Stereoselective Synthesis of Functionalized Tetrahydro-1H-1,2-diazepines by N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation.
Zhu, Shi-Ya; Zhang, Yuanzhen; Wang, Wei; Hui, Xin-Ping; Organic letters 19 (2017) 5380–5383; doi:10.1021/acs.orglett.7b02657

data_1547357
_publ_section_title
;
 Stereoselective Synthesis of Functionalized Tetrahydro-1H-1,2-diazepines
 by N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5380
_journal_page_last               5383
_journal_paper_doi               10.1021/acs.orglett.7b02657
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H25 N2 O5 S2'
_chemical_formula_sum            'C25 H25 N2 O5 S2'
_chemical_formula_weight         497.59
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8958(4)
_cell_length_b                   16.9193(6)
_cell_length_c                   18.2874(8)
_cell_measurement_reflns_used    1905
_cell_measurement_temperature    290.84(10)
_cell_measurement_theta_max      25.2150
_cell_measurement_theta_min      3.7800
_cell_volume                     2443.04(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      290.84(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9958
_diffrn_measured_fraction_theta_max 0.8234
_diffrn_measurement_details
;
  1 omega  -10.00   19.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000    0.0000 29

  2 omega  -38.00   87.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -19.0000  -60.0000 125

  3 omega   22.00   93.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   38.0000  -30.0000 71
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0310886000
_diffrn_orient_matrix_UB_12      0.0128707000
_diffrn_orient_matrix_UB_13      -0.0343641000
_diffrn_orient_matrix_UB_21      -0.0842314000
_diffrn_orient_matrix_UB_22      -0.0031115000
_diffrn_orient_matrix_UB_23      0.0132013000
_diffrn_orient_matrix_UB_31      0.0034578000
_diffrn_orient_matrix_UB_32      0.0397767000
_diffrn_orient_matrix_UB_33      0.0121880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9361
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.5926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                3297
_reflns_number_total             4547
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02657_si_002.cif
_cod_data_source_block           zhushy_1227
_cod_depositor_comments          'Adding full bibliography for 1547357.cif.'
_cod_original_cell_volume        2443.03(18)
_cod_database_code               1547357
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17), C18(H18), C20(H20),
 C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C25(H25A,H25B,H25C)
;
_olex2_date_sample_data_collection 2016-12-27
_olex2_submission_special_instructions 'No special instructions were received'