Diastereoselective synthesis of tetrahydrobenzo[b]azocines by Lu(OTf)3-catalyzed [4+4] cycloaddition of donor–acceptor cyclobutanes with anthranils
Hou, Meifeng; Li, Jiajun; Rao, Fucai; Chen, Zuliang; Wei, Yingjing; Chemical Communications  (2022) –; doi:10.1039/D2CC00829G

data_7130016
_publ_section_title
;
 Diastereoselective synthesis of tetrahydrobenzo[b]azocines by
 Lu(OTf)3-catalyzed [4+4] cycloaddition of donor--acceptor cyclobutanes
 with anthranils
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00829G
_journal_year                    2022
_chemical_formula_moiety         'C20 H25 N O4'
_chemical_formula_sum            'C20 H25 N O4'
_chemical_formula_weight         343.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bnf2j
_audit_creation_date             2022-04-05
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-05 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.54260(10)
_cell_length_b                   14.9631(2)
_cell_length_c                   12.0246(2)
_cell_measurement_reflns_used    5679
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      70.9940
_cell_measurement_theta_min      4.7240
_cell_volume                     1715.65(4)
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_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    -11.00  15.00   0.50    0.50    --   42.30 -38.00-150.00   52
  2  \w     80.00 105.00   0.50    0.50    --   42.30  77.00   0.00   50
  3  \w     24.00  78.00   0.50    0.50    --   42.30 -38.00-150.00  108
  4  \w     61.00  86.00   0.50    0.50    --   42.30 -82.00 -90.00   50
  5  \w     82.00 132.00   0.50    0.50    --   42.30  77.00 -60.00  100
  6  \w    -45.00 -15.00   0.50    0.50    --   42.30 -38.00-150.00   60
  7  \w     -4.00  86.00   0.50    0.50    --   42.30 -82.00-120.00  180
  8  \w     97.00 122.00   0.50    0.50    --   42.30  77.00-180.00   50
  9  \w     21.00  51.00   0.50    0.50    --  101.60 -82.00-150.00   60
 10  \w     57.00  90.00   0.50    0.50    --  101.60 -63.00 -90.00   66
 11  \w     13.00 131.00   0.50    0.50    --  101.60 -50.00  30.00  236
 12  \w     55.00 103.00   0.50    0.50    --  101.60 -82.00-150.00   96
 13  \w     56.00 144.00   0.50    0.50    --  101.60 -82.00 -90.00  176
 14  \w    108.00 134.00   0.50    0.50    --  101.60  82.00 -30.00   52
 15  \w     96.00 126.00   0.50    0.50    --  101.60 -63.00 -90.00   60
 16  \w     13.00 184.00   0.50    0.50    --  101.60 -12.00-180.00  342
 17  \w     47.00 128.00   0.50    0.50    --  101.60 -82.00 160.38  162
;
_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      -0.0661262000
_diffrn_orient_matrix_UB_12      -0.0172206000
_diffrn_orient_matrix_UB_13      0.1128599000
_diffrn_orient_matrix_UB_21      0.0084013000
_diffrn_orient_matrix_UB_22      0.1005237000
_diffrn_orient_matrix_UB_23      0.0266167000
_diffrn_orient_matrix_UB_31      -0.1472305000
_diffrn_orient_matrix_UB_32      0.0136415000
_diffrn_orient_matrix_UB_33      -0.0547999000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8689
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.588
_diffrn_reflns_theta_min         4.720
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95221
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0490P)^2^+0.3795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2885
_reflns_number_total             3264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00829g2.cif
_cod_data_source_block           1-81
_cod_database_code               7130016
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.903
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C4(H4), C13(H13), C14(H14), C16(H16), C17(H17), C5(H5)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_shelx_res_checksum              82994
_shelx_hkl_checksum              66511
_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 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.814