The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-Aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction. Access to Privileged Chemical Structures and Scope and Limitations of the Method.
Bell, Abbegail C.; Boomsma, Alex B.; Flikweert, Niecia E.; Hohlman, Robert M.; Zhang, Shiyuan; Blankespoor, Ronald L.; Biros, Shannon M.; Staples, Richard J.; Brickner, Steven J.; Barbachyn, Michael Robert; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03400

data_4038328
_publ_section_title
;
 The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones
 and Tetrahydro-3-Aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation
 Reaction. Access to Privileged Chemical Structures and Scope and
 Limitations of the Method.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03400
_journal_year                    2020
_chemical_formula_moiety         'I, C16 H16 I N2 O2, 0.5(C7 H8)'
_chemical_formula_sum            'C19.5 H20 I2 N2 O2'
_chemical_formula_weight         568.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-07-18
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4039(16)
_cell_length_b                   7.6320(8)
_cell_length_c                   32.433(3)
_cell_measurement_reflns_used    9540
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.51
_cell_volume                     4060.4(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            46879
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.374
_diffrn_reflns_theta_min         2.483
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.113
_exptl_absorpt_correction_T_max  0.9478
_exptl_absorpt_correction_T_min  0.4921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1278 before and 0.0695 after correction. The Ratio of minimum to maximum transmission is 0.5192. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_description       needle
_exptl_crystal_F_000             2184
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.06
_refine_diff_density_max         3.393
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.203
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         7435
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0560P)^2^+41.9177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6767
_reflns_number_total             7435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03400_si_002.cif
_cod_data_source_block           MRB615A
_cod_original_formula_sum        'C19.50 H20 I2 N2 O2'
_cod_database_code               4038328
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.835
_shelx_estimated_absorpt_t_min   0.412
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.52(8) 0.48(8)
2. 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
3. Restrained distances
 C2R-C1R
 1.45 with sigma of 0.02
 C2S-C1S
 1.45 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(C1S) = Uiso(C1R)
5. Others
 Fixed Sof: C1R(0.5) H1RA(0.5) H1RB(0.5) H1RC(0.5) C1S(0.5) H1SA(0.5)
 H1SB(0.5) H1SC(0.5) C5R(0.5) H5R(0.5) C6R(0.5) H6R(0.5) C7R(0.5) H7R(0.5)
 C2R(0.5) C3R(0.5) H3R(0.5) C4R(0.5) H4R(0.5) C5S(0.5) H5S(0.5) C6S(0.5)
 H6S(0.5) C7S(0.5) H7S(0.5) C2S(0.5) C3S(0.5) H3S(0.5) C4S(0.5) H4S(0.5)
6.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2B(H2B)
6.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C3A(H3AA,H3AB), C9A(H9AA,H9AB), C1B(H1BA,H1BB), C3B(H3BA,
 H3BB), C9B(H9BA,H9BB)
6.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C11A(H11A), C12A(H12A), C13A(H13A),
 C14A(H14A), C15A(H15A), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C11B(H11B),
 C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B), C5R(H5R), C6R(H6R), C7R(H7R),
 C3R(H3R), C4R(H4R), C5S(H5S), C6S(H6S), C7S(H7S), C3S(H3S), C4S(H4S)
6.d Fitted hexagon refined as free rotating group:
 C5R(C6R,C7R,C2R,C3R,C4R), C5S(C6S,C7S,C2S,C3S,C4S)
6.e Idealised Me refined as rotating group:
 C1R(H1RA,H1RB,H1RC), C1S(H1SA,H1SB,H1SC)
;
_shelx_res_checksum              91782
_shelx_hkl_checksum              770
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'mp 136-7'
_olex2_submission_special_instructions 'No special instructions were received'