#------------------------------------------------------------------------------
#$Date: 2023-01-20 12:11:43 +0200 (Fri, 20 Jan 2023) $
#$Revision: 280468 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106511.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_8106511
loop_
_publ_author_name
'Li, Jiangtao'
_publ_section_title
;
 Crystal structure of
 4a-Hydroxy-9-(2-nitro-phenyl)-3,4,4a,5,6,7,9,9a-octahydro-2H-xanthene-1,8-dione,
 C19H19NO6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              283
_journal_page_last               284
_journal_paper_doi               10.1515/ncrs-2016-0240
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C19 H19 N O6'
_chemical_formula_weight         357.35
_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_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.973(9)
_cell_angle_beta                 99.137(10)
_cell_angle_gamma                102.164(7)
_cell_formula_units_Z            2
_cell_length_a                   7.009(3)
_cell_length_b                   8.081(3)
_cell_length_c                   15.218(8)
_cell_measurement_reflns_used    1761
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.66
_cell_volume                     805.6(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3958
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0520
_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)+(0.0500P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                2238
_reflns_number_total             2809
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0240_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        805.5(6)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               8106511
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
N1 N 0.2619(3) 0.2025(2) 0.03365(13) 0.0239(5) Uani 1 1 d . . .
O1 O 0.0038(2) 0.39301(19) 0.35661(10) 0.0200(4) Uani 1 1 d . . .
O2 O -0.1200(2) 0.4203(2) 0.21191(11) 0.0216(4) Uani 1 1 d . . .
O3 O 0.3066(2) 0.0937(2) 0.30759(11) 0.0257(4) Uani 1 1 d . . .
O4 O 0.6635(2) 0.59710(19) 0.32322(11) 0.0234(4) Uani 1 1 d . . .
O5 O 0.1659(3) 0.1179(2) -0.04237(12) 0.0388(5) Uani 1 1 d . . .
O6 O 0.3628(3) 0.1421(2) 0.08635(11) 0.0287(4) Uani 1 1 d . . .
C1 C 0.1884(3) 0.5045(3) 0.37956(15) 0.0190(5) Uani 1 1 d . . .
C2 C 0.2187(3) 0.6304(3) 0.47093(16) 0.0217(5) Uani 1 1 d . . .
H2A H 0.2497 0.5734 0.5196 0.026 Uiso 1 1 calc R . .
H2B H 0.0965 0.6662 0.4765 0.026 Uiso 1 1 calc R . .
C3 C 0.3874(3) 0.7901(3) 0.48140(16) 0.0225(5) Uani 1 1 d . . .
H3A H 0.3454 0.8603 0.4411 0.027 Uiso 1 1 calc R . .
H3B H 0.4196 0.8608 0.5442 0.027 Uiso 1 1 calc R . .
C4 C 0.5707(3) 0.7358(3) 0.45769(16) 0.0226(5) Uani 1 1 d . . .
H4A H 0.6721 0.8392 0.4592 0.027 Uiso 1 1 calc R . .
H4B H 0.6237 0.6815 0.5040 0.027 Uiso 1 1 calc R . .
C5 C 0.5285(3) 0.6100(3) 0.36444(16) 0.0189(5) Uani 1 1 d . . .
C6 C 0.3243(3) 0.5011(3) 0.32663(15) 0.0190(5) Uani 1 1 d . . .
C7 C 0.2817(3) 0.3763(3) 0.23290(15) 0.0181(5) Uani 1 1 d . . .
H7A H 0.3935 0.3213 0.2312 0.022 Uiso 1 1 calc R . .
C8 C 0.0935(3) 0.2295(3) 0.22259(15) 0.0180(5) Uani 1 1 d . . .
H8A H 0.0426 0.1741 0.1569 0.022 Uiso 1 1 calc R . .
C9 C -0.0707(3) 0.3002(3) 0.26035(15) 0.0191(5) Uani 1 1 d . . .
C10 C -0.2514(3) 0.1578(3) 0.25860(16) 0.0218(5) Uani 1 1 d . . .
H10A H -0.3166 0.0996 0.1952 0.026 Uiso 1 1 calc R . .
H10B H -0.3455 0.2104 0.2875 0.026 Uiso 1 1 calc R . .
C11 C -0.1976(3) 0.0229(3) 0.30786(16) 0.0226(5) Uani 1 1 d . . .
H11A H -0.3163 -0.0696 0.3012 0.027 Uiso 1 1 calc R . .
H11B H -0.1474 0.0776 0.3729 0.027 Uiso 1 1 calc R . .
C12 C -0.0388(3) -0.0554(3) 0.26848(16) 0.0224(5) Uani 1 1 d . . .
H12A H 0.0025 -0.1328 0.3044 0.027 Uiso 1 1 calc R . .
H12B H -0.0946 -0.1235 0.2057 0.027 Uiso 1 1 calc R . .
C13 C 0.1393(3) 0.0882(3) 0.27051(15) 0.0196(5) Uani 1 1 d . . .
C14 C 0.2738(3) 0.4696(3) 0.15464(15) 0.0193(5) Uani 1 1 d . . .
C15 C 0.2769(3) 0.6461(3) 0.17247(16) 0.0221(5) Uani 1 1 d . . .
H15A H 0.2815 0.7060 0.2323 0.027 Uiso 1 1 calc R . .
C16 C 0.2734(4) 0.7359(3) 0.10385(17) 0.0252(5) Uani 1 1 d . . .
H16A H 0.2804 0.8550 0.1188 0.030 Uiso 1 1 calc R . .
C17 C 0.2596(3) 0.6507(3) 0.01414(17) 0.0248(5) Uani 1 1 d . . .
H17A H 0.2555 0.7112 -0.0316 0.030 Uiso 1 1 calc R . .
C18 C 0.2520(3) 0.4746(3) -0.00753(16) 0.0235(5) Uani 1 1 d . . .
H18A H 0.2406 0.4144 -0.0680 0.028 Uiso 1 1 calc R . .
C19 C 0.2616(3) 0.3883(3) 0.06288(16) 0.0204(5) Uani 1 1 d . . .
H2 H -0.211(4) 0.463(4) 0.244(2) 0.038(8) Uiso 1 1 d . . .
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
O5 N1 O6 123.38(19) . .
O5 N1 C19 118.42(18) . .
O6 N1 C19 118.19(18) . .
C1 O1 C9 117.16(17) . .
C9 O2 H2 101.5(18) . .
C6 C1 O1 124.0(2) . .
C6 C1 C2 125.0(2) . .
O1 C1 C2 111.01(19) . .
C1 C2 C3 110.68(19) . .
C1 C2 H2A 109.5 . .
C3 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 108.1 . .
C4 C3 C2 110.43(18) . .
C4 C3 H3A 109.6 . .
C2 C3 H3A 109.6 . .
C4 C3 H3B 109.6 . .
C2 C3 H3B 109.6 . .
H3A C3 H3B 108.1 . .
C5 C4 C3 113.03(19) . .
C5 C4 H4A 109.0 . .
C3 C4 H4A 109.0 . .
C5 C4 H4B 109.0 . .
C3 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
O4 C5 C6 121.6(2) . .
O4 C5 C4 120.3(2) . .
C6 C5 C4 118.1(2) . .
C1 C6 C5 119.0(2) . .
C1 C6 C7 122.7(2) . .
C5 C6 C7 118.1(2) . .
C6 C7 C14 112.71(18) . .
C6 C7 C8 109.31(19) . .
C14 C7 C8 113.91(17) . .
C6 C7 H7A 106.8 . .
C14 C7 H7A 106.8 . .
C8 C7 H7A 106.8 . .
C9 C8 C13 109.01(18) . .
C9 C8 C7 111.80(18) . .
C13 C8 C7 111.89(17) . .
C9 C8 H8A 108.0 . .
C13 C8 H8A 108.0 . .
C7 C8 H8A 108.0 . .
O2 C9 O1 107.79(17) . .
O2 C9 C10 112.31(18) . .
O1 C9 C10 105.43(18) . .
O2 C9 C8 108.37(18) . .
O1 C9 C8 109.60(17) . .
C10 C9 C8 113.17(18) . .
C9 C10 C11 112.52(18) . .
C9 C10 H10A 109.1 . .
C11 C10 H10A 109.1 . .
C9 C10 H10B 109.1 . .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
C10 C11 C12 110.93(19) . .
C10 C11 H11A 109.5 . .
C12 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 108.0 . .
C13 C12 C11 110.06(18) . .
C13 C12 H12A 109.6 . .
C11 C12 H12A 109.6 . .
C13 C12 H12B 109.6 . .
C11 C12 H12B 109.6 . .
H12A C12 H12B 108.2 . .
O3 C13 C12 122.7(2) . .
O3 C13 C8 121.9(2) . .
C12 C13 C8 115.43(18) . .
C15 C14 C19 115.3(2) . .
C15 C14 C7 120.4(2) . .
C19 C14 C7 124.27(19) . .
C16 C15 C14 122.2(2) . .
C16 C15 H15A 118.9 . .
C14 C15 H15A 118.9 . .
C17 C16 C15 120.7(2) . .
C17 C16 H16A 119.7 . .
C15 C16 H16A 119.7 . .
C16 C17 C18 119.4(2) . .
C16 C17 H17A 120.3 . .
C18 C17 H17A 120.3 . .
C17 C18 C19 118.9(2) . .
C17 C18 H18A 120.6 . .
C19 C18 H18A 120.6 . .
C18 C19 C14 123.5(2) . .
C18 C19 N1 114.9(2) . .
C14 C19 N1 121.61(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 O5 1.221(2) .
N1 O6 1.229(2) .
N1 C19 1.475(3) .
O1 C1 1.357(3) .
O1 C9 1.455(3) .
O2 C9 1.401(3) .
O2 H2 0.94(3) .
O3 C13 1.205(3) .
O4 C5 1.226(3) .
C1 C6 1.343(3) .
C1 C2 1.497(3) .
C2 C3 1.517(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.514(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.509(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.467(3) .
C6 C7 1.510(3) .
C7 C14 1.536(3) .
C7 C8 1.539(3) .
C7 H7A 0.9800 .
C8 C9 1.527(3) .
C8 C13 1.537(3) .
C8 H8A 0.9800 .
C9 C10 1.514(3) .
C10 C11 1.522(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.533(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.506(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C14 C15 1.391(3) .
C14 C19 1.395(3) .
C15 C16 1.390(3) .
C15 H15A 0.9300 .
C16 C17 1.374(3) .
C16 H16A 0.9300 .
C17 C18 1.381(3) .
C17 H17A 0.9300 .
C18 C19 1.395(3) .
C18 H18A 0.9300 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C9 O1 C1 C6 -18.2(3) . . . .
C9 O1 C1 C2 161.76(17) . . . .
C6 C1 C2 C3 19.9(3) . . . .
O1 C1 C2 C3 -160.02(17) . . . .
C1 C2 C3 C4 -49.9(2) . . . .
C2 C3 C4 C5 53.3(2) . . . .
C3 C4 C5 O4 156.7(2) . . . .
C3 C4 C5 C6 -25.2(3) . . . .
O1 C1 C6 C5 -170.85(18) . . . .
C2 C1 C6 C5 9.2(3) . . . .
O1 C1 C6 C7 2.9(3) . . . .
C2 C1 C6 C7 -177.04(19) . . . .
O4 C5 C6 C1 171.6(2) . . . .
C4 C5 C6 C1 -6.5(3) . . . .
O4 C5 C6 C7 -2.4(3) . . . .
C4 C5 C6 C7 179.46(18) . . . .
C1 C6 C7 C14 111.9(2) . . . .
C5 C6 C7 C14 -74.3(2) . . . .
C1 C6 C7 C8 -15.9(3) . . . .
C5 C6 C7 C8 157.90(18) . . . .
C6 C7 C8 C9 42.6(2) . . . .
C14 C7 C8 C9 -84.5(2) . . . .
C6 C7 C8 C13 -80.0(2) . . . .
C14 C7 C8 C13 152.92(19) . . . .
C1 O1 C9 O2 -72.9(2) . . . .
C1 O1 C9 C10 167.00(17) . . . .
C1 O1 C9 C8 44.9(2) . . . .
C13 C8 C9 O2 -176.20(16) . . . .
C7 C8 C9 O2 59.6(2) . . . .
C13 C8 C9 O1 66.4(2) . . . .
C7 C8 C9 O1 -57.8(2) . . . .
C13 C8 C9 C10 -50.9(2) . . . .
C7 C8 C9 C10 -175.17(18) . . . .
O2 C9 C10 C11 177.71(19) . . . .
O1 C9 C10 C11 -65.2(2) . . . .
C8 C9 C10 C11 54.6(3) . . . .
C9 C10 C11 C12 -55.1(3) . . . .
C10 C11 C12 C13 54.0(2) . . . .
C11 C12 C13 O3 124.8(2) . . . .
C11 C12 C13 C8 -54.7(3) . . . .
C9 C8 C13 O3 -127.0(2) . . . .
C7 C8 C13 O3 -2.9(3) . . . .
C9 C8 C13 C12 52.5(2) . . . .
C7 C8 C13 C12 176.65(19) . . . .
C6 C7 C14 C15 -8.8(3) . . . .
C8 C7 C14 C15 116.5(2) . . . .
C6 C7 C14 C19 171.8(2) . . . .
C8 C7 C14 C19 -63.0(3) . . . .
C19 C14 C15 C16 -1.6(3) . . . .
C7 C14 C15 C16 178.9(2) . . . .
C14 C15 C16 C17 2.3(4) . . . .
C15 C16 C17 C18 -0.9(4) . . . .
C16 C17 C18 C19 -1.0(3) . . . .
C17 C18 C19 C14 1.6(3) . . . .
C17 C18 C19 N1 -177.2(2) . . . .
C15 C14 C19 C18 -0.3(3) . . . .
C7 C14 C19 C18 179.1(2) . . . .
C15 C14 C19 N1 178.49(19) . . . .
C7 C14 C19 N1 -2.1(3) . . . .
O5 N1 C19 C18 -34.0(3) . . . .
O6 N1 C19 C18 144.3(2) . . . .
O5 N1 C19 C14 147.2(2) . . . .
O6 N1 C19 C14 -34.5(3) . . . .
