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_1518405
_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         'C24 H31 N3, 0.5(H2 O)'
_chemical_formula_sum            'C24 H32 N3 O0.5'
_chemical_formula_weight         370.52
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                88.988(5)
_cell_angle_beta                 75.801(5)
_cell_angle_gamma                78.453(5)
_cell_formula_units_Z            4
_cell_length_a                   10.0498(5)
_cell_length_b                   13.3126(7)
_cell_length_c                   16.9593(10)
_cell_measurement_reflns_used    3243
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      26.0780
_cell_measurement_theta_min      3.3140
_cell_volume                     2153.9(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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9931
_diffrn_measured_fraction_theta_max 0.8275
_diffrn_measurement_details
;
  1 omega  -59.00   35.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -57.0000 -180.0000 94

  2 omega  -16.00   79.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   57.0000  -30.0000 95

  3 omega  -20.00   53.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -99.0000   90.0000 73
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0112240000
_diffrn_orient_matrix_UB_12      0.0137781000
_diffrn_orient_matrix_UB_13      -0.0413514000
_diffrn_orient_matrix_UB_21      -0.0566855000
_diffrn_orient_matrix_UB_22      0.0426233000
_diffrn_orient_matrix_UB_23      0.0107907000
_diffrn_orient_matrix_UB_31      0.0467609000
_diffrn_orient_matrix_UB_32      0.0308860000
_diffrn_orient_matrix_UB_33      0.0060722000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13745
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.974
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83442
_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    1.143
_exptl_crystal_description
;
;
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         8455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0471P)^2^+0.5495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5576
_reflns_number_total             8455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502815p_si_002.cif
_cod_data_source_block           3n
_cod_depositor_comments
;
Adding full bibliography for 1518404--1518405.cif.

2019-01-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C24 H31 N3), H2 O'
_cod_original_formula_sum        'C48 H64 N6 O'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     741.05
_cod_database_code               1518405
_shelxl_version_number           2013-3
_chemical_oxdiff_formula         'C20 N3 H30'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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 Ternary CH refined with riding coordinates:
 C14(H14), C17(H17), C20(H20), C38(H38), C41(H41), C44(H44)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C22(H22a,H22b), C23(H23a,H23b), C24(H24a,H24b), C45(H45a,
 H45b), C46(H46a,H46b), C47(H47a,H47b), C48(H48a,H48b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C27(H27),
 C28(H28), C29(H29), C30(H30), C34(H34), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C18(H18a,H18b,H18c), C19(H19a,H19b,
 H19c), C39(H39a,H39b,H39c), C40(H40a,H40b,H40c), C42(H42a,H42b,H42c), C43(H43a,
 H43b,H43c)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'