Stereoselective [4 + 3] annulation of azadienes and ethyl 4-bromo-3-oxobutanoate: construction of benzindeno-fused azepine derivatives.
Shen, Jinhui; Yu, Aimin; Meng, Xiangtai; Organic & biomolecular chemistry 19 (2021) 9026–9030; doi:10.1039/d1ob01749g

data_7158322
_publ_section_title
;
 Stereoselective [4 + 3] annulation of azadienes and ethyl
 4-bromo-3-oxobutanoate: construction of benzindeno-fused azepine
 derivatives.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9026
_journal_page_last               9030
_journal_paper_doi               10.1039/d1ob01749g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C29 H27 N O5 S'
_chemical_formula_sum            'C29 H27 N O5 S'
_chemical_formula_weight         501.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-07 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                97.036(14)
_cell_angle_beta                 110.448(14)
_cell_angle_gamma                105.848(14)
_cell_formula_units_Z            2
_cell_length_a                   10.9106(16)
_cell_length_b                   11.628(2)
_cell_length_c                   11.7739(19)
_cell_measurement_reflns_used    1483
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      32.8570
_cell_measurement_theta_min      3.1980
_cell_volume                     1306.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      2.00  41.00   1.00   55.00    --   30.00  54.00-120.00   39
  2  \w     83.00 108.00   1.00   55.00    --   30.00  54.00 120.00   25
  3  \w    -74.00  12.00   1.00   55.00    --   30.00  54.00 120.00   86
  4  \w    -74.00 108.00   1.00   55.00    --   30.00  54.00 -30.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0186961000
_diffrn_orient_matrix_UB_12      0.0105189000
_diffrn_orient_matrix_UB_13      -0.0608669000
_diffrn_orient_matrix_UB_21      -0.0646737000
_diffrn_orient_matrix_UB_22      0.0017050000
_diffrn_orient_matrix_UB_23      -0.0004998000
_diffrn_orient_matrix_UB_31      0.0301582000
_diffrn_orient_matrix_UB_32      0.0644718000
_diffrn_orient_matrix_UB_33      0.0261786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.724
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
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    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     436
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0691
_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^)+(0.1011P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.2161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2596
_reflns_number_total             4571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01749g2.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7158322--7158326.cif.'
_cod_database_code               7158322
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.87
_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. Restrained distances
 H1A-C1
 0.96 with sigma of 0.002
 C1-H1B
 0.96 with sigma of 0.002
 H00A-H00C = H1B-H1A
 1.566 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
C007 \\sim C008 \\sim C009 \\sim C00A \\sim C00B \\sim C00C \\sim C00D \\sim
C00E \\sim C00G \\sim C00H \\sim C00I \\sim C00J \\sim C00K \\sim C00L \\sim
C00M \\sim C00N \\sim C00O \\sim C00P \\sim C00Q \\sim C00R \\sim C00S \\sim
C00T \\sim C00U \\sim C00V \\sim C00W \\sim C00X \\sim C00Y \\sim C1 \\sim C0AA
\\sim C2: within 2.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
4. Others
 Fixed Sof: C0AA(0.5) H0AA(0.5) H0AB(0.5) H0AC(0.5) C2(0.5) H2A(0.5) H2B(0.5)
 H2C(0.5)
5.a Ternary CH refined with riding coordinates:
 C007(H007), C00B(H00B)
5.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00C), C00M(H00D,H00F)
5.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00K(H00K), C00L(H00L), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X)
5.d Idealised Me refined as rotating group:
 C00Y(H00H,H00I,H00J), C0AA(H0AA,H0AB,H0AC), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              34426
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.842