#------------------------------------------------------------------------------
#$Date: 2023-01-26 03:36:31 +0200 (Thu, 26 Jan 2023) $
#$Revision: 280615 $
#$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, B\'arbara'
'Vieira, Sandra I.'
'Silva, Artur M. S.'
'Guieu, Samuel'
'Cunha, \^Angela'
'Nunes da Silva, Raquel'
_publ_section_title
;
 Curcumin-based molecular probes for fluorescence imaging of fungi
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01872A
_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/[\s^2^(Fo^2^)+(0.0715P)^2^+0.9850P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            d2ob01872a2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1696.1(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7159117
_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
_shelx_res_file
;
TITL orange_a.res in C2/c
    shelx.res
    created by SHELXL-2018/3 at 23:44:24 on 26-Oct-2020
CELL  0.71073  11.6910  10.8177  13.5812   90.000   99.087   90.000
ZERR     4.00   0.0019   0.0018   0.0023    0.000    0.005    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    O
UNIT  84 80 16
MERG   2
FMAP   2
PLAN   20
SIZE     0.200   0.300   0.500
ACTA
BOND   $H
CONF
L.S.  99
TEMP  -123.00
WGHT    0.071500    0.985000
FVAR       0.08928
O01   3    0.891356    0.698787    0.345648    11.00000    0.04774    0.03198 =
         0.03044   -0.00190   -0.00039    0.00644
O02   3    0.555264    0.315536   -0.162911    11.00000    0.03653    0.02783 =
         0.04249    0.00233   -0.00019    0.00159
C11   1    0.952462    0.631404    0.428050    11.00000    0.03341    0.04087 =
         0.02888    0.00105    0.00289    0.00473
AFIX 137
H11A  2    0.902212    0.566504    0.447868    11.00000   -1.50000
H11C  2    0.975302    0.687757    0.484213    11.00000   -1.50000
H11B  2    1.021782    0.593733    0.408586    11.00000   -1.50000
AFIX   0
C08   1    0.842828    0.633235    0.263659    11.00000    0.02870    0.02946 =
         0.02600    0.00055    0.00679    0.00233
C09   1    0.778621    0.702423    0.187311    11.00000    0.04172    0.02521 =
         0.03108    0.00149    0.00730    0.00928
AFIX  43
H09   2    0.773129    0.789536    0.194086    11.00000   -1.20000
AFIX   0
C10   1    0.723364    0.645455    0.102513    11.00000    0.03579    0.03042 =
         0.02806    0.00501    0.00579    0.00940
AFIX  43
H10   2    0.678629    0.693736    0.052068    11.00000   -1.20000
AFIX   0
C05   1    0.731745    0.517041    0.088940    11.00000    0.02501    0.02788 =
         0.02786    0.00371    0.00813    0.00133
C04   1    0.673761    0.452470    0.000623    11.00000    0.02559    0.02830 =
         0.03275    0.00178    0.00752    0.00124
AFIX  43
H04   2    0.681741    0.365100   -0.000285    11.00000   -1.20000
AFIX   0
C03   1    0.610308    0.504855   -0.079329    11.00000    0.03303    0.02954 =
         0.03051    0.00023    0.00546    0.00325
AFIX  43
H03   2    0.601430    0.592156   -0.079802    11.00000   -1.20000
AFIX   0
C02   1    0.554088    0.435381   -0.165691    11.00000    0.02351    0.03128 =
         0.03293    0.00049    0.00699    0.00132
C01   1    0.500000    0.499074   -0.250000    10.50000    0.03315    0.02502 =
         0.03105    0.00000    0.00345    0.00000
AFIX  43
H01   2    0.499997    0.586893   -0.249999    10.50000   -1.20000
AFIX   0
C06   1    0.798215    0.450251    0.164790    11.00000    0.02963    0.02269 =
         0.03354    0.00465    0.00695   -0.00034
AFIX  43
H06   2    0.806406    0.363590    0.156975    11.00000   -1.20000
AFIX   0
C07   1    0.853144    0.506419    0.251834    11.00000    0.02830    0.02790 =
         0.03061    0.00682    0.00511    0.00244
AFIX  43
H07   2    0.897337    0.458346    0.302737    11.00000   -1.20000
AFIX   0
H02   2    0.506155    0.290056   -0.227963    10.50000   -1.50000
HKLF    4  1.0  1.00  0.00  0.00  0.00  1.00  0.00  0.00  0.00  1.00




REM  orange_a.res in C2/c
REM wR2 = 0.1483, GooF = S = 1.084, Restrained GooF = 1.084 for all data
REM R1 = 0.0465 for 1602 Fo > 4sig(Fo) and 0.0646 for all 2127 data
REM 118 parameters refined using 0 restraints

END

WGHT      0.0714      0.9919

REM Highest difference peak  0.256,  deepest hole -0.227,  1-sigma level  0.048
Q1    1   0.4268  0.2243 -0.2012  11.00000  0.05    0.26
Q2    1   0.6844  0.4835  0.0560  11.00000  0.05    0.24
Q3    1   0.8468  0.4881  0.1970  11.00000  0.05    0.22
Q4    1   0.8342  0.6649  0.2125  11.00000  0.05    0.22
Q5    1   0.4486  0.4677 -0.2770  11.00000  0.05    0.21
Q6    1   0.6069  0.4841 -0.0195  11.00000  0.05    0.21
Q7    1   0.7435  0.4859  0.1431  11.00000  0.05    0.21
Q8    1   0.4957  0.4692 -0.2995  11.00000  0.05    0.20
Q9    1   0.8772  0.5768  0.2461  11.00000  0.05    0.20
Q10   1   0.7826  0.6833  0.1320  11.00000  0.05    0.20
Q11   1   0.6795  0.4806 -0.0529  11.00000  0.05    0.20
Q12   1   0.7974  0.4803  0.2209  11.00000  0.05    0.20
Q13   1   0.5867  0.4768 -0.1267  11.00000  0.05    0.20
Q14   1   0.5631  0.4659 -0.1111  11.00000  0.05    0.20
Q15   1   0.6976  0.5716  0.1033  11.00000  0.05    0.19
Q16   1   0.5157  0.3665 -0.1426  11.00000  0.05    0.17
Q17   1   0.9127  0.6709  0.2954  11.00000  0.05    0.16
Q18   1   0.8139  0.5685  0.2711  11.00000  0.05    0.15
Q19   1   0.5903  0.4637  0.0338  11.00000  0.05    0.15
Q20   1   0.8594  0.6649  0.3162  11.00000  0.05    0.15
;
_shelx_res_checksum              93586
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O01 0.0477(6) 0.0320(6) 0.0304(5) -0.0019(4) -0.0004(4) 0.0064(4)
O02 0.0365(6) 0.0278(6) 0.0425(6) 0.0023(4) -0.0002(5) 0.0016(4)
C11 0.0334(7) 0.0409(8) 0.0289(7) 0.0010(6) 0.0029(5) 0.0047(6)
C08 0.0287(7) 0.0295(7) 0.0260(6) 0.0005(5) 0.0068(5) 0.0023(5)
C09 0.0417(8) 0.0252(7) 0.0311(7) 0.0015(5) 0.0073(6) 0.0093(6)
C10 0.0358(7) 0.0304(7) 0.0281(7) 0.0050(5) 0.0058(5) 0.0094(6)
C05 0.0250(6) 0.0279(7) 0.0279(6) 0.0037(5) 0.0081(5) 0.0013(5)
C04 0.0256(6) 0.0283(7) 0.0327(7) 0.0018(5) 0.0075(5) 0.0012(5)
C03 0.0330(7) 0.0295(7) 0.0305(7) 0.0002(5) 0.0055(5) 0.0033(5)
C02 0.0235(6) 0.0313(7) 0.0329(7) 0.0005(5) 0.0070(5) 0.0013(5)
C01 0.0331(10) 0.0250(9) 0.0310(10) 0.000 0.0035(7) 0.000
C06 0.0296(7) 0.0227(6) 0.0335(7) 0.0046(5) 0.0070(5) -0.0003(5)
C07 0.0283(7) 0.0279(7) 0.0306(7) 0.0068(5) 0.0051(5) 0.0024(5)
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) . . . . ?