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_4121624
_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         'C11 H11 N3 O2 S, 0.5(C2 H4 Cl2), H2 O'
_chemical_formula_sum            'C12 H15 Cl N3 O3 S'
_chemical_formula_weight         316.78
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.711(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.464(4)
_cell_length_b                   5.2123(6)
_cell_length_c                   16.8968(17)
_cell_measurement_reflns_used    4411
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.953
_cell_measurement_theta_min      2.462
_cell_volume                     2885.9(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.782
_diffrn_reflns_theta_min         1.243
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.0921
_exptl_absorpt_correction_T_min  0.0670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1100 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.7275.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       Blade
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+11.5946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2011
_reflns_number_total             2768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5007838_si_004.cif
_cod_data_source_block           PFLJ315
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' 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_database_code               4121624
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All H(H,H) groups
2. Restrained distances
 O1S-H1S
 0.9 with sigma of 0.02
 H1SE-O1S
 0.9 with sigma of 0.02
 H1S-H1SE
 1.4 with sigma of 0.02
 N3-H3B = N3-H3A
 0.9 with sigma of 0.02
 O1S-H1SF
 0.9 with sigma of 0.02
 H1SF-H1S
 1.4 with sigma of 0.02
3. Others
 Sof(C1SB)=Sof(H1SC)=Sof(H1SD)=1-FVAR(1)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=FVAR(1)
 Fixed Sof: H1SE(0.5) H1SF(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C1S(H1SA,H1SB), C1SB(H1SC,H1SD)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_shelx_res_checksum              53091
_shelx_hkl_checksum              59502