Rhodium-Catalyzed Oxidative Coupling of Benzoic Acids with Terminal Alkynes: An Efficient Access to 3-Ylidenephthalides
Liu, Yang; Yang, Yudong; Shi, Yang; Wang, Xiaojie; Zhang, Luoqiang; Cheng, Yangyang; You, Jingsong; Organometallics 35 (2016) 1350–; doi:10.1021/acs.organomet.6b00107

data_4086506
_publ_section_title
;
 Rhodium-Catalyzed Oxidative Coupling of Benzoic Acids with Terminal
 Alkynes: An Efficient Access to 3-Ylidenephthalides
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              1350
_journal_paper_doi               10.1021/acs.organomet.6b00107
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C19 H28 O3 Si'
_chemical_formula_sum            'C19 H28 O3 Si'
_chemical_formula_weight         332.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2951(4)
_cell_length_b                   14.1131(4)
_cell_length_c                   20.4113(5)
_cell_measurement_reflns_used    4400
_cell_measurement_temperature    290.6(4)
_cell_measurement_theta_max      72.4020
_cell_measurement_theta_min      4.5910
_cell_volume                     3829.88(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.6(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   10.00  104.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -120.0000 94

  2 omega  -31.00   53.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   90.0000 84

  3 omega    1.00   75.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -120.0000 74

  4 omega  -31.00   63.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000 -150.0000 94

  5 omega   43.00  104.00   1.0000    2.6700
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000    0.0000 61

  6 omega  102.00  160.00   1.0000   10.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 58

  7 omega   51.00   89.00   1.0000   10.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 38

  8 omega   56.00   87.00   1.0000   10.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 31

  9 omega   64.00   94.00   1.0000   10.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 30

 10 omega   40.00  109.00   1.0000   10.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 69

 11 omega  104.00  142.00   1.0000   10.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 38

 12 omega   59.00   94.00   1.0000   10.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0514639000
_diffrn_orient_matrix_UB_12      -0.0058135000
_diffrn_orient_matrix_UB_13      0.0675048000
_diffrn_orient_matrix_UB_21      0.1038506000
_diffrn_orient_matrix_UB_22      -0.0036569000
_diffrn_orient_matrix_UB_23      0.0334410000
_diffrn_orient_matrix_UB_31      0.0006602000
_diffrn_orient_matrix_UB_32      0.1089063000
_diffrn_orient_matrix_UB_33      0.0047056000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10700
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         5.058
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+1.1670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1957
_refine_ls_wR_factor_ref         0.2061
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2971
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00107_si_002.cif
_cod_data_source_block           ly-168
_cod_depositor_comments
;Removing empty '_publ_contact_author_name' and
 '_exptl_crystal_description'.
;
_cod_database_code               4086506
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00J(H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00B), C00C(H00C), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00G(H00A,H00G,H00H), C00H(H00I,H00J,H00K), C00I(H00L,H00M,H00N), C00K(H00P,
 H00Q,H00R), C00L(H00S,H00T,H00U), C00M(H00V,H00W,H00X), C00N(H00Y,H,HA)
;
_shelx_res_checksum              41310
_shelx_hkl_checksum              30500
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-26
_olex2_submission_special_instructions 'No special instructions were received'