#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/35/4113554.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_4113554
loop_
_publ_author_name
'Tomoaki Hamada'
'Kei Manabe'
'Shunpei Ishikawa'
'Satoshi Nagayama'
'Motoo Shiro'
'Shū Kobayashi'
_publ_section_title
;
 Catalytic Asymmetric Aldol Reactions in Aqueous Media Using Chiral
 Bis-pyridino-18-crown-6-Rare Earth Metal Triflate Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2989
_journal_page_last               2996
_journal_paper_doi               10.1021/ja028698z
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C22 H30 Ce1.33 N6 O16'
_chemical_formula_weight         820.87
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      146
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   27.433(3)
_cell_length_b                   27.439(5)
_cell_length_c                   10.784(4)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    123.2
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      12.2
_cell_volume                     7030(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SAPI91
_diffrn_measured_fraction_theta_full 1.7832
_diffrn_measured_fraction_theta_max 1.7832
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            23179
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_exptl_absorpt_coefficient_mu    2.006
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_description       block
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         3.27
_refine_diff_density_min         -8.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     408
_refine_ls_number_reflns         4757
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.0410
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.12600(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                3688
_reflns_number_total             8510
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja028698zsi20030105_093047_1.cif
_cod_data_source_block           001013TH
_cod_original_cell_volume        7028(3)
_cod_original_sg_symbol_H-M      'R 3 '
_cod_original_formula_sum        'C22 H30 Ce1.33 N6 O16 '
_cod_database_code               4113554
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y,x-y,z
-x+y,-x,z
2/3+x,1/3+y,1/3+z
2/3-y,1/3+x-y,1/3+z
2/3-x+y,1/3-x,1/3+z
1/3+x,2/3+y,2/3+z
1/3-y,2/3+x-y,2/3+z
1/3-x+y,2/3-x,2/3+z
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_calc_flag
_atom_site_refinement_flags
Ce(1) Ce 0.50187(1) 0.00114(1) 0.0013 0.01591(9) Uani 1.00 d .
Ce(2) Ce 0.0000 0.0000 0.00002(6) 0.01706(9) Uani 1.00 d SP
O(1) O 0.5526(2) 0.1081(2) 0.0166(6) 0.0197(9) Uani 1.00 d .
O(2) O 0.6091(2) 0.0545(2) 0.0175(6) 0.0210(9) Uani 1.00 d .
O(3) O 0.4491(2) -0.0973(2) -0.1001(6) 0.0225(10) Uani 1.00 d .
O(4) O 0.3970(2) -0.0598(2) 0.0354(6) 0.0226(10) Uani 1.00 d .
O(5) O 0.5262(2) -0.0474(2) 0.1789(6) 0.027(1) Uani 1.00 d .
O(6) O 0.4919(2) 0.0051(2) 0.2369(7) 0.029(1) Uani 1.00 d .
O(7) O 0.5118(2) -0.0408(2) 0.3761(6) 0.031(1) Uani 1.00 d .
O(8) O 0.4606(2) 0.0323(2) -0.1727(6) 0.032(1) Uani 1.00 d .
O(9) O 0.5233(2) 0.0120(2) -0.2338(6) 0.026(1) Uani 1.00 d .
O(10) O 0.4871(2) 0.0455(2) -0.3665(6) 0.028(1) Uani 1.00 d .
O(11) O 0.0629(2) 0.0606(2) -0.1874(7) 0.028(1) Uani 1.00 d .
O(12) O 0.0285(2) 0.1036(2) -0.0801(7) 0.026(1) Uani 1.00 d .
O(13) O 0.0806(3) 0.1442(3) -0.2444(8) 0.056(2) Uani 1.00 d .
O(14) O -0.0758(2) 0.0273(2) 0.0715(7) 0.028(1) Uani 1.00 d .
O(15) O 0.0006(2) 0.0632(2) 0.1796(7) 0.028(1) Uani 1.00 d .
O(16) O -0.0651(2) 0.0828(2) 0.2261(7) 0.044(1) Uani 1.00 d .
N(1) N 0.4458(2) 0.0514(2) 0.0798(7) 0.018(1) Uani 1.00 d .
N(2) N 0.5594(2) -0.0489(2) -0.0716(7) 0.022(1) Uani 1.00 d .
N(3) N 0.5101(2) -0.0282(2) 0.2683(7) 0.022(1) Uani 1.00 d .
N(4) N 0.4907(2) 0.0310(2) -0.2628(7) 0.021(1) Uani 1.00 d .
N(5) N -0.0471(2) 0.0583(2) 0.1608(7) 0.027(1) Uani 1.00 d .
N(6) N 0.0577(2) 0.1041(2) -0.1719(8) 0.028(1) Uani 1.00 d .
C(1) C 0.3905(2) 0.0192(2) 0.1071(7) 0.023(1) Uani 1.00 d .
C(2) C 0.3567(2) 0.0432(3) 0.1338(8) 0.026(1) Uani 1.00 d .
C(3) C 0.3813(3) 0.1009(3) 0.1366(8) 0.029(2) Uani 1.00 d .
C(4) C 0.4381(2) 0.1338(2) 0.1117(7) 0.023(1) Uani 1.00 d .
C(5) C 0.4690(2) 0.1073(2) 0.0831(7) 0.020(1) Uani 1.00 d .
C(6) C 0.5306(2) 0.1427(2) 0.0598(8) 0.026(1) Uani 1.00 d .
C(7) C 0.6128(2) 0.1418(2) -0.0121(7) 0.022(1) Uani 1.00 d .
C(8) C 0.6224(3) 0.1457(3) -0.1498(8) 0.029(1) Uani 1.00 d .
C(9) C 0.6406(3) 0.1139(2) 0.0566(8) 0.023(1) Uani 1.00 d .
C(10) C 0.6384(3) 0.1174(3) 0.1967(8) 0.032(2) Uani 1.00 d .
C(11) C 0.6397(3) 0.0257(3) 0.0389(8) 0.026(1) Uani 1.00 d .
C(12) C 0.6120(2) -0.0295(2) -0.0307(7) 0.020(1) Uani 1.00 d .
C(13) C 0.6404(3) -0.0589(3) -0.0455(8) 0.026(1) Uani 1.00 d .
C(14) C 0.6136(3) -0.1098(3) -0.1094(8) 0.029(2) Uani 1.00 d .
C(15) C 0.5595(3) -0.1301(3) -0.1534(7) 0.025(1) Uani 1.00 d .
C(16) C 0.5338(2) -0.0980(2) -0.1336(7) 0.021(1) Uani 1.00 d .
C(17) C 0.4760(3) -0.1178(3) -0.1831(8) 0.027(1) Uani 1.00 d .
C(18) C 0.3877(2) -0.1312(2) -0.1035(8) 0.026(1) Uani 1.00 d .
C(19) C 0.3641(3) -0.1161(3) -0.2146(9) 0.034(2) Uani 1.00 d .
C(20) C 0.3691(3) -0.1208(2) 0.0210(9) 0.030(2) Uani 1.00 d .
C(21) C 0.3840(3) -0.1471(3) 0.1283(9) 0.037(2) Uani 1.00 d .
C(22) C 0.3659(3) -0.0426(3) 0.1127(8) 0.031(2) Uani 1.00 d .
H(2) H 0.3176 0.0199 0.1493 0.0315 Uiso 1.00 calc .
H(3) H 0.3595 0.1179 0.1551 0.0347 Uiso 1.00 calc .
H(4) H 0.4558 0.1737 0.1137 0.0272 Uiso 1.00 calc .
H(6a) H 0.5491 0.1609 0.1341 0.0315 Uiso 1.00 calc .
H(6b) H 0.5368 0.1701 -0.0017 0.0315 Uiso 1.00 calc .
H(7) H 0.6268 0.1787 0.0199 0.0266 Uiso 1.00 calc .
H(8a) H 0.6053 0.1089 -0.1845 0.0344 Uiso 1.00 calc .
H(8b) H 0.6063 0.1660 -0.1864 0.0344 Uiso 1.00 calc .
H(8c) H 0.6617 0.1648 -0.1664 0.0344 Uiso 1.00 calc .
H(9) H 0.6787 0.1300 0.0305 0.0279 Uiso 1.00 calc .
H(10a) H 0.6637 0.1549 0.2226 0.0383 Uiso 1.00 calc .
H(10b) H 0.6013 0.1071 0.2213 0.0383 Uiso 1.00 calc .
H(10c) H 0.6489 0.0926 0.2332 0.0383 Uiso 1.00 calc .
H(11a) H 0.6773 0.0483 0.0104 0.0316 Uiso 1.00 calc .
H(11b) H 0.6399 0.0187 0.1248 0.0316 Uiso 1.00 calc .
H(13) H 0.6772 -0.0448 -0.0132 0.0311 Uiso 1.00 calc .
H(14) H 0.6324 -0.1305 -0.1230 0.0352 Uiso 1.00 calc .
H(15) H 0.5403 -0.1651 -0.1964 0.0305 Uiso 1.00 calc .
H(17a) H 0.4553 -0.1577 -0.1863 0.0320 Uiso 1.00 calc .
H(17b) H 0.4782 -0.1032 -0.2644 0.0320 Uiso 1.00 calc .
H(18) H 0.3772 -0.1698 -0.1094 0.0310 Uiso 1.00 calc .
H(19a) H 0.3298 -0.1480 -0.2400 0.0412 Uiso 1.00 calc .
H(19b) H 0.3574 -0.0864 -0.1931 0.0412 Uiso 1.00 calc .
H(19c) H 0.3904 -0.1043 -0.2810 0.0412 Uiso 1.00 calc .
H(20) H 0.3295 -0.1357 0.0193 0.0358 Uiso 1.00 calc .
H(21a) H 0.3781 -0.1335 0.2043 0.0450 Uiso 1.00 calc .
H(21b) H 0.3609 -0.1869 0.1247 0.0450 Uiso 1.00 calc .
H(21c) H 0.4224 -0.1372 0.1217 0.0450 Uiso 1.00 calc .
H(22a) H 0.3279 -0.0603 0.0846 0.0366 Uiso 1.00 calc .
H(22b) H 0.3669 -0.0534 0.1955 0.0366 Uiso 1.00 calc .
O(11*) O -0.0606(2) 0.0022(2) -0.1874(7) 0.028(1) Uani 1.00 d .
O(11') O -0.0022(2) -0.0629(2) -0.1874(7) 0.028(1) Uani 1.00 d .
O(12*) O -0.1036(2) -0.0751(2) -0.0801(7) 0.026(1) Uani 1.00 d .
O(12') O 0.0751(2) -0.0285(2) -0.0801(7) 0.026(1) Uani 1.00 d .
O(14*) O -0.0273(2) -0.1031(2) 0.0715(7) 0.028(1) Uani 1.00 d .
O(14') O 0.1031(2) 0.0758(2) 0.0715(7) 0.028(1) Uani 1.00 d .
O(15*) O -0.0632(2) -0.0626(2) 0.1796(7) 0.028(1) Uani 1.00 d .
O(15') O 0.0626(2) -0.0006(2) 0.1796(7) 0.028(1) Uani 1.00 d .
N(6*) N -0.1041(2) -0.0464(2) -0.1719(8) 0.028(1) Uani 1.00 d .
N(6') N 0.0464(2) -0.0577(2) -0.1719(8) 0.028(1) Uani 1.00 d .
N(5*) N -0.0583(2) -0.1054(2) 0.1608(7) 0.027(1) Uani 1.00 d .
N(5') N 0.1054(2) 0.0471(2) 0.1608(7) 0.027(1) Uani 1.00 d .
O(13*) O -0.1442(3) -0.0636(3) -0.2444(8) 0.056(2) Uani 1.00 d .
O(13') O 0.0636(3) -0.0806(3) -0.2444(8) 0.056(2) Uani 1.00 d .
O(16*) O -0.0828(2) -0.1479(2) 0.2261(7) 0.044(1) Uani 1.00 d .
O(16') O 0.1479(2) 0.0651(2) 0.2261(7) 0.044(1) Uani 1.00 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Ce Ce -0.249 2.633
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
