Sequential meta-/ortho-C–H Functionalizations by One-Pot Ruthenium(II/III) Catalysis
Korvorapun, Korkit; Kaplaneris, Nikolaos; Rogge, Torben; Warratz, Svenja; Stückl, A. Claudia; Ackermann, Lutz; ACS Catalysis 8 (2018) 886–; doi:10.1021/acscatal.7b03648

data_4514336
_publ_section_title
;
 Sequential meta-/ortho-C--H Functionalizations by One-Pot
 Ruthenium(II/III) Catalysis
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              886
_journal_paper_doi               10.1021/acscatal.7b03648
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C34 H33 Br N4 O2'
_chemical_formula_sum            'C34 H33 Br N4 O2'
_chemical_formula_weight         609.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                104.927(3)
_cell_angle_beta                 95.326(4)
_cell_angle_gamma                99.344(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4938(10)
_cell_length_b                   10.8107(10)
_cell_length_c                   16.6719(19)
_cell_measurement_reflns_used    1657
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.45
_cell_volume                     1445.0(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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, 2015)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            47834
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_min         2.455
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.461
_exptl_absorpt_correction_T_max  0.3452
_exptl_absorpt_correction_T_min  0.2804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1224 before and 0.0443 after correction. The Ratio of minimum to maximum transmission is 0.8123. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.478
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         8840
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0433P)^2^+1.3084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8097
_reflns_number_total             8840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03648_si_006.cif
_cod_data_source_block           mo_0133_cg_0m
_cod_depositor_comments
'Adding full bibliography for 4514336--4514340.cif.'
_cod_database_code               4514336
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.892
_shelx_estimated_absorpt_t_min   0.518
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C31A \\sim C32A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C31B \\sim C32B: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
3. Others
 Sof(O1B)=Sof(O2B)=Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(C30B)=Sof(H30D)=Sof(H30E)=
 Sof(H30F)=Sof(C31B)=Sof(H31C)=Sof(H31D)=Sof(C32B)=Sof(H32C)=Sof(H32D)=
 Sof(H33C)=Sof(H33D)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=
 Sof(H30C)=Sof(C31A)=Sof(H31A)=Sof(H31B)=Sof(C32A)=Sof(H32A)=Sof(H32B)=
 Sof(H33A)=Sof(H33B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C25(H25), C28A(H28A), C28B(H28B)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C31A(H31A,H31B), C31B(H31C,H31D), C32A(H32A,H32B), C32B(H32C,
 H32D), C33(H33A,H33B), C33(H33C,H33D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C16(H16), C18(H18),
 C19(H19), C21(H21), C24(H24)
4.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C30A(H30A,H30B,H30C), C30B(H30D,
 H30E,H30F), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              12655
_shelx_hkl_checksum              84154
_olex2_submission_special_instructions 'No special instructions were received'