#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/73/1507364.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_1507364
loop_
_publ_author_name
'Shin, Dong-Yun'
'Jung, Jae-Kyung'
'Seo, Seung-Yong'
'Lee, Yong-Sil'
'Paek, Seung-Mann'
'Chung, Young Keun'
'Shin, Dong Mok'
'Suh, Young-Ger'
_publ_section_title
;
 Stereoselective formation of N-acyliminium ion via chiral N,O-acetal TMS
 ether and its application to the synthesis of beta-amino acids.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3635
_journal_page_last               3638
_journal_paper_doi               10.1021/ol035289e
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C21 H27 N O3 Si'
_chemical_formula_weight         369.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2287(3)
_cell_length_b                   9.9625(3)
_cell_length_c                   23.3118(6)
_cell_measurement_reflns_used    3867
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.998
_cell_volume                     2143.31(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP 32'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6910
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.128
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(19)
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0522
_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)+(0.0525P)²+0.3692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                2745
_reflns_number_total             3874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035289esi20030712_120133.cif
_cod_data_source_block           or
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'ORTHORHOMBIC' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1507364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
Si1 Si 0.91030(10) 0.64892(10) 0.83086(4) 0.0829(3) Uani 1 1 d .
O1 O 0.8102(3) 0.8274(2) 0.98972(10) 0.0924(7) Uani 1 1 d .
O2 O 0.9370(2) 0.68633(18) 1.04516(9) 0.0820(6) Uani 1 1 d .
O3 O 0.8263(2) 0.55414(19) 0.87785(8) 0.0728(6) Uani 1 1 d .
N1 N 0.8027(3) 0.5983(2) 0.97606(9) 0.0635(6) Uani 1 1 d .
C1 C 0.8449(3) 0.7142(3) 1.00131(14) 0.0718(8) Uani 1 1 d .
C2 C 0.9875(3) 0.5491(3) 1.03909(13) 0.0680(8) Uani 1 1 d .
H2 H 1.0776 0.5501 1.0168 0.102 Uiso 1 1 calc R
C3 C 0.8686(3) 0.4805(3) 1.00258(11) 0.0638(7) Uani 1 1 d .
H3 H 0.9147 0.4257 0.9728 0.096 Uiso 1 1 calc R
C4 C 1.0195(3) 0.4906(3) 1.09715(13) 0.0706(8) Uani 1 1 d .
C5 C 1.1246(4) 0.3930(3) 1.10184(15) 0.0825(9) Uani 1 1 d .
H5 H 1.1759 0.3669 1.0694 0.099 Uiso 1 1 calc R
C6 C 1.1550(4) 0.3332(4) 1.15414(18) 0.1021(11) Uani 1 1 d .
H6 H 1.2251 0.2664 1.1567 0.122 Uiso 1 1 calc R
C7 C 1.0806(6) 0.3733(5) 1.20226(18) 0.1176(14) Uani 1 1 d .
H7 H 1.1017 0.3350 1.2377 0.141 Uiso 1 1 calc R
C8 C 0.9753(6) 0.4701(6) 1.19805(17) 0.1261(17) Uani 1 1 d .
H8 H 0.9233 0.4950 1.2305 0.151 Uiso 1 1 calc R
C9 C 0.9455(4) 0.5312(4) 1.14584(16) 0.1017(12) Uani 1 1 d .
H9 H 0.8763 0.5988 1.1436 0.122 Uiso 1 1 calc R
C10 C 0.7640(4) 0.3945(3) 1.03608(12) 0.0717(8) Uani 1 1 d .
C11 C 0.7890(4) 0.2583(3) 1.04026(16) 0.0957(11) Uani 1 1 d .
H11 H 0.8672 0.2200 1.0212 0.115 Uiso 1 1 calc R
C12 C 0.6974(7) 0.1784(5) 1.0729(3) 0.141(2) Uani 1 1 d .
H12 H 0.7159 0.0869 1.0759 0.169 Uiso 1 1 calc R
C13 C 0.5808(8) 0.2318(7) 1.1005(2) 0.148(3) Uani 1 1 d .
H13 H 0.5195 0.1771 1.1219 0.178 Uiso 1 1 calc R
C14 C 0.5548(5) 0.3670(6) 1.09663(16) 0.1201(15) Uani 1 1 d .
H14 H 0.4764 0.4045 1.1159 0.144 Uiso 1 1 calc R
C15 C 0.6451(4) 0.4480(4) 1.06396(13) 0.0892(10) Uani 1 1 d .
H15 H 0.6254 0.5393 1.0608 0.107 Uiso 1 1 calc R
C16 C 0.7279(3) 0.5974(3) 0.92103(11) 0.0629(7) Uani 1 1 d .
H16 H 0.6966 0.6891 0.9121 0.094 Uiso 1 1 calc R
C17 C 0.5972(4) 0.5067(3) 0.92040(12) 0.0746(8) Uani 1 1 d .
H17A H 0.5333 0.5308 0.9518 0.112 Uiso 1 1 calc R
H17B H 0.6281 0.4146 0.9261 0.112 Uiso 1 1 calc R
C18 C 0.5150(4) 0.5174(4) 0.86397(14) 0.0995(11) Uani 1 1 d .
H18A H 0.5781 0.4939 0.8328 0.149 Uiso 1 1 calc R
H18B H 0.4811 0.6077 0.8589 0.149 Uiso 1 1 calc R
H18C H 0.4337 0.4572 0.8646 0.149 Uiso 1 1 calc R
C19 C 0.9469(7) 0.5368(6) 0.77039(17) 0.163(2) Uani 1 1 d .
H19A H 0.8613 0.4858 0.7617 0.244 Uiso 1 1 calc R
H19B H 1.0243 0.4768 0.7802 0.244 Uiso 1 1 calc R
H19C H 0.9741 0.5889 0.7375 0.244 Uiso 1 1 calc R
C20 C 0.7940(6) 0.7847(5) 0.8066(3) 0.174(3) Uani 1 1 d .
H20A H 0.7983 0.8575 0.8335 0.261 Uiso 1 1 calc R
H20B H 0.6960 0.7530 0.8037 0.261 Uiso 1 1 calc R
H20C H 0.8262 0.8154 0.7697 0.261 Uiso 1 1 calc R
C21 C 1.0806(6) 0.7060(6) 0.8607(3) 0.184(3) Uani 1 1 d .
H21A H 1.0631 0.7502 0.8966 0.277 Uiso 1 1 calc R
H21B H 1.1256 0.7677 0.8345 0.277 Uiso 1 1 calc R
H21C H 1.1433 0.6305 0.8667 0.277 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
O3 Si1 C21 109.6(2)
O3 Si1 C20 110.93(17)
C21 Si1 C20 113.5(3)
O3 Si1 C19 104.5(2)
C21 Si1 C19 109.1(3)
C20 Si1 C19 108.9(3)
C1 O2 C2 108.7(2)
C16 O3 Si1 126.84(17)
C1 N1 C16 121.6(2)
C1 N1 C3 112.5(2)
C16 N1 C3 124.5(2)
O1 C1 N1 128.7(3)
O1 C1 O2 121.9(3)
N1 C1 O2 109.4(3)
O2 C2 C4 109.9(2)
O2 C2 C3 104.0(2)
C4 C2 C3 117.6(2)
N1 C3 C10 114.1(2)
N1 C3 C2 100.0(2)
C10 C3 C2 114.8(2)
C5 C4 C9 119.2(3)
C5 C4 C2 118.9(3)
C9 C4 C2 121.9(3)
C4 C5 C6 121.1(4)
C7 C6 C5 119.5(4)
C8 C7 C6 120.0(4)
C7 C8 C9 120.7(4)
C4 C9 C8 119.5(4)
C11 C10 C15 118.6(3)
C11 C10 C3 119.2(3)
C15 C10 C3 122.2(3)
C10 C11 C12 120.1(4)
C13 C12 C11 121.0(5)
C12 C13 C14 119.4(5)
C13 C14 C15 120.2(5)
C10 C15 C14 120.7(4)
O3 C16 N1 108.8(2)
O3 C16 C17 108.8(2)
N1 C16 C17 113.0(2)
C16 C17 C18 111.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 O3 1.641(2)
Si1 C21 1.810(5)
Si1 C20 1.817(4)
Si1 C19 1.830(5)
O1 C1 1.203(4)
O2 C1 1.358(4)
O2 C2 1.452(3)
O3 C16 1.422(3)
N1 C1 1.354(4)
N1 C16 1.457(3)
N1 C3 1.459(4)
C2 C4 1.503(4)
C2 C3 1.548(4)
C3 C10 1.509(4)
C4 C5 1.378(4)
C4 C9 1.385(4)
C5 C6 1.386(5)
C6 C7 1.374(6)
C7 C8 1.372(6)
C8 C9 1.388(6)
C10 C11 1.380(5)
C10 C15 1.382(5)
C11 C12 1.388(6)
C12 C13 1.362(8)
C13 C14 1.371(8)
C14 C15 1.388(5)
C16 C17 1.507(4)
C17 C18 1.523(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21200309
