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_7122186
_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 H20 N2 O'
_chemical_formula_sum            'C19 H20 N2 O'
_chemical_formula_weight         292.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2018-05-31 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   41.133(3)
_cell_length_b                   13.3359(14)
_cell_length_c                   11.1564(8)
_cell_measurement_reflns_used    5845
_cell_measurement_temperature    149.9(4)
_cell_measurement_theta_max      26.5890
_cell_measurement_theta_min      3.7410
_cell_volume                     6119.8(9)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.910
_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     -1.00  51.00   1.00   22.50    --   20.18  57.00   0.00   52
  2  \w    -49.00  52.00   1.00   22.50    --   20.18 -77.00  30.00  101
  3  \w    -42.00  52.00   1.00   22.50    --   20.18 -77.00 150.00   94
  4  \w      1.00  82.00   1.00   22.50    --   20.18  37.00 -60.00   81
;
_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      0.0169092000
_diffrn_orient_matrix_UB_12      0.0104263000
_diffrn_orient_matrix_UB_13      0.0028203000
_diffrn_orient_matrix_UB_21      -0.0033963000
_diffrn_orient_matrix_UB_22      0.0520813000
_diffrn_orient_matrix_UB_23      0.0029939000
_diffrn_orient_matrix_UB_31      -0.0005942000
_diffrn_orient_matrix_UB_32      -0.0026641000
_diffrn_orient_matrix_UB_33      0.0634021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19398
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.136
_diffrn_reflns_theta_min         3.212
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15901
_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    0.635
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         7118
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0785
_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^)+(0.1370P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2542
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                4664
_reflns_number_total             7118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05178j2.cif
_cod_data_source_block           adjp201
_cod_depositor_comments
'Adding full bibliography for 7122184--7122186.cif.'
_cod_database_code               7122186
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H30N2O3
_chemical_oxdiff_usercomment     'astl 61 oaw1 aw/stl'
_reflns_odcompleteness_completeness 99.63
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00H(H00C,H00E), C00J(H00H,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C10(H10), C7(H7), C6(H6), C00D(H00D), C00F(H00F), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_date_sample_data_collection 2017-03-25
_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 2.632
_oxdiff_exptl_absorpt_empirical_full_min 0.403