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#$Date: 2019-10-10 04:06:14 +0300 (Thu, 10 Oct 2019) $
#$Revision: 219233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/13/7701341.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_7701341
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 H24 Cu F6 N4 O6'
_chemical_formula_sum            'C24 H24 Cu F6 N4 O6'
_chemical_formula_weight         642.01
_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             2019-07-11
_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                114.584(4)
_cell_angle_beta                 99.527(4)
_cell_angle_gamma                98.514(4)
_cell_formula_units_Z            1
_cell_length_a                   8.5478(4)
_cell_length_b                   9.2084(4)
_cell_length_c                   10.0669(5)
_cell_measurement_reflns_used    4575
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.7710
_cell_measurement_theta_min      3.9410
_cell_volume                     689.52(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0271
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.528
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79683
_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    1.546
_exptl_crystal_description       block
_exptl_crystal_F_000             327
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0336
_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)+(0.0496P)²+0.1282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2552
_reflns_number_total             2713
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03346g2.cif
_cod_data_source_block           4b
_cod_database_code               7701341
_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   0.844
_shelx_estimated_absorpt_t_min   0.668
_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
 C1-F1A = C1-F1B = C1-F2A = C1-F2B = C1-F3A = C1-F3B
 1.32 with sigma of 0.005
 F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.02
 F1B-F2B \\sim F1B-F3B \\sim F2B-F3B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C1, F1A, F2A, F3A, F1B, F2B, F3B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F3A)=Sof(F1A)=Sof(F2A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C6(H6), C7(H7), C3(H3A)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), 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 0.04472(14) Uani 1 2 d S T P . .
O2 O 0.72057(18) 0.38488(18) 0.49493(17) 0.0533(4) Uani 1 1 d . . . . .
O1 O 0.44064(19) 0.40755(18) 0.63448(16) 0.0530(4) Uani 1 1 d . . . . .
N1 N 0.6339(2) 0.7143(2) 0.68351(18) 0.0456(4) Uani 1 1 d . . . . .
O3 O 0.8875(2) 1.3823(2) 1.2828(2) 0.0705(5) Uani 1 1 d D . . . .
N2 N 0.8151(2) 1.2237(2) 1.1696(2) 0.0552(4) Uani 1 1 d . . . . .
C8 C 0.7943(2) 1.0242(2) 0.9260(2) 0.0428(4) Uani 1 1 d . . . . .
C11 C 0.8704(3) 1.1913(2) 1.0515(2) 0.0478(5) Uani 1 1 d . . . . .
C9 C 0.6630(3) 0.9208(3) 0.9342(2) 0.0495(5) Uani 1 1 d . . . . .
H9 H 0.626798 0.954018 1.022051 0.059 Uiso 1 1 calc R . . . .
C10 C 0.5873(3) 0.7712(3) 0.8140(2) 0.0499(5) Uani 1 1 d . . . . .
H10 H 0.499553 0.705634 0.822557 0.060 Uiso 1 1 calc R . . . .
C6 C 0.7631(3) 0.8093(3) 0.6771(2) 0.0516(5) Uani 1 1 d . . . . .
H6 H 0.800071 0.770322 0.589753 0.062 Uiso 1 1 calc R . . . .
C7 C 0.8452(3) 0.9623(3) 0.7926(2) 0.0498(5) Uani 1 1 d . . . . .
H7 H 0.934211 1.023954 0.781664 0.060 Uiso 1 1 calc R . . . .
C4 C 0.7470(3) 0.2978(3) 0.5583(3) 0.0556(5) Uani 1 1 d . . . . .
C2 C 0.5110(3) 0.3155(3) 0.6746(2) 0.0553(5) Uani 1 1 d . . . . .
F3A F 0.2658(4) 0.1828(7) 0.6941(6) 0.1050(17) Uani 0.611(9) 1 d D U . A 1
C3 C 0.6479(3) 0.2621(4) 0.6461(3) 0.0707(7) Uani 1 1 d . . . . .
H3A H 0.679681 0.195361 0.688636 0.085 Uiso 1 1 calc R . . . .
C5 C 0.8945(3) 0.2264(4) 0.5432(4) 0.0809(8) Uani 1 1 d . . . . .
H5A H 0.905713 0.190238 0.441756 0.121 Uiso 1 1 calc GR . . . .
H5B H 0.881206 0.134601 0.565957 0.121 Uiso 1 1 calc GR . . . .
H5C H 0.990584 0.308931 0.612193 0.121 Uiso 1 1 calc GR . . . .
C12 C 0.9985(4) 1.3088(3) 1.0367(3) 0.0738(7) Uani 1 1 d . . . . .
H12A H 1.043569 1.404081 1.132530 0.111 Uiso 1 1 calc GR . . . .
H12B H 0.950673 1.341577 0.963581 0.111 Uiso 1 1 calc GR . . . .
H12C H 1.083753 1.256318 1.004419 0.111 Uiso 1 1 calc GR . . . .
F1A F 0.4063(12) 0.3717(8) 0.8881(7) 0.210(5) Uani 0.611(9) 1 d D U . A 1
C1 C 0.4212(4) 0.2563(3) 0.7680(3) 0.0835(8) Uani 1 1 d D U . . .
F2A F 0.4708(8) 0.1407(12) 0.7930(13) 0.193(5) Uani 0.611(9) 1 d D U . A 1
H3 H 0.840(4) 1.386(4) 1.347(3) 0.096(11) Uiso 1 1 d D . . . .
F1B F 0.3315(11) 0.3518(13) 0.8340(10) 0.135(5) Uani 0.389(9) 1 d D U . A 2
F2B F 0.5221(9) 0.2773(11) 0.8926(6) 0.106(3) Uani 0.389(9) 1 d D U . A 2
F3B F 0.351(2) 0.1028(9) 0.7032(12) 0.256(10) Uani 0.389(9) 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
O2 Cu1 O2 180.0 . 2_666
O1 Cu1 O2 87.62(6) 2_666 2_666
O1 Cu1 O2 87.63(6) . .
O1 Cu1 O2 92.38(6) . 2_666
O1 Cu1 O2 92.38(6) 2_666 .
O1 Cu1 O1 180.0 . 2_666
O1 Cu1 N1 89.63(6) 2_666 .
O1 Cu1 N1 90.37(6) . .
O1 Cu1 N1 89.63(6) . 2_666
O1 Cu1 N1 90.37(6) 2_666 2_666
N1 Cu1 O2 91.33(6) 2_666 2_666
N1 Cu1 O2 88.67(6) 2_666 .
N1 Cu1 O2 88.67(6) . 2_666
N1 Cu1 O2 91.33(6) . .
N1 Cu1 N1 180.0 2_666 .
C4 O2 Cu1 123.56(15) . .
C2 O1 Cu1 126.93(15) . .
C10 N1 Cu1 120.91(14) . .
C6 N1 Cu1 122.17(13) . .
C6 N1 C10 116.75(18) . .
N2 O3 H3 101(3) . .
C11 N2 O3 112.26(18) . .
C9 C8 C11 121.08(18) . .
C7 C8 C11 122.77(19) . .
C7 C8 C9 116.13(19) . .
N2 C11 C8 114.25(19) . .
N2 C11 C12 124.5(2) . .
C8 C11 C12 121.27(19) . .
C8 C9 H9 119.8 . .
C10 C9 C8 120.49(19) . .
C10 C9 H9 119.8 . .
N1 C10 C9 123.05(19) . .
N1 C10 H10 118.5 . .
C9 C10 H10 118.5 . .
N1 C6 H6 118.1 . .
N1 C6 C7 123.76(19) . .
C7 C6 H6 118.1 . .
C8 C7 H7 120.1 . .
C6 C7 C8 119.73(19) . .
C6 C7 H7 120.1 . .
O2 C4 C3 124.1(2) . .
O2 C4 C5 118.2(2) . .
C3 C4 C5 117.7(2) . .
O1 C2 C3 130.8(2) . .
O1 C2 C1 111.8(2) . .
C3 C2 C1 117.4(2) . .
C4 C3 H3A 116.6 . .
C2 C3 C4 126.8(2) . .
C2 C3 H3A 116.6 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
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 . .
F3A C1 C2 110.7(3) . .
F1A C1 C2 114.3(4) . .
F1A C1 F3A 101.4(5) . .
F1A C1 F2A 112.0(5) . .
F2A C1 C2 115.2(3) . .
F2A C1 F3A 101.6(4) . .
F1B C1 C2 113.4(5) . .
F1B C1 F2B 96.6(5) . .
F2B C1 C2 111.6(4) . .
F3B C1 C2 115.1(5) . .
F3B C1 F1B 114.4(9) . .
F3B C1 F2B 103.8(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 2.2935(15) 2_666
Cu1 O2 2.2935(15) .
Cu1 O1 1.9681(14) .
Cu1 O1 1.9681(14) 2_666
Cu1 N1 2.0531(17) 2_666
Cu1 N1 2.0531(17) .
O2 C4 1.239(3) .
O1 C2 1.264(3) .
N1 C10 1.350(2) .
N1 C6 1.332(3) .
O3 N2 1.389(2) .
O3 H3 0.803(10) .
N2 C11 1.288(3) .
C8 C11 1.484(3) .
C8 C9 1.397(3) .
C8 C7 1.395(3) .
C11 C12 1.493(3) .
C9 H9 0.9300 .
C9 C10 1.368(3) .
C10 H10 0.9300 .
C6 H6 0.9300 .
C6 C7 1.380(3) .
C7 H7 0.9300 .
C4 C3 1.419(4) .
C4 C5 1.507(3) .
C2 C3 1.363(4) .
C2 C1 1.520(3) .
F3A C1 1.328(4) .
C3 H3A 0.9300 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
F1A C1 1.276(4) .
C1 F2A 1.303(4) .
C1 F1B 1.298(5) .
C1 F2B 1.321(4) .
C1 F3B 1.279(4) .
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 O2 0.803(10) 1.949(10) 2.751(2) 177(4) 1_566 yes
