#------------------------------------------------------------------------------
#$Date: 2019-11-23 01:06:35 +0200 (Sat, 23 Nov 2019) $
#$Revision: 231729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/63/4346331.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_4346331
loop_
_publ_author_name
'Aulakh, Darpandeep'
'Varghese, Juby R.'
'Wriedt, Mario'
_publ_section_title
;
 The Importance of Polymorphism in Metal-Organic Framework Studies.
;
_journal_issue                   17
_journal_name_full               'Inorganic chemistry'
_journal_page_first              8679
_journal_page_last               8684
_journal_paper_doi               10.1021/acs.inorgchem.5b01311
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C14 H18 Eu N3 O9'
_chemical_formula_sum            'C14 H18 Eu N3 O9'
_chemical_formula_weight         524.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 96.136(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.200(7)
_cell_length_b                   10.737(4)
_cell_length_c                   10.684(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1961.8(13)
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_molecular_graphics    'SHELXP-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_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 area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14145
_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         28.342
_diffrn_reflns_theta_min         2.240
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.247
_exptl_absorpt_correction_T_max  0.774
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.241
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2451
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b01311_si_003.cif
_cod_data_source_block           jv356_290k
_cod_original_cell_volume        1961.7(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4346331
_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           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.5000 0.54320(3) 0.2500 0.03127(11) Uani 1 2 d S T P . .
O1 O 0.4152(2) 0.5801(4) 0.3975(3) 0.0663(11) Uani 1 1 d . . . . .
O2 O 0.4043(2) 0.5244(3) 0.5930(3) 0.0512(9) Uani 1 1 d . . . . .
O11 O 0.4575(3) 0.3286(4) 0.3159(4) 0.0814(13) Uani 1 1 d . . . . .
O12 O 0.5000 0.1540(7) 0.2500 0.199(6) Uani 1 2 d S T P . .
O21 O 0.4321(2) 0.7288(4) 0.1628(3) 0.0668(10) Uani 1 1 d . . . . .
N11 N 0.5000 0.2680(7) 0.2500 0.097(3) Uani 1 2 d S T P . .
C1 C 0.3836(2) 0.5856(4) 0.4967(4) 0.0380(10) Uani 1 1 d . . . . .
C2 C 0.3144(2) 0.6716(4) 0.4985(4) 0.0341(9) Uani 1 1 d . . . . .
C3 C 0.2802(3) 0.6892(4) 0.6088(4) 0.0414(10) Uani 1 1 d . . . . .
H3 H 0.3003 0.6486 0.6820 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2158(2) 0.7672(5) 0.6106(4) 0.0426(11) Uani 1 1 d . . . . .
H4 H 0.1929 0.7784 0.6848 0.051 Uiso 1 1 calc R U . . .
N21' N 0.3641(6) 0.8645(11) 0.0386(10) 0.091(4) Uani 0.65 1 d D . P A 1
C21' C 0.4003(6) 0.7573(9) 0.0664(8) 0.071(3) Uani 0.65 1 d D . P A 1
H21' H 0.4001 0.6993 0.0018 0.085 Uiso 0.65 1 calc R U P A 1
C22' C 0.3517(9) 0.9587(12) 0.1256(14) 0.113(5) Uiso 0.65 1 d D . P A 1
H22A H 0.3088 0.9359 0.1716 0.169 Uiso 0.65 1 calc R U P A 1
H22B H 0.3397 1.0355 0.0816 0.169 Uiso 0.65 1 calc R U P A 1
H22C H 0.3980 0.9692 0.1831 0.169 Uiso 0.65 1 calc R U P A 1
C23' C 0.3193(9) 0.8808(18) -0.0911(14) 0.139(5) Uiso 0.65 1 d D . P A 1
H23A H 0.3476 0.9363 -0.1402 0.208 Uiso 0.65 1 calc R U P A 1
H23B H 0.2686 0.9149 -0.0825 0.208 Uiso 0.65 1 calc R U P A 1
H23C H 0.3136 0.8014 -0.1323 0.208 Uiso 0.65 1 calc R U P A 1
N21 N 0.4100(11) 0.9061(18) 0.043(2) 0.091(4) Uani 0.35 1 d D . P A 2
C21 C 0.4527(12) 0.8211(17) 0.1079(18) 0.078(6) Uani 0.35 1 d D . P A 2
H21 H 0.5065 0.8334 0.1129 0.094 Uiso 0.35 1 calc R U P A 2
C22 C 0.4282(18) 1.018(2) -0.007(3) 0.149(12) Uiso 0.35 1 d D . P A 2
H22D H 0.4093 1.0838 0.0420 0.223 Uiso 0.35 1 calc R U P A 2
H22E H 0.4042 1.0234 -0.0922 0.223 Uiso 0.35 1 calc R U P A 2
H22F H 0.4839 1.0244 -0.0061 0.223 Uiso 0.35 1 calc R U P A 2
C23 C 0.3225(14) 0.867(3) 0.033(4) 0.150 Uiso 0.35 1 d D U P A 2
H23D H 0.2943 0.9249 0.0797 0.225 Uiso 0.35 1 calc R U P A 2
H23E H 0.3183 0.7850 0.0666 0.225 Uiso 0.35 1 calc R U P A 2
H23F H 0.3010 0.8681 -0.0539 0.225 Uiso 0.35 1 calc R U P A 2
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 O1 160.1(2) . 2_655
O1 Eu1 O2 95.51(14) . 6_565
O1 Eu1 O2 90.65(12) 2_655 6_565
O1 Eu1 O2 90.65(12) . 5_666
O1 Eu1 O2 95.51(14) 2_655 5_666
O2 Eu1 O2 143.80(18) 6_565 5_666
O1 Eu1 O21 78.92(13) . .
O1 Eu1 O21 84.86(16) 2_655 .
O2 Eu1 O21 73.03(12) 6_565 .
O2 Eu1 O21 142.99(13) 5_666 .
O1 Eu1 O21 84.85(16) . 2_655
O1 Eu1 O21 78.92(14) 2_655 2_655
O2 Eu1 O21 142.99(13) 6_565 2_655
O2 Eu1 O21 73.03(13) 5_666 2_655
O21 Eu1 O21 70.74(19) . 2_655
O1 Eu1 O11 124.77(16) . 2_655
O1 Eu1 O11 75.13(16) 2_655 2_655
O2 Eu1 O11 73.78(14) 6_565 2_655
O2 Eu1 O11 73.47(14) 5_666 2_655
O21 Eu1 O11 140.74(14) . 2_655
O21 Eu1 O11 134.88(15) 2_655 2_655
O1 Eu1 O11 75.13(16) . .
O1 Eu1 O11 124.77(16) 2_655 .
O2 Eu1 O11 73.47(14) 6_565 .
O2 Eu1 O11 73.78(14) 5_666 .
O21 Eu1 O11 134.88(15) . .
O21 Eu1 O11 140.74(14) 2_655 .
O11 Eu1 O11 49.7(2) 2_655 .
O1 Eu1 N11 99.95(11) . .
O1 Eu1 N11 99.95(11) 2_655 .
O2 Eu1 N11 71.90(9) 6_565 .
O2 Eu1 N11 71.90(9) 5_666 .
O21 Eu1 N11 144.63(9) . .
O21 Eu1 N11 144.63(9) 2_655 .
O11 Eu1 N11 24.85(11) 2_655 .
O11 Eu1 N11 24.85(11) . .
C1 O1 Eu1 164.2(3) . .
C1 O2 Eu1 151.3(3) . 5_666
N11 O11 Eu1 96.5(4) . .
C21' O21 Eu1 135.9(5) . .
C21 O21 Eu1 133.8(9) . .
O12 N11 O11 121.4(3) . 2_655
O12 N11 O11 121.3(3) . .
O11 N11 O11 117.3(7) 2_655 .
O12 N11 Eu1 180.0 . .
O11 N11 Eu1 58.6(3) 2_655 .
O11 N11 Eu1 58.7(3) . .
O2 C1 O1 124.7(4) . .
O2 C1 C2 118.0(4) . .
O1 C1 C2 117.2(4) . .
C3 C2 C4 119.6(4) . 7_566
C3 C2 C1 120.2(4) . .
C4 C2 C1 120.2(4) 7_566 .
C2 C3 C4 120.4(4) . .
C2 C4 C3 120.0(4) 7_566 .
C21' N21' C22' 125.2(10) . .
C21' N21' C23' 118.9(12) . .
C22' N21' C23' 115.0(10) . .
O21 C21' N21' 126.6(10) . .
C21 N21 C22 133(2) . .
C21 N21 C23 109(2) . .
C22 N21 C23 118.1(19) . .
O21 C21 N21 129.7(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Eu1 O1 2.293(3) .
Eu1 O1 2.293(3) 2_655
Eu1 O2 2.337(3) 6_565
Eu1 O2 2.337(3) 5_666
Eu1 O21 2.444(4) .
Eu1 O21 2.444(4) 2_655
Eu1 O11 2.540(4) 2_655
Eu1 O11 2.540(4) .
Eu1 N11 2.955(7) .
O1 C1 1.243(5) .
O2 C1 1.240(6) .
O2 Eu1 2.337(3) 5_666
O11 N11 1.250(5) .
O12 N11 1.224(10) .
O21 C21' 1.153(9) .
O21 C21 1.223(19) .
N11 O11 1.250(6) 2_655
C1 C2 1.508(5) .
C2 C3 1.386(6) .
C2 C4 1.390(6) 7_566
C3 C4 1.390(6) .
C4 C2 1.390(6) 7_566
N21' C21' 1.328(10) .
N21' C22' 1.406(16) .
N21' C23' 1.521(16) .
N21 C21 1.322(15) .
N21 C22 1.36(2) .
N21 C23 1.55(2) .
