#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/47/2214773.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_2214773
loop_
_publ_author_name
'Zhe Li'
'Jian-Hua Xu'
'Mohd Mustaqim Rosli'
'Hoong-Kun Fun'
_publ_section_title
;
 rac-5-Methoxy-3-phenyl-2,3-dihydro-1H-inden-1-one
;
_journal_coeditor_code           KP2119
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3435
_journal_page_last               o3435
_journal_paper_doi               10.1107/S1600536807032850
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H14 O2'
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27
_chemical_name_common
;
 (rac)-5-methoxy-3-phenyl-2,3-dihydro-1H-inden-1-one
;
_chemical_name_systematic
;
 (rac)-5-methoxy-3-phenyl-2,3-dihydro-1H-inden-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 99.106(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3603(4)
_cell_length_b                   6.4935(3)
_cell_length_c                   23.1904(11)
_cell_measurement_reflns_used    2136
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.47
_cell_volume                     1243.09(10)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and Platon (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
;
Bruker SMART APEX II CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10552
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.8255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.2830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                1867
_reflns_number_total             2548
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2119.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214773
_cod_database_fobs_code          2214773
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
O O1 0.38826(13) 0.31089(17) 0.44441(5) 0.0249(3) Uani d . 1
O O2 -0.23284(14) 0.90321(17) 0.44183(5) 0.0278(3) Uani d . 1
C C1 -0.04029(19) 0.4488(2) 0.40722(7) 0.0190(4) Uani d . 1
C C2 0.09832(19) 0.3295(2) 0.41001(7) 0.0200(4) Uani d . 1
H H2A 0.0945 0.1997 0.3929 0.024 Uiso calc R 1
C C3 0.24286(19) 0.4095(2) 0.43906(7) 0.0200(4) Uani d . 1
C C4 0.2491(2) 0.6039(2) 0.46562(7) 0.0210(4) Uani d . 1
H H4A 0.3470 0.6540 0.4852 0.025 Uiso calc R 1
C C5 0.1107(2) 0.7207(2) 0.46284(7) 0.0209(4) Uani d . 1
H H5A 0.1136 0.8492 0.4807 0.025 Uiso calc R 1
C C6 -0.03402(19) 0.6422(2) 0.43267(7) 0.0190(4) Uani d . 1
C C7 -0.1958(2) 0.7364(3) 0.42384(7) 0.0207(4) Uani d . 1
C C8 -0.3095(2) 0.5888(2) 0.38705(8) 0.0244(4) Uani d . 1
H H8A -0.3491 0.6492 0.3492 0.029 Uiso calc R 1
H H8B -0.4016 0.5574 0.4063 0.029 Uiso calc R 1
C C9 -0.21166(19) 0.3908(2) 0.37976(7) 0.0203(4) Uani d . 1
H H9A -0.2500 0.2814 0.4033 0.024 Uiso calc R 1
C C10 -0.22593(19) 0.3160(3) 0.31726(7) 0.0224(4) Uani d . 1
C C11 -0.1548(2) 0.4245(3) 0.27661(8) 0.0329(5) Uani d . 1
H H11A -0.0954 0.5428 0.2880 0.039 Uiso calc R 1
C C12 -0.1708(3) 0.3590(4) 0.21911(9) 0.0444(6) Uani d . 1
H H12A -0.1222 0.4332 0.1923 0.053 Uiso calc R 1
C C13 -0.2583(3) 0.1846(4) 0.20172(9) 0.0486(6) Uani d . 1
H H13A -0.2695 0.1413 0.1631 0.058 Uiso calc R 1
C C14 -0.3292(3) 0.0744(3) 0.24132(9) 0.0438(6) Uani d . 1
H H14A -0.3887 -0.0434 0.2295 0.053 Uiso calc R 1
C C15 -0.3120(2) 0.1388(3) 0.29928(8) 0.0313(5) Uani d . 1
H H15A -0.3587 0.0622 0.3261 0.038 Uiso calc R 1
C C16 0.3922(2) 0.1130(3) 0.41791(9) 0.0361(5) Uani d . 1
H H16A 0.4997 0.0572 0.4266 0.054 Uiso calc R 1
H H16B 0.3619 0.1258 0.3764 0.054 Uiso calc R 1
H H16C 0.3176 0.0227 0.4329 0.054 Uiso calc R 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
C3 O1 C16 117.73(13)
C6 C1 C2 120.77(15)
C6 C1 C9 111.87(14)
C2 C1 C9 127.33(14)
C1 C2 C3 118.06(15)
C1 C2 H2A 121.0
C3 C2 H2A 121.0
O1 C3 C2 124.33(14)
O1 C3 C4 114.39(14)
C2 C3 C4 121.28(15)
C5 C4 C3 120.22(15)
C5 C4 H4A 119.9
C3 C4 H4A 119.9
C4 C5 C6 118.57(15)
C4 C5 H5A 120.7
C6 C5 H5A 120.7
C1 C6 C5 121.08(15)
C1 C6 C7 110.26(14)
C5 C6 C7 128.63(15)
O2 C7 C6 126.94(16)
O2 C7 C8 125.77(16)
C6 C7 C8 107.28(13)
C7 C8 C9 106.95(13)
C7 C8 H8A 110.3
C9 C8 H8A 110.3
C7 C8 H8B 110.3
C9 C8 H8B 110.3
H8A C8 H8B 108.6
C10 C9 C1 113.98(13)
C10 C9 C8 114.08(13)
C1 C9 C8 103.19(13)
C10 C9 H9A 108.4
C1 C9 H9A 108.4
C8 C9 H9A 108.4
C11 C10 C15 118.44(16)
C11 C10 C9 120.72(16)
C15 C10 C9 120.84(16)
C10 C11 C12 120.84(19)
C10 C11 H11A 119.6
C12 C11 H11A 119.6
C13 C12 C11 120.1(2)
C13 C12 H12A 120.0
C11 C12 H12A 120.0
C14 C13 C12 120.01(19)
C14 C13 H13A 120.0
C12 C13 H13A 120.0
C13 C14 C15 120.0(2)
C13 C14 H14A 120.0
C15 C14 H14A 120.0
C10 C15 C14 120.59(19)
C10 C15 H15A 119.7
C14 C15 H15A 119.7
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.3622(18)
O1 C16 1.427(2)
O2 C7 1.2181(19)
C1 C6 1.385(2)
C1 C2 1.387(2)
C1 C9 1.520(2)
C2 C3 1.388(2)
C2 H2A 0.9300
C3 C4 1.401(2)
C4 C5 1.376(2)
C4 H4A 0.9300
C5 C6 1.395(2)
C5 H5A 0.9300
C6 C7 1.469(2)
C7 C8 1.515(2)
C8 C9 1.547(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.515(2)
C9 H9A 0.9800
C10 C11 1.384(2)
C10 C15 1.386(2)
C11 C12 1.386(3)
C11 H11A 0.9300
C12 C13 1.374(3)
C12 H12A 0.9300
C13 C14 1.370(3)
C13 H13A 0.9300
C14 C15 1.393(3)
C14 H14A 0.9300
C15 H15A 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 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
_geom_hbond_publ_flag
C4 H4A O1 3_666 0.93 2.544 3.442(2) 163 y
C5 H5A O2 3_576 0.93 2.498 3.344(2) 151 y
C16 H16A O2 1_645 0.96 2.424 3.382(2) 176 y
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
C6 C1 C2 C3 0.1(2)
C9 C1 C2 C3 -177.78(15)
C16 O1 C3 C2 0.6(2)
C16 O1 C3 C4 -179.31(14)
C1 C2 C3 O1 -178.98(14)
C1 C2 C3 C4 0.9(2)
O1 C3 C4 C5 179.27(14)
C2 C3 C4 C5 -0.6(2)
C3 C4 C5 C6 -0.7(2)
C2 C1 C6 C5 -1.4(2)
C9 C1 C6 C5 176.78(14)
C2 C1 C6 C7 -179.85(14)
C9 C1 C6 C7 -1.66(18)
C4 C5 C6 C1 1.7(2)
C4 C5 C6 C7 179.80(15)
C1 C6 C7 O2 178.15(16)
C5 C6 C7 O2 -0.1(3)
C1 C6 C7 C8 -2.76(18)
C5 C6 C7 C8 178.95(16)
O2 C7 C8 C9 -174.98(15)
C6 C7 C8 C9 5.91(18)
C6 C1 C9 C10 129.44(15)
C2 C1 C9 C10 -52.5(2)
C6 C1 C9 C8 5.19(17)
C2 C1 C9 C8 -176.77(15)
C7 C8 C9 C10 -130.75(15)
C7 C8 C9 C1 -6.57(17)
C1 C9 C10 C11 -47.9(2)
C8 C9 C10 C11 70.3(2)
C1 C9 C10 C15 132.82(16)
C8 C9 C10 C15 -109.00(18)
C15 C10 C11 C12 0.8(3)
C9 C10 C11 C12 -178.50(16)
C10 C11 C12 C13 0.1(3)
C11 C12 C13 C14 -0.4(3)
C12 C13 C14 C15 -0.2(3)
C11 C10 C15 C14 -1.4(3)
C9 C10 C15 C14 177.89(16)
C13 C14 C15 C10 1.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072742
