#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/99/2239924.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_2239924
loop_
_publ_author_name
'Koh, Dongsoo'
_publ_section_title
;
 Crystal structure of
 (E)-3-(2,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1034
_journal_page_last               o1035
_journal_paper_doi               10.1107/S1600536814018704
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C21 H18 O4'
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_chemical_name_systematic
(E)-3-(2,4-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.804(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1148(9)
_cell_length_b                   14.7489(9)
_cell_length_c                   15.5929(10)
_cell_measurement_reflns_used    4341
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.35
_cell_measurement_theta_min      4.34
_cell_volume                     3242.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_source         'Bruker ImuS'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8800
_diffrn_reflns_theta_full        66.49
_diffrn_reflns_theta_max         66.49
_diffrn_reflns_theta_min         4.34
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0490P)²+1.9580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                2505
_reflns_number_total             2755
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2770sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2239924
_cod_database_fobs_code          2239924
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.46036(6) 0.17828(6) 1.03233(6) 0.0275(2) Uani d . 1 1
O O2 0.19523(6) 0.11183(7) 0.85783(7) 0.0345(3) Uani d . 1 1
O O3 0.17234(6) -0.10692(6) 0.63594(6) 0.0266(2) Uani d . 1 1
O O4 0.59612(6) 0.24290(6) 1.12130(6) 0.0251(2) Uani d . 1 1
C C1 0.51556(9) 0.13224(8) 0.98872(8) 0.0210(3) Uani d . 1 1
C C2 0.47622(9) 0.07880(8) 0.91593(8) 0.0223(3) Uani d . 1 1
H H2A 0.5173 0.0432 0.8832 0.027 Uiso calc R 1 1
C C3 0.38286(9) 0.07983(8) 0.89525(8) 0.0213(3) Uani d . 1 1
H H3A 0.3454 0.1177 0.9294 0.026 Uiso calc R 1 1
C C4 0.33198(8) 0.03012(8) 0.82693(8) 0.0201(3) Uani d . 1 1
C C5 0.23466(9) 0.04712(8) 0.80855(8) 0.0226(3) Uani d . 1 1
C C6 0.18419(9) 0.00040(9) 0.74439(8) 0.0240(3) Uani d . 1 1
H H6A 0.1190 0.0134 0.7324 0.029 Uiso calc R 1 1
C C7 0.22926(9) -0.06572(9) 0.69744(8) 0.0215(3) Uani d . 1 1
C C8 0.32474(9) -0.08523(9) 0.71418(8) 0.0233(3) Uani d . 1 1
H H8A 0.3557 -0.1302 0.6822 0.028 Uiso calc R 1 1
C C9 0.37358(9) -0.03735(9) 0.77878(8) 0.0222(3) Uani d . 1 1
H H9A 0.4386 -0.0512 0.7908 0.027 Uiso calc R 1 1
C C10 0.09670(11) 0.13031(13) 0.84355(13) 0.0516(5) Uani d . 1 1
H H10A 0.0772 0.1763 0.8845 0.077 Uiso calc R 1 1
H H10B 0.0603 0.0746 0.8514 0.077 Uiso calc R 1 1
H H10C 0.0847 0.1528 0.7849 0.077 Uiso calc R 1 1
C C11 0.21279(10) -0.17857(10) 0.58794(9) 0.0339(3) Uani d . 1 1
H H11A 0.1648 -0.2029 0.5466 0.051 Uiso calc R 1 1
H H11B 0.2349 -0.2269 0.6272 0.051 Uiso calc R 1 1
H H11C 0.2665 -0.1551 0.5571 0.051 Uiso calc R 1 1
C C12 0.61749(8) 0.13277(8) 1.01100(8) 0.0193(3) Uani d . 1 1
C C13 0.65294(8) 0.18928(8) 1.07709(7) 0.0190(3) Uani d . 1 1
C C14 0.75210(8) 0.19224(8) 1.10073(7) 0.0193(3) Uani d . 1 1
C C15 0.78867(9) 0.25063(8) 1.16617(8) 0.0220(3) Uani d . 1 1
H H15A 0.7470 0.2893 1.1952 0.026 Uiso calc R 1 1
C C16 0.88385(9) 0.25175(9) 1.18786(8) 0.0251(3) Uani d . 1 1
H H16A 0.9081 0.2916 1.2315 0.030 Uiso calc R 1 1
C C17 0.94584(9) 0.19415(9) 1.14567(8) 0.0259(3) Uani d . 1 1
H H17A 1.0117 0.1946 1.1616 0.031 Uiso calc R 1 1
C C18 0.91205(9) 0.13741(9) 1.08185(8) 0.0246(3) Uani d . 1 1
H H18A 0.9549 0.0991 1.0537 0.030 Uiso calc R 1 1
C C19 0.81422(9) 0.13491(8) 1.05720(8) 0.0203(3) Uani d . 1 1
C C20 0.77706(9) 0.07710(9) 0.99071(8) 0.0228(3) Uani d . 1 1
H H20A 0.8185 0.0382 0.9617 0.027 Uiso calc R 1 1
C C21 0.68288(9) 0.07699(8) 0.96827(8) 0.0216(3) Uani d . 1 1
H H21A 0.6599 0.0387 0.9229 0.026 Uiso calc R 1 1
H H4O 0.5337(15) 0.2284(14) 1.0965(13) 0.059(6) Uiso d . 1 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'
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
C5 O2 C10 117.97(11)
C7 O3 C11 117.44(10)
C13 O4 H4O 102.7(12)
O1 C1 C12 119.77(11)
O1 C1 C2 119.13(11)
C12 C1 C2 121.11(11)
C3 C2 C1 120.65(11)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C2 C3 C4 127.94(12)
C2 C3 H3A 116.0
C4 C3 H3A 116.0
C9 C4 C5 116.67(11)
C9 C4 C3 123.29(11)
C5 C4 C3 120.00(11)
O2 C5 C6 123.18(11)
O2 C5 C4 115.50(11)
C6 C5 C4 121.32(12)
C5 C6 C7 119.80(11)
C5 C6 H6A 120.1
C7 C6 H6A 120.1
O3 C7 C8 124.91(11)
O3 C7 C6 114.42(11)
C8 C7 C6 120.67(11)
C9 C8 C7 118.31(12)
C9 C8 H8A 120.8
C7 C8 H8A 120.8
C8 C9 C4 123.21(12)
C8 C9 H9A 118.4
C4 C9 H9A 118.4
O2 C10 H10A 109.5
O2 C10 H10B 109.5
H10A C10 H10B 109.5
O2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O3 C11 H11A 109.5
O3 C11 H11B 109.5
H11A C11 H11B 109.5
O3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C21 118.15(11)
C13 C12 C1 119.35(11)
C21 C12 C1 122.50(11)
O4 C13 C12 121.93(11)
O4 C13 C14 116.85(11)
C12 C13 C14 121.22(11)
C15 C14 C19 119.82(11)
C15 C14 C13 121.53(11)
C19 C14 C13 118.65(11)
C16 C15 C14 120.33(12)
C16 C15 H15A 119.8
C14 C15 H15A 119.8
C15 C16 C17 120.18(12)
C15 C16 H16A 119.9
C17 C16 H16A 119.9
C18 C17 C16 120.48(12)
C18 C17 H17A 119.8
C16 C17 H17A 119.8
C17 C18 C19 120.94(12)
C17 C18 H18A 119.5
C19 C18 H18A 119.5
C14 C19 C18 118.24(11)
C14 C19 C20 119.51(11)
C18 C19 C20 122.24(11)
C21 C20 C19 120.66(11)
C21 C20 H20A 119.7
C19 C20 H20A 119.7
C20 C21 C12 121.79(11)
C20 C21 H21A 119.1
C12 C21 H21A 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2580(15)
O2 C5 1.3612(16)
O2 C10 1.4239(17)
O3 C7 1.3635(15)
O3 C11 1.4299(17)
O4 C13 1.3408(15)
O4 H4O 0.97(2)
C1 C12 1.4634(17)
C1 C2 1.4683(18)
C2 C3 1.3414(18)
C2 H2A 0.9500
C3 C4 1.4537(17)
C3 H3A 0.9500
C4 C9 1.3936(18)
C4 C5 1.4119(17)
C5 C6 1.3832(18)
C6 C7 1.3919(18)
C6 H6A 0.9500
C7 C8 1.3902(18)
C8 C9 1.3858(18)
C8 H8A 0.9500
C9 H9A 0.9500
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.3987(17)
C12 C21 1.4258(17)
C13 C14 1.4306(17)
C14 C15 1.4133(17)
C14 C19 1.4152(17)
C15 C16 1.3693(18)
C15 H15A 0.9500
C16 C17 1.4059(19)
C16 H16A 0.9500
C17 C18 1.3680(19)
C17 H17A 0.9500
C18 C19 1.4156(17)
C18 H18A 0.9500
C19 C20 1.4227(18)
C20 C21 1.3580(17)
C20 H20A 0.9500
C21 H21A 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
O4 H4O O1 . 0.97(2) 1.59(2) 2.4990(10) 155.1(19)
C10 H10A O1 7_557 0.98 2.57 3.538(2) 167
C11 H11B O2 4_546 0.98 2.58 3.442(2) 147
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
O1 C1 C2 C3 0.91(18)
C12 C1 C2 C3 -179.00(11)
C1 C2 C3 C4 -178.69(11)
C2 C3 C4 C9 9.1(2)
C2 C3 C4 C5 -173.07(12)
C10 O2 C5 C6 1.6(2)
C10 O2 C5 C4 -178.52(14)
C9 C4 C5 O2 178.52(11)
C3 C4 C5 O2 0.59(17)
C9 C4 C5 C6 -1.56(18)
C3 C4 C5 C6 -179.48(11)
O2 C5 C6 C7 -179.17(12)
C4 C5 C6 C7 0.91(19)
C11 O3 C7 C8 3.18(17)
C11 O3 C7 C6 -177.12(11)
C5 C6 C7 O3 -179.88(11)
C5 C6 C7 C8 -0.17(19)
O3 C7 C8 C9 179.82(11)
C6 C7 C8 C9 0.13(18)
C7 C8 C9 C4 -0.87(19)
C5 C4 C9 C8 1.56(18)
C3 C4 C9 C8 179.41(11)
O1 C1 C12 C13 -4.21(17)
C2 C1 C12 C13 175.70(11)
O1 C1 C12 C21 175.23(11)
C2 C1 C12 C21 -4.86(18)
C21 C12 C13 O4 -179.06(10)
C1 C12 C13 O4 0.41(17)
C21 C12 C13 C14 0.81(17)
C1 C12 C13 C14 -179.73(10)
O4 C13 C14 C15 -1.54(17)
C12 C13 C14 C15 178.59(11)
O4 C13 C14 C19 178.34(10)
C12 C13 C14 C19 -1.53(17)
C19 C14 C15 C16 -0.24(18)
C13 C14 C15 C16 179.64(11)
C14 C15 C16 C17 -0.57(19)
C15 C16 C17 C18 0.90(19)
C16 C17 C18 C19 -0.38(19)
C15 C14 C19 C18 0.74(17)
C13 C14 C19 C18 -179.15(11)
C15 C14 C19 C20 -179.25(11)
C13 C14 C19 C20 0.86(17)
C17 C18 C19 C14 -0.43(18)
C17 C18 C19 C20 179.56(12)
C14 C19 C20 C21 0.52(18)
C18 C19 C20 C21 -179.47(12)
C19 C20 C21 C12 -1.29(19)
C13 C12 C21 C20 0.62(18)
C1 C12 C21 C20 -178.83(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5729332
