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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dbr61
_database_code_depnum_ccdc_archive 'CCDC 2258238'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-16
_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         'C14 H13 N O4'
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.3019(4)
_cell_length_b                   6.9207(3)
_cell_length_c                   16.2735(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.713(4)
_cell_angle_gamma                90
_cell_volume                     1246.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7823
_cell_measurement_temperature    299.03
_cell_measurement_theta_max      26.7090
_cell_measurement_theta_min      2.0850
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60390
_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    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.849
_diffrn_reflns_theta_min         2.445
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.03
_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 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  50.00   0.50    3.00    --   16.22  18.00 -24.00   52
  2  ω     69.00  94.00   0.50    3.00    --   16.22  18.00 -24.00   50
  3  ω    -37.00  22.00   0.50    3.00    --  -14.97 -94.00-120.00  118
  4  ω    -61.00  63.00   0.50    3.00    --  -14.97  18.00 -24.00  248
  5  ω    -39.00  49.00   0.50    3.00    --  -14.97  45.00 -30.00  176
  6  ω    -69.00 -10.00   0.50    3.00    --  -14.97 125.00  90.00  118
  7  ω    -63.00 -12.00   0.50    3.00    --  -14.97 125.00   0.00  102
  8  ω    -57.00  12.00   0.50    3.00    --   16.22 -30.00 120.00  138
  9  ω    -62.00  59.00   0.50    3.00    --   16.22 -18.00 167.00  242
 10  ω    -70.00  10.00   0.50    3.00    --  -14.97 -30.00 150.00  160
 11  ω    -85.00  -2.00   0.50    3.00    --  -14.97 -61.00 120.00  166
 12  ω    -93.00   7.00   0.50    3.00    --  -14.97 -18.00 167.00  200
;
_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      0.0457897000
_diffrn_orient_matrix_UB_12      0.0078411000
_diffrn_orient_matrix_UB_13      0.0368148000
_diffrn_orient_matrix_UB_21      0.0426512000
_diffrn_orient_matrix_UB_22      0.0239511000
_diffrn_orient_matrix_UB_23      -0.0248252000
_diffrn_orient_matrix_UB_31      -0.0138760000
_diffrn_orient_matrix_UB_32      0.0993795000
_diffrn_orient_matrix_UB_33      0.0031042000
_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                1982
_reflns_number_total             2593
_reflns_odcompleteness_completeness 99.53
_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         0.466
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0765
_refine_ls_restrained_S_all      1.076
_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)+(0.1084P)²+0.9247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2144
_refine_ls_wR_factor_ref         0.2262
_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:
 C13(H13A,H13B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C6(H6), C3(H3), C2(H2)
;
_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
O3 O 0.75128(19) 0.3895(3) 0.75125(12) 0.0547(6) Uani 1 1 d . . . . .
O4 O 0.7074(2) -0.0247(4) 0.53333(16) 0.0789(8) Uani 1 1 d . . . . .
O2 O 0.2973(3) 0.9990(4) 0.69547(19) 0.0874(9) Uani 1 1 d . . . . .
N1 N 0.2565(3) 0.8467(5) 0.66383(18) 0.0667(8) Uani 1 1 d . . . . .
C8 C 0.6985(2) 0.2543(4) 0.61562(15) 0.0429(6) Uani 1 1 d . . . . .
C9 C 0.7731(2) 0.3813(4) 0.68192(16) 0.0440(6) Uani 1 1 d . . . . .
C4 C 0.5001(2) 0.4284(4) 0.60654(15) 0.0433(6) Uani 1 1 d . . . . .
C7 C 0.5794(2) 0.2769(4) 0.58680(15) 0.0455(6) Uani 1 1 d . . . . .
H7 H 0.542523 0.183282 0.549170 0.055 Uiso 1 1 calc R . . . .
O1 O 0.1493(2) 0.8091(5) 0.6483(2) 0.1037(11) Uani 1 1 d . . . . .
C5 C 0.5366(2) 0.6195(4) 0.62306(17) 0.0481(7) Uani 1 1 d . . . . .
H5 H 0.615616 0.654657 0.621863 0.058 Uiso 1 1 calc R . . . .
C14 C 0.7628(3) 0.0898(4) 0.58385(17) 0.0516(7) Uani 1 1 d . . . . .
C6 C 0.4576(3) 0.7572(4) 0.64111(17) 0.0507(7) Uani 1 1 d . . . . .
H6 H 0.482384 0.884526 0.651492 0.061 Uiso 1 1 calc R . . . .
C1 C 0.3408(2) 0.7025(4) 0.64349(16) 0.0492(7) Uani 1 1 d . . . . .
C3 C 0.3794(3) 0.3811(5) 0.6063(2) 0.0565(8) Uani 1 1 d . . . . .
H3 H 0.352339 0.255945 0.592768 0.068 Uiso 1 1 calc R . . . .
C2 C 0.3002(3) 0.5164(5) 0.6258(2) 0.0607(8) Uani 1 1 d . . . . .
H2 H 0.220894 0.482906 0.627058 0.073 Uiso 1 1 calc R . . . .
C13 C 0.8951(3) 0.0725(5) 0.6170(2) 0.0617(8) Uani 1 1 d . . . . .
H13A H 0.922511 -0.052345 0.601247 0.074 Uiso 1 1 calc R . . . .
H13B H 0.910585 0.078276 0.677844 0.074 Uiso 1 1 calc R . . . .
C10 C 0.8745(3) 0.4971(5) 0.6596(2) 0.0672(9) Uani 1 1 d . . . . .
H10A H 0.847062 0.629380 0.649519 0.081 Uiso 1 1 calc R . . . .
H10B H 0.940827 0.498306 0.707961 0.081 Uiso 1 1 calc R . . . .
C12 C 0.9681(3) 0.2324(5) 0.5842(3) 0.0755(11) Uani 1 1 d . . . . .
H12A H 1.050140 0.228942 0.616822 0.091 Uiso 1 1 calc R . . . .
H12B H 0.971938 0.202229 0.526619 0.091 Uiso 1 1 calc R . . . .
C11 C 0.9217(4) 0.4317(6) 0.5867(3) 0.0794(11) Uani 1 1 d . . . . .
H11A H 0.986517 0.518914 0.580538 0.095 Uiso 1 1 calc R . . . .
H11B H 0.857825 0.448491 0.537559 0.095 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 C9 1.204(3) . ?
O4 C14 1.219(4) . ?
O2 N1 1.221(4) . ?
N1 O1 1.215(4) . ?
N1 C1 1.463(4) . ?
C8 C9 1.509(4) . ?
C8 C7 1.342(4) . ?
C8 C14 1.498(4) . ?
C9 C10 1.502(4) . ?
C4 C7 1.457(4) . ?
C4 C5 1.395(4) . ?
C4 C3 1.402(4) . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C14 C13 1.489(5) . ?
C6 H6 0.9300 . ?
C6 C1 1.381(4) . ?
C1 C2 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.376(5) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.539(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.467(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.479(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 C1 118.5(3) . . ?
O1 N1 O2 123.2(3) . . ?
O1 N1 C1 118.3(3) . . ?
C7 C8 C9 123.8(2) . . ?
C7 C8 C14 119.3(3) . . ?
C14 C8 C9 116.8(2) . . ?
O3 C9 C8 120.4(2) . . ?
O3 C9 C10 120.8(3) . . ?
C10 C9 C8 118.7(2) . . ?
C5 C4 C7 123.6(2) . . ?
C5 C4 C3 118.1(3) . . ?
C3 C4 C7 118.3(3) . . ?
C8 C7 C4 128.7(2) . . ?
C8 C7 H7 115.7 . . ?
C4 C7 H7 115.7 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
O4 C14 C8 120.6(3) . . ?
O4 C14 C13 122.2(3) . . ?
C13 C14 C8 117.2(3) . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C1 118.7(3) . . ?
C1 C6 H6 120.6 . . ?
C6 C1 N1 119.3(3) . . ?
C2 C1 N1 118.7(3) . . ?
C2 C1 C6 122.0(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C14 C13 C12 112.7(3) . . ?
H13A C13 H13B 107.8 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C9 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 C9 116.8(3) . . ?
C11 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C11 C12 C13 116.3(3) . . ?
C11 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11A 107.3 . . ?
C10 C11 H11B 107.3 . . ?
C12 C11 H11A 107.3 . . ?
C12 C11 H11B 107.3 . . ?
H11A C11 H11B 106.9 . . ?

_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.546
####################################################################### 
# 
# 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_dbr54
_database_code_depnum_ccdc_archive 'CCDC 2258240'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_audit_creation_date             2022-12-15
_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         'C18 H22 O3'
_chemical_formula_sum            'C18 H22 O3'
_chemical_formula_weight         286.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   8.6941(4)
_cell_length_b                   17.9069(10)
_cell_length_c                   10.1924(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1586.80(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4760
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      22.0080
_cell_measurement_theta_min      2.2690
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70880
_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            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9467
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.275
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   9.00   0.50   11.17    --  -15.60 -45.00  60.00   58
  2  ω      8.00  44.00   0.50   11.17    --   16.22 -94.00  30.00   72
  3  ω     11.00  72.00   0.50   11.17    --   16.22-127.00  87.00  122
  4  ω    -37.00   4.00   0.50   11.17    --   16.22 -94.00  30.00   82
  5  ω    -74.00 -28.00   0.50   11.17    --  -15.60 -45.00  60.00   92
  6  ω    -51.00 -10.00   0.50   11.17    --  -15.60 125.00  30.00   82
  7  ω    -86.00 -24.00   0.50   11.17    --  -15.60 151.00  57.00  124
  8  ω    -70.00 -26.00   0.50   11.17    --  -15.60 125.00 150.00   88
  9  ω    -97.00  63.00   0.50   11.17    --  -15.60  -9.00 -80.00  320
;
_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      0.0629045000
_diffrn_orient_matrix_UB_12      -0.0112128000
_diffrn_orient_matrix_UB_13      0.0244118000
_diffrn_orient_matrix_UB_21      0.0505886000
_diffrn_orient_matrix_UB_22      -0.0012810000
_diffrn_orient_matrix_UB_23      -0.0310715000
_diffrn_orient_matrix_UB_31      0.0112399000
_diffrn_orient_matrix_UB_32      0.0686543000
_diffrn_orient_matrix_UB_33      0.0033869000
_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         0.662
_reflns_Friedel_fraction_full    0.750
_reflns_Friedel_fraction_max     0.749
_reflns_number_gt                1948
_reflns_number_total             2473
_reflns_odcompleteness_completeness 99.89
_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         0.116
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.040
_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)+(0.0574P)²+0.0363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1091
_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:
 C16(H16A,H16B), C2(H2A,H2B), C8(H8A,H8B), C5(H5A,H5B), C15(H15A,H15B), C3(H3A,
 H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.6112(3) 0.46896(14) 0.5180(3) 0.0686(7) Uani 1 1 d . . . . .
O2 O 0.7849(3) 0.62102(14) 0.1850(2) 0.0715(7) Uani 1 1 d . . . . .
C6 C 0.7267(4) 0.5675(2) 0.2383(3) 0.0534(8) Uani 1 1 d . . . . .
C9 C 0.6616(4) 0.65639(18) 0.5846(4) 0.0537(8) Uani 1 1 d . . . . .
C1 C 0.7032(4) 0.50324(18) 0.4526(3) 0.0515(8) Uani 1 1 d . . . . .
C7 C 0.6573(3) 0.57357(17) 0.3759(3) 0.0486(8) Uani 1 1 d . . . . .
O3 O 0.1691(3) 0.5964(3) 0.3285(4) 0.1356(16) Uani 1 1 d . . . . .
C16 C 0.4179(3) 0.6390(2) 0.2760(3) 0.0555(8) Uani 1 1 d . . . . .
H16A H 0.449627 0.686811 0.311457 0.067 Uiso 1 1 calc R . . . .
H16B H 0.463028 0.634099 0.189368 0.067 Uiso 1 1 calc R . . . .
C2 C 0.8658(4) 0.4763(2) 0.4408(3) 0.0611(9) Uani 1 1 d . . . . .
H2A H 0.899863 0.456040 0.524175 0.073 Uiso 1 1 calc R . . . .
H2B H 0.932641 0.517672 0.418026 0.073 Uiso 1 1 calc R . . . .
C10 C 0.7152(4) 0.6180(2) 0.6919(4) 0.0612(9) Uani 1 1 d . . . . .
H10 H 0.791024 0.581982 0.680253 0.073 Uiso 1 1 calc R . . . .
C17 C 0.2466(4) 0.6383(2) 0.2631(4) 0.0667(10) Uani 1 1 d . . . . .
C8 C 0.7242(4) 0.64299(18) 0.4489(3) 0.0583(9) Uani 1 1 d . . . . .
H8A H 0.834907 0.637202 0.455088 0.070 Uiso 1 1 calc R . . . .
H8B H 0.704294 0.686999 0.396066 0.070 Uiso 1 1 calc R . . . .
C5 C 0.7196(4) 0.4930(2) 0.1711(3) 0.0632(9) Uani 1 1 d . . . . .
H5A H 0.707840 0.500571 0.077421 0.076 Uiso 1 1 calc R . . . .
H5B H 0.630256 0.465859 0.202255 0.076 Uiso 1 1 calc R . . . .
C15 C 0.4804(3) 0.57755(17) 0.3628(3) 0.0517(8) Uani 1 1 d . . . . .
H15A H 0.444268 0.530061 0.329006 0.062 Uiso 1 1 calc R . . . .
H15B H 0.437112 0.583702 0.449851 0.062 Uiso 1 1 calc R . . . .
C3 C 0.8757(4) 0.4157(2) 0.3345(4) 0.0686(10) Uani 1 1 d . . . . .
H3A H 0.972514 0.389269 0.343790 0.082 Uiso 1 1 calc R . . . .
H3B H 0.793400 0.379959 0.348047 0.082 Uiso 1 1 calc R . . . .
C11 C 0.6599(5) 0.6314(2) 0.8159(4) 0.0722(11) Uani 1 1 d . . . . .
H11 H 0.699529 0.605018 0.886874 0.087 Uiso 1 1 calc R . . . .
C12 C 0.5475(5) 0.6831(3) 0.8355(5) 0.0832(12) Uani 1 1 d . . . . .
H12 H 0.509750 0.692050 0.919387 0.100 Uiso 1 1 calc R . . . .
C14 C 0.5467(5) 0.7088(2) 0.6068(4) 0.0824(13) Uani 1 1 d . . . . .
H14 H 0.506765 0.735751 0.536576 0.099 Uiso 1 1 calc R . . . .
C18 C 0.1773(4) 0.6893(2) 0.1643(4) 0.0739(11) Uani 1 1 d . . . . .
H18A H 0.067331 0.684327 0.166143 0.111 Uiso 1 1 calc GR . . . .
H18B H 0.214724 0.676589 0.078593 0.111 Uiso 1 1 calc GR . . . .
H18C H 0.204947 0.739929 0.184441 0.111 Uiso 1 1 calc GR . . . .
C4 C 0.8645(4) 0.4462(2) 0.1965(4) 0.0749(11) Uani 1 1 d . . . . .
H4A H 0.866165 0.404796 0.135180 0.090 Uiso 1 1 calc R . . . .
H4B H 0.954273 0.476840 0.179176 0.090 Uiso 1 1 calc R . . . .
C13 C 0.4912(6) 0.7214(3) 0.7312(5) 0.0980(15) Uani 1 1 d . . . . .
H13 H 0.414136 0.756687 0.744066 0.118 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 1.209(3) . ?
O2 C6 1.212(4) . ?
C6 C7 1.531(5) . ?
C6 C5 1.501(5) . ?
C9 C10 1.373(5) . ?
C9 C8 1.505(5) . ?
C9 C14 1.390(5) . ?
C1 C7 1.535(4) . ?
C1 C2 1.499(4) . ?
C7 C8 1.561(4) . ?
C7 C15 1.545(4) . ?
O3 C17 1.209(5) . ?
C16 C17 1.496(5) . ?
C16 C15 1.512(4) . ?
C2 C3 1.536(5) . ?
C10 C11 1.374(6) . ?
C17 C18 1.487(5) . ?
C5 C4 1.534(5) . ?
C3 C4 1.512(5) . ?
C11 C12 1.361(6) . ?
C12 C13 1.356(7) . ?
C14 C13 1.376(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
O2 C6 C7 121.3(3) . . ?
O2 C6 C5 121.1(3) . . ?
C5 C6 C7 117.7(3) . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 C14 116.9(4) . . ?
C14 C9 C8 121.2(3) . . ?
O1 C1 C7 121.7(3) . . ?
O1 C1 C2 120.3(3) . . ?
C2 C1 C7 118.0(3) . . ?
C6 C7 C1 107.8(3) . . ?
C6 C7 C8 110.3(3) . . ?
C6 C7 C15 108.5(2) . . ?
C1 C7 C8 108.3(3) . . ?
C1 C7 C15 109.9(2) . . ?
C15 C7 C8 112.0(3) . . ?
C17 C16 C15 113.8(3) . . ?
C1 C2 C3 109.7(3) . . ?
C9 C10 C11 121.8(3) . . ?
O3 C17 C16 120.7(4) . . ?
O3 C17 C18 121.9(4) . . ?
C18 C17 C16 117.3(4) . . ?
C9 C8 C7 115.5(3) . . ?
C6 C5 C4 112.0(3) . . ?
C16 C15 C7 116.2(2) . . ?
C4 C3 C2 113.4(3) . . ?
C12 C11 C10 120.3(4) . . ?
C13 C12 C11 119.3(4) . . ?
C13 C14 C9 120.9(4) . . ?
C3 C4 C5 114.0(3) . . ?
C12 C13 C14 120.8(4) . . ?

_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 1.690
_oxdiff_exptl_absorpt_empirical_full_min 0.553
####################################################################### 
# 
# 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_dbr56
_database_code_depnum_ccdc_archive 'CCDC 2258242'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9700(5)
_cell_length_b                   11.1812(6)
_cell_length_c                   7.9888(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.788(7)
_cell_angle_gamma                90
_cell_volume                     665.57(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4304
_cell_measurement_temperature    299.0(2)
_cell_measurement_theta_max      25.6050
_cell_measurement_theta_min      2.7100
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50160
_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_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7906
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.009
_diffrn_reflns_theta_min         2.727
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  41.00   0.50    7.00    --   16.22 -45.00   0.00  190
  2  ω     10.00  71.00   0.50    7.00    --   16.22-125.00   0.00  122
  3  ω    -37.00  21.00   0.50    7.00    --  -15.60 -94.00 -60.00  116
  4  ω    -31.00  21.00   0.50    7.00    --  -15.60 -96.00-109.00  104
  5  ω    -40.00  55.00   0.50    7.00    --  -15.60  45.00-103.00  190
  6  ω    -37.00  53.00   0.50    7.00    --   16.22 -94.00-180.00  180
  7  ω     10.00  71.00   0.50    7.00    --   16.22-125.00-150.00  122
  8  ω     10.00  71.00   0.50    7.00    --   16.22-125.00-120.00  122
  9  ω    -70.00 -10.00   0.50    7.00    --  -15.60 125.00 -90.00  120
 10  ω    -89.00 -36.00   0.50    7.00    --  -15.60 -30.00  90.00  106
 11  ω    -54.00  41.00   0.50    7.00    --   16.22 -45.00 106.00  190
 12  ω    -37.00  21.00   0.50    7.00    --  -15.60 -94.00 150.00  116
 13  ω    -17.00  45.00   0.50    7.00    --   16.22  87.00 104.00  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      -0.0203180000
_diffrn_orient_matrix_UB_12      0.0356860000
_diffrn_orient_matrix_UB_13      -0.0780932000
_diffrn_orient_matrix_UB_21      -0.0912145000
_diffrn_orient_matrix_UB_22      0.0025479000
_diffrn_orient_matrix_UB_23      -0.0071280000
_diffrn_orient_matrix_UB_31      0.0182902000
_diffrn_orient_matrix_UB_32      0.0524028000
_diffrn_orient_matrix_UB_33      0.0535366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.802
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                2006
_reflns_number_total             2639
_reflns_odcompleteness_completeness 99.03
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/1 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      0.978
_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)+(0.0445P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0974
_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:
 C10(H10A,H10B), C5(H5A,H5B), C2(H2A,H2B), C12(H12A,H12B), C9(H9A,H9B), C4(H4A,
 H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C16(H16)
;
_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 -0.9376(3) -0.4617(2) -0.4787(3) 0.0566(6) Uani 1 1 d . . . . .
O2 O -0.5428(3) -0.7202(2) -0.0368(3) 0.0698(7) Uani 1 1 d . . . . .
O003 O -0.4344(4) -0.4765(3) -0.7257(2) 0.0805(8) Uani 1 1 d . . . . .
C6 C -0.3786(4) -0.5036(2) -0.2651(3) 0.0371(6) Uani 1 1 d . . . . .
C7 C -0.3539(4) -0.4707(3) -0.4148(3) 0.0437(7) Uani 1 1 d . . . . .
H7 H -0.2579 -0.4202 -0.4041 0.052 Uiso 1 1 calc R U . . .
C11 C -0.5276(4) -0.5870(3) -0.2658(3) 0.0410(7) Uani 1 1 d . . . . .
C1 C -0.4523(4) -0.6827(3) -0.1185(4) 0.0485(8) Uani 1 1 d . . . . .
C13 C -0.7762(4) -0.4258(3) -0.3533(4) 0.0447(7) Uani 1 1 d . . . . .
C14 C -0.7483(5) -0.3110(3) -0.3794(4) 0.0507(8) Uani 1 1 d . . . . .
H14 H -0.6490 -0.2659 -0.3132 0.061 Uiso 1 1 calc R U . . .
C8 C -0.4672(4) -0.5083(3) -0.5949(4) 0.0487(7) Uani 1 1 d . . . . .
C10 C -0.6018(4) -0.6573(3) -0.4436(4) 0.0506(8) Uani 1 1 d . . . . .
H10A H -0.5199 -0.7223 -0.4401 0.061 Uiso 1 1 calc R U . . .
H10B H -0.7161 -0.6925 -0.4530 0.061 Uiso 1 1 calc R U . . .
C5 C -0.2528(4) -0.4569(3) -0.0874(3) 0.0515(8) Uani 1 1 d . . . . .
H5A H -0.3150 -0.4550 -0.0028 0.062 Uiso 1 1 calc R U . . .
H5B H -0.2180 -0.3757 -0.1027 0.062 Uiso 1 1 calc R U . . .
C15 C -0.8973(5) -0.2701(3) -0.5262(4) 0.0595(9) Uani 1 1 d . . . . .
H15 H -0.9148 -0.1934 -0.5741 0.071 Uiso 1 1 calc R U . . .
C16 C -1.0072(5) -0.3628(3) -0.5820(4) 0.0609(9) Uani 1 1 d . . . . .
H16 H -1.1159 -0.3610 -0.6777 0.073 Uiso 1 1 calc R U . . .
C2 C -0.2649(5) -0.7289(3) -0.0818(4) 0.0602(9) Uani 1 1 d . . . . .
H2A H -0.2411 -0.7295 -0.1928 0.072 Uiso 1 1 calc R U . . .
H2B H -0.2571 -0.8106 -0.0391 0.072 Uiso 1 1 calc R U . . .
C12 C -0.6745(4) -0.5172(3) -0.2216(4) 0.0502(8) Uani 1 1 d . . . . .
H12A H -0.7597 -0.5747 -0.2075 0.060 Uiso 1 1 calc R U . . .
H12B H -0.6184 -0.4780 -0.1070 0.060 Uiso 1 1 calc R U . . .
C9 C -0.6284(4) -0.5826(3) -0.6099(3) 0.0518(8) Uani 1 1 d . . . . .
H9A H -0.6547 -0.6353 -0.7126 0.062 Uiso 1 1 calc R U . . .
H9B H -0.7309 -0.5304 -0.6305 0.062 Uiso 1 1 calc R U . . .
C4 C -0.0852(4) -0.5338(3) -0.0117(4) 0.0605(10) Uani 1 1 d . . . . .
H4A H -0.0347 -0.5469 -0.1043 0.073 Uiso 1 1 calc R U . . .
H4B H 0.0032 -0.4910 0.0856 0.073 Uiso 1 1 calc R U . . .
C3 C -0.1212(5) -0.6537(4) 0.0566(4) 0.0728(11) Uani 1 1 d . . . . .
H3A H -0.1579 -0.6404 0.1586 0.087 Uiso 1 1 calc R U . . .
H3B H -0.0101 -0.6989 0.0984 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.381(3) . ?
O1 C16 1.374(4) . ?
O2 C1 1.206(4) . ?
O003 C8 1.217(3) . ?
C6 C7 1.330(3) . ?
C6 C11 1.508(4) . ?
C6 C5 1.511(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.463(4) . ?
C11 C1 1.545(4) . ?
C11 C10 1.546(4) . ?
C11 C12 1.549(4) . ?
C1 C2 1.508(4) . ?
C13 C14 1.331(4) . ?
C13 C12 1.484(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.417(4) . ?
C8 C9 1.498(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.519(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.522(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.327(5) . ?
C16 H16 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.530(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.512(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 C13 106.0(2) . . ?
C7 C6 C11 122.3(2) . . ?
C7 C6 C5 119.2(3) . . ?
C11 C6 C5 118.4(2) . . ?
C6 C7 H7 117.7 . . ?
C6 C7 C8 124.6(3) . . ?
C8 C7 H7 117.7 . . ?
C6 C11 C1 109.5(2) . . ?
C6 C11 C10 111.2(2) . . ?
C6 C11 C12 110.2(2) . . ?
C1 C11 C10 105.4(2) . . ?
C1 C11 C12 107.2(2) . . ?
C10 C11 C12 113.1(2) . . ?
O2 C1 C11 120.5(3) . . ?
O2 C1 C2 121.1(3) . . ?
C2 C1 C11 118.4(3) . . ?
O1 C13 C12 116.6(3) . . ?
C14 C13 O1 109.3(3) . . ?
C14 C13 C12 134.1(3) . . ?
C13 C14 H14 126.2 . . ?
C13 C14 C15 107.7(3) . . ?
C15 C14 H14 126.2 . . ?
O003 C8 C7 121.0(3) . . ?
O003 C8 C9 122.2(3) . . ?
C7 C8 C9 116.8(2) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C9 C10 C11 114.4(2) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C6 C5 C4 112.0(2) . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C14 C15 H15 126.7 . . ?
C16 C15 C14 106.6(3) . . ?
C16 C15 H15 126.7 . . ?
O1 C16 H16 124.8 . . ?
C15 C16 O1 110.4(3) . . ?
C15 C16 H16 124.8 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.9(3) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C11 C12 H12A 108.1 . . ?
C11 C12 H12B 108.1 . . ?
C13 C12 C11 116.9(2) . . ?
C13 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C8 C9 C10 112.7(2) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C3 C4 C5 113.1(3) . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 C2 114.5(3) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 0.4(4) . . . . ?
O1 C13 C12 C11 95.1(3) . . . . ?
O2 C1 C2 C3 -92.7(3) . . . . ?
O003 C8 C9 C10 153.8(3) . . . . ?
C6 C7 C8 O003 -178.5(3) . . . . ?
C6 C7 C8 C9 4.1(5) . . . . ?
C6 C11 C1 O2 144.9(3) . . . . ?
C6 C11 C1 C2 -35.9(4) . . . . ?
C6 C11 C10 C9 -43.0(3) . . . . ?
C6 C11 C12 C13 65.3(3) . . . . ?
C6 C5 C4 C3 -72.2(3) . . . . ?
C7 C6 C11 C1 134.3(3) . . . . ?
C7 C6 C11 C10 18.2(4) . . . . ?
C7 C6 C11 C12 -108.0(3) . . . . ?
C7 C6 C5 C4 -85.9(3) . . . . ?
C7 C8 C9 C10 -28.9(4) . . . . ?
C11 C6 C7 C8 1.2(5) . . . . ?
C11 C6 C5 C4 93.7(3) . . . . ?
C11 C1 C2 C3 88.2(3) . . . . ?
C11 C10 C9 C8 48.9(4) . . . . ?
C1 C11 C10 C9 -161.5(3) . . . . ?
C1 C11 C12 C13 -175.6(3) . . . . ?
C1 C2 C3 C4 -73.9(4) . . . . ?
C13 O1 C16 C15 0.0(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C13 C12 C11 -85.8(4) . . . . ?
C14 C15 C16 O1 0.2(4) . . . . ?
C10 C11 C1 O2 -95.4(3) . . . . ?
C10 C11 C1 C2 83.8(3) . . . . ?
C10 C11 C12 C13 -59.8(3) . . . . ?
C5 C6 C7 C8 -179.2(3) . . . . ?
C5 C6 C11 C1 -45.3(3) . . . . ?
C5 C6 C11 C10 -161.4(3) . . . . ?
C5 C6 C11 C12 72.4(3) . . . . ?
C5 C4 C3 C2 56.2(4) . . . . ?
C16 O1 C13 C14 -0.3(3) . . . . ?
C16 O1 C13 C12 179.0(3) . . . . ?
C12 C11 C1 O2 25.3(4) . . . . ?
C12 C11 C1 C2 -155.5(3) . . . . ?
C12 C11 C10 C9 81.7(3) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?

_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 4.092
_oxdiff_exptl_absorpt_empirical_full_min 0.454
####################################################################### 
# 
# 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_dbr44
_database_code_depnum_ccdc_archive 'CCDC 2258239'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_audit_creation_date             2022-06-15
_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         'C14 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.4952(7)
_cell_length_b                   5.8210(3)
_cell_length_c                   14.2222(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.011(5)
_cell_angle_gamma                90
_cell_volume                     1266.06(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4751
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      24.2260
_cell_measurement_theta_min      2.6510
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72612
_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            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15553
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.903
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  58.00   0.50    4.00    --  -14.97  30.00 -60.00   66
  2  ω     25.00  94.00   0.50    4.00    --   16.22  10.00-113.00  138
  3  ω     21.00  54.00   0.50    4.00    --   16.22-125.00-180.00   66
  4  ω    -37.00  22.00   0.50    4.00    --  -14.97 -94.00-120.00  118
  5  ω     23.00  49.00   0.50    4.00    --   16.22-125.00 -60.00   52
  6  ω     19.00  45.00   0.50    4.00    --   16.22 -94.00   0.00   52
  7  ω    -37.00   1.00   0.50    4.00    --   16.22 -94.00   0.00   76
  8  ω    -65.00  94.00   0.50    4.00    --   16.22 -10.00  73.00  318
  9  ω    -15.00  17.00   0.50    4.00    --  -14.97  30.00 -60.00   64
 10  ω     -9.00  88.00   0.50    4.00    --   16.22  30.00 -90.00  194
 11  ω    -53.00 -12.00   0.50    4.00    --  -14.97 125.00  60.00   82
 12  ω    -38.00 -13.00   0.50    4.00    --  -14.97 125.00 150.00   50
 13  ω    -96.00  63.00   0.50    4.00    --  -14.97 -10.00  73.00  318
 14  ω    -68.00 -11.00   0.50    4.00    --  -14.97 125.00 -60.00  114
 15  ω    -92.00  66.00   0.50    4.00    --  -14.97  10.00-113.00  316
;
_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      -0.0454850000
_diffrn_orient_matrix_UB_12      -0.0151804000
_diffrn_orient_matrix_UB_13      -0.0122111000
_diffrn_orient_matrix_UB_21      -0.0072911000
_diffrn_orient_matrix_UB_22      0.0048362000
_diffrn_orient_matrix_UB_23      -0.0523948000
_diffrn_orient_matrix_UB_31      0.0054215000
_diffrn_orient_matrix_UB_32      -0.1207667000
_diffrn_orient_matrix_UB_33      -0.0005153000
_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                1651
_reflns_number_total             2646
_reflns_odcompleteness_completeness 99.72
_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         0.276
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.050
_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)+(0.1215P)²+0.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.2185
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 1.12
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 1.12
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.12A with sigma of 0.04 and
sigma for terminal atoms of 0.08
All non-hydrogen atoms have similar U: within 1.12A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3), C2(H2)
;
_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
O3 O 0.81378(12) 0.7983(3) 0.42025(15) 0.0731(6) Uani 1 1 d . U . . .
O4 O 0.94197(11) 0.2846(3) 0.53800(13) 0.0755(6) Uani 1 1 d . U . . .
O1 O 0.35473(12) 0.5298(4) 0.29547(17) 0.0974(8) Uani 1 1 d . U . . .
N1 N 0.41046(14) 0.6629(5) 0.34878(17) 0.0723(7) Uani 1 1 d . U . . .
O2 O 0.39356(12) 0.8523(5) 0.37339(19) 0.1051(9) Uani 1 1 d . U . . .
C8 C 0.80817(13) 0.3911(4) 0.40844(16) 0.0490(6) Uani 1 1 d . U . . .
H8 H 0.771606 0.293756 0.352376 0.059 Uiso 1 1 calc R . . . .
C14 C 0.80949(13) 0.6327(5) 0.36764(18) 0.0537(6) Uani 1 1 d . U . . .
C9 C 0.90094(13) 0.2974(4) 0.44716(17) 0.0536(6) Uani 1 1 d . U . . .
C1 C 0.50218(14) 0.5924(5) 0.38412(18) 0.0546(6) Uani 1 1 d . U . . .
C4 C 0.67545(14) 0.4613(4) 0.45343(16) 0.0528(6) Uani 1 1 d . U . . .
C5 C 0.65116(14) 0.6711(4) 0.47960(18) 0.0595(7) Uani 1 1 d . U . . .
H5 H 0.694130 0.769471 0.521089 0.071 Uiso 1 1 calc R . . . .
C6 C 0.56474(15) 0.7389(5) 0.44581(19) 0.0600(7) Uani 1 1 d . U . . .
H6 H 0.549277 0.880457 0.464411 0.072 Uiso 1 1 calc R . . . .
C7 C 0.76995(14) 0.3889(5) 0.49136(18) 0.0605(7) Uani 1 1 d . U . . .
H7A H 0.775104 0.235089 0.519293 0.073 Uiso 1 1 calc R . . . .
H7B H 0.803954 0.491228 0.545626 0.073 Uiso 1 1 calc R . . . .
C13 C 0.80417(15) 0.6534(5) 0.26072(19) 0.0626(7) Uani 1 1 d . U . . .
H13A H 0.802280 0.815147 0.243570 0.075 Uiso 1 1 calc R . . . .
H13B H 0.749756 0.584687 0.216168 0.075 Uiso 1 1 calc R . . . .
C3 C 0.61031(15) 0.3179(5) 0.39194(18) 0.0604(7) Uani 1 1 d . U . . .
H3 H 0.625459 0.175056 0.374170 0.072 Uiso 1 1 calc R . . . .
C2 C 0.52278(15) 0.3819(5) 0.35602(19) 0.0634(7) Uani 1 1 d . U . . .
H2 H 0.479497 0.284759 0.314178 0.076 Uiso 1 1 calc R . . . .
C10 C 0.94007(14) 0.2246(5) 0.3728(2) 0.0639(7) Uani 1 1 d . U . . .
H10A H 0.946432 0.058793 0.376898 0.077 Uiso 1 1 calc R . . . .
H10B H 0.998432 0.289217 0.394483 0.077 Uiso 1 1 calc R . . . .
C11 C 0.89225(15) 0.2874(5) 0.26265(19) 0.0673(8) Uani 1 1 d . U . . .
H11A H 0.924161 0.223407 0.223717 0.081 Uiso 1 1 calc R . . . .
H11B H 0.835174 0.214820 0.239080 0.081 Uiso 1 1 calc R . . . .
C12 C 0.87968(15) 0.5410(5) 0.24000(19) 0.0696(8) Uani 1 1 d . U . . .
H12A H 0.870242 0.564350 0.169135 0.083 Uiso 1 1 calc R . . . .
H12B H 0.933379 0.619724 0.280050 0.083 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 C14 1.206(3) . ?
O4 C9 1.215(3) . ?
O1 N1 1.224(3) . ?
N1 O2 1.220(3) . ?
N1 C1 1.463(3) . ?
C8 H8 0.9800 . ?
C8 C14 1.524(3) . ?
C8 C9 1.520(3) . ?
C8 C7 1.532(3) . ?
C14 C13 1.495(3) . ?
C9 C10 1.492(3) . ?
C1 C6 1.372(3) . ?
C1 C2 1.371(4) . ?
C4 C5 1.379(3) . ?
C4 C7 1.506(3) . ?
C4 C3 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.530(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.390(3) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.511(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.508(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C1 118.4(3) . . ?
O2 N1 O1 123.4(2) . . ?
O2 N1 C1 118.2(2) . . ?
C14 C8 H8 108.4 . . ?
C14 C8 C7 111.7(2) . . ?
C9 C8 H8 108.4 . . ?
C9 C8 C14 108.24(17) . . ?
C9 C8 C7 111.53(18) . . ?
C7 C8 H8 108.4 . . ?
O3 C14 C8 120.5(2) . . ?
O3 C14 C13 122.3(2) . . ?
C13 C14 C8 117.3(2) . . ?
O4 C9 C8 119.4(2) . . ?
O4 C9 C10 121.3(2) . . ?
C10 C9 C8 119.30(19) . . ?
C6 C1 N1 118.6(2) . . ?
C2 C1 N1 119.2(2) . . ?
C2 C1 C6 122.2(2) . . ?
C5 C4 C7 121.2(2) . . ?
C5 C4 C3 118.0(2) . . ?
C3 C4 C7 120.8(2) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C4 C7 C8 113.03(18) . . ?
C4 C7 H7A 109.0 . . ?
C4 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C14 C13 C12 114.8(2) . . ?
H13A C13 H13B 107.5 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C4 C3 H3 119.2 . . ?
C4 C3 C2 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C9 C10 H10A 107.8 . . ?
C9 C10 H10B 107.8 . . ?
C9 C10 C11 118.01(19) . . ?
H10A C10 H10B 107.1 . . ?
C11 C10 H10A 107.8 . . ?
C11 C10 H10B 107.8 . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C10 115.8(2) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C11 C12 C13 115.7(2) . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?

_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 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.545
####################################################################### 
# 
# 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_dbr59
_database_code_depnum_ccdc_archive 'CCDC 2258241'
loop_
_audit_author_name
_audit_author_address
'Prof. Raghavaiah Pallepogu '
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H20 O2'
_chemical_formula_sum            'C18 H20 O2'
_chemical_formula_weight         268.34
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3138(4)
_cell_length_b                   12.6070(6)
_cell_length_c                   15.9123(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1467.19(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8513
_cell_measurement_temperature    299.2(2)
_cell_measurement_theta_max      23.5440
_cell_measurement_theta_min      2.0600
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63664
_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_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17583
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.924
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.2(2)
_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 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  43.00   0.50    7.00    --   16.22 -55.00 -60.00  192
  2  ω     10.00  71.00   0.50    7.00    --   16.22-125.00 -30.00  122
  3  ω    -37.00  22.00   0.50    7.00    --  -14.97 -94.00-120.00  118
  4  ω    -30.00  22.00   0.50    7.00    --  -14.97 -97.00-156.00  104
  5  ω    -46.00  58.00   0.50    7.00    --  -14.97  77.00-180.00  208
  6  ω    -69.00 -10.00   0.50    7.00    --  -14.97 125.00 -90.00  118
  7  ω    -69.00 -10.00   0.50    7.00    --  -14.97 125.00 -60.00  118
  8  ω    -69.00 -10.00   0.50    7.00    --  -14.97 125.00   0.00  118
  9  ω    -69.00 -10.00   0.50    7.00    --  -14.97 125.00 -30.00  118
 10  ω    -46.00  58.00   0.50    7.00    --  -14.97  77.00  90.00  208
 11  ω    -37.00  22.00   0.50    7.00    --  -14.97 -94.00  90.00  118
 12  ω    -87.00  16.00   0.50    7.00    --  -14.97 -75.00  88.00  206
 13  ω    -85.00 -60.00   0.50    7.00    --  -14.97 -61.00 -30.00   50
;
_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      0.0201653000
_diffrn_orient_matrix_UB_12      0.0411145000
_diffrn_orient_matrix_UB_13      0.0289763000
_diffrn_orient_matrix_UB_21      0.0889262000
_diffrn_orient_matrix_UB_22      -0.0212625000
_diffrn_orient_matrix_UB_23      0.0059051000
_diffrn_orient_matrix_UB_31      0.0331473000
_diffrn_orient_matrix_UB_32      0.0319423000
_diffrn_orient_matrix_UB_33      -0.0333534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                2378
_reflns_number_total             3074
_reflns_odcompleteness_completeness 99.83
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/1 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 864 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_coef       0.055(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.044
_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)+(0.0495P)²+0.0495P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1021
_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:
 C12(H12A,H12B), C8(H8A,H8B), C9(H9A,H9B), C2(H2A,H2B), C5(H5A,H5B), C4(H4A,
 H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C18(H18), C15(H15), C17(H17), C16(H16)
;
_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 0.2359(3) 0.85482(12) 0.77239(11) 0.0735(5) Uani 1 1 d . . . . .
C13 C 0.4436(3) 0.66543(16) 0.57933(14) 0.0534(5) Uani 1 1 d . . . . .
C6 C 0.3894(3) 0.59031(15) 0.76671(13) 0.0495(5) Uani 1 1 d . . . . .
O2 O 0.2143(3) 0.35362(14) 0.67769(18) 0.1138(9) Uani 1 1 d . . . . .
C7 C 0.2799(3) 0.67631(14) 0.72443(13) 0.0480(5) Uani 1 1 d . . . . .
C11 C 0.3600(3) 0.48826(17) 0.75072(15) 0.0589(6) Uani 1 1 d . . . . .
H11 H 0.4309 0.4388 0.7794 0.071 Uiso 1 1 calc R U . . .
C1 C 0.2308(3) 0.76163(16) 0.78981(14) 0.0543(5) Uani 1 1 d . . . . .
C12 C 0.3965(4) 0.73022(16) 0.65557(14) 0.0587(6) Uani 1 1 d . . . . .
H12A H 0.3320 0.7932 0.6369 0.070 Uiso 1 1 calc R U . . .
H12B H 0.5100 0.7536 0.6811 0.070 Uiso 1 1 calc R U . . .
C8 C 0.0953(3) 0.63349(17) 0.69149(14) 0.0580(6) Uani 1 1 d . . . . .
H8A H 0.0111 0.6277 0.7384 0.070 Uiso 1 1 calc R U . . .
H8B H 0.0447 0.6845 0.6522 0.070 Uiso 1 1 calc R U . . .
C14 C 0.5815(3) 0.59051(18) 0.58098(17) 0.0658(7) Uani 1 1 d . . . . .
H14 H 0.6447 0.5776 0.6307 0.079 Uiso 1 1 calc R U . . .
C9 C 0.1077(4) 0.52624(18) 0.64814(15) 0.0647(6) Uani 1 1 d . . . . .
H9A H -0.0145 0.4969 0.6433 0.078 Uiso 1 1 calc R U . . .
H9B H 0.1544 0.5367 0.5917 0.078 Uiso 1 1 calc R U . . .
C10 C 0.2252(3) 0.44845(18) 0.69174(17) 0.0660(6) Uani 1 1 d . . . . .
C18 C 0.3549(4) 0.6830(2) 0.50433(15) 0.0673(7) Uani 1 1 d . . . . .
H18 H 0.2621 0.7334 0.5017 0.081 Uiso 1 1 calc R U . . .
C2 C 0.1785(4) 0.7265(2) 0.87656(15) 0.0696(7) Uani 1 1 d . . . . .
H2A H 0.1235 0.6566 0.8738 0.083 Uiso 1 1 calc R U . . .
H2B H 0.0884 0.7751 0.8994 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5364(4) 0.62203(19) 0.82701(17) 0.0710(7) Uani 1 1 d . . . . .
H5A H 0.5857 0.6901 0.8099 0.085 Uiso 1 1 calc R U . . .
H5B H 0.6346 0.5705 0.8242 0.085 Uiso 1 1 calc R U . . .
C15 C 0.6256(5) 0.5351(2) 0.5095(2) 0.0913(9) Uani 1 1 d . . . . .
H15 H 0.7178 0.4843 0.5117 0.110 Uiso 1 1 calc R U . . .
C17 C 0.4016(5) 0.6271(3) 0.43321(18) 0.0879(9) Uani 1 1 d . . . . .
H17 H 0.3402 0.6401 0.3831 0.105 Uiso 1 1 calc R U . . .
C16 C 0.5373(6) 0.5527(3) 0.4356(2) 0.0960(11) Uani 1 1 d . . . . .
H16 H 0.5687 0.5148 0.3875 0.115 Uiso 1 1 calc R U . . .
C4 C 0.4702(5) 0.6303(2) 0.91789(18) 0.0873(9) Uani 1 1 d . . . . .
H4A H 0.4070 0.5653 0.9325 0.105 Uiso 1 1 calc R U . . .
H4B H 0.5759 0.6364 0.9544 0.105 Uiso 1 1 calc R U . . .
C3 C 0.3440(5) 0.7231(3) 0.93447(18) 0.0918(10) Uani 1 1 d . . . . .
H3A H 0.4125 0.7884 0.9280 0.110 Uiso 1 1 calc R U . . .
H3B H 0.3019 0.7195 0.9922 0.110 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.208(2) . ?
C13 C12 1.502(3) . ?
C13 C14 1.382(3) . ?
C13 C18 1.376(3) . ?
C6 C7 1.507(3) . ?
C6 C11 1.329(3) . ?
C6 C5 1.496(3) . ?
O2 C10 1.219(3) . ?
C7 C1 1.539(3) . ?
C7 C12 1.546(3) . ?
C7 C8 1.545(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.451(3) . ?
C1 C2 1.499(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.521(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.477(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.376(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.521(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.528(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.366(5) . ?
C16 H16 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.513(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C13 C12 121.5(2) . . ?
C18 C13 C12 120.3(2) . . ?
C18 C13 C14 118.1(2) . . ?
C11 C6 C7 121.7(2) . . ?
C11 C6 C5 119.9(2) . . ?
C5 C6 C7 118.44(18) . . ?
C6 C7 C1 108.97(17) . . ?
C6 C7 C12 109.83(18) . . ?
C6 C7 C8 111.38(16) . . ?
C1 C7 C12 107.49(16) . . ?
C1 C7 C8 105.66(17) . . ?
C8 C7 C12 113.28(18) . . ?
C6 C11 H11 117.7 . . ?
C6 C11 C10 124.7(2) . . ?
C10 C11 H11 117.7 . . ?
O1 C1 C7 121.2(2) . . ?
O1 C1 C2 120.4(2) . . ?
C2 C1 C7 118.40(19) . . ?
C13 C12 C7 117.36(16) . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C7 C12 H12A 108.0 . . ?
C7 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.35(19) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.32(19) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
O2 C10 C11 120.2(3) . . ?
O2 C10 C9 121.8(2) . . ?
C11 C10 C9 118.01(19) . . ?
C13 C18 H18 119.6 . . ?
C13 C18 C17 120.9(3) . . ?
C17 C18 H18 119.6 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.3(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C6 C5 C4 113.4(2) . . ?
H5A C5 H5B 107.7 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.3 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C3 C4 C5 114.3(2) . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 C2 113.7(2) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -87.0(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C13 C18 C17 C16 0.1(4) . . . . ?
C6 C7 C1 O1 139.8(2) . . . . ?
C6 C7 C1 C2 -39.4(3) . . . . ?
C6 C7 C12 C13 68.3(3) . . . . ?
C6 C7 C8 C9 -43.1(3) . . . . ?
C6 C11 C10 O2 176.1(3) . . . . ?
C6 C11 C10 C9 -2.1(4) . . . . ?
C6 C5 C4 C3 -70.2(3) . . . . ?
C7 C6 C11 C10 0.9(4) . . . . ?
C7 C6 C5 C4 91.1(3) . . . . ?
C7 C1 C2 C3 92.2(3) . . . . ?
C7 C8 C9 C10 43.2(3) . . . . ?
C11 C6 C7 C1 138.0(2) . . . . ?
C11 C6 C7 C12 -104.5(2) . . . . ?
C11 C6 C7 C8 21.8(3) . . . . ?
C11 C6 C5 C4 -89.9(3) . . . . ?
C1 C7 C12 C13 -173.24(19) . . . . ?
C1 C7 C8 C9 -161.29(18) . . . . ?
C1 C2 C3 C4 -74.1(3) . . . . ?
C12 C13 C14 C15 -177.8(2) . . . . ?
C12 C13 C18 C17 177.4(2) . . . . ?
C12 C7 C1 O1 20.8(3) . . . . ?
C12 C7 C1 C2 -158.4(2) . . . . ?
C12 C7 C8 C9 81.3(2) . . . . ?
C8 C7 C1 O1 -100.4(3) . . . . ?
C8 C7 C1 C2 80.3(2) . . . . ?
C8 C7 C12 C13 -56.9(3) . . . . ?
C8 C9 C10 O2 161.5(3) . . . . ?
C8 C9 C10 C11 -20.4(3) . . . . ?
C14 C13 C12 C7 -78.5(3) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C18 C13 C12 C7 104.6(3) . . . . ?
C18 C13 C14 C15 -0.8(4) . . . . ?
C18 C17 C16 C15 -0.1(5) . . . . ?
C5 C6 C7 C1 -43.0(3) . . . . ?
C5 C6 C7 C12 74.5(2) . . . . ?
C5 C6 C7 C8 -159.2(2) . . . . ?
C5 C6 C11 C10 -178.1(2) . . . . ?
C5 C4 C3 C2 54.5(4) . . . . ?

_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 2.597
_oxdiff_exptl_absorpt_empirical_full_min 0.474
