Sulfation made simple: A strategy for synthesising sulfated molecules
Gill, Daniel; Male, Louise; Jones, Alan Morenc; Chemical Communications  (2019) –; doi:10.1039/C9CC01057B

data_7123129
_publ_section_title
;
 Sulfation made simple: A strategy for synthesising sulfated molecules
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01057B
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H27 N1 O3 S1'
_chemical_formula_sum            'C12 H27 N O3 S'
_chemical_formula_weight         265.40
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-28 deposited with the CCDC.    2019-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   14.3352(2)
_cell_length_b                   14.3352(2)
_cell_length_c                   12.2455(2)
_cell_measurement_reflns_used    7878
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4740
_cell_measurement_theta_min      8.0000
_cell_volume                     2179.29(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_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    -83.00  38.00   1.00    1.00    --  -42.02  19.00-150.00  121
  2  \w     17.00 116.00   1.00    1.00    --   42.02  38.00 -60.00   99
  3  \w     23.00  98.00   1.00    1.00    --   42.02-125.00-150.00   75
  4  \w     76.00 178.00   1.00    1.00    --  105.92  64.00-120.26  102
  5  \w     78.00 178.00   1.00    1.00    --  105.92  30.00 -30.00  100
  6  \w     73.00 178.00   1.00    1.00    --  105.92  77.00-120.00  105
  7  \w     33.00 121.00   1.00    1.00    --  105.92-125.00  60.00   88
  8  \w     77.00 178.00   1.00    1.00    --  105.92  61.00 -90.00  101
  9  \w     23.00 109.00   1.00    1.00    --  105.92 -94.00  90.00   86
 10  \w     94.00 178.00   1.00    1.00    --  105.92 125.00  30.00   84
 11  \w     73.00 178.00   1.00    1.00    --  105.92  77.00 -90.00  105
 12  \w     76.00 178.00   1.00    1.00    --  105.92  64.00-110.48  102
 13  \w   -123.00 -77.00   1.00    1.00    --  -42.02 -85.00 170.00   46
 14  \w     14.00 115.00   1.00    1.00    --   42.02  57.00-180.00  101
 15  \w      9.00 118.00   1.00    1.00    --   42.02  77.00  60.00  109
 16  \w     73.00 178.00   1.00    1.00    --  105.92  77.00   0.00  105
 17  \w     77.00 178.00   1.00    1.00    --  105.92  61.00-180.00  101
 18  \w     77.00 178.00   1.00    1.00    --  105.92  61.00  60.00  101
 19  \w     73.00 110.00   1.00    1.00    --  105.92  77.00 120.00   37
 20  \w     30.00 139.00   1.00    1.00    --  105.92 -77.00-171.00  109
 21  \w     80.00 178.00   1.00    1.00    --  105.92  45.00 120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1202345000
_diffrn_orient_matrix_UB_12      -0.0866809000
_diffrn_orient_matrix_UB_13      -0.0015475000
_diffrn_orient_matrix_UB_21      -0.0260575000
_diffrn_orient_matrix_UB_22      0.0725262000
_diffrn_orient_matrix_UB_23      0.0715152000
_diffrn_orient_matrix_UB_31      -0.0162106000
_diffrn_orient_matrix_UB_32      0.0512946000
_diffrn_orient_matrix_UB_33      -0.1034665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8776
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.846
_diffrn_reflns_theta_min         8.070
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.969
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 478 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         977
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0209
_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^)+(0.0325P)^2^+1.2029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0570
_reflns_Friedel_coverage         0.974
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                973
_reflns_number_total             977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01057b2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2179.28(8)
_cod_database_code               7123129
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H27 N1 O3 S1'
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              86522
_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.900