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#$Date: 2016-03-24 02:29:14 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179581 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/46/4504681.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_4504681
loop_
_publ_author_name
'Zhang, Jie-Peng'
'Lin, Yan-Yong'
'Huang, Xiao-Chun'
'Chen, Xiao-Ming'
_publ_section_title
;
 From One- to Three-Dimensional Architectures:  Supramolecular
 Isomerism of Copper(I) 3,5-Di(4-pyridyl)-1,2,4-triazolate Involving in
 Situ Ligand Synthesis
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              519
_journal_paper_doi               10.1021/cg050453l
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C12 H19 Cu N6 O4'
_chemical_formula_weight         374.87
_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                 90.256(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2065(8)
_cell_length_b                   25.574(2)
_cell_length_c                   6.8104(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1603.5(2)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '/w scan'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            6728
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    1.391
_exptl_absorpt_correction_T_max  0.7683
_exptl_absorpt_correction_T_min  0.7224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0419
_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)+(0.0687P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                2840
_reflns_number_total             3491
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050453lsi20050902_093943.cif
_cod_data_source_block           compound_3
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4504681
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
Cu1 Cu 0.30598(3) 0.342874(9) 0.64010(4) 0.03977(12) Uani 1 1 d .
C1 C 0.2255(2) 0.10058(7) 0.6827(3) 0.0294(4) Uani 1 1 d .
C2 C 0.2454(2) 0.15721(7) 0.6647(3) 0.0301(4) Uani 1 1 d .
C3 C 0.1300(2) 0.19157(8) 0.6890(4) 0.0425(5) Uani 1 1 d .
H3A H 0.0375 0.1787 0.7139 0.051 Uiso 1 1 calc R
C4 C 0.1526(2) 0.24441(8) 0.6762(4) 0.0435(5) Uani 1 1 d .
H4A H 0.0726 0.2663 0.6899 0.052 Uiso 1 1 calc R
C5 C 0.3937(2) 0.23360(8) 0.6208(4) 0.0385(5) Uani 1 1 d .
H5A H 0.4851 0.2476 0.5964 0.046 Uiso 1 1 calc R
C6 C 0.3803(2) 0.17964(8) 0.6298(4) 0.0381(5) Uani 1 1 d .
H6A H 0.4615 0.1585 0.6126 0.046 Uiso 1 1 calc R
C7 C 0.1356(2) 0.02689(7) 0.7250(3) 0.0284(4) Uani 1 1 d .
C8 C 0.0337(2) -0.01680(7) 0.7582(3) 0.0292(4) Uani 1 1 d .
C9 C -0.1150(2) -0.00894(8) 0.7528(3) 0.0330(4) Uani 1 1 d .
H9A H -0.1526 0.0243 0.7312 0.040 Uiso 1 1 calc R
C10 C -0.2079(2) -0.05115(7) 0.7799(3) 0.0335(4) Uani 1 1 d .
H10A H -0.3074 -0.0452 0.7722 0.040 Uiso 1 1 calc R
C11 C -0.0174(2) -0.10641(8) 0.8263(3) 0.0383(5) Uani 1 1 d .
H11A H 0.0180 -0.1397 0.8535 0.046 Uiso 1 1 calc R
C12 C 0.0811(2) -0.06676(8) 0.7984(3) 0.0370(5) Uani 1 1 d .
H12A H 0.1801 -0.0737 0.8068 0.044 Uiso 1 1 calc R
N1 N 0.33769(17) 0.06719(6) 0.6810(3) 0.0336(4) Uani 1 1 d .
N2 N 0.27820(18) 0.01896(6) 0.7099(3) 0.0335(4) Uani 1 1 d .
N3 N 0.09632(16) 0.07709(6) 0.7087(2) 0.0276(3) Uani 1 1 d .
N4 N 0.28288(17) 0.26662(7) 0.6452(3) 0.0357(4) Uani 1 1 d .
N5 N -0.16208(18) -0.09974(6) 0.8165(3) 0.0330(4) Uani 1 1 d .
N6 N 0.5007(2) 0.37747(9) 0.5870(4) 0.0510(5) Uani 1 1 d .
H61 H 0.571(3) 0.3549(13) 0.544(5) 0.062(8) Uiso 1 1 d .
H62 H 0.545(4) 0.3984(14) 0.683(5) 0.083(10) Uiso 1 1 d .
H63 H 0.486(4) 0.3997(14) 0.484(6) 0.079(11) Uiso 1 1 d .
O1 O 0.7558(3) 0.30818(10) 0.4754(4) 0.0689(6) Uani 1 1 d .
H11 H 0.788(4) 0.2779(17) 0.422(6) 0.095(12) Uiso 1 1 d .
H12 H 0.783(4) 0.3259(14) 0.399(5) 0.063(10) Uiso 1 1 d .
O2 O 0.60339(19) 0.43065(6) 0.9814(3) 0.0464(4) Uani 1 1 d .
H21 H 0.616(3) 0.4636(12) 0.925(4) 0.060(8) Uiso 1 1 d .
H22 H 0.530(3) 0.4358(10) 1.033(4) 0.045(8) Uiso 1 1 d .
O3 O 0.81631(19) 0.37300(7) 1.1568(3) 0.0483(4) Uani 1 1 d .
H31 H 0.889(3) 0.3933(12) 1.164(4) 0.056(8) Uiso 1 1 d .
H32 H 0.753(3) 0.3946(12) 1.110(4) 0.055(8) Uiso 1 1 d .
O4 O 0.7702(3) 0.29434(8) 0.8755(4) 0.0732(7) Uani 1 1 d .
H41 H 0.802(4) 0.3213(15) 0.958(5) 0.076(10) Uiso 1 1 d .
H42 H 0.770(5) 0.3025(16) 0.761(7) 0.096(15) Uiso 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'
O O 0.0106 0.0060 '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
N4 Cu1 N5 130.91(7) . 2_556
N4 Cu1 N6 122.10(9) . .
N5 Cu1 N6 106.99(8) 2_556 .
N1 C1 N3 113.49(16) . .
N1 C1 C2 122.19(17) . .
N3 C1 C2 124.29(17) . .
C3 C2 C6 116.34(17) . .
C3 C2 C1 121.32(18) . .
C6 C2 C1 122.31(18) . .
C4 C3 C2 120.04(19) . .
C4 C3 H3A 120.0 . .
C2 C3 H3A 120.0 . .
N4 C4 C3 124.2(2) . .
N4 C4 H4A 117.9 . .
C3 C4 H4A 117.9 . .
N4 C5 C6 123.78(19) . .
N4 C5 H5A 118.1 . .
C6 C5 H5A 118.1 . .
C5 C6 C2 119.85(19) . .
C5 C6 H6A 120.1 . .
C2 C6 H6A 120.1 . .
N2 C7 N3 113.93(16) . .
N2 C7 C8 121.56(17) . .
N3 C7 C8 124.51(17) . .
C12 C8 C9 116.90(17) . .
C12 C8 C7 122.08(17) . .
C9 C8 C7 121.01(17) . .
C8 C9 C10 119.50(18) . .
C8 C9 H9A 120.2 . .
C10 C9 H9A 120.2 . .
N5 C10 C9 123.63(18) . .
N5 C10 H10A 118.2 . .
C9 C10 H10A 118.2 . .
N5 C11 C12 123.62(18) . .
N5 C11 H11A 118.2 . .
C12 C11 H11A 118.2 . .
C11 C12 C8 120.23(18) . .
C11 C12 H12A 119.9 . .
C8 C12 H12A 119.9 . .
C1 N1 N2 105.36(15) . .
C7 N2 N1 105.65(15) . .
C7 N3 C1 101.57(15) . .
C5 N4 C4 115.78(18) . .
C5 N4 Cu1 122.92(14) . .
C4 N4 Cu1 121.29(14) . .
C10 N5 C11 116.07(17) . .
C10 N5 Cu1 120.11(13) . 2_546
C11 N5 Cu1 123.80(13) . 2_546
Cu1 N6 H61 114.1(19) . .
Cu1 N6 H62 120(2) . .
H61 N6 H62 106(3) . .
Cu1 N6 H63 106(2) . .
H61 N6 H63 104(3) . .
H62 N6 H63 104(3) . .
H11 O1 H12 97(4) . .
H21 O2 H22 98(3) . .
H31 O3 H32 99(3) . .
H41 O4 H42 113(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N4 1.9619(18) .
Cu1 N5 2.0000(16) 2_556
Cu1 N6 2.033(2) .
C1 N1 1.340(2) .
C1 N3 1.345(2) .
C1 C2 1.465(3) .
C2 C3 1.389(3) .
C2 C6 1.390(3) .
C3 C4 1.370(3) .
C3 H3A 0.9300 .
C4 N4 1.345(3) .
C4 H4A 0.9300 .
C5 N4 1.335(3) .
C5 C6 1.387(3) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 N2 1.333(2) .
C7 N3 1.338(2) .
C7 C8 1.477(2) .
C8 C12 1.377(3) .
C8 C9 1.384(3) .
C9 C10 1.390(3) .
C9 H9A 0.9300 .
C10 N5 1.335(2) .
C10 H10A 0.9300 .
C11 N5 1.344(3) .
C11 C12 1.374(3) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
N1 N2 1.364(2) .
N5 Cu1 2.0000(16) 2_546
N6 H61 0.92(3) .
N6 H62 0.94(4) .
N6 H63 0.91(4) .
O1 H11 0.91(4) .
O1 H12 0.74(4) .
O2 H21 0.93(3) .
O2 H22 0.77(3) .
O3 H31 0.85(3) .
O3 H32 0.86(3) .
O4 H41 0.94(4) .
O4 H42 0.80(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H61 O1 0.92(3) 2.13(4) 3.041(3) 171(3) .
N6 H62 O2 0.94(4) 2.26(4) 3.152(3) 160(3) .
N6 H63 N1 0.91(4) 2.61(4) 3.445(3) 152(3) 4_565
O1 H12 O3 0.74(4) 2.06(4) 2.789(3) 168(4) 1_554
O1 H11 O4 0.91(4) 1.88(4) 2.712(3) 152(4) 4_565
O2 H22 N1 0.77(3) 2.04(3) 2.804(3) 168(3) 4_566
O2 H21 N2 0.93(3) 1.95(3) 2.828(2) 156(3) 2_656
O3 H31 N3 0.85(3) 2.07(3) 2.897(2) 163(3) 4_666
O3 H32 O2 0.86(3) 1.87(3) 2.724(2) 169(3) .
O4 H42 O1 0.80(5) 1.96(5) 2.750(4) 169(4) .
O4 H41 O3 0.94(4) 1.89(4) 2.809(3) 165(3) .
