Ru-Catalyzed Meta-C-H Benzylation of Arenes with Toluene Derivatives.
Li, Bo; Fang, Sheng-Long; Huang, Dan-Ying; Shi, Bing-Feng; Organic letters 19 (2017) 3950–3953; doi:10.1021/acs.orglett.7b01529

data_1547126
_publ_section_title
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 Ru-Catalyzed Meta-C-H Benzylation of Arenes with Toluene Derivatives.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3950
_journal_page_last               3953
_journal_paper_doi               10.1021/acs.orglett.7b01529
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C18 H15 Cl N2 O'
_chemical_formula_sum            'C18 H15 Cl N2 O'
_chemical_formula_weight         310.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.102(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6030(7)
_cell_length_b                   7.7040(7)
_cell_length_c                   16.6899(11)
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      29.3802
_cell_measurement_theta_min      3.1715
_cell_volume                     1485.99(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0266381000
_diffrn_orient_matrix_UB_12      0.0276185000
_diffrn_orient_matrix_UB_13      -0.0344155000
_diffrn_orient_matrix_UB_21      -0.0196940000
_diffrn_orient_matrix_UB_22      -0.0763499000
_diffrn_orient_matrix_UB_23      -0.0207434000
_diffrn_orient_matrix_UB_31      -0.0516333000
_diffrn_orient_matrix_UB_32      0.0434157000
_diffrn_orient_matrix_UB_33      -0.0144139000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6045
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.3075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                2089
_reflns_number_total             2712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b01529_si_002.cif
_cod_data_source_block           160719_libo8_89b
_cod_database_code               1547126
_chemical_oxdiff_formula         'c10 h10 n2 o2 Cl1'
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;