B(C6F5)3 mediated arene hydrogenation/transannulation of para-methoxyanilines.
Longobardi, Lauren E.; Mahdi, Tayseer; Stephan, Douglas W.; Dalton transactions (Cambridge, England : 2003) 44 (2015) 7114–7117; doi:10.1039/c5dt00921a

data_7702024
_publ_section_title
;
 B(C6F5)3 mediated arene hydrogenation/transannulation of
 para-methoxyanilines.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7114
_journal_page_last               7117
_journal_paper_doi               10.1039/c5dt00921a
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C19 H3 B F15 O, C9 H18 N, 0.5(C Cl2)'
_chemical_formula_sum            'C28.5 H21 B Cl F15 N O'
_chemical_formula_weight         724.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_Int_Tables_number      60
_audit_creation_date             2015-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-02-01 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.750(5)
_cell_length_b                   16.032(4)
_cell_length_c                   20.783(6)
_cell_measurement_reflns_used    9681
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.27
_cell_volume                     5914(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      149.7
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            47407
_diffrn_reflns_theta_full        24.9981
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0959 before and 0.0658 after correction.
The Ratio of minimum to maximum transmission is 0.9034.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6278
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2915.9611
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.9518
_refine_diff_density_min         -0.6230
_refine_diff_density_rms         0.1465
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             11.8974
_refine_ls_goodness_of_fit_ref   1.0628
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0628
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0811
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0916P)^2^+37.3813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2300
_refine_ls_wR_factor_ref         0.2505
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              0
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                3516
_reflns_number_total             5198
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5dt00921a2.cif
_cod_data_source_block           tm103_0ma
_cod_database_code               7702024
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl1b(0.5) Cl1a(0.5)
3.a Ternary CH refined with riding coordinates:
 N1(H1), C20(H20), C23(H23), C26(H26)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C22(H22a,H22b), C24(H24a,H24b), C25(H25a,H25b)
3.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c)
;
_olex2_submission_special_instructions 'No special instructions were received'