Organocatalytic enantioselective construction of axially chiral (1<i>H</i>)-isochromen-1-imines.
Wang, Ying; Yang, Yang; Xu, Shiyu; Huang, Aima; Chen, Lu; Xie, Yubao; Liu, Pengyutian; Hong, Liang; Li, Guofeng; Organic & biomolecular chemistry 20 (2022) 3277–3282; doi:10.1039/d2ob00379a

data_7158625
_publ_section_title
;
 Organocatalytic enantioselective construction of axially chiral
 (1<i>H</i>)-isochromen-1-imines.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3277
_journal_page_last               3282
_journal_paper_doi               10.1039/d2ob00379a
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H16 I N O2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C25.5 H17 Cl I N O2'
_chemical_formula_weight         531.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-10-01 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.3440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.46880(10)
_cell_length_b                   15.04240(10)
_cell_length_c                   14.45880(10)
_cell_measurement_reflns_used    39394
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1570
_cell_measurement_theta_min      3.1570
_cell_volume                     2205.93(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_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    -78.00 -48.00   0.50    0.05    --  -46.62  -6.00  31.00   60
  2  \w    -35.00  -7.00   0.50    0.05    --  -46.62   6.00-153.00   56
  3  \w     34.00  59.00   0.50    0.05    --   46.62   6.00-153.00   50
  4  \w     10.00  35.00   0.50    0.05    --   46.62  -6.00  31.00   50
  5  \w    -90.00 -65.00   0.50    0.18    -- -100.00   6.00-153.00   50
  6  \w   -152.00-112.00   0.50    0.18    -- -100.00  -6.00  31.00   80
  7  \w    108.00 152.00   0.50    0.18    --  107.00   6.00-153.00   88
  8  \w     35.00 118.00   0.50    0.18    --  107.00  -6.00  31.00  166
  9  \w    -63.00 -30.00   0.50    0.05    --  -46.62 -57.00 -90.00   66
 10  \w    -81.00 -33.00   0.50    0.05    --  -46.62 -19.00 -60.00   96
 11  \w    -58.00 -31.00   0.50    0.05    --  -46.62 -57.00 -30.00   54
 12  \w    -70.00 -32.00   0.50    0.05    --  -46.62 -38.00   0.00   76
 13  \w    -55.00 -24.00   0.50    0.05    --  -46.62 -77.00 -90.00   62
 14  \w    -54.00 -28.00   0.50    0.05    --  -46.62 -68.00 -53.11   52
 15  \w    -53.00 -27.00   0.50    0.05    --  -46.62 -77.00 -30.00   52
 16  \w     27.00  64.00   0.50    0.05    --   46.62  77.00  30.00   74
 17  \w     23.00  75.00   0.50    0.05    --   46.62  77.00 -60.00  104
 18  \w     28.00  62.00   0.50    0.05    --   46.62  77.00   0.00   68
 19  \w     16.00  89.00   0.50    0.05    --   46.62-125.00-150.00  146
 20  \w     23.00  76.00   0.50    0.05    --   46.62  77.00 -90.00  106
 21  \w     23.00  48.00   0.50    0.05    --   46.62  77.00 -30.00   50
 22  \w     32.00  77.00   0.50    0.05    --   46.62  38.00   0.00   90
 23  \w     34.00  70.00   0.50    0.05    --   46.62  57.00 -30.00   72
 24  \w     46.00  73.00   0.50    0.05    --   46.62  38.00-120.00   54
 25  \w     83.00 115.00   0.50    0.05    --   46.62  38.00   0.00   64
 26  \w   -114.00 -80.00   0.50    0.18    -- -100.00 -68.00   1.32   68
 27  \w   -102.00 -76.00   0.50    0.18    -- -100.00 -78.00 -77.11   52
 28  \w   -113.00 -78.00   0.50    0.18    -- -100.00 -73.00-118.26   70
 29  \w   -163.00-138.00   0.50    0.18    -- -100.00 -78.00 -77.11   50
 30  \w   -173.00-117.00   0.50    0.18    -- -100.00 -77.00-120.00  112
 31  \w   -172.00 -87.00   0.50    0.18    -- -100.00 -53.00 -65.09  170
 32  \w   -116.00 -74.00   0.50    0.18    -- -100.00 -83.00   2.45   84
 33  \w   -101.00 -76.00   0.50    0.18    -- -100.00 -77.00-120.00   50
 34  \w   -173.00-110.00   0.50    0.18    -- -100.00 -77.00-150.00  126
 35  \w   -106.00 -76.00   0.50    0.18    -- -100.00 -77.00-150.00   60
 36  \w   -102.00 -73.00   0.50    0.18    -- -100.00 -83.00 -88.48   58
 37  \w   -164.00-138.00   0.50    0.18    -- -100.00 -80.00 -15.54   52
 38  \w   -170.00 -83.00   0.50    0.18    -- -100.00 -61.00 -90.00  174
 39  \w   -100.00 -75.00   0.50    0.18    -- -100.00 -82.00-129.49   50
 40  \w   -161.00-135.00   0.50    0.18    -- -100.00 -68.00   1.32   52
 41  \w   -164.00-125.00   0.50    0.18    -- -100.00 -83.00   2.45   78
 42  \w   -101.00 -75.00   0.50    0.18    -- -100.00 -82.00 -57.19   52
 43  \w   -164.00-138.00   0.50    0.18    -- -100.00 -82.00-129.49   52
 44  \w   -101.00 -76.00   0.50    0.18    -- -100.00 -78.00 -42.10   50
 45  \w   -102.00 -77.00   0.50    0.18    -- -100.00 -75.00   3.86   50
 46  \w    -98.00 -73.00   0.50    0.18    -- -100.00 -83.00-101.04   50
 47  \w   -104.00 -78.00   0.50    0.18    -- -100.00 -86.00  40.32   52
 48  \w   -118.00 -73.00   0.50    0.18    -- -100.00 -83.00 -78.40   90
 49  \w   -101.00 -76.00   0.50    0.18    -- -100.00 -77.00-145.61   50
 50  \w   -101.00 -76.00   0.50    0.18    -- -100.00 -77.00  30.00   50
 51  \w   -162.00-136.00   0.50    0.18    -- -100.00 -77.00-145.61   52
 52  \w   -107.00 -81.00   0.50    0.18    -- -100.00 -66.00 -87.86   52
 53  \w   -118.00 -75.00   0.50    0.18    -- -100.00 -83.00 -39.18   86
 54  \w   -101.00 -75.00   0.50    0.18    -- -100.00 -79.00 -12.46   52
 55  \w    -74.00 -28.00   0.50    0.18    -- -100.00  77.00 120.00   92
 56  \w   -162.00-136.00   0.50    0.18    -- -100.00 -83.00 -39.18   52
 57  \w   -107.00 -81.00   0.50    0.18    -- -100.00 -66.00-114.57   52
 58  \w   -108.00 -82.00   0.50    0.18    -- -100.00 -64.00-146.26   52
 59  \w   -105.00 -80.00   0.50    0.18    -- -100.00 -67.00-130.34   50
 60  \w   -105.00 -76.00   0.50    0.18    -- -100.00 -77.00 -90.00   58
 61  \w   -106.00 -76.00   0.50    0.18    -- -100.00 -77.00   0.00   60
 62  \w   -172.00 -74.00   0.50    0.18    -- -100.00 -82.00 -20.45  196
 63  \w   -172.00-125.00   0.50    0.18    -- -100.00 -45.00   0.00   94
 64  \w   -120.00 -85.00   0.50    0.18    -- -100.00 -45.00   0.00   70
 65  \w   -123.00 -95.00   0.50    0.18    -- -100.00  77.00 120.00   56
 66  \w   -122.00 -81.00   0.50    0.18    -- -100.00 -67.00 -67.60   82
 67  \w   -110.00 -76.00   0.50    0.18    -- -100.00 -80.00 -15.54   68
 68  \w   -169.00-108.00   0.50    0.18    -- -100.00 -83.00-101.04  122
 69  \w   -106.00 -75.00   0.50    0.18    -- -100.00 -80.00 -28.23   62
 70  \w   -111.00 -79.00   0.50    0.18    -- -100.00 -74.00  48.81   64
 71  \w   -130.00 -82.00   0.50    0.18    -- -100.00 -61.00 -30.00   96
 72  \w   -107.00 -81.00   0.50    0.18    -- -100.00 -66.00 -63.46   52
 73  \w     34.00 109.00   0.50    0.18    --  107.00 -94.00 -60.00  150
 74  \w     35.00  85.00   0.50    0.18    --  107.00 -94.00 -90.00  100
 75  \w     90.00 122.00   0.50    0.18    --  107.00 -61.00 -90.00   64
 76  \w     43.00  69.00   0.50    0.18    --  107.00 -61.00 -90.00   52
 77  \w     73.00 108.00   0.50    0.18    --  107.00 -94.00 -30.00   70
 78  \w    136.00 165.00   0.50    0.18    --  107.00  61.00-150.00   58
 79  \w     36.00  69.00   0.50    0.18    --  107.00 -94.00 -30.00   66
 80  \w     36.00 108.00   0.50    0.18    --  107.00 -94.00-120.00  144
 81  \w     37.00  70.00   0.50    0.18    --  107.00 -94.00  90.00   66
 82  \w     34.00  86.00   0.50    0.18    --  107.00 -94.00   0.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0834837000
_diffrn_orient_matrix_UB_12      0.0044503000
_diffrn_orient_matrix_UB_13      -0.1038859000
_diffrn_orient_matrix_UB_21      -0.1267451000
_diffrn_orient_matrix_UB_22      -0.0077205000
_diffrn_orient_matrix_UB_23      0.0354136000
_diffrn_orient_matrix_UB_31      -0.0059862000
_diffrn_orient_matrix_UB_32      0.1020141000
_diffrn_orient_matrix_UB_33      0.0072621000
_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  0.0351
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49680
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.753
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       block
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 3615 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         8565
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0349P)^2^+2.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0698
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                8348
_reflns_number_total             8565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00379a2.cif
_cod_data_source_block           yangy_201109_3
_cod_depositor_comments
;
          Adding full bibliography for 7158625.cif.

2024-10-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C51 H34 Cl2 I2 N2 O4'
_cod_original_formula_weight         1063.50
_cod_original_formula_moiety         '2(C25 H16 I N O2), C H2 Cl2'
_cod_original_formula_units_Z            2
_cod_database_code               7158625
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.569
_shelx_estimated_absorpt_t_min   0.412
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C60(H60A,H60B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C26(H26), C8(H8), C43(H43), C5(H5), C7(H7), C18(H18), C6(H6),
 C24(H24), C27(H27), C19(H19), C57(H57), C25(H25), C16(H16), C47(H47), C36(H36),
  C34(H34), C56(H56), C42(H42), C48(H48), C53(H53), C37(H37), C35(H35),
 C14(H14), C45(H45), C46(H46), C54(H54), C28(H28), C17(H17), C55(H55)
2.c Tetrahedral OH refined with riding coordinates:
 O50(H50)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_shelx_res_checksum              98935
_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 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.819