Double Protonation of Amino-Substituted Pyridine and Pyrimidine Tungsten Complexes: Friedel‒Crafts-like Coupling to Aromatic Heterocycles
Pienkos, Jared A.; Knisely, Anne T.; MacLeod, Brianna L.; Myers, Jeffery T.; Shivokevich, Philip J.; Teran, Victor; Sabat, Michal; Myers, William H.; Harman, W. Dean; Organometallics 33 (2014) 5464–; doi:10.1021/om5007402

data_4084418
_publ_section_title
;
 Double Protonation of Amino-Substituted Pyridine and Pyrimidine Tungsten
 Complexes: Friedel--Crafts-like Coupling to Aromatic Heterocycles
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5464
_journal_paper_doi               10.1021/om5007402
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C25 H36 B F3 N9 O5 P S W'
_chemical_formula_weight         857.32
_chemical_name_systematic
; 
 ? 
;
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                81.0170(10)
_cell_angle_beta                 80.9620(10)
_cell_angle_gamma                81.8830(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0494(4)
_cell_length_b                   11.8081(4)
_cell_length_c                   14.2552(5)
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      37.12
_cell_measurement_theta_min      3.46
_cell_volume                     1638.25(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_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  0.0133
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.996
_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       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23039
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.189
_exptl_absorpt_coefficient_mu    3.705
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.190
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_refine_diff_density_max         0.531
_refine_diff_density_min         -0.802
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_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0131
_refine_ls_R_factor_gt           0.0131
_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^)+(0.0189P)^2^+1.1246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0345
_refine_ls_wR_factor_ref         0.0346
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6654
_reflns_number_total             6675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5007402_si_002.cif
_cod_data_source_block           mo_jared327jap1073_0m_a
_cod_depositor_comments
;Adding full bibliography for 4084418.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4084418
_shelx_estimated_absorpt_t_min   0.305
_shelx_estimated_absorpt_t_max   0.572
_shelxl_version_number           2013-4
_shelx_res_checksum              96853
_shelx_hkl_checksum              40029