Manganese-Catalyzed Directed Methylation of C(sp(2))-H Bonds at 25 °C with High Catalytic Turnover.
Sato, Takenari; Yoshida, Takumi; Al Mamari, Hamad H.; Ilies, Laurean; Nakamura, Eiichi; Organic letters 19 (2017) 5458–5461; doi:10.1021/acs.orglett.7b02778

data_1547179
_publ_section_title
;
 Manganese-Catalyzed Directed Methylation of C(sp(2))-H Bonds at 25 \%C
 with High Catalytic Turnover.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5458
_journal_page_last               5461
_journal_paper_doi               10.1021/acs.orglett.7b02778
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30
_chemical_melting_point          143.5(5)
_chemical_name_common            MePyNaph
_chemical_name_systematic        3-methyl-N-(naphthalen-1-yl)picolinamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.616(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4154(6)
_cell_length_b                   6.0240(2)
_cell_length_c                   15.0935(6)
_cell_measurement_reflns_used    13222
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.226
_cell_measurement_theta_min      5.882
_cell_volume                     1306.44(9)
_computing_cell_refinement       'Rapid Auto (Rigaku)'
_computing_data_collection       'Rapid Auto (Rigaku)'
_computing_data_reduction        'Rapid Auto (Rigaku)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Rapid II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13222
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         5.882
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Empirical Absorption Correction March 2001 T Higashi'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0725P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1615
_reflns_number_total             2385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02778_si_002.cif
_cod_data_source_block           MePyNaph
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '143-144' was changed to '143.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1547179.cif.
;
_cod_database_code               1547179
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.651
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              17296
_shelx_hkl_checksum              11092