#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/54/1505483.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_1505483
loop_
_publ_author_name
'Wooten, Alfred J.'
'Carroll, Patrick J.'
'Walsh, Patrick J.'
_publ_section_title
;
 Impact of Na- and K-C pi-interactions on the structure and binding of
 M3(sol)n(BINOLate)3Ln catalysts.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3359
_journal_page_last               3362
_journal_paper_doi               10.1021/ol0713234
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C84 H84 Eu Na3 O12'
_chemical_formula_weight         1506.44
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_Int_Tables_number      173
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            2
_cell_length_a                   15.152(9)
_cell_length_b                   15.152(9)
_cell_length_c                   18.20(2)
_cell_measurement_temperature    143(1)
_cell_volume                     3619(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13126
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6016
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.747
_refine_diff_density_min         -1.356
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0477P)²+5.2564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                4230
_reflns_number_total             4780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0713234-file005.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P 63     '
_cod_database_code               1505483
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.0000 0.0000 0.53392(6) 0.02058(10) Uani 1 3 d S . .
Na1 Na 0.20645(16) -0.03776(17) 0.48163(13) 0.0377(5) Uani 1 1 d . . .
O1 O 0.1462(2) 0.0685(2) 0.46328(19) 0.0260(7) Uani 1 1 d . . .
O2 O 0.0824(2) 0.1650(2) 0.57561(19) 0.0235(7) Uani 1 1 d . . .
O3 O 0.3087(4) -0.0651(4) 0.5640(2) 0.0557(12) Uani 1 1 d . B .
O4 O 0.3364(3) 0.0291(4) 0.3909(3) 0.0537(12) Uani 1 1 d . . .
C1 C 0.1786(4) 0.1553(4) 0.4271(3) 0.0268(10) Uani 1 1 d . . .
C2 C 0.1550(4) 0.1493(4) 0.3501(3) 0.0284(10) Uani 1 1 d . . .
H2 H 0.1184 0.0855 0.3280 0.038 Uiso 1 1 calc R . .
C3 C 0.1849(4) 0.2343(4) 0.3085(3) 0.0359(12) Uani 1 1 d . . .
H3 H 0.1711 0.2285 0.2584 0.048 Uiso 1 1 calc R . .
C4 C 0.2372(4) 0.3317(4) 0.3420(3) 0.0338(12) Uani 1 1 d . . .
C5 C 0.2675(4) 0.4222(4) 0.3009(4) 0.0430(15) Uani 1 1 d . . .
H5 H 0.2534 0.4167 0.2508 0.057 Uiso 1 1 calc R . .
C6 C 0.3154(5) 0.5144(5) 0.3312(4) 0.0454(15) Uani 1 1 d . . .
H6 H 0.3355 0.5723 0.3027 0.060 Uiso 1 1 calc R . .
C7 C 0.3351(4) 0.5231(4) 0.4077(4) 0.0443(15) Uani 1 1 d . . .
H7 H 0.3669 0.5872 0.4294 0.059 Uiso 1 1 calc R . .
C8 C 0.3087(4) 0.4394(4) 0.4502(3) 0.0361(12) Uani 1 1 d . . .
H8 H 0.3240 0.4477 0.5001 0.048 Uiso 1 1 calc R . .
C9 C 0.2573(4) 0.3384(4) 0.4192(3) 0.0302(11) Uani 1 1 d . . .
C10 C 0.2310(4) 0.2495(3) 0.4617(3) 0.0250(10) Uani 1 1 d . . .
C11 C 0.2579(3) 0.2568(3) 0.5413(3) 0.0242(10) Uani 1 1 d . . .
C12 C 0.3620(4) 0.3046(4) 0.5648(3) 0.0329(12) Uani 1 1 d . . .
C13 C 0.4445(4) 0.3430(4) 0.5139(3) 0.0320(13) Uani 1 1 d . . .
H13 H 0.4310 0.3373 0.4638 0.043 Uiso 1 1 calc R . .
C14 C 0.5452(4) 0.3890(4) 0.5380(5) 0.0439(13) Uani 1 1 d . . .
H14 H 0.5972 0.4129 0.5033 0.058 Uiso 1 1 calc R . .
C15 C 0.5706(5) 0.4004(5) 0.6127(4) 0.0481(16) Uani 1 1 d . . .
H15 H 0.6381 0.4315 0.6281 0.064 Uiso 1 1 calc R . .
C16 C 0.4902(4) 0.3631(4) 0.6633(4) 0.0415(14) Uani 1 1 d . . .
H16 H 0.5052 0.3700 0.7133 0.055 Uiso 1 1 calc R . .
C17 C 0.3860(4) 0.3148(4) 0.6407(3) 0.0379(13) Uani 1 1 d . . .
C18 C 0.3073(4) 0.2746(5) 0.6915(3) 0.0373(12) Uani 1 1 d . . .
H18 H 0.3225 0.2809 0.7414 0.050 Uiso 1 1 calc R . .
C19 C 0.2088(4) 0.2263(4) 0.6698(3) 0.0328(11) Uani 1 1 d . . .
H19 H 0.1570 0.1987 0.7048 0.044 Uiso 1 1 calc R . .
C20 C 0.1837(4) 0.2176(4) 0.5931(3) 0.0257(10) Uani 1 1 d . . .
C21 C 0.3542(8) -0.1239(8) 0.5703(4) 0.078(3) Uani 1 1 d DU . .
H21A H 0.4275 -0.0822 0.5647 0.104 Uiso 0.65 1 calc PR A 1
H21B H 0.3286 -0.1766 0.5330 0.104 Uiso 0.65 1 calc PR A 1
H21C H 0.4148 -0.0956 0.5398 0.104 Uiso 0.35 1 calc PR A 2
H21D H 0.3077 -0.1925 0.5533 0.104 Uiso 0.35 1 calc PR A 2
C22 C 0.328(2) -0.1711(12) 0.6466(8) 0.122(9) Uani 0.65 1 d PDU B 1
H22A H 0.2649 -0.2362 0.6465 0.162 Uiso 0.65 1 calc PR B 1
H22B H 0.3821 -0.1798 0.6669 0.162 Uiso 0.65 1 calc PR B 1
C22' C 0.383(3) -0.128(3) 0.6493(10) 0.096(10) Uani 0.35 1 d PDU B 2
H22C H 0.4552 -0.0817 0.6581 0.128 Uiso 0.35 1 calc PR B 2
H22D H 0.3650 -0.1960 0.6642 0.128 Uiso 0.35 1 calc PR B 2
C23 C 0.3161(11) -0.0906(11) 0.6879(5) 0.115(4) Uani 1 1 d DU . .
H23A H 0.2534 -0.1225 0.7162 0.152 Uiso 0.65 1 calc PR B 1
H23B H 0.3726 -0.0545 0.7216 0.152 Uiso 0.65 1 calc PR B 1
H23C H 0.2480 -0.1470 0.6972 0.152 Uiso 0.35 1 calc PR B 2
H23D H 0.3463 -0.0568 0.7340 0.152 Uiso 0.35 1 calc PR B 2
C24 C 0.3138(7) -0.0178(8) 0.6338(5) 0.073(2) Uani 1 1 d U B .
H24A H 0.2546 -0.0101 0.6413 0.097 Uiso 1 1 calc R . .
H24B H 0.3749 0.0486 0.6373 0.097 Uiso 1 1 calc R . .
C25 C 0.3912(6) 0.1348(5) 0.3751(6) 0.073(3) Uani 1 1 d . . .
H25A H 0.4041 0.1739 0.4201 0.097 Uiso 1 1 calc R . .
H25B H 0.3521 0.1526 0.3422 0.097 Uiso 1 1 calc R . .
C26 C 0.4864(8) 0.1573(9) 0.3411(6) 0.093(3) Uani 1 1 d . . .
H26A H 0.5434 0.2060 0.3705 0.124 Uiso 1 1 calc R . .
H26B H 0.4918 0.1861 0.2926 0.124 Uiso 1 1 calc R . .
C27 C 0.4871(5) 0.0579(7) 0.3355(4) 0.0593(19) Uani 1 1 d . . .
H27A H 0.4746 0.0323 0.2855 0.079 Uiso 1 1 calc R . .
H27B H 0.5514 0.0658 0.3523 0.079 Uiso 1 1 calc R . .
C28 C 0.4022(5) -0.0101(6) 0.3849(4) 0.0493(15) Uani 1 1 d . . .
H28A H 0.3662 -0.0785 0.3648 0.066 Uiso 1 1 calc R . .
H28B H 0.4285 -0.0128 0.4329 0.066 Uiso 1 1 calc 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
O2 Eu1 O2 109.63(9) . 3
O2 Eu1 O2 109.63(9) . 5
O2 Eu1 O2 109.63(9) 3 5
O2 Eu1 O1 76.53(13) . 3
O2 Eu1 O1 79.47(13) 3 3
O2 Eu1 O1 165.38(12) 5 3
O2 Eu1 O1 165.38(12) . 5
O2 Eu1 O1 76.53(13) 3 5
O2 Eu1 O1 79.47(13) 5 5
O1 Eu1 O1 92.04(13) 3 5
O2 Eu1 O1 79.47(13) . .
O2 Eu1 O1 165.38(12) 3 .
O2 Eu1 O1 76.53(13) 5 .
O1 Eu1 O1 92.04(13) 3 .
O1 Eu1 O1 92.04(13) 5 .
O2 Eu1 C1 152.98(12) . 5
O2 Eu1 C1 96.33(12) 3 5
O2 Eu1 C1 66.46(13) 5 5
O1 Eu1 C1 101.83(14) 3 5
O1 Eu1 C1 20.74(11) 5 5
O1 Eu1 C1 73.60(12) . 5
O2 Eu1 C1 96.33(12) . 3
O2 Eu1 C1 66.46(13) 3 3
O2 Eu1 C1 152.98(12) 5 3
O1 Eu1 C1 20.74(11) 3 3
O1 Eu1 C1 73.60(12) 5 3
O1 Eu1 C1 101.83(14) . 3
C1 Eu1 C1 87.03(15) 5 3
O2 Eu1 C1 66.46(13) . .
O2 Eu1 C1 152.98(12) 3 .
O2 Eu1 C1 96.33(12) 5 .
O1 Eu1 C1 73.60(12) 3 .
O1 Eu1 C1 101.84(14) 5 .
O1 Eu1 C1 20.74(11) . .
C1 Eu1 C1 87.03(15) 5 .
C1 Eu1 C1 87.03(15) 3 .
O2 Eu1 C20 20.47(11) . .
O2 Eu1 C20 126.13(13) 3 .
O2 Eu1 C20 91.09(11) 5 .
O1 Eu1 C20 92.43(12) 3 .
O1 Eu1 C20 157.34(12) 5 .
O1 Eu1 C20 65.61(13) . .
C1 Eu1 C20 137.14(12) 5 .
C1 Eu1 C20 113.10(12) 3 .
C1 Eu1 C20 58.44(14) . .
O2 Eu1 C20 91.09(11) . 3
O2 Eu1 C20 20.47(11) 3 3
O2 Eu1 C20 126.13(13) 5 3
O1 Eu1 C20 65.61(13) 3 3
O1 Eu1 C20 92.43(12) 5 3
O1 Eu1 C20 157.34(12) . 3
C1 Eu1 C20 113.10(12) 5 3
C1 Eu1 C20 58.44(14) 3 3
C1 Eu1 C20 137.14(12) . 3
C20 Eu1 C20 109.62(10) . 3
O2 Eu1 C20 126.13(13) . 5
O2 Eu1 C20 91.09(11) 3 5
O2 Eu1 C20 20.47(11) 5 5
O1 Eu1 C20 157.34(12) 3 5
O1 Eu1 C20 65.61(13) 5 5
O1 Eu1 C20 92.43(12) . 5
C1 Eu1 C20 58.44(14) 5 5
C1 Eu1 C20 137.14(12) 3 5
C1 Eu1 C20 113.10(12) . 5
C20 Eu1 C20 109.62(10) . 5
C20 Eu1 C20 109.62(10) 3 5
O1 Na1 O3 140.22(19) . .
O1 Na1 O4 97.98(16) . .
O3 Na1 O4 92.27(19) . .
O1 Na1 O2 76.34(13) . 5
O3 Na1 O2 89.27(17) . 5
O4 Na1 O2 172.59(17) . 5
O1 Na1 C10 99.17(14) . 5
O3 Na1 C10 107.67(18) . 5
O4 Na1 C10 121.86(18) . 5
O2 Na1 C10 64.34(14) 5 5
O1 Na1 C9 117.72(16) . 5
O3 Na1 C9 98.59(18) . 5
O4 Na1 C9 97.76(18) . 5
O2 Na1 C9 89.17(14) 5 5
C10 Na1 C9 27.17(13) 5 5
O1 Na1 Eu1 38.83(9) . .
O3 Na1 Eu1 124.60(15) . .
O4 Na1 Eu1 136.19(13) . .
O2 Na1 Eu1 39.13(8) 5 .
C10 Na1 Eu1 72.57(10) 5 .
C9 Na1 Eu1 98.82(11) 5 .
C1 O1 Na1 134.9(3) . .
C1 O1 Eu1 121.2(3) . .
Na1 O1 Eu1 103.78(14) . .
C20 O2 Eu1 123.6(3) . .
C20 O2 Na1 113.2(3) . 3
Eu1 O2 Na1 100.09(14) . 3
C21 O3 C24 109.2(6) . .
C21 O3 Na1 139.4(5) . .
C24 O3 Na1 110.6(4) . .
C28 O4 C25 109.0(5) . .
C28 O4 Na1 119.3(4) . .
C25 O4 Na1 121.0(4) . .
O1 C1 C10 122.2(5) . .
O1 C1 C2 117.6(4) . .
C10 C1 C2 120.2(4) . .
O1 C1 Eu1 38.1(2) . .
C10 C1 Eu1 108.6(3) . .
C2 C1 Eu1 116.9(3) . .
C3 C2 C1 121.8(5) . .
C2 C3 C4 119.6(5) . .
C3 C4 C5 121.3(5) . .
C3 C4 C9 119.0(5) . .
C5 C4 C9 119.6(5) . .
C6 C5 C4 122.5(6) . .
C5 C6 C7 119.0(5) . .
C8 C7 C6 121.4(6) . .
C7 C8 C9 121.1(6) . .
C10 C9 C4 121.1(5) . .
C10 C9 C8 122.6(5) . .
C4 C9 C8 116.3(5) . .
C10 C9 Na1 68.8(3) . 3
C4 C9 Na1 100.7(3) . 3
C8 C9 Na1 103.3(3) . 3
C1 C10 C9 118.1(5) . .
C1 C10 C11 120.6(4) . .
C9 C10 C11 121.2(4) . .
C1 C10 Na1 88.7(3) . 3
C9 C10 Na1 84.0(3) . 3
C11 C10 Na1 96.6(3) . 3
C20 C11 C12 118.5(5) . .
C20 C11 C10 120.4(4) . .
C12 C11 C10 121.1(5) . .
C17 C12 C13 117.6(5) . .
C17 C12 C11 120.2(5) . .
C13 C12 C11 122.2(5) . .
C14 C13 C12 121.2(6) . .
C13 C14 C15 122.1(6) . .
C14 C15 C16 117.3(5) . .
C15 C16 C17 122.2(6) . .
C18 C17 C12 119.0(5) . .
C18 C17 C16 121.4(6) . .
C12 C17 C16 119.6(6) . .
C19 C18 C17 121.2(5) . .
C18 C19 C20 120.2(5) . .
C11 C20 O2 122.5(4) . .
C11 C20 C19 120.8(5) . .
O2 C20 C19 116.6(4) . .
C11 C20 Eu1 108.4(3) . .
O2 C20 Eu1 36.0(2) . .
C19 C20 Eu1 117.9(3) . .
O3 C21 C22' 110.5(10) . .
O3 C21 C22 106.3(10) . .
C22' C21 C22 29.3(16) . .
C23 C22 C21 100.6(10) . .
C21 C22' C23 99.4(12) . .
C24 C23 C22 108.8(9) . .
C24 C23 C22' 103.2(13) . .
C22 C23 C22' 28.9(15) . .
O3 C24 C23 103.3(7) . .
O4 C25 C26 107.7(7) . .
C25 C26 C27 107.3(8) . .
C28 C27 C26 102.4(6) . .
O4 C28 C27 107.9(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Eu1 O2 2.294(3) .
Eu1 O2 2.294(3) 3
Eu1 O2 2.294(3) 5
Eu1 O1 2.311(4) 3
Eu1 O1 2.311(4) 5
Eu1 O1 2.311(4) .
Eu1 C1 3.205(5) 5
Eu1 C1 3.205(5) 3
Eu1 C1 3.205(5) .
Eu1 C20 3.256(5) .
Eu1 C20 3.256(5) 3
Eu1 C20 3.256(5) 5
Na1 O1 2.237(4) .
Na1 O3 2.337(5) .
Na1 O4 2.374(5) .
Na1 O2 2.374(4) 5
Na1 C10 2.910(6) 5
Na1 C9 3.105(6) 5
O1 C1 1.326(6) .
O2 C20 1.367(6) .
O2 Na1 2.374(4) 3
O3 C21 1.377(8) .
O3 C24 1.441(9) .
O4 C28 1.396(7) .
O4 C25 1.417(8) .
C1 C10 1.389(7) .
C1 C2 1.439(7) .
C2 C3 1.362(7) .
C3 C4 1.417(8) .
C4 C5 1.422(8) .
C4 C9 1.430(8) .
C5 C6 1.331(9) .
C6 C7 1.416(10) .
C7 C8 1.362(8) .
C8 C9 1.441(8) .
C9 C10 1.426(7) .
C9 Na1 3.105(6) 3
C10 C11 1.495(8) .
C10 Na1 2.910(6) 3
C11 C20 1.355(7) .
C11 C12 1.432(7) .
C12 C17 1.419(9) .
C12 C13 1.426(8) .
C13 C14 1.393(7) .
C14 C15 1.401(10) .
C15 C16 1.401(10) .
C16 C17 1.429(8) .
C17 C18 1.386(9) .
C18 C19 1.352(8) .
C19 C20 1.436(8) .
C21 C22' 1.511(18) .
C21 C22 1.521(15) .
C22 C23 1.517(16) .
C22' C23 1.552(18) .
C23 C24 1.491(14) .
C25 C26 1.446(12) .
C26 C27 1.514(14) .
C27 C28 1.483(10) .
