Copper(i)-catalyzed asymmetric intramolecular C-arylation with ureas as the additives: highly enantioselective formation of spirooxindoles
Ma, Haowen; Feng, Jiajie; Zhou, Wei; Chen, Chen; Deng, Zhuoji; Zhou, Fengtao; Ouyang, Yifan; Zhang, Xinhao; Cai, Qian; Organic & Biomolecular Chemistry 19 (2021) 7480–7484; doi:10.1039/D1OB01327K

data_7158265
_publ_section_title
;
 Copper(i)-catalyzed asymmetric intramolecular C-arylation with ureas as
 the additives: highly enantioselective formation of spirooxindoles
;
_journal_issue                   34
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              7480
_journal_page_last               7484
_journal_paper_doi               10.1039/D1OB01327K
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H13 N O2'
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24
_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     direct
_audit_block_doi                 10.5517/ccdc.csd.cc26mh8m
_audit_creation_date             2019-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-16 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.887(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8556(3)
_cell_length_b                   6.92143(19)
_cell_length_c                   9.4280(3)
_cell_measurement_reflns_used    5299
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      73.2880
_cell_measurement_theta_min      4.9880
_cell_volume                     536.22(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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   -121.00   0.00   1.00    1.00    --  -40.73 -19.00 -90.00  121
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00   0.00  100
  3  \w      8.00 117.00   1.00    1.00    --   40.73  77.00  60.00  109
  4  \w     23.00  97.00   1.00    1.00    --   40.73-125.00-180.00   74
  5  \w      1.00  82.00   1.00    1.00    --   40.73 -99.00 -60.00   81
  6  \w    -34.00  65.00   1.00    1.00    --   40.73 -37.00 150.00   99
  7  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00 -30.00  104
  8  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  60.00   97
  9  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00 120.00   99
 10  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  30.00  104
 11  \w     81.00 171.00   1.00    1.00    --  106.95  45.00  30.00   90
 12  \w     81.00 108.00   1.00    1.00    --  106.95  61.00 -30.00   27
 13  \w     74.00 101.00   1.00    1.00    --  106.95  77.00   0.00   27
 14  \w     35.00 121.00   1.00    1.00    --  106.95-125.00-180.00   86
 15  \w    152.00 178.00   1.00    1.00    --  106.95  61.00 -60.00   26
 16  \w     85.00 112.00   1.00    1.00    --  106.95  45.00 -30.00   27
 17  \w     78.00 107.00   1.00    1.00    --  106.95  61.00 -60.00   29
 18  \w     74.00 101.00   1.00    1.00    --  106.95  77.00 -30.00   27
 19  \w     78.00 114.00   1.00    1.00    --  106.95  61.00  30.00   36
 20  \w    124.00 176.00   1.00    1.00    --  106.95  30.00 -60.00   52
 21  \w     81.00 123.00   1.00    1.00    --  106.95  61.00   0.00   42
 22  \w     95.00 170.00   1.00    1.00    --  106.95 125.00 -30.00   75
 23  \w     50.00 139.00   1.00    1.00    --  106.95 -77.00 -30.00   89
 24  \w     78.00 104.00   1.00    1.00    --  106.95  61.00   0.00   26
 25  \w    153.00 178.00   1.00    1.00    --  106.95   0.00 -30.00   25
 26  \w   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00 120.00  109
 27  \w   -115.00 -13.00   1.00    1.00    --  -41.48 -57.00 -90.00  102
 28  \w   -115.00 -13.00   1.00    1.00    --  -41.48 -57.00 150.00  102
 29  \w   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00-120.00  109
 30  \w   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00 -90.00  109
 31  \w    -33.00  66.00   1.00    1.00    --   41.48 -37.00 -30.00   99
 32  \w     17.00 116.00   1.00    1.00    --   41.48  37.00-150.00   99
 33  \w     74.00 173.00   1.00    1.00    --  106.95  77.00-150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1305269000
_diffrn_orient_matrix_UB_12      -0.1177409000
_diffrn_orient_matrix_UB_13      0.1250066000
_diffrn_orient_matrix_UB_21      -0.1092033000
_diffrn_orient_matrix_UB_22      -0.0045988000
_diffrn_orient_matrix_UB_23      0.0945549000
_diffrn_orient_matrix_UB_31      -0.0785302000
_diffrn_orient_matrix_UB_32      -0.1889194000
_diffrn_orient_matrix_UB_33      -0.0801640000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7302
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.351
_diffrn_reflns_theta_min         5.056
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 849 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0697P)^2^+0.0933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                2015
_reflns_number_total             2055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01327k2.cif
_cod_data_source_block           cc1
_cod_depositor_comments
'Adding full bibliography for 7158265--7158267.cif.'
_cod_database_code               7158265
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 2.587
_oxdiff_exptl_absorpt_empirical_full_min 0.419