#------------------------------------------------------------------------------
#$Date: 2018-01-30 16:30:45 +0200 (Tue, 30 Jan 2018) $
#$Revision: 205898 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/97/2009716.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_2009716
loop_
_publ_author_name
'Zukerman-Schpector, J.'
'Castellano, E.E.'
'Rodrigues Fho, E.'
'Cursino V., I.J.'
_publ_section_title
;
 A new quassinoid isolated from Picrolemma pseudocoffea
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              794
_journal_page_last               797
_journal_paper_doi               10.1107/S0108270193011357
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C25 H30 O12'
_chemical_formula_weight         521.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_type_scat_source           SHELX76
_cell_angle_alpha                90.
_cell_angle_beta                 99.440(10)
_cell_angle_gamma                90.
_cell_formula_units_Z            2
_cell_length_a                   8.3720(10)
_cell_length_b                   6.257(2)
_cell_length_c                   22.299(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    292
_cell_measurement_theta_max      21
_cell_measurement_theta_min      9
_cell_volume                     1152.3(4)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.011
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3476
_diffrn_reflns_theta_max         30
_diffrn_standards_decay_%        +-0.8
_diffrn_standards_interval_time  30
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.13
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.50
_exptl_crystal_description       irregular
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.80
_refine_ls_number_parameters     335
_refine_ls_number_reflns         2657
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(|Fₒ|)+0.0003|Fₒ|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.049
_reflns_number_observed          2657
_reflns_number_total             3398
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            li1066.cif
_cod_data_source_block           li1066_structure_1_of_1
_cod_depositor_comments
;
 Adding _atom_site_type_symbol label and values.

 Antanas Vaitkus
 2013-04-09

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '
1/[\s^2^(|F~o~|)+0.0003|F~o~|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(|F~o~|)+0.0003|F~o~|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1152.2(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2009716
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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
O(1) O .1203(2) .3782(5) .22420(10)
O(2) O .2415(3) .5885(5) .29540(10)
O(3) O .1588(2) .3245(4) .38640(10)
O(4) O .3431(2) .1466(5) .34420(10)
O(5) O -.1911(3) -.1317(6) .42990(10)
O(6) O .0615(3) -.1282(5) .41130(10)
O(7) O -.1826(2) -.1660(4) .29550(10)
O(8) O -.2414(2) .3298(5) .37320(10)
O(9) O -.4763(2) .0763(6) .24120(10)
O(10) O -.5903(3) .7045(5) .07710(10)
O(11) O -.7726(3) .7952(6) .13560(10)
C(1) C -.4326(3) .4776(5) .14470(10)
C(2) C -.4506(4) .5799(6) .08530(10)
C(3) C -.3559(4) .5586(7) .04420(10)
C(4) C -.2041(4) .4271(7) .05710(10)
C(5) C -.1575(3) .3794(6) .12610(10)
C(6) C -.0210(4) .2146(6) .13660(10)
C(7) C .0392(3) .1752(6) .20280(10)
C(8) C -.0917(3) .1203(5) .23990(10)
C(9) C -.2378(3) .2770(5) .22690(10)
C(10) C -.3034(3) .3063(5) .15740(10)
C(11) C -.3640(3) .2296(6) .26860(10)
C(12) C -.2897(3) .1569(6) .33390(10)
C(13) C -.1419(3) .0150(5) .33520(10)
C(14) C -.0100(3) .1204(5) .30650(10)
C(15) C .0584(3) .3368(5) .32740(10)
C(16) C .1513(3) .4397(6) .28190(10)
C(17) C -.1427(3) -.1146(6) .23640(10)
C(18) C -.5529(4) .5476(7) .1719(2)
C(19) C -.6535(4) .6943(6) .1307(2)
C(20) C -.0954(3) -.0863(6) .39780(10)
C(21) C .1134(5) -.2480(8) .4667(2)
C(22) C .2988(3) .2181(6) .38890(10)
C(23) C .3889(4) .2023(8) .4518(2)
C(24) C -.3817(4) .1074(6) .12390(10)
C(25) C -.0692(5) .5480(9) .0331(2)
Ow O .4871(3) .1258(5) .60940(10)
H(C3) H -.3725 .6180 .0046
H(C5) H -.1112 .5236 .1473
H(C6) H .0677 .2666 .1198
H'(C6) H -.0736 .0779 .1171
H(C7) H .1385 .0777 .2159
H(C9) H -.1776 .4165 .2374
H(C11) H -.4177 .3578 .2752
H(C12) H -.3628 .0782 .3535
H(C14) H .0823 .0296 .3157
H(C15) H -.0159 .4349 .3346
H(C17) H -.2309 -.1400 .2053
H`(C17) H -.0579 -.2079 .2331
H(C18) H -.5764 .5172 .2148
H(C21) H .2236 -.2725 .4730
H`(C21) H .0823 -.1721 .5005
H"(C21) H .0557 -.3836 .4639
H(C23) H .4898 .1264 .4537
H'(C23) H .4149 .3423 .4690
H"(C23) H .3269 .1296 .4782
H(C24) H -.2925 -.0249 .1238
H'(C24) H -.4405 .1453 .0846
H"(C24) H -.4593 .0333 .1398
H(C25) H .0251 .4995 .0376
H'(C25) H -.1161 .5624 -.0039
H"(C25) H -.0631 .6572 .0597
H(08) H -.3080 .4060 .3755
H(09) H -.5381 .0297 .2596
H(OW) H .5779 .1484 .6407
H'(OW) H .4225 .2409 .5973
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
C(7) O(1) C(16) 124.6(2) yes
C(20) O(6) C(21) 116.3(3) yes
C(2) O(10) C(19) 107.0(3) yes
C(2) C(1) C(18) 107.2(3) yes
O(10) C(2) C(1) 109.0(3) yes
C(1) C(2) C(3) 127.3(3) yes
C(3) C(4) C(5) 111.2(3) yes
C(5) C(4) C(25) 111.2(3) yes
C(4) C(5) C(10) 114.1(2) yes
C(5) C(6) C(7) 112.6(3) yes
O(1) C(7) C(8) 110.6(2) yes
C(7) C(8) C(9) 111.8(2) yes
C(7) C(8) C(17) 114.2(2) yes
C(9) C(8) C(17) 113.0(2) yes
C(8) C(9) C(10) 113.2(2) yes
C(10) C(9) C(11) 117.0(2) yes
C(1) C(10) C(9) 113.0(2) yes
C(5) C(10) C(9) 107.5(2) yes
C(9) C(10) C(24) 115.9(2) yes
O(9) C(11) C(12) 110.0(3) yes
C(15) O(3) C(22) 116.0(2) yes
C(13) O(7) C(17) 108.5(2) yes
C(2) C(1) C(10) 116.4(3) yes
C(10) C(1) C(18) 135.8(3) yes
O(10) C(2) C(3) 123.7(3) yes
C(2) C(3) C(4) 120.7(3) yes
C(3) C(4) C(25) 108.2(3) yes
C(4) C(5) C(6) 110.0(3) yes
C(6) C(5) C(10) 110.6(2) yes
O(1) C(7) C(6) 103.8(2) yes
C(6) C(7) C(8) 114.7(2) yes
C(7) C(8) C(14) 106.3(2) yes
C(9) C(8) C(14) 113.1(2) yes
C(14) C(8) C(17) 97.3(2) yes
C(8) C(9) C(11) 111.1(2) yes
C(1) C(10) C(5) 107.1(2) yes
C(1) C(10) C(24) 104.3(2) yes
C(5) C(10) C(24) 108.6(2) yes
O(9) C(11) C(9) 110.0(2) yes
C(9) C(11) C(12) 114.3(2) yes
O(8) C(12) C(11) 112.8(3) yes
C(11) C(12) C(13) 112.8(3) yes
O(7) C(13) C(14) 101.4(2) yes
C(12) C(13) C(14) 112.7(2) yes
C(14) C(13) C(20) 118.3(2) yes
C(8) C(14) C(15) 112.7(2) yes
O(3) C(15) C(14) 111.6(2) yes
C(14) C(15) C(16) 112.5(2) yes
O(1) C(16) C(15) 119.0(3) yes
O(7) C(17) C(8) 105.7(2) yes
O(10) C(19) O(11) 119.7(3) yes
O(11) C(19) C(18) 132.4(4) yes
O(5) C(20) C(13) 123.6(3) yes
O(3) C(22) O(4) 122.4(3) yes
O(4) C(22) C(23) 125.4(3) yes
O(8) C(12) C(13) 106.7(2) yes
O(7) C(13) C(12) 109.7(2) yes
O(7) C(13) C(20) 103.6(2) yes
C(12) C(13) C(20) 110.2(2) yes
C(8) C(14) C(13) 99.7(2) yes
C(13) C(14) C(15) 121.6(2) yes
O(3) C(15) C(16) 110.3(2) yes
O(1) C(16) O(2) 118.7(3) yes
O(2) C(16) C(15) 121.9(3) yes
C(1) C(18) C(19) 108.7(3) yes
O(10) C(19) C(18) 108.0(3) yes
O(5) C(20) O(6) 123.7(3) yes
O(6) C(20) C(13) 112.6(3) yes
O(3) C(22) C(23) 112.2(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(7) 1.482(4) yes
O(2) C(16) 1.205(4) yes
O(3) C(22) 1.341(4) yes
O(5) C(20) 1.193(4) yes
O(6) C(21) 1.449(5) yes
O(7) C(17) 1.448(3) yes
O(9) C(11) 1.410(4) yes
O(10) C(19) 1.386(4) yes
C(1) C(2) 1.456(4) yes
C(1) C(18) 1.332(4) yes
C(3) C(4) 1.502(5) yes
C(4) C(25) 1.527(6) yes
C(5) C(10) 1.571(4) yes
C(7) C(8) 1.517(4) yes
C(8) C(14) 1.530(3) yes
C(9) C(10) 1.568(4) yes
C(10) C(24) 1.541(5) yes
C(12) C(13) 1.519(4) yes
C(13) C(20) 1.524(4) yes
C(15) C(16) 1.519(4) yes
C(22) C(23) 1.483(5) yes
O(1) C(16) 1.327(4) yes
O(3) C(15) 1.442(3) yes
O(4) C(22) 1.205(4) yes
O(6) C(20) 1.325(4) yes
O(7) C(13) 1.443(4) yes
O(8) C(12) 1.409(4) yes
O(10) C(2) 1.392(4) yes
O(11) C(19) 1.200(5) yes
C(1) C(10) 1.516(4) yes
C(2) C(3) 1.313(5) yes
C(4) C(5) 1.553(4) yes
C(5) C(6) 1.528(5) yes
C(6) C(7) 1.500(4) yes
C(8) C(9) 1.557(4) yes
C(8) C(17) 1.529(5) yes
C(9) C(11) 1.546(4) yes
C(11) C(12) 1.555(4) yes
C(13) C(14) 1.515(4) yes
C(14) C(15) 1.514(4) yes
C(18) C(19) 1.464(5) yes
