#------------------------------------------------------------------------------
#$Date: 2024-04-05 07:51:22 +0200 (Fri 05 de Apr de 2024) $
#$Revision: 291083 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/13/1571380.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_1571380
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 Br2 Cu N4'
_chemical_formula_sum            'C5 H6 Br2 Cu N4'
_chemical_formula_weight         345.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-02-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.924(2)
_cell_length_b                   6.3937(16)
_cell_length_c                   15.626(4)
_cell_measurement_reflns_used    3887
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.61
_cell_volume                     891.6(4)
_computing_cell_refinement       'SAINT+ V8.40b (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX II Ver. 2019.11-0. (Bruker-AXS, 2019)'
_computing_data_reduction        'SAINT+ Ver. 2019.1-0. (Bruker-AXS, 2019)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker smart APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11741
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.943
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'EIGENMANN GmbH'
_exptl_absorpt_coefficient_mu    11.360
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1167
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0328
_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)+(0.0464P)²+1.7170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                981
_reflns_number_total             1167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Crystals-CIFS.cif
_cod_data_source_block           5
_cod_original_cell_volume        891.5(4)
_cod_database_code               1571380
_shelx_shelxl_version_number     2019/1
_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   0.600
_shelx_estimated_absorpt_t_min   0.092
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N3-H3A \\sim N3-H3B \\sim N2-H2
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
Br1 Br 0.38401(6) 0.250000 0.46404(4) 0.03182(18) Uani 1 2 d S T P . .
Br2 Br 0.46035(7) 0.250000 0.68549(4) 0.0429(2) Uani 1 2 d S T P . .
Cu1 Cu 0.60198(7) 0.250000 0.55262(4) 0.0313(2) Uani 1 2 d S T P . .
N1 N 0.7487(5) 0.250000 0.4507(3) 0.0254(9) Uani 1 2 d S T P . .
N2 N 0.7916(5) 0.250000 0.6148(3) 0.0320(11) Uani 1 2 d DS T P . .
N3 N 1.0564(5) 0.250000 0.5980(4) 0.0362(11) Uani 1 2 d DS T P . .
H3A H 1.073(10) 0.250000 0.660(3) 0.07(2) Uiso 1 2 d DS . P . .
H3B H 1.135(5) 0.250000 0.554(3) 0.015(13) Uiso 1 2 d DS . P . .
N4 N 1.0101(5) 0.250000 0.4253(4) 0.0374(12) Uani 1 2 d S T P . .
C5 C 0.9140(5) 0.250000 0.5699(4) 0.0263(11) Uani 1 2 d S T P . .
C4 C 0.8916(5) 0.250000 0.4759(4) 0.0238(10) Uani 1 2 d S T P . .
C1 C 0.7225(6) 0.250000 0.3661(4) 0.0361(13) Uani 1 2 d S T P . .
H1 H 0.622509 0.250000 0.345336 0.043 Uiso 1 2 calc R U P . .
C2 C 0.8415(7) 0.250000 0.3092(4) 0.0417(15) Uani 1 2 d S T P . .
H2A H 0.824853 0.250000 0.249196 0.050 Uiso 1 2 calc R U P . .
C3 C 0.9831(7) 0.250000 0.3418(5) 0.0472(17) Uani 1 2 d S T P . .
H3 H 1.065499 0.250000 0.303269 0.057 Uiso 1 2 calc R U P . .
H2 H 0.807(8) 0.250000 0.676(3) 0.05(2) Uiso 1 2 d DS . P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 '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
Br1 Cu1 Br2 94.11(3) . . ?
N1 Cu1 Br1 93.99(12) . . ?
N1 Cu1 Br2 171.91(13) . . ?
N2 Cu1 Br1 174.43(14) . . ?
N2 Cu1 Br2 91.46(14) . . ?
N2 Cu1 N1 80.44(19) . . ?
C4 N1 Cu1 112.3(4) . . ?
C4 N1 C1 117.2(5) . . ?
C1 N1 Cu1 130.6(4) . . ?
Cu1 N2 H2 128(5) . . ?
C5 N2 Cu1 117.4(4) . . ?
C5 N2 H2 114(5) . . ?
H3A N3 H3B 126(6) . . ?
C5 N3 H3A 118(5) . . ?
C5 N3 H3B 117(3) . . ?
C4 N4 C3 116.3(5) . . ?
N2 C5 N3 128.2(6) . . ?
N2 C5 C4 115.0(4) . . ?
N3 C5 C4 116.8(5) . . ?
N1 C4 C5 114.9(4) . . ?
N4 C4 N1 126.1(5) . . ?
N4 C4 C5 119.1(5) . . ?
N1 C1 H1 120.0 . . ?
N1 C1 C2 119.9(5) . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 C1 118.2(6) . . ?
C3 C2 H2A 120.9 . . ?
N4 C3 C2 122.4(6) . . ?
N4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
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
Br1 Cu1 2.3873(9) . ?
Br2 Cu1 2.4306(10) . ?
Cu1 N1 2.062(4) . ?
Cu1 N2 1.951(5) . ?
N1 C4 1.335(7) . ?
N1 C1 1.342(7) . ?
N2 C5 1.299(7) . ?
N2 H2 0.97(4) . ?
N3 H3A 0.98(4) . ?
N3 H3B 0.98(4) . ?
N3 C5 1.344(7) . ?
N4 C4 1.320(7) . ?
N4 C3 1.327(9) . ?
C5 C4 1.482(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(8) . ?
C2 H2A 0.9500 . ?
C2 C3 1.362(9) . ?
C3 H3 0.9500 . ?
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 C4 N4 180.000(1) . . . . ?
Cu1 N1 C4 C5 0.000(1) . . . . ?
Cu1 N1 C1 C2 180.000(1) . . . . ?
Cu1 N2 C5 N3 180.000(1) . . . . ?
Cu1 N2 C5 C4 0.000(1) . . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
N2 C5 C4 N1 0.000(2) . . . . ?
N2 C5 C4 N4 180.000(1) . . . . ?
N3 C5 C4 N1 180.000(1) . . . . ?
N3 C5 C4 N4 0.000(1) . . . . ?
C4 N1 C1 C2 0.000(1) . . . . ?
C4 N4 C3 C2 0.000(1) . . . . ?
C1 N1 C4 N4 0.000(1) . . . . ?
C1 N1 C4 C5 180.000(1) . . . . ?
C1 C2 C3 N4 0.000(1) . . . . ?
C3 N4 C4 N1 0.000(1) . . . . ?
C3 N4 C4 C5 180.000(1) . . . . ?
