Reductive cyclisations of amidines involving aminal radicals.
Huang, Huan-Ming; Adams, Ralph W.; Procter, David J.; Chemical communications (Cambridge, England) 54 (2018) 10160–10163; doi:10.1039/c8cc05178j

data_7122185
_publ_section_title
;
 Reductive cyclisations of amidines involving aminal radicals.
;
_journal_issue                   72
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10160
_journal_page_last               10163
_journal_paper_doi               10.1039/c8cc05178j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-05-31 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.637(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0010(11)
_cell_length_b                   6.9737(7)
_cell_length_c                   20.129(2)
_cell_measurement_reflns_used    2316
_cell_measurement_temperature    149.9(5)
_cell_measurement_theta_max      27.3130
_cell_measurement_theta_min      3.7070
_cell_volume                     1541.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -72.00 -46.00   1.00   50.00    --  -17.61 122.00   8.00   26
  2  \w     29.00  58.00   1.00   50.00    --   19.02 -99.00 -60.00   29
  3  \w    -42.00  28.00   1.00   50.00    --   19.02 -57.00 -90.00   70
  4  \w     20.00  88.00   1.00   50.00    --   19.02  57.00 -30.00   68
  5  \w    -10.00  84.00   1.00   50.00    --   19.02  77.00-120.00   94
  6  \w    -50.00  37.00   1.00   50.00    --   19.02 -57.00-180.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0380531000
_diffrn_orient_matrix_UB_12      0.0094251000
_diffrn_orient_matrix_UB_13      -0.0296111000
_diffrn_orient_matrix_UB_21      -0.0521483000
_diffrn_orient_matrix_UB_22      -0.0027209000
_diffrn_orient_matrix_UB_23      0.0189752000
_diffrn_orient_matrix_UB_31      0.0021279000
_diffrn_orient_matrix_UB_32      0.1012263000
_diffrn_orient_matrix_UB_33      0.0032517000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9930
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         3.461
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0431P)^2^+0.0572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1996
_reflns_number_total             2826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05178j2.cif
_cod_data_source_block           s4650a
_cod_depositor_comments
'Adding full bibliography for 7122184--7122186.cif.'
_cod_database_code               7122185
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              15274
_olex2_date_sample_data_collection 2017-03-14
_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 1.545
_oxdiff_exptl_absorpt_empirical_full_min 0.667