#------------------------------------------------------------------------------
#$Date: 2019-10-10 04:06:14 +0300 (Thu, 10 Oct 2019) $
#$Revision: 219233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/13/7701345.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_7701345
loop_
_publ_author_name
'Kodrin, Ivan'
'Borovina, Mladen'
'Šmital, Luka'
'Valdés-Martínez, Jesús'
'Aakeröy, Christer B'
'Đaković, Marijana'
_publ_section_title
;
 Exploring and predicting intermolecular binding preferences in
 crystalline Cu(ii) coordination complexes.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/c9dt03346g
_journal_year                    2019
_chemical_formula_moiety         'C24 H18 Cu F12 N4 O6'
_chemical_formula_sum            'C24 H18 Cu F12 N4 O6'
_chemical_formula_weight         749.96
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.    2019-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                117.344(6)
_cell_angle_beta                 90.254(7)
_cell_angle_gamma                98.312(6)
_cell_formula_units_Z            1
_cell_length_a                   6.7979(6)
_cell_length_b                   10.8757(6)
_cell_length_c                   11.5285(8)
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.1450
_cell_measurement_theta_min      3.8680
_cell_volume                     746.70(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5527
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.546
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_description       block
_exptl_crystal_F_000             375
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0467
_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)+(0.0519P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2054
_reflns_number_total             2604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03346g2.cif
_cod_data_source_block           4a
_cod_database_code               7701345
_shelx_shelxl_version_number     2018/3
_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_max   0.755
_shelx_estimated_absorpt_t_min   0.652
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
 C5-F6A = C5-F4A = C5-F5A = C5-F5B = C5-F6B = C5-F4B
 1.32 with sigma of 0.01
 F6A-F4A \\sim F6A-F5A \\sim F4A-F5A \\sim F5B-F6B \\sim F5B-F4B \\sim F6B-F4B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F4A, F5A, F6A, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F5B, F6B, F4B, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F5B)=Sof(F6B)=Sof(F4B)=1-FVAR(1)
 Sof(F6A)=Sof(F4A)=Sof(F5A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C3(H3A)
5.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
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
Cu1 Cu 0.500000 0.500000 0.500000 0.0457(2) Uani 1 2 d S T P . .
O1 O 0.3543(3) 0.6210(2) 0.6533(2) 0.0539(6) Uani 1 1 d . . . . .
O2 O 0.6649(3) 0.4552(2) 0.6439(2) 0.0572(6) Uani 1 1 d . . . . .
N1 N 0.2861(4) 0.3291(2) 0.4588(2) 0.0452(6) Uani 1 1 d . . . . .
F2 F 0.2795(5) 0.7956(3) 0.9850(2) 0.1166(10) Uani 1 1 d . . . . .
F1 F 0.0792(4) 0.7376(3) 0.8185(3) 0.1114(9) Uani 1 1 d . . . . .
F3 F 0.3372(5) 0.8885(2) 0.8580(3) 0.1150(10) Uani 1 1 d . . . . .
O3 O -0.4722(4) -0.1317(3) 0.3633(3) 0.0847(9) Uani 1 1 d D . . . .
N2 N -0.3247(4) -0.0118(3) 0.4120(3) 0.0624(8) Uani 1 1 d . . . . .
F6A F 0.8293(13) 0.5740(8) 0.9594(6) 0.098(3) Uani 0.644(16) 1 d D U . A 1
C2 C 0.3889(5) 0.6556(3) 0.7727(3) 0.0525(8) Uani 1 1 d . . . . .
C4 C 0.6428(5) 0.5120(3) 0.7625(3) 0.0521(8) Uani 1 1 d . . . . .
C6 C 0.1021(5) 0.3416(3) 0.4978(3) 0.0518(8) Uani 1 1 d . . . . .
H6 H 0.075702 0.431393 0.551582 0.062 Uiso 1 1 calc R . . . .
C11 C -0.1794(5) -0.0273(3) 0.3400(3) 0.0559(8) Uani 1 1 d . . . . .
C8 C -0.0170(5) 0.0951(3) 0.3837(3) 0.0473(7) Uani 1 1 d . . . . .
C7 C -0.0500(5) 0.2314(3) 0.4640(3) 0.0526(8) Uani 1 1 d . . . . .
H7 H -0.175035 0.247340 0.494407 0.063 Uiso 1 1 calc R . . . .
C9 C 0.1741(5) 0.0811(3) 0.3448(3) 0.0610(9) Uani 1 1 d . . . . .
H9 H 0.204361 -0.007527 0.291183 0.073 Uiso 1 1 calc R . . . .
C10 C 0.3194(5) 0.1973(3) 0.3850(3) 0.0587(9) Uani 1 1 d . . . . .
H10 H 0.447609 0.184034 0.359774 0.070 Uiso 1 1 calc R . . . .
C5 C 0.7699(6) 0.4698(4) 0.8443(3) 0.0701(10) Uani 1 1 d D U . . .
C3 C 0.5169(6) 0.6093(4) 0.8306(3) 0.0647(10) Uani 1 1 d . . . . .
H3A H 0.520373 0.644722 0.921079 0.078 Uiso 1 1 calc R . . . .
C1 C 0.2712(7) 0.7699(4) 0.8613(4) 0.0748(11) Uani 1 1 d . . . . .
F4A F 0.6785(17) 0.3710(10) 0.8644(11) 0.152(4) Uani 0.644(16) 1 d D U . A 1
F5A F 0.9409(15) 0.4357(16) 0.7915(7) 0.132(4) Uani 0.644(16) 1 d D U . A 1
C12 C -0.1691(7) -0.1594(4) 0.2163(4) 0.1026(16) Uani 1 1 d . . . . .
H12A H -0.132038 -0.228831 0.237780 0.154 Uiso 1 1 calc GR . . . .
H12B H -0.071569 -0.139934 0.164444 0.154 Uiso 1 1 calc GR . . . .
H12C H -0.297186 -0.193831 0.167630 0.154 Uiso 1 1 calc GR . . . .
H3 H -0.547(5) -0.100(4) 0.421(3) 0.103(17) Uiso 1 1 d D . . . .
F5B F 0.830(3) 0.3505(11) 0.7737(9) 0.090(4) Uani 0.356(16) 1 d D U . A 2
F6B F 0.910(3) 0.5637(17) 0.920(2) 0.151(9) Uani 0.356(16) 1 d D U . A 2
F4B F 0.655(3) 0.435(2) 0.921(2) 0.140(7) Uani 0.356(16) 1 d D U . A 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'
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
O1 Cu1 O1 180.00(10) 2_666 .
O1 Cu1 O2 93.61(8) 2_666 .
O1 Cu1 O2 86.39(8) . .
O1 Cu1 O2 86.39(8) 2_666 2_666
O1 Cu1 O2 93.61(8) . 2_666
O1 Cu1 N1 89.59(9) 2_666 .
O1 Cu1 N1 90.41(9) 2_666 2_666
O1 Cu1 N1 89.59(9) . 2_666
O1 Cu1 N1 90.41(9) . .
O2 Cu1 O2 180.0 2_666 .
N1 Cu1 O2 90.13(9) 2_666 .
N1 Cu1 O2 89.87(9) 2_666 2_666
N1 Cu1 O2 90.13(9) . 2_666
N1 Cu1 O2 89.87(9) . .
N1 Cu1 N1 180.0 . 2_666
C2 O1 Cu1 128.0(2) . .
C4 O2 Cu1 122.8(2) . .
C6 N1 Cu1 122.2(2) . .
C6 N1 C10 115.8(3) . .
C10 N1 Cu1 121.9(2) . .
N2 O3 H3 97(3) . .
C11 N2 O3 112.5(3) . .
O1 C2 C3 129.5(3) . .
O1 C2 C1 112.1(3) . .
C3 C2 C1 118.4(3) . .
O2 C4 C5 115.1(3) . .
O2 C4 C3 128.3(3) . .
C3 C4 C5 116.7(3) . .
N1 C6 H6 117.8 . .
N1 C6 C7 124.4(3) . .
C7 C6 H6 117.8 . .
N2 C11 C8 116.2(3) . .
N2 C11 C12 123.4(3) . .
C8 C11 C12 120.4(3) . .
C7 C8 C11 121.7(3) . .
C9 C8 C11 122.1(3) . .
C9 C8 C7 116.2(3) . .
C6 C7 C8 119.8(3) . .
C6 C7 H7 120.1 . .
C8 C7 H7 120.1 . .
C8 C9 H9 119.8 . .
C10 C9 C8 120.4(3) . .
C10 C9 H9 119.8 . .
N1 C10 C9 123.4(3) . .
N1 C10 H10 118.3 . .
C9 C10 H10 118.3 . .
F6A C5 C4 112.0(5) . .
F6A C5 F5A 103.0(6) . .
F4A C5 F6A 106.0(6) . .
F4A C5 C4 113.6(5) . .
F4A C5 F5A 109.9(6) . .
F5A C5 C4 111.6(4) . .
F5B C5 C4 112.4(5) . .
F5B C5 F4B 99.5(7) . .
F6B C5 C4 116.0(10) . .
F6B C5 F5B 112.2(10) . .
F6B C5 F4B 105.6(11) . .
F4B C5 C4 109.6(9) . .
C2 C3 C4 124.5(3) . .
C2 C3 H3A 117.8 . .
C4 C3 H3A 117.8 . .
F2 C1 F1 107.1(4) . .
F2 C1 F3 108.0(3) . .
F2 C1 C2 114.5(3) . .
F1 C1 C2 111.5(3) . .
F3 C1 F1 105.4(4) . .
F3 C1 C2 109.9(3) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 2.023(2) 2_666
Cu1 O1 2.023(2) .
Cu1 O2 2.266(2) .
Cu1 O2 2.266(2) 2_666
Cu1 N1 2.049(2) .
Cu1 N1 2.049(2) 2_666
O1 C2 1.260(4) .
O2 C4 1.235(3) .
N1 C6 1.335(4) .
N1 C10 1.344(4) .
F2 C1 1.320(4) .
F1 C1 1.331(5) .
F3 C1 1.321(5) .
O3 N2 1.402(4) .
O3 H3 0.817(10) .
N2 C11 1.273(4) .
F6A C5 1.300(6) .
C2 C3 1.373(5) .
C2 C1 1.535(5) .
C4 C5 1.533(5) .
C4 C3 1.404(4) .
C6 H6 0.9300 .
C6 C7 1.366(4) .
C11 C8 1.483(4) .
C11 C12 1.499(5) .
C8 C7 1.394(4) .
C8 C9 1.383(4) .
C7 H7 0.9300 .
C9 H9 0.9300 .
C9 C10 1.372(4) .
C10 H10 0.9300 .
C5 F4A 1.277(7) .
C5 F5A 1.335(6) .
C5 F5B 1.303(7) .
C5 F6B 1.268(9) .
C5 F4B 1.331(8) .
C3 H3A 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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
O3 H3 N2 0.817(10) 2.026(14) 2.827(4) 167(4) 2_456 yes
