Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions.
Mateo, Pierre; Cinqualbre, Joséphine E; Meyer Mojzes, Melinda; Schenk, Kurt; Renaud, Philippe; The Journal of organic chemistry 82 (2017) 12318–12327; doi:10.1021/acs.joc.7b02150

data_4033037
_publ_section_title
;
 Reductive Alkylation of Tertiary Lactams via Addition of Organocopper
 (RCu) Reagents to Thioiminium Ions.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12318
_journal_page_last               12327
_journal_paper_doi               10.1021/acs.joc.7b02150
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C15 H26 B N'
_chemical_formula_sum            'C15 H26 B N'
_chemical_formula_weight         231.18
_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
_audit_creation_date             02-07-2017
_audit_creation_method           'SHELXL-2016/6, STOE X-RED32'
_cell_angle_alpha                90
_cell_angle_beta                 115.06(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.350(3)
_cell_length_b                   5.9252(12)
_cell_length_c                   17.079(3)
_cell_measurement_reflns_used    14492
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.27
_cell_volume                     1498.8(6)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area X-Red32 1.63.2.0 (STOE, 2017) 
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
360 frames, detector distance = 90 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.8 mm diameter'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30883
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.691
_diffrn_reflns_theta_min         2.271
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           43.000
_diffrn_source_power             2.365
_diffrn_source_target            Molybdenum
_diffrn_source_type              'water-cooled anode'
_diffrn_source_voltage           55
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.024
_exptl_crystal_description       Parallelepipide
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3390
_exptl_crystal_size_mid          0.1780
_exptl_crystal_size_min          0.1780
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0705
_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^)+(0.0953P)^2^+0.1402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.2107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2432
_reflns_number_total             4600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02150_si_002.cif
_cod_data_source_block           global
_cod_depositor_comments          'Adding full bibliography for 4033037.cif.'
_cod_database_code               4033037
_shelx_shelxl_version_number     2016/6
_audit_contact_author            'Kurt J. Schenk'
_exptl_absorpt_special_details
;
The habitus of the measured crystal consists of a {010} Pinacoid and a
{101} Prism.
;
_shelx_res_checksum              63442
_shelx_hkl_checksum              55581