Development of Biligands Magnesium Catalysis in Asymmetric Conjugate Reactions of C3-Pyrrolyl-Oxindoles.
Wang, Kezhou; Wang, Linqing; Liu, Xihong; Li, Dan; Zhu, Haiyong; Wang, Pengxin; Liu, Yuyang; Yang, Dongxu; Wang, Rui; Organic letters 19 (2017) 4351–4354; doi:10.1021/acs.orglett.7b02044

data_1547082
_publ_section_title
;
 Development of Biligands Magnesium Catalysis in Asymmetric Conjugate
 Reactions of C3-Pyrrolyl-Oxindoles.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4351
_journal_page_last               4354
_journal_paper_doi               10.1021/acs.orglett.7b02044
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H21 Cl N2 O'
_chemical_formula_sum            'C24 H21 Cl N2 O'
_chemical_formula_weight         388.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5290(5)
_cell_length_b                   8.7083(6)
_cell_length_c                   29.448(2)
_cell_measurement_reflns_used    1658
_cell_measurement_temperature    291.0(2)
_cell_measurement_theta_max      27.0080
_cell_measurement_theta_min      4.1230
_cell_volume                     1930.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      291.0(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -16.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -150.0000 31

  2 omega  -34.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  150.0000 117

  3 omega  -11.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  150.0000 26

  4 omega  -50.00  -24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -38.0000 -120.0000 26

  5 omega   -8.00   43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   90.0000 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0343920000
_diffrn_orient_matrix_UB_12      -0.0230335000
_diffrn_orient_matrix_UB_13      0.0213706000
_diffrn_orient_matrix_UB_21      -0.0140693000
_diffrn_orient_matrix_UB_22      0.0752108000
_diffrn_orient_matrix_UB_23      0.0085946000
_diffrn_orient_matrix_UB_31      -0.0863906000
_diffrn_orient_matrix_UB_32      -0.0215731000
_diffrn_orient_matrix_UB_33      0.0070753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7559
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.014
_diffrn_reflns_theta_min         3.410
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0387P)^2^+0.3202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2676
_reflns_number_total             3795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02044_si_002.cif
_cod_data_source_block           wangkzh_0328
_cod_original_cell_volume        1930.7(2)
_cod_database_code               1547082
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2017-03-28
_olex2_submission_special_instructions 'No special instructions were received'