# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_d-koo2-r
_database_code_depnum_ccdc_archive 'CCDC 1818348'
loop_
_audit_author_name
_audit_author_address
'DURGA PRASAD KAROTHU' 'NEW YORK UNIVERSITY ABU DHABI'
_audit_update_record             
;
2018-06-29 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2018-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H18 O4'
_chemical_formula_sum            'C22 H18 O4'
_chemical_formula_weight         346.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'C 2 c b'
_space_group_name_Hall           'C -2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, -z'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1, -z+1/2'
'x+1/2, -y+1, z+1/2'

_cell_length_a                   7.4743(5)
_cell_length_b                   15.2098(8)
_cell_length_c                   14.2562(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1620.68(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2229
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.5970
_cell_measurement_theta_min      2.8560
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.001
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11806
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.001
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         2.678
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0839
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   64.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615  -99.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   72.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615 -113.0000  -47.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   64.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615  -99.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615   37.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615    0.0000 -150.0000 146

#__ type_ start__ end____ width___ exp.time_
  6 omega  -88.00    2.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177  -57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega  -96.00  -34.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177 -179.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega    0.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615   57.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   81.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615  179.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 10 omega   -8.00   92.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615   77.0000  -30.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0082578000
_diffrn_orient_matrix_UB_12      0.0289539000
_diffrn_orient_matrix_UB_13      -0.0387786000
_diffrn_orient_matrix_UB_21      -0.0076082000
_diffrn_orient_matrix_UB_22      0.0365624000
_diffrn_orient_matrix_UB_23      0.0306586000
_diffrn_orient_matrix_UB_31      0.0941799000
_diffrn_orient_matrix_UB_32      0.0003881000
_diffrn_orient_matrix_UB_33      0.0058223000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     1.002
_reflns_number_gt                1133
_reflns_number_total             1427
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1427
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0754
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0841P)²+5.1342P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1856
_refine_ls_wR_factor_ref         0.2021
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C1_$1
 1.54 with sigma of 0.02
 C5-C6 \\sim C1-C1_$1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C1) = Uanis(C2)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
4.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C7(H7), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
C11 C 0.5563(9) 0.3973(4) 0.0953(4) 0.0300(14) Uani 1 1 d . . . . .
H11 H 0.5163 0.4282 0.0431 0.036 Uiso 1 1 calc R . . . .
C5 C 0.5376(9) 0.4345(4) 0.1850(4) 0.0328(16) Uani 1 1 d D . . . .
O2 O 0.5849(10) 0.4197(3) 0.3522(3) 0.0598(19) Uani 1 1 d . . . . .
C9 C 0.6330(9) 0.3157(4) 0.0836(4) 0.0307(15) Uani 1 1 d . . . . .
C8 C 0.6918(9) 0.2697(4) 0.1632(4) 0.0348(16) Uani 1 1 d . . . . .
H8 H 0.7429 0.2144 0.1558 0.042 Uiso 1 1 calc R . . . .
O1 O 0.4134(8) 0.5705(3) 0.1319(3) 0.0488(15) Uani 1 1 d . . . . .
C7 C 0.6756(10) 0.3044(4) 0.2519(5) 0.0371(17) Uani 1 1 d . . . . .
H7 H 0.7171 0.2741 0.3041 0.045 Uiso 1 1 calc R . . . .
C10 C 0.6564(10) 0.2771(4) -0.0130(4) 0.0377(17) Uani 1 1 d . . . . .
H10A H 0.7118 0.2204 -0.0081 0.057 Uiso 1 1 calc R . . . .
H10B H 0.7308 0.3152 -0.0499 0.057 Uiso 1 1 calc R . . . .
H10C H 0.5417 0.2712 -0.0426 0.057 Uiso 1 1 calc R . . . .
C6 C 0.5940(11) 0.3877(4) 0.2610(5) 0.042(2) Uani 1 1 d D . . . .
C3 C 0.4551(14) 0.5522(5) 0.2947(5) 0.057(3) Uani 1 1 d . . . . .
H3 H 0.4047 0.6066 0.3086 0.068 Uiso 1 1 calc R . . . .
C2 C 0.518(2) 0.5013(5) 0.3652(5) 0.096(3) Uani 1 1 d . . . . .
C4 C 0.4647(10) 0.5234(4) 0.1979(5) 0.043(2) Uani 1 1 d . . . . .
C1 C 0.515(2) 0.5287(5) 0.4651(5) 0.096(3) Uani 1 1 d D . . . .
H1A H 0.6170 0.5668 0.4747 0.115 Uiso 1 1 calc R . . . .
H1B H 0.4090 0.5650 0.4730 0.115 Uiso 1 1 calc R . . . .


_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
C11 C5 1.404(9) . ?
C11 C9 1.377(9) . ?
C5 C6 1.364(9) . ?
C5 C4 1.470(9) . ?
O2 C6 1.389(8) . ?
O2 C2 1.350(9) . ?
C9 C8 1.404(9) . ?
C9 C10 1.507(9) . ?
C8 C7 1.375(9) . ?
O1 C4 1.242(8) . ?
C7 C6 1.411(9) . ?
C3 C2 1.354(12) . ?
C3 C4 1.450(10) . ?
C2 C1 1.485(10) . ?
C1 C1 1.324(12) 2_566 ?

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 C11 C5 121.0(6) . . ?
C11 C5 C4 121.4(6) . . ?
C6 C5 C11 118.8(5) . . ?
C6 C5 C4 119.7(6) . . ?
C2 O2 C6 118.0(6) . . ?
C11 C9 C8 118.7(5) . . ?
C11 C9 C10 120.7(5) . . ?
C8 C9 C10 120.6(5) . . ?
C7 C8 C9 121.6(6) . . ?
C8 C7 C6 117.9(6) . . ?
C5 C6 O2 123.0(6) . . ?
C5 C6 C7 121.9(6) . . ?
O2 C6 C7 115.0(6) . . ?
C2 C3 C4 121.1(7) . . ?
O2 C2 C3 123.6(7) . . ?
O2 C2 C1 113.4(7) . . ?
C3 C2 C1 123.0(7) . . ?
O1 C4 C5 123.4(6) . . ?
O1 C4 C3 122.1(6) . . ?
C3 C4 C5 114.5(6) . . ?
C1 C1 C2 122.5(9) 2_566 . ?

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
C11 C5 C6 O2 178.5(7) . . . . ?
C11 C5 C6 C7 2.1(10) . . . . ?
C11 C5 C4 O1 1.0(11) . . . . ?
C11 C5 C4 C3 -179.7(7) . . . . ?
C11 C9 C8 C7 -0.4(10) . . . . ?
C5 C11 C9 C8 0.3(10) . . . . ?
C5 C11 C9 C10 -178.6(7) . . . . ?
O2 C2 C1 C1 -22.5(15) . . . 2_566 ?
C9 C11 C5 C6 -1.1(9) . . . . ?
C9 C11 C5 C4 176.7(7) . . . . ?
C9 C8 C7 C6 1.3(11) . . . . ?
C8 C7 C6 C5 -2.2(11) . . . . ?
C8 C7 C6 O2 -178.9(7) . . . . ?
C10 C9 C8 C7 178.5(7) . . . . ?
C6 C5 C4 O1 178.8(7) . . . . ?
C6 C5 C4 C3 -1.8(10) . . . . ?
C6 O2 C2 C3 2.2(18) . . . . ?
C6 O2 C2 C1 179.9(9) . . . . ?
C3 C2 C1 C1 155.3(9) . . . 2_566 ?
C2 O2 C6 C5 -0.6(13) . . . . ?
C2 O2 C6 C7 176.0(10) . . . . ?
C2 C3 C4 C5 3.3(14) . . . . ?
C2 C3 C4 O1 -177.4(10) . . . . ?
C4 C5 C6 O2 0.6(11) . . . . ?
C4 C5 C6 C7 -175.8(7) . . . . ?
C4 C3 C2 O2 -3.6(19) . . . . ?
C4 C3 C2 C1 178.8(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
