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_7158621
_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         'C7 H11 N O4'
_chemical_formula_sum            'C7 H11 N O4'
_chemical_formula_weight         173.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4660(12)
_cell_length_b                   10.025(2)
_cell_length_c                   15.193(4)
_cell_measurement_reflns_used    3129
_cell_measurement_temperature    146.15
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.43
_cell_volume                     832.5(3)
_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      146.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0906
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7535
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.140
_diffrn_reflns_theta_max         25.140
_diffrn_reflns_theta_min         2.681
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3594
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1479 before and 0.0869 after correction.
The Ratio of minimum to maximum transmission is 0.4823.
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    1.382
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0359P)^2^+0.2121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1317
_reflns_number_total             1488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00230b5.cif
_cod_data_source_block           test5_a_pl
_cod_depositor_comments
'Adding full bibliography for 7158619--7158621.cif.'
_cod_database_code               7158621
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O4(H4), N1(H1)
2.b Ternary CH refined with riding coordinates:
 C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'