#------------------------------------------------------------------------------
#$Date: 2016-02-16 21:30:59 +0100 (mar 16 de feb de 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/72/4027231.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_4027231
loop_
_publ_author_name
'Murali Mohan Guru'
'Tharmalingam Punniyamurthy'
_publ_section_title
;
 Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3-
 and 1,2,4-Triazoles from Bisarylhydrazones via C-H
 Functionalization/C-C/N-N/C-N Bonds Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5063
_journal_page_last               5073
_journal_paper_doi               10.1021/jo300592t
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C12 H8 Cl2 N2'
_chemical_formula_weight         251.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.268(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8369(15)
_cell_length_b                   4.7221(8)
_cell_length_c                   11.6470(18)
_cell_measurement_temperature    298(2)
_cell_volume                     540.88(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4644
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADBAS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.018(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   1.018
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.3020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                1296
_reflns_number_total             1338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300592t_si_005.cif
_cod_data_source_block           2h'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C12 H8 Cl2 N2 '
_cod_database_code               4027231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
Cl1 Cl 0.08346(4) 0.90367(9) 0.16637(4) 0.04321(17) Uani 1 1 d .
N1 N 0.45590(14) 0.0528(3) -0.03275(12) 0.0387(3) Uani 1 1 d .
C1 C 0.38619(16) 0.3468(4) 0.13752(14) 0.0381(4) Uani 1 1 d .
H1 H 0.4544 0.2700 0.1844 0.046 Uiso 1 1 calc R
C2 C 0.37223(15) 0.2606(3) 0.02289(14) 0.0352(3) Uani 1 1 d .
C3 C 0.27086(17) 0.3799(4) -0.04648(14) 0.0398(4) Uani 1 1 d .
H3 H 0.2624 0.3251 -0.1230 0.048 Uiso 1 1 calc R
C4 C 0.18258(16) 0.5781(4) -0.00373(14) 0.0384(4) Uani 1 1 d .
H4 H 0.1149 0.6567 -0.0507 0.046 Uiso 1 1 calc R
C5 C 0.19620(14) 0.6585(3) 0.11026(13) 0.0317(3) Uani 1 1 d .
C6 C 0.29783(16) 0.5475(4) 0.18099(13) 0.0359(3) Uani 1 1 d .
H6 H 0.3069 0.6067 0.2569 0.043 Uiso 1 1 calc R
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
Cl1 0.0394(2) 0.0395(3) 0.0511(3) -0.00231(17) 0.00916(17) 0.00737(16)
N1 0.0355(7) 0.0393(8) 0.0414(7) 0.0018(6) -0.0003(5) -0.0001(6)
C1 0.0318(7) 0.0383(9) 0.0439(8) 0.0064(7) -0.0034(6) 0.0029(6)
C2 0.0318(7) 0.0307(8) 0.0433(8) 0.0009(6) 0.0071(6) -0.0015(6)
C3 0.0417(8) 0.0417(9) 0.0359(8) -0.0036(6) 0.0013(6) 0.0019(7)
C4 0.0368(8) 0.0409(9) 0.0373(8) 0.0015(7) -0.0028(6) 0.0047(7)
C5 0.0295(7) 0.0276(7) 0.0382(7) 0.0007(6) 0.0056(5) -0.0008(6)
C6 0.0364(7) 0.0377(9) 0.0336(7) 0.0001(6) -0.0004(6) -0.0015(6)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
N1 N1 C2 113.14(17) 3_655
C6 C1 C2 119.82(14) .
C6 C1 H1 120.1 .
C2 C1 H1 120.1 .
C3 C2 C1 119.40(15) .
C3 C2 N1 115.07(14) .
C1 C2 N1 125.53(14) .
C4 C3 C2 121.03(15) .
C4 C3 H3 119.5 .
C2 C3 H3 119.5 .
C3 C4 C5 118.98(15) .
C3 C4 H4 120.5 .
C5 C4 H4 120.5 .
C6 C5 C4 121.34(14) .
C6 C5 Cl1 119.09(12) .
C4 C5 Cl1 119.57(12) .
C5 C6 C1 119.40(14) .
C5 C6 H6 120.3 .
C1 C6 H6 120.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.7406(15) .
N1 N1 1.246(3) 3_655
N1 C2 1.444(2) .
C1 C6 1.389(2) .
C1 C2 1.400(2) .
C1 H1 0.9300 .
C2 C3 1.389(2) .
C3 C4 1.377(2) .
C3 H3 0.9300 .
C4 C5 1.384(2) .
C4 H4 0.9300 .
C5 C6 1.384(2) .
C6 H6 0.9300 .
