Rapid construction of indole-fused 8–10 membered lactones via a tandem reaction
Li, Zhen; Ma, Shiqiang; Liu, Fuhai; Ma, Ruize; Zhao, Jipeng; Xie, Xingang; She, Xuegong; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01110G

data_7158790
_publ_section_title
;
 Rapid construction of indole-fused 8--10 membered lactones via a tandem
 reaction
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01110G
_journal_year                    2022
_chemical_formula_moiety         'C17 H21 N O2'
_chemical_formula_sum            'C17 H21 N O2'
_chemical_formula_weight         271.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-05-03 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.489(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8106(2)
_cell_length_b                   17.8042(2)
_cell_length_c                   9.8334(2)
_cell_measurement_reflns_used    11077
_cell_measurement_temperature    295.99(10)
_cell_measurement_theta_max      77.3510
_cell_measurement_theta_min      4.9830
_cell_volume                     1495.08(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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_environment      air
_diffrn_ambient_temperature      295.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.938
_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     96.00 167.00   0.50    0.06    --  107.75  37.00   0.00  142
  2  \w    144.00 175.00   0.50    0.06    --  107.75  80.00  73.00   62
  3  \w    116.00 171.00   0.50    0.06    --  107.75  37.00 -30.00  110
  4  \w    116.00 173.00   0.50    0.06    --  107.75  19.00-150.00  114
  5  \w    -24.00  29.00   0.50    0.05    --   47.57 -80.00 -50.00  106
  6  \w    -25.00  23.00   0.50    0.05    --   47.57 -19.00 -30.00   96
  7  \w    -12.00  13.00   0.50    0.05    --   47.57 -19.00 -60.00   50
  8  \w    -25.00  39.00   0.50    0.05    --   47.57 -37.00-150.00  128
  9  \w    -25.00   0.00   0.50    0.05    --   47.57 -19.00-150.00   50
 10  \w     49.00 113.00   0.50    0.06    --  107.75 -80.00 -50.00  128
 11  \w     35.00  61.00   0.50    0.06    --  107.75 -57.00  90.00   52
 12  \w     35.00  60.00   0.50    0.06    --  107.75 -57.00 150.00   50
 13  \w     36.00  62.00   0.50    0.06    --  107.75 -57.00   0.00   52
 14  \w     36.00  62.00   0.50    0.06    --  107.75 -57.00-120.00   52
 15  \w    -69.00 -44.00   0.50    0.05    --  -47.57  80.00  73.00   50
 16  \w    -41.00  15.00   0.50    0.05    --  -47.57  80.00  73.00  112
 17  \w    -68.00 -27.00   0.50    0.06    -- -100.00  57.00  90.00   82
 18  \w    -61.00 -30.00   0.50    0.06    -- -100.00  57.00 120.00   62
 19  \w    -76.00 -51.00   0.50    0.06    -- -100.00  80.00  73.00   50
 20  \w    -69.00 -27.00   0.50    0.06    -- -100.00  57.00  60.00   84
 21  \w    -67.00 -42.00   0.50    0.06    -- -100.00  57.00 -60.00   50
 22  \w    -68.00 -32.00   0.50    0.06    -- -100.00  57.00 -90.00   72
 23  \w   -151.00 -87.00   0.50    0.06    -- -100.00 -80.00 -50.00  128
 24  \w   -154.00-128.00   0.50    0.06    -- -100.00 -80.00 -50.00   52
 25  \w     71.00 103.00   0.50    0.05    --   47.57-154.00  77.00   64
 26  \w    -26.00  23.00   0.50    0.05    --   47.57 -19.00-120.00   98
 27  \w     36.00  62.00   0.50    0.05    --   47.57  57.00-180.00   52
 28  \w     -6.00  29.00   0.50    0.05    --   47.57 -37.00 -90.00   70
 29  \w     88.00 120.00   0.50    0.05    --   47.57  57.00-180.00   64
 30  \w     12.00  39.00   0.50    0.05    --   47.57 -37.00  90.00   54
 31  \w    -57.00 -27.00   0.50    0.06    -- -100.00 125.00  60.00   60
 32  \w   -168.00-142.00   0.50    0.06    -- -100.00-125.00-180.00   52
 33  \w    -83.00 -57.00   0.50    0.06    -- -100.00  77.00 -90.00   52
 34  \w   -119.00 -87.00   0.50    0.06    -- -100.00-125.00-180.00   64
 35  \w   -107.00 -60.00   0.50    0.06    -- -100.00 125.00   0.00   94
 36  \w   -111.00 -85.00   0.50    0.06    -- -100.00 125.00  60.00   52
 37  \w   -172.00-109.00   0.50    0.06    -- -100.00 -37.00 150.00  126
 38  \w     58.00  96.00   0.50    0.06    --  107.75-120.00-124.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1784948000
_diffrn_orient_matrix_UB_12      -0.0116072000
_diffrn_orient_matrix_UB_13      0.0953445000
_diffrn_orient_matrix_UB_21      0.0250088000
_diffrn_orient_matrix_UB_22      0.0851672000
_diffrn_orient_matrix_UB_23      -0.0051055000
_diffrn_orient_matrix_UB_31      -0.0060236000
_diffrn_orient_matrix_UB_32      0.0101050000
_diffrn_orient_matrix_UB_33      0.1525723000
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14667
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.485
_diffrn_reflns_theta_min         4.968
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0110(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.2189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2695
_reflns_number_total             2988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01110g2.cif
_cod_data_source_block           lizhen_0218-2_auto
_cod_database_code               7158790
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.845
_reflns_odcompleteness_completeness 98.74
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C12(H12), C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              11588
_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 3.567
_oxdiff_exptl_absorpt_empirical_full_min 0.385