Total synthesis and biological evaluation of seven new anti-inflammatory oxacyclododecindione-type macrolactones.
Weber, Carina; Vierengel, Nina; Walter, Thorsten; Behrendt, Torsten; Lucas, Tobias; Erkel, Gerhard; Opatz, Till; Organic & biomolecular chemistry 18 (2020) 5906–5917; doi:10.1039/d0ob00958j

data_7157584
_publ_section_title
;
 Total synthesis and biological evaluation of seven new anti-inflammatory
 oxacyclododecindione-type macrolactones.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5906
_journal_page_last               5917
_journal_paper_doi               10.1039/d0ob00958j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C33 H36 O5'
_chemical_formula_sum            'C33 H36 O5'
_chemical_formula_weight         512.62
_chemical_name_systematic
(E)-11,13-bis(benzyloxy)-4,5,5,9-tetramethyl-4,5,6,7-tetrahydro-2H-benzo[d][1]oxacyclododecine-2,10(1H)-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-04-21 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.1727(9)
_cell_length_b                   29.8856(16)
_cell_length_c                   8.3703(3)
_cell_measurement_reflns_used    16314
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      65.85
_cell_measurement_theta_min      2.41
_cell_volume                     5796.7(4)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED32'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      ' 521 frames, detector distance = 40 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'X-ray mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24930
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.052
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'Incoatec microSource Cu'
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       needle
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       0.0048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.1103
_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^)+(0.1754P)^2^+12.4961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2688
_refine_ls_wR_factor_ref         0.3518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2975
_reflns_number_total             5222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00958j2.cif
_cod_data_source_block           12
_cod_depositor_comments
;Adding full bibliography for 7157584--7157586.cif.

 Adding full bibliography for 7157584--7157586.cif.
;
_cod_database_code               7157584
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.684
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              45991
_shelx_fab_checksum              27081