Capture-Collapse Heterocyclization: 1,3-Diazepanes by C-N Reductive Elimination from Rhodacyclopentanones.
McCreanor, Niall G.; Stanton, Steven; Bower, John F.; Journal of the American Chemical Society 138 (2016) 11465–11468; doi:10.1021/jacs.6b07046

data_4130806
_publ_section_title
;
 Capture-Collapse Heterocyclization: 1,3-Diazepanes by C-N Reductive
 Elimination from Rhodacyclopentanones.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11465
_journal_page_last               11468
_journal_paper_doi               10.1021/jacs.6b07046
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C18 H18 N2 O2 S'
_chemical_formula_sum            'C18 H18 N2 O2 S'
_chemical_formula_weight         326.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7132(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4142(5)
_cell_length_b                   10.5216(3)
_cell_length_c                   19.1349(6)
_cell_measurement_reflns_used    5744
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.31
_cell_volume                     3235.85(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14563
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.962
_diffrn_reflns_theta_min         2.174
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0534 before and 0.0389 after correction.
The Ratio of minimum to maximum transmission is 0.9109.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0436P)^2^+2.4354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3362
_reflns_number_total             3885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07046_si_004.cif
_cod_data_source_block           testm1
_cod_database_code               4130806
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              2178
_shelx_hkl_checksum              54733
_olex2_submission_special_instructions 'No special instructions were received'