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_4035980
_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         'C9 H9 N O5 S2'
_chemical_formula_sum            'C9 H9 N O5 S2'
_chemical_formula_weight         275.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.069(5)
_cell_angle_beta                 83.880(5)
_cell_angle_gamma                89.814(5)
_cell_formula_units_Z            4
_cell_length_a                   8.2394(5)
_cell_length_b                   10.4297(7)
_cell_length_c                   13.8617(8)
_cell_measurement_reflns_used    6594
_cell_measurement_temperature    294.00(11)
_cell_measurement_theta_max      27.3020
_cell_measurement_theta_min      2.7450
_cell_volume                     1162.74(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -20.00  25.00   1.00    3.76    --  -17.15 -99.00-180.00   45
  2  \w    -39.00  52.00   1.00    3.76    --  -17.15  57.00  60.00   91
  3  \w    -86.00   4.00   1.00    3.76    --  -17.15 -57.00 -90.00   90
  4  \w    -25.00  92.00   1.00    3.76    --   18.79  19.00-120.00  117
  5  \w    -20.00  61.00   1.00    3.76    --   18.79 -99.00  60.00   81
  6  \w     -7.00  91.00   1.00    3.76    --   18.79  38.00-150.00   98
  7  \w    -93.00 -35.00   1.00    3.76    --  -17.15-178.00  30.00   58
  8  \w    -39.00  52.00   1.00    3.76    --  -17.15  57.00-180.00   91
  9  \w    -86.00   4.00   1.00    3.76    --  -17.15 -57.00  30.00   90
 10  \w    -20.00  61.00   1.00    3.76    --   18.79 -99.00 -90.00   81
 11  \w     34.00  95.00   1.00    3.76    --   18.79-178.00  30.00   61
 12  \w    -50.00  39.00   1.00    3.76    --   18.79 -57.00-150.00   89
 13  \w    -20.00  18.00   1.00    3.76    --  -17.15 -99.00  60.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0667731000
_diffrn_orient_matrix_UB_12      0.0392139000
_diffrn_orient_matrix_UB_13      -0.0148525000
_diffrn_orient_matrix_UB_21      -0.0494420000
_diffrn_orient_matrix_UB_22      -0.0569767000
_diffrn_orient_matrix_UB_23      0.0053033000
_diffrn_orient_matrix_UB_31      -0.0243956000
_diffrn_orient_matrix_UB_32      0.0038662000
_diffrn_orient_matrix_UB_33      0.0499931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18288
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.153
_diffrn_reflns_theta_min         2.486
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0486P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3594
_reflns_number_total             5528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02785_si_003.cif
_cod_data_source_block           wdb1007
_cod_original_cell_volume        1162.75(12)
_cod_database_code               4035980
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C9 H9 N1 O5 S2'
_chemical_oxdiff_usercomment     'SFA-SFCA-10a Philippe Gilles'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.800
_reflns_odcompleteness_completeness 99.94
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C13(H13), C23(H23), C29(H29), C30(H30)
2.c Aromatic/amide H refined with riding coordinates and stretchable bonds:
 N14(H14), N31(H31)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.348
_oxdiff_exptl_absorpt_empirical_full_min 0.372