# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_ap1502
_database_code_depnum_ccdc_archive 'CCDC 2271607'
loop_
_audit_author_name
_audit_author_address
'PRIYANKA PATIL'
;XRD SAIF, IIT Madras
India
;
_audit_update_record             
;
2023-06-22 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 N O2'
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.5905(13)
_cell_length_b                   9.8247(13)
_cell_length_c                   17.961(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.033(5)
_cell_angle_gamma                90
_cell_volume                     1634.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      72.08
_cell_measurement_theta_min      4.79
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5958
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1305 before and 0.0854 after correction.
The Ratio of minimum to maximum transmission is 0.7906.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25224
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.307
_diffrn_reflns_theta_min         4.794
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2498
_reflns_number_total             3215
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0154(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.055
_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)+(0.1274P)²+0.1089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.1913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P)
;
_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
O001 O 0.69611(16) 0.61139(16) 0.38717(9) 0.0697(4) Uani 1 1 d . . . . .
O002 O 0.74107(16) 0.77998(16) 0.27189(9) 0.0687(4) Uani 1 1 d . . . . .
N003 N 0.47252(18) 0.84420(17) 0.42494(10) 0.0613(4) Uani 1 1 d . . . . .
C004 C 0.38792(17) 0.48464(18) 0.35562(10) 0.0513(4) Uani 1 1 d . . . . .
C005 C 0.38405(19) 0.61474(18) 0.39665(9) 0.0522(4) Uani 1 1 d . . . . .
C006 C 0.3858(2) 0.4861(2) 0.27767(10) 0.0565(4) Uani 1 1 d . . . . .
H006 H 0.383035 0.568849 0.252181 0.068 Uiso 1 1 calc R U . . .
C007 C 0.60847(19) 0.70025(19) 0.36078(10) 0.0557(4) Uani 1 1 d . . . . .
C008 C 0.47989(19) 0.72164(18) 0.39370(10) 0.0539(4) Uani 1 1 d . . . . .
C009 C 0.2815(2) 0.63819(19) 0.43777(10) 0.0560(4) Uani 1 1 d . . . . .
H009 H 0.218219 0.568923 0.442406 0.067 Uiso 1 1 calc R U . . .
C00A C 0.27259(19) 0.7636(2) 0.47192(10) 0.0562(4) Uani 1 1 d . . . . .
C00B C 0.3705(2) 0.8637(2) 0.46230(12) 0.0614(5) Uani 1 1 d . . . . .
H00B H 0.364012 0.949262 0.483276 0.074 Uiso 1 1 calc R U . . .
C00C C 0.6210(2) 0.79063(19) 0.29953(11) 0.0580(4) Uani 1 1 d . . . . .
C00D C 0.1624(2) 0.7955(2) 0.51423(11) 0.0588(4) Uani 1 1 d . . . . .
C00E C 0.3918(2) 0.3598(2) 0.39229(12) 0.0622(5) Uani 1 1 d . . . . .
H00E H 0.391515 0.356810 0.444004 0.075 Uiso 1 1 calc R U . . .
C00F C 0.3879(2) 0.3659(2) 0.23783(12) 0.0650(5) Uani 1 1 d . . . . .
H00F H 0.385302 0.368282 0.185722 0.078 Uiso 1 1 calc R U . . .
C00G C 0.1922(2) 0.8878(2) 0.57473(12) 0.0689(5) Uani 1 1 d . . . . .
H00G H 0.283043 0.927893 0.590092 0.083 Uiso 1 1 calc R U . . .
C00H C 0.5319(3) 0.8864(2) 0.25948(15) 0.0724(6) Uani 1 1 d . . . . .
H00H H 0.442994 0.912521 0.266567 0.087 Uiso 1 1 calc R U . . .
C00I C 0.0261(2) 0.7365(3) 0.49299(12) 0.0722(6) Uani 1 1 d . . . . .
H00I H 0.004033 0.674549 0.452485 0.087 Uiso 1 1 calc R U . . .
C00J C 0.3961(3) 0.2394(2) 0.35249(14) 0.0721(5) Uani 1 1 d . . . . .
H00J H 0.400613 0.156345 0.377860 0.087 Uiso 1 1 calc R U . . .
C00K C 0.3938(2) 0.2426(2) 0.27510(14) 0.0707(5) Uani 1 1 d . . . . .
H00K H 0.396237 0.161944 0.248394 0.085 Uiso 1 1 calc R U . . .
C00L C 0.7236(3) 0.8724(2) 0.21413(14) 0.0733(6) Uani 1 1 d . . . . .
H00L H 0.789677 0.887005 0.185112 0.088 Uiso 1 1 calc R U . . .
C00M C 0.0877(3) 0.9207(3) 0.61247(13) 0.0778(6) Uani 1 1 d . . . . .
H00M H 0.108861 0.982809 0.652928 0.093 Uiso 1 1 calc R U . . .
C00N C -0.0773(3) 0.7691(3) 0.53159(15) 0.0828(7) Uani 1 1 d . . . . .
H00N H -0.167600 0.727796 0.517491 0.099 Uiso 1 1 calc R U . . .
C00O C -0.0467(3) 0.8624(3) 0.59061(14) 0.0781(6) Uani 1 1 d . . . . .
H00O H -0.116821 0.885918 0.615643 0.094 Uiso 1 1 calc R U . . .
C00P C 0.5999(3) 0.9395(3) 0.20439(16) 0.0819(7) Uani 1 1 d . . . . .
H00P H 0.564863 1.007757 0.168551 0.098 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
O001 C007 1.219(2) . ?
O002 C00C 1.3710(19) . ?
O002 C00L 1.356(3) . ?
N003 C008 1.338(2) . ?
N003 C00B 1.336(2) . ?
C004 C005 1.481(2) . ?
C004 C006 1.395(2) . ?
C004 C00E 1.388(2) . ?
C005 C008 1.406(2) . ?
C005 C009 1.394(2) . ?
C006 H006 0.9300 . ?
C006 C00F 1.384(3) . ?
C007 C008 1.514(2) . ?
C007 C00C 1.443(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.389(3) . ?
C00A C00B 1.401(3) . ?
C00A C00D 1.487(2) . ?
C00B H00B 0.9300 . ?
C00C C00H 1.347(3) . ?
C00D C00G 1.387(3) . ?
C00D C00I 1.390(3) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.389(3) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.378(3) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.386(3) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.419(3) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.387(3) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.385(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00P 1.328(4) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.371(4) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.374(3) . ?
C00O H00O 0.9300 . ?
C00P H00P 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
C00L O002 C00C 106.09(16) . . ?
C00B N003 C008 117.69(16) . . ?
C006 C004 C005 119.66(15) . . ?
C00E C004 C005 121.85(15) . . ?
C00E C004 C006 118.48(16) . . ?
C008 C005 C004 121.68(14) . . ?
C009 C005 C004 121.24(15) . . ?
C009 C005 C008 117.04(16) . . ?
C004 C006 H006 119.6 . . ?
C00F C006 C004 120.79(18) . . ?
C00F C006 H006 119.6 . . ?
O001 C007 C008 119.78(16) . . ?
O001 C007 C00C 123.48(15) . . ?
C00C C007 C008 116.73(16) . . ?
N003 C008 C005 123.39(15) . . ?
N003 C008 C007 115.19(15) . . ?
C005 C008 C007 121.18(15) . . ?
C005 C009 H009 119.5 . . ?
C00A C009 C005 120.90(16) . . ?
C00A C009 H009 119.5 . . ?
C009 C00A C00B 116.63(15) . . ?
C009 C00A C00D 123.13(17) . . ?
C00B C00A C00D 120.19(17) . . ?
N003 C00B C00A 124.26(17) . . ?
N003 C00B H00B 117.9 . . ?
C00A C00B H00B 117.9 . . ?
O002 C00C C007 118.23(17) . . ?
C00H C00C O002 109.66(17) . . ?
C00H C00C C007 132.07(16) . . ?
C00G C00D C00A 120.59(17) . . ?
C00G C00D C00I 118.44(16) . . ?
C00I C00D C00A 120.95(17) . . ?
C004 C00E H00E 119.7 . . ?
C004 C00E C00J 120.62(18) . . ?
C00J C00E H00E 119.7 . . ?
C006 C00F H00F 119.9 . . ?
C00K C00F C006 120.21(19) . . ?
C00K C00F H00F 119.9 . . ?
C00D C00G H00G 119.8 . . ?
C00M C00G C00D 120.5(2) . . ?
C00M C00G H00G 119.8 . . ?
C00C C00H H00H 126.7 . . ?
C00C C00H C00P 106.63(19) . . ?
C00P C00H H00H 126.7 . . ?
C00D C00I H00I 119.7 . . ?
C00N C00I C00D 120.7(2) . . ?
C00N C00I H00I 119.7 . . ?
C00E C00J H00J 119.9 . . ?
C00K C00J C00E 120.2(2) . . ?
C00K C00J H00J 119.9 . . ?
C00F C00K C00J 119.74(18) . . ?
C00F C00K H00K 120.1 . . ?
C00J C00K H00K 120.1 . . ?
O002 C00L H00L 124.4 . . ?
C00P C00L O002 111.21(17) . . ?
C00P C00L H00L 124.4 . . ?
C00G C00M H00M 119.7 . . ?
C00O C00M C00G 120.5(2) . . ?
C00O C00M H00M 119.7 . . ?
C00I C00N H00N 119.9 . . ?
C00O C00N C00I 120.1(2) . . ?
C00O C00N H00N 119.9 . . ?
C00M C00O C00N 119.77(18) . . ?
C00M C00O H00O 120.1 . . ?
C00N C00O H00O 120.1 . . ?
C00H C00P H00P 126.8 . . ?
C00L C00P C00H 106.4(2) . . ?
C00L C00P H00P 126.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C007 C008 N003 118.6(2) . . . . ?
O001 C007 C008 C005 -56.0(3) . . . . ?
O001 C007 C00C O002 -3.0(3) . . . . ?
O001 C007 C00C C00H 174.3(2) . . . . ?
O002 C00C C00H C00P -0.6(3) . . . . ?
O002 C00L C00P C00H -0.3(3) . . . . ?
C004 C005 C008 N003 174.63(18) . . . . ?
C004 C005 C008 C007 -11.2(3) . . . . ?
C004 C005 C009 C00A -175.79(17) . . . . ?
C004 C006 C00F C00K -0.8(3) . . . . ?
C004 C00E C00J C00K -1.2(3) . . . . ?
C005 C004 C006 C00F -179.35(17) . . . . ?
C005 C004 C00E C00J -179.67(19) . . . . ?
C005 C009 C00A C00B 0.4(3) . . . . ?
C005 C009 C00A C00D 177.97(17) . . . . ?
C006 C004 C005 C008 -50.9(3) . . . . ?
C006 C004 C005 C009 126.80(19) . . . . ?
C006 C004 C00E C00J 1.1(3) . . . . ?
C006 C00F C00K C00J 0.7(3) . . . . ?
C007 C00C C00H C00P -178.1(2) . . . . ?
C008 N003 C00B C00A 1.1(3) . . . . ?
C008 C005 C009 C00A 2.0(3) . . . . ?
C008 C007 C00C O002 175.77(16) . . . . ?
C008 C007 C00C C00H -6.9(3) . . . . ?
C009 C005 C008 N003 -3.2(3) . . . . ?
C009 C005 C008 C007 170.97(17) . . . . ?
C009 C00A C00B N003 -2.1(3) . . . . ?
C009 C00A C00D C00G 150.0(2) . . . . ?
C009 C00A C00D C00I -31.7(3) . . . . ?
C00A C00D C00G C00M 177.9(2) . . . . ?
C00A C00D C00I C00N -178.5(2) . . . . ?
C00B N003 C008 C005 1.6(3) . . . . ?
C00B N003 C008 C007 -172.82(18) . . . . ?
C00B C00A C00D C00G -32.6(3) . . . . ?
C00B C00A C00D C00I 145.8(2) . . . . ?
C00C O002 C00L C00P 0.0(3) . . . . ?
C00C C007 C008 N003 -60.2(2) . . . . ?
C00C C007 C008 C005 125.19(19) . . . . ?
C00C C00H C00P C00L 0.5(3) . . . . ?
C00D C00A C00B N003 -179.8(2) . . . . ?
C00D C00G C00M C00O 0.1(4) . . . . ?
C00D C00I C00N C00O 1.2(4) . . . . ?
C00E C004 C005 C008 129.89(19) . . . . ?
C00E C004 C005 C009 -52.4(3) . . . . ?
C00E C004 C006 C00F -0.1(3) . . . . ?
C00E C00J C00K C00F 0.3(3) . . . . ?
C00G C00D C00I C00N -0.1(4) . . . . ?
C00G C00M C00O C00N 1.0(4) . . . . ?
C00I C00D C00G C00M -0.5(4) . . . . ?
C00I C00N C00O C00M -1.6(4) . . . . ?
C00L O002 C00C C007 178.29(18) . . . . ?
C00L O002 C00C C00H 0.4(2) . . . . ?


_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_AKASPGNAP160201_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2349633'
loop_
_audit_author_name
_audit_author_address
'PROF JAGADEESH PRASAD D'
;Mangalore University
India
;
_audit_update_record             
;
2024-04-19 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
(3,5-diphenylpyridin-2-yl)(9H-fluoren-2-yl)methanone
_chemical_name_common            PYRIDINE
_chemical_melting_point          188
_chemical_formula_moiety         C31H21NO
_chemical_formula_sum            'C31 H21 N O'
_chemical_formula_weight         423.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5417(11)
_cell_length_b                   11.2513(12)
_cell_length_c                   11.7206(13)
_cell_angle_alpha                63.057(3)
_cell_angle_beta                 66.650(3)
_cell_angle_gamma                78.851(3)
_cell_volume                     1137.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.98

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26455
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3964
_reflns_number_gt                3428
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3964
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.22879(13) 0.19090(12) 0.61407(12) 0.0616(3) Uani 1 1 d . . . . .
N1 N 0.16548(13) 0.50659(13) 0.48078(13) 0.0491(3) Uani 1 1 d . . . . .
C16 C 0.26672(15) 0.42902(14) 0.65464(15) 0.0425(3) Uani 1 1 d . . . . .
C20 C 0.35834(16) 0.33396(14) 0.72591(16) 0.0463(4) Uani 1 1 d . . . . .
C17 C 0.20377(16) 0.53613(15) 0.68669(16) 0.0459(4) Uani 1 1 d . . . . .
H17 H 0.217706 0.546846 0.755004 0.055 Uiso 1 1 calc R U . . .
C10 C 0.70427(16) 0.28532(16) 0.03941(16) 0.0471(4) Uani 1 1 d . . . . .
C15 C 0.24064(15) 0.41820(15) 0.55182(15) 0.0429(3) Uani 1 1 d . . . . .
C7 C 0.43591(16) 0.18482(16) 0.37636(16) 0.0482(4) Uani 1 1 d . . . . .
H7 H 0.399982 0.103495 0.446973 0.058 Uiso 1 1 calc R U . . .
C2 C 0.38598(15) 0.30353(15) 0.39081(15) 0.0440(4) Uani 1 1 d . . . . .
C5 C 0.59109(15) 0.31171(15) 0.14956(15) 0.0445(4) Uani 1 1 d . . . . .
C18 C 0.12060(15) 0.62714(15) 0.61845(16) 0.0460(4) Uani 1 1 d . . . . .
C1 C 0.28300(15) 0.29529(16) 0.52393(16) 0.0452(4) Uani 1 1 d . . . . .
C19 C 0.10747(16) 0.60812(16) 0.51438(17) 0.0494(4) Uani 1 1 d . . . . .
H19 H 0.054963 0.670053 0.465114 0.059 Uiso 1 1 calc R U . . .
C6 C 0.53944(16) 0.18918(15) 0.25592(16) 0.0462(4) Uani 1 1 d . . . . .
C9 C 0.71988(17) 0.14855(16) 0.08005(16) 0.0499(4) Uani 1 1 d . . . . .
C26 C 0.04898(17) 0.73980(16) 0.65383(18) 0.0503(4) Uani 1 1 d . . . . .
C3 C 0.43830(17) 0.42536(16) 0.28181(16) 0.0501(4) Uani 1 1 d . . . . .
H3 H 0.404258 0.504402 0.291091 0.060 Uiso 1 1 calc R U . . .
C4 C 0.53974(17) 0.43013(16) 0.16056(17) 0.0514(4) Uani 1 1 d . . . . .
H4 H 0.572669 0.511449 0.087950 0.062 Uiso 1 1 calc R U . . .
C21 C 0.48906(17) 0.30124(16) 0.65153(19) 0.0535(4) Uani 1 1 d . . . . .
H21 H 0.516933 0.335118 0.556835 0.064 Uiso 1 1 calc R U . . .
C14 C 0.82441(19) 0.09607(19) -0.00179(19) 0.0600(5) Uani 1 1 d . . . . .
H14 H 0.836052 0.004332 0.025805 0.072 Uiso 1 1 calc R U . . .
C25 C 0.3188(2) 0.28147(18) 0.86705(19) 0.0615(5) Uani 1 1 d . . . . .
H25 H 0.231400 0.300804 0.918989 0.074 Uiso 1 1 calc R U . . .
C11 C 0.79085(19) 0.37252(19) -0.08631(18) 0.0602(5) Uani 1 1 d . . . . .
H11 H 0.779721 0.464372 -0.114735 0.072 Uiso 1 1 calc R U . . .
C8 C 0.61296(19) 0.07635(17) 0.21916(18) 0.0572(4) Uani 1 1 d . . . . .
H8A H 0.550488 0.027320 0.214229 0.069 Uiso 1 1 calc R U . . .
H8B H 0.656050 0.015448 0.284411 0.069 Uiso 1 1 calc R U . . .
C13 C 0.91101(19) 0.1828(2) -0.1253(2) 0.0653(5) Uani 1 1 d . . . . .
H13 H 0.982434 0.148736 -0.180946 0.078 Uiso 1 1 calc R U . . .
C22 C 0.5779(2) 0.21899(18) 0.7168(2) 0.0679(5) Uani 1 1 d . . . . .
H22 H 0.664681 0.197268 0.665874 0.081 Uiso 1 1 calc R U . . .
C12 C 0.8941(2) 0.3182(2) -0.16769(19) 0.0668(5) Uani 1 1 d . . . . .
H12 H 0.952811 0.374379 -0.252460 0.080 Uiso 1 1 calc R U . . .
C31 C -0.0804(2) 0.7832(2) 0.6471(2) 0.0727(6) Uani 1 1 d . . . . .
H31 H -0.123900 0.740767 0.620750 0.087 Uiso 1 1 calc R U . . .
C23 C 0.5388(2) 0.1693(2) 0.8561(3) 0.0770(6) Uani 1 1 d . . . . .
H23 H 0.599274 0.115161 0.899690 0.092 Uiso 1 1 calc R U . . .
C29 C -0.0857(2) 0.9511(2) 0.7197(3) 0.0851(7) Uani 1 1 d . . . . .
H29 H -0.130650 1.021774 0.741505 0.102 Uiso 1 1 calc R U . . .
C27 C 0.1090(2) 0.8044(2) 0.6953(3) 0.0768(6) Uani 1 1 d . . . . .
H27 H 0.196052 0.776966 0.701344 0.092 Uiso 1 1 calc R U . . .
C24 C 0.4101(3) 0.1998(2) 0.9309(2) 0.0797(6) Uani 1 1 d . . . . .
H24 H 0.383477 0.165484 1.025504 0.096 Uiso 1 1 calc R U . . .
C30 C -0.1465(2) 0.8886(3) 0.6789(3) 0.0876(7) Uani 1 1 d . . . . .
H30 H -0.233268 0.917192 0.672494 0.105 Uiso 1 1 calc R U . . .
C28 C 0.0419(3) 0.9090(2) 0.7281(3) 0.0954(8) Uani 1 1 d . . . . .
H28 H 0.083979 0.950992 0.756061 0.114 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 1.2160(19) . ?
N1 C15 1.333(2) . ?
N1 C19 1.334(2) . ?
C16 C17 1.392(2) . ?
C16 C15 1.397(2) . ?
C16 C20 1.485(2) . ?
C20 C25 1.387(2) . ?
C20 C21 1.392(2) . ?
C17 C18 1.387(2) . ?
C10 C9 1.386(2) . ?
C10 C11 1.392(2) . ?
C10 C5 1.472(2) . ?
C15 C1 1.508(2) . ?
C7 C6 1.387(2) . ?
C7 C2 1.397(2) . ?
C2 C3 1.401(2) . ?
C2 C1 1.479(2) . ?
C5 C4 1.381(2) . ?
C5 C6 1.395(2) . ?
C18 C19 1.391(2) . ?
C18 C26 1.485(2) . ?
C6 C8 1.499(2) . ?
C9 C14 1.381(2) . ?
C9 C8 1.512(2) . ?
C26 C31 1.377(2) . ?
C26 C27 1.381(2) . ?
C3 C4 1.384(2) . ?
C21 C22 1.382(2) . ?
C14 C13 1.377(3) . ?
C25 C24 1.392(3) . ?
C11 C12 1.384(3) . ?
C13 C12 1.371(3) . ?
C22 C23 1.370(3) . ?
C31 C30 1.381(3) . ?
C23 C24 1.369(3) . ?
C29 C30 1.362(3) . ?
C29 C28 1.363(3) . ?
C27 C28 1.380(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 N1 C19 117.62(13) . . ?
C17 C16 C15 116.52(13) . . ?
C17 C16 C20 120.72(13) . . ?
C15 C16 C20 122.75(13) . . ?
C25 C20 C21 118.53(15) . . ?
C25 C20 C16 120.89(15) . . ?
C21 C20 C16 120.49(14) . . ?
C18 C17 C16 121.11(14) . . ?
C9 C10 C11 120.74(15) . . ?
C9 C10 C5 108.60(14) . . ?
C11 C10 C5 130.63(15) . . ?
N1 C15 C16 123.87(14) . . ?
N1 C15 C1 114.37(13) . . ?
C16 C15 C1 121.42(13) . . ?
C6 C7 C2 119.49(14) . . ?
C7 C2 C3 119.46(14) . . ?
C7 C2 C1 118.30(14) . . ?
C3 C2 C1 122.19(14) . . ?
C4 C5 C6 121.30(14) . . ?
C4 C5 C10 130.80(14) . . ?
C6 C5 C10 107.85(13) . . ?
C17 C18 C19 116.67(14) . . ?
C17 C18 C26 122.02(14) . . ?
C19 C18 C26 121.31(14) . . ?
O1 C1 C2 121.96(14) . . ?
O1 C1 C15 117.55(13) . . ?
C2 C1 C15 120.49(13) . . ?
N1 C19 C18 124.11(14) . . ?
C7 C6 C5 119.90(14) . . ?
C7 C6 C8 129.18(14) . . ?
C5 C6 C8 110.90(14) . . ?
C14 C9 C10 120.56(16) . . ?
C14 C9 C8 128.98(16) . . ?
C10 C9 C8 110.44(14) . . ?
C31 C26 C27 117.51(16) . . ?
C31 C26 C18 121.09(14) . . ?
C27 C26 C18 121.40(15) . . ?
C4 C3 C2 121.14(15) . . ?
C5 C4 C3 118.65(15) . . ?
C22 C21 C20 120.77(18) . . ?
C13 C14 C9 118.44(17) . . ?
C20 C25 C24 119.90(19) . . ?
C12 C11 C10 117.88(18) . . ?
C6 C8 C9 102.12(13) . . ?
C12 C13 C14 121.33(17) . . ?
C23 C22 C21 120.27(19) . . ?
C13 C12 C11 121.01(18) . . ?
C26 C31 C30 121.10(17) . . ?
C24 C23 C22 119.69(18) . . ?
C30 C29 C28 119.29(19) . . ?
C28 C27 C26 121.12(18) . . ?
C23 C24 C25 120.8(2) . . ?
C29 C30 C31 120.54(18) . . ?
C29 C28 C27 120.44(19) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.028


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
####################################################################### 
# 
# 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_AKASPGNOX08_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2349642'
loop_
_audit_author_name
_audit_author_address
'JAGADEESH PRASAD D'
;Mangalore University
India
;
_audit_update_record             
;
2024-04-19 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
(5-(3,4-dimethoxyphenyl)oxazol-2-yl)(phenyl)methanone
_chemical_name_common            OXAZOLE
_chemical_melting_point          136
_chemical_formula_moiety         C18H15NO4
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.048(2)
_cell_length_b                   8.244(2)
_cell_length_c                   23.019(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.925(7)
_cell_angle_gamma                90
_cell_volume                     1516.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9739
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      25.86

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31025
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2644
_reflns_number_gt                2436
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0005P)²+9.1677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2644
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2573
_refine_ls_wR_factor_gt          0.2551
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8224(4) 0.2869(5) 0.50558(15) 0.0420(9) Uani 1 1 d . . . . .
O1 O 0.4459(5) 0.6247(5) 0.70300(16) 0.0462(10) Uani 1 1 d . . . . .
O2 O 0.2466(5) 0.4247(5) 0.64614(17) 0.0499(11) Uani 1 1 d . . . . .
O4 O 1.1198(5) 0.1777(6) 0.47952(19) 0.0631(13) Uani 1 1 d . . . . .
N1 N 0.6867(6) 0.1401(6) 0.43454(19) 0.0438(11) Uani 1 1 d . . . . .
C2 C 0.5085(6) 0.5509(6) 0.6569(2) 0.0365(12) Uani 1 1 d . . . . .
C7 C 0.3976(6) 0.4404(6) 0.6258(2) 0.0355(11) Uani 1 1 d . . . . .
C9 C 0.6550(6) 0.2904(6) 0.5130(2) 0.0366(12) Uani 1 1 d . . . . .
C12 C 1.0001(7) 0.1572(7) 0.4424(2) 0.0387(12) Uani 1 1 d . . . . .
C5 C 0.6070(6) 0.3810(6) 0.5624(2) 0.0361(12) Uani 1 1 d . . . . .
C3 C 0.6644(7) 0.5744(7) 0.6403(2) 0.0431(13) Uani 1 1 d . . . . .
H3 H 0.737796 0.647039 0.660936 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5735(7) 0.1989(7) 0.4699(2) 0.0427(13) Uani 1 1 d . . . . .
H10 H 0.458947 0.178729 0.464879 0.051 Uiso 1 1 calc R U . . .
C4 C 0.7136(7) 0.4907(7) 0.5930(2) 0.0432(13) Uani 1 1 d . . . . .
H4 H 0.819270 0.508697 0.581729 0.052 Uiso 1 1 calc R U . . .
C11 C 0.8315(7) 0.1940(7) 0.4582(2) 0.0398(12) Uani 1 1 d . . . . .
C13 C 1.0205(7) 0.0965(6) 0.3832(2) 0.0411(13) Uani 1 1 d . . . . .
C6 C 0.4465(6) 0.3564(7) 0.5790(2) 0.0381(12) Uani 1 1 d . . . . .
H6 H 0.373364 0.283537 0.558401 0.046 Uiso 1 1 calc R U . . .
C14 C 1.1633(7) 0.0040(7) 0.3779(3) 0.0491(14) Uani 1 1 d . . . . .
H14 H 1.237613 -0.021001 0.410799 0.059 Uiso 1 1 calc R U . . .
C18 C 0.9138(8) 0.1357(7) 0.3344(2) 0.0506(15) Uani 1 1 d . . . . .
H18 H 0.819022 0.197835 0.337870 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1397(8) 0.2974(10) 0.6217(3) 0.069(2) Uani 1 1 d . . . . .
H8A H 0.106408 0.318955 0.580938 0.104 Uiso 1 1 calc R U . . .
H8B H 0.042177 0.291827 0.641845 0.104 Uiso 1 1 calc R U . . .
H8C H 0.198614 0.196064 0.625773 0.104 Uiso 1 1 calc R U . . .
C17 C 0.9471(10) 0.0827(9) 0.2796(3) 0.0638(19) Uani 1 1 d . . . . .
H17 H 0.874398 0.108487 0.246314 0.077 Uiso 1 1 calc R U . . .
C15 C 1.1927(9) -0.0494(8) 0.3237(3) 0.0625(19) Uani 1 1 d . . . . .
H15 H 1.285274 -0.114717 0.320373 0.075 Uiso 1 1 calc R U . . .
C16 C 1.0894(11) -0.0089(8) 0.2749(3) 0.070(2) Uani 1 1 d . . . . .
H16 H 1.114012 -0.042592 0.238306 0.083 Uiso 1 1 calc R U . . .
C1 C 0.5463(10) 0.7446(11) 0.7333(4) 0.091(3) Uani 1 1 d . . . . .
H1A H 0.647947 0.696344 0.751554 0.136 Uiso 1 1 calc R U . . .
H1B H 0.486769 0.792457 0.762755 0.136 Uiso 1 1 calc R U . . .
H1C H 0.572485 0.826921 0.706362 0.136 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
O3 C11 1.342(6) . ?
O3 C9 1.379(6) . ?
O1 C2 1.371(6) . ?
O1 C1 1.408(7) . ?
O2 C7 1.360(6) . ?
O2 C8 1.429(7) . ?
O4 C12 1.220(6) . ?
N1 C11 1.303(7) . ?
N1 C10 1.381(7) . ?
C2 C3 1.368(7) . ?
C2 C7 1.409(7) . ?
C7 C6 1.377(7) . ?
C9 C10 1.351(7) . ?
C9 C5 1.451(7) . ?
C12 C11 1.478(7) . ?
C12 C13 1.480(7) . ?
C5 C4 1.380(7) . ?
C5 C6 1.405(7) . ?
C3 C4 1.388(7) . ?
C13 C18 1.367(8) . ?
C13 C14 1.397(8) . ?
C14 C15 1.369(8) . ?
C18 C17 1.392(8) . ?
C17 C16 1.387(10) . ?
C15 C16 1.357(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C9 105.2(4) . . ?
C2 O1 C1 117.0(4) . . ?
C7 O2 C8 117.0(4) . . ?
C11 N1 C10 104.7(4) . . ?
O1 C2 C3 126.0(5) . . ?
O1 C2 C7 114.3(4) . . ?
C3 C2 C7 119.7(5) . . ?
O2 C7 C6 125.0(5) . . ?
O2 C7 C2 115.1(4) . . ?
C6 C7 C2 120.0(5) . . ?
C10 C9 O3 107.0(4) . . ?
C10 C9 C5 135.3(5) . . ?
O3 C9 C5 117.7(4) . . ?
O4 C12 C11 118.1(5) . . ?
O4 C12 C13 121.7(5) . . ?
C11 C12 C13 120.2(5) . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 C9 121.9(5) . . ?
C6 C5 C9 118.6(5) . . ?
C2 C3 C4 120.4(5) . . ?
C9 C10 N1 109.4(5) . . ?
C5 C4 C3 120.5(5) . . ?
N1 C11 O3 113.6(5) . . ?
N1 C11 C12 129.0(5) . . ?
O3 C11 C12 117.3(5) . . ?
C18 C13 C14 120.0(5) . . ?
C18 C13 C12 123.2(5) . . ?
C14 C13 C12 116.7(5) . . ?
C7 C6 C5 119.9(5) . . ?
C15 C14 C13 119.3(6) . . ?
C13 C18 C17 120.0(6) . . ?
C16 C17 C18 119.5(7) . . ?
C16 C15 C14 121.3(7) . . ?
C15 C16 C17 119.9(6) . . ?

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
