#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/44/1514487.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1514487
loop_
_publ_author_name
'Collett, Christopher J.'
'Massey, Richard S.'
'Maguire, Oliver R.'
'Batsanov, Andrei S.'
'O'Donoghue, AnnMarie C.'
'Smith, Andrew D.'
_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-(α-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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0479P)²] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl Cl 0.12595(5) 0.39192(11) 0.49093(5) 0.0360(3) Uani 1 1 d .
O1 O 0.23223(13) 0.5485(3) 0.40609(13) 0.0297(7) Uani 1 1 d .
H1 H 0.2008(19) 0.499(4) 0.4322(18) 0.043(13) Uiso 1 1 d .
O2 O 0.02974(18) 0.6509(4) 0.4492(2) 0.0687(13) Uani 1 1 d .
D1 D -0.006(3) 0.645(5) 0.469(2) 0.071(19) Uiso 1 1 d .
D2 D 0.054(3) 0.564(7) 0.458(3) 0.16(3) Uiso 1 1 d .
N1 N 0.16169(13) 0.8017(3) 0.43724(15) 0.0217(7) Uani 1 1 d .
N2 N 0.08776(14) 0.9303(3) 0.37832(16) 0.0262(8) Uani 1 1 d .
N3 N 0.11341(14) 0.8182(3) 0.34079(14) 0.0228(7) Uani 1 1 d .
C1 C 0.15797(17) 0.7411(4) 0.37650(19) 0.0221(9) Uani 1 1 d .
C2 C 0.19348(17) 0.7772(4) 0.50423(18) 0.0268(9) Uani 1 1 d .
H2C H 0.2441 0.7612 0.5004 0.032 Uiso 1 1 calc R
H2D H 0.1718 0.6964 0.5278 0.032 Uiso 1 1 calc R
C3 C 0.17741(18) 0.9165(4) 0.54060(19) 0.0306(10) Uani 1 1 d .
H3A H 0.2185 0.9789 0.5394 0.037 Uiso 1 1 calc R
H3B H 0.1652 0.8985 0.5887 0.037 Uiso 1 1 calc R
C4 C 0.11582(18) 0.9863(4) 0.50333(17) 0.0284(9) Uani 1 1 d .
H4A H 0.0714 0.9683 0.5270 0.034 Uiso 1 1 calc R
H4B H 0.1227 1.0889 0.4985 0.034 Uiso 1 1 calc R
C5 C 0.11824(17) 0.9144(4) 0.43652(18) 0.0224(9) Uani 1 1 d .
C6 C 0.19913(17) 0.6158(4) 0.35151(18) 0.0241(9) Uani 1 1 d .
H6 H 0.1668 0.5479 0.3291 0.029 Uiso 1 1 calc R
C7 C 0.25249(18) 0.6647(4) 0.30014(18) 0.0225(9) Uani 1 1 d .
C8 C 0.31225(17) 0.7333(4) 0.32234(18) 0.0244(9) Uani 1 1 d .
H8 H 0.3204 0.7453 0.3696 0.029 Uiso 1 1 calc R
C9 C 0.35973(18) 0.7838(4) 0.27570(19) 0.0259(9) Uani 1 1 d .
H9 H 0.4003 0.8302 0.2915 0.031 Uiso 1 1 calc R
C10 C 0.34938(18) 0.7681(4) 0.20613(19) 0.0256(9) Uani 1 1 d .
C11 C 0.28980(17) 0.6981(4) 0.18493(19) 0.0283(10) Uani 1 1 d .
H11 H 0.2818 0.6847 0.1378 0.034 Uiso 1 1 calc R
C12 C 0.24191(18) 0.6477(4) 0.23154(19) 0.0287(10) Uani 1 1 d .
H12 H 0.2014 0.6009 0.2159 0.034 Uiso 1 1 calc R
C13 C 0.40164(18) 0.8204(4) 0.15517(18) 0.0336(10) Uani 1 1 d .
H13A H 0.4028 0.9233 0.1561 0.050 Uiso 1 1 calc R
H13B H 0.3884 0.7884 0.1097 0.050 Uiso 1 1 calc R
H13C H 0.4476 0.7834 0.1666 0.050 Uiso 1 1 calc R
C14 C 0.09056(17) 0.8012(4) 0.27180(18) 0.0228(9) Uani 1 1 d .
C15 C 0.05196(18) 0.6851(4) 0.2543(2) 0.0298(10) Uani 1 1 d .
H15 H 0.0417 0.6138 0.2866 0.036 Uiso 1 1 calc R
C16 C 0.02851(18) 0.6759(4) 0.1875(2) 0.0375(11) Uani 1 1 d .
H16 H 0.0017 0.5969 0.1740 0.045 Uiso 1 1 calc R
C17 C 0.04352(19) 0.7793(4) 0.1406(2) 0.0361(11) Uani 1 1 d .
H17 H 0.0270 0.7713 0.0953 0.043 Uiso 1 1 calc R
C18 C 0.08257(19) 0.8945(5) 0.1597(2) 0.0361(10) Uani 1 1 d .
H18 H 0.0931 0.9657 0.1275 0.043 Uiso 1 1 calc R
C19 C 0.10640(17) 0.9060(4) 0.22599(19) 0.0298(10) Uani 1 1 d .
H19 H 0.1332 0.9849 0.2396 0.036 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 139.4(3)
C1 N1 C5 107.4(3)
C5 N1 C2 112.9(3)
C5 N2 N3 102.7(3)
N2 N3 C14 118.7(3)
C1 N3 N2 111.8(3)
C1 N3 C14 129.5(3)
N1 C1 N3 105.7(3)
N1 C1 C6 127.3(3)
N3 C1 C6 126.9(3)
N1 C2 C3 101.4(3)
C2 C3 C4 107.7(3)
C5 C4 C3 101.5(3)
N1 C5 C4 111.9(3)
N2 C5 N1 112.3(3)
N2 C5 C4 135.7(3)
O1 C6 C1 110.4(3)
O1 C6 C7 110.0(3)
C1 C6 C7 109.3(3)
C8 C7 C6 119.7(3)
C12 C7 C6 121.3(3)
C12 C7 C8 119.0(3)
C9 C8 C7 120.1(3)
C8 C9 C10 121.4(3)
C9 C10 C13 121.6(3)
C11 C10 C9 117.7(3)
C11 C10 C13 120.7(3)
C12 C11 C10 121.1(3)
C7 C12 C11 120.7(3)
C15 C14 N3 119.5(3)
C15 C14 C19 122.5(3)
C19 C14 N3 118.0(3)
C14 C15 C16 117.5(4)
C17 C16 C15 121.2(4)
C16 C17 C18 119.9(4)
C17 C18 C19 119.9(4)
C14 C19 C18 119.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.404(4)
N1 C1 1.330(4)
N1 C2 1.473(4)
N1 C5 1.361(4)
N2 N3 1.389(4)
N2 C5 1.297(4)
N3 C1 1.330(4)
N3 C14 1.437(4)
C1 C6 1.514(5)
C2 C3 1.537(5)
C3 C4 1.545(5)
C4 C5 1.483(5)
C6 C7 1.515(5)
C7 C8 1.394(5)
C7 C12 1.375(5)
C8 C9 1.383(5)
C9 C10 1.392(5)
C10 C11 1.391(5)
C10 C13 1.506(5)
C11 C12 1.387(5)
C14 C15 1.376(5)
C14 C19 1.379(5)
C15 C16 1.394(5)
C16 C17 1.379(5)
C17 C18 1.381(5)
C18 C19 1.387(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl 0.93(4) 2.11(4) 3.033(3) 177(3) .
O2 D1 Cl 0.79(5) 2.47(5) 3.249(4) 169(5) 5_566
O2 D2 Cl 0.97(7) 2.24(7) 3.191(4) 168(5) .
