First total synthesis of versicotide A, B and C
Posada, Laura; Davyt, Danilo; Serra, Gloria; RSC Advances 10 (2020) 43653–43659; doi:10.1039/D0RA09635K

data_7241787
_publ_section_title
;
 First total synthesis of versicotide A, B and C
;
_journal_issue                   71
_journal_name_full               'RSC Advances'
_journal_page_first              43653
_journal_page_last               43659
_journal_paper_doi               10.1039/D0RA09635K
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H29 N5 O5, C H4 O'
_chemical_formula_sum            'C26 H33 N5 O6'
_chemical_formula_weight         511.57
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-18 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.461(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9455(3)
_cell_length_b                   8.2022(3)
_cell_length_c                   15.9136(6)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      73.51
_cell_measurement_theta_min      2.78
_cell_volume                     1295.78(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.877
_diffrn_reflns_theta_min         2.782
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1193 before and 0.0882 after correction. The Ratio of minimum to maximum transmission is 0.6348. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(12)
_refine_ls_extinction_coef       0.0127(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0583P)^2^+0.2149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                4496
_reflns_number_total             5186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra09635k2.cif
_cod_data_source_block           cu_200311_aplp_lp153_0m_a
_cod_database_code               7241787
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H11)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H5), C7(H6), C18(H18), C9(H8), C19(H19), C21(H21), C20(H20), C10(H9), C8(H7)
2.c Idealised Me refined as rotating group:
 C3(H2,H4,H3), C14(H16,H17,H15), C25(H29,H28,H27), C24(H24,H26,H25), C13(H12,
 H14,H13), C26(H32,H30,H31)
;
_shelx_res_checksum              17844
_olex2_submission_special_instructions 'No special instructions were received'