Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases.
Miller, Duncan C.; Carbain, Benoit; Beale, Gary S.; Alhasan, Sari F.; Reeves, Helen L.; Baisch, Ulrich; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Organic & biomolecular chemistry 13 (2015) 5279–5284; doi:10.1039/c5ob00211g

data_7154394
_publ_section_title
;
 Regioselective sulfamoylation at low temperature enables concise
 syntheses of putative small molecule inhibitors of sulfatases.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5279
_journal_page_last               5284
_journal_paper_doi               10.1039/c5ob00211g
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H18 N2 O9 S2'
_chemical_formula_sum            'C8 H18 N2 O9 S2'
_chemical_formula_weight         350.36
_chemical_name_systematic
'((2R,3S,4R,5R,6S)-3,4-Dihydroxy-6-methoxy-5-(methylsulfonamido) tetrahydro-2H-pyran-2-yl)methyl sulfamate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-01-16 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9598(3)
_cell_length_b                   9.8111(3)
_cell_length_c                   17.7241(6)
_cell_measurement_reflns_used    4127
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      28.5405
_cell_measurement_theta_min      3.2958
_cell_volume                     1384.15(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details
;
  1 omega  -69.00   54.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038    0.0000 -180.0000 123

  2 omega  -32.00   18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   98.0000 -173.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0578957000
_diffrn_orient_matrix_UB_12      -0.0048367000
_diffrn_orient_matrix_UB_13      0.0302917000
_diffrn_orient_matrix_UB_21      -0.0610395000
_diffrn_orient_matrix_UB_22      0.0276960000
_diffrn_orient_matrix_UB_23      0.0247987000
_diffrn_orient_matrix_UB_31      -0.0295927000
_diffrn_orient_matrix_UB_32      -0.0665846000
_diffrn_orient_matrix_UB_33      0.0081980000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6197
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.540
_diffrn_reflns_theta_min         3.296
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Slow evaporation of methanolic solution'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0373P)^2^+0.2723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                2848
_reflns_number_total             2944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00211g2.cif
_cod_data_source_block           1043886_RJG60
_cod_depositor_comments          'Adding full bibliography for 7154394.cif.'
_cod_original_cell_volume        1384.15(9)
_cod_database_code               7154394
_chemical_oxdiff_formula         'C20 H20 N4 O2'
_shelx_estimated_absorpt_t_max   0.881
_shelx_estimated_absorpt_t_min   0.846
_reflns_odcompleteness_completeness 98.44
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C4(H4A), C5(H5A)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              52641
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_completion    2014-12-15
_olex2_date_sample_data_collection 2011-08-11
_olex2_submission_original_sample_id '10 (RJG60)'
_olex2_submission_special_instructions 'No special instructions were received'