# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_dbr
_database_code_depnum_ccdc_archive 'CCDC 2395504'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2023-11-03
_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 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27
_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/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                   17.739(2)
_cell_length_b                   5.4252(6)
_cell_length_c                   12.7285(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.676(5)
_cell_angle_gamma                90
_cell_volume                     1218.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1483 before and 0.0814 after correction.
The Ratio of minimum to maximum transmission is 0.8357.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.137
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42117
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_min         2.308
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_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                2230
_reflns_number_total             2792
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.073
_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)+(0.0695P)²+0.2255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1332
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C9(H9), C17(H17), C7(H7), C8(H8), C13(H13), C16(H16),
 C15(H15), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.25703(7) -0.0152(2) 0.48242(9) 0.0628(3) Uani 1 1 d . . . . .
O2 O 0.36809(7) 0.2862(2) 0.42916(9) 0.0679(4) Uani 1 1 d . . . . .
C10 C 0.33770(7) 0.5327(2) 0.68387(10) 0.0366(3) Uani 1 1 d . . . . .
C2 C 0.24605(7) 0.1931(2) 0.64268(10) 0.0382(3) Uani 1 1 d . . . . .
C5 C 0.36989(7) 0.5139(2) 0.58773(10) 0.0384(3) Uani 1 1 d . . . . .
C1 C 0.27619(7) 0.3698(2) 0.70759(10) 0.0378(3) Uani 1 1 d . . . . .
H1 H 0.256518 0.389794 0.772126 0.045 Uiso 1 1 calc R . . . .
C3 C 0.27814(8) 0.1494(3) 0.54240(10) 0.0426(3) Uani 1 1 d . . . . .
C12 C 0.14252(7) 0.0931(2) 0.76092(11) 0.0409(3) Uani 1 1 d . . . . .
C4 C 0.34251(8) 0.3199(3) 0.51254(10) 0.0434(3) Uani 1 1 d . . . . .
C6 C 0.42638(8) 0.6761(3) 0.56457(12) 0.0462(3) Uani 1 1 d . . . . .
H6 H 0.447381 0.662972 0.500686 0.055 Uiso 1 1 calc R . . . .
C9 C 0.36399(8) 0.7151(3) 0.75479(11) 0.0445(3) Uani 1 1 d . . . . .
H9 H 0.343596 0.729012 0.819092 0.053 Uiso 1 1 calc R . . . .
C11 C 0.18217(8) 0.0255(3) 0.66585(12) 0.0462(3) Uani 1 1 d . . . . .
H11A H 0.145021 0.023104 0.604589 0.055 Uiso 1 1 calc R . . . .
H11B H 0.202012 -0.140399 0.675653 0.055 Uiso 1 1 calc R . . . .
C17 C 0.09458(9) 0.2948(3) 0.75923(13) 0.0518(4) Uani 1 1 d . . . . .
H17 H 0.088490 0.394141 0.699451 0.062 Uiso 1 1 calc R . . . .
C7 C 0.45154(8) 0.8566(3) 0.63576(13) 0.0506(4) Uani 1 1 d . . . . .
H7 H 0.489471 0.964892 0.619943 0.061 Uiso 1 1 calc R . . . .
C8 C 0.42035(8) 0.8766(3) 0.73068(12) 0.0504(4) Uani 1 1 d . . . . .
H8 H 0.437214 0.998927 0.778553 0.060 Uiso 1 1 calc R . . . .
C13 C 0.15158(9) -0.0471(3) 0.85186(13) 0.0540(4) Uani 1 1 d . . . . .
H13 H 0.184472 -0.181017 0.855597 0.065 Uiso 1 1 calc R . . . .
C16 C 0.05569(9) 0.3506(3) 0.84483(15) 0.0620(4) Uani 1 1 d . . . . .
H16 H 0.023547 0.486360 0.842300 0.074 Uiso 1 1 calc R . . . .
C15 C 0.06436(10) 0.2063(4) 0.93364(15) 0.0648(5) Uani 1 1 d . . . . .
H15 H 0.037687 0.242378 0.991061 0.078 Uiso 1 1 calc R . . . .
C14 C 0.11246(11) 0.0089(4) 0.93721(14) 0.0677(5) Uani 1 1 d . . . . .
H14 H 0.118858 -0.088344 0.997611 0.081 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 C3 1.2100(17) . ?
O2 C4 1.2086(16) . ?
C10 C5 1.4043(18) . ?
C10 C1 1.4589(18) . ?
C10 C9 1.3886(18) . ?
C2 C1 1.3415(18) . ?
C2 C3 1.4673(18) . ?
C2 C11 1.5046(18) . ?
C5 C4 1.4722(19) . ?
C5 C6 1.3870(19) . ?
C3 C4 1.546(2) . ?
C12 C11 1.504(2) . ?
C12 C17 1.384(2) . ?
C12 C13 1.381(2) . ?
C6 C7 1.378(2) . ?
C9 C8 1.387(2) . ?
C17 C16 1.380(2) . ?
C7 C8 1.382(2) . ?
C13 C14 1.380(2) . ?
C16 C15 1.371(3) . ?
C15 C14 1.367(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 C10 C1 120.88(12) . . ?
C9 C10 C5 118.62(12) . . ?
C9 C10 C1 120.47(12) . . ?
C1 C2 C3 119.07(12) . . ?
C1 C2 C11 124.96(12) . . ?
C3 C2 C11 115.93(11) . . ?
C10 C5 C4 118.82(12) . . ?
C6 C5 C10 120.24(12) . . ?
C6 C5 C4 120.94(12) . . ?
C2 C1 C10 124.47(12) . . ?
O1 C3 C2 123.07(13) . . ?
O1 C3 C4 118.45(12) . . ?
C2 C3 C4 118.47(11) . . ?
C17 C12 C11 121.04(13) . . ?
C13 C12 C11 120.99(13) . . ?
C13 C12 C17 117.95(14) . . ?
O2 C4 C5 123.41(13) . . ?
O2 C4 C3 118.42(13) . . ?
C5 C4 C3 118.17(11) . . ?
C7 C6 C5 120.32(14) . . ?
C8 C9 C10 120.63(13) . . ?
C12 C11 C2 115.56(11) . . ?
C16 C17 C12 121.03(15) . . ?
C6 C7 C8 119.93(14) . . ?
C7 C8 C9 120.25(14) . . ?
C14 C13 C12 120.85(16) . . ?
C15 C16 C17 120.10(16) . . ?
C14 C15 C16 119.57(16) . . ?
C15 C14 C13 120.48(17) . . ?

_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_dbr74
_database_code_depnum_ccdc_archive 'CCDC 2395506'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2023-09-22
_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 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27
_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/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                   5.42680(10)
_cell_length_b                   10.2243(2)
_cell_length_c                   22.7209(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.593(2)
_cell_angle_gamma                90
_cell_volume                     1256.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8443
_cell_measurement_temperature    298.7
_cell_measurement_theta_max      26.4340
_cell_measurement_theta_min      2.1760
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48608
_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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.111
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_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       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15230
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.881
_diffrn_reflns_theta_min         2.185
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.7
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  22.00   0.50    7.00    --  -14.97 -94.00 -60.00   80
  2  ω      9.00  70.00   0.50    7.00    --   16.22-124.00 -17.00  122
  3  ω     14.00  71.00   0.50    7.00    --   16.22-125.00   0.00  114
  4  ω      7.00  33.00   0.50    7.00    --   16.22 -15.00 -90.00   52
  5  ω     -6.00  85.00   0.50    7.00    --   16.22  45.00 -90.00  182
  6  ω    -37.00  18.00   0.50    7.00    --  -14.97 -94.00-180.00  110
  7  ω    -43.00 -18.00   0.50    7.00    --   16.22 -15.00 -90.00   50
  8  ω    -85.00  10.00   0.50    7.00    --  -14.97 -45.00 -60.00  190
  9  ω    -85.00  10.00   0.50    7.00    --  -14.97 -45.00-150.00  190
 10  ω    -83.00 -23.00   0.50    7.00    --  -14.97 148.00-133.00  120
 11  ω    -63.00 -34.00   0.50    7.00    --  -14.97 125.00  30.00   58
 12  ω    -69.00  -9.00   0.50    7.00    --  -14.97 124.00  62.00  120
 13  ω    -41.00  59.00   0.50    7.00    --  -14.97  30.00 120.00  200
 14  ω    -57.00  40.00   0.50    7.00    --   16.22 -30.00 120.00  194
 15  ω     23.00  85.00   0.50    7.00    --   16.22-148.00 178.00  124
;
_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      -0.0089740000
_diffrn_orient_matrix_UB_12      0.0633510000
_diffrn_orient_matrix_UB_13      0.0123659000
_diffrn_orient_matrix_UB_21      -0.0206831000
_diffrn_orient_matrix_UB_22      0.0268842000
_diffrn_orient_matrix_UB_23      -0.0287574000
_diffrn_orient_matrix_UB_31      -0.1291380000
_diffrn_orient_matrix_UB_32      -0.0087323000
_diffrn_orient_matrix_UB_33      0.0012089000
_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                2057
_reflns_number_total             2616
_reflns_odcompleteness_completeness 99.63
_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         0.152
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.068
_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)+(0.0668P)²+0.1333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C17(H17), C13(H13), C2(H2), C15(H15), C16(H16), C4(H4),
 C14(H14), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.16934(18) 0.63838(10) 0.35408(5) 0.0600(3) Uani 1 1 d . . . . .
O2 O 0.9969(2) 0.38106(11) 0.42134(5) 0.0660(3) Uani 1 1 d . . . . .
C9 C 0.5121(2) 0.61514(12) 0.42373(5) 0.0431(3) Uani 1 1 d . . . . .
C10 C 0.3691(2) 0.58639(13) 0.36642(6) 0.0436(3) Uani 1 1 d . . . . .
C6 C 0.6901(2) 0.42248(13) 0.34327(5) 0.0444(3) Uani 1 1 d . . . . .
C1 C 0.4760(2) 0.49205(13) 0.32574(5) 0.0446(3) Uani 1 1 d . . . . .
C12 C 0.4095(2) 0.85520(13) 0.43366(5) 0.0440(3) Uani 1 1 d . . . . .
C7 C 0.8159(2) 0.44477(13) 0.40296(6) 0.0462(3) Uani 1 1 d . . . . .
C8 C 0.7156(2) 0.54694(13) 0.43966(6) 0.0479(3) Uani 1 1 d . . . . .
H8 H 0.798991 0.565052 0.476107 0.058 Uiso 1 1 calc R . . . .
C11 C 0.4123(3) 0.72019(14) 0.46130(6) 0.0514(4) Uani 1 1 d . . . . .
H11A H 0.511584 0.723186 0.498732 0.062 Uiso 1 1 calc R . . . .
H11B H 0.245020 0.697189 0.469445 0.062 Uiso 1 1 calc R . . . .
C5 C 0.7831(3) 0.33137(14) 0.30543(7) 0.0566(4) Uani 1 1 d . . . . .
H5 H 0.925604 0.284555 0.317147 0.068 Uiso 1 1 calc R . . . .
C17 C 0.2277(3) 0.94312(15) 0.44532(7) 0.0567(4) Uani 1 1 d . . . . .
H17 H 0.105702 0.918110 0.469546 0.068 Uiso 1 1 calc R . . . .
C13 C 0.5870(3) 0.89456(15) 0.39692(7) 0.0557(4) Uani 1 1 d . . . . .
H13 H 0.712073 0.837080 0.388359 0.067 Uiso 1 1 calc R . . . .
C2 C 0.3582(3) 0.47090(16) 0.26966(6) 0.0591(4) Uani 1 1 d . . . . .
H2 H 0.215883 0.517377 0.257480 0.071 Uiso 1 1 calc R . . . .
C15 C 0.3984(3) 1.10543(15) 0.38531(7) 0.0624(4) Uani 1 1 d . . . . .
H15 H 0.394753 1.189063 0.369165 0.075 Uiso 1 1 calc R . . . .
C16 C 0.2225(3) 1.06766(16) 0.42180(8) 0.0644(4) Uani 1 1 d . . . . .
H16 H 0.099446 1.125987 0.430759 0.077 Uiso 1 1 calc R . . . .
C4 C 0.6625(3) 0.31067(17) 0.25020(7) 0.0694(5) Uani 1 1 d . . . . .
H4 H 0.723216 0.248896 0.225022 0.083 Uiso 1 1 calc R . . . .
C14 C 0.5795(3) 1.01922(16) 0.37281(8) 0.0654(4) Uani 1 1 d . . . . .
H14 H 0.698789 1.044405 0.347885 0.078 Uiso 1 1 calc R . . . .
C3 C 0.4536(4) 0.38075(18) 0.23229(7) 0.0713(5) Uani 1 1 d . . . . .
H3 H 0.376025 0.367388 0.194777 0.086 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 C10 1.2197(15) . ?
O2 C7 1.2243(16) . ?
C9 C10 1.4909(18) . ?
C9 C8 1.3313(18) . ?
C9 C11 1.4999(18) . ?
C10 C1 1.4855(18) . ?
C6 C1 1.3933(19) . ?
C6 C7 1.4861(18) . ?
C6 C5 1.3896(19) . ?
C1 C2 1.3957(19) . ?
C12 C11 1.5161(18) . ?
C12 C17 1.3760(19) . ?
C12 C13 1.3842(19) . ?
C7 C8 1.4680(19) . ?
C8 H8 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.384(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.380(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(2) . ?
C15 C14 1.367(2) . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.375(3) . ?
C14 H14 0.9300 . ?
C3 H3 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 C9 C11 116.86(12) . . ?
C8 C9 C10 119.78(12) . . ?
C8 C9 C11 123.36(12) . . ?
O1 C10 C9 120.39(12) . . ?
O1 C10 C1 121.60(12) . . ?
C1 C10 C9 118.01(11) . . ?
C1 C6 C7 119.61(12) . . ?
C5 C6 C1 120.09(12) . . ?
C5 C6 C7 120.30(13) . . ?
C6 C1 C10 120.79(11) . . ?
C6 C1 C2 119.49(13) . . ?
C2 C1 C10 119.71(13) . . ?
C17 C12 C11 119.92(12) . . ?
C17 C12 C13 118.07(13) . . ?
C13 C12 C11 122.00(12) . . ?
O2 C7 C6 121.81(13) . . ?
O2 C7 C8 120.57(12) . . ?
C8 C7 C6 117.62(12) . . ?
C9 C8 C7 123.73(12) . . ?
C9 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
C9 C11 C12 114.11(10) . . ?
C9 C11 H11A 108.7 . . ?
C9 C11 H11B 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.64(15) . . ?
C4 C5 H5 120.2 . . ?
C12 C17 H17 119.3 . . ?
C12 C17 C16 121.38(13) . . ?
C16 C17 H17 119.3 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.37(14) . . ?
C14 C13 H13 119.8 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.85(15) . . ?
C3 C2 H2 120.1 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.45(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.07(14) . . ?
C15 C16 H16 120.0 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.49(15) . . ?
C3 C4 H4 119.8 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.65(14) . . ?
C15 C14 H14 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.42(15) . . ?
C4 C3 H3 119.8 . . ?

_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 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.561
####################################################################### 
# 
# 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_dbr041_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2395505'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-08-27
_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      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                   19.0585(16)
_cell_length_b                   5.6006(5)
_cell_length_c                   13.1682(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.843(3)
_cell_angle_gamma                90
_cell_volume                     1358.66(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7655
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.07
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1165 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.8364. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.360
_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          0.19
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1418
_diffrn_reflns_av_unetI/netI     0.1448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27669
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.188
_diffrn_reflns_theta_min         2.211
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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                2012
_reflns_number_total             3677
_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         0.382
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1783
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      0.976
_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)+(0.0803P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1622
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C17(H17), C16(H16), C14(H14), C7(H7), C6(H6), C5(H5), C13(H13), C4(H4)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O3 O 0.43498(8) 0.9075(3) 0.08374(8) 0.0511(4) Uani 1 1 d . . . . .
O2 O 0.22813(9) 0.9742(3) 0.58096(9) 0.0619(5) Uani 1 1 d . . . . .
O1 O 0.12269(9) 0.6737(4) 0.60225(10) 0.0730(6) Uani 1 1 d . . . . .
C10 C 0.23505(10) 0.8043(3) 0.41945(11) 0.0346(4) Uani 1 1 d . . . . .
C9 C 0.20520(10) 0.6426(3) 0.34632(11) 0.0361(4) Uani 1 1 d . . . . .
H9 H 0.221694 0.637521 0.285722 0.043 Uiso 1 1 calc R . . . .
C15 C 0.39993(10) 0.9042(3) 0.16293(11) 0.0371(4) Uani 1 1 d . . . . .
C12 C 0.32855(10) 0.9430(3) 0.32295(11) 0.0363(4) Uani 1 1 d . . . . .
C8 C 0.14868(10) 0.4738(3) 0.35470(11) 0.0358(4) Uani 1 1 d . . . . .
C1 C 0.20681(10) 0.8252(4) 0.51395(11) 0.0393(4) Uani 1 1 d . . . . .
C3 C 0.12017(10) 0.4735(4) 0.44344(11) 0.0385(4) Uani 1 1 d . . . . .
C17 C 0.37651(11) 0.7578(4) 0.32212(12) 0.0427(4) Uani 1 1 d . . . . .
H17 H 0.384953 0.644969 0.375694 0.051 Uiso 1 1 calc R . . . .
C16 C 0.41242(11) 0.7369(3) 0.24262(13) 0.0423(4) Uani 1 1 d . . . . .
H16 H 0.444496 0.611430 0.243255 0.051 Uiso 1 1 calc R . . . .
C2 C 0.14630(11) 0.6543(4) 0.52608(12) 0.0440(5) Uani 1 1 d . . . . .
C14 C 0.35052(12) 1.0851(4) 0.16097(13) 0.0468(5) Uani 1 1 d . . . . .
H14 H 0.340805 1.194690 0.106057 0.056 Uiso 1 1 calc R . . . .
C11 C 0.29475(11) 0.9745(4) 0.41430(12) 0.0408(4) Uani 1 1 d . . . . .
H11A H 0.332826 0.959694 0.478909 0.049 Uiso 1 1 calc R . . . .
H11B H 0.275755 1.135631 0.411779 0.049 Uiso 1 1 calc R . . . .
C7 C 0.12347(11) 0.3042(4) 0.27701(13) 0.0460(5) Uani 1 1 d . . . . .
H7 H 0.141411 0.302258 0.217648 0.055 Uiso 1 1 calc R . . . .
C6 C 0.07191(12) 0.1379(4) 0.28702(15) 0.0536(5) Uani 1 1 d . . . . .
H6 H 0.055998 0.024053 0.234770 0.064 Uiso 1 1 calc R . . . .
C18 C 0.48906(12) 0.7314(4) 0.08683(14) 0.0551(6) Uani 1 1 d . . . . .
H18A H 0.512147 0.760010 0.031171 0.083 Uiso 1 1 calc GR . . . .
H18B H 0.467001 0.576084 0.078186 0.083 Uiso 1 1 calc GR . . . .
H18C H 0.524613 0.738916 0.153216 0.083 Uiso 1 1 calc GR . . . .
C5 C 0.04377(12) 0.1395(4) 0.37430(15) 0.0547(5) Uani 1 1 d . . . . .
H5 H 0.008966 0.028022 0.380603 0.066 Uiso 1 1 calc R . . . .
C13 C 0.31543(11) 1.1042(4) 0.24021(13) 0.0437(4) Uani 1 1 d . . . . .
H13 H 0.282377 1.227429 0.238102 0.052 Uiso 1 1 calc R . . . .
C4 C 0.06802(12) 0.3087(4) 0.45182(14) 0.0497(5) Uani 1 1 d . . . . .
H4 H 0.049027 0.311605 0.510203 0.060 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
O3 C15 1.3751(16) . ?
O3 C18 1.420(2) . ?
O2 C1 1.207(2) . ?
O1 C2 1.2048(18) . ?
C10 C9 1.338(2) . ?
C10 C1 1.4816(18) . ?
C10 C11 1.499(2) . ?
C9 C8 1.458(2) . ?
C15 C16 1.381(2) . ?
C15 C14 1.379(2) . ?
C12 C17 1.384(2) . ?
C12 C11 1.513(2) . ?
C12 C13 1.387(2) . ?
C8 C3 1.4093(19) . ?
C8 C7 1.389(2) . ?
C1 C2 1.538(3) . ?
C3 C2 1.477(3) . ?
C3 C4 1.381(2) . ?
C17 C16 1.395(2) . ?
C14 C13 1.380(2) . ?
C7 C6 1.385(3) . ?
C6 C5 1.387(3) . ?
C5 C4 1.383(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
C15 O3 C18 117.33(14) . . ?
C9 C10 C1 118.62(16) . . ?
C9 C10 C11 125.83(13) . . ?
C1 C10 C11 115.54(14) . . ?
C10 C9 C8 124.77(13) . . ?
O3 C15 C16 124.23(17) . . ?
O3 C15 C14 115.98(15) . . ?
C14 C15 C16 119.78(15) . . ?
C17 C12 C11 120.65(15) . . ?
C17 C12 C13 117.90(15) . . ?
C13 C12 C11 121.39(17) . . ?
C3 C8 C9 120.85(15) . . ?
C7 C8 C9 120.70(14) . . ?
C7 C8 C3 118.41(18) . . ?
O2 C1 C10 122.82(17) . . ?
O2 C1 C2 118.38(14) . . ?
C10 C1 C2 118.78(15) . . ?
C8 C3 C2 118.76(17) . . ?
C4 C3 C8 120.36(16) . . ?
C4 C3 C2 120.87(15) . . ?
C12 C17 C16 121.38(16) . . ?
C15 C16 C17 119.41(17) . . ?
O1 C2 C1 118.69(18) . . ?
O1 C2 C3 123.23(19) . . ?
C3 C2 C1 118.07(13) . . ?
C15 C14 C13 120.23(16) . . ?
C10 C11 C12 116.41(14) . . ?
C6 C7 C8 120.67(16) . . ?
C7 C6 C5 120.59(19) . . ?
C4 C5 C6 119.3(2) . . ?
C14 C13 C12 121.24(17) . . ?
C3 C4 C5 120.68(17) . . ?

_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_dbr037_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2395507'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-08-27
_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 H11 F O2'
_chemical_formula_sum            'C17 H11 F O2'
_chemical_formula_weight         266.26
_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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.4575(11)
_cell_length_b                   7.5249(6)
_cell_length_c                   21.8542(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.640(3)
_cell_angle_gamma                90
_cell_volume                     2536.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6138
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1512 before and 0.0805 after correction. The Ratio of minimum to maximum transmission is 0.8232. 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    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23412
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.971
_diffrn_reflns_theta_min         1.867
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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                2054
_reflns_number_total             3052
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.099
_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)+(0.0875P)²+0.2116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1642
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C1(H1), C15(H15), C7(H7), C17(H17), C16(H16), C6(H6), C5(H5)
;
_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
O2 O 0.31512(10) -0.0357(2) 0.39300(6) 0.0634(4) Uani 1 1 d . . . . .
F1 F 0.40254(11) 0.70374(17) 0.27530(8) 0.0910(5) Uani 1 1 d . . . . .
O1 O 0.50698(11) 0.3317(2) 0.55903(8) 0.0767(5) Uani 1 1 d . . . . .
C9 C 0.35770(11) 0.0472(2) 0.43129(8) 0.0407(3) Uani 1 1 d . . . . .
C3 C 0.37980(11) 0.1618(2) 0.53888(8) 0.0416(3) Uani 1 1 d . . . . .
C12 C 0.42092(10) 0.2350(2) 0.30740(7) 0.0391(3) Uani 1 1 d . . . . .
C8 C 0.32986(10) 0.06608(19) 0.49522(7) 0.0388(3) Uani 1 1 d . . . . .
C10 C 0.44103(10) 0.1314(2) 0.41641(8) 0.0408(3) Uani 1 1 d . . . . .
C2 C 0.46162(12) 0.2461(2) 0.52245(8) 0.0470(4) Uani 1 1 d . . . . .
C4 C 0.35284(14) 0.1775(2) 0.59843(9) 0.0526(4) Uani 1 1 d . . . . .
H4 H 0.386150 0.241431 0.627751 0.063 Uiso 1 1 calc R . . . .
C13 C 0.43247(12) 0.4173(2) 0.31300(8) 0.0467(4) Uani 1 1 d . . . . .
H13 H 0.468158 0.464638 0.344779 0.056 Uiso 1 1 calc R . . . .
C1 C 0.48758(11) 0.2222(2) 0.45932(9) 0.0469(4) Uani 1 1 d . . . . .
H1 H 0.539364 0.273211 0.448765 0.056 Uiso 1 1 calc R . . . .
C15 C 0.33589(13) 0.4645(2) 0.22343(8) 0.0514(4) Uani 1 1 d . . . . .
H15 H 0.307969 0.542277 0.195596 0.062 Uiso 1 1 calc R . . . .
C7 C 0.25328(12) -0.0138(2) 0.51085(9) 0.0504(4) Uani 1 1 d . . . . .
H7 H 0.219567 -0.077735 0.481757 0.060 Uiso 1 1 calc R . . . .
C17 C 0.36632(12) 0.1695(2) 0.25997(8) 0.0470(4) Uani 1 1 d . . . . .
H17 H 0.358020 0.047584 0.255987 0.056 Uiso 1 1 calc R . . . .
C11 C 0.46846(12) 0.1091(2) 0.35212(8) 0.0491(4) Uani 1 1 d . . . . .
H11A H 0.457430 -0.012307 0.338932 0.059 Uiso 1 1 calc R . . . .
H11B H 0.530313 0.130351 0.351670 0.059 Uiso 1 1 calc R . . . .
C14 C 0.38987(13) 0.5264(2) 0.27040(9) 0.0507(4) Uani 1 1 d . . . . .
C16 C 0.32388(12) 0.2840(3) 0.21834(8) 0.0531(4) Uani 1 1 d . . . . .
H16 H 0.287122 0.238428 0.186841 0.064 Uiso 1 1 calc R . . . .
C6 C 0.22748(14) 0.0027(3) 0.57059(11) 0.0606(5) Uani 1 1 d . . . . .
H6 H 0.176539 -0.051201 0.581464 0.073 Uiso 1 1 calc R . . . .
C5 C 0.27706(15) 0.0986(3) 0.61360(9) 0.0602(5) Uani 1 1 d . . . . .
H5 H 0.259041 0.109794 0.653219 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
O2 C9 1.205(2) . ?
F1 C14 1.352(2) . ?
O1 C2 1.214(2) . ?
C9 C8 1.495(2) . ?
C9 C10 1.490(2) . ?
C3 C8 1.390(2) . ?
C3 C2 1.480(3) . ?
C3 C4 1.397(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.385(2) . ?
C12 C11 1.517(2) . ?
C8 C7 1.389(2) . ?
C10 C1 1.333(2) . ?
C10 C11 1.503(2) . ?
C2 C1 1.472(2) . ?
C4 C5 1.373(3) . ?
C13 C14 1.377(3) . ?
C15 C14 1.363(3) . ?
C15 C16 1.374(3) . ?
C7 C6 1.395(3) . ?
C17 C16 1.387(2) . ?
C6 C5 1.378(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
O2 C9 C8 121.42(16) . . ?
O2 C9 C10 120.68(16) . . ?
C10 C9 C8 117.89(14) . . ?
C8 C3 C2 120.12(15) . . ?
C8 C3 C4 119.88(17) . . ?
C4 C3 C2 120.00(17) . . ?
C13 C12 C11 120.40(16) . . ?
C17 C12 C13 119.12(16) . . ?
C17 C12 C11 120.47(16) . . ?
C3 C8 C9 120.71(15) . . ?
C7 C8 C9 119.26(16) . . ?
C7 C8 C3 120.02(16) . . ?
C9 C10 C11 117.13(15) . . ?
C1 C10 C9 120.00(15) . . ?
C1 C10 C11 122.88(16) . . ?
O1 C2 C3 122.32(18) . . ?
O1 C2 C1 120.11(17) . . ?
C1 C2 C3 117.57(15) . . ?
C5 C4 C3 119.87(19) . . ?
C14 C13 C12 118.46(17) . . ?
C10 C1 C2 123.69(15) . . ?
C14 C15 C16 118.14(17) . . ?
C8 C7 C6 119.34(19) . . ?
C12 C17 C16 120.67(17) . . ?
C10 C11 C12 112.27(13) . . ?
F1 C14 C13 118.32(19) . . ?
F1 C14 C15 118.39(17) . . ?
C15 C14 C13 123.28(17) . . ?
C15 C16 C17 120.33(18) . . ?
C5 C6 C7 120.37(18) . . ?
C4 C5 C6 120.52(18) . . ?

_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_dbr026_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2395508'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2023-12-15
_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 H11 Cl O2'
_chemical_formula_sum            'C17 H11 Cl O2'
_chemical_formula_weight         282.71
_chemical_absolute_configuration syn
_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'
Cl Cl 0.1484 0.1585 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.9955(2)
_cell_length_b                   5.9148(3)
_cell_length_c                   11.7073(7)
_cell_angle_alpha                103.743(2)
_cell_angle_beta                 98.978(2)
_cell_angle_gamma                97.252(2)
_cell_volume                     327.06(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1519 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.8712.
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    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             146
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10940
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.227
_diffrn_reflns_theta_min         1.825
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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         0.989
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2512
_reflns_number_total             2920
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.021
_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)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C12(H12), C13(H13), C14(H14), C2(H2), C15(H15), C5(H5), C3(H3), C4(H4)
;
_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
O1 O 0.8437(6) 0.3088(4) 0.7386(2) 0.0617(7) Uani 1 1 d . . . . .
O2 O 0.3868(5) 0.8435(4) 0.4828(2) 0.0553(7) Uani 1 1 d . . . . .
C8 C 0.6693(6) 0.5568(5) 0.4916(3) 0.0353(6) Uani 1 1 d . . . . .
C9 C 0.7780(6) 0.4239(5) 0.5578(3) 0.0387(7) Uani 1 1 d . . . . .
C10 C 0.7388(6) 0.4325(5) 0.6826(3) 0.0404(7) Uani 1 1 d . . . . .
C7 C 0.7073(6) 0.5484(6) 0.3653(3) 0.0436(7) Uani 1 1 d . . . . .
H7A H 0.861720 0.469698 0.349417 0.052 Uiso 1 1 calc R . . . .
H7B H 0.750655 0.708396 0.358242 0.052 Uiso 1 1 calc R . . . .
C16 C 0.4526(6) 0.7460(5) 0.6675(3) 0.0372(6) Uani 1 1 d . . . . .
C11 C 0.5696(6) 0.6036(5) 0.7340(3) 0.0385(6) Uani 1 1 d . . . . .
C17 C 0.4952(6) 0.7254(5) 0.5425(2) 0.0382(6) Uani 1 1 d . . . . .
C6 C 0.4539(6) 0.4200(5) 0.2724(2) 0.0394(6) Uani 1 1 d . . . . .
C1 C 0.3253(7) 0.1982(5) 0.2717(3) 0.0489(7) Uani 1 1 d . . . . .
H1 H 0.395780 0.123867 0.328573 0.059 Uiso 1 1 calc R . . . .
C12 C 0.5228(7) 0.6243(6) 0.8510(3) 0.0507(8) Uani 1 1 d . . . . .
H12 H 0.596713 0.528894 0.895937 0.061 Uiso 1 1 calc R . . . .
C13 C 0.3695(8) 0.7836(6) 0.8987(3) 0.0569(9) Uani 1 1 d . . . . .
H13 H 0.339992 0.796417 0.976305 0.068 Uiso 1 1 calc R . . . .
C14 C 0.2569(7) 0.9267(6) 0.8332(3) 0.0535(8) Uani 1 1 d . . . . .
H14 H 0.154447 1.036261 0.867076 0.064 Uiso 1 1 calc R . . . .
C2 C 0.0921(8) 0.0868(7) 0.1867(3) 0.0624(10) Uani 1 1 d . . . . .
H2 H 0.005695 -0.061681 0.187213 0.075 Uiso 1 1 calc R . . . .
C15 C 0.2966(7) 0.9067(6) 0.7183(3) 0.0481(8) Uani 1 1 d . . . . .
H15 H 0.218509 1.001450 0.674086 0.058 Uiso 1 1 calc R . . . .
C5 C 0.3467(8) 0.5244(7) 0.1849(3) 0.0570(8) Uani 1 1 d . . . . .
H5 H 0.431428 0.672492 0.183024 0.068 Uiso 1 1 calc R . . . .
C3 C -0.0128(8) 0.1933(7) 0.1016(3) 0.0675(11) Uani 1 1 d . . . . .
H3 H -0.170271 0.118078 0.044965 0.081 Uiso 1 1 calc R . . . .
C4 C 0.1150(9) 0.4091(8) 0.1007(4) 0.0717(11) Uani 1 1 d . . . . .
H4 H 0.045200 0.480414 0.042464 0.086 Uiso 1 1 calc R . . . .
Cl1 Cl 0.98195(13) 0.22299(12) 0.50522(8) 0.0519(2) Uani 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
O1 C10 1.207(4) . ?
O2 C17 1.216(4) . ?
C8 C9 1.333(4) . ?
C8 C7 1.510(5) . ?
C8 C17 1.484(4) . ?
C9 C10 1.494(4) . ?
C9 Cl1 1.727(3) . ?
C10 C11 1.479(4) . ?
C7 C6 1.516(4) . ?
C16 C11 1.397(4) . ?
C16 C17 1.490(4) . ?
C16 C15 1.389(4) . ?
C11 C12 1.404(4) . ?
C6 C1 1.384(4) . ?
C6 C5 1.390(5) . ?
C1 C2 1.384(5) . ?
C12 C13 1.361(5) . ?
C13 C14 1.384(5) . ?
C14 C15 1.369(5) . ?
C2 C3 1.372(6) . ?
C5 C4 1.378(5) . ?
C3 C4 1.356(6) . ?

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 C8 C7 124.6(3) . . ?
C9 C8 C17 119.3(3) . . ?
C17 C8 C7 116.1(3) . . ?
C8 C9 C10 124.4(3) . . ?
C8 C9 Cl1 122.2(2) . . ?
C10 C9 Cl1 113.4(2) . . ?
O1 C10 C9 121.6(3) . . ?
O1 C10 C11 122.1(3) . . ?
C11 C10 C9 116.3(3) . . ?
C8 C7 C6 112.5(2) . . ?
C11 C16 C17 120.1(3) . . ?
C15 C16 C11 119.7(3) . . ?
C15 C16 C17 120.2(3) . . ?
C16 C11 C10 120.9(3) . . ?
C16 C11 C12 118.9(3) . . ?
C12 C11 C10 120.2(3) . . ?
O2 C17 C8 120.6(3) . . ?
O2 C17 C16 120.4(3) . . ?
C8 C17 C16 119.0(2) . . ?
C1 C6 C7 121.5(3) . . ?
C1 C6 C5 118.5(3) . . ?
C5 C6 C7 120.0(3) . . ?
C6 C1 C2 120.1(3) . . ?
C13 C12 C11 120.2(3) . . ?
C12 C13 C14 120.8(3) . . ?
C15 C14 C13 119.9(3) . . ?
C3 C2 C1 120.6(4) . . ?
C14 C15 C16 120.5(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C3 C2 119.5(3) . . ?
C3 C4 C5 121.1(4) . . ?

_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_dbr047_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2395509'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-05
_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         'C16 H16 O3, C16 H15 O3'
_chemical_formula_sum            'C32 H31 O6'
_chemical_formula_weight         511.57
_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                   6.8522(5)
_cell_length_b                   12.7911(11)
_cell_length_c                   15.3647(12)
_cell_angle_alpha                94.719(3)
_cell_angle_beta                 102.333(3)
_cell_angle_gamma                90.643(3)
_cell_volume                     1310.56(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1492 before and 0.0796 after correction. The Ratio of minimum to maximum transmission is 0.8851. 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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.141
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            59611
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_min         1.362
_diffrn_ambient_temperature      301.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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                3965
_reflns_number_total             6530
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      1.079
_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)+(0.1088P)²+0.4820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2310
_refine_ls_wR_factor_ref         0.2523
_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:
 C27(H27A,H27B), C11(H11A,H11B), C9(H9A,H9B), C26(H26A,H26B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C5(H5), C18(H18), C6(H6), C2(H2), C22(H22), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C31(H31A,H31B,
 H31C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_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
O1 O -0.0526(3) 0.35880(13) 0.07418(11) 0.0593(5) Uani 1 1 d . . . . .
H1 H -0.064601 0.399698 0.035112 0.089 Uiso 1 1 calc GR . . . .
O2 O -0.0449(3) 0.56339(13) 0.07980(10) 0.0614(5) Uani 1 1 d . . . . .
O4 O 0.3793(3) 0.32834(15) 0.55211(11) 0.0676(5) Uani 1 1 d . . . . .
H4 H 0.344949 0.373203 0.517181 0.101 Uiso 1 1 calc GR . . . .
O6 O 0.5317(3) 0.31709(14) 0.86116(12) 0.0681(5) Uani 1 1 d . . . . .
O3 O 0.0933(3) 0.38247(15) 0.38518(12) 0.0743(6) Uani 1 1 d . . . . .
O5 O 0.3841(3) 0.53194(15) 0.57387(11) 0.0693(5) Uani 1 1 d . . . . .
C1 C -0.0185(3) 0.41279(18) 0.15427(14) 0.0452(5) Uani 1 1 d . . . . .
C29 C 0.4685(3) 0.54741(17) 0.73435(13) 0.0389(5) Uani 1 1 d . . . . .
C20 C 0.5080(3) 0.48562(17) 0.80733(13) 0.0405(5) Uani 1 1 d . . . . .
C4 C 0.0516(3) 0.54228(18) 0.31770(13) 0.0422(5) Uani 1 1 d . . . . .
C14 C -0.0165(3) 0.52980(17) 0.15324(13) 0.0419(5) Uani 1 1 d . . . . .
C17 C 0.4222(3) 0.37344(18) 0.63573(15) 0.0479(5) Uani 1 1 d . . . . .
C30 C 0.4231(3) 0.49066(18) 0.64426(14) 0.0450(5) Uani 1 1 d . . . . .
C13 C 0.0183(3) 0.59533(17) 0.23899(13) 0.0395(5) Uani 1 1 d . . . . .
C28 C 0.4737(3) 0.65817(17) 0.74855(14) 0.0427(5) Uani 1 1 d . . . . .
C19 C 0.5019(3) 0.36799(18) 0.79583(15) 0.0462(5) Uani 1 1 d . . . . .
C12 C 0.0206(3) 0.70635(17) 0.24381(13) 0.0413(5) Uani 1 1 d . . . . .
C23 C 0.5144(3) 0.70521(18) 0.83688(15) 0.0465(5) Uani 1 1 d . . . . .
C3 C 0.0551(3) 0.42590(19) 0.31572(15) 0.0493(5) Uani 1 1 d . . . . .
C7 C 0.0614(3) 0.76278(19) 0.32886(14) 0.0477(5) Uani 1 1 d . . . . .
C21 C 0.5528(3) 0.53378(19) 0.89330(14) 0.0487(5) Uani 1 1 d . . . . .
H21 H 0.582336 0.493378 0.941808 0.058 Uiso 1 1 calc R . . . .
C5 C 0.0842(3) 0.5998(2) 0.39988(14) 0.0523(6) Uani 1 1 d . . . . .
H5 H 0.102947 0.565629 0.452021 0.063 Uiso 1 1 calc R . . . .
C18 C 0.4606(3) 0.31714(19) 0.70634(16) 0.0504(5) Uani 1 1 d . . . . .
H18 H 0.460637 0.244311 0.697771 0.060 Uiso 1 1 calc R . . . .
C6 C 0.0890(3) 0.7073(2) 0.40459(15) 0.0541(6) Uani 1 1 d . . . . .
H6 H 0.111566 0.744635 0.460541 0.065 Uiso 1 1 calc R . . . .
C2 C 0.0132(3) 0.36511(18) 0.22994(16) 0.0494(5) Uani 1 1 d . . . . .
H2 H 0.008375 0.292216 0.227436 0.059 Uiso 1 1 calc R . . . .
C22 C 0.5538(3) 0.6412(2) 0.90726(15) 0.0521(6) Uani 1 1 d . . . . .
H22 H 0.581628 0.672178 0.965634 0.063 Uiso 1 1 calc R . . . .
C27 C 0.4357(4) 0.7257(2) 0.67028(16) 0.0598(6) Uani 1 1 d . . . . .
H27A H 0.513849 0.700432 0.627598 0.072 Uiso 1 1 calc R . . . .
H27B H 0.295667 0.718496 0.640609 0.072 Uiso 1 1 calc R . . . .
C11 C -0.0198(4) 0.76430(19) 0.16011(15) 0.0574(6) Uani 1 1 d . . . . .
H11A H 0.093127 0.756633 0.131513 0.069 Uiso 1 1 calc R . . . .
H11B H -0.136236 0.732177 0.118887 0.069 Uiso 1 1 calc R . . . .
C8 C 0.0738(4) 0.8830(2) 0.34230(17) 0.0612(6) Uani 1 1 d . . . . .
C24 C 0.5193(4) 0.8245(2) 0.85995(18) 0.0608(6) Uani 1 1 d . . . . .
C15 C 0.2699(5) 0.9197(3) 0.4087(2) 0.0891(10) Uani 1 1 d . . . . .
H15A H 0.280858 0.994899 0.413744 0.134 Uiso 1 1 calc GR . . . .
H15B H 0.381607 0.891044 0.387328 0.134 Uiso 1 1 calc GR . . . .
H15C H 0.269031 0.895812 0.466248 0.134 Uiso 1 1 calc GR . . . .
C16 C -0.1008(5) 0.9238(3) 0.3818(2) 0.0854(10) Uani 1 1 d . . . . .
H16A H -0.099108 0.893341 0.436951 0.128 Uiso 1 1 calc GR . . . .
H16B H -0.224464 0.904875 0.340330 0.128 Uiso 1 1 calc GR . . . .
H16C H -0.088233 0.998808 0.392717 0.128 Uiso 1 1 calc GR . . . .
C32 C 0.7319(5) 0.8621(2) 0.9042(2) 0.0873(10) Uani 1 1 d . . . . .
H32A H 0.818866 0.845604 0.863954 0.131 Uiso 1 1 calc GR . . . .
H32B H 0.776053 0.827801 0.957956 0.131 Uiso 1 1 calc GR . . . .
H32C H 0.734700 0.936668 0.918685 0.131 Uiso 1 1 calc GR . . . .
C31 C 0.3837(6) 0.8527(3) 0.9253(3) 0.1055(13) Uani 1 1 d . . . . .
H31A H 0.443070 0.830450 0.982924 0.158 Uiso 1 1 calc GR . . . .
H31B H 0.255487 0.818006 0.903585 0.158 Uiso 1 1 calc GR . . . .
H31C H 0.367608 0.927249 0.930181 0.158 Uiso 1 1 calc GR . . . .
C9 C 0.0735(7) 0.9309(3) 0.2542(2) 0.0993(12) Uani 1 1 d . . . . .
H9A H 0.035357 1.003543 0.260186 0.119 Uiso 1 1 calc R . . . .
H9B H 0.208786 0.930832 0.244396 0.119 Uiso 1 1 calc R . . . .
C25 C 0.4435(7) 0.8811(3) 0.7770(3) 0.1078(13) Uani 1 1 d . . . . .
H25 H 0.369452 0.941359 0.779437 0.129 Uiso 1 1 calc R . . . .
C26 C 0.4879(8) 0.8405(3) 0.6979(3) 0.1203(16) Uani 1 1 d . . . . .
H26A H 0.630196 0.851094 0.702250 0.144 Uiso 1 1 calc R . . . .
H26B H 0.419105 0.880850 0.650456 0.144 Uiso 1 1 calc R . . . .
C10 C -0.0548(8) 0.8796(3) 0.1776(2) 0.1172(15) Uani 1 1 d . . . . .
H10A H -0.039914 0.914748 0.125693 0.141 Uiso 1 1 calc R . . . .
H10B H -0.191815 0.887627 0.183988 0.141 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 C1 1.334(3) . ?
O2 C14 1.218(2) . ?
O4 C17 1.335(3) . ?
O6 C19 1.223(3) . ?
O3 C3 1.224(3) . ?
O5 C30 1.222(3) . ?
C1 C14 1.498(3) . ?
C1 C2 1.335(3) . ?
C29 C20 1.406(3) . ?
C29 C30 1.478(3) . ?
C29 C28 1.415(3) . ?
C20 C19 1.500(3) . ?
C20 C21 1.381(3) . ?
C4 C13 1.413(3) . ?
C4 C3 1.487(3) . ?
C4 C5 1.382(3) . ?
C14 C13 1.475(3) . ?
C17 C30 1.494(3) . ?
C17 C18 1.332(3) . ?
C13 C12 1.416(3) . ?
C28 C23 1.408(3) . ?
C28 C27 1.518(3) . ?
C19 C18 1.441(3) . ?
C12 C7 1.411(3) . ?
C12 C11 1.513(3) . ?
C23 C22 1.393(3) . ?
C23 C24 1.536(3) . ?
C3 C2 1.445(3) . ?
C7 C6 1.392(3) . ?
C7 C8 1.533(3) . ?
C21 C22 1.372(3) . ?
C5 C6 1.370(4) . ?
C27 C26 1.511(4) . ?
C11 C10 1.509(4) . ?
C8 C15 1.545(4) . ?
C8 C16 1.530(4) . ?
C8 C9 1.532(4) . ?
C24 C32 1.524(4) . ?
C24 C31 1.532(4) . ?
C24 C25 1.515(4) . ?
C9 C10 1.416(5) . ?
C25 C26 1.378(5) . ?

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
O1 C1 C14 115.49(19) . . ?
O1 C1 C2 121.9(2) . . ?
C2 C1 C14 122.6(2) . . ?
C20 C29 C30 116.64(19) . . ?
C20 C29 C28 120.43(18) . . ?
C28 C29 C30 122.93(18) . . ?
C29 C20 C19 122.46(19) . . ?
C21 C20 C29 119.5(2) . . ?
C21 C20 C19 117.99(18) . . ?
C13 C4 C3 122.37(19) . . ?
C5 C4 C13 119.3(2) . . ?
C5 C4 C3 118.3(2) . . ?
O2 C14 C1 116.13(19) . . ?
O2 C14 C13 124.9(2) . . ?
C13 C14 C1 118.93(18) . . ?
O4 C17 C30 115.4(2) . . ?
C18 C17 O4 121.9(2) . . ?
C18 C17 C30 122.7(2) . . ?
O5 C30 C29 125.2(2) . . ?
O5 C30 C17 115.6(2) . . ?
C29 C30 C17 119.19(18) . . ?
C4 C13 C14 116.91(19) . . ?
C4 C13 C12 120.63(18) . . ?
C12 C13 C14 122.46(18) . . ?
C29 C28 C27 120.90(19) . . ?
C23 C28 C29 118.87(18) . . ?
C23 C28 C27 120.2(2) . . ?
O6 C19 C20 120.4(2) . . ?
O6 C19 C18 121.3(2) . . ?
C18 C19 C20 118.34(19) . . ?
C13 C12 C11 121.27(18) . . ?
C7 C12 C13 118.58(19) . . ?
C7 C12 C11 120.1(2) . . ?
C28 C23 C24 123.2(2) . . ?
C22 C23 C28 118.9(2) . . ?
C22 C23 C24 117.9(2) . . ?
O3 C3 C4 120.8(2) . . ?
O3 C3 C2 120.7(2) . . ?
C2 C3 C4 118.56(19) . . ?
C12 C7 C8 123.2(2) . . ?
C6 C7 C12 118.8(2) . . ?
C6 C7 C8 118.0(2) . . ?
C22 C21 C20 120.1(2) . . ?
C6 C5 C4 120.0(2) . . ?
C17 C18 C19 120.6(2) . . ?
C5 C6 C7 122.5(2) . . ?
C1 C2 C3 120.5(2) . . ?
C21 C22 C23 122.2(2) . . ?
C26 C27 C28 113.0(2) . . ?
C10 C11 C12 113.5(2) . . ?
C7 C8 C15 109.9(2) . . ?
C16 C8 C7 110.0(2) . . ?
C16 C8 C15 107.9(2) . . ?
C16 C8 C9 110.2(3) . . ?
C9 C8 C7 111.2(2) . . ?
C9 C8 C15 107.6(3) . . ?
C32 C24 C23 109.6(2) . . ?
C32 C24 C31 108.4(3) . . ?
C31 C24 C23 110.3(2) . . ?
C25 C24 C23 110.9(2) . . ?
C25 C24 C32 110.3(3) . . ?
C25 C24 C31 107.3(3) . . ?
C10 C9 C8 115.4(3) . . ?
C26 C25 C24 117.9(3) . . ?
C25 C26 C27 116.9(3) . . ?
C9 C10 C11 115.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
