#------------------------------------------------------------------------------
#$Date: 2020-07-07 08:07:55 +0300 (Tue, 07 Jul 2020) $
#$Revision: 254055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022184.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_2022184
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          'C16 H12 O2'
_chemical_formula_moiety         'C16 H12 O2'
_chemical_formula_sum            'C16 H12 O2'
_chemical_formula_weight         236.26
_chemical_name_systematic
;
(E)-3-Benzylidenechroman-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                89.744(3)
_cell_angle_beta                 84.862(3)
_cell_angle_gamma                74.199(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7718(3)
_cell_length_b                   8.6069(3)
_cell_length_c                   9.0857(3)
_cell_measurement_reflns_used    3741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.8010
_cell_measurement_theta_min      3.7290
_cell_volume                     582.31(4)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.489
_diffrn_reflns_theta_min         3.301
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0402
_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)+(0.0597P)²+0.1583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                2120
_reflns_number_total             2425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yf3205sup1.cif
_cod_data_source_block           compound_V_AAG5
_cod_database_code               2022184
_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 0.56491(12) 0.96012(10) 0.67017(9) 0.0203(2) Uani d 1 . .
O O4 0.31184(12) 0.69758(10) 0.94932(9) 0.0221(2) Uani d 1 . .
C C9 0.43926(16) 1.03656(15) 0.78021(13) 0.0174(3) Uani d 1 . .
C C4 0.38354(17) 0.77597(15) 0.86245(13) 0.0175(3) Uani d 1 . .
C C12 0.74274(17) 0.43694(14) 0.64267(13) 0.0182(3) Uani d 1 . .
C C3 0.52016(17) 0.69819(15) 0.73982(13) 0.0172(3) Uani d 1 . .
C C10 0.34234(16) 0.95369(14) 0.87368(13) 0.0177(3) Uani d 1 . .
C C8 0.41493(18) 1.20162(15) 0.79971(14) 0.0208(3) Uani d 1 . .
H H8 0.4843 1.2560 0.7383 0.025 Uiso calc 1 . .
C C11 0.60958(17) 0.54181(15) 0.74961(13) 0.0181(3) Uani d 1 . .
H H11 0.5826 0.4918 0.8389 0.022 Uiso calc 1 . .
C C5 0.21682(17) 1.04169(16) 0.98441(14) 0.0207(3) Uani d 1 . .
H H5 0.1504 0.9873 1.0488 0.025 Uiso calc 1 . .
C C13 0.74448(17) 0.45644(15) 0.48910(14) 0.0201(3) Uani d 1 . .
H H13 0.6581 0.5435 0.4503 0.024 Uiso calc 1 . .
C C6 0.18851(18) 1.20637(16) 1.00108(14) 0.0236(3) Uani d 1 . .
H H6 0.1009 1.2652 1.0748 0.028 Uiso calc 1 . .
C C17 0.87029(18) 0.30509(15) 0.69590(14) 0.0225(3) Uani d 1 . .
H H17 0.8701 0.2881 0.7993 0.027 Uiso calc 1 . .
C C7 0.28933(18) 1.28633(15) 0.90890(14) 0.0225(3) Uani d 1 . .
H H7 0.2714 1.3993 0.9214 0.027 Uiso calc 1 . .
C C2 0.54324(18) 0.80948(14) 0.61596(13) 0.0194(3) Uani d 1 . .
H H2A 0.6499 0.7553 0.5486 0.023 Uiso calc 1 . .
H H2B 0.4369 0.8322 0.5587 0.023 Uiso calc 1 . .
C C16 0.99632(18) 0.19957(16) 0.59981(16) 0.0262(3) Uani d 1 . .
H H16 1.0826 0.1117 0.6377 0.031 Uiso calc 1 . .
C C15 0.99711(18) 0.22168(16) 0.44774(16) 0.0257(3) Uani d 1 . .
H H15 1.0836 0.1492 0.3819 0.031 Uiso calc 1 . .
C C14 0.87098(18) 0.35004(16) 0.39325(15) 0.0234(3) Uani d 1 . .
H H14 0.8711 0.3653 0.2896 0.028 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 . . 115.34(9) ?
O1 C9 C8 . . 116.88(11) ?
O1 C9 C10 . . 122.40(11) ?
C8 C9 C10 . . 120.69(12) ?
O4 C4 C10 . . 122.27(11) ?
O4 C4 C3 . . 122.37(11) ?
C10 C4 C3 . . 115.35(10) ?
C13 C12 C17 . . 118.03(11) ?
C13 C12 C11 . . 123.52(11) ?
C17 C12 C11 . . 118.37(11) ?
C11 C3 C4 . . 118.95(11) ?
C11 C3 C2 . . 126.81(11) ?
C4 C3 C2 . . 114.23(10) ?
C5 C10 C9 . . 118.55(11) ?
C5 C10 C4 . . 121.13(11) ?
C9 C10 C4 . . 120.13(11) ?
C7 C8 C9 . . 119.77(11) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C3 C11 C12 . . 129.45(11) ?
C3 C11 H11 . . 115.3 ?
C12 C11 H11 . . 115.3 ?
C6 C5 C10 . . 120.84(12) ?
C6 C5 H5 . . 119.6 ?
C10 C5 H5 . . 119.6 ?
C14 C13 C12 . . 120.78(12) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C5 C6 C7 . . 119.76(12) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C16 C17 C12 . . 120.92(12) ?
C16 C17 H17 . . 119.5 ?
C12 C17 H17 . . 119.5 ?
C8 C7 C6 . . 120.34(12) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
O1 C2 C3 . . 111.90(10) ?
O1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
O1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C17 C16 C15 . . 120.25(12) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C14 C15 C16 . . 119.59(12) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
C15 C14 C13 . . 120.42(12) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
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 . 1.3664(14) ?
O1 C2 . 1.4462(14) ?
O4 C4 . 1.2288(15) ?
C9 C8 . 1.3912(17) ?
C9 C10 . 1.4035(17) ?
C4 C10 . 1.4770(17) ?
C4 C3 . 1.4915(17) ?
C12 C13 . 1.4040(17) ?
C12 C17 . 1.4045(17) ?
C12 C11 . 1.4659(17) ?
C3 C11 . 1.3428(17) ?
C3 C2 . 1.5046(16) ?
C10 C5 . 1.4022(17) ?
C8 C7 . 1.3834(18) ?
C8 H8 . 0.9500 ?
C11 H11 . 0.9500 ?
C5 C6 . 1.3808(18) ?
C5 H5 . 0.9500 ?
C13 C14 . 1.3882(18) ?
C13 H13 . 0.9500 ?
C6 C7 . 1.4000(19) ?
C6 H6 . 0.9500 ?
C17 C16 . 1.3842(18) ?
C17 H17 . 0.9500 ?
C7 H7 . 0.9500 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C16 C15 . 1.394(2) ?
C16 H16 . 0.9500 ?
C15 C14 . 1.3852(19) ?
C15 H15 . 0.9500 ?
C14 H14 . 0.9500 ?
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_667 0.95 2.56 3.4153(15) 149.7
C17 H17 O4 2_667 0.95 2.56 3.4050(16) 148.1
C7 H7 O4 1_565 0.95 2.69 3.6131(16) 165.5
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
C2 O1 C9 C8 . . . . -158.11(11) ?
C2 O1 C9 C10 . . . . 24.05(16) ?
O4 C4 C3 C11 . . . . -21.46(17) ?
C10 C4 C3 C11 . . . . 157.66(11) ?
O4 C4 C3 C2 . . . . 159.17(12) ?
C10 C4 C3 C2 . . . . -21.72(14) ?
O1 C9 C10 C5 . . . . 179.55(10) ?
C8 C9 C10 C5 . . . . 1.79(18) ?
O1 C9 C10 C4 . . . . 4.49(18) ?
C8 C9 C10 C4 . . . . -173.27(11) ?
O4 C4 C10 C5 . . . . -0.65(18) ?
C3 C4 C10 C5 . . . . -179.76(10) ?
O4 C4 C10 C9 . . . . 174.29(11) ?
C3 C4 C10 C9 . . . . -4.83(16) ?
O1 C9 C8 C7 . . . . 179.78(11) ?
C10 C9 C8 C7 . . . . -2.35(18) ?
C4 C3 C11 C12 . . . . 177.04(11) ?
C2 C3 C11 C12 . . . . -3.7(2) ?
C13 C12 C11 C3 . . . . -29.7(2) ?
C17 C12 C11 C3 . . . . 153.47(13) ?
C9 C10 C5 C6 . . . . 0.20(18) ?
C4 C10 C5 C6 . . . . 175.21(11) ?
C17 C12 C13 C14 . . . . -1.21(18) ?
C11 C12 C13 C14 . . . . -178.02(11) ?
C10 C5 C6 C7 . . . . -1.62(19) ?
C13 C12 C17 C16 . . . . 1.34(18) ?
C11 C12 C17 C16 . . . . 178.32(11) ?
C9 C8 C7 C6 . . . . 0.90(19) ?
C5 C6 C7 C8 . . . . 1.08(19) ?
C9 O1 C2 C3 . . . . -50.13(14) ?
C11 C3 C2 O1 . . . . -130.51(13) ?
C4 C3 C2 O1 . . . . 48.81(14) ?
C12 C17 C16 C15 . . . . -0.8(2) ?
C17 C16 C15 C14 . . . . 0.0(2) ?
C16 C15 C14 C13 . . . . 0.1(2) ?
C12 C13 C14 C15 . . . . 0.52(19) ?

_cod_database_fobs_code 2022184
