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_7126918
_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 ad
_chemical_formula_moiety         'C22 H21 Cl N4 O4 S'
_chemical_formula_sum            'C22 H21 Cl N4 O4 S'
_chemical_formula_weight         472.94
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8791(3)
_cell_length_b                   12.8935(3)
_cell_length_c                   14.4464(3)
_cell_measurement_reflns_used    3604
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.9760
_cell_measurement_theta_min      3.7040
_cell_volume                     2212.66(9)
_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 10.4115
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6611
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.634
_diffrn_reflns_theta_min         4.597
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.731
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_correction_T_min  0.465
_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    1.420
_exptl_crystal_description       blocks
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.219
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 1493 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.023(10)
_refine_ls_extinction_coef       0.0040(2)
_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   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0292P)^2^+0.5501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                3846
_reflns_number_total             4203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04413j10.cif
_cod_data_source_block           15
_cod_depositor_comments
'Adding full bibliography for 7126916--7126919.cif.'
_cod_original_cell_volume        2212.67(9)
_cod_database_code               7126918
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              22037
_shelx_hkl_checksum              51144