Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1<i>H</i>-azepines.
Craig, Donald; Spreadbury, Samuel R. J.; White, Andrew J. P.; Chemical communications (Cambridge, England) 56 (2020) 9803–9806; doi:10.1039/d0cc04413j

data_7126916
_publ_section_title
;
 Synthesis and hetero-Diels-Alder reactions of enantiomerically pure
 dihydro-1<i>H</i>-azepines.
;
_journal_issue                   68
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9803
_journal_page_last               9806
_journal_paper_doi               10.1039/d0cc04413j
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H17 Cl2 N O2 S'
_chemical_formula_sum            'C14 H17 Cl2 N O2 S'
_chemical_formula_weight         334.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-06-24 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.025(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9152(7)
_cell_length_b                   7.6328(5)
_cell_length_c                   16.9893(11)
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4900
_cell_measurement_theta_min      3.4090
_cell_volume                     1542.96(17)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.809
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5498
_diffrn_reflns_point_group_measured_fraction_full 0.725
_diffrn_reflns_point_group_measured_fraction_max 0.579
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_min         2.875
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       tablets
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       0.0068(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         4430
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0581P)^2^+0.5061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.334
_reflns_Friedel_fraction_full    0.419
_reflns_Friedel_fraction_max     0.313
_reflns_number_gt                3437
_reflns_number_total             4430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04413j10.cif
_cod_data_source_block           2a-3a
_cod_depositor_comments
'Adding full bibliography for 7126916--7126919.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126916
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              91823
_shelx_hkl_checksum              34913