Synthesis of N-Acyl Sulfamates from Fluorosulfates and Amides.
Gilles, Philippe; Veryser, Cedrick; Vangrunderbeeck, Sarah; Ceusters, Sam; Van Meervelt, Luc; De Borggraeve, Wim M.; The Journal of organic chemistry 84 (2019) 1070–1078; doi:10.1021/acs.joc.8b02785

data_4035979
_publ_section_title
;
 Synthesis of N-Acyl Sulfamates from Fluorosulfates and Amides.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1070
_journal_page_last               1078
_journal_paper_doi               10.1021/acs.joc.8b02785
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C8 H8 Br N O4 S'
_chemical_formula_sum            'C8 H8 Br N O4 S'
_chemical_formula_weight         294.12
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.570(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5450(3)
_cell_length_b                   10.3342(3)
_cell_length_c                   8.9226(2)
_cell_measurement_reflns_used    7413
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      25.9570
_cell_measurement_theta_min      2.9740
_cell_volume                     1062.47(5)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       MAR
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
'#__ type_ start__ end____ width___ exp.time_ 1 phi 20.00 260.00 2.0000 180.0000 omega____ theta____ kappa____ phi______ frames 57.0000 0.0000 -134.0000 - 120'
_diffrn_measurement_device       diffractometer
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '\p scans'
_diffrn_orient_matrix_UB_11      -0.0457845000
_diffrn_orient_matrix_UB_12      0.0411177000
_diffrn_orient_matrix_UB_13      0.0198210000
_diffrn_orient_matrix_UB_21      0.0338794000
_diffrn_orient_matrix_UB_22      0.0204475000
_diffrn_orient_matrix_UB_23      0.0647494000
_diffrn_orient_matrix_UB_31      0.0233305000
_diffrn_orient_matrix_UB_32      0.0509778000
_diffrn_orient_matrix_UB_33      -0.0420125000
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9135
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.536
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.058
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0383P)^2^+0.8197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1994
_reflns_number_total             2063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02785_si_002.cif
_cod_data_source_block           wdb1006
_cod_database_code               4035979
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C8 H8 N1 O4 S Br'
_shelx_estimated_absorpt_t_max   0.563
_shelx_estimated_absorpt_t_min   0.323
_reflns_odcompleteness_completeness 95.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), N12(H12)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              53703
_shelx_hkl_checksum              18404
_olex2_submission_special_instructions 'No special instructions were received'