<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_7131055
_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         'C18 H19 Cl N4'
_chemical_formula_sum            'C18 H19 Cl N4'
_chemical_formula_weight         326.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2021-04-13 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                65.854(3)
_cell_angle_beta                 83.509(3)
_cell_angle_gamma                69.754(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4208(3)
_cell_length_b                   10.0653(3)
_cell_length_c                   10.3448(3)
_cell_measurement_reflns_used    6700
_cell_measurement_temperature    299.7(5)
_cell_measurement_theta_max      74.6430
_cell_measurement_theta_min      4.6830
_cell_volume                     839.33(5)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      299.8(5)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9580
_diffrn_measured_fraction_theta_max 0.9563
_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   -102.00 -19.00   0.50    0.77    --  -38.50 -72.00 -73.00  166
  2  \w     30.00 113.00   0.50    0.77    --   49.56  72.00  56.00  166
  3  \w    -14.00  69.00   0.50    0.77    --   49.56 -72.00 -73.00  166
  4  \w     84.00 166.00   0.50    9.28    --  102.63  72.00  56.00  164
  5  \w     39.00 122.00   0.50    9.28    --  102.63 -72.00 -73.00  166
  6  \w    -44.00 -13.50   0.50    0.77    --  -38.50  19.00  30.00   61
  7  \w    -58.00  25.00   0.50    0.77    --  -38.50  72.00  56.00  166
  8  \w      7.00  86.00   0.50    0.77    --   49.56 -99.00 150.00  158
  9  \w     92.00 166.00   0.50    9.28    --  102.63  56.00  42.85  148
 10  \w     34.00 107.00   0.50    9.28    --  102.63 -94.00-120.00  146
 11  \w     97.00 168.00   0.50    9.28    --  102.63 125.00 -30.00  142
 12  \w     98.00 167.00   0.50    9.28    --  102.63  45.00  60.00  138
 13  \w     35.00 106.00   0.50    9.28    --  102.63 -30.00  30.00  142
 14  \w     35.00 106.00   0.50    9.28    --  102.63 -30.00-120.00  142
 15  \w     34.00 107.00   0.50    9.28    --  102.63 -94.00  30.00  146
 16  \w     38.00 112.00   0.50    9.28    --  102.63-125.00-120.00  148
 17  \w     34.00 107.00   0.50    9.28    --  102.63 -94.00  90.00  146
 18  \w     35.00 106.00   0.50    9.28    --  102.63 -30.00  90.00  142
 19  \w    103.00 167.00   0.50    9.28    --  102.63  77.00 150.00  128
 20  \w     38.00 126.00   0.50    9.28    --  102.63 -77.00-120.00  176
 21  \w     40.00 116.00   0.50    9.28    --  102.63 -61.00   0.00  152
 22  \w     98.00 167.00   0.50    9.28    --  102.63  45.00 -60.00  138
 23  \w     34.00 111.00   0.50    9.28    --  102.63 -15.00-120.00  154
 24  \w     34.00 107.00   0.50    9.28    --  102.63 -94.00 120.00  146
 25  \w    103.00 167.00   0.50    9.28    --  102.63  77.00-120.00  128
 26  \w    103.00 167.00   0.50    9.28    --  102.63  77.00 -30.00  128
 27  \w     34.00 107.00   0.50    9.28    --  102.63 -94.00 -60.00  146
 28  \w     38.00 107.00   0.50    9.28    --  102.63 -45.00  60.00  138
 29  \w     38.00 107.00   0.50    0.77    --   49.56  57.00 150.00  138
 30  \w     38.00 113.00   0.50    0.77    --   49.56  57.00-150.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11437
_diffrn_reflns_theta_full        75.5422
_diffrn_reflns_theta_max         75.54
_diffrn_reflns_theta_min         4.69
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60124
_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    1.2931
_exptl_crystal_description       cube
_exptl_crystal_F_000             345.6211
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.1538
_refine_diff_density_min         -0.2920
_refine_diff_density_rms         0.0466
_refine_ls_d_res_high            0.7961
_refine_ls_d_res_low             9.4345
_refine_ls_goodness_of_fit_ref   1.0307
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0307
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.0016
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2838
_reflns_number_total             3328
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2cc06048e2.cif
_cod_data_source_block           pbtn-purine
_cod_depositor_comments
'Adding full bibliography for 7131054--7131055.cif.'
_cod_database_code               7131055
_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 Ternary CH refined with riding coordinates:
 C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C38(H38a,H38b)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C26(H26), C30(H30), C36(H36), C24(H24), C31(H31), C37(H37)
2.d Idealised Me refined as rotating group:
 C40(H40a,H40b,H40c), C32(H32a,H32b,H32c), C41(H41a,H41b,H41c)
;
_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
;