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#$Date: 2024-04-05 08:51:22 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291083 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/13/1571384.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_1571384
loop_
_publ_author_name
'Yamba, Zaina'
'Peoble, Anna'
'Novikov, Egor'
'Castañeda, Raúl'
'Timofeeva, Tatiana'
_publ_section_title
;
 Interplay of Isomorphs and Polymorphs of Amidino-Copper(II) Complexes
 with Different Halides
;
_journal_issue                   4
_journal_name_full               Crystals
_journal_page_first              319
_journal_paper_doi               10.3390/cryst14040319
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C5 H6 Cl2 Cu N4'
_chemical_formula_sum            'C5 H6 Cl2 Cu N4'
_chemical_formula_weight         256.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-27
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.036(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4622(12)
_cell_length_b                   10.6392(14)
_cell_length_c                   9.6678(13)
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      29.25
_cell_measurement_theta_min      2.87
_cell_volume                     859.6(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16659
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.500
_diffrn_reflns_theta_min         2.867
_exptl_absorpt_coefficient_mu    3.106
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0969 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.6380.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_description       needle
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0269
_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)+(0.0374P)²+0.2373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2213
_reflns_number_total             2610
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Crystals-CIFS.cif
_cod_data_source_block           9
_cod_database_code               1571384
_shelx_shelxl_version_number     2017/1
_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   0.653
_shelx_estimated_absorpt_t_min   0.370
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-H2 \\sim N3-H3B \\sim N3-H3A
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C1(H1), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Cu1 Cu 0.19404(2) 0.48702(2) 0.59915(2) 0.02949(8) Uani 1 1 d . . . . .
Cl1 Cl 0.05414(5) 0.66586(4) 0.54834(5) 0.03743(11) Uani 1 1 d . . . . .
Cl2 Cl 0.15851(6) 0.48502(5) 0.82516(5) 0.04171(12) Uani 1 1 d . . . . .
N1 N 0.28464(16) 0.48643(13) 0.41336(15) 0.0282(3) Uani 1 1 d . . . . .
N2 N 0.33409(17) 0.34070(15) 0.62906(16) 0.0345(3) Uani 1 1 d D . . . .
H2 H 0.342(2) 0.2971(19) 0.698(2) 0.041(6) Uiso 1 1 d D . . . .
N3 N 0.5135(2) 0.21293(17) 0.5306(2) 0.0412(4) Uani 1 1 d D . . . .
H3A H 0.552(2) 0.198(2) 0.460(2) 0.044(6) Uiso 1 1 d D . . . .
H3B H 0.506(3) 0.160(2) 0.587(2) 0.059(8) Uiso 1 1 d D . . . .
N4 N 0.45063(19) 0.35859(16) 0.29349(16) 0.0390(3) Uani 1 1 d . . . . .
C1 C 0.3169(2) 0.5370(2) 0.1813(2) 0.0408(4) Uani 1 1 d . . . . .
H1 H 0.294421 0.589765 0.101366 0.049 Uiso 1 1 calc R U . . .
C2 C 0.25114(19) 0.56098(18) 0.30054(18) 0.0339(4) Uani 1 1 d . . . . .
H2A H 0.181624 0.630811 0.302776 0.041 Uiso 1 1 calc R U . . .
C3 C 0.38294(17) 0.38924(16) 0.40308(16) 0.0274(3) Uani 1 1 d . . . . .
C4 C 0.41175(17) 0.30781(16) 0.53072(17) 0.0296(3) Uani 1 1 d . . . . .
C5 C 0.4160(2) 0.4344(2) 0.18133(19) 0.0420(4) Uani 1 1 d . . . . .
H5 H 0.461475 0.416545 0.099671 0.050 Uiso 1 1 calc R U . . .
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'
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
Cl2 Cu1 Cl1 94.233(18) . . ?
N1 Cu1 Cl1 93.85(4) . . ?
N1 Cu1 Cl2 166.00(4) . . ?
N2 Cu1 Cl1 172.85(5) . . ?
N2 Cu1 Cl2 91.10(5) . . ?
N2 Cu1 N1 79.99(6) . . ?
C2 N1 Cu1 130.27(12) . . ?
C3 N1 Cu1 112.77(11) . . ?
C3 N1 C2 116.73(15) . . ?
Cu1 N2 H2 123.7(15) . . ?
C4 N2 Cu1 118.47(12) . . ?
C4 N2 H2 117.8(15) . . ?
H3A N3 H3B 122(3) . . ?
C4 N3 H3A 119.3(16) . . ?
C4 N3 H3B 114.8(18) . . ?
C3 N4 C5 115.53(16) . . ?
C2 C1 H1 120.9 . . ?
C5 C1 H1 120.9 . . ?
C5 C1 C2 118.17(17) . . ?
N1 C2 C1 120.51(17) . . ?
N1 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
N1 C3 C4 114.08(14) . . ?
N4 C3 N1 126.99(16) . . ?
N4 C3 C4 118.90(15) . . ?
N2 C4 N3 127.91(17) . . ?
N2 C4 C3 114.59(15) . . ?
N3 C4 C3 117.49(15) . . ?
N4 C5 C1 122.06(17) . . ?
N4 C5 H5 119.0 . . ?
C1 C5 H5 119.0 . . ?
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 Cl1 2.2541(5) . ?
Cu1 Cl2 2.2520(6) . ?
Cu1 N1 2.0607(15) . ?
Cu1 N2 1.9503(15) . ?
N1 C2 1.342(2) . ?
N1 C3 1.341(2) . ?
N2 H2 0.805(16) . ?
N2 C4 1.286(2) . ?
N3 H3A 0.820(16) . ?
N3 H3B 0.797(17) . ?
N3 C4 1.327(2) . ?
N4 C3 1.322(2) . ?
N4 C5 1.346(3) . ?
C1 H1 0.9500 . ?
C1 C5 1.376(3) . ?
C2 C1 1.381(3) . ?
C2 H2A 0.9500 . ?
C4 C3 1.496(2) . ?
C5 H5 0.9500 . ?
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
_geom_hbond_publ_flag
N3 H3A Cl2 0.820(16) 2.58(2) 3.2640(18) 141(2) 4_665 yes
N3 H3B Cl2 0.797(17) 2.55(2) 3.2525(19) 148(2) 2_546 yes
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
Cu1 N1 C2 C1 -174.45(13) . . . . ?
Cu1 N1 C3 N4 175.08(14) . . . . ?
Cu1 N1 C3 C4 -3.19(16) . . . . ?
Cu1 N2 C4 N3 179.23(15) . . . . ?
Cu1 N2 C4 C3 0.08(19) . . . . ?
N1 C2 C1 C5 0.5(3) . . . . ?
N2 C4 C3 N1 2.2(2) . . . . ?
N2 C4 C3 N4 -176.26(15) . . . . ?
N3 C4 C3 N1 -177.07(15) . . . . ?
N3 C4 C3 N4 4.5(2) . . . . ?
C2 N1 C3 N4 -0.1(2) . . . . ?
C2 N1 C3 C4 -178.35(13) . . . . ?
C2 C1 C5 N4 -0.4(3) . . . . ?
C3 N1 C2 C1 -0.3(2) . . . . ?
C3 N4 C5 C1 0.1(3) . . . . ?
C5 N4 C3 N1 0.2(3) . . . . ?
C5 N4 C3 C4 178.39(15) . . . . ?
