#------------------------------------------------------------------------------
#$Date: 2018-01-17 08:27:03 +0200 (Wed, 17 Jan 2018) $
#$Revision: 205311 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/09/2020915.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020915
loop_
_publ_author_name
'Perdih, Franc'
_publ_section_title
;
 Copper(II) bis(4,4,4-trifluoro-1-phenylbutane-1,3-dionate) complexes with
 pyridin-2-one, 3-hydroxypyridine and 3-hydroxypyridin-2-one ligands:
 molecular structures and hydrogen-bonded networks
;
_journal_coeditor_code           KU3208
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              960
_journal_page_last               967
_journal_paper_doi               10.1107/S2053229617014875
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '[Cu (C10 H6 F3 O2)2 (C5 H5 N O2)2]'
_chemical_formula_moiety         'C30 H22 Cu F6 N2 O8'
_chemical_formula_sum            'C30 H22 Cu F6 N2 O8'
_chemical_formula_weight         716.03
_chemical_name_systematic
Bis(3-hydroxypyridin-2-one-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ²O,O')copper(II)
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                108.710(2)
_cell_angle_beta                 101.727(2)
_cell_angle_gamma                93.650(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5950(3)
_cell_length_b                   9.6764(4)
_cell_length_c                   10.7507(4)
_cell_measurement_reflns_used    3204
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     725.61(5)
_computing_cell_refinement
;
DENZO-SMN (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
KappaCCD Reference Manual (Nonius, 1998)
;
_computing_data_reduction
;
DENZO-SMN (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare et al.,  1999)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.055
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5704
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         3.527
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SCALEPACK; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       block
_exptl_crystal_F_000             363
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0328
_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)+(0.0388P)²+0.3054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                2905
_reflns_number_total             3300
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ku3208sup1.cif
_cod_data_source_block           III
_cod_database_code               2020915
_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   0.816
_shelx_estimated_absorpt_t_max   0.920
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.5000 0.0000 0.0000 0.03159(11) Uani d 1 . .
F F1A 0.0866(12) -0.4652(6) -0.3582(8) 0.0752(17) Uani d 0.70(3) A 1
F F2A 0.2240(12) -0.3169(12) -0.4232(7) 0.081(2) Uani d 0.70(3) A 1
F F3A -0.0052(11) -0.2623(14) -0.3483(10) 0.082(2) Uani d 0.70(3) A 1
F F1B 0.044(4) -0.447(3) -0.3514(16) 0.099(6) Uani d 0.30(3) A 2
F F2B 0.240(3) -0.345(2) -0.4194(19) 0.080(5) Uani d 0.30(3) A 2
F F3B 0.027(4) -0.235(4) -0.359(2) 0.107(8) Uani d 0.30(3) A 2
O O1 0.49487(17) -0.15660(13) 0.07642(12) 0.0332(3) Uani d 1 . .
O O2 0.34867(18) -0.12645(14) -0.17153(12) 0.0349(3) Uani d 1 . .
O O3 0.23113(18) 0.05953(15) 0.10040(13) 0.0369(3) Uani d 1 . .
O O4 0.4467(2) 0.07809(19) 0.35085(14) 0.0486(4) Uani d 1 . .
H H4 0.4806 0.0951 0.2889 0.073 Uiso calc 1 . .
N N1 -0.0005(2) -0.07098(18) 0.13890(16) 0.0376(4) Uani d 1 . .
H H1 -0.0672 -0.0750 0.0626 0.045 Uiso calc 1 . .
C C1 0.1407(3) -0.3234(2) -0.3307(2) 0.0412(4) Uani d 1 . .
C C2 0.2618(2) -0.25088(19) -0.18802(17) 0.0323(4) Uani d 1 . .
C C3 0.2636(3) -0.3231(2) -0.09762(19) 0.0391(4) Uani d 1 . .
H H3 0.1823 -0.4088 -0.1226 0.047 Uiso calc 1 . .
C C4 0.3834(2) -0.27387(18) 0.03228(17) 0.0306(4) Uani d 1 . .
C C5 0.3844(3) -0.36172(19) 0.12376(19) 0.0335(4) Uani d 1 . .
C C6 0.4900(3) -0.3036(2) 0.2549(2) 0.0416(4) Uani d 1 . .
H H6 0.5594 -0.2115 0.2838 0.050 Uiso calc 1 . .
C C7 0.4934(4) -0.3812(3) 0.3432(2) 0.0543(6) Uani d 1 . .
H H7 0.5647 -0.3415 0.4310 0.065 Uiso calc 1 . .
C C8 0.3902(4) -0.5179(3) 0.3004(3) 0.0591(6) Uani d 1 . .
H H8 0.3925 -0.5705 0.3593 0.071 Uiso calc 1 . .
C C9 0.2853(4) -0.5760(3) 0.1720(3) 0.0614(7) Uani d 1 . .
H H9 0.2160 -0.6680 0.1441 0.074 Uiso calc 1 . .
C C10 0.2804(4) -0.4995(2) 0.0826(2) 0.0496(5) Uani d 1 . .
H H10 0.2078 -0.5400 -0.0048 0.059 Uiso calc 1 . .
C C11 0.1710(2) 0.00097(19) 0.17594(17) 0.0309(4) Uani d 1 . .
C C12 0.2756(3) 0.0047(2) 0.30454(18) 0.0355(4) Uani d 1 . .
C C13 0.2041(3) -0.0627(3) 0.3800(2) 0.0455(5) Uani d 1 . .
H H13 0.2740 -0.0601 0.4627 0.055 Uiso calc 1 . .
C C14 0.0255(3) -0.1360(3) 0.3337(2) 0.0527(6) Uani d 1 . .
H H14 -0.0234 -0.1830 0.3846 0.063 Uiso calc 1 . .
C C15 -0.0745(3) -0.1373(3) 0.2139(2) 0.0485(5) Uani d 1 . .
H H15 -0.1939 -0.1836 0.1828 0.058 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O3 2_655 . 97.30(5) yes
O1 Cu1 O3 . . 82.70(5) yes
O2 Cu1 O2 2_655 . 180.00(6) ?
O2 Cu1 O1 2_655 . 88.07(5) ?
O2 Cu1 O1 . . 91.93(5) yes
O2 Cu1 O1 2_655 2_655 91.93(5) ?
O2 Cu1 O1 . 2_655 88.07(5) yes
O2 Cu1 O3 . . 92.53(5) yes
O2 Cu1 O3 2_655 . 87.47(5) yes
O1 Cu1 O1 . 2_655 180.0 ?
C4 O1 Cu1 . . 127.16(11) ?
C2 O2 Cu1 . . 123.14(11) ?
C12 O4 H4 . . 109.5 ?
C11 N1 C15 . . 124.59(16) ?
C11 N1 H1 . . 117.7 ?
C15 N1 H1 . . 117.7 ?
F2A C1 F3A . . 107.4(7) ?
F1B C1 F2B . . 108.5(13) ?
F1B C1 F3B . . 106.5(14) ?
F2B C1 F3B . . 106.1(16) ?
F2A C1 F1A . . 105.9(5) ?
F3A C1 F1A . . 106.6(6) ?
F1B C1 C2 . . 115.2(7) ?
F2A C1 C2 . . 112.2(4) ?
F3A C1 C2 . . 112.1(5) ?
F2B C1 C2 . . 109.7(9) ?
F3B C1 C2 . . 110.3(9) ?
F1A C1 C2 . . 112.3(3) ?
O2 C2 C3 . . 129.03(16) ?
O2 C2 C1 . . 112.62(15) ?
C3 C2 C1 . . 118.35(16) ?
C2 C3 C4 . . 123.16(17) ?
C2 C3 H3 . . 118.4 ?
C4 C3 H3 . . 118.4 ?
O1 C4 C3 . . 122.91(16) ?
O1 C4 C5 . . 116.62(16) ?
C3 C4 C5 . . 120.47(16) ?
C6 C5 C10 . . 118.77(17) ?
C6 C5 C4 . . 119.01(16) ?
C10 C5 C4 . . 122.22(18) ?
C7 C6 C5 . . 120.7(2) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C8 C7 C6 . . 119.6(2) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C9 C8 C7 . . 120.2(2) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C10 . . 120.8(2) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C9 C10 C5 . . 119.9(2) ?
C9 C10 H10 . . 120.1 ?
C5 C10 H10 . . 120.1 ?
O3 C11 N1 . . 121.10(16) ?
O3 C11 C12 . . 123.72(17) ?
N1 C11 C12 . . 115.18(16) ?
O4 C12 C13 . . 120.18(17) ?
O4 C12 C11 . . 118.92(16) ?
C13 C12 C11 . . 120.89(18) ?
C12 C13 C14 . . 120.31(18) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.0(2) ?
C15 C14 H14 . . 120.5 ?
C13 C14 H14 . . 120.5 ?
C14 C15 N1 . . 120.0(2) ?
C14 C15 H15 . . 120.0 ?
N1 C15 H15 . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 2_655 1.9315(12) ?
Cu1 O1 . 1.9434(11) yes
Cu1 O2 . 1.9315(12) yes
Cu1 O1 2_655 1.9434(11) ?
Cu1 O3 . 2.5127(14) yes
F1A C1 . 1.325(5) ?
F2A C1 . 1.297(6) ?
F3A C1 . 1.297(10) ?
F1B C1 . 1.292(12) ?
F2B C1 . 1.308(15) ?
F3B C1 . 1.31(2) ?
O1 C4 . 1.264(2) ?
O2 C2 . 1.277(2) ?
O3 C11 . 1.266(2) ?
O4 C12 . 1.355(2) ?
O4 H4 . 0.8200 ?
N1 C11 . 1.355(2) ?
N1 C15 . 1.360(2) ?
N1 H1 . 0.8600 ?
C1 C2 . 1.531(2) ?
C2 C3 . 1.366(2) ?
C3 C4 . 1.416(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.491(2) ?
C5 C6 . 1.386(3) ?
C5 C10 . 1.394(3) ?
C6 C7 . 1.385(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.381(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.361(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.385(3) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.436(2) ?
C12 C13 . 1.361(3) ?
C13 C14 . 1.403(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.351(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4 O2 2_655 0.82 2.06 2.8380(19) 159.5
O4 H4 O3 . 0.82 2.39 2.7970(18) 111.3
N1 H1 O3 2 0.86 1.99 2.842(2) 172.5
C15 H15 O1 1_455 0.93 2.48 3.271(2) 143.4
C9 H9 O3 1_545 0.93 2.54 3.338(3) 144
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Cu1 O2 C2 C3 -4.2(3)
Cu1 O2 C2 C1 175.55(12)
F1B C1 C2 O2 -177.4(18)
F2A C1 C2 O2 45.2(7)
F3A C1 C2 O2 -75.7(6)
F2B C1 C2 O2 59.8(12)
F3B C1 C2 O2 -57(2)
F1A C1 C2 O2 164.4(5)
F1B C1 C2 C3 2.4(18)
F2A C1 C2 C3 -134.9(6)
F3A C1 C2 C3 104.1(6)
F2B C1 C2 C3 -120.4(12)
F3B C1 C2 C3 123(2)
F1A C1 C2 C3 -15.8(5)
O2 C2 C3 C4 -6.7(4)
C1 C2 C3 C4 173.51(18)
Cu1 O1 C4 C3 13.0(3)
Cu1 O1 C4 C5 -167.84(12)
C2 C3 C4 O1 2.0(3)
C2 C3 C4 C5 -177.11(18)
O1 C4 C5 C6 7.1(3)
C3 C4 C5 C6 -173.70(18)
O1 C4 C5 C10 -173.96(18)
C3 C4 C5 C10 5.3(3)
C10 C5 C6 C7 0.4(3)
C4 C5 C6 C7 179.44(19)
C5 C6 C7 C8 -0.1(4)
C6 C7 C8 C9 -0.2(4)
C7 C8 C9 C10 0.1(4)
C8 C9 C10 C5 0.2(4)
C6 C5 C10 C9 -0.5(3)
C4 C5 C10 C9 -179.5(2)
C15 N1 C11 O3 179.61(19)
C15 N1 C11 C12 -0.3(3)
O3 C11 C12 O4 1.9(3)
N1 C11 C12 O4 -178.15(17)
O3 C11 C12 C13 -178.84(19)
N1 C11 C12 C13 1.1(3)
O4 C12 C13 C14 178.6(2)
C11 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 -0.6(4)
C13 C14 C15 N1 1.4(4)
C11 N1 C15 C14 -0.9(4)

_cod_database_fobs_code 2020915
