Copper-catalyzed decarboxylative cyclization via tandem C-P and C-N bond formation: access to 2-phosphorylmethyl indoles.
Wang, Bao-Cheng; Wang, Ya-Ni; Zhang, Mao-Mao; Xiao, Wen-Jing; Lu, Liang-Qiu; Chemical communications (Cambridge, England) 54 (2018) 3154–3157; doi:10.1039/c8cc00739j

data_7121361
_publ_section_title
;
 Copper-catalyzed decarboxylative cyclization via tandem C-P and C-N bond
 formation: access to 2-phosphorylmethyl indoles.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3154
_journal_page_last               3157
_journal_paper_doi               10.1039/c8cc00739j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C28 H24 N O3 P S'
_chemical_formula_sum            'C28 H24 N O3 P S'
_chemical_formula_weight         485.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-01-20 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.658(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.966(4)
_cell_length_b                   13.056(3)
_cell_length_c                   11.101(3)
_cell_measurement_reflns_used    1826
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      19.3507
_cell_measurement_theta_min      2.4901
_cell_volume                     2494.6(10)
_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)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_unetI/netI     0.1088
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.195
_diffrn_reflns_theta_min         1.958
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         7968
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0609
_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/[\s^2^(Fo^2^)+(0.0662P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3509
_reflns_number_total             7968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00739j2.cif
_cod_data_source_block           complex1
_cod_depositor_comments          'Adding full bibliography for 7121361.cif.'
_cod_database_code               7121361
_shelx_shelxl_version_number     2018/1
_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. Restrained distances
 C6-C5 \\sim C7-C6 \\sim C8-C7 \\sim C8-C3 \\sim C4-C3 \\sim C5-C4
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              63223
_olex2_submission_special_instructions 'No special instructions were received'