#------------------------------------------------------------------------------
#$Date: 2019-11-23 01:56:05 +0200 (Sat, 23 Nov 2019) $
#$Revision: 231821 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/65/4346516.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_4346516
loop_
_publ_author_name
'Zhao, Dian'
'Rao, Xingtang'
'Yu, Jiancan'
'Cui, Yuanjing'
'Yang, Yu'
'Qian, Guodong'
_publ_section_title
;
 Design and Synthesis of an MOF Thermometer with High Sensitivity in the
 Physiological Temperature Range.
;
_journal_issue                   23
_journal_name_full               'Inorganic chemistry'
_journal_page_first              11193
_journal_page_last               11199
_journal_paper_doi               10.1021/acs.inorgchem.5b01623
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C20 H22 Eu N3 O9, C3 H7 N O'
_chemical_formula_sum            'C23 H29 Eu N4 O10'
_chemical_formula_weight         673.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.6210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2044(2)
_cell_length_b                   13.7387(2)
_cell_length_c                   14.6444(3)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.32
_cell_volume                     2765.31(8)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33881
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.065
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.327
_exptl_absorpt_correction_T_max  0.541
_exptl_absorpt_correction_T_min  0.435
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.087
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0292P)²+2.5621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5663
_reflns_number_total             6304
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b01623_si_002.cif
_cod_data_source_block           EuL7
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4346516
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Eu1 Eu 0.13244(2) 0.93369(2) 0.01870(2) 0.02318(5) Uani 1 1 d . . .
O1 O -0.05855(14) 0.92073(12) 0.04522(13) 0.0358(4) Uani 1 1 d . . .
O2 O 0.06179(13) 0.82415(13) 0.11248(14) 0.0406(4) Uani 1 1 d . . .
O3 O 0.01695(13) 0.88236(14) -0.12031(13) 0.0387(4) Uani 1 1 d . . .
O4 O 0.12207(13) 1.03366(14) 0.14952(13) 0.0363(4) Uani 1 1 d . . .
O5 O 0.17628(15) 0.76822(14) -0.02009(14) 0.0447(5) Uani 1 1 d . . .
O6 O 0.22041(18) 0.94936(17) -0.10195(16) 0.0547(6) Uani 1 1 d . . .
O7 O 0.8124(7) 0.6017(7) -0.0749(6) 0.259(5) Uani 1 1 d . . .
O8 O 0.27308(17) 0.89081(18) 0.15206(17) 0.0585(6) Uani 1 1 d . . .
O9 O 0.29047(17) 1.0227(2) 0.08002(18) 0.0659(7) Uani 1 1 d . . .
O22 O 0.3885(2) 0.9923(3) 0.2167(2) 0.1061(12) Uani 1 1 d . . .
N1 N 0.2558(3) 0.8891(2) -0.2322(2) 0.0645(8) Uani 1 1 d . . .
N2 N 0.1301(2) 0.6248(2) -0.0938(2) 0.0610(8) Uani 1 1 d . . .
N3 N 0.6580(5) 0.6643(4) -0.1202(3) 0.1087(15) Uani 1 1 d . . .
N4 N 0.31908(19) 0.9690(3) 0.1506(2) 0.0595(8) Uani 1 1 d . . .
C1 C -0.02532(18) 0.84981(17) 0.09826(16) 0.0294(5) Uani 1 1 d . . .
C2 C -0.09116(17) 0.79300(18) 0.14378(17) 0.0303(5) Uani 1 1 d . . .
C3 C -0.19180(19) 0.8019(2) 0.11216(18) 0.0350(5) Uani 1 1 d . . .
C4 C -0.25320(18) 0.7432(2) 0.14919(19) 0.0363(6) Uani 1 1 d . . .
C5 C -0.21185(18) 0.82459(19) -0.28100(18) 0.0351(5) Uani 1 1 d . . .
C6 C -0.11143(17) 0.83086(18) -0.24611(17) 0.0305(5) Uani 1 1 d . . .
C7 C -0.06902(17) 0.89908(18) -0.16550(16) 0.0291(5) Uani 1 1 d . . .
C8 C -0.05118(18) 0.72760(18) 0.21571(17) 0.0309(5) Uani 1 1 d . . .
C11 C -0.36115(19) 0.7541(2) 0.1162(2) 0.0414(6) Uani 1 1 d . . .
C12 C -0.4025(2) 0.8451(3) 0.0935(3) 0.0546(8) Uani 1 1 d . . .
C13 C -0.5026(3) 0.8555(3) 0.0655(3) 0.0648(10) Uani 1 1 d . . .
C14 C -0.5628(2) 0.7762(3) 0.0581(3) 0.0653(10) Uani 1 1 d . . .
C15 C -0.5219(2) 0.6856(3) 0.0794(3) 0.0660(10) Uani 1 1 d . . .
C16 C -0.4218(2) 0.6744(3) 0.1092(2) 0.0534(8) Uani 1 1 d . . .
C23 C 0.2031(4) 0.9250(3) -0.1821(3) 0.0837(15) Uani 1 1 d . . .
H23 H 0.1385 0.9339 -0.2147 0.100 Uiso 1 1 calc R U .
C24 C 0.3558(6) 0.8676(8) -0.1926(5) 0.200(5) Uani 1 1 d . . .
H24A H 0.3950 0.9201 -0.2058 0.299 Uiso 1 1 calc R U .
H24B H 0.3726 0.8086 -0.2198 0.299 Uiso 1 1 calc R U .
H24C H 0.3672 0.8597 -0.1256 0.299 Uiso 1 1 calc R U .
C25 C 0.2247(6) 0.8585(5) -0.3275(4) 0.158(4) Uani 1 1 d . . .
H25A H 0.2042 0.7918 -0.3297 0.238 Uiso 1 1 calc R U .
H25B H 0.2775 0.8647 -0.3571 0.238 Uiso 1 1 calc R U .
H25C H 0.1713 0.8984 -0.3602 0.238 Uiso 1 1 calc R U .
C26 C 0.1169(3) 0.7018(2) -0.0471(2) 0.0515(7) Uani 1 1 d . . .
C27 C 0.2195(4) 0.6103(4) -0.1222(4) 0.115(2) Uani 1 1 d . . .
H27A H 0.2599 0.6669 -0.1063 0.172 Uiso 1 1 calc R U .
H27B H 0.2047 0.5997 -0.1891 0.172 Uiso 1 1 calc R U .
H27C H 0.2531 0.5546 -0.0900 0.172 Uiso 1 1 calc R U .
C28 C 0.0546(5) 0.5505(3) -0.1221(4) 0.1022(18) Uani 1 1 d . . .
H28A H -0.0025 0.5702 -0.1031 0.153 Uiso 1 1 calc R U .
H28B H 0.0779 0.4898 -0.0924 0.153 Uiso 1 1 calc R U .
H28C H 0.0387 0.5427 -0.1894 0.153 Uiso 1 1 calc R U .
C31 C 0.7527(8) 0.6705(6) -0.0952(5) 0.148(3) Uani 1 1 d . . .
H31 H 0.7789 0.7328 -0.0921 0.177 Uiso 1 1 calc R U .
C32 C 0.6013(5) 0.7476(5) -0.1412(4) 0.120(2) Uani 1 1 d . . .
H32A H 0.5338 0.7298 -0.1580 0.179 Uiso 0.5 1 calc R U P
H32B H 0.6169 0.7810 -0.1930 0.179 Uiso 0.5 1 calc R U P
H32C H 0.6141 0.7895 -0.0870 0.179 Uiso 0.5 1 calc R U P
H32D H 0.6428 0.8037 -0.1340 0.179 Uiso 0.5 1 calc R U P
H32E H 0.5596 0.7525 -0.0990 0.179 Uiso 0.5 1 calc R U P
H32F H 0.5624 0.7440 -0.2051 0.179 Uiso 0.5 1 calc R U P
C33 C 0.6164(10) 0.5707(6) -0.1178(9) 0.242(7) Uani 1 1 d . . .
H33A H 0.5468 0.5756 -0.1375 0.363 Uiso 0.5 1 calc R U P
H33B H 0.6355 0.5454 -0.0547 0.363 Uiso 0.5 1 calc R U P
H33C H 0.6389 0.5278 -0.1596 0.363 Uiso 0.5 1 calc R U P
H33D H 0.6673 0.5237 -0.0970 0.363 Uiso 0.5 1 calc R U P
H33E H 0.5786 0.5538 -0.1798 0.363 Uiso 0.5 1 calc R U P
H33F H 0.5753 0.5714 -0.0749 0.363 Uiso 0.5 1 calc R U P
H3 H -0.220(2) 0.849(2) 0.060(2) 0.043(8) Uiso 1 1 d . . .
H4 H 0.020(2) 0.725(2) 0.241(2) 0.035(7) Uiso 1 1 d . . .
H6 H 0.055(3) 0.695(3) -0.037(3) 0.072(12) Uiso 1 1 d . . .
H7 H -0.256(2) 0.867(2) -0.252(2) 0.038(8) Uiso 1 1 d . . .
H8 H -0.363(3) 0.905(3) 0.104(3) 0.060(10) Uiso 1 1 d . . .
H10 H -0.638(3) 0.782(3) 0.044(3) 0.066(11) Uiso 1 1 d . . .
H11 H -0.393(3) 0.607(3) 0.127(3) 0.065(11) Uiso 1 1 d . . .
H15 H -0.561(3) 0.626(3) 0.070(3) 0.078(12) Uiso 1 1 d . . .
H16 H -0.533(4) 0.921(3) 0.043(3) 0.093(15) 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'
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
O1 Eu1 O3 76.59(7) 3_575 .
O1 Eu1 O4 73.60(6) 3_575 .
O3 Eu1 O4 133.46(6) . .
O1 Eu1 O6 83.91(8) 3_575 .
O3 Eu1 O6 76.86(8) . .
O4 Eu1 O6 133.00(7) . .
O1 Eu1 O2 123.37(6) 3_575 .
O3 Eu1 O2 90.35(7) . .
O4 Eu1 O2 77.55(7) . .
O6 Eu1 O2 146.64(7) . .
O1 Eu1 O5 144.17(7) 3_575 .
O3 Eu1 O5 71.84(7) . .
O4 Eu1 O5 141.78(7) . .
O6 Eu1 O5 72.90(8) . .
O2 Eu1 O5 73.85(7) . .
O1 Eu1 O8 134.96(7) 3_575 .
O3 Eu1 O8 147.85(7) . .
O4 Eu1 O8 72.94(7) . .
O6 Eu1 O8 97.70(9) . .
O2 Eu1 O8 76.88(8) . .
O5 Eu1 O8 76.26(7) . .
O1 Eu1 O9 89.83(9) 3_575 .
O3 Eu1 O9 144.22(8) . .
O4 Eu1 O9 70.40(8) . .
O6 Eu1 O9 68.78(8) . .
O2 Eu1 O9 124.10(8) . .
O5 Eu1 O9 106.05(9) . .
O8 Eu1 O9 50.72(9) . .
O1 Eu1 O1 76.18(6) 3_575 .
O3 Eu1 O1 67.79(6) . .
O4 Eu1 O1 70.89(6) . .
O6 Eu1 O1 142.46(7) . .
O2 Eu1 O1 48.42(5) . .
O5 Eu1 O1 106.24(6) . .
O8 Eu1 O1 118.90(7) . .
O9 Eu1 O1 141.14(7) . .
O1 Eu1 N4 111.44(9) 3_575 .
O3 Eu1 N4 159.65(7) . .
O4 Eu1 N4 66.50(7) . .
O6 Eu1 N4 85.27(9) . .
O2 Eu1 N4 99.58(9) . .
O5 Eu1 N4 93.79(8) . .
O8 Eu1 N4 25.62(9) . .
O9 Eu1 N4 25.46(9) . .
O1 Eu1 N4 131.55(7) . .
O1 Eu1 C1 100.36(7) 3_575 .
O3 Eu1 C1 78.30(7) . .
O4 Eu1 C1 72.96(7) . .
O6 Eu1 C1 153.05(7) . .
O2 Eu1 C1 23.71(6) . .
O5 Eu1 C1 89.55(7) . .
O8 Eu1 C1 97.74(8) . .
O9 Eu1 C1 137.23(7) . .
O1 Eu1 C1 24.72(6) . .
N4 Eu1 C1 116.87(8) . .
O1 Eu1 Eu1 42.42(5) 3_575 3_575
O3 Eu1 Eu1 66.72(4) . 3_575
O4 Eu1 Eu1 67.11(4) . 3_575
O6 Eu1 Eu1 119.35(7) . 3_575
O2 Eu1 Eu1 81.59(4) . 3_575
O5 Eu1 Eu1 131.17(5) . 3_575
O8 Eu1 Eu1 137.74(6) . 3_575
O9 Eu1 Eu1 122.63(7) . 3_575
O1 Eu1 Eu1 33.76(3) . 3_575
N4 Eu1 Eu1 132.07(6) . 3_575
C1 Eu1 Eu1 58.12(5) . 3_575
C1 O1 Eu1 165.14(17) . 3_575
C1 O1 Eu1 84.88(14) . .
Eu1 O1 Eu1 103.82(6) 3_575 .
C1 O2 Eu1 105.34(15) . .
C7 O3 Eu1 140.10(16) . .
C7 O4 Eu1 137.37(16) 3_575 .
C26 O5 Eu1 124.3(2) . .
C23 O6 Eu1 133.0(3) . .
N4 O8 Eu1 95.85(19) . .
N4 O9 Eu1 94.75(19) . .
C23 N1 C25 126.9(5) . .
C23 N1 C24 121.1(5) . .
C25 N1 C24 111.7(5) . .
C26 N2 C27 121.2(4) . .
C26 N2 C28 121.6(4) . .
C27 N2 C28 117.2(4) . .
C31 N3 C32 120.5(7) . .
C31 N3 C33 117.3(8) . .
C32 N3 C33 122.1(8) . .
O22 N4 O9 121.5(4) . .
O22 N4 O8 121.4(4) . .
O9 N4 O8 117.1(3) . .
O22 N4 Eu1 168.2(2) . .
O9 N4 Eu1 59.79(15) . .
O8 N4 Eu1 58.54(14) . .
O2 C1 O1 121.4(2) . .
O2 C1 C2 118.8(2) . .
O1 C1 C2 119.9(2) . .
O2 C1 Eu1 50.96(12) . .
O1 C1 Eu1 70.40(13) . .
C2 C1 Eu1 169.51(17) . .
C8 C2 C3 119.8(2) . .
C8 C2 C1 119.5(2) . .
C3 C2 C1 120.7(2) . .
C2 C3 C4 120.7(2) . .
C3 C4 C5 118.8(2) . 4_576
C3 C4 C11 120.5(2) . .
C5 C4 C11 120.7(2) 4_576 .
C6 C5 C4 120.8(2) . 4_575
C8 C6 C5 119.7(2) 4_575 .
C8 C6 C7 120.6(2) 4_575 .
C5 C6 C7 119.7(2) . .
O4 C7 O3 126.0(2) 3_575 .
O4 C7 C6 117.7(2) 3_575 .
O3 C7 C6 116.3(2) . .
C6 C8 C2 120.2(2) 4_576 .
C16 C11 C12 118.7(3) . .
C16 C11 C4 120.9(3) . .
C12 C11 C4 120.4(3) . .
C13 C12 C11 120.4(3) . .
C14 C13 C12 120.9(4) . .
C13 C14 C15 118.8(3) . .
C14 C15 C16 120.8(4) . .
C11 C16 C15 120.4(3) . .
O6 C23 N1 132.5(5) . .
O5 C26 N2 126.3(4) . .
O7 C31 N3 127.2(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Eu1 O1 2.3413(17) 3_575
Eu1 O3 2.3763(17) .
Eu1 O4 2.3917(17) .
Eu1 O6 2.417(2) .
Eu1 O2 2.4194(17) .
Eu1 O5 2.4611(18) .
Eu1 O8 2.486(2) .
Eu1 O9 2.515(2) .
Eu1 O1 2.8415(19) .
Eu1 N4 2.900(3) .
Eu1 C1 3.004(2) .
Eu1 Eu1 4.0908(2) 3_575
O1 C1 1.261(3) .
O1 Eu1 2.3413(17) 3_575
O2 C1 1.252(3) .
O3 C7 1.254(3) .
O4 C7 1.251(3) 3_575
O5 C26 1.238(4) .
O6 C23 1.185(5) .
O7 C31 1.253(9) .
O8 N4 1.260(4) .
O9 N4 1.251(4) .
O22 N4 1.238(4) .
N1 C23 1.272(5) .
N1 C25 1.417(6) .
N1 C24 1.423(8) .
N2 C26 1.298(4) .
N2 C27 1.445(6) .
N2 C28 1.463(6) .
N3 C31 1.305(10) .
N3 C32 1.388(7) .
N3 C33 1.419(9) .
C1 C2 1.497(3) .
C2 C8 1.392(3) .
C2 C3 1.392(3) .
C3 C4 1.394(4) .
C4 C5 1.397(4) 4_576
C4 C11 1.494(4) .
C5 C6 1.391(3) .
C5 C4 1.398(4) 4_575
C6 C8 1.390(3) 4_575
C6 C7 1.509(3) .
C7 O4 1.251(3) 3_575
C8 C6 1.390(3) 4_576
C11 C16 1.381(4) .
C11 C12 1.386(4) .
C12 C13 1.385(5) .
C13 C14 1.372(6) .
C14 C15 1.376(6) .
C15 C16 1.387(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H23 O3 0.93 2.57 3.060(5) 113.5 .
C25 H25A O2 0.96 2.55 3.376(6) 144.8 4_575
C32 H32D O9 0.96 2.61 3.526(8) 158.8 3_675
