Copper/guanidine-catalyzed asymmetric alkynylation of isatin-derived ketimines.
Chen, Quangang; Xie, Lihua; Li, Zhaojing; Tang, Yu; Zhao, Peng; Lin, Lili; Feng, Xiaoming; Liu, Xiaohua; Chemical communications (Cambridge, England) 54 (2018) 678–681; doi:10.1039/c7cc08920a

data_7121022
_publ_section_title
;
 Copper/guanidine-catalyzed asymmetric alkynylation of isatin-derived
 ketimines.
;
_journal_issue                   6
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              678
_journal_page_last               681
_journal_paper_doi               10.1039/c7cc08920a
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H25 Cl N2 O3'
_chemical_formula_sum            'C27 H25 Cl N3 O3'
_chemical_formula_weight         474.95
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-06 deposited with the CCDC.
2017-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5916(2)
_cell_length_b                   14.4910(4)
_cell_length_c                   14.7866(3)
_cell_measurement_reflns_used    8537
_cell_measurement_temperature    296.31(10)
_cell_measurement_theta_max      72.5060
_cell_measurement_theta_min      4.3270
_cell_volume                     2483.76(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      296.31(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -90.0000 66

  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000   60.0000 84

  3 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000   60.0000 66

  4 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  -90.0000 88

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -120.0000 84

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000 -180.0000 74

  7 omega   39.00  109.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

  8 omega   98.00  177.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   86.0000   87.0000 79

  9 omega   38.00   91.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 10 omega   39.00  109.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 11 omega   41.00  126.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 85

 12 omega   40.00   98.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 13 omega   38.00   91.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 14 omega   38.00   91.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 15 omega   57.00  150.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -120.0000 93

 16 omega   91.00  176.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

 17 omega    9.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000    0.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0681602000
_diffrn_orient_matrix_UB_12      -0.0840659000
_diffrn_orient_matrix_UB_13      0.0347413000
_diffrn_orient_matrix_UB_21      -0.0070898000
_diffrn_orient_matrix_UB_22      -0.0443074000
_diffrn_orient_matrix_UB_23      -0.0944647000
_diffrn_orient_matrix_UB_31      0.1139227000
_diffrn_orient_matrix_UB_32      0.0478441000
_diffrn_orient_matrix_UB_33      -0.0264693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14531
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.823
_diffrn_reflns_theta_min         4.848
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1992 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0913P)^2^+0.1949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4738
_reflns_number_total             4857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08920a2.cif
_cod_data_source_block           fxm-cqg72-150k
_cod_depositor_comments          'Adding full bibliography for 7121022.cif.'
_cod_original_cell_volume        2483.77(10)
_cod_database_code               7121022
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.80
_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 Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00U(H00U), C00V(H00V)
2.c Idealised Me refined as rotating group:
 C00W(H00C,H00D,H00E), C00X(H00L,H00M,H00P), C00Y(H00S,H00W,H00X)
;
_olex2_date_sample_data_collection 2017-06-28
_olex2_submission_special_instructions 'No special instructions were received'