#------------------------------------------------------------------------------
#$Date: 2019-12-20 12:08:49 +0200 (Fri, 20 Dec 2019) $
#$Revision: 245430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556692.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_1556692
loop_
_publ_author_name
'Butsch, K.'
'Sandleben, A.'
'Dokoohaki, M.H.'
'Zolghadr, A.R.'
'Klein, A.'
_publ_section_title
;
 Pyridine-2,6-Dicarboxylic Acid Esters (pydicR2) as O,N,O-Pincer Ligands
 in CuII Complexes
;
_journal_name_full               Inorganics
_journal_page_first              53
_journal_paper_doi               10.3390/inorganics7040053
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C14 H6 Cl2 Cu3 N2 O14'
_chemical_formula_sum            'C14 H6 Cl2 Cu3 N2 O14'
_chemical_formula_weight         687.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                69.01(3)
_cell_angle_beta                 66.97(3)
_cell_angle_gamma                89.04(4)
_cell_formula_units_Z            1
_cell_length_a                   8.185(3)
_cell_length_b                   9.500(3)
_cell_length_c                   9.682(2)
_cell_measurement_reflns_used    7681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.208
_cell_measurement_theta_min      2.320
_cell_volume                     640.2(4)
_computing_cell_refinement       'X-AREA (STOE & Cie 2001)'
_computing_data_collection       'X-AREA (STOE & Cie 2001)'
_computing_data_reduction        'X-RED (STOE & Cie 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'w scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7681
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.208
_diffrn_reflns_theta_min         2.320
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  56.1
_exptl_absorpt_correction_T_min  4.7
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
The absorption correction (X-RED; Stoe & Cie, 2001) 
was performed after optimizing the crystal shape 
using X-SHAPE (Stoe & Cie, 1999).
;
_exptl_crystal_colour            turquoise
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             337
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         3.793
_refine_diff_density_min         -1.489
_refine_diff_density_rms         0.266
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0813
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1609P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2361
_refine_ls_wR_factor_ref         0.2593
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1626
_reflns_number_total             2849
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Inorganics-2019-7-53.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1556692
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.65739(15) 0.43788(14) 0.07937(12) 0.0244(4) Uani 1 1 d . . . . .
Cu2 Cu 0.000000 0.000000 0.500000 0.0386(5) Uani 1 2 d S . P . .
Cl1 Cl 0.6056(3) 0.3862(3) -0.1064(3) 0.0302(6) Uani 1 1 d . . . . .
O1 O 0.8613(9) 0.6171(8) -0.0749(7) 0.0280(15) Uani 1 1 d . . . . .
O2 O 0.4960(9) 0.2605(8) 0.2861(7) 0.0302(15) Uani 1 1 d . . . . .
O3 O 1.0533(11) 0.7831(10) -0.0741(9) 0.048(2) Uani 1 1 d . . . . .
O4 O 0.4169(11) 0.1640(9) 0.5561(8) 0.0404(19) Uani 1 1 d . . . . .
O5 O 0.1391(13) 0.2057(11) 0.3612(9) 0.055(2) Uani 1 1 d . . . . .
O6 O -0.1671(10) 0.0496(9) 0.3945(8) 0.0403(19) Uani 1 1 d . . . . .
N1 N 0.7308(10) 0.4724(9) 0.2325(8) 0.0211(16) Uani 1 1 d . . . . .
C1 C 0.5105(13) 0.2559(12) 0.4177(10) 0.028(2) Uani 1 1 d . . . . .
C2 C 0.6503(12) 0.3804(12) 0.3879(10) 0.026(2) Uani 1 1 d . . . . .
C3 C 0.6900(13) 0.4070(12) 0.5013(11) 0.030(2) Uani 1 1 d . . . . .
H3 H 0.635832 0.341706 0.609941 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8133(14) 0.5339(14) 0.4515(12) 0.038(3) Uani 1 1 d . . . . .
H4 H 0.838835 0.555375 0.528011 0.045 Uiso 1 1 calc R U . . .
C5 C 0.9001(14) 0.6305(13) 0.2848(12) 0.033(2) Uani 1 1 d . . . . .
H5 H 0.983230 0.715125 0.249203 0.039 Uiso 1 1 calc R U . . .
C6 C 0.8549(13) 0.5926(12) 0.1783(11) 0.026(2) Uani 1 1 d . . . . .
C7 C 0.9315(13) 0.6758(12) -0.0061(10) 0.027(2) Uani 1 1 d . . . . .
O7 O 0.216(5) -0.0497(17) 0.257(2) 0.27(2) 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'
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'
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'
H H 0.0000 0.0000 '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
N1 Cu1 O2 80.6(3) . .
N1 Cu1 O1 79.6(3) . .
O2 Cu1 O1 159.7(2) . .
N1 Cu1 Cl1 172.7(2) . .
O2 Cu1 Cl1 100.9(2) . .
O1 Cu1 Cl1 98.13(19) . .
N1 Cu1 Cl1 96.9(2) . 2_665
O2 Cu1 Cl1 92.1(2) . 2_665
O1 Cu1 Cl1 94.7(2) . 2_665
Cl1 Cu1 Cl1 90.24(9) . 2_665
O6 Cu2 O6 180.0 . 2_556
O6 Cu2 O5 90.3(3) . 2_556
O6 Cu2 O5 89.7(3) 2_556 2_556
O6 Cu2 O5 89.7(3) . .
O6 Cu2 O5 90.3(3) 2_556 .
O5 Cu2 O5 180.0 2_556 .
Cu1 Cl1 Cu1 89.76(9) . 2_665
C7 O1 Cu1 115.8(6) . .
C1 O2 Cu1 114.2(6) . .
C2 N1 C6 123.0(8) . .
C2 N1 Cu1 118.5(7) . .
C6 N1 Cu1 118.5(6) . .
O4 C1 O2 124.4(9) . .
O4 C1 C2 121.4(8) . .
O2 C1 C2 114.1(8) . .
N1 C2 C3 120.3(9) . .
N1 C2 C1 112.5(7) . .
C3 C2 C1 127.2(8) . .
C2 C3 C4 118.8(9) . .
C2 C3 H3 120.6 . .
C4 C3 H3 120.6 . .
C3 C4 C5 120.4(9) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C6 C5 C4 116.7(10) . .
C6 C5 H5 121.7 . .
C4 C5 H5 121.7 . .
N1 C6 C5 120.8(9) . .
N1 C6 C7 112.5(8) . .
C5 C6 C7 126.7(10) . .
O3 C7 O1 126.7(8) . .
O3 C7 C6 119.9(9) . .
O1 C7 C6 113.3(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.928(7) .
Cu1 O2 2.045(7) .
Cu1 O1 2.059(7) .
Cu1 Cl1 2.212(2) .
Cu1 Cl1 2.692(3) 2_665
Cu2 O6 1.965(7) .
Cu2 O6 1.965(7) 2_556
Cu2 O5 1.979(9) 2_556
Cu2 O5 1.979(9) .
O1 C7 1.289(12) .
O2 C1 1.311(10) .
O3 C7 1.227(13) .
O4 C1 1.235(11) .
N1 C2 1.328(11) .
N1 C6 1.343(13) .
C1 C2 1.528(15) .
C2 C3 1.362(12) .
C3 C4 1.397(16) .
C3 H3 0.9300 .
C4 C5 1.420(14) .
C4 H4 0.9300 .
C5 C6 1.377(13) .
C5 H5 0.9300 .
C6 C7 1.528(12) .
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
Cu1 O2 C1 O4 175.2(9) . . . .
Cu1 O2 C1 C2 -2.3(10) . . . .
C6 N1 C2 C3 1.1(14) . . . .
Cu1 N1 C2 C3 -175.7(7) . . . .
C6 N1 C2 C1 178.1(8) . . . .
Cu1 N1 C2 C1 1.3(11) . . . .
O4 C1 C2 N1 -176.8(9) . . . .
O2 C1 C2 N1 0.8(12) . . . .
O4 C1 C2 C3 0.0(16) . . . .
O2 C1 C2 C3 177.6(9) . . . .
N1 C2 C3 C4 1.3(14) . . . .
C1 C2 C3 C4 -175.2(10) . . . .
C2 C3 C4 C5 -2.1(16) . . . .
C3 C4 C5 C6 0.5(16) . . . .
C2 N1 C6 C5 -2.8(14) . . . .
Cu1 N1 C6 C5 174.0(7) . . . .
C2 N1 C6 C7 177.8(8) . . . .
Cu1 N1 C6 C7 -5.4(10) . . . .
C4 C5 C6 N1 1.9(15) . . . .
C4 C5 C6 C7 -178.7(10) . . . .
Cu1 O1 C7 O3 -179.7(9) . . . .
Cu1 O1 C7 C6 3.5(10) . . . .
N1 C6 C7 O3 -176.1(9) . . . .
C5 C6 C7 O3 4.5(16) . . . .
N1 C6 C7 O1 1.0(12) . . . .
C5 C6 C7 O1 -178.4(9) . . . .
