . ?
C8 C3 C2 C15 179.2(3) . . . . ?
C8 C3 C4 C5 1.5(5) . . . . ?
C8 C7 C6 C5 0.0(6) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C15 C20 C19 C18 1.3(6) . . . . ?
C17 C16 C15 C2 -180.0(3) . . . . ?
C17 C16 C15 C20 0.2(5) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
C13 C12 C11 C10 -0.3(5) . . . . ?
C2 C3 C8 P1 1.0(3) . . . . ?
C2 C3 C8 C7 -179.4(3) . . . . ?
C2 C3 C4 C5 -179.7(3) . . . . ?
C2 C15 C20 C19 178.9(3) . . . . ?
C4 C3 C8 P1 179.9(2) . . . . ?
C4 C3 C8 C7 -0.5(5) . . . . ?
C4 C3 C2 C1 -177.5(3) . . . . ?
C4 C3 C2 C15 0.4(4) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C26 C21 C22 C23 -0.3(5) . . . . ?
C20 C15 C2 C1 -122.4(4) . . . . ?
C20 C15 C2 C3 59.9(4) . . . . ?
C22 C21 C26 C25 0.0(5) . . . . ?
C27 O2 C12 C11 -3.9(5) . . . . ?
C27 O2 C12 C13 176.4(3) . . . . ?
C23 C24 C25 C26 -1.2(6) . . . . ?
C25 C24 C23 C22 0.9(6) . . . . ?
C28 O3 C18 C17 -175.9(4) . . . . ?
C28 O3 C18 C19 5.4(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_221119huanghy2_0m
_database_code_depnum_ccdc_archive 'CCDC 2300783'
loop_
_audit_author_name
_audit_author_address
'haiyang huang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_audit_creation_date             2023-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H25 O P, 1[HCCl3]'
_chemical_formula_sum            'C28 H25 O P'
_chemical_formula_weight         408.45
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.961(2)
_cell_length_b                   9.9168(16)
_cell_length_c                   21.452(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.577(3)
_cell_angle_gamma                90
_cell_volume                     2846.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2409
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.235
_cell_measurement_theta_min      2.280
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0886 before and 0.0341 after correction.
The Ratio of minimum to maximum transmission is 0.9032.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.953
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.1130
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16736
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Smart APEX-II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2888
_reflns_number_total             6460
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6460
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      0.836
_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)+(0.0666P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C12(H12), C15(H15), C3(H3), C5(H5), C2(H2), C22(H22),
 C9(H9), C28(H28), C18(H18), C10(H10), C19(H19), C20(H20), C27(H27), C24(H24),
 C21(H21), C26(H26), C25(H25)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.53464(4) 0.37313(6) 0.72827(3) 0.0531(2) Uani 1 1 d . . . . .
O1 O 0.57362(12) 0.37006(18) 0.67079(9) 0.0733(5) Uani 1 1 d . . . . .
C1 C 0.36662(14) 0.4758(2) 0.76216(10) 0.0408(5) Uani 1 1 d . . . . .
C8 C 0.26651(16) 0.5169(2) 0.61049(11) 0.0471(6) Uani 1 1 d . . . . .
C16 C 0.40763(15) 0.4370(2) 0.70771(11) 0.0438(5) Uani 1 1 d . . . . .
C6 C 0.33092(15) 0.3811(2) 0.79762(11) 0.0471(6) Uani 1 1 d . . . . .
H6 H 0.3307 0.2902 0.7869 0.057 Uiso 1 1 calc R U . . .
C13 C 0.18762(16) 0.5359(2) 0.63738(11) 0.0496(6) Uani 1 1 d . . . . .
H13 H 0.1944 0.5075 0.6797 0.059 Uiso 1 1 calc R U . . .
C4 C 0.29481(17) 0.5539(3) 0.86730(11) 0.0540(6) Uani 1 1 d . U . . .
C17 C 0.53624(16) 0.2069(2) 0.76237(12) 0.0511(6) Uani 1 1 d . . . . .
C12 C 0.10001(17) 0.5958(2) 0.60248(12) 0.0566(6) Uani 1 1 d . . . . .
H12 H 0.0489 0.6068 0.6219 0.068 Uiso 1 1 calc R U . . .
C11 C 0.08519(19) 0.6405(2) 0.53914(13) 0.0622(7) Uani 1 1 d . . . . .
C15 C 0.36374(17) 0.4582(2) 0.64423(12) 0.0501(6) Uani 1 1 d . . . . .
H15 H 0.4014 0.4311 0.6170 0.060 Uiso 1 1 calc R U . . .
C3 C 0.33103(17) 0.6487(2) 0.83173(12) 0.0584(6) Uani 1 1 d . U . . .
H3 H 0.3318 0.7394 0.8429 0.070 Uiso 1 1 calc R U . . .
C23 C 0.60838(16) 0.4787(2) 0.79174(13) 0.0552(7) Uani 1 1 d . . . . .
C5 C 0.29543(16) 0.4212(3) 0.84904(12) 0.0554(6) Uani 1 1 d . . . . .
H5 H 0.2713 0.3560 0.8718 0.066 Uiso 1 1 calc R U . . .
C2 C 0.36593(16) 0.6103(2) 0.78015(12) 0.0523(6) Uani 1 1 d . . . . .
H2 H 0.3894 0.6758 0.7571 0.063 Uiso 1 1 calc R U . . .
C22 C 0.46012(18) 0.1154(3) 0.73578(13) 0.0604(7) Uani 1 1 d . . . . .
H22 H 0.4028 0.1451 0.7048 0.073 Uiso 1 1 calc R U . . .
C9 C 0.2501(2) 0.5564(3) 0.54587(12) 0.0688(8) Uani 1 1 d . . . . .
H9 H 0.2994 0.5414 0.5253 0.083 Uiso 1 1 calc R U . . .
C28 C 0.59654(19) 0.4851(3) 0.85386(14) 0.0671(7) Uani 1 1 d . . . . .
H28 H 0.5485 0.4316 0.8642 0.081 Uiso 1 1 calc R U . . .
C18 C 0.62008(17) 0.1582(3) 0.80908(13) 0.0662(7) Uani 1 1 d . . . . .
H18 H 0.6721 0.2167 0.8286 0.079 Uiso 1 1 calc R U . . .
C10 C 0.1614(2) 0.6175(3) 0.51198(13) 0.0771(8) Uani 1 1 d . . . . .
H10 H 0.1533 0.6439 0.4692 0.092 Uiso 1 1 calc R U . . .
C19 C 0.6268(2) 0.0235(3) 0.82675(15) 0.0782(8) Uani 1 1 d . . . . .
H19 H 0.6837 -0.0075 0.8576 0.094 Uiso 1 1 calc R U . . .
C20 C 0.5516(2) -0.0638(3) 0.79968(15) 0.0779(9) Uani 1 1 d . . . . .
H20 H 0.5568 -0.1541 0.8119 0.093 Uiso 1 1 calc R U . . .
C7 C 0.2559(2) 0.5971(3) 0.92333(13) 0.0859(9) Uani 1 1 d . . . . .
H7A H 0.3112 0.6114 0.9614 0.129 Uiso 1 1 calc R U . . .
H7B H 0.2133 0.5279 0.9320 0.129 Uiso 1 1 calc R U . . .
H7C H 0.2187 0.6793 0.9122 0.129 Uiso 1 1 calc R U . . .
C27 C 0.6553(2) 0.5702(3) 0.90060(15) 0.0832(9) Uani 1 1 d . . . . .
H27 H 0.6460 0.5746 0.9418 0.100 Uiso 1 1 calc R U . . .
C24 C 0.6817(2) 0.5588(3) 0.77839(16) 0.0763(8) Uani 1 1 d . . . . .
H24 H 0.6913 0.5559 0.7372 0.092 Uiso 1 1 calc R U . . .
C14 C -0.0100(2) 0.7123(3) 0.50340(14) 0.0917(10) Uani 1 1 d . . . . .
H14A H -0.0646 0.6776 0.5175 0.138 Uiso 1 1 calc R U . . .
H14B H -0.0232 0.6978 0.4575 0.138 Uiso 1 1 calc R U . . .
H14C H -0.0029 0.8072 0.5125 0.138 Uiso 1 1 calc R U . . .
C21 C 0.4675(2) -0.0172(3) 0.75402(15) 0.0732(8) Uani 1 1 d . . . . .
H21 H 0.4155 -0.0763 0.7355 0.088 Uiso 1 1 calc R U . . .
C26 C 0.7281(2) 0.6487(3) 0.8859(2) 0.0988(11) Uani 1 1 d . . . . .
H26 H 0.7683 0.7052 0.9172 0.119 Uiso 1 1 calc R U . . .
C25 C 0.7403(2) 0.6423(3) 0.8249(2) 0.1026(12) Uani 1 1 d . . . . .
H25 H 0.7889 0.6952 0.8148 0.123 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 1.4832(17) . ?
P1 C16 1.815(2) . ?
P1 C17 1.801(2) . ?
P1 C23 1.792(3) . ?
C1 C16 1.490(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.390(3) . ?
C8 C13 1.394(3) . ?
C8 C15 1.464(3) . ?
C8 C9 1.395(3) . ?
C16 C15 1.341(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.374(3) . ?
C4 C3 1.394(3) . ?
C4 C5 1.374(3) . ?
C4 C7 1.515(3) . ?
C17 C22 1.390(3) . ?
C17 C18 1.392(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.387(3) . ?
C11 C10 1.370(4) . ?
C11 C14 1.510(3) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.384(3) . ?
C23 C28 1.390(3) . ?
C23 C24 1.389(3) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.368(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C28 H28 0.9300 . ?
C28 C27 1.386(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C10 H10 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.357(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C27 H27 0.9300 . ?
C27 C26 1.386(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.372(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C21 H21 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.369(4) . ?
C25 H25 0.9300 . ?

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 C16 111.71(10) . . ?
O1 P1 C17 110.72(10) . . ?
O1 P1 C23 112.10(11) . . ?
C17 P1 C16 108.43(10) . . ?
C23 P1 C16 106.89(11) . . ?
C23 P1 C17 106.76(11) . . ?
C6 C1 C16 122.23(19) . . ?
C6 C1 C2 117.7(2) . . ?
C2 C1 C16 120.01(19) . . ?
C13 C8 C15 125.4(2) . . ?
C13 C8 C9 116.6(2) . . ?
C9 C8 C15 118.0(2) . . ?
C1 C16 P1 117.83(16) . . ?
C15 C16 P1 115.67(17) . . ?
C15 C16 C1 126.1(2) . . ?
C1 C6 H6 119.8 . . ?
C1 C6 C5 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C3 C4 C7 120.8(2) . . ?
C5 C4 C3 117.2(2) . . ?
C5 C4 C7 122.0(2) . . ?
C22 C17 P1 120.76(18) . . ?
C22 C17 C18 117.1(2) . . ?
C18 C17 P1 121.35(19) . . ?
C13 C12 H12 118.9 . . ?
C13 C12 C11 122.2(2) . . ?
C11 C12 H12 118.9 . . ?
C12 C11 C14 120.8(3) . . ?
C10 C11 C12 116.5(2) . . ?
C10 C11 C14 122.7(3) . . ?
C8 C15 H15 114.5 . . ?
C16 C15 C8 130.9(2) . . ?
C16 C15 H15 114.5 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C28 C23 P1 123.75(18) . . ?
C24 C23 P1 118.4(2) . . ?
C24 C23 C28 117.9(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 C6 122.2(2) . . ?
C4 C5 H5 118.9 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.6(2) . . ?
C21 C22 H22 119.2 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.9(3) . . ?
C27 C28 H28 119.6 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C11 C10 C9 122.4(2) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.9(3) . . ?
C26 C27 H27 120.1 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.1(3) . . ?
C25 C24 H24 119.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C27 C26 H26 120.3 . . ?
C25 C26 C27 119.4(3) . . ?
C25 C26 H26 120.3 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H25 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C16 C15 C8 -175.16(19) . . . . ?
P1 C17 C22 C21 169.5(2) . . . . ?
P1 C17 C18 C19 -169.0(2) . . . . ?
P1 C23 C28 C27 -179.2(2) . . . . ?
P1 C23 C24 C25 179.7(2) . . . . ?
O1 P1 C16 C1 -166.24(15) . . . . ?
O1 P1 C16 C15 6.8(2) . . . . ?
O1 P1 C17 C22 -81.7(2) . . . . ?
O1 P1 C17 C18 88.2(2) . . . . ?
O1 P1 C23 C28 -170.96(19) . . . . ?
O1 P1 C23 C24 9.0(2) . . . . ?
C1 C16 C15 C8 -2.8(4) . . . . ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C8 C13 C12 C11 -0.1(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C16 P1 C17 C22 41.2(2) . . . . ?
C16 P1 C17 C18 -148.94(19) . . . . ?
C16 P1 C23 C28 66.3(2) . . . . ?
C16 P1 C23 C24 -113.7(2) . . . . ?
C16 C1 C6 C5 178.49(19) . . . . ?
C16 C1 C2 C3 -178.1(2) . . . . ?
C6 C1 C16 P1 -79.3(2) . . . . ?
C6 C1 C16 C15 108.5(3) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C13 C8 C15 C16 -15.9(4) . . . . ?
C13 C8 C9 C10 3.2(4) . . . . ?
C13 C12 C11 C10 2.3(4) . . . . ?
C13 C12 C11 C14 -176.9(2) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C17 P1 C16 C1 71.48(18) . . . . ?
C17 P1 C16 C15 -115.52(19) . . . . ?
C17 P1 C23 C28 -49.6(2) . . . . ?
C17 P1 C23 C24 130.40(19) . . . . ?
C17 C22 C21 C20 0.0(4) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C12 C11 C10 C9 -1.7(4) . . . . ?
C15 C8 C13 C12 177.9(2) . . . . ?
C15 C8 C9 C10 -177.4(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C23 P1 C16 C1 -43.27(19) . . . . ?
C23 P1 C16 C15 129.73(19) . . . . ?
C23 P1 C17 C22 156.07(18) . . . . ?
C23 P1 C17 C18 -34.1(2) . . . . ?
C23 C28 C27 C26 -1.0(4) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C2 C1 C16 P1 98.8(2) . . . . ?
C2 C1 C16 C15 -73.3(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C22 C17 C18 C19 1.2(4) . . . . ?
C9 C8 C13 C12 -2.7(3) . . . . ?
C9 C8 C15 C16 164.8(2) . . . . ?
C28 C23 C24 C25 -0.4(4) . . . . ?
C28 C27 C26 C25 0.8(5) . . . . ?
C18 C17 C22 C21 -0.8(4) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C7 C4 C3 C2 -179.5(2) . . . . ?
C7 C4 C5 C6 179.9(2) . . . . ?
C27 C26 C25 C24 -0.3(5) . . . . ?
C24 C23 C28 C27 0.8(4) . . . . ?
C14 C11 C10 C9 177.4(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.591 0.000 403.8 128.3 '2.2 HCCl3'
2 0.500 -0.552 0.500 403.8 128.3 '2.2 HCCl3'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
