#------------------------------------------------------------------------------
#$Date: 2020-07-07 08:07:55 +0300 (Tue, 07 Jul 2020) $
#$Revision: 254055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022182.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_2022182
loop_
_publ_author_name
'Małecka, Magdalena'
'Kusz, Joachim'
'Eriksson, Lars'
'Adamus-Grabicka, Angelika'
'Budzisz, Elżbieta'
_publ_section_title
;
 The relationship between Hirshfeld potential and cytotoxic activity: a
 study along a series of flavonoid and chromanone derivatives
;
_journal_coeditor_code           YF3205
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322962000813X
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C23 H18 O2'
_chemical_formula_moiety         'C23 H18 O2'
_chemical_formula_sum            'C23 H18 O2'
_chemical_formula_weight         326.37
_chemical_name_systematic
;
(E)-3-(3-Methylbenzylidene)-2-phenylchroman-4-one
;
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                104.378(3)
_cell_angle_beta                 109.425(3)
_cell_angle_gamma                91.902(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9094(3)
_cell_length_b                   9.6578(3)
_cell_length_c                   10.9044(4)
_cell_measurement_reflns_used    3948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.0590
_cell_measurement_theta_min      3.5000
_cell_volume                     850.24(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 1999)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7284
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         3.071
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0439P)²+0.2079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                2999
_reflns_number_total             3509
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yf3205sup1.cif
_cod_data_source_block           compound_III_AAG1
_cod_database_code               2022182
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O O1 0.57118(10) 0.44640(9) 0.37188(8) 0.0200(2) Uani d 1 . .
O O4 0.38766(10) 0.03505(9) 0.32719(8) 0.0229(2) Uani d 1 . .
C C21 0.66313(13) 0.29543(13) 0.20350(11) 0.0170(2) Uani d 1 . .
C C12 0.89045(14) 0.16807(12) 0.54388(12) 0.0192(3) Uani d 1 . .
C C2 0.66990(14) 0.33222(12) 0.35024(11) 0.0172(2) Uani d 1 . .
H H2 0.7834 0.3701 0.4101 0.021 Uiso calc 1 . .
C C3 0.61964(14) 0.20436(12) 0.39022(11) 0.0176(2) Uani d 1 . .
C C11 0.71562(14) 0.13781(13) 0.47467(11) 0.0188(3) Uani d 1 . .
H H11 0.6638 0.0611 0.4920 0.023 Uiso calc 1 . .
C C9 0.40917(14) 0.40489(13) 0.31451(11) 0.0188(3) Uani d 1 . .
C C4 0.44417(14) 0.15501(13) 0.33244(11) 0.0179(2) Uani d 1 . .
C C26 0.66779(14) 0.15547(13) 0.13257(12) 0.0204(3) Uani d 1 . .
H H26 0.6718 0.0796 0.1744 0.024 Uiso calc 1 . .
C C10 0.34138(14) 0.26263(13) 0.28726(11) 0.0188(3) Uani d 1 . .
C C13 0.99590(15) 0.20421(13) 0.48267(12) 0.0221(3) Uani d 1 . .
H H13 0.9549 0.2119 0.3926 0.026 Uiso calc 1 . .
C C17 0.95460(15) 0.15826(13) 0.67717(12) 0.0203(3) Uani d 1 . .
H H17 0.8844 0.1306 0.7185 0.024 Uiso calc 1 . .
C C16 1.11883(15) 0.18806(13) 0.75045(12) 0.0215(3) Uani d 1 . .
C C5 0.17385(15) 0.22886(14) 0.22882(12) 0.0228(3) Uani d 1 . .
H H5 0.1266 0.1325 0.2086 0.027 Uiso calc 1 . .
C C22 0.65751(14) 0.40519(13) 0.14018(12) 0.0208(3) Uani d 1 . .
H H22 0.6544 0.5013 0.1876 0.025 Uiso calc 1 . .
C C25 0.66659(15) 0.12572(14) 0.00015(12) 0.0230(3) Uani d 1 . .
H H25 0.6695 0.0297 -0.0476 0.028 Uiso calc 1 . .
C C24 0.66114(14) 0.23528(14) -0.06185(12) 0.0221(3) Uani d 1 . .
H H24 0.6607 0.2149 -0.1518 0.027 Uiso calc 1 . .
C C14 1.16003(15) 0.22879(14) 0.55301(13) 0.0249(3) Uani d 1 . .
H H14 1.2311 0.2514 0.5103 0.030 Uiso calc 1 . .
C C15 1.22082(15) 0.22054(13) 0.68555(12) 0.0234(3) Uani d 1 . .
H H15 1.3335 0.2373 0.7327 0.028 Uiso calc 1 . .
C C23 0.65634(15) 0.37523(14) 0.00852(12) 0.0232(3) Uani d 1 . .
H H23 0.6522 0.4508 -0.0336 0.028 Uiso calc 1 . .
C C8 0.31165(16) 0.51168(14) 0.28802(12) 0.0243(3) Uani d 1 . .
H H8 0.3579 0.6084 0.3085 0.029 Uiso calc 1 . .
C C6 0.07720(15) 0.33358(16) 0.20038(13) 0.0274(3) Uani d 1 . .
H H6 -0.0359 0.3095 0.1599 0.033 Uiso calc 1 . .
C C7 0.14682(16) 0.47552(15) 0.23157(13) 0.0279(3) Uani d 1 . .
H H7 0.0801 0.5482 0.2138 0.033 Uiso calc 1 . .
C C18 1.18325(16) 0.18957(15) 0.89766(12) 0.0283(3) Uani d 1 . .
H H18A 1.1300 0.1062 0.9099 0.042 Uiso calc 1 . .
H H18B 1.1624 0.2785 0.9527 0.042 Uiso calc 1 . .
H H18C 1.2991 0.1850 0.9259 0.042 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C2 . . 115.14(9) ?
C26 C21 C22 . . 118.86(11) ?
C26 C21 C2 . . 121.58(10) ?
C22 C21 C2 . . 119.53(11) ?
C13 C12 C17 . . 118.55(11) ?
C13 C12 C11 . . 123.22(10) ?
C17 C12 C11 . . 118.22(11) ?
O1 C2 C3 . . 110.50(9) ?
O1 C2 C21 . . 109.10(9) ?
C3 C2 C21 . . 113.52(9) ?
O1 C2 H2 . . 107.8 ?
C3 C2 H2 . . 107.8 ?
C21 C2 H2 . . 107.8 ?
C11 C3 C4 . . 118.88(10) ?
C11 C3 C2 . . 126.48(11) ?
C4 C3 C2 . . 114.58(10) ?
C3 C11 C12 . . 128.46(11) ?
C3 C11 H11 . . 115.8 ?
C12 C11 H11 . . 115.8 ?
O1 C9 C8 . . 117.18(11) ?
O1 C9 C10 . . 122.27(11) ?
C8 C9 C10 . . 120.51(11) ?
O4 C4 C10 . . 121.96(11) ?
O4 C4 C3 . . 122.58(11) ?
C10 C4 C3 . . 115.40(10) ?
C21 C26 C25 . . 120.37(11) ?
C21 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?
C9 C10 C5 . . 118.78(11) ?
C9 C10 C4 . . 119.87(11) ?
C5 C10 C4 . . 121.05(11) ?
C14 C13 C12 . . 120.24(11) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C16 C17 C12 . . 121.63(11) ?
C16 C17 H17 . . 119.2 ?
C12 C17 H17 . . 119.2 ?
C17 C16 C15 . . 118.32(11) ?
C17 C16 C18 . . 120.52(11) ?
C15 C16 C18 . . 121.13(11) ?
C6 C5 C10 . . 120.87(12) ?
C6 C5 H5 . . 119.6 ?
C10 C5 H5 . . 119.6 ?
C23 C22 C21 . . 120.62(12) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C24 C25 C26 . . 120.39(12) ?
C24 C25 H25 . . 119.8 ?
C26 C25 H25 . . 119.8 ?
C25 C24 C23 . . 119.46(11) ?
C25 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
C13 C14 C15 . . 120.26(12) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.92(11) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C24 C23 C22 . . 120.31(11) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C7 C8 C9 . . 119.42(12) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
C5 C6 C7 . . 119.48(12) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C8 C7 C6 . . 120.90(12) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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
O1 C9 . 1.3682(14) ?
O1 C2 . 1.4555(14) ?
O4 C4 . 1.2281(14) ?
C21 C26 . 1.3903(17) ?
C21 C22 . 1.3953(17) ?
C21 C2 . 1.5305(15) ?
C12 C13 . 1.4004(17) ?
C12 C17 . 1.4027(16) ?
C12 C11 . 1.4695(16) ?
C2 C3 . 1.5086(16) ?
C2 H2 . 1.0000 ?
C3 C11 . 1.3413(17) ?
C3 C4 . 1.4881(15) ?
C11 H11 . 0.9500 ?
C9 C8 . 1.3938(17) ?
C9 C10 . 1.4012(17) ?
C4 C10 . 1.4762(17) ?
C26 C25 . 1.3969(16) ?
C26 H26 . 0.9500 ?
C10 C5 . 1.4043(16) ?
C13 C14 . 1.3868(17) ?
C13 H13 . 0.9500 ?
C17 C16 . 1.3937(17) ?
C17 H17 . 0.9500 ?
C16 C15 . 1.3942(18) ?
C16 C18 . 1.5105(16) ?
C5 C6 . 1.3771(19) ?
C5 H5 . 0.9500 ?
C22 C23 . 1.3887(17) ?
C22 H22 . 0.9500 ?
C25 C24 . 1.3841(18) ?
C25 H25 . 0.9500 ?
C24 C23 . 1.3885(18) ?
C24 H24 . 0.9500 ?
C14 C15 . 1.3885(18) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C23 H23 . 0.9500 ?
C8 C7 . 1.3839(18) ?
C8 H8 . 0.9500 ?
C6 C7 . 1.397(2) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
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
C11 H11 O4 2_656 0.95 2.54 3.3635(14) 145.4
C17 H17 O4 2_656 0.95 2.69 3.5025(15) 144.2
C24 H24 O4 2_655 0.95 2.60 3.2731(15) 128.1
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
C9 O1 C2 C3 . . . . -51.97(12) ?
C9 O1 C2 C21 . . . . 73.51(11) ?
C26 C21 C2 O1 . . . . -145.49(10) ?
C22 C21 C2 O1 . . . . 36.67(14) ?
C26 C21 C2 C3 . . . . -21.79(15) ?
C22 C21 C2 C3 . . . . 160.38(10) ?
O1 C2 C3 C11 . . . . -127.71(12) ?
C21 C2 C3 C11 . . . . 109.35(13) ?
O1 C2 C3 C4 . . . . 49.49(12) ?
C21 C2 C3 C4 . . . . -73.45(13) ?
C4 C3 C11 C12 . . . . -179.62(11) ?
C2 C3 C11 C12 . . . . -2.5(2) ?
C13 C12 C11 C3 . . . . -39.46(19) ?
C17 C12 C11 C3 . . . . 141.43(13) ?
C2 O1 C9 C8 . . . . -157.01(10) ?
C2 O1 C9 C10 . . . . 25.25(14) ?
C11 C3 C4 O4 . . . . -20.52(17) ?
C2 C3 C4 O4 . . . . 162.05(11) ?
C11 C3 C4 C10 . . . . 156.80(11) ?
C2 C3 C4 C10 . . . . -20.63(14) ?
C22 C21 C26 C25 . . . . -0.10(17) ?
C2 C21 C26 C25 . . . . -177.95(11) ?
O1 C9 C10 C5 . . . . 179.68(10) ?
C8 C9 C10 C5 . . . . 2.01(17) ?
O1 C9 C10 C4 . . . . 5.84(16) ?
C8 C9 C10 C4 . . . . -171.83(10) ?
O4 C4 C10 C9 . . . . 169.98(10) ?
C3 C4 C10 C9 . . . . -7.36(15) ?
O4 C4 C10 C5 . . . . -3.72(17) ?
C3 C4 C10 C5 . . . . 178.94(10) ?
C17 C12 C13 C14 . . . . 0.34(18) ?
C11 C12 C13 C14 . . . . -178.77(12) ?
C13 C12 C17 C16 . . . . 2.12(18) ?
C11 C12 C17 C16 . . . . -178.73(11) ?
C12 C17 C16 C15 . . . . -3.55(18) ?
C12 C17 C16 C18 . . . . 174.54(12) ?
C9 C10 C5 C6 . . . . -0.92(17) ?
C4 C10 C5 C6 . . . . 172.84(11) ?
C26 C21 C22 C23 . . . . 0.09(17) ?
C2 C21 C22 C23 . . . . 177.99(11) ?
C21 C26 C25 C24 . . . . 0.16(18) ?
C26 C25 C24 C23 . . . . -0.21(18) ?
C12 C13 C14 C15 . . . . -1.3(2) ?
C13 C14 C15 C16 . . . . -0.2(2) ?
C17 C16 C15 C14 . . . . 2.57(19) ?
C18 C16 C15 C14 . . . . -175.51(12) ?
C25 C24 C23 C22 . . . . 0.20(18) ?
C21 C22 C23 C24 . . . . -0.15(18) ?
O1 C9 C8 C7 . . . . -179.21(10) ?
C10 C9 C8 C7 . . . . -1.43(17) ?
C10 C5 C6 C7 . . . . -0.74(18) ?
C9 C8 C7 C6 . . . . -0.26(18) ?
C5 C6 C7 C8 . . . . 1.35(19) ?

_cod_database_fobs_code 2022182
