# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_HIF-4
_database_code_depnum_ccdc_archive 'CCDC 1834972'
loop_
_audit_author_name
_audit_author_address
'Abdul Ajees Abdul Salam'
;Manipal Academy of Higher Education
India
;
_audit_update_record             
;
2018-04-05 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        '3-(2-Hydroxybenzyl) chroman-4-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.0638(14)
_cell_length_b                   8.9307(9)
_cell_length_c                   12.9341(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.465(12)
_cell_angle_gamma                90
_cell_volume                     1321.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17821
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'NUMABS (Rigaku 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17821
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         31.178
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3945
_reflns_number_gt                2277
_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       'CrystalClear SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0498P)²+0.3332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C10 C 0.14040(14) 0.88678(19) 0.18221(13) 0.0477(4) Uani 1 1 d . . . . .
C3 C 0.34338(15) 0.98825(19) 0.26680(14) 0.0494(4) Uani 1 1 d . . . . .
H3 H 0.380710 1.061063 0.323901 0.059 Uiso 1 1 calc R U . . .
C9 C 0.16148(15) 0.89497(19) 0.08250(13) 0.0484(4) Uani 1 1 d . . . . .
C1' C 0.54227(15) 0.89588(19) 0.26626(13) 0.0480(4) Uani 1 1 d . . . . .
O1 O 0.25617(11) 0.96527(15) 0.07007(10) 0.0605(4) Uani 1 1 d . . . . .
O2 O 0.21533(12) 0.93300(19) 0.37126(11) 0.0770(5) Uani 1 1 d . . . . .
C2' C 0.62994(15) 0.9565(2) 0.35485(14) 0.0500(4) Uani 1 1 d . . . . .
O3 O 0.60440(14) 0.9717(2) 0.44891(12) 0.0799(5) Uani 1 1 d . . . . .
C4 C 0.23059(15) 0.9379(2) 0.28186(14) 0.0511(4) Uani 1 1 d . . . . .
C3' C 0.73713(17) 0.9972(2) 0.34506(17) 0.0598(5) Uani 1 1 d . . . . .
H3' H 0.794956 1.036963 0.404540 0.072 Uiso 1 1 calc R U . . .
C11 C 0.42631(15) 0.8524(2) 0.27810(15) 0.0536(4) Uani 1 1 d . . . . .
H11A H 0.439323 0.806355 0.348886 0.064 Uiso 1 1 calc R U . . .
H11B H 0.389160 0.778747 0.222873 0.064 Uiso 1 1 calc R U . . .
C6' C 0.56604(19) 0.8786(2) 0.16912(16) 0.0658(5) Uani 1 1 d . . . . .
H6' H 0.509007 0.838538 0.109167 0.079 Uiso 1 1 calc R U . . .
C8 C 0.08493(17) 0.8289(2) -0.01015(15) 0.0630(5) Uani 1 1 d . . . . .
H8 H 0.100541 0.832652 -0.076054 0.076 Uiso 1 1 calc R U . . .
C5 C 0.03793(16) 0.8163(2) 0.18562(17) 0.0664(6) Uani 1 1 d . . . . .
H5 H 0.020997 0.812306 0.250888 0.080 Uiso 1 1 calc R U . . .
C7 C -0.01261(19) 0.7589(3) -0.00393(19) 0.0747(6) Uani 1 1 d . . . . .
H7 H -0.063178 0.714381 -0.066018 0.090 Uiso 1 1 calc R U . . .
C4' C 0.7576(2) 0.9785(2) 0.2475(2) 0.0735(6) Uani 1 1 d . . . . .
H4' H 0.829462 1.005996 0.241016 0.088 Uiso 1 1 calc R U . . .
C5' C 0.6727(2) 0.9196(3) 0.15916(19) 0.0807(7) Uani 1 1 d . . . . .
H5' H 0.686905 0.907343 0.093085 0.097 Uiso 1 1 calc R U . . .
C6 C -0.03836(18) 0.7525(3) 0.0927(2) 0.0788(7) Uani 1 1 d . . . . .
H6 H -0.106302 0.705693 0.095347 0.095 Uiso 1 1 calc R U . . .
C2 C 0.31533(16) 1.0646(2) 0.15749(15) 0.0569(5) Uani 1 1 d . . . . .
H2A H 0.266381 1.151178 0.156211 0.068 Uiso 1 1 calc R U . . .
H2B H 0.387188 1.099380 0.146989 0.068 Uiso 1 1 calc R U . . .
O3H H 0.669(2) 1.003(3) 0.507(2) 0.102(8) Uiso 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
C10 C9 1.393(2) . ?
C10 C5 1.400(2) . ?
C10 C4 1.471(2) . ?
C3 C4 1.503(2) . ?
C3 C2 1.508(2) . ?
C3 C11 1.550(2) . ?
C3 H3 0.9800 . ?
C9 O1 1.357(2) . ?
C9 C8 1.392(2) . ?
C1' C6' 1.383(2) . ?
C1' C2' 1.399(2) . ?
C1' C11 1.506(2) . ?
O1 C2 1.436(2) . ?
O2 C4 1.228(2) . ?
C2' O3 1.353(2) . ?
C2' C3' 1.387(2) . ?
O3 O3H 0.94(3) . ?
C3' C4' 1.370(3) . ?
C3' H3' 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6' C5' 1.382(3) . ?
C6' H6' 0.9300 . ?
C8 C7 1.357(3) . ?
C8 H8 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C7 C6 1.382(3) . ?
C7 H7 0.9300 . ?
C4' C5' 1.375(3) . ?
C4' H4' 0.9300 . ?
C5' H5' 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

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
C9 C10 C5 118.33(16) . . ?
C9 C10 C4 119.56(15) . . ?
C5 C10 C4 121.81(16) . . ?
C4 C3 C2 108.25(14) . . ?
C4 C3 C11 109.72(14) . . ?
C2 C3 C11 112.87(15) . . ?
C4 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C11 C3 H3 108.6 . . ?
O1 C9 C8 116.62(16) . . ?
O1 C9 C10 122.78(15) . . ?
C8 C9 C10 120.60(17) . . ?
C6' C1' C2' 117.81(17) . . ?
C6' C1' C11 122.03(17) . . ?
C2' C1' C11 120.16(16) . . ?
C9 O1 C2 114.80(14) . . ?
O3 C2' C3' 122.70(17) . . ?
O3 C2' C1' 116.53(16) . . ?
C3' C2' C1' 120.76(17) . . ?
C2' O3 O3H 112.6(15) . . ?
O2 C4 C10 121.60(16) . . ?
O2 C4 C3 122.99(16) . . ?
C10 C4 C3 115.33(15) . . ?
C4' C3' C2' 119.83(19) . . ?
C4' C3' H3' 120.1 . . ?
C2' C3' H3' 120.1 . . ?
C1' C11 C3 112.41(14) . . ?
C1' C11 H11A 109.1 . . ?
C3 C11 H11A 109.1 . . ?
C1' C11 H11B 109.1 . . ?
C3 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C5' C6' C1' 121.5(2) . . ?
C5' C6' H6' 119.3 . . ?
C1' C6' H6' 119.3 . . ?
C7 C8 C9 119.71(19) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C6 C5 C10 120.59(19) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C3' C4' C5' 120.5(2) . . ?
C3' C4' H4' 119.8 . . ?
C5' C4' H4' 119.8 . . ?
C4' C5' C6' 119.6(2) . . ?
C4' C5' H5' 120.2 . . ?
C6' C5' H5' 120.2 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O1 C2 C3 111.52(14) . . ?
O1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
O1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?

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
C5 C10 C9 O1 177.75(16) . . . . ?
C4 C10 C9 O1 -8.4(3) . . . . ?
C5 C10 C9 C8 -2.7(3) . . . . ?
C4 C10 C9 C8 171.13(17) . . . . ?
C8 C9 O1 C2 164.13(16) . . . . ?
C10 C9 O1 C2 -16.3(2) . . . . ?
C6' C1' C2' O3 -179.80(17) . . . . ?
C11 C1' C2' O3 0.5(2) . . . . ?
C6' C1' C2' C3' -0.2(3) . . . . ?
C11 C1' C2' C3' -179.95(16) . . . . ?
C9 C10 C4 O2 179.77(17) . . . . ?
C5 C10 C4 O2 -6.6(3) . . . . ?
C9 C10 C4 C3 -3.2(2) . . . . ?
C5 C10 C4 C3 170.43(17) . . . . ?
C2 C3 C4 O2 -147.56(18) . . . . ?
C11 C3 C4 O2 88.9(2) . . . . ?
C2 C3 C4 C10 35.5(2) . . . . ?
C11 C3 C4 C10 -88.08(18) . . . . ?
O3 C2' C3' C4' 179.82(18) . . . . ?
C1' C2' C3' C4' 0.3(3) . . . . ?
C6' C1' C11 C3 -98.3(2) . . . . ?
C2' C1' C11 C3 81.4(2) . . . . ?
C4 C3 C11 C1' -178.76(14) . . . . ?
C2 C3 C11 C1' 60.43(19) . . . . ?
C2' C1' C6' C5' 0.0(3) . . . . ?
C11 C1' C6' C5' 179.71(19) . . . . ?
O1 C9 C8 C7 -178.88(18) . . . . ?
C10 C9 C8 C7 1.6(3) . . . . ?
C9 C10 C5 C6 2.0(3) . . . . ?
C4 C10 C5 C6 -171.76(18) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
C2' C3' C4' C5' -0.1(3) . . . . ?
C3' C4' C5' C6' -0.1(3) . . . . ?
C1' C6' C5' C4' 0.2(3) . . . . ?
C8 C7 C6 C5 -1.2(4) . . . . ?
C10 C5 C6 C7 0.0(3) . . . . ?
C9 O1 C2 C3 51.4(2) . . . . ?
C4 C3 C2 O1 -59.98(19) . . . . ?
C11 C3 C2 O1 61.67(19) . . . . ?

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
O3 O3H O2 0.94(3) 1.83(3) 2.768(2) 174(2) 3_676
O3 O3H O2 0.94(3) 1.83(3) 2.768(2) 174(2) 3_676

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methonal'
####################################################################### 
# 
# 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_HIF-13
_database_code_depnum_ccdc_archive 'CCDC 1834992'
loop_
_audit_author_name
_audit_author_address
'Abdul Ajees Abdul Salam'
;Manipal Academy of Higher Education
India
;
_audit_update_record             
;
2018-04-05 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        '3-(2,4-Dimethoxybenzyl) chroman-4-one'
_chemical_name_common            '3-(2,4-Dimethoxybenzyl) chroman-4-one'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 O4'
_chemical_formula_sum            'C18 H18 O4'
_chemical_formula_weight         298.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0110 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                   7.385(7)
_cell_length_b                   27.33(3)
_cell_length_c                   8.364(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.630(11)
_cell_angle_gamma                90
_cell_volume                     1522(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11862
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_density_meas      None
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 72+'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11860
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.084
_diffrn_reflns_theta_max         25.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2768
_reflns_number_gt                1554
_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       'CrystalClear SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_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
O4' O 0.3619(3) 0.28671(7) 0.8429(2) 0.0685(6) Uani 1 1 d . . . . .
C1' C 0.6603(4) 0.34809(8) 0.5669(3) 0.0431(6) Uani 1 1 d . . . . .
O2 O 0.8603(3) 0.40279(7) 0.1943(3) 0.0732(7) Uani 1 1 d . . . . .
C3' C 0.3669(4) 0.30659(9) 0.5614(3) 0.0427(7) Uani 1 1 d . . . . .
H3' H 0.241243 0.292589 0.497068 0.051 Uiso 1 1 calc R U . . .
C2' C 0.4701(4) 0.32758(8) 0.4748(3) 0.0396(6) Uani 1 1 d . . . . .
C3 C 0.6973(4) 0.41804(9) 0.3828(3) 0.0428(6) Uani 1 1 d . . . . .
H3 H 0.551344 0.415332 0.314625 0.051 Uiso 1 1 calc R U . . .
C4 C 0.7834(4) 0.43217(10) 0.2554(3) 0.0468(7) Uani 1 1 d . . . . .
C11 C 0.7741(4) 0.36887(9) 0.4711(3) 0.0521(7) Uani 1 1 d . . . . .
H11A H 0.768249 0.345677 0.381150 0.062 Uiso 1 1 calc R U . . .
H11B H 0.913941 0.372423 0.554830 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7634(3) 0.48394(10) 0.2063(3) 0.0434(7) Uani 1 1 d . . . . .
C4' C 0.4529(4) 0.30664(9) 0.7452(3) 0.0477(7) Uani 1 1 d . . . . .
O1 O 0.6590(3) 0.50485(6) 0.4348(3) 0.0612(6) Uani 1 1 d . . . . .
C9 C 0.6998(4) 0.51749(10) 0.2967(3) 0.0483(7) Uani 1 1 d . . . . .
C2 C 0.7376(4) 0.45897(9) 0.5153(3) 0.0531(7) Uani 1 1 d . . . . .
H2A H 0.678986 0.450506 0.595384 0.064 Uiso 1 1 calc R U . . .
H2B H 0.881545 0.462087 0.585205 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7759(4) 0.54941(12) 0.0180(4) 0.0630(8) Uani 1 1 d . . . . .
H6 H 0.804874 0.560509 -0.073465 0.076 Uiso 1 1 calc R U . . .
C5' C 0.6380(4) 0.32752(10) 0.8402(3) 0.0546(8) Uani 1 1 d . . . . .
H5' H 0.695068 0.328117 0.963490 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7077(4) 0.58128(11) 0.1070(4) 0.0656(9) Uani 1 1 d . . . . .
H7 H 0.686747 0.613926 0.072415 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1758(5) 0.26277(11) 0.7528(4) 0.0716(9) Uani 1 1 d . . . . .
H13A H 0.077183 0.285779 0.678349 0.107 Uiso 1 1 calc R U . . .
H13B H 0.134004 0.249343 0.837563 0.107 Uiso 1 1 calc R U . . .
H13C H 0.189584 0.236887 0.681263 0.107 Uiso 1 1 calc R U . . .
C8 C 0.6702(4) 0.56588(10) 0.2452(4) 0.0596(8) Uani 1 1 d . . . . .
H8 H 0.624860 0.587970 0.304413 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8005(4) 0.50111(11) 0.0659(4) 0.0550(8) Uani 1 1 d . . . . .
H5 H 0.842765 0.479265 0.003717 0.066 Uiso 1 1 calc R U . . .
O2' O 0.3970(2) 0.32961(6) 0.2943(2) 0.0517(5) Uani 1 1 d . . . . .
C12 C 0.2015(4) 0.31106(11) 0.1908(3) 0.0642(8) Uani 1 1 d . . . . .
H12A H 0.197286 0.276962 0.216578 0.096 Uiso 1 1 calc R U . . .
H12B H 0.168594 0.315022 0.067266 0.096 Uiso 1 1 calc R U . . .
H12C H 0.106155 0.328638 0.218577 0.096 Uiso 1 1 calc R U . . .
C6' C 0.7376(4) 0.34753(10) 0.7498(4) 0.0558(8) Uani 1 1 d . . . . .
H6' H 0.863280 0.361395 0.815054 0.067 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
O4' C4' 1.375(3) . ?
O4' C13 1.410(3) . ?
C1' C6' 1.382(3) . ?
C1' C2' 1.394(3) . ?
C1' C11 1.501(3) . ?
O2 C4 1.216(3) . ?
C3' C2' 1.383(3) . ?
C3' C4' 1.386(3) . ?
C3' H3' 0.9300 . ?
C2' O2' 1.367(3) . ?
C3 C4 1.509(3) . ?
C3 C2 1.511(4) . ?
C3 C11 1.520(3) . ?
C3 H3 0.9800 . ?
C4 C10 1.463(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.393(4) . ?
C10 C5 1.397(3) . ?
C4' C5' 1.374(4) . ?
O1 C9 1.358(3) . ?
O1 C2 1.423(3) . ?
C9 C8 1.378(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C6 C5 1.368(4) . ?
C6 C7 1.375(4) . ?
C6 H6 0.9300 . ?
C5' C6' 1.376(3) . ?
C5' H5' 0.9300 . ?
C7 C8 1.367(4) . ?
C7 H7 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?
O2' C12 1.418(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C6' H6' 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
C4' O4' C13 118.7(2) . . ?
C6' C1' C2' 116.2(2) . . ?
C6' C1' C11 122.4(2) . . ?
C2' C1' C11 121.3(2) . . ?
C2' C3' C4' 119.2(2) . . ?
C2' C3' H3' 120.4 . . ?
C4' C3' H3' 120.4 . . ?
O2' C2' C3' 123.5(2) . . ?
O2' C2' C1' 114.6(2) . . ?
C3' C2' C1' 121.9(2) . . ?
C4 C3 C2 108.6(2) . . ?
C4 C3 C11 112.7(2) . . ?
C2 C3 C11 112.6(2) . . ?
C4 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C11 C3 H3 107.5 . . ?
O2 C4 C10 121.9(3) . . ?
O2 C4 C3 122.9(2) . . ?
C10 C4 C3 115.1(2) . . ?
C1' C11 C3 114.6(2) . . ?
C1' C11 H11A 108.6 . . ?
C3 C11 H11A 108.6 . . ?
C1' C11 H11B 108.6 . . ?
C3 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C9 C10 C5 118.0(3) . . ?
C9 C10 C4 120.0(2) . . ?
C5 C10 C4 121.9(2) . . ?
C5' C4' O4' 116.1(2) . . ?
C5' C4' C3' 120.4(2) . . ?
O4' C4' C3' 123.5(3) . . ?
C9 O1 C2 115.6(2) . . ?
O1 C9 C8 116.5(3) . . ?
O1 C9 C10 123.0(2) . . ?
C8 C9 C10 120.5(3) . . ?
O1 C2 C3 113.3(2) . . ?
O1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
O1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C4' C5' C6' 118.8(3) . . ?
C4' C5' H5' 120.6 . . ?
C6' C5' H5' 120.6 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
O4' C13 H13A 109.5 . . ?
O4' C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4' C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C6 C5 C10 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C2' O2' C12 118.09(19) . . ?
O2' C12 H12A 109.5 . . ?
O2' C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2' C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5' C6' C1' 123.3(3) . . ?
C5' C6' H6' 118.3 . . ?
C1' C6' H6' 118.3 . . ?

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
C4' C3' C2' O2' -179.5(2) . . . . ?
C4' C3' C2' C1' 1.2(4) . . . . ?
C6' C1' C2' O2' 178.8(2) . . . . ?
C11 C1' C2' O2' -1.9(3) . . . . ?
C6' C1' C2' C3' -1.8(4) . . . . ?
C11 C1' C2' C3' 177.4(2) . . . . ?
C2 C3 C4 O2 144.0(3) . . . . ?
C11 C3 C4 O2 18.5(3) . . . . ?
C2 C3 C4 C10 -37.5(3) . . . . ?
C11 C3 C4 C10 -163.0(2) . . . . ?
C6' C1' C11 C3 -106.1(3) . . . . ?
C2' C1' C11 C3 74.7(3) . . . . ?
C4 C3 C11 C1' -167.1(2) . . . . ?
C2 C3 C11 C1' 69.6(3) . . . . ?
O2 C4 C10 C9 -171.3(2) . . . . ?
C3 C4 C10 C9 10.2(3) . . . . ?
O2 C4 C10 C5 10.8(4) . . . . ?
C3 C4 C10 C5 -167.8(2) . . . . ?
C13 O4' C4' C5' -177.1(2) . . . . ?
C13 O4' C4' C3' 3.2(4) . . . . ?
C2' C3' C4' C5' 0.3(4) . . . . ?
C2' C3' C4' O4' 180.0(2) . . . . ?
C2 O1 C9 C8 -164.4(2) . . . . ?
C2 O1 C9 C10 17.1(3) . . . . ?
C5 C10 C9 O1 179.9(2) . . . . ?
C4 C10 C9 O1 1.8(4) . . . . ?
C5 C10 C9 C8 1.5(4) . . . . ?
C4 C10 C9 C8 -176.5(2) . . . . ?
C9 O1 C2 C3 -47.5(3) . . . . ?
C4 C3 C2 O1 56.9(3) . . . . ?
C11 C3 C2 O1 -177.5(2) . . . . ?
O4' C4' C5' C6' 179.2(2) . . . . ?
C3' C4' C5' C6' -1.1(4) . . . . ?
C5 C6 C7 C8 2.0(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
O1 C9 C8 C7 -179.9(2) . . . . ?
C10 C9 C8 C7 -1.4(4) . . . . ?
C7 C6 C5 C10 -1.9(4) . . . . ?
C9 C10 C5 C6 0.2(4) . . . . ?
C4 C10 C5 C6 178.1(2) . . . . ?
C3' C2' O2' C12 2.8(3) . . . . ?
C1' C2' O2' C12 -177.9(2) . . . . ?
C4' C5' C6' C1' 0.4(4) . . . . ?
C2' C1' C6' C5' 1.0(4) . . . . ?
C11 C1' C6' C5' -178.2(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
C3 H3 O2' 0.98 2.58 3.144(4) 116.8 .

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
