Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent
Collett, Christopher J.; Massey, Richard S.; Maguire, Oliver R.; Batsanov, Andrei S.; O'Donoghue, AnnMarie C.; Smith, Andrew D.; Chemical Science 4 (2013) 1514–; doi:10.1039/c2sc22137c

data_1514488
_publ_section_title
;
 Mechanistic insights into the triazolylidene-catalysed Stetter and
 benzoin reactions: role of the N-aryl substituent
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1514
_journal_paper_doi               10.1039/c2sc22137c
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'Cl 1-,C18 H17 F N3 O 1+,D2 O'
_chemical_formula_sum            'C18 H17 Cl D2 F N3 O2'
_chemical_formula_weight         365.82
_chemical_name_systematic
;2-phenyl-3-(\a-hydroxy-parafluorobenzyl)-6,7-dihydro-5H-pyrrolo[2,1-
c][1,2,4]triazol-2-ium chloride deuterohydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-03-29
_audit_creation_method
;
Olex2 1.1-beta (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.8845(8)
_cell_length_b                   9.4266(4)
_cell_length_c                   19.2915(9)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.16
_cell_volume                     3434.2(3)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'A short history of SHELX (Sheldrick, 2008)/Bruker'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2008)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 6000 CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+1.9833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                2497
_reflns_number_total             3029
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2sc22137c.txt
_cod_data_source_block           37
_cod_database_code               1514488