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_4106972
_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_moiety         'C8 H9 Br1 O3'
_chemical_formula_sum            'C8 H9 Br O3'
_chemical_formula_weight         233.06
_chemical_melting_point          589(1)
_chemical_name_systematic        6-Bromo-2,3-dimethoxyphenol
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             11-08-09
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 110.0260(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2095(4)
_cell_length_b                   11.1209(4)
_cell_length_c                   9.1577(3)
_cell_measurement_reflns_used    1896
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     881.20(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6706
_diffrn_reflns_theta_full        26.079
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         5.333
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.628
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9017
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.0010953
_refine_ls_shift/su_mean         0.0000286
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 45.0 72.1 44.6 19.7 5.10 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0636
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0636
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              0
_reflns_limit_k_min              -14
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                1800
_reflns_number_total             1989
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.16
_oxford_diffrn_Wilson_scale      1.90
_oxford_refine_ls_r_factor_ref   0.0309
_oxford_refine_ls_scale          0.7199(16)
_oxford_reflns_number_all        1989
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '8091441 011210'
_cod_data_source_file            ja207835w_si_002.cif
_cod_data_source_block           15
_cod_depositor_comments
;
 Adding the _chemical_name_systematic data item.

 Antanas Vaitkus,
 2018-09-12
;
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C8 H9 Br1 O3'
_cod_database_code               4106972
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE O   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 123,X'S) H   ( 121,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;