Remote stereocontrol in the synthesis of acyclic 1,4-diols and 1,4-aminoalcohols from 2-sulfinyl dienes.
Fernández de la Pradilla, Roberto; Velado, Marina; Colomer, Ignacio; Simal, Carmen; Viso, Alma; Gornitzka, Heinz; Hemmert, Catherine; Organic letters 16 (2014) 5200–5203; doi:10.1021/ol502592y

data_1517828
_publ_section_title
;
 Remote stereocontrol in the synthesis of acyclic 1,4-diols and
 1,4-aminoalcohols from 2-sulfinyl dienes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5200
_journal_page_last               5203
_journal_paper_doi               10.1021/ol502592y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C33 H26 N4 O13'
_chemical_formula_weight         686.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 98.394(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.994(4)
_cell_length_b                   6.1028(7)
_cell_length_c                   16.831(2)
_cell_measurement_reflns_used    2237
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.22
_cell_measurement_theta_min      2.93
_cell_volume                     3251.1(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.1229
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21864
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         5.120
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 1143 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6198
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0401P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                3240
_reflns_number_total             6198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502592y_si_002.cif
_cod_data_source_block           6
_cod_depositor_comments
;Adding full bibliography for 1517828.cif.

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_cell_volume        3251.2(7)
_cod_database_code               1517828
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2014-3
_shelx_res_checksum              24021
_shelx_hkl_checksum              23350