# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 
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data_cxy1119_0m
_database_code_depnum_ccdc_archive 'CCDC 1977604'
loop_
_audit_author_name
_audit_author_address
'Jun WANG'
;Southern University of Science and Technology 
China
;
_audit_update_record             
;
2020-01-14 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_audit_creation_date             2020-01-06
_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         'C22 H21 O2 P'
_chemical_formula_sum            'C22 H21 O2 P'
_chemical_formula_weight         348.36
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.0977(4)
_cell_length_b                   8.3134(6)
_cell_length_c                   18.1062(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.792(2)
_cell_angle_gamma                90
_cell_volume                     909.38(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1294 before and 0.0620 after correction. The Ratio of minimum to maximum transmission is 0.6873. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.692
_diffrn_reflns_theta_min         2.271
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5262
_reflns_number_total             5613
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.429
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.077
_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)+(0.0796P)²+0.4168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21)
2.c X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 -0.59907(9) -0.62423(7) -0.82843(3) 0.01126(14) Uani 1 1 d . . . . .
O2 O -0.7684(3) -0.7526(2) -0.83341(11) 0.0158(4) Uani 1 1 d . . . . .
O1 O -0.4313(3) -0.6367(2) -0.88832(10) 0.0147(3) Uani 1 1 d . . . . .
C22 C -0.2088(4) -0.5902(4) -0.73703(16) 0.0214(6) Uani 1 1 d . . . . .
H22A H -0.118274 -0.575390 -0.690544 0.026 Uiso 1 1 calc R . . . .
H22B H -0.144583 -0.588909 -0.781985 0.026 Uiso 1 1 calc R . . . .
C1 C -0.8948(4) -0.1250(4) -0.88335(16) 0.0212(5) Uani 1 1 d . . . . .
H1 H -0.956018 -0.021927 -0.895923 0.025 Uiso 1 1 calc R . . . .
C2 C -0.6927(4) -0.1377(3) -0.83832(15) 0.0185(5) Uani 1 1 d . . . . .
H2 H -0.616739 -0.043395 -0.819519 0.022 Uiso 1 1 calc R . . . .
C3 C -0.6009(4) -0.2885(3) -0.82059(15) 0.0167(5) Uani 1 1 d . . . . .
H3 H -0.461822 -0.296905 -0.790069 0.020 Uiso 1 1 calc R . . . .
C4 C -0.7134(4) -0.4277(3) -0.84770(14) 0.0120(4) Uani 1 1 d . . . . .
C5 C -0.4267(4) -0.6130(4) -0.73919(13) 0.0136(4) Uani 1 1 d . . . . .
C6 C -0.5316(4) -0.6155(4) -0.66960(13) 0.0136(4) Uani 1 1 d . . . . .
C7 C -0.6956(4) -0.7264(3) -0.65749(15) 0.0147(5) Uani 1 1 d . . . . .
H7 H -0.748628 -0.800739 -0.695610 0.018 Uiso 1 1 calc R . . . .
C8 C -0.7818(4) -0.7288(3) -0.59018(15) 0.0148(5) Uani 1 1 d . . . . .
H8 H -0.890767 -0.806672 -0.582741 0.018 Uiso 1 1 calc R . . . .
C9 C -0.7115(4) -0.6191(4) -0.53312(13) 0.0141(4) Uani 1 1 d . . . . .
C10 C -0.8024(4) -0.6206(4) -0.46089(13) 0.0152(4) Uani 1 1 d . . . . .
C11 C -0.6839(5) -0.5509(4) -0.39733(16) 0.0207(5) Uani 1 1 d . . . . .
H11 H -0.544831 -0.502016 -0.400668 0.025 Uiso 1 1 calc R . . . .
C12 C -0.7661(5) -0.5519(4) -0.32933(16) 0.0253(6) Uani 1 1 d . . . . .
H12 H -0.683599 -0.502735 -0.287027 0.030 Uiso 1 1 calc R . . . .
C13 C -0.9668(5) -0.6240(5) -0.32283(15) 0.0266(6) Uani 1 1 d . . . . .
H13 H -1.021853 -0.625789 -0.276209 0.032 Uiso 1 1 calc R . . . .
C14 C -1.0078(5) -0.2625(4) -0.9101(2) 0.0265(7) Uani 1 1 d . . . . .
H14 H -1.146369 -0.253567 -0.940866 0.032 Uiso 1 1 calc R . . . .
C15 C -0.9179(5) -0.4136(3) -0.89180(17) 0.0199(5) Uani 1 1 d . . . . .
H15 H -0.996677 -0.507625 -0.909517 0.024 Uiso 1 1 calc R . . . .
C16 C -0.3245(4) -0.7915(3) -0.89810(16) 0.0162(5) Uani 1 1 d . . . . .
H16A H -0.332144 -0.859988 -0.853792 0.019 Uiso 1 1 calc R . . . .
H16B H -0.166582 -0.774091 -0.903132 0.019 Uiso 1 1 calc R . . . .
C17 C -0.4381(5) -0.8744(4) -0.96647(16) 0.0221(6) Uani 1 1 d . . . . .
H17A H -0.436320 -0.804172 -1.009851 0.033 Uiso 1 1 calc GR . . . .
H17B H -0.591566 -0.898288 -0.959830 0.033 Uiso 1 1 calc GR . . . .
H17C H -0.360451 -0.974893 -0.974341 0.033 Uiso 1 1 calc GR . . . .
C18 C -0.4606(5) -0.5056(3) -0.61289(16) 0.0181(5) Uani 1 1 d . . . . .
H18 H -0.350325 -0.428649 -0.620147 0.022 Uiso 1 1 calc R . . . .
C19 C -0.5489(5) -0.5075(3) -0.54617(15) 0.0184(5) Uani 1 1 d . . . . .
H19 H -0.498048 -0.431418 -0.508547 0.022 Uiso 1 1 calc R . . . .
C20 C -1.0870(6) -0.6936(5) -0.38532(18) 0.0276(6) Uani 1 1 d . . . . .
H20 H -1.225030 -0.743486 -0.381307 0.033 Uiso 1 1 calc R . . . .
C21 C -1.0069(5) -0.6912(4) -0.45401(16) 0.0216(5) Uani 1 1 d . . . . .
H21 H -1.092090 -0.737898 -0.496441 0.026 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 O2 1.479(2) . ?
P1 O1 1.5921(18) . ?
P1 C4 1.792(2) . ?
P1 C5 1.806(2) . ?
O1 C16 1.463(3) . ?
C22 H22A 0.9500 . ?
C22 H22B 0.9500 . ?
C22 C5 1.337(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(4) . ?
C1 C14 1.388(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(4) . ?
C4 C15 1.392(4) . ?
C5 C6 1.488(3) . ?
C6 C7 1.399(4) . ?
C6 C18 1.399(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.401(4) . ?
C9 C10 1.488(3) . ?
C9 C19 1.401(4) . ?
C10 C11 1.399(4) . ?
C10 C21 1.399(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(5) . ?
C13 H13 0.9500 . ?
C13 C20 1.388(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.502(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.388(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.396(4) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O1 114.77(11) . . ?
O2 P1 C4 113.35(12) . . ?
O2 P1 C5 114.12(12) . . ?
O1 P1 C4 101.30(11) . . ?
O1 P1 C5 105.24(11) . . ?
C4 P1 C5 106.89(13) . . ?
C16 O1 P1 118.52(17) . . ?
H22A C22 H22B 120.0 . . ?
C5 C22 H22A 120.0 . . ?
C5 C22 H22B 120.0 . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C14 120.1(3) . . ?
C14 C1 H1 119.9 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 P1 121.77(19) . . ?
C15 C4 P1 118.88(19) . . ?
C15 C4 C3 119.3(2) . . ?
C22 C5 P1 119.3(2) . . ?
C22 C5 C6 121.1(2) . . ?
C6 C5 P1 119.46(16) . . ?
C7 C6 C5 122.7(2) . . ?
C18 C6 C5 119.1(2) . . ?
C18 C6 C7 118.2(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.5(2) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 121.9(2) . . ?
C19 C9 C8 117.4(2) . . ?
C19 C9 C10 120.7(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 C21 117.9(2) . . ?
C21 C10 C9 121.6(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C20 119.2(3) . . ?
C20 C13 H13 120.4 . . ?
C1 C14 H14 120.0 . . ?
C1 C14 C15 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C4 C15 C14 120.4(3) . . ?
C4 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O1 C16 H16A 109.7 . . ?
O1 C16 H16B 109.7 . . ?
O1 C16 C17 109.9(2) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18 119.5 . . ?
C19 C18 C6 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C9 C19 H19 119.3 . . ?
C18 C19 C9 121.4(2) . . ?
C18 C19 H19 119.3 . . ?
C13 C20 H20 119.7 . . ?
C13 C20 C21 120.7(3) . . ?
C21 C20 H20 119.7 . . ?
C10 C21 H21 119.7 . . ?
C20 C21 C10 120.6(3) . . ?
C20 C21 H21 119.7 . . ?

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 O1 C16 C17 101.3(2) . . . . ?
P1 C4 C15 C14 -177.7(2) . . . . ?
P1 C5 C6 C7 46.8(3) . . . . ?
P1 C5 C6 C18 -134.8(2) . . . . ?
O2 P1 O1 C16 -49.0(2) . . . . ?
O2 P1 C4 C3 156.2(2) . . . . ?
O2 P1 C4 C15 -24.8(3) . . . . ?
O2 P1 C5 C22 137.4(3) . . . . ?
O2 P1 C5 C6 -47.6(3) . . . . ?
O1 P1 C4 C3 -80.3(2) . . . . ?
O1 P1 C4 C15 98.6(2) . . . . ?
O1 P1 C5 C22 10.7(3) . . . . ?
O1 P1 C5 C6 -174.3(2) . . . . ?
C22 C5 C6 C7 -138.3(3) . . . . ?
C22 C5 C6 C18 40.1(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C14 C15 C4 -1.0(5) . . . . ?
C2 C1 C14 C15 -0.1(5) . . . . ?
C2 C3 C4 P1 178.4(2) . . . . ?
C2 C3 C4 C15 -0.6(4) . . . . ?
C3 C4 C15 C14 1.3(4) . . . . ?
C4 P1 O1 C16 -171.49(18) . . . . ?
C4 P1 C5 C22 -96.4(3) . . . . ?
C4 P1 C5 C6 78.6(2) . . . . ?
C5 P1 O1 C16 77.3(2) . . . . ?
C5 P1 C4 C3 29.6(2) . . . . ?
C5 P1 C4 C15 -151.4(2) . . . . ?
C5 C6 C7 C8 177.1(2) . . . . ?
C5 C6 C18 C19 -177.9(2) . . . . ?
C6 C7 C8 C9 1.4(4) . . . . ?
C6 C18 C19 C9 0.1(4) . . . . ?
C7 C6 C18 C19 0.6(4) . . . . ?
C7 C8 C9 C10 -180.0(2) . . . . ?
C7 C8 C9 C19 -0.6(4) . . . . ?
C8 C9 C10 C11 158.4(3) . . . . ?
C8 C9 C10 C21 -21.4(4) . . . . ?
C8 C9 C19 C18 -0.1(4) . . . . ?
C9 C10 C11 C12 -179.7(3) . . . . ?
C9 C10 C21 C20 178.9(3) . . . . ?
C10 C9 C19 C18 179.3(3) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C11 C10 C21 C20 -1.0(5) . . . . ?
C11 C12 C13 C20 -0.8(6) . . . . ?
C12 C13 C20 C21 -0.1(6) . . . . ?
C13 C20 C21 C10 1.0(5) . . . . ?
C14 C1 C2 C3 0.9(4) . . . . ?
C18 C6 C7 C8 -1.3(4) . . . . ?
C19 C9 C10 C11 -20.9(4) . . . . ?
C19 C9 C10 C21 159.3(3) . . . . ?
C21 C10 C11 C12 0.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
