#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/81/7218179.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_7218179
loop_
_publ_author_name
'Cinčić, Dominik'
'Friščić, Tomislav'
_publ_section_title
;
 Synthesis of an extended halogen-bonded metal--organic structure in a
 one-pot mechanochemical reaction that combines covalent bonding,
 coordination chemistry and supramolecular synthesis
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              10169
_journal_paper_doi               10.1039/C4CE01815J
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C38 H28 Cu N2 O4, C6 F4 I2'
_chemical_formula_sum            'C44 H28 Cu F4 I2 N2 O4'
_chemical_formula_weight         1042.02
_chemical_name_systematic
;
Tetrafluoro-1,4-diiodobenzene bis(N-(4-acetophenyl)-2-oxy-1-naphthaldiminato)-copper(ii)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                82.472(5)
_cell_angle_beta                 82.927(5)
_cell_angle_gamma                86.586(5)
_cell_formula_units_Z            1
_cell_length_a                   8.093(5)
_cell_length_b                   9.502(5)
_cell_length_c                   12.751(5)
_cell_measurement_temperature    295
_cell_volume                     963.8(9)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11870
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         3.787
_exptl_absorpt_coefficient_mu    2.235
_exptl_absorpt_correction_T_max  0.77617
_exptl_absorpt_correction_T_min  0.41600
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             509
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0417P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3055
_reflns_number_total             4192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01815j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7218179.cif.'
_cod_database_code               7218179
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
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
C1 C 0.2306(4) 0.9380(3) -0.1821(3) 0.0431(7) Uani 1 1 d . . .
C2 C 0.3672(4) 0.9883(4) -0.2558(3) 0.0539(9) Uani 1 1 d . . .
H2 H 0.4243 1.0648 -0.2421 0.065 Uiso 1 1 calc R U .
C3 C 0.4157(4) 0.9277(4) -0.3451(3) 0.0567(9) Uani 1 1 d . . .
H3 H 0.5033 0.9653 -0.3926 0.068 Uiso 1 1 calc R U .
C4 C 0.3368(4) 0.8080(4) -0.3685(3) 0.0519(9) Uani 1 1 d . . .
C5 C 0.3947(5) 0.7423(4) -0.4599(3) 0.0621(10) Uani 1 1 d . . .
H5 H 0.4835 0.7797 -0.5065 0.074 Uiso 1 1 calc R U .
C6 C 0.3218(6) 0.6239(5) -0.4809(4) 0.0731(13) Uani 1 1 d . . .
H6 H 0.3619 0.5797 -0.5404 0.088 Uiso 1 1 calc R U .
C7 C 0.1883(5) 0.5716(4) -0.4123(4) 0.0655(11) Uani 1 1 d . . .
H7 H 0.1356 0.4939 -0.4282 0.079 Uiso 1 1 calc R U .
C8 C 0.1305(5) 0.6303(4) -0.3215(3) 0.0589(10) Uani 1 1 d . . .
H8 H 0.0433 0.5896 -0.2753 0.071 Uiso 1 1 calc R U .
C9 C 0.2026(4) 0.7525(3) -0.2974(3) 0.0448(8) Uani 1 1 d . . .
C10 C 0.1452(4) 0.8208(3) -0.2026(3) 0.0410(7) Uani 1 1 d . . .
C11 C 0.0025(4) 0.7734(3) -0.1352(3) 0.0425(8) Uani 1 1 d . . .
H023 H -0.0412 0.6905 -0.1495 0.051 Uiso 1 1 calc R U .
C12 C -0.2203(4) 0.7618(3) -0.0020(3) 0.0391(7) Uani 1 1 d . . .
C13 C -0.2020(4) 0.6415(3) 0.0674(3) 0.0539(9) Uani 1 1 d . . .
H13 H -0.0961 0.6060 0.0809 0.065 Uiso 1 1 calc R U .
C14 C -0.3411(4) 0.5724(3) 0.1175(3) 0.0548(9) Uani 1 1 d . . .
H14 H -0.3277 0.4903 0.1647 0.066 Uiso 1 1 calc R U .
C15 C -0.5001(4) 0.6229(3) 0.0988(3) 0.0397(7) Uani 1 1 d . . .
C16 C -0.5166(4) 0.7446(4) 0.0284(3) 0.0510(9) Uani 1 1 d . . .
H16 H -0.6224 0.7801 0.0145 0.061 Uiso 1 1 calc R U .
C17 C -0.3781(4) 0.8144(4) -0.0218(3) 0.0531(9) Uani 1 1 d . . .
H17 H -0.3908 0.8967 -0.0689 0.064 Uiso 1 1 calc R U .
C18 C -0.6511(4) 0.5497(3) 0.1527(3) 0.0462(8) Uani 1 1 d . . .
C19 C -0.6314(5) 0.4271(4) 0.2360(3) 0.0686(11) Uani 1 1 d . . .
H19A H -0.7388 0.3912 0.2631 0.103 Uiso 1 1 calc R U .
H19B H -0.5805 0.4572 0.2929 0.103 Uiso 1 1 calc R U .
H19C H -0.5621 0.3536 0.2057 0.103 Uiso 1 1 calc R U .
C20 C 0.0749(4) 1.1250(3) -0.5030(3) 0.0533(9) Uani 1 1 d . . .
C21 C -0.0289(4) 1.0793(3) -0.4130(3) 0.0474(8) Uani 1 1 d . . .
C22 C -0.1039(4) 0.9496(4) -0.4111(3) 0.0510(8) Uani 1 1 d . . .
N1 N -0.0751(3) 0.8323(2) -0.0553(2) 0.0409(6) Uani 1 1 d . . .
O1 O 0.1928(3) 1.0035(2) -0.09889(19) 0.0513(6) Uani 1 1 d . . .
O2 O -0.7893(3) 0.5886(3) 0.1297(2) 0.0638(7) Uani 1 1 d . . .
F1 F 0.1534(3) 1.2476(2) -0.5092(2) 0.0753(7) Uani 1 1 d . . .
F2 F -0.2032(3) 0.8983(2) -0.3258(2) 0.0713(6) Uani 1 1 d . . .
Cu1 Cu 0.0000 1.0000 0.0000 0.04035(15) Uani 1 2 d S . P
I1 I -0.08204(4) 1.19808(3) -0.28691(2) 0.07013(13) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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 C1 C10 123.9(3) . .
O1 C1 C2 117.0(3) . .
C10 C1 C2 119.1(3) . .
C3 C2 C1 121.5(3) . .
C2 C3 C4 121.8(3) . .
C9 C4 C5 120.2(3) . .
C9 C4 C3 119.1(3) . .
C5 C4 C3 120.7(4) . .
C6 C5 C4 120.8(4) . .
C5 C6 C7 118.9(4) . .
C8 C7 C6 122.1(4) . .
C7 C8 C9 120.5(4) . .
C4 C9 C8 117.5(3) . .
C4 C9 C10 119.5(3) . .
C8 C9 C10 123.0(3) . .
C11 C10 C1 120.9(3) . .
C11 C10 C9 120.1(3) . .
C1 C10 C9 119.0(3) . .
N1 C11 C10 127.5(3) . .
C13 C12 C17 119.9(3) . .
C13 C12 N1 119.7(3) . .
C17 C12 N1 120.4(3) . .
C12 C13 C14 119.9(3) . .
C13 C14 C15 121.2(3) . .
C16 C15 C14 118.3(3) . .
C16 C15 C18 120.0(3) . .
C14 C15 C18 121.8(3) . .
C15 C16 C17 120.8(3) . .
C16 C17 C12 119.9(3) . .
O2 C18 C19 119.8(3) . .
O2 C18 C15 121.2(3) . .
C19 C18 C15 119.1(3) . .
F1 C20 C22 117.3(4) . 2_574
F1 C20 C21 120.0(3) . .
C22 C20 C21 122.6(3) 2_574 .
C20 C21 C22 117.0(3) . .
C20 C21 I1 122.4(2) . .
C22 C21 I1 120.6(3) . .
F2 C22 C20 119.6(3) . 2_574
F2 C22 C21 120.1(3) . .
C20 C22 C21 120.3(4) 2_574 .
C11 N1 C12 115.3(2) . .
C11 N1 Cu1 124.9(2) . .
C12 N1 Cu1 119.67(19) . .
C1 O1 Cu1 130.58(19) . .
O1 Cu1 O1 180.0 2_575 .
O1 Cu1 N1 89.34(10) 2_575 .
O1 Cu1 N1 90.66(10) . .
O1 Cu1 N1 90.66(10) 2_575 2_575
O1 Cu1 N1 89.34(10) . 2_575
N1 Cu1 N1 180.0 . 2_575
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.295(4) .
C1 C10 1.414(4) .
C1 C2 1.422(5) .
C2 C3 1.348(5) .
C3 C4 1.419(5) .
C4 C9 1.407(5) .
C4 C5 1.410(5) .
C5 C6 1.372(6) .
C6 C7 1.377(6) .
C7 C8 1.369(5) .
C8 C9 1.414(5) .
C9 C10 1.460(4) .
C10 C11 1.412(5) .
C11 N1 1.302(4) .
C12 C13 1.363(5) .
C12 C17 1.384(4) .
C12 N1 1.439(4) .
C13 C14 1.381(5) .
C14 C15 1.383(4) .
C15 C16 1.379(5) .
C15 C18 1.490(5) .
C16 C17 1.381(5) .
C18 O2 1.215(4) .
C18 C19 1.485(5) .
C20 F1 1.349(4) .
C20 C22 1.370(5) 2_574
C20 C21 1.373(5) .
C21 C22 1.402(5) .
C21 I1 2.072(3) .
C22 F2 1.326(4) .
C22 C20 1.370(5) 2_574
N1 Cu1 1.980(2) .
O1 Cu1 1.881(2) .
Cu1 O1 1.881(2) 2_575
Cu1 N1 1.980(2) 2_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199216
