Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis
Donohoe, Timothy J.; Jones, Christopher R.; Barbosa, Luiz C. A.; Journal of the American Chemical Society 133 (2011) 16418–16421; doi:10.1021/ja207835w

data_4121884
_publ_section_title
;
 Total Synthesis of (+-)-Streptonigrin: De Novo Construction of a
 Pentasubstituted Pyridine using Ring-Closing Metathesis
;
_journal_coden_ASTM              JACSAT
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16418
_journal_page_last               16421
_journal_paper_doi               10.1021/ja207835w
_journal_volume                  133
_journal_year                    2011
_chemical_compound_source        synthetic
_chemical_formula_sum            'C9 H9 F3 N2 O5 S'
_chemical_formula_weight         302.22
_chemical_melting_point          117.5(5)
_chemical_name_systematic
;
 Methyl 5-amino-3-methyl-6-(trifluoromethylsulfonyloxy)picolinate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-05-06
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                90
_cell_angle_beta                 95.4317(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.4956(3)
_cell_length_b                   12.5285(5)
_cell_length_c                   21.3048(7)
_cell_measurement_reflns_used    2697
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2523.16(15)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4660
_diffrn_reflns_theta_full        25.845
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         5.333
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.58
_refine_ls_extinction_coef       210(40)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9341
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000456
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 5.26P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1199
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1199
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2035
_reflns_number_total             2855
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.58
_oxford_diffrn_Wilson_scale      13.81
_oxford_refine_ls_r_factor_ref   0.0755
_oxford_refine_ls_scale          0.2890(5)
_oxford_reflns_number_all        2855
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '5061937 027aki10'
_cod_duplicate_entry             4106973
_cod_data_source_file            ja207835w_si_003.cif
_cod_data_source_block           13
_cod_depositor_comments
;
 Adding the _chemical_name_systematic data item.

 Antanas Vaitkus,
 2018-09-12

The following automatic conversions were performed:

'_chemical_melting_point' value '117-118' was changed to '117.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 
;
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               4121884