# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_A1K7A11
_database_code_depnum_ccdc_archive 'CCDC 2172047'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2022-05-11 deposited with the CCDC.	2023-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
(3E,5E)-3-benzylidene-5-(4-nitrobenzylidene)dihydro-2H-pyran-4(3H)-one
;
_chemical_formula_moiety         'C19 H15 N O4'
_chemical_formula_sum            'C19 H15 N O4'
_chemical_formula_iupac          'C19 H15 N O4'
_chemical_formula_weight         321.32

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'
N N 0.0061 0.0033 '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                   7.5877(4)
_cell_length_b                   7.2192(4)
_cell_length_c                   28.0023(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.5070(10)
_cell_angle_gamma                90
_cell_volume                     1533.83(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2850
_cell_measurement_theta_min      1.454
_cell_measurement_theta_max      26.729
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.186
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.988
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.901
_diffrn_reflns_number            24896
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.454
_diffrn_reflns_theta_max         26.729
_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
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3262
_reflns_number_gt                2850
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         3262
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.5545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2019)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;

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 -0.32508(16) 0.6976(2) -0.15387(5) 0.0703(4) Uani 1 1 d . . . . .
O2 O -0.16115(18) 0.5255(2) -0.19751(5) 0.0798(4) Uani 1 1 d . . . . .
O3 O 0.71000(14) 0.7812(2) 0.01037(4) 0.0708(4) Uani 1 1 d . . . . .
O4 O 0.30539(14) 0.68285(17) 0.09411(4) 0.0539(3) Uani 1 1 d . . . . .
N1 N -0.18561(17) 0.6204(2) -0.16233(5) 0.0513(3) Uani 1 1 d . . . . .
C1 C 0.23546(17) 0.69275(19) -0.06442(5) 0.0368(3) Uani 1 1 d . . . . .
C2 C 0.26412(18) 0.6197(2) -0.10970(5) 0.0411(3) Uani 1 1 d . . . . .
H2 H 0.378162 0.588637 -0.118585 0.049 Uiso 1 1 calc R U . . .
C3 C 0.12725(19) 0.5924(2) -0.14169(5) 0.0423(3) Uani 1 1 d . . . . .
H3 H 0.147391 0.541166 -0.171616 0.051 Uiso 1 1 calc R U . . .
C4 C -0.03952(18) 0.64298(19) -0.12818(5) 0.0393(3) Uani 1 1 d . . . . .
C5 C -0.07372(19) 0.7177(2) -0.08424(5) 0.0454(3) Uani 1 1 d . . . . .
H5 H -0.187833 0.751522 -0.076101 0.054 Uiso 1 1 calc R U . . .
C6 C 0.06367(19) 0.7418(2) -0.05224(5) 0.0448(3) Uani 1 1 d . . . . .
H6 H 0.041600 0.791403 -0.022231 0.054 Uiso 1 1 calc R U . . .
C7 C 0.38933(18) 0.7217(2) -0.03336(5) 0.0403(3) Uani 1 1 d . . . . .
H7 H 0.496814 0.723396 -0.049062 0.048 Uiso 1 1 calc R U . . .
C8 C 0.40033(17) 0.74602(19) 0.01377(5) 0.0382(3) Uani 1 1 d . . . . .
C9 C 0.57861(18) 0.7828(2) 0.03507(5) 0.0420(3) Uani 1 1 d . . . . .
C10 C 0.58892(18) 0.82720(19) 0.08686(5) 0.0372(3) Uani 1 1 d . . . . .
C11 C 0.41995(19) 0.8177(2) 0.11433(5) 0.0461(4) Uani 1 1 d . . . . .
H11A H 0.445436 0.786103 0.147338 0.055 Uiso 1 1 calc R U . . .
H11B H 0.362768 0.937884 0.113781 0.055 Uiso 1 1 calc R U . . .
C12 C 0.24838(19) 0.7373(3) 0.04774(5) 0.0490(4) Uani 1 1 d . . . . .
H12A H 0.192562 0.857981 0.049484 0.059 Uiso 1 1 calc R U . . .
H12B H 0.161719 0.649494 0.035877 0.059 Uiso 1 1 calc R U . . .
C13 C 0.74777(18) 0.86477(19) 0.10560(5) 0.0392(3) Uani 1 1 d . . . . .
H13 H 0.840759 0.853469 0.084384 0.047 Uiso 1 1 calc R U . . .
C14 C 0.79921(18) 0.92056(19) 0.15385(5) 0.0382(3) Uani 1 1 d . . . . .
C15 C 0.9736(2) 0.8908(2) 0.16801(5) 0.0474(4) Uani 1 1 d . . . . .
H15 H 1.050513 0.832369 0.147173 0.057 Uiso 1 1 calc R U . . .
C16 C 1.0341(2) 0.9463(3) 0.21224(6) 0.0588(4) Uani 1 1 d . . . . .
H16 H 1.150418 0.923623 0.221233 0.071 Uiso 1 1 calc R U . . .
C17 C 0.9228(3) 1.0350(3) 0.24302(6) 0.0609(5) Uani 1 1 d . . . . .
H17 H 0.963743 1.073189 0.272828 0.073 Uiso 1 1 calc R U . . .
C18 C 0.7506(3) 1.0674(2) 0.22986(6) 0.0556(4) Uani 1 1 d . . . . .
H18 H 0.675650 1.127991 0.250797 0.067 Uiso 1 1 calc R U . . .
C19 C 0.6881(2) 1.0105(2) 0.18572(5) 0.0453(3) Uani 1 1 d . . . . .
H19 H 0.571210 1.032422 0.177244 0.054 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 N1 1.2209(18) . ?
O2 N1 1.2156(18) . ?
O3 C9 1.2185(18) . ?
O4 C11 1.4197(18) . ?
O4 C12 1.4204(17) . ?
N1 C4 1.4666(18) . ?
C1 C2 1.3918(19) . ?
C1 C6 1.3960(19) . ?
C1 C7 1.4647(18) . ?
C2 C3 1.3798(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3334(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.4974(19) . ?
C8 C12 1.502(2) . ?
C9 C10 1.4863(19) . ?
C10 C13 1.3382(19) . ?
C10 C11 1.5025(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.4597(19) . ?
C13 H13 0.9300 . ?
C14 C19 1.393(2) . ?
C14 C15 1.395(2) . ?
C15 C16 1.377(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(2) . ?
C18 H18 0.9300 . ?
C19 H19 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
C11 O4 C12 110.80(12) . . ?
O2 N1 O1 123.58(14) . . ?
O2 N1 C4 118.10(13) . . ?
O1 N1 C4 118.31(14) . . ?
C2 C1 C6 118.19(12) . . ?
C2 C1 C7 117.70(12) . . ?
C6 C1 C7 124.04(13) . . ?
C3 C2 C1 121.52(13) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 C3 C2 118.25(13) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 122.28(13) . . ?
C5 C4 N1 118.76(13) . . ?
C3 C4 N1 118.94(13) . . ?
C4 C5 C6 119.01(13) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 120.74(13) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C1 130.48(13) . . ?
C8 C7 H7 114.8 . . ?
C1 C7 H7 114.8 . . ?
C7 C8 C9 117.78(13) . . ?
C7 C8 C12 125.42(13) . . ?
C9 C8 C12 116.80(12) . . ?
O3 C9 C10 121.31(13) . . ?
O3 C9 C8 120.85(13) . . ?
C10 C9 C8 117.80(12) . . ?
C13 C10 C9 117.76(12) . . ?
C13 C10 C11 125.32(13) . . ?
C9 C10 C11 116.86(12) . . ?
O4 C11 C10 110.45(12) . . ?
O4 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
O4 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O4 C12 C8 111.17(12) . . ?
O4 C12 H12A 109.4 . . ?
C8 C12 H12A 109.4 . . ?
O4 C12 H12B 109.4 . . ?
C8 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C10 C13 C14 130.66(13) . . ?
C10 C13 H13 114.7 . . ?
C14 C13 H13 114.7 . . ?
C19 C14 C15 117.87(13) . . ?
C19 C14 C13 124.27(13) . . ?
C15 C14 C13 117.77(13) . . ?
C16 C15 C14 121.26(15) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.93(16) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.04(15) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.47(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.43(15) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?

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 C3 -1.3(2) . . . . ?
C7 C1 C2 C3 -178.32(13) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 N1 178.06(13) . . . . ?
O2 N1 C4 C5 -167.28(16) . . . . ?
O1 N1 C4 C5 12.6(2) . . . . ?
O2 N1 C4 C3 14.1(2) . . . . ?
O1 N1 C4 C3 -165.99(15) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
N1 C4 C5 C6 -179.01(14) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C7 C1 C6 C5 177.14(14) . . . . ?
C2 C1 C7 C8 -162.09(15) . . . . ?
C6 C1 C7 C8 21.0(2) . . . . ?
C1 C7 C8 C9 -176.74(14) . . . . ?
C1 C7 C8 C12 4.1(3) . . . . ?
C7 C8 C9 O3 -3.6(2) . . . . ?
C12 C8 C9 O3 175.64(16) . . . . ?
C7 C8 C9 C10 174.46(13) . . . . ?
C12 C8 C9 C10 -6.3(2) . . . . ?
O3 C9 C10 C13 -0.2(2) . . . . ?
C8 C9 C10 C13 -178.32(13) . . . . ?
O3 C9 C10 C11 -177.59(16) . . . . ?
C8 C9 C10 C11 4.3(2) . . . . ?
C12 O4 C11 C10 -66.43(16) . . . . ?
C13 C10 C11 O4 -146.79(14) . . . . ?
C9 C10 C11 O4 30.34(18) . . . . ?
C11 O4 C12 C8 64.52(17) . . . . ?
C7 C8 C12 O4 152.65(15) . . . . ?
C9 C8 C12 O4 -26.6(2) . . . . ?
C9 C10 C13 C14 176.86(14) . . . . ?
C11 C10 C13 C14 -6.0(3) . . . . ?
C10 C13 C14 C19 -24.8(2) . . . . ?
C10 C13 C14 C15 158.80(15) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
C13 C14 C15 C16 177.39(15) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C14 -0.4(2) . . . . ?
C15 C14 C19 C18 -0.1(2) . . . . ?
C13 C14 C19 C18 -176.47(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
C5 H5 O3 0.93 2.56 3.1620(18) 123.0 1_455 yes
C2 H2 O1 0.93 2.59 3.4102(19) 147.5 1_655 yes

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_A1K10A10
_database_code_depnum_ccdc_archive 'CCDC 2172048'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2022-05-11 deposited with the CCDC.	2023-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
(2E,5E)-2-benzylidene-5-(2,3-dimethoxybenzylidene)cyclopentanone
;
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_iupac          'C21 H20 O3'
_chemical_formula_weight         320.37

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   16.154(2)
_cell_length_b                   6.9813(10)
_cell_length_c                   28.997(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3270.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2623
_cell_measurement_theta_min      1.404
_cell_measurement_theta_max      25.347
_cell_measurement_temperature    150(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.194
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.988
_exptl_special_details           
;
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.301
_diffrn_reflns_number            57033
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.404
_diffrn_reflns_theta_max         25.347
_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
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             2992
_reflns_number_gt                2623
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0146P)²+4.2071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2019)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;

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 0.10409(10) 0.1072(2) 0.16956(6) 0.0408(4) Uani 1 1 d . . . . .
O2 O 0.14532(11) 0.4216(3) 0.21617(6) 0.0489(5) Uani 1 1 d . . . . .
O3 O 0.02606(10) -0.2416(3) 0.03233(6) 0.0428(4) Uani 1 1 d . . . . .
C1 C 0.12653(14) 0.2649(3) 0.09683(9) 0.0361(5) Uani 1 1 d . . . . .
C2 C 0.12498(14) 0.2710(3) 0.14481(9) 0.0356(5) Uani 1 1 d . . . . .
C3 C 0.14809(14) 0.4352(4) 0.16897(9) 0.0388(6) Uani 1 1 d . . . . .
C4 C 0.17201(14) 0.5974(4) 0.14479(10) 0.0431(6) Uani 1 1 d . . . . .
H4 H 0.1873 0.7104 0.1609 0.052 Uiso 1 1 calc R U . . .
C5 C 0.17355(14) 0.5940(3) 0.09711(10) 0.0429(6) Uani 1 1 d . . . . .
H5 H 0.1902 0.7052 0.0807 0.051 Uiso 1 1 calc R U . . .
C6 C 0.15136(14) 0.4322(3) 0.07323(10) 0.0415(6) Uani 1 1 d . . . . .
H6 H 0.1527 0.4328 0.0405 0.050 Uiso 1 1 calc R U . . .
C7 C 0.02382(16) 0.1177(4) 0.19020(9) 0.0463(6) Uani 1 1 d . . . . .
H7A H 0.0171 0.0122 0.2122 0.069 Uiso 1 1 calc R U . . .
H7B H -0.0186 0.1080 0.1662 0.069 Uiso 1 1 calc R U . . .
H7C H 0.0179 0.2401 0.2064 0.069 Uiso 1 1 calc R U . . .
C8 C 0.16035(18) 0.5934(4) 0.24129(10) 0.0568(8) Uani 1 1 d . . . . .
H8A H 0.1538 0.5687 0.2744 0.085 Uiso 1 1 calc R U . . .
H8B H 0.1208 0.6919 0.2316 0.085 Uiso 1 1 calc R U . . .
H8C H 0.2168 0.6379 0.2352 0.085 Uiso 1 1 calc R U . . .
C9 C 0.10013(14) 0.0913(3) 0.07268(9) 0.0370(6) Uani 1 1 d . . . . .
H9 H 0.0696 0.0026 0.0908 0.044 Uiso 1 1 calc R U . . .
C10 C 0.11260(14) 0.0394(3) 0.02889(8) 0.0353(5) Uani 1 1 d . . . . .
C11 C 0.07701(13) -0.1422(3) 0.01166(8) 0.0356(6) Uani 1 1 d . . . . .
C12 C 0.11160(13) -0.1831(3) -0.03459(8) 0.0349(5) Uani 1 1 d . . . . .
C13 C 0.16969(14) -0.0223(3) -0.04778(8) 0.0381(6) Uani 1 1 d . . . . .
H13A H 0.1538 0.0325 -0.0780 0.046 Uiso 1 1 calc R U . . .
H13B H 0.2273 -0.0699 -0.0498 0.046 Uiso 1 1 calc R U . . .
C14 C 0.16204(15) 0.1303(3) -0.00939(8) 0.0398(6) Uani 1 1 d . . . . .
H14A H 0.2175 0.1682 0.0019 0.048 Uiso 1 1 calc R U . . .
H14B H 0.1334 0.2457 -0.0212 0.048 Uiso 1 1 calc R U . . .
C15 C 0.08736(14) -0.3402(3) -0.05773(8) 0.0368(6) Uani 1 1 d . . . . .
H15 H 0.0499 -0.4203 -0.0414 0.044 Uiso 1 1 calc R U . . .
C16 C 0.10911(14) -0.4078(3) -0.10365(8) 0.0344(5) Uani 1 1 d . . . . .
C17 C 0.06035(15) -0.5514(3) -0.12342(9) 0.0408(6) Uani 1 1 d . . . . .
H17 H 0.0161 -0.6052 -0.1062 0.049 Uiso 1 1 calc R U . . .
C18 C 0.07545(16) -0.6163(4) -0.16752(10) 0.0467(7) Uani 1 1 d . . . . .
H18 H 0.0404 -0.7112 -0.1806 0.056 Uiso 1 1 calc R U . . .
C19 C 0.14073(16) -0.5452(4) -0.19294(10) 0.0450(6) Uani 1 1 d . . . . .
H19 H 0.1509 -0.5906 -0.2233 0.054 Uiso 1 1 calc R U . . .
C20 C 0.19114(15) -0.4067(4) -0.17346(9) 0.0425(6) Uani 1 1 d . . . . .
H20 H 0.2369 -0.3586 -0.1905 0.051 Uiso 1 1 calc R U . . .
C21 C 0.17610(14) -0.3380(3) -0.12996(9) 0.0380(6) Uani 1 1 d . . . . .
H21 H 0.2112 -0.2422 -0.1174 0.046 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 1.391(3) . ?
O1 C7 1.430(3) . ?
O2 C3 1.373(3) . ?
O2 C8 1.424(3) . ?
O3 C11 1.232(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.412(3) . ?
C1 C9 1.463(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.336(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.479(3) . ?
C10 C14 1.508(3) . ?
C11 C12 1.481(3) . ?
C12 C15 1.344(3) . ?
C12 C13 1.512(3) . ?
C13 C14 1.546(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.456(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.398(3) . ?
C16 C21 1.411(3) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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 C7 113.19(18) . . ?
C3 O2 C8 116.5(2) . . ?
C2 C1 C6 117.7(2) . . ?
C2 C1 C9 119.9(2) . . ?
C6 C1 C9 122.4(2) . . ?
O1 C2 C1 119.7(2) . . ?
O1 C2 C3 118.8(2) . . ?
C1 C2 C3 121.5(2) . . ?
O2 C3 C4 124.8(2) . . ?
O2 C3 C2 115.8(2) . . ?
C4 C3 C2 119.5(2) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 129.5(2) . . ?
C10 C9 H9 115.3 . . ?
C1 C9 H9 115.3 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 C14 131.7(2) . . ?
C11 C10 C14 108.5(2) . . ?
O3 C11 C10 125.3(2) . . ?
O3 C11 C12 125.7(2) . . ?
C10 C11 C12 108.95(19) . . ?
C15 C12 C11 120.0(2) . . ?
C15 C12 C13 131.3(2) . . ?
C11 C12 C13 108.7(2) . . ?
C12 C13 C14 106.26(19) . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
C14 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C10 C14 C13 106.41(19) . . ?
C10 C14 H14A 110.4 . . ?
C13 C14 H14A 110.4 . . ?
C10 C14 H14B 110.4 . . ?
C13 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C12 C15 C16 130.6(2) . . ?
C12 C15 H15 114.7 . . ?
C16 C15 H15 114.7 . . ?
C17 C16 C21 117.3(2) . . ?
C17 C16 C15 118.1(2) . . ?
C21 C16 C15 124.6(2) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 118.9(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?

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
C7 O1 C2 C1 -107.6(2) . . . . ?
C7 O1 C2 C3 75.7(3) . . . . ?
C6 C1 C2 O1 -177.5(2) . . . . ?
C9 C1 C2 O1 4.7(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C9 C1 C2 C3 -178.7(2) . . . . ?
C8 O2 C3 C4 6.5(3) . . . . ?
C8 O2 C3 C2 -173.7(2) . . . . ?
O1 C2 C3 O2 -2.2(3) . . . . ?
C1 C2 C3 O2 -178.8(2) . . . . ?
O1 C2 C3 C4 177.6(2) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
O2 C3 C4 C5 179.1(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C9 C1 C6 C5 178.2(2) . . . . ?
C2 C1 C9 C10 -164.3(2) . . . . ?
C6 C1 C9 C10 18.0(4) . . . . ?
C1 C9 C10 C11 -177.9(2) . . . . ?
C1 C9 C10 C14 5.1(4) . . . . ?
C9 C10 C11 O3 10.7(3) . . . . ?
C14 C10 C11 O3 -171.6(2) . . . . ?
C9 C10 C11 C12 -170.1(2) . . . . ?
C14 C10 C11 C12 7.6(2) . . . . ?
O3 C11 C12 C15 0.2(3) . . . . ?
C10 C11 C12 C15 -179.0(2) . . . . ?
O3 C11 C12 C13 178.2(2) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C15 C12 C13 C14 171.9(2) . . . . ?
C11 C12 C13 C14 -5.8(2) . . . . ?
C9 C10 C14 C13 166.3(2) . . . . ?
C11 C10 C14 C13 -11.0(2) . . . . ?
C12 C13 C14 C10 10.2(2) . . . . ?
C11 C12 C15 C16 177.3(2) . . . . ?
C13 C12 C15 C16 -0.2(4) . . . . ?
C12 C15 C16 C17 -165.2(2) . . . . ?
C12 C15 C16 C21 14.6(4) . . . . ?
C21 C16 C17 C18 -2.5(3) . . . . ?
C15 C16 C17 C18 177.3(2) . . . . ?
C16 C17 C18 C19 2.0(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C21 -1.1(4) . . . . ?
C19 C20 C21 C16 0.5(4) . . . . ?
C17 C16 C21 C20 1.3(3) . . . . ?
C15 C16 C21 C20 -178.5(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
C14 H14B O3 0.99 2.60 3.206(3) 119.9 5
C17 H17 O3 0.95 2.49 3.319(3) 146.0 5_545

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042

