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#$Date: 2023-05-22 12:18:06 +0300 (Mon, 22 May 2023) $
#$Revision: 283934 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107241.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_8107241
loop_
_publ_author_name
'Li, Yijv'
'Zhao, Nengwu'
'Ye, Jianghai'
'Xu, Fangfang'
'Luo, Shuntong'
'Lang, Tianqiong'
_publ_section_title
;
 The crystal structure of Chrysosplenol D, C18H16O8
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              877
_journal_page_last               879
_journal_paper_doi               10.1515/ncrs-2022-0257
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C18 H16 O8'
_chemical_formula_sum            'C18 H16 O8'
_chemical_formula_weight         360.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 103.5820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5762(6)
_cell_length_b                   6.6791(3)
_cell_length_c                   17.4240(7)
_cell_measurement_reflns_used    4974
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.552
_cell_measurement_theta_min      3.279
_cell_volume                     1648.89(12)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26956
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         30.552
_diffrn_reflns_theta_min         3.279
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0611P)²+0.3950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4066
_reflns_number_total             4974
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0257_suppl.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8107241
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67411(6) 0.37707(13) 0.47987(5) 0.03476(18) Uani 1 1 d . . . . .
O2 O 0.78874(6) 0.25446(13) 0.32164(5) 0.03709(19) Uani 1 1 d . . . . .
O3 O 0.90108(6) 0.55706(14) 0.39832(5) 0.0398(2) Uani 1 1 d . . . . .
O4 O 0.94321(6) 0.81128(15) 0.51429(6) 0.0405(2) Uani 1 1 d . . . . .
O5 O 0.89493(6) 0.97839(12) 0.64258(5) 0.03456(18) Uani 1 1 d . . . . .
O6 O 0.74024(7) 0.86607(14) 0.68375(5) 0.0422(2) Uani 1 1 d . . . . .
O7 O 0.50979(7) -0.12550(14) 0.20154(5) 0.0396(2) Uani 1 1 d . . . . .
H7 H 0.5469(11) -0.066(3) 0.1725(7) 0.059 Uiso 1 1 calc R U . . .
O8 O 0.45890(8) -0.36848(16) 0.30770(6) 0.0542(3) Uani 1 1 d . . . . .
H8A H 0.4522(13) -0.383(2) 0.2579(14) 0.081 Uiso 1 1 calc R U . . .
C2 C 0.69411(8) 0.28595(16) 0.41562(6) 0.0310(2) Uani 1 1 d . . . . .
C3 C 0.76907(8) 0.34384(16) 0.38656(6) 0.0309(2) Uani 1 1 d . . . . .
C4 C 0.83054(7) 0.50306(16) 0.42306(6) 0.0296(2) Uani 1 1 d . . . . .
C5 C 0.86423(7) 0.74856(16) 0.53425(6) 0.0287(2) Uani 1 1 d . . . . .
C6 C 0.83902(8) 0.83410(15) 0.59814(6) 0.0285(2) Uani 1 1 d . . . . .
C7 C 0.75824(8) 0.76715(16) 0.62150(6) 0.0299(2) Uani 1 1 d . . . . .
C8 C 0.70351(8) 0.61126(17) 0.58245(6) 0.0320(2) Uani 1 1 d . . . . .
H8 H 0.651550 0.563469 0.599227 0.038 Uiso 1 1 calc R U . . .
C9 C 0.72943(7) 0.52961(16) 0.51738(6) 0.0288(2) Uani 1 1 d . . . . .
C10 C 0.80759(7) 0.59516(16) 0.49085(6) 0.0283(2) Uani 1 1 d . . . . .
C11 C 0.62949(8) 0.12028(17) 0.38662(6) 0.0318(2) Uani 1 1 d . . . . .
C12 C 0.60149(8) 0.07936(17) 0.30565(6) 0.0314(2) Uani 1 1 d . . . . .
H12 H 0.622033 0.161017 0.269816 0.038 Uiso 1 1 calc R U . . .
C13 C 0.54364(7) -0.08138(16) 0.27893(6) 0.0291(2) Uani 1 1 d . . . . .
C14 C 0.51408(9) -0.20721(18) 0.33272(7) 0.0352(2) Uani 1 1 d . . . . .
C15 C 0.54088(10) -0.1654(2) 0.41268(7) 0.0438(3) Uani 1 1 d . . . . .
H15 H 0.520808 -0.247764 0.448553 0.053 Uiso 1 1 calc R U . . .
C16 C 0.59745(9) -0.0013(2) 0.43945(7) 0.0403(3) Uani 1 1 d . . . . .
H16 H 0.614086 0.027568 0.493154 0.048 Uiso 1 1 calc R U . . .
C17 C 0.83729(11) 0.0663(2) 0.33716(10) 0.0519(3) Uani 1 1 d . . . . .
H17A H 0.851323 0.016904 0.289449 0.078 Uiso 1 1 calc R U . . .
H17B H 0.798009 -0.028368 0.355880 0.078 Uiso 1 1 calc R U . . .
H17C H 0.894982 0.084574 0.376523 0.078 Uiso 1 1 calc R U . . .
C18 C 0.88594(13) 1.1704(2) 0.60732(9) 0.0513(4) Uani 1 1 d . . . . .
H18A H 0.896200 1.160883 0.555000 0.077 Uiso 1 1 calc R U . . .
H18B H 0.931818 1.259098 0.638408 0.077 Uiso 1 1 calc R U . . .
H18C H 0.823700 1.221443 0.604635 0.077 Uiso 1 1 calc R U . . .
C19 C 0.65910(11) 0.8102(2) 0.71101(9) 0.0525(4) Uani 1 1 d . . . . .
H19A H 0.604113 0.818154 0.668153 0.079 Uiso 1 1 calc R U . . .
H19B H 0.652004 0.899301 0.752467 0.079 Uiso 1 1 calc R U . . .
H19C H 0.666467 0.675578 0.730773 0.079 Uiso 1 1 calc R U . . .
H9 H 0.9458(15) 0.744(4) 0.4711(13) 0.079(6) 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'
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
C2 O1 C9 120.61(9) . .
C3 O2 C17 114.58(10) . .
C5 O4 H9 105.8(14) . .
C6 O5 C18 114.08(9) . .
C7 O6 C19 118.29(10) . .
C13 O7 H7 109.5 . .
C14 O8 H8A 109.5 . .
C3 C2 O1 121.49(9) . .
C3 C2 C11 126.36(10) . .
O1 C2 C11 112.09(9) . .
C2 C3 O2 121.68(10) . .
C2 C3 C4 121.04(9) . .
O2 C3 C4 117.28(9) . .
O3 C4 C3 122.35(10) . .
O3 C4 C10 121.67(10) . .
C3 C4 C10 115.97(9) . .
O4 C5 C6 119.16(10) . .
O4 C5 C10 120.90(9) . .
C6 C5 C10 119.94(9) . .
C5 C6 O5 120.69(10) . .
C5 C6 C7 120.21(9) . .
O5 C6 C7 119.01(9) . .
O6 C7 C8 124.34(10) . .
O6 C7 C6 114.31(9) . .
C8 C7 C6 121.35(9) . .
C9 C8 C7 117.36(10) . .
C9 C8 H8 121.3 . .
C7 C8 H8 121.3 . .
O1 C9 C8 116.12(9) . .
O1 C9 C10 120.72(9) . .
C8 C9 C10 123.15(10) . .
C9 C10 C5 117.91(9) . .
C9 C10 C4 120.17(9) . .
C5 C10 C4 121.89(9) . .
C16 C11 C12 119.34(10) . .
C16 C11 C2 120.18(10) . .
C12 C11 C2 120.45(10) . .
C13 C12 C11 120.22(10) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
O7 C13 C12 123.85(10) . .
O7 C13 C14 116.00(10) . .
C12 C13 C14 120.13(10) . .
O8 C14 C15 119.39(10) . .
O8 C14 C13 120.99(10) . .
C15 C14 C13 119.62(10) . .
C14 C15 C16 120.25(11) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C15 C16 C11 120.40(10) . .
C15 C16 H16 119.8 . .
C11 C16 H16 119.8 . .
O2 C17 H17A 109.5 . .
O2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
O2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O5 C18 H18A 109.5 . .
O5 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O5 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O6 C19 H19A 109.5 . .
O6 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O6 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3644(13) .
O1 C9 1.3668(13) .
O2 C3 1.3677(12) .
O2 C17 1.4366(17) .
O3 C4 1.2574(13) .
O4 C5 1.3454(13) .
O4 H9 0.88(2) .
O5 C6 1.3770(13) .
O5 C18 1.4146(15) .
O6 C7 1.3474(13) .
O6 C19 1.4239(16) .
O7 C13 1.3551(12) .
O7 H7 0.91(2) .
O8 C14 1.3537(14) .
O8 H8A 0.86(2) .
C2 C3 1.3635(15) .
C2 C11 1.4641(15) .
C3 C4 1.4390(15) .
C4 C10 1.4392(14) .
C5 C6 1.3757(15) .
C5 C10 1.4177(14) .
C6 C7 1.4062(15) .
C7 C8 1.3887(15) .
C8 C9 1.3881(14) .
C8 H8 0.9300 .
C9 C10 1.3967(14) .
C11 C16 1.3881(16) .
C11 C12 1.4004(15) .
C12 C13 1.3770(15) .
C12 H12 0.9300 .
C13 C14 1.4000(15) .
C14 C15 1.3841(16) .
C15 C16 1.3849(17) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
