Ligand-promoted ruthenium-catalyzed meta C-H chlorination of arenes using N-chloro-2,10-camphorsultam.
Fan, Zhoulong; Lu, Heng; Cheng, Zhen; Zhang, Ao; Chemical communications (Cambridge, England) 54 (2018) 6008–6011; doi:10.1039/c8cc03195a

data_7121671
_publ_section_title
;
 Ligand-promoted ruthenium-catalyzed meta C-H chlorination of arenes using
 N-chloro-2,10-camphorsultam.
;
_journal_issue                   47
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6008
_journal_page_last               6011
_journal_paper_doi               10.1039/c8cc03195a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C12 H6 F6 N2 O8 Ru2'
_chemical_formula_sum            'C12 H6 F6 N2 O8 Ru2'
_chemical_formula_weight         622.33
_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     dual
_audit_creation_date             2017-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-16 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.799(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2908(11)
_cell_length_b                   8.8234(7)
_cell_length_c                   15.2802(12)
_cell_measurement_reflns_used    2955
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.146
_cell_measurement_theta_min      2.73
_cell_volume                     1886.0(3)
_computing_cell_refinement       'SAINT v8.34A (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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16475
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         1.456
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0881 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.8219. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.192
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH-MeCN'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.2820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3519
_reflns_number_total             4342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03195a2.cif
_cod_data_source_block           mo_2017932_0m
_cod_depositor_comments
'Adding full bibliography for 7121669--7121671.cif.'
_cod_database_code               7121671
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.647
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F0AA-C12 \\sim F4-C12 \\sim F6-C12 \\sim F1AA-C12 \\sim F5-C12 \\sim F2AA-C12
 with sigma of 0.02
 F6-C12 \\sim F1AA-C12 \\sim F5-C12 \\sim F2AA-C12 \\sim F4-C12 \\sim F0AA-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F6) \\sim Ueq, Uanis(F1AA) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F2AA)
\\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F0AA) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: F6(0.5) F5(0.5) F4(0.5) F1AA(0.5) F0AA(0.5) F2AA(0.5)
5.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'