#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:38:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179416 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/13/4331319.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_4331319
loop_
_publ_author_name
'Xiao-Yan Chen'
'George S. Goff'
'William C. Ewing'
'Brian L. Scott'
'Wolfgang Runde'
_publ_section_title
;
 Solid-State and Solution-State Coordination Chemistry of Lanthanide(III)
 Complexes with α-Hydroxyisobutyric Acid
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              13254
_journal_page_last               13263
_journal_paper_doi               10.1021/ic301775d
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C8 H20 Ho N O12'
_chemical_formula_weight         487.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 92.136(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8084(16)
_cell_length_b                   8.4031(15)
_cell_length_c                   20.874(4)
_cell_measurement_temperature    120(1)
_cell_volume                     1544.0(5)
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8316
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.185
_exptl_absorpt_correction_T_max  0.9034
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         3.003
_refine_diff_density_min         -5.470
_refine_diff_density_rms         0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.566
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.566
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0525
_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)+(0.0304P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1760
_reflns_number_total             1835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301775d_si_001_8.cif
_cod_data_source_block           apx1463
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4331319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Ho1 Ho 0.0000 0.39925(6) 0.2500 0.00825(19) Uani 1 2 d S
N1 N 0.6733(16) 0.1780(17) 0.0228(7) 0.015(3) Uani 0.50 1 d P
O1 O -0.0090(7) 0.2634(7) 0.1496(3) 0.0156(13) Uani 1 1 d .
O2 O 0.1861(7) 0.2061(7) 0.2384(3) 0.0156(13) Uani 1 1 d .
O3 O 0.2889(7) -0.0016(7) 0.1892(3) 0.0143(13) Uani 1 1 d .
O4 O 0.1054(8) 0.5838(8) 0.1827(3) 0.0211(14) Uani 1 1 d .
O5 O 0.5793(9) 0.0862(9) 0.0515(4) 0.0312(17) Uani 1 1 d .
O6 O 0.6806(17) 0.185(2) -0.0378(7) 0.021(4) Uani 0.50 1 d P
O6' O 0.7631(18) 0.2668(18) 0.0545(7) 0.020(3) Uani 0.50 1 d P
C1 C 0.0863(10) 0.1313(9) 0.1335(4) 0.0127(17) Uani 1 1 d .
C2 C -0.0110(11) -0.0164(11) 0.1235(5) 0.021(2) Uani 1 1 d .
H2A H -0.0626 -0.0398 0.1621 0.031 Uiso 1 1 calc R
H2B H 0.0524 -0.1048 0.1129 0.031 Uiso 1 1 calc R
H2C H -0.0844 0.0019 0.0891 0.031 Uiso 1 1 calc R
C3 C 0.1718(11) 0.1717(12) 0.0743(5) 0.022(2) Uani 1 1 d .
H3A H 0.1030 0.1707 0.0375 0.033 Uiso 1 1 calc R
H3B H 0.2506 0.0945 0.0686 0.033 Uiso 1 1 calc R
H3C H 0.2162 0.2755 0.0790 0.033 Uiso 1 1 calc R
C4 C 0.1954(10) 0.1088(10) 0.1912(5) 0.0149(17) Uani 1 1 d .
H1 H -0.066(18) 0.26(2) 0.114(8) 0.080 Uiso 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'
Ho Ho -0.2175 4.6783 '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
O4 Ho1 O4 95.7(3) . 2
O4 Ho1 O2 146.3(2) . 2
O4 Ho1 O2 96.0(2) 2 2
O4 Ho1 O2 96.0(2) . .
O4 Ho1 O2 146.3(2) 2 .
O2 Ho1 O2 91.5(3) 2 .
O4 Ho1 O3 76.4(2) . 4
O4 Ho1 O3 76.3(2) 2 4
O2 Ho1 O3 137.2(2) 2 4
O2 Ho1 O3 76.0(2) . 4
O4 Ho1 O3 76.3(2) . 3_455
O4 Ho1 O3 76.4(2) 2 3_455
O2 Ho1 O3 76.0(2) 2 3_455
O2 Ho1 O3 137.2(2) . 3_455
O3 Ho1 O3 138.7(3) 4 3_455
O4 Ho1 O1 77.8(2) . .
O4 Ho1 O1 148.7(2) 2 .
O2 Ho1 O1 75.9(2) 2 .
O2 Ho1 O1 64.9(2) . .
O3 Ho1 O1 129.8(2) 4 .
O3 Ho1 O1 72.4(2) 3_455 .
O4 Ho1 O1 148.7(2) . 2
O4 Ho1 O1 77.8(2) 2 2
O2 Ho1 O1 64.9(2) 2 2
O2 Ho1 O1 75.9(2) . 2
O3 Ho1 O1 72.4(2) 4 2
O3 Ho1 O1 129.8(2) 3_455 2
O1 Ho1 O1 122.8(3) . 2
O6' N1 O6 116.2(15) . .
O6' N1 O5 120.8(16) . .
O6 N1 O5 123.0(15) . .
O6' N1 O6 21.4(9) . 7_655
O6 N1 O6 94.8(13) . 7_655
O5 N1 O6 142.2(13) . 7_655
O6' N1 O6' 96.2(12) . 7_655
O6 N1 O6' 20.1(9) . 7_655
O5 N1 O6' 143.0(13) . 7_655
O6 N1 O6' 74.7(8) 7_655 7_655
C1 O1 Ho1 125.0(5) . .
C1 O1 H1 98(10) . .
Ho1 O1 H1 137(10) . .
C4 O2 Ho1 126.0(5) . .
C4 O3 Ho1 139.0(6) . 3_545
O6' O6 N1 124(3) 7_655 .
O6' O6 N1 38.5(18) 7_655 7_655
N1 O6 N1 85.2(13) . 7_655
O6 O6' N1 120(3) 7_655 .
O6 O6' N1 36.3(18) 7_655 7_655
N1 O6' N1 83.8(12) . 7_655
O1 C1 C3 109.3(7) . .
O1 C1 C2 109.4(7) . .
C3 C1 C2 111.5(8) . .
O1 C1 C4 105.5(7) . .
C3 C1 C4 110.8(7) . .
C2 C1 C4 110.1(7) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
O3 C4 O2 124.1(8) . .
O3 C4 C1 117.8(8) . .
O2 C4 C1 118.1(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ho1 O4 2.311(6) .
Ho1 O4 2.311(6) 2
Ho1 O2 2.326(6) 2
Ho1 O2 2.326(6) .
Ho1 O3 2.363(6) 4
Ho1 O3 2.363(6) 3_455
Ho1 O1 2.385(6) .
Ho1 O1 2.385(6) 2
N1 O6' 1.26(2) .
N1 O6 1.27(2) .
N1 O5 1.294(17) .
N1 O6 1.75(2) 7_655
N1 O6' 1.79(2) 7_655
O1 C1 1.439(10) .
O1 H1 0.88(17) .
O2 C4 1.286(10) .
O3 C4 1.243(10) .
O3 Ho1 2.363(6) 3_545
O6 O6' 0.738(16) 7_655
O6 N1 1.75(2) 7_655
O6' O6 0.738(16) 7_655
O6' N1 1.79(2) 7_655
C1 C3 1.511(13) .
C1 C2 1.518(12) .
C1 C4 1.523(12) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
