Towards sustainable synthesis of pyren-1-yl azoliums via electrochemical oxidative C–N coupling
de Robillard, Guillaume; Makni, Oumayma; Cattey, Hélène; Andrieu, Jacques; Devillers, Charles H.; Green Chem. 17 (2015) 4669–; doi:10.1039/C5GC01142F

data_7220980
_publ_section_title
;
 Towards sustainable synthesis of pyren-1-yl azoliums via electrochemical
 oxidative C--N coupling
;
_journal_issue                   9
_journal_name_full               'Green Chem.'
_journal_page_first              4669
_journal_paper_doi               10.1039/C5GC01142F
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'B F4, C24 H17 N2, C2 H3 N'
_chemical_formula_sum            'C26 H20 B F4 N3'
_chemical_formula_weight         461.26
_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
_audit_creation_date             2015-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-04-09 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                75.320(2)
_cell_angle_beta                 78.092(2)
_cell_angle_gamma                74.019(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5758(6)
_cell_length_b                   10.4878(7)
_cell_length_c                   12.8368(8)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.575
_cell_measurement_theta_min      2.788
_cell_volume                     1062.06(12)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            52383
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_min         2.788
_diffrn_source                   'X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0527 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.9706.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.5707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4020
_reflns_number_total             4913
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {f3b9cbf9-bde3-4536-90f6-5c511b720a68}
_cod_data_source_file            c5gc01142f2.cif
_cod_data_source_block           mo_1411cd49_0m_a
_cod_depositor_comments
'Adding full bibliography for 7220979--7220980.cif.'
_cod_database_code               7220980
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C20(H20), C4(H4), C24(H24), C15(H15), C7(H7), C13(H13), C14(H14),
 C23(H23), C6(H6), C21(H21), C16(H16), C22(H22), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              48796
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with grease'
_olex2_submission_special_instructions 'No special instructions were received'