#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:52:50 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179267 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/87/4318731.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_4318731
loop_
_publ_author_name
'Christophe Lescop'
'Dominique Luneau'
'Paul Rey'
'Guillaume Bussière'
'Christian Reber'
_publ_contact_author
;
       Dominique LUNEAU
       Laboratoire de Chimie Inorganique et Biologique (UMR 5046)
       DRFMC
       CEA-Grenoble
       38054 Grenoble, France
;
_publ_contact_author_email       luneau@drfmc.ceng.cea.fr
_publ_contact_author_fax         '33 438 785 090'
_publ_contact_author_phone       '33 438 784 462'
_publ_section_title
;
 Synthesis, Structures, and Magnetic and Optical Properties of a Series of
 Europium(III) and Gadolinium(III) Complexes with Chelating Nitronyl and
 Imino Nitroxide Free Radicals
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5566
_journal_page_last               5574
_journal_paper_doi               10.1021/ic0257928
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C27 H19 Eu F18 N3 O7'
_chemical_formula_weight         991.41
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.736(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6171(14)
_cell_length_b                   31.574(5)
_cell_length_c                   12.2073(17)
_cell_measurement_temperature    298(2)
_cell_volume                     3663.7(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23419
_diffrn_reflns_theta_full        29.02
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1932
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.289
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0757P)²+1.8219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                6754
_reflns_number_total             8906
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0257928_8.cif
_cod_data_source_block           cl444_compound_4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4318731
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu Eu 0.338660(14) 0.361667(4) 0.225015(10) 0.04618(4) Uani 1 1 d . . .
O2 O -0.0444(3) 0.32405(9) -0.1654(2) 0.0996(9) Uani 1 1 d . . .
N3 N 0.2260(2) 0.29369(7) 0.13651(17) 0.0498(6) Uani 1 1 d . . .
N2 N 0.0105(3) 0.35018(9) -0.0918(2) 0.0734(8) Uani 1 1 d . . .
N1 N 0.1339(3) 0.37210(7) 0.0674(2) 0.0521(6) Uani 1 1 d . . .
C1 C 0.0909(3) 0.33934(9) 0.0090(2) 0.0513(7) Uani 1 1 d . . .
C3 C 0.0250(4) 0.39633(12) -0.1118(3) 0.0873(12) Uani 1 1 d . . .
C2 C 0.0646(4) 0.41101(10) 0.0105(3) 0.0716(10) Uani 1 1 d . . .
C7 C 0.1432(6) 0.40132(17) -0.1798(4) 0.1277(19) Uani 1 1 d . . .
H7A H 0.1121 0.3917 -0.2541 0.192 Uiso 1 1 calc R . .
H7B H 0.2226 0.3848 -0.1472 0.192 Uiso 1 1 calc R . .
H7C H 0.1698 0.4306 -0.1810 0.192 Uiso 1 1 calc R . .
C6 C -0.1141(5) 0.41445(15) -0.1719(4) 0.148(2) Uani 1 1 d . . .
H6A H -0.1308 0.4040 -0.2465 0.221 Uiso 1 1 calc R . .
H6B H -0.1087 0.4448 -0.1728 0.221 Uiso 1 1 calc R . .
H6C H -0.1897 0.4059 -0.1338 0.221 Uiso 1 1 calc R . .
C4 C -0.0614(4) 0.42003(13) 0.0676(4) 0.1026(15) Uani 1 1 d . . .
H4A H -0.0299 0.4289 0.1424 0.154 Uiso 1 1 calc R . .
H4B H -0.1173 0.3948 0.0679 0.154 Uiso 1 1 calc R . .
H4C H -0.1171 0.4421 0.0285 0.154 Uiso 1 1 calc R . .
C5 C 0.1681(5) 0.44758(11) 0.0242(4) 0.1040(15) Uani 1 1 d . . .
H5A H 0.1884 0.4553 0.1011 0.156 Uiso 1 1 calc R . .
H5B H 0.1279 0.4714 -0.0181 0.156 Uiso 1 1 calc R . .
H5C H 0.2534 0.4392 -0.0016 0.156 Uiso 1 1 calc R . .
C9 C 0.2668(4) 0.25555(9) 0.1759(2) 0.0641(9) Uani 1 1 d . . .
H9A H 0.3356 0.2541 0.2382 0.077 Uiso 1 1 calc R . .
C13 C 0.1269(3) 0.29566(9) 0.0454(2) 0.0484(7) Uani 1 1 d . . .
C12 C 0.0680(4) 0.25958(10) -0.0055(3) 0.0701(10) Uani 1 1 d . . .
H12A H -0.0003 0.2615 -0.0680 0.084 Uiso 1 1 calc R . .
C11 C 0.1118(4) 0.22013(10) 0.0378(3) 0.0740(10) Uani 1 1 d . . .
H11A H 0.0727 0.1955 0.0047 0.089 Uiso 1 1 calc R . .
C10 C 0.2119(4) 0.21804(10) 0.1289(3) 0.0706(10) Uani 1 1 d . . .
H10A H 0.2430 0.1920 0.1590 0.085 Uiso 1 1 calc R . .
O1H O 0.4557(2) 0.42482(7) 0.19734(17) 0.0683(6) Uani 1 1 d . . .
O2H O 0.4696(2) 0.38369(6) 0.40043(16) 0.0627(6) Uani 1 1 d . . .
O3H O 0.1852(2) 0.40799(7) 0.30233(19) 0.0689(6) Uani 1 1 d . . .
O4H O 0.2464(2) 0.32346(6) 0.36335(16) 0.0585(5) Uani 1 1 d . . .
O5H O 0.4203(2) 0.35301(8) 0.04849(18) 0.0678(6) Uani 1 1 d . . .
O6H O 0.5487(2) 0.32210(7) 0.25329(17) 0.0642(6) Uani 1 1 d . . .
C2H C 0.5278(4) 0.45095(10) 0.2560(3) 0.0675(9) Uani 1 1 d . . .
C1H C 0.5742(5) 0.48924(15) 0.1940(4) 0.1115(15) Uani 1 1 d . . .
C3H C 0.5739(4) 0.44893(11) 0.3692(3) 0.0829(11) Uani 1 1 d . . .
H3HA H 0.6282 0.4709 0.4036 0.099 Uiso 1 1 calc R . .
C4H C 0.5411(4) 0.41520(10) 0.4319(3) 0.0651(9) Uani 1 1 d . . .
C5H C 0.6018(7) 0.41543(14) 0.5547(3) 0.135(2) Uani 1 1 d . . .
C7H C 0.1363(4) 0.40698(11) 0.3912(3) 0.0728(10) Uani 1 1 d . . .
C6H C 0.0715(7) 0.44765(15) 0.4228(5) 0.1291(19) Uani 1 1 d . . .
C8H C 0.1298(4) 0.37344(13) 0.4611(3) 0.0794(11) Uani 1 1 d . . .
H8HA H 0.0879 0.3773 0.5242 0.095 Uiso 1 1 calc R . .
C9H C 0.1834(3) 0.33378(11) 0.4412(3) 0.0637(9) Uani 1 1 d . . .
C10H C 0.1666(5) 0.29888(16) 0.5221(4) 0.1060(15) Uani 1 1 d . . .
C12H C 0.5322(4) 0.34026(10) 0.0216(3) 0.0650(9) Uani 1 1 d . . .
C11H C 0.5329(6) 0.34334(17) -0.1045(3) 0.1078(15) Uani 1 1 d . . .
C13H C 0.6496(4) 0.32531(11) 0.0879(3) 0.0742(10) Uani 1 1 d . . .
H13A H 0.7309 0.3201 0.0574 0.089 Uiso 1 1 calc R . .
C14H C 0.6496(3) 0.31779(11) 0.1992(3) 0.0656(9) Uani 1 1 d . . .
C15H C 0.7844(5) 0.30230(17) 0.2684(4) 0.1054(16) Uani 1 1 d . . .
F1 F 0.6303(4) 0.47694(12) 0.1087(3) 0.1983(15) Uani 1 1 d . . .
F2 F 0.6524(4) 0.51545(11) 0.2518(3) 0.2327(16) Uani 1 1 d . . .
F3 F 0.4646(5) 0.51120(9) 0.1499(3) 0.1719(15) Uani 1 1 d . . .
F4 F 0.6912(7) 0.38794(14) 0.5786(3) 0.328(2) Uani 1 1 d . . .
F5 F 0.6490(5) 0.44906(9) 0.5958(2) 0.1903(17) Uani 1 1 d . . .
F6 F 0.5177(6) 0.3999(2) 0.6119(3) 0.303(3) Uani 1 1 d . . .
F7 F 0.0167(5) 0.44894(12) 0.5053(4) 0.2584(17) Uani 1 1 d . . .
F8 F -0.0065(5) 0.46459(13) 0.3524(4) 0.305(2) Uani 1 1 d . . .
F9 F 0.1617(5) 0.47612(11) 0.4433(6) 0.295(3) Uani 1 1 d . . .
F10 F 0.0910(6) 0.26791(13) 0.4701(4) 0.228(2) Uani 1 1 d . . .
F11 F 0.0881(5) 0.30627(13) 0.5934(3) 0.2190(15) Uani 1 1 d . . .
F12 F 0.2721(4) 0.28096(14) 0.5614(4) 0.2637(16) Uani 1 1 d . . .
F13 F 0.5230(4) 0.38258(11) -0.1373(2) 0.1553(12) Uani 1 1 d . . .
F14 F 0.6509(4) 0.32904(14) -0.1335(2) 0.1743(15) Uani 1 1 d . . .
F15 F 0.4298(5) 0.32282(13) -0.1589(2) 0.1791(16) Uani 1 1 d . . .
F16 F 0.8157(3) 0.32332(13) 0.3595(3) 0.1696(14) Uani 1 1 d . . .
F17 F 0.8910(3) 0.29947(15) 0.2173(3) 0.1762(17) Uani 1 1 d . . .
F18 F 0.7680(3) 0.26338(12) 0.3057(3) 0.1608(13) Uani 1 1 d . . .
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'
Eu Eu -0.1578 3.6682 '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
_geom_angle_publ_flag
O1H Eu O4H 141.44(7) . . ?
O1H Eu O6H 93.01(8) . . ?
O4H Eu O6H 91.80(7) . . ?
O1H Eu O3H 82.77(8) . . ?
O4H Eu O3H 72.89(8) . . ?
O6H Eu O3H 147.14(7) . . ?
O1H Eu O2H 71.65(7) . . ?
O4H Eu O2H 73.40(7) . . ?
O6H Eu O2H 72.71(7) . . ?
O3H Eu O2H 75.05(8) . . ?
O1H Eu O5H 74.88(8) . . ?
O4H Eu O5H 142.13(7) . . ?
O6H Eu O5H 71.53(8) . . ?
O3H Eu O5H 136.87(8) . . ?
O2H Eu O5H 128.77(8) . . ?
O1H Eu N1 96.55(7) . . ?
O4H Eu N1 105.93(8) . . ?
O6H Eu N1 136.38(8) . . ?
O3H Eu N1 76.43(8) . . ?
O2H Eu N1 150.24(8) . . ?
O5H Eu N1 70.21(8) . . ?
O1H Eu N3 146.44(7) . . ?
O4H Eu N3 72.11(7) . . ?
O6H Eu N3 85.18(7) . . ?
O3H Eu N3 115.75(8) . . ?
O2H Eu N3 138.03(7) . . ?
O5H Eu N3 72.78(8) . . ?
N1 Eu N3 64.12(7) . . ?
C9 N3 C13 118.1(2) . . ?
C9 N3 Eu 121.39(18) . . ?
C13 N3 Eu 120.49(17) . . ?
O2 N2 C1 125.4(3) . . ?
O2 N2 C3 123.9(3) . . ?
C1 N2 C3 109.4(3) . . ?
C1 N1 C2 108.4(2) . . ?
C1 N1 Eu 117.31(18) . . ?
C2 N1 Eu 133.18(18) . . ?
N1 C1 N2 112.3(3) . . ?
N1 C1 C13 123.0(2) . . ?
N2 C1 C13 124.7(2) . . ?
N2 C3 C7 106.8(4) . . ?
N2 C3 C6 110.3(3) . . ?
C7 C3 C6 111.8(4) . . ?
N2 C3 C2 98.6(3) . . ?
C7 C3 C2 113.6(3) . . ?
C6 C3 C2 114.6(4) . . ?
N1 C2 C5 109.3(3) . . ?
N1 C2 C4 105.6(3) . . ?
C5 C2 C4 111.3(3) . . ?
N1 C2 C3 103.0(3) . . ?
C5 C2 C3 113.2(3) . . ?
C4 C2 C3 113.7(3) . . ?
N3 C9 C10 123.4(3) . . ?
N3 C13 C12 121.5(3) . . ?
N3 C13 C1 113.2(2) . . ?
C12 C13 C1 125.2(3) . . ?
C13 C12 C11 119.3(3) . . ?
C10 C11 C12 119.4(3) . . ?
C11 C10 C9 118.4(3) . . ?
C2H O1H Eu 136.6(2) . . ?
C4H O2H Eu 134.21(19) . . ?
C7H O3H Eu 132.1(2) . . ?
C9H O4H Eu 133.9(2) . . ?
C12H O5H Eu 133.3(2) . . ?
C14H O6H Eu 133.7(2) . . ?
O1H C2H C3H 127.9(3) . . ?
O1H C2H C1H 114.9(3) . . ?
C3H C2H C1H 117.2(3) . . ?
F2 C1H F3 104.9(4) . . ?
F2 C1H F1 111.0(5) . . ?
F3 C1H F1 103.6(4) . . ?
F2 C1H C2H 115.9(4) . . ?
F3 C1H C2H 110.2(4) . . ?
F1 C1H C2H 110.4(4) . . ?
C4H C3H C2H 121.6(3) . . ?
O2H C4H C3H 127.8(3) . . ?
O2H C4H C5H 114.9(3) . . ?
C3H C4H C5H 117.2(3) . . ?
F5 C5H F6 110.0(5) . . ?
F5 C5H F4 108.2(5) . . ?
F6 C5H F4 94.5(5) . . ?
F5 C5H C4H 117.9(3) . . ?
F6 C5H C4H 111.4(4) . . ?
F4 C5H C4H 112.4(4) . . ?
O3H C7H C8H 128.4(3) . . ?
O3H C7H C6H 115.3(4) . . ?
C8H C7H C6H 116.2(4) . . ?
F8 C6H F7 106.4(6) . . ?
F8 C6H F9 99.5(5) . . ?
F7 C6H F9 100.7(5) . . ?
F8 C6H C7H 116.4(5) . . ?
F7 C6H C7H 119.6(5) . . ?
F9 C6H C7H 111.4(5) . . ?
C7H C8H C9H 122.4(3) . . ?
O4H C9H C8H 127.3(3) . . ?
O4H C9H C10H 115.0(3) . . ?
C8H C9H C10H 117.8(3) . . ?
F12 C10H F11 111.8(4) . . ?
F12 C10H F10 102.3(5) . . ?
F11 C10H F10 97.2(4) . . ?
F12 C10H C9H 116.1(4) . . ?
F11 C10H C9H 117.0(4) . . ?
F10 C10H C9H 109.4(4) . . ?
O5H C12H C13H 128.8(3) . . ?
O5H C12H C11H 112.3(3) . . ?
C13H C12H C11H 118.9(3) . . ?
F15 C11H F13 107.8(4) . . ?
F15 C11H F14 108.5(4) . . ?
F13 C11H F14 105.6(4) . . ?
F15 C11H C12H 111.4(4) . . ?
F13 C11H C12H 110.9(4) . . ?
F14 C11H C12H 112.4(4) . . ?
C12H C13H C14H 121.2(3) . . ?
O6H C14H C13H 127.8(3) . . ?
O6H C14H C15H 113.8(3) . . ?
C13H C14H C15H 118.4(3) . . ?
F17 C15H F16 110.8(4) . . ?
F17 C15H F18 104.3(4) . . ?
F16 C15H F18 101.8(4) . . ?
F17 C15H C14H 115.5(4) . . ?
F16 C15H C14H 112.5(4) . . ?
F18 C15H C14H 110.7(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu O1H 2.339(2) . ?
Eu O4H 2.356(2) . ?
Eu O6H 2.355(2) . ?
Eu O3H 2.373(2) . ?
Eu O2H 2.4156(19) . ?
Eu O5H 2.419(2) . ?
Eu N1 2.557(2) . ?
Eu N3 2.568(2) . ?
O2 N2 1.273(4) . ?
N3 C9 1.334(4) . ?
N3 C13 1.352(3) . ?
N2 C1 1.393(4) . ?
N2 C3 1.488(5) . ?
N1 C1 1.288(4) . ?
N1 C2 1.515(4) . ?
C1 C13 1.474(4) . ?
C3 C7 1.514(6) . ?
C3 C6 1.534(6) . ?
C3 C2 1.555(5) . ?
C2 C5 1.517(5) . ?
C2 C4 1.514(6) . ?
C9 C10 1.385(4) . ?
C13 C12 1.377(4) . ?
C12 C11 1.393(5) . ?
C11 C10 1.358(5) . ?
O1H C2H 1.235(4) . ?
O2H C4H 1.237(4) . ?
O3H C7H 1.247(4) . ?
O4H C9H 1.246(4) . ?
O5H C12H 1.238(4) . ?
O6H C14H 1.261(4) . ?
C2H C3H 1.387(5) . ?
C2H C1H 1.529(5) . ?
C1H F2 1.259(5) . ?
C1H F3 1.308(6) . ?
C1H F1 1.303(6) . ?
C3H C4H 1.376(5) . ?
C4H C5H 1.524(5) . ?
C5H F5 1.231(5) . ?
C5H F6 1.247(7) . ?
C5H F4 1.225(7) . ?
C7H C8H 1.367(5) . ?
C7H C6H 1.503(6) . ?
C6H F8 1.179(7) . ?
C6H F7 1.206(7) . ?
C6H F9 1.248(7) . ?
C8H C9H 1.390(5) . ?
C9H C10H 1.505(5) . ?
C10H F12 1.197(6) . ?
C10H F11 1.258(6) . ?
C10H F10 1.322(6) . ?
C12H C13H 1.370(5) . ?
C12H C11H 1.543(5) . ?
C11H F15 1.282(6) . ?
C11H F13 1.301(6) . ?
C11H F14 1.318(6) . ?
C13H C14H 1.379(5) . ?
C14H C15H 1.517(5) . ?
C15H F17 1.282(5) . ?
C15H F16 1.291(6) . ?
C15H F18 1.329(6) . ?
