# Supplementary Information (SI) for Chemical Communications.
# 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_PO_04NO
_database_code_depnum_ccdc_archive 'CCDC 2343452'
loop_
_audit_author_name
_audit_author_address
'Pooja Sah'
;IISERB
India
;
_audit_update_record             
;
2024-03-26 deposited with the CCDC.	2024-12-29 downloaded from the CCDC.
;
_audit_creation_date             2024-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   6.151(3)
_cell_length_b                   14.019(7)
_cell_length_c                   7.211(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.579(17)
_cell_angle_gamma                90
_cell_volume                     618.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    99.00
_cell_measurement_theta_max      30.244
_cell_measurement_theta_min      2.906
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1433 before and 0.1010 after correction.
The Ratio of minimum to maximum transmission is 0.6137.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.189
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_unetI/netI     0.1445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10262
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.244
_diffrn_reflns_theta_min         2.906
_diffrn_ambient_temperature      99.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.751
_reflns_Friedel_fraction_max     0.621
_reflns_number_gt                1775
_reflns_number_total             2984
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     274
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.013
_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)+0.1485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1762
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C13-C14 \\sim C13A-C12A
 with sigma of 0.02
 C15-C10 \\sim C11A-C10
 with sigma of 0.02
 C15-C14 \\sim C11A-C12A
 with sigma of 0.02
 C11-C12 \\sim C15A-C14A
 with sigma of 0.02
 C10-C11 \\sim C10-C15A
 with sigma of 0.02
 C15-C13 \\sim C11A-C13A
 with sigma of 0.04
 C13-C12 \\sim C13A-C14A
 with sigma of 0.02
 C11-C13 \\sim C15A-C13A
 with sigma of 0.04
 C10-C14 \\sim C10-C12A
 with sigma of 0.04
 C10-C12 \\sim C10-C14A
 with sigma of 0.04
 C14-C12 \\sim C12A-C14A
 with sigma of 0.04
 C14-O3 \\sim C12A-O1A
 with sigma of 0.04
 C12-O3 \\sim C14A-O1A
 with sigma of 0.04
 C13-O3 \\sim C13A-O1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 2A
4. Others
 Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C15A)=Sof(H15C)=Sof(C13A)=
 Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C14A)=Sof(H14C)=Sof(O1A)=1-FVAR(1)
 Sof(C15)=Sof(H15B)=Sof(H15A)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C13)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(C12)=Sof(H12)=Sof(O3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10A), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15B,H15A), C14(H14A,H14B), C11A(H11A,H11B), C12A(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2), C11(H11), C12(H12), C15A(H15C), C14A(H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     DUAL
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.8141(6) 0.3837(3) 0.1768(5) 0.0427(9) Uani 1 1 d . U . . .
O1 O 1.0504(6) 0.4755(3) 0.0659(5) 0.0425(9) Uani 1 1 d . U . . .
N1 N 0.8812(6) 0.4627(3) 0.1386(5) 0.0338(8) Uani 1 1 d . U . . .
C4 C 0.5232(8) 0.7035(3) 0.2804(6) 0.0276(7) Uani 1 1 d . U . . .
C7 C 0.4061(7) 0.7893(4) 0.3384(6) 0.0290(7) Uani 1 1 d . U . . .
C5 C 0.4498(7) 0.6121(3) 0.3149(6) 0.0287(8) Uani 1 1 d . U . . .
H5 H 0.319663 0.604224 0.374234 0.034 Uiso 1 1 calc R U . . .
C3 C 0.7108(7) 0.7132(4) 0.1873(6) 0.0302(8) Uani 1 1 d . U . . .
H3 H 0.759060 0.775169 0.157182 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5620(7) 0.5326(4) 0.2649(6) 0.0296(8) Uani 1 1 d . U . . .
H6 H 0.509914 0.470273 0.287508 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4621(8) 0.8743(4) 0.2824(7) 0.0321(9) Uani 1 1 d . U . . .
C2 C 0.8262(7) 0.6353(3) 0.1386(6) 0.0301(8) Uani 1 1 d . U . . .
H2 H 0.954565 0.642809 0.076677 0.036 Uiso 1 1 calc R U . . .
C1 C 0.7533(7) 0.5460(4) 0.1806(6) 0.0301(7) Uani 1 1 d . U . . .
C9 C 0.5148(11) 0.9578(4) 0.2285(9) 0.0409(12) Uani 1 1 d . U . . .
C15 C 0.348(2) 0.7714(12) 0.679(2) 0.0317(10) Uani 0.572(10) 1 d D U P A 1
H15B H 0.431851 0.711062 0.691035 0.038 Uiso 0.572(10) 1 calc R U P A 1
H15A H 0.451721 0.824890 0.704507 0.038 Uiso 0.572(10) 1 calc R U P A 1
C10 C 0.2328(7) 0.7806(3) 0.4748(6) 0.0304(7) Uani 1 1 d D U . . .
H10A H 0.139506 0.724450 0.434724 0.037 Uiso 0.428(10) 1 calc R U P A 2
H10 H 0.145127 0.721587 0.444431 0.037 Uiso 0.572(10) 1 calc R U P A 1
C11 C 0.084(4) 0.8629(14) 0.470(3) 0.0318(9) Uani 0.572(10) 1 d D U P A 1
H11 H 0.043618 0.891312 0.351657 0.038 Uiso 0.572(10) 1 calc R U P A 1
C13 C 0.024(2) 0.8596(10) 0.7931(17) 0.0332(9) Uani 0.572(10) 1 d D U P A 1
C14 C 0.1783(16) 0.7727(7) 0.8219(14) 0.0320(9) Uani 0.572(10) 1 d D U P A 1
H14A H 0.254530 0.774871 0.949180 0.038 Uiso 0.572(10) 1 calc R U P A 1
H14B H 0.091128 0.713300 0.810166 0.038 Uiso 0.572(10) 1 calc R U P A 1
C12 C -0.0003(15) 0.9010(7) 0.6162(12) 0.0330(9) Uani 0.572(10) 1 d D U P A 1
H12 H -0.079959 0.958907 0.599678 0.040 Uiso 0.572(10) 1 calc R U P A 1
O3 O -0.0722(17) 0.8900(9) 0.9226(14) 0.0370(16) Uani 0.572(10) 1 d D U P A 1
C11A C 0.083(5) 0.8708(19) 0.455(4) 0.0318(10) Uani 0.428(10) 1 d D U P A 2
H11A H 0.171130 0.929583 0.477054 0.038 Uiso 0.428(10) 1 calc R U P A 2
H11B H 0.004345 0.873989 0.328926 0.038 Uiso 0.428(10) 1 calc R U P A 2
C15A C 0.324(3) 0.7626(16) 0.662(3) 0.0317(10) Uani 0.428(10) 1 d D U P A 2
H15C H 0.456316 0.727615 0.680480 0.038 Uiso 0.428(10) 1 calc R U P A 2
C13A C 0.048(3) 0.8468(14) 0.805(2) 0.0331(9) Uani 0.428(10) 1 d D U P A 2
C12A C -0.0789(19) 0.8606(10) 0.6028(15) 0.0329(9) Uani 0.428(10) 1 d D U P A 2
H12A H -0.174824 0.804922 0.572365 0.040 Uiso 0.428(10) 1 calc R U P A 2
H12B H -0.171945 0.918217 0.601988 0.040 Uiso 0.428(10) 1 calc R U P A 2
C14A C 0.235(2) 0.7914(10) 0.8082(19) 0.0326(10) Uani 0.428(10) 1 d D U P A 2
H14C H 0.303460 0.773193 0.926618 0.039 Uiso 0.428(10) 1 calc R U P A 2
O1A O -0.024(2) 0.8792(13) 0.9466(19) 0.0369(17) Uani 0.428(10) 1 d D U P A 2
H9A H 0.419(8) 0.983(4) 0.129(7) 0.033(14) Uiso 1 1 d . . . . .
H9B H 0.631(9) 0.993(4) 0.311(8) 0.051(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N1 1.224(5) . ?
O1 N1 1.223(5) . ?
N1 C1 1.456(6) . ?
C4 C7 1.483(6) . ?
C4 C5 1.390(6) . ?
C4 C3 1.397(6) . ?
C7 C8 1.315(7) . ?
C7 C10 1.524(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.367(6) . ?
C6 H6 0.9500 . ?
C6 C1 1.389(6) . ?
C8 C9 1.284(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.374(6) . ?
C9 H9A 0.95(5) . ?
C9 H9B 1.01(6) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 C10 1.577(15) . ?
C15 C14 1.536(18) . ?
C10 H10A 1.0000 . ?
C10 H10 1.0000 . ?
C10 C11 1.473(18) . ?
C10 C11A 1.56(2) . ?
C10 C15A 1.434(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.33(2) . ?
C13 C14 1.547(15) . ?
C13 C12 1.395(14) . ?
C13 O3 1.228(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C12 H12 0.9500 . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.53(2) . ?
C15A H15C 0.9500 . ?
C15A C14A 1.30(2) . ?
C13A C12A 1.599(19) . ?
C13A C14A 1.387(17) . ?
C13A O1A 1.234(14) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C14A H14C 0.9500 . ?

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 118.6(4) . . ?
O1 N1 O2 123.3(4) . . ?
O1 N1 C1 118.1(4) . . ?
C5 C4 C7 121.5(4) . . ?
C5 C4 C3 118.3(4) . . ?
C3 C4 C7 120.2(4) . . ?
C4 C7 C10 120.5(4) . . ?
C8 C7 C4 120.0(4) . . ?
C8 C7 C10 119.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H3 119.3 . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C1 118.2(4) . . ?
C1 C6 H6 120.9 . . ?
C9 C8 C7 179.3(5) . . ?
C3 C2 H2 120.6 . . ?
C3 C2 C1 118.9(4) . . ?
C1 C2 H2 120.6 . . ?
C6 C1 N1 118.7(4) . . ?
C2 C1 N1 119.4(4) . . ?
C2 C1 C6 121.9(4) . . ?
C8 C9 H9A 115(3) . . ?
C8 C9 H9B 117(3) . . ?
H9A C9 H9B 127(4) . . ?
H15B C15 H15A 108.1 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 C10 110.6(10) . . ?
C7 C10 C15 109.3(7) . . ?
C7 C10 H10A 107.1 . . ?
C7 C10 H10 108.7 . . ?
C7 C10 C11A 108.7(9) . . ?
C15 C10 H10 108.7 . . ?
C11 C10 C7 113.2(8) . . ?
C11 C10 C15 108.1(9) . . ?
C11 C10 H10 108.7 . . ?
C11A C10 H10A 107.1 . . ?
C15A C10 C7 112.9(9) . . ?
C15A C10 H10A 107.1 . . ?
C15A C10 C11A 113.6(12) . . ?
C10 C11 H11 117.2 . . ?
C12 C11 C10 125.6(13) . . ?
C12 C11 H11 117.2 . . ?
C12 C13 C14 117.3(9) . . ?
O3 C13 C14 120.3(10) . . ?
O3 C13 C12 122.4(10) . . ?
C15 C14 C13 111.6(10) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C11 C12 C13 123.0(11) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C10 C11A H11A 110.5 . . ?
C10 C11A H11B 110.5 . . ?
H11A C11A H11B 108.7 . . ?
C12A C11A C10 106.2(13) . . ?
C12A C11A H11A 110.5 . . ?
C12A C11A H11B 110.5 . . ?
C10 C15A H15C 118.2 . . ?
C14A C15A C10 123.6(17) . . ?
C14A C15A H15C 118.2 . . ?
C14A C13A C12A 114.2(11) . . ?
O1A C13A C12A 121.9(13) . . ?
O1A C13A C14A 123.8(14) . . ?
C11A C12A C13A 110.8(14) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C13A C12A H12A 109.5 . . ?
C13A C12A H12B 109.5 . . ?
H12A C12A H12B 108.1 . . ?
C15A C14A C13A 125.3(15) . . ?
C15A C14A H14C 117.4 . . ?
C13A C14A H14C 117.4 . . ?

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
O2 N1 C1 C6 0.9(6) . . . . ?
O2 N1 C1 C2 -180.0(4) . . . . ?
O1 N1 C1 C6 -179.3(4) . . . . ?
O1 N1 C1 C2 -0.2(6) . . . . ?
C4 C7 C10 C15 78.9(8) . . . . ?
C4 C7 C10 C11 -160.6(12) . . . . ?
C4 C7 C10 C11A -159.9(15) . . . . ?
C4 C7 C10 C15A 73.2(11) . . . . ?
C4 C5 C6 C1 0.8(7) . . . . ?
C4 C3 C2 C1 0.8(7) . . . . ?
C7 C4 C5 C6 -178.4(4) . . . . ?
C7 C4 C3 C2 177.5(4) . . . . ?
C7 C10 C11 C12 -143.4(18) . . . . ?
C7 C10 C11A C12A -176.9(15) . . . . ?
C7 C10 C15A C14A 149.3(17) . . . . ?
C5 C4 C7 C8 -171.0(5) . . . . ?
C5 C4 C7 C10 13.8(6) . . . . ?
C5 C4 C3 C2 -3.0(7) . . . . ?
C5 C6 C1 N1 175.9(4) . . . . ?
C5 C6 C1 C2 -3.2(6) . . . . ?
C3 C4 C7 C8 8.5(7) . . . . ?
C3 C4 C7 C10 -166.8(4) . . . . ?
C3 C4 C5 C6 2.2(7) . . . . ?
C3 C2 C1 N1 -176.7(4) . . . . ?
C3 C2 C1 C6 2.4(7) . . . . ?
C8 C7 C10 C15 -96.4(8) . . . . ?
C8 C7 C10 C11 24.1(13) . . . . ?
C8 C7 C10 C11A 24.9(15) . . . . ?
C8 C7 C10 C15A -102.1(10) . . . . ?
C15 C10 C11 C12 -22(2) . . . . ?
C10 C15 C14 C13 -52.1(15) . . . . ?
C10 C11 C12 C13 -8(3) . . . . ?
C10 C11A C12A C13A 55(2) . . . . ?
C10 C15A C14A C13A -3(3) . . . . ?
C14 C15 C10 C7 174.3(9) . . . . ?
C14 C15 C10 C11 50.6(14) . . . . ?
C14 C13 C12 C11 8(2) . . . . ?
C12 C13 C14 C15 23.3(17) . . . . ?
O3 C13 C14 C15 -156.5(14) . . . . ?
O3 C13 C12 C11 -172.6(19) . . . . ?
C11A C10 C15A C14A 25(2) . . . . ?
C15A C10 C11A C12A -50(2) . . . . ?
C12A C13A C14A C15A 9(3) . . . . ?
C14A C13A C12A C11A -37(2) . . . . ?
O1A C13A C12A C11A 146(2) . . . . ?
O1A C13A C14A C15A -174(2) . . . . ?

_olex2_submission_original_sample_id PO_04NO
_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_PO_04_89
_database_code_depnum_ccdc_archive 'CCDC 2343455'
loop_
_audit_author_name
_audit_author_address
'Pooja Sah'
;IISERB
India
;
_audit_update_record             
;
2024-03-26 deposited with the CCDC.	2024-12-29 downloaded from the CCDC.
;
_audit_creation_date             2024-02-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N O3'
_chemical_formula_sum            'C15 H17 N O3'
_chemical_formula_weight         259.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   7.1533(11)
_cell_length_b                   12.457(3)
_cell_length_c                   14.899(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1327.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1364
_cell_measurement_temperature    99.00
_cell_measurement_theta_max      33.550
_cell_measurement_theta_min      2.131
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.4869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.6522.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.1163
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10550
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.550
_diffrn_reflns_theta_min         2.131
_diffrn_ambient_temperature      99.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                2663
_reflns_number_total             4670
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     194
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0753
_refine_ls_restrained_S_all      1.081
_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)+(0.0874P)²+0.0339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.2105
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C13 \\sim C14A-C13A
 with sigma of 0.02
 C15-C13 \\sim C15A-C13A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.04
 C9-C14 \\sim C9-C14A
 with sigma of 0.02
 C12-C13 \\sim C12-C13A
 with sigma of 0.02
 C12-C15 \\sim C12-C15A
 with sigma of 0.04
 C9-C13 \\sim C9-C13A
 with sigma of 0.04
 C14-C12 \\sim C14A-C12
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O3 \\sim C2 \\sim C4 \\sim C14A \\sim C3 \\sim C14 \\sim N1 \\sim C15 \\sim C8
\\sim C13 \\sim O2 \\sim C12 \\sim C6 \\sim C13A \\sim C7 \\sim C15A \\sim C1
\\sim C10 \\sim C11 \\sim C5 \\sim O1 \\sim C9: within 2A with sigma of 0.002
and sigma for terminal atoms of 0.004 within 2A
C6 \\sim C3 \\sim N1 \\sim O1 \\sim C2 \\sim C1 \\sim C8 \\sim O2 \\sim C7
\\sim C5 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal atoms
of 0.004 within 2A
C6 \\sim C1 \\sim C2 \\sim C7 \\sim C3 \\sim N1 \\sim C5 \\sim O1 \\sim O2
\\sim C4 \\sim C8: within 2A with sigma of 0.002 and sigma for terminal atoms
of 0.004 within 2A
4. Others
 Sof(H12C)=Sof(H12D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C13A)=Sof(H13A)=
 Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H12A)=Sof(H12B)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=Sof(C13)=Sof(H13)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C13A(H13A)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C14(H14A,H14B), C12(H12A,H12B), C12(H12C,H12D),
 C14A(H14C,H14D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C2(H2), C10(H10)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_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 0.5802(4) 0.7027(3) 0.83756(16) 0.0572(8) Uani 1 1 d . U . . .
O2 O 0.4779(4) 0.5394(3) 0.84501(15) 0.0554(8) Uani 1 1 d . U . . .
N1 N 0.5173(4) 0.6209(3) 0.80274(17) 0.0428(7) Uani 1 1 d . U . . .
C4 C 0.4452(5) 0.6178(2) 0.52183(18) 0.0295(5) Uani 1 1 d . U . . .
C8 C 0.6072(5) 0.5768(3) 0.37676(18) 0.0313(6) Uani 1 1 d . U . . .
H8A H 0.709863 0.626307 0.393274 0.038 Uiso 1 1 calc R U . . .
H8B H 0.639438 0.504603 0.399875 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4987(5) 0.7113(3) 0.56522(19) 0.0317(6) Uani 1 1 d . U . . .
H3 H 0.518696 0.774782 0.531278 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4256(5) 0.6149(3) 0.42117(17) 0.0312(6) Uani 1 1 d . U . . .
H7A H 0.393861 0.687497 0.398901 0.037 Uiso 1 1 calc R U . . .
H7B H 0.322450 0.565779 0.404582 0.037 Uiso 1 1 calc R U . . .
C1 C 0.4921(5) 0.6201(3) 0.70503(19) 0.0346(6) Uani 1 1 d . U . . .
C5 C 0.4165(5) 0.5255(3) 0.57213(19) 0.0348(6) Uani 1 1 d . U . . .
H5 H 0.381037 0.461043 0.542624 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4386(5) 0.5255(3) 0.6646(2) 0.0356(6) Uani 1 1 d . U . . .
H6 H 0.417479 0.462363 0.698880 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5235(5) 0.7133(3) 0.65773(19) 0.0347(6) Uani 1 1 d . U . . .
H2 H 0.561085 0.777245 0.687470 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5914(5) 0.5720(2) 0.27620(17) 0.0303(5) Uani 1 1 d D U . . .
C10 C 0.5730(5) 0.4795(2) 0.23301(19) 0.0329(6) Uani 1 1 d . U . . .
H10 H 0.570687 0.415221 0.267319 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5561(5) 0.4711(3) 0.1354(2) 0.0355(6) Uani 1 1 d . U . . .
C14 C 0.5657(12) 0.6791(6) 0.2272(5) 0.0330(8) Uani 0.526(9) 1 d D U P A 1
H14A H 0.431650 0.698764 0.226954 0.040 Uiso 0.526(9) 1 calc R U P A 1
H14B H 0.635145 0.736059 0.259355 0.040 Uiso 0.526(9) 1 calc R U P A 1
O3 O 0.5369(4) 0.38406(19) 0.09888(16) 0.0488(7) Uani 1 1 d . U . . .
C12 C 0.5658(6) 0.5728(3) 0.0834(2) 0.0410(6) Uani 1 1 d D U . . .
H12A H 0.439045 0.588551 0.060186 0.049 Uiso 0.526(9) 1 calc R U P A 1
H12B H 0.647694 0.560539 0.030833 0.049 Uiso 0.526(9) 1 calc R U P A 1
H12C H 0.691994 0.577855 0.056462 0.049 Uiso 0.474(9) 1 calc R U P A 2
H12D H 0.475158 0.567753 0.033363 0.049 Uiso 0.474(9) 1 calc R U P A 2
C15 C 0.5775(18) 0.7742(10) 0.0777(10) 0.0390(16) Uani 0.526(9) 1 d D U P A 1
H15A H 0.447688 0.792815 0.091790 0.058 Uiso 0.526(9) 1 calc R U P A 1
H15B H 0.589189 0.759878 0.013281 0.058 Uiso 0.526(9) 1 calc R U P A 1
H15C H 0.659449 0.834158 0.094168 0.058 Uiso 0.526(9) 1 calc R U P A 1
C13 C 0.6356(13) 0.6716(5) 0.1319(4) 0.0355(8) Uani 0.526(9) 1 d D U P A 1
H13 H 0.775291 0.668478 0.133643 0.043 Uiso 0.526(9) 1 calc R U P A 1
C14A C 0.6221(13) 0.6725(7) 0.2239(5) 0.0334(9) Uani 0.474(9) 1 d D U P A 2
H14C H 0.758181 0.684397 0.216957 0.040 Uiso 0.474(9) 1 calc R U P A 2
H14D H 0.570495 0.733911 0.258103 0.040 Uiso 0.474(9) 1 calc R U P A 2
C13A C 0.5305(15) 0.6696(6) 0.1301(4) 0.0355(8) Uani 0.474(9) 1 d D U P A 2
H13A H 0.392441 0.679307 0.136687 0.043 Uiso 0.474(9) 1 calc R U P A 2
C15A C 0.615(2) 0.7705(11) 0.0788(12) 0.0381(16) Uani 0.474(9) 1 d D U P A 2
H15D H 0.738571 0.752112 0.054739 0.057 Uiso 0.474(9) 1 calc R U P A 2
H15E H 0.627229 0.830829 0.120681 0.057 Uiso 0.474(9) 1 calc R U P A 2
H15F H 0.531891 0.790871 0.029433 0.057 Uiso 0.474(9) 1 calc R U P A 2


_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 N1 1.228(4) . ?
O2 N1 1.228(4) . ?
N1 C1 1.467(4) . ?
C4 C3 1.385(4) . ?
C4 C7 1.507(4) . ?
C4 C5 1.388(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.533(5) . ?
C8 C9 1.504(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.390(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 C6 1.378(5) . ?
C1 C2 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9500 . ?
C2 H2 0.9500 . ?
C9 C10 1.326(4) . ?
C9 C14 1.532(8) . ?
C9 C14A 1.491(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.463(4) . ?
C11 O3 1.221(4) . ?
C11 C12 1.487(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.507(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C13 1.513(7) . ?
C12 C13A 1.415(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C13 1.568(11) . ?
C13 H13 1.0000 . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C14A C13A 1.544(10) . ?
C13A H13A 1.0000 . ?
C13A C15A 1.591(13) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?

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 118.0(3) . . ?
O2 N1 O1 123.6(3) . . ?
O2 N1 C1 118.3(3) . . ?
C3 C4 C7 120.7(3) . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 C7 120.2(3) . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C9 C8 C7 112.2(3) . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C7 C8 111.0(3) . . ?
C4 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C6 C1 N1 118.3(3) . . ?
C2 C1 N1 118.8(3) . . ?
C2 C1 C6 122.9(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C3 C2 H2 120.9 . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2 120.9 . . ?
C8 C9 C14 116.7(4) . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 C14 120.9(4) . . ?
C10 C9 C14A 119.4(4) . . ?
C14A C9 C8 118.4(4) . . ?
C9 C10 H10 118.2 . . ?
C9 C10 C11 123.5(3) . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 117.0(3) . . ?
O3 C11 C10 121.1(3) . . ?
O3 C11 C12 122.0(3) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C13 C14 C9 110.8(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
C11 C12 H12C 107.9 . . ?
C11 C12 H12D 107.9 . . ?
C11 C12 C13 117.4(3) . . ?
H12A C12 H12B 107.2 . . ?
H12C C12 H12D 107.2 . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C13A C12 C11 117.5(3) . . ?
C13A C12 H12C 107.9 . . ?
C13A C12 H12D 107.9 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
C14 C13 C12 113.0(6) . . ?
C14 C13 C15 110.3(8) . . ?
C14 C13 H13 108.1 . . ?
C12 C13 C15 109.2(8) . . ?
C12 C13 H13 108.1 . . ?
C15 C13 H13 108.1 . . ?
C9 C14A H14C 109.0 . . ?
C9 C14A H14D 109.0 . . ?
C9 C14A C13A 113.0(6) . . ?
H14C C14A H14D 107.8 . . ?
C13A C14A H14C 109.0 . . ?
C13A C14A H14D 109.0 . . ?
C12 C13A C14A 112.9(7) . . ?
C12 C13A H13A 109.1 . . ?
C12 C13A C15A 111.7(9) . . ?
C14A C13A H13A 109.1 . . ?
C14A C13A C15A 104.8(9) . . ?
C15A C13A H13A 109.1 . . ?
C13A C15A H15D 109.5 . . ?
C13A C15A H15E 109.5 . . ?
C13A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

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 N1 C1 C6 174.0(3) . . . . ?
O1 N1 C1 C2 -5.7(5) . . . . ?
O2 N1 C1 C6 -4.7(5) . . . . ?
O2 N1 C1 C2 175.6(3) . . . . ?
N1 C1 C6 C5 -179.5(3) . . . . ?
N1 C1 C2 C3 -179.9(3) . . . . ?
C4 C3 C2 C1 -0.5(5) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C8 C9 C14 C13 154.8(6) . . . . ?
C8 C9 C14A C13A -157.7(6) . . . . ?
C3 C4 C7 C8 93.2(4) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C7 C4 C3 C2 -177.6(3) . . . . ?
C7 C4 C5 C6 178.3(3) . . . . ?
C7 C8 C9 C10 -104.4(4) . . . . ?
C7 C8 C9 C14 66.1(5) . . . . ?
C7 C8 C9 C14A 83.7(5) . . . . ?
C5 C4 C3 C2 0.0(5) . . . . ?
C5 C4 C7 C8 -84.4(4) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C9 C8 C7 C4 179.5(3) . . . . ?
C9 C10 C11 O3 -179.0(4) . . . . ?
C9 C10 C11 C12 1.7(6) . . . . ?
C9 C14 C13 C12 47.6(9) . . . . ?
C9 C14 C13 C15 170.2(7) . . . . ?
C9 C14A C13A C12 -46.4(11) . . . . ?
C9 C14A C13A C15A -168.1(8) . . . . ?
C10 C9 C14 C13 -34.7(9) . . . . ?
C10 C9 C14A C13A 30.2(10) . . . . ?
C10 C11 C12 C13 13.7(6) . . . . ?
C10 C11 C12 C13A -19.7(7) . . . . ?
C11 C12 C13 C14 -39.2(9) . . . . ?
C11 C12 C13 C15 -162.4(7) . . . . ?
C11 C12 C13A C14A 41.5(10) . . . . ?
C11 C12 C13A C15A 159.3(7) . . . . ?
C14 C9 C10 C11 9.6(6) . . . . ?
O3 C11 C12 C13 -165.6(5) . . . . ?
O3 C11 C12 C13A 161.0(6) . . . . ?
C14A C9 C10 C11 -8.5(7) . . . . ?

_olex2_submission_original_sample_id PO_04_89
_olex2_submission_special_instructions 'No special instructions were received'
