#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:30:56 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157804.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_7157804
loop_
_publ_author_name
'Gao, Yu-Qi'
'Hou, Yi'
'Chen, Junhan'
'Zhen, Yanxia'
'Xu, Dongyang'
'Zhang, Hongli'
'Wei, Hongbo'
'Xie, Weiqing'
_publ_section_title
;
 Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem
 asymmetric Michael/cyclization promoted by chiral phosphoric acid.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              348
_journal_page_last               354
_journal_paper_doi               10.1039/d0ob02140g
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 O5'
_chemical_formula_sum            'C17 H16 O5'
_chemical_formula_weight         300.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-13 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5125(9)
_cell_length_b                   10.2643(10)
_cell_length_c                   14.9575(14)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.05
_cell_measurement_theta_min      4.65
_cell_volume                     1460.4(2)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26596
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_min         5.226
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0290
_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)+(0.0463P)²+0.0728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2643
_reflns_number_total             2874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02140g2.cif
_cod_data_source_block           664
_cod_depositor_comments          'Adding full bibliography for 7157804.cif.'
_cod_database_code               7157804
_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.
;
_shelx_estimated_absorpt_t_min   0.850
_shelx_estimated_absorpt_t_max   0.936
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 0.19889(13) 0.16357(13) 0.68047(9) 0.0543(3) Uani 1 1 d . . . . .
O2 O 0.39856(16) 0.57351(13) 0.62293(11) 0.0664(4) Uani 1 1 d . . . . .
O3 O 0.43078(17) 0.51098(15) 0.41879(10) 0.0719(4) Uani 1 1 d . . . . .
O4 O 0.71907(14) 0.44182(15) 0.54945(11) 0.0650(4) Uani 1 1 d . . . . .
O5 O 0.64850(16) 0.63482(14) 0.49631(11) 0.0661(4) Uani 1 1 d . . . . .
C1 C 0.5660(2) 0.0896(2) 0.62614(15) 0.0575(5) Uani 1 1 d . . . . .
H1A H 0.647847 0.130122 0.606575 0.069 Uiso 1 1 calc R U . . .
C2 C 0.5683(3) -0.0418(2) 0.64510(15) 0.0662(6) Uani 1 1 d . . . . .
H2A H 0.651025 -0.088976 0.638079 0.079 Uiso 1 1 calc R U . . .
C3 C 0.4480(3) -0.10322(19) 0.67448(15) 0.0674(6) Uani 1 1 d . . . . .
H3A H 0.449127 -0.192196 0.686206 0.081 Uiso 1 1 calc R U . . .
C4 C 0.3264(2) -0.0329(2) 0.68645(14) 0.0597(5) Uani 1 1 d . . . . .
H4A H 0.245286 -0.073393 0.707247 0.072 Uiso 1 1 calc R U . . .
C5 C 0.32643(19) 0.09932(17) 0.66705(12) 0.0464(4) Uani 1 1 d . . . . .
C6 C 0.19615(18) 0.29552(18) 0.67251(12) 0.0452(4) Uani 1 1 d . . . . .
C7 C 0.0588(2) 0.3507(2) 0.70318(14) 0.0573(5) Uani 1 1 d . . . . .
H7A H 0.057615 0.355045 0.767958 0.069 Uiso 1 1 calc R U . . .
H7B H -0.017156 0.294007 0.684275 0.069 Uiso 1 1 calc R U . . .
C8 C 0.0362(2) 0.4851(2) 0.66519(17) 0.0683(6) Uani 1 1 d . . . . .
H8A H -0.045279 0.524573 0.693210 0.082 Uiso 1 1 calc R U . . .
H8B H 0.017996 0.478646 0.601534 0.082 Uiso 1 1 calc R U . . .
C9 C 0.1638(2) 0.5703(2) 0.68071(17) 0.0667(6) Uani 1 1 d . . . . .
H9A H 0.173732 0.586657 0.744264 0.080 Uiso 1 1 calc R U . . .
H9B H 0.149798 0.653439 0.651197 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2975(2) 0.50833(18) 0.64586(12) 0.0521(4) Uani 1 1 d . . . . .
C11 C 0.30468(18) 0.36589(17) 0.64220(11) 0.0422(4) Uani 1 1 d . . . . .
C12 C 0.43995(17) 0.30528(16) 0.61006(11) 0.0406(3) Uani 1 1 d . . . . .
H12A H 0.518284 0.349529 0.639876 0.049 Uiso 1 1 calc R U . . .
C13 C 0.44430(18) 0.16264(17) 0.63560(11) 0.0433(4) Uani 1 1 d . . . . .
C14 C 0.45990(18) 0.31951(18) 0.50777(12) 0.0472(4) Uani 1 1 d . . . . .
H14A H 0.533896 0.260455 0.489094 0.057 Uiso 1 1 calc R U . . .
H14B H 0.373907 0.291871 0.478529 0.057 Uiso 1 1 calc R U . . .
C15 C 0.49594(18) 0.45385(19) 0.47514(11) 0.0485(4) Uani 1 1 d . . . . .
C16 C 0.63456(19) 0.50961(18) 0.51251(13) 0.0510(4) Uani 1 1 d . . . . .
C17 C 0.7766(3) 0.6931(2) 0.53129(19) 0.0820(7) Uani 1 1 d . . . . .
H17A H 0.778402 0.784130 0.516608 0.123 Uiso 1 1 calc R U . . .
H17B H 0.779078 0.682861 0.595063 0.123 Uiso 1 1 calc R U . . .
H17C H 0.856721 0.650767 0.505277 0.123 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
_geom_angle_publ_flag
C6 O1 C5 118.35(14) . . ?
C16 O5 C17 114.85(18) . . ?
C2 C1 C13 121.4(2) . . ?
C2 C1 H1A 119.3 . . ?
C13 C1 H1A 119.3 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 119.98(18) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C13 C5 C4 122.18(18) . . ?
C13 C5 O1 122.23(15) . . ?
C4 C5 O1 115.59(17) . . ?
C11 C6 O1 123.51(16) . . ?
C11 C6 C7 124.94(17) . . ?
O1 C6 C7 111.54(16) . . ?
C6 C7 C8 110.82(16) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 110.89(19) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 112.21(18) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O2 C10 C11 120.02(17) . . ?
O2 C10 C9 121.86(17) . . ?
C11 C10 C9 118.10(17) . . ?
C6 C11 C10 119.34(16) . . ?
C6 C11 C12 122.91(16) . . ?
C10 C11 C12 117.60(16) . . ?
C11 C12 C13 109.99(14) . . ?
C11 C12 C14 112.37(14) . . ?
C13 C12 C14 109.70(14) . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C14 C12 H12A 108.2 . . ?
C5 C13 C1 117.31(16) . . ?
C5 C13 C12 121.32(15) . . ?
C1 C13 C12 121.34(17) . . ?
C15 C14 C12 115.82(14) . . ?
C15 C14 H14A 108.3 . . ?
C12 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C12 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O3 C15 C14 123.99(18) . . ?
O3 C15 C16 121.01(18) . . ?
C14 C15 C16 114.70(15) . . ?
O4 C16 O5 125.81(19) . . ?
O4 C16 C15 121.69(17) . . ?
O5 C16 C15 112.47(16) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.360(2) . ?
O1 C5 1.395(2) . ?
O2 C10 1.220(2) . ?
O3 C15 1.199(2) . ?
O4 C16 1.198(2) . ?
O5 C16 1.315(2) . ?
O5 C17 1.455(3) . ?
C1 C2 1.378(3) . ?
C1 C13 1.387(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4A 0.9300 . ?
C5 C13 1.379(3) . ?
C6 C11 1.339(2) . ?
C6 C7 1.496(2) . ?
C7 C8 1.507(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.465(2) . ?
C11 C12 1.508(2) . ?
C12 C13 1.514(2) . ?
C12 C14 1.549(2) . ?
C12 H12A 0.9800 . ?
C14 C15 1.502(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.542(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
_geom_torsion_publ_flag
C13 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C13 0.4(3) . . . . ?
C3 C4 C5 O1 179.67(18) . . . . ?
C6 O1 C5 C13 -8.1(2) . . . . ?
C6 O1 C5 C4 172.62(17) . . . . ?
C5 O1 C6 C11 8.2(3) . . . . ?
C5 O1 C6 C7 -170.77(15) . . . . ?
C11 C6 C7 C8 21.1(3) . . . . ?
O1 C6 C7 C8 -159.95(17) . . . . ?
C6 C7 C8 C9 -50.0(2) . . . . ?
C7 C8 C9 C10 54.0(3) . . . . ?
C8 C9 C10 O2 153.8(2) . . . . ?
C8 C9 C10 C11 -27.7(3) . . . . ?
O1 C6 C11 C10 -172.92(17) . . . . ?
C7 C6 C11 C10 5.9(3) . . . . ?
O1 C6 C11 C12 2.6(3) . . . . ?
C7 C6 C11 C12 -178.57(17) . . . . ?
O2 C10 C11 C6 176.08(18) . . . . ?
C9 C10 C11 C6 -2.4(3) . . . . ?
O2 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C12 -178.16(17) . . . . ?
C6 C11 C12 C13 -11.9(2) . . . . ?
C10 C11 C12 C13 163.62(15) . . . . ?
C6 C11 C12 C14 110.59(19) . . . . ?
C10 C11 C12 C14 -73.9(2) . . . . ?
C4 C5 C13 C1 -1.8(3) . . . . ?
O1 C5 C13 C1 179.00(17) . . . . ?
C4 C5 C13 C12 176.62(17) . . . . ?
O1 C5 C13 C12 -2.6(3) . . . . ?
C2 C1 C13 C5 1.7(3) . . . . ?
C2 C1 C13 C12 -176.70(18) . . . . ?
C11 C12 C13 C5 11.7(2) . . . . ?
C14 C12 C13 C5 -112.36(17) . . . . ?
C11 C12 C13 C1 -169.94(16) . . . . ?
C14 C12 C13 C1 66.0(2) . . . . ?
C11 C12 C14 C15 72.81(19) . . . . ?
C13 C12 C14 C15 -164.50(15) . . . . ?
C12 C14 C15 O3 -125.51(19) . . . . ?
C12 C14 C15 C16 60.7(2) . . . . ?
C17 O5 C16 O4 -3.0(3) . . . . ?
C17 O5 C16 C15 179.11(17) . . . . ?
O3 C15 C16 O4 -159.73(19) . . . . ?
C14 C15 C16 O4 14.3(2) . . . . ?
O3 C15 C16 O5 18.2(2) . . . . ?
C14 C15 C16 O5 -167.78(16) . . . . ?
