Twisted N-Acyl-hydantoins: Rotationally Inverted Urea-Imides of Relevance in N-C(O) Cross-coupling.
Szostak, Roman; Liu, Chengwei; Lalancette, Roger; Szostak, Michal; The Journal of organic chemistry 83 (2018) 14676–14682; doi:10.1021/acs.joc.8b02691

data_4035688
_publ_section_title
;
 Twisted N-Acyl-hydantoins: Rotationally Inverted Urea-Imides of Relevance
 in N-C(O) Cross-coupling.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14676
_journal_page_last               14682
_journal_paper_doi               10.1021/acs.joc.8b02691
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C10 H8 N2 O3'
_chemical_formula_sum            'C10 H8 N2 O3'
_chemical_formula_weight         204.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.641(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0445(3)
_cell_length_b                   5.4776(1)
_cell_length_c                   15.3754(5)
_cell_measurement_reflns_used    5734
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.81
_cell_measurement_theta_min      4.07
_cell_volume                     914.18(4)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
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_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
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_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8191
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.824
_diffrn_reflns_theta_min         4.073
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.106
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_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0314P)^2^+0.3728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0685
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1536
_reflns_number_total             1637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02691_si_002.cif
_cod_data_source_block           180711RAL_CHENGWEI_HYDANTOIN_100K_0m_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035688
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.633
_shelx_estimated_absorpt_t_max   0.906
_shelx_res_checksum              85926
_shelx_hkl_checksum              67021