# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_dbr005_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2127414'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2021-09-30
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 O3'
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.29
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5942(3)
_cell_length_b                   10.5681(6)
_cell_length_c                   11.9447(6)
_cell_angle_alpha                102.226(2)
_cell_angle_beta                 92.692(2)
_cell_angle_gamma                90.534(2)
_cell_volume                     689.26(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1084 before and 0.0842 after correction. The Ratio of minimum to maximum transmission is 0.9012. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41553
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         1.747
_diffrn_ambient_temperature      299.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2214
_reflns_number_total             3181
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0745
_refine_ls_restrained_S_all      1.140
_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)+(0.1214P)²+0.0219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.1981
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3A), C2(H2), C17(H17), C16(H16), C13(H13), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.76851(19) 0.47218(11) 0.56293(10) 0.0452(4) Uani 1 1 d . . . . .
O3 O 0.91754(19) 0.31900(11) 0.37122(10) 0.0441(3) Uani 1 1 d . . . . .
H3 H 0.969506 0.388923 0.408356 0.066 Uiso 1 1 calc GR . . . .
O2 O 0.2950(2) 0.02847(12) 0.39253(12) 0.0596(4) Uani 1 1 d . . . . .
C9 C 0.7282(3) 0.28142(14) 0.42217(13) 0.0346(4) Uani 1 1 d . . . . .
C5 C 0.4525(3) 0.33112(15) 0.58765(13) 0.0342(4) Uani 1 1 d . . . . .
C8 C 0.6094(3) 0.16986(14) 0.37579(13) 0.0356(4) Uani 1 1 d . . . . .
C10 C 0.6576(2) 0.37017(14) 0.52855(13) 0.0335(4) Uani 1 1 d . . . . .
C4 C 0.3326(3) 0.21421(15) 0.54292(13) 0.0354(4) Uani 1 1 d . . . . .
C7 C 0.4057(3) 0.12916(15) 0.43350(14) 0.0381(4) Uani 1 1 d . . . . .
C12 C 0.6280(3) 0.14198(14) 0.16005(14) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.1779(3) 0.38018(18) 0.74071(14) 0.0461(4) Uani 1 1 d . . . . .
C6 C 0.3756(3) 0.41371(16) 0.68577(14) 0.0410(4) Uani 1 1 d . . . . .
H6 H 0.456890 0.491794 0.714772 0.049 Uiso 1 1 calc R . . . .
C3 C 0.1406(3) 0.17853(17) 0.59881(15) 0.0433(4) Uani 1 1 d . . . . .
H3A H 0.061978 0.099407 0.570891 0.052 Uiso 1 1 calc R . . . .
C11 C 0.6821(3) 0.08606(16) 0.26475(14) 0.0426(4) Uani 1 1 d . . . . .
H11A H 0.600522 0.002645 0.254030 0.051 Uiso 1 1 calc R . . . .
H11B H 0.852685 0.071374 0.270748 0.051 Uiso 1 1 calc R . . . .
C2 C 0.0648(3) 0.26136(18) 0.69714(15) 0.0475(5) Uani 1 1 d . . . . .
H2 H -0.064329 0.236440 0.734345 0.057 Uiso 1 1 calc R . . . .
C17 C 0.7785(4) 0.1188(2) 0.07067(17) 0.0616(6) Uani 1 1 d . . . . .
H17 H 0.917537 0.072999 0.077609 0.074 Uiso 1 1 calc R . . . .
C16 C 0.7292(4) 0.1616(2) -0.02889(18) 0.0726(6) Uani 1 1 d . . . . .
H16 H 0.832123 0.142351 -0.088821 0.087 Uiso 1 1 calc R . . . .
C13 C 0.4276(3) 0.2129(2) 0.14788(17) 0.0598(5) Uani 1 1 d . . . . .
H13 H 0.323228 0.231295 0.207275 0.072 Uiso 1 1 calc R . . . .
C15 C 0.5314(4) 0.2316(2) -0.03990(18) 0.0669(6) Uani 1 1 d . . . . .
H15 H 0.499145 0.261968 -0.106545 0.080 Uiso 1 1 calc R . . . .
C14 C 0.3791(4) 0.2572(2) 0.0484(2) 0.0731(7) Uani 1 1 d . . . . .
H14 H 0.242150 0.304703 0.041362 0.088 Uiso 1 1 calc R . . . .
C18 C 0.0856(4) 0.4721(2) 0.84279(19) 0.0703(6) Uani 1 1 d . . . . .
H18A H 0.205147 0.485732 0.904713 0.105 Uiso 1 1 calc GR . . . .
H18B H -0.056942 0.435922 0.866272 0.105 Uiso 1 1 calc GR . . . .
H18C H 0.049750 0.553270 0.822505 0.105 Uiso 1 1 calc GR . . . .


_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 C10 1.2215(18) . ?
O3 C9 1.3433(17) . ?
O2 C7 1.2222(19) . ?
C9 C8 1.347(2) . ?
C9 C10 1.483(2) . ?
C5 C10 1.475(2) . ?
C5 C4 1.390(2) . ?
C5 C6 1.393(2) . ?
C8 C7 1.466(2) . ?
C8 C11 1.506(2) . ?
C4 C7 1.498(2) . ?
C4 C3 1.381(2) . ?
C12 C11 1.512(2) . ?
C12 C17 1.373(3) . ?
C12 C13 1.373(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.388(3) . ?
C1 C18 1.505(3) . ?
C3 C2 1.394(3) . ?
C17 C16 1.376(3) . ?
C16 C15 1.353(3) . ?
C13 C14 1.383(3) . ?
C15 C14 1.371(3) . ?

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
O3 C9 C8 120.49(14) . . ?
O3 C9 C10 116.46(13) . . ?
C8 C9 C10 123.04(14) . . ?
C4 C5 C10 119.76(14) . . ?
C4 C5 C6 120.52(14) . . ?
C6 C5 C10 119.69(14) . . ?
C9 C8 C7 119.81(14) . . ?
C9 C8 C11 120.91(14) . . ?
C7 C8 C11 119.29(14) . . ?
O1 C10 C9 119.24(13) . . ?
O1 C10 C5 122.83(14) . . ?
C5 C10 C9 117.92(13) . . ?
C5 C4 C7 120.57(13) . . ?
C3 C4 C5 119.34(15) . . ?
C3 C4 C7 120.06(15) . . ?
O2 C7 C8 120.77(15) . . ?
O2 C7 C4 120.37(14) . . ?
C8 C7 C4 118.84(14) . . ?
C17 C12 C11 119.86(15) . . ?
C13 C12 C11 122.67(15) . . ?
C13 C12 C17 117.43(16) . . ?
C6 C1 C18 120.75(17) . . ?
C2 C1 C6 118.31(16) . . ?
C2 C1 C18 120.92(17) . . ?
C1 C6 C5 120.48(16) . . ?
C4 C3 C2 119.87(16) . . ?
C8 C11 C12 114.49(13) . . ?
C1 C2 C3 121.43(15) . . ?
C12 C17 C16 121.83(18) . . ?
C15 C16 C17 120.24(19) . . ?
C12 C13 C14 120.83(18) . . ?
C16 C15 C14 119.18(19) . . ?
C15 C14 C13 120.47(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dbr23
_database_code_depnum_ccdc_archive 'CCDC 2127416'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2021-04-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O4'
_chemical_formula_sum            'C17 H12 O4'
_chemical_formula_weight         280.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.4584(4)
_cell_length_b                   3.9248(2)
_cell_length_c                   31.2078(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.455(4)
_cell_angle_gamma                90
_cell_volume                     1275.19(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3769
_cell_measurement_temperature    298.0(7)
_cell_measurement_theta_max      26.5150
_cell_measurement_theta_min      2.4480
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            9480
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.937
_diffrn_reflns_theta_min         1.956
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.0(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  89.00   0.50   10.08    --   16.22  30.00 -30.00  198
  2  ω     67.00  92.00   0.50   10.08    --   16.22   8.00 -56.00   50
  3  ω     41.00  66.00   0.50   10.08    --  -14.97   8.00 -56.00   50
  4  ω     -5.00  33.00   0.50   10.08    --   16.22   8.00 -56.00   76
  5  ω    -40.00  -8.00   0.50   10.08    --  -14.97   8.00 -56.00   64
  6  ω     17.00  68.00   0.50   10.08    --   16.22-125.00   0.00  102
  7  ω    -52.00 -13.00   0.50   10.08    --   16.22   8.00 -56.00   78
  8  ω    -36.00  20.00   0.50   10.08    --  -14.97 -94.00-120.00  112
  9  ω    -36.00  38.00   0.50   10.08    --   16.22 -94.00-150.00  148
 10  ω    -66.00 -39.00   0.50   10.08    --  -14.97 125.00-180.00   54
 11  ω    -55.00 -28.00   0.50   10.08    --  -14.97 125.00-150.00   54
 12  ω    -80.00   6.00   0.50   10.08    --  -14.97 -30.00 120.00  172
 13  ω     -9.00  16.00   0.50   10.08    --   16.22  -8.00 128.00   50
 14  ω    -40.00 -15.00   0.50   10.08    --  -14.97  -8.00 128.00   50
 15  ω    -44.00 -19.00   0.50   10.08    --  -14.97 -61.00 120.00   50
 16  ω    -72.00 -47.00   0.50   10.08    --  -14.97 -61.00 120.00   50
 17  ω    -52.00 -25.00   0.50   10.08    --  -14.97 125.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0398719000
_diffrn_orient_matrix_UB_12      -0.0268364000
_diffrn_orient_matrix_UB_13      0.0193845000
_diffrn_orient_matrix_UB_21      -0.0552007000
_diffrn_orient_matrix_UB_22      -0.0121278000
_diffrn_orient_matrix_UB_23      0.0114710000
_diffrn_orient_matrix_UB_31      -0.0022399000
_diffrn_orient_matrix_UB_32      -0.1783697000
_diffrn_orient_matrix_UB_33      -0.0036815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1741
_reflns_number_total             2604
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1474
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C5(H5), C1(H1), C14(H14), C2(H2), C4(H4), C3(H3A)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O3 O 0.56228(12) 0.0463(3) 0.45751(4) 0.0500(4) Uani 1 1 d . . . . .
O4 O 0.34540(10) 0.5131(4) 0.33208(4) 0.0547(4) Uani 1 1 d . . . . .
O2 O 0.77663(11) 0.1059(3) 0.42142(4) 0.0551(4) Uani 1 1 d . . . . .
O1 O 0.91325(11) 0.6551(4) 0.28259(4) 0.0547(4) Uani 1 1 d . . . . .
C10 C 0.68531(15) 0.3830(4) 0.35802(5) 0.0355(4) Uani 1 1 d . . . . .
C11 C 0.57051(15) 0.4833(4) 0.33560(5) 0.0355(4) Uani 1 1 d . . . . .
C6 C 0.32105(15) 0.2672(5) 0.41744(5) 0.0369(4) Uani 1 1 d . . . . .
C9 C 0.68195(15) 0.2189(4) 0.40015(5) 0.0376(4) Uani 1 1 d . . . . .
C8 C 0.55612(15) 0.1902(5) 0.41811(5) 0.0373(4) Uani 1 1 d . . . . .
C12 C 0.44526(15) 0.4345(4) 0.35333(5) 0.0386(5) Uani 1 1 d . . . . .
C16 C 0.80255(16) 0.4343(4) 0.34153(5) 0.0398(5) Uani 1 1 d . . . . .
H16 H 0.878538 0.367049 0.357147 0.048 Uiso 1 1 calc R . . . .
C7 C 0.44384(15) 0.2911(4) 0.39743(5) 0.0359(4) Uani 1 1 d . . . . .
C15 C 0.80511(16) 0.5869(5) 0.30150(6) 0.0418(5) Uani 1 1 d . . . . .
C13 C 0.57475(16) 0.6353(5) 0.29542(5) 0.0413(5) Uani 1 1 d . . . . .
H13 H 0.498854 0.704623 0.279924 0.050 Uiso 1 1 calc R . . . .
C5 C 0.31247(16) 0.3997(5) 0.45849(6) 0.0427(5) Uani 1 1 d . . . . .
H5 H 0.383755 0.503100 0.473139 0.051 Uiso 1 1 calc R . . . .
C1 C 0.21328(15) 0.1131(4) 0.39631(6) 0.0429(5) Uani 1 1 d . . . . .
H1 H 0.217142 0.024652 0.368814 0.051 Uiso 1 1 calc R . . . .
C14 C 0.69001(17) 0.6840(5) 0.27843(6) 0.0460(5) Uani 1 1 d . . . . .
H14 H 0.691240 0.782315 0.251357 0.055 Uiso 1 1 calc R . . . .
C2 C 0.10064(17) 0.0902(5) 0.41578(6) 0.0485(5) Uani 1 1 d . . . . .
H2 H 0.029440 -0.016472 0.401509 0.058 Uiso 1 1 calc R . . . .
C4 C 0.19872(17) 0.3785(5) 0.47762(6) 0.0486(5) Uani 1 1 d . . . . .
H4 H 0.193717 0.468640 0.504969 0.058 Uiso 1 1 calc R . . . .
C3 C 0.09294(17) 0.2243(5) 0.45626(6) 0.0504(5) Uani 1 1 d . . . . .
H3A H 0.016444 0.210727 0.469115 0.060 Uiso 1 1 calc R . . . .
C17 C 1.03372(16) 0.5543(5) 0.30388(6) 0.0533(5) Uani 1 1 d . . . . .
H17A H 1.101655 0.629559 0.287518 0.080 Uiso 1 1 calc GR . . . .
H17B H 1.036423 0.310616 0.306438 0.080 Uiso 1 1 calc GR . . . .
H17C H 1.044349 0.654825 0.332037 0.080 Uiso 1 1 calc GR . . . .
H3 H 0.6428(18) 0.016(5) 0.4633(7) 0.074(7) 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
O3 C8 1.3488(19) . ?
O3 H3 0.852(18) . ?
O4 C12 1.2225(17) . ?
O2 C9 1.2219(18) . ?
O1 C15 1.3511(19) . ?
O1 C17 1.4234(18) . ?
C10 C11 1.388(2) . ?
C10 C9 1.468(2) . ?
C10 C16 1.389(2) . ?
C11 C12 1.482(2) . ?
C11 C13 1.393(2) . ?
C6 C7 1.483(2) . ?
C6 C5 1.393(2) . ?
C6 C1 1.389(2) . ?
C9 C8 1.483(2) . ?
C8 C7 1.345(2) . ?
C12 C7 1.488(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.388(2) . ?
C15 C14 1.396(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(2) . ?
C14 H14 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.376(2) . ?
C3 H3A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C8 O3 H3 102.3(16) . . ?
C15 O1 C17 118.80(14) . . ?
C11 C10 C9 118.87(15) . . ?
C11 C10 C16 121.61(15) . . ?
C16 C10 C9 119.52(14) . . ?
C10 C11 C12 121.88(15) . . ?
C10 C11 C13 118.37(16) . . ?
C13 C11 C12 119.75(14) . . ?
C5 C6 C7 119.84(15) . . ?
C1 C6 C7 121.55(15) . . ?
C1 C6 C5 118.60(16) . . ?
O2 C9 C10 123.98(16) . . ?
O2 C9 C8 118.00(15) . . ?
C10 C9 C8 118.02(14) . . ?
O3 C8 C9 114.16(13) . . ?
C7 C8 O3 121.64(16) . . ?
C7 C8 C9 124.19(15) . . ?
O4 C12 C11 120.30(15) . . ?
O4 C12 C7 120.94(16) . . ?
C11 C12 C7 118.76(14) . . ?
C10 C16 H16 120.4 . . ?
C15 C16 C10 119.29(15) . . ?
C15 C16 H16 120.4 . . ?
C6 C7 C12 119.90(13) . . ?
C8 C7 C6 122.05(15) . . ?
C8 C7 C12 118.05(16) . . ?
O1 C15 C16 124.54(16) . . ?
O1 C15 C14 115.94(16) . . ?
C16 C15 C14 119.51(16) . . ?
C11 C13 H13 119.7 . . ?
C14 C13 C11 120.69(15) . . ?
C14 C13 H13 119.7 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.51(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.51(17) . . ?
C2 C1 H1 119.7 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.51(16) . . ?
C13 C14 H14 119.7 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.39(17) . . ?
C3 C2 H2 119.8 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.13(18) . . ?
C3 C4 H4 119.9 . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 C2 119.85(18) . . ?
C4 C3 H3A 120.1 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_olex2_submission_original_sample_id DBR23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.614
_oxdiff_exptl_absorpt_empirical_full_min 0.353
####################################################################### 
# 
# 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_dbr29a
_database_code_depnum_ccdc_archive 'CCDC 2127417'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 O4'
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4420(5)
_cell_length_b                   10.6713(15)
_cell_length_c                   12.7912(18)
_cell_angle_alpha                71.516(13)
_cell_angle_beta                 87.083(9)
_cell_angle_gamma                75.865(10)
_cell_volume                     682.89(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2237
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      24.4020
_cell_measurement_theta_min      2.0670
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2382
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.073
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  17.00   0.50   12.00    --  -15.60 -94.00 -60.00  108
  2  ω     19.00  44.00   0.50   12.00    --   16.22-130.00 -34.00   50
  3  ω    -28.00  -2.00   0.50   12.00    --  -15.60 -30.00 -90.00   52
  4  ω    -15.00  40.00   0.50   12.00    --   16.22 -30.00 -90.00  110
  5  ω     57.00  88.00   0.50   12.00    --   16.22  30.00-120.00   62
  6  ω      8.00  43.00   0.50   12.00    --   16.22  30.00-120.00   70
  7  ω    -30.00  21.00   0.50   12.00    --  -15.60 -94.00 -30.00  102
  8  ω    -56.00 -22.00   0.50   12.00    --   16.22 -30.00 -90.00   68
  9  ω    -86.00 -45.00   0.50   12.00    --  -15.60 -30.00 -90.00   82
 10  ω    -87.00 -49.00   0.50   12.00    --  -15.60 -30.00   0.00   76
 11  ω      6.00  32.00   0.50   12.00    --   16.22 -30.00  60.00   52
 12  ω     -7.00  86.00   0.50   12.00    --   16.22  45.00  90.00  186
 13  ω     49.00  75.00   0.50   12.00    --   16.22  45.00 120.00   52
 14  ω     10.00  35.00   0.50   12.00    --   16.22  45.00 120.00   50
 15  ω    -43.00 -18.00   0.50   12.00    --  -15.60 130.00  37.00   50
 16  ω    -55.00 -29.00   0.50   12.00    --   16.22 -30.00  60.00   52
 17  ω    -37.00 -11.00   0.50   12.00    --   16.22 -94.00  90.00   52
 18  ω     47.00  75.00   0.50   12.00    --   16.22-139.00 150.00   56
 19  ω    -37.00  21.00   0.50   12.00    --  -15.60 -94.00 150.00  116
 20  ω    -85.00  16.00   0.50   12.00    --  -15.60 -77.00 150.00  202
 21  ω    -65.00 -17.00   0.50   12.00    --  -15.60 139.00-148.00   96
 22  ω    -46.00  36.00   0.50   12.00    --   16.22 -45.00-180.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0007871000
_diffrn_orient_matrix_UB_12      0.0192100000
_diffrn_orient_matrix_UB_13      -0.0584023000
_diffrn_orient_matrix_UB_21      0.0067740000
_diffrn_orient_matrix_UB_22      0.0664032000
_diffrn_orient_matrix_UB_23      -0.0024336000
_diffrn_orient_matrix_UB_31      0.1342894000
_diffrn_orient_matrix_UB_32      -0.0208714000
_diffrn_orient_matrix_UB_33      0.0021548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1280
_reflns_number_total             2382
_reflns_odcompleteness_completeness 97.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0775
_refine_ls_restrained_S_all      1.017
_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)+(0.1013P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1854
_refine_ls_wR_factor_ref         0.2290
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.861(4)
 0.139(4)
2. 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, All O(H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.34A with sigma of 0.04 and
sigma for terminal atoms of 0.08
All non-hydrogen atoms have similar U: within 1.34A with sigma of 0.04 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C7(H7), C3(H3), C14(H14), C15(H15), C18(H18), C16(H16), C17(H17)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
5.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O4 O 0.9096(5) 0.4914(3) 0.3355(2) 0.0530(8) Uani 1 1 d . U . . .
H4 H 0.9634 0.5051 0.3885 0.079 Uiso 1 1 calc GR . . . .
O1 O 0.0870(5) -0.0010(3) 0.6359(2) 0.0546(8) Uani 1 1 d . U . . .
O3 O 0.8066(5) 0.4074(3) 0.5489(2) 0.0548(8) Uani 1 1 d . U . . .
O2 O 0.3685(5) 0.2441(3) 0.2700(2) 0.0616(8) Uani 1 1 d . U . . .
C5 C 0.5404(6) 0.2697(3) 0.5294(3) 0.0416(9) Uani 1 1 d . U . . .
C6 C 0.4273(6) 0.2273(3) 0.4551(3) 0.0387(9) Uani 1 1 d . U . . .
C2 C 0.2355(6) 0.0884(4) 0.6062(3) 0.0449(9) Uani 1 1 d . U . . .
C4 C 0.4952(7) 0.2235(4) 0.6411(3) 0.0484(10) Uani 1 1 d . U . . .
H4A H 0.5661 0.2545 0.6899 0.058 Uiso 1 1 calc R . . . .
C10 C 0.7552(6) 0.4073(3) 0.3701(3) 0.0410(9) Uani 1 1 d . U . . .
C7 C 0.2775(6) 0.1367(3) 0.4941(3) 0.0423(9) Uani 1 1 d . U . . .
H7 H 0.2035 0.1074 0.4450 0.051 Uiso 1 1 calc R . . . .
C8 C 0.4762(7) 0.2779(4) 0.3352(3) 0.0470(10) Uani 1 1 d . U . . .
C11 C 0.7050(6) 0.3626(4) 0.4888(3) 0.0445(9) Uani 1 1 d . U . . .
C13 C 0.5692(7) 0.5697(4) 0.1206(3) 0.0466(10) Uani 1 1 d . U . . .
C9 C 0.6472(6) 0.3690(3) 0.2969(3) 0.0456(10) Uani 1 1 d . U . . .
C3 C 0.3457(7) 0.1318(4) 0.6805(3) 0.0495(10) Uani 1 1 d . U . . .
H3 H 0.3188 0.0993 0.7556 0.059 Uiso 1 1 calc R . . . .
C12 C 0.6927(7) 0.4198(4) 0.1746(3) 0.0509(10) Uani 1 1 d . U . . .
H12A H 0.6278 0.3668 0.1383 0.061 Uiso 1 1 calc R . . . .
H12B H 0.8739 0.4048 0.1635 0.061 Uiso 1 1 calc R . . . .
C1 C 0.0341(7) -0.0533(4) 0.7499(3) 0.0576(11) Uani 1 1 d . U . . .
H1A H -0.0704 -0.1164 0.7589 0.086 Uiso 1 1 calc GR . . . .
H1B H -0.0530 0.0203 0.7760 0.086 Uiso 1 1 calc GR . . . .
H1C H 0.1902 -0.0991 0.7915 0.086 Uiso 1 1 calc GR . . . .
C14 C 0.3263(7) 0.6261(4) 0.1464(3) 0.0581(11) Uani 1 1 d . U . . .
H14 H 0.2368 0.5717 0.1973 0.070 Uiso 1 1 calc R . . . .
C15 C 0.2162(8) 0.7615(5) 0.0977(4) 0.0700(13) Uani 1 1 d . U . . .
H15 H 0.0520 0.7976 0.1154 0.084 Uiso 1 1 calc R . . . .
C18 C 0.6931(8) 0.6529(4) 0.0439(3) 0.0631(12) Uani 1 1 d . U . . .
H18 H 0.8552 0.6166 0.0242 0.076 Uiso 1 1 calc R . . . .
C16 C 0.3444(10) 0.8445(5) 0.0234(4) 0.0738(13) Uani 1 1 d . U . . .
H16 H 0.2705 0.9369 -0.0074 0.089 Uiso 1 1 calc R . . . .
C17 C 0.5822(9) 0.7897(5) -0.0048(4) 0.0767(14) Uani 1 1 d . U . . .
H17 H 0.6697 0.8443 -0.0567 0.092 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
O4 H4 0.8200 . ?
O4 C10 1.336(4) . ?
O1 C2 1.350(4) . ?
O1 C1 1.428(4) . ?
O3 C11 1.237(4) . ?
O2 C8 1.230(4) . ?
C5 C6 1.399(5) . ?
C5 C4 1.386(5) . ?
C5 C11 1.454(5) . ?
C6 C7 1.374(5) . ?
C6 C8 1.489(5) . ?
C2 C7 1.389(5) . ?
C2 C3 1.397(5) . ?
C4 H4A 0.9300 . ?
C4 C3 1.381(5) . ?
C10 C11 1.472(5) . ?
C10 C9 1.344(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.464(5) . ?
C13 C12 1.520(5) . ?
C13 C14 1.383(5) . ?
C13 C18 1.370(5) . ?
C9 C12 1.514(5) . ?
C3 H3 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.371(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.384(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(6) . ?
C17 H17 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
C10 O4 H4 109.5 . . ?
C2 O1 C1 118.6(3) . . ?
C6 C5 C11 119.6(4) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C11 120.3(4) . . ?
C5 C6 C8 119.7(3) . . ?
C7 C6 C5 119.5(4) . . ?
C7 C6 C8 120.8(4) . . ?
O1 C2 C7 115.8(4) . . ?
O1 C2 C3 124.0(4) . . ?
C7 C2 C3 120.2(3) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4A 119.7 . . ?
O4 C10 C11 117.8(3) . . ?
O4 C10 C9 119.8(3) . . ?
C9 C10 C11 122.3(3) . . ?
C6 C7 C2 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O2 C8 C6 119.2(3) . . ?
O2 C8 C9 121.3(4) . . ?
C9 C8 C6 119.5(4) . . ?
O3 C11 C5 123.4(4) . . ?
O3 C11 C10 117.4(3) . . ?
C5 C11 C10 119.2(4) . . ?
C14 C13 C12 120.9(3) . . ?
C18 C13 C12 121.2(3) . . ?
C18 C13 C14 117.9(4) . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 C12 121.8(3) . . ?
C8 C9 C12 118.5(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C9 C12 C13 113.6(3) . . ?
C9 C12 H12A 108.8 . . ?
C9 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C13 C18 H18 119.3 . . ?
C13 C18 C17 121.4(4) . . ?
C17 C18 H18 119.3 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 H16 120.5 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.762
_oxdiff_exptl_absorpt_empirical_full_min 0.281
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.861(4)
2 0.139(4)

####################################################################### 
# 
# 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_dbr006_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2127415'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O3'
_chemical_formula_sum            'C17 H12 O3'
_chemical_formula_weight         264.27
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.3812(7)
_cell_length_b                   5.5547(3)
_cell_length_c                   18.6375(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.036(2)
_cell_angle_gamma                90
_cell_volume                     1278.59(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1060 before and 0.0723 after correction. The Ratio of minimum to maximum transmission is 0.9273. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38499
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.043
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1931
_reflns_number_total             2249
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.287
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      1.287
_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)+(0.1197P)²+0.1518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.1975
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C16(H16), C15(H15), C3(H3), C4(H4), C1(H1A), C2(H2)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.53731(13) 0.8927(3) 0.38735(7) 0.0570(5) Uani 1 1 d . . . . .
H1 H 0.535797 0.951024 0.427675 0.086 Uiso 1 1 calc GR . . . .
O2 O 0.36385(11) 0.2600(2) 0.25882(7) 0.0494(4) Uani 1 1 d . . . . .
O3 O 0.42455(13) 0.7764(3) 0.49893(8) 0.0600(5) Uani 1 1 d . . . . .
C6 C 0.53046(15) 0.6064(3) 0.26027(10) 0.0394(5) Uani 1 1 d . . . . .
C12 C 0.37923(14) 0.3741(3) 0.31477(9) 0.0384(5) Uani 1 1 d . . . . .
C7 C 0.45947(15) 0.5698(3) 0.32071(10) 0.0393(5) Uani 1 1 d . . . . .
C10 C 0.33047(15) 0.4523(3) 0.44092(9) 0.0417(5) Uani 1 1 d . . . . .
C5 C 0.60912(16) 0.4351(4) 0.24889(10) 0.0462(5) Uani 1 1 d . . . . .
H5 H 0.614955 0.298695 0.277849 0.055 Uiso 1 1 calc R . . . .
C13 C 0.24110(15) 0.1309(4) 0.37316(10) 0.0447(5) Uani 1 1 d . . . . .
H13 H 0.231705 0.041825 0.330926 0.054 Uiso 1 1 calc R . . . .
C8 C 0.46875(14) 0.7070(4) 0.38081(10) 0.0433(5) Uani 1 1 d . . . . .
C14 C 0.18053(16) 0.0735(4) 0.43113(11) 0.0479(5) Uani 1 1 d . . . . .
C16 C 0.27182(18) 0.3927(4) 0.49942(11) 0.0525(6) Uani 1 1 d . . . . .
H16 H 0.282740 0.477759 0.542291 0.063 Uiso 1 1 calc R . . . .
C9 C 0.40694(15) 0.6538(4) 0.44477(9) 0.0440(5) Uani 1 1 d . . . . .
C15 C 0.19754(17) 0.2075(4) 0.49385(11) 0.0534(6) Uani 1 1 d . . . . .
H15 H 0.157852 0.171500 0.533024 0.064 Uiso 1 1 calc R . . . .
C3 C 0.66968(18) 0.6653(4) 0.15134(11) 0.0551(6) Uani 1 1 d . . . . .
H3 H 0.716795 0.686432 0.115132 0.066 Uiso 1 1 calc R . . . .
C11 C 0.31492(14) 0.3181(3) 0.37747(9) 0.0397(5) Uani 1 1 d . . . . .
C4 C 0.67884(17) 0.4657(4) 0.19482(12) 0.0524(6) Uani 1 1 d . . . . .
H4 H 0.731906 0.351146 0.187898 0.063 Uiso 1 1 calc R . . . .
C1 C 0.52171(18) 0.8057(4) 0.21622(11) 0.0521(6) Uani 1 1 d . . . . .
H1A H 0.469306 0.921606 0.223271 0.063 Uiso 1 1 calc R . . . .
C17 C 0.09896(18) -0.1270(4) 0.42473(13) 0.0598(6) Uani 1 1 d . . . . .
H17A H 0.032613 -0.068294 0.401283 0.090 Uiso 1 1 calc GR . . . .
H17B H 0.085640 -0.184843 0.471834 0.090 Uiso 1 1 calc GR . . . .
H17C H 0.126517 -0.255930 0.396983 0.090 Uiso 1 1 calc GR . . . .
C2 C 0.5909(2) 0.8339(4) 0.16133(12) 0.0598(6) Uani 1 1 d . . . . .
H2 H 0.583941 0.967372 0.131237 0.072 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
O1 C8 1.336(2) . ?
O2 C12 1.224(2) . ?
O3 C9 1.225(2) . ?
C6 C7 1.491(3) . ?
C6 C5 1.388(3) . ?
C6 C1 1.378(3) . ?
C12 C7 1.472(3) . ?
C12 C11 1.493(3) . ?
C7 C8 1.353(2) . ?
C10 C16 1.392(3) . ?
C10 C9 1.464(3) . ?
C10 C11 1.400(2) . ?
C5 C4 1.383(3) . ?
C13 C14 1.395(3) . ?
C13 C11 1.383(3) . ?
C8 C9 1.491(3) . ?
C14 C15 1.390(3) . ?
C14 C17 1.502(3) . ?
C16 C15 1.379(3) . ?
C3 C4 1.374(3) . ?
C3 C2 1.374(3) . ?
C1 C2 1.389(3) . ?

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
C5 C6 C7 118.64(17) . . ?
C1 C6 C7 122.26(17) . . ?
C1 C6 C5 119.09(18) . . ?
O2 C12 C7 120.71(17) . . ?
O2 C12 C11 119.98(17) . . ?
C7 C12 C11 119.31(15) . . ?
C12 C7 C6 118.33(15) . . ?
C8 C7 C6 121.91(17) . . ?
C8 C7 C12 119.74(16) . . ?
C16 C10 C9 120.98(17) . . ?
C16 C10 C11 119.12(19) . . ?
C11 C10 C9 119.90(16) . . ?
C4 C5 C6 120.51(19) . . ?
C11 C13 C14 121.06(18) . . ?
O1 C8 C7 121.78(17) . . ?
O1 C8 C9 116.03(15) . . ?
C7 C8 C9 122.13(17) . . ?
C13 C14 C17 120.20(19) . . ?
C15 C14 C13 118.12(19) . . ?
C15 C14 C17 121.68(18) . . ?
C15 C16 C10 120.05(19) . . ?
O3 C9 C10 122.85(18) . . ?
O3 C9 C8 118.51(18) . . ?
C10 C9 C8 118.61(15) . . ?
C16 C15 C14 121.59(18) . . ?
C4 C3 C2 120.02(19) . . ?
C10 C11 C12 120.08(17) . . ?
C13 C11 C12 119.86(16) . . ?
C13 C11 C10 120.05(17) . . ?
C3 C4 C5 120.0(2) . . ?
C6 C1 C2 120.18(19) . . ?
C3 C2 C1 120.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
