#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:38:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178788 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/42/4104257.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_4104257
loop_
_publ_author_name
'Ryan A. Shenvi'
'E. J. Corey'
_publ_section_title
;
 A Short and Efficient Synthesis of (-)-7-Methylomuralide, a Potent
 Proteasome Inhibitor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5746
_journal_page_last               5747
_journal_paper_doi               10.1021/ja901400q
_journal_volume                  131
_journal_year                    2009
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C20 H25 N O7'
_chemical_formula_moiety         'C20 H25 N O7'
_chemical_formula_structural     'C20 H25 N O7'
_chemical_formula_sum            'C20 H25 N O7'
_chemical_formula_weight         391.41
_chemical_name_common            RAS-2-OCbz
_chemical_name_systematic
; 
Methyl 2-(1-(benzyloxycarbonyloxy)-2-methylpropyl)-4,4-
dimethyl-3,5-dioxopyrrolidine-2-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.129(1)
_cell_angle_beta                 78.693(1)
_cell_angle_gamma                88.859(1)
_cell_formula_units_Z            2
_cell_length_a                   9.0015(1)
_cell_length_b                   9.1400(1)
_cell_length_c                   12.5776(1)
_cell_measurement_reflns_used    11624
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.23
_cell_volume                     1014.084(18)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'ω scans, 3225 0.5° rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29386
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0514P)²+0.2622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                4010
_reflns_number_total             4666
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja901400q_si_003.cif
_cod_data_source_block           ejc158
_cod_database_code               4104257
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.59688(11) 0.05546(10) 0.60627(8) 0.0268(2) Uani 1 1 d .
H1 H 0.6058(17) 0.0717(17) 0.5383(13) 0.040 Uiso 1 1 d .
C2 C 0.68819(12) 0.12787(12) 0.67057(8) 0.0255(2) Uani 1 1 d .
C3 C 0.61971(12) 0.06799(12) 0.78690(9) 0.0274(2) Uani 1 1 d .
C4 C 0.49743(12) -0.04070(12) 0.78086(9) 0.0274(2) Uani 1 1 d .
C5 C 0.48907(12) -0.03307(12) 0.66108(9) 0.0274(2) Uani 1 1 d .
C6 C 0.67039(12) 0.29548(12) 0.66646(9) 0.0277(2) Uani 1 1 d .
H6 H 0.7387 0.3403 0.7098 0.033 Uiso 1 1 calc R
O7 O 0.51245(9) 0.32197(9) 0.71753(7) 0.03158(19) Uani 1 1 d .
C8 C 0.48685(14) 0.40143(12) 0.80741(9) 0.0309(2) Uani 1 1 d .
O9 O 0.58134(11) 0.45354(11) 0.84877(8) 0.0449(2) Uani 1 1 d .
O10 O 0.33754(10) 0.41048(11) 0.83995(7) 0.0409(2) Uani 1 1 d .
C11 C 0.28232(17) 0.48557(15) 0.94053(10) 0.0411(3) Uani 1 1 d .
H11A H 0.3682 0.5319 0.9645 0.049 Uiso 1 1 calc R
H11B H 0.2368 0.4137 0.9977 0.049 Uiso 1 1 calc R
C12 C 0.16654(13) 0.60008(13) 0.92553(9) 0.0305(2) Uani 1 1 d .
C13 C 0.11545(14) 0.69212(14) 1.01117(10) 0.0368(3) Uani 1 1 d .
H13 H 0.1547 0.6814 1.0759 0.044 Uiso 1 1 calc R
C14 C 0.00745(16) 0.79957(16) 1.00249(13) 0.0477(3) Uani 1 1 d .
H14 H -0.0275 0.8617 1.0616 0.057 Uiso 1 1 calc R
C15 C -0.04962(17) 0.81702(17) 0.90893(14) 0.0509(4) Uani 1 1 d .
H15 H -0.1231 0.8914 0.9032 0.061 Uiso 1 1 calc R
C16 C 0.00030(18) 0.72631(18) 0.82394(13) 0.0510(4) Uani 1 1 d .
H16 H -0.0389 0.7378 0.7593 0.061 Uiso 1 1 calc R
C17 C 0.10809(17) 0.61776(16) 0.83233(11) 0.0437(3) Uani 1 1 d .
H17 H 0.1418 0.5552 0.7733 0.052 Uiso 1 1 calc R
C18 C 0.69466(15) 0.36757(13) 0.55326(10) 0.0348(3) Uani 1 1 d .
H18 H 0.6153 0.3308 0.5157 0.042 Uiso 1 1 calc R
C19 C 0.6736(2) 0.53365(15) 0.56203(13) 0.0502(4) Uani 1 1 d .
H19A H 0.5723 0.5560 0.6038 0.075 Uiso 1 1 calc R
H19B H 0.6848 0.5788 0.4892 0.075 Uiso 1 1 calc R
H19C H 0.7503 0.5725 0.5987 0.075 Uiso 1 1 calc R
C20 C 0.84885(17) 0.33092(17) 0.48449(11) 0.0472(3) Uani 1 1 d .
H20A H 0.8558 0.2256 0.4716 0.071 Uiso 1 1 calc R
H20B H 0.9287 0.3583 0.5227 0.071 Uiso 1 1 calc R
H20C H 0.8613 0.3853 0.4149 0.071 Uiso 1 1 calc R
C21 C 0.85289(13) 0.07068(13) 0.64700(9) 0.0307(2) Uani 1 1 d .
O22 O 0.88863(10) -0.04567(10) 0.60856(8) 0.0436(2) Uani 1 1 d .
O23 O 0.94459(10) 0.16269(11) 0.68092(8) 0.0400(2) Uani 1 1 d .
C24 C 1.10337(15) 0.1176(2) 0.66285(14) 0.0534(4) Uani 1 1 d .
H24A H 1.1609 0.1883 0.6949 0.080 Uiso 1 1 calc R
H24B H 1.1437 0.1134 0.5847 0.080 Uiso 1 1 calc R
H24C H 1.1124 0.0206 0.6968 0.080 Uiso 1 1 calc R
O25 O 0.66173(11) 0.10391(10) 0.86678(7) 0.0401(2) Uani 1 1 d .
C26 C 0.54823(17) -0.19488(14) 0.81170(12) 0.0437(3) Uani 1 1 d .
H26A H 0.6456 -0.2194 0.7652 0.066 Uiso 1 1 calc R
H26B H 0.4722 -0.2659 0.8019 0.066 Uiso 1 1 calc R
H26C H 0.5594 -0.1979 0.8877 0.066 Uiso 1 1 calc R
C27 C 0.34743(14) 0.00190(16) 0.85370(10) 0.0376(3) Uani 1 1 d .
H27A H 0.3188 0.1019 0.8346 0.056 Uiso 1 1 calc R
H27B H 0.3587 -0.0031 0.9297 0.056 Uiso 1 1 calc R
H27C H 0.2686 -0.0658 0.8436 0.056 Uiso 1 1 calc R
O28 O 0.39789(10) -0.09937(10) 0.62060(7) 0.0377(2) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C2 116.02(9)
C5 N1 H1 121.2(10)
C2 N1 H1 122.7(10)
N1 C2 C6 113.04(9)
N1 C2 C21 111.42(9)
C6 C2 C21 114.90(9)
N1 C2 C3 101.61(9)
C6 C2 C3 109.46(9)
C21 C2 C3 105.24(8)
O25 C3 C4 126.97(10)
O25 C3 C2 123.63(10)
C4 C3 C2 109.40(9)
C3 C4 C5 102.62(9)
C3 C4 C27 111.33(10)
C5 C4 C27 112.40(9)
C3 C4 C26 109.90(10)
C5 C4 C26 109.64(10)
C27 C4 C26 110.68(10)
O28 C5 N1 125.07(10)
O28 C5 C4 124.78(10)
N1 C5 C4 110.15(9)
O7 C6 C18 107.12(9)
O7 C6 C2 104.12(9)
C18 C6 C2 115.83(9)
O7 C6 H6 109.8
C18 C6 H6 109.8
C2 C6 H6 109.8
C8 O7 C6 116.94(9)
O9 C8 O10 127.40(11)
O9 C8 O7 126.01(11)
O10 C8 O7 106.59(10)
C8 O10 C11 116.54(10)
O10 C11 C12 110.78(10)
O10 C11 H11A 109.5
C12 C11 H11A 109.5
O10 C11 H11B 109.5
C12 C11 H11B 109.5
H11A C11 H11B 108.1
C17 C12 C13 118.93(11)
C17 C12 C11 123.61(11)
C13 C12 C11 117.46(11)
C14 C13 C12 120.16(12)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 120.52(13)
C15 C14 H14 119.7
C13 C14 H14 119.7
C16 C15 C14 119.63(13)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C17 120.13(14)
C15 C16 H16 119.9
C17 C16 H16 119.9
C12 C17 C16 120.61(13)
C12 C17 H17 119.7
C16 C17 H17 119.7
C20 C18 C6 112.87(10)
C20 C18 C19 110.23(12)
C6 C18 C19 109.89(10)
C20 C18 H18 107.9
C6 C18 H18 107.9
C19 C18 H18 107.9
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
O22 C21 O23 125.77(11)
O22 C21 C2 123.00(11)
O23 C21 C2 111.10(10)
C21 O23 C24 115.25(11)
O23 C24 H24A 109.5
O23 C24 H24B 109.5
H24A C24 H24B 109.5
O23 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C4 C26 H26A 109.5
C4 C26 H26B 109.5
H26A C26 H26B 109.5
C4 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
C4 C27 H27A 109.5
C4 C27 H27B 109.5
H27A C27 H27B 109.5
C4 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.3432(15)
N1 C2 1.4439(13)
N1 H1 0.851(16)
C2 C6 1.5374(15)
C2 C21 1.5382(15)
C2 C3 1.5582(15)
C3 O25 1.1982(14)
C3 C4 1.5118(16)
C4 C5 1.5224(15)
C4 C27 1.5269(16)
C4 C26 1.5341(17)
C5 O28 1.2264(14)
C6 O7 1.4597(13)
C6 C18 1.5269(16)
C6 H6 1.0000
O7 C8 1.3429(14)
C8 O9 1.1945(15)
C8 O10 1.3278(15)
O10 C11 1.4543(14)
C11 C12 1.4960(17)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C17 1.3795(18)
C12 C13 1.3889(16)
C13 C14 1.3849(19)
C13 H13 0.9500
C14 C15 1.377(2)
C14 H14 0.9500
C15 C16 1.374(2)
C15 H15 0.9500
C16 C17 1.390(2)
C16 H16 0.9500
C17 H17 0.9500
C18 C20 1.5220(19)
C18 C19 1.5309(18)
C18 H18 1.0000
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 O22 1.1946(15)
C21 O23 1.3266(15)
O23 C24 1.4559(15)
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
C26 H26A 0.9800
C26 H26B 0.9800
C26 H26C 0.9800
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
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
C5 N1 C2 C6 -116.73(11)
C5 N1 C2 C21 112.09(11)
C5 N1 C2 C3 0.46(12)
N1 C2 C3 O25 -178.29(11)
C6 C2 C3 O25 -58.53(14)
C21 C2 C3 O25 65.46(14)
N1 C2 C3 C4 2.51(11)
C6 C2 C3 C4 122.27(9)
C21 C2 C3 C4 -113.74(10)
O25 C3 C4 C5 176.69(11)
C2 C3 C4 C5 -4.14(11)
O25 C3 C4 C27 56.25(15)
C2 C3 C4 C27 -124.58(10)
O25 C3 C4 C26 -66.74(15)
C2 C3 C4 C26 112.43(10)
C2 N1 C5 O28 177.40(11)
C2 N1 C5 C4 -3.24(13)
C3 C4 C5 O28 -176.17(11)
C27 C4 C5 O28 -56.47(15)
C26 C4 C5 O28 67.07(15)
C3 C4 C5 N1 4.46(12)
C27 C4 C5 N1 124.16(11)
C26 C4 C5 N1 -112.30(11)
N1 C2 C6 O7 64.61(11)
C21 C2 C6 O7 -165.97(8)
C3 C2 C6 O7 -47.86(10)
N1 C2 C6 C18 -52.71(13)
C21 C2 C6 C18 76.70(12)
C3 C2 C6 C18 -165.18(9)
C18 C6 O7 C8 -117.42(10)
C2 C6 O7 C8 119.38(10)
C6 O7 C8 O9 0.77(17)
C6 O7 C8 O10 -179.49(9)
O9 C8 O10 C11 -3.58(19)
O7 C8 O10 C11 176.68(10)
C8 O10 C11 C12 128.98(12)
O10 C11 C12 C17 7.42(19)
O10 C11 C12 C13 -173.05(11)
C17 C12 C13 C14 0.05(19)
C11 C12 C13 C14 -179.50(13)
C12 C13 C14 C15 -0.4(2)
C13 C14 C15 C16 0.5(2)
C14 C15 C16 C17 -0.1(3)
C13 C12 C17 C16 0.3(2)
C11 C12 C17 C16 179.81(14)
C15 C16 C17 C12 -0.2(2)
O7 C6 C18 C20 -172.06(10)
C2 C6 C18 C20 -56.42(14)
O7 C6 C18 C19 64.46(13)
C2 C6 C18 C19 -179.91(11)
N1 C2 C21 O22 -21.64(16)
C6 C2 C21 O22 -151.85(11)
C3 C2 C21 O22 87.69(13)
N1 C2 C21 O23 162.20(9)
C6 C2 C21 O23 31.99(13)
C3 C2 C21 O23 -88.48(11)
O22 C21 O23 C24 3.56(18)
C2 C21 O23 C24 179.60(11)
