C-H Methylation of Heteroarenes Inspired by Radical SAM Methyl Transferase.
Gui, Jinghan; Zhou, Qianghui; Pan, Chung-Mao; Yabe, Yuki; Burns, Aaron C.; Collins, Michael R.; Ornelas, Martha A.; Ishihara, Yoshihiro; Baran, Phil S.; Journal of the American Chemical Society 136 (2014) 4853–4856; doi:10.1021/ja5007838

data_4121625
_publ_section_title
;
 C-H Methylation of Heteroarenes Inspired by Radical SAM Methyl
 Transferase.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4853
_journal_page_last               4856
_journal_paper_doi               10.1021/ja5007838
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         '2(C7 H7 O4 S2), H12 O6 Zn'
_chemical_formula_sum            'C14 H26 O14 S4 Zn'
_chemical_formula_weight         611.96
_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                 92.858(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2053(5)
_cell_length_b                   32.8177(19)
_cell_length_c                   8.8796(5)
_cell_measurement_reflns_used    6029
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.48
_cell_volume                     2388.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.907
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15248
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.61
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_T_max  0.9313
_exptl_absorpt_correction_T_min  0.8691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.073
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         7586
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+3.8044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1536
_reflns_number_gt                5794
_reflns_number_total             7586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5007838_si_003.cif
_cod_data_source_block           baran345a3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/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      P2(1)
_cod_database_code               4121625