Diastereoselective intermolecular ene reactions: synthesis of 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles.
Watson, Lynsey J.; Harrington, Ross W.; Clegg, William; Hall, Michael J.; Organic & biomolecular chemistry 10 (2012) 6649–6655; doi:10.1039/c2ob26009c

data_7152540
_publ_section_title
;
 Diastereoselective intermolecular ene reactions: synthesis of
 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6649
_journal_page_last               6655
_journal_paper_doi               10.1039/c2ob26009c
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C27 H24 F3 N3 O5'
_chemical_formula_sum            'C27 H24 F3 N3 O5'
_chemical_formula_weight         527.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.027(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.988(10)
_cell_length_b                   7.353(7)
_cell_length_c                   29.70(3)
_cell_measurement_reflns_used    4077
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.34
_cell_volume                     2390(4)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Crystal Logic diffractometer and Rigaku Saturn 724+ CCD'
_diffrn_measurement_method       'thick-slice \w scans'
_diffrn_radiation_monochromator  'double crystal silicon'
_diffrn_radiation_source         'Diamond Light Source Station I19'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21186
_diffrn_reflns_theta_full        21.25
_diffrn_reflns_theta_max         21.25
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.20(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.681
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     396
_refine_ls_restrained_S_all      2.564
_refine_ls_R_factor_all          0.2693
_refine_ls_R_factor_gt           0.2297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6078
_refine_ls_wR_factor_ref         0.6335
_reflns_number_gt                1923
_reflns_number_total             2913
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2ob26009c.txt
_cod_data_source_block           mjh68_compound_9c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152540