Redox-neutral rhodium(III)-catalyzed divergent synthesis of tetrasubstituted 1,3-enynes and alkynylated benzofurans.
Gong, Xin; Yu, Na; Gu, Linghui; Li, Zheyu; Ma, Wenbo; Zhao, Fei; Organic & biomolecular chemistry 21 (2022) 147–152; doi:10.1039/d2ob01800d

data_7159024
_publ_section_title
;
 Redox-neutral rhodium(III)-catalyzed divergent synthesis of
 tetrasubstituted 1,3-enynes and alkynylated benzofurans.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              147
_journal_page_last               152
_journal_paper_doi               10.1039/d2ob01800d
_journal_volume                  21
_journal_year                    2022
_chemical_formula_moiety         'C18 H22 Cl N O2'
_chemical_formula_sum            'C18 H22 Cl N O2'
_chemical_formula_weight         319.81
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-14
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-08-12 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.377(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3131(9)
_cell_length_b                   8.5318(4)
_cell_length_c                   11.6113(4)
_cell_measurement_reflns_used    1671
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      69.8420
_cell_measurement_theta_min      2.6070
_cell_volume                     1710.13(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     52.00  83.00   0.50    3.00    --   42.30 -82.00-180.00   62
  2  \w     83.00 132.00   0.50    3.00    --   42.30  77.00-150.00   98
  3  \w    -21.00  85.00   0.50    3.00    --   42.30 -82.00  30.00  212
  4  \w     17.00 107.00   0.50    3.00    --   42.30  57.00-180.00  180
  5  \w    -32.00  12.00   0.50    3.00    --   42.30 -82.00-180.00   88
  6  \w     55.00 144.00   0.50    6.00    --  101.60  38.00 -30.00  178
  7  \w     17.00  88.00   0.50    6.00    --  101.60 -50.00-150.00  142
  8  \w     43.00 133.00   0.50    6.00    --  101.60 -63.00 120.00  180
  9  \w     67.00 132.00   0.50    6.00    --  101.60 -50.00 120.00  130
 10  \w     98.00 130.00   0.50    6.00    --  101.60 -77.00  30.00   64
 11  \w     79.00 172.00   0.50    6.00    --  101.60  38.00 -60.00  186
 12  \w     14.00 120.00   0.50    6.00    --  101.60 -82.00   0.00  212
 13  \w     32.00 127.00   0.50    6.00    --  101.60 -63.00   0.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0809545000
_diffrn_orient_matrix_UB_12      0.0712769000
_diffrn_orient_matrix_UB_13      0.0285030000
_diffrn_orient_matrix_UB_21      -0.0372291000
_diffrn_orient_matrix_UB_22      0.1605849000
_diffrn_orient_matrix_UB_23      0.0203403000
_diffrn_orient_matrix_UB_31      -0.0049938000
_diffrn_orient_matrix_UB_32      -0.0414983000
_diffrn_orient_matrix_UB_33      0.1284032000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8611
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.820
_diffrn_reflns_theta_min         2.560
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0703
_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^)+(0.1131P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.1931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2350
_reflns_number_total             3275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01800d2.cif
_cod_data_source_block           gx-41_2
_cod_depositor_comments          'Adding full bibliography for 7159024.cif.'
_cod_database_code               7159024
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H O N Cl'
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              37209
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.882
_oxdiff_exptl_absorpt_empirical_full_min 0.437