#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:52:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153444.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_7153444
loop_
_publ_author_name
'Mukhopadhyay, Chhanda'
'Tapaswi, Pradip Kumar'
'Butcher, Ray J.'
_publ_section_title
;
 A ligand-free copper (1) catalysed intramolecular N-arylation of
 diazoaminobenzenes in PEG-water: an expeditious protocol towards
 regiospecific 1-aryl benzotriazoles.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4720
_journal_page_last               4729
_journal_paper_doi               10.1039/c0ob00177e
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C12 H8 I N3'
_chemical_formula_sum            'C12 H8 I N3'
_chemical_formula_weight         321.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 100.517(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8821(3)
_cell_length_b                   7.5462(2)
_cell_length_c                   14.9402(4)
_cell_measurement_reflns_used    3113
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      73.8445
_cell_measurement_theta_min      4.5348
_cell_volume                     1095.41(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3982
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.03
_diffrn_reflns_theta_min         4.98
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    22.751
_exptl_absorpt_correction_T_max  0.205
_exptl_absorpt_correction_T_min  0.018
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.4986
_exptl_crystal_size_mid          0.2473
_exptl_crystal_size_min          0.1987
_refine_diff_density_max         1.418
_refine_diff_density_min         -1.139
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0341
_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)+(0.0717P)²+0.4096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                2015
_reflns_number_total             2160
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0ob00177e.txt
_cod_data_source_block           cm09-3
_cod_original_cell_volume        1095.40(6)
_cod_database_code               7153444
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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
I I 0.01119(2) 0.79969(3) 0.601790(14) 0.02896(13) Uani 1 1 d .
N1 N 0.3348(3) 1.0156(4) 0.4368(2) 0.0235(5) Uani 1 1 d .
N2 N 0.3270(3) 1.0279(4) 0.5221(2) 0.0236(6) Uani 1 1 d .
N3 N 0.3200(3) 0.8606(4) 0.5568(2) 0.0226(5) Uani 1 1 d .
C1 C 0.3343(3) 0.8392(5) 0.4133(2) 0.0201(6) Uani 1 1 d .
C2 C 0.3469(3) 0.7565(5) 0.3307(2) 0.0240(6) Uani 1 1 d .
H2A H 0.3555 0.8236 0.2782 0.029 Uiso 1 1 calc R
C3 C 0.3462(3) 0.5734(5) 0.3293(2) 0.0258(7) Uani 1 1 d .
H3A H 0.3550 0.5134 0.2747 0.031 Uiso 1 1 calc R
C4 C 0.3326(3) 0.4727(5) 0.4076(3) 0.0271(7) Uani 1 1 d .
H4A H 0.3303 0.3470 0.4036 0.033 Uiso 1 1 calc R
C5 C 0.3226(4) 0.5525(5) 0.4891(2) 0.0254(7) Uani 1 1 d .
H5A H 0.3149 0.4851 0.5417 0.031 Uiso 1 1 calc R
C6 C 0.3244(3) 0.7383(5) 0.4906(2) 0.0217(6) Uani 1 1 d .
C7 C 0.3239(4) 0.8317(4) 0.6517(2) 0.0218(6) Uani 1 1 d .
C8 C 0.2037(4) 0.8000(4) 0.6858(3) 0.0224(7) Uani 1 1 d .
C9 C 0.2137(4) 0.7728(5) 0.7793(3) 0.0239(7) Uani 1 1 d .
H9A H 0.1330 0.7512 0.8037 0.029 Uiso 1 1 calc R
C10 C 0.3415(4) 0.7770(5) 0.8368(3) 0.0263(7) Uani 1 1 d .
H10A H 0.3474 0.7577 0.9003 0.032 Uiso 1 1 calc R
C11 C 0.4596(4) 0.8089(5) 0.8024(3) 0.0265(8) Uani 1 1 d .
H11A H 0.5463 0.8116 0.8423 0.032 Uiso 1 1 calc R
C12 C 0.4524(4) 0.8371(5) 0.7098(3) 0.0259(7) Uani 1 1 d .
H12A H 0.5336 0.8597 0.6860 0.031 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
N2 N1 C1 108.8(3)
N1 N2 N3 108.8(3)
C6 N3 N2 109.8(3)
C6 N3 C7 128.3(3)
N2 N3 C7 121.5(3)
N1 C1 C6 108.2(3)
N1 C1 C2 130.9(3)
C6 C1 C2 120.8(3)
C3 C2 C1 117.1(3)
C3 C2 H2A 121.5
C1 C2 H2A 121.5
C2 C3 C4 121.5(3)
C2 C3 H3A 119.2
C4 C3 H3A 119.2
C5 C4 C3 121.8(3)
C5 C4 H4A 119.1
C3 C4 H4A 119.1
C4 C5 C6 116.6(3)
C4 C5 H5A 121.7
C6 C5 H5A 121.7
N3 C6 C1 104.3(3)
N3 C6 C5 133.5(3)
C1 C6 C5 122.2(3)
C8 C7 C12 121.0(3)
C8 C7 N3 121.1(3)
C12 C7 N3 117.8(3)
C7 C8 C9 118.6(3)
C7 C8 I 121.8(3)
C9 C8 I 119.6(3)
C10 C9 C8 120.3(3)
C10 C9 H9A 119.8
C8 C9 H9A 119.8
C11 C10 C9 120.5(4)
C11 C10 H10A 119.7
C9 C10 H10A 119.7
C10 C11 C12 120.3(4)
C10 C11 H11A 119.8
C12 C11 H11A 119.8
C11 C12 C7 119.2(3)
C11 C12 H12A 120.4
C7 C12 H12A 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I C8 2.079(4)
N1 N2 1.294(4)
N1 C1 1.377(5)
N2 N3 1.372(4)
N3 C6 1.360(5)
N3 C7 1.428(5)
C1 C6 1.401(5)
C1 C2 1.409(5)
C2 C3 1.382(5)
C2 H2A 0.9500
C3 C4 1.423(5)
C3 H3A 0.9500
C4 C5 1.378(5)
C4 H4A 0.9500
C5 C6 1.402(5)
C5 H5A 0.9500
C7 C8 1.396(5)
C7 C12 1.402(5)
C8 C9 1.398(5)
C9 C10 1.392(6)
C9 H9A 0.9500
C10 C11 1.380(5)
C10 H10A 0.9500
C11 C12 1.390(5)
C11 H11A 0.9500
C12 H12A 0.9500
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
C1 N1 N2 N3 -0.5(4)
N1 N2 N3 C6 0.4(4)
N1 N2 N3 C7 173.9(3)
N2 N1 C1 C6 0.5(4)
N2 N1 C1 C2 -176.8(3)
N1 C1 C2 C3 178.3(3)
C6 C1 C2 C3 1.2(5)
C1 C2 C3 C4 0.4(5)
C2 C3 C4 C5 -1.5(5)
C3 C4 C5 C6 1.0(5)
N2 N3 C6 C1 -0.1(4)
C7 N3 C6 C1 -173.0(3)
N2 N3 C6 C5 179.0(4)
C7 N3 C6 C5 6.1(6)
N1 C1 C6 N3 -0.2(4)
C2 C1 C6 N3 177.4(3)
N1 C1 C6 C5 -179.4(3)
C2 C1 C6 C5 -1.8(5)
C4 C5 C6 N3 -178.3(4)
C4 C5 C6 C1 0.6(5)
C6 N3 C7 C8 -87.5(5)
N2 N3 C7 C8 100.3(4)
C6 N3 C7 C12 92.8(4)
N2 N3 C7 C12 -79.3(4)
C12 C7 C8 C9 -0.3(5)
N3 C7 C8 C9 -180.0(3)
C12 C7 C8 I 177.9(3)
N3 C7 C8 I -1.7(4)
C7 C8 C9 C10 -0.1(5)
I C8 C9 C10 -178.4(3)
C8 C9 C10 C11 0.3(6)
C9 C10 C11 C12 -0.1(6)
C10 C11 C12 C7 -0.4(5)
C8 C7 C12 C11 0.6(5)
N3 C7 C12 C11 -179.8(3)
