#------------------------------------------------------------------------------
#$Date: 2022-09-14 04:48:47 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277824 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567638.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_1567638
loop_
_publ_author_name
'Sung, Jiha'
_publ_section_title
;
 3-(2,3-Dimethoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one
;
_journal_coeditor_code           HB4411
_journal_issue                   9
_journal_name_full               IUCrData
_journal_page_first              x220885
_journal_paper_doi               10.1107/S2414314622008859
_journal_volume                  7
_journal_year                    2022
_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
;
3-(2,3-Dimethoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                94.261(4)
_cell_angle_beta                 107.335(4)
_cell_angle_gamma                112.326(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3312(14)
_cell_length_b                   9.6506(16)
_cell_length_c                   11.797(2)
_cell_measurement_reflns_used    2013
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.91
_cell_measurement_theta_min      2.65
_cell_volume                     818.4(2)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5181
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.8943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.2044
_reflns_number_gt                2136
_reflns_number_total             3202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb4411sup1.cif
_cod_data_source_block           I
_cod_database_code               1567638
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5916(4) 0.4265(4) 0.1200(3) 0.0387(7) Uani d . 1 1 . .
O O1 0.7393(3) 0.5280(3) 0.1255(2) 0.0534(7) Uani d . 1 1 . .
C C2 0.4897(5) 0.4555(4) 0.1987(3) 0.0467(8) Uani d . 1 1 . .
H H2A 0.5804 0.5215 0.2782 0.056 Uiso calc R 1 1 . .
H H2B 0.4162 0.5101 0.1594 0.056 Uiso calc R 1 1 . .
C C3 0.3641(4) 0.3088(4) 0.2179(3) 0.0404(8) Uani d . 1 1 . .
H H3 0.4419 0.2569 0.2588 0.048 Uiso calc R 1 1 . .
O O2 0.2359(3) 0.2101(2) 0.10246(19) 0.0406(6) Uani d . 1 1 . .
C C4 0.2501(4) 0.3214(4) 0.2935(3) 0.0387(7) Uani d . 1 1 . .
C C5 0.2559(4) 0.2556(3) 0.3936(3) 0.0368(7) Uani d . 1 1 . .
O O3 0.3634(3) 0.1743(3) 0.4229(2) 0.0470(6) Uani d . 1 1 . .
C C6 0.5292(5) 0.2525(5) 0.5253(4) 0.0649(11) Uani d . 1 1 . .
H H6A 0.6015 0.3530 0.5121 0.097 Uiso calc R 1 1 . .
H H6B 0.6025 0.1923 0.5364 0.097 Uiso calc R 1 1 . .
H H6C 0.4983 0.2664 0.5979 0.097 Uiso calc R 1 1 . .
C C7 0.1468(4) 0.2610(4) 0.4626(3) 0.0396(7) Uani d . 1 1 . .
O O4 0.1617(3) 0.1893(3) 0.5578(2) 0.0501(6) Uani d . 1 1 . .
C C8 0.0315(5) 0.1696(5) 0.6180(4) 0.0558(10) Uani d . 1 1 . .
H H8A 0.0463 0.2702 0.6546 0.084 Uiso calc R 1 1 . .
H H8B 0.0537 0.1122 0.6816 0.084 Uiso calc R 1 1 . .
H H8C -0.0947 0.1128 0.5590 0.084 Uiso calc R 1 1 . .
C C9 0.0321(5) 0.3356(4) 0.4296(3) 0.0443(8) Uani d . 1 1 . .
H H9 -0.0429 0.3403 0.4753 0.053 Uiso calc R 1 1 . .
C C10 0.0275(5) 0.4029(4) 0.3300(3) 0.0474(8) Uani d . 1 1 . .
H H10 -0.0501 0.4549 0.3083 0.057 Uiso calc R 1 1 . .
C C11 0.1337(5) 0.3958(4) 0.2616(3) 0.0452(8) Uani d . 1 1 . .
H H11 0.1277 0.4416 0.1928 0.054 Uiso calc R 1 1 . .
C C12 0.3185(4) 0.1820(4) 0.0248(3) 0.0366(7) Uani d . 1 1 . .
C C13 0.2063(4) 0.0489(4) -0.0672(3) 0.0425(8) Uani d . 1 1 . .
H H13 0.0818 -0.0104 -0.0740 0.051 Uiso calc R 1 1 . .
C C14 0.2764(5) 0.0057(4) -0.1459(3) 0.0427(8) Uani d . 1 1 . .
H H14 0.1997 -0.0838 -0.2083 0.051 Uiso calc R 1 1 . .
C C15 0.4630(4) 0.0918(4) -0.1370(3) 0.0378(7) Uani d . 1 1 . .
C C16 0.5352(5) 0.0391(4) -0.2161(3) 0.0428(8) Uani d . 1 1 . .
H H16 0.4571 -0.0510 -0.2778 0.051 Uiso calc R 1 1 . .
C C17 0.7169(5) 0.1166(4) -0.2048(3) 0.0482(9) Uani d . 1 1 . .
H H17 0.7653 0.0800 -0.2577 0.058 Uiso calc R 1 1 . .
C C18 0.8306(5) 0.2500(4) -0.1150(3) 0.0474(9) Uani d . 1 1 . .
H H18 0.9572 0.3027 -0.1065 0.057 Uiso calc R 1 1 . .
C C19 0.7633(5) 0.3060(4) -0.0389(3) 0.0438(8) Uani d . 1 1 . .
H H19 0.8427 0.3985 0.0200 0.053 Uiso calc R 1 1 . .
C C20 0.5757(4) 0.2274(4) -0.0469(3) 0.0366(7) Uani d . 1 1 . .
C C21 0.4989(4) 0.2770(3) 0.0347(3) 0.0364(7) Uani 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 0.0033 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
O1 C1 C21 . . 123.8(3) ?
O1 C1 C2 . . 119.8(3) ?
C21 C1 C2 . . 116.4(3) ?
C3 C2 C1 . . 110.8(3) ?
C3 C2 H2A . . 109.5 ?
C1 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108.1 ?
O2 C3 C2 . . 109.8(3) ?
O2 C3 C4 . . 107.0(2) ?
C2 C3 C4 . . 116.2(3) ?
O2 C3 H3 . . 107.8 ?
C2 C3 H3 . . 107.8 ?
C4 C3 H3 . . 107.8 ?
C12 O2 C3 . . 114.2(2) ?
C5 C4 C11 . . 118.8(3) ?
C5 C4 C3 . . 120.3(3) ?
C11 C4 C3 . . 120.9(3) ?
C4 C5 O3 . . 119.6(3) ?
C4 C5 C7 . . 121.4(3) ?
O3 C5 C7 . . 118.9(3) ?
C5 O3 C6 . . 114.0(3) ?
O3 C6 H6A . . 109.5 ?
O3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
O3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O4 C7 C9 . . 125.0(3) ?
O4 C7 C5 . . 116.0(3) ?
C9 C7 C5 . . 119.0(3) ?
C7 O4 C8 . . 117.8(3) ?
O4 C8 H8A . . 109.5 ?
O4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C7 . . 119.7(3) ?
C10 C9 H9 . . 120.1 ?
C7 C9 H9 . . 120.1 ?
C11 C10 C9 . . 121.1(3) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C4 . . 120.0(3) ?
C10 C11 H11 . . 120.0 ?
C4 C11 H11 . . 120.0 ?
O2 C12 C21 . . 123.3(3) ?
O2 C12 C13 . . 114.5(3) ?
C21 C12 C13 . . 122.3(3) ?
C14 C13 C12 . . 119.7(3) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C13 C14 C15 . . 121.3(3) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
C20 C15 C16 . . 120.5(3) ?
C20 C15 C14 . . 119.6(3) ?
C16 C15 C14 . . 119.9(3) ?
C17 C16 C15 . . 120.6(3) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C18 . . 119.5(3) ?
C16 C17 H17 . . 120.2 ?
C18 C17 H17 . . 120.2 ?
C19 C18 C17 . . 121.2(3) ?
C19 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
C18 C19 C20 . . 120.8(3) ?
C18 C19 H19 . . 119.6 ?
C20 C19 H19 . . 119.6 ?
C15 C20 C19 . . 117.4(3) ?
C15 C20 C21 . . 119.2(3) ?
C19 C20 C21 . . 123.4(3) ?
C12 C21 C20 . . 117.7(3) ?
C12 C21 C1 . . 117.6(3) ?
C20 C21 C1 . . 124.5(3) ?
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
C1 O1 . 1.227(4) ?
C1 C21 . 1.471(4) ?
C1 C2 . 1.507(4) ?
C2 C3 . 1.488(5) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 O2 . 1.439(4) ?
C3 C4 . 1.513(4) ?
C3 H3 . 1.0000 ?
O2 C12 . 1.366(3) ?
C4 C5 . 1.379(4) ?
C4 C11 . 1.396(5) ?
C5 O3 . 1.389(4) ?
C5 C7 . 1.400(4) ?
O3 C6 . 1.419(4) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 O4 . 1.362(4) ?
C7 C9 . 1.388(5) ?
O4 C8 . 1.428(4) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.381(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.379(5) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 C21 . 1.394(4) ?
C12 C13 . 1.406(4) ?
C13 C14 . 1.352(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.423(4) ?
C14 H14 . 0.9500 ?
C15 C20 . 1.410(4) ?
C15 C16 . 1.410(4) ?
C16 C17 . 1.369(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.396(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.367(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.424(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.449(4) ?
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
C13 H13 O2 2 0.95 2.52 3.454(4) 169
C18 H18 O1 2_765 0.95 2.52 3.452(4) 166
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
O1 C1 C2 C3 . . . . -156.5(3) ?
C21 C1 C2 C3 . . . . 26.8(4) ?
C1 C2 C3 O2 . . . . -57.2(4) ?
C1 C2 C3 C4 . . . . -178.8(3) ?
C2 C3 O2 C12 . . . . 55.5(3) ?
C4 C3 O2 C12 . . . . -177.5(3) ?
O2 C3 C4 C5 . . . . 111.0(3) ?
C2 C3 C4 C5 . . . . -125.9(3) ?
O2 C3 C4 C11 . . . . -67.2(4) ?
C2 C3 C4 C11 . . . . 55.9(4) ?
C11 C4 C5 O3 . . . . 176.6(3) ?
C3 C4 C5 O3 . . . . -1.6(4) ?
C11 C4 C5 C7 . . . . 0.5(5) ?
C3 C4 C5 C7 . . . . -177.7(3) ?
C4 C5 O3 C6 . . . . 105.9(4) ?
C7 C5 O3 C6 . . . . -77.9(4) ?
C4 C5 C7 O4 . . . . 178.7(3) ?
O3 C5 C7 O4 . . . . 2.6(4) ?
C4 C5 C7 C9 . . . . -0.6(5) ?
O3 C5 C7 C9 . . . . -176.7(3) ?
C9 C7 O4 C8 . . . . 9.5(5) ?
C5 C7 O4 C8 . . . . -169.8(3) ?
O4 C7 C9 C10 . . . . -179.3(3) ?
C5 C7 C9 C10 . . . . 0.0(5) ?
C7 C9 C10 C11 . . . . 0.7(5) ?
C9 C10 C11 C4 . . . . -0.8(5) ?
C5 C4 C11 C10 . . . . 0.2(5) ?
C3 C4 C11 C10 . . . . 178.4(3) ?
C3 O2 C12 C21 . . . . -21.5(4) ?
C3 O2 C12 C13 . . . . 158.7(3) ?
O2 C12 C13 C14 . . . . -176.9(3) ?
C21 C12 C13 C14 . . . . 3.3(5) ?
C12 C13 C14 C15 . . . . 0.6(5) ?
C13 C14 C15 C20 . . . . -2.0(5) ?
C13 C14 C15 C16 . . . . 176.4(3) ?
C20 C15 C16 C17 . . . . 1.6(5) ?
C14 C15 C16 C17 . . . . -176.8(3) ?
C15 C16 C17 C18 . . . . -0.8(5) ?
C16 C17 C18 C19 . . . . -0.9(5) ?
C17 C18 C19 C20 . . . . 1.7(5) ?
C16 C15 C20 C19 . . . . -0.8(5) ?
C14 C15 C20 C19 . . . . 177.6(3) ?
C16 C15 C20 C21 . . . . -178.7(3) ?
C14 C15 C20 C21 . . . . -0.3(5) ?
C18 C19 C20 C15 . . . . -0.9(5) ?
C18 C19 C20 C21 . . . . 177.0(3) ?
O2 C12 C21 C20 . . . . 174.8(3) ?
C13 C12 C21 C20 . . . . -5.5(5) ?
O2 C12 C21 C1 . . . . -10.3(5) ?
C13 C12 C21 C1 . . . . 169.4(3) ?
C15 C20 C21 C12 . . . . 3.9(4) ?
C19 C20 C21 C12 . . . . -173.9(3) ?
C15 C20 C21 C1 . . . . -170.6(3) ?
C19 C20 C21 C1 . . . . 11.6(5) ?
O1 C1 C21 C12 . . . . -170.1(3) ?
C2 C1 C21 C12 . . . . 6.4(4) ?
O1 C1 C21 C20 . . . . 4.4(5) ?
C2 C1 C21 C20 . . . . -179.1(3) ?

_cod_database_fobs_code 1567638
