#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:08:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179615 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/79/4507915.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_4507915
loop_
_publ_author_name
'Hou, Guang-Feng'
'Li, Hong-Xing'
'Li, Wei-Zuo'
'Yan, Peng-Fei'
'Su, Xiao-Hong'
'Li, Guang-Ming'
_publ_section_title
;
 Two Series of Luminescent Flexible Polycarboxylate Lanthanide
 Coordination Complexes with Double Layer and Rectangle Metallomacrocycle
 Structures
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3374
_journal_paper_doi               10.1021/cg400174r
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C24 H44 Eu2 N2 O26'
_chemical_formula_sum            'C24 H44 Eu2 N2 O26'
_chemical_formula_weight         1080.53
_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                 111.261(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.709(11)
_cell_length_b                   8.793(5)
_cell_length_c                   14.599(7)
_cell_measurement_reflns_used    13712
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.99
_cell_volume                     3554(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_collection       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16919
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.600
_exptl_absorpt_correction_T_max  0.6106
_exptl_absorpt_correction_T_min  0.3793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.00016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0216
_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)+(0.0157P)²+5.1664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0437
_refine_ls_wR_factor_ref         0.0453
_reflns_number_gt                3329
_reflns_number_total             4062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400174r_si_002.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4507915
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
C1 C 0.07460(8) 0.3513(3) 0.21675(18) 0.0215(5) Uani 1 1 d .
C2 C 0.08264(9) 0.5058(3) 0.2341(2) 0.0281(6) Uani 1 1 d .
H2 H 0.1127 0.5388 0.2764 0.034 Uiso 1 1 calc R
C3 C 0.04687(9) 0.6123(3) 0.1900(2) 0.0275(6) Uani 1 1 d .
H3 H 0.0531 0.7154 0.2025 0.033 Uiso 1 1 calc R
C4 C 0.00202(8) 0.5644(3) 0.12749(19) 0.0243(5) Uani 1 1 d .
C5 C -0.00708(9) 0.4104(3) 0.1114(2) 0.0282(6) Uani 1 1 d .
H5 H -0.0375 0.3776 0.0705 0.034 Uiso 1 1 calc R
C6 C 0.02876(9) 0.3050(3) 0.1556(2) 0.0272(6) Uani 1 1 d .
H6 H 0.0222 0.2018 0.1444 0.033 Uiso 1 1 calc R
C7 C -0.02510(9) 0.8186(3) 0.0858(2) 0.0313(6) Uani 1 1 d .
H7A H 0.0036 0.8357 0.0702 0.038 Uiso 1 1 calc R
H7B H -0.0182 0.8518 0.1529 0.038 Uiso 1 1 calc R
C8 C -0.06664(9) 0.9129(3) 0.0167(2) 0.0269(6) Uani 1 1 d .
C9 C 0.10348(9) 0.0853(3) 0.2534(2) 0.0276(6) Uani 1 1 d .
H9A H 0.0785 0.0617 0.1906 0.033 Uiso 1 1 calc R
H9B H 0.0915 0.0580 0.3049 0.033 Uiso 1 1 calc R
C10 C 0.14879(9) -0.0080(3) 0.26531(18) 0.0245(5) Uani 1 1 d .
C11 C 0.14778(9) 0.2893(3) 0.35683(19) 0.0256(6) Uani 1 1 d .
H11A H 0.1583 0.1973 0.3953 0.031 Uiso 1 1 calc R
H11B H 0.1308 0.3511 0.3890 0.031 Uiso 1 1 calc R
C12 C 0.19200(9) 0.3758(3) 0.35716(18) 0.0234(5) Uani 1 1 d .
Eu1 Eu 0.178547(4) 0.253317(15) 0.129466(8) 0.01815(5) Uani 1 1 d .
N1 N 0.11390(7) 0.2477(3) 0.25854(16) 0.0259(4) Uani 1 1 d .
O1 O 0.19910(6) 0.3958(2) 0.27790(13) 0.0267(4) Uani 1 1 d .
O2 O 0.21941(7) 0.4266(3) 0.43809(14) 0.0380(5) Uani 1 1 d .
O3 O 0.18271(6) 0.0580(2) 0.24803(13) 0.0268(4) Uani 1 1 d .
O4 O 0.14916(7) -0.1443(2) 0.28720(15) 0.0334(4) Uani 1 1 d .
O5 O -0.03597(6) 0.6614(2) 0.07850(15) 0.0305(4) Uani 1 1 d .
O6 O -0.10305(6) 0.8463(2) -0.04176(14) 0.0283(4) Uani 1 1 d .
O7 O -0.05985(8) 1.0516(2) 0.0224(2) 0.0563(7) Uani 1 1 d .
O8 O 0.12462(6) 0.4571(2) 0.05582(15) 0.0342(5) Uani 1 1 d .
H81 H 0.0962 0.4258 0.0222 0.051 Uiso 1 1 d R
H82 H 0.1242 0.5522 0.0679 0.051 Uiso 1 1 d R
O9 O 0.22559(6) 0.4820(2) 0.12120(13) 0.0298(4) Uani 1 1 d .
H91 H 0.2178 0.5303 0.0667 0.045 Uiso 1 1 d R
H92 H 0.2539 0.4944 0.1645 0.045 Uiso 1 1 d R
O10 O 0.18765(10) 0.2758(3) -0.02915(16) 0.0510(7) Uani 1 1 d .
H101 H 0.2001 0.3492 -0.0500 0.076 Uiso 1 1 d R
H102 H 0.1768 0.2085 -0.0742 0.076 Uiso 1 1 d R
O11 O 0.26430(6) 0.1949(2) 0.20221(15) 0.0311(4) Uani 1 1 d .
H111 H 0.2738 0.1024 0.2113 0.047 Uiso 1 1 d R
H112 H 0.2879 0.2542 0.2080 0.047 Uiso 1 1 d R
O12 O 0.19083(7) 0.0025(2) 0.05954(15) 0.0346(5) Uani 1 1 d .
H121 H 0.1788 -0.0778 0.0743 0.052 Uiso 1 1 d R
H122 H 0.2199 -0.0151 0.0655 0.052 Uiso 1 1 d R
O13 O 0.13041(8) 0.7634(2) 0.08317(16) 0.0391(5) Uani 1 1 d .
H131 H 0.1343 0.7689 0.1441 0.059 Uiso 1 1 d R
H132 H 0.1070 0.8213 0.0501 0.059 Uiso 1 1 d R
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
C2 C1 C6 117.9(2) . .
C2 C1 N1 119.1(2) . .
C6 C1 N1 123.0(2) . .
C1 C2 C3 121.6(2) . .
C1 C2 H2 119.2 . .
C3 C2 H2 119.2 . .
C4 C3 C2 119.6(3) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C5 119.6(2) . .
C3 C4 O5 124.3(2) . .
C5 C4 O5 116.2(2) . .
C6 C5 C4 120.4(2) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C1 120.8(3) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
O5 C7 C8 111.9(2) . .
O5 C7 H7A 109.2 . .
C8 C7 H7A 109.2 . .
O5 C7 H7B 109.2 . .
C8 C7 H7B 109.2 . .
H7A C7 H7B 107.9 . .
O7 C8 O6 126.0(3) . .
O7 C8 C7 114.8(2) . .
O6 C8 C7 119.2(2) . .
N1 C9 C10 110.9(2) . .
N1 C9 H9A 109.5 . .
C10 C9 H9A 109.5 . .
N1 C9 H9B 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 108.0 . .
O4 C10 O3 124.2(2) . .
O4 C10 C9 118.2(2) . .
O3 C10 C9 117.6(2) . .
N1 C11 C12 114.5(2) . .
N1 C11 H11A 108.6 . .
C12 C11 H11A 108.6 . .
N1 C11 H11B 108.6 . .
C12 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
O2 C12 O1 123.3(2) . .
O2 C12 C11 116.7(2) . .
O1 C12 C11 120.0(2) . .
O6 Eu1 O1 125.41(6) 5_565 .
O6 Eu1 O8 71.15(7) 5_565 .
O1 Eu1 O8 85.62(8) . .
O6 Eu1 O3 85.11(7) 5_565 .
O1 Eu1 O3 78.00(8) . .
O8 Eu1 O3 135.30(7) . .
O6 Eu1 O11 144.40(7) 5_565 .
O1 Eu1 O11 80.31(7) . .
O8 Eu1 O11 141.40(7) . .
O3 Eu1 O11 76.29(6) . .
O6 Eu1 O10 85.65(8) 5_565 .
O1 Eu1 O10 137.90(7) . .
O8 Eu1 O10 78.37(8) . .
O3 Eu1 O10 138.29(7) . .
O11 Eu1 O10 88.42(9) . .
O6 Eu1 O9 136.98(7) 5_565 .
O1 Eu1 O9 69.78(7) . .
O8 Eu1 O9 70.52(7) . .
O3 Eu1 O9 136.96(6) . .
O11 Eu1 O9 70.89(7) . .
O10 Eu1 O9 68.19(7) . .
O6 Eu1 O12 72.39(7) 5_565 .
O1 Eu1 O12 143.53(7) . .
O8 Eu1 O12 130.50(7) . .
O3 Eu1 O12 71.88(8) . .
O11 Eu1 O12 73.06(7) . .
O10 Eu1 O12 66.55(7) . .
O9 Eu1 O12 121.68(7) . .
O6 Eu1 N1 69.22(7) 5_565 .
O1 Eu1 N1 58.24(6) . .
O8 Eu1 N1 79.94(7) . .
O3 Eu1 N1 56.02(6) . .
O11 Eu1 N1 120.40(7) . .
O10 Eu1 N1 151.02(8) . .
O9 Eu1 N1 121.38(6) . .
O12 Eu1 N1 116.14(6) . .
C1 N1 C9 118.5(2) . .
C1 N1 C11 114.9(2) . .
C9 N1 C11 110.6(2) . .
C1 N1 Eu1 108.42(15) . .
C9 N1 Eu1 98.58(15) . .
C11 N1 Eu1 103.33(14) . .
C12 O1 Eu1 133.44(17) . .
C10 O3 Eu1 129.26(16) . .
C4 O5 C7 116.14(19) . .
C8 O6 Eu1 167.77(18) . 5_565
Eu1 O8 H81 112.3 . .
Eu1 O8 H82 134.3 . .
H81 O8 H82 110.4 . .
Eu1 O9 H91 118.7 . .
Eu1 O9 H92 119.2 . .
H91 O9 H92 119.0 . .
Eu1 O10 H101 127.8 . .
Eu1 O10 H102 122.3 . .
H101 O10 H102 109.8 . .
Eu1 O11 H111 120.2 . .
Eu1 O11 H112 127.3 . .
H111 O11 H112 110.7 . .
Eu1 O12 H121 119.2 . .
Eu1 O12 H122 114.2 . .
H121 O12 H122 109.1 . .
H131 O13 H132 109.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.386(4) .
C1 C6 1.391(3) .
C1 N1 1.431(3) .
C2 C3 1.387(4) .
C2 H2 0.9300 .
C3 C4 1.380(3) .
C3 H3 0.9300 .
C4 C5 1.385(4) .
C4 O5 1.388(3) .
C5 C6 1.382(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 O5 1.415(3) .
C7 C8 1.525(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 O7 1.234(3) .
C8 O6 1.254(3) .
C9 N1 1.457(3) .
C9 C10 1.531(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O4 1.239(3) .
C10 O3 1.265(3) .
C11 N1 1.469(3) .
C11 C12 1.516(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 O2 1.249(3) .
C12 O1 1.262(3) .
Eu1 O6 2.3139(19) 5_565
Eu1 O1 2.383(2) .
Eu1 O8 2.384(2) .
Eu1 O3 2.410(2) .
Eu1 O11 2.433(2) .
Eu1 O10 2.435(2) .
Eu1 O9 2.477(2) .
Eu1 O12 2.511(2) .
Eu1 N1 3.141(2) .
O6 Eu1 2.3139(18) 5_565
O8 H81 0.8544 .
O8 H82 0.8551 .
O9 H91 0.8561 .
O9 H92 0.8556 .
O10 H101 0.8531 .
O10 H102 0.8562 .
O11 H111 0.8550 .
O11 H112 0.8525 .
O12 H121 0.8535 .
O12 H122 0.8511 .
O13 H131 0.8554 .
O13 H132 0.8552 .
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
O8 H81 O5 0.85 2.01 2.850(3) 167.3 5_565
O8 H82 O13 0.86 1.87 2.718(3) 170.4 .
O9 H91 O2 0.86 1.93 2.733(3) 154.9 6_565
O9 H92 O3 0.86 1.94 2.782(3) 169.8 4
O10 H101 O2 0.85 2.08 2.880(3) 156.3 6_565
O10 H102 O4 0.86 1.97 2.758(3) 152.6 6
O11 H111 O1 0.85 1.97 2.820(3) 172.6 4_545
O11 H111 O9 0.85 2.66 3.111(3) 114.4 4_545
O11 H112 O4 0.85 2.05 2.889(3) 167.4 4
O12 H121 O13 0.85 2.04 2.866(3) 161.9 1_545
O12 H122 O2 0.85 1.89 2.737(3) 171.3 4_545
O13 H131 O4 0.86 2.12 2.939(3) 161.5 1_565
O13 H132 O7 0.86 1.81 2.660(3) 176.9 5_575
