Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.
Petersen, Kimberly S.; Posner, Gary H.; Organic letters 10 (2008) 4685–4687; doi:10.1021/ol8020513

data_1504936
_publ_section_title
;
 Asymmetric, organocatalytic, three-step synthesis of
 gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4685
_journal_page_last               4687
_journal_paper_doi               10.1021/ol8020513
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H16 O3 S'
_chemical_formula_sum            'C16 H16 O3 S'
_chemical_formula_weight         288.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_audit_creation_date
;
'Tue Jun 17 10:57:45 2008'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
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_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.35380(10)
_cell_length_b                   13.5189(3)
_cell_length_c                   20.0587(5)
_cell_measurement_reflns_used    7319
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.4984
_cell_measurement_theta_min      3.7989
_cell_volume                     1451.80(6)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      'see scan set'
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_measurement_method       ' omega scans'
_diffrn_orient_matrix_UB_11      -0.0502083738
_diffrn_orient_matrix_UB_12      -0.0328240744
_diffrn_orient_matrix_UB_13      0.0240920128
_diffrn_orient_matrix_UB_21      0.0084979479
_diffrn_orient_matrix_UB_22      -0.0394915677
_diffrn_orient_matrix_UB_23      -0.0232083425
_diffrn_orient_matrix_UB_31      0.1222792220
_diffrn_orient_matrix_UB_32      -0.0107950658
_diffrn_orient_matrix_UB_33      0.0114984852
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14904
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_diffrn_source_power             2
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.8134
_exptl_crystal_size_mid          0.0724
_exptl_crystal_size_min          0.0595
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2711
_reflns_number_total             3300
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8020513_si_002.cif
_cod_data_source_block           x0464
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               1504936
_audit_creation_method_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_collection_reference
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_cell_refinment_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_cell_measurement_resolution_max 0.77
_jhu_your_name_here              'Dr. Amy A Sarjeant'
_jhu_your_lab_here               'NCB 240'
_jhu_your_phone_number_here      x6-8569
_jhu_your_email_here             xray@jhu.edu
_jhu_institutional_source        'Posner Lab'
_jhu_submitting_scientist        'Kim Petersen'
_jhu_scientist_phone             x6-4529
_jhu_scientist_email             kpeter20@jhu.edu
_jhu_identifying_number          x0464
_jhu_xray_labbook                II-126
_jhu_crystalization_labbook      KP5-138-2
_jhu_crystalization_solvent      'Methylene Chloride, Ethyl Acetate'
_jhu_crystalization_method
;
;
_jhu_diffraction_detector_distance 50
_jhu_quality_factor              1