#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011748.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011748
loop_
_publ_author_name
'Cox, Philip J.'
'Meng, Yanhui'
'Sarker, Satyajit D.'
'Deng, Qinying'
'Xu, Guo'
_publ_section_title
;
 Nodosin
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              203
_journal_page_last               204
_journal_paper_doi               10.1107/S0108270100017406
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C20 H26 O6'
_chemical_formula_sum            'C20 H26 O6'
_chemical_formula_weight         362.41
_chemical_name_common            Nodosin
_chemical_name_systematic
;
Nodosin
;
_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'
_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                   7.474(3)
_cell_length_b                   15.262(6)
_cell_length_c                   15.870(8)
_cell_measurement_reflns_used    6964
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.85
_cell_volume                     1810.3(14)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and  COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full .933
_diffrn_measured_fraction_theta_max .933
_diffrn_measurement_device_type  'Enraf Nonius kappaCCD area detector'
_diffrn_measurement_method
;
φ and ω scans to fill Ewald sphere
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0717
_diffrn_reflns_av_sigmaI/netI    .0911
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6964
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    .097
_exptl_absorpt_correction_T_max  .99
_exptl_absorpt_correction_T_min  .95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .075
_exptl_crystal_size_min          .075
_refine_diff_density_max         .212
_refine_diff_density_min         -.210
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   'not reliably determined'
_refine_ls_extinction_coef       .022(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          .0885
_refine_ls_R_factor_gt           .0470
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0392P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1030
_reflns_number_gt                1534
_reflns_number_total             2220
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1432.cif
_cod_data_source_block           I
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (25 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

'_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 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (25
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (42
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (79
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2011748
_cod_database_fobs_code          2011748
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .1276(3) -.02306(14) -.24840(15) .0318(6) Uani d . 1 . . O
H1 .216(5) -.050(2) -.278(2) .049(12) Uiso d . 1 . . H
O2 .3339(3) .05284(14) -.16645(13) .0304(6) Uani d . 1 . . O
O3 .0567(3) .16159(13) .04022(13) .0281(5) Uani d . 1 . . O
O4 .0819(3) .06953(15) .14519(14) .0376(6) Uani d . 1 . . O
O5 .1684(3) -.09942(15) .06004(14) .0381(6) Uani d . 1 . . O
O6 -.3190(3) .08013(14) -.12022(14) .0294(6) Uani d . 1 . . O
H6 -.423(5) .070(2) -.140(2) .037(11) Uiso d . 1 . . H
C1 -.0074(4) .17544(19) -.0467(2) .0250(7) Uani d . 1 . . C
H1A -.1411 .1723 -.0468 .029(2) Uiso calc R 1 . . H
C2 .0479(5) .26616(19) -.0727(2) .0298(8) Uani d . 1 . . C
H2A .1791 .2729 -.0668 .029(2) Uiso calc R 1 . . H
H2B -.0112 .3102 -.0364 .029(2) Uiso calc R 1 . . H
C3 -.0067(5) .2799(2) -.1642(2) .0322(8) Uani d . 1 . . C
H3A -.1367 .2691 -.1700 .029(2) Uiso calc R 1 . . H
H3B .0168 .3415 -.1803 .029(2) Uiso calc R 1 . . H
C4 .0943(4) .2193(2) -.2236(2) .0293(8) Uani d . 1 . . C
C5 .0602(4) .12166(18) -.19773(18) .0223(7) Uani d . 1 . . C
H5 -.0589 .1033 -.2204 .029(2) Uiso calc R 1 . . H
C6 .2019(4) .0596(2) -.2318(2) .0256(7) Uani d . 1 . . C
H6A .2567 .0843 -.2841 .029(2) Uiso calc R 1 . . H
C7 .2643(4) .0852(2) -.08756(19) .0274(7) Uani d . 1 . . C
H7A .3253 .1402 -.0713 .029(2) Uiso calc R 1 . . H
H7B .2825 .0415 -.0423 .029(2) Uiso calc R 1 . . H
C8 .0649(4) .10143(19) -.10162(18) .0217(7) Uani d . 1 . . C
C9 .0350(4) .0818(2) .07301(19) .0265(8) Uani d . 1 . . C
C10 -.0567(4) .0113(2) .02202(19) .0241(7) Uani d . 1 . . C
C11 -.0379(4) .01631(19) -.07722(19) .0223(7) Uani d . 1 . . C
H11 .0416 -.0335 -.0937 .029(2) Uiso calc R 1 . . H
C12 -.2170(4) .0005(2) -.12226(19) .0236(7) Uani d . 1 . . C
H12 -.1907 -.0135 -.1826 .029(2) Uiso calc R 1 . . H
C13 -.3202(4) -.07723(19) -.08453(19) .0267(7) Uani d . 1 . . C
H13A -.2770 -.1318 -.1114 .029(2) Uiso calc R 1 . . H
H13B -.4484 -.0707 -.0989 .029(2) Uiso calc R 1 . . H
C14 -.3028(4) -.0869(2) .01186(19) .0283(8) Uani d . 1 . . C
H14 -.4148 -.1110 .0374 .029(2) Uiso calc R 1 . . H
C15 -.2544(4) .0032(2) .0495(2) .0285(7) Uani d . 1 . . C
H15A -.2665 .0035 .1117 .029(2) Uiso calc R 1 . . H
H15B -.3288 .0506 .0253 .029(2) Uiso calc R 1 . . H
C16 .0147(5) -.0800(2) .0440(2) .0300(8) Uani d . 1 . . C
C17 -.1414(4) -.1404(2) .0360(2) .0305(8) Uani d . 1 . . C
C18 -.1260(5) -.2261(2) .0489(2) .0408(9) Uani d . 1 . . C
H18A -.0134 -.2505 .0637 .029(2) Uiso calc R 1 . . H
H18B -.2277 -.2630 .0434 .029(2) Uiso calc R 1 . . H
C19 .0169(5) .2312(2) -.3125(2) .0389(9) Uani d . 1 . . C
H19A .0808 .1929 -.3519 .051(5) Uiso calc R 1 . . H
H19B .0310 .2923 -.3300 .051(5) Uiso calc R 1 . . H
H19C -.1104 .2158 -.3122 .051(5) Uiso calc R 1 . . H
C20 .2939(5) .2458(2) -.2266(2) .0344(9) Uani d . 1 . . C
H20A .3468 .2389 -.1705 .051(5) Uiso calc R 1 . . H
H20B .3041 .3070 -.2445 .051(5) Uiso calc R 1 . . H
H20C .3573 .2082 -.2667 .051(5) Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C6 O2 C7 110.8(2) n
C9 O3 C1 117.1(2) n
O3 C1 C2 107.4(2) n
O3 C1 C8 108.2(2) n
C2 C1 C8 115.3(3) n
C1 C2 C3 108.4(3) n
C4 C3 C2 112.0(3) n
C3 C4 C19 108.1(3) n
C3 C4 C20 109.8(3) n
C19 C4 C20 107.7(3) n
C3 C4 C5 109.6(3) n
C19 C4 C5 106.9(3) n
C20 C4 C5 114.4(3) n
C6 C5 C8 102.1(2) n
C6 C5 C4 112.7(3) n
C8 C5 C4 116.2(2) n
O1 C6 O2 110.1(2) n
O1 C6 C5 110.6(3) n
O2 C6 C5 105.5(2) n
O2 C7 C8 106.3(2) n
C1 C8 C7 112.5(3) n
C1 C8 C5 113.9(2) n
C7 C8 C5 101.4(2) y
C1 C8 C11 107.5(2) n
C7 C8 C11 108.0(3) n
C5 C8 C11 113.4(2) n
O4 C9 O3 118.3(3) n
O4 C9 C10 121.9(3) n
O3 C9 C10 119.7(3) n
C9 C10 C16 111.6(3) n
C9 C10 C15 109.9(3) n
C16 C10 C15 101.2(3) y
C9 C10 C11 117.3(3) y
C16 C10 C11 103.8(2) n
C15 C10 C11 111.7(2) n
C12 C11 C8 116.4(2) y
C12 C11 C10 112.2(2) n
C8 C11 C10 109.3(2) n
O6 C12 C13 112.3(2) n
O6 C12 C11 108.6(2) n
C13 C12 C11 112.2(3) n
C12 C13 C14 114.7(3) n
C17 C14 C15 101.4(3) n
C17 C14 C13 111.8(3) n
C15 C14 C13 108.6(3) n
C14 C15 C10 100.8(3) n
O5 C16 C17 127.4(3) y
O5 C16 C10 126.8(3) y
C17 C16 C10 105.7(3) y
C18 C17 C16 121.8(3) y
C18 C17 C14 130.0(3) y
C16 C17 C14 108.2(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.403(4) y
O2 C6 . 1.435(4) n
O2 C7 . 1.443(4) n
O3 C9 . 1.335(4) n
O3 C1 . 1.475(4) n
O4 C9 . 1.212(4) n
O5 C16 . 1.213(4) y
O6 C12 . 1.435(4) y
C1 C2 . 1.503(4) y
C1 C8 . 1.526(4) n
C2 C3 . 1.522(5) n
C3 C4 . 1.521(4) n
C4 C19 . 1.535(4) n
C4 C20 . 1.546(5) n
C4 C5 . 1.566(4) n
C5 C6 . 1.521(4) n
C5 C8 . 1.557(4) n
C7 C8 . 1.527(4) n
C8 C11 . 1.558(4) n
C9 C10 . 1.510(4) n
C10 C16 . 1.533(4) n
C10 C15 . 1.546(4) n
C10 C11 . 1.583(4) y
C11 C12 . 1.537(4) n
C12 C13 . 1.536(4) n
C13 C14 . 1.542(4) n
C14 C17 . 1.507(5) n
C14 C15 . 1.542(4) n
C16 C17 . 1.492(5) n
C17 C18 . 1.329(4) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O4 2_554 .91(3) 1.96(4) 2.841(3) 162(3)
O6 H6 O2 1_455 .85(4) 1.88(4) 2.728(3) 171(3)
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_publ_flag
C9 O3 C1 C2 -174.3(3) n
C9 O3 C1 C8 -49.2(3) n
O3 C1 C2 C3 176.5(2) n
C8 C1 C2 C3 55.8(4) n
C1 C2 C3 C4 -65.1(3) n
C2 C3 C4 C19 174.3(3) n
C2 C3 C4 C20 -68.5(3) n
C2 C3 C4 C5 58.1(4) n
C3 C4 C5 C6 -159.8(3) n
C19 C4 C5 C6 83.3(3) n
C20 C4 C5 C6 -35.9(4) n
C3 C4 C5 C8 -42.5(4) n
C19 C4 C5 C8 -159.4(3) n
C20 C4 C5 C8 81.4(4) n
C7 O2 C6 O1 -103.5(3) n
C7 O2 C6 C5 15.7(3) n
C8 C5 C6 O1 86.3(3) n
C4 C5 C6 O1 -148.3(3) n
C8 C5 C6 O2 -32.7(3) n
C4 C5 C6 O2 92.7(3) n
C6 O2 C7 C8 8.5(3) n
O3 C1 C8 C7 -47.2(3) n
C2 C1 C8 C7 73.1(3) n
O3 C1 C8 C5 -161.8(2) n
C2 C1 C8 C5 -41.5(4) n
O3 C1 C8 C11 71.6(3) n
C2 C1 C8 C11 -168.1(3) n
O2 C7 C8 C1 -150.2(2) n
O2 C7 C8 C5 -28.1(3) n
O2 C7 C8 C11 91.3(3) n
C6 C5 C8 C1 157.6(3) n
C4 C5 C8 C1 34.5(4) n
C6 C5 C8 C7 36.5(3) n
C4 C5 C8 C7 -86.5(3) n
C6 C5 C8 C11 -79.0(3) n
C4 C5 C8 C11 157.9(3) n
C1 O3 C9 O4 -177.9(3) n
C1 O3 C9 C10 -1.7(4) y
O4 C9 C10 C16 -34.6(4) n
O3 C9 C10 C16 149.3(3) n
O4 C9 C10 C15 76.8(4) n
O3 C9 C10 C15 -99.2(3) n
O4 C9 C10 C11 -154.2(3) n
O3 C9 C10 C11 29.7(4) n
C1 C8 C11 C12 86.0(3) n
C7 C8 C11 C12 -152.4(3) n
C5 C8 C11 C12 -40.9(4) n
C1 C8 C11 C10 -42.5(3) n
C7 C8 C11 C10 79.1(3) n
C5 C8 C11 C10 -169.3(2) n
C9 C10 C11 C12 -135.2(3) n
C16 C10 C11 C12 101.2(3) n
C15 C10 C11 C12 -7.1(4) y
C9 C10 C11 C8 -4.4(4) y
C16 C10 C11 C8 -128.0(3) n
C15 C10 C11 C8 123.7(3) n
C8 C11 C12 O6 -46.8(3) n
C10 C11 C12 O6 80.2(3) n
C8 C11 C12 C13 -171.5(2) n
C10 C11 C12 C13 -44.4(3) n
O6 C12 C13 C14 -86.2(3) n
C11 C12 C13 C14 36.4(4) n
C12 C13 C14 C17 -87.3(3) n
C12 C13 C14 C15 23.7(4) n
C17 C14 C15 C10 44.5(3) n
C13 C14 C15 C10 -73.3(3) n
C9 C10 C15 C14 -163.4(2) n
C16 C10 C15 C14 -45.3(3) n
C11 C10 C15 C14 64.6(3) n
C9 C10 C16 O5 -37.8(4) n
C15 C10 C16 O5 -154.6(3) n
C11 C10 C16 O5 89.5(4) n
C9 C10 C16 C17 145.8(3) n
C15 C10 C16 C17 29.0(3) n
C11 C10 C16 C17 -86.9(3) n
O5 C16 C17 C18 2.1(5) n
C10 C16 C17 C18 178.5(3) n
O5 C16 C17 C14 -177.6(3) n
C10 C16 C17 C14 -1.2(3) y
C15 C14 C17 C18 153.2(4) n
C13 C14 C17 C18 -91.3(4) n
C15 C14 C17 C16 -27.1(3) n
C13 C14 C17 C16 88.4(3) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8423576
