Enantioselective Organocatalytic Desymmetrization of Cyclopentene-1,3-diones through Formal C(sp<sup>2</sup>)-H Amidation.
Liang, Hao; Zhou, Xiaotong; Zheng, Liyao; Wang, Jun; The Journal of organic chemistry 84 (2019) 11306–11315; doi:10.1021/acs.joc.9b01678

data_4033820
_publ_section_title
;
 Enantioselective Organocatalytic Desymmetrization of
 Cyclopentene-1,3-diones through Formal C(sp<sup>2</sup>)-H Amidation.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11306
_journal_page_last               11315
_journal_paper_doi               10.1021/acs.joc.9b01678
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration s
_chemical_formula_sum            'C2.42 H2.06 N0.12 O0.36'
_chemical_formula_weight         38.71
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.4190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            33
_cell_length_a                   6.54770(10)
_cell_length_b                   12.07930(10)
_cell_length_c                   20.9684(3)
_cell_measurement_reflns_used    9135
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8260
_cell_measurement_theta_min      4.1790
_cell_volume                     1657.92(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15315
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.104
_diffrn_reflns_theta_min         4.218
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89922
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0576P)^2^+0.0449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                6244
_reflns_number_total             6518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01678_si_002.cif
_cod_data_source_block           2221_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4033820
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              60
_shelx_hkl_checksum              11859