#------------------------------------------------------------------------------
#$Date: 2023-03-02 12:40:01 +0200 (Thu, 02 Mar 2023) $
#$Revision: 281263 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106826.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_8106826
loop_
_publ_author_name
'Benites, Julio'
'Valderrama, Jaime A.'
'Ríos, David'
'Cárdenas, Alejandro'
'Brito, Iván'
_publ_section_title
;
 Crystal structure of
 (2,5-dihydroxyphenyl)-(4-hydroxy-3,5-dimethoxyphenyl)methanone, C15H14O6
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              205
_journal_page_last               206
_journal_paper_doi               10.1515/ncrs-2015-0090
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C15 H14 O6'
_chemical_formula_sum            'C15 H14 O6'
_chemical_formula_weight         290.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_update_record
;
2015-05-05 # Formatted by publCIF
;
_cell_angle_alpha                94.942(3)
_cell_angle_beta                 112.199(4)
_cell_angle_gamma                102.752(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2996(5)
_cell_length_b                   8.3739(4)
_cell_length_c                   10.7565(5)
_cell_measurement_temperature    299(2)
_cell_volume                     663.09(7)
_computing_cell_refinement       APEX2(Bruker,2007)
_computing_data_collection       APEX2(Bruker,2007)
_computing_data_reduction        APEX2(Bruker,2007)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      299.52
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS D8-Venture,Triumph-I\mS-Cu'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1196
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29337
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        58.998
_diffrn_reflns_theta_max         58.998
_diffrn_reflns_theta_min         4.520
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0606P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1850
_reflns_number_total             1900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0090_suppl.cif
_cod_data_source_block           cu_scan_0m_p-1
_cod_original_cell_volume        663.09(6)
_cod_database_code               8106826
_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.
;
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H9(0.068) H12(0.051) H8(0.072) H7'A(0.07) H7'B(0.07) H7'C(0.07)
 H2'(0.033) H6(0.037) H6'(0.031) H8'A(0.055) H8'B(0.055) H8'C(0.055) H3(0.046)
 H4(0.043)
 Fixed X: H7'A(-0.3082) H7'B(-0.5033) H7'C(-0.4328) H2'(-0.1221) H6(0.0694)
 H6'(0.2194) H8'A(0.2186) H8'B(0.2502) H8'C(0.3317) H3(0.5221) H4(0.4128)
 Fixed Y: H7'A(-0.1889) H7'B(-0.2433) H7'C(-0.0686) H2'(0.0654) H6(0.5742)
 H6'(0.4249) H8'A(0.5556) H8'B(0.4886) H8'C(0.4262) H3(0.7632) H4(0.9493)
 Fixed Z: H7'A(0.1804) H7'B(0.0626) H7'C(0.1589) H2'(0.2817) H6(0.3115)
 H6'(0.2047) H8'A(0.0252) H8'B(-0.102) H8'C(0.0357) H3(0.7474) H4(0.6155)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
O11 O -0.32944(15) -0.08004(14) 0.02397(12) 0.0351(3) Uani 1 1 d . . . . .
O9 O 0.1465(2) 0.88408(15) 0.37241(13) 0.0457(4) Uani 1 1 d . . . . .
H9 H 0.174(3) 0.987(3) 0.420(3) 0.068 Uiso 1 1 d R . . . .
O12 O -0.22233(16) 0.06576(14) -0.14716(12) 0.0343(3) Uani 1 1 d . . . . .
H12 H -0.163(3) 0.106(3) -0.194(2) 0.051 Uiso 1 1 d R . . . .
O13 O 0.06985(15) 0.32724(14) -0.06565(11) 0.0337(3) Uani 1 1 d . . . . .
O10 O 0.19886(18) 0.21253(14) 0.49173(12) 0.0411(4) Uani 1 1 d . . . . .
O8 O 0.4318(2) 0.44927(16) 0.69079(13) 0.0482(4) Uani 1 1 d . . . . .
H8 H 0.364(4) 0.337(3) 0.639(3) 0.072 Uiso 1 1 d R . . . .
C7' C -0.3990(3) -0.1508(2) 0.1136(2) 0.0466(5) Uani 1 1 d . . . . .
H7'A H -0.3082 -0.1889 0.1804 0.070 Uiso 1 1 calc GR . . . .
H7'B H -0.5033 -0.2433 0.0626 0.070 Uiso 1 1 calc GR . . . .
H7'C H -0.4328 -0.0686 0.1589 0.070 Uiso 1 1 calc GR . . . .
C3' C -0.1803(2) 0.05478(18) 0.08102(17) 0.0256(4) Uani 1 1 d . . . . .
C2' C -0.0860(2) 0.11675(19) 0.21963(16) 0.0272(4) Uani 1 1 d . . . . .
H2' H -0.1221 0.0654 0.2817 0.033 Uiso 1 1 calc R . . . .
C1' C 0.0631(2) 0.25623(18) 0.26623(16) 0.0262(4) Uani 1 1 d . . . . .
C7 C 0.1664(2) 0.31596(19) 0.41523(17) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.2313(2) 0.49555(19) 0.47416(16) 0.0267(4) Uani 1 1 d . . . . .
C6 C 0.1608(2) 0.6115(2) 0.39899(17) 0.0307(4) Uani 1 1 d . . . . .
H6 H 0.0694 0.5742 0.3115 0.037 Uiso 1 1 calc R . . . .
C5 C 0.2245(2) 0.7791(2) 0.45248(17) 0.0311(4) Uani 1 1 d . . . . .
C4' C -0.1243(2) 0.12864(18) -0.01222(16) 0.0248(4) Uani 1 1 d . . . . .
C6' C 0.1201(2) 0.33147(18) 0.17372(16) 0.0262(4) Uani 1 1 d . . . . .
H6' H 0.2194 0.4249 0.2047 0.031 Uiso 1 1 calc R . . . .
C5' C 0.0279(2) 0.26612(18) 0.03572(16) 0.0246(4) Uani 1 1 d . . . . .
C8' C 0.2307(2) 0.4602(2) -0.02323(19) 0.0370(4) Uani 1 1 d . . . . .
H8'A H 0.2186 0.5556 0.0252 0.055 Uiso 1 1 calc GR . . . .
H8'B H 0.2502 0.4886 -0.1020 0.055 Uiso 1 1 calc GR . . . .
H8'C H 0.3317 0.4262 0.0357 0.055 Uiso 1 1 calc GR . . . .
C2 C 0.3639(2) 0.5546(2) 0.60817(17) 0.0310(4) Uani 1 1 d . . . . .
C3 C 0.4313(3) 0.7243(2) 0.65972(18) 0.0381(5) Uani 1 1 d . . . . .
H3 H 0.5221 0.7632 0.7474 0.046 Uiso 1 1 calc R . . . .
C4 C 0.3641(3) 0.8354(2) 0.58152(18) 0.0361(4) Uani 1 1 d . . . . .
H4 H 0.4128 0.9493 0.6155 0.043 Uiso 1 1 calc R . . . .
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
C3' O11 C7' 116.70(13) . .
C5 O9 H9 112.3(16) . .
C4' O12 H12 110.1(15) . .
C5' O13 C8' 116.67(13) . .
C2 O8 H8 105.6(15) . .
O11 C7' H7'A 109.5 . .
O11 C7' H7'B 109.5 . .
O11 C7' H7'C 109.5 . .
H7'A C7' H7'B 109.5 . .
H7'A C7' H7'C 109.5 . .
H7'B C7' H7'C 109.5 . .
O11 C3' C2' 124.88(15) . .
O11 C3' C4' 114.82(14) . .
C2' C3' C4' 120.29(14) . .
C3' C2' H2' 120.0 . .
C3' C2' C1' 119.94(15) . .
C1' C2' H2' 120.0 . .
C2' C1' C7 118.90(14) . .
C2' C1' C6' 120.23(14) . .
C6' C1' C7 120.75(14) . .
O10 C7 C1' 119.36(14) . .
O10 C7 C1 119.76(14) . .
C1 C7 C1' 120.88(14) . .
C6 C1 C7 121.08(15) . .
C6 C1 C2 118.25(14) . .
C2 C1 C7 120.66(14) . .
C1 C6 H6 119.4 . .
C5 C6 C1 121.11(15) . .
C5 C6 H6 119.4 . .
O9 C5 C4 123.09(15) . .
C6 C5 O9 117.34(15) . .
C6 C5 C4 119.55(15) . .
O12 C4' C3' 118.36(14) . .
O12 C4' C5' 122.30(15) . .
C3' C4' C5' 119.33(15) . .
C1' C6' H6' 120.3 . .
C5' C6' C1' 119.43(14) . .
C5' C6' H6' 120.3 . .
O13 C5' C4' 113.85(14) . .
O13 C5' C6' 125.38(14) . .
C6' C5' C4' 120.76(15) . .
O13 C8' H8'A 109.5 . .
O13 C8' H8'B 109.5 . .
O13 C8' H8'C 109.5 . .
H8'A C8' H8'B 109.5 . .
H8'A C8' H8'C 109.5 . .
H8'B C8' H8'C 109.5 . .
O8 C2 C1 121.91(15) . .
O8 C2 C3 117.96(15) . .
C3 C2 C1 120.13(15) . .
C2 C3 H3 119.9 . .
C4 C3 C2 120.15(16) . .
C4 C3 H3 119.9 . .
C5 C4 H4 119.7 . .
C3 C4 C5 120.59(15) . .
C3 C4 H4 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C7' 1.408(2) .
O11 C3' 1.3684(19) .
O9 H9 0.90(3) .
O9 C5 1.376(2) .
O12 H12 0.87(2) .
O12 C4' 1.3539(19) .
O13 C5' 1.370(2) .
O13 C8' 1.423(2) .
O10 C7 1.2482(19) .
O8 H8 0.98(3) .
O8 C2 1.365(2) .
C7' H7'A 0.9600 .
C7' H7'B 0.9600 .
C7' H7'C 0.9600 .
C3' C2' 1.382(2) .
C3' C4' 1.392(2) .
C2' H2' 0.9300 .
C2' C1' 1.393(2) .
C1' C7 1.479(2) .
C1' C6' 1.394(2) .
C7 C1 1.474(2) .
C1 C6 1.403(2) .
C1 C2 1.404(2) .
C6 H6 0.9300 .
C6 C5 1.373(2) .
C5 C4 1.387(3) .
C4' C5' 1.397(2) .
C6' H6' 0.9300 .
C6' C5' 1.380(2) .
C8' H8'A 0.9600 .
C8' H8'B 0.9600 .
C8' H8'C 0.9600 .
C2 C3 1.385(2) .
C3 H3 0.9300 .
C3 C4 1.376(3) .
C4 H4 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
O11 C3' C2' C1' -179.32(14) . . . .
O11 C3' C4' O12 1.9(2) . . . .
O11 C3' C4' C5' -179.31(13) . . . .
O9 C5 C4 C3 176.93(17) . . . .
O12 C4' C5' O13 -1.5(2) . . . .
O12 C4' C5' C6' 177.15(14) . . . .
O10 C7 C1 C6 -163.75(16) . . . .
O10 C7 C1 C2 15.3(3) . . . .
O8 C2 C3 C4 -178.48(17) . . . .
C7' O11 C3' C2' 5.5(2) . . . .
C7' O11 C3' C4' -175.35(15) . . . .
C3' C2' C1' C7 -177.49(14) . . . .
C3' C2' C1' C6' -1.4(2) . . . .
C3' C4' C5' O13 179.78(13) . . . .
C3' C4' C5' C6' -1.6(2) . . . .
C2' C3' C4' O12 -178.90(13) . . . .
C2' C3' C4' C5' -0.1(2) . . . .
C2' C1' C7 O10 41.6(2) . . . .
C2' C1' C7 C1 -138.46(16) . . . .
C2' C1' C6' C5' -0.3(2) . . . .
C1' C7 C1 C6 16.3(2) . . . .
C1' C7 C1 C2 -164.62(16) . . . .
C1' C6' C5' O13 -179.75(14) . . . .
C1' C6' C5' C4' 1.8(2) . . . .
C7 C1' C6' C5' 175.75(14) . . . .
C7 C1 C6 C5 -178.30(16) . . . .
C7 C1 C2 O8 -2.9(3) . . . .
C7 C1 C2 C3 176.34(16) . . . .
C1 C6 C5 O9 -179.35(15) . . . .
C1 C6 C5 C4 1.7(3) . . . .
C1 C2 C3 C4 2.2(3) . . . .
C6 C1 C2 O8 176.15(16) . . . .
C6 C1 C2 C3 -4.6(3) . . . .
C6 C5 C4 C3 -4.2(3) . . . .
C4' C3' C2' C1' 1.6(2) . . . .
C6' C1' C7 O10 -134.44(17) . . . .
C6' C1' C7 C1 45.5(2) . . . .
C8' O13 C5' C4' -175.84(13) . . . .
C8' O13 C5' C6' 5.6(2) . . . .
C2 C1 C6 C5 2.6(3) . . . .
C2 C3 C4 C5 2.2(3) . . . .
loop_
_publcif_info_cif.paper_type
E
