#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024341.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_4024341
loop_
_publ_author_name
'Qiong Li'
'Shao-Bo Yang'
'Zhihui Zhang'
'Lei Li'
'Peng-Fei Xu'
_publ_contact_author_address
;
 State Key Laboratory of Applied Organic Chemistry,
 Lanzhou University, 73000, CHINA
;
_publ_contact_author_email       ' xupf@lzu.edu.cn '
_publ_contact_author_fax         ' 86-931-8915557 '
_publ_contact_author_name        'Peng-Fei Xu'
_publ_contact_author_phone       ' 86-931-8912281 '
_publ_section_title
;
Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-Amino Acids:
Application to the Synthesis of a Key Intermediate for Lactacystin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1627
_journal_page_last               1631
_journal_paper_doi               10.1021/jo8023973
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C20 H25 N O4 '
_chemical_formula_sum            'C20 H25 N O4'
_chemical_formula_weight         343.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             'Sat Jun 19 18:59:12 2004'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.349(4)
_cell_length_b                   13.271(4)
_cell_length_c                   13.249(5)
_cell_measurement_reflns_used    4392
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1819(1)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular
Structure Corporation, 1991)
;
_computing_data_reduction
;
teXsan (Molecular Structure Corporation, 1999)
;
_computing_molecular_graphics    'ORTEPIII(Johnson, 1996)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 28.57
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14838
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4134
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.0006
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00063|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0597
_reflns_number_gt                3467
_reflns_number_total             2359
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo8023973_si_009.cif
_cod_data_source_block           '_compd-3i'
_cod_original_sg_symbol_H-M      'P 21 21 21   '
_cod_original_formula_sum        'C20 H25 N O4 '
_cod_database_code               4024341
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O(1) O -0.8237(1) -0.0917(1) -0.7128(1) 0.0307(4) Uani 1.00 d . . .
O(2) O -0.8868(2) 0.0039(1) -0.5865(1) 0.0426(4) Uani 1.00 d . . .
O(3) O -0.9107(1) -0.2597(1) -0.5340(1) 0.0360(4) Uani 1.00 d . . .
O(4) O -0.5937(2) -0.3893(1) -0.1424(1) 0.0502(5) Uani 1.00 d . . .
N(1) N -0.6444(1) -0.1942(1) -0.5842(1) 0.0281(4) Uani 1.00 d . . .
C(1) C -0.7786(2) -0.1924(1) -0.7385(1) 0.0258(4) Uani 1.00 d . . .
C(2) C -0.8264(2) -0.0689(2) -0.6140(2) 0.0312(5) Uani 1.00 d . . .
C(3) C -0.7469(2) -0.1319(2) -0.5400(1) 0.0286(5) Uani 1.00 d . . .
C(4) C -0.6635(2) -0.2212(1) -0.6750(1) 0.0268(5) Uani 1.00 d . . .
C(5) C -0.5674(2) -0.2657(2) -0.7469(2) 0.0313(5) Uani 1.00 d . . .
C(6) C -0.6289(2) -0.3592(2) -0.7969(2) 0.0368(6) Uani 1.00 d . . .
C(7) C -0.7323(2) -0.3148(2) -0.8680(2) 0.0338(5) Uani 1.00 d . . .
C(8) C -0.7258(2) -0.2003(1) -0.8469(1) 0.0256(4) Uani 1.00 d . . .
C(9) C -0.5770(2) -0.1847(2) -0.8320(2) 0.0297(5) Uani 1.00 d . . .
C(10) C -0.5378(2) -0.0787(2) -0.7981(2) 0.0365(5) Uani 1.00 d . . .
C(11) C -0.4961(2) -0.2105(2) -0.9248(2) 0.0389(6) Uani 1.00 d . . .
C(12) C -0.7913(2) -0.1343(2) -0.9237(2) 0.0331(5) Uani 1.00 d . . .
C(13) C -0.8383(2) -0.1936(2) -0.4718(1) 0.0300(5) Uani 1.00 d . . .
C(14) C -0.7643(2) -0.2476(2) -0.3884(1) 0.0301(5) Uani 1.00 d . . .
C(15) C -0.7225(2) -0.1938(2) -0.3038(2) 0.0337(5) Uani 1.00 d . . .
C(16) C -0.6629(2) -0.2427(2) -0.2241(2) 0.0369(5) Uani 1.00 d . . .
C(17) C -0.6449(2) -0.3466(2) -0.2276(2) 0.0363(5) Uani 1.00 d . . .
C(18) C -0.6807(2) -0.3995(2) -0.3133(2) 0.0381(6) Uani 1.00 d . . .
C(19) C -0.7409(2) -0.3491(2) -0.3926(2) 0.0352(5) Uani 1.00 d . . .
C(20) C -0.5780(3) -0.4957(2) -0.1412(2) 0.0613(8) Uani 1.00 d . . .
H(1) H -0.8477 -0.2408 -0.7288 0.0310 Uiso 1.00 calc . . .
H(2) H -0.7039 -0.0842 -0.4959 0.0343 Uiso 1.00 calc . . .
H(3) H -0.4815 -0.2760 -0.7195 0.0375 Uiso 1.00 calc . . .
H(4) H -0.5649 -0.3970 -0.8347 0.0441 Uiso 1.00 calc . . .
H(5) H -0.6682 -0.4027 -0.7466 0.0441 Uiso 1.00 calc . . .
H(6) H -0.7118 -0.3292 -0.9380 0.0405 Uiso 1.00 calc . . .
H(7) H -0.8172 -0.3413 -0.8521 0.0405 Uiso 1.00 calc . . .
H(8) H -0.4465 -0.0780 -0.7817 0.0438 Uiso 1.00 calc . . .
H(9) H -0.5547 -0.0311 -0.8521 0.0438 Uiso 1.00 calc . . .
H(10) H -0.5875 -0.0599 -0.7389 0.0438 Uiso 1.00 calc . . .
H(11) H -0.5191 -0.2772 -0.9487 0.0467 Uiso 1.00 calc . . .
H(12) H -0.5126 -0.1615 -0.9776 0.0467 Uiso 1.00 calc . . .
H(13) H -0.4052 -0.2092 -0.9071 0.0467 Uiso 1.00 calc . . .
H(14) H -0.7818 -0.0642 -0.9043 0.0397 Uiso 1.00 calc . . .
H(15) H -0.7519 -0.1448 -0.9893 0.0397 Uiso 1.00 calc . . .
H(16) H -0.8823 -0.1513 -0.9271 0.0397 Uiso 1.00 calc . . .
H(17) H -0.8982 -0.1471 -0.4402 0.0360 Uiso 1.00 calc . . .
H(18) H -0.7353 -0.1215 -0.3010 0.0404 Uiso 1.00 calc . . .
H(19) H -0.6337 -0.2046 -0.1659 0.0442 Uiso 1.00 calc . . .
H(20) H -0.6640 -0.4712 -0.3180 0.0457 Uiso 1.00 calc . . .
H(21) H -0.7668 -0.3867 -0.4521 0.0422 Uiso 1.00 calc . . .
H(22) H -0.6614 -0.5278 -0.1505 0.0736 Uiso 1.00 calc . . .
H(23) H -0.5204 -0.5157 -0.1953 0.0736 Uiso 1.00 calc . . .
H(24) H -0.5417 -0.5163 -0.0769 0.0736 Uiso 1.00 calc . . .
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)
;
O O 0.011 0.006
;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)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) O(1) C(2) 116.2(2) . . . yes
C(17) O(4) C(20) 117.7(2) . . . yes
C(3) N(1) C(4) 115.1(2) . . . yes
O(1) C(1) C(4) 110.8(2) . . . yes
O(1) C(1) C(8) 113.3(2) . . . yes
C(4) C(1) C(8) 102.9(2) . . . yes
O(1) C(2) O(2) 119.0(2) . . . yes
O(1) C(2) C(3) 119.4(2) . . . yes
O(2) C(2) C(3) 121.5(2) . . . yes
N(1) C(3) C(2) 116.2(2) . . . yes
N(1) C(3) C(13) 112.2(2) . . . yes
C(2) C(3) C(13) 109.6(2) . . . yes
N(1) C(4) C(1) 125.5(2) . . . yes
N(1) C(4) C(5) 127.5(2) . . . yes
C(1) C(4) C(5) 105.6(2) . . . yes
C(4) C(5) C(6) 108.4(2) . . . yes
C(4) C(5) C(9) 98.3(1) . . . yes
C(6) C(5) C(9) 102.6(2) . . . yes
C(5) C(6) C(7) 103.9(2) . . . yes
C(6) C(7) C(8) 103.6(2) . . . yes
C(1) C(8) C(7) 102.7(2) . . . yes
C(1) C(8) C(9) 102.9(2) . . . yes
C(1) C(8) C(12) 115.6(2) . . . yes
C(7) C(8) C(9) 101.3(2) . . . yes
C(7) C(8) C(12) 115.5(2) . . . yes
C(9) C(8) C(12) 116.8(2) . . . yes
C(5) C(9) C(8) 93.6(2) . . . yes
C(5) C(9) C(10) 113.8(2) . . . yes
C(5) C(9) C(11) 113.1(2) . . . yes
C(8) C(9) C(10) 114.8(2) . . . yes
C(8) C(9) C(11) 114.1(2) . . . yes
C(10) C(9) C(11) 107.3(2) . . . yes
O(3) C(13) C(3) 108.2(2) . . . yes
O(3) C(13) C(14) 113.3(2) . . . yes
C(3) C(13) C(14) 111.5(2) . . . yes
C(13) C(14) C(15) 119.8(2) . . . yes
C(13) C(14) C(19) 121.4(2) . . . yes
C(15) C(14) C(19) 118.7(2) . . . yes
C(14) C(15) C(16) 120.7(2) . . . yes
C(15) C(16) C(17) 119.9(2) . . . yes
O(4) C(17) C(16) 115.7(2) . . . yes
O(4) C(17) C(18) 124.7(2) . . . yes
C(16) C(17) C(18) 119.6(2) . . . yes
C(17) C(18) C(19) 119.7(2) . . . yes
C(14) C(19) C(18) 121.3(2) . . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.456(2) . . yes
O(1) C(2) 1.343(3) . . yes
O(2) C(2) 1.207(3) . . yes
O(3) C(13) 1.417(3) . . yes
O(4) C(17) 1.369(3) . . yes
O(4) C(20) 1.422(4) . . yes
N(1) C(3) 1.468(3) . . yes
N(1) C(4) 1.270(3) . . yes
C(1) C(4) 1.508(3) . . yes
C(1) C(8) 1.540(3) . . yes
C(2) C(3) 1.529(3) . . yes
C(3) C(13) 1.543(3) . . yes
C(4) C(5) 1.498(3) . . yes
C(5) C(6) 1.544(3) . . yes
C(5) C(9) 1.562(3) . . yes
C(6) C(7) 1.543(3) . . yes
C(7) C(8) 1.546(3) . . yes
C(8) C(9) 1.566(3) . . yes
C(8) C(12) 1.504(3) . . yes
C(9) C(10) 1.531(3) . . yes
C(9) C(11) 1.526(3) . . yes
C(13) C(14) 1.524(3) . . yes
C(14) C(15) 1.397(3) . . yes
C(14) C(19) 1.370(3) . . yes
C(15) C(16) 1.385(3) . . yes
C(16) C(17) 1.392(3) . . yes
C(17) C(18) 1.385(3) . . yes
C(18) C(19) 1.393(3) . . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) O(4) 3.398(2) . 3_444 ?
O(1) C(20) 3.467(3) . 3_444 ?
O(1) C(17) 3.514(3) . 3_444 ?
O(2) C(12) 3.323(3) . 2_355 ?
O(2) C(18) 3.597(3) . 3_444 ?
O(3) N(1) 2.946(2) . 3_444 ?
O(3) C(20) 3.545(3) . 2_344 ?
O(4) C(12) 3.265(3) . 3_544 ?
N(1) C(13) 3.578(3) . 3_544 ?
C(11) C(12) 3.573(3) . 3_543 ?
C(12) C(20) 3.539(4) . 3_444 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O(1) C(1) C(4) N(1) 33.3(3) . . . . yes
O(1) C(1) C(4) C(5) -134.2(2) . . . . yes
O(1) C(1) C(8) C(7) -160.2(2) . . . . yes
O(1) C(1) C(8) C(9) 94.9(2) . . . . yes
O(1) C(1) C(8) C(12) -33.6(2) . . . . yes
O(1) C(2) C(3) N(1) 17.2(3) . . . . yes
O(1) C(2) C(3) C(13) -111.4(2) . . . . yes
O(2) C(2) O(1) C(1) -164.8(2) . . . . yes
O(2) C(2) C(3) N(1) -159.2(2) . . . . yes
O(2) C(2) C(3) C(13) 72.2(3) . . . . yes
O(3) C(13) C(3) N(1) -68.9(2) . . . . yes
O(3) C(13) C(3) C(2) 61.8(2) . . . . yes
O(3) C(13) C(14) C(15) -160.1(2) . . . . yes
O(3) C(13) C(14) C(19) 17.8(3) . . . . yes
O(4) C(17) C(16) C(15) -175.5(2) . . . . yes
O(4) C(17) C(18) C(19) 175.2(2) . . . . yes
N(1) C(3) C(13) C(14) 56.3(2) . . . . yes
N(1) C(4) C(1) C(8) 154.7(2) . . . . yes
N(1) C(4) C(5) C(6) 132.1(2) . . . . yes
N(1) C(4) C(5) C(9) -121.6(2) . . . . yes
C(1) O(1) C(2) C(3) 18.7(3) . . . . yes
C(1) C(4) N(1) C(3) 1.5(3) . . . . yes
C(1) C(4) C(5) C(6) -60.7(2) . . . . yes
C(1) C(4) C(5) C(9) 45.6(2) . . . . yes
C(1) C(8) C(7) C(6) -68.4(2) . . . . yes
C(1) C(8) C(9) C(5) 50.6(2) . . . . yes
C(1) C(8) C(9) C(10) -67.7(2) . . . . yes
C(1) C(8) C(9) C(11) 167.9(2) . . . . yes
C(2) O(1) C(1) C(4) -41.6(2) . . . . yes
C(2) O(1) C(1) C(8) -156.6(2) . . . . yes
C(2) C(3) N(1) C(4) -27.0(3) . . . . yes
C(2) C(3) C(13) C(14) -173.0(2) . . . . yes
C(3) N(1) C(4) C(5) 166.3(2) . . . . yes
C(3) C(13) C(14) C(15) 77.6(2) . . . . yes
C(3) C(13) C(14) C(19) -104.5(2) . . . . yes
C(4) N(1) C(3) C(13) 100.3(2) . . . . yes
C(4) C(1) C(8) C(7) 80.1(2) . . . . yes
C(4) C(1) C(8) C(9) -24.8(2) . . . . yes
C(4) C(1) C(8) C(12) -153.2(2) . . . . yes
C(4) C(5) C(6) C(7) 71.1(2) . . . . yes
C(4) C(5) C(9) C(8) -57.6(2) . . . . yes
C(4) C(5) C(9) C(10) 61.5(2) . . . . yes
C(4) C(5) C(9) C(11) -175.7(2) . . . . yes
C(5) C(4) C(1) C(8) -12.9(2) . . . . yes
C(5) C(6) C(7) C(8) -3.4(2) . . . . yes
C(5) C(9) C(8) C(7) -55.4(2) . . . . yes
C(5) C(9) C(8) C(12) 178.3(2) . . . . yes
C(6) C(5) C(9) C(8) 53.5(2) . . . . yes
C(6) C(5) C(9) C(10) 172.6(2) . . . . yes
C(6) C(5) C(9) C(11) -64.6(2) . . . . yes
C(6) C(7) C(8) C(9) 37.7(2) . . . . yes
C(6) C(7) C(8) C(12) 164.9(2) . . . . yes
C(7) C(6) C(5) C(9) -32.3(2) . . . . yes
C(7) C(8) C(9) C(10) -173.7(2) . . . . yes
C(7) C(8) C(9) C(11) 61.8(2) . . . . yes
C(10) C(9) C(8) C(12) 60.0(2) . . . . yes
C(11) C(9) C(8) C(12) -64.4(2) . . . . yes
C(13) C(14) C(15) C(16) 175.6(2) . . . . yes
C(13) C(14) C(19) C(18) -175.7(2) . . . . yes
C(14) C(15) C(16) C(17) -0.4(3) . . . . yes
C(14) C(19) C(18) C(17) 0.8(3) . . . . yes
C(15) C(14) C(19) C(18) 2.2(3) . . . . yes
C(15) C(16) C(17) C(18) 3.4(3) . . . . yes
C(16) C(15) C(14) C(19) -2.4(3) . . . . yes
C(16) C(17) O(4) C(20) 177.7(2) . . . . yes
C(16) C(17) C(18) C(19) -3.6(3) . . . . yes
C(18) C(17) O(4) C(20) -1.1(3) . . . . yes
C(18) C(17) O(4) C(20) -1.1(3) . . . . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658901
