#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/37/1503709.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_1503709
loop_
_publ_author_name
'Guo, Huijuan'
'Sun, Bingda'
'Gao, Hao'
'Chen, Xulin'
'Liu, Shuchun'
'Yao, Xinsheng'
'Liu, Xingzhong'
'Che, Yongsheng'
_publ_section_title
;
 Diketopiperazines from the Cordyceps-colonizing fungus Epicoccum nigrum.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              2115
_journal_page_last               2119
_journal_paper_doi               10.1021/np900654a
_journal_volume                  72
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 N2 O7 S2, H2 O'
_chemical_formula_sum            'C18 H20 N2 O8 S2'
_chemical_formula_weight         456.48
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.861(2)
_cell_length_b                   6.3257(13)
_cell_length_c                   13.029(3)
_cell_measurement_reflns_used    334
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     887.9(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10618
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.9386
_exptl_absorpt_correction_T_min  0.9321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.2510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                3834
_reflns_number_total             3947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np900654a_si_002.cif
_cod_data_source_block           sa140
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1503709
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
S1 S 0.15756(4) 0.97040(7) 0.74872(4) 0.01810(11) Uani 1 1 d .
S1' S -0.15442(4) 0.75008(7) 0.81277(4) 0.01680(11) Uani 1 1 d .
O1 O 0.11767(13) 0.5641(3) 0.57535(11) 0.0226(3) Uani 1 1 d .
O1' O 0.04393(14) 0.5167(3) 0.97414(11) 0.0246(3) Uani 1 1 d .
O2 O 0.57910(14) 0.8319(3) 0.89155(12) 0.0235(3) Uani 1 1 d .
O2' O -0.41149(13) 0.4292(3) 0.71047(12) 0.0240(3) Uani 1 1 d .
O3 O 0.34828(13) 0.9312(3) 1.03811(11) 0.0219(3) Uani 1 1 d .
H3A H 0.3565 1.0620 1.0478 0.033 Uiso 1 1 calc R
O3' O -0.29801(14) 0.8760(3) 0.52756(11) 0.0235(3) Uani 1 1 d .
H3'A H -0.2617 0.9497 0.4870 0.035 Uiso 1 1 calc R
O4' O -0.28522(13) 0.4386(3) 0.50294(11) 0.0229(3) Uani 1 1 d .
H4'A H -0.3361 0.5205 0.4693 0.034 Uiso 1 1 calc R
O5 O -0.49759(14) 0.5526(3) 0.38892(13) 0.0297(4) Uani 1 1 d .
H5A H -0.5244 0.6646 0.3595 0.036 Uiso 1 1 d R
H5B H -0.5583 0.4997 0.4138 0.036 Uiso 1 1 d R
N1' N -0.01374(15) 0.5127(3) 0.69398(12) 0.0157(3) Uani 1 1 d .
N1 N 0.16786(15) 0.5965(3) 0.85116(12) 0.0158(3) Uani 1 1 d .
C1 C 0.09330(18) 0.5824(3) 0.66474(15) 0.0164(4) Uani 1 1 d .
C1' C 0.05731(17) 0.5467(3) 0.88400(15) 0.0166(4) Uani 1 1 d .
C2 C 0.18367(19) 0.6809(3) 0.74966(15) 0.0166(4) Uani 1 1 d .
C2' C -0.05073(17) 0.5231(3) 0.79847(14) 0.0153(4) Uani 1 1 d .
C3 C 0.32046(18) 0.6274(3) 0.74261(15) 0.0181(4) Uani 1 1 d .
H3B H 0.3567 0.7276 0.6964 0.022 Uiso 1 1 calc R
H3C H 0.3289 0.4818 0.7164 0.022 Uiso 1 1 calc R
C3' C -0.12263(19) 0.3167(3) 0.80205(15) 0.0181(4) Uani 1 1 d .
H3'B H -0.1754 0.3170 0.8587 0.022 Uiso 1 1 calc R
H3'C H -0.0664 0.1930 0.8099 0.022 Uiso 1 1 calc R
C4 C 0.38479(18) 0.6485(3) 0.85625(15) 0.0174(4) Uani 1 1 d .
H4A H 0.4354 0.5195 0.8763 0.021 Uiso 1 1 calc R
C4' C -0.20150(18) 0.3197(3) 0.69474(15) 0.0175(4) Uani 1 1 d .
H4'B H -0.2337 0.1758 0.6739 0.021 Uiso 1 1 calc R
C5' C -0.30606(18) 0.4773(3) 0.69859(14) 0.0181(4) Uani 1 1 d .
C5 C 0.46642(19) 0.8430(3) 0.86742(15) 0.0182(4) Uani 1 1 d .
C6' C -0.26439(18) 0.7063(3) 0.69511(15) 0.0167(4) Uani 1 1 d .
H6'A H -0.3383 0.7992 0.6984 0.020 Uiso 1 1 calc R
C6 C 0.40324(19) 1.0518(4) 0.84440(16) 0.0206(4) Uani 1 1 d .
H6A H 0.4078 1.0904 0.7713 0.025 Uiso 1 1 calc R
H6B H 0.4470 1.1624 0.8888 0.025 Uiso 1 1 calc R
C7 C 0.26647(18) 1.0432(3) 0.86362(15) 0.0186(4) Uani 1 1 d .
H7A H 0.2432 1.1881 0.8851 0.022 Uiso 1 1 calc R
C7' C -0.20847(18) 0.7580(4) 0.59390(15) 0.0183(4) Uani 1 1 d .
H7'A H -0.1315 0.8444 0.6108 0.022 Uiso 1 1 calc R
C8 C 0.25331(18) 0.8936(3) 0.95460(15) 0.0181(4) Uani 1 1 d .
H8A H 0.1695 0.9092 0.9779 0.022 Uiso 1 1 calc R
C8' C -0.17682(18) 0.5522(4) 0.54085(15) 0.0189(4) Uani 1 1 d .
H8'A H -0.1248 0.5809 0.4843 0.023 Uiso 1 1 calc R
C9 C 0.27478(18) 0.6653(3) 0.92310(15) 0.0171(4) Uani 1 1 d .
H9A H 0.2883 0.5705 0.9849 0.021 Uiso 1 1 calc R
C9' C -0.10944(18) 0.4015(3) 0.62246(15) 0.0176(4) Uani 1 1 d .
H9'A H -0.0717 0.2806 0.5881 0.021 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'
S S 0.1246 0.1234 '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
C7 S1 C2 99.17(9)
C6' S1' C2' 97.96(9)
C8 O3 H3A 109.5
C7' O3' H3'A 109.5
C8' O4' H4'A 109.5
H5A O5 H5B 105.6
C1 N1' C2' 126.62(16)
C1 N1' C9' 122.72(16)
C2' N1' C9' 110.58(15)
C1' N1 C2 125.46(16)
C1' N1 C9 121.83(16)
C2 N1 C9 107.31(15)
O1 C1 N1' 122.34(18)
O1 C1 C2 122.10(18)
N1' C1 C2 115.55(16)
O1' C1' N1 123.87(18)
O1' C1' C2' 121.15(17)
N1 C1' C2' 114.96(16)
N1 C2 C1 111.84(16)
N1 C2 C3 101.49(16)
C1 C2 C3 114.00(16)
N1 C2 S1 109.45(14)
C1 C2 S1 108.47(14)
C3 C2 S1 111.44(14)
N1' C2' C1' 114.06(15)
N1' C2' C3' 101.02(15)
C1' C2' C3' 114.34(16)
N1' C2' S1' 111.70(13)
C1' C2' S1' 105.88(13)
C3' C2' S1' 109.94(13)
C2 C3 C4 104.14(15)
C2 C3 H3B 110.9
C4 C3 H3B 110.9
C2 C3 H3C 110.9
C4 C3 H3C 110.9
H3B C3 H3C 108.9
C2' C3' C4' 100.91(15)
C2' C3' H3'B 111.6
C4' C3' H3'B 111.6
C2' C3' H3'C 111.6
C4' C3' H3'C 111.6
H3'B C3' H3'C 109.4
C5 C4 C3 110.34(17)
C5 C4 C9 111.73(17)
C3 C4 C9 104.57(15)
C5 C4 H4A 110.0
C3 C4 H4A 110.0
C9 C4 H4A 110.0
C5' C4' C3' 108.05(16)
C5' C4' C9' 110.14(17)
C3' C4' C9' 103.18(15)
C5' C4' H4'B 111.7
C3' C4' H4'B 111.7
C9' C4' H4'B 111.7
O2' C5' C4' 124.2(2)
O2' C5' C6' 122.17(19)
C4' C5' C6' 113.49(17)
O2 C5 C6 121.16(19)
O2 C5 C4 122.15(19)
C6 C5 C4 116.67(17)
C5' C6' C7' 112.05(16)
C5' C6' S1' 106.43(13)
C7' C6' S1' 113.12(13)
C5' C6' H6'A 108.4
C7' C6' H6'A 108.4
S1' C6' H6'A 108.4
C5 C6 C7 111.26(18)
C5 C6 H6A 109.4
C7 C6 H6A 109.4
C5 C6 H6B 109.4
C7 C6 H6B 109.4
H6A C6 H6B 108.0
C8 C7 C6 109.46(16)
C8 C7 S1 111.06(14)
C6 C7 S1 114.20(14)
C8 C7 H7A 107.3
C6 C7 H7A 107.3
S1 C7 H7A 107.3
O3' C7' C8' 110.22(16)
O3' C7' C6' 108.31(16)
C8' C7' C6' 109.74(17)
O3' C7' H7'A 109.5
C8' C7' H7'A 109.5
C6' C7' H7'A 109.5
O3 C8 C9 104.08(16)
O3 C8 C7 110.97(16)
C9 C8 C7 110.04(16)
O3 C8 H8A 110.5
C9 C8 H8A 110.5
C7 C8 H8A 110.5
O4' C8' C7' 111.39(16)
O4' C8' C9' 103.21(17)
C7' C8' C9' 109.14(15)
O4' C8' H8'A 111.0
C7' C8' H8'A 111.0
C9' C8' H8'A 111.0
N1 C9 C8 108.51(16)
N1 C9 C4 102.87(16)
C8 C9 C4 111.46(16)
N1 C9 H9A 111.2
C8 C9 H9A 111.2
C4 C9 H9A 111.2
N1' C9' C8' 111.97(17)
N1' C9' C4' 103.41(15)
C8' C9' C4' 109.86(16)
N1' C9' H9'A 110.5
C8' C9' H9'A 110.5
C4' C9' H9'A 110.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.845(2)
S1 C2 1.853(2)
S1' C6' 1.841(2)
S1' C2' 1.848(2)
O1 C1 1.232(2)
O1' C1' 1.216(2)
O2 C5 1.226(3)
O2' C5' 1.214(2)
O3 C8 1.421(2)
O3 H3A 0.8400
O3' C7' 1.427(2)
O3' H3'A 0.8400
O4' C8' 1.414(2)
O4' H4'A 0.8400
O5 H5A 0.8401
O5 H5B 0.8400
N1' C1 1.343(2)
N1' C2' 1.469(2)
N1' C9' 1.483(2)
N1 C1' 1.362(2)
N1 C2 1.456(3)
N1 C9 1.463(2)
C1 C2 1.517(3)
C1' C2' 1.520(3)
C2 C3 1.538(3)
C2' C3' 1.525(3)
C3 C4 1.561(3)
C3 H3B 0.9900
C3 H3C 0.9900
C3' C4' 1.545(3)
C3' H3'B 0.9900
C3' H3'C 0.9900
C4 C5 1.512(3)
C4 C9 1.569(3)
C4 H4A 1.0000
C4' C5' 1.517(3)
C4' C9' 1.547(3)
C4' H4'B 1.0000
C5' C6' 1.520(3)
C5 C6 1.501(3)
C6' C7' 1.555(3)
C6' H6'A 1.0000
C6 C7 1.538(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.538(3)
C7 H7A 1.0000
C7' C8' 1.533(3)
C7' H7'A 1.0000
C8 C9 1.528(3)
C8 H8A 1.0000
C8' C9' 1.542(3)
C8' H8'A 1.0000
C9 H9A 1.0000
C9' H9'A 1.0000
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.84 1.97 2.776(2) 159.8 2_657
O3' H3'A O1 0.84 1.99 2.778(2) 156.3 2_556
O4' H4'A O5 0.84 1.94 2.679(2) 147.0 .
O5 H5A O2' 0.84 1.99 2.829(2) 179.7 2_456
O5 H5B O3' 0.84 1.98 2.823(2) 179.7 2_446
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
C2' N1' C1 O1 178.79(19)
C9' N1' C1 O1 2.2(3)
C2' N1' C1 C2 0.1(3)
C9' N1' C1 C2 -176.47(17)
C2 N1 C1' O1' -164.9(2)
C9 N1 C1' O1' -14.2(3)
C2 N1 C1' C2' 17.1(3)
C9 N1 C1' C2' 167.78(18)
C1' N1 C2 C1 -37.9(3)
C9 N1 C2 C1 167.91(16)
C1' N1 C2 C3 -159.83(18)
C9 N1 C2 C3 46.00(19)
C1' N1 C2 S1 82.3(2)
C9 N1 C2 S1 -71.86(17)
O1 C1 C2 N1 -151.42(19)
N1' C1 C2 N1 27.3(2)
O1 C1 C2 C3 -37.0(3)
N1' C1 C2 C3 141.71(18)
O1 C1 C2 S1 87.8(2)
N1' C1 C2 S1 -93.50(18)
C7 S1 C2 N1 52.93(15)
C7 S1 C2 C1 175.19(13)
C7 S1 C2 C3 -58.52(15)
C1 N1' C2' C1' -21.3(3)
C9' N1' C2' C1' 155.65(17)
C1 N1' C2' C3' -144.40(18)
C9' N1' C2' C3' 32.50(19)
C1 N1' C2' S1' 98.76(19)
C9' N1' C2' S1' -84.34(17)
O1' C1' C2' N1' -165.65(19)
N1 C1' C2' N1' 12.5(3)
O1' C1' C2' C3' -50.1(3)
N1 C1' C2' C3' 128.03(18)
O1' C1' C2' S1' 71.1(2)
N1 C1' C2' S1' -110.77(16)
C6' S1' C2' N1' 48.89(14)
C6' S1' C2' C1' 173.60(13)
C6' S1' C2' C3' -62.40(14)
N1 C2 C3 C4 -33.92(19)
C1 C2 C3 C4 -154.32(17)
S1 C2 C3 C4 82.49(17)
N1' C2' C3' C4' -44.35(17)
C1' C2' C3' C4' -167.30(16)
S1' C2' C3' C4' 73.77(15)
C2 C3 C4 C5 -108.55(18)
C2 C3 C4 C9 11.7(2)
C2' C3' C4' C5' -75.60(18)
C2' C3' C4' C9' 41.03(18)
C3' C4' C5' O2' -99.6(2)
C9' C4' C5' O2' 148.35(19)
C3' C4' C5' C6' 75.5(2)
C9' C4' C5' C6' -36.5(2)
C3 C4 C5 O2 -117.4(2)
C9 C4 C5 O2 126.7(2)
C3 C4 C5 C6 60.8(2)
C9 C4 C5 C6 -55.0(2)
O2' C5' C6' C7' -123.87(19)
C4' C5' C6' C7' 60.9(2)
O2' C5' C6' S1' 112.00(18)
C4' C5' C6' S1' -63.26(18)
C2' S1' C6' C5' 51.70(14)
C2' S1' C6' C7' -71.77(15)
O2 C5 C6 C7 -154.77(19)
C4 C5 C6 C7 26.9(2)
C5 C6 C7 C8 33.6(2)
C5 C6 C7 S1 -91.60(18)
C2 S1 C7 C8 -45.86(15)
C2 S1 C7 C6 78.51(17)
C5' C6' C7' O3' 104.20(19)
S1' C6' C7' O3' -135.49(15)
C5' C6' C7' C8' -16.2(2)
S1' C6' C7' C8' 104.15(16)
C6 C7 C8 O3 45.0(2)
S1 C7 C8 O3 171.99(13)
C6 C7 C8 C9 -69.7(2)
S1 C7 C8 C9 57.34(18)
O3' C7' C8' O4' -51.4(2)
C6' C7' C8' O4' 67.8(2)
O3' C7' C8' C9' -164.70(16)
C6' C7' C8' C9' -45.5(2)
C1' N1 C9 C8 -75.3(2)
C2 N1 C9 C8 79.97(18)
C1' N1 C9 C4 166.48(18)
C2 N1 C9 C4 -38.21(19)
O3 C8 C9 N1 169.09(15)
C7 C8 C9 N1 -71.95(19)
O3 C8 C9 C4 -78.33(18)
C7 C8 C9 C4 40.6(2)
C5 C4 C9 N1 134.00(17)
C3 C4 C9 N1 14.64(19)
C5 C4 C9 C8 17.9(2)
C3 C4 C9 C8 -101.44(19)
C1 N1' C9' C8' -71.4(2)
C2' N1' C9' C8' 111.51(18)
C1 N1' C9' C4' 170.34(17)
C2' N1' C9' C4' -6.7(2)
O4' C8' C9' N1' -162.63(15)
C7' C8' C9' N1' -44.1(2)
O4' C8' C9' C4' -48.3(2)
C7' C8' C9' C4' 70.2(2)
C5' C4' C9' N1' 93.50(18)
C3' C4' C9' N1' -21.64(19)
C5' C4' C9' C8' -26.2(2)
C3' C4' C9' C8' -141.31(17)
