#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/73/4027341.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_4027341
loop_
_publ_author_name
'Wendy S. Brotherton'
'Ronald J. Clark'
'Lei Zhu'
_publ_section_title
;
 Synthesis of 5-Iodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ
 Generated Copper(I) Catalyst and Electrophilic Triiodide Ion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6443
_journal_page_last               6455
_journal_paper_doi               10.1021/jo300841c
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C14 H11 I N4'
_chemical_formula_sum            'C14 H11 I N4'
_chemical_formula_weight         362.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2998(7)
_cell_length_b                   12.7159(11)
_cell_length_c                   24.849(2)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.95
_cell_volume                     2622.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29065
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    2.433
_exptl_absorpt_correction_T_max  0.9005
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.990
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0177
_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/[σ²(Fo²)+(0.0176P)²+2.6994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0410
_refine_ls_wR_factor_ref         0.0435
_reflns_number_gt                2836
_reflns_number_total             3276
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300841c_si_001_1.cif
_cod_data_source_block           zhu126
_cod_original_sg_symbol_Hall     -P2ac2ab
_cod_database_code               4027341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
I1 I 0.995098(12) 0.482267(8) 0.182492(4) 0.02183(4) Uani 1 1 d .
C1 C 0.7169(2) 0.76239(14) 0.06303(7) 0.0266(4) Uani 1 1 d .
H1 H 0.7123 0.8292 0.0801 0.032 Uiso 1 1 calc R
C2 C 0.6254(2) 0.74371(17) 0.01737(8) 0.0337(4) Uani 1 1 d .
H2 H 0.5588 0.7980 0.0034 0.040 Uiso 1 1 calc R
C3 C 0.6299(3) 0.64697(17) -0.00801(7) 0.0367(5) Uani 1 1 d .
H3 H 0.5659 0.6343 -0.0390 0.044 Uiso 1 1 calc R
C4 C 0.7284(3) 0.56913(17) 0.01224(8) 0.0387(5) Uani 1 1 d .
H4 H 0.7326 0.5027 -0.0052 0.046 Uiso 1 1 calc R
C5 C 0.8218(2) 0.58672(15) 0.05792(7) 0.0313(4) Uani 1 1 d .
H5 H 0.8896 0.5325 0.0713 0.038 Uiso 1 1 calc R
C6 C 0.8160(2) 0.68379(13) 0.08408(6) 0.0215(3) Uani 1 1 d .
C7 C 0.91083(19) 0.70749(12) 0.13295(6) 0.0199(3) Uani 1 1 d .
C8 C 0.97996(18) 0.64448(13) 0.17187(7) 0.0189(3) Uani 1 1 d .
C9 C 1.1415(2) 0.69311(13) 0.25622(6) 0.0215(3) Uani 1 1 d .
H9A H 1.2122 0.7542 0.2634 0.026 Uiso 1 1 calc R
H9B H 1.2112 0.6310 0.2504 0.026 Uiso 1 1 calc R
C10 C 1.03564(19) 0.67397(13) 0.30468(6) 0.0190(3) Uani 1 1 d .
C11 C 1.0216(2) 0.57402(14) 0.32739(7) 0.0244(3) Uani 1 1 d .
H11 H 1.0789 0.5160 0.3128 0.029 Uiso 1 1 calc R
C12 C 0.9221(2) 0.56125(14) 0.37175(7) 0.0291(4) Uani 1 1 d .
H12 H 0.9097 0.4940 0.3879 0.035 Uiso 1 1 calc R
C13 C 0.8414(2) 0.64732(14) 0.39217(7) 0.0277(4) Uani 1 1 d .
H13 H 0.7725 0.6405 0.4225 0.033 Uiso 1 1 calc R
C14 C 0.8631(2) 0.74378(14) 0.36748(7) 0.0253(3) Uani 1 1 d .
H14 H 0.8078 0.8029 0.3818 0.030 Uiso 1 1 calc R
N1 N 0.93994(18) 0.81012(11) 0.14671(6) 0.0236(3) Uani 1 1 d .
N2 N 1.02335(18) 0.81327(12) 0.19156(6) 0.0239(3) Uani 1 1 d .
N3 N 1.04823(17) 0.71318(11) 0.20721(5) 0.0192(3) Uani 1 1 d .
N4 N 0.95783(18) 0.75838(12) 0.32449(6) 0.0218(3) Uani 1 1 d .
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'
N N 0.0061 0.0033 '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
C2 C1 C6 120.46(17)
C2 C1 H1 119.8
C6 C1 H1 119.8
C1 C2 C3 120.72(19)
C1 C2 H2 119.6
C3 C2 H2 119.6
C4 C3 C2 119.22(18)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 120.81(19)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C6 120.17(18)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 118.60(16)
C1 C6 C7 118.40(15)
C5 C6 C7 123.00(16)
N1 C7 C8 107.73(14)
N1 C7 C6 119.53(14)
C8 C7 C6 132.72(15)
N3 C8 C7 104.62(14)
N3 C8 I1 121.89(12)
C7 C8 I1 133.49(12)
N3 C9 C10 112.52(13)
N3 C9 H9A 109.1
C10 C9 H9A 109.1
N3 C9 H9B 109.1
C10 C9 H9B 109.1
H9A C9 H9B 107.8
N4 C10 C11 122.57(16)
N4 C10 C9 116.25(15)
C11 C10 C9 121.18(15)
C12 C11 C10 118.54(16)
C12 C11 H11 120.7
C10 C11 H11 120.7
C13 C12 C11 119.24(16)
C13 C12 H12 120.4
C11 C12 H12 120.4
C12 C13 C14 118.50(16)
C12 C13 H13 120.8
C14 C13 H13 120.8
N4 C14 C13 123.58(17)
N4 C14 H14 118.2
C13 C14 H14 118.2
N2 N1 C7 109.50(14)
N1 N2 N3 107.29(13)
N2 N3 C8 110.86(13)
N2 N3 C9 119.05(13)
C8 N3 C9 130.08(14)
C14 N4 C10 117.57(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C8 2.0833(16)
C1 C2 1.386(2)
C1 C6 1.396(2)
C1 H1 0.9500
C2 C3 1.383(3)
C2 H2 0.9500
C3 C4 1.379(3)
C3 H3 0.9500
C4 C5 1.392(3)
C4 H4 0.9500
C5 C6 1.396(2)
C5 H5 0.9500
C6 C7 1.478(2)
C7 N1 1.371(2)
C7 C8 1.381(2)
C8 N3 1.362(2)
C9 N3 1.466(2)
C9 C10 1.510(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 N4 1.346(2)
C10 C11 1.395(2)
C11 C12 1.387(3)
C11 H11 0.9500
C12 C13 1.380(3)
C12 H12 0.9500
C13 C14 1.383(2)
C13 H13 0.9500
C14 N4 1.339(2)
C14 H14 0.9500
N1 N2 1.313(2)
N2 N3 1.347(2)
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
C6 C1 C2 C3 0.3(3)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C5 0.5(3)
C3 C4 C5 C6 0.4(3)
C2 C1 C6 C5 0.6(3)
C2 C1 C6 C7 -179.78(16)
C4 C5 C6 C1 -0.9(3)
C4 C5 C6 C7 179.50(17)
C1 C6 C7 N1 -20.1(2)
C5 C6 C7 N1 159.54(17)
C1 C6 C7 C8 158.21(18)
C5 C6 C7 C8 -22.2(3)
N1 C7 C8 N3 -0.24(18)
C6 C7 C8 N3 -178.68(17)
N1 C7 C8 I1 -179.54(12)
C6 C7 C8 I1 2.0(3)
N3 C9 C10 N4 -71.87(18)
N3 C9 C10 C11 108.61(17)
N4 C10 C11 C12 0.7(3)
C9 C10 C11 C12 -179.79(15)
C10 C11 C12 C13 -0.4(3)
C11 C12 C13 C14 -0.1(3)
C12 C13 C14 N4 0.4(3)
C8 C7 N1 N2 0.29(19)
C6 C7 N1 N2 178.98(14)
C7 N1 N2 N3 -0.22(19)
N1 N2 N3 C8 0.06(18)
N1 N2 N3 C9 179.01(14)
C7 C8 N3 N2 0.11(18)
I1 C8 N3 N2 179.52(11)
C7 C8 N3 C9 -178.68(15)
I1 C8 N3 C9 0.7(2)
C10 C9 N3 N2 97.64(17)
C10 C9 N3 C8 -83.7(2)
C13 C14 N4 C10 -0.1(3)
C11 C10 N4 C14 -0.4(2)
C9 C10 N4 C14 -179.96(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659511
