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#$Date: 2016-03-22 12:40:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178958 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/87/4118784.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_4118784
loop_
_publ_author_name
'K. C. Nicolaou'
'Min Lu'
'Sotirios Totokotsopoulos'
'Philipp Heretsch'
'Denis Giguère'
'Ya-Ping Sun'
'David Sarlah'
'Thu H. Nguyen'
'Ian C. Wolf'
'Donald F. Smee'
'Craig W. Day'
'Selina Bopp'
'Elizabeth A. Winzeler'
_publ_section_title
;
 Synthesis and Biological Evaluation of Epidithio-, Epitetrathio-, and
 bis-(Methylthio)diketopiperazines: Synthetic Methodology,
 Enantioselective Total Synthesis of Epicoccin G, 8,8'-epi-ent-Rostratin
 B, Gliotoxin, Gliotoxin G, Emethallicin E, and Haematocin and Discovery
 of New Antiviral and Antimalarial Agents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17320
_journal_page_last               17332
_journal_paper_doi               10.1021/ja308429f
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 102.8440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.0261(18)
_cell_length_b                   7.0220(6)
_cell_length_c                   10.1269(8)
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.26
_cell_measurement_theta_min      2.43
_cell_volume                     1596.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'φ and ω 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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7651
_diffrn_reflns_theta_full        24.77
_diffrn_reflns_theta_max         24.77
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       Parallalepiped
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.6(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2426
_reflns_number_total             2743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja308429f_si_004.cif
_cod_data_source_block           grst_0m
_cod_database_code               4118784
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.84748(10) 0.2766(3) 0.5560(2) 0.0826(6) Uani 1 1 d .
H1 H 0.8192 0.2494 0.4940 0.124 Uiso 1 1 calc R
O2 O 0.75411(9) 0.2875(2) 0.3467(2) 0.0707(5) Uani 1 1 d .
O3 O 0.74101(8) 0.9394(2) 0.08416(18) 0.0638(5) Uani 1 1 d .
O4 O 0.63577(10) 0.9855(3) -0.0933(2) 0.0858(6) Uani 1 1 d .
H4 H 0.6709 0.9918 -0.0535 0.129 Uiso 1 1 calc R
N1 N 0.78716(8) 0.5904(3) 0.34194(18) 0.0476(5) Uani 1 1 d .
N2 N 0.69239(8) 0.6776(3) 0.13188(18) 0.0466(5) Uani 1 1 d .
C1 C 0.92214(12) 0.8059(5) 0.5153(3) 0.0735(8) Uani 1 1 d .
H1A H 0.9381 0.9277 0.5166 0.088 Uiso 1 1 calc R
C2 C 0.94830(13) 0.6668(5) 0.6184(3) 0.0829(9) Uani 1 1 d .
H2 H 0.9864 0.6870 0.6710 0.099 Uiso 1 1 calc R
C3 C 0.91888(12) 0.5140(5) 0.6379(3) 0.0758(9) Uani 1 1 d .
H3 H 0.9367 0.4266 0.7034 0.091 Uiso 1 1 calc R
C4 C 0.85714(11) 0.4763(4) 0.5573(2) 0.0604(6) Uani 1 1 d .
H4A H 0.8286 0.5379 0.6026 0.073 Uiso 1 1 calc R
C5 C 0.84936(10) 0.5584(3) 0.4169(2) 0.0509(6) Uani 1 1 d .
H5 H 0.8694 0.4754 0.3630 0.061 Uiso 1 1 calc R
C6 C 0.87530(10) 0.7565(4) 0.4198(2) 0.0555(6) Uani 1 1 d .
C7 C 0.83840(10) 0.8687(4) 0.3069(3) 0.0556(6) Uani 1 1 d .
H7A H 0.8511 0.8476 0.2229 0.067 Uiso 1 1 calc R
H7B H 0.8404 1.0038 0.3273 0.067 Uiso 1 1 calc R
C8 C 0.77653(10) 0.7919(3) 0.2987(2) 0.0493(5) Uani 1 1 d .
H8 H 0.7588 0.8590 0.3649 0.059 Uiso 1 1 calc R
C9 C 0.74633(10) 0.4550(4) 0.3078(2) 0.0507(6) Uani 1 1 d .
C10 C 0.68695(10) 0.5152(3) 0.2218(2) 0.0495(5) Uani 1 1 d .
H10 H 0.6606 0.5518 0.2813 0.059 Uiso 1 1 calc R
C11 C 0.73515(9) 0.8080(3) 0.1609(2) 0.0463(5) Uani 1 1 d .
C12 C 0.65625(11) 0.3625(4) 0.1240(2) 0.0579(6) Uani 1 1 d .
H12A H 0.6849 0.2867 0.0898 0.070 Uiso 1 1 calc R
H12B H 0.6322 0.2792 0.1665 0.070 Uiso 1 1 calc R
C13 C 0.61831(11) 0.4790(4) 0.0136(2) 0.0563(6) Uani 1 1 d .
C14 C 0.65049(10) 0.6622(3) -0.0006(2) 0.0507(6) Uani 1 1 d .
H14 H 0.6736 0.6437 -0.0700 0.061 Uiso 1 1 calc R
C15 C 0.60852(12) 0.8296(4) -0.0431(3) 0.0689(7) Uani 1 1 d .
H15 H 0.5933 0.8718 0.0351 0.083 Uiso 1 1 calc R
C16 C 0.55723(13) 0.7648(5) -0.1523(3) 0.0860(9) Uani 1 1 d .
H16 H 0.5390 0.8524 -0.2174 0.103 Uiso 1 1 calc R
C17 C 0.53665(14) 0.5877(6) -0.1600(4) 0.0918(11) Uani 1 1 d .
H17 H 0.5037 0.5551 -0.2275 0.110 Uiso 1 1 calc R
C18 C 0.56522(12) 0.4449(5) -0.0640(3) 0.0756(8) Uani 1 1 d .
H18 H 0.5462 0.3296 -0.0571 0.091 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C5 124.95(19)
C9 N1 C8 122.99(19)
C5 N1 C8 111.88(18)
C11 N2 C14 123.73(19)
C11 N2 C10 123.66(18)
C14 N2 C10 112.07(18)
C6 C1 C2 119.1(3)
C3 C2 C1 120.8(3)
C2 C3 C4 121.6(3)
O1 C4 C3 107.9(2)
O1 C4 C5 112.5(2)
C3 C4 C5 110.2(2)
N1 C5 C4 116.08(19)
N1 C5 C6 101.73(18)
C4 C5 C6 111.7(2)
C1 C6 C7 130.9(3)
C1 C6 C5 120.6(2)
C7 C6 C5 108.4(2)
C6 C7 C8 102.92(19)
N1 C8 C7 103.46(19)
N1 C8 C11 111.89(18)
C7 C8 C11 114.74(19)
O2 C9 N1 123.5(2)
O2 C9 C10 119.8(2)
N1 C9 C10 116.6(2)
N2 C10 C9 112.36(18)
N2 C10 C12 103.44(18)
C9 C10 C12 114.1(2)
O3 C11 N2 123.8(2)
O3 C11 C8 120.3(2)
N2 C11 C8 115.92(19)
C13 C12 C10 102.1(2)
C18 C13 C12 130.8(3)
C18 C13 C14 120.5(3)
C12 C13 C14 108.6(2)
N2 C14 C13 102.24(19)
N2 C14 C15 116.6(2)
C13 C14 C15 113.1(2)
O4 C15 C16 108.1(3)
O4 C15 C14 113.3(2)
C16 C15 C14 108.7(2)
C17 C16 C15 122.7(3)
C16 C17 C18 120.4(3)
C13 C18 C17 119.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.420(3)
O2 C9 1.241(3)
O3 C11 1.232(3)
O4 C15 1.411(3)
N1 C9 1.327(3)
N1 C5 1.481(3)
N1 C8 1.485(3)
N2 C11 1.329(3)
N2 C14 1.472(3)
N2 C10 1.482(3)
C1 C6 1.325(4)
C1 C2 1.459(4)
C2 C3 1.307(4)
C3 C4 1.497(4)
C4 C5 1.508(3)
C5 C6 1.512(3)
C6 C7 1.490(3)
C7 C8 1.508(3)
C8 C11 1.509(3)
C9 C10 1.509(3)
C10 C12 1.523(3)
C12 C13 1.499(4)
C13 C18 1.320(4)
C13 C14 1.508(4)
C14 C15 1.522(3)
C15 C16 1.498(4)
C16 C17 1.327(5)
C17 C18 1.449(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
C6 C1 C2 C3 -16.5(5)
C1 C2 C3 C4 -0.9(5)
C2 C3 C4 O1 154.9(3)
C2 C3 C4 C5 31.6(4)
C9 N1 C5 C4 -61.5(3)
C8 N1 C5 C4 123.1(2)
C9 N1 C5 C6 177.0(2)
C8 N1 C5 C6 1.7(2)
O1 C4 C5 N1 79.2(3)
C3 C4 C5 N1 -160.3(2)
O1 C4 C5 C6 -164.8(2)
C3 C4 C5 C6 -44.3(3)
C2 C1 C6 C7 177.2(3)
C2 C1 C6 C5 -0.3(4)
N1 C5 C6 C1 155.7(2)
C4 C5 C6 C1 31.3(3)
N1 C5 C6 C7 -22.3(2)
C4 C5 C6 C7 -146.8(2)
C1 C6 C7 C8 -143.6(3)
C5 C6 C7 C8 34.2(2)
C9 N1 C8 C7 -156.7(2)
C5 N1 C8 C7 18.8(2)
C9 N1 C8 C11 -32.7(3)
C5 N1 C8 C11 142.80(19)
C6 C7 C8 N1 -31.2(2)
C6 C7 C8 C11 -153.4(2)
C5 N1 C9 O2 7.4(4)
C8 N1 C9 O2 -177.8(2)
C5 N1 C9 C10 -175.2(2)
C8 N1 C9 C10 -0.4(3)
C11 N2 C10 C9 -28.3(3)
C14 N2 C10 C9 143.5(2)
C11 N2 C10 C12 -151.9(2)
C14 N2 C10 C12 19.9(2)
O2 C9 C10 N2 -152.2(2)
N1 C9 C10 N2 30.3(3)
O2 C9 C10 C12 -34.8(3)
N1 C9 C10 C12 147.7(2)
C14 N2 C11 O3 6.5(3)
C10 N2 C11 O3 177.3(2)
C14 N2 C11 C8 -175.61(19)
C10 N2 C11 C8 -4.8(3)
N1 C8 C11 O3 -147.6(2)
C7 C8 C11 O3 -30.2(3)
N1 C8 C11 N2 34.4(3)
C7 C8 C11 N2 151.8(2)
N2 C10 C12 C13 -31.4(2)
C9 C10 C12 C13 -153.7(2)
C10 C12 C13 C18 -145.9(3)
C10 C12 C13 C14 33.5(3)
C11 N2 C14 C13 172.12(19)
C10 N2 C14 C13 0.3(2)
C11 N2 C14 C15 -64.1(3)
C10 N2 C14 C15 124.1(2)
C18 C13 C14 N2 158.1(2)
C12 C13 C14 N2 -21.4(2)
C18 C13 C14 C15 31.9(3)
C12 C13 C14 C15 -147.5(2)
N2 C14 C15 O4 78.8(3)
C13 C14 C15 O4 -163.2(2)
N2 C14 C15 C16 -161.0(2)
C13 C14 C15 C16 -42.9(3)
O4 C15 C16 C17 154.1(3)
C14 C15 C16 C17 30.7(5)
C15 C16 C17 C18 -2.5(5)
C12 C13 C18 C17 176.9(3)
C14 C13 C18 C17 -2.4(4)
C16 C17 C18 C13 -13.7(5)
