Phosphinodifluoroalkylation of alkynes using P(O)H compounds and ethyl difluoroiodoacetate
Zhang, Pengbo; Ying, Jianxi; Tang, Guo; Zhao, Yufen; Organic Chemistry Frontiers 4 (2017) 2054–; doi:10.1039/C7QO00466D

data_1553823
_publ_section_title
;
 Phosphinodifluoroalkylation of alkynes using P(O)H compounds and ethyl
 difluoroiodoacetate
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2054
_journal_paper_doi               10.1039/C7QO00466D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C24 H21 F2 O3 P'
_chemical_formula_sum            'C24 H21 F2 O3 P'
_chemical_formula_weight         426.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-03-10 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.571(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.317(4)
_cell_length_b                   8.8649(15)
_cell_length_c                   22.042(4)
_cell_measurement_reflns_used    8180
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.745
_cell_measurement_theta_min      2.480
_cell_volume                     4259.3(13)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9943
_diffrn_measured_fraction_theta_max 0.9943
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17795
_diffrn_reflns_theta_full        25.9990
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.661395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.03 (Bruker,200?) was used for absorption correction. R(int) was 0.1268 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.6614. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3298
_exptl_crystal_description       block
_exptl_crystal_F_000             1777.8731
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2762
_refine_diff_density_min         -0.2661
_refine_diff_density_rms         0.0509
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             10.8992
_refine_ls_goodness_of_fit_ref   1.0601
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0601
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+3.7640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              26
_reflns_limit_h_min              -31
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                3723
_reflns_number_total             4161
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7qo00466d2.cif
_cod_data_source_block           z0223m
_cod_original_cell_volume        4259.4(12)
_cod_database_code               1553823
_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. Others
 Fixed Sof: C25(0.5) H25a(0.5) H25b(0.5) C26(0.55) H26a(0.55) H26b(0.55)
 H26c(0.55) C24(0.45) H24a(0.45) H24b(0.45) H24c(0.45) C23(0.5) H23a(0.5)
 H23b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C23(H23a,H23b)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C20(H20), C8(H8), C12(H12), C9(H9), C5(H5), C6(H6), C4(H4),
 C14(H14), C10(H10), C18(H18), C15(H15), C3(H3), C17(H17), C16(H16), C2(H2)
3.c Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'