#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228448.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_2228448
loop_
_publ_author_name
'Ee, Gwendoline Cheng Lian'
'Teo, Siow Hwa'
'Kwong, Huey Chong'
'Mohamed Tahir, Mohamed Ibrahim'
'Silong, Sidik'
_publ_section_title
;
 12-Acetyl-6-hydroxy-3,3,9,9-tetramethylfuro[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione
;
_journal_coeditor_code           KP2279
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3331
_journal_page_last               o3332
_journal_paper_doi               10.1107/S1600536810048592
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C24 H20 O7'
_chemical_formula_moiety         'C24 H20 O7'
_chemical_formula_sum            'C24 H20 O7'
_chemical_formula_weight         420.42
_chemical_melting_point          189
_chemical_name_common            'Artonol B'
_chemical_name_systematic
;
12-Acetyl-6-hydroxy-3,3,9,9-tetramethylfuro[3,4-b]pyrano[3,2-
h]xanthene-7,11(3H,9H)-dione
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 96.318(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.511(2)
_cell_length_b                   5.3275(2)
_cell_length_c                   20.0218(8)
_cell_measurement_reflns_used    8995
_cell_measurement_temperature    150
_cell_measurement_theta_max      3.4694
_cell_measurement_theta_min      71.9650
_cell_volume                     3870.8(3)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini E'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17338
_diffrn_reflns_theta_full        72.111
_diffrn_reflns_theta_max         72.111
_diffrn_reflns_theta_min         4.444
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_correction_T_min  0.7798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.0002873
_refine_ls_shift/su_mean         0.0000212
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(F²) + (0.07P)² + 3.68P], where P=[max(Fo²,0) + 2Fc²]/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1102
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                3383
_reflns_number_total             3813
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            kp2279.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2228448
_cod_database_fobs_code          2228448
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
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.12808(2) 0.38440(18) 0.09348(4) 0.0198 Uani 1.0000 . .
C C2 0.10246(3) 0.5702(2) 0.07942(6) 0.0185 Uani 1.0000 . .
C C3 0.09197(4) 0.7295(2) 0.12975(6) 0.0191 Uani 1.0000 . .
C C4 0.10576(4) 0.6903(3) 0.19901(6) 0.0202 Uani 1.0000 . .
O O5 0.09659(3) 0.82336(19) 0.24578(5) 0.0261 Uani 1.0000 . .
C C6 0.13177(3) 0.4810(2) 0.21237(6) 0.0195 Uani 1.0000 . .
C C7 0.14301(4) 0.3455(3) 0.15819(6) 0.0190 Uani 1.0000 . .
C C8 0.16981(4) 0.1566(3) 0.16701(7) 0.0197 Uani 1.0000 . .
C C9 0.18272(4) 0.0989(2) 0.23308(7) 0.0201 Uani 1.0000 . .
C C10 0.17096(4) 0.2259(3) 0.28733(6) 0.0204 Uani 1.0000 . .
C C11 0.14611(4) 0.4195(3) 0.27803(7) 0.0205 Uani 1.0000 . .
H H111 0.1386 0.5096 0.3144 0.0256 Uiso 1.0000 . .
C C12 0.18915(4) 0.1142(3) 0.35190(7) 0.0224 Uani 1.0000 . .
O O13 0.21047(3) -0.09518(18) 0.32781(5) 0.0251 Uani 1.0000 . .
C C14 0.20880(4) -0.1013(3) 0.25958(7) 0.0223 Uani 1.0000 . .
O O15 0.22540(3) -0.2519(2) 0.23027(5) 0.0287 Uani 1.0000 . .
C C16 0.21617(4) 0.2917(3) 0.39064(7) 0.0288 Uani 1.0000 . .
H H163 0.2033 0.4353 0.4063 0.0429 Uiso 1.0000 . .
H H162 0.2289 0.2059 0.4301 0.0439 Uiso 1.0000 . .
H H161 0.2342 0.3494 0.3624 0.0428 Uiso 1.0000 . .
C C17 0.16119(4) 0.0067(3) 0.39501(7) 0.0277 Uani 1.0000 . .
H H171 0.1481 0.1395 0.4145 0.0409 Uiso 1.0000 . .
H H172 0.1737 -0.0925 0.4316 0.0407 Uiso 1.0000 . .
H H173 0.1438 -0.0978 0.3681 0.0410 Uiso 1.0000 . .
C C18 0.18478(4) 0.0411(3) 0.10628(7) 0.0213 Uani 1.0000 . .
O O19 0.17671(3) -0.1689(2) 0.08765(6) 0.0334 Uani 1.0000 . .
C C20 0.20997(4) 0.2106(3) 0.07285(7) 0.0271 Uani 1.0000 . .
H H203 0.2185 0.1277 0.0339 0.0398 Uiso 1.0000 . .
H H202 0.2306 0.2608 0.1047 0.0413 Uiso 1.0000 . .
H H201 0.1967 0.3604 0.0575 0.0414 Uiso 1.0000 . .
C C21 0.06673(4) 0.9261(2) 0.11022(7) 0.0208 Uani 1.0000 . .
O O22 0.05637(3) 1.08580(19) 0.15665(5) 0.0275 Uani 1.0000 . .
H H221 0.0674 1.0316 0.1953 0.0432 Uiso 1.0000 . .
C C23 0.05232(4) 0.9535(3) 0.04379(7) 0.0221 Uani 1.0000 . .
C C24 0.06218(4) 0.7823(2) -0.00367(6) 0.0198 Uani 1.0000 . .
C C25 0.08781(4) 0.5891(2) 0.01261(6) 0.0194 Uani 1.0000 . .
C C26 0.09776(4) 0.4252(3) -0.04086(7) 0.0215 Uani 1.0000 . .
C C27 0.07852(4) 0.4357(3) -0.10100(7) 0.0225 Uani 1.0000 . .
C C28 0.04539(4) 0.6033(3) -0.11489(6) 0.0220 Uani 1.0000 . .
O O29 0.04714(3) 0.81622(18) -0.06783(5) 0.0252 Uani 1.0000 . .
C C30 0.04382(5) 0.7261(3) -0.18347(7) 0.0318 Uani 1.0000 . .
H H301 0.0229 0.8361 -0.1902 0.0461 Uiso 1.0000 . .
H H302 0.0663 0.8214 -0.1864 0.0468 Uiso 1.0000 . .
H H303 0.0418 0.6015 -0.2176 0.0477 Uiso 1.0000 . .
C C31 0.01040(4) 0.4563(3) -0.10626(8) 0.0307 Uani 1.0000 . .
H H311 0.0115 0.3962 -0.0603 0.0455 Uiso 1.0000 . .
H H313 -0.0111 0.5621 -0.1161 0.0455 Uiso 1.0000 . .
H H312 0.0084 0.3170 -0.1366 0.0447 Uiso 1.0000 . .
H H271 0.0845 0.3337 -0.1366 0.0260 Uiso 1.0000 . .
H H261 0.1176 0.3146 -0.0317 0.0269 Uiso 1.0000 . .
H H231 0.0354 1.0844 0.0313 0.0277 Uiso 1.0000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 'International Tables Vol C 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C7 . . . 119.81(10) no
O1 C2 C3 . . . 121.60(11) no
O1 C2 C25 . . . 115.63(11) no
C3 C2 C25 . . . 122.77(12) no
C2 C3 C4 . . . 120.74(12) no
C2 C3 C21 . . . 117.93(12) no
C4 C3 C21 . . . 121.32(12) no
C3 C4 O5 . . . 123.14(12) no
C3 C4 C6 . . . 115.85(11) no
O5 C4 C6 . . . 121.01(12) no
C4 C6 C7 . . . 119.24(12) no
C4 C6 C11 . . . 121.07(12) no
C7 C6 C11 . . . 119.68(12) no
C6 C7 O1 . . . 122.41(12) no
C6 C7 C8 . . . 122.17(12) no
O1 C7 C8 . . . 115.41(11) no
C7 C8 C9 . . . 116.00(12) no
C7 C8 C18 . . . 119.90(11) no
C9 C8 C18 . . . 123.96(12) no
C8 C9 C10 . . . 122.38(12) no
C8 C9 C14 . . . 129.44(12) no
C10 C9 C14 . . . 108.15(12) no
C9 C10 C11 . . . 121.15(12) no
C9 C10 C12 . . . 109.47(12) no
C11 C10 C12 . . . 129.38(12) no
C6 C11 C10 . . . 118.48(12) no
C6 C11 H111 . . . 120.0 no
C10 C11 H111 . . . 121.6 no
C10 C12 O13 . . . 102.52(10) no
C10 C12 C16 . . . 113.10(12) no
O13 C12 C16 . . . 107.61(11) no
C10 C12 C17 . . . 112.04(11) no
O13 C12 C17 . . . 108.25(11) no
C16 C12 C17 . . . 112.61(12) no
C12 O13 C14 . . . 112.35(10) no
C9 C14 O13 . . . 107.28(11) no
C9 C14 O15 . . . 130.08(13) no
O13 C14 O15 . . . 122.60(12) no
C12 C16 H163 . . . 110.2 no
C12 C16 H162 . . . 110.1 no
H163 C16 H162 . . . 108.0 no
C12 C16 H161 . . . 110.3 no
H163 C16 H161 . . . 109.0 no
H162 C16 H161 . . . 109.1 no
C12 C17 H171 . . . 110.4 no
C12 C17 H172 . . . 110.0 no
H171 C17 H172 . . . 107.9 no
C12 C17 H173 . . . 110.0 no
H171 C17 H173 . . . 109.1 no
H172 C17 H173 . . . 109.4 no
C8 C18 O19 . . . 121.81(13) no
C8 C18 C20 . . . 113.98(11) no
O19 C18 C20 . . . 124.21(13) no
C18 C20 H203 . . . 110.5 no
C18 C20 H202 . . . 110.0 no
H203 C20 H202 . . . 111.0 no
C18 C20 H201 . . . 109.1 no
H203 C20 H201 . . . 108.3 no
H202 C20 H201 . . . 107.9 no
C3 C21 O22 . . . 119.96(12) no
C3 C21 C23 . . . 120.59(12) no
O22 C21 C23 . . . 119.44(12) no
C21 O22 H221 . . . 105.3 no
C21 C23 C24 . . . 119.16(12) no
C21 C23 H231 . . . 120.0 no
C24 C23 H231 . . . 120.8 no
C23 C24 C25 . . . 122.48(12) no
C23 C24 O29 . . . 116.88(12) no
C25 C24 O29 . . . 120.57(12) no
C24 C25 C2 . . . 116.94(12) no
C24 C25 C26 . . . 118.80(12) no
C2 C25 C26 . . . 124.25(12) no
C25 C26 C27 . . . 119.42(12) no
C25 C26 H261 . . . 118.9 no
C27 C26 H261 . . . 121.7 no
C26 C27 C28 . . . 121.82(12) no
C26 C27 H271 . . . 121.3 no
C28 C27 H271 . . . 116.8 no
C27 C28 O29 . . . 111.21(11) no
C27 C28 C30 . . . 111.89(12) no
O29 C28 C30 . . . 104.02(11) no
C27 C28 C31 . . . 109.92(12) no
O29 C28 C31 . . . 107.55(11) no
C30 C28 C31 . . . 112.06(12) no
C28 O29 C24 . . . 119.33(10) no
C28 C30 H301 . . . 110.0 no
C28 C30 H302 . . . 109.4 no
H301 C30 H302 . . . 109.6 no
C28 C30 H303 . . . 110.0 no
H301 C30 H303 . . . 109.1 no
H302 C30 H303 . . . 108.8 no
C28 C31 H311 . . . 109.2 no
C28 C31 H313 . . . 110.4 no
H311 C31 H313 . . . 109.4 no
C28 C31 H312 . . . 109.4 no
H311 C31 H312 . . . 109.8 no
H313 C31 H312 . . . 108.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . . 1.3696(16) no
O1 C7 . . 1.3651(15) no
C2 C3 . . 1.4025(18) no
C2 C25 . . 1.3886(18) no
C3 C4 . . 1.4375(18) no
C3 C21 . . 1.4213(18) no
C4 O5 . . 1.2490(16) no
C4 C6 . . 1.4700(18) no
C6 C7 . . 1.4016(18) no
C6 C11 . . 1.3996(18) no
C7 C8 . . 1.4009(19) no
C8 C9 . . 1.3891(18) no
C8 C18 . . 1.5175(18) no
C9 C10 . . 1.3875(19) no
C9 C14 . . 1.4879(18) no
C10 C11 . . 1.3727(19) no
C10 C12 . . 1.5093(18) no
C11 H111 . . 0.938 no
C12 O13 . . 1.4715(17) no
C12 C16 . . 1.5166(19) no
C12 C17 . . 1.5196(19) no
O13 C14 . . 1.3610(17) no
C14 O15 . . 1.1973(17) no
C16 H163 . . 0.969 no
C16 H162 . . 0.984 no
C16 H161 . . 0.962 no
C17 H171 . . 0.961 no
C17 H172 . . 0.975 no
C17 H173 . . 0.962 no
C18 O19 . . 1.2052(18) no
C18 C20 . . 1.4982(19) no
C20 H203 . . 0.976 no
C20 H202 . . 0.968 no
C20 H201 . . 0.967 no
C21 O22 . . 1.3449(16) no
C21 C23 . . 1.3833(19) no
O22 H221 . . 0.880 no
C23 C24 . . 1.3926(19) no
C23 H231 . . 0.947 no
C24 C25 . . 1.4050(19) no
C24 O29 . . 1.3524(15) no
C25 C26 . . 1.4582(18) no
C26 C27 . . 1.3269(19) no
C26 H261 . . 0.937 no
C27 C28 . . 1.5048(19) no
C27 H271 . . 0.941 no
C28 O29 . . 1.4714(16) no
C28 C30 . . 1.5162(18) no
C28 C31 . . 1.524(2) no
C30 H301 . . 0.960 no
C30 H302 . . 0.972 no
C30 H303 . . 0.950 no
C31 H311 . . 0.972 no
C31 H313 . . 0.970 no
C31 H312 . . 0.957 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C16 H161 O15 . . 7_555 0.96 2.55 3.4062(19) 148 yes
C20 H202 O13 . . 7_555 0.97 2.53 3.4918(19) 171 yes
O22 H221 O5 . . . 0.88 1.78 2.5922(19) 153 yes
C31 H313 O22 . . 2_575 0.97 2.57 3.5170(19) 165 yes
C27 H271 O5 . . 6_564 0.94 2.58 3.4923(19) 163 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8916129
