A surprising switch in absolute configuration of anti-inflammatory macrolactones.
Tauber, Johannes; Rohr, Markus; Walter, Thorsten; Schollmeyer, Dieter; Rahn-Hotze, Karin; Erkel, Gerhard; Opatz, Till; Organic & biomolecular chemistry 14 (2016) 3695–3698; doi:10.1039/c6ob00430j

data_7155046
_publ_section_title
;
 A surprising switch in absolute configuration of anti-inflammatory
 macrolactones.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3695
_journal_page_last               3698
_journal_paper_doi               10.1039/c6ob00430j
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H21 Cl O5, H2 O'
_chemical_formula_sum            'C18 H23 Cl O6'
_chemical_formula_weight         370.81
_chemical_name_systematic        (14S,15R)-14-deoxyoxacyclododecindione
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
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_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-18 deposited with the CCDC.
2016-03-22 downloaded from the CCDC.
;
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_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.54
_cell_volume                     901.71(9)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
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_diffrn_measurement_details      ' 158 frames, detector distance = 70 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6802
_diffrn_reflns_point_group_measured_fraction_full 0.997
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.209
_diffrn_reflns_theta_min         2.542
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.243
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_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EE/PE'
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.309
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_refine_ls_abs_structure_details
;
 Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.8603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3448
_reflns_number_total             4421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00430j2.cif
_cod_data_source_block           4
_cod_depositor_comments          'Adding full bibliography for 7155046.cif.'
_cod_database_code               7155046
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              82718