#------------------------------------------------------------------------------
#$Date: 2020-07-29 08:30:20 +0300 (Wed, 29 Jul 2020) $
#$Revision: 254647 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558687.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_1558687
loop_
_publ_author_name
'Detert, Heiner'
'Kluge, Laura'
'Schollmeyer, Dieter'
_publ_section_title
;
 Methyl
 3,3,6,6-tetramethyl-1,8-dioxo-4,5,7,9-tetrahydro-2H-xanthene-9-carboxylate
;
_journal_coeditor_code           GG4005
_journal_issue                   7
_journal_name_full               IUCrData
_journal_page_first              x201018
_journal_paper_doi               10.1107/S2414314620010184
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C19 H24 O5'
_chemical_formula_moiety         'C19 H24 O5'
_chemical_formula_sum            'C19 H24 O5'
_chemical_formula_weight         332.38
_chemical_name_systematic
'Methyl 3,3,6,6-tetramethyl-1,8-dioxo-4,5,7,9-tetrahydro-2H-xanthene-9-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 113.295(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1494(10)
_cell_length_b                   9.6899(6)
_cell_length_c                   14.8185(13)
_cell_measurement_reflns_used    9146
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.58
_cell_volume                     1734.2(2)
_computing_cell_refinement
;
X-AREA Recipe (Stoe & Cie, 2019)
;
_computing_data_collection
;
X-AREA WinXpose (Stoe & Cie, 2019)
;
_computing_data_reduction
;
X-AREA Integrate (Stoe & Cie, 2019)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR-2004 (Burla et al.,  2005)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8583
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.949
_diffrn_reflns_theta_min         2.580
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0577P)²+2.4014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1845
_reflns_number_gt                2784
_reflns_number_total             4123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            gg4005sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1558687
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6910(2) 0.3522(3) 0.3759(2) 0.0290(5) Uani d 1 . .
H H1 0.715526 0.337644 0.320767 0.035 Uiso calc 1 . .
C C2 0.7343(2) 0.2359(3) 0.4490(2) 0.0284(5) Uani d 1 . .
C C3 0.8403(2) 0.1694(3) 0.4650(2) 0.0292(5) Uani d 1 . .
C C4 0.8801(2) 0.0564(3) 0.5415(2) 0.0327(6) Uani d 1 . .
H H4A 0.962100 0.056545 0.570806 0.039 Uiso calc 1 . .
H H4B 0.855649 -0.033835 0.508675 0.039 Uiso calc 1 . .
C C5 0.8385(2) 0.0705(3) 0.6237(2) 0.0302(6) Uani d 1 . .
C C6 0.7113(2) 0.0808(3) 0.5759(2) 0.0313(6) Uani d 1 . .
H H6A 0.679951 -0.010095 0.548221 0.038 Uiso calc 1 . .
H H6B 0.683107 0.105346 0.626632 0.038 Uiso calc 1 . .
C C7 0.67398(19) 0.1865(3) 0.49633(19) 0.0270(5) Uani d 1 . .
O O8 0.56625(14) 0.22547(18) 0.47408(13) 0.0293(4) Uani d 1 . .
C C9 0.5126(2) 0.2955(3) 0.38683(19) 0.0283(5) Uani d 1 . .
C C10 0.3910(2) 0.3002(3) 0.3590(2) 0.0301(6) Uani d 1 . .
H H10A 0.375949 0.313286 0.418829 0.036 Uiso calc 1 . .
H H10B 0.358002 0.211094 0.328896 0.036 Uiso calc 1 . .
C C11 0.3362(2) 0.4177(3) 0.2862(2) 0.0312(6) Uani d 1 . .
C C12 0.3794(2) 0.4120(3) 0.2043(2) 0.0329(6) Uani d 1 . .
H H12A 0.354823 0.324715 0.167285 0.040 Uiso calc 1 . .
H H12B 0.347003 0.489267 0.158080 0.040 Uiso calc 1 . .
C C13 0.5040(2) 0.4207(3) 0.2430(2) 0.0302(5) Uani d 1 . .
C C14 0.5668(2) 0.3511(3) 0.33598(19) 0.0276(5) Uani d 1 . .
C C15 0.7354(2) 0.4908(3) 0.4252(2) 0.0307(6) Uani d 1 . .
O O16 0.68175(18) 0.5800(2) 0.4402(2) 0.0579(7) Uani d 1 . .
O O17 0.84313(17) 0.5003(2) 0.4521(2) 0.0606(8) Uani d 1 . .
C C18 0.8958(3) 0.6248(3) 0.5039(3) 0.0611(11) Uani d 1 . .
H H18A 0.976272 0.616654 0.525273 0.092 Uiso calc 1 . .
H H18B 0.877556 0.637293 0.561397 0.092 Uiso calc 1 . .
H H18C 0.869276 0.704400 0.460044 0.092 Uiso calc 1 . .
O O19 0.89116(15) 0.19842(19) 0.41368(14) 0.0334(4) Uani d 1 . .
C C20 0.8901(2) 0.1983(3) 0.6859(2) 0.0369(6) Uani d 1 . .
H H20A 0.971000 0.190656 0.712677 0.055 Uiso calc 1 . .
H H20B 0.865283 0.204928 0.740014 0.055 Uiso calc 1 . .
H H20C 0.867042 0.281133 0.644830 0.055 Uiso calc 1 . .
C C21 0.8723(2) -0.0569(3) 0.6899(2) 0.0407(7) Uani d 1 . .
H H21A 0.841283 -0.139699 0.650705 0.061 Uiso calc 1 . .
H H21B 0.844160 -0.048635 0.741779 0.061 Uiso calc 1 . .
H H21C 0.953273 -0.063927 0.719617 0.061 Uiso calc 1 . .
C C22 0.3647(2) 0.5576(3) 0.3387(2) 0.0386(7) Uani d 1 . .
H H22A 0.332418 0.631853 0.290953 0.058 Uiso calc 1 . .
H H22B 0.445306 0.568687 0.369190 0.058 Uiso calc 1 . .
H H22C 0.334574 0.561723 0.389470 0.058 Uiso calc 1 . .
C C23 0.2108(2) 0.3990(3) 0.2434(2) 0.0386(7) Uani d 1 . .
H H23A 0.175703 0.475736 0.198843 0.058 Uiso calc 1 . .
H H23B 0.184611 0.397602 0.296837 0.058 Uiso calc 1 . .
H H23C 0.191455 0.311806 0.207127 0.058 Uiso calc 1 . .
O O24 0.55164(16) 0.4811(2) 0.19806(15) 0.0394(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
C14 C1 C2 . . 108.7(2) ?
C14 C1 C15 . . 110.2(2) ?
C2 C1 C15 . . 110.4(2) ?
C14 C1 H1 . . 109.2 ?
C2 C1 H1 . . 109.2 ?
C15 C1 H1 . . 109.2 ?
C7 C2 C3 . . 118.7(2) ?
C7 C2 C1 . . 120.7(2) ?
C3 C2 C1 . . 120.5(2) ?
O19 C3 C2 . . 121.0(2) ?
O19 C3 C4 . . 121.2(2) ?
C2 C3 C4 . . 117.7(2) ?
C3 C4 C5 . . 114.0(2) ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4B . . 108.8 ?
C5 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C4 C5 C21 . . 109.6(2) ?
C4 C5 C20 . . 109.8(2) ?
C21 C5 C20 . . 108.6(2) ?
C4 C5 C6 . . 107.8(2) ?
C21 C5 C6 . . 109.6(2) ?
C20 C5 C6 . . 111.5(2) ?
C7 C6 C5 . . 111.5(2) ?
C7 C6 H6A . . 109.3 ?
C5 C6 H6A . . 109.3 ?
C7 C6 H6B . . 109.3 ?
C5 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
C2 C7 O8 . . 123.0(2) ?
C2 C7 C6 . . 125.6(2) ?
O8 C7 C6 . . 111.4(2) ?
C7 O8 C9 . . 117.1(2) ?
C14 C9 O8 . . 122.5(2) ?
C14 C9 C10 . . 125.8(2) ?
O8 C9 C10 . . 111.7(2) ?
C9 C10 C11 . . 111.8(2) ?
C9 C10 H10A . . 109.2 ?
C11 C10 H10A . . 109.2 ?
C9 C10 H10B . . 109.2 ?
C11 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C23 C11 C12 . . 110.2(2) ?
C23 C11 C22 . . 108.8(2) ?
C12 C11 C22 . . 109.9(2) ?
C23 C11 C10 . . 109.5(2) ?
C12 C11 C10 . . 108.1(2) ?
C22 C11 C10 . . 110.2(2) ?
C13 C12 C11 . . 112.6(2) ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
O24 C13 C14 . . 120.7(2) ?
O24 C13 C12 . . 122.0(2) ?
C14 C13 C12 . . 117.2(2) ?
C9 C14 C13 . . 119.2(2) ?
C9 C14 C1 . . 121.3(2) ?
C13 C14 C1 . . 119.4(2) ?
O16 C15 O17 . . 122.7(3) ?
O16 C15 C1 . . 125.7(2) ?
O17 C15 C1 . . 111.6(2) ?
C15 O17 C18 . . 116.8(2) ?
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 ?
C5 C20 H20A . . 109.5 ?
C5 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C5 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C5 C21 H21A . . 109.5 ?
C5 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C5 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C11 C22 H22A . . 109.5 ?
C11 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C11 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C11 C23 H23A . . 109.5 ?
C11 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C11 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 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 C14 . 1.501(3) ?
C1 C2 . 1.510(4) ?
C1 C15 . 1.530(4) ?
C1 H1 . 1.0000 ?
C2 C7 . 1.337(3) ?
C2 C3 . 1.468(3) ?
C3 O19 . 1.228(3) ?
C3 C4 . 1.513(4) ?
C4 C5 . 1.526(4) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C21 . 1.529(4) ?
C5 C20 . 1.533(4) ?
C5 C6 . 1.541(3) ?
C6 C7 . 1.490(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 O8 . 1.374(3) ?
O8 C9 . 1.381(3) ?
C9 C14 . 1.338(3) ?
C9 C10 . 1.486(3) ?
C10 C11 . 1.538(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C23 . 1.526(3) ?
C11 C12 . 1.532(4) ?
C11 C22 . 1.534(4) ?
C12 C13 . 1.508(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 O24 . 1.229(3) ?
C13 C14 . 1.461(4) ?
C15 O16 . 1.191(3) ?
C15 O17 . 1.314(3) ?
O17 C18 . 1.450(4) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
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
C6 H6B O24 4_566 0.99 2.50 3.324(4) 140
C18 H18A O17 3_766 0.98 2.53 3.451(5) 156
C18 H18A O19 3_766 0.98 2.41 3.093(4) 126
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
C14 C1 C2 C7 . . . . -25.2(3) ?
C15 C1 C2 C7 . . . . 95.7(3) ?
C14 C1 C2 C3 . . . . 151.0(2) ?
C15 C1 C2 C3 . . . . -88.1(3) ?
C7 C2 C3 O19 . . . . 170.0(2) ?
C1 C2 C3 O19 . . . . -6.3(4) ?
C7 C2 C3 C4 . . . . -5.4(4) ?
C1 C2 C3 C4 . . . . 178.2(2) ?
O19 C3 C4 C5 . . . . 156.8(2) ?
C2 C3 C4 C5 . . . . -27.7(3) ?
C3 C4 C5 C21 . . . . 173.5(2) ?
C3 C4 C5 C20 . . . . -67.3(3) ?
C3 C4 C5 C6 . . . . 54.3(3) ?
C4 C5 C6 C7 . . . . -49.8(3) ?
C21 C5 C6 C7 . . . . -168.9(2) ?
C20 C5 C6 C7 . . . . 70.8(3) ?
C3 C2 C7 O8 . . . . -168.6(2) ?
C1 C2 C7 O8 . . . . 7.7(4) ?
C3 C2 C7 C6 . . . . 9.2(4) ?
C1 C2 C7 C6 . . . . -174.5(2) ?
C5 C6 C7 C2 . . . . 20.1(4) ?
C5 C6 C7 O8 . . . . -161.9(2) ?
C2 C7 O8 C9 . . . . 13.7(3) ?
C6 C7 O8 C9 . . . . -164.4(2) ?
C7 O8 C9 C14 . . . . -14.7(4) ?
C7 O8 C9 C10 . . . . 165.5(2) ?
C14 C9 C10 C11 . . . . -20.5(4) ?
O8 C9 C10 C11 . . . . 159.3(2) ?
C9 C10 C11 C23 . . . . 167.9(2) ?
C9 C10 C11 C12 . . . . 47.7(3) ?
C9 C10 C11 C22 . . . . -72.5(3) ?
C23 C11 C12 C13 . . . . -176.3(2) ?
C22 C11 C12 C13 . . . . 63.7(3) ?
C10 C11 C12 C13 . . . . -56.7(3) ?
C11 C12 C13 O24 . . . . -144.6(3) ?
C11 C12 C13 C14 . . . . 36.9(3) ?
O8 C9 C14 C13 . . . . 178.5(2) ?
C10 C9 C14 C13 . . . . -1.7(4) ?
O8 C9 C14 C1 . . . . -5.9(4) ?
C10 C9 C14 C1 . . . . 173.9(2) ?
O24 C13 C14 C9 . . . . 174.9(3) ?
C12 C13 C14 C9 . . . . -6.5(4) ?
O24 C13 C14 C1 . . . . -0.8(4) ?
C12 C13 C14 C1 . . . . 177.8(2) ?
C2 C1 C14 C9 . . . . 24.4(3) ?
C15 C1 C14 C9 . . . . -96.7(3) ?
C2 C1 C14 C13 . . . . -160.0(2) ?
C15 C1 C14 C13 . . . . 78.9(3) ?
C14 C1 C15 O16 . . . . 7.8(4) ?
C2 C1 C15 O16 . . . . -112.2(3) ?
C14 C1 C15 O17 . . . . -173.5(2) ?
C2 C1 C15 O17 . . . . 66.4(3) ?
O16 C15 O17 C18 . . . . 1.4(5) ?
C1 C15 O17 C18 . . . . -177.2(3) ?

_cod_database_fobs_code 1558687
