A ligand-free copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes in PEG-water: an expeditious protocol towards regiospecific 1-aryl benzotriazoles.
Mukhopadhyay, Chhanda; Tapaswi, Pradip Kumar; Butcher, Ray J.; Organic & biomolecular chemistry 8 (2010) 4720–4729; doi:10.1039/c0ob00177e

data_7153444
_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 &amp; 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
_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       '\w 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/[\s^2^(Fo^2^)+(0.0717P)^2^+0.4096P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_cod_data_source_file            c0ob00177e.txt
_cod_data_source_block           cm09-3
_cod_original_cell_volume        1095.40(6)
_cod_database_code               7153444