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_4516227
_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         'C H Cl3, C19 H12 N2'
_chemical_formula_sum            'C20 H13 Cl3 N2'
_chemical_formula_weight         387.67
_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             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                 104.883(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0701(3)
_cell_length_b                   12.5560(3)
_cell_length_c                   10.8819(3)
_cell_measurement_reflns_used    7300
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.9350
_cell_measurement_theta_min      4.9270
_cell_volume                     1725.90(8)
_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 1.000
_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    -26.00  66.00   0.50    0.05    --   42.80 -32.00  82.00  184
  2  \w     24.00  49.00   0.50    0.05    --   76.50 -32.00  82.00   50
  3  \w     -2.00  64.00   0.50    0.05    --   42.80 -57.00   0.00  132
  4  \w     46.00  72.00   0.50    0.05    --   42.80  32.00-117.00   52
  5  \w     95.00 121.00   0.50    0.05    --   76.50  32.00-117.00   52
  6  \w     72.00 112.00   0.50    0.05    --   42.80 125.00   0.00   80
  7  \w     88.00 117.00   0.50    0.05    --   42.80 125.00  90.00   58
  8  \w      9.00  34.00   0.50    0.05    --  -42.80  32.00-117.00   50
  9  \w     74.00 123.00   0.50    0.05    --   76.50 125.00-180.00   98
 10  \w    -52.00 -27.00   0.50    0.05    -- -106.00   0.00-150.00   50
 11  \w   -119.00 -68.00   0.50    0.05    -- -106.00   0.00-150.00  102
 12  \w   -129.00 -27.00   0.50    0.05    -- -106.00  32.00-117.00  204
 13  \w    -85.00 -28.00   0.50    0.05    -- -106.00  37.00  60.00  114
 14  \w    -84.00 -31.00   0.50    0.05    -- -106.00  37.00  90.00  106
 15  \w    -78.00 -52.00   0.50    0.05    -- -106.00  57.00  90.00   52
 16  \w    -76.00 -49.00   0.50    0.05    --  -42.80 -32.00  82.00   54
 17  \w   -127.00 -89.00   0.50    0.05    -- -106.00  57.00  90.00   76
 18  \w   -133.00 -25.00   0.50    0.05    -- -106.00  19.00  60.00  216
 19  \w   -114.00 -67.00   0.50    0.05    -- -106.00 125.00   0.00   94
 20  \w   -133.00 -72.00   0.50    0.05    -- -106.00  77.00 120.00  122
 21  \w   -154.00-129.00   0.50    0.05    -- -106.00 -32.00  82.00   50
 22  \w   -171.00 -83.00   0.50    0.05    -- -106.00 -37.00  60.00  176
 23  \w   -177.00-124.00   0.50    0.05    -- -106.00-125.00-150.00  106
 24  \w   -156.00-130.00   0.50    0.05    -- -106.00   0.00-150.00   52
 25  \w   -128.00 -57.00   0.50    0.05    -- -106.00  57.00-150.00  142
;
_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      0.0057075000
_diffrn_orient_matrix_UB_12      -0.0479315000
_diffrn_orient_matrix_UB_13      0.1319129000
_diffrn_orient_matrix_UB_21      -0.1204532000
_diffrn_orient_matrix_UB_22      0.0148660000
_diffrn_orient_matrix_UB_23      -0.0227652000
_diffrn_orient_matrix_UB_31      -0.0184266000
_diffrn_orient_matrix_UB_32      -0.1119575000
_diffrn_orient_matrix_UB_33      -0.0594351000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.097
_diffrn_reflns_theta_min         3.499
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64981
_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            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0695P)^2^+0.3699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3202
_reflns_number_total             3467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04254_si_003.cif
_cod_data_source_block           kg_190625
_cod_database_code               4516227
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C20 H13 N2 Cl3'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C17(H17), C16(H16), C14(H14), C9(H9), C25(H25), C10(H10), C22(H22),
 C11(H11), C12(H12), C24(H24), C23(H23)
;
_shelx_res_checksum              86851
_shelx_hkl_checksum              8820
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.787