#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:14:58 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179445 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/42/4334213.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_4334213
loop_
_publ_author_name
'Xiao-Yan Chen'
'George S. Goff'
'Brian L. Scott'
'Michael T. Janicke'
'Wolfgang Runde'
_publ_section_title
;
 Solid-State and Solution-State Coordination Chemistry of Lanthanide(III)
 Complexes with (Pyrazol-1-yl)acetic Acid
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3217
_journal_page_last               3224
_journal_paper_doi               10.1021/ic302696m
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C15 H23 Ce N6 O10'
_chemical_formula_weight         587.51
_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                 117.433(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8937(5)
_cell_length_b                   29.3072(18)
_cell_length_c                   9.3379(6)
_cell_measurement_temperature    120(1)
_cell_volume                     2160.2(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.936
_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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24390
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.172
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_description       needle
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.477
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5131
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.379
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0291P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                4337
_reflns_number_total             5131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302696m_si_001_2.cif
_cod_data_source_block           apx1516
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4334213
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
Ce1 Ce 0.26002(2) 0.003316(6) 0.01508(2) 0.01121(7) Uani 1 1 d .
N1 N 0.4913(4) 0.16921(10) 0.0178(3) 0.0182(7) Uani 1 1 d .
N2 N 0.5359(4) 0.18931(11) 0.1609(4) 0.0246(7) Uani 1 1 d .
N3 N 0.3430(4) 0.10789(10) 0.4763(3) 0.0164(6) Uani 1 1 d .
N4 N 0.2530(4) 0.10120(11) 0.5579(4) 0.0210(7) Uani 1 1 d .
N5 N 0.1280(4) -0.15852(11) 0.1473(4) 0.0274(8) Uani 1 1 d .
N6 N 0.2552(4) -0.17641(12) 0.2781(5) 0.0355(9) Uani 1 1 d .
O1 O 0.5221(3) 0.04562(8) 0.0065(3) 0.0150(5) Uani 1 1 d .
O2 O 0.3437(3) 0.08949(8) 0.0463(3) 0.0159(5) Uani 1 1 d .
O3 O 0.2404(3) 0.03769(9) 0.2539(3) 0.0195(5) Uani 1 1 d .
O4 O 0.5030(3) 0.01961(8) 0.3127(3) 0.0170(5) Uani 1 1 d .
O5 O 0.0194(3) -0.03952(8) 0.0803(3) 0.0151(5) Uani 1 1 d .
O6 O 0.2662(3) -0.07303(8) 0.1551(3) 0.0142(5) Uani 1 1 d .
O7 O 0.0806(3) -0.05311(8) -0.2029(3) 0.0152(5) Uani 1 1 d D
O8 O 0.1743(3) 0.03523(9) -0.2686(3) 0.0185(5) Uani 1 1 d .
O9 O 0.7521(4) 0.14349(10) 0.4476(4) 0.0358(7) Uani 1 1 d .
O10 O 0.8440(3) 0.05440(8) 0.4610(3) 0.0189(5) Uani 1 1 d .
C1 C 0.4694(4) 0.08481(11) 0.0229(4) 0.0136(7) Uani 1 1 d .
C2 C 0.5663(5) 0.12593(11) 0.0089(5) 0.0203(8) Uani 1 1 d .
H2A H 0.6818 0.1247 0.0949 0.024 Uiso 1 1 calc R
H2B H 0.5705 0.1243 -0.0929 0.024 Uiso 1 1 calc R
C3 C 0.4477(5) 0.22777(13) 0.1253(5) 0.0328(10) Uani 1 1 d .
H3 H 0.4521 0.2488 0.2017 0.039 Uiso 1 1 calc R
C4 C 0.3481(5) 0.23283(14) -0.0395(6) 0.0415(12) Uani 1 1 d .
H4 H 0.2762 0.2569 -0.0937 0.050 Uiso 1 1 calc R
C5 C 0.3796(5) 0.19431(13) -0.1045(5) 0.0326(10) Uani 1 1 d .
H5 H 0.3321 0.1870 -0.2136 0.039 Uiso 1 1 calc R
C6 C 0.3972(4) 0.04165(11) 0.3408(4) 0.0153(7) Uani 1 1 d .
C7 C 0.4657(4) 0.07391(12) 0.4839(4) 0.0188(8) Uani 1 1 d .
H7A H 0.5016 0.0563 0.5821 0.023 Uiso 1 1 calc R
H7B H 0.5645 0.0894 0.4892 0.023 Uiso 1 1 calc R
C8 C 0.2991(5) 0.14567(13) 0.3883(5) 0.0308(10) Uani 1 1 d .
H8 H 0.3446 0.1566 0.3231 0.037 Uiso 1 1 calc R
C9 C 0.1708(5) 0.16578(14) 0.4132(5) 0.0334(10) Uani 1 1 d .
H9 H 0.1135 0.1929 0.3694 0.040 Uiso 1 1 calc R
C10 C 0.1481(5) 0.13658(14) 0.5170(5) 0.0261(9) Uani 1 1 d .
H10 H 0.0685 0.1411 0.5541 0.031 Uiso 1 1 calc R
C11 C 0.1157(4) -0.07404(11) 0.1282(4) 0.0122(7) Uani 1 1 d .
C12 C 0.0370(4) -0.11800(12) 0.1473(5) 0.0217(8) Uani 1 1 d .
H12A H 0.0298 -0.1167 0.2477 0.026 Uiso 1 1 calc R
H12B H -0.0776 -0.1202 0.0601 0.026 Uiso 1 1 calc R
C13 C 0.1081(6) -0.18149(15) 0.0114(5) 0.0369(11) Uani 1 1 d .
H13 H 0.0292 -0.1748 -0.0941 0.044 Uiso 1 1 calc R
C14 C 0.2239(6) -0.21564(15) 0.0584(6) 0.0382(11) Uani 1 1 d .
H14 H 0.2413 -0.2371 -0.0059 0.046 Uiso 1 1 calc R
C15 C 0.3121(5) -0.21102(14) 0.2282(6) 0.0376(11) Uani 1 1 d .
H15 H 0.3994 -0.2301 0.2960 0.045 Uiso 1 1 calc R
H1A H 0.213(7) 0.0549(19) -0.314(7) 0.080 Uiso 1 1 d .
H1B H 0.071(7) 0.0384(19) -0.337(7) 0.080 Uiso 1 1 d .
H1C H 0.097(7) -0.0559(18) -0.307(4) 0.080 Uiso 1 1 d D
H1D H -0.046(3) -0.0540(17) -0.232(6) 0.080 Uiso 1 1 d 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'
Ce Ce -0.2486 2.6331 '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
O5 Ce1 O1 155.78(8) 3 3_655
O5 Ce1 O3 71.22(8) 3 .
O1 Ce1 O3 132.36(7) 3_655 .
O5 Ce1 O7 80.42(7) 3 .
O1 Ce1 O7 77.59(7) 3_655 .
O3 Ce1 O7 134.01(7) . .
O5 Ce1 O8 72.55(8) 3 .
O1 Ce1 O8 89.90(8) 3_655 .
O3 Ce1 O8 131.02(8) . .
O7 Ce1 O8 68.42(8) . .
O5 Ce1 O6 109.84(7) 3 .
O1 Ce1 O6 72.91(7) 3_655 .
O3 Ce1 O6 83.82(8) . .
O7 Ce1 O6 72.52(7) . .
O8 Ce1 O6 139.88(8) . .
O5 Ce1 O2 79.15(7) 3 .
O1 Ce1 O2 111.92(7) 3_655 .
O3 Ce1 O2 69.37(8) . .
O7 Ce1 O2 139.64(7) . .
O8 Ce1 O2 72.37(8) . .
O6 Ce1 O2 147.57(7) . .
O5 Ce1 O4 119.93(7) 3 .
O1 Ce1 O4 84.28(7) 3_655 .
O3 Ce1 O4 50.19(7) . .
O7 Ce1 O4 149.63(7) . .
O8 Ce1 O4 136.30(8) . .
O6 Ce1 O4 78.98(7) . .
O2 Ce1 O4 69.97(7) . .
O5 Ce1 O1 122.57(7) 3 .
O1 Ce1 O1 62.83(9) 3_655 .
O3 Ce1 O1 104.91(7) . .
O7 Ce1 O1 120.89(7) . .
O8 Ce1 O1 69.47(7) . .
O6 Ce1 O1 127.03(7) . .
O2 Ce1 O1 49.25(7) . .
O4 Ce1 O1 69.42(7) . .
O5 Ce1 O5 61.50(9) 3 .
O1 Ce1 O5 117.61(7) 3_655 .
O3 Ce1 O5 67.26(7) . .
O7 Ce1 O5 67.53(7) . .
O8 Ce1 O5 119.82(7) . .
O6 Ce1 O5 48.38(7) . .
O2 Ce1 O5 128.39(7) . .
O4 Ce1 O5 100.89(7) . .
O1 Ce1 O5 170.31(7) . .
O5 Ce1 C6 94.49(9) 3 .
O1 Ce1 C6 109.72(8) 3_655 .
O3 Ce1 C6 25.22(8) . .
O7 Ce1 C6 152.91(8) . .
O8 Ce1 C6 135.57(9) . .
O6 Ce1 C6 84.54(8) . .
O2 Ce1 C6 63.40(8) . .
O4 Ce1 C6 25.57(8) . .
O1 Ce1 C6 84.35(8) . .
O5 Ce1 C6 86.57(8) . .
O5 Ce1 C1 100.21(8) 3 .
O1 Ce1 C1 87.89(8) 3_655 .
O3 Ce1 C1 87.46(8) . .
O7 Ce1 C1 133.70(8) . .
O8 Ce1 C1 67.84(8) . .
O6 Ce1 C1 143.89(8) . .
O2 Ce1 C1 24.22(8) . .
O4 Ce1 C1 68.69(8) . .
O1 Ce1 C1 25.07(8) . .
O5 Ce1 C1 152.08(8) . .
C6 Ce1 C1 73.34(9) . .
C5 N1 N2 111.8(3) . .
C5 N1 C2 127.7(3) . .
N2 N1 C2 120.5(3) . .
C3 N2 N1 104.7(3) . .
C8 N3 N4 112.9(3) . .
C8 N3 C7 127.0(3) . .
N4 N3 C7 120.0(3) . .
C10 N4 N3 104.2(3) . .
N6 N5 C13 110.3(3) . .
N6 N5 C12 124.5(4) . .
C13 N5 C12 124.9(3) . .
C15 N6 N5 106.4(4) . .
C1 O1 Ce1 150.4(2) . 3_655
C1 O1 Ce1 92.32(19) . .
Ce1 O1 Ce1 117.17(9) 3_655 .
C1 O2 Ce1 96.1(2) . .
C6 O3 Ce1 95.7(2) . .
C6 O4 Ce1 89.10(19) . .
C11 O5 Ce1 151.4(2) . 3
C11 O5 Ce1 88.57(18) . .
Ce1 O5 Ce1 118.50(9) 3 .
C11 O6 Ce1 98.55(19) . .
O2 C1 O1 122.0(3) . .
O2 C1 C2 121.3(3) . .
O1 C1 C2 116.7(3) . .
O2 C1 Ce1 59.63(17) . .
O1 C1 Ce1 62.61(17) . .
C2 C1 Ce1 174.4(2) . .
N1 C2 C1 113.1(3) . .
N2 C3 C4 111.8(4) . .
C5 C4 C3 104.3(4) . .
N1 C5 C4 107.3(4) . .
O3 C6 O4 122.0(3) . .
O3 C6 C7 120.2(3) . .
O4 C6 C7 117.7(3) . .
O3 C6 Ce1 59.05(18) . .
O4 C6 Ce1 65.33(18) . .
C7 C6 Ce1 163.7(2) . .
N3 C7 C6 113.3(3) . .
N3 C8 C9 106.3(4) . .
C10 C9 C8 104.6(4) . .
N4 C10 C9 112.1(4) . .
O6 C11 O5 122.8(3) . .
O6 C11 C12 120.6(3) . .
O5 C11 C12 116.6(3) . .
O6 C11 Ce1 57.48(16) . .
O5 C11 Ce1 66.69(17) . .
C12 C11 Ce1 166.3(2) . .
N5 C12 C11 114.3(3) . .
C14 C13 N5 107.9(4) . .
C13 C14 C15 103.8(4) . .
N6 C15 C14 111.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ce1 O5 2.461(2) 3
Ce1 O1 2.492(2) 3_655
Ce1 O3 2.525(2) .
Ce1 O7 2.536(2) .
Ce1 O8 2.572(2) .
Ce1 O6 2.579(2) .
Ce1 O2 2.611(2) .
Ce1 O4 2.663(2) .
Ce1 O1 2.674(2) .
Ce1 O5 2.779(2) .
Ce1 C6 2.930(3) .
Ce1 C1 3.009(3) .
N1 C5 1.337(5) .
N1 N2 1.342(4) .
N1 C2 1.453(4) .
N2 C3 1.325(5) .
N3 C8 1.326(5) .
N3 N4 1.350(4) .
N3 C7 1.455(4) .
N4 C10 1.328(5) .
N5 N6 1.331(4) .
N5 C13 1.374(5) .
N5 C12 1.437(4) .
N6 C15 1.311(5) .
O1 C1 1.276(4) .
O1 Ce1 2.492(2) 3_655
O2 C1 1.242(4) .
O3 C6 1.255(4) .
O4 C6 1.264(4) .
O5 C11 1.266(4) .
O5 Ce1 2.461(2) 3
O6 C11 1.243(4) .
C1 C2 1.522(5) .
C3 C4 1.385(6) .
C4 C5 1.371(6) .
C6 C7 1.516(5) .
C8 C9 1.395(5) .
C9 C10 1.376(6) .
C11 C12 1.516(5) .
C13 C14 1.356(6) .
C14 C15 1.415(6) .
