# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GK-015
_audit_block_doi                 10.5517/ccdc.csd.cc25kv9x
_database_code_depnum_ccdc_archive 'CCDC 2013149'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.jnatprod.0c00932 2020
loop_
_audit_author_name
_audit_author_address
'Eric Sperlich'
;University Potsdam
Germany
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
'7-Hydroxy-3-(4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)- 4H-chromen-4-one'
_chemical_name_common            ?
_chemical_melting_point_gt       470
_chemical_melting_point_lt       472
_chemical_formula_moiety         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
_chemical_formula_weight         336.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   14.8274(4)
_cell_length_b                   8.16970(10)
_cell_length_c                   15.5656(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.139(2)
_cell_angle_gamma                90
_cell_volume                     1720.67(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    288(2)
_cell_measurement_reflns_used    35834
_cell_measurement_theta_min      1.43
_cell_measurement_theta_max      29.76

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_exptl_crystal_size_rad          0.306
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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_absorpt_correction_T_min  0.4076
_exptl_absorpt_correction_T_max  0.9589

_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_ambient_temperature      288(2)
_diffrn_measurement_method       'rotation method, δ omega = 1.0 deg'
_diffrn_measurement_details      
; 360 frames, detector distance = 100 mm
;

_diffrn_reflns_number            22586
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.599
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3955
_reflns_number_gt                3600
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.2448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0142(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3955
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.029

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GK-13
_database_code_depnum_ccdc_archive 'CCDC 2121813'
loop_
_audit_author_name
_audit_author_address
'Eric Sperlich'
;University Potsdam
Germany
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 3-(3-allyl-4-methoxyphenyl)-7-(methoxymethoxy)-4H-chromen-4-one
;
_chemical_name_common            ?
_chemical_melting_point          480
_chemical_formula_moiety         'C21 H20 O5'
_chemical_formula_sum            'C21 H20 O5'
_chemical_formula_weight         352.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.9139(2)
_cell_length_b                   14.6001(4)
_cell_length_c                   6.6911(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1750.02(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    41826
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      36.07

_exptl_crystal_description       'long prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_exptl_crystal_size_rad          0.1622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.0186
_exptl_absorpt_correction_T_max  0.9755
_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.
;

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Genix Microfocus'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.3 mm diameter'
_diffrn_ambient_temperature      210
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 3214 frames, detector distance = 60 mm
;
_diffrn_reflns_number            58225
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.013
_diffrn_reflns_theta_max         33.142
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6617
_reflns_number_gt                5353
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_structure_solution    'SHELXSL-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+0.0236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6617
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.32592(7) -0.17194(8) 0.8025(2) 0.0347(3) Uani 1 1 d . . . . .
O2 O 0.44939(7) 0.09234(8) 1.05662(18) 0.0294(3) Uani 1 1 d . . . . .
O3 O 0.45675(8) 0.20871(9) 0.5009(2) 0.0371(3) Uani 1 1 d . . . . .
O4 O 0.64884(8) 0.54848(8) 0.7890(2) 0.0378(3) Uani 1 1 d . . . . .
O5 O 0.30045(8) -0.18478(9) 1.1466(2) 0.0372(3) Uani 1 1 d . . . . .
C1 C 0.35616(10) -0.05132(12) 0.5872(3) 0.0313(4) Uani 1 1 d . . . . .
H1 H 0.333719 -0.084356 0.482650 0.038 Uiso 1 1 calc R U . . .
C2 C 0.35754(8) -0.08775(11) 0.7819(3) 0.0276(3) Uani 1 1 d . . . . .
C3 C 0.39008(8) -0.03953(11) 0.9377(3) 0.0267(3) Uani 1 1 d . . . . .
H3 H 0.391585 -0.063944 1.067610 0.032 Uiso 1 1 calc R U . . .
C4 C 0.42056(8) 0.04636(10) 0.8959(3) 0.0249(3) Uani 1 1 d . . . . .
C5 C 0.42045(8) 0.08424(11) 0.7057(2) 0.0245(3) Uani 1 1 d . . . . .
C6 C 0.38787(9) 0.03301(12) 0.5505(3) 0.0300(3) Uani 1 1 d . . . . .
H6 H 0.387734 0.056655 0.419862 0.036 Uiso 1 1 calc R U . . .
C7 C 0.48050(9) 0.17565(11) 1.0253(3) 0.0282(3) Uani 1 1 d . . . . .
H7 H 0.500130 0.206298 1.137136 0.034 Uiso 1 1 calc R U . . .
C8 C 0.48569(8) 0.21841(10) 0.8466(2) 0.0249(3) Uani 1 1 d . . . . .
C9 C 0.45432(8) 0.17426(11) 0.6688(3) 0.0253(3) Uani 1 1 d . . . . .
C10 C 0.52566(8) 0.30724(10) 0.8308(2) 0.0248(3) Uani 1 1 d . . . . .
C11 C 0.49592(8) 0.38129(12) 0.7280(3) 0.0286(3) Uani 1 1 d . . . . .
H11 H 0.448846 0.375794 0.667034 0.034 Uiso 1 1 calc R U . . .
C12 C 0.53490(9) 0.46375(11) 0.7137(3) 0.0295(3) Uani 1 1 d . . . . .
H12 H 0.513641 0.513986 0.646758 0.035 Uiso 1 1 calc R U . . .
C13 C 0.60540(9) 0.47118(11) 0.7991(3) 0.0281(3) Uani 1 1 d . . . . .
C14 C 0.63832(9) 0.39654(11) 0.8969(3) 0.0272(3) Uani 1 1 d . . . . .
C15 C 0.59685(8) 0.31664(10) 0.9146(3) 0.0262(3) Uani 1 1 d . . . . .
H15 H 0.617335 0.267017 0.985303 0.031 Uiso 1 1 calc R U . . .
C16 C 0.61793(14) 0.62701(13) 0.6924(4) 0.0460(5) Uani 1 1 d . . . . .
H16A H 0.652736 0.677711 0.702112 0.069 Uiso 1 1 calc R U . . .
H16B H 0.571317 0.643574 0.756691 0.069 Uiso 1 1 calc R U . . .
H16C H 0.608756 0.613084 0.552806 0.069 Uiso 1 1 calc R U . . .
C17 C 0.33926(11) -0.22074(11) 0.9856(3) 0.0355(4) Uani 1 1 d . . . . .
H17A H 0.324767 -0.284933 0.967605 0.043 Uiso 1 1 calc R U . . .
H17B H 0.392814 -0.219276 1.015374 0.043 Uiso 1 1 calc R U . . .
C18 C 0.22206(12) -0.20189(16) 1.1407(4) 0.0492(5) Uani 1 1 d . . . . .
H18A H 0.201102 -0.193403 1.273115 0.074 Uiso 1 1 calc R U . . .
H18B H 0.213226 -0.264272 1.096831 0.074 Uiso 1 1 calc R U . . .
H18C H 0.198567 -0.159623 1.048253 0.074 Uiso 1 1 calc R U . . .
C19 C 0.71763(9) 0.40113(13) 0.9719(3) 0.0346(4) Uani 1 1 d . . . . .
H19A H 0.738261 0.338966 0.971118 0.042 Uiso 1 1 calc R U . . .
H19B H 0.746866 0.437603 0.877063 0.042 Uiso 1 1 calc R U . . .
C20 C 0.72846(11) 0.44052(14) 1.1757(3) 0.0416(4) Uani 1 1 d . . . . .
H20 H 0.778065 0.451574 1.214596 0.050 Uiso 1 1 calc R U . . .
C21 C 0.67712(13) 0.46134(15) 1.3058(4) 0.0475(5) Uani 1 1 d . . . . .
H21A H 0.626521 0.451767 1.275022 0.057 Uiso 1 1 calc R U . . .
H21B H 0.690673 0.485951 1.430411 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.3603(19) . ?
O1 C17 1.438(2) . ?
O2 C7 1.354(2) . ?
O2 C4 1.369(2) . ?
O3 C9 1.232(2) . ?
O4 C13 1.3725(18) . ?
O4 C16 1.428(2) . ?
O5 C17 1.386(3) . ?
O5 C18 1.427(3) . ?
C1 C6 1.378(2) . ?
C1 C2 1.408(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.386(2) . ?
C3 C4 1.396(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(2) . ?
C5 C6 1.406(2) . ?
C5 C9 1.468(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.352(2) . ?
C7 H7 0.9400 . ?
C8 C9 1.465(2) . ?
C8 C10 1.485(2) . ?
C10 C11 1.388(2) . ?
C10 C15 1.400(2) . ?
C11 C12 1.395(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.391(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.401(2) . ?
C14 C15 1.388(2) . ?
C14 C19 1.508(2) . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 C20 1.493(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C21 1.302(3) . ?
C20 H20 0.9400 . ?
C21 H21A 0.9400 . ?
C21 H21B 0.9400 . ?

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 C17 117.69(14) . . ?
C7 O2 C4 118.30(13) . . ?
C13 O4 C16 117.57(15) . . ?
C17 O5 C18 113.96(17) . . ?
C6 C1 C2 119.68(16) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
O1 C2 C3 123.93(17) . . ?
O1 C2 C1 115.32(15) . . ?
C3 C2 C1 120.75(15) . . ?
C2 C3 C4 118.04(15) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
O2 C4 C5 121.71(13) . . ?
O2 C4 C3 115.50(14) . . ?
C5 C4 C3 122.77(14) . . ?
C4 C5 C6 117.76(14) . . ?
C4 C5 C9 120.69(14) . . ?
C6 C5 C9 121.55(15) . . ?
C1 C6 C5 120.98(16) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 O2 125.43(15) . . ?
C8 C7 H7 117.3 . . ?
O2 C7 H7 117.3 . . ?
C7 C8 C9 119.25(14) . . ?
C7 C8 C10 119.95(14) . . ?
C9 C8 C10 120.76(14) . . ?
O3 C9 C8 123.19(14) . . ?
O3 C9 C5 122.23(15) . . ?
C8 C9 C5 114.57(14) . . ?
C11 C10 C15 118.15(14) . . ?
C11 C10 C8 122.03(14) . . ?
C15 C10 C8 119.77(14) . . ?
C10 C11 C12 120.93(14) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.59(15) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O4 C13 C12 123.97(15) . . ?
O4 C13 C14 115.09(14) . . ?
C12 C13 C14 120.90(14) . . ?
C15 C14 C13 117.91(14) . . ?
C15 C14 C19 120.88(15) . . ?
C13 C14 C19 121.14(14) . . ?
C14 C15 C10 122.42(14) . . ?
C14 C15 H15 118.8 . . ?
C10 C15 H15 118.8 . . ?
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 . . ?
O5 C17 O1 113.06(14) . . ?
O5 C17 H17A 109.0 . . ?
O1 C17 H17A 109.0 . . ?
O5 C17 H17B 109.0 . . ?
O1 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C14 116.32(16) . . ?
C20 C19 H19A 108.2 . . ?
C14 C19 H19A 108.2 . . ?
C20 C19 H19B 108.2 . . ?
C14 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C19 127.50(19) . . ?
C21 C20 H20 116.2 . . ?
C19 C20 H20 116.2 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?

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
C17 O1 C2 C3 -12.1(2) . . . . ?
C17 O1 C2 C1 167.23(15) . . . . ?
C6 C1 C2 O1 -178.98(15) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
O1 C2 C3 C4 179.98(15) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C7 O2 C4 C5 -2.1(2) . . . . ?
C7 O2 C4 C3 179.29(14) . . . . ?
C2 C3 C4 O2 177.62(14) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
O2 C4 C5 C6 -178.36(14) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
O2 C4 C5 C9 2.5(2) . . . . ?
C3 C4 C5 C9 -179.01(14) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C9 C5 C6 C1 -179.89(15) . . . . ?
C4 O2 C7 C8 0.1(2) . . . . ?
O2 C7 C8 C9 1.4(3) . . . . ?
O2 C7 C8 C10 -176.01(14) . . . . ?
C7 C8 C9 O3 179.98(16) . . . . ?
C10 C8 C9 O3 -2.6(2) . . . . ?
C7 C8 C9 C5 -0.9(2) . . . . ?
C10 C8 C9 C5 176.46(13) . . . . ?
C4 C5 C9 O3 178.16(16) . . . . ?
C6 C5 C9 O3 -0.9(2) . . . . ?
C4 C5 C9 C8 -0.9(2) . . . . ?
C6 C5 C9 C8 179.98(14) . . . . ?
C7 C8 C10 C11 -133.66(18) . . . . ?
C9 C8 C10 C11 49.0(2) . . . . ?
C7 C8 C10 C15 49.0(2) . . . . ?
C9 C8 C10 C15 -128.43(16) . . . . ?
C15 C10 C11 C12 -2.0(3) . . . . ?
C8 C10 C11 C12 -179.39(16) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C16 O4 C13 C12 2.9(3) . . . . ?
C16 O4 C13 C14 -179.49(18) . . . . ?
C11 C12 C13 O4 178.36(17) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
O4 C13 C14 C15 179.16(16) . . . . ?
C12 C13 C14 C15 -3.2(3) . . . . ?
O4 C13 C14 C19 -3.8(2) . . . . ?
C12 C13 C14 C19 173.86(18) . . . . ?
C13 C14 C15 C10 3.0(3) . . . . ?
C19 C14 C15 C10 -174.09(16) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C8 C10 C15 C14 177.05(15) . . . . ?
C18 O5 C17 O1 72.0(2) . . . . ?
C2 O1 C17 O5 73.1(2) . . . . ?
C15 C14 C19 C20 -96.6(2) . . . . ?
C13 C14 C19 C20 86.4(2) . . . . ?
C14 C19 C20 C21 8.9(3) . . . . ?

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 O5 0.94 2.46 3.005(2) 116.8 . yes
C7 H7 O3 0.94 2.56 3.247(2) 130.6 1_556 yes
C18 H18C O4 0.97 2.54 3.504(3) 174.6 4_455 yes

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.041

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GK13B
_database_code_depnum_ccdc_archive 'CCDC 2121812'
loop_
_audit_author_name
_audit_author_address
'Eric Sperlich'
;University Potsdam
Germany
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 3-(3-allyl-4-methoxyphenyl)-7-hydroxy-4H-chromen-4-one
;
_chemical_name_common            ?
_chemical_melting_point          377
_chemical_formula_moiety         'C19 H16 O4'
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.0184(16)
_cell_length_b                   8.4831(17)
_cell_length_c                   11.867(2)
_cell_angle_alpha                104.02(3)
_cell_angle_beta                 94.03(3)
_cell_angle_gamma                101.24(3)
_cell_volume                     762.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    31569
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      36.15

_exptl_crystal_description       'long prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.125
_exptl_crystal_size_rad          0.183
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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_absorpt_correction_T_min  0.1598
_exptl_absorpt_correction_T_max  0.9749

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   Mo
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_ambient_temperature      210
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 3190 frames, detector distance = 60 mm
;
_diffrn_reflns_number            21354
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.692
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4636
_reflns_number_gt                3467
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²+0.0213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4636
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.058

