#------------------------------------------------------------------------------
#$Date: 2020-10-13 07:16:19 +0300 (Tue, 13 Oct 2020) $
#$Revision: 258326 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/13/7241390.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_7241390
loop_
_publ_author_name
'Du, Yanqing'
'Liang, Fengying'
'Hu, Mixia'
'Bu, Ren'
'Wang, Meiling'
'Tsuda, Akihiko'
'Eerdun, Chaolu'
_publ_section_title
;
 Hydroxychalcone dyes that serve as color indicators for pH and fluoride
 ions
;
_journal_issue                   61
_journal_name_full               'RSC Advances'
_journal_page_first              37463
_journal_page_last               37472
_journal_paper_doi               10.1039/D0RA06719A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-07-23
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-07-23 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.105(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1097(7)
_cell_length_b                   8.0041(5)
_cell_length_c                   14.2334(8)
_cell_measurement_reflns_used    5202
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      52.63
_cell_measurement_theta_min      3.79
_cell_volume                     1329.50(14)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16319
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        52.709
_diffrn_reflns_theta_max         52.709
_diffrn_reflns_theta_min         3.788
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.866
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0038(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         1528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0880P)²+1.4567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1191
_reflns_number_total             1529
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra06719a2.cif
_cod_data_source_block           cu_170417a_0m
_cod_database_code               7241390
_shelx_shelxl_version_number     2014/7
_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. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C14(H14), C13(H13), C12(H12), C11(H11), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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 0.8714(2) 0.3431(4) 0.9431(2) 0.0659(9) Uani 1 1 d . . . . .
O3 O 0.6942(2) 0.6126(4) 0.47742(19) 0.0661(10) Uani 1 1 d . . . . .
O2 O 0.8706(2) 0.4761(5) 0.6181(2) 0.0722(11) Uani 1 1 d . . . . .
H2 H 0.821(5) 0.526(7) 0.557(5) 0.108 Uiso 1 1 d . U . . .
O4 O 0.4111(3) 0.9556(5) 0.2194(3) 0.0897(12) Uani 1 1 d . . . . .
H4 H 0.3808 1.0099 0.1646 0.135 Uiso 1 1 calc R U . . .
C1 C 0.9781(4) 0.2567(6) 0.9789(3) 0.0694(13) Uani 1 1 d . . . . .
H1A H 0.9708 0.1703 0.9294 0.104 Uiso 1 1 calc R U . . .
H1B H 0.9984 0.2078 1.0467 0.104 Uiso 1 1 calc R U . . .
H1C H 1.0366 0.3339 0.9846 0.104 Uiso 1 1 calc R U . . .
C2 C 0.8248(4) 0.4145(5) 0.8458(3) 0.0485(11) Uani 1 1 d . . . . .
C3 C 0.8751(3) 0.4136(5) 0.7796(3) 0.0513(11) Uani 1 1 d . . . . .
H3 H 0.9468 0.3652 0.8012 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8183(3) 0.4851(5) 0.6809(3) 0.0467(11) Uani 1 1 d . . . . .
C5 C 0.7108(3) 0.5603(5) 0.6461(3) 0.0416(10) Uani 1 1 d . . . . .
C6 C 0.6507(3) 0.6291(5) 0.5398(3) 0.0471(11) Uani 1 1 d . . . . .
C7 C 0.5420(3) 0.7153(5) 0.5041(3) 0.0485(11) Uani 1 1 d . . . . .
H7 H 0.5082 0.7203 0.5490 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4887(3) 0.7872(5) 0.4098(3) 0.0478(11) Uani 1 1 d . . . . .
H8 H 0.5257 0.7798 0.3676 0.057 Uiso 1 1 calc R U . . .
C9 C 0.3804(3) 0.8757(5) 0.3644(3) 0.0419(10) Uani 1 1 d . . . . .
C14 C 0.3083(3) 0.8825(5) 0.4123(3) 0.0514(11) Uani 1 1 d . . . . .
H14 H 0.3305 0.8289 0.4766 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2055(4) 0.9662(5) 0.3671(3) 0.0576(12) Uani 1 1 d . . . . .
H13 H 0.1594 0.9698 0.4010 0.069 Uiso 1 1 calc R U . . .
C12 C 0.1713(4) 1.0442(5) 0.2721(3) 0.0577(12) Uani 1 1 d . . . . .
H12 H 0.1015 1.1001 0.2413 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2388(3) 1.0411(5) 0.2215(3) 0.0541(11) Uani 1 1 d . . . . .
H11 H 0.2151 1.0944 0.1569 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3429(3) 0.9574(5) 0.2679(3) 0.0467(11) Uani 1 1 d . . . . .
C15 C 0.6637(3) 0.5617(5) 0.7173(3) 0.0498(11) Uani 1 1 d . . . . .
H15 H 0.5931 0.6127 0.6974 0.060 Uiso 1 1 calc R U . . .
C16 C 0.7187(4) 0.4904(5) 0.8145(3) 0.0562(12) Uani 1 1 d . . . . .
H16 H 0.6855 0.4925 0.8600 0.067 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'
N N 0.0311 0.0180 '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
C2 O1 C1 118.6(3) . . ?
C4 O2 H2 105(4) . . ?
C10 O4 H4 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.3(4) . . ?
O1 C2 C16 115.4(3) . . ?
C3 C2 C16 120.3(4) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
O2 C4 C3 116.7(4) . . ?
O2 C4 C5 121.3(3) . . ?
C3 C4 C5 121.9(3) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 C15 116.7(3) . . ?
C15 C5 C6 122.5(4) . . ?
O3 C6 C5 119.1(3) . . ?
O3 C6 C7 119.3(3) . . ?
C7 C6 C5 121.5(3) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 C6 122.6(4) . . ?
C8 C7 H7 118.7 . . ?
C7 C8 H8 115.9 . . ?
C7 C8 C9 128.3(4) . . ?
C9 C8 H8 115.9 . . ?
C14 C9 C8 123.0(3) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 C14 116.7(4) . . ?
C9 C14 H14 119.0 . . ?
C13 C14 C9 121.9(4) . . ?
C13 C14 H14 119.0 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.2 . . ?
C13 C12 H12 119.6 . . ?
C13 C12 C11 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C10 119.3(4) . . ?
C10 C11 H11 120.4 . . ?
O4 C10 C9 118.6(4) . . ?
O4 C10 C11 119.8(4) . . ?
C11 C10 C9 121.6(3) . . ?
C5 C15 H15 119.1 . . ?
C16 C15 C5 121.7(4) . . ?
C16 C15 H15 119.1 . . ?
C2 C16 H16 120.1 . . ?
C15 C16 C2 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
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 C1 1.430(5) . ?
O1 C2 1.359(4) . ?
O3 C6 1.262(4) . ?
O2 H2 0.91(6) . ?
O2 C4 1.354(4) . ?
O4 H4 0.8200 . ?
O4 C10 1.355(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.373(5) . ?
C2 C16 1.393(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(5) . ?
C4 C5 1.399(5) . ?
C5 C6 1.458(5) . ?
C5 C15 1.407(5) . ?
C6 C7 1.451(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.329(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.449(5) . ?
C9 C14 1.396(5) . ?
C9 C10 1.393(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.375(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.366(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.371(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.388(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(5) . ?
C16 H16 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.91(6) 1.68(6) 2.517(4) 152(5) .
O4 H4 O3 0.82 1.98 2.794(4) 172.4 2_655
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
O1 C2 C3 C4 177.8(4) . . . . ?
O1 C2 C16 C15 -178.3(4) . . . . ?
O3 C6 C7 C8 -4.3(6) . . . . ?
O2 C4 C5 C6 1.0(6) . . . . ?
O2 C4 C5 C15 179.5(4) . . . . ?
C1 O1 C2 C3 -2.0(6) . . . . ?
C1 O1 C2 C16 177.5(4) . . . . ?
C2 C3 C4 O2 -178.1(4) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C2 C16 C15 1.1(6) . . . . ?
C3 C4 C5 C6 -177.6(4) . . . . ?
C3 C4 C5 C15 0.9(6) . . . . ?
C4 C5 C6 O3 3.6(6) . . . . ?
C4 C5 C6 C7 -176.7(4) . . . . ?
C4 C5 C15 C16 -1.3(6) . . . . ?
C5 C6 C7 C8 176.1(4) . . . . ?
C5 C15 C16 C2 0.4(6) . . . . ?
C6 C5 C15 C16 177.1(4) . . . . ?
C6 C7 C8 C9 179.6(4) . . . . ?
C7 C8 C9 C14 -7.1(6) . . . . ?
C7 C8 C9 C10 173.7(4) . . . . ?
C8 C9 C14 C13 -179.5(4) . . . . ?
C8 C9 C10 O4 -1.6(6) . . . . ?
C8 C9 C10 C11 179.0(4) . . . . ?
C9 C14 C13 C12 0.6(6) . . . . ?
C14 C9 C10 O4 179.1(4) . . . . ?
C14 C9 C10 C11 -0.2(6) . . . . ?
C14 C13 C12 C11 -0.5(6) . . . . ?
C13 C12 C11 C10 0.0(6) . . . . ?
C12 C11 C10 O4 -179.0(4) . . . . ?
C12 C11 C10 C9 0.3(6) . . . . ?
C10 C9 C14 C13 -0.3(6) . . . . ?
C15 C5 C6 O3 -174.7(4) . . . . ?
C15 C5 C6 C7 4.9(6) . . . . ?
C16 C2 C3 C4 -1.6(6) . . . . ?
