#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:14:58 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179445 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/42/4334214.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_4334214
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 N6 O10 Pr'
_chemical_formula_weight         588.30
_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                 117.643(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8744(5)
_cell_length_b                   29.2893(17)
_cell_length_c                   9.3719(6)
_cell_measurement_temperature    120(1)
_cell_volume                     2157.9(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 1.000
_diffrn_measured_fraction_theta_max 0.944
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24265
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.39
_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    2.322
_exptl_absorpt_correction_T_max  0.8732
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5115
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.912
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0175P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0632
_reflns_number_gt                4829
_reflns_number_total             5115
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302696m_si_001_3.cif
_cod_data_source_block           apx1493
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4334214
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
Pr1 Pr 0.739114(15) 1.003395(4) 0.985053(15) 0.00932(5) Uani 1 1 d .
N1 N 0.6522(3) 1.10667(7) 0.5232(2) 0.0133(4) Uani 1 1 d .
N2 N 0.7410(3) 1.09974(7) 0.4408(3) 0.0173(5) Uani 1 1 d .
N3 N 0.8720(3) 0.84189(7) 0.8539(3) 0.0191(5) Uani 1 1 d .
N4 N 0.7446(3) 0.82395(8) 0.7211(3) 0.0240(5) Uani 1 1 d .
N5 N 0.4914(2) 0.83112(7) 1.0179(2) 0.0151(5) Uani 1 1 d .
N6 N 0.5357(3) 0.81134(7) 1.1613(3) 0.0209(5) Uani 1 1 d .
O1 O 0.4953(2) 1.01910(6) 0.6908(2) 0.0140(4) Uani 1 1 d .
O2 O 0.7578(2) 1.03709(6) 0.7476(2) 0.0162(4) Uani 1 1 d .
O3 O 0.9814(2) 0.96099(5) 0.9185(2) 0.0129(3) Uani 1 1 d .
O4 O 0.73380(19) 0.92789(5) 0.84574(19) 0.0119(3) Uani 1 1 d .
O5 O 0.52196(19) 0.95461(6) 1.00615(19) 0.0129(4) Uani 1 1 d .
O6 O 0.3442(2) 0.91078(5) 1.0466(2) 0.0140(4) Uani 1 1 d .
O7 O 0.9204(2) 0.94744(6) 1.2002(2) 0.0133(4) Uani 1 1 d D
O8 O 0.8223(2) 1.03487(6) 1.2655(2) 0.0165(4) Uani 1 1 d .
O9 O 0.8477(2) 0.94615(6) 0.4592(2) 0.0166(4) Uani 1 1 d .
O10 O 0.7549(2) 0.85659(6) 0.4465(2) 0.0257(4) Uani 1 1 d .
C1 C 0.6002(3) 1.04108(8) 0.6608(3) 0.0131(5) Uani 1 1 d .
C2 C 0.5304(3) 1.07311(9) 0.5185(3) 0.0158(5) Uani 1 1 d .
H2A H 0.4920 1.0553 0.4205 0.019 Uiso 1 1 calc R
H2B H 0.4323 1.0888 0.5145 0.019 Uiso 1 1 calc R
C3 C 0.6989(4) 1.14487(9) 0.6107(3) 0.0217(6) Uani 1 1 d .
H3 H 0.6544 1.1561 0.6763 0.026 Uiso 1 1 calc R
C4 C 0.8269(4) 1.16478(9) 0.5851(3) 0.0246(6) Uani 1 1 d .
H4 H 0.8852 1.1918 0.6282 0.029 Uiso 1 1 calc R
C5 C 0.8475(3) 1.13509(9) 0.4808(3) 0.0210(6) Uani 1 1 d .
H5 H 0.9266 1.1393 0.4429 0.025 Uiso 1 1 calc R
C6 C 0.8844(3) 0.92645(8) 0.8714(3) 0.0109(5) Uani 1 1 d .
C7 C 0.9614(3) 0.88258(8) 0.8490(3) 0.0190(6) Uani 1 1 d .
H7A H 0.9628 0.8838 0.7462 0.023 Uiso 1 1 calc R
H7B H 1.0784 0.8806 0.9327 0.023 Uiso 1 1 calc R
C8 C 0.8935(4) 0.81915(10) 0.9878(3) 0.0270(6) Uani 1 1 d .
H8 H 0.9729 0.8259 1.0931 0.032 Uiso 1 1 calc R
C9 C 0.7780(4) 0.78464(10) 0.9403(4) 0.0285(7) Uani 1 1 d .
H9 H 0.7619 0.7630 1.0046 0.034 Uiso 1 1 calc R
C10 C 0.6890(4) 0.78911(9) 0.7733(4) 0.0284(7) Uani 1 1 d .
H10 H 0.6011 0.7699 0.7065 0.034 Uiso 1 1 calc R
C11 C 0.4693(3) 0.91539(8) 1.0222(3) 0.0114(5) Uani 1 1 d .
C12 C 0.5648(3) 0.87434(8) 1.0075(3) 0.0160(5) Uani 1 1 d .
H12A H 0.5670 0.8759 0.9051 0.019 Uiso 1 1 calc R
H12B H 0.6815 0.8757 1.0922 0.019 Uiso 1 1 calc R
C13 C 0.3786(4) 0.80552(9) 0.8955(3) 0.0265(6) Uani 1 1 d .
H13 H 0.3310 0.8125 0.7864 0.032 Uiso 1 1 calc R
C14 C 0.3468(4) 0.76711(10) 0.9618(4) 0.0358(8) Uani 1 1 d .
H14 H 0.2745 0.7429 0.9084 0.043 Uiso 1 1 calc R
C15 C 0.4474(4) 0.77265(9) 1.1269(4) 0.0293(7) Uani 1 1 d .
H15 H 0.4523 0.7518 1.2038 0.035 Uiso 1 1 calc R
H3A H 0.917(6) 1.0370(15) 1.326(5) 0.080 Uiso 1 1 d .
H1B H 0.904(6) 0.9465(15) 1.273(5) 0.080 Uiso 1 1 d .
H1A H 1.043(3) 0.9481(13) 1.228(5) 0.080 Uiso 1 1 d D
H3B H 0.776(6) 1.0523(14) 1.306(5) 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'
Pr Pr -0.2180 2.8214 '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
O3 Pr1 O5 155.38(5) 3_777 .
O3 Pr1 O2 71.76(6) 3_777 .
O5 Pr1 O2 132.14(5) . .
O3 Pr1 O7 79.63(6) 3_777 .
O5 Pr1 O7 78.01(5) . .
O2 Pr1 O7 133.34(5) . .
O3 Pr1 O8 72.88(6) 3_777 .
O5 Pr1 O8 89.44(6) . .
O2 Pr1 O8 131.70(6) . .
O7 Pr1 O8 68.75(6) . .
O3 Pr1 O4 109.45(5) 3_777 .
O5 Pr1 O4 73.23(5) . .
O2 Pr1 O4 83.14(5) . .
O7 Pr1 O4 72.51(5) . .
O8 Pr1 O4 140.06(6) . .
O3 Pr1 O6 79.37(5) 3_777 3_677
O5 Pr1 O6 112.10(5) . 3_677
O2 Pr1 O6 69.54(5) . 3_677
O7 Pr1 O6 139.83(6) . 3_677
O8 Pr1 O6 72.48(6) . 3_677
O4 Pr1 O6 147.29(5) . 3_677
O3 Pr1 O1 120.76(5) 3_777 .
O5 Pr1 O1 83.85(5) . .
O2 Pr1 O1 50.51(5) . .
O7 Pr1 O1 149.38(5) . .
O8 Pr1 O1 135.99(6) . .
O4 Pr1 O1 78.77(5) . .
O6 Pr1 O1 70.12(5) 3_677 .
O3 Pr1 O5 122.72(5) 3_777 3_677
O5 Pr1 O5 62.83(6) . 3_677
O2 Pr1 O5 105.23(5) . 3_677
O7 Pr1 O5 121.26(5) . 3_677
O8 Pr1 O5 68.93(5) . 3_677
O4 Pr1 O5 127.31(5) . 3_677
O6 Pr1 O5 49.45(5) 3_677 3_677
O1 Pr1 O5 69.38(5) . 3_677
O3 Pr1 O3 61.19(6) 3_777 .
O5 Pr1 O3 117.97(5) . .
O2 Pr1 O3 66.57(5) . .
O7 Pr1 O3 67.49(5) . .
O8 Pr1 O3 120.41(5) . .
O4 Pr1 O3 48.33(5) . .
O6 Pr1 O3 127.77(5) 3_677 .
O1 Pr1 O3 100.79(5) . .
O5 Pr1 O3 170.15(5) 3_677 .
O3 Pr1 C1 95.15(6) 3_777 .
O5 Pr1 C1 109.45(6) . .
O2 Pr1 C1 25.37(6) . .
O7 Pr1 C1 152.39(6) . .
O8 Pr1 C1 135.88(6) . .
O4 Pr1 C1 84.06(6) . .
O6 Pr1 C1 63.52(6) 3_677 .
O1 Pr1 C1 25.75(6) . .
O5 Pr1 C1 84.49(6) 3_677 .
O3 Pr1 C1 86.14(6) . .
O3 Pr1 C11 100.33(6) 3_777 3_677
O5 Pr1 C11 88.00(6) . 3_677
O2 Pr1 C11 87.79(6) . 3_677
O7 Pr1 C11 133.96(6) . 3_677
O8 Pr1 C11 67.47(6) . 3_677
O4 Pr1 C11 144.14(6) . 3_677
O6 Pr1 C11 24.32(6) 3_677 3_677
O1 Pr1 C11 68.86(6) . 3_677
O5 Pr1 C11 25.19(6) 3_677 3_677
O3 Pr1 C11 151.59(6) . 3_677
C1 Pr1 C11 73.58(6) . 3_677
C3 N1 N2 112.4(2) . .
C3 N1 C2 127.1(2) . .
N2 N1 C2 120.4(2) . .
C5 N2 N1 104.3(2) . .
N4 N3 C8 111.3(2) . .
N4 N3 C7 122.2(2) . .
C8 N3 C7 126.3(2) . .
C10 N4 N3 104.9(2) . .
N6 N5 C13 111.6(2) . .
N6 N5 C12 120.8(2) . .
C13 N5 C12 127.5(2) . .
C15 N6 N5 105.0(2) . .
C1 O1 Pr1 89.43(14) . .
C1 O2 Pr1 95.70(14) . .
C6 O3 Pr1 151.38(15) . 3_777
C6 O3 Pr1 87.93(13) . .
Pr1 O3 Pr1 118.81(6) 3_777 .
C6 O4 Pr1 99.61(14) . .
C11 O5 Pr1 150.42(15) . .
C11 O5 Pr1 92.32(14) . 3_677
Pr1 O5 Pr1 117.17(6) . 3_677
C11 O6 Pr1 96.04(14) . 3_677
O2 C1 O1 121.4(2) . .
O2 C1 C2 120.5(2) . .
O1 C1 C2 118.0(2) . .
O2 C1 Pr1 58.92(12) . .
O1 C1 Pr1 64.83(12) . .
C2 C1 Pr1 163.46(17) . .
N1 C2 C1 113.65(19) . .
N1 C3 C4 106.9(2) . .
C5 C4 C3 104.1(2) . .
N2 C5 C4 112.3(2) . .
O4 C6 O3 122.4(2) . .
O4 C6 C7 121.0(2) . .
O3 C6 C7 116.6(2) . .
O4 C6 Pr1 56.47(12) . .
O3 C6 Pr1 67.31(12) . .
C7 C6 Pr1 166.93(17) . .
N3 C7 C6 113.9(2) . .
N3 C8 C9 107.6(3) . .
C8 C9 C10 104.2(3) . .
N4 C10 C9 112.0(3) . .
O6 C11 O5 121.9(2) . .
O6 C11 C12 121.2(2) . .
O5 C11 C12 116.9(2) . .
O6 C11 Pr1 59.64(12) . 3_677
O5 C11 Pr1 62.49(12) . 3_677
C12 C11 Pr1 174.20(16) . 3_677
N5 C12 C11 113.5(2) . .
N5 C13 C14 107.3(2) . .
C13 C14 C15 104.3(2) . .
N6 C15 C14 111.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pr1 O3 2.4446(16) 3_777
Pr1 O5 2.4796(16) .
Pr1 O2 2.5092(17) .
Pr1 O7 2.5157(17) .
Pr1 O8 2.5500(18) .
Pr1 O4 2.5573(16) .
Pr1 O6 2.5979(16) 3_677
Pr1 O1 2.6384(16) .
Pr1 O5 2.6580(16) 3_677
Pr1 O3 2.7927(16) .
Pr1 C1 2.915(2) .
Pr1 C11 2.994(2) 3_677
N1 C3 1.334(3) .
N1 N2 1.351(3) .
N1 C2 1.446(3) .
N2 C5 1.333(3) .
N3 N4 1.341(3) .
N3 C8 1.354(4) .
N3 C7 1.444(3) .
N4 C10 1.322(3) .
N5 N6 1.344(3) .
N5 C13 1.347(3) .
N5 C12 1.448(3) .
N6 C15 1.329(3) .
O1 C1 1.266(3) .
O2 C1 1.255(3) .
O3 C6 1.267(3) .
O3 Pr1 2.4447(16) 3_777
O4 C6 1.244(3) .
O5 C11 1.275(3) .
O5 Pr1 2.6579(16) 3_677
O6 C11 1.240(3) .
O6 Pr1 2.5980(16) 3_677
C1 C2 1.508(3) .
C3 C4 1.394(4) .
C4 C5 1.382(4) .
C6 C7 1.515(3) .
C8 C9 1.360(4) .
C9 C10 1.395(4) .
C11 C12 1.514(3) .
C11 Pr1 2.994(2) 3_677
C13 C14 1.376(4) .
C14 C15 1.391(4) .
