#------------------------------------------------------------------------------
#$Date: 2017-07-05 04:58:34 +0300 (Wed, 05 Jul 2017) $
#$Revision: 198446 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/86/7228633.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_7228633
loop_
_publ_author_name
'Valdes-Martinez, Jesus'
'Martínez-Vargas, Sergio'
'Dorazco-Gonzalez, Alejandro'
'Barquera-Lozada, Jose Enrique'
'Ortega, Simon Hernandez'
'Toscano, Ruben Alfredo'
_publ_section_title
;
 Interaction Between Aromatic Rings as Organizing Tools and
 Semicoordination in Cu(II) Compounds.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00871F
_journal_year                    2017
_chemical_formula_moiety         'C46 H22 Cu2 F8 N6 O8, 6(H2 O)'
_chemical_formula_sum            'C46 H34 Cu2 F8 N6 O14'
_chemical_formula_weight         1173.87
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-26 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                107.106(2)
_cell_angle_beta                 100.958(2)
_cell_angle_gamma                96.022(2)
_cell_formula_units_Z            1
_cell_length_a                   9.6850(10)
_cell_length_b                   10.5570(10)
_cell_length_c                   12.3960(10)
_cell_measurement_reflns_used    6095
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.17
_cell_volume                     1171.67(19)
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13175
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.426
_diffrn_reflns_theta_min         1.767
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.8677
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       prism
_exptl_crystal_F_000             594
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0409
_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)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3355
_reflns_number_total             4281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00871f2.cif
_cod_data_source_block           Compound_2
_cod_database_code               7228633
_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.
;
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 0.16818(3) -0.03740(3) 0.77400(3) 0.04241(13) Uani 1 1 d . . . . .
F1 F 0.23931(17) 0.12249(16) 0.52502(13) 0.0558(4) Uani 1 1 d . . . . .
F2 F -0.0808(2) 0.42493(19) 0.57023(16) 0.0722(5) Uani 1 1 d . . . . .
F3 F 0.0443(3) 0.53018(19) 0.79891(17) 0.0905(7) Uani 1 1 d . . . . .
F4 F 0.2623(2) 0.42644(18) 0.89240(14) 0.0773(6) Uani 1 1 d . . . . .
O1 O 0.3541(2) 0.1011(2) 0.77215(18) 0.0589(5) Uani 1 1 d . . . . .
O2 O 0.5015(2) 0.2817(3) 0.7849(2) 0.0921(9) Uani 1 1 d . . . . .
O3 O 0.0974(2) -0.11485(19) 0.60816(15) 0.0483(5) Uani 1 1 d . . . . .
O4 O -0.0549(2) -0.2492(2) 0.65515(16) 0.0632(6) Uani 1 1 d . . . . .
N1 N 0.0288(2) 0.0928(2) 0.8064(2) 0.0471(6) Uani 1 1 d . . . . .
C2 C 0.0447(3) 0.1590(3) 0.9207(3) 0.0541(8) Uani 1 1 d . . . . .
C3 C -0.0387(4) 0.2566(3) 0.9561(3) 0.0730(10) Uani 1 1 d . . . . .
H3 H -0.0256 0.3040 1.0345 0.088 Uiso 1 1 calc R U . . .
C4 C -0.1389(4) 0.2825(4) 0.8763(4) 0.0833(12) Uani 1 1 d . . . . .
H4 H -0.1950 0.3471 0.8998 0.100 Uiso 1 1 calc R U . . .
C5 C -0.1565(4) 0.2130(3) 0.7616(4) 0.0704(9) Uani 1 1 d . . . . .
H5 H -0.2255 0.2285 0.7058 0.084 Uiso 1 1 calc R U . . .
C6 C -0.0704(3) 0.1197(3) 0.7298(3) 0.0549(8) Uani 1 1 d . . . . .
H6 H -0.0819 0.0732 0.6514 0.066 Uiso 1 1 calc R U . . .
N7 N 0.2101(2) 0.0152(2) 0.94157(19) 0.0468(6) Uani 1 1 d . . . . .
C8 C 0.1491(3) 0.1155(3) 0.9983(2) 0.0531(8) Uani 1 1 d . . . . .
C9 C 0.1855(4) 0.1609(4) 1.1194(3) 0.0664(9) Uani 1 1 d . . . . .
H9 H 0.1455 0.2301 1.1611 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2816(4) 0.1010(4) 1.1756(3) 0.0741(11) Uani 1 1 d . . . . .
H10 H 0.3073 0.1313 1.2562 0.089 Uiso 1 1 calc R U . . .
C11 C 0.3409(4) -0.0029(4) 1.1155(3) 0.0645(9) Uani 1 1 d . . . . .
H11 H 0.4056 -0.0431 1.1543 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3006(3) -0.0456(3) 0.9951(2) 0.0486(7) Uani 1 1 d . . . . .
N13 N 0.2941(2) -0.1729(2) 0.80065(19) 0.0446(6) Uani 1 1 d . . . . .
C14 C 0.3461(3) -0.1567(3) 0.9141(3) 0.0486(7) Uani 1 1 d . . . . .
C15 C 0.4320(3) -0.2421(3) 0.9481(3) 0.0622(9) Uani 1 1 d . . . . .
H15 H 0.4664 -0.2304 1.0263 0.075 Uiso 1 1 calc R U . . .
C16 C 0.4653(3) -0.3435(4) 0.8645(3) 0.0680(9) Uani 1 1 d . . . . .
H16 H 0.5228 -0.4016 0.8855 0.082 Uiso 1 1 calc R U . . .
C17 C 0.4134(3) -0.3593(3) 0.7496(3) 0.0626(8) Uani 1 1 d . . . . .
H17 H 0.4358 -0.4276 0.6919 0.075 Uiso 1 1 calc R U . . .
C18 C 0.3276(3) -0.2722(3) 0.7210(3) 0.0531(7) Uani 1 1 d . . . . .
H18 H 0.2919 -0.2835 0.6431 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2583(3) 0.2717(3) 0.7103(2) 0.0441(7) Uani 1 1 d . . . . .
C20 C 0.1907(3) 0.2238(3) 0.5939(2) 0.0405(6) Uani 1 1 d . . . . .
C21 C 0.0772(3) 0.2710(3) 0.5432(2) 0.0389(6) Uani 1 1 d . . . . .
C22 C 0.0306(3) 0.3754(3) 0.6142(2) 0.0492(7) Uani 1 1 d . . . . .
C23 C 0.0931(4) 0.4283(3) 0.7304(3) 0.0567(8) Uani 1 1 d . . . . .
C24 C 0.2044(3) 0.3758(3) 0.7765(2) 0.0527(8) Uani 1 1 d . . . . .
C25 C 0.3822(3) 0.2140(3) 0.7608(2) 0.0516(7) Uani 1 1 d . . . . .
C26 C -0.0077(3) -0.2093(3) 0.5843(2) 0.0415(6) Uani 1 1 d . . . . .
O5 O 0.6676(6) 0.5907(7) 0.5726(5) 0.118(2) Uani 0.810(4) 1 d . U P A 1
H5A H 0.7563 0.6046 0.5748 0.177 Uiso 0.810(4) 1 d R U P A 1
H5B H 0.6005 0.6140 0.5316 0.177 Uiso 0.810(4) 1 d R U P A 1
O6 O 0.5501(4) 0.3318(3) 0.5623(3) 0.1113(15) Uani 0.810(4) 1 d . . P A 1
H6A H 0.5307 0.3185 0.6225 0.167 Uiso 0.810(4) 1 d R U P A 1
H6B H 0.5865 0.4099 0.5650 0.167 Uiso 0.810(4) 1 d R U P A 1
O7 O 0.4891(6) 0.9354(5) 0.5827(4) 0.1349(19) Uani 0.810(4) 1 d . U P A 1
H7A H 0.4482 0.9778 0.6337 0.202 Uiso 0.810(4) 1 d R U P A 1
H7B H 0.4790 0.8542 0.5396 0.202 Uiso 0.810(4) 1 d R U P A 1
O5B O 0.699(3) 0.584(3) 0.628(3) 0.112(6) Uani 0.190(4) 1 d . U P A 2
H5C H 0.7854 0.5761 0.6501 0.168 Uiso 0.190(4) 1 d R U P A 2
H5D H 0.6793 0.5638 0.5550 0.168 Uiso 0.190(4) 1 d R U P A 2
O6B O 0.7009(12) 0.4911(12) 0.7971(12) 0.082(5) Uani 0.190(4) 1 d . . P A 2
H6C H 0.6323 0.4277 0.7852 0.123 Uiso 0.190(4) 1 d R U P A 2
H6D H 0.6976 0.5214 0.7405 0.123 Uiso 0.190(4) 1 d R U P A 2
O7B O 0.364(2) 0.8784(16) 0.4986(15) 0.106(4) Uani 0.190(4) 1 d . U P A 2
H7C H 0.2919 0.8862 0.5287 0.159 Uiso 0.190(4) 1 d R U P A 2
H7D H 0.4291 0.9385 0.4981 0.159 Uiso 0.190(4) 1 d R U P 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'
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'
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_3
O3 Cu1 N7 168.98(8) .
O3 Cu1 N13 98.94(9) .
N7 Cu1 N13 79.89(10) .
O3 Cu1 N1 98.62(9) .
N7 Cu1 N1 80.27(10) .
N13 Cu1 N1 157.79(9) .
O3 Cu1 O1 97.34(8) .
N7 Cu1 O1 93.64(8) .
N13 Cu1 O1 91.02(8) .
N1 Cu1 O1 100.12(8) .
O3 Cu1 O4 52.57(7) .
N7 Cu1 O4 116.41(8) .
N13 Cu1 O4 88.84(8) .
N1 Cu1 O4 91.09(8) .
O1 Cu1 O4 149.39(7) .
C25 O1 Cu1 139.3(2) .
C26 O3 Cu1 110.31(16) .
C26 O4 Cu1 71.73(16) .
C6 N1 C2 118.7(3) .
C6 N1 Cu1 127.9(2) .
C2 N1 Cu1 113.4(2) .
N1 C2 C3 120.0(3) .
N1 C2 C8 114.6(3) .
C3 C2 C8 125.4(3) .
C4 C3 C2 120.2(4) .
C4 C3 H3 119.9 .
C2 C3 H3 119.9 .
C3 C4 C5 119.4(4) .
C3 C4 H4 120.3 .
C5 C4 H4 120.3 .
C4 C5 C6 118.8(4) .
C4 C5 H5 120.6 .
C6 C5 H5 120.6 .
N1 C6 C5 122.9(3) .
N1 C6 H6 118.5 .
C5 C6 H6 118.5 .
C12 N7 C8 123.3(3) .
C12 N7 Cu1 118.8(2) .
C8 N7 Cu1 117.8(2) .
N7 C8 C9 118.6(3) .
N7 C8 C2 113.2(3) .
C9 C8 C2 128.1(3) .
C10 C9 C8 118.5(3) .
C10 C9 H9 120.7 .
C8 C9 H9 120.7 .
C9 C10 C11 121.8(3) .
C9 C10 H10 119.1 .
C11 C10 H10 119.1 .
C10 C11 C12 117.7(3) .
C10 C11 H11 121.2 .
C12 C11 H11 121.2 .
N7 C12 C11 120.0(3) .
N7 C12 C14 112.9(2) .
C11 C12 C14 127.0(3) .
C18 N13 C14 118.7(3) .
C18 N13 Cu1 127.60(19) .
C14 N13 Cu1 113.7(2) .
N13 C14 C15 121.4(3) .
N13 C14 C12 114.4(3) .
C15 C14 C12 124.2(3) .
C16 C15 C14 118.9(3) .
C16 C15 H15 120.6 .
C14 C15 H15 120.6 .
C15 C16 C17 119.8(3) .
C15 C16 H16 120.1 .
C17 C16 H16 120.1 .
C16 C17 C18 118.8(3) .
C16 C17 H17 120.6 .
C18 C17 H17 120.6 .
N13 C18 C17 122.5(3) .
N13 C18 H18 118.8 .
C17 C18 H18 118.8 .
C24 C19 C20 114.9(3) .
C24 C19 C25 122.8(3) .
C20 C19 C25 122.3(3) .
F1 C20 C21 117.5(2) .
F1 C20 C19 117.4(2) .
C21 C20 C19 125.0(3) .
C22 C21 C20 116.7(2) .
C22 C21 C26 122.2(2) 2_556
C20 C21 C26 121.1(2) 2_556
F2 C22 C23 119.0(3) .
F2 C22 C21 119.6(3) .
C23 C22 C21 121.4(3) .
F3 C23 C22 120.3(3) .
F3 C23 C24 120.4(3) .
C22 C23 C24 119.3(3) .
F4 C24 C23 118.6(3) .
F4 C24 C19 118.7(3) .
C23 C24 C19 122.7(3) .
O2 C25 O1 126.0(3) .
O2 C25 C19 116.8(3) .
O1 C25 C19 117.2(2) .
O4 C26 O3 125.4(2) .
O4 C26 C21 120.0(2) 2_556
O3 C26 C21 114.6(2) 2_556
H5A O5 H5B 127.7 .
H6A O6 H6B 120.3 .
H7A O7 H7B 135.1 .
H5C O5B H5D 107.7 .
H6C O6B H6D 113.1 .
H7C O7B H7D 130.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.9293(18) .
Cu1 N7 1.934(2) .
Cu1 N13 2.034(2) .
Cu1 N1 2.036(2) .
Cu1 O1 2.206(2) .
Cu1 O4 2.771(2) .
F1 C20 1.348(3) .
F2 C22 1.340(3) .
F3 C23 1.350(3) .
F4 C24 1.358(3) .
O1 C25 1.249(3) .
O2 C25 1.227(3) .
O3 C26 1.272(3) .
O4 C26 1.219(3) .
N1 C6 1.331(4) .
N1 C2 1.353(4) .
C2 C3 1.397(4) .
C2 C8 1.465(4) .
C3 C4 1.358(5) .
C3 H3 0.9300 .
C4 C5 1.363(5) .
C4 H4 0.9300 .
C5 C6 1.375(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
N7 C12 1.329(4) .
N7 C8 1.348(4) .
C8 C9 1.395(4) .
C9 C10 1.374(5) .
C9 H9 0.9300 .
C10 C11 1.379(5) .
C10 H10 0.9300 .
C11 C12 1.389(4) .
C11 H11 0.9300 .
C12 C14 1.471(4) .
N13 C18 1.328(4) .
N13 C14 1.353(3) .
C14 C15 1.389(4) .
C15 C16 1.368(5) .
C15 H15 0.9300 .
C16 C17 1.371(5) .
C16 H16 0.9300 .
C17 C18 1.379(4) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 C24 1.380(4) .
C19 C20 1.381(4) .
C19 C25 1.515(4) .
C20 C21 1.374(4) .
C21 C22 1.371(4) .
C21 C26 1.507(4) 2_556
C22 C23 1.370(4) .
C23 C24 1.370(4) .
C26 C21 1.507(4) 2_556
O5 H5A 0.8500 .
O5 H5B 0.8502 .
O6 H6A 0.8501 .
O6 H6B 0.8502 .
O7 H7A 0.8500 .
O7 H7B 0.8501 .
O5B H5C 0.8500 .
O5B H5D 0.8500 .
O6B H6C 0.8500 .
O6B H6D 0.8496 .
O7B H7C 0.8500 .
O7B H7D 0.8502 .
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
O5 H5A O4 0.85 2.13 2.848(6) 142.2 1_665
O5 H5A F2 0.85 2.59 3.145(7) 124.4 1_655
O5 H5B O6 0.85 1.93 2.782(7) 179.2 2_666
O6 H6A O2 0.85 2.22 3.068(5) 174.6 .
O6 H6B O5 0.85 1.95 2.805(7) 178.9 .
O7 H7A O1 0.85 2.24 3.085(4) 175.9 1_565
O7 H7B O6 0.85 1.95 2.805(6) 178.2 2_666
O5B H5C O4 0.85 2.26 2.72(3) 114.1 1_665
O5B H5C F2 0.85 2.28 2.92(3) 131.9 1_655
O6B H6C O2 0.85 1.89 2.726(12) 168.7 .
O6B H6D O5B 0.85 1.71 2.55(3) 177.5 .
O7B H7C O3 0.85 2.29 3.133(17) 174.3 1_565
O7B H7D O7B 0.85 2.62 3.47(4) 178.3 2_676
