#------------------------------------------------------------------------------
#$Date: 2019-11-22 08:39:00 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/32/2243207.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_2243207
loop_
_publ_author_name
'Suchojad, Kamil'
'Dołega, Anna'
'Adamus-Grabicka, Angelika'
'Budzisz, Elżbieta'
'Małecka, Magdalena'
_publ_section_title
;
 Crystal structures of (E)-3-(4-hydroxybenzylidene)chroman-4-one
 and (E)-3-(3-hydroxybenzylidene)-2-phenylchroman-4-one
;
_journal_coeditor_code           RZ5266
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1907
_journal_page_last               1913
_journal_paper_doi               10.1107/S2056989019015639
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C22 H16 O3'
_chemical_formula_moiety         'C22 H16 O3'
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.37
_chemical_melting_point          210
_chemical_name_systematic
;
(E)-3-(3-Hydroxybenzylidene)-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
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                91.992(12)
_cell_angle_beta                 98.282(10)
_cell_angle_gamma                97.568(10)
_cell_formula_units_Z            2
_cell_length_a                   5.3969(6)
_cell_length_b                   11.6576(16)
_cell_length_c                   12.944(2)
_cell_measurement_reflns_used    3650
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      3.53
_cell_volume                     797.66(19)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2002), XRED32 (Stoe & Cie, 2002)
;
_computing_publication_material
;
SHELXL2014/7 (Sheldrick, 2015b), publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         3.531
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.292
_refine_ls_extinction_coef       0.041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0676
_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)+(0.1159P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1999
_reflns_number_gt                1804
_reflns_number_total             3281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rz5266sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        797.68(19)
_cod_database_code               2243207
_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
O O1 0.1107(4) 0.13471(17) 0.24184(16) 0.0423(6) Uani d 1
O O4 0.7889(4) 0.30522(17) 0.39197(16) 0.0432(6) Uani d 1
O O3 -0.1593(4) 0.6939(2) 0.44060(17) 0.0503(6) Uani d 1
H H3 -0.0545 0.6964 0.4956 0.075 Uiso calc 1
C C10 0.5289(5) 0.1266(2) 0.3391(2) 0.0365(7) Uani d 1
C C17 0.1145(5) 0.5660(2) 0.3820(2) 0.0390(7) Uani d 1
H H17 0.1940 0.5611 0.4518 0.047 Uiso calc 1
C C9 0.2888(5) 0.0736(3) 0.2913(2) 0.0386(7) Uani d 1
C C3 0.3849(5) 0.3163(3) 0.2945(2) 0.0378(7) Uani d 1
C C7 0.3920(6) -0.1113(3) 0.3446(2) 0.0453(8) Uani d 1
H H7 0.3455 -0.1925 0.3474 0.054 Uiso calc 1
C C5 0.6977(6) 0.0575(3) 0.3885(2) 0.0405(7) Uani d 1
H H5 0.8608 0.0925 0.4207 0.049 Uiso calc 1
C C4 0.5884(5) 0.2528(3) 0.3452(2) 0.0370(7) Uani d 1
C C15 -0.1803(6) 0.6487(3) 0.2598(2) 0.0431(8) Uani d 1
H H15 -0.3077 0.6973 0.2454 0.052 Uiso calc 1
C C16 -0.0743(5) 0.6358(3) 0.3619(2) 0.0401(7) Uani d 1
C C11 0.3763(5) 0.4240(3) 0.3311(2) 0.0385(7) Uani d 1
H H11 0.5114 0.4544 0.3843 0.046 Uiso calc 1
C C12 0.1891(5) 0.5030(2) 0.3014(2) 0.0378(7) Uani d 1
C C8 0.2210(6) -0.0459(3) 0.2943(2) 0.0431(7) Uani d 1
H H8 0.0587 -0.0818 0.2620 0.052 Uiso calc 1
C C13 0.0823(6) 0.5165(3) 0.1989(3) 0.0442(8) Uani d 1
H H13 0.1332 0.4755 0.1427 0.053 Uiso calc 1
C C14 -0.0998(6) 0.5905(3) 0.1791(2) 0.0440(8) Uani d 1
H H14 -0.1694 0.6010 0.1090 0.053 Uiso calc 1
C C2 0.2058(5) 0.2476(2) 0.2083(2) 0.0376(7) Uani d 1
H H2 0.0587 0.2908 0.1899 0.045 Uiso calc 1
C C21 0.3266(5) 0.2321(3) 0.1100(2) 0.0387(7) Uani d 1
C C22 0.2451(7) 0.1373(3) 0.0408(2) 0.0517(9) Uani d 1
H H22 0.1084 0.0819 0.0531 0.062 Uiso calc 1
C C6 0.6322(6) -0.0602(3) 0.3915(2) 0.0440(8) Uani d 1
H H6 0.7491 -0.1062 0.4251 0.053 Uiso calc 1
C C26 0.5228(6) 0.3134(3) 0.0894(2) 0.0493(8) Uani d 1
H H26 0.5783 0.3797 0.1357 0.059 Uiso calc 1
C C23 0.3612(8) 0.1222(3) -0.0467(3) 0.0632(11) Uani d 1
H H23 0.3042 0.0566 -0.0938 0.076 Uiso calc 1
C C24 0.5596(7) 0.2024(4) -0.0654(3) 0.0593(10) Uani d 1
H H24 0.6417 0.1913 -0.1244 0.071 Uiso calc 1
C C25 0.6382(6) 0.2991(3) 0.0022(3) 0.0558(9) Uani d 1
H H25 0.7716 0.3556 -0.0114 0.067 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 0.0030 0.0020 '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 0.0110 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
C9 O1 C2 115.9(2)
C16 O3 H3 109.5
C5 C10 C9 118.8(3)
C5 C10 C4 121.1(3)
C9 C10 C4 119.8(2)
C12 C17 C16 120.9(3)
C12 C17 H17 119.5
C16 C17 H17 119.5
O1 C9 C8 117.0(3)
O1 C9 C10 122.8(3)
C8 C9 C10 120.2(3)
C11 C3 C4 118.3(3)
C11 C3 C2 127.3(3)
C4 C3 C2 114.4(2)
C8 C7 C6 121.1(3)
C8 C7 H7 119.5
C6 C7 H7 119.5
C6 C5 C10 121.2(3)
C6 C5 H5 119.4
C10 C5 H5 119.4
O4 C4 C10 123.2(3)
O4 C4 C3 121.2(3)
C10 C4 C3 115.6(3)
C14 C15 C16 119.6(3)
C14 C15 H15 120.2
C16 C15 H15 120.2
O3 C16 C15 118.4(2)
O3 C16 C17 121.8(3)
C15 C16 C17 119.8(3)
C3 C11 C12 129.9(3)
C3 C11 H11 115.1
C12 C11 H11 115.1
C17 C12 C13 118.9(2)
C17 C12 C11 117.1(3)
C13 C12 C11 124.1(3)
C7 C8 C9 119.4(3)
C7 C8 H8 120.3
C9 C8 H8 120.3
C12 C13 C14 119.7(3)
C12 C13 H13 120.1
C14 C13 H13 120.1
C15 C14 C13 121.0(3)
C15 C14 H14 119.5
C13 C14 H14 119.5
O1 C2 C3 111.0(2)
O1 C2 C21 109.4(2)
C3 C2 C21 112.3(2)
O1 C2 H2 108.0
C3 C2 H2 108.0
C21 C2 H2 108.0
C22 C21 C26 118.9(3)
C22 C21 C2 121.1(3)
C26 C21 C2 120.1(3)
C21 C22 C23 120.6(3)
C21 C22 H22 119.7
C23 C22 H22 119.7
C5 C6 C7 119.3(3)
C5 C6 H6 120.3
C7 C6 H6 120.3
C25 C26 C21 120.7(3)
C25 C26 H26 119.6
C21 C26 H26 119.6
C24 C23 C22 120.1(3)
C24 C23 H23 120.0
C22 C23 H23 120.0
C23 C24 C25 119.7(3)
C23 C24 H24 120.2
C25 C24 H24 120.2
C26 C25 C24 120.0(4)
C26 C25 H25 120.0
C24 C25 H25 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.369(3)
O1 C2 1.453(3)
O4 C4 1.234(3)
O3 C16 1.370(4)
O3 H3 0.8400
C10 C5 1.397(4)
C10 C9 1.405(4)
C10 C4 1.460(4)
C17 C12 1.392(4)
C17 C16 1.388(4)
C17 H17 0.9500
C9 C8 1.396(4)
C3 C11 1.335(4)
C3 C4 1.492(4)
C3 C2 1.499(4)
C7 C8 1.380(4)
C7 C6 1.396(4)
C7 H7 0.9500
C5 C6 1.374(4)
C5 H5 0.9500
C15 C14 1.378(4)
C15 C16 1.383(4)
C15 H15 0.9500
C11 C12 1.475(4)
C11 H11 0.9500
C12 C13 1.391(4)
C8 H8 0.9500
C13 C14 1.393(4)
C13 H13 0.9500
C14 H14 0.9500
C2 C21 1.526(4)
C2 H2 1.0000
C21 C22 1.381(4)
C21 C26 1.388(4)
C22 C23 1.387(5)
C22 H22 0.9500
C6 H6 0.9500
C26 C25 1.381(4)
C26 H26 0.9500
C23 C24 1.381(5)
C23 H23 0.9500
C24 C25 1.383(5)
C24 H24 0.9500
C25 H25 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
O3 H3 O4 2_666 0.84 1.89 2.728(3) 172.4
C17 H17 O4 2_666 0.95 2.49 3.184(4) 129.6
C6 H6 O3 1_645 0.95 2.45 3.265(4) 143.3
C11 H11 O4 . 0.95 2.43 2.807(3) 103.1

_cod_database_fobs_code 2243207
