#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/05/4020530.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_4020530
loop_
_publ_author_name
'Youjun Yang'
'Jorge O. Escobedo'
'Alexander Wong'
'Corin M. Schowalter'
'Michael C. Touchy'
'Lijuan Jiao'
'William E. Crowe'
'Frank R. Fronczek'
'Robert M. Strongin'
_publ_section_title
;
 A Convenient Preparation of Xanthene Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6907
_journal_page_last               6912
_journal_paper_doi               10.1021/jo051002a
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C23 H24 O5'
_chemical_formula_sum            'C23 H24 O5'
_chemical_formula_weight         380.42
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                93.876(6)
_cell_angle_beta                 98.152(6)
_cell_angle_gamma                107.681(6)
_cell_formula_units_Z            4
_cell_length_a                   8.4475(10)
_cell_length_b                   11.312(2)
_cell_length_c                   21.111(4)
_cell_measurement_temperature    105
_cell_volume                     1889.5(5)
_diffrn_ambient_temperature      105
_exptl_crystal_density_diffrn    1.337
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1  '
_cod_database_code               4020530
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.86910(12) 0.95802(9) 1.15517(5) 0.0244(2) Uani 1 1 d . . .
O2A O 0.35464(11) 0.80460(9) 0.99607(4) 0.0198(2) Uani 1 1 d . . .
O3A O 0.92149(12) 0.76283(9) 0.70050(4) 0.0211(2) Uani 1 1 d . . .
O4A O 0.74472(12) 0.61820(8) 0.89893(4) 0.0192(2) Uani 1 1 d . . .
O5A O 0.42949(12) 0.84680(8) 0.87683(5) 0.0198(2) Uani 1 1 d . . .
H50A H 0.364(2) 0.8490(14) 0.9052(8) 0.030 Uiso 1 1 d . . .
C1A C 0.52433(16) 0.76495(11) 0.89820(6) 0.0152(2) Uani 1 1 d . . .
C2A C 0.61723(16) 0.81610(11) 0.96714(6) 0.0150(2) Uani 1 1 d . . .
C3A C 0.79167(16) 0.85300(11) 0.98475(6) 0.0172(3) Uani 1 1 d . . .
H3A H 0.8578 0.8448 0.9529 0.021 Uiso 1 1 calc R . .
C4A C 0.87262(16) 0.90138(11) 1.04719(7) 0.0185(3) Uani 1 1 d . . .
H4A H 0.9921 0.9263 1.0574 0.022 Uiso 1 1 calc R . .
C5A C 0.77834(16) 0.91321(11) 1.09466(6) 0.0172(3) Uani 1 1 d . . .
C6A C 0.60348(16) 0.88068(11) 1.07906(6) 0.0162(2) Uani 1 1 d . . .
H6A H 0.5382 0.8899 1.1111 0.019 Uiso 1 1 calc R . .
C7A C 0.52588(16) 0.83432(11) 1.01560(6) 0.0153(2) Uani 1 1 d . . .
C8A C 0.64199(16) 0.76709(11) 0.84888(6) 0.0154(2) Uani 1 1 d . . .
C9A C 0.64391(16) 0.84264(11) 0.79932(6) 0.0173(3) Uani 1 1 d . . .
H9A H 0.5773 0.8969 0.7984 0.021 Uiso 1 1 calc R . .
C10A C 0.73997(16) 0.84140(12) 0.75112(6) 0.0178(3) Uani 1 1 d . . .
H10A H 0.7392 0.8946 0.7182 0.021 Uiso 1 1 calc R . .
C11A C 0.83682(16) 0.76205(11) 0.75144(6) 0.0166(3) Uani 1 1 d . . .
C12A C 0.84278(16) 0.68748(11) 0.80101(6) 0.0172(3) Uani 1 1 d . . .
H12A H 0.9123 0.6353 0.8021 0.021 Uiso 1 1 calc R . .
C13A C 0.74550(16) 0.69003(11) 0.84917(6) 0.0159(2) Uani 1 1 d . . .
C14A C 0.39704(15) 0.63179(11) 0.89280(6) 0.0148(2) Uani 1 1 d . . .
C15A C 0.28680(16) 0.58519(12) 0.83448(6) 0.0191(3) Uani 1 1 d . . .
H15A H 0.2942 0.6346 0.7997 0.023 Uiso 1 1 calc R . .
C16A C 0.16630(17) 0.46749(12) 0.82649(6) 0.0208(3) Uani 1 1 d . . .
H16A H 0.0913 0.4376 0.7867 0.025 Uiso 1 1 calc R . .
C17A C 0.15561(17) 0.39384(12) 0.87657(7) 0.0197(3) Uani 1 1 d . . .
H17A H 0.0737 0.3133 0.8712 0.024 Uiso 1 1 calc R . .
C18A C 0.26506(17) 0.43841(12) 0.93445(7) 0.0196(3) Uani 1 1 d . . .
H18A H 0.2589 0.3880 0.9688 0.024 Uiso 1 1 calc R . .
C19A C 0.38477(16) 0.55744(11) 0.94248(6) 0.0174(3) Uani 1 1 d . . .
H19A H 0.4586 0.5876 0.9825 0.021 Uiso 1 1 calc R . .
C20A C 0.77985(18) 0.98024(13) 1.20493(6) 0.0228(3) Uani 1 1 d . . .
H20A H 0.7221 1.0407 1.1929 0.034 Uiso 1 1 calc R . .
H20B H 0.8596 1.0137 1.2453 0.034 Uiso 1 1 calc R . .
H20C H 0.6966 0.9016 1.2108 0.034 Uiso 1 1 calc R . .
C21A C 0.25312(17) 0.81746(14) 1.04327(7) 0.0240(3) Uani 1 1 d . . .
H21A H 0.2671 0.7646 1.0772 0.036 Uiso 1 1 calc R . .
H21B H 0.1344 0.7917 1.0228 0.036 Uiso 1 1 calc R . .
H21C H 0.2883 0.9049 1.0622 0.036 Uiso 1 1 calc R . .
C22A C 1.04551(18) 0.70007(13) 0.70376(7) 0.0248(3) Uani 1 1 d . . .
H22A H 1.1314 0.7358 0.7422 0.037 Uiso 1 1 calc R . .
H22B H 1.0987 0.7105 0.6653 0.037 Uiso 1 1 calc R . .
H22C H 0.9914 0.6109 0.7060 0.037 Uiso 1 1 calc R . .
C23A C 0.86563(18) 0.55264(13) 0.90612(7) 0.0228(3) Uani 1 1 d . . .
H23A H 0.8436 0.4910 0.8684 0.034 Uiso 1 1 calc R . .
H23B H 0.8567 0.5100 0.9450 0.034 Uiso 1 1 calc R . .
H23C H 0.9794 0.6121 0.9099 0.034 Uiso 1 1 calc R . .
O1B O 0.72271(12) 0.03312(9) 0.35891(5) 0.0238(2) Uani 1 1 d . . .
O2B O 1.20533(11) 0.21576(8) 0.52023(5) 0.0208(2) Uani 1 1 d . . .
O3B O 0.61849(12) 0.27399(9) 0.80773(4) 0.0214(2) Uani 1 1 d . . .
O4B O 0.79666(12) 0.40000(8) 0.60674(4) 0.01885(19) Uani 1 1 d . . .
O5B O 1.12825(12) 0.18613(8) 0.64216(5) 0.0201(2) Uani 1 1 d . . .
H50B H 1.197(2) 0.1794(14) 0.6163(8) 0.030 Uiso 1 1 d . . .
C1B C 1.02710(16) 0.25893(11) 0.61506(6) 0.0153(2) Uani 1 1 d . . .
C2B C 0.93747(16) 0.19585(11) 0.54751(6) 0.0150(2) Uani 1 1 d . . .
C3B C 0.76399(16) 0.15098(11) 0.52954(6) 0.0164(3) Uani 1 1 d . . .
H3B H 0.6961 0.1592 0.5607 0.020 Uiso 1 1 calc R . .
C4B C 0.68401(16) 0.09409(11) 0.46753(6) 0.0165(3) Uani 1 1 d . . .
H4B H 0.5645 0.0640 0.4569 0.020 Uiso 1 1 calc R . .
C5B C 0.78283(16) 0.08256(11) 0.42188(6) 0.0171(3) Uani 1 1 d . . .
C6B C 0.95826(16) 0.12260(11) 0.43834(6) 0.0183(3) Uani 1 1 d . . .
H6B H 1.0255 0.1125 0.4072 0.022 Uiso 1 1 calc R . .
C7B C 1.03356(15) 0.17705(11) 0.50023(6) 0.0160(2) Uani 1 1 d . . .
C8B C 0.90632(16) 0.26061(11) 0.66296(6) 0.0149(2) Uani 1 1 d . . .
C9B C 0.90582(16) 0.19090(11) 0.71516(6) 0.0163(2) Uani 1 1 d . . .
H9B H 0.9748 0.1383 0.7184 0.020 Uiso 1 1 calc R . .
C10B C 0.80831(16) 0.19546(11) 0.76252(6) 0.0169(3) Uani 1 1 d . . .
H10B H 0.8102 0.1463 0.7972 0.020 Uiso 1 1 calc R . .
C11B C 0.70834(16) 0.27270(11) 0.75847(6) 0.0163(3) Uani 1 1 d . . .
C12B C 0.70160(16) 0.34221(11) 0.70671(6) 0.0163(2) Uani 1 1 d . . .
H12B H 0.6311 0.3936 0.7037 0.020 Uiso 1 1 calc R . .
C13B C 0.79964(16) 0.33559(11) 0.65925(6) 0.0152(2) Uani 1 1 d . . .
C14B C 1.14510(15) 0.39367(11) 0.61488(6) 0.0153(2) Uani 1 1 d . . .
C15B C 1.26308(16) 0.44862(12) 0.67000(6) 0.0197(3) Uani 1 1 d . . .
H15B H 1.2669 0.4035 0.7062 0.024 Uiso 1 1 calc R . .
C16B C 1.37558(17) 0.56838(12) 0.67302(7) 0.0220(3) Uani 1 1 d . . .
H16B H 1.4564 0.6042 0.7109 0.026 Uiso 1 1 calc R . .
C17B C 1.36943(17) 0.63520(12) 0.62070(7) 0.0217(3) Uani 1 1 d . . .
H17B H 1.4464 0.7170 0.6225 0.026 Uiso 1 1 calc R . .
C18B C 1.25079(17) 0.58264(12) 0.56561(7) 0.0213(3) Uani 1 1 d . . .
H18B H 1.2454 0.6287 0.5298 0.026 Uiso 1 1 calc R . .
C19B C 1.13911(17) 0.46158(12) 0.56294(6) 0.0182(3) Uani 1 1 d . . .
H19B H 1.0583 0.4256 0.5251 0.022 Uiso 1 1 calc R . .
C20B C 0.54598(18) -0.00915(13) 0.33828(7) 0.0261(3) Uani 1 1 d . . .
H20D H 0.4946 -0.0798 0.3611 0.039 Uiso 1 1 calc R . .
H20E H 0.5206 -0.0357 0.2918 0.039 Uiso 1 1 calc R . .
H20F H 0.5003 0.0588 0.3476 0.039 Uiso 1 1 calc R . .
C21B C 1.30741(17) 0.20567(13) 0.47300(7) 0.0239(3) Uani 1 1 d . . .
H21D H 1.2820 0.1176 0.4567 0.036 Uiso 1 1 calc R . .
H21E H 1.4267 0.2404 0.4926 0.036 Uiso 1 1 calc R . .
H21F H 1.2836 0.2522 0.4373 0.036 Uiso 1 1 calc R . .
C22B C 0.50301(19) 0.34481(13) 0.80331(7) 0.0255(3) Uani 1 1 d . . .
H22D H 0.5638 0.4319 0.7991 0.038 Uiso 1 1 calc R . .
H22E H 0.4519 0.3413 0.8423 0.038 Uiso 1 1 calc R . .
H22F H 0.4145 0.3096 0.7656 0.038 Uiso 1 1 calc R . .
C23B C 0.68411(18) 0.47261(12) 0.59998(7) 0.0219(3) Uani 1 1 d . . .
H23D H 0.5682 0.4182 0.5985 0.033 Uiso 1 1 calc R . .
H23E H 0.6923 0.5118 0.5600 0.033 Uiso 1 1 calc R . .
H23F H 0.7147 0.5375 0.6368 0.033 Uiso 1 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C5A 1.3693(16) . ?
O1A C20A 1.4281(16) . ?
O2A C7A 1.3756(15) . ?
O2A C21A 1.4310(15) . ?
O3A C11A 1.3725(15) . ?
O3A C22A 1.4298(16) . ?
O4A C13A 1.3703(15) . ?
O4A C23A 1.4310(15) . ?
O5A C1A 1.4516(15) . ?
O5A H50A 0.876(17) . ?
C1A C8A 1.5346(17) . ?
C1A C2A 1.5347(18) . ?
C1A C14A 1.5480(17) . ?
C2A C3A 1.3907(18) . ?
C2A C7A 1.4059(17) . ?
C3A C4A 1.3871(18) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3891(18) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3933(18) . ?
C6A C7A 1.3951(18) . ?
C6A H6A 0.9500 . ?
C8A C9A 1.3939(17) . ?
C8A C13A 1.4095(17) . ?
C9A C10A 1.3904(17) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.3858(18) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3928(18) . ?
C12A C13A 1.3989(17) . ?
C12A H12A 0.9500 . ?
C14A C19A 1.3838(17) . ?
C14A C15A 1.3965(18) . ?
C15A C16A 1.3911(18) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.3858(19) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.3838(19) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.3992(18) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
O1B C5B 1.3688(15) . ?
O1B C20B 1.4145(17) . ?
O2B C7B 1.3751(15) . ?
O2B C21B 1.4279(15) . ?
O3B C11B 1.3734(15) . ?
O3B C22B 1.4357(16) . ?
O4B C13B 1.3684(15) . ?
O4B C23B 1.4320(15) . ?
O5B C1B 1.4450(15) . ?
O5B H50B 0.866(17) . ?
C1B C2B 1.5311(17) . ?
C1B C8B 1.5381(17) . ?
C1B C14B 1.5478(17) . ?
C2B C3B 1.3834(18) . ?
C2B C7B 1.4165(17) . ?
C3B C4B 1.3984(18) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3857(17) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3953(18) . ?
C6B C7B 1.3814(18) . ?
C6B H6B 0.9500 . ?
C8B C9B 1.3974(17) . ?
C8B C13B 1.4109(17) . ?
C9B C10B 1.3905(17) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3862(18) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3934(18) . ?
C12B C13B 1.3993(17) . ?
C12B H12B 0.9500 . ?
C14B C19B 1.3846(18) . ?
C14B C15B 1.3894(18) . ?
C15B C16B 1.3898(18) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.384(2) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.387(2) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3994(18) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9008933
