#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/12/2221225.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_2221225
loop_
_publ_author_name
'Niedziałkowski, Paweł'
'Ossowski, Tadeusz'
'Sikorski, Artur'
_publ_section_title
;
 Methyl 7-methoxy-9-oxo-9H-xanthene-2-carboxylate
;
_journal_coeditor_code           XU2476
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o484
_journal_page_last               o485
_journal_paper_doi               10.1107/S1600536809003602
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H12 O5'
_chemical_formula_moiety         'C16 H12 O5'
_chemical_formula_sum            'C16 H12 O5'
_chemical_formula_weight         284.26
_chemical_name_systematic
;
Methyl 7-methoxy-9-oxo-9H-xanthene-2-carboxylate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.266(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7709(4)
_cell_length_b                   10.5375(8)
_cell_length_c                   26.7854(19)
_cell_measurement_reflns_used    2126
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.99
_cell_volume                     1344.40(18)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4002
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23842
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0382
_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)+(0.0471P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                1051
_reflns_number_total             2366
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2476.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221225
_cod_database_fobs_code          2221225
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4869(4) 0.3741(2) 0.37390(8) 0.0507(6) Uani d . 1 . .
H H1 0.4950 0.4005 0.3409 0.061 Uiso calc R 1 . .
C C2 0.6568(4) 0.4321(2) 0.41017(8) 0.0531(6) Uani d . 1 . .
C C3 0.6434(5) 0.3912(2) 0.45962(9) 0.0678(7) Uani d . 1 . .
H H3 0.7584 0.4289 0.4846 0.081 Uiso calc R 1 . .
C C4 0.4634(5) 0.2964(3) 0.47187(9) 0.0735(7) Uani d . 1 . .
H H4 0.4548 0.2703 0.5049 0.088 Uiso calc R 1 . .
C C5 -0.2272(5) -0.0083(2) 0.43087(9) 0.0742(7) Uani d . 1 . .
H H5 -0.2221 -0.0287 0.4647 0.089 Uiso calc R 1 . .
C C6 -0.4064(5) -0.0705(2) 0.39752(9) 0.0723(7) Uani d . 1 . .
H H6 -0.5229 -0.1337 0.4089 0.087 Uiso calc R 1 . .
C C7 -0.4169(4) -0.0408(2) 0.34712(9) 0.0570(6) Uani d . 1 . .
C C8 -0.2448(4) 0.0520(2) 0.33022(8) 0.0506(6) Uani d . 1 . .
H H8 -0.2514 0.0723 0.2964 0.061 Uiso calc R 1 . .
C C9 0.1240(4) 0.2157(2) 0.34601(8) 0.0485(5) Uani d . 1 . .
O O10 0.1221(3) 0.14529(15) 0.44927(5) 0.0685(5) Uani d . 1 . .
C C11 0.3026(4) 0.2770(2) 0.38514(7) 0.0469(5) Uani d . 1 . .
C C12 0.2945(4) 0.2399(2) 0.43445(8) 0.0567(6) Uani d . 1 . .
C C13 -0.0592(4) 0.1163(2) 0.36375(7) 0.0459(5) Uani d . 1 . .
C C14 -0.0538(4) 0.0853(2) 0.41369(8) 0.0567(6) Uani d . 1 . .
C C15 0.8493(5) 0.5368(2) 0.39863(10) 0.0616(6) Uani d . 1 . .
O O16 0.9949(4) 0.59309(17) 0.42912(7) 0.0897(6) Uani d . 1 . .
O O17 0.8478(3) 0.56064(15) 0.34987(6) 0.0748(5) Uani d . 1 . .
C C18 1.0307(5) 0.6610(2) 0.33454(10) 0.0877(8) Uani d . 1 . .
H H18A 0.9931 0.6783 0.2996 0.132 Uiso calc R 1 . .
H H18B 1.2228 0.6352 0.3403 0.132 Uiso calc R 1 . .
H H18C 0.9978 0.7362 0.3536 0.132 Uiso calc R 1 . .
O O19 -0.6050(3) -0.10926(15) 0.31785(6) 0.0734(5) Uani d . 1 . .
C C20 -0.6235(5) -0.0814(3) 0.26581(9) 0.0837(8) Uani d . 1 . .
H H20A -0.7623 -0.1351 0.2493 0.126 Uiso calc R 1 . .
H H20B -0.4446 -0.0962 0.2522 0.126 Uiso calc R 1 . .
H H20C -0.6760 0.0058 0.2609 0.126 Uiso calc R 1 . .
O O21 0.1291(3) 0.24526(14) 0.30176(5) 0.0657(5) Uani 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C11 . . 121.9(2) ?
C2 C1 H1 . . 119.1 ?
C11 C1 H1 . . 119.1 ?
C1 C2 C3 . . 118.4(2) ?
C1 C2 C15 . . 122.2(2) ?
C3 C2 C15 . . 119.4(2) ?
C4 C3 C2 . . 121.0(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C12 . . 119.2(2) ?
C3 C4 H4 . . 120.4 ?
C12 C4 H4 . . 120.4 ?
C6 C5 C14 . . 119.2(2) ?
C6 C5 H5 . . 120.4 ?
C14 C5 H5 . . 120.4 ?
C5 C6 C7 . . 121.0(2) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
O19 C7 C8 . . 125.1(2) ?
O19 C7 C6 . . 115.3(2) ?
C8 C7 C6 . . 119.6(2) ?
C7 C8 C13 . . 120.2(2) ?
C7 C8 H8 . . 119.9 ?
C13 C8 H8 . . 119.9 ?
O21 C9 C13 . . 122.78(19) ?
O21 C9 C11 . . 122.5(2) ?
C13 C9 C11 . . 114.73(19) ?
C12 O10 C14 . . 118.97(16) ?
C12 C11 C1 . . 117.8(2) ?
C12 C11 C9 . . 120.9(2) ?
C1 C11 C9 . . 121.22(19) ?
O10 C12 C11 . . 122.33(19) ?
O10 C12 C4 . . 116.0(2) ?
C11 C12 C4 . . 121.6(2) ?
C14 C13 C8 . . 119.0(2) ?
C14 C13 C9 . . 120.5(2) ?
C8 C13 C9 . . 120.44(19) ?
C13 C14 C5 . . 121.0(2) ?
C13 C14 O10 . . 122.5(2) ?
C5 C14 O10 . . 116.5(2) ?
O16 C15 O17 . . 123.1(2) ?
O16 C15 C2 . . 124.7(2) ?
O17 C15 C2 . . 112.2(2) ?
C15 O17 C18 . . 116.59(19) ?
O17 C18 H18A . . 109.5 ?
O17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C7 O19 C20 . . 117.16(17) ?
O19 C20 H20A . . 109.5 ?
O19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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 . 1.373(3) ?
C1 C11 . 1.394(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.398(3) ?
C2 C15 . 1.480(3) ?
C3 C4 . 1.369(3) ?
C3 H3 . 0.9300 ?
C4 C12 . 1.384(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.368(3) ?
C5 C14 . 1.383(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.9300 ?
C7 O19 . 1.364(2) ?
C7 C8 . 1.370(3) ?
C8 C13 . 1.400(3) ?
C8 H8 . 0.9300 ?
C9 O21 . 1.227(2) ?
C9 C13 . 1.461(3) ?
C9 C11 . 1.462(3) ?
O10 C12 . 1.366(2) ?
O10 C14 . 1.386(2) ?
C11 C12 . 1.380(3) ?
C13 C14 . 1.376(3) ?
C15 O16 . 1.199(2) ?
C15 O17 . 1.330(3) ?
O17 C18 . 1.446(3) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
O19 C20 . 1.422(3) ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
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
_geom_hbond_publ_flag
C3 H3 O16 3_766 0.93 2.54 3.362(3) 147 y
C20 H20A O21 2_445 0.96 2.50 3.454(3) 173 y
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 C1 C2 C3 . . . . 0.3(3) ?
C11 C1 C2 C15 . . . . -178.91(19) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
C15 C2 C3 C4 . . . . 178.6(2) ?
C2 C3 C4 C12 . . . . 0.6(4) ?
C14 C5 C6 C7 . . . . -0.2(4) ?
C5 C6 C7 O19 . . . . -179.7(2) ?
C5 C6 C7 C8 . . . . 0.2(4) ?
O19 C7 C8 C13 . . . . -179.99(19) ?
C6 C7 C8 C13 . . . . 0.1(3) ?
C2 C1 C11 C12 . . . . 0.1(3) ?
C2 C1 C11 C9 . . . . -179.66(19) ?
O21 C9 C11 C12 . . . . -179.0(2) ?
C13 C9 C11 C12 . . . . 0.7(3) ?
O21 C9 C11 C1 . . . . 0.8(3) ?
C13 C9 C11 C1 . . . . -179.53(17) ?
C14 O10 C12 C11 . . . . -0.8(3) ?
C14 O10 C12 C4 . . . . 179.6(2) ?
C1 C11 C12 O10 . . . . -179.70(17) ?
C9 C11 C12 O10 . . . . 0.1(3) ?
C1 C11 C12 C4 . . . . -0.2(3) ?
C9 C11 C12 C4 . . . . 179.6(2) ?
C3 C4 C12 O10 . . . . 179.4(2) ?
C3 C4 C12 C11 . . . . -0.1(4) ?
C7 C8 C13 C14 . . . . -0.3(3) ?
C7 C8 C13 C9 . . . . -179.76(19) ?
O21 C9 C13 C14 . . . . 178.94(19) ?
C11 C9 C13 C14 . . . . -0.7(3) ?
O21 C9 C13 C8 . . . . -1.6(3) ?
C11 C9 C13 C8 . . . . 178.67(18) ?
C8 C13 C14 C5 . . . . 0.3(3) ?
C9 C13 C14 C5 . . . . 179.7(2) ?
C8 C13 C14 O10 . . . . -179.42(18) ?
C9 C13 C14 O10 . . . . 0.0(3) ?
C6 C5 C14 C13 . . . . -0.1(4) ?
C6 C5 C14 O10 . . . . 179.7(2) ?
C12 O10 C14 C13 . . . . 0.8(3) ?
C12 O10 C14 C5 . . . . -178.9(2) ?
C1 C2 C15 O16 . . . . 177.5(2) ?
C3 C2 C15 O16 . . . . -1.7(4) ?
C1 C2 C15 O17 . . . . -3.8(3) ?
C3 C2 C15 O17 . . . . 177.05(19) ?
O16 C15 O17 C18 . . . . -0.8(3) ?
C2 C15 O17 C18 . . . . -179.59(18) ?
C8 C7 O19 C20 . . . . -0.2(3) ?
C6 C7 O19 C20 . . . . 179.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9812496
