#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:38:22 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180309 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/23/7152392.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_7152392
loop_
_publ_author_name
'Chevallier, Floris'
'Blin, Thomas'
'Nagaradja, Elisabeth'
'Lassagne, Frédéric'
'Roisnel, Thierry'
'Halauko, Yury S.'
'Matulis, Vadim E.'
'Ivashkevich, Oleg A.'
'Mongin, Florence'
_publ_section_title
;
 Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4878
_journal_page_last               4885
_journal_paper_doi               10.1039/c2ob25554e
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C9 H7 I2 N3 O'
_chemical_formula_sum            'C9 H7 I2 N3 O'
_chemical_formula_weight         426.98
_chemical_name_systematic
;
?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P -2n -2ac'
_symmetry_space_group_name_H-M   'P c 21 n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2011-09-01T14:51:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1304(2)
_cell_length_b                   12.9948(5)
_cell_length_c                   21.5358(9)
_cell_measurement_reflns_used    3199
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.46
_cell_measurement_wavelength     0.71073
_cell_volume                     1155.91(9)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999),
CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4879
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    5.419
_exptl_absorpt_correction_T_max  0.614
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0153P)²+0.6044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0502
_reflns_number_gt                2273
_reflns_number_total             2314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25554e.txt
_cod_data_source_block           job_d
_cod_database_code               7152392
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x+1/2, y, z+1/2'
'x+1/2, 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
C1 C -0.1046(10) 0.0950(5) 0.21453(19) 0.0187(8) Uani 1 1 d .
C2 C -0.0515(16) -0.0019(5) 0.2384(2) 0.0305(14) Uani 1 1 d .
H2 H -0.0869 -0.0221 0.2802 0.037 Uiso 1 1 calc R
N3 N 0.0585(12) -0.0631(3) 0.1928(2) 0.0285(11) Uani 1 1 d .
N4 N 0.0658(9) -0.0006(3) 0.14375(19) 0.0176(9) Uani 1 1 d .
N5 N -0.0313(9) 0.0974(4) 0.15450(16) 0.0186(8) Uani 1 1 d .
C6 C 0.1791(12) -0.0329(4) 0.0838(2) 0.0168(9) Uani 1 1 d .
C7 C 0.1089(12) 0.0292(4) 0.0329(2) 0.0187(10) Uani 1 1 d .
H7 H -0.0111 0.0911 0.0377 0.022 Uiso 1 1 calc R
C8 C 0.2186(11) -0.0016(4) -0.0250(2) 0.0166(10) Uani 1 1 d .
C9 C 0.3970(12) -0.0917(4) -0.0322(2) 0.0200(11) Uani 1 1 d .
C10 C 0.4580(13) -0.1532(4) 0.0193(2) 0.0210(11) Uani 1 1 d .
H10 H 0.5729 -0.216 0.0145 0.025 Uiso 1 1 calc R
C11 C 0.3510(13) -0.1229(4) 0.0780(2) 0.0213(11) Uani 1 1 d .
H11 H 0.3964 -0.164 0.1134 0.026 Uiso 1 1 calc R
O12 O 0.4928(9) -0.1151(3) -0.09118(15) 0.0233(8) Uani 1 1 d .
C13 C 0.6739(15) -0.2084(5) -0.0998(3) 0.0276(13) Uani 1 1 d .
H13A H 0.8703 -0.2062 -0.0743 0.041 Uiso 1 1 calc R
H13B H 0.7339 -0.2153 -0.1436 0.041 Uiso 1 1 calc R
H13C H 0.5411 -0.2674 -0.0874 0.041 Uiso 1 1 calc R
I1 I -0.25664(8) 0.22870(3) 0.258362(12) 0.01886(8) Uani 1 1 d .
I2 I 0.10601(7) 0.09051(3) -0.102028(12) 0.02184(8) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.021(2) 0.0155(19) 0.0199(19) -0.005(3) 0.0008(18) -0.001(3)
C2 0.050(4) 0.024(3) 0.017(3) 0.002(2) 0.000(3) 0.009(3)
N3 0.047(3) 0.019(2) 0.020(2) 0.0037(17) 0.004(2) 0.010(2)
N4 0.022(2) 0.0109(18) 0.020(2) 0.0004(16) 0.0021(17) 0.0033(17)
N5 0.0228(19) 0.0128(17) 0.0202(16) 0.000(2) 0.0025(15) 0.002(2)
C6 0.018(2) 0.015(2) 0.018(2) -0.0033(19) 0.002(2) -0.002(2)
C7 0.017(2) 0.013(2) 0.026(3) -0.0043(19) -0.001(2) -0.001(2)
C8 0.013(2) 0.017(2) 0.019(2) 0.002(2) 0.0005(19) -0.002(2)
C9 0.021(3) 0.018(2) 0.021(2) -0.0034(19) 0.003(2) -0.003(2)
C10 0.024(3) 0.013(2) 0.027(3) -0.001(2) 0.002(2) 0.000(2)
C11 0.025(3) 0.016(2) 0.023(3) 0.003(2) -0.002(2) 0.002(2)
O12 0.0289(19) 0.0214(19) 0.0197(17) -0.0046(14) 0.0048(16) 0.0055(17)
C13 0.029(3) 0.026(3) 0.027(3) -0.008(2) 0.003(2) 0.007(3)
I1 0.02352(16) 0.01588(13) 0.01720(13) -0.00121(16) 0.00264(12) 0.00471(13)
I2 0.02282(16) 0.02271(14) 0.02000(13) 0.00366(16) -0.00111(12) 0.00266(19)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
N5 C1 C2 110.4(5)
N5 C1 I1 119.5(5)
C2 C1 I1 130.1(4)
N3 C2 C1 108.8(5)
N3 C2 H2 125.6
C1 C2 H2 125.6
N4 N3 C2 103.1(4)
N3 N4 N5 115.5(4)
N3 N4 C6 122.8(4)
N5 N4 C6 121.7(4)
C1 N5 N4 102.2(4)
C11 C6 C7 121.9(5)
C11 C6 N4 120.0(5)
C7 C6 N4 118.1(4)
C8 C7 C6 118.2(5)
C8 C7 H7 120.9
C6 C7 H7 120.9
C7 C8 C9 121.1(5)
C7 C8 I2 118.3(4)
C9 C8 I2 120.6(4)
O12 C9 C10 124.2(5)
O12 C9 C8 116.4(4)
C10 C9 C8 119.3(5)
C9 C10 C11 120.2(5)
C9 C10 H10 119.9
C11 C10 H10 119.9
C6 C11 C10 119.1(5)
C6 C11 H11 120.4
C10 C11 H11 120.4
C9 O12 C13 117.4(4)
O12 C13 H13A 109.5
O12 C13 H13B 109.5
H13A C13 H13B 109.5
O12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N5 1.328(5)
C1 C2 1.378(9)
C1 I1 2.075(6)
C2 N3 1.342(7)
C2 H2 0.95
N3 N4 1.333(6)
N4 N5 1.355(6)
N4 C6 1.436(6)
C6 C11 1.373(7)
C6 C7 1.393(7)
C7 C8 1.385(7)
C7 H7 0.95
C8 C9 1.392(7)
C8 I2 2.098(5)
C9 O12 1.365(6)
C9 C10 1.389(7)
C10 C11 1.396(7)
C10 H10 0.95
C11 H11 0.95
O12 C13 1.437(7)
C13 H13A 0.98
C13 H13B 0.98
C13 H13C 0.98
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N5 C1 C2 N3 0.1(7)
I1 C1 C2 N3 -177.5(4)
C1 C2 N3 N4 -0.1(7)
C2 N3 N4 N5 0.2(6)
C2 N3 N4 C6 178.1(5)
C2 C1 N5 N4 0.1(5)
I1 C1 N5 N4 177.9(3)
N3 N4 N5 C1 -0.2(5)
C6 N4 N5 C1 -178.1(4)
N3 N4 C6 C11 -14.4(7)
N5 N4 C6 C11 163.3(4)
N3 N4 C6 C7 165.5(5)
N5 N4 C6 C7 -16.8(7)
C11 C6 C7 C8 -0.3(7)
N4 C6 C7 C8 179.8(4)
C6 C7 C8 C9 -0.6(7)
C6 C7 C8 I2 178.9(4)
C7 C8 C9 O12 179.9(4)
I2 C8 C9 O12 0.4(6)
C7 C8 C9 C10 1.8(7)
I2 C8 C9 C10 -177.7(4)
O12 C9 C10 C11 179.9(5)
C8 C9 C10 C11 -2.2(8)
C7 C6 C11 C10 -0.1(8)
N4 C6 C11 C10 179.8(5)
C9 C10 C11 C6 1.4(8)
C10 C9 O12 C13 -1.3(7)
C8 C9 O12 C13 -179.3(5)
