Asymmetric synthesis of 3-substituted tetrahydro-2-benzazepines.
Quick, Matthias P.; Fröhlich, Roland; Schepmann, Dirk; Wünsch, Bernhard; Organic & biomolecular chemistry 13 (2015) 7265–7281; doi:10.1039/c5ob00731c

data_7154501
_publ_section_title
;
 Asymmetric synthesis of 3-substituted tetrahydro-2-benzazepines.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7265
_journal_page_last               7281
_journal_paper_doi               10.1039/c5ob00731c
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-23 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.139(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4874(6)
_cell_length_b                   7.3181(4)
_cell_length_c                   15.1101(13)
_cell_measurement_reflns_used    1263
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     806.26(11)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4431
_diffrn_reflns_theta_full        66.54
_diffrn_reflns_theta_max         66.54
_diffrn_reflns_theta_min         6.01
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.7457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2009
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0598P)^2^+0.2392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                1805
_reflns_number_total             2009
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00731c2.cif
_cod_data_source_block           fro5799
_cod_depositor_comments
'Adding full bibliography for 7154501--7154502.cif.'
_cod_original_cell_volume        806.26(10)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7154501