#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/37/2213785.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_2213785
loop_
_publ_author_name
'Janusz B. Kyzioł'
'Ewa M. Nowakowska'
'Zaleski, Jacek'
_publ_section_title
;
 β-(3,6,9-Trimethyl-9-xanthenyl)propionic acid
;
_journal_coeditor_code           HB2378
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2834
_journal_page_last               o2834
_journal_paper_doi               10.1107/S1600536807021332
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H20 O3'
_chemical_formula_moiety         'C19 H20 O3'
_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_weight         296.35
_chemical_name_systematic
;
β-(3,6,9-Trimethyl-9-xanthenyl)propionic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 110.645(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5042(9)
_cell_length_b                   14.3969(11)
_cell_length_c                   11.2404(9)
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    85.0(2)
_cell_measurement_theta_max      29.44
_cell_measurement_theta_min      2.69
_cell_volume                     1590.7(2)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      85.0(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω-scan
_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  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12735
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.44
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0677P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                2929
_reflns_number_total             4411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hb2378.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'NONE' changed to 'none' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_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.

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

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'NONE' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213785
_cod_database_fobs_code          2213785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_calc_flag
_atom_site_occupancy
C C1 0.54653(11) 0.27029(8) 0.62341(10) 0.0160(2) Uani d 1
H H1 0.6202(14) 0.3115(9) 0.6747(13) 0.023(3) Uiso d 1
C C2 0.41988(11) 0.27971(8) 0.63464(11) 0.0166(2) Uani d 1
H H2 0.4057(13) 0.3257(9) 0.6905(13) 0.021(3) Uiso d 1
C C3 0.31129(11) 0.22389(7) 0.56366(10) 0.0153(2) Uani d 1
C C4 0.33408(11) 0.15899(7) 0.48222(11) 0.0159(2) Uani d 1
H H4 0.2591(13) 0.1191(9) 0.4271(12) 0.019(3) Uiso d 1
C C5 0.58806(12) 0.00426(8) 0.27792(10) 0.0160(2) Uani d 1
H H5 0.5021(13) -0.0277(8) 0.2353(12) 0.018(3) Uiso d 1
C C6 0.70170(12) -0.01383(8) 0.24647(11) 0.0174(2) Uani d 1
C C7 0.82073(12) 0.03521(8) 0.31188(11) 0.0198(3) Uani d 1
H H7 0.9041(14) 0.0249(9) 0.2919(13) 0.022(3) Uiso d 1
C C8 0.82337(12) 0.10053(8) 0.40325(11) 0.0184(2) Uani d 1
H H8 0.9108(15) 0.1358(9) 0.4460(13) 0.026(4) Uiso d 1
C C9 0.71229(11) 0.19491(7) 0.53293(10) 0.0125(2) Uani d 1
O O10 0.47112(8) 0.08046(5) 0.39100(7) 0.01616(18) Uani d 1
C C11 0.57152(11) 0.20465(7) 0.54259(10) 0.0124(2) Uani d 1
C C12 0.46221(11) 0.14936(7) 0.47324(10) 0.0131(2) Uani d 1
C C13 0.59229(11) 0.06962(7) 0.37053(10) 0.0134(2) Uani d 1
C C14 0.70842(11) 0.12055(7) 0.43461(10) 0.0132(2) Uani d 1
C C21 0.81734(11) 0.16763(7) 0.66432(10) 0.0131(2) Uani d 1
H H21A 0.8232(12) 0.2171(9) 0.7274(12) 0.016(3) Uiso d 1
H H21B 0.9093(13) 0.1643(9) 0.6583(12) 0.020(3) Uiso d 1
C C22 0.78051(12) 0.07679(8) 0.71238(11) 0.0176(2) Uani d 1
H H22A 0.6909(15) 0.0772(10) 0.7165(14) 0.030(4) Uiso d 1
H H22B 0.7760(15) 0.0259(10) 0.6524(15) 0.034(4) Uiso d 1
C C23 0.87758(11) 0.04535(7) 0.83856(10) 0.0142(2) Uani d 1
O O24 0.82955(9) -0.02352(6) 0.88773(9) 0.0309(2) Uani d 1
H H24 0.8952(18) -0.0415(12) 0.9649(18) 0.051(5) Uiso d 1
O O25 0.98967(8) 0.07885(6) 0.89079(8) 0.0206(2) Uani d 1
C C26 0.75498(12) 0.28876(8) 0.49252(11) 0.0172(2) Uani d 1
H H26A 0.8466(14) 0.2862(9) 0.4846(12) 0.023(3) Uiso d 1
H H26B 0.7580(12) 0.3375(9) 0.5566(12) 0.019(3) Uiso d 1
H H26C 0.6906(15) 0.3085(9) 0.4072(14) 0.025(4) Uiso d 1
C C27 0.17292(12) 0.23341(9) 0.57411(13) 0.0213(3) Uani d 1
H H27A 0.1353(14) 0.1730(11) 0.5853(13) 0.026(4) Uiso d 1
H H27B 0.1723(16) 0.2743(11) 0.6474(15) 0.039(4) Uiso d 1
H H27C 0.1077(17) 0.2583(11) 0.4953(16) 0.042(4) Uiso d 1
C C28 0.69469(15) -0.08295(10) 0.14359(13) 0.0252(3) Uani d 1
H H28A 0.6348(17) -0.1350(12) 0.1440(16) 0.049(5) Uiso d 1
H H28B 0.6580(18) -0.0541(12) 0.0595(18) 0.053(5) Uiso d 1
H H28C 0.7874(17) -0.1085(11) 0.1545(15) 0.042(4) Uiso d 1
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 0.0016 '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 0.0060 '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
C2 C1 C11 122.08(10) ?
C2 C1 H1 118.0(8) ?
C11 C1 H1 119.9(8) ?
C1 C2 C3 120.63(10) ?
C1 C2 H2 120.2(8) ?
C3 C2 H2 119.2(8) ?
C4 C3 C2 118.01(10) n
C4 C3 C27 120.60(10) ?
C2 C3 C27 121.39(10) ?
C3 C4 C12 120.76(10) ?
C3 C4 H4 121.2(7) ?
C12 C4 H4 118.1(7) ?
C6 C5 C13 121.01(10) ?
C6 C5 H5 121.2(7) ?
C13 C5 H5 117.8(7) ?
C5 C6 C7 117.56(10) y
C5 C6 C28 120.46(11) ?
C7 C6 C28 121.97(11) ?
C8 C7 C6 120.87(11) ?
C8 C7 H7 118.9(8) ?
C6 C7 H7 120.2(8) ?
C7 C8 C14 122.13(11) ?
C7 C8 H8 118.1(8) ?
C14 C8 H8 119.7(8) ?
C11 C9 C14 109.64(8) n
C11 C9 C26 109.27(9) n
C14 C9 C26 109.70(9) n
C11 C9 C21 109.72(8) n
C14 C9 C21 109.86(8) n
C26 C9 C21 108.63(9) ?
C13 O10 C12 118.49(8) n
C12 C11 C1 116.40(10) n
C12 C11 C9 122.50(9) n
C1 C11 C9 121.11(9) ?
O10 C12 C11 123.34(9) ?
O10 C12 C4 114.55(9) ?
C11 C12 C4 122.11(10) ?
O10 C13 C14 123.20(10) ?
O10 C13 C5 114.39(9) ?
C14 C13 C5 122.40(10) ?
C13 C14 C8 116.00(10) ?
C13 C14 C9 122.67(9) ?
C8 C14 C9 121.33(10) ?
C22 C21 C9 111.88(9) ?
C22 C21 H21A 108.9(7) ?
C9 C21 H21A 110.1(7) ?
C22 C21 H21B 111.0(7) ?
C9 C21 H21B 109.3(7) ?
H21A C21 H21B 105.5(10) ?
C23 C22 C21 115.13(9) ?
C23 C22 H22A 108.0(9) ?
C21 C22 H22A 113.0(8) ?
C23 C22 H22B 106.0(9) ?
C21 C22 H22B 110.8(9) ?
H22A C22 H22B 103.1(12) ?
O25 C23 O24 122.99(10) n
O25 C23 C22 123.97(10) n
O24 C23 C22 113.04(9) n
C23 O24 H24 109.4(11) ?
C9 C26 H26A 112.5(8) ?
C9 C26 H26B 110.0(7) ?
H26A C26 H26B 107.7(10) ?
C9 C26 H26C 111.3(8) ?
H26A C26 H26C 105.8(10) ?
H26B C26 H26C 109.3(10) ?
C3 C27 H27A 111.9(8) ?
C3 C27 H27B 113.5(9) ?
H27A C27 H27B 107.0(12) ?
C3 C27 H27C 110.5(9) ?
H27A C27 H27C 104.8(13) ?
H27B C27 H27C 108.7(12) ?
C6 C28 H28A 111.0(10) ?
C6 C28 H28B 110.9(10) ?
H28A C28 H28B 107.1(14) ?
C6 C28 H28C 111.4(9) ?
H28A C28 H28C 108.3(13) ?
H28B C28 H28C 107.9(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.3865(15) ?
C1 C11 1.3984(15) ?
C1 H1 0.984(14) ?
C2 C3 1.3935(15) ?
C2 H2 0.960(13) ?
C3 C4 1.3867(16) ?
C3 C27 1.5052(16) ?
C4 C12 1.3916(15) ?
C4 H4 0.995(13) ?
C5 C6 1.3840(16) ?
C5 C13 1.3922(15) ?
C5 H5 0.976(13) ?
C6 C7 1.3978(16) ?
C6 C28 1.5076(16) ?
C7 C8 1.3855(16) ?
C7 H7 0.989(14) ?
C8 C14 1.4020(15) ?
C8 H8 1.010(14) ?
C9 C11 1.5268(14) n
C9 C14 1.5289(15) n
C9 C26 1.5416(15) n
C9 C21 1.5504(15) n
O10 C13 1.3799(13) n
O10 C12 1.3813(12) n
C11 C12 1.3887(14) ?
C13 C14 1.3874(15) ?
C21 C22 1.5164(15) ?
C21 H21A 0.991(12) ?
C21 H21B 0.993(13) ?
C22 C23 1.4954(15) ?
C22 H22A 0.958(15) ?
C22 H22B 0.986(15) ?
C23 O25 1.2150(13) n
C23 O24 1.3190(14) n
O24 H24 0.935(18) ?
C26 H26A 0.998(13) ?
C26 H26B 0.998(14) ?
C26 H26C 1.001(14) ?
C27 H27A 0.981(15) ?
C27 H27B 1.015(16) ?
C27 H27C 0.977(17) ?
C28 H28A 0.979(18) ?
C28 H28B 0.978(19) ?
C28 H28C 1.007(17) ?
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
O24 H24 O25 3_757 0.935(18) 1.732(19) 2.6654(12) 176.9(17)
C2 H2 O10 4_566 0.960(13) 2.507(14) 3.3989(14) 154.6(10)
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
C11 C1 C2 C3 -0.69(17)
C1 C2 C3 C4 0.11(16)
C1 C2 C3 C27 -179.71(11)
C2 C3 C4 C12 0.82(16)
C27 C3 C4 C12 -179.36(10)
C13 C5 C6 C7 0.60(16)
C13 C5 C6 C28 -178.39(11)
C5 C6 C7 C8 -1.04(17)
C28 C6 C7 C8 177.93(11)
C6 C7 C8 C14 0.08(18)
C2 C1 C11 C12 0.31(16)
C2 C1 C11 C9 -179.34(10)
C14 C9 C11 C12 2.30(13)
C26 C9 C11 C12 122.56(11)
C21 C9 C11 C12 -118.44(10)
C14 C9 C11 C1 -178.06(9)
C26 C9 C11 C1 -57.80(13)
C21 C9 C11 C1 61.20(12)
C13 O10 C12 C11 -4.13(14)
C13 O10 C12 C4 176.28(9)
C1 C11 C12 O10 -178.93(9)
C9 C11 C12 O10 0.72(15)
C1 C11 C12 C4 0.64(15)
C9 C11 C12 C4 -179.71(9)
C3 C4 C12 O10 178.37(9)
C3 C4 C12 C11 -1.23(16)
C12 O10 C13 C14 4.26(15)
C12 O10 C13 C5 -174.54(9)
C6 C5 C13 O10 179.65(9)
C6 C5 C13 C14 0.84(17)
O10 C13 C14 C8 179.55(9)
C5 C13 C14 C8 -1.75(16)
O10 C13 C14 C9 -0.99(16)
C5 C13 C14 C9 177.72(10)
C7 C8 C14 C13 1.29(16)
C7 C8 C14 C9 -178.18(10)
C11 C9 C14 C13 -2.18(14)
C26 C9 C14 C13 -122.18(11)
C21 C9 C14 C13 118.47(11)
C11 C9 C14 C8 177.26(9)
C26 C9 C14 C8 57.25(13)
C21 C9 C14 C8 -62.09(13)
C11 C9 C21 C22 59.23(12)
C14 C9 C21 C22 -61.37(12)
C26 C9 C21 C22 178.62(9)
C9 C21 C22 C23 179.65(9)
C21 C22 C23 O25 -12.54(17)
C21 C22 C23 O24 167.94(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124447
