Total synthesis of the reported structure of ceanothine D <i>via</i> a novel macrocyclization strategy.
Lee, Jisun; Joullié, Madeleine M; Chemical science 9 (2018) 2432–2436; doi:10.1039/c8sc00234g

data_1548838
_publ_section_title
;
 Total synthesis of the reported structure of ceanothine D <i>via</i> a
 novel macrocyclization strategy.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              2432
_journal_page_last               2436
_journal_paper_doi               10.1039/c8sc00234g
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H26 N4 O6 S'
_chemical_formula_sum            'C18 H26 N4 O6 S'
_chemical_formula_weight         426.49
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-03 deposited with the CCDC.
2018-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                82.789(3)
_cell_angle_beta                 85.375(3)
_cell_angle_gamma                84.403(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4225(5)
_cell_length_b                   16.5812(10)
_cell_length_c                   21.1102(14)
_cell_measurement_reflns_used    9134
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.56
_cell_volume                     2559.1(3)
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            55465
_diffrn_reflns_point_group_measured_fraction_full 0.830
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.491
_diffrn_reflns_theta_min         1.243
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 5153 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1061
_refine_ls_number_reflns         15564
_refine_ls_number_restraints     879
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0833P)^2^+3.6118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1696
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.681
_reflns_Friedel_fraction_max     0.669
_reflns_number_gt                14407
_reflns_number_total             15564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc00234g2.cif
_cod_data_source_block           7059
_cod_depositor_comments          'Adding full bibliography for 1548838.cif.'
_cod_database_code               1548838
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.931
_platon_squeeze_void_probe_radius 1.20