Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.
Zou, Yike; Li, Xiangqin; Yang, Yun; Berritt, Simon; Melvin, Jason; Gonzales, Stephen; Spafford, Matthew; Smith, 3rd, Amos B; Journal of the American Chemical Society 140 (2018) 9502–9511; doi:10.1021/jacs.8b04053

data_4132447
_publ_section_title
;
 Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a
 Unified Synthetic Strategy.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9502
_journal_page_last               9511
_journal_paper_doi               10.1021/jacs.8b04053
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C21 H27 Cl I N O4'
_chemical_formula_sum            'C21 H27 Cl I N O4'
_chemical_formula_weight         519.78
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                87.487(3)
_cell_angle_beta                 79.010(3)
_cell_angle_gamma                73.201(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9976(10)
_cell_length_b                   11.0632(16)
_cell_length_c                   15.736(2)
_cell_measurement_reflns_used    9501
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.10
_cell_volume                     1144.8(3)
_computing_data_collection       'Bruker APEX3 v2016.1-0'
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_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CMOS area detector'
_diffrn_measurement_device_type  'Bruker D8QUEST'
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            90517
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         3.095
_diffrn_source                   'sealed tube'
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_exptl_absorpt_correction_T_max  0.745554
_exptl_absorpt_correction_T_min  0.603024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       irregular
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.121
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+2.7358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                4857
_reflns_number_total             5223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b04053_si_004.cif
_cod_data_source_block           1453
_cod_original_cell_volume        1144.7(3)
_cod_database_code               4132447