Synthesis of Oxazolidinones: Rhodium-Catalyzed C–H Amination of N-Mesyloxycarbamates.
Lebel, Helene; Mamani Laparra, Laura; Khalifa, Maroua; Trudel, Carl; Audubert, Clément; Szponarski, Mathieu; Dicaire-Leduc, Cédric; Azek, Emna; Ernzerhof, Matthias; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00378A

data_7155568
_publ_section_title
;
 Synthesis of Oxazolidinones: Rhodium-Catalyzed C--H Amination of
 N-Mesyloxycarbamates.
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00378A
_journal_year                    2017
_chemical_formula_moiety         'C10 H11 N O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-02-15 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.32966(13)
_cell_length_b                   8.77119(8)
_cell_length_c                   14.61018(13)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.766
_cell_measurement_theta_min      5.043
_cell_volume                     1836.33(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_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      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23996
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.961
_diffrn_reflns_theta_min         5.915
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0678 before and 0.0349 after correction.
The Ratio of minimum to maximum transmission is 0.9147.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1548 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0479P)^2^+0.2421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0742
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                3412
_reflns_number_total             3449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00378a4.cif
_cod_data_source_block           hele69
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7155568
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.867
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C24(H24), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C28(H28), C29(H29), C30(H30),
 C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              70177
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'