A "Motif-Oriented" Total Synthesis of Nannocystin Ax. Preparation and Biological Assessment of Analogues.
Meng, Zhanchao; Souillart, Laetitia; Monks, Brendan; Huwyler, Nikolas; Herrmann, Jennifer; Müller, Rolf; Fürstner, Alois; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02871

data_4033345
_publ_section_title
;
 A &quot;Motif-Oriented&quot; Total Synthesis of Nannocystin Ax.
 Preparation and Biological Assessment of Analogues.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02871
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C48 H55 Cl2 N3 O9, H2 O'
_chemical_formula_sum            'C48 H57 Cl2 N3 O10'
_chemical_formula_weight         906.86
_chemical_name_systematic
;
 MFA-MA-148_80K
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                MFA-MA-148_80K
_audit_creation_date             2017-05-19
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.286(2)
_cell_length_b                   13.899(5)
_cell_length_c                   33.15(2)
_cell_measurement_reflns_used    33214
_cell_measurement_temperature    80(2)
_cell_measurement_theta_max      26.847
_cell_measurement_theta_min      0.487
_cell_volume                     4739(3)
_computing_cell_refinement       'XDS V. 1 March 2015'
_computing_data_collection       'P11 Crystallography Control GUI'
_computing_data_reduction        'XDS V. 1 March 2015'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_structure_refinement  'SHELXL-2014/7 (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      80(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'P11 beamline PETRA III Pilatus 6M detector'
_diffrn_measurement_method       'CCD \f-scans'
_diffrn_radiation_monochromator  'LN2 cooled double crystal'
_diffrn_radiation_source         'PETRAIII, Hamburg'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.5636
_diffrn_reflns_av_R_equivalents  0.1809
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            279411
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        19.765
_diffrn_reflns_theta_max         23.739
_diffrn_reflns_theta_min         0.974
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             1920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  isopropanol, water'
_exptl_crystal_size_max          0.061
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 4899 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         14482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0733P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                12315
_reflns_number_total             14482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02871_si_002.cif
_cod_data_source_block           10701_10702_10703
_cod_original_cell_volume        4739(4)
_cod_database_code               4033345
_shelx_res_checksum              38276
_shelx_hkl_checksum              78679
_shelx_shelxl_version_number     2014/7