Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate
Ghosh, Koushik; Nishii, Yuji; Miura, Masahiro; ACS Catalysis  (2019) 11455–; doi:10.1021/acscatal.9b04254

data_4516226
_publ_section_title
;
 Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an
 Oxidizing Acetylene Surrogate
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11455
_journal_paper_doi               10.1021/acscatal.9b04254
_journal_year                    2019
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3719(6)
_cell_length_b                   6.4267(3)
_cell_length_c                   25.3093(11)
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.6400
_cell_measurement_theta_min      4.6240
_cell_volume                     2337.67(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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    -21.00   5.00   0.50    0.05    --  -42.80  24.00  21.00   52
  2  \w    -70.00 -45.00   0.50    0.22    -- -106.00 125.00   0.00   50
  3  \w    -80.00 -32.00   0.50    0.22    -- -106.00  77.00  30.00   96
  4  \w    -99.00 -44.00   0.50    0.22    -- -106.00 114.00-136.00  110
  5  \w   -114.00 -78.00   0.50    0.22    -- -106.00 125.00   0.00   72
  6  \w   -108.00 -54.00   0.50    0.22    -- -106.00 125.00  30.00  108
  7  \w   -134.00 -92.00   0.50    0.22    -- -106.00  77.00  30.00   84
  8  \w   -166.00 -91.00   0.50    0.22    -- -106.00 -37.00 150.00  150
  9  \w   -119.00 -93.00   0.50    0.22    -- -106.00-104.00  35.00   52
 10  \w   -102.00 -70.00   0.50    0.22    -- -106.00-125.00 -30.00   64
 11  \w   -117.00 -43.00   0.50    0.05    --  -42.80-171.00  -8.00  148
 12  \w   -105.00 -80.00   0.50    0.22    -- -106.00 -24.00-142.00   50
 13  \w   -169.00-139.00   0.50    0.22    -- -106.00-125.00 -30.00   60
 14  \w   -173.00-127.00   0.50    0.22    -- -106.00 -24.00-142.00   92
 15  \w     73.00 117.00   0.50    0.05    --   42.80 125.00  60.00   88
 16  \w    110.00 152.00   0.50    0.22    --   76.50 104.00 135.00   84
 17  \w     72.00 117.00   0.50    0.05    --   42.80 125.00  90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0163073000
_diffrn_orient_matrix_UB_12      -0.0180772000
_diffrn_orient_matrix_UB_13      0.0599951000
_diffrn_orient_matrix_UB_21      0.0291011000
_diffrn_orient_matrix_UB_22      -0.2306298000
_diffrn_orient_matrix_UB_23      -0.0018724000
_diffrn_orient_matrix_UB_31      0.1018496000
_diffrn_orient_matrix_UB_32      0.0630197000
_diffrn_orient_matrix_UB_33      0.0100894000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9683
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.208
_diffrn_reflns_theta_min         3.493
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.066
_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     173
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0676P)^2^+0.5234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2059
_reflns_number_total             2337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04254_si_002.cif
_cod_data_source_block           KG_190816
_cod_database_code               4516226
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C16 O N2 H12'
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.790
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 Aromatic/amide H refined with riding coordinates:
 C8(H8), C2(H2), C7(H7), C5(H5), C3(H3), C15(H15), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              14415
_shelx_hkl_checksum              36838
_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 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.541