#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/77/4107724.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_4107724
loop_
_publ_author_name
'Akihiro Nojiri'
'Naoya Kumagai'
'Masakatsu Shibasaki'
_publ_section_title
;
 Asymmetric Catalysis via Dynamic Substrate/Ligand/Rare Earth Metal
 Conglomerate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5630
_journal_page_last               5631
_journal_paper_doi               10.1021/ja800326d
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C19 H26 N2 O3 '
_chemical_formula_sum            'C19 H26 N2 O3'
_chemical_formula_weight         330.43
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.2546(13)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   15.2764(3)
_cell_length_b                   12.2814(2)
_cell_length_c                   21.5584(4)
_cell_measurement_reflns_used    11267
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.7
_cell_volume                     3818.44(12)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3444
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424.00
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       11(12)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2599
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0078Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2175
_reflns_number_gt                2372
_reflns_number_total             3444
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja800326d-file004.cif
_cod_data_source_block           '_071229kumagai'
_cod_original_cell_volume        3818.41(13)
_cod_original_formula_sum        'C19 H26 N2 O3 '
_cod_database_code               4107724
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O(1) O -0.04610(15) 0.40723(17) 0.45199(11) 0.0316(6) Uani 1.00 1 d .
O(2) O 0.25802(15) 0.30064(18) 0.29490(11) 0.0320(6) Uani 1.00 1 d .
O(3) O 0.11742(15) 0.38543(18) 0.25682(11) 0.0341(6) Uani 1.00 1 d .
N(4) N 0.17100(18) 0.3078(2) 0.35846(13) 0.0292(7) Uani 1.00 1 d .
N(5) N 0.19675(19) 0.3516(2) 0.54295(14) 0.0352(8) Uani 1.00 1 d .
C(6) C 0.0867(2) 0.3228(2) 0.37480(15) 0.0237(8) Uani 1.00 1 d .
C(7) C 0.0617(2) 0.2172(2) 0.40195(16) 0.0279(8) Uani 1.00 1 d .
C(8) C -0.0013(2) 0.4530(2) 0.42283(15) 0.0266(8) Uani 1.00 1 d .
C(9) C 0.0981(2) 0.4189(2) 0.42581(15) 0.0242(8) Uani 1.00 1 d .
C(10) C 0.1356(2) 0.5245(2) 0.40518(16) 0.0307(9) Uani 1.00 1 d .
C(11) C 0.2858(2) 0.3289(2) 0.23755(15) 0.0285(8) Uani 1.00 1 d .
C(12) C 0.1762(2) 0.3352(2) 0.29874(16) 0.0283(9) Uani 1.00 1 d .
C(13) C 0.0323(2) 0.0173(2) 0.38843(16) 0.0319(9) Uani 1.00 1 d .
C(14) C 0.0370(2) 0.1228(2) 0.35311(15) 0.0315(9) Uani 1.00 1 d .
C(15) C 0.2896(2) 0.4518(2) 0.23092(18) 0.0366(10) Uani 1.00 1 d .
C(16) C 0.2212(2) 0.2743(2) 0.17612(18) 0.0388(10) Uani 1.00 1 d .
C(17) C -0.0302(2) 0.5507(2) 0.37824(17) 0.0314(9) Uani 1.00 1 d .
C(18) C 0.0505(2) 0.5753(2) 0.35389(16) 0.0326(9) Uani 1.00 1 d .
C(19) C -0.0483(2) -0.0121(2) 0.40083(17) 0.0406(10) Uani 1.00 1 d .
C(20) C 0.1102(3) -0.0484(2) 0.41219(18) 0.0434(11) Uani 1.00 1 d .
C(21) C 0.3827(2) 0.2802(3) 0.25576(18) 0.0388(10) Uani 1.00 1 d .
C(22) C -0.0503(3) -0.1078(3) 0.43529(18) 0.0529(13) Uani 1.00 1 d .
C(23) C 0.1531(2) 0.3820(2) 0.49183(16) 0.0268(8) Uani 1.00 1 d .
C(24) C 0.0266(3) -0.1732(3) 0.45788(19) 0.0558(13) Uani 1.00 1 d .
C(25) C 0.1069(3) -0.1437(3) 0.44683(18) 0.0524(12) Uani 1.00 1 d .
H(1) H -0.1060 -0.1238 0.4454 0.066 Uiso 1.00 1 c R
H(2) H -0.1047 0.0354 0.3857 0.050 Uiso 1.00 1 c R
H(3) H 0.0241 -0.2354 0.4812 0.070 Uiso 1.00 1 c R
H(4) H 0.1668 -0.1848 0.4653 0.066 Uiso 1.00 1 c R
H(5) H 0.0882 0.1144 0.3321 0.039 Uiso 1.00 1 c R
H(6) H -0.0233 0.1358 0.3170 0.040 Uiso 1.00 1 c R
H(7) H 0.1146 0.1949 0.4407 0.035 Uiso 1.00 1 c R
H(8) H 0.0072 0.2321 0.4182 0.035 Uiso 1.00 1 c R
H(9) H -0.0891 0.5350 0.3435 0.038 Uiso 1.00 1 c R
H(10) H -0.0394 0.6107 0.4056 0.038 Uiso 1.00 1 c R
H(11) H 0.0612 0.6552 0.3493 0.040 Uiso 1.00 1 c R
H(12) H 0.1966 0.5088 0.3892 0.037 Uiso 1.00 1 c R
H(13) H 0.1583 0.5708 0.4424 0.037 Uiso 1.00 1 c R
H(14) H 0.4212 0.3139 0.2964 0.049 Uiso 1.00 1 c R
H(15) H 0.4096 0.3008 0.2182 0.049 Uiso 1.00 1 c R
H(16) H 0.3766 0.1970 0.2605 0.049 Uiso 1.00 1 c R
H(17) H 0.3171 0.4679 0.1939 0.047 Uiso 1.00 1 c R
H(18) H 0.3316 0.4820 0.2698 0.047 Uiso 1.00 1 c R
H(19) H 0.2263 0.4876 0.2222 0.047 Uiso 1.00 1 c R
H(20) H 0.2482 0.2818 0.1400 0.048 Uiso 1.00 1 c R
H(21) H 0.2198 0.1981 0.1833 0.048 Uiso 1.00 1 c R
H(23) H 0.1566 0.3053 0.1645 0.048 Uiso 1.00 1 c R
H(24) H 0.0362 0.3437 0.3304 0.030 Uiso 1.00 1 c R
H(25) H 0.2150 0.2662 0.3847 0.037 Uiso 1.00 1 c R
H(26) H 0.1661 -0.0295 0.4045 0.057 Uiso 1.00 1 c R
H(27) H 0.0430 0.5404 0.3115 0.040 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, 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_publ_flag
C(11) O(2) C(12) 120.4(2) yes
C(6) N(4) C(12) 122.1(2) yes
N(4) C(6) C(7) 109.9(2) yes
N(4) C(6) C(9) 111.1(2) yes
C(7) C(6) C(9) 110.6(2) yes
C(6) C(7) C(14) 114.7(2) yes
O(1) C(8) C(9) 124.4(2) yes
O(1) C(8) C(17) 127.1(2) yes
C(9) C(8) C(17) 108.5(2) yes
C(6) C(9) C(8) 106.8(2) yes
C(6) C(9) C(10) 113.1(2) yes
C(6) C(9) C(23) 109.9(2) yes
C(8) C(9) C(10) 102.2(2) yes
C(8) C(9) C(23) 111.2(2) yes
C(10) C(9) C(23) 113.1(2) yes
C(9) C(10) C(18) 104.1(2) yes
O(2) C(11) C(15) 110.1(2) yes
O(2) C(11) C(16) 110.0(2) yes
O(2) C(11) C(21) 102.4(2) yes
C(15) C(11) C(16) 112.9(2) yes
C(15) C(11) C(21) 110.5(2) yes
C(16) C(11) C(21) 110.3(2) yes
O(2) C(12) O(3) 126.1(3) yes
O(2) C(12) N(4) 109.0(2) yes
O(3) C(12) N(4) 124.9(3) yes
C(14) C(13) C(19) 120.6(2) yes
C(14) C(13) C(20) 120.3(3) yes
C(19) C(13) C(20) 118.9(2) yes
C(7) C(14) C(13) 110.1(2) yes
C(8) C(17) C(18) 106.1(2) yes
C(10) C(18) C(17) 105.1(2) yes
C(13) C(19) C(22) 119.8(2) yes
C(13) C(20) C(25) 120.4(4) yes
C(19) C(22) C(24) 121.0(4) yes
N(5) C(23) C(9) 178.7(3) yes
C(22) C(24) C(25) 119.5(3) yes
C(20) C(25) C(24) 120.3(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(8) 1.210(4) yes
O(2) C(11) 1.475(4) yes
O(2) C(12) 1.348(4) yes
O(3) C(12) 1.212(3) yes
N(4) C(6) 1.455(4) yes
N(4) C(12) 1.358(4) yes
N(5) C(23) 1.146(3) yes
C(6) C(7) 1.522(4) yes
C(6) C(9) 1.583(4) yes
C(7) C(14) 1.527(3) yes
C(8) C(9) 1.556(4) yes
C(8) C(17) 1.510(3) yes
C(9) C(10) 1.541(4) yes
C(9) C(23) 1.466(4) yes
C(10) C(18) 1.534(3) yes
C(11) C(15) 1.519(3) yes
C(11) C(16) 1.522(3) yes
C(11) C(21) 1.523(4) yes
C(13) C(14) 1.517(3) yes
C(13) C(19) 1.391(4) yes
C(13) C(20) 1.388(4) yes
C(17) C(18) 1.521(5) yes
C(19) C(22) 1.396(4) yes
C(20) C(25) 1.398(4) yes
C(22) C(24) 1.373(5) yes
C(24) C(25) 1.373(6) yes
