#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/55/7015533.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_7015533
loop_
_publ_author_name
'Brotherton, Wendy S.'
'Guha, Pampa M.'
'Phan, Hoa'
'Clark, Ronald J.'
'Shatruk, Michael'
'Zhu, Lei'
_publ_section_title
;
 Tridentate complexes of
 2,6-bis(4-substituted-1,2,3-triazol-1-ylmethyl)pyridine and its
 organic azide precursors: an application of the copper(II)
 acetate-accelerated azide-alkyne cycloaddition.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3655
_journal_page_last               3665
_journal_paper_doi               10.1039/c0dt01702g
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C7 H7 Cl2 Cu N7'
_chemical_formula_sum            'C7 H7 Cl2 Cu N7'
_chemical_formula_weight         323.64
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.7560(10)
_cell_angle_beta                 94.2700(10)
_cell_angle_gamma                107.2860(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1364(4)
_cell_length_b                   9.0635(5)
_cell_length_c                   10.3618(5)
_cell_measurement_reflns_used    5977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.94
_cell_measurement_theta_min      2.52
_cell_volume                     595.15(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.731
_diffrn_measured_fraction_theta_max 0.731
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8719
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    2.271
_exptl_absorpt_correction_T_max  0.8217
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flat
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0247
_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)+(0.0264P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0593
_reflns_number_gt                2909
_reflns_number_total             3312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01702g.txt
_cod_data_source_block           zhu41
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        595.15(5)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7015533
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cu1 Cu 0.69485(3) 0.70098(2) 0.76787(2) 0.02191(6) Uani 1 1 d . . .
Cl1 Cl 0.63224(6) 0.78401(5) 0.99709(4) 0.02595(9) Uani 1 1 d . . .
Cl2 Cl 0.55426(7) 0.83200(6) 0.66570(5) 0.03144(10) Uani 1 1 d . . .
C1 C 0.7319(2) 0.3889(2) 0.75957(16) 0.0223(3) Uani 1 1 d . . .
C2 C 0.8245(3) 0.2831(2) 0.78059(18) 0.0280(4) Uani 1 1 d . . .
H2 H 0.7512 0.1688 0.7571 0.034 Uiso 1 1 calc R . .
C3 C 1.0276(3) 0.3468(2) 0.83690(19) 0.0294(4) Uani 1 1 d . . .
H3 H 1.0941 0.2765 0.8540 0.035 Uiso 1 1 calc R . .
C4 C 1.1326(2) 0.5129(2) 0.86796(18) 0.0267(4) Uani 1 1 d . . .
H4 H 1.2714 0.5578 0.9061 0.032 Uiso 1 1 calc R . .
C5 C 1.0317(2) 0.6124(2) 0.84246(17) 0.0227(3) Uani 1 1 d . . .
C6 C 0.5124(2) 0.3317(2) 0.70269(19) 0.0259(3) Uani 1 1 d . . .
H6A H 0.4738 0.2297 0.6189 0.031 Uiso 1 1 calc R . .
H6B H 0.4337 0.3075 0.7727 0.031 Uiso 1 1 calc R . .
C7 C 1.1318(2) 0.7945(2) 0.8715(2) 0.0289(4) Uani 1 1 d . . .
H7A H 1.1588 0.8580 0.9725 0.035 Uiso 1 1 calc R . .
H7B H 1.2603 0.8137 0.8384 0.035 Uiso 1 1 calc R . .
N1 N 0.83405(19) 0.55095(17) 0.79115(14) 0.0206(3) Uani 1 1 d . . .
N2 N 0.9951(2) 0.84853(19) 0.79761(16) 0.0282(3) Uani 1 1 d . . .
N3 N 1.0664(2) 0.91944(19) 0.71858(16) 0.0295(3) Uani 1 1 d . . .
N4 N 1.1138(3) 0.9854(2) 0.6456(2) 0.0462(5) Uani 1 1 d . . .
N5 N 0.4751(2) 0.46695(18) 0.66765(16) 0.0261(3) Uani 1 1 d . . .
N6 N 0.3092(2) 0.43165(19) 0.59428(15) 0.0271(3) Uani 1 1 d . . .
N7 N 0.1658(2) 0.4140(2) 0.52922(18) 0.0389(4) 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'
Cl Cl 0.1484 0.1585 '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 Cu1 N5 77.64(6) . . ?
N1 Cu1 N2 78.48(6) . . ?
N5 Cu1 N2 146.78(6) . . ?
N1 Cu1 Cl2 159.62(4) . . ?
N5 Cu1 Cl2 95.59(4) . . ?
N2 Cu1 Cl2 98.86(4) . . ?
N1 Cu1 Cl1 95.96(4) . . ?
N5 Cu1 Cl1 103.72(4) . . ?
N2 Cu1 Cl1 101.42(5) . . ?
Cl2 Cu1 Cl1 104.345(18) . . ?
N1 C1 C2 121.40(15) . . ?
N1 C1 C6 116.38(15) . . ?
C2 C1 C6 122.22(15) . . ?
C1 C2 C3 118.65(16) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.81(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 118.80(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 121.15(15) . . ?
N1 C5 C7 115.70(15) . . ?
C4 C5 C7 123.14(15) . . ?
N5 C6 C1 106.87(13) . . ?
N5 C6 H6A 110.3 . . ?
C1 C6 H6A 110.3 . . ?
N5 C6 H6B 110.3 . . ?
C1 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
N2 C7 C5 107.67(13) . . ?
N2 C7 H7A 110.2 . . ?
C5 C7 H7A 110.2 . . ?
N2 C7 H7B 110.2 . . ?
C5 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C5 N1 C1 120.15(14) . . ?
C5 N1 Cu1 119.44(11) . . ?
C1 N1 Cu1 120.38(11) . . ?
N3 N2 C7 116.26(14) . . ?
N3 N2 Cu1 124.85(12) . . ?
C7 N2 Cu1 112.10(10) . . ?
N4 N3 N2 173.5(2) . . ?
N6 N5 C6 116.40(14) . . ?
N6 N5 Cu1 128.20(12) . . ?
C6 N5 Cu1 114.95(10) . . ?
N7 N6 N5 173.94(19) . . ?
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
Cu1 N1 1.9677(14) . ?
Cu1 N5 2.0978(15) . ?
Cu1 N2 2.0997(14) . ?
Cu1 Cl2 2.2127(5) . ?
Cu1 Cl1 2.3697(5) . ?
C1 N1 1.347(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.501(2) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.347(2) . ?
C5 C7 1.507(2) . ?
C6 N5 1.474(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.480(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N2 N3 1.244(2) . ?
N3 N4 1.119(2) . ?
N5 N6 1.252(2) . ?
N6 N7 1.121(2) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.6(2) . . . . ?
C6 C1 C2 C3 -178.44(16) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 N1 1.4(2) . . . . ?
C3 C4 C5 C7 -179.60(16) . . . . ?
N1 C1 C6 N5 12.3(2) . . . . ?
C2 C1 C6 N5 -168.60(15) . . . . ?
N1 C5 C7 N2 -16.2(2) . . . . ?
C4 C5 C7 N2 164.81(15) . . . . ?
C4 C5 N1 C1 -2.1(2) . . . . ?
C7 C5 N1 C1 178.86(14) . . . . ?
C4 C5 N1 Cu1 176.17(12) . . . . ?
C7 C5 N1 Cu1 -2.87(19) . . . . ?
C2 C1 N1 C5 1.1(2) . . . . ?
C6 C1 N1 C5 -179.85(14) . . . . ?
C2 C1 N1 Cu1 -177.19(12) . . . . ?
C6 C1 N1 Cu1 1.90(19) . . . . ?
N5 Cu1 N1 C5 171.10(13) . . . . ?
N2 Cu1 N1 C5 14.36(12) . . . . ?
Cl2 Cu1 N1 C5 98.79(16) . . . . ?
Cl1 Cu1 N1 C5 -86.12(11) . . . . ?
N5 Cu1 N1 C1 -10.64(12) . . . . ?
N2 Cu1 N1 C1 -167.38(13) . . . . ?
Cl2 Cu1 N1 C1 -82.95(16) . . . . ?
Cl1 Cu1 N1 C1 92.14(12) . . . . ?
C5 C7 N2 N3 -126.07(16) . . . . ?
C5 C7 N2 Cu1 26.56(17) . . . . ?
N1 Cu1 N2 N3 127.05(16) . . . . ?
N5 Cu1 N2 N3 82.30(18) . . . . ?
Cl2 Cu1 N2 N3 -32.41(16) . . . . ?
Cl1 Cu1 N2 N3 -139.11(15) . . . . ?
N1 Cu1 N2 C7 -22.80(12) . . . . ?
N5 Cu1 N2 C7 -67.56(16) . . . . ?
Cl2 Cu1 N2 C7 177.74(11) . . . . ?
Cl1 Cu1 N2 C7 71.04(12) . . . . ?
C1 C6 N5 N6 166.64(14) . . . . ?
C1 C6 N5 Cu1 -20.42(17) . . . . ?
N1 Cu1 N5 N6 -170.52(15) . . . . ?
N2 Cu1 N5 N6 -125.59(15) . . . . ?
Cl2 Cu1 N5 N6 -10.00(15) . . . . ?
Cl1 Cu1 N5 N6 96.27(14) . . . . ?
N1 Cu1 N5 C6 17.53(11) . . . . ?
N2 Cu1 N5 C6 62.47(16) . . . . ?
Cl2 Cu1 N5 C6 178.06(11) . . . . ?
Cl1 Cu1 N5 C6 -75.68(12) . . . . ?
