#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:02:12 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179359 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/56/4325651.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_4325651
loop_
_publ_author_name
'Galina V. Romanenko'
'Ksenia Yu. Maryunina'
'Artem S. Bogomyakov'
'Renad Z. Sagdeev'
'Victor I. Ovcharenko'
_publ_section_title
;
 Relationship between the Thermally Induced Reorientations of Aromatic
 Solvate Molecules in Cu(hfac)2- Nitroxide Breathing Crystals and the
 Character of the Magnetic Anomaly
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6597
_journal_page_last               6609
_journal_paper_doi               10.1021/ic200444e
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C28 H27 Cu F15 N4 O6'
_chemical_formula_weight         864.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.726(8)
_cell_angle_beta                 108.913(7)
_cell_angle_gamma                99.893(8)
_cell_formula_units_Z            2
_cell_length_a                   10.5673(10)
_cell_length_b                   13.1006(13)
_cell_length_c                   13.4701(13)
_cell_measurement_reflns_used    2007
_cell_measurement_temperature    40(2)
_cell_measurement_theta_max      21.68
_cell_measurement_theta_min      2.55
_cell_volume                     1694.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      40(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.1758
_diffrn_reflns_av_sigmaI/netI    0.2471
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26847
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.4869
_exptl_absorpt_correction_T_min  0.3763
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       bulk
_exptl_crystal_F_000             870
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         8262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.802
_refine_ls_R_factor_all          0.1844
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                2921
_reflns_number_total             8262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic200444e_si_002_56.cif
_cod_data_source_block           f3f3f040
_cod_database_code               4325651
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.0000 0.0000 0.0000 0.0340(3) Uani 1 2 d S
O1 O 0.1518(4) 0.1324(3) 0.0355(3) 0.0451(10) Uani 1 1 d .
C1 C 0.3284(6) 0.2562(5) 0.0255(5) 0.0454(15) Uani 1 1 d .
F1 F 0.255(2) 0.3109(16) -0.0472(14) 0.078(5) Uani 0.50 1 d P
F2 F 0.3533(19) 0.3171(15) 0.1203(16) 0.099(7) Uani 0.50 1 d P
F3 F 0.4370(3) 0.2700(2) -0.0058(3) 0.0559(9) Uani 1 1 d .
F2A F 0.3989(17) 0.2872(12) 0.1328(13) 0.053(4) Uani 0.50 1 d P
F1A F 0.247(2) 0.3176(12) -0.0043(14) 0.055(4) Uani 0.50 1 d P
C2 C 0.2505(6) 0.1421(4) 0.0022(4) 0.0415(14) Uani 1 1 d .
C3 C 0.2932(6) 0.0628(4) -0.0527(4) 0.0409(14) Uani 1 1 d .
H3A H 0.3691 0.0821 -0.0747 0.049 Uiso 1 1 calc R
C4 C 0.2255(6) -0.0436(5) -0.0752(4) 0.0421(14) Uani 1 1 d .
C5 C 0.2768(6) -0.1227(4) -0.1410(5) 0.0462(15) Uani 1 1 d .
F4 F 0.1748(3) -0.1724(2) -0.2338(2) 0.0543(9) Uani 1 1 d .
F5 F 0.3115(4) -0.1983(3) -0.0882(3) 0.0676(10) Uani 1 1 d .
F6 F 0.3845(4) -0.0798(3) -0.1644(3) 0.0755(11) Uani 1 1 d .
O2 O 0.1295(4) -0.0855(3) -0.0506(3) 0.0441(10) Uani 1 1 d .
Cu2 Cu 0.5000 0.5000 0.5000 0.0347(3) Uani 1 2 d S
O3 O 0.5106(3) 0.4430(2) 0.6294(3) 0.0357(9) Uani 1 1 d .
C6 C 0.4880(6) 0.4288(5) 0.7941(4) 0.0403(14) Uani 1 1 d .
F7 F 0.6229(3) 0.4370(3) 0.8360(2) 0.0539(9) Uani 1 1 d .
F8 F 0.4250(3) 0.3255(2) 0.7758(2) 0.0486(8) Uani 1 1 d .
F9 F 0.4540(3) 0.4811(2) 0.8719(2) 0.0486(8) Uani 1 1 d .
C7 C 0.4453(5) 0.4693(4) 0.6908(4) 0.0334(13) Uani 1 1 d .
C8 C 0.3458(5) 0.5265(4) 0.6730(4) 0.0322(12) Uani 1 1 d .
H8A H 0.3070 0.5409 0.7266 0.039 Uiso 1 1 calc R
C9 C 0.2993(5) 0.5642(4) 0.5796(4) 0.0294(12) Uani 1 1 d .
C10 C 0.1876(5) 0.6247(4) 0.5634(4) 0.0360(13) Uani 1 1 d .
F10 F 0.1298(3) 0.6230(2) 0.6394(2) 0.0424(8) Uani 1 1 d .
F11 F 0.2376(3) 0.7279(2) 0.5694(2) 0.0439(8) Uani 1 1 d .
F12 F 0.0867(3) 0.5855(2) 0.4680(2) 0.0449(8) Uani 1 1 d .
O4 O 0.3444(3) 0.5573(2) 0.5034(3) 0.0328(8) Uani 1 1 d .
O01 O 0.0592(4) -0.0150(3) 0.1578(3) 0.0398(9) Uani 1 1 d .
N1 N 0.1793(5) -0.0305(3) 0.2104(3) 0.0363(11) Uani 1 1 d .
C01 C 0.2001(6) -0.1375(4) 0.2307(4) 0.0392(14) Uani 1 1 d .
C02 C 0.1254(5) -0.2235(4) 0.1253(4) 0.0429(14) Uani 1 1 d .
H02A H 0.0257 -0.2312 0.1040 0.064 Uiso 1 1 calc R
H02B H 0.1475 -0.2915 0.1368 0.064 Uiso 1 1 calc R
H02C H 0.1555 -0.2025 0.0683 0.064 Uiso 1 1 calc R
C03 C 0.1332(6) -0.1593(4) 0.3120(4) 0.0536(16) Uani 1 1 d .
H03A H 0.1795 -0.1045 0.3787 0.080 Uiso 1 1 calc R
H03B H 0.1412 -0.2292 0.3272 0.080 Uiso 1 1 calc R
H03C H 0.0357 -0.1582 0.2826 0.080 Uiso 1 1 calc R
C04 C 0.3571(5) -0.1166(4) 0.2741(4) 0.0338(13) Uani 1 1 d .
C05 C 0.4192(5) -0.1301(4) 0.1860(4) 0.0375(13) Uani 1 1 d .
H05A H 0.5197 -0.1153 0.2193 0.056 Uiso 1 1 calc R
H05B H 0.3939 -0.0805 0.1395 0.056 Uiso 1 1 calc R
H05C H 0.3838 -0.2031 0.1429 0.056 Uiso 1 1 calc R
C06 C 0.4182(6) -0.1733(4) 0.3608(4) 0.0483(16) Uani 1 1 d .
H06A H 0.5188 -0.1545 0.3834 0.073 Uiso 1 1 calc R
H06B H 0.3841 -0.2502 0.3328 0.073 Uiso 1 1 calc R
H06C H 0.3915 -0.1519 0.4226 0.073 Uiso 1 1 calc R
N2 N 0.3934(5) 0.0009(3) 0.3196(3) 0.0360(11) Uani 1 1 d .
O02 O 0.5136(4) 0.0520(3) 0.3833(3) 0.0446(10) Uani 1 1 d .
C07 C 0.2878(6) 0.0470(4) 0.2765(4) 0.0341(13) Uani 1 1 d .
C08 C 0.2914(5) 0.1583(4) 0.2992(4) 0.0307(12) Uani 1 1 d .
C09 C 0.4019(5) 0.2420(4) 0.3718(4) 0.0315(12) Uani 1 1 d .
H09A H 0.4895 0.2331 0.4130 0.038 Uiso 1 1 calc R
N3 N 0.3658(4) 0.3351(3) 0.3741(3) 0.0327(10) Uani 1 1 d .
N4 N 0.2349(4) 0.3114(3) 0.3055(3) 0.0332(10) Uani 1 1 d .
C041 C 0.1602(5) 0.3973(4) 0.2890(4) 0.0332(12) Uani 1 1 d .
H04A H 0.2278 0.4642 0.2995 0.040 Uiso 1 1 calc R
H04B H 0.1191 0.4076 0.3451 0.040 Uiso 1 1 calc R
C042 C 0.0490(5) 0.3782(4) 0.1813(4) 0.0393(14) Uani 1 1 d .
H04C H -0.0224 0.3137 0.1710 0.047 Uiso 1 1 calc R
H04D H 0.0879 0.3665 0.1240 0.047 Uiso 1 1 calc R
C043 C -0.0159(5) 0.4739(4) 0.1733(4) 0.0418(14) Uani 1 1 d .
H04E H -0.0454 0.4892 0.2355 0.050 Uiso 1 1 calc R
H04F H 0.0552 0.5366 0.1784 0.050 Uiso 1 1 calc R
C044 C -0.1384(6) 0.4591(4) 0.0707(4) 0.0573(17) Uani 1 1 d .
H04G H -0.1742 0.5233 0.0718 0.086 Uiso 1 1 calc R
H04H H -0.2104 0.3982 0.0655 0.086 Uiso 1 1 calc R
H04I H -0.1098 0.4461 0.0085 0.086 Uiso 1 1 calc R
C010 C 0.1848(5) 0.2070(4) 0.2600(4) 0.0330(13) Uani 1 1 d .
H01A H 0.0944 0.1735 0.2108 0.040 Uiso 1 1 calc R
C1S C 0.1281(6) 0.2208(4) 0.5339(4) 0.0365(13) Uani 1 1 d .
F1S F 0.0693(3) 0.2668(2) 0.4553(2) 0.0450(8) Uani 1 1 d .
F2S F 0.1237(3) 0.2760(2) 0.6252(2) 0.0476(8) Uani 1 1 d .
F3S F 0.2629(3) 0.2367(2) 0.5477(2) 0.0475(8) Uani 1 1 d .
C2S C 0.0614(5) 0.1049(4) 0.5143(4) 0.0325(12) Uani 1 1 d .
C3S C -0.0708(5) 0.0655(4) 0.4459(4) 0.0384(13) Uani 1 1 d .
H3SA H -0.1194 0.1104 0.4074 0.046 Uiso 1 1 calc R
C4S C -0.1346(5) -0.0388(4) 0.4319(4) 0.0377(13) Uani 1 1 d .
H4SA H -0.2282 -0.0657 0.3858 0.057 Uiso 1 1 calc R
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_1
_geom_angle_site_symmetry_3
O1 Cu1 O1 180.00(15) 2 .
O1 Cu1 O01 92.75(13) 2 2
O1 Cu1 O01 87.25(13) . 2
O1 Cu1 O01 87.25(13) 2 .
O1 Cu1 O01 92.75(13) . .
O01 Cu1 O01 180.00(18) 2 .
O1 Cu1 O2 93.07(14) 2 .
O1 Cu1 O2 86.93(14) . .
O01 Cu1 O2 81.17(13) 2 .
O01 Cu1 O2 98.83(13) . .
O1 Cu1 O2 86.93(14) 2 2
O1 Cu1 O2 93.07(14) . 2
O01 Cu1 O2 98.83(13) 2 2
O01 Cu1 O2 81.17(13) . 2
O2 Cu1 O2 180.0 . 2
C2 O1 Cu1 126.4(3) . .
F1A C1 F2 80.9(11) . .
F1A C1 F3 114.1(8) . .
F2 C1 F3 112.7(10) . .
F1A C1 F2A 109.8(10) . .
F2 C1 F2A 29.0(9) . .
F3 C1 F2A 97.5(8) . .
F1A C1 F1 25.4(9) . .
F2 C1 F1 103.2(11) . .
F3 C1 F1 93.9(8) . .
F2A C1 F1 130.5(10) . .
F1A C1 C2 111.9(10) . .
F2 C1 C2 118.0(11) . .
F3 C1 C2 114.8(5) . .
F2A C1 C2 107.6(8) . .
F1 C1 C2 110.7(9) . .
F1A F1 C1 66(4) . .
F2A F2 C1 78(3) . .
F2A F2 F1A 127(3) . .
C1 F2 F1A 48.7(9) . .
F2 F2A C1 73(3) . .
F1 F1A C1 89(4) . .
F1 F1A F2 131(5) . .
C1 F1A F2 50.4(10) . .
O1 C2 C3 128.8(5) . .
O1 C2 C1 112.7(5) . .
C3 C2 C1 118.5(5) . .
C4 C3 C2 120.7(5) . .
O2 C4 C3 129.9(5) . .
O2 C4 C5 114.1(5) . .
C3 C4 C5 116.0(5) . .
F6 C5 F4 107.7(5) . .
F6 C5 F5 107.5(5) . .
F4 C5 F5 106.3(4) . .
F6 C5 C4 115.2(5) . .
F4 C5 C4 109.7(5) . .
F5 C5 C4 110.1(5) . .
C4 O2 Cu1 123.4(4) . .
O4 Cu2 O4 179.999(2) 2_666 .
O4 Cu2 O3 92.37(13) 2_666 2_666
O4 Cu2 O3 87.63(13) . 2_666
O4 Cu2 O3 87.63(13) 2_666 .
O4 Cu2 O3 92.37(13) . .
O3 Cu2 O3 179.999(1) 2_666 .
O4 Cu2 N3 84.23(13) 2_666 .
O4 Cu2 N3 95.78(13) . .
O3 Cu2 N3 85.19(13) 2_666 .
O3 Cu2 N3 94.81(13) . .
O4 Cu2 N3 95.77(13) 2_666 2_666
O4 Cu2 N3 84.23(13) . 2_666
O3 Cu2 N3 94.81(13) 2_666 2_666
O3 Cu2 N3 85.19(13) . 2_666
N3 Cu2 N3 180.00(14) . 2_666
C7 O3 Cu2 122.9(3) . .
F7 C6 F9 106.3(4) . .
F7 C6 F8 107.3(4) . .
F9 C6 F8 106.5(4) . .
F7 C6 C7 113.0(4) . .
F9 C6 C7 112.9(4) . .
F8 C6 C7 110.5(4) . .
O3 C7 C8 127.9(5) . .
O3 C7 C6 112.6(4) . .
C8 C7 C6 119.4(5) . .
C7 C8 C9 122.8(5) . .
O4 C9 C8 126.9(5) . .
O4 C9 C10 112.6(4) . .
C8 C9 C10 120.5(4) . .
F12 C10 F11 107.9(4) . .
F12 C10 F10 107.3(4) . .
F11 C10 F10 105.9(4) . .
F12 C10 C9 111.7(4) . .
F11 C10 C9 111.3(4) . .
F10 C10 C9 112.5(4) . .
C9 O4 Cu2 125.6(3) . .
N1 O01 Cu1 123.1(3) . .
O01 N1 C07 124.3(4) . .
O01 N1 C01 122.8(4) . .
C07 N1 C01 110.4(4) . .
N1 C01 C03 105.6(4) . .
N1 C01 C04 101.4(4) . .
C03 C01 C04 114.7(4) . .
N1 C01 C02 109.7(4) . .
C03 C01 C02 109.1(4) . .
C04 C01 C02 115.5(4) . .
N2 C04 C06 110.1(4) . .
N2 C04 C01 99.9(4) . .
C06 C04 C01 115.7(4) . .
N2 C04 C05 105.1(4) . .
C06 C04 C05 111.1(4) . .
C01 C04 C05 113.8(4) . .
O02 N2 C07 124.5(4) . .
O02 N2 C04 123.0(4) . .
C07 N2 C04 112.2(4) . .
N1 C07 N2 107.9(4) . .
N1 C07 C08 126.0(5) . .
N2 C07 C08 126.1(5) . .
C010 C08 C09 104.6(4) . .
C010 C08 C07 127.5(5) . .
C09 C08 C07 127.8(5) . .
N3 C09 C08 110.7(4) . .
C09 N3 N4 104.9(4) . .
C09 N3 Cu2 125.2(3) . .
N4 N3 Cu2 129.1(3) . .
N3 N4 C010 113.4(4) . .
N3 N4 C041 119.6(4) . .
C010 N4 C041 127.1(4) . .
N4 C041 C042 115.2(4) . .
C041 C042 C043 110.0(4) . .
C044 C043 C042 114.4(4) . .
N4 C010 C08 106.3(5) . .
F1S C1S F2S 106.9(4) . .
F1S C1S F3S 107.5(4) . .
F2S C1S F3S 105.5(4) . .
F1S C1S C2S 113.6(4) . .
F2S C1S C2S 111.0(4) . .
F3S C1S C2S 111.9(4) . .
C3S C2S C4S 120.1(5) . 2_556
C3S C2S C1S 120.0(5) . .
C4S C2S C1S 119.8(5) 2_556 .
C2S C3S C4S 120.3(5) . .
C3S C4S C2S 119.5(5) . 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 2.026(4) 2
Cu1 O1 2.026(4) .
Cu1 O01 2.063(3) 2
Cu1 O01 2.063(3) .
Cu1 O2 2.120(4) .
Cu1 O2 2.120(4) 2
O1 C2 1.257(6) .
C1 F1A 1.29(2) .
C1 F2 1.318(18) .
C1 F3 1.339(6) .
C1 F2A 1.353(18) .
C1 F1 1.41(2) .
C1 C2 1.510(7) .
F1 F1A 0.61(2) .
F2 F2A 0.67(2) .
F2 F1A 1.69(3) .
C2 C3 1.405(7) .
C3 C4 1.392(7) .
C4 O2 1.233(6) .
C4 C5 1.542(7) .
C5 F6 1.333(6) .
C5 F4 1.336(6) .
C5 F5 1.339(6) .
Cu2 O4 1.932(3) 2_666
Cu2 O4 1.932(3) .
Cu2 O3 1.977(3) 2_666
Cu2 O3 1.977(3) .
Cu2 N3 2.415(4) .
Cu2 N3 2.415(4) 2_666
O3 C7 1.282(6) .
C6 F7 1.331(6) .
C6 F9 1.344(5) .
C6 F8 1.349(6) .
C6 C7 1.522(7) .
C7 C8 1.374(6) .
C8 C9 1.392(6) .
C9 O4 1.263(5) .
C9 C10 1.509(7) .
C10 F12 1.332(5) .
C10 F11 1.344(5) .
C10 F10 1.352(5) .
O01 N1 1.306(5) .
N1 C07 1.342(6) .
N1 C01 1.507(6) .
C01 C03 1.519(7) .
C01 C04 1.529(7) .
C01 C02 1.546(7) .
C04 N2 1.501(6) .
C04 C06 1.507(6) .
C04 C05 1.533(6) .
N2 O02 1.275(5) .
N2 C07 1.365(6) .
C07 C08 1.435(6) .
C08 C010 1.385(6) .
C08 C09 1.419(6) .
C09 N3 1.338(5) .
N3 N4 1.342(5) .
N4 C010 1.345(6) .
N4 C041 1.486(6) .
C041 C042 1.494(6) .
C042 C043 1.529(6) .
C043 C044 1.515(7) .
C1S F1S 1.329(5) .
C1S F2S 1.348(5) .
C1S F3S 1.350(5) .
C1S C2S 1.504(7) .
C2S C3S 1.357(7) .
C2S C4S 1.389(6) 2_556
C3S C4S 1.372(6) .
C4S C2S 1.389(6) 2_556
