Rhodium-catalyzed denitrogenative transannulation of 1,2,3-triazolyl-carbamates: efficient access to 4-aminooxazolidinones
Pal, Kuntal; Volla, Chandra M. R.; Organic Chemistry Frontiers 4 (2017) 1380–; doi:10.1039/C7QO00101K

data_1553738
_publ_section_title
;
 Rhodium-catalyzed denitrogenative transannulation of
 1,2,3-triazolyl-carbamates: efficient access to 4-aminooxazolidinones
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1380
_journal_paper_doi               10.1039/C7QO00101K
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C17 H13 Br N2 O4 S'
_chemical_formula_sum            'C17 H13 Br N2 O4 S'
_chemical_formula_weight         421.26
_chemical_name_systematic
N-(3-(4-bromophenyl)-5-methylene-2-oxooxazolidin-4-yl)-4-methylbenzenesulfonamide
_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
_audit_block_doi                 10.5517/ccdc.csd.cc1m6dmv
_audit_creation_date             2016-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-07-25 deposited with the CCDC.
2017-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.033(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5147(10)
_cell_length_b                   7.024(3)
_cell_length_c                   15.730(9)
_cell_measurement_reflns_used    4577
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      3.2
_cell_volume                     1767.4(13)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 108.0000
	             XTD: 45.2501
	          2theta: -19.8241
scan:
	Number of images: 115
	           Slice: -52.5000 - 5.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 36.0000
	             XTD: 45.2501
	          2theta: -19.8241
scan:
	Number of images: 61
	           Slice: -59.0000 - -28.5000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -180.0000
	             XTD: 45.2501
	          2theta: -19.8241
scan:
	Number of images: 258
	           Slice: -59.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -36.0000
	             XTD: 45.2501
	          2theta: -19.8241
scan:
	Number of images: 140
	           Slice: -52.5000 - 17.5000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -180.0000
	             XTD: 45.2501
	          2theta: -19.8241
scan:
	Number of images: 162
	           Slice: -74.0000 - 7.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -180.0000
	             XTD: 45.2501
	          2theta: -19.8241
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.005541
_diffrn_orient_matrix_UB_12      -0.061942
_diffrn_orient_matrix_UB_13      -0.006363
_diffrn_orient_matrix_UB_21      0.139167
_diffrn_orient_matrix_UB_22      -0.009520
_diffrn_orient_matrix_UB_23      -0.028524
_diffrn_orient_matrix_UB_31      0.009674
_diffrn_orient_matrix_UB_32      -0.035541
_diffrn_orient_matrix_UB_33      0.059060
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.167
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.468
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       Prism
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1:1 mixture of chloroform and acetone'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0451P)^2^+1.5376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2673
_reflns_number_total             3113
_reflns_shell_number_unique_all  5047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00101k2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1553738
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N008(H008)
2.b Ternary CH refined with riding coordinates:
 C009(H009)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
2.d Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'