Axially chiral dimethylaminobenzimidazoles and their preliminary evaluation as acyl-transfer reagents.
Toman, Daniel; Nemec, Ivan; Kurka, Ondřej; Přibylka, Adam; Cankař, Petr; Organic & biomolecular chemistry 23 (2025) 2672–2682; doi:10.1039/d4ob02052a

data_7160364
_publ_section_title
;
 Axially chiral dimethylaminobenzimidazoles and their preliminary
 evaluation as acyl-transfer reagents.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2672
_journal_page_last               2682
_journal_paper_doi               10.1039/d4ob02052a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H25 N4, Cl, H2 O'
_chemical_formula_sum            'C23 H27 Cl N4 O'
_chemical_formula_weight         410.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-02
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-12-02 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.13520(10)
_cell_length_b                   11.23990(10)
_cell_length_c                   18.2950(2)
_cell_measurement_reflns_used    8454
_cell_measurement_temperature    99.98(15)
_cell_measurement_theta_max      68.3090
_cell_measurement_theta_min      4.6030
_cell_volume                     2084.14(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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    -16.00  25.00   0.50    0.50    --  -42.75  70.00 -99.00   82
  2  \w    -45.00 -20.00   0.50    0.50    --  -42.75  70.00 -99.00   50
  3  \w    -45.00 -20.00   0.50    0.50    --  -42.75 -70.00 129.00   50
  4  \w    -21.00  15.00   0.50    0.50    --   44.32 -70.00 129.00   72
  5  \w     41.00  66.00   0.50    0.50    --   44.32 -70.00 129.00   50
  6  \w   -146.00 -93.00   0.50    3.50    --  -93.31 -70.00 129.00  106
  7  \w    -81.00 -56.00   0.50    3.50    --  -93.31  70.00 -99.00   50
  8  \w     29.00  64.00   0.50    3.50    --   94.87 -70.00 129.00   70
  9  \w      6.00  31.00   0.50    0.50    --  -42.75  11.00  60.00   50
 10  \w     65.00 104.00   0.50    0.50    --   44.32 138.00   0.00   78
 11  \w    -21.00  30.00   0.50    0.50    --   44.32 -32.00   0.00  102
 12  \w    -21.00  18.00   0.50    0.50    --   44.32 -11.00 -30.00   78
 13  \w    -20.00  28.00   0.50    0.50    --   44.32 -21.00 -60.00   96
 14  \w    -19.00  15.00   0.50    0.50    --   44.32 -21.00 120.00   68
 15  \w     29.00  54.00   0.50    0.50    --   44.32  70.00 -99.00   50
 16  \w     77.00 102.00   0.50    0.50    --   44.32  70.00 -99.00   50
 17  \w    -54.00 -28.00   0.50    3.50    --  -93.31  50.00  90.00   52
 18  \w   -127.00-101.00   0.50    3.50    --  -93.31 -25.00-180.00   52
 19  \w   -158.00-131.00   0.50    3.50    --  -93.31 -25.00-180.00   54
 20  \w    -51.00 -26.00   0.50    3.50    --  -93.31  59.00-120.00   50
 21  \w    -61.00 -32.00   0.50    3.50    --  -93.31 117.00   0.00   58
 22  \w   -108.00 -73.00   0.50    3.50    --  -93.31 117.00   0.00   70
 23  \w   -106.00 -38.00   0.50    3.50    --  -93.31  77.00  30.00  136
 24  \w    -80.00 -30.00   0.50    3.50    --  -93.31  68.00  90.00  100
 25  \w   -158.00 -95.00   0.50    3.50    --  -93.31 -68.00  90.00  126
 26  \w     29.00  55.00   0.50    3.50    --   94.87 -50.00-120.00   52
 27  \w     45.00  70.00   0.50    3.50    --   94.87 -68.00  60.00   50
 28  \w    129.00 157.00   0.50    3.50    --   94.87  68.00-150.00   56
 29  \w     93.00 118.00   0.50    3.50    --   94.87  70.00 -99.00   50
 30  \w     73.00 100.00   0.50    3.50    --   94.87  68.00-150.00   54
 31  \w     31.00  56.00   0.50    3.50    --   94.87 -50.00  90.00   50
 32  \w     54.00 105.00   0.50    3.50    --   94.87 -96.00 120.00  102
 33  \w     25.00  51.00   0.50    3.50    --   94.87 -96.00 120.00   52
 34  \w     90.00 163.00   0.50    3.50    --   94.87  25.00 -30.00  146
 35  \w     31.00  56.00   0.50    3.50    --   94.87 -59.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0973157000
_diffrn_orient_matrix_UB_12      -0.0094567000
_diffrn_orient_matrix_UB_13      0.0644624000
_diffrn_orient_matrix_UB_21      0.0517695000
_diffrn_orient_matrix_UB_22      -0.1258220000
_diffrn_orient_matrix_UB_23      0.0170682000
_diffrn_orient_matrix_UB_31      0.1046065000
_diffrn_orient_matrix_UB_32      0.0535525000
_diffrn_orient_matrix_UB_33      0.0514457000
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10810
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.402
_diffrn_reflns_theta_min         4.617
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.022(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0395P)^2^+0.3485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3700
_reflns_number_total             3796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02052a2.cif
_cod_data_source_block           Sa5fHCl
_cod_depositor_comments
'Adding full bibliography for 7160364--7160367.cif.'
_cod_database_code               7160364
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O Cl'
_chemical_oxdiff_usercomment     'DT B'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.978(13)
 0.022(13)
2. 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,H) groups
3.a Free rotating group:
 O1(H1D,H1E)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C20(H20A,H20B), C22(H22A,H22B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C12(H12), C13(H13), C9(H9), C8(H8), C7(H7), C6(H6),
 C15(H15), C17(H17), C16(H16)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              54745
_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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.804