Amino Acid-Derived trans- N-Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility.
Amer, Mostafa Mahmoud; Abas, Hossay; Leonard, Daniel J.; Ward, John W.; Clayden, Jonathan; The Journal of organic chemistry 84 (2019) 7199–7206; doi:10.1021/acs.joc.9b00727

data_4034604
_publ_section_title
;
 Amino Acid-Derived trans- N-Chloroformylimidazolidinones: Scalable,
 Stereoselective Synthesis, Structure, and Utility.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7199
_journal_page_last               7206
_journal_paper_doi               10.1021/acs.joc.9b00727
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H25 Cl N2 O4'
_chemical_formula_sum            'C18 H25 Cl N2 O4'
_chemical_formula_weight         368.85
_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     iterative
_audit_creation_date             2018-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8127(2)
_cell_length_b                   12.4251(3)
_cell_length_c                   16.7855(4)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.80
_cell_measurement_theta_min      2.43
_cell_volume                     1837.99(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31523
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.188
_diffrn_reflns_theta_min         2.039
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0695 before and 0.0471 after correction. The Ratio of minimum to maximum transmission is 0.8359. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.488
_exptl_crystal_size_min          0.334
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1655 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.030(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4106
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+0.7373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3956
_reflns_number_total             4106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00727_si_002.cif
_cod_data_source_block           m_m39_compound_2c
_cod_database_code               4034604
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.890
_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. Restrained distances
 C9A-Cl1A
 1.78 with sigma of 0.004
 C9A-O2A
 1.22 with sigma of 0.005
 N2-C9A
 1.34 with sigma of 0.005
 O2A-Cl1A
 2.63 with sigma of 0.01
 N2-O2A
 2.29 with sigma of 0.01
 N2-Cl1A
 2.62 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Cl1A) = Uanis(O2) = Uanis(O2A)
Uanis(C9) = Uanis(C9A)
4. Others
 Sof(C9A)=Sof(Cl1A)=Sof(O2A)=1-FVAR(1)
 Sof(C9)=Sof(Cl1)=Sof(O2)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C16(H16)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C17(H17A,
 H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              62583
_shelx_hkl_checksum              40609
_olex2_submission_special_instructions 'No special instructions were received'