Diastereoselective construction of carbo-bridged polyheterocycles by a three-component tandem annulation reaction.
Wang, Maorui; Zhang, Min; Organic & biomolecular chemistry 21 (2023) 6342–6347; doi:10.1039/d3ob01013a

data_7159489
_publ_section_title
;
 Diastereoselective construction of carbo-bridged polyheterocycles by a
 three-component tandem annulation reaction.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6342
_journal_page_last               6347
_journal_paper_doi               10.1039/d3ob01013a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C24 H23 N3 O5'
_chemical_formula_sum            'C24 H23 N3 O5'
_chemical_formula_weight         433.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.121(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.1728(5)
_cell_length_b                   12.7276(3)
_cell_length_c                   19.2357(6)
_cell_measurement_reflns_used    9463
_cell_measurement_temperature    299(1)
_cell_measurement_theta_max      77.5740
_cell_measurement_theta_min      4.2910
_cell_volume                     4177.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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    -21.00   4.00   0.50    0.50    --   -0.90  80.00  82.00   50
  2  \w    -29.00  -4.00   0.50    0.50    --   -0.90 -80.00 -40.00   50
  3  \w     -1.00  24.00   0.50    0.50    --    0.90  80.00  82.00   50
  4  \w    -24.00  18.00   0.50    0.50    --    0.90 -80.00 -40.00   84
  5  \w    114.00 139.00   0.50    1.50    --  105.10  80.00  82.00   50
  6  \w     76.00 101.00   0.50    1.50    --  105.10 -80.00 -40.00   50
  7  \w    -39.00  33.00   0.50    0.50    --   -0.90 -82.00 120.00  144
  8  \w     49.00  74.00   0.50    0.50    --    0.90  38.00 -60.00   50
  9  \w    -39.00  34.00   0.50    0.50    --    0.90 -82.00 -90.00  146
 10  \w     82.00 193.00   0.50    1.50    --  105.10  82.00  60.00  222
 11  \w    162.00 194.00   0.50    1.50    --  105.10  77.00-180.00   64
 12  \w     82.00 188.00   0.50    1.50    --  105.10  82.00 120.00  212
 13  \w     86.00 142.00   0.50    1.50    --  105.10  82.00 150.00  112
 14  \w     83.00 143.00   0.50    1.50    --  105.10  77.00-180.00  120
 15  \w    153.00 194.00   0.50    1.50    --  105.10  82.00 150.00   82
 16  \w     19.00  97.00   0.50    1.50    --  105.10 -38.00   0.00  156
 17  \w    132.00 187.00   0.50    1.50    --  105.10  82.00   0.00  110
 18  \w     86.00 127.00   0.50    1.50    --  105.10  82.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0330452000
_diffrn_orient_matrix_UB_12      0.0950504000
_diffrn_orient_matrix_UB_13      -0.0249803000
_diffrn_orient_matrix_UB_21      0.0358198000
_diffrn_orient_matrix_UB_22      0.0428453000
_diffrn_orient_matrix_UB_23      0.0841438000
_diffrn_orient_matrix_UB_31      0.0760059000
_diffrn_orient_matrix_UB_32      -0.0614345000
_diffrn_orient_matrix_UB_33      0.0200078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13079
_diffrn_reflns_theta_full        77.78
_diffrn_reflns_theta_max         77.78
_diffrn_reflns_theta_min         4.33
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0558P)^2^+2.9318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                3839
_reflns_number_total             4302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ob01013a2.cif
_cod_data_source_block           wrj-210125wym
_cod_depositor_comments          'Adding full bibliography for 7159489.cif.'
_cod_database_code               7159489
_chemical_oxdiff_formula         'C H N O '
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_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 1.876
_oxdiff_exptl_absorpt_empirical_full_min 0.548