Total Synthesis of Berkeleylactone A.
Ferko, Branislav; Zeman, Marián; Formica, Michele; Veselý, Sebastián; Doháňošová, Jana; Moncol, Ján; Olejníková, Petra; Berkeš, Dušan; Jakubec, Pavol; Dixon, Darren J.; Caletková, Ol'ga; The Journal of organic chemistry 84 (2019) 7159–7165; doi:10.1021/acs.joc.9b00850

data_4034612
_publ_section_title
;
 Total Synthesis of Berkeleylactone A.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7159
_journal_page_last               7165
_journal_paper_doi               10.1021/acs.joc.9b00850
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H32 O7 S, 0.5(H2 O)'
_chemical_formula_sum            'C19 H33 O7.5 S'
_chemical_formula_weight         413.51
_chemical_melting_point          ?
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2019-01-27
_audit_creation_method           CRYSTALS_ver_14.61_build_6999
_cell_angle_alpha                90
_cell_angle_beta                 98.775(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.58460(2)
_cell_length_b                   5.024300(10)
_cell_length_c                   19.56580(2)
_cell_measurement_reflns_used    49377
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.09
_cell_measurement_theta_min      4.15
_cell_volume                     2097.026(18)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.136.0 (STOE, 2017)'
_computing_data_reduction
;
X-Area Integrate 1.71.2.0 (STOE, 2017) X-Area LANA 1.71.6.0 (STOE, 2017)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_unetI/netI     0.070
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36157
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.605
_diffrn_reflns_theta_min         4.145
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_correction_T_min  0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'STOE LANA (Koziskova et al., 2016)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             891.994
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.28
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 566 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   -0.024(9)
_refine_ls_extinction_coef       15(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0202
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.0048806
_refine_ls_shift/su_mean         0.0002357
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 5.46P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0786
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0786
_reflns_limit_h_max              25
_reflns_limit_h_min              -26
_reflns_limit_k_max              5
_reflns_limit_k_min              -2
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                2589
_reflns_number_total             2821
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0343
_oxford_refine_ls_scale          0.5329(10)
_oxford_reflns_number_all        2818
_oxford_structure_analysis_title 'THIS IS THE DEFAULT SETTING FOR THE TITLE, P'
_cod_data_source_file            jo9b00850_si_002.cif
_cod_data_source_block           14a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

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

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2022-01-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2097.026(15)
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_original_formula_moiety     '2(C19 H32 O7 S), H2 O'
_cod_original_formula_sum        'C38 H66 O15 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     827.03
_cod_database_code               4034612
_oxford_refine_reflns_threshold_expression_ref I>-2.0\s(I)
_oxford_hooft_y                  -0.145(10)
_oxford_bijvoet_difference       -0.024(9)