#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024336.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_4024336
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         'C19 H22 F N O3'
_chemical_formula_sum            'C19 H22 F N O3'
_chemical_formula_weight         331.38
_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                   10.4278(8)
_cell_length_b                   12.2750(10)
_cell_length_c                   13.8915(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1778.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10007
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2962
_reflns_number_total             3488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8023973_si_004.cif
_cod_data_source_block           compd-2f
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4024336
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+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
_atom_site_disorder_assembly
_atom_site_disorder_group
F F 0.79525(16) -1.49534(13) -1.02268(12) 0.0898(5) Uani 1 1 d . . .
O1 O 0.8434(2) -1.73356(13) -1.26574(11) 0.0722(5) Uani 1 1 d . . .
O2 O 0.89970(15) -1.89278(11) -1.20797(9) 0.0517(4) Uani 1 1 d . . .
O3 O 1.04848(11) -1.74972(12) -1.05326(12) 0.0562(4) Uani 1 1 d . . .
H3A H 1.0392 -1.8006 -1.0908 0.084 Uiso 1 1 calc R . .
N N 0.77698(13) -1.83856(11) -1.03115(10) 0.0365(3) Uani 1 1 d . . .
C1 C 0.9215(2) -2.07612(16) -1.13097(16) 0.0510(5) Uani 1 1 d . . .
H1A H 0.9488 -2.1049 -1.1935 0.061 Uiso 1 1 calc R . .
C2 C 0.92935(18) -1.95271(15) -1.12048(14) 0.0438(4) Uani 1 1 d . . .
H2A H 1.0142 -1.9317 -1.0965 0.053 Uiso 1 1 calc R . .
C3 C 0.85803(19) -1.79044(16) -1.19669(13) 0.0470(4) Uani 1 1 d . . .
C4 C 0.82460(17) -1.75135(14) -1.09507(13) 0.0394(4) Uani 1 1 d . . .
H4A H 0.7533 -1.7000 -1.1026 0.047 Uiso 1 1 calc R . .
C5 C 0.82884(16) -1.93027(13) -1.04491(12) 0.0357(4) Uani 1 1 d . . .
C6 C 0.78836(19) -2.03921(15) -1.00425(13) 0.0434(4) Uani 1 1 d . . .
C7 C 0.9105(2) -2.08806(19) -0.95739(18) 0.0655(6) Uani 1 1 d . . .
H7A H 0.8896 -2.1520 -0.9194 0.079 Uiso 1 1 calc R . .
H7B H 0.9524 -2.0350 -0.9163 0.079 Uiso 1 1 calc R . .
C8 C 0.9972(2) -2.1186(2) -1.0439(2) 0.0733(7) Uani 1 1 d . . .
H8A H 1.0802 -2.0834 -1.0391 0.088 Uiso 1 1 calc R . .
H8B H 1.0095 -2.1968 -1.0478 0.088 Uiso 1 1 calc R . .
C9 C 0.7823(2) -2.10478(16) -1.10114(13) 0.0447(4) Uani 1 1 d . . .
C10 C 0.6814(2) -2.06392(18) -1.17106(15) 0.0547(5) Uani 1 1 d . . .
H10A H 0.6931 -1.9873 -1.1816 0.082 Uiso 1 1 calc R . .
H10B H 0.5976 -2.0767 -1.1447 0.082 Uiso 1 1 calc R . .
H10C H 0.6897 -2.1020 -1.2311 0.082 Uiso 1 1 calc R . .
C11 C 0.7611(3) -2.22739(18) -1.08672(18) 0.0673(6) Uani 1 1 d . . .
H11A H 0.7589 -2.2630 -1.1482 0.101 Uiso 1 1 calc R . .
H11B H 0.6812 -2.2391 -1.0540 0.101 Uiso 1 1 calc R . .
H11C H 0.8299 -2.2569 -1.0489 0.101 Uiso 1 1 calc R . .
C12 C 0.6693(3) -2.03719(18) -0.94209(16) 0.0612(6) Uani 1 1 d . . .
H12A H 0.5995 -2.0062 -0.9779 0.092 Uiso 1 1 calc R . .
H12B H 0.6851 -1.9940 -0.8857 0.092 Uiso 1 1 calc R . .
H12C H 0.6476 -2.1102 -0.9232 0.092 Uiso 1 1 calc R . .
C13 C 0.93705(16) -1.68456(14) -1.05350(14) 0.0411(4) Uani 1 1 d . . .
H13A H 0.9523 -1.6224 -1.0963 0.049 Uiso 1 1 calc R . .
C14 C 0.90628(17) -1.64060(15) -0.95398(14) 0.0436(4) Uani 1 1 d . . .
C15 C 0.8373(2) -1.54672(19) -0.94231(17) 0.0579(5) Uani 1 1 d . . .
C16 C 0.8103(3) -1.5014(3) -0.8530(2) 0.0850(9) Uani 1 1 d . . .
H16A H 0.7640 -1.4369 -0.8474 0.102 Uiso 1 1 calc R . .
C17 C 0.8548(3) -1.5560(4) -0.7728(2) 0.0910(10) Uani 1 1 d . . .
H17A H 0.8375 -1.5282 -0.7119 0.109 Uiso 1 1 calc R . .
C18 C 0.9246(3) -1.6509(3) -0.78133(18) 0.0797(8) Uani 1 1 d . . .
H18A H 0.9546 -1.6866 -0.7267 0.096 Uiso 1 1 calc R . .
C19 C 0.9492(2) -1.6921(2) -0.87114(17) 0.0626(6) Uani 1 1 d . . .
H19A H 0.9959 -1.7564 -0.8767 0.075 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C3 O2 C2 116.49(14) . . ?
C5 N C4 114.27(14) . . ?
C2 C1 C8 103.58(18) . . ?
C2 C1 C9 104.47(15) . . ?
C8 C1 C9 101.15(18) . . ?
O2 C2 C5 109.97(14) . . ?
O2 C2 C1 114.31(16) . . ?
C5 C2 C1 102.18(15) . . ?
O1 C3 O2 119.70(18) . . ?
O1 C3 C4 121.82(19) . . ?
O2 C3 C4 118.42(15) . . ?
N C4 C3 113.81(14) . . ?
N C4 C13 114.56(14) . . ?
C3 C4 C13 109.79(15) . . ?
N C5 C2 124.42(16) . . ?
N C5 C6 127.74(16) . . ?
C2 C5 C6 107.00(14) . . ?
C5 C6 C12 115.34(16) . . ?
C5 C6 C7 105.63(16) . . ?
C12 C6 C7 116.17(17) . . ?
C5 C6 C9 98.30(14) . . ?
C12 C6 C9 117.70(18) . . ?
C7 C6 C9 101.22(16) . . ?
C6 C7 C8 104.32(18) . . ?
C1 C8 C7 103.23(17) . . ?
C10 C9 C11 107.93(18) . . ?
C10 C9 C1 113.79(17) . . ?
C11 C9 C1 113.11(18) . . ?
C10 C9 C6 114.04(16) . . ?
C11 C9 C6 113.38(17) . . ?
C1 C9 C6 94.32(15) . . ?
O3 C13 C14 111.92(16) . . ?
O3 C13 C4 109.00(14) . . ?
C14 C13 C4 111.65(15) . . ?
C15 C14 C19 117.1(2) . . ?
C15 C14 C13 121.22(18) . . ?
C19 C14 C13 121.68(18) . . ?
F C15 C14 117.68(19) . . ?
F C15 C16 119.0(2) . . ?
C14 C15 C16 123.4(2) . . ?
C17 C16 C15 117.3(3) . . ?
C16 C17 C18 121.2(2) . . ?
C19 C18 C17 119.3(3) . . ?
C18 C19 C14 121.8(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F C15 1.355(3) . ?
O1 C3 1.196(2) . ?
O2 C3 1.338(3) . ?
O2 C2 1.454(2) . ?
O3 C13 1.411(2) . ?
N C5 1.263(2) . ?
N C4 1.477(2) . ?
C1 C2 1.524(3) . ?
C1 C8 1.536(3) . ?
C1 C9 1.550(3) . ?
C2 C5 1.509(3) . ?
C3 C4 1.531(3) . ?
C4 C13 1.543(2) . ?
C5 C6 1.512(2) . ?
C6 C12 1.513(3) . ?
C6 C7 1.551(3) . ?
C6 C9 1.570(3) . ?
C7 C8 1.549(4) . ?
C9 C10 1.517(3) . ?
C9 C11 1.534(3) . ?
C13 C14 1.518(3) . ?
C14 C15 1.368(3) . ?
C14 C19 1.387(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.380(5) . ?
C17 C18 1.379(5) . ?
C18 C19 1.370(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658899
