#------------------------------------------------------------------------------
#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159117.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_7159117
loop_
_publ_author_name
'Ferreira, Joana R. M.'
'Alves, Mariana'
'Sousa, Bárbara'
'Vieira, Sandra I.'
'Silva, Artur M. S.'
'Guieu, Samuel'
'Cunha, Ângela'
'Nunes da Silva, Raquel'
_publ_section_title
;
 Curcumin-based molecular probes for fluorescence imaging of fungi
;
_journal_issue                   7
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1531
_journal_page_last               1536
_journal_paper_doi               10.1039/D2OB01872A
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
_chemical_formula_weight         336.37
_chemical_name_systematic
(1E,4Z,6E)-5-hydroxy-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-23 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.087(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6910(19)
_cell_length_b                   10.8177(18)
_cell_length_c                   13.581(2)
_cell_measurement_reflns_used    5722
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.58
_cell_volume                     1696.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_min         2.580
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: tetrahydrofuran'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6585
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0465
_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)+(0.0715P)²+0.9850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1602
_reflns_number_total             2127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01872a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7159117--7159118.cif.'
_cod_original_cell_volume        1696.1(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7159117
#BEGIN Tags that were not found in dictionaries:
_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   0.956
_shelx_estimated_absorpt_t_max   0.982
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O01 O 0.89136(10) 0.69879(9) 0.34565(7) 0.0374(3) Uani 1 1 d . . . . .
O02 O 0.55526(9) 0.31554(10) -0.16291(8) 0.0363(3) Uani 1 1 d . . . . .
C11 C 0.95246(13) 0.63140(14) 0.42805(10) 0.0346(3) Uani 1 1 d . . . . .
H11A H 0.902212 0.566504 0.447868 0.052 Uiso 1 1 calc R U . . .
H11C H 0.975302 0.687757 0.484213 0.052 Uiso 1 1 calc R U . . .
H11B H 1.021782 0.593733 0.408586 0.052 Uiso 1 1 calc R U . . .
C08 C 0.84283(11) 0.63323(13) 0.26366(10) 0.0278(3) Uani 1 1 d . . . . .
C09 C 0.77862(13) 0.70242(13) 0.18731(11) 0.0325(3) Uani 1 1 d . . . . .
H09 H 0.773129 0.789536 0.194086 0.039 Uiso 1 1 calc R U . . .
C10 C 0.72336(13) 0.64545(13) 0.10251(10) 0.0313(3) Uani 1 1 d . . . . .
H10 H 0.678629 0.693736 0.052068 0.038 Uiso 1 1 calc R U . . .
C05 C 0.73174(11) 0.51704(12) 0.08894(10) 0.0265(3) Uani 1 1 d . . . . .
C04 C 0.67376(11) 0.45247(13) 0.00062(10) 0.0286(3) Uani 1 1 d . . . . .
H04 H 0.681741 0.365100 -0.000285 0.034 Uiso 1 1 calc R U . . .
C03 C 0.61031(12) 0.50485(14) -0.07933(10) 0.0310(3) Uani 1 1 d . . . . .
H03 H 0.601430 0.592156 -0.079802 0.037 Uiso 1 1 calc R U . . .
C02 C 0.55409(11) 0.43538(14) -0.16569(9) 0.0290(3) Uani 1 1 d . . . . .
C01 C 0.500000 0.49907(18) -0.250000 0.0299(4) Uani 1 2 d S T P . .
H01 H 0.499997 0.586893 -0.249999 0.036 Uiso 1 2 calc R U P . .
C06 C 0.79822(11) 0.45025(12) 0.16479(10) 0.0284(3) Uani 1 1 d . . . . .
H06 H 0.806406 0.363590 0.156975 0.034 Uiso 1 1 calc R U . . .
C07 C 0.85314(11) 0.50642(13) 0.25183(10) 0.0289(3) Uani 1 1 d . . . . .
H07 H 0.897337 0.458346 0.302737 0.035 Uiso 1 1 calc R U . . .
H02 H 0.506(4) 0.290(3) -0.228(3) 0.043 Uiso 0.5 1 d . U P . .
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
_geom_angle_publ_flag
C08 O01 C11 117.75(11) . . ?
C02 O02 H02 104.2(17) . . ?
O01 C11 H11A 109.5 . . ?
O01 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
O01 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
O01 C08 C07 125.08(12) . . ?
O01 C08 C09 115.60(12) . . ?
C07 C08 C09 119.31(12) . . ?
C10 C09 C08 120.53(13) . . ?
C10 C09 H09 119.7 . . ?
C08 C09 H09 119.7 . . ?
C09 C10 C05 121.29(12) . . ?
C09 C10 H10 119.4 . . ?
C05 C10 H10 119.4 . . ?
C06 C05 C10 117.28(12) . . ?
C06 C05 C04 119.53(12) . . ?
C10 C05 C04 123.19(12) . . ?
C03 C04 C05 126.12(13) . . ?
C03 C04 H04 116.9 . . ?
C05 C04 H04 116.9 . . ?
C04 C03 C02 123.71(14) . . ?
C04 C03 H03 118.1 . . ?
C02 C03 H03 118.1 . . ?
O02 C02 C01 121.16(13) . . ?
O02 C02 C03 119.35(12) . . ?
C01 C02 C03 119.49(14) . . ?
C02 C01 C02 120.99(18) . 2_654 ?
C02 C01 H01 119.5 . . ?
C02 C01 H01 119.5 2_654 . ?
C05 C06 C07 122.07(12) . . ?
C05 C06 H06 119.0 . . ?
C07 C06 H06 119.0 . . ?
C08 C07 C06 119.50(12) . . ?
C08 C07 H07 120.3 . . ?
C06 C07 H07 120.3 . . ?
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
O01 C08 1.3657(16) . ?
O01 C11 1.4288(16) . ?
O02 C02 1.2970(18) . ?
O02 H02 1.01(4) . ?
C11 H11A 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11B 0.9800 . ?
C08 C07 1.3887(19) . ?
C08 C09 1.3975(18) . ?
C09 C10 1.3742(19) . ?
C09 H09 0.9500 . ?
C10 C05 1.4068(19) . ?
C10 H10 0.9500 . ?
C05 C06 1.3908(17) . ?
C05 C04 1.4592(18) . ?
C04 C03 1.3402(18) . ?
C04 H04 0.9500 . ?
C03 C02 1.4591(18) . ?
C03 H03 0.9500 . ?
C02 C01 1.3989(16) . ?
C01 H01 0.9500 . ?
C06 C07 1.3926(18) . ?
C06 H06 0.9500 . ?
C07 H07 0.9500 . ?
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
C11 O01 C08 C07 -3.5(2) . . . . ?
C11 O01 C08 C09 176.60(12) . . . . ?
O01 C08 C09 C10 -178.22(12) . . . . ?
C07 C08 C09 C10 1.9(2) . . . . ?
C08 C09 C10 C05 -1.5(2) . . . . ?
C09 C10 C05 C06 0.0(2) . . . . ?
C09 C10 C05 C04 179.42(12) . . . . ?
C06 C05 C04 C03 -177.72(13) . . . . ?
C10 C05 C04 C03 2.9(2) . . . . ?
C05 C04 C03 C02 -179.93(12) . . . . ?
C04 C03 C02 O02 6.7(2) . . . . ?
C04 C03 C02 C01 -173.24(11) . . . . ?
O02 C02 C01 C02 -0.34(9) . . . 2_654 ?
C03 C02 C01 C02 179.60(13) . . . 2_654 ?
C10 C05 C06 C07 1.09(19) . . . . ?
C04 C05 C06 C07 -178.37(11) . . . . ?
O01 C08 C07 C06 179.29(12) . . . . ?
C09 C08 C07 C06 -0.8(2) . . . . ?
C05 C06 C07 C08 -0.7(2) . . . . ?
