Cascading Auto-oxidative Biproline Guanylations Form Optically Active Dispacamide Dimers and Permit an Eight-Step Synthesis of (-)-Ageliferin.
Ding, Hui; Roberts, Andrew G.; Chiang, Rocky; Harran, Patrick G.; The Journal of organic chemistry 83 (2018) 7231–7238; doi:10.1021/acs.joc.8b00631

data_4035439
_publ_section_title
;
 Cascading Auto-oxidative Biproline Guanylations Form Optically Active
 Dispacamide Dimers and Permit an Eight-Step Synthesis of (-)-Ageliferin.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7231
_journal_page_last               7238
_journal_paper_doi               10.1021/acs.joc.8b00631
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unkl
_chemical_formula_moiety         'C24 H30 N4 O6, C2 H6 O S'
_chemical_formula_sum            'C26 H36 N4 O7 S'
_chemical_formula_weight         548.65
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc10mvl2
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-06-03 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.289(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.808(6)
_cell_length_b                   7.964(3)
_cell_length_c                   21.315(7)
_cell_measurement_reflns_used    3274
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.36
_cell_measurement_theta_min      3.56
_cell_volume                     2797.1(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1464
_diffrn_reflns_av_sigmaI/netI    0.1581
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21673
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.56
_diffrn_reflns_theta_min         3.56
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     702
_refine_ls_number_reflns         6181
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                3197
_reflns_number_total             6181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00631_si_003.cif
_cod_data_source_block           har1304s
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2797.2(17)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4035439