#------------------------------------------------------------------------------
#$Date: 2022-06-14 01:37:09 +0300 (Tue, 14 Jun 2022) $
#$Revision: 276008 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/50/7245064.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245064
loop_
_publ_author_name
'Sperlich, Eric'
'Kelling, Alexandra'
'Kwesiga, George'
'Schmidt, Bernd'
_publ_section_title
;
 Intermolecular interactions in the solid-state structures of isoflavones:
 the relationship between supramolecular structure, torsion angle, and
 macroscopic properties
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00169A
_journal_year                    2022
_chemical_formula_moiety         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
_chemical_formula_weight         336.37
_chemical_melting_point_gt       470
_chemical_melting_point_lt       472
_chemical_name_systematic
'7-Hydroxy-3-(4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)- 4H-chromen-4-one'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc25kv9x
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-07-13 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.139(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8274(4)
_cell_length_b                   8.16970(10)
_cell_length_c                   15.5656(4)
_cell_measurement_reflns_used    35834
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      29.76
_cell_measurement_theta_min      1.43
_cell_volume                     1720.67(7)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.86, Darmstadt 2018
SHELXL-2014/7 (Sheldrick, 2014)
DIAMOND. Crystal Impact GbR (Brandenburg,1999)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      288(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      ' 360 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, δ omega = 1.0 deg'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22586
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.599
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9589
_exptl_absorpt_correction_T_min  0.4076
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_exptl_crystal_size_rad          0.306
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0142(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0397
_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)+(0.0608P)²+0.2448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3600
_reflns_number_total             3955
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00169a2.cif
_cod_data_source_block           GK-015
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7245064
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65611(9) 0.96337(15) 0.18621(10) 0.0583(3) Uani 1 1 d . . . . .
H1 H 0.7293(11) 0.9841(19) 0.2219(10) 0.071(4) Uiso 1 1 d . . . . .
C2 C 0.59537(8) 1.10169(13) 0.15291(8) 0.0502(3) Uani 1 1 d . . . . .
C3 C 0.49481(8) 1.08375(13) 0.10315(8) 0.0491(2) Uani 1 1 d . . . . .
H3 H 0.4506(10) 1.1755(18) 0.0779(10) 0.064(4) Uiso 1 1 d . . . . .
C4 C 0.45609(8) 0.92712(13) 0.08811(8) 0.0464(2) Uani 1 1 d . . . . .
C5 C 0.51330(8) 0.78717(13) 0.12221(8) 0.0483(2) Uani 1 1 d . . . . .
C6 C 0.61548(9) 0.81079(15) 0.17149(9) 0.0571(3) Uani 1 1 d . . . . .
H6 H 0.6576(11) 0.7177(19) 0.1941(11) 0.069(4) Uiso 1 1 d . . . . .
C7 C 0.31385(9) 0.76743(14) 0.02265(9) 0.0564(3) Uani 1 1 d . . . . .
H7 H 0.2429(11) 0.7760(16) -0.0129(9) 0.059(3) Uiso 1 1 d . . . . .
C8 C 0.36084(9) 0.62487(13) 0.05423(8) 0.0510(3) Uani 1 1 d . . . . .
C9 C 0.46773(9) 0.62619(13) 0.10695(8) 0.0523(3) Uani 1 1 d . . . . .
C10 C 0.30244(9) 0.47135(13) 0.03126(8) 0.0508(3) Uani 1 1 d . . . . .
C11 C 0.24300(10) 0.43318(16) -0.06107(9) 0.0605(3) Uani 1 1 d . . . . .
H11 H 0.2441(12) 0.508(2) -0.1093(11) 0.076(4) Uiso 1 1 d . . . . .
C12 C 0.18495(10) 0.29331(16) -0.08374(8) 0.0619(3) Uani 1 1 d . . . . .
H12 H 0.1443(12) 0.2667(19) -0.1491(12) 0.077(4) Uiso 1 1 d . . . . .
C13 C 0.18588(8) 0.19071(13) -0.01312(8) 0.0511(3) Uani 1 1 d . . . . .
C14 C 0.24441(8) 0.22653(13) 0.08168(7) 0.0471(2) Uani 1 1 d . . . . .
C15 C 0.30226(8) 0.36581(13) 0.10186(8) 0.0483(2) Uani 1 1 d . . . . .
H15 H 0.3435(9) 0.3910(15) 0.1681(10) 0.055(3) Uiso 1 1 d . . . . .
C16 C 0.24353(10) 0.11007(15) 0.15693(8) 0.0558(3) Uani 1 1 d . . . . .
H16A H 0.2714(10) 0.0041(18) 0.1480(10) 0.064(4) Uiso 1 1 d . . . . .
H16B H 0.1724(12) 0.0830(18) 0.1438(11) 0.074(4) Uiso 1 1 d . . . . .
C17 C 0.29613(9) 0.16868(15) 0.25622(8) 0.0549(3) Uani 1 1 d . . . . .
H17 H 0.2695(10) 0.2693(18) 0.2728(9) 0.058(3) Uiso 1 1 d . . . . .
C18 C 0.37348(9) 0.10167(14) 0.32500(8) 0.0540(3) Uani 1 1 d . . . . .
C19 C 0.41179(12) 0.1698(2) 0.42311(9) 0.0687(3) Uani 1 1 d . . . . .
H19A H 0.4848(13) 0.184(2) 0.4492(12) 0.085(5) Uiso 1 1 d . . . . .
H19B H 0.3821(13) 0.279(2) 0.4264(12) 0.089(5) Uiso 1 1 d . . . . .
H19C H 0.3991(13) 0.087(2) 0.4676(13) 0.089(5) Uiso 1 1 d . . . . .
C20 C 0.42706(12) -0.0473(2) 0.31462(12) 0.0720(4) Uani 1 1 d . . . . .
H20 H 0.3988(13) -0.096(2) 0.2508(14) 0.092(5) Uiso 1 1 d . . . . .
H20A H 0.4962(17) -0.024(3) 0.3332(15) 0.111(7) Uiso 1 1 d . . . . .
H20B H 0.4254(15) -0.143(3) 0.3604(15) 0.112(6) Uiso 1 1 d . . . . .
C21 C 0.07205(16) 0.0053(2) -0.12292(12) 0.0856(5) Uani 1 1 d . . . . .
H21A H 0.0425(15) -0.097(3) -0.1171(13) 0.099(6) Uiso 1 1 d . . . . .
H21B H 0.1153(17) -0.016(3) -0.1562(17) 0.124(8) Uiso 1 1 d . . . . .
H21C H 0.0220(15) 0.094(3) -0.1559(14) 0.103(6) Uiso 1 1 d . . . . .
O1 O 0.64040(7) 1.24917(11) 0.17145(7) 0.0634(2) Uani 1 1 d . . . . .
H100 H 0.5948(15) 1.328(2) 0.1537(14) 0.100(6) Uiso 1 1 d . . . . .
O2 O 0.35622(6) 0.91650(9) 0.03641(6) 0.0570(2) Uani 1 1 d . . . . .
O3 O 0.51609(7) 0.49936(11) 0.13670(8) 0.0760(3) Uani 1 1 d . . . . .
O4 O 0.13172(7) 0.04966(11) -0.02845(6) 0.0637(2) Uani 1 1 d . . . . .
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_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.jnatprod.0c00932 2020
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.06(11) . . ?
C6 C1 H1 123.2(9) . . ?
C2 C1 H1 116.7(9) . . ?
O1 C2 C3 122.80(10) . . ?
O1 C2 C1 116.89(10) . . ?
C3 C2 C1 120.31(10) . . ?
C2 C3 C4 118.19(10) . . ?
C2 C3 H3 122.9(8) . . ?
C4 C3 H3 118.9(8) . . ?
O2 C4 C3 115.64(9) . . ?
O2 C4 C5 121.05(10) . . ?
C3 C4 C5 123.31(10) . . ?
C4 C5 C6 116.64(10) . . ?
C4 C5 C9 120.71(10) . . ?
C6 C5 C9 122.65(9) . . ?
C1 C6 C5 121.46(10) . . ?
C1 C6 H6 119.3(9) . . ?
C5 C6 H6 119.3(9) . . ?
C8 C7 O2 125.99(11) . . ?
C8 C7 H7 123.4(8) . . ?
O2 C7 H7 110.6(8) . . ?
C7 C8 C9 118.81(10) . . ?
C7 C8 C10 118.76(10) . . ?
C9 C8 C10 122.40(9) . . ?
O3 C9 C5 122.50(11) . . ?
O3 C9 C8 122.36(11) . . ?
C5 C9 C8 115.14(9) . . ?
C11 C10 C15 118.28(11) . . ?
C11 C10 C8 120.25(10) . . ?
C15 C10 C8 121.40(10) . . ?
C10 C11 C12 121.13(11) . . ?
C10 C11 H11 117.0(9) . . ?
C12 C11 H11 121.8(9) . . ?
C13 C12 C11 119.71(11) . . ?
C13 C12 H12 119.9(9) . . ?
C11 C12 H12 120.4(9) . . ?
O4 C13 C12 124.02(10) . . ?
O4 C13 C14 115.17(10) . . ?
C12 C13 C14 120.81(11) . . ?
C15 C14 C13 118.05(10) . . ?
C15 C14 C16 122.88(9) . . ?
C13 C14 C16 119.05(10) . . ?
C14 C15 C10 122.00(10) . . ?
C14 C15 H15 118.2(7) . . ?
C10 C15 H15 119.8(8) . . ?
C17 C16 C14 115.62(10) . . ?
C17 C16 H16A 110.7(8) . . ?
C14 C16 H16A 107.7(8) . . ?
C17 C16 H16B 109.7(9) . . ?
C14 C16 H16B 108.6(9) . . ?
H16A C16 H16B 103.8(12) . . ?
C18 C17 C16 127.97(12) . . ?
C18 C17 H17 115.9(8) . . ?
C16 C17 H17 116.1(7) . . ?
C17 C18 C20 124.78(12) . . ?
C17 C18 C19 120.72(12) . . ?
C20 C18 C19 114.46(12) . . ?
C18 C19 H19A 110.8(10) . . ?
C18 C19 H19B 112.9(10) . . ?
H19A C19 H19B 107.5(14) . . ?
C18 C19 H19C 109.9(10) . . ?
H19A C19 H19C 105.6(13) . . ?
H19B C19 H19C 110.0(14) . . ?
C18 C20 H20 114.1(10) . . ?
C18 C20 H20A 110.7(13) . . ?
H20 C20 H20A 110.0(16) . . ?
C18 C20 H20B 111.4(11) . . ?
H20 C20 H20B 105.2(15) . . ?
H20A C20 H20B 104.9(17) . . ?
O4 C21 H21A 103.8(12) . . ?
O4 C21 H21B 108.9(14) . . ?
H21A C21 H21B 108.1(18) . . ?
O4 C21 H21C 111.1(11) . . ?
H21A C21 H21C 113.6(16) . . ?
H21B C21 H21C 111.0(18) . . ?
C2 O1 H100 109.6(12) . . ?
C7 O2 C4 118.23(8) . . ?
C13 O4 C21 117.94(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3625(17) . ?
C1 C2 1.4053(15) . ?
C1 H1 1.011(15) . ?
C2 O1 1.3503(14) . ?
C2 C3 1.3783(16) . ?
C3 C4 1.3827(15) . ?
C3 H3 0.967(15) . ?
C4 O2 1.3687(13) . ?
C4 C5 1.3929(14) . ?
C5 C6 1.4037(16) . ?
C5 C9 1.4531(15) . ?
C6 H6 0.955(16) . ?
C7 C8 1.3429(15) . ?
C7 O2 1.3467(14) . ?
C7 H7 0.971(14) . ?
C8 C9 1.4566(17) . ?
C8 C10 1.4824(16) . ?
C9 O3 1.2372(13) . ?
C10 C11 1.3796(17) . ?
C10 C15 1.3977(15) . ?
C11 C12 1.3866(18) . ?
C11 H11 0.975(16) . ?
C12 C13 1.3779(17) . ?
C12 H12 0.972(16) . ?
C13 O4 1.3686(14) . ?
C13 C14 1.4032(15) . ?
C14 C15 1.3817(15) . ?
C14 C16 1.5132(15) . ?
C15 H15 0.982(13) . ?
C16 C17 1.4967(17) . ?
C16 H16A 0.993(15) . ?
C16 H16B 1.013(16) . ?
C17 C18 1.3255(17) . ?
C17 H17 0.991(14) . ?
C18 C20 1.4977(19) . ?
C18 C19 1.5017(18) . ?
C19 H19A 0.995(18) . ?
C19 H19B 1.003(19) . ?
C19 H19C 1.039(18) . ?
C20 H20 0.990(19) . ?
C20 H20A 0.96(2) . ?
C20 H20B 1.06(2) . ?
C21 O4 1.4185(17) . ?
C21 H21A 0.97(2) . ?
C21 H21B 0.99(2) . ?
C21 H21C 1.01(2) . ?
O1 H100 0.89(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H100 O3 0.89(2) 1.77(2) 2.6557(13) 170.7(19) 1_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 178.85(11) . . . . ?
C6 C1 C2 C3 -1.66(19) . . . . ?
O1 C2 C3 C4 -179.93(10) . . . . ?
C1 C2 C3 C4 0.62(17) . . . . ?
C2 C3 C4 O2 -178.51(10) . . . . ?
C2 C3 C4 C5 1.27(17) . . . . ?
O2 C4 C5 C6 177.74(10) . . . . ?
C3 C4 C5 C6 -2.03(17) . . . . ?
O2 C4 C5 C9 -2.48(16) . . . . ?
C3 C4 C5 C9 177.75(10) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C4 C5 C6 C1 0.92(18) . . . . ?
C9 C5 C6 C1 -178.85(12) . . . . ?
O2 C7 C8 C9 -1.29(19) . . . . ?
O2 C7 C8 C10 -179.16(11) . . . . ?
C4 C5 C9 O3 -179.54(12) . . . . ?
C6 C5 C9 O3 0.22(19) . . . . ?
C4 C5 C9 C8 0.32(16) . . . . ?
C6 C5 C9 C8 -179.92(11) . . . . ?
C7 C8 C9 O3 -178.66(12) . . . . ?
C10 C8 C9 O3 -0.87(18) . . . . ?
C7 C8 C9 C5 1.48(16) . . . . ?
C10 C8 C9 C5 179.27(10) . . . . ?
C7 C8 C10 C11 54.25(16) . . . . ?
C9 C8 C10 C11 -123.54(13) . . . . ?
C7 C8 C10 C15 -122.74(13) . . . . ?
C9 C8 C10 C15 59.47(15) . . . . ?
C15 C10 C11 C12 -0.45(19) . . . . ?
C8 C10 C11 C12 -177.54(12) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C11 C12 C13 O4 -179.60(12) . . . . ?
C11 C12 C13 C14 0.43(19) . . . . ?
O4 C13 C14 C15 178.88(10) . . . . ?
C12 C13 C14 C15 -1.16(17) . . . . ?
O4 C13 C14 C16 0.29(15) . . . . ?
C12 C13 C14 C16 -179.74(11) . . . . ?
C13 C14 C15 C10 1.10(16) . . . . ?
C16 C14 C15 C10 179.63(11) . . . . ?
C11 C10 C15 C14 -0.32(17) . . . . ?
C8 C10 C15 C14 176.73(10) . . . . ?
C15 C14 C16 C17 9.95(17) . . . . ?
C13 C14 C16 C17 -171.54(11) . . . . ?
C14 C16 C17 C18 -118.61(14) . . . . ?
C16 C17 C18 C20 2.6(2) . . . . ?
C16 C17 C18 C19 -174.89(12) . . . . ?
C8 C7 O2 C4 -0.86(19) . . . . ?
C3 C4 O2 C7 -177.46(10) . . . . ?
C5 C4 O2 C7 2.76(16) . . . . ?
C12 C13 O4 C21 0.9(2) . . . . ?
C14 C13 O4 C21 -179.12(14) . . . . ?
