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_7158267
_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 H14 N2 O2'
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc26mhbp
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-11-16 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9560(2)
_cell_length_b                   8.4636(3)
_cell_length_c                   19.6496(6)
_cell_measurement_reflns_used    7797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4830
_cell_measurement_theta_min      2.2070
_cell_volume                     1156.83(6)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(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 0.991
_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   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 150.00   99
  2  \w     23.00  97.00   1.00    1.00    --   40.98-125.00  30.00   74
  3  \w     16.00 115.00   1.00    1.00    --   40.98  38.00  30.00   99
  4  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  90.00   97
  5  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00 -60.00   99
  6  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 -30.00   84
  7  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  30.00   84
  8  \w    101.00 178.00   1.00    1.00    --  106.95  94.00 -69.00   77
  9  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00 120.00   99
 10  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 -90.00  100
 11  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  90.00  109
 12  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-120.00  104
 13  \w     54.00 178.00   1.00    1.00    --  106.95  15.00   0.00  124
 14  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00 -30.00   84
 15  \w     79.00 178.00   1.00    1.00    --  106.95  30.00-180.00   99
 16  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00 -60.00  101
 17  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 150.00   81
;
_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      -0.0588678000
_diffrn_orient_matrix_UB_12      -0.0941738000
_diffrn_orient_matrix_UB_13      0.0638272000
_diffrn_orient_matrix_UB_21      -0.0619750000
_diffrn_orient_matrix_UB_22      -0.1394510000
_diffrn_orient_matrix_UB_23      -0.0453380000
_diffrn_orient_matrix_UB_31      0.2042519000
_diffrn_orient_matrix_UB_32      -0.0693182000
_diffrn_orient_matrix_UB_33      0.0046764000
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10363
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.661
_diffrn_reflns_theta_min         4.500
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79451
_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    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0591P)^2^+0.1410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2235
_reflns_number_total             2300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01327k2.cif
_cod_data_source_block           zhou-1-58
_cod_depositor_comments
'Adding full bibliography for 7158265--7158267.cif.'
_cod_database_code               7158267
_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:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              54045
_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 3.934
_oxdiff_exptl_absorpt_empirical_full_min 0.425