Facile synthesis of enantioenriched phenol-sulfoxides and their aluminum complexes.
Tang, Yani; Sun, Yuji; Liu, Jiyong; Duttwyler, Simon; Organic & biomolecular chemistry 14 (2016) 5580–5585; doi:10.1039/c6ob00136j

data_7155041
_publ_section_title
;
 Facile synthesis of enantioenriched phenol-sulfoxides and their aluminum
 complexes.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5580
_journal_page_last               5585
_journal_paper_doi               10.1039/c6ob00136j
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H16 Al Br O2 S'
_chemical_formula_sum            'C15 H16 Al Br O2 S'
_chemical_formula_weight         367.23
_chemical_name_systematic
;
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-01-15 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0842(5)
_cell_length_b                   12.4461(8)
_cell_length_c                   16.7654(9)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4673
_cell_measurement_theta_min      2.9986
_cell_volume                     1686.88(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0652661000
_diffrn_orient_matrix_UB_12      -0.0124823000
_diffrn_orient_matrix_UB_13      0.0266940000
_diffrn_orient_matrix_UB_21      0.0441722000
_diffrn_orient_matrix_UB_22      0.0249432000
_diffrn_orient_matrix_UB_23      0.0315441000
_diffrn_orient_matrix_UB_31      -0.0385521000
_diffrn_orient_matrix_UB_32      0.0496902000
_diffrn_orient_matrix_UB_33      -0.0091088000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11251
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack (1983), 1296 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.017(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2327
_reflns_number_total             3071
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00136j2.cif
_cod_data_source_block           151228_tyn306_3rd
_cod_depositor_comments
'Adding full bibliography for 7155041--7155045.cif.'
_cod_database_code               7155041
_chemical_oxdiff_formula         'c10 h10 O2 s1 Al1 Br1'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;