Biomimetic total syntheses of renifolin F and antiarone K.
Ahamad, Jarish; Khan, Faiz Ahmed; Organic & biomolecular chemistry 22 (2024) 4877–4881; doi:10.1039/d4ob00651h

data_7159956
_publ_section_title
;
 Biomimetic total syntheses of renifolin F and antiarone K.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4877
_journal_page_last               4881
_journal_paper_doi               10.1039/d4ob00651h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H28 O5'
_chemical_formula_sum            'C24 H28 O5'
_chemical_formula_weight         396.487
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-18 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.123(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9416(10)
_cell_length_b                   7.4402(10)
_cell_length_c                   28.624(4)
_cell_measurement_reflns_used    6596
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      24.382
_cell_measurement_theta_min      2.829
_cell_volume                     2116.8(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            37971
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9989
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.16
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   cylinder
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1378 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.9355.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             848.562
_exptl_crystal_preparation
;
The single crystal  was obtained by dissolving in  CH 3 Cl:  Hex (1:2)
and allowed the solvents to slowly evaporate at room temperature.
;
_exptl_crystal_recrystallization_method 'crystalysed slowly at room temperature'
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.2713
_refine_diff_density_min         -0.3092
_refine_diff_density_rms         0.0691
_refine_ls_d_res_high            0.7787
_refine_ls_d_res_low             9.4471
_refine_ls_goodness_of_fit_ref   1.0614
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0614
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.3866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              -11
_reflns_number_gt                3002
_reflns_number_total             4687
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00651h2.cif
_cod_data_source_block           mo_FAK_JA_405_1_0m
_cod_depositor_comments          'Adding full bibliography for 7159956.cif.'
_cod_original_cell_volume        2116.9(5)
_cod_database_code               7159956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C20(H20), C16(H16), C12(H12), C5(H5)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C17(H17a,H17b,H17c), C1a(H1aa,H1ab,H1ac), C1b(H1ba,H1bb,
 H1bc), C1c(H1ca,H1cb,H1cc), C1d(H1da,H1db,H1dc)
;
_olex2_submission_special_instructions 'No special instructions were received'