# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1561888'
_audit_update_record             
;
2017-07-13 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        daidzein
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 O4'
_chemical_formula_weight         254.23

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 212121'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8600(8)
_cell_length_b                   11.430(2)
_cell_length_c                   25.629(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1130.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3756
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      67.72

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10932
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2560
_reflns_number_gt                1827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(18)
_refine_ls_number_reflns         2560
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6602(5) 0.31025(14) 0.44129(6) 0.0353(5) Uani 1 1 d . . .
O4 O 0.1167(5) 0.28239(14) 0.14773(6) 0.0450(5) Uani 1 1 d . . .
H8 H 0.0267 0.2178 0.1444 0.068 Uiso 1 1 calc R . .
O2 O 0.1684(6) 0.56698(15) 0.35846(6) 0.0500(6) Uani 1 1 d . . .
O3 O 0.5977(6) 0.51668(16) 0.59876(6) 0.0537(6) Uani 1 1 d . . .
H4 H 0.5314 0.5789 0.6111 0.081 Uiso 1 1 calc R . .
C9 C 0.5599(7) 0.4112(2) 0.46619(9) 0.0295(6) Uani 1 1 d . . .
C1 C 0.5850(7) 0.2986(2) 0.38966(9) 0.0313(6) Uani 1 1 d . . .
H1 H 0.6508 0.2291 0.3736 0.038 Uiso 1 1 calc R . .
C8 C 0.6266(8) 0.4168(2) 0.51933(9) 0.0333(6) Uani 1 1 d . . .
H5 H 0.7371 0.3551 0.5361 0.040 Uiso 1 1 calc R . .
C2 C 0.4249(6) 0.3783(2) 0.35981(9) 0.0272(6) Uani 1 1 d . . .
C4 C 0.3944(7) 0.50153(19) 0.43917(8) 0.0272(6) Uani 1 1 d . . .
C12 C 0.1278(7) 0.2188(2) 0.23800(9) 0.0316(6) Uani 1 1 d . . .
H7 H 0.0327 0.1468 0.2291 0.038 Uiso 1 1 calc R . .
C13 C 0.1954(7) 0.3012(2) 0.19978(9) 0.0323(6) Uani 1 1 d . . .
C5 C 0.3007(8) 0.6003(2) 0.46828(9) 0.0354(7) Uani 1 1 d . . .
H2 H 0.1942 0.6628 0.4515 0.043 Uiso 1 1 calc R . .
C3 C 0.3189(8) 0.4901(2) 0.38361(9) 0.0323(6) Uani 1 1 d . . .
C7 C 0.5280(7) 0.5144(2) 0.54690(9) 0.0362(7) Uani 1 1 d . . .
C10 C 0.3450(7) 0.3512(2) 0.30424(9) 0.0294(6) Uani 1 1 d . . .
C15 C 0.4135(7) 0.4318(2) 0.26491(9) 0.0346(7) Uani 1 1 d . . .
H10 H 0.5095 0.5038 0.2736 0.041 Uiso 1 1 calc R . .
C11 C 0.2028(7) 0.2443(2) 0.28974(9) 0.0312(7) Uani 1 1 d . . .
H6 H 0.1568 0.1887 0.3153 0.037 Uiso 1 1 calc R . .
C6 C 0.3619(8) 0.6071(2) 0.52092(9) 0.0364(7) Uani 1 1 d . . .
H3 H 0.2934 0.6731 0.5395 0.044 Uiso 1 1 calc R . .
C14 C 0.3419(7) 0.4074(2) 0.21305(9) 0.0362(7) Uani 1 1 d . . .
H9 H 0.3923 0.4622 0.1873 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0473(12) 0.0298(9) 0.0288(9) -0.0008(8) -0.0030(9) 0.0103(10)
O4 0.0735(15) 0.0354(10) 0.0262(10) 0.0010(8) -0.0092(11) -0.0089(12)
O2 0.0761(15) 0.0392(11) 0.0347(10) -0.0003(9) -0.0138(12) 0.0193(12)
O3 0.0832(17) 0.0526(12) 0.0254(10) -0.0069(9) -0.0073(11) 0.0123(13)
C9 0.0318(16) 0.0263(13) 0.0304(14) -0.0022(11) 0.0004(12) -0.0008(13)
C1 0.0363(17) 0.0309(14) 0.0268(14) -0.0074(11) 0.0008(13) -0.0013(14)
C8 0.0411(17) 0.0300(13) 0.0289(14) 0.0053(11) -0.0045(14) 0.0043(14)
C2 0.0276(16) 0.0280(13) 0.0260(13) 0.0003(11) -0.0004(13) -0.0043(13)
C4 0.0300(15) 0.0246(12) 0.0270(13) 0.0003(11) -0.0013(12) -0.0012(13)
C12 0.0379(17) 0.0257(13) 0.0311(14) -0.0042(11) 0.0003(14) -0.0032(14)
C13 0.0357(17) 0.0355(14) 0.0257(14) -0.0021(12) -0.0013(13) 0.0015(14)
C5 0.0409(17) 0.0281(14) 0.0373(15) -0.0056(12) -0.0035(14) 0.0042(14)
C3 0.0347(16) 0.0302(14) 0.0320(14) 0.0033(12) 0.0000(13) -0.0013(14)
C7 0.0429(19) 0.0384(16) 0.0273(14) -0.0051(13) -0.0003(12) -0.0058(14)
C10 0.0296(16) 0.0303(14) 0.0284(13) -0.0025(11) -0.0007(13) 0.0039(13)
C15 0.0373(18) 0.0302(14) 0.0362(16) -0.0012(12) 0.0020(14) -0.0070(14)
C11 0.0347(17) 0.0297(13) 0.0291(14) 0.0023(11) 0.0007(13) 0.0005(12)
C6 0.0442(18) 0.0276(13) 0.0373(15) -0.0092(12) 0.0030(15) 0.0007(15)
C14 0.0461(18) 0.0325(15) 0.0300(15) 0.0050(12) 0.0010(15) -0.0007(15)

_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 C1 1.361(3) . ?
O1 C9 1.374(3) . ?
O4 C13 1.385(3) . ?
O4 H8 0.8200 . ?
O2 C3 1.235(3) . ?
O3 C7 1.356(3) . ?
O3 H4 0.8200 . ?
C9 C8 1.388(3) . ?
C9 C4 1.398(3) . ?
C1 C2 1.340(3) . ?
C1 H1 0.9300 . ?
C8 C7 1.374(3) . ?
C8 H5 0.9300 . ?
C2 C3 1.474(3) . ?
C2 C10 1.490(3) . ?
C4 C5 1.401(3) . ?
C4 C3 1.459(3) . ?
C12 C13 1.384(3) . ?
C12 C11 1.388(3) . ?
C12 H7 0.9300 . ?
C13 C14 1.381(3) . ?
C5 C6 1.372(3) . ?
C5 H2 0.9300 . ?
C7 C6 1.406(3) . ?
C10 C11 1.389(3) . ?
C10 C15 1.391(3) . ?
C15 C14 1.386(3) . ?
C15 H10 0.9300 . ?
C11 H6 0.9300 . ?
C6 H3 0.9300 . ?
C14 H9 0.9300 . ?

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
C1 O1 C9 118.27(19) . . ?
C13 O4 H8 109.5 . . ?
C7 O3 H4 109.5 . . ?
O1 C9 C8 116.3(2) . . ?
O1 C9 C4 121.3(2) . . ?
C8 C9 C4 122.4(2) . . ?
C2 C1 O1 125.9(2) . . ?
C2 C1 H1 117.0 . . ?
O1 C1 H1 117.0 . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H5 120.3 . . ?
C9 C8 H5 120.3 . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 C10 120.0(2) . . ?
C3 C2 C10 121.2(2) . . ?
C9 C4 C5 116.7(2) . . ?
C9 C4 C3 120.6(2) . . ?
C5 C4 C3 122.7(2) . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H7 120.2 . . ?
C11 C12 H7 120.2 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 O4 117.6(2) . . ?
C12 C13 O4 122.3(2) . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H2 119.2 . . ?
C4 C5 H2 119.2 . . ?
O2 C3 C4 122.7(2) . . ?
O2 C3 C2 122.1(2) . . ?
C4 C3 C2 115.2(2) . . ?
O3 C7 C8 117.7(2) . . ?
O3 C7 C6 122.7(2) . . ?
C8 C7 C6 119.6(2) . . ?
C11 C10 C15 117.6(2) . . ?
C11 C10 C2 121.3(2) . . ?
C15 C10 C2 121.0(2) . . ?
C14 C15 C10 121.5(2) . . ?
C14 C15 H10 119.2 . . ?
C10 C15 H10 119.2 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H6 119.2 . . ?
C10 C11 H6 119.2 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H3 119.9 . . ?
C7 C6 H3 119.9 . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H9 120.2 . . ?
C15 C14 H9 120.2 . . ?

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
O4 H8 O2 0.82 1.88 2.701(2) 175.9 3_545
O3 H4 O4 0.82 1.93 2.745(2) 173.6 2_565

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
