<i>N</i>-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective <i>trans</i>-propenylation of aryl C(sp<sup>2</sup>)-H bond.
Biswal, Pragati; Nanda, Tanmayee; Banjare, Shyam Kumar; Mohanty, Smruti Ranjan; Mishra, Ranjit; Ravikumar, Ponneri C.; Chemical communications (Cambridge, England) 59 (2022) 199–202; doi:10.1039/d2cc06048e

data_7131054
_publ_section_title
;
 <i>N</i>-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed
 stereoselective <i>trans</i>-propenylation of aryl C(sp<sup>2</sup>)-H
 bond.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              199
_journal_page_last               202
_journal_paper_doi               10.1039/d2cc06048e
_journal_volume                  59
_journal_year                    2022
_chemical_formula_moiety         '4(C22 H23 Cl N O2 Rh)'
_chemical_formula_sum            'C22 H23 Cl N O2 Rh'
_chemical_formula_weight         471.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-03
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2021-04-05 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.79550(10)
_cell_length_b                   7.59350(10)
_cell_length_c                   15.85550(10)
_cell_measurement_reflns_used    21820
_cell_measurement_temperature    299.7(3)
_cell_measurement_theta_max      75.2650
_cell_measurement_theta_min      3.8910
_cell_volume                     1901.19(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      air
_diffrn_ambient_temperature      299.7(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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   -103.00 -17.00   0.50    1.58    --  -38.50 149.00 109.00  172
  2  \w    -85.00  -4.00   0.50    1.58    --  -38.50 123.00 -53.00  162
  3  \w     98.00 168.00   0.50    9.07    --  102.63 123.00 -53.00  140
  4  \w     37.00 111.00   0.50    9.07    --  102.63-123.00-134.00  148
  5  \w     40.00 130.00   0.50    9.07    --  102.63-149.00  62.00  180
  6  \w    -44.00  31.00   0.50    1.58    --  -38.50  19.00  60.00  150
  7  \w     26.00  99.00   0.50    1.58    --   49.56-123.00-134.00  146
  8  \w     39.00 117.00   0.50    1.58    --   49.56-149.00  62.00  156
  9  \w     83.00 166.00   0.50    9.07    --  102.63 149.00 109.00  166
 10  \w     95.00 171.00   0.50    9.07    --  102.63  15.00  30.00  152
 11  \w     40.00 116.00   0.50    9.07    --  102.63 -61.00-150.00  152
 12  \w     38.00 107.00   0.50    9.07    --  102.63 -45.00   0.00  138
 13  \w     40.00 116.00   0.50    9.07    --  102.63 -61.00   0.00  152
 14  \w     34.00 111.00   0.50    9.07    --  102.63 -15.00 150.00  154
 15  \w    100.00 170.00   0.50    9.07    --  102.63  34.00 -52.67  140
 16  \w   -102.00 -20.00   0.50    1.58    --  -38.50 -71.00 119.24  164
 17  \w   -102.00 -19.00   0.50    1.58    --  -38.50 -72.00  14.01  166
 18  \w     38.00 113.00   0.50    1.58    --   49.56  57.00-150.00  150
 19  \w     38.00 113.00   0.50    1.58    --   49.56  57.00 -30.00  150
 20  \w     38.00 113.00   0.50    1.58    --   49.56  57.00 -90.00  150
 21  \w     95.00 171.00   0.50    9.07    --  102.63  15.00-120.00  152
 22  \w     90.00 165.00   0.50    9.07    --  102.63  61.00 -30.00  150
 23  \w     95.00 171.00   0.50    9.07    --  102.63  15.00 150.00  152
 24  \w     38.00 112.00   0.50    9.07    --  102.63-125.00-180.00  148
 25  \w     98.00 167.00   0.50    9.07    --  102.63  45.00 -90.00  138
 26  \w     98.00 167.00   0.50    9.07    --  102.63  45.00-180.00  138
 27  \w     90.00 165.00   0.50    9.07    --  102.63  61.00  30.00  150
 28  \w     86.00 166.00   0.50    9.07    --  102.63  67.00  98.70  160
 29  \w     34.00 107.00   0.50    9.07    --  102.63 -94.00-120.00  146
 30  \w     99.00 171.00   0.50    9.07    --  102.63  30.00  90.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0971855000
_diffrn_orient_matrix_UB_12      0.0155352000
_diffrn_orient_matrix_UB_13      -0.0065540000
_diffrn_orient_matrix_UB_21      0.0048488000
_diffrn_orient_matrix_UB_22      0.0170586000
_diffrn_orient_matrix_UB_23      -0.0965896000
_diffrn_orient_matrix_UB_31      -0.0070895000
_diffrn_orient_matrix_UB_32      -0.2015400000
_diffrn_orient_matrix_UB_33      -0.0086573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27928
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.498
_diffrn_reflns_theta_min         3.903
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.692
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0300P)^2^+1.4070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3752
_reflns_number_total             3854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06048e2.cif
_cod_data_source_block           pcr-pb-tn-1nt-oxobri
_cod_depositor_comments
'Adding full bibliography for 7131054--7131055.cif.'
_cod_database_code               7131054
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C88 H92 Cl4 N4 O8 Rh4 '
_diffrn_oxdiff_digest_frames
;
019b0c825c075912e9e569d5cf7e05600a00032a855
;
_diffrn_oxdiff_digest_hkl
;
016d6fd758c798ae5b06d1b61459b41135e26b
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C2(H2), C8(H8), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C18(H18A,H18B,
 H18C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              18801
_shelx_hkl_checksum              54753
_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 2.462
_oxdiff_exptl_absorpt_empirical_full_min 0.671