#------------------------------------------------------------------------------
#$Date: 2019-10-10 04:06:14 +0300 (Thu, 10 Oct 2019) $
#$Revision: 219233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/13/7701344.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_7701344
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         'C34 H22 Cu F12 N4 O6'
_chemical_formula_sum            'C34 H22 Cu F12 N4 O6'
_chemical_formula_weight         874.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 103.836(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3294(5)
_cell_length_b                   22.7479(6)
_cell_length_c                   7.3599(3)
_cell_measurement_reflns_used    3317
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.5670
_cell_measurement_theta_min      3.4860
_cell_volume                     1841.76(12)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0346
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.136
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80142
_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    1.576
_exptl_crystal_description       block
_exptl_crystal_F_000             878
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0431
_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)+(0.0551P)²+0.4885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2879
_reflns_number_total             3611
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03346g2.cif
_cod_data_source_block           5a-II
_cod_database_code               7701344
_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   0.872
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C5-F4A = C5-F4B = C5-F5A = C5-F5B = C5-F6A = C5-F6B
 1.32 with sigma of 0.005
 F4A-F5A \\sim F4A-F6A \\sim F5A-F6A \\sim F4B-F5B \\sim F4B-F6B \\sim F5B-F6B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F5B, F6B, F4B, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4A, F5A, F6A, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O3B)=Sof(H3B)=1-FVAR(1)
 Sof(O3A)=Sof(H3A)=FVAR(1)
 Sof(F6B)=Sof(F4B)=Sof(F5B)=1-FVAR(2)
 Sof(F4A)=Sof(F6A)=Sof(F5A)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C7(H7), C6(H6), C3(H3), C17(H17), C13(H13), C15(H15),
 C16(H16), C14(H14)
5.b Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O3B(H3B)
;
loop_
_space_group_symop_operation_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_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 0.04720(15) Uani 1 2 d S T P . .
O1 O 0.40324(16) 0.44279(7) 0.6216(3) 0.0619(5) Uani 1 1 d . . . . .
O2 O 0.55688(17) 0.42237(8) 0.3575(2) 0.0630(5) Uani 1 1 d . . . . .
N1 N 0.35257(18) 0.51312(8) 0.2870(3) 0.0499(5) Uani 1 1 d . . . . .
F3 F 0.3705(2) 0.30297(8) 0.7962(3) 0.1069(7) Uani 1 1 d . . . . .
N2 N 0.04158(19) 0.53938(10) -0.3239(3) 0.0617(6) Uani 1 1 d . . . . .
F2 F 0.3986(2) 0.38228(11) 0.9460(3) 0.1270(9) Uani 1 1 d . . . . .
F1 F 0.24088(19) 0.37058(11) 0.7303(4) 0.1301(9) Uani 1 1 d . . . . .
C8 C 0.1648(2) 0.54766(10) -0.0151(3) 0.0510(6) Uani 1 1 d . . . . .
C10 C 0.2470(2) 0.53304(11) 0.3128(3) 0.0545(6) Uani 1 1 d . . . . .
H10 H 0.236385 0.534836 0.434086 0.065 Uiso 1 1 calc R . . . .
C9 C 0.1530(2) 0.55110(12) 0.1674(3) 0.0565(6) Uani 1 1 d . . . . .
H9 H 0.081635 0.565592 0.192076 0.068 Uiso 1 1 calc R . . . .
C12 C 0.0028(2) 0.62431(12) -0.1445(3) 0.0572(6) Uani 1 1 d . . . . .
C7 C 0.2727(2) 0.52452(13) -0.0417(3) 0.0635(7) Uani 1 1 d . . . . .
H7 H 0.284140 0.520245 -0.161968 0.076 Uiso 1 1 calc R . . . .
C2 C 0.4219(2) 0.38832(11) 0.6391(3) 0.0554(6) Uani 1 1 d . . . . .
C4 C 0.5542(2) 0.37238(11) 0.4236(4) 0.0593(6) Uani 1 1 d . . . . .
C11 C 0.0667(2) 0.56950(11) -0.1731(3) 0.0559(6) Uani 1 1 d . . . . .
C6 C 0.3626(3) 0.50793(12) 0.1106(4) 0.0639(7) Uani 1 1 d . . . . .
H6 H 0.434039 0.492297 0.089632 0.077 Uiso 1 1 calc R . . . .
C3 C 0.4915(2) 0.35291(11) 0.5539(4) 0.0662(7) Uani 1 1 d . . . . .
H3 H 0.496969 0.313250 0.585461 0.079 Uiso 1 1 calc R . . . .
C17 C 0.0683(3) 0.67100(13) -0.0501(4) 0.0739(8) Uani 1 1 d . . . . .
H17 H 0.152412 0.668231 -0.010139 0.089 Uiso 1 1 calc R . . . .
C13 C -0.1225(3) 0.62976(15) -0.2042(4) 0.0770(8) Uani 1 1 d . . . . .
H13 H -0.168327 0.599263 -0.269925 0.092 Uiso 1 1 calc R . . . .
C1 C 0.3572(3) 0.36048(13) 0.7779(4) 0.0706(7) Uani 1 1 d . . . . .
O3A O -0.0473(3) 0.56542(17) -0.4742(4) 0.0851(13) Uani 0.638(5) 1 d . . . A 1
H3A H -0.061319 0.543131 -0.564372 0.128 Uiso 0.638(5) 1 calc GR . . A 1
C15 C -0.1128(4) 0.72596(18) -0.0735(5) 0.0999(12) Uani 1 1 d . . . . .
H15 H -0.151852 0.760166 -0.050548 0.120 Uiso 1 1 calc R . . . .
C16 C 0.0104(4) 0.72174(16) -0.0143(5) 0.0944(11) Uani 1 1 d . . . . .
H16 H 0.055310 0.752775 0.049776 0.113 Uiso 1 1 calc R . . . .
C14 C -0.1793(3) 0.68053(18) -0.1660(5) 0.0980(11) Uani 1 1 d . . . . .
H14 H -0.263510 0.683641 -0.203725 0.118 Uiso 1 1 calc R . . . .
C5 C 0.6331(3) 0.32751(13) 0.3543(5) 0.0918(10) Uani 1 1 d D U . . .
O3B O 0.1013(6) 0.4833(3) -0.3216(9) 0.083(2) Uani 0.362(5) 1 d . . . A 2
H3B H 0.081876 0.468443 -0.425988 0.125 Uiso 0.362(5) 1 calc GR . . A 2
F4A F 0.5923(14) 0.3131(7) 0.1791(10) 0.210(9) Uani 0.475(16) 1 d D U . B 1
F6A F 0.7431(6) 0.3482(3) 0.3635(18) 0.130(5) Uani 0.475(16) 1 d D U . B 1
F5A F 0.6495(11) 0.2774(3) 0.4408(17) 0.135(5) Uani 0.475(16) 1 d D U . B 1
F6B F 0.6606(10) 0.3439(3) 0.2001(12) 0.137(4) Uani 0.525(16) 1 d D U . B 2
F4B F 0.5751(11) 0.2787(3) 0.3032(19) 0.167(6) Uani 0.525(16) 1 d D U . B 2
F5B F 0.7298(9) 0.3167(6) 0.4882(13) 0.208(8) Uani 0.525(16) 1 d D U . B 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 180.0 . 3_666
O1 Cu1 O2 86.97(7) . .
O1 Cu1 O2 86.97(7) 3_666 3_666
O1 Cu1 O2 93.03(7) 3_666 .
O1 Cu1 O2 93.03(7) . 3_666
O2 Cu1 O2 180.0 3_666 .
N1 Cu1 O1 89.80(8) 3_666 .
N1 Cu1 O1 90.20(8) . .
N1 Cu1 O1 89.80(8) . 3_666
N1 Cu1 O1 90.20(8) 3_666 3_666
N1 Cu1 O2 88.26(7) 3_666 .
N1 Cu1 O2 88.26(7) . 3_666
N1 Cu1 O2 91.74(7) . .
N1 Cu1 O2 91.74(7) 3_666 3_666
N1 Cu1 N1 180.0 . 3_666
C2 O1 Cu1 125.32(16) . .
C4 O2 Cu1 120.37(17) . .
C10 N1 Cu1 122.83(16) . .
C10 N1 C6 117.1(2) . .
C6 N1 Cu1 119.64(17) . .
C11 N2 O3A 114.7(2) . .
C11 N2 O3B 117.2(3) . .
C9 C8 C7 116.8(2) . .
C9 C8 C11 120.8(2) . .
C7 C8 C11 122.3(2) . .
N1 C10 C9 122.9(2) . .
C10 C9 C8 120.0(2) . .
C17 C12 C11 119.7(2) . .
C17 C12 C13 118.4(3) . .
C13 C12 C11 121.9(3) . .
C6 C7 C8 119.7(2) . .
O1 C2 C3 129.0(2) . .
O1 C2 C1 112.4(2) . .
C3 C2 C1 118.6(2) . .
O2 C4 C3 128.7(2) . .
O2 C4 C5 114.3(2) . .
C3 C4 C5 117.0(2) . .
N2 C11 C8 118.0(2) . .
N2 C11 C12 124.0(2) . .
C12 C11 C8 117.9(2) . .
N1 C6 C7 123.3(2) . .
C2 C3 C4 124.6(2) . .
C16 C17 C12 121.0(3) . .
C14 C13 C12 120.1(3) . .
F3 C1 C2 114.6(3) . .
F2 C1 F3 105.8(3) . .
F2 C1 C2 110.6(2) . .
F1 C1 F3 106.7(2) . .
F1 C1 F2 107.4(3) . .
F1 C1 C2 111.3(2) . .
C14 C15 C16 120.6(3) . .
C15 C16 C17 119.6(3) . .
C15 C14 C13 120.4(3) . .
F4A C5 C4 113.7(5) . .
F4A C5 F6A 104.3(8) . .
F6A C5 C4 111.5(4) . .
F5A C5 C4 116.8(4) . .
F5A C5 F4A 103.9(6) . .
F5A C5 F6A 105.4(6) . .
F6B C5 C4 112.4(4) . .
F6B C5 F5B 112.2(7) . .
F4B C5 C4 111.9(5) . .
F4B C5 F6B 101.7(5) . .
F4B C5 F5B 109.4(7) . .
F5B C5 C4 109.0(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 2.0410(17) .
Cu1 O1 2.0410(17) 3_666
Cu1 O2 2.2264(17) .
Cu1 O2 2.2264(17) 3_666
Cu1 N1 2.021(2) 3_666
Cu1 N1 2.021(2) .
O1 C2 1.258(3) .
O2 C4 1.240(3) .
N1 C10 1.334(3) .
N1 C6 1.335(3) .
F3 C1 1.320(3) .
N2 C11 1.277(3) .
N2 O3A 1.434(3) .
N2 O3B 1.442(6) .
F2 C1 1.311(3) .
F1 C1 1.300(3) .
C8 C9 1.383(3) .
C8 C7 1.387(3) .
C8 C11 1.488(3) .
C10 C9 1.380(3) .
C12 C11 1.482(4) .
C12 C17 1.384(4) .
C12 C13 1.388(4) .
C7 C6 1.375(4) .
C2 C3 1.378(4) .
C2 C1 1.530(4) .
C4 C3 1.395(4) .
C4 C5 1.523(4) .
C17 C16 1.384(4) .
C13 C14 1.383(5) .
C15 C16 1.363(5) .
C15 C14 1.361(5) .
C5 F4A 1.303(4) .
C5 F6A 1.320(4) .
C5 F5A 1.298(4) .
C5 F6B 1.301(4) .
C5 F4B 1.299(4) .
C5 F5B 1.310(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
O3A H3A N2 0.82 2.08 2.818(4) 149.2 3_564 yes
O3B H3B N2 0.82 2.04 2.771(6) 148.9 3_564 yes
