Stereochemistry of Chiral Sulfoxides used for the Synthesis of Antitumor Antibiotic Analogues of Sparsomycin
Hempel, A.; Camerman, N.; Grierson, J.; Mastropaolo, D.; Camerman, A.; Acta Crystallographica Section C 52 (1996) 3207–3210; doi:10.1107/S0108270196009948

data_2005825
_publ_section_title
;
 Stereochemistry of Chiral Sulfoxides used for the Synthesis of
 Antitumor Antibiotic Analogues of Sparsomycin
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              3207
_journal_page_last               3210
_journal_paper_doi               10.1107/S0108270196009948
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C18 H27 N O2 S'
_chemical_formula_sum            'C18 H27 N O2 S'
_chemical_formula_weight         321.47
_chemical_melting_point          352.5(5)
_chemical_name_systematic
;
[(S)-(4,5-dihydro-2-phenyl-4-oxazolyl)methyl]-(R)-sulfinyloctane
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.93(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.828(1)
_cell_length_b                   34.865(6)
_cell_length_c                   5.317(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     884.2(3)
_computing_cell_refinement       'Siemens P3 software'
_computing_data_collection       'Siemens P3 software'
_computing_data_reduction        'Siemens P3 software'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1995)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       'Siemens R3m/V 4-circle-diffractometer'
_diffrn_measurement_method       2\q/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.1028
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2237
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.142
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.20(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.668
_refine_ls_goodness_of_fit_obs   0.698
_refine_ls_hydrogen_treatment    'hydrogens riding on parent atoms'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.668
_refine_ls_restrained_S_obs      0.697
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_obs          0.0445
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[s^2^(Fo^2^)+( 0.1118P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1326
_refine_ls_wR_factor_obs         0.1083
_reflns_number_observed          1065
_reflns_number_total             1638
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sx1014.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '352-353' was changed to '352.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1/[s^2^(Fo^2^)+(
0.1118P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[s^2^(Fo^2^)+( 0.1118P)^2^] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2005825