#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/72/4027228.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_4027228
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            'C20 H15 Cl2 N3 O'
_chemical_formula_weight         384.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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            4
_cell_length_a                   9.8152(6)
_cell_length_b                   10.6246(5)
_cell_length_c                   17.8012(8)
_cell_measurement_temperature    298(2)
_cell_volume                     1856.35(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18741
_diffrn_reflns_theta_full        24.84
_diffrn_reflns_theta_max         24.84
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADBAS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             792.0
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_coef       0.0051(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                2075
_reflns_number_total             3195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300592t_si_002.cif
_cod_data_source_block           1c''
_cod_original_cell_volume        1856.36(17)
_cod_database_code               4027228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.18497(17) 0.76309(11) -0.02914(8) 0.1056(6) Uani 1 1 d .
Cl2 Cl 0.17347(16) -0.49522(13) 0.31805(8) 0.1084(5) Uani 1 1 d .
N3 N 0.1371(3) 0.1445(3) 0.06597(17) 0.0572(8) Uani 1 1 d .
C5 C 0.2564(6) 0.5832(4) 0.0690(3) 0.0774(12) Uani 1 1 d .
H5 H 0.3165 0.6421 0.0888 0.093 Uiso 1 1 calc R
C3 C 0.0878(5) 0.5268(4) -0.0222(3) 0.0733(13) Uani 1 1 d .
H3 H 0.0326 0.5486 -0.0627 0.088 Uiso 1 1 calc R
C1 C 0.1625(4) 0.3736(3) 0.0696(2) 0.0580(10) Uani 1 1 d .
C6 C 0.2473(5) 0.4637(4) 0.0996(3) 0.0739(12) Uani 1 1 d .
H6 H 0.2998 0.4438 0.1415 0.089 Uiso 1 1 calc R
C2 C 0.0828(4) 0.4057(4) 0.0077(2) 0.0694(12) Uani 1 1 d .
H2 H 0.0258 0.3457 -0.0138 0.083 Uiso 1 1 calc R
C4 C 0.1749(5) 0.6136(4) 0.0087(3) 0.0692(12) Uani 1 1 d .
C7 C 0.2087(4) -0.1415(4) 0.1802(2) 0.0535(9) Uani 1 1 d .
C10 C 0.1849(5) -0.3564(4) 0.2664(2) 0.0727(13) Uani 1 1 d .
C12 C 0.0835(4) -0.2009(4) 0.1896(2) 0.0656(11) Uani 1 1 d .
H12 H 0.0069 -0.1673 0.1663 0.079 Uiso 1 1 calc R
C9 C 0.3101(5) -0.2995(4) 0.2592(3) 0.0767(13) Uani 1 1 d .
H9 H 0.3863 -0.3329 0.2830 0.092 Uiso 1 1 calc R
C8 C 0.3211(4) -0.1929(4) 0.2164(2) 0.0665(12) Uani 1 1 d .
H8 H 0.4056 -0.1540 0.2114 0.080 Uiso 1 1 calc R
C11 C 0.0705(5) -0.3066(4) 0.2319(2) 0.0725(12) Uani 1 1 d .
H11 H -0.0140 -0.3450 0.2376 0.087 Uiso 1 1 calc R
C13 C 0.1639(4) 0.1321(3) -0.0144(2) 0.0582(10) Uani 1 1 d .
C18 C 0.2869(5) 0.1737(4) -0.0425(2) 0.0710(12) Uani 1 1 d .
H18 H 0.3548 0.2041 -0.0108 0.085 Uiso 1 1 calc R
C16 C 0.2075(7) 0.1193(5) -0.1648(3) 0.0982(18) Uani 1 1 d .
H16 H 0.2219 0.1151 -0.2163 0.118 Uiso 1 1 calc R
C14 C 0.0638(5) 0.0820(4) -0.0592(2) 0.0768(13) Uani 1 1 d .
H14 H -0.0178 0.0532 -0.0390 0.092 Uiso 1 1 calc R
C15 C 0.0885(7) 0.0760(5) -0.1355(3) 0.1020(18) Uani 1 1 d .
H15 H 0.0230 0.0419 -0.1673 0.122 Uiso 1 1 calc R
C17 C 0.3055(6) 0.1685(5) -0.1201(3) 0.0931(16) Uani 1 1 d .
H17 H 0.3856 0.1990 -0.1412 0.112 Uiso 1 1 calc R
O2 O 0.3460(3) 0.0147(3) 0.11986(17) 0.0702(8) Uani 1 1 d .
C19 C 0.2308(4) -0.0261(4) 0.1332(2) 0.0551(10) Uani 1 1 d .
N7 N 0.1207(3) 0.0306(3) 0.10506(18) 0.0569(8) Uani 1 1 d D
H7 H 0.0412 -0.0020 0.1108 0.068 Uiso 1 1 calc RD
C20 C 0.1544(4) 0.2493(4) 0.1085(3) 0.0638(11) Uani 1 1 d .
N6 N 0.1600(4) 0.2447(3) 0.17656(17) 0.0710(11) Uani 1 1 d D
H6A H 0.1273 0.1850 0.1900 0.107 Uiso 1 1 calc RD
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C20 N3 N7 116.4(3)
C20 N3 C13 126.6(3)
N7 N3 C13 115.4(3)
C4 C5 C6 119.0(5)
C4 C3 C2 119.3(4)
C6 C1 C2 118.4(4)
C6 C1 C20 117.9(4)
C2 C1 C20 123.6(4)
C1 C6 C5 121.6(4)
C1 C2 C3 120.6(4)
C3 C4 C5 121.1(4)
C3 C4 Cl1 119.8(4)
C5 C4 Cl1 119.1(4)
C8 C7 C12 117.9(4)
C8 C7 C19 117.6(3)
C12 C7 C19 124.4(3)
C9 C10 C11 121.0(4)
C9 C10 Cl2 118.7(4)
C11 C10 Cl2 120.3(4)
C11 C12 C7 121.6(4)
C8 C9 C10 119.1(4)
C9 C8 C7 121.3(4)
C12 C11 C10 119.0(4)
C14 C13 C18 122.6(4)
C14 C13 N3 118.4(4)
C18 C13 N3 118.9(4)
C13 C18 C17 117.4(5)
C17 C16 C15 121.1(5)
C13 C14 C15 117.6(5)
C16 C15 C14 120.8(5)
C16 C17 C18 120.3(5)
O2 C19 N7 120.8(4)
O2 C19 C7 121.8(3)
N7 C19 C7 117.4(3)
C19 N7 N3 118.8(3)
N6 C20 N3 121.9(4)
N6 C20 C1 119.8(4)
N3 C20 C1 118.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.728(5)
Cl2 C10 1.741(4)
N3 C20 1.357(5)
N3 N7 1.405(4)
N3 C13 1.460(5)
C5 C4 1.377(7)
C5 C6 1.385(6)
C3 C4 1.373(6)
C3 C2 1.394(6)
C1 C6 1.377(6)
C1 C2 1.393(6)
C1 C20 1.493(6)
C7 C8 1.389(5)
C7 C12 1.390(5)
C7 C19 1.501(5)
C10 C9 1.376(6)
C10 C11 1.385(6)
C12 C11 1.359(6)
C9 C8 1.369(6)
C13 C14 1.374(6)
C13 C18 1.379(6)
C18 C17 1.395(7)
C16 C17 1.353(8)
C16 C15 1.359(8)
C14 C15 1.381(7)
O2 C19 1.234(5)
C19 N7 1.335(5)
C20 N6 1.214(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659496
