Enantioselective Total Syntheses of Citrinadins A and B. Stereochemical Revision of Their Assigned Structures.
Bian, Zhiguo; Marvin, Christopher C.; Pettersson, Martin; Martin, Stephen F.; Journal of the American Chemical Society 136 (2014) 14184–; doi:10.1021/ja5074646

data_4122700
_publ_section_title
;
 Enantioselective Total Syntheses of Citrinadins A and B. Stereochemical
 Revision of Their Assigned Structures.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14184
_journal_paper_doi               10.1021/ja5074646
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C23 H33 N3 O3 Br 1+, C2 H3 O2 1-, 3 C H2 Cl2'
_chemical_formula_sum            'C28 H42 Br Cl6 N3 O5'
_chemical_formula_weight         793.26
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.013(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.344(2)
_cell_length_b                   14.187(3)
_cell_length_c                   15.306(3)
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    153(2)
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_cell_measurement_theta_min      2.0
_cell_volume                     1750.0(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury 2 CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0000
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_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7980
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
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_platon_squeeze_details
;
;
_refine_diff_density_max         1.294
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.094(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         7980
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0806
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1030P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2225
_reflns_number_gt                5674
_reflns_number_total             7980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5074646_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4122695--4122702.cif.
;
_cod_original_cell_volume        1749.9(7)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4122700