Concise Approach to the Carbocyclic Core of the Naturally Occurring Sphingomyelinase Inhibitor Scyphostatin
Goverdhan Mehta; Nagi Reddy Modugu; Journal of Organic Chemistry 78 (2013) 3367–3373; doi:10.1021/jo3028196

data_4028081
_publ_contact_author_address
;
School of Chemistry
University of Hyderabad
Gachibowli
Hyderabad 500046, India.
;
_publ_contact_author_email       gmsc@uohyd.ernet.in
_publ_contact_author_fax         +91-40-23012460
_publ_contact_author_name        'Mehta, Goverdhan'
_publ_contact_author_phone       +91-40-23010785
_publ_section_title
;
 Concise Approach to the Carbocyclic Core of the Naturally Occurring
 Sphingomyelinase Inhibitor Scyphostatin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3367
_journal_page_last               3373
_journal_paper_doi               10.1021/jo3028196
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C17 H22 O4'
_chemical_formula_sum            'C17 H22 O4'
_chemical_formula_weight         290.35
_chemical_name_systematic
;
(1S*,2R*,4R*,8R*,9S*,10S*,11R*)-9-hydroxy-6,6-dimethyl-8-(prop-2-en-1-yl)-
5,7-dioxatetracyclo[9.2.1.0^2,10^.0^4,8^]tetradec-12-en-3-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
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_audit_creation_date             2012-09-24T21:46:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 122.23(5)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   28.465(14)
_cell_length_b                   16.248(3)
_cell_length_c                   23.16(3)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.96
_cell_measurement_theta_min      2.71
_cell_volume                     9061(14)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.1561
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16988
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         7671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.2131
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1072P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2776
_reflns_number_gt                3101
_reflns_number_total             7671
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3028196_si_002.cif
_cod_data_source_block           platon_acc
_cod_original_cell_volume        9063(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4028081