data_20200929jiangshicun2_0m
_audit_creation_date               2020-09-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C21 H16 F O2 P'
_chemical_formula_sum              'C21 H16 F O2 P'
_chemical_formula_weight           350.31
_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' 0.0181 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'
 'F' 'F' 0.0727 0.0534 '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'

_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/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     5.83740(10)
_cell_length_b                     15.9288(4)
_cell_length_c                     21.4209(5)
_cell_angle_alpha                  90
_cell_angle_beta                   93.9030(10)
_cell_angle_gamma                  90
_cell_volume                       1987.16(8)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9087
_cell_measurement_temperature      273.15
_cell_measurement_theta_max        72.054
_cell_measurement_theta_min        2.774
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      1.386
_exptl_absorpt_correction_T_max    0.7536
_exptl_absorpt_correction_T_min    0.3107
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1420 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.4123.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_lustre       .
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.171
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               728
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0514
_diffrn_reflns_av_unetI/netI       0.0375
_diffrn_reflns_Laue_measured_fraction_full  0.995
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         19
_diffrn_reflns_limit_k_min         -19
_diffrn_reflns_limit_l_max         26
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              21994
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           72.101
_diffrn_reflns_theta_min           3.460
_diffrn_ambient_temperature        273.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_source_current             1.1
_diffrn_source_power               0.055
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3734
_reflns_number_total               3889
_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 V8.38A (Bruker, 2018)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.380
_refine_diff_density_min           -0.430
_refine_diff_density_rms           0.056
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       226
_refine_ls_number_reflns           3889
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0488
_refine_ls_R_factor_gt             0.0477
_refine_ls_restrained_S_all        1.030
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0838P)²+0.4811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1337
_refine_ls_wR_factor_ref           0.1346
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C18(H18), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_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 0.09790(6) 0.35581(2) 0.46175(2) 0.03790(15) Uani 1 1 d . . . . .
 O1 O -0.15288(19) 0.37364(8) 0.45707(6) 0.0514(3) Uani 1 1 d . . . . .
 O2 O 0.0097(3) 0.53300(9) 0.29282(6) 0.0675(4) Uani 1 1 d . . . . .
 F3 F 0.7664(3) 0.36237(11) 0.23647(8) 0.1030(5) Uani 1 1 d . . . . .
 C1 C 0.2690(3) 0.44604(9) 0.44227(7) 0.0419(3) Uani 1 1 d . . . . .
 H1A H 0.244396 0.491420 0.471259 0.050 Uiso 1 1 calc R U . . .
 H1B H 0.430557 0.431273 0.446175 0.050 Uiso 1 1 calc R U . . .
 C2 C 0.3244(3) 0.45544(9) 0.32187(7) 0.0445(3) Uani 1 1 d . . . . .
 C19 C 0.2005(3) 0.32345(9) 0.53915(7) 0.0424(3) Uani 1 1 d . . . . .
 C20 C 0.4157(3) 0.34408(12) 0.56683(8) 0.0532(4) Uani 1 1 d . . . . .
 H20 H 0.518253 0.374527 0.544340 0.064 Uiso 1 1 calc R U . . .
 C21 C 0.2781(4) 0.15129(14) 0.32344(11) 0.0745(6) Uani 1 1 d . . . . .
 H21 H 0.312673 0.109579 0.295196 0.089 Uiso 1 1 calc R U . . .
 C18 C 0.0742(4) 0.19172(15) 0.31688(11) 0.0793(7) Uani 1 1 d . . . . .
 H18 H -0.030281 0.178573 0.283600 0.095 Uiso 1 1 calc R U . . .
 C3 C 0.0207(3) 0.25262(13) 0.35959(9) 0.0634(5) Uani 1 1 d . . . . .
 H3 H -0.120379 0.279828 0.354887 0.076 Uiso 1 1 calc R U . . .
 C4 C 0.1736(3) 0.27351(9) 0.40901(7) 0.0427(3) Uani 1 1 d . . . . .
 C5 C 0.2046(3) 0.47447(9) 0.37689(7) 0.0428(3) Uani 1 1 d . . . . .
 C6 C 0.1967(3) 0.49254(11) 0.27189(8) 0.0543(4) Uani 1 1 d . . . . .
 C7 C 0.2538(4) 0.48668(14) 0.21078(9) 0.0713(6) Uani 1 1 d . . . . .
 H7 H 0.165021 0.511780 0.178248 0.086 Uiso 1 1 calc R U . . .
 C8 C 0.4484(4) 0.44193(15) 0.20022(10) 0.0739(6) Uani 1 1 d . . . . .
 H8 H 0.494674 0.436159 0.159745 0.089 Uiso 1 1 calc R U . . .
 C9 C 0.3280(4) 0.27334(14) 0.66080(9) 0.0712(6) Uani 1 1 d . . . . .
 H9 H 0.370083 0.256718 0.701592 0.085 Uiso 1 1 calc R U . . .
 C10 C 0.1165(4) 0.25179(16) 0.63377(11) 0.0776(6) Uani 1 1 d . . . . .
 H10 H 0.016521 0.220007 0.656136 0.093 Uiso 1 1 calc R U . . .
 C11 C 0.0513(3) 0.27707(13) 0.57347(10) 0.0628(5) Uani 1 1 d . . . . .
 H11 H -0.093382 0.262957 0.555729 0.075 Uiso 1 1 calc R U . . .
 C12 C 0.4329(4) 0.17186(15) 0.37160(13) 0.0806(7) Uani 1 1 d . . . . .
 H12 H 0.573640 0.144313 0.375670 0.097 Uiso 1 1 calc R U . . .
 C13 C 0.3836(3) 0.23311(13) 0.41447(11) 0.0676(5) Uani 1 1 d . . . . .
 H13 H 0.491222 0.247044 0.446824 0.081 Uiso 1 1 calc R U . . .
 C14 C 0.5218(3) 0.41098(12) 0.31067(9) 0.0563(4) Uani 1 1 d . . . . .
 H14 H 0.612958 0.386213 0.342872 0.068 Uiso 1 1 calc R U . . .
 C15 C 0.5747(4) 0.40567(14) 0.24958(10) 0.0674(5) Uani 1 1 d . . . . .
 C16 C 0.0211(3) 0.51984(11) 0.35631(9) 0.0559(4) Uani 1 1 d . . . . .
 H16 H -0.087231 0.540265 0.382345 0.067 Uiso 1 1 calc R U . . .
 C17 C 0.4782(4) 0.31952(14) 0.62773(9) 0.0652(5) Uani 1 1 d . . . . .
 H17 H 0.621399 0.334206 0.646207 0.078 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 1.4879(11) . ?
 P1 C1 1.8149(15) . ?
 P1 C19 1.7994(16) . ?
 P1 C4 1.8050(15) . ?
 O2 C6 1.369(2) . ?
 O2 C16 1.373(2) . ?
 F3 C15 1.360(3) . ?
 C1 H1A 0.9700 . ?
 C1 H1B 0.9700 . ?
 C1 C5 1.495(2) . ?
 C2 C5 1.443(2) . ?
 C2 C6 1.394(2) . ?
 C2 C14 1.387(2) . ?
 C19 C20 1.392(2) . ?
 C19 C11 1.390(2) . ?
 C20 H20 0.9300 . ?
 C20 C17 1.387(2) . ?
 C21 H21 0.9300 . ?
 C21 C18 1.352(3) . ?
 C21 C12 1.365(3) . ?
 C18 H18 0.9300 . ?
 C18 C3 1.384(3) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.378(2) . ?
 C4 C13 1.382(2) . ?
 C5 C16 1.342(2) . ?
 C6 C7 1.376(3) . ?
 C7 H7 0.9300 . ?
 C7 C8 1.373(3) . ?
 C8 H8 0.9300 . ?
 C8 C15 1.374(3) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.371(3) . ?
 C9 C17 1.377(3) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.381(3) . ?
 C11 H11 0.9300 . ?
 C12 H12 0.9300 . ?
 C12 C13 1.384(3) . ?
 C13 H13 0.9300 . ?
 C14 H14 0.9300 . ?
 C14 C15 1.368(3) . ?
 C16 H16 0.9300 . ?
 C17 H17 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 C1 112.81(7) . . ?
 O1 P1 C19 112.38(7) . . ?
 O1 P1 C4 112.23(7) . . ?
 C19 P1 C1 106.55(7) . . ?
 C19 P1 C4 106.76(7) . . ?
 C4 P1 C1 105.62(7) . . ?
 C6 O2 C16 105.46(13) . . ?
 P1 C1 H1A 109.6 . . ?
 P1 C1 H1B 109.6 . . ?
 H1A C1 H1B 108.1 . . ?
 C5 C1 P1 110.36(10) . . ?
 C5 C1 H1A 109.6 . . ?
 C5 C1 H1B 109.6 . . ?
 C6 C2 C5 105.96(14) . . ?
 C14 C2 C5 134.65(15) . . ?
 C14 C2 C6 119.39(16) . . ?
 C20 C19 P1 123.99(12) . . ?
 C11 C19 P1 117.30(13) . . ?
 C11 C19 C20 118.68(16) . . ?
 C19 C20 H20 119.8 . . ?
 C17 C20 C19 120.42(17) . . ?
 C17 C20 H20 119.8 . . ?
 C18 C21 H21 120.1 . . ?
 C18 C21 C12 119.83(18) . . ?
 C12 C21 H21 120.1 . . ?
 C21 C18 H18 119.9 . . ?
 C21 C18 C3 120.1(2) . . ?
 C3 C18 H18 119.9 . . ?
 C18 C3 H3 119.5 . . ?
 C4 C3 C18 120.90(18) . . ?
 C4 C3 H3 119.5 . . ?
 C3 C4 P1 118.85(13) . . ?
 C3 C4 C13 118.48(15) . . ?
 C13 C4 P1 122.59(13) . . ?
 C2 C5 C1 126.63(14) . . ?
 C16 C5 C1 127.96(15) . . ?
 C16 C5 C2 105.37(14) . . ?
 O2 C6 C2 110.17(15) . . ?
 O2 C6 C7 126.42(18) . . ?
 C7 C6 C2 123.40(18) . . ?
 C6 C7 H7 121.7 . . ?
 C8 C7 C6 116.67(19) . . ?
 C8 C7 H7 121.7 . . ?
 C7 C8 H8 120.1 . . ?
 C7 C8 C15 119.87(18) . . ?
 C15 C8 H8 120.1 . . ?
 C10 C9 H9 119.9 . . ?
 C10 C9 C17 120.21(18) . . ?
 C17 C9 H9 119.9 . . ?
 C9 C10 H10 119.8 . . ?
 C9 C10 C11 120.32(19) . . ?
 C11 C10 H10 119.8 . . ?
 C19 C11 H11 119.8 . . ?
 C10 C11 C19 120.46(19) . . ?
 C10 C11 H11 119.8 . . ?
 C21 C12 H12 119.5 . . ?
 C21 C12 C13 120.9(2) . . ?
 C13 C12 H12 119.5 . . ?
 C4 C13 C12 119.71(19) . . ?
 C4 C13 H13 120.1 . . ?
 C12 C13 H13 120.1 . . ?
 C2 C14 H14 121.9 . . ?
 C15 C14 C2 116.20(18) . . ?
 C15 C14 H14 121.9 . . ?
 F3 C15 C8 117.40(19) . . ?
 F3 C15 C14 118.1(2) . . ?
 C14 C15 C8 124.5(2) . . ?
 O2 C16 H16 123.5 . . ?
 C5 C16 O2 113.04(15) . . ?
 C5 C16 H16 123.5 . . ?
 C20 C17 H17 120.1 . . ?
 C9 C17 C20 119.9(2) . . ?
 C9 C17 H17 120.1 . . ?

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 C5 C2 -99.07(16) . . . . ?
 P1 C1 C5 C16 78.17(19) . . . . ?
 P1 C19 C20 C17 177.35(15) . . . . ?
 P1 C19 C11 C10 -178.48(17) . . . . ?
 P1 C4 C13 C12 -178.50(19) . . . . ?
 O1 P1 C1 C5 -59.46(12) . . . . ?
 O1 P1 C19 C20 -144.78(14) . . . . ?
 O1 P1 C19 C11 33.33(16) . . . . ?
 O1 P1 C4 C3 18.01(18) . . . . ?
 O1 P1 C4 C13 -165.05(16) . . . . ?
 O2 C6 C7 C8 -179.19(19) . . . . ?
 C1 P1 C19 C20 -20.74(16) . . . . ?
 C1 P1 C19 C11 157.38(14) . . . . ?
 C1 P1 C4 C3 -105.30(16) . . . . ?
 C1 P1 C4 C13 71.64(17) . . . . ?
 C1 C5 C16 O2 -178.15(15) . . . . ?
 C2 C5 C16 O2 -0.5(2) . . . . ?
 C2 C6 C7 C8 -0.4(3) . . . . ?
 C2 C14 C15 F3 -179.75(18) . . . . ?
 C2 C14 C15 C8 0.9(3) . . . . ?
 C19 P1 C1 C5 176.77(10) . . . . ?
 C19 P1 C4 C3 141.56(16) . . . . ?
 C19 P1 C4 C13 -41.50(18) . . . . ?
 C19 C20 C17 C9 1.0(3) . . . . ?
 C20 C19 C11 C10 -0.3(3) . . . . ?
 C21 C18 C3 C4 0.5(4) . . . . ?
 C21 C12 C13 C4 0.7(4) . . . . ?
 C18 C21 C12 C13 0.7(4) . . . . ?
 C18 C3 C4 P1 178.03(19) . . . . ?
 C18 C3 C4 C13 1.0(3) . . . . ?
 C3 C4 C13 C12 -1.5(3) . . . . ?
 C4 P1 C1 C5 63.48(12) . . . . ?
 C4 P1 C19 C20 91.76(15) . . . . ?
 C4 P1 C19 C11 -90.12(15) . . . . ?
 C5 C2 C6 O2 0.41(19) . . . . ?
 C5 C2 C6 C7 -178.55(18) . . . . ?
 C5 C2 C14 C15 178.17(18) . . . . ?
 C6 O2 C16 C5 0.7(2) . . . . ?
 C6 C2 C5 C1 177.76(15) . . . . ?
 C6 C2 C5 C16 0.02(18) . . . . ?
 C6 C2 C14 C15 -1.2(3) . . . . ?
 C6 C7 C8 C15 0.1(3) . . . . ?
 C7 C8 C15 F3 -179.7(2) . . . . ?
 C7 C8 C15 C14 -0.4(4) . . . . ?
 C9 C10 C11 C19 1.0(4) . . . . ?
 C10 C9 C17 C20 -0.2(3) . . . . ?
 C11 C19 C20 C17 -0.7(3) . . . . ?
 C12 C21 C18 C3 -1.3(4) . . . . ?
 C14 C2 C5 C1 -1.6(3) . . . . ?
 C14 C2 C5 C16 -179.39(19) . . . . ?
 C14 C2 C6 O2 179.93(16) . . . . ?
 C14 C2 C6 C7 1.0(3) . . . . ?
 C16 O2 C6 C2 -0.7(2) . . . . ?
 C16 O2 C6 C7 178.3(2) . . . . ?
 C17 C9 C10 C11 -0.8(4) . . . . ?

_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 -0.303 0.000 0.500 194.5 60.7 '1 hexane'
 2 -0.748 0.500 0.000 194.5 60.7 '1 hexane'

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