#------------------------------------------------------------------------------
#$Date: 2021-07-13 10:27:24 +0300 (Tue, 13 Jul 2021) $
#$Revision: 267489 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/41/1564115.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_1564115
loop_
_publ_author_name
'Li, Jun-Xia'
'Du, Zhong-Xiang'
'Zhang, Lu-Lu'
'Liu, Duo-Li'
'Pan, Qiu-Yue'
_publ_section_title
;
 Doubly mononuclear cocrystal and oxalato-bridged binuclear copper
 compounds containing flexible 2-((3,5,6-trichloropyridin-2-yl)oxy)acetate
 tectons: Synthesis, crystal analysis and magnetic properties
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119890
_journal_paper_doi               10.1016/j.ica.2020.119890
_journal_volume                  512
_journal_year                    2020
_chemical_formula_moiety         'C36 H22 Cl6 Cu2 N6 O10, 2(C2 H6 O)'
_chemical_formula_sum            'C40 H34 Cl6 Cu2 N6 O12'
_chemical_formula_weight         1130.51
_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
_atom_sites_solution_primary     iterative
_cell_angle_alpha                94.019(4)
_cell_angle_beta                 102.129(5)
_cell_angle_gamma                106.347(5)
_cell_formula_units_Z            1
_cell_length_a                   7.7129(4)
_cell_length_b                   9.8035(5)
_cell_length_c                   16.0541(9)
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    291.2(2)
_cell_measurement_theta_max      25.2530
_cell_measurement_theta_min      3.9230
_cell_volume                     1127.97(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      291.2(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -12.00  14.00   1.00   10.00    --  -13.80  19.00-180.00   26
  2  ω    -30.00   8.00   1.00   10.00    --  -13.80 -86.00 114.00   38
  3  ω    -28.00  52.00   1.00   10.00    --  -13.80  57.00  90.00   80
  4  ω    -12.00  19.00   1.00   10.00    --  -13.80 -99.00   0.00   31
  5  ω    -52.00  42.00   1.00   10.00    --   14.82 -77.00-150.00   94
  6  ω    -10.00  80.00   1.00   10.00    --   14.82  77.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0283681000
_diffrn_orient_matrix_UB_12      -0.0438393000
_diffrn_orient_matrix_UB_13      -0.0404816000
_diffrn_orient_matrix_UB_21      -0.0928127000
_diffrn_orient_matrix_UB_22      -0.0225081000
_diffrn_orient_matrix_UB_23      0.0047200000
_diffrn_orient_matrix_UB_31      -0.0181017000
_diffrn_orient_matrix_UB_32      0.0580219000
_diffrn_orient_matrix_UB_33      -0.0205102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8846
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.415
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0499
_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)+(0.0272P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3454
_reflns_number_total             4683
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-512-119890.cif
_cod_data_source_block           cu2
_cod_database_code               1564115
_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.
;
_shelx_estimated_absorpt_t_max   0.772
_shelx_estimated_absorpt_t_min   0.726
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C19(H19), C20(H20), C17(H17), C12(H12), C18(H18),
 C11(H11), C3(H3)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
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 0.28053(5) 0.24757(4) 0.52356(3) 0.02755(13) Uani 1 1 d . . . . .
Cl1 Cl 0.68841(14) -0.10758(10) 0.91940(6) 0.0558(3) Uani 1 1 d . . . . .
Cl2 Cl 0.73886(15) 0.40827(12) 1.08036(7) 0.0647(3) Uani 1 1 d . . . . .
Cl3 Cl 0.73073(15) 0.52448(10) 0.90072(7) 0.0633(3) Uani 1 1 d . . . . .
O1 O 0.4926(3) 0.2146(2) 0.59721(14) 0.0357(6) Uani 1 1 d . . . . .
O2 O 0.3381(3) 0.0581(3) 0.67042(15) 0.0486(7) Uani 1 1 d . . . . .
O3 O 0.6673(3) 0.0418(2) 0.76921(14) 0.0338(5) Uani 1 1 d . . . . .
O4 O 0.2002(3) 0.0551(2) 0.45985(13) 0.0302(5) Uani 1 1 d . . . . .
O5 O -0.0068(3) -0.1615(2) 0.44391(14) 0.0310(5) Uani 1 1 d . . . . .
O6 O 0.2495(3) -0.0098(3) 0.82398(17) 0.0543(7) Uani 1 1 d . . . . .
H6 H 0.2983 0.0115 0.7840 0.081 Uiso 1 1 calc GR . . . .
N1 N 0.6980(3) 0.2651(3) 0.83798(17) 0.0324(7) Uani 1 1 d . . . . .
N2 N 0.1747(3) 0.3367(3) 0.42311(17) 0.0282(6) Uani 1 1 d . . . . .
N3 N 0.3462(3) 0.4478(3) 0.58086(16) 0.0273(6) Uani 1 1 d . . . . .
C16 C 0.1853(4) 0.4752(3) 0.4425(2) 0.0258(7) Uani 1 1 d . . . . .
C15 C 0.2828(4) 0.5393(3) 0.5322(2) 0.0273(7) Uani 1 1 d . . . . .
C14 C 0.3077(4) 0.6781(3) 0.5659(2) 0.0368(8) Uani 1 1 d . . . . .
H14 H 0.2654 0.7400 0.5314 0.044 Uiso 1 1 calc R . . . .
C13 C 0.3960(5) 0.7249(4) 0.6513(2) 0.0445(9) Uani 1 1 d . . . . .
H13 H 0.4114 0.8177 0.6756 0.053 Uiso 1 1 calc R . . . .
C19 C 0.0175(5) 0.3393(4) 0.2797(2) 0.0472(10) Uani 1 1 d . . . . .
H19 H -0.0384 0.2911 0.2243 0.057 Uiso 1 1 calc R . . . .
C20 C 0.0911(4) 0.2707(4) 0.3434(2) 0.0391(9) Uani 1 1 d . . . . .
H20 H 0.0822 0.1747 0.3304 0.047 Uiso 1 1 calc R . . . .
C17 C 0.1101(4) 0.5496(4) 0.3812(2) 0.0358(8) Uani 1 1 d . . . . .
H17 H 0.1153 0.6445 0.3954 0.043 Uiso 1 1 calc R . . . .
C12 C 0.4614(4) 0.6313(4) 0.7003(2) 0.0457(9) Uani 1 1 d . . . . .
H12 H 0.5227 0.6607 0.7580 0.055 Uiso 1 1 calc R . . . .
C18 C 0.0281(5) 0.4796(4) 0.2994(2) 0.0462(10) Uani 1 1 d . . . . .
H18 H -0.0206 0.5279 0.2570 0.055 Uiso 1 1 calc R . . . .
C11 C 0.4351(4) 0.4953(4) 0.6631(2) 0.0383(9) Uani 1 1 d . . . . .
H11 H 0.4807 0.4332 0.6963 0.046 Uiso 1 1 calc R . . . .
C1 C 0.7168(4) 0.3468(4) 0.9104(2) 0.0368(9) Uani 1 1 d . . . . .
C2 C 0.7242(4) 0.2985(4) 0.9889(2) 0.0390(9) Uani 1 1 d . . . . .
C3 C 0.7160(4) 0.1555(4) 0.9926(2) 0.0407(9) Uani 1 1 d . . . . .
H3 H 0.7221 0.1188 1.0446 0.049 Uiso 1 1 calc R . . . .
C4 C 0.6988(4) 0.0701(3) 0.9187(2) 0.0323(8) Uani 1 1 d . . . . .
C5 C 0.6882(4) 0.1277(3) 0.8412(2) 0.0285(7) Uani 1 1 d . . . . .
C6 C 0.6673(4) 0.1062(3) 0.69135(19) 0.0328(8) Uani 1 1 d . . . . .
H6A H 0.6988 0.0461 0.6500 0.039 Uiso 1 1 calc R . . . .
H6B H 0.7625 0.1989 0.7038 0.039 Uiso 1 1 calc R . . . .
C7 C 0.4800(4) 0.1263(3) 0.6516(2) 0.0295(7) Uani 1 1 d . . . . .
C8 C 0.0542(4) -0.0322(3) 0.47165(19) 0.0241(7) Uani 1 1 d . . . . .
C9 C 0.1957(6) 0.2210(5) 0.8378(4) 0.1004(19) Uani 1 1 d . . . . .
H9A H 0.2257 0.2498 0.7853 0.151 Uiso 1 1 calc GR . . . .
H9B H 0.3060 0.2528 0.8838 0.151 Uiso 1 1 calc GR . . . .
H9C H 0.1043 0.2630 0.8507 0.151 Uiso 1 1 calc GR . . . .
C10 C 0.1217(5) 0.0659(5) 0.8279(3) 0.0676(13) Uani 1 1 d . . . . .
H10A H 0.0664 0.0400 0.8758 0.081 Uiso 1 1 calc R . . . .
H10B H 0.0228 0.0345 0.7758 0.081 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'
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'
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
O1 Cu1 O4 92.48(8) . .
O1 Cu1 O5 116.85(8) . 2_556
O1 Cu1 N2 149.46(10) . .
O1 Cu1 N3 92.38(9) . .
O4 Cu1 O5 80.43(8) . 2_556
O4 Cu1 N2 94.52(9) . .
O4 Cu1 N3 175.06(9) . .
N2 Cu1 O5 93.63(9) . 2_556
N3 Cu1 O5 98.10(9) . 2_556
N3 Cu1 N2 80.83(10) . .
C7 O1 Cu1 123.7(2) . .
C5 O3 C6 117.2(2) . .
C8 O4 Cu1 116.92(19) . .
C8 O5 Cu1 107.80(18) . 2_556
C10 O6 H6 109.5 . .
C1 N1 C5 118.2(3) . .
C16 N2 Cu1 114.5(2) . .
C20 N2 Cu1 126.6(2) . .
C20 N2 C16 118.9(3) . .
C15 N3 Cu1 115.6(2) . .
C11 N3 Cu1 125.6(2) . .
C11 N3 C15 118.6(3) . .
N2 C16 C15 114.8(3) . .
N2 C16 C17 121.3(3) . .
C17 C16 C15 123.9(3) . .
N3 C15 C16 114.1(3) . .
N3 C15 C14 121.3(3) . .
C14 C15 C16 124.6(3) . .
C15 C14 H14 120.3 . .
C15 C14 C13 119.4(3) . .
C13 C14 H14 120.3 . .
C14 C13 H13 120.6 . .
C14 C13 C12 118.8(3) . .
C12 C13 H13 120.6 . .
C20 C19 H19 120.7 . .
C18 C19 H19 120.7 . .
C18 C19 C20 118.6(3) . .
N2 C20 C19 122.5(3) . .
N2 C20 H20 118.8 . .
C19 C20 H20 118.8 . .
C16 C17 H17 120.8 . .
C18 C17 C16 118.4(3) . .
C18 C17 H17 120.8 . .
C13 C12 H12 120.4 . .
C11 C12 C13 119.2(3) . .
C11 C12 H12 120.4 . .
C19 C18 C17 120.3(3) . .
C19 C18 H18 119.9 . .
C17 C18 H18 119.9 . .
N3 C11 C12 122.5(3) . .
N3 C11 H11 118.7 . .
C12 C11 H11 118.7 . .
N1 C1 Cl3 115.3(3) . .
N1 C1 C2 124.1(3) . .
C2 C1 Cl3 120.7(3) . .
C1 C2 Cl2 122.0(3) . .
C1 C2 C3 117.8(3) . .
C3 C2 Cl2 120.2(3) . .
C2 C3 H3 120.6 . .
C4 C3 C2 118.9(3) . .
C4 C3 H3 120.6 . .
C3 C4 Cl1 121.0(3) . .
C3 C4 C5 119.4(3) . .
C5 C4 Cl1 119.7(3) . .
O3 C5 C4 118.6(3) . .
N1 C5 O3 119.8(3) . .
N1 C5 C4 121.6(3) . .
O3 C6 H6A 109.1 . .
O3 C6 H6B 109.1 . .
O3 C6 C7 112.6(2) . .
H6A C6 H6B 107.8 . .
C7 C6 H6A 109.1 . .
C7 C6 H6B 109.1 . .
O1 C7 C6 112.2(3) . .
O2 C7 O1 126.8(3) . .
O2 C7 C6 120.9(3) . .
O4 C8 C8 115.9(3) . 2_556
O5 C8 O4 126.0(3) . .
O5 C8 C8 118.1(3) . 2_556
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C10 C9 H9A 109.5 . .
C10 C9 H9B 109.5 . .
C10 C9 H9C 109.5 . .
O6 C10 C9 116.0(3) . .
O6 C10 H10A 108.3 . .
O6 C10 H10B 108.3 . .
C9 C10 H10A 108.3 . .
C9 C10 H10B 108.3 . .
H10A C10 H10B 107.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9278(19) .
Cu1 O4 1.948(2) .
Cu1 O5 2.228(2) 2_556
Cu1 N2 2.019(2) .
Cu1 N3 1.986(2) .
Cl1 C4 1.722(3) .
Cl2 C2 1.723(4) .
Cl3 C1 1.735(3) .
O1 C7 1.271(3) .
O2 C7 1.222(4) .
O3 C5 1.334(4) .
O3 C6 1.440(3) .
O4 C8 1.267(3) .
O5 Cu1 2.2279(19) 2_556
O5 C8 1.235(3) .
O6 H6 0.8200 .
O6 C10 1.399(4) .
N1 C1 1.322(4) .
N1 C5 1.333(4) .
N2 C16 1.348(4) .
N2 C20 1.331(4) .
N3 C15 1.356(3) .
N3 C11 1.336(4) .
C16 C15 1.478(4) .
C16 C17 1.391(4) .
C15 C14 1.375(4) .
C14 H14 0.9300 .
C14 C13 1.377(4) .
C13 H13 0.9300 .
C13 C12 1.382(4) .
C19 H19 0.9300 .
C19 C20 1.374(4) .
C19 C18 1.365(5) .
C20 H20 0.9300 .
C17 H17 0.9300 .
C17 C18 1.370(5) .
C12 H12 0.9300 .
C12 C11 1.364(4) .
C18 H18 0.9300 .
C11 H11 0.9300 .
C1 C2 1.372(4) .
C2 C3 1.392(4) .
C3 H3 0.9300 .
C3 C4 1.363(4) .
C4 C5 1.398(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 C7 1.524(4) .
C8 C8 1.569(6) 2_556
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C9 C10 1.450(5) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
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
O6 H6 O2 0.82 1.98 2.769(3) 162.7 .
