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_7158620
_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         'C13 H25 N O5'
_chemical_formula_sum            'C13 H25 N O5'
_chemical_formula_weight         275.34
_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_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                 99.659(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7002(11)
_cell_length_b                   6.0652(7)
_cell_length_c                   11.8500(12)
_cell_measurement_reflns_used    5627
_cell_measurement_temperature    126(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      3.86
_cell_volume                     758.15(14)
_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      126.44
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6668
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         3.863
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1325 before and 0.0717 after correction. The Ratio of minimum to maximum transmission is 0.6810. 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    1.206
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0065P)^2^+1.1304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2515
_reflns_number_total             2586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00230b5.cif
_cod_data_source_block           test1_a
_cod_depositor_comments
'Adding full bibliography for 7158619--7158621.cif.'
_cod_database_code               7158620
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.950
_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.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00D,H00E), C00D(H00F,H00G)
2.c Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00F(H00H,H00I,H00J), C00G(H00K,H00L,H00M), C00H(H00N,
 H00O,H00P), C00I(H00Q,H00R,H00S), C00J(H00T,H00U,H00V)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'