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#$Date: 2024-06-08 00:39:51 +0200 (Sat 08 de Jun de 2024) $
#$Revision: 292263 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/88/7248820.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_7248820
loop_
_publ_author_name
'Delegkou, Maria-Ioanna'
'Panagiotou, Nikos'
'Papatriantafyllopoulou, Constantina'
'Tasiopoulos, Anastasios'
'Papaioannou, Dionissios A.'
'Perlepes, Spyros'
'Nastopoulos, Vassilios'
_publ_section_title
;
 Solvatomorphism with polar protic/aprotic and non-polar solvents in a
 series of complexes derived from the
 5-phenylimidazole/tetrafluoroborate/copper(II) reaction system
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D4CE00304G
_journal_year                    2024
_chemical_formula_moiety         'C36 H32 B2 Cu F8 N8, 0.70(C6 H14 O)'
_chemical_formula_sum            'C40.2 H41.8 B2 Cu F8 N8 O0.7'
_chemical_formula_weight         885.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-03-21 deposited with the CCDC.	2024-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                96.464(8)
_cell_angle_beta                 96.268(8)
_cell_angle_gamma                106.150(7)
_cell_formula_units_Z            1
_cell_length_a                   8.7016(6)
_cell_length_b                   9.8158(8)
_cell_length_c                   12.9608(14)
_cell_measurement_reflns_used    2212
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7740
_cell_measurement_theta_min      3.5970
_cell_volume                     1045.07(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
'PLATON v.270519 (Spek, 2009); MERCURY v.2020.3.0 (Macrae et al. 2020)'
_computing_publication_material
'WINGX v.2018.3 (Farrugia, 2012); OLEX2 v.1.3.0 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution
'SIR92 (Altomare et al., 1994); SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova with Atlas CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0777
_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       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            3674
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.894
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Nitromethane/diisopropyl ether'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0855
_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)+(0.0845P)²+4.7851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2155
_refine_ls_wR_factor_ref         0.2269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3069
_reflns_number_total             3674
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00304g2.cif
_cod_data_source_block           16
_cod_original_cell_volume        1045.07(16)
_cod_original_formula_sum        'C40.20 H41.80 B2 Cu F8 N8 O0.70'
_cod_database_code               7248820
_shelx_shelxl_version_number     2019/3
_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   0.894
_shelx_estimated_absorpt_t_max   0.931
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.500000 0.000000 1.000000 0.0168(3) Uani 1 2 d S . P . .
N1A N 0.1168(6) -0.0733(6) 0.7614(4) 0.0235(12) Uani 1 1 d D . . . .
H1A H 0.014(3) -0.110(8) 0.744(6) 0.035 Uiso 1 1 d D U . . .
C2A C 0.1831(7) -0.0573(7) 0.8619(5) 0.0215(13) Uani 1 1 d . . . . .
H2A H 0.123236 -0.075678 0.918525 0.026 Uiso 1 1 calc R U . . .
N3A N 0.3418(6) -0.0130(5) 0.8720(4) 0.0187(11) Uani 1 1 d . . . . .
C4A C 0.3781(8) 0.0010(7) 0.7715(5) 0.0263(15) Uani 1 1 d . . . . .
H4A H 0.484259 0.031956 0.754057 0.032 Uiso 1 1 calc R U . . .
C5A C 0.2389(8) -0.0363(8) 0.7012(5) 0.0262(15) Uani 1 1 d . . . . .
C6A C 0.2089(6) -0.0495(6) 0.5860(4) 0.0361(16) Uani 1 1 d G . . . .
C7A C 0.0752(7) -0.1514(6) 0.5292(4) 0.058(2) Uani 1 1 d G . . . .
H7A H -0.000300 -0.211979 0.564407 0.070 Uiso 1 1 calc R U . . .
C8A C 0.0508(8) -0.1655(7) 0.4212(4) 0.065(3) Uani 1 1 d G . . . .
H8A H -0.041440 -0.235797 0.382004 0.078 Uiso 1 1 calc R U . . .
C9A C 0.1602(8) -0.0777(8) 0.3701(4) 0.061(2) Uani 1 1 d G . . . .
H9A H 0.143406 -0.087461 0.295676 0.074 Uiso 1 1 calc R U . . .
C10A C 0.2939(7) 0.0241(8) 0.4270(4) 0.074(3) Uani 1 1 d G U . . .
H10A H 0.369392 0.084695 0.391752 0.088 Uiso 1 1 calc R U . . .
C11A C 0.3183(7) 0.0382(8) 0.5349(4) 0.064(3) Uani 1 1 d G U . . .
H11A H 0.410533 0.108515 0.574156 0.076 Uiso 1 1 calc R U . . .
N1B N 0.7450(6) 0.3924(5) 0.9277(4) 0.0192(11) Uani 1 1 d D . . . .
H1B H 0.762(9) 0.483(3) 0.928(6) 0.029 Uiso 1 1 d D U . . .
C2B C 0.6242(7) 0.3001(7) 0.9631(5) 0.0201(13) Uani 1 1 d . . . . .
H2B H 0.534241 0.322991 0.987881 0.024 Uiso 1 1 calc R U . . .
N3B N 0.6489(6) 0.1732(5) 0.9585(4) 0.0175(11) Uani 1 1 d . . . . .
C4B C 0.7893(7) 0.1844(6) 0.9177(5) 0.0195(13) Uani 1 1 d . . . . .
H4B H 0.836133 0.108608 0.905029 0.023 Uiso 1 1 calc R U . . .
C5B C 0.8522(7) 0.3213(7) 0.8980(5) 0.0198(13) Uani 1 1 d . . . . .
C6B C 1.0018(7) 0.3883(7) 0.8572(5) 0.0197(13) Uani 1 1 d . . . . .
C7B C 1.0280(8) 0.5198(7) 0.8189(5) 0.0262(15) Uani 1 1 d . . . . .
H7B H 0.947353 0.568130 0.819283 0.031 Uiso 1 1 calc R U . . .
C8B C 1.1692(8) 0.5795(8) 0.7808(6) 0.0315(16) Uani 1 1 d . . . . .
H8B H 1.186449 0.669287 0.756080 0.038 Uiso 1 1 calc R U . . .
C9B C 1.2861(8) 0.5085(8) 0.7786(6) 0.0326(17) Uani 1 1 d . . . . .
H9B H 1.383468 0.549704 0.752128 0.039 Uiso 1 1 calc R U . . .
C10B C 1.2621(8) 0.3787(8) 0.8144(6) 0.0286(15) Uani 1 1 d . . . . .
H10B H 1.341792 0.329644 0.811452 0.034 Uiso 1 1 calc R U . . .
C11B C 1.1213(8) 0.3192(7) 0.8550(5) 0.0235(14) Uani 1 1 d . . . . .
H11B H 1.106495 0.230777 0.881437 0.028 Uiso 1 1 calc R U . . .
B B 0.7328(9) -0.2122(8) 0.8699(6) 0.0231(15) Uani 1 1 d . . . . .
F1 F 0.6041(5) -0.1571(4) 0.8751(4) 0.0362(10) Uani 1 1 d . . . . .
F2 F 0.7837(6) -0.2103(7) 0.7722(4) 0.0631(16) Uani 1 1 d . . . . .
F3 F 0.6843(5) -0.3522(4) 0.8910(4) 0.0409(11) Uani 1 1 d . . . . .
F4 F 0.8617(4) -0.1321(4) 0.9453(3) 0.0326(9) Uani 1 1 d . . . . .
O O 0.527(2) 0.557(2) 0.5325(16) 0.083(5) Uani 0.35 1 d D U P C .
C12 C 0.606(2) 0.3915(18) 0.6471(12) 0.081(5) Uani 0.7 1 d D U P C .
H12A H 0.684246 0.337452 0.655557 0.122 Uiso 0.7 1 calc R U P . .
H12B H 0.496329 0.327395 0.645338 0.122 Uiso 0.7 1 calc R U P . .
H12C H 0.629264 0.469434 0.706274 0.122 Uiso 0.7 1 calc R U P . .
C13 C 0.6166(17) 0.4540(18) 0.5454(13) 0.086(4) Uani 0.7 1 d D U P . .
H13A H 0.569219 0.372128 0.486960 0.129 Uiso 0.35 1 calc R U P A 1
H13B H 0.719642 0.530473 0.574928 0.129 Uiso 0.35 1 calc R U P B 2
C14A C 0.789(3) 0.509(3) 0.538(3) 0.065(6) Uani 0.35 1 d D U P C 1
H14A H 0.832757 0.428005 0.523283 0.097 Uiso 0.35 1 calc R U P C 1
H14B H 0.846052 0.567281 0.604902 0.097 Uiso 0.35 1 calc R U P C 1
H14C H 0.803179 0.567394 0.481661 0.097 Uiso 0.35 1 calc R U P C 1
C14B C 0.697(4) 0.377(3) 0.476(3) 0.079(7) Uani 0.35 1 d D U P C 2
H14D H 0.742736 0.314117 0.515142 0.118 Uiso 0.35 1 calc R U P C 2
H14E H 0.783149 0.446067 0.450399 0.118 Uiso 0.35 1 calc R U P C 2
H14F H 0.617588 0.319109 0.416550 0.118 Uiso 0.35 1 calc R U P C 2
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
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
N3B Cu N3B 180.0 2_657 . ?
N3B Cu N3A 90.8(2) 2_657 . ?
N3B Cu N3A 89.2(2) . . ?
N3B Cu N3A 89.2(2) 2_657 2_657 ?
N3B Cu N3A 90.8(2) . 2_657 ?
N3A Cu N3A 180.0 . 2_657 ?
C2A N1A C5A 108.7(5) . . ?
C2A N1A H1A 119(5) . . ?
C5A N1A H1A 132(5) . . ?
N3A C2A N1A 111.1(5) . . ?
N3A C2A H2A 124.5 . . ?
N1A C2A H2A 124.5 . . ?
C2A N3A C4A 105.6(5) . . ?
C2A N3A Cu 127.5(4) . . ?
C4A N3A Cu 126.2(4) . . ?
C5A C4A N3A 110.2(6) . . ?
C5A C4A H4A 124.9 . . ?
N3A C4A H4A 124.9 . . ?
C4A C5A N1A 104.5(6) . . ?
C4A C5A C6A 132.4(6) . . ?
N1A C5A C6A 123.0(6) . . ?
C7A C6A C11A 120.0 . . ?
C7A C6A C5A 120.5(4) . . ?
C11A C6A C5A 119.4(4) . . ?
C6A C7A C8A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C11A C10A C9A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C11A C6A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C6A C11A H11A 120.0 . . ?
C2B N1B C5B 108.6(5) . . ?
C2B N1B H1B 128(5) . . ?
C5B N1B H1B 123(5) . . ?
N3B C2B N1B 110.0(5) . . ?
N3B C2B H2B 125.0 . . ?
N1B C2B H2B 125.0 . . ?
C2B N3B C4B 106.9(5) . . ?
C2B N3B Cu 124.8(4) . . ?
C4B N3B Cu 128.3(4) . . ?
N3B C4B C5B 109.6(5) . . ?
N3B C4B H4B 125.2 . . ?
C5B C4B H4B 125.2 . . ?
C4B C5B N1B 104.9(5) . . ?
C4B C5B C6B 130.8(6) . . ?
N1B C5B C6B 124.3(6) . . ?
C11B C6B C7B 118.5(6) . . ?
C11B C6B C5B 119.4(6) . . ?
C7B C6B C5B 122.1(6) . . ?
C8B C7B C6B 120.7(6) . . ?
C8B C7B H7B 119.6 . . ?
C6B C7B H7B 119.6 . . ?
C7B C8B C9B 119.9(7) . . ?
C7B C8B H8B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C10B C9B C8B 120.3(7) . . ?
C10B C9B H9B 119.8 . . ?
C8B C9B H9B 119.8 . . ?
C9B C10B C11B 120.1(6) . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C10B C11B C6B 120.5(6) . . ?
C10B C11B H11B 119.8 . . ?
C6B C11B H11B 119.8 . . ?
F1 B F2 111.9(6) . . ?
F1 B F4 109.6(6) . . ?
F2 B F4 108.5(5) . . ?
F1 B F3 107.8(5) . . ?
F2 B F3 109.9(6) . . ?
F4 B F3 109.0(6) . . ?
O O C13 65.9(10) 2_666 . ?
O O C13 63.3(10) 2_666 2_666 ?
C13 O C13 129.2(16) . 2_666 ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O C13 C14A 114.4(18) . . ?
O C13 C14B 135(2) . . ?
O C13 C12 114.8(15) . . ?
C14A C13 C12 106.5(16) . . ?
C14B C13 C12 109.7(17) . . ?
O C13 H13A 106.9 . . ?
C14A C13 H13A 106.9 . . ?
C12 C13 H13A 106.9 . . ?
O C13 H13B 93.0 . . ?
C14B C13 H13B 93.0 . . ?
C12 C13 H13B 93.0 . . ?
C13 C14A H14A 109.5 . . ?
C13 C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13 C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13 C14B H14D 109.5 . . ?
C13 C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13 C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
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
Cu N3B 1.998(5) 2_657 ?
Cu N3B 1.998(5) . ?
Cu N3A 2.005(5) . ?
Cu N3A 2.005(5) 2_657 ?
N1A C2A 1.340(8) . ?
N1A C5A 1.378(9) . ?
N1A H1A 0.86(2) . ?
C2A N3A 1.315(8) . ?
C2A H2A 0.9500 . ?
N3A C4A 1.385(8) . ?
C4A C5A 1.367(9) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.472(8) . ?
C6A C7A 1.377(4) . ?
C6A C11A 1.377(4) . ?
C7A C8A 1.377(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.377(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.377(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.377(4) . ?
C10A H10A 0.9500 . ?
C11A H11A 0.9500 . ?
N1B C2B 1.343(8) . ?
N1B C5B 1.373(8) . ?
N1B H1B 0.86(2) . ?
C2B N3B 1.318(8) . ?
C2B H2B 0.9500 . ?
N3B C4B 1.364(8) . ?
C4B C5B 1.368(9) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.469(9) . ?
C6B C11B 1.391(9) . ?
C6B C7B 1.403(9) . ?
C7B C8B 1.376(9) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.385(10) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.374(10) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.389(9) . ?
C10B H10B 0.9500 . ?
C11B H11B 0.9500 . ?
B F1 1.377(8) . ?
B F2 1.386(9) . ?
B F4 1.388(9) . ?
B F3 1.389(9) . ?
O O 1.26(4) 2_666 ?
O C13 1.454(10) . ?
O C13 1.487(10) 2_666 ?
C12 C13 1.516(10) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14A 1.46(2) . ?
C13 C14B 1.46(2) . ?
C13 H13A 1.0000 . ?
C13 H13B 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
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
N1A H1A F2 0.86(2) 2.06(4) 2.862(7) 155(7) 1_455 yes
N1B H1B F3 0.86(2) 2.00(4) 2.782(6) 150(7) 1_565 yes
