Construction of 1,2,4-Triazole Derivatives via Cyclocondensation of Alkylidene Dihydropyridines and Aryldiazonium Salts.
Joshi, Madhur S.; Pigge, F. Christopher; Organic letters 18 (2016) 5916–5919; doi:10.1021/acs.orglett.6b03019

data_1544524
_publ_section_title
;
 Construction of 1,2,4-Triazole Derivatives via Cyclocondensation of
 Alkylidene Dihydropyridines and Aryldiazonium Salts.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5916
_journal_page_last               5919
_journal_paper_doi               10.1021/acs.orglett.6b03019
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'B F4, C17 H18 Br N4'
_chemical_formula_sum            'C17 H18 B Br F4 N4'
_chemical_formula_weight         445.07
_chemical_name_systematic
'1-(4-bromophenyl)-4,5-diethyl-3-(pyridin-4-yl)-4H-1,2,4-triazol-1-ium tetrafluoroborate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.31 svn.r3340 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.604(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3019(9)
_cell_length_b                   20.691(2)
_cell_length_c                   10.1070(10)
_cell_measurement_reflns_used    34954
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      51.56
_cell_measurement_theta_min      4.509
_cell_volume                     1932.3(3)
_computing_cell_refinement       'apexII (Bruker AXS, 2010)'
_computing_data_collection       'apexII (Bruker AXS, 2010)'
_computing_data_reduction        'apexII (Bruker AXS, 2010)'
_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      190.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            34152
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.931
_diffrn_reflns_theta_min         2.414
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0634 before and 0.0378 after correction.
The Ratio of minimum to maximum transmission is 0.8645.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       irregular
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0550P)^2^+1.8660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3533
_reflns_number_total             4584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03019_si_002.cif
_cod_data_source_block           fcp168
_cod_depositor_comments
;Adding full bibliography for 1544524.cif.

 Adding full bibliography for 1544524.cif.
;
_cod_database_code               1544524
_shelx_estimated_absorpt_t_max   0.736
_shelx_estimated_absorpt_t_min   0.484
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12A) = Uanis(C12B)
3. Rigid body (RIGU) restrains
 N15A, C12A, C13A, C14A, C16A, C17A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N15B, C12B, C13B, C14B, C16B, C17B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{N15A, C12A, C13A, C14A, C16A, C17A} sigma for 1-2: 0.02, 1-3: 0.04
as
{N15B, C12B, C13B, C14B, C16B, C17B}
5. Others
 Sof(N15B)=Sof(C12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C16B)=
 Sof(H16B)=Sof(C17B)=Sof(H17B)=1-FVAR(1)
 Sof(N15A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C16A)=
 Sof(H16A)=Sof(C17A)=Sof(H17A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13A(H13A), C14A(H14A), C16A(H16A),
 C17A(H17A), C13B(H13B), C14B(H14B), C16B(H16B), C17B(H17B)
6.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              27777
_shelx_hkl_checksum              47122
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'