Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities.
Dermenci, Alpay; Selig, Philipp S.; Domaoal, Robert A.; Spasov, Krasimir A.; Anderson, Karen S.; Miller, Scott J.; Chemical science (Royal Society of Chemistry : 2010) 2 (2011) 1568–; doi:10.1039/C1SC00221J

data_1515608
_publ_section_title
;
 Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based
 Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their
 Putative anti-HIV Activities.
;
_journal_issue                   8
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              1568
_journal_paper_doi               10.1039/C1SC00221J
_journal_volume                  2
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H20 O4 '
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.31
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2009-12-16
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.2838(7)
_cell_length_b                   9.5550(9)
_cell_length_c                   19.3652(19)
_cell_measurement_reflns_used    11789
_cell_measurement_temperature    223.1
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1347.8(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 6.85
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13934
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1293 Friedel Pairs'
_refine_ls_abs_structure_Flack   -1.8(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3088
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.1034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                2230
_reflns_number_total             3088
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c1sc00221j.txt
_cod_data_source_block           '_AD02'
_cod_original_formula_sum        'C14 H20 O4 '
_cod_database_code               1515608