Total synthesis and stereochemical assignment of bipolamide A acetate.
Auddy, Sourya Shankar; Saha, Sanu; Goswami, Rajib Kumar; Organic & biomolecular chemistry 20 (2022) 3348–3358; doi:10.1039/d2ob00230b

data_7158619
_publ_section_title
;
 Total synthesis and stereochemical assignment of bipolamide A acetate.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3348
_journal_page_last               3358
_journal_paper_doi               10.1039/d2ob00230b
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H27 N O4'
_chemical_formula_sum            'C15 H27 N O4'
_chemical_formula_weight         285.37
_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   mixed
_audit_creation_date             2022-03-01
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-03-02 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.978(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.537(6)
_cell_length_b                   10.802(6)
_cell_length_c                   15.329(8)
_cell_measurement_reflns_used    3493
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.31
_cell_volume                     1738.2(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      302.81
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_av_unetI/netI     0.1326
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16934
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.391
_diffrn_reflns_theta_min         2.310
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1382 before and 0.0977 after correction. The Ratio of minimum to maximum transmission is 0.6324. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5685
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0933
_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^)+(0.0513P)^2^+0.8769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.2079
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.795
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                3064
_reflns_number_total             5685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00230b5.cif
_cod_data_source_block           test6_a
_cod_depositor_comments
'Adding full bibliography for 7158619--7158621.cif.'
_cod_original_cell_volume        1738.2(16)
_cod_database_code               7158619
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.966
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C20) = Uanis(C22)
3.a Ternary CH refined with riding coordinates:
 C18(H18), C3(H3A)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C2(H2A,H2B)
3.c X=CH2 refined with riding coordinates:
 C22(H22A,H22B), C6(H6A,H6B)
3.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C21(H21A,H21B,H21C), C10(H10A,
 H10B,H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C7(H7A,H7B,
 H7C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
3.e Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'