Propargyl Alcohols as One-Carbon Synthons: Redox-Neutral Rhodium(III)-Catalyzed C-H Bond Activation for the Synthesis of Isoindolinones Bearing a Quaternary Carbon.
Wu, Xiaowei; Wang, Bao; Zhou, Yu; Liu, Hong; Organic letters 19 (2017) 1294–1297; doi:10.1021/acs.orglett.7b00089

data_1545330
_publ_section_title
;
 Propargyl Alcohols as One-Carbon Synthons: Redox-Neutral
 Rhodium(III)-Catalyzed C-H Bond Activation for the Synthesis of
 Isoindolinones Bearing a Quaternary Carbon.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1294
_journal_page_last               1297
_journal_paper_doi               10.1021/acs.orglett.7b00089
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C17 H14 I N O2, C H Cl3'
_chemical_formula_sum            'C18 H15 Cl3 I N O2'
_chemical_formula_weight         510.56
_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_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.901(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0239(5)
_cell_length_b                   9.3470(3)
_cell_length_c                   25.5660(6)
_cell_measurement_reflns_used    4940
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.49
_cell_volume                     3912.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_number            4516
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_min         1.656
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_T_max  0.745557
_exptl_absorpt_correction_T_min  0.471338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0969 before and 0.0450 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1285 before and 0.0487 after correction.
 The Ratio of minimum to maximum transmission is 0.63.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 52459 reflections, Rint = 0.0497
 (31164 with I > 3sig(I), Rint = 0.0451)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0700P)^2^+6.6910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4039
_reflns_number_total             4516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00089_si_002.cif
_cod_data_source_block           mm
_cod_depositor_comments          'Adding full bibliography for 1545330.cif.'
_cod_database_code               1545330
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C15(H15), C12(H12), C13(H13), C5(H5), C14(H14), C6(H6)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'