#------------------------------------------------------------------------------
#$Date: 2025-07-05 12:10:14 +0200 (Sat 05 de Jul de 2025) $
#$Revision: 300370 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/35/1573580.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1573580
loop_
_publ_author_name
'Pham, Phuong-Truc T.'
'Bader, Mamoun M.'
_publ_section_title
;
 4-Chlorocurcumin
;
_journal_coeditor_code           HB4501
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x241243
_journal_paper_doi               10.1107/S2414314624012434
_journal_volume                  10
_journal_year                    2025
_chemical_formula_iupac          'C21 H19 Cl O6'
_chemical_formula_moiety         'C21 H19 Cl O6'
_chemical_formula_sum            'C21 H19 Cl O6'
_chemical_formula_weight         402.81
_chemical_name_common
;
4-Chlorocurcumin
;
_chemical_name_systematic
;
4-Chloro-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
;
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0131(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7520(3)
_cell_length_b                   7.27831(16)
_cell_length_c                   15.9369(3)
_cell_measurement_reflns_used    8805
_cell_measurement_temperature    298
_cell_measurement_theta_max      73.7100
_cell_measurement_theta_min      2.8760
_cell_volume                     1913.53(7)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Olex2 1.5-ac5-024 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5-ac5-024 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device
'Rigaku Oxford Diffraction RO, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13358
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.828
_diffrn_reflns_theta_min         2.678
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.324
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0362
_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)+(0.0595P)²+0.3344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                3247
_reflns_number_total             3710
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4501.cif
_cod_data_source_block           I
_cod_database_code               1573580
#BEGIN Tags that were not found in dictionaries:
_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   0.681
_shelx_estimated_absorpt_t_max   0.773
#END Tags that were not found in dictionaries
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.43756(2) 0.67682(7) 0.37034(2) 0.06172(16) Uani d 1 . .
O O1 0.50652(7) 0.79498(18) 0.61198(7) 0.0570(3) Uani d 1 . .
H H1 0.550936 0.829843 0.603374 0.086 Uiso calc 1 . .
O O2 0.61937(6) 0.85947(18) 0.53705(7) 0.0565(3) Uani d 1 . .
O O3 0.04255(6) 0.4600(2) 0.66977(7) 0.0641(4) Uani d 1 . .
H H3 0.041337 0.463367 0.720969 0.096 Uiso calc 1 . .
O O4 0.15138(7) 0.56430(19) 0.80133(6) 0.0581(3) Uani d 1 . .
O O5 0.87723(7) 0.9296(2) 0.13546(7) 0.0682(4) Uani d 1 . .
H H5 0.922848 0.967388 0.154746 0.102 Uiso calc 1 . .
O O6 0.94585(6) 1.00942(19) 0.29885(6) 0.0573(3) Uani d 1 . .
C C1 0.49645(8) 0.7455(2) 0.46575(9) 0.0434(3) Uani d 1 . .
C C2 0.46339(8) 0.7392(2) 0.54077(9) 0.0443(3) Uani d 1 . .
C C3 0.38188(9) 0.6737(2) 0.54378(10) 0.0477(4) Uani d 1 . .
H H3A 0.349488 0.633170 0.493829 0.057 Uiso calc 1 . .
C C4 0.35239(9) 0.6703(2) 0.61630(10) 0.0474(4) Uani d 1 . .
H H4 0.387375 0.707950 0.665095 0.057 Uiso calc 1 . .
C C5 0.27120(8) 0.6139(2) 0.62761(9) 0.0426(3) Uani d 1 . .
C C6 0.21122(9) 0.5600(2) 0.56049(9) 0.0476(4) Uani d 1 . .
H H6 0.222603 0.557438 0.505431 0.057 Uiso calc 1 . .
C C7 0.13493(9) 0.5102(2) 0.57431(9) 0.0508(4) Uani d 1 . .
H H7 0.095275 0.475143 0.528788 0.061 Uiso calc 1 . .
C C8 0.11786(8) 0.5126(2) 0.65602(9) 0.0459(3) Uani d 1 . .
C C9 0.17684(8) 0.5667(2) 0.72415(9) 0.0437(3) Uani d 1 . .
C C10 0.25293(9) 0.6168(2) 0.71009(9) 0.0451(3) Uani d 1 . .
H H10 0.292303 0.652633 0.755702 0.054 Uiso calc 1 . .
C C11 0.20933(11) 0.6084(3) 0.87479(10) 0.0649(5) Uani d 1 . .
H H11A 0.229870 0.730055 0.868938 0.097 Uiso calc 1 . .
H H11B 0.253195 0.521893 0.880651 0.097 Uiso calc 1 . .
H H11C 0.184072 0.603208 0.924386 0.097 Uiso calc 1 . .
C C12 0.57657(9) 0.8078(2) 0.46588(9) 0.0435(3) Uani d 1 . .
C C13 0.61302(9) 0.8162(2) 0.38921(10) 0.0464(4) Uani d 1 . .
H H13 0.582583 0.783486 0.336848 0.056 Uiso calc 1 . .
C C14 0.68960(9) 0.8704(2) 0.39371(10) 0.0453(3) Uani d 1 . .
H H14 0.716934 0.901139 0.447769 0.054 Uiso calc 1 . .
C C15 0.73604(8) 0.8876(2) 0.32490(9) 0.0423(3) Uani d 1 . .
C C16 0.70374(9) 0.8547(2) 0.24003(10) 0.0487(4) Uani d 1 . .
H H16 0.649540 0.821538 0.224812 0.058 Uiso calc 1 . .
C C17 0.75172(9) 0.8709(2) 0.17775(10) 0.0521(4) Uani d 1 . .
H H17 0.729421 0.848662 0.121046 0.063 Uiso calc 1 . .
C C18 0.83262(9) 0.9199(2) 0.19931(9) 0.0471(3) Uani d 1 . .
C C19 0.86553(8) 0.9572(2) 0.28391(9) 0.0434(3) Uani d 1 . .
C C20 0.81761(8) 0.9398(2) 0.34580(9) 0.0442(3) Uani d 1 . .
H H20 0.839899 0.963208 0.402395 0.053 Uiso calc 1 . .
C C21 0.98395(10) 1.0319(3) 0.38498(10) 0.0639(5) Uani d 1 . .
H H21A 1.038542 1.074016 0.386889 0.096 Uiso calc 1 . .
H H21B 0.984627 0.916388 0.414174 0.096 Uiso calc 1 . .
H H21C 0.954454 1.120490 0.412132 0.096 Uiso calc 1 . .
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'
Cl Cl 0.3639 0.7018 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1 . . 109.5 ?
C8 O3 H3 . . 109.5 ?
C9 O4 C11 . . 117.50(12) ?
C18 O5 H5 . . 109.5 ?
C19 O6 C21 . . 117.40(11) ?
C2 C1 Cl1 . . 119.25(11) ?
C2 C1 C12 . . 121.57(13) ?
C12 C1 Cl1 . . 119.18(11) ?
O1 C2 C1 . . 119.47(13) ?
O1 C2 C3 . . 117.12(13) ?
C1 C2 C3 . . 123.41(14) ?
C2 C3 H3A . . 119.1 ?
C4 C3 C2 . . 121.73(15) ?
C4 C3 H3A . . 119.1 ?
C3 C4 H4 . . 116.4 ?
C3 C4 C5 . . 127.22(15) ?
C5 C4 H4 . . 116.4 ?
C6 C5 C4 . . 123.22(13) ?
C6 C5 C10 . . 118.65(13) ?
C10 C5 C4 . . 118.13(13) ?
C5 C6 H6 . . 119.5 ?
C7 C6 C5 . . 121.05(13) ?
C7 C6 H6 . . 119.5 ?
C6 C7 H7 . . 120.1 ?
C8 C7 C6 . . 119.71(14) ?
C8 C7 H7 . . 120.1 ?
O3 C8 C7 . . 119.61(13) ?
O3 C8 C9 . . 120.14(12) ?
C7 C8 C9 . . 120.26(13) ?
O4 C9 C8 . . 114.02(12) ?
O4 C9 C10 . . 126.09(13) ?
C10 C9 C8 . . 119.89(13) ?
C5 C10 H10 . . 119.8 ?
C9 C10 C5 . . 120.45(14) ?
C9 C10 H10 . . 119.8 ?
O4 C11 H11A . . 109.5 ?
O4 C11 H11B . . 109.5 ?
O4 C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O2 C12 C1 . . 118.50(13) ?
O2 C12 C13 . . 118.38(13) ?
C1 C12 C13 . . 123.13(14) ?
C12 C13 H13 . . 119.8 ?
C14 C13 C12 . . 120.44(14) ?
C14 C13 H13 . . 119.8 ?
C13 C14 H14 . . 115.8 ?
C13 C14 C15 . . 128.36(15) ?
C15 C14 H14 . . 115.8 ?
C16 C15 C14 . . 123.40(13) ?
C16 C15 C20 . . 118.51(12) ?
C20 C15 C14 . . 118.09(13) ?
C15 C16 H16 . . 119.8 ?
C17 C16 C15 . . 120.45(14) ?
C17 C16 H16 . . 119.8 ?
C16 C17 H17 . . 119.7 ?
C18 C17 C16 . . 120.54(14) ?
C18 C17 H17 . . 119.7 ?
O5 C18 C17 . . 117.85(13) ?
O5 C18 C19 . . 122.41(13) ?
C17 C18 C19 . . 119.74(13) ?
O6 C19 C18 . . 115.56(12) ?
O6 C19 C20 . . 124.95(13) ?
C20 C19 C18 . . 119.49(13) ?
C15 C20 H20 . . 119.4 ?
C19 C20 C15 . . 121.25(13) ?
C19 C20 H20 . . 119.4 ?
O6 C21 H21A . . 109.5 ?
O6 C21 H21B . . 109.5 ?
O6 C21 H21C . . 109.5 ?
H21A C21 H21B . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.7359(15) ?
O1 H1 . 0.8200 ?
O1 C2 . 1.2999(18) ?
O2 C12 . 1.2881(19) ?
O3 H3 . 0.8200 ?
O3 C8 . 1.3718(17) ?
O4 C9 . 1.3703(16) ?
O4 C11 . 1.422(2) ?
O5 H5 . 0.8200 ?
O5 C18 . 1.3650(17) ?
O6 C19 . 1.3785(16) ?
O6 C21 . 1.4190(18) ?
C1 C2 . 1.4030(19) ?
C1 C12 . 1.4164(19) ?
C2 C3 . 1.4550(19) ?
C3 H3A . 0.9300 ?
C3 C4 . 1.334(2) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.4614(19) ?
C5 C6 . 1.391(2) ?
C5 C10 . 1.4007(19) ?
C6 H6 . 0.9300 ?
C6 C7 . 1.383(2) ?
C7 H7 . 0.9300 ?
C7 C8 . 1.381(2) ?
C8 C9 . 1.392(2) ?
C9 C10 . 1.381(2) ?
C10 H10 . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.459(2) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.332(2) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.4561(19) ?
C15 C16 . 1.387(2) ?
C15 C20 . 1.4016(19) ?
C16 H16 . 0.9300 ?
C16 C17 . 1.387(2) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.386(2) ?
C18 C19 . 1.392(2) ?
C19 C20 . 1.3814(19) ?
C20 H20 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 1_555 0.82 1.70 2.4506(16) 151
O3 H3 O4 1_555 0.82 2.18 2.6395(15) 115
O5 H5 O6 1_555 0.82 2.28 2.7200(15) 114
O3 H3 O6 4_476 0.82 2.20 2.8398(15) 135
O5 H5 O3 4_675 0.82 2.05 2.8439(16) 164
C11 H11B O2 2_646 0.96 2.59 3.477(2) 154
C17 H17 O2 4_575 0.93 2.57 3.3206(19) 138
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C1 C2 O1 . . . . -178.22(12) ?
Cl1 C1 C2 C3 . . . . 1.4(2) ?
Cl1 C1 C12 O2 . . . . 179.55(11) ?
Cl1 C1 C12 C13 . . . . -0.5(2) ?
O1 C2 C3 C4 . . . . -0.2(2) ?
O2 C12 C13 C14 . . . . 2.2(2) ?
O3 C8 C9 O4 . . . . -1.1(2) ?
O3 C8 C9 C10 . . . . 179.02(15) ?
O4 C9 C10 C5 . . . . -179.74(14) ?
O5 C18 C19 O6 . . . . 1.6(2) ?
O5 C18 C19 C20 . . . . -178.20(16) ?
O6 C19 C20 C15 . . . . 179.36(15) ?
C1 C2 C3 C4 . . . . -179.78(15) ?
C1 C12 C13 C14 . . . . -177.78(15) ?
C2 C1 C12 O2 . . . . 0.0(2) ?
C2 C1 C12 C13 . . . . 179.96(14) ?
C2 C3 C4 C5 . . . . 177.85(15) ?
C3 C4 C5 C6 . . . . -2.2(3) ?
C3 C4 C5 C10 . . . . 178.62(16) ?
C4 C5 C6 C7 . . . . -179.12(15) ?
C4 C5 C10 C9 . . . . 179.31(14) ?
C5 C6 C7 C8 . . . . -0.4(3) ?
C6 C5 C10 C9 . . . . 0.1(2) ?
C6 C7 C8 O3 . . . . -178.88(15) ?
C6 C7 C8 C9 . . . . 0.6(2) ?
C7 C8 C9 O4 . . . . 179.38(15) ?
C7 C8 C9 C10 . . . . -0.5(2) ?
C8 C9 C10 C5 . . . . 0.1(2) ?
C10 C5 C6 C7 . . . . 0.0(2) ?
C11 O4 C9 C8 . . . . 176.77(15) ?
C11 O4 C9 C10 . . . . -3.4(2) ?
C12 C1 C2 O1 . . . . 1.3(2) ?
C12 C1 C2 C3 . . . . -179.07(14) ?
C12 C13 C14 C15 . . . . -179.93(14) ?
C13 C14 C15 C16 . . . . 2.7(3) ?
C13 C14 C15 C20 . . . . -177.12(16) ?
C14 C15 C16 C17 . . . . -178.99(15) ?
C14 C15 C20 C19 . . . . 179.38(15) ?
C15 C16 C17 C18 . . . . 0.1(3) ?
C16 C15 C20 C19 . . . . -0.5(2) ?
C16 C17 C18 O5 . . . . 178.57(16) ?
C16 C17 C18 C19 . . . . -1.5(3) ?
C17 C18 C19 O6 . . . . -178.37(15) ?
C17 C18 C19 C20 . . . . 1.8(2) ?
C18 C19 C20 C15 . . . . -0.9(2) ?
C20 C15 C16 C17 . . . . 0.9(2) ?
C21 O6 C19 C18 . . . . -174.18(16) ?
C21 O6 C19 C20 . . . . 5.6(2) ?
