Total synthesis of the purported structure of sclerophytin f.
Clark, J. Stephen; Delion, Laetitia; Farrugia, Louis J.; Organic letters 16 (2014) 4300–4303; doi:10.1021/ol5020152

data_1517231
_publ_section_title
;
 Total synthesis of the purported structure of sclerophytin f.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4300
_journal_page_last               4303
_journal_paper_doi               10.1021/ol5020152
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_compound_source        'as described'
_chemical_formula_moiety         'C20 H32 O4'
_chemical_formula_sum            'C20 H32 O4'
_chemical_formula_weight         336.45
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2014-03-13T10:47:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.624(3)
_cell_length_b                   16.550(10)
_cell_length_c                   19.160(12)
_cell_measurement_reflns_used    6365
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.45
_cell_measurement_wavelength     0.71073
_cell_volume                     1783.4(18)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT-2014/3 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.727
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      -0.075183
_diffrn_orient_matrix_UB_12      -0.054442
_diffrn_orient_matrix_UB_13      0.005765
_diffrn_orient_matrix_UB_21      0.087264
_diffrn_orient_matrix_UB_22      -0.019957
_diffrn_orient_matrix_UB_23      -0.041955
_diffrn_orient_matrix_UB_31      0.135629
_diffrn_orient_matrix_UB_32      -0.017338
_diffrn_orient_matrix_UB_33      0.03019
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.097
_diffrn_reflns_Laue_measured_fraction_full 0.727
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13824
_diffrn_reflns_point_group_measured_fraction_full 0.713
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         22.443
_diffrn_reflns_theta_min         1.626
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.655
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(10)
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                1850
_reflns_number_total             2295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5020152_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1517229--1517231.cif.'
_cod_original_cell_volume        1783.3(19)
_cod_database_code               1517231
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.998