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#$Date: 2020-10-03 04:23:35 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256968 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/92/1559256.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_1559256
loop_
_publ_author_name
'Chevalier, Aline'
'Osypenko, Artem'
'Lehn, Jean-Marie'
'Meyer, Daniel'
_publ_section_title
;
 Phase transfer of metal cations by induced dynamic carrier agents:
 biphasic extraction based on dynamic covalent chemistry
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04098C
_journal_year                    2020
_chemical_formula_moiety         'C16 H16 Cl Cu2 N6 O2'
_chemical_formula_sum            'C16 H16 Cl Cu2 N6 O2'
_chemical_formula_weight         486.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.512(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3690(4)
_cell_length_b                   8.7013(5)
_cell_length_c                   12.1951(6)
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.31
_cell_measurement_theta_min      5.08
_cell_volume                     918.42(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9027
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.646
_diffrn_reflns_theta_max         66.646
_diffrn_reflns_theta_min         5.083
_diffrn_source                   'Cu-ImuS microfocus tube'
_exptl_absorpt_coefficient_mu    4.415
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       needle
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0526
_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)+(0.0759P)²+1.7138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1165
_reflns_number_total             1622
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04098c2.cif
_cod_data_source_block           jmlac190709
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               1559256
_shelx_shelxl_version_number     2014/7
_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_min   0.307
_shelx_estimated_absorpt_t_max   0.667
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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_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
C1 C 0.2800(6) 0.8253(8) 0.5710(5) 0.0411(15) Uani 1 1 d . . . . .
H1 H 0.2200 0.8274 0.6186 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2313(6) 0.9104(7) 0.4679(6) 0.0412(15) Uani 1 1 d . . . . .
H2 H 0.1408 0.9719 0.4456 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3163(7) 0.9044(7) 0.3983(5) 0.0394(15) Uani 1 1 d . . . . .
H3 H 0.2834 0.9603 0.3259 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4501(6) 0.8170(6) 0.4331(5) 0.0313(12) Uani 1 1 d . . . . .
H4 H 0.5095 0.8107 0.3851 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4943(6) 0.7394(6) 0.5399(4) 0.0277(11) Uani 1 1 d . . . . .
C6 C 0.6392(6) 0.6543(6) 0.5903(4) 0.0271(11) Uani 1 1 d . . . . .
H6 H 0.7135 0.6559 0.5548 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7833(6) 0.4071(7) 0.8263(5) 0.0310(12) Uani 1 1 d . . . . .
C8 C 0.9216(6) 0.3097(8) 0.8957(6) 0.0433(16) Uani 1 1 d . . . . .
H8A H 0.9476 0.3245 0.9808 0.065 Uiso 1 1 calc R U . . .
H8B H 1.0096 0.3401 0.8760 0.065 Uiso 1 1 calc R U . . .
H8C H 0.8973 0.2013 0.8754 0.065 Uiso 1 1 calc R U . . .
N1 N 0.4069(5) 0.7408(6) 0.6064(4) 0.0343(11) Uani 1 1 d . . . . .
N2 N 0.6609(5) 0.5772(5) 0.6850(4) 0.0264(10) Uani 1 1 d . . . . .
N3 N 0.7982(5) 0.4994(5) 0.7431(4) 0.0278(10) Uani 1 1 d . . . . .
O1 O 0.6634(4) 0.3981(5) 0.8481(3) 0.0402(10) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.57407(13) 0.7500 0.0280(3) Uani 1 2 d S T P . .
Cu2 Cu 1.0000 0.57292(14) 0.7500 0.0314(3) Uani 1 2 d S T P . .
Cl1 Cl 1.0000 0.8369(2) 0.7500 0.0448(6) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 C1 C2 122.6(6) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.5(6) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 117.7(6) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 121.9(5) . . ?
N1 C5 C6 115.5(4) . . ?
C4 C5 C6 122.6(5) . . ?
N2 C6 C5 116.5(5) . . ?
N2 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
O1 C7 N3 124.0(5) . . ?
O1 C7 C8 119.5(5) . . ?
N3 C7 C8 116.5(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 C5 118.9(5) . . ?
C1 N1 Cu1 131.6(4) . . ?
C5 N1 Cu1 109.1(3) . . ?
C6 N2 N3 120.8(4) . . ?
C6 N2 Cu1 119.5(4) . . ?
N3 N2 Cu1 119.7(3) . . ?
C7 N3 N2 109.5(4) . . ?
C7 N3 Cu2 122.6(3) . . ?
N2 N3 Cu2 123.5(3) . . ?
C7 O1 Cu1 109.8(4) . . ?
N2 Cu1 N2 178.4(3) . 2_656 ?
N2 Cu1 O1 106.07(16) . 2_656 ?
N2 Cu1 O1 75.09(16) 2_656 2_656 ?
N2 Cu1 O1 75.09(16) . . ?
N2 Cu1 O1 106.07(16) 2_656 . ?
O1 Cu1 O1 90.3(2) 2_656 . ?
N2 Cu1 N1 78.37(18) . . ?
N2 Cu1 N1 100.55(17) 2_656 . ?
O1 Cu1 N1 92.62(17) 2_656 . ?
O1 Cu1 N1 153.07(16) . . ?
N2 Cu1 N1 100.55(17) . 2_656 ?
N2 Cu1 N1 78.37(18) 2_656 2_656 ?
O1 Cu1 N1 153.07(16) 2_656 2_656 ?
O1 Cu1 N1 92.62(17) . 2_656 ?
N1 Cu1 N1 96.7(3) . 2_656 ?
N3 Cu2 N3 142.0(3) . 2_756 ?
N3 Cu2 Cl1 108.99(14) . . ?
N3 Cu2 Cl1 108.99(14) 2_756 . ?
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
C1 N1 1.322(7) . ?
C1 C2 1.378(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9500 . ?
C5 N1 1.355(7) . ?
C5 C6 1.460(7) . ?
C6 N2 1.283(7) . ?
C6 H6 0.9500 . ?
C7 O1 1.253(6) . ?
C7 N3 1.342(7) . ?
C7 C8 1.508(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 Cu1 2.183(5) . ?
N2 N3 1.385(6) . ?
N2 Cu1 1.953(4) . ?
N3 Cu2 1.967(4) . ?
O1 Cu1 2.172(4) . ?
Cu1 N2 1.953(4) 2_656 ?
Cu1 O1 2.172(4) 2_656 ?
Cu1 N1 2.183(5) 2_656 ?
Cu2 N3 1.967(4) 2_756 ?
Cu2 Cl1 2.297(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 1.4(9) . . . . ?
C1 C2 C3 C4 -1.5(9) . . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C4 C5 N1 3.5(8) . . . . ?
C3 C4 C5 C6 -174.9(5) . . . . ?
N1 C5 C6 N2 7.0(7) . . . . ?
C4 C5 C6 N2 -174.6(5) . . . . ?
C2 C1 N1 C5 1.1(9) . . . . ?
C2 C1 N1 Cu1 -171.5(4) . . . . ?
C4 C5 N1 C1 -3.6(8) . . . . ?
C6 C5 N1 C1 174.8(5) . . . . ?
C4 C5 N1 Cu1 170.5(4) . . . . ?
C6 C5 N1 Cu1 -11.0(6) . . . . ?
C5 C6 N2 N3 -176.5(4) . . . . ?
C5 C6 N2 Cu1 2.0(6) . . . . ?
O1 C7 N3 N2 -1.7(8) . . . . ?
C8 C7 N3 N2 178.2(5) . . . . ?
O1 C7 N3 Cu2 155.5(5) . . . . ?
C8 C7 N3 Cu2 -24.6(7) . . . . ?
C6 N2 N3 C7 -169.4(5) . . . . ?
Cu1 N2 N3 C7 12.1(5) . . . . ?
C6 N2 N3 Cu2 33.7(6) . . . . ?
Cu1 N2 N3 Cu2 -144.8(3) . . . . ?
N3 C7 O1 Cu1 -7.7(7) . . . . ?
C8 C7 O1 Cu1 172.4(4) . . . . ?
