#------------------------------------------------------------------------------
#$Date: 2022-06-14 01:37:09 +0300 (Tue, 14 Jun 2022) $
#$Revision: 276008 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/50/7245066.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_7245066
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         'C19 H16 O4'
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32
_chemical_melting_point          377
_chemical_name_systematic
;
 3-(3-allyl-4-methoxyphenyl)-7-hydroxy-4H-chromen-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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-11-12 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                104.02(3)
_cell_angle_beta                 94.03(3)
_cell_angle_gamma                101.24(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0184(16)
_cell_length_b                   8.4831(17)
_cell_length_c                   11.867(2)
_cell_measurement_reflns_used    31569
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      36.15
_cell_measurement_theta_min      2.54
_cell_volume                     762.3(3)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_molecular_graphics    'Diamond (Blankenburg, 2020)'
_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
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      210
_diffrn_detector                 Pilatus200K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      ' 3190 frames, detector distance = 60 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21354
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         2.692
_diffrn_source                   Mo
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.1598
_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    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'long prism'
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.125
_exptl_crystal_size_rad          0.183
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0465
_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)+(0.0882P)²+0.0213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3467
_reflns_number_total             4636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00169a2.cif
_cod_data_source_block           GK13B
_cod_original_cell_volume        762.2(3)
_cod_database_code               7245066
_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_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
O1 O 0.68892(10) 0.23242(10) 0.03984(7) 0.0324(2) Uani 1 1 d . . . . .
O2 O 0.48042(10) 0.70381(9) 0.21950(7) 0.0326(2) Uani 1 1 d . . . . .
O3 O -0.01687(10) 0.44355(11) 0.14174(9) 0.0451(3) Uani 1 1 d . . . . .
O4 O -0.30105(11) 1.07753(10) 0.38035(7) 0.0331(2) Uani 1 1 d . . . . .
C1 C 0.39073(14) 0.20949(13) 0.03867(10) 0.0308(2) Uani 1 1 d . . . . .
H1 H 0.372858 0.097195 -0.003421 0.037 Uiso 1 1 calc R U . . .
C2 C 0.55876(13) 0.30728(13) 0.07166(9) 0.0246(2) Uani 1 1 d . . . . .
C3 C 0.58671(13) 0.47230(12) 0.13353(9) 0.0244(2) Uani 1 1 d . . . . .
H3 H 0.698461 0.537624 0.156753 0.029 Uiso 1 1 calc R U . . .
C4 C 0.44533(13) 0.53887(12) 0.16042(9) 0.0229(2) Uani 1 1 d . . . . .
C5 C 0.27683(12) 0.44592(12) 0.13011(8) 0.0230(2) Uani 1 1 d . . . . .
C6 C 0.25376(14) 0.27822(13) 0.06800(10) 0.0299(2) Uani 1 1 d . . . . .
H6 H 0.142232 0.211973 0.046174 0.036 Uiso 1 1 calc R U . . .
C7 C 0.34786(14) 0.77552(13) 0.24719(10) 0.0307(2) Uani 1 1 d . . . . .
H7 H 0.374050 0.889276 0.286805 0.037 Uiso 1 1 calc R U . . .
C8 C 0.18135(13) 0.69867(13) 0.22316(9) 0.0246(2) Uani 1 1 d . . . . .
C9 C 0.13420(13) 0.52217(13) 0.16271(9) 0.0260(2) Uani 1 1 d . . . . .
C10 C 0.05056(13) 0.79594(13) 0.25927(9) 0.0245(2) Uani 1 1 d . . . . .
C11 C 0.02799(14) 0.92444(14) 0.20998(9) 0.0286(2) Uani 1 1 d . . . . .
H11 H 0.092994 0.946629 0.150480 0.034 Uiso 1 1 calc R U . . .
C12 C -0.08926(15) 1.02029(14) 0.24753(9) 0.0295(2) Uani 1 1 d . . . . .
H12 H -0.104502 1.106055 0.213044 0.035 Uiso 1 1 calc R U . . .
C13 C -0.18423(13) 0.98874(13) 0.33658(9) 0.0251(2) Uani 1 1 d . . . . .
C14 C -0.16442(13) 0.85945(12) 0.38748(8) 0.0236(2) Uani 1 1 d . . . . .
C15 C -0.04777(13) 0.76512(13) 0.34754(9) 0.0249(2) Uani 1 1 d . . . . .
H15 H -0.034137 0.677678 0.380665 0.030 Uiso 1 1 calc R U . . .
C16 C -0.3335(2) 1.20268(19) 0.32635(16) 0.0547(4) Uani 1 1 d . . . . .
H16A H -0.420359 1.254279 0.363661 0.082 Uiso 1 1 calc R U . . .
H16B H -0.373511 1.152797 0.243940 0.082 Uiso 1 1 calc R U . . .
H16C H -0.228804 1.286377 0.334605 0.082 Uiso 1 1 calc R U . . .
C17 C -0.26720(14) 0.82699(14) 0.48498(10) 0.0299(2) Uani 1 1 d . . . . .
H17A H -0.206371 0.899315 0.559755 0.036 Uiso 1 1 calc R U . . .
H17B H -0.377997 0.856914 0.473340 0.036 Uiso 1 1 calc R U . . .
C18 C -0.29789(15) 0.65038(15) 0.49181(10) 0.0334(3) Uani 1 1 d . . . . .
H18 H -0.361188 0.568847 0.426589 0.040 Uiso 1 1 calc R U . . .
C19 C -0.2446(2) 0.5990(2) 0.58041(13) 0.0528(4) Uani 1 1 d . . . . .
H19A H -0.180824 0.676222 0.647492 0.063 Uiso 1 1 calc R U . . .
H19B H -0.270017 0.484888 0.577025 0.063 Uiso 1 1 calc R U . . .
H100 H 0.790(3) 0.311(3) 0.0731(18) 0.079 Uiso 1 1 d . U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H100 106.2(12) . . ?
C7 O2 C4 118.19(8) . . ?
C13 O4 C16 117.38(9) . . ?
C6 C1 C2 119.94(10) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
O1 C2 C3 122.21(9) . . ?
O1 C2 C1 117.20(9) . . ?
C3 C2 C1 120.59(10) . . ?
C2 C3 C4 118.08(9) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
O2 C4 C3 115.59(9) . . ?
O2 C4 C5 121.32(9) . . ?
C3 C4 C5 123.10(9) . . ?
C4 C5 C6 117.10(10) . . ?
C4 C5 C9 120.46(9) . . ?
C6 C5 C9 122.45(9) . . ?
C1 C6 C5 121.18(10) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 O2 125.70(10) . . ?
C8 C7 H7 117.2 . . ?
O2 C7 H7 117.2 . . ?
C7 C8 C9 119.25(10) . . ?
C7 C8 C10 119.02(10) . . ?
C9 C8 C10 121.74(9) . . ?
O3 C9 C5 122.87(10) . . ?
O3 C9 C8 122.08(10) . . ?
C5 C9 C8 115.05(9) . . ?
C11 C10 C15 118.55(10) . . ?
C11 C10 C8 120.86(9) . . ?
C15 C10 C8 120.53(9) . . ?
C12 C11 C10 120.83(9) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.63(10) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
O4 C13 C12 123.90(9) . . ?
O4 C13 C14 115.41(9) . . ?
C12 C13 C14 120.69(9) . . ?
C15 C14 C13 118.37(9) . . ?
C15 C14 C17 121.32(9) . . ?
C13 C14 C17 120.30(9) . . ?
C14 C15 C10 121.92(9) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C14 113.60(9) . . ?
C18 C17 H17A 108.8 . . ?
C14 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C14 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 125.83(13) . . ?
C19 C18 H18 117.1 . . ?
C17 C18 H18 117.1 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
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
O1 C2 1.3538(12) . ?
O1 H100 0.94(2) . ?
O2 C7 1.3462(13) . ?
O2 C4 1.3681(13) . ?
O3 C9 1.2394(13) . ?
O4 C13 1.3670(13) . ?
O4 C16 1.4211(15) . ?
C1 C6 1.3683(15) . ?
C1 C2 1.4104(15) . ?
C1 H1 0.9400 . ?
C2 C3 1.3804(15) . ?
C3 C4 1.3853(14) . ?
C3 H3 0.9400 . ?
C4 C5 1.3984(14) . ?
C5 C6 1.4041(15) . ?
C5 C9 1.4510(14) . ?
C6 H6 0.9400 . ?
C7 C8 1.3438(15) . ?
C7 H7 0.9400 . ?
C8 C9 1.4560(15) . ?
C8 C10 1.4811(14) . ?
C10 C11 1.3907(15) . ?
C10 C15 1.3984(14) . ?
C11 C12 1.3874(15) . ?
C11 H11 0.9400 . ?
C12 C13 1.3925(15) . ?
C12 H12 0.9400 . ?
C13 C14 1.4030(14) . ?
C14 C15 1.3821(14) . ?
C14 C17 1.5145(14) . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.4932(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.3075(18) . ?
C18 H18 0.9400 . ?
C19 H19A 0.9400 . ?
C19 H19B 0.9400 . ?
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
_geom_hbond_publ_flag
C3 H3 O3 0.94 2.56 3.2316(14) 128.2 1_655 yes
O1 H100 O3 0.94(2) 1.74(2) 2.6716(16) 174.5(19) 1_655 yes
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 -179.82(9) . . . . ?
C6 C1 C2 C3 0.03(17) . . . . ?
O1 C2 C3 C4 178.89(9) . . . . ?
C1 C2 C3 C4 -0.95(15) . . . . ?
C7 O2 C4 C3 179.51(9) . . . . ?
C7 O2 C4 C5 -0.52(15) . . . . ?
C2 C3 C4 O2 -178.58(9) . . . . ?
C2 C3 C4 C5 1.45(15) . . . . ?
O2 C4 C5 C6 179.06(9) . . . . ?
C3 C4 C5 C6 -0.98(15) . . . . ?
O2 C4 C5 C9 -1.11(15) . . . . ?
C3 C4 C5 C9 178.85(9) . . . . ?
C2 C1 C6 C5 0.46(17) . . . . ?
C4 C5 C6 C1 -0.01(16) . . . . ?
C9 C5 C6 C1 -179.83(10) . . . . ?
C4 O2 C7 C8 0.87(17) . . . . ?
O2 C7 C8 C9 0.46(17) . . . . ?
O2 C7 C8 C10 -179.72(10) . . . . ?
C4 C5 C9 O3 -177.22(10) . . . . ?
C6 C5 C9 O3 2.60(17) . . . . ?
C4 C5 C9 C8 2.29(14) . . . . ?
C6 C5 C9 C8 -177.89(9) . . . . ?
C7 C8 C9 O3 177.54(11) . . . . ?
C10 C8 C9 O3 -2.28(16) . . . . ?
C7 C8 C9 C5 -1.98(14) . . . . ?
C10 C8 C9 C5 178.21(9) . . . . ?
C7 C8 C10 C11 65.49(14) . . . . ?
C9 C8 C10 C11 -114.69(12) . . . . ?
C7 C8 C10 C15 -111.68(12) . . . . ?
C9 C8 C10 C15 68.13(14) . . . . ?
C15 C10 C11 C12 0.10(16) . . . . ?
C8 C10 C11 C12 -177.13(10) . . . . ?
C10 C11 C12 C13 0.72(17) . . . . ?
C16 O4 C13 C12 3.82(17) . . . . ?
C16 O4 C13 C14 -176.04(11) . . . . ?
C11 C12 C13 O4 179.19(10) . . . . ?
C11 C12 C13 C14 -0.96(16) . . . . ?
O4 C13 C14 C15 -179.76(9) . . . . ?
C12 C13 C14 C15 0.38(15) . . . . ?
O4 C13 C14 C17 -0.65(14) . . . . ?
C12 C13 C14 C17 179.49(10) . . . . ?
C13 C14 C15 C10 0.46(15) . . . . ?
C17 C14 C15 C10 -178.64(10) . . . . ?
C11 C10 C15 C14 -0.70(16) . . . . ?
C8 C10 C15 C14 176.54(9) . . . . ?
C15 C14 C17 C18 -28.13(15) . . . . ?
C13 C14 C17 C18 152.79(10) . . . . ?
C14 C17 C18 C19 118.04(14) . . . . ?
