#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/74/2007493.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007493
loop_
_publ_author_name
'Elerman, Yalc̨in'
'Elmali, Ayhan'
'Özbey, Süheyla'
_publ_section_title
;
 Bis[N-(2-bromo-4-methylphenyl)naphthaldiminato]copper(II)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1072
_journal_page_last               1074
_journal_paper_doi               10.1107/S0108270198003345
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          '[Cu (C18 H13 Br N O)2]'
_chemical_formula_moiety         'C36 H26 Br2 Cu N2 O2'
_chemical_formula_sum            'C36 H26 Br2 Cu N2 O2'
_chemical_formula_weight         741.95
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2550(10)
_cell_length_b                   12.524(2)
_cell_length_c                   13.538(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.43
_cell_measurement_theta_min      4.12
_cell_volume                     1520.4(4)
_computing_cell_refinement       'MolEN (Fair, 1990)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        MolEN
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2762
_diffrn_reflns_theta_max         26.14
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        3.2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.383
_exptl_absorpt_correction_T_max  0.713
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(MolEN; Fair, 1990)'
_exptl_crystal_colour            purple-red
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             742
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.326
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.208
_refine_ls_goodness_of_fit_obs   1.387
_refine_ls_hydrogen_treatment
'H-atom parameters were constrained to parent sites'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.208
_refine_ls_restrained_S_obs      1.387
_refine_ls_R_factor_all          0.098
_refine_ls_R_factor_obs          .056
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + 3.7194P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.097
_refine_ls_wR_factor_obs         .090
_reflns_number_observed          1866
_reflns_number_total             2760
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ab1532.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^) +
3.7194P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo^2^) + 3.7194P] where P =
(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2007493
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0 0 0 .0377(3) Uani d S 1 . Cu
Br1 -.35161(7) .07438(6) -.04250(6) .0625(2) Uani d . 1 . Br
N1 -.0282(5) .1428(3) .0568(3) .0357(11) Uani d . 1 . N
O1 .0409(4) -.0583(3) .1319(3) .0445(10) Uani d . 1 . O
C1 .1142(6) -.0103(4) .2136(4) .0382(13) Uani d . 1 . C
C2 .1867(6) -.0776(5) .2956(4) .0442(15) Uani d . 1 . C
H2 .1811(6) -.1513(5) .2873(4) .100 Uiso calc R 1 . H
C3 .2633(6) -.0363(5) .3853(5) .047(2) Uani d . 1 . C
H3 .3089(6) -.0825(5) .4375(5) .100 Uiso calc R 1 . H
C4 .2766(6) .0761(5) .4028(4) .0443(14) Uani d . 1 . C
C5 .3551(7) .1177(6) .4972(5) .058(2) Uani d . 1 . C
H5 .4021(7) .0716(6) .5491(5) .100 Uiso calc R 1 . H
C6 .3630(7) .2256(6) .5132(5) .068(2) Uani d . 1 . C
H6 .4154(7) .2527(6) .5758(5) .100 Uiso calc R 1 . H
C7 .2927(7) .2944(6) .4363(5) .063(2) Uani d . 1 . C
H7 .2973(7) .3676(6) .4482(5) .100 Uiso calc R 1 . H
C8 .2165(7) .2566(5) .3430(5) .051(2) Uani d . 1 . C
H8 .1712(7) .3046(5) .2924(5) .100 Uiso calc R 1 . H
C9 .2056(6) .1461(5) .3223(4) .0393(14) Uani d . 1 . C
C10 .1231(6) .1016(4) .2267(4) .0349(13) Uani d . 1 . C
C11 .0389(6) .1705(4) .1489(4) .0369(14) Uani d . 1 . C
H11 .0316(6) .2418(4) .1662(4) .100 Uiso calc R 1 . H
C12 -.1109(6) .2226(4) -.0098(4) .0363(13) Uani d . 1 . C
C13 -.0472(7) .3186(4) -.0279(4) .0426(15) Uani d . 1 . C
H13 .0497(7) .3348(4) .0080(4) .100 Uiso calc R 1 . H
C14 -.1257(8) .3907(5) -.0986(5) .051(2) Uani d . 1 . C
H14 -.0804(8) .4544(5) -.1096(5) .100 Uiso calc R 1 . H
C15 -.2700(8) .3700(5) -.1533(5) .056(2) Uani d . 1 . C
C16 -.3536(9) .4461(6) -.2335(5) .081(2) Uani d . 1 . C
H16A -.2919 .5069 -.2371 .100 Uiso calc . 1 . H
H16B -.4430 .4691 -.2160 .100 Uiso calc . 1 . H
H16C -.3790 .4107 -.2984 .100 Uiso calc . 1 . H
C17 -.3351(7) .2766(5) -.1338(4) .049(2) Uani d . 1 . C
H17 -.4328(7) .2615(5) -.1687(4) .100 Uiso calc R 1 . H
C18 -.2576(6) .2046(4) -.0629(4) .0405(14) Uani d . 1 . C
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 3 . 180.0 ?
O1 Cu1 N1 3 3 89.8(2) ?
O1 Cu1 N1 . 3 90.2(2) y
O1 Cu1 N1 3 . 90.2(2) ?
O1 Cu1 N1 . . 89.8(2) ?
N1 Cu1 N1 3 . 180.0 ?
C11 N1 C12 . . 118.2(4) y
C11 N1 Cu1 . . 122.3(4) y
C12 N1 Cu1 . . 119.0(3) y
C1 O1 Cu1 . . 124.8(3) y
O1 C1 C10 . . 124.8(5) y
O1 C1 C2 . . 116.0(5) y
C10 C1 C2 . . 119.2(5) ?
C3 C2 C1 . . 121.1(6) ?
C3 C2 H2 . . 119.5(4) ?
C1 C2 H2 . . 119.5(3) ?
C2 C3 C4 . . 122.2(6) ?
C2 C3 H3 . . 118.9(4) ?
C4 C3 H3 . . 118.9(3) ?
C5 C4 C9 . . 120.3(6) ?
C5 C4 C3 . . 121.4(6) ?
C9 C4 C3 . . 118.3(5) ?
C6 C5 C4 . . 120.4(7) ?
C6 C5 H5 . . 119.8(4) ?
C4 C5 H5 . . 119.8(4) ?
C5 C6 C7 . . 120.0(6) ?
C5 C6 H6 . . 120.0(4) ?
C7 C6 H6 . . 120.0(4) ?
C8 C7 C6 . . 121.2(7) ?
C8 C7 H7 . . 119.4(4) ?
C6 C7 H7 . . 119.4(4) ?
C7 C8 C9 . . 121.1(6) ?
C7 C8 H8 . . 119.4(4) ?
C9 C8 H8 . . 119.4(4) ?
C8 C9 C4 . . 117.0(5) ?
C8 C9 C10 . . 123.6(5) ?
C4 C9 C10 . . 119.4(5) ?
C1 C10 C11 . . 120.0(5) ?
C1 C10 C9 . . 119.8(5) ?
C11 C10 C9 . . 119.9(5) ?
N1 C11 C10 . . 126.2(5) y
N1 C11 H11 . . 116.9(3) ?
C10 C11 H11 . . 116.9(3) ?
C13 C12 C18 . . 117.0(5) ?
C13 C12 N1 . . 122.1(5) y
C18 C12 N1 . . 120.9(5) y
C14 C13 C12 . . 120.9(6) ?
C14 C13 H13 . . 119.5(4) ?
C12 C13 H13 . . 119.5(3) ?
C15 C14 C13 . . 121.4(6) ?
C15 C14 H14 . . 119.3(4) ?
C13 C14 H14 . . 119.3(4) ?
C17 C15 C14 . . 118.0(6) ?
C17 C15 C16 . . 120.5(7) ?
C14 C15 C16 . . 121.6(6) ?
C15 C16 H16A . . 109.5(7) ?
C15 C16 H16B . . 109.5(6) ?
H16A C16 H16B . . 109.5(7) ?
C15 C16 H16C . . 109.5(6) ?
H16A C16 H16C . . 109.5(7) ?
H16B C16 H16C . . 109.5(8) ?
C15 C17 C18 . . 120.9(6) ?
C15 C17 H17 . . 119.5(4) ?
C18 C17 H17 . . 119.5(4) ?
C17 C18 C12 . . 121.8(5) ?
C17 C18 Br1 . . 118.9(5) y
C12 C18 Br1 . . 119.3(4) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 3 1.880(4) y
Cu1 O1 . 1.880(4) ?
Cu1 N1 3 1.990(4) y
Cu1 N1 . 1.990(4) ?
Br1 C18 . 1.900(6) y
N1 C11 . 1.295(6) y
N1 C12 . 1.434(6) y
O1 C1 . 1.293(6) y
C1 C10 . 1.413(7) ?
C1 C2 . 1.423(7) ?
C2 C3 . 1.349(8) ?
C2 H2 . .93 ?
C3 C4 . 1.427(8) ?
C3 H3 . .93 ?
C4 C5 . 1.404(8) ?
C4 C9 . 1.427(8) ?
C5 C6 . 1.368(9) ?
C5 H5 . .93 ?
C6 C7 . 1.384(9) ?
C6 H6 . .93 ?
C7 C8 . 1.370(8) ?
C7 H7 . .93 ?
C8 C9 . 1.411(8) ?
C8 H8 . .93 ?
C9 C10 . 1.442(7) ?
C10 C11 . 1.433(7) ?
C11 H11 . .93 ?
C12 C13 . 1.387(7) ?
C12 C18 . 1.389(7) ?
C13 C14 . 1.384(8) ?
C13 H13 . .93 ?
C14 C15 . 1.382(8) ?
C14 H14 . .93 ?
C15 C17 . 1.371(8) ?
C15 C16 . 1.506(8) ?
C16 H16A . .960(8) ?
C16 H16B . .960(8) ?
C16 H16C . .960(8) ?
C17 C18 . 1.382(7) ?
C17 H17 . .93 ?
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_site_symmetry_1
_geom_torsion
O1 Cu1 N1 C11 3 -151.9(4)
O1 Cu1 N1 C11 . 28.1(4)
N1 Cu1 N1 C11 3 0.0(3)
O1 Cu1 N1 C12 3 20.3(4)
O1 Cu1 N1 C12 . -159.7(4)
N1 Cu1 N1 C12 3 0.0(3)
O1 Cu1 O1 C1 3 0.0(2)
N1 Cu1 O1 C1 3 143.0(4)
N1 Cu1 O1 C1 . -37.0(4)
Cu1 O1 C1 C10 . 27.0(8)
Cu1 O1 C1 C2 . -154.6(4)
O1 C1 C2 C3 . -178.4(5)
C10 C1 C2 C3 . 0.1(8)
C1 C2 C3 C4 . -0.3(9)
C2 C3 C4 C5 . 179.1(6)
C2 C3 C4 C9 . 0.2(9)
C9 C4 C5 C6 . 0.7(10)
C3 C4 C5 C6 . -178.1(6)
C4 C5 C6 C7 . 0.2(11)
C5 C6 C7 C8 . -1.0(11)
C6 C7 C8 C9 . 0.7(10)
C7 C8 C9 C4 . 0.3(9)
C7 C8 C9 C10 . 178.0(6)
C5 C4 C9 C8 . -1.0(8)
C3 C4 C9 C8 . 177.9(5)
C5 C4 C9 C10 . -178.8(5)
C3 C4 C9 C10 . 0.1(8)
O1 C1 C10 C11 . 4.6(9)
C2 C1 C10 C11 . -173.8(5)
O1 C1 C10 C9 . 178.5(5)
C2 C1 C10 C9 . 0.2(8)
C8 C9 C10 C1 . -178.0(5)
C4 C9 C10 C1 . -0.3(8)
C8 C9 C10 C11 . -4.0(9)
C4 C9 C10 C11 . 173.7(5)
C12 N1 C11 C10 . 178.3(5)
Cu1 N1 C11 C10 . -9.4(8)
C1 C10 C11 N1 . -13.0(9)
C9 C10 C11 N1 . 173.0(5)
C11 N1 C12 C13 . 54.3(7)
Cu1 N1 C12 C13 . -118.3(5)
C11 N1 C12 C18 . -128.8(6)
Cu1 N1 C12 C18 . 58.7(6)
C18 C12 C13 C14 . -2.3(8)
N1 C12 C13 C14 . 174.8(5)
C12 C13 C14 C15 . 0.2(9)
C13 C14 C15 C17 . 1.5(9)
C13 C14 C15 C16 . -177.4(6)
C14 C15 C17 C18 . -1.2(9)
C16 C15 C17 C18 . 177.8(6)
C15 C17 C18 C12 . -1.0(9)
C15 C17 C18 Br1 . -177.9(5)
C13 C12 C18 C17 . 2.6(8)
N1 C12 C18 C17 . -174.5(5)
C13 C12 C18 Br1 . 179.6(4)
N1 C12 C18 Br1 . 2.5(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139056119
