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#$Date: 2016-03-25 15:14:08 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179915 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/10/7021021.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_7021021
loop_
_publ_author_name
'Maekawa, Masahiko'
'Miyazaki, Takeshi'
'Sugimoto, Kunihisa'
'Okubo, Takashi'
'Kuroda-Sowa, Takayoshi'
'Munakata, Megumu'
'Kitagawa, Susumu'
_publ_section_title
;
 Structural diversity among copper(i) ethylene adducts of
 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4258
_journal_page_last               4266
_journal_paper_doi               10.1039/c2dt32649c
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C16 H16 Cl Cu2 N6 O4'
_chemical_formula_sum            'C16 H16 Cl Cu2 N6 O4'
_chemical_formula_weight         518.88
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 115.142(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.978(10)
_cell_length_b                   5.116(3)
_cell_length_c                   22.301(13)
_cell_measurement_reflns_used    3831
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1856.8(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.1
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13451
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    2.473
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.106
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0514
_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)+(0.0387P)²+4.4307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                3155
_reflns_number_total             4245
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2dt32649c.txt
_cod_data_source_block           {[Cu2(bptz-)(C2H4)2]ClO4}2
_cod_original_cell_volume        1856.7(18)
_cod_database_code               7021021
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.92902(3) 0.06812(11) 0.07355(2) 0.01508(14) Uani 1 1 d .
Cu2 Cu 1.06004(3) 0.06452(11) 0.41836(2) 0.01613(14) Uani 1 1 d .
Cl1 Cl 1.00355(7) 0.23327(19) 0.24792(5) 0.0214(2) Uani 1 1 d .
O1 O 1.0867(2) 0.2863(8) 0.25344(19) 0.0447(10) Uani 1 1 d .
O2 O 0.9483(2) 0.3539(7) 0.18800(17) 0.0368(9) Uani 1 1 d .
O3 O 0.9998(3) 0.3389(7) 0.30508(19) 0.0463(10) Uani 1 1 d .
O4 O 0.9915(2) -0.0443(6) 0.24515(15) 0.0254(7) Uani 1 1 d .
N1 N 1.0473(2) -0.0310(7) 0.11157(16) 0.0155(7) Uani 1 1 d .
N2 N 0.9639(2) 0.3390(7) 0.02885(16) 0.0140(7) Uani 1 1 d .
N3 N 0.91570(19) 0.5244(7) -0.01678(16) 0.0148(7) Uani 1 1 d .
N4 N 0.9411(2) -0.0271(7) 0.38625(16) 0.0155(7) Uani 1 1 d .
N5 N 1.0320(2) 0.3355(7) 0.46822(17) 0.0155(7) Uani 1 1 d .
N6 N 1.0832(2) 0.5170(7) 0.51277(16) 0.0159(8) Uani 1 1 d .
C1 C 1.0858(3) -0.2188(9) 0.15610(19) 0.0182(9) Uani 1 1 d .
H1 H 1.0548 -0.3277 0.1715 0.022 Uiso 1 1 calc R
C2 C 1.1698(3) -0.2566(9) 0.1799(2) 0.0212(9) Uani 1 1 d .
H2 H 1.1957 -0.3928 0.2108 0.025 Uiso 1 1 calc R
C3 C 1.2158(2) -0.0970(9) 0.1590(2) 0.0210(10) Uani 1 1 d .
H3 H 1.2735 -0.1215 0.1751 0.025 Uiso 1 1 calc R
C4 C 1.1765(2) 0.1001(8) 0.1140(2) 0.0163(8) Uani 1 1 d .
H4 H 1.2067 0.2150 0.0993 0.020 Uiso 1 1 calc R
C5 C 1.0924(2) 0.1261(8) 0.09114(19) 0.0143(8) Uani 1 1 d .
C6 C 1.0443(2) 0.3279(8) 0.04218(19) 0.0132(8) Uani 1 1 d .
C8 C 0.8563(2) -0.1758(9) 0.0927(2) 0.0176(9) Uani 1 1 d .
H8A H 0.8496 -0.3525 0.0730 0.021 Uiso 1 1 calc R
H8B H 0.8610 -0.1755 0.1386 0.021 Uiso 1 1 calc R
C9 C 0.8103(2) 0.0196(9) 0.0520(2) 0.0204(10) Uani 1 1 d .
H9A H 0.7853 0.1471 0.0714 0.025 Uiso 1 1 calc R
H9B H 0.7739 -0.0300 0.0058 0.025 Uiso 1 1 calc R
C10 C 0.8981(3) -0.2102(9) 0.3422(2) 0.0190(9) Uani 1 1 d .
H10 H 0.9262 -0.3244 0.3251 0.023 Uiso 1 1 calc R
C11 C 0.8140(3) -0.2383(9) 0.3206(2) 0.0221(10) Uani 1 1 d .
H11 H 0.7849 -0.3689 0.2891 0.027 Uiso 1 1 calc R
C12 C 0.7727(3) -0.0744(9) 0.3455(2) 0.0208(9) Uani 1 1 d .
H12 H 0.7151 -0.0915 0.3314 0.025 Uiso 1 1 calc R
C13 C 0.8167(2) 0.1161(9) 0.3914(2) 0.0186(9) Uani 1 1 d .
H13 H 0.7899 0.2319 0.4092 0.022 Uiso 1 1 calc R
C14 C 0.9010(2) 0.1325(8) 0.41065(19) 0.0128(8) Uani 1 1 d .
C15 C 0.9526(2) 0.3329(8) 0.45876(19) 0.0148(8) Uani 1 1 d .
C17 C 1.1293(2) -0.1865(9) 0.3952(2) 0.0183(9) Uani 1 1 d .
H17A H 1.1384 -0.3609 0.4164 0.022 Uiso 1 1 calc R
H17B H 1.1204 -0.1912 0.3482 0.022 Uiso 1 1 calc R
C18 C 1.1765(2) 0.0153(9) 0.4331(2) 0.0211(10) Uani 1 1 d .
H18A H 1.1982 0.1406 0.4106 0.025 Uiso 1 1 calc R
H18B H 1.2162 -0.0289 0.4787 0.025 Uiso 1 1 calc R
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'
Cu Cu 0.3201 1.2651 '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
_geom_angle_site_symmetry_1
N2 Cu1 C8 159.80(15) .
N2 Cu1 N1 83.23(14) .
C8 Cu1 N1 115.54(16) .
N2 Cu1 C9 120.42(16) .
C8 Cu1 C9 40.24(18) .
N1 Cu1 C9 155.63(17) .
N5 Cu2 C18 119.89(16) .
N5 Cu2 N4 82.89(14) .
C18 Cu2 N4 156.58(17) .
N5 Cu2 C17 158.73(16) .
C18 Cu2 C17 40.25(18) .
N4 Cu2 C17 116.39(16) .
O3 Cl1 O2 113.6(2) .
O3 Cl1 O4 110.7(2) .
O2 Cl1 O4 110.9(2) .
O3 Cl1 O1 106.8(3) .
O2 Cl1 O1 106.1(2) .
O4 Cl1 O1 108.4(2) .
C1 N1 C5 118.7(4) .
C1 N1 Cu1 128.2(3) .
C5 N1 Cu1 112.9(3) .
C6 N2 N3 117.8(3) .
C6 N2 Cu1 113.8(3) .
N3 N2 Cu1 128.3(3) .
C6 N3 N2 114.8(3) 3_765
C10 N4 C14 118.6(3) .
C10 N4 Cu2 128.5(3) .
C14 N4 Cu2 112.8(3) .
C15 N5 N6 117.0(3) .
C15 N5 Cu2 114.3(3) .
N6 N5 Cu2 128.6(2) .
C15 N6 N5 115.0(3) 3_766
N1 C1 C2 121.3(4) .
N1 C1 H1 119.4 .
C2 C1 H1 119.4 .
C3 C2 C1 120.1(4) .
C3 C2 H2 120.0 .
C1 C2 H2 120.0 .
C2 C3 C4 118.7(4) .
C2 C3 H3 120.6 .
C4 C3 H3 120.6 .
C5 C4 C3 118.7(4) .
C5 C4 H4 120.7 .
C3 C4 H4 120.7 .
N1 C5 C4 122.5(4) .
N1 C5 C6 114.7(3) .
C4 C5 C6 122.9(4) .
N3 C6 N2 127.5(4) 3_765
N3 C6 C5 117.3(3) 3_765
N2 C6 C5 115.2(3) .
C9 C8 Cu1 70.4(2) .
C9 C8 H8A 116.6 .
Cu1 C8 H8A 116.6 .
C9 C8 H8B 116.6 .
Cu1 C8 H8B 116.6 .
H8A C8 H8B 113.6 .
C8 C9 Cu1 69.3(2) .
C8 C9 H9A 116.7 .
Cu1 C9 H9A 116.7 .
C8 C9 H9B 116.7 .
Cu1 C9 H9B 116.7 .
H9A C9 H9B 113.7 .
N4 C10 C11 122.1(4) .
N4 C10 H10 119.0 .
C11 C10 H10 119.0 .
C12 C11 C10 119.4(4) .
C12 C11 H11 120.3 .
C10 C11 H11 120.3 .
C11 C12 C13 119.1(4) .
C11 C12 H12 120.4 .
C13 C12 H12 120.4 .
C14 C13 C12 118.2(4) .
C14 C13 H13 120.9 .
C12 C13 H13 120.9 .
N4 C14 C13 122.6(4) .
N4 C14 C15 115.5(3) .
C13 C14 C15 121.8(4) .
N6 C15 N5 128.0(4) 3_766
N6 C15 C14 117.6(4) 3_766
N5 C15 C14 114.4(4) .
C18 C17 Cu2 69.4(2) .
C18 C17 H17A 116.7 .
Cu2 C17 H17A 116.7 .
C18 C17 H17B 116.7 .
Cu2 C17 H17B 116.7 .
H17A C17 H17B 113.7 .
C17 C18 Cu2 70.3(2) .
C17 C18 H18A 116.6 .
Cu2 C18 H18A 116.6 .
C17 C18 H18B 116.6 .
Cu2 C18 H18B 116.6 .
H18A C18 H18B 113.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.959(3) .
Cu1 C8 1.980(4) .
Cu1 N1 1.992(4) .
Cu1 C9 1.994(4) .
Cu2 N5 1.972(4) .
Cu2 C18 1.992(4) .
Cu2 N4 2.000(4) .
Cu2 C17 2.004(4) .
Cl1 O3 1.412(4) .
Cl1 O2 1.423(3) .
Cl1 O4 1.434(3) .
Cl1 O1 1.472(4) .
N1 C1 1.343(5) .
N1 C5 1.350(5) .
N2 C6 1.348(5) .
N2 N3 1.392(5) .
N3 C6 1.325(5) 3_765
N4 C10 1.340(5) .
N4 C14 1.348(5) .
N5 C15 1.352(5) .
N5 N6 1.386(5) .
N6 C15 1.324(5) 3_766
C1 C2 1.385(6) .
C1 H1 0.9500 .
C2 C3 1.378(6) .
C2 H2 0.9500 .
C3 C4 1.386(6) .
C3 H3 0.9500 .
C4 C5 1.382(5) .
C4 H4 0.9500 .
C5 C6 1.484(6) .
C6 N3 1.325(5) 3_765
C8 C9 1.367(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.386(6) .
C10 H10 0.9500 .
C11 C12 1.381(6) .
C11 H11 0.9500 .
C12 C13 1.392(6) .
C12 H12 0.9500 .
C13 C14 1.390(5) .
C13 H13 0.9500 .
C14 C15 1.489(6) .
C15 N6 1.324(5) 3_766
C17 C18 1.375(6) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
N2 Cu1 N1 C1 177.1(4) .
C8 Cu1 N1 C1 -10.8(4) .
C9 Cu1 N1 C1 -16.1(6) .
N2 Cu1 N1 C5 1.1(3) .
C8 Cu1 N1 C5 173.3(3) .
C9 Cu1 N1 C5 167.9(4) .
C8 Cu1 N2 C6 -157.6(4) .
N1 Cu1 N2 C6 1.6(3) .
C9 Cu1 N2 C6 -172.1(3) .
C8 Cu1 N2 N3 18.0(7) .
N1 Cu1 N2 N3 177.2(3) .
C9 Cu1 N2 N3 3.5(4) .
C6 N2 N3 C6 -0.2(6) 3_765
Cu1 N2 N3 C6 -175.6(3) 3_765
N5 Cu2 N4 C10 177.3(4) .
C18 Cu2 N4 C10 -15.4(7) .
C17 Cu2 N4 C10 -12.2(4) .
N5 Cu2 N4 C14 1.6(3) .
C18 Cu2 N4 C14 168.9(4) .
C17 Cu2 N4 C14 172.2(3) .
C18 Cu2 N5 C15 -173.8(3) .
N4 Cu2 N5 C15 0.4(3) .
C17 Cu2 N5 C15 -155.7(4) .
C18 Cu2 N5 N6 3.3(4) .
N4 Cu2 N5 N6 177.5(3) .
C17 Cu2 N5 N6 21.4(7) .
C15 N5 N6 C15 0.3(6) 3_766
Cu2 N5 N6 C15 -176.8(3) 3_766
C5 N1 C1 C2 -1.4(6) .
Cu1 N1 C1 C2 -177.2(3) .
N1 C1 C2 C3 1.3(7) .
C1 C2 C3 C4 0.0(6) .
C2 C3 C4 C5 -1.0(6) .
C1 N1 C5 C4 0.3(6) .
Cu1 N1 C5 C4 176.7(3) .
C1 N1 C5 C6 -179.7(4) .
Cu1 N1 C5 C6 -3.4(4) .
C3 C4 C5 N1 0.9(6) .
C3 C4 C5 C6 -179.0(4) .
N3 N2 C6 N3 0.2(7) 3_765
Cu1 N2 C6 N3 176.3(3) 3_765
N3 N2 C6 C5 -179.9(3) .
Cu1 N2 C6 C5 -3.8(4) .
N1 C5 C6 N3 -175.3(4) 3_765
C4 C5 C6 N3 4.6(6) 3_765
N1 C5 C6 N2 4.8(5) .
C4 C5 C6 N2 -175.3(4) .
N2 Cu1 C8 C9 -19.6(6) .
N1 Cu1 C8 C9 -176.6(3) .
N2 Cu1 C9 C8 172.3(2) .
N1 Cu1 C9 C8 7.5(6) .
C14 N4 C10 C11 0.6(6) .
Cu2 N4 C10 C11 -174.8(3) .
N4 C10 C11 C12 -0.5(7) .
C10 C11 C12 C13 0.3(7) .
C11 C12 C13 C14 -0.2(6) .
C10 N4 C14 C13 -0.6(6) .
Cu2 N4 C14 C13 175.5(3) .
C10 N4 C14 C15 -179.3(4) .
Cu2 N4 C14 C15 -3.2(4) .
C12 C13 C14 N4 0.4(6) .
C12 C13 C14 C15 179.1(4) .
N6 N5 C15 N6 -0.3(7) 3_766
Cu2 N5 C15 N6 177.2(3) 3_766
N6 N5 C15 C14 -179.7(3) .
Cu2 N5 C15 C14 -2.2(4) .
N4 C14 C15 N6 -175.8(4) 3_766
C13 C14 C15 N6 5.5(6) 3_766
N4 C14 C15 N5 3.6(5) .
C13 C14 C15 N5 -175.1(4) .
N5 Cu2 C17 C18 -24.7(6) .
N4 Cu2 C17 C18 -178.0(3) .
N5 Cu2 C18 C17 169.9(2) .
N4 Cu2 C18 C17 4.5(6) .
