#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:03:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180057 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/03/7050357.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_7050357
loop_
_publ_author_name
'Ray, Umasankar'
'Banerjee, Debasis'
'Mostafa, Golam'
'Lu, Tian-Huey'
'Sinha, Chittaranjan'
_publ_section_title
;
 Copper coordination compounds of chelating imidazole-azo-aryl ligand.
 The molecular structures of
 bis[1-ethyl-2-(p-tolylazo)imidazole]-bis-(azido)copper(ii) and
 bis[1-methyl-2-(phenylazo)imidazole]-bis(thiocyanato)copper(ii)
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1437
_journal_paper_doi               10.1039/b406445c
_journal_volume                  28
_journal_year                    2004
_chemical_formula_sum            'C24 H28 Cu N14'
_chemical_formula_weight         576.14
_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                   11.8632(8)
_cell_length_b                   17.6782(13)
_cell_length_c                   26.703(2)
_cell_measurement_temperature    293(2)
_cell_volume                     5600.2(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31899
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.821
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             2392
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0546
_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/[\\s²(Fo²)+(0.0613P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                3521
_reflns_number_total             6480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b406445c.txt
_cod_data_source_block           b
_cod_original_cell_volume        5600.1(7)
_cod_database_code               7050357
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.24027(3) 0.030542(19) 0.137057(12) 0.05354(13) Uani 1 1 d . . .
N1 N 0.34440(19) -0.05493(12) 0.11886(9) 0.0517(6) Uani 1 1 d . . .
N2 N 0.49269(19) -0.10895(13) 0.08369(9) 0.0553(6) Uani 1 1 d . . .
N3 N 0.48376(19) 0.02526(13) 0.07782(8) 0.0516(6) Uani 1 1 d . . .
N4 N 0.41932(19) 0.08037(13) 0.08688(8) 0.0508(5) Uani 1 1 d . . .
N5 N 0.3239(2) 0.04783(13) 0.20157(9) 0.0588(6) Uani 1 1 d . . .
N6 N 0.3615(2) 0.03662(13) 0.28259(9) 0.0562(6) Uani 1 1 d . . .
N7 N 0.2132(2) -0.04110(12) 0.25153(9) 0.0543(6) Uani 1 1 d . . .
N8 N 0.16231(19) -0.05804(13) 0.21142(9) 0.0554(6) Uani 1 1 d . . .
N9 N 0.1419(2) 0.00304(15) 0.08095(10) 0.0663(7) Uani 1 1 d . . .
N10 N 0.1873(2) -0.01368(14) 0.04229(11) 0.0655(7) Uani 1 1 d . . .
N11 N 0.2278(3) -0.03047(18) 0.00448(12) 0.0930(10) Uani 1 1 d . . .
N12 N 0.1588(2) 0.12561(17) 0.15058(11) 0.0792(9) Uani 1 1 d . . .
N13 N 0.0744(3) 0.14309(14) 0.13201(11) 0.0720(8) Uani 1 1 d . . .
C1 C 0.3351(3) -0.13141(16) 0.12302(11) 0.0611(8) Uani 1 1 d . . .
H1 H 0.2757 -0.1569 0.1383 0.073 Uiso 1 1 calc R . .
C2 C 0.4256(3) -0.16444(17) 0.10153(12) 0.0629(8) Uani 1 1 d . . .
H2 H 0.4393 -0.2161 0.0994 0.076 Uiso 1 1 calc R . .
C3 C 0.4401(2) -0.04295(15) 0.09447(10) 0.0493(7) Uani 1 1 d . . .
C4 C 0.4587(2) 0.15071(15) 0.06851(10) 0.0497(7) Uani 1 1 d . . .
C5 C 0.5637(2) 0.16223(17) 0.04761(11) 0.0583(7) Uani 1 1 d . . .
H5 H 0.6157 0.1229 0.0461 0.070 Uiso 1 1 calc R . .
C6 C 0.5907(3) 0.23242(17) 0.02914(11) 0.0634(8) Uani 1 1 d . . .
H6 H 0.6619 0.2402 0.0156 0.076 Uiso 1 1 calc R . .
C7 C 0.5148(3) 0.29188(16) 0.03012(11) 0.0622(8) Uani 1 1 d . . .
C8 C 0.4106(3) 0.27924(16) 0.05075(11) 0.0627(8) Uani 1 1 d . . .
H8 H 0.3582 0.3184 0.0516 0.075 Uiso 1 1 calc R . .
C9 C 0.3821(2) 0.20966(15) 0.07027(10) 0.0564(7) Uani 1 1 d . . .
H9 H 0.3115 0.2023 0.0846 0.068 Uiso 1 1 calc R . .
C10 C 0.6037(3) -0.11857(18) 0.06053(12) 0.0677(9) Uani 1 1 d . . .
H10A H 0.6306 -0.0700 0.0485 0.081 Uiso 1 1 calc R . .
H10B H 0.5973 -0.1523 0.0320 0.081 Uiso 1 1 calc R . .
C11 C 0.6865(3) -0.1505(2) 0.09719(14) 0.0920(11) Uani 1 1 d . . .
H11A H 0.7585 -0.1563 0.0812 0.138 Uiso 1 1 calc R . .
H11B H 0.6605 -0.1989 0.1087 0.138 Uiso 1 1 calc R . .
H11C H 0.6937 -0.1168 0.1252 0.138 Uiso 1 1 calc R . .
C12 C 0.5455(3) 0.36892(18) 0.00919(15) 0.0907(11) Uani 1 1 d . . .
H12A H 0.6210 0.3675 -0.0037 0.136 Uiso 1 1 calc R . .
H12B H 0.5407 0.4061 0.0353 0.136 Uiso 1 1 calc R . .
H12C H 0.4942 0.3819 -0.0173 0.136 Uiso 1 1 calc R . .
C13 C 0.4091(3) 0.09503(19) 0.21395(12) 0.0717(9) Uani 1 1 d . . .
H13 H 0.4457 0.1274 0.1918 0.086 Uiso 1 1 calc R . .
C14 C 0.4338(3) 0.08840(18) 0.26350(12) 0.0702(9) Uani 1 1 d . . .
H14 H 0.4896 0.1144 0.2809 0.084 Uiso 1 1 calc R . .
C15 C 0.2960(2) 0.01306(16) 0.24379(10) 0.0522(7) Uani 1 1 d . . .
C16 C 0.0771(2) -0.11359(16) 0.21654(11) 0.0537(7) Uani 1 1 d . . .
C17 C 0.0314(2) -0.14112(17) 0.17288(11) 0.0606(8) Uani 1 1 d . . .
H17 H 0.0568 -0.1228 0.1422 0.073 Uiso 1 1 calc R . .
C18 C -0.0510(3) -0.19532(18) 0.17407(13) 0.0658(8) Uani 1 1 d . . .
H18 H -0.0792 -0.2143 0.1441 0.079 Uiso 1 1 calc R . .
C19 C -0.0932(3) -0.22233(17) 0.21859(13) 0.0651(8) Uani 1 1 d . . .
C20 C -0.0468(3) -0.1946(2) 0.26187(13) 0.0827(10) Uani 1 1 d . . .
H20 H -0.0730 -0.2128 0.2924 0.099 Uiso 1 1 calc R . .
C21 C 0.0363(3) -0.1413(2) 0.26169(12) 0.0774(10) Uani 1 1 d . . .
H21 H 0.0656 -0.1235 0.2918 0.093 Uiso 1 1 calc R . .
C22 C 0.3533(3) 0.01107(17) 0.33486(11) 0.0647(8) Uani 1 1 d . . .
H22A H 0.4253 0.0188 0.3513 0.078 Uiso 1 1 calc R . .
H22B H 0.3371 -0.0427 0.3354 0.078 Uiso 1 1 calc R . .
C23 C 0.2639(3) 0.0520(2) 0.36336(13) 0.0920(12) Uani 1 1 d . . .
H23A H 0.2617 0.0334 0.3971 0.138 Uiso 1 1 calc R . .
H23B H 0.1921 0.0436 0.3477 0.138 Uiso 1 1 calc R . .
H23C H 0.2803 0.1051 0.3636 0.138 Uiso 1 1 calc R . .
C24 C -0.1870(3) -0.2801(2) 0.21981(16) 0.0987(12) Uani 1 1 d . . .
H24A H -0.2048 -0.2922 0.2540 0.148 Uiso 1 1 calc R . .
H24B H -0.1633 -0.3251 0.2026 0.148 Uiso 1 1 calc R . .
H24C H -0.2526 -0.2597 0.2036 0.148 Uiso 1 1 calc R . .
N14 N -0.0125(3) 0.16336(17) 0.11504(16) 0.1062(12) 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'
Cu Cu 0.3201 1.2651 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu N4 68.70(8) . . ?
N4 Cu N9 99.93(9) . . ?
N9 Cu N12 93.42(11) . . ?
N9 Cu N5 170.38(11) . . ?
N12 Cu N5 87.44(11) . . ?
N9 Cu N1 89.69(10) . . ?
N12 Cu N1 170.23(11) . . ?
N5 Cu N1 91.04(9) . . ?
N8 Cu N9 102.41(9) . . ?
N8 Cu N12 101.08(10) . . ?
C3 N1 C1 105.6(2) . . ?
C3 N1 Cu 121.64(18) . . ?
C1 N1 Cu 132.6(2) . . ?
C2 N2 C3 106.2(2) . . ?
C2 N2 C10 126.5(2) . . ?
C3 N2 C10 127.2(2) . . ?
N4 N3 C3 112.6(2) . . ?
N3 N4 C4 114.3(2) . . ?
C15 N5 C13 105.3(2) . . ?
C15 N5 Cu 122.34(19) . . ?
C13 N5 Cu 132.2(2) . . ?
C14 N6 C15 106.4(2) . . ?
C14 N6 C22 127.4(3) . . ?
C15 N6 C22 126.3(2) . . ?
N8 N7 C15 112.0(2) . . ?
N7 N8 C16 115.0(2) . . ?
N10 N9 Cu 116.8(2) . . ?
N11 N10 N9 177.9(4) . . ?
N13 N12 Cu 124.9(3) . . ?
N12 N13 N14 176.7(4) . . ?
C2 C1 N1 109.3(3) . . ?
N2 C2 C1 107.7(3) . . ?
N1 C3 N2 111.2(2) . . ?
N1 C3 N3 128.1(2) . . ?
N2 C3 N3 120.6(2) . . ?
C5 C4 C9 119.7(3) . . ?
C5 C4 N4 124.5(3) . . ?
C9 C4 N4 115.7(2) . . ?
C6 C5 C4 119.2(3) . . ?
C5 C6 C7 121.9(3) . . ?
C8 C7 C6 118.0(3) . . ?
C8 C7 C12 120.7(3) . . ?
C6 C7 C12 121.3(3) . . ?
C7 C8 C9 121.2(3) . . ?
C8 C9 C4 119.9(3) . . ?
N2 C10 C11 111.0(3) . . ?
N5 C13 C14 110.2(3) . . ?
N6 C14 C13 106.7(3) . . ?
N5 C15 N6 111.3(3) . . ?
N5 C15 N7 128.5(3) . . ?
N6 C15 N7 120.1(3) . . ?
C17 C16 C21 118.3(3) . . ?
C17 C16 N8 116.4(3) . . ?
C21 C16 N8 125.3(3) . . ?
C18 C17 C16 120.6(3) . . ?
C17 C18 C19 121.5(3) . . ?
C20 C19 C18 117.3(3) . . ?
C20 C19 C24 121.3(3) . . ?
C18 C19 C24 121.4(3) . . ?
C21 C20 C19 122.3(3) . . ?
C20 C21 C16 119.9(3) . . ?
N6 C22 C23 112.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N9 1.960(3) . ?
Cu N12 1.972(3) . ?
Cu N4 2.661(2) . ?
Cu N5 2.011(2) . ?
Cu N1 2.011(2) . ?
Cu N8 2.693(2) . ?
N1 C3 1.326(3) . ?
N1 C1 1.361(3) . ?
N2 C2 1.350(4) . ?
N2 C3 1.354(3) . ?
N2 C10 1.464(4) . ?
N3 N4 1.262(3) . ?
N3 C3 1.386(3) . ?
N4 C4 1.416(3) . ?
N5 C15 1.326(3) . ?
N5 C13 1.352(4) . ?
N6 C14 1.354(4) . ?
N6 C15 1.360(3) . ?
N6 C22 1.470(4) . ?
N7 N8 1.266(3) . ?
N7 C15 1.387(4) . ?
N8 C16 1.415(3) . ?
N9 N10 1.201(4) . ?
N10 N11 1.156(4) . ?
N12 N13 1.159(4) . ?
N13 N14 1.182(4) . ?
C1 C2 1.351(4) . ?
C4 C5 1.381(4) . ?
C4 C9 1.383(4) . ?
C5 C6 1.373(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.372(4) . ?
C7 C12 1.517(4) . ?
C8 C9 1.378(4) . ?
C10 C11 1.498(4) . ?
C13 C14 1.360(4) . ?
C16 C17 1.375(4) . ?
C16 C21 1.389(4) . ?
C17 C18 1.370(4) . ?
C18 C19 1.375(4) . ?
C19 C20 1.370(4) . ?
C19 C24 1.511(4) . ?
C20 C21 1.364(4) . ?
C22 C23 1.492(4) . ?
