Oxidant-switchable selective synthesis of 2-aminobenzimidazoles via C-H amination/acetoxylation of guanidines.
Chi, Yue; Zhang, Wen-Xiong; Xi, Zhenfeng; Organic letters 16 (2014) 6274–6277; doi:10.1021/ol502815p

data_1518404
_publ_section_title
;
 Oxidant-switchable selective synthesis of 2-aminobenzimidazoles via C-H
 amination/acetoxylation of guanidines.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6274
_journal_page_last               6277
_journal_paper_doi               10.1021/ol502815p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C15 H21 N3 O2'
_chemical_formula_sum            'C15 H21 N3 O2'
_chemical_formula_weight         275.35
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-22
_audit_creation_method
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Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
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_cell_angle_alpha                90
_cell_angle_beta                 98.400(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8144(15)
_cell_length_b                   9.3105(8)
_cell_length_c                   9.4113(7)
_cell_measurement_reflns_used    1822
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      27.9970
_cell_measurement_theta_min      3.7210
_cell_volume                     1457.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100.00(18)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8383
_diffrn_measurement_details
;
  1 omega   36.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000    0.0000 55

  2 omega  -41.00   30.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000   60.0000 71

  3 omega    1.00   83.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   57.0000 -180.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0402597000
_diffrn_orient_matrix_UB_12      -0.0249257000
_diffrn_orient_matrix_UB_13      0.0090944000
_diffrn_orient_matrix_UB_21      -0.0056709000
_diffrn_orient_matrix_UB_22      -0.0333836000
_diffrn_orient_matrix_UB_23      0.0655976000
_diffrn_orient_matrix_UB_31      -0.0126612000
_diffrn_orient_matrix_UB_32      -0.0638348000
_diffrn_orient_matrix_UB_33      -0.0377678000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6822
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.094
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description
;
;
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0508P)^2^+0.7274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1935
_reflns_number_total             2864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502815p_si_002.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 1518404--1518405.cif.'
_cod_database_code               1518404
_shelxl_version_number           2013-3
_chemical_oxdiff_formula         'C61 H41 Li Yb Si2 O'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.056) H1B(0.056) H1C(0.056) H4(0.024) H7(0.026) H8(0.026)
 H10(0.025) H11A(0.043) H11B(0.043) H11C(0.043) H12A(0.04) H12B(0.04)
 H12C(0.04) H13(0.026) H14A(0.043) H14B(0.043) H14C(0.043) H15A(0.039)
 H15B(0.039) H15C(0.039) H3(0.022)
 Fixed X: H1A(1.0498) H1B(1.1059) H1C(1.0311) H4(0.8425) H7(0.7658) H8(0.8691)
 H10(0.6665) H11A(0.7969) H11B(0.7831) H11C(0.8341) H12A(0.7332) H12B(0.6873)
 H12C(0.6394) H13(0.5349) H14A(0.6451) H14B(0.5605) H14C(0.6127) H15A(0.5009)
 H15B(0.4453) H15C(0.4556) H3(0.6015)
 Fixed Y: H1A(0.7989) H1B(0.7784) H1C(0.8864) H4(0.6584) H7(0.342) H8(0.5106)
 H10(0.4919) H11A(0.4081) H11B(0.5573) H11C(0.5531) H12A(0.74) H12B(0.7403)
 H12C(0.7019) H13(0.2076) H14A(0.0455) H14B(-0.0345) H14C(0.0057) H15A(0.1457)
 H15B(0.0993) H15C(0.2655) H3(0.3312)
 Fixed Z: H1A(0.014) H1B(0.1653) H1C(0.1517) H4(0.3265) H7(-0.0647) H8(-
 0.0712) H10(0.5314) H11A(0.6084) H11B(0.6855) H11C(0.5547) H12A(0.4173)
 H12B(0.5548) H12C(0.3998) H13(0.1979) H14A(0.2554) H14B(0.2513) H14C(0.4021)
 H15A(0.4803) H15B(0.3349) H15C(0.3767) H3(0.4499)
;
_olex2_submission_special_instructions 'No special instructions were received'