#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023354.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_4023354
loop_
_publ_author_name
'Christopher J. Hayes'
'Alexandra E. Sherlock'
'Martin P. Green'
'Claire Wilson'
'Alexander J. Blake'
'Matthew D. Selby'
'Jeremy C. Prodger'
_publ_section_title
;
 Enantioselective Total Syntheses of Omuralide, 7-epi-Omuralide,
 and (+)-Lactacystin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2041
_journal_page_last               2051
_journal_paper_doi               10.1021/jo7027695
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H22 Br N O2'
_chemical_formula_weight         352.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   'geom,  sp2 bound Me from difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.117(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.947(2)
_cell_length_b                   5.9259(8)
_cell_length_c                   12.668(2)
_cell_measurement_reflns_used    2756
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      3.3
_cell_volume                     861.6(2)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction
'Bruker SAINT; Bruker SHELXTL v6.12 (Bruker, 2'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7623
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.389
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL v6.12'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                3143
_reflns_number_total             3856
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo7027695-File001.cif
_cod_data_source_block           brenep
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'P 21'
_cod_database_code               4023354
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
Br Br 0.77329(3) 0.15232(11) 0.55622(3) 0.05216(15) Uani 1 1 d . . .
N N 0.4604(2) -0.0950(5) 0.7507(2) 0.0281(6) Uani 1 1 d . . .
O1 O 0.3746(2) -0.1413(4) 1.00763(19) 0.0341(6) Uani 1 1 d . . .
C2 C 0.2537(3) -0.1692(6) 0.9594(3) 0.0277(7) Uani 1 1 d . . .
H2A H 0.2375 -0.3298 0.9361 0.033 Uiso 1 1 calc R . .
O3 O 0.21225(18) -0.0263(4) 0.86733(18) 0.0246(5) Uani 1 1 d . . .
C4 C 0.2680(3) -0.0732(5) 0.7827(3) 0.0230(7) Uani 1 1 d . . .
H4A H 0.2558 -0.2364 0.7628 0.028 Uiso 1 1 calc R . .
C5 C 0.3988(3) -0.0339(6) 0.8308(3) 0.0277(7) Uani 1 1 d . . .
H5A H 0.4141 0.1276 0.8529 0.033 Uiso 1 1 calc R . .
C6 C 0.4387(3) -0.1854(7) 0.9300(3) 0.0350(8) Uani 1 1 d . . .
H6A H 0.4278 -0.3451 0.9064 0.042 Uiso 1 1 calc R . .
H6B H 0.5227 -0.1606 0.9652 0.042 Uiso 1 1 calc R . .
C11 C 0.1905(3) -0.1119(6) 1.0430(3) 0.0266(7) Uani 1 1 d . . .
C12 C 0.2120(3) 0.0914(5) 1.0996(3) 0.0315(9) Uani 1 1 d . . .
H12A H 0.2678 0.1938 1.0864 0.038 Uiso 1 1 calc R . .
C13 C 0.1518(3) 0.1450(9) 1.1756(2) 0.0338(7) Uani 1 1 d . . .
H13A H 0.1668 0.2842 1.2141 0.041 Uiso 1 1 calc R . .
C14 C 0.0701(3) -0.0024(7) 1.1957(3) 0.0345(8) Uani 1 1 d . . .
H14A H 0.0294 0.0348 1.2480 0.041 Uiso 1 1 calc R . .
C15 C 0.0487(3) -0.2025(7) 1.1393(3) 0.0331(8) Uani 1 1 d . . .
H15A H -0.0078 -0.3035 1.1522 0.040 Uiso 1 1 calc R . .
C16 C 0.1091(3) -0.2593(6) 1.0632(3) 0.0285(8) Uani 1 1 d . . .
H16A H 0.0942 -0.3992 1.0253 0.034 Uiso 1 1 calc R . .
C1' C 0.5367(3) 0.0415(6) 0.7383(3) 0.0267(7) Uani 1 1 d . . .
H1'A H 0.5507 0.1755 0.7811 0.032 Uiso 1 1 calc R . .
C2' C 0.6047(3) -0.0003(6) 0.6593(3) 0.0290(8) Uani 1 1 d . . .
C2A' C 0.5784(3) -0.2057(7) 0.5897(3) 0.0401(9) Uani 1 1 d . . .
H2A1 H 0.5041 -0.1856 0.5333 0.060 Uiso 1 1 calc R . .
H2A2 H 0.5731 -0.3363 0.6355 0.060 Uiso 1 1 calc R . .
H2A3 H 0.6406 -0.2307 0.5543 0.060 Uiso 1 1 calc R . .
C3' C 0.6811(2) 0.1577(9) 0.6547(2) 0.0309(7) Uani 1 1 d . . .
H3'A H 0.6899 0.2815 0.7039 0.037 Uiso 1 1 calc R . .
C1" C 0.2104(3) 0.0656(6) 0.6810(3) 0.0294(9) Uani 1 1 d . . .
H1"A H 0.2543 0.0378 0.6257 0.035 Uiso 1 1 calc R . .
C2" C 0.2149(4) 0.3155(7) 0.7044(4) 0.0413(10) Uani 1 1 d . . .
H2"A H 0.2960 0.3620 0.7360 0.062 Uiso 1 1 calc R . .
H2"B H 0.1699 0.3488 0.7565 0.062 Uiso 1 1 calc R . .
H2"C H 0.1816 0.3982 0.6358 0.062 Uiso 1 1 calc R . .
C1A" C 0.0854(3) -0.0144(7) 0.6311(3) 0.0398(9) Uani 1 1 d . . .
H1AA H 0.0853 -0.1769 0.6167 0.060 Uiso 1 1 calc R . .
H1AB H 0.0516 0.0661 0.5620 0.060 Uiso 1 1 calc R . .
H1AC H 0.0392 0.0163 0.6824 0.060 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'
Br Br -0.2901 2.4595 '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
C1' N C5 116.8(3) . . ?
C2 O1 C6 111.1(3) . . ?
O1 C2 O3 111.6(3) . . ?
O1 C2 C11 108.8(3) . . ?
O3 C2 C11 108.5(3) . . ?
C2 O3 C4 111.8(2) . . ?
O3 C4 C1" 109.4(3) . . ?
O3 C4 C5 107.9(3) . . ?
C1" C4 C5 115.3(3) . . ?
N C5 C6 109.2(3) . . ?
N C5 C4 110.0(3) . . ?
C6 C5 C4 107.0(3) . . ?
O1 C6 C5 111.0(3) . . ?
C16 C11 C12 119.3(3) . . ?
C16 C11 C2 120.4(3) . . ?
C12 C11 C2 120.3(3) . . ?
C13 C12 C11 120.0(3) . . ?
C14 C13 C12 120.7(4) . . ?
C15 C14 C13 119.2(3) . . ?
C14 C15 C16 120.7(3) . . ?
C11 C16 C15 120.0(3) . . ?
N C1' C2' 122.0(3) . . ?
C3' C2' C1' 115.4(3) . . ?
C3' C2' C2A' 126.1(3) . . ?
C1' C2' C2A' 118.4(3) . . ?
C2' C3' Br 123.9(3) . . ?
C2" C1" C4 112.4(4) . . ?
C2" C1" C1A" 111.3(4) . . ?
C4 C1" C1A" 110.1(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
Br C3' 1.879(3) . ?
N C1' 1.260(4) . ?
N C5 1.455(4) . ?
O1 C2 1.413(4) . ?
O1 C6 1.428(4) . ?
C2 O3 1.415(4) . ?
C2 C11 1.499(4) . ?
O3 C4 1.438(4) . ?
C4 C1" 1.522(5) . ?
C4 C5 1.529(4) . ?
C5 C6 1.510(5) . ?
C11 C16 1.384(5) . ?
C11 C12 1.389(5) . ?
C12 C13 1.388(4) . ?
C13 C14 1.385(5) . ?
C14 C15 1.371(5) . ?
C15 C16 1.396(5) . ?
C1' C2' 1.475(5) . ?
C2' C3' 1.320(5) . ?
C2' C2A' 1.485(5) . ?
C1" C2" 1.509(6) . ?
C1" C1A" 1.526(5) . ?
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
C6 O1 C2 O3 -58.0(4) . . . . ?
C6 O1 C2 C11 -177.7(3) . . . . ?
O1 C2 O3 C4 60.8(3) . . . . ?
C11 C2 O3 C4 -179.3(3) . . . . ?
C2 O3 C4 C1" 173.5(3) . . . . ?
C2 O3 C4 C5 -60.4(3) . . . . ?
C1' N C5 C6 -108.3(3) . . . . ?
C1' N C5 C4 134.5(3) . . . . ?
O3 C4 C5 N 175.9(3) . . . . ?
C1" C4 C5 N -61.6(4) . . . . ?
O3 C4 C5 C6 57.3(3) . . . . ?
C1" C4 C5 C6 179.9(3) . . . . ?
C2 O1 C6 C5 57.5(4) . . . . ?
N C5 C6 O1 -176.1(3) . . . . ?
C4 C5 C6 O1 -57.0(4) . . . . ?
O1 C2 C11 C16 -129.3(3) . . . . ?
O3 C2 C11 C16 109.0(3) . . . . ?
O1 C2 C11 C12 51.6(4) . . . . ?
O3 C2 C11 C12 -70.0(4) . . . . ?
C16 C11 C12 C13 -0.1(5) . . . . ?
C2 C11 C12 C13 179.0(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C12 C11 C16 C15 0.5(5) . . . . ?
C2 C11 C16 C15 -178.6(3) . . . . ?
C14 C15 C16 C11 -0.8(5) . . . . ?
C5 N C1' C2' -179.7(3) . . . . ?
N C1' C2' C3' 179.6(3) . . . . ?
N C1' C2' C2A' 2.5(5) . . . . ?
C1' C2' C3' Br -176.9(2) . . . . ?
C2A' C2' C3' Br 0.0(5) . . . . ?
O3 C4 C1" C2" 57.9(4) . . . . ?
C5 C4 C1" C2" -63.9(4) . . . . ?
O3 C4 C1" C1A" -66.9(4) . . . . ?
C5 C4 C1" C1A" 171.3(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658662
