Trimerization and cyclization of reactive P-functionalities confined within OCO pincers
Chinen, Beatrice L.; Hyvl, Jakub; Brayton, Daniel F.; Riek, Matthew M.; Yoshida, Wesley Y.; Chapp, Timothy W.; Rheingold, Arnold L.; Cain, Matthew F.; RSC Advances 11 (2021) 28602–28613; doi:10.1039/D1RA05926B

data_7243447
_publ_section_title
;
 Trimerization and cyclization of reactive P-functionalities confined
 within OCO pincers
;
_journal_issue                   46
_journal_name_full               'RSC Advances'
_journal_page_first              28602
_journal_page_last               28613
_journal_paper_doi               10.1039/D1RA05926B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H13 F12 O2 P'
_chemical_formula_sum            'C20 H13 F12 O2 P'
_chemical_formula_weight         544.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-08 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.203(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4519(4)
_cell_length_b                   14.3030(9)
_cell_length_c                   11.4008(6)
_cell_measurement_reflns_used    3393
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      69.60
_cell_measurement_theta_min      3.88
_cell_volume                     1051.31(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6831
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.023
_diffrn_reflns_theta_min         3.880
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.334
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.4062
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0950 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.7782.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3721
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+1.0023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                3241
_reflns_number_total             3721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra05926b2.cif
_cod_data_source_block           cain100_0m_b
_cod_database_code               7243447
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.616
_shelx_estimated_absorpt_t_min   0.551
_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. Uiso/Uaniso restraints and constraints
Uanis(P1) = Uanis(P1')
Uanis(C17) = Uanis(C1')
Uanis(C18) = Uanis(O1')
Uanis(O2) = Uanis(O2')
3. Others
 Sof(P1')=1-FVAR(1)
 Sof(P1)=FVAR(1)
 Sof(O1')=Sof(O2')=Sof(C1')=Sof(H1'A)=Sof(H1'B)=Sof(H1'C)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C1'(H1'A,H1'B,H1'C)
;
_shelx_res_checksum              30192
_olex2_submission_special_instructions 'No special instructions were received'