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_1514487
_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-,C19 H20 N3 O 1+,D2 O'
_chemical_formula_sum            'C19 H20 Cl D2 N3 O2'
_chemical_formula_weight         361.85
_chemical_name_systematic
;2-phenyl-3-(\a-hydroxy-paramethylbenzyl)-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             2011-03-23
_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                   19.2697(16)
_cell_length_b                   9.5129(8)
_cell_length_c                   19.6896(16)
_cell_measurement_reflns_used    2675
_cell_measurement_temperature    120
_cell_measurement_theta_max      21.86
_cell_measurement_theta_min      2.32
_cell_volume                     3609.3(5)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2008)/Bruker'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 6000 CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.027797
_diffrn_orient_matrix_UB_12      0.013986
_diffrn_orient_matrix_UB_13      0.043283
_diffrn_orient_matrix_UB_21      0.048747
_diffrn_orient_matrix_UB_22      0.025085
_diffrn_orient_matrix_UB_23      0.012652
_diffrn_orient_matrix_UB_31      -0.023013
_diffrn_orient_matrix_UB_32      0.036250
_diffrn_orient_matrix_UB_33      -0.025460
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1899
_diffrn_reflns_av_unetI/netI     0.1240
_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       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33554
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.07
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                1513
_reflns_number_total             3182
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2sc22137c.txt
_cod_data_source_block           36
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_source_target' value 'MO' changed to 'Mo' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               1514487