#------------------------------------------------------------------------------
#$Date: 2019-12-20 12:08:49 +0200 (Fri, 20 Dec 2019) $
#$Revision: 245430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556691.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_1556691
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         'C15 H25 Cl3 Cu N2 O4'
_chemical_formula_sum            'C15 H25 Cl3 Cu N2 O4'
_chemical_formula_weight         467.26
_chemical_name_common            (HNEt3)[(pydicOMe2)CuCl3]
_chemical_name_systematic
'Triethylammonium (Pyridine-2,6-dicarboxyl-dimethyl) trichlorido cuprate'
_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   mixed
_cell_angle_alpha                93.846(5)
_cell_angle_beta                 92.271(5)
_cell_angle_gamma                107.216(5)
_cell_formula_units_Z            2
_cell_length_a                   7.706(5)
_cell_length_b                   10.274(5)
_cell_length_c                   13.666(5)
_cell_measurement_reflns_used    12435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.162
_cell_measurement_theta_min      2.462
_cell_volume                     1029.1(9)
_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 0.911
_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  0.1258
_diffrn_reflns_av_unetI/netI     0.2004
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12435
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.162
_diffrn_reflns_theta_min         2.462
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_T_max  56.3
_exptl_absorpt_correction_T_min  4.9
_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            green
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             482
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.684
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.684
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1758
_reflns_number_total             4604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Inorganics-2019-7-53.cif
_cod_data_source_block           1
_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               1556691
_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 1.15119(9) 0.31440(6) 0.24730(5) 0.03367(16) Uani 1 1 d . . . . .
Cl1 Cl 0.97705(17) 0.08852(11) 0.24231(9) 0.0500(4) Uani 1 1 d . . . . .
Cl2 Cl 1.35495(17) 0.26276(11) 0.14989(9) 0.0460(3) Uani 1 1 d . . . . .
Cl3 Cl 1.30884(17) 0.54408(11) 0.27029(9) 0.0505(4) Uani 1 1 d . . . . .
O1 O 1.2367(4) 0.2834(3) 0.4246(2) 0.0440(8) Uani 1 1 d . . . . .
O2 O 0.9295(5) 0.3794(3) 0.1364(2) 0.0621(10) Uani 1 1 d . . . . .
O3 O 1.0702(5) 0.2311(4) 0.5551(2) 0.0665(11) Uani 1 1 d . . . . .
O4 O 0.7631(4) 0.5201(3) 0.1653(2) 0.0542(9) Uani 1 1 d . . . . .
N1 N 0.9583(5) 0.3558(3) 0.3347(3) 0.0328(9) Uani 1 1 d . . . . .
N2 N 1.3088(5) -0.0549(4) 0.1898(3) 0.0363(10) Uani 1 1 d . . . . .
C1 C 1.1032(6) 0.2769(4) 0.4668(3) 0.0377(12) Uani 1 1 d . . . . .
C2 C 0.9510(6) 0.3263(4) 0.4284(3) 0.0337(11) Uani 1 1 d . . . . .
C3 C 0.8144(6) 0.3464(4) 0.4868(3) 0.0429(12) Uani 1 1 d . . . . .
H3 H 0.811106 0.324790 0.551876 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6869(7) 0.3978(5) 0.4470(4) 0.0508(14) Uani 1 1 d . . . . .
H4 H 0.595174 0.411829 0.484704 0.061 Uiso 1 1 calc R U . . .
C5 C 0.6943(6) 0.4293(4) 0.3499(4) 0.0463(13) Uani 1 1 d . . . . .
H5 H 0.608191 0.464587 0.321423 0.056 Uiso 1 1 calc R U . . .
C6 C 0.8329(6) 0.4068(4) 0.2965(3) 0.0345(11) Uani 1 1 d . . . . .
C7 C 0.8478(6) 0.4335(4) 0.1905(4) 0.0423(12) Uani 1 1 d . . . . .
C9 C 0.7492(8) 0.5364(5) 0.0608(4) 0.0751(18) Uani 1 1 d . . . . .
H9A H 0.685149 0.601718 0.049738 0.113 Uiso 1 1 calc R U . . .
H9B H 0.869071 0.568102 0.037351 0.113 Uiso 1 1 calc R U . . .
H9C H 0.684296 0.450034 0.026374 0.113 Uiso 1 1 calc R U . . .
C8 C 1.2178(8) 0.1897(7) 0.6030(4) 0.095(2) Uani 1 1 d . . . . .
H8A H 1.182367 0.158226 0.665883 0.142 Uiso 1 1 calc R U . . .
H8B H 1.241263 0.117346 0.562629 0.142 Uiso 1 1 calc R U . . .
H8C H 1.325973 0.266460 0.611650 0.142 Uiso 1 1 calc R U . . .
C10 C 1.3157(7) -0.0864(5) 0.2952(3) 0.0554(14) Uani 1 1 d . . . . .
H10A H 1.195361 -0.102569 0.319712 0.066 Uiso 1 1 calc R U . . .
H10B H 1.350179 -0.169419 0.299259 0.066 Uiso 1 1 calc R U . . .
C11 C 1.4478(9) 0.0269(6) 0.3587(4) 0.089(2) Uani 1 1 d . . . . .
H11A H 1.569064 0.036421 0.339403 0.134 Uiso 1 1 calc R U . . .
H11B H 1.439447 0.006223 0.426108 0.134 Uiso 1 1 calc R U . . .
H11C H 1.419522 0.110803 0.351237 0.134 Uiso 1 1 calc R U . . .
C12 C 1.4863(6) -0.0311(4) 0.1433(3) 0.0414(12) Uani 1 1 d . . . . .
H12A H 1.578833 0.037603 0.184555 0.050 Uiso 1 1 calc R U . . .
H12B H 1.476374 0.005574 0.080469 0.050 Uiso 1 1 calc R U . . .
C13 C 1.5480(7) -0.1554(5) 0.1272(4) 0.0637(16) Uani 1 1 d . . . . .
H13A H 1.549630 -0.196785 0.188005 0.095 Uiso 1 1 calc R U . . .
H13B H 1.668211 -0.129802 0.103579 0.095 Uiso 1 1 calc R U . . .
H13C H 1.465853 -0.219561 0.079523 0.095 Uiso 1 1 calc R U . . .
C14 C 1.1536(6) -0.1603(5) 0.1330(3) 0.0486(13) Uani 1 1 d . . . . .
H14A H 1.176237 -0.248362 0.131197 0.058 Uiso 1 1 calc R U . . .
H14B H 1.042448 -0.168067 0.166154 0.058 Uiso 1 1 calc R U . . .
C15 C 1.1292(8) -0.1245(5) 0.0307(4) 0.0743(17) Uani 1 1 d . . . . .
H15A H 1.154557 -0.027204 0.030352 0.111 Uiso 1 1 calc R U . . .
H15B H 1.006085 -0.168819 0.005720 0.111 Uiso 1 1 calc R U . . .
H15C H 1.211178 -0.154232 -0.010021 0.111 Uiso 1 1 calc R U . . .
H22 H 1.277(5) 0.022(4) 0.192(2) 0.020(11) 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'
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
N1 Cu1 Cl2 178.13(12) . .
N1 Cu1 Cl3 87.33(10) . .
Cl2 Cu1 Cl3 94.44(6) . .
N1 Cu1 Cl1 86.14(10) . .
Cl2 Cu1 Cl1 92.13(6) . .
Cl3 Cu1 Cl1 172.87(6) . .
C1 O3 C8 115.2(4) . .
C7 O4 C9 115.7(4) . .
C6 N1 C2 118.8(4) . .
C6 N1 Cu1 120.0(3) . .
C2 N1 Cu1 121.1(3) . .
C12 N2 C10 114.0(4) . .
C12 N2 C14 113.8(3) . .
C10 N2 C14 110.1(3) . .
O1 C1 O3 125.5(5) . .
O1 C1 C2 123.7(4) . .
O3 C1 C2 110.7(4) . .
N1 C2 C3 121.7(5) . .
N1 C2 C1 115.2(4) . .
C3 C2 C1 123.1(4) . .
C4 C3 C2 119.0(5) . .
C3 C4 C5 119.6(4) . .
C6 C5 C4 118.4(5) . .
N1 C6 C5 122.5(4) . .
N1 C6 C7 115.5(4) . .
C5 C6 C7 122.0(5) . .
O2 C7 O4 125.2(5) . .
O2 C7 C6 122.3(5) . .
O4 C7 C6 112.5(4) . .
C11 C10 N2 112.4(4) . .
N2 C12 C13 114.7(4) . .
C15 C14 N2 111.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.065(4) .
Cu1 Cl2 2.2546(16) .
Cu1 Cl3 2.3057(17) .
Cu1 Cl1 2.3063(17) .
O1 C1 1.186(5) .
O2 C7 1.200(5) .
O3 C1 1.331(5) .
O3 C8 1.472(6) .
O4 C7 1.306(5) .
O4 C9 1.452(5) .
N1 C6 1.334(5) .
N1 C2 1.335(5) .
N2 C12 1.492(5) .
N2 C10 1.499(5) .
N2 C14 1.501(5) .
C1 C2 1.499(6) .
C2 C3 1.400(5) .
C3 C4 1.358(6) .
C4 C5 1.386(6) .
C5 C6 1.383(6) .
C6 C7 1.494(6) .
C10 C11 1.495(7) .
C12 C13 1.496(6) .
C14 C15 1.488(6) .
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
C8 O3 C1 O1 1.8(7) . . . .
C8 O3 C1 C2 -175.6(4) . . . .
C6 N1 C2 C3 0.6(6) . . . .
Cu1 N1 C2 C3 -176.2(3) . . . .
C6 N1 C2 C1 -176.7(3) . . . .
Cu1 N1 C2 C1 6.5(5) . . . .
O1 C1 C2 N1 11.8(6) . . . .
O3 C1 C2 N1 -170.7(4) . . . .
O1 C1 C2 C3 -165.5(4) . . . .
O3 C1 C2 C3 12.0(6) . . . .
N1 C2 C3 C4 -0.3(6) . . . .
C1 C2 C3 C4 176.8(4) . . . .
C2 C3 C4 C5 0.0(7) . . . .
C3 C4 C5 C6 0.0(7) . . . .
C2 N1 C6 C5 -0.6(6) . . . .
Cu1 N1 C6 C5 176.2(3) . . . .
C2 N1 C6 C7 -178.4(3) . . . .
Cu1 N1 C6 C7 -1.6(5) . . . .
C4 C5 C6 N1 0.3(6) . . . .
C4 C5 C6 C7 178.0(4) . . . .
C9 O4 C7 O2 8.3(7) . . . .
C9 O4 C7 C6 -171.5(4) . . . .
N1 C6 C7 O2 20.3(6) . . . .
C5 C6 C7 O2 -157.6(4) . . . .
N1 C6 C7 O4 -159.9(4) . . . .
C5 C6 C7 O4 22.3(6) . . . .
C12 N2 C10 C11 60.1(5) . . . .
C14 N2 C10 C11 -170.6(4) . . . .
C10 N2 C12 C13 69.3(5) . . . .
C14 N2 C12 C13 -58.1(6) . . . .
C12 N2 C14 C15 -57.0(5) . . . .
C10 N2 C14 C15 173.7(4) . . . .
