#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/20/2202007.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_2202007
loop_
_publ_author_name
'V. Rajakannan'
'M. S. Sripathi'
'S. Selvanayagam'
'D. Velmurugan'
'Uma. D. Murthy'
'M. Vishwas'
'S. P. Thyagarajan'
'S. Shanmuga Sundara Raj'
'Hoong-Kun Fun'
_publ_section_title
;
 Phyllanthin from the plant Phyllanthus amarus
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o203
_journal_page_last               o205
_journal_paper_doi               10.1107/S1600536803001119
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C24 H34 O6'
_chemical_formula_moiety         'C24 H34 O6'
_chemical_formula_sum            'C24 H34 O6'
_chemical_formula_weight         418.51
_chemical_name_systematic
;
Phyllanthin from the plant phyllanthus amarus
;
_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                 117.3280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   22.6091(7)
_cell_length_b                   5.3506(2)
_cell_length_c                   11.0871(4)
_cell_measurement_reflns_used    2451
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.85
_cell_volume                     1191.54(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.906
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_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  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4350
_diffrn_reflns_theta_full        29.44
_diffrn_reflns_theta_max         29.44
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1651
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0656
_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)+(0.1P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1710
_refine_ls_wR_factor_ref         0.1814
_reflns_number_gt                1138
_reflns_number_total             1651
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6023.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_original_sg_symbol_H-M      'C 2'
_cod_database_code               2202007
_cod_database_fobs_code          2202007
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_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
C1 0.18603(14) 0.2388(5) 0.1763(3) 0.0525(7) Uani d . 1 . . C
H1 0.1671 0.1193 0.1083 0.063 Uiso calc R 1 . . H
C2 0.25446(14) 0.2525(6) 0.2500(3) 0.0504(6) Uani d . 1 . . C
C3 0.28296(14) 0.4318(7) 0.3520(3) 0.0551(7) Uani d . 1 . . C
C4 0.24336(15) 0.5915(7) 0.3788(3) 0.0591(8) Uani d . 1 . . C
H4 0.2623 0.7113 0.4466 0.071 Uiso calc R 1 . . H
C5 0.17412(16) 0.5739(7) 0.3037(4) 0.0655(8) Uani d . 1 . . C
H5 0.1473 0.6818 0.3229 0.079 Uiso calc R 1 . . H
C6 0.14496(13) 0.3996(6) 0.2019(3) 0.0541(7) Uani d . 1 . . C
C7 0.27271(18) -0.0825(7) 0.1282(3) 0.0688(9) Uani d . 1 . . C
H7A 0.3089 -0.1735 0.1263 0.103 Uiso calc R 1 . . H
H7B 0.2471 -0.0031 0.0420 0.103 Uiso calc R 1 . . H
H7C 0.2448 -0.1955 0.1464 0.103 Uiso calc R 1 . . H
C8 0.3824(2) 0.6355(12) 0.5097(4) 0.1026(16) Uani d . 1 . . C
H8A 0.4299 0.6195 0.5491 0.154 Uiso calc R 1 . . H
H8B 0.3690 0.6311 0.5802 0.154 Uiso calc R 1 . . H
H8C 0.3690 0.7914 0.4618 0.154 Uiso calc R 1 . . H
C9 0.06954(14) 0.3821(6) 0.1186(4) 0.0660(9) Uani d . 1 . . C
H9A 0.0501 0.3564 0.1795 0.079 Uiso calc R 1 . . H
H9B 0.0586 0.2381 0.0590 0.079 Uiso calc R 1 . . H
C10 0.03874(11) 0.6173(5) 0.0326(3) 0.0516(7) Uani d . 1 . . C
H10 0.0546 0.7616 0.0937 0.062 Uiso calc R 1 . . H
C11 0.06378(15) 0.6467(7) -0.0710(4) 0.0624(8) Uani d . 1 . . C
H11A 0.1121 0.6417 -0.0261 0.075 Uiso calc R 1 . . H
H11B 0.0476 0.5094 -0.1352 0.075 Uiso calc R 1 . . H
C12 0.0643(2) 0.9193(13) -0.2370(5) 0.1028(15) Uani d . 1 . . C
H12A 0.0472 1.0765 -0.2810 0.154 Uiso calc R 1 . . H
H12B 0.0490 0.7878 -0.3033 0.154 Uiso calc R 1 . . H
H12C 0.1121 0.9237 -0.1928 0.154 Uiso calc R 1 . . H
O1 0.29828(10) 0.1008(5) 0.2311(2) 0.0712(7) Uani d . 1 . . O
O2 0.35194(10) 0.4356(6) 0.4181(2) 0.0763(8) Uani d . 1 . . O
O3 0.04179(12) 0.8754(6) -0.1407(3) 0.0810(9) Uani d . 1 . . O
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 0.0000 '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'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.3(3) ?
C2 C1 H1 . . 119.3 ?
C6 C1 H1 . . 119.3 ?
O1 C2 C1 . . 124.8(3) y
O1 C2 C3 . . 115.7(2) y
C1 C2 C3 . . 119.4(2) ?
C4 C3 O2 . . 124.5(3) y
C4 C3 C2 . . 120.1(2) ?
O2 C3 C2 . . 115.3(3) y
C3 C4 C5 . . 119.7(3) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C5 C4 . . 121.1(3) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C1 . . 118.3(2) ?
C5 C6 C9 . . 121.3(3) ?
C1 C6 C9 . . 120.4(3) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C6 C9 C10 . . 112.8(2) ?
C6 C9 H9A . . 109.0 ?
C10 C9 H9A . . 109.0 ?
C6 C9 H9B . . 109.0 ?
C10 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C11 C10 C9 . . 109.7(2) ?
C11 C10 C10 . 2 112.5(3) ?
C9 C10 C10 . 2 112.34(17) ?
C11 C10 H10 . . 107.4 ?
C9 C10 H10 . . 107.4 ?
C10 C10 H10 2 . 107.4 ?
O3 C11 C10 . . 110.3(3) ?
O3 C11 H11A . . 109.6 ?
C10 C11 H11A . . 109.6 ?
O3 C11 H11B . . 109.6 ?
C10 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
O3 C12 H12A . . 109.5 ?
O3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 O1 C7 . . 118.6(2) ?
C3 O2 C8 . . 116.7(3) ?
C12 O3 C11 . . 113.8(4) ?
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
C1 C2 . 1.381(4) y
C1 C6 . 1.387(4) y
C1 H1 . 0.9300 ?
C2 O1 . 1.369(4) y
C2 C3 . 1.395(4) y
C3 C4 . 1.365(4) y
C3 O2 . 1.386(3) y
C4 C5 . 1.399(4) y
C4 H4 . 0.9300 ?
C5 C6 . 1.377(4) y
C5 H5 . 0.9300 ?
C6 C9 . 1.524(4) y
C7 O1 . 1.411(4) y
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 O2 . 1.417(6) y
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.539(4) y
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.504(4) y
C10 C10 2 1.558(5) y
C10 H10 . 0.9800 ?
C11 O3 . 1.411(5) y
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O3 . 1.397(5) y
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 O1 . . 179.9(3) ?
C6 C1 C2 C3 . . -0.1(4) ?
O1 C2 C3 C4 . . -179.8(3) ?
C1 C2 C3 C4 . . 0.2(4) ?
O1 C2 C3 O2 . . 1.5(4) ?
C1 C2 C3 O2 . . -178.5(3) ?
O2 C3 C4 C5 . . 178.7(3) ?
C2 C3 C4 C5 . . 0.2(5) ?
C3 C4 C5 C6 . . -0.7(5) ?
C4 C5 C6 C1 . . 0.8(5) ?
C4 C5 C6 C9 . . -179.2(3) ?
C2 C1 C6 C5 . . -0.4(4) ?
C2 C1 C6 C9 . . 179.6(3) ?
C5 C6 C9 C10 . . 64.7(4) y
C1 C6 C9 C10 . . -115.3(3) y
C6 C9 C10 C11 . . 63.8(3) ?
C6 C9 C10 C10 . 2 -170.3(3) ?
C9 C10 C11 O3 . . -173.6(2) ?
C10 C10 C11 O3 2 . 60.6(3) y
C1 C2 O1 C7 . . 0.8(5) y
C3 C2 O1 C7 . . -179.2(3) y
C4 C3 O2 C8 . . -6.6(5) y
C2 C3 O2 C8 . . 172.1(3) y
C10 C11 O3 C12 . . 178.7(3) y
