Total synthesis of (+)-oridamycins A and B.
Murmu, Ranjit; Kundu, Sourav; Majhi, Moumita; Pal, Souvik; Mondal, Abhishek; Bisai, Alakesh; Chemical communications (Cambridge, England) 60 (2024) 9737–9740; doi:10.1039/d4cc03070b

data_7133463
_publ_section_title
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 Total synthesis of (+)-oridamycins A and B.
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_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9737
_journal_page_last               9740
_journal_paper_doi               10.1039/d4cc03070b
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H27 N O3'
_chemical_formula_sum            'C24 H27 N O3'
_chemical_formula_weight         377.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2jhg4n
_audit_creation_date             2024-03-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-07 deposited with the CCDC.	2024-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.44500(10)
_cell_length_b                   10.94740(10)
_cell_length_c                   11.98780(10)
_cell_measurement_reflns_used    189
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.852
_cell_measurement_theta_min      3.706
_cell_volume                     968.676(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12042
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.133
_diffrn_reflns_theta_min         3.719
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.92107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.11(11)
_refine_ls_extinction_coef       0.0067(7)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0436P)^2^+0.1215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                3264
_reflns_number_total             3340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03070b3.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7133463.cif.'
_cod_database_code               7133463
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C11(H11), C9(H9)
1.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C7(H7A,H7B), C8(H8A,H8B)
1.c Aromatic/amide H refined with riding coordinates:
 N17(H17), C4(H4), C20(H20), C19(H19), C15(H15), C21(H21), C18(H18)
1.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C)
1.e Idealised tetrahedral OH refined as rotating group:
 O26(H26)
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_shelx_res_checksum              17242
_shelx_hkl_checksum              69287
_olex2_submission_special_instructions 'No special instructions were received'