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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2175751'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;SAIF, Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2024-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.36

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.9636(8)
_cell_length_b                   5.4254(2)
_cell_length_c                   18.4927(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.262(2)
_cell_angle_gamma                90
_cell_volume                     1616.24(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6442
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      26.75

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'SADABS, Bruker 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36607
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.603
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3517
_reflns_number_gt                2630
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.1059P)²+0.6217P] 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         3517
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1990
_refine_ls_wR_factor_gt          0.1820
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
C1 C 0.60609(17) 0.5913(5) 0.65939(14) 0.0520(6) Uani 1 1 d . . . . .
C2 C 0.65684(18) 0.3765(5) 0.66395(14) 0.0546(7) Uani 1 1 d . . . . .
H2 H 0.674586 0.292154 0.710019 0.066 Uiso 1 1 calc R U . . .
C3 C 0.68025(15) 0.2899(5) 0.60583(13) 0.0447(6) Uani 1 1 d . . . . .
C4 C 0.64936(14) 0.4132(4) 0.53251(13) 0.0388(5) Uani 1 1 d . . . . .
C5 C 0.66781(14) 0.3446(4) 0.46805(13) 0.0412(5) Uani 1 1 d . . . . .
H5 H 0.701771 0.208240 0.470484 0.049 Uiso 1 1 calc R U . . .
C6 C 0.63741(13) 0.4722(4) 0.39852(13) 0.0375(5) Uani 1 1 d . . . . .
C7 C 0.65808(14) 0.3997(4) 0.33313(13) 0.0405(5) Uani 1 1 d . . . . .
H7 H 0.691806 0.263125 0.334989 0.049 Uiso 1 1 calc R U . . .
C8 C 0.62806(13) 0.5320(4) 0.26718(13) 0.0372(5) Uani 1 1 d . . . . .
C9 C 0.63670(14) 0.5114(4) 0.19161(13) 0.0393(5) Uani 1 1 d . . . . .
C10 C 0.67799(15) 0.3454(5) 0.15904(15) 0.0466(6) Uani 1 1 d . . . . .
H10 H 0.709180 0.217964 0.187850 0.056 Uiso 1 1 calc R U . . .
C11 C 0.67206(17) 0.3722(5) 0.08317(15) 0.0537(7) Uani 1 1 d . . . . .
H11 H 0.699338 0.262057 0.060684 0.064 Uiso 1 1 calc R U . . .
C12 C 0.62540(17) 0.5637(5) 0.04023(15) 0.0552(7) Uani 1 1 d . . . . .
H12 H 0.621944 0.579119 -0.010756 0.066 Uiso 1 1 calc R U . . .
C13 C 0.58419(17) 0.7309(5) 0.07169(14) 0.0513(6) Uani 1 1 d . . . . .
H13 H 0.553277 0.858471 0.042725 0.062 Uiso 1 1 calc R U . . .
C14 C 0.59027(14) 0.7029(4) 0.14791(13) 0.0409(5) Uani 1 1 d . . . . .
C15 C 0.57603(13) 0.7428(4) 0.26452(13) 0.0382(5) Uani 1 1 d . . . . .
C16 C 0.55435(14) 0.8181(4) 0.32653(13) 0.0403(5) Uani 1 1 d . . . . .
H16 H 0.520224 0.954400 0.323591 0.048 Uiso 1 1 calc R U . . .
C17 C 0.58512(13) 0.6837(4) 0.39475(13) 0.0378(5) Uani 1 1 d . . . . .
C18 C 0.56557(14) 0.7520(4) 0.46130(13) 0.0408(5) Uani 1 1 d . . . . .
H18 H 0.531346 0.886909 0.460121 0.049 Uiso 1 1 calc R U . . .
C19 C 0.59663(14) 0.6213(4) 0.52648(13) 0.0405(5) Uani 1 1 d . . . . .
C20 C 0.73776(17) 0.0744(5) 0.61570(15) 0.0531(7) Uani 1 1 d . . . . .
H20A H 0.747326 0.039421 0.568249 0.080 Uiso 1 1 calc R U . . .
H20B H 0.789566 0.112506 0.653690 0.080 Uiso 1 1 calc R U . . .
H20C H 0.713285 -0.066915 0.631497 0.080 Uiso 1 1 calc R U . . .
C21 C 0.48963(16) 1.0263(5) 0.16298(14) 0.0479(6) Uani 1 1 d . . . . .
H21A H 0.500032 1.117231 0.121731 0.057 Uiso 1 1 calc R U . . .
H21B H 0.490191 1.142585 0.202977 0.057 Uiso 1 1 calc R U . . .
C22 C 0.40551(19) 0.9065(7) 0.1344(2) 0.0755(9) Uani 1 1 d . . . . .
H22A H 0.363845 1.030772 0.115536 0.113 Uiso 1 1 calc R U . . .
H22B H 0.404431 0.793469 0.094196 0.113 Uiso 1 1 calc R U . . .
H22C H 0.394598 0.818803 0.175380 0.113 Uiso 1 1 calc R U . . .
N1 N 0.55525(13) 0.8457(4) 0.19236(11) 0.0439(5) Uani 1 1 d . . . . .
O1 O 0.58850(15) 0.6850(5) 0.71126(11) 0.0736(7) Uani 1 1 d . . . . .
O2 O 0.57590(11) 0.7045(3) 0.58945(9) 0.0492(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.203(3) . ?
C1 O2 1.377(3) . ?
C1 C2 1.436(4) . ?
C2 C3 1.342(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.454(3) . ?
C3 C20 1.497(4) . ?
C4 C5 1.375(3) . ?
C4 C19 1.423(3) . ?
C5 C6 1.408(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(3) . ?
C6 C17 1.439(3) . ?
C7 C8 1.368(3) . ?
C7 H7 0.9300 . ?
C8 C15 1.436(3) . ?
C8 C9 1.454(3) . ?
C9 C10 1.389(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C14 N1 1.391(3) . ?
C15 C16 1.372(3) . ?
C15 N1 1.386(3) . ?
C16 C17 1.408(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.420(3) . ?
C18 C19 1.355(3) . ?
C18 H18 0.9300 . ?
C19 O2 1.393(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N1 1.454(3) . ?
C21 C22 1.505(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 116.6(3) . . ?
O1 C1 C2 126.2(3) . . ?
O2 C1 C2 117.2(2) . . ?
C3 C2 C1 124.0(2) . . ?
C3 C2 H2 118.0 . . ?
C1 C2 H2 118.0 . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 C20 121.4(2) . . ?
C4 C3 C20 120.2(2) . . ?
C5 C4 C19 117.1(2) . . ?
C5 C4 C3 124.8(2) . . ?
C19 C4 C3 118.2(2) . . ?
C4 C5 C6 122.7(2) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 C17 118.7(2) . . ?
C7 C6 C17 119.6(2) . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C15 120.1(2) . . ?
C7 C8 C9 134.0(2) . . ?
C15 C8 C9 105.91(19) . . ?
C10 C9 C14 120.0(2) . . ?
C10 C9 C8 133.1(2) . . ?
C14 C9 C8 106.87(19) . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 118.0(2) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C13 C14 N1 129.0(2) . . ?
C13 C14 C9 121.1(2) . . ?
N1 C14 C9 109.9(2) . . ?
C16 C15 N1 129.1(2) . . ?
C16 C15 C8 122.1(2) . . ?
N1 C15 C8 108.8(2) . . ?
C15 C16 C17 118.3(2) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C18 121.3(2) . . ?
C16 C17 C6 120.4(2) . . ?
C18 C17 C6 118.3(2) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 O2 116.4(2) . . ?
C18 C19 C4 123.0(2) . . ?
O2 C19 C4 120.6(2) . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 C22 111.8(2) . . ?
N1 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N1 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 N1 C14 108.54(19) . . ?
C15 N1 C21 124.4(2) . . ?
C14 N1 C21 125.0(2) . . ?
C1 O2 C19 121.6(2) . . ?

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 -174.5(3) . . . . ?
O2 C1 C2 C3 4.1(4) . . . . ?
C1 C2 C3 C4 -3.1(4) . . . . ?
C1 C2 C3 C20 176.0(2) . . . . ?
C2 C3 C4 C5 -179.8(2) . . . . ?
C20 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C19 0.7(3) . . . . ?
C20 C3 C4 C19 -178.3(2) . . . . ?
C19 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C6 -179.0(2) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
C4 C5 C6 C17 0.2(3) . . . . ?
C5 C6 C7 C8 -179.0(2) . . . . ?
C17 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C15 0.0(3) . . . . ?
C6 C7 C8 C9 179.7(2) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C15 C8 C9 C10 -179.0(2) . . . . ?
C7 C8 C9 C14 179.7(2) . . . . ?
C15 C8 C9 C14 -0.6(2) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C8 C9 C10 C11 178.0(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 N1 179.8(2) . . . . ?
C12 C13 C14 C9 0.0(4) . . . . ?
C10 C9 C14 C13 0.2(4) . . . . ?
C8 C9 C14 C13 -178.5(2) . . . . ?
C10 C9 C14 N1 -179.6(2) . . . . ?
C8 C9 C14 N1 1.7(3) . . . . ?
C7 C8 C15 C16 -0.3(3) . . . . ?
C9 C8 C15 C16 179.9(2) . . . . ?
C7 C8 C15 N1 179.0(2) . . . . ?
C9 C8 C15 N1 -0.7(2) . . . . ?
N1 C15 C16 C17 -178.7(2) . . . . ?
C8 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 179.7(2) . . . . ?
C15 C16 C17 C6 -0.4(3) . . . . ?
C5 C6 C17 C16 179.2(2) . . . . ?
C7 C6 C17 C16 0.2(3) . . . . ?
C5 C6 C17 C18 -0.9(3) . . . . ?
C7 C6 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C19 -179.3(2) . . . . ?
C6 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 O2 178.53(19) . . . . ?
C17 C18 C19 C4 0.0(4) . . . . ?
C5 C4 C19 C18 -0.7(3) . . . . ?
C3 C4 C19 C18 178.9(2) . . . . ?
C5 C4 C19 O2 -179.1(2) . . . . ?
C3 C4 C19 O2 0.4(3) . . . . ?
C16 C15 N1 C14 -178.9(2) . . . . ?
C8 C15 N1 C14 1.8(3) . . . . ?
C16 C15 N1 C21 -14.8(4) . . . . ?
C8 C15 N1 C21 165.9(2) . . . . ?
C13 C14 N1 C15 178.0(2) . . . . ?
C9 C14 N1 C15 -2.2(3) . . . . ?
C13 C14 N1 C21 14.0(4) . . . . ?
C9 C14 N1 C21 -166.2(2) . . . . ?
C22 C21 N1 C15 -81.1(3) . . . . ?
C22 C21 N1 C14 80.4(3) . . . . ?
O1 C1 O2 C19 175.9(2) . . . . ?
C2 C1 O2 C19 -2.8(4) . . . . ?
C18 C19 O2 C1 -177.8(2) . . . . ?
C4 C19 O2 C1 0.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16 O1 0.93 2.63 3.545(3) 169.3 3_676 yes
C21 H21B O1 0.97 2.55 3.399(3) 146.2 3_676 yes

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_141
_database_code_depnum_ccdc_archive 'CCDC 2292825'
loop_
_audit_author_name
_audit_author_address
Nitisha
;SAIF, Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2024-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 N O2'
_chemical_formula_sum            'C26 H17 N O2'
_chemical_formula_weight         375.40

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                   7.6312(4)
_cell_length_b                   9.6106(5)
_cell_length_c                   12.8959(8)
_cell_angle_alpha                72.286(3)
_cell_angle_beta                 81.389(3)
_cell_angle_gamma                88.455(3)
_cell_volume                     890.62(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4621
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.09

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            12192
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3140
_reflns_number_gt                2442
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0474P)²+0.1963P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0074(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3140
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.40735(19) 1.30035(16) 0.36235(12) 0.0360(4) Uani 1 1 d . . . . .
C2 C 0.4099(2) 1.42383(17) 0.39596(14) 0.0450(4) Uani 1 1 d . . . . .
H2 H 0.3534 1.4232 0.4652 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4983(2) 1.54863(18) 0.32468(15) 0.0512(5) Uani 1 1 d . . . . .
H3 H 0.5010 1.6324 0.3462 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5824(2) 1.54907(18) 0.22183(15) 0.0494(4) Uani 1 1 d . . . . .
H4 H 0.6421 1.6335 0.1756 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5804(2) 1.42771(17) 0.18584(14) 0.0438(4) Uani 1 1 d . . . . .
H5 H 0.6367 1.4293 0.1163 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4915(2) 1.30363(16) 0.25720(12) 0.0369(4) Uani 1 1 d . . . . .
C7 C 0.37592(19) 1.07380(16) 0.33918(11) 0.0342(4) Uani 1 1 d . . . . .
C8 C 0.3202(2) 0.93236(16) 0.36167(12) 0.0365(4) Uani 1 1 d . . . . .
H8 H 0.3420 0.8842 0.3086 0.044 Uiso 1 1 calc R U . . .
C9 C 0.22861(19) 0.86126(16) 0.46753(11) 0.0332(3) Uani 1 1 d . . . . .
C10 C 0.1741(2) 0.71361(16) 0.49785(12) 0.0372(4) Uani 1 1 d . . . . .
H10 H 0.1921 0.6631 0.4462 0.045 Uiso 1 1 calc R U . . .
C11 C 0.09543(19) 0.64474(16) 0.60194(12) 0.0362(4) Uani 1 1 d . . . . .
C12 C -0.0144(2) 0.4147(2) 0.72978(14) 0.0503(4) Uani 1 1 d . . . . .
C13 C -0.0593(2) 0.48935(19) 0.81138(13) 0.0484(4) Uani 1 1 d . . . . .
H13 H -0.1142 0.4358 0.8810 0.058 Uiso 1 1 calc R U . . .
C14 C -0.0261(2) 0.63178(19) 0.79216(12) 0.0417(4) Uani 1 1 d . . . . .
C15 C 0.05726(19) 0.71649(17) 0.68309(12) 0.0357(4) Uani 1 1 d . . . . .
C16 C 0.10275(19) 0.86259(17) 0.65320(12) 0.0368(4) Uani 1 1 d . . . . .
H16 H 0.0746 0.9129 0.7045 0.044 Uiso 1 1 calc R U . . .
C17 C 0.19072(18) 0.93848(16) 0.54731(11) 0.0333(3) Uani 1 1 d . . . . .
C18 C 0.24167(19) 1.08687(16) 0.51810(12) 0.0358(4) Uani 1 1 d . . . . .
H18 H 0.2122 1.1392 0.5680 0.043 Uiso 1 1 calc R U . . .
C19 C 0.33464(19) 1.15399(16) 0.41615(12) 0.0336(3) Uani 1 1 d . . . . .
C20 C 0.56428(19) 1.12213(16) 0.15400(12) 0.0356(4) Uani 1 1 d . . . . .
C21 C 0.5560(2) 1.20420(17) 0.04609(12) 0.0413(4) Uani 1 1 d . . . . .
H21 H 0.4840 1.2854 0.0314 0.050 Uiso 1 1 calc R U . . .
C22 C 0.6538(2) 1.16603(19) -0.03949(13) 0.0471(4) Uani 1 1 d . . . . .
H22 H 0.6488 1.2225 -0.1117 0.057 Uiso 1 1 calc R U . . .
C23 C 0.7586(2) 1.04520(19) -0.01893(14) 0.0503(5) Uani 1 1 d . . . . .
H23 H 0.8252 1.0202 -0.0769 0.060 Uiso 1 1 calc R U . . .
C24 C 0.7645(2) 0.96110(18) 0.08830(15) 0.0483(4) Uani 1 1 d . . . . .
H24 H 0.8341 0.8784 0.1023 0.058 Uiso 1 1 calc R U . . .
C25 C 0.6682(2) 0.99848(17) 0.17486(13) 0.0407(4) Uani 1 1 d . . . . .
H25 H 0.6728 0.9412 0.2469 0.049 Uiso 1 1 calc R U . . .
C26 C -0.0691(2) 0.7044(2) 0.88014(14) 0.0575(5) Uani 1 1 d . . . . .
H26A H -0.1221 0.6342 0.9472 0.086 Uiso 1 1 calc R U . . .
H26B H -0.1504 0.7819 0.8576 0.086 Uiso 1 1 calc R U . . .
H26C H 0.0377 0.7439 0.8921 0.086 Uiso 1 1 calc R U . . .
N1 N 0.47107(17) 1.16641(13) 0.24233(10) 0.0390(3) Uani 1 1 d . . . . .
O1 O 0.05555(15) 0.49745(11) 0.62587(9) 0.0467(3) Uani 1 1 d . . . . .
O2 O -0.0322(2) 0.28532(14) 0.74460(11) 0.0726(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(2) . ?
C1 C6 1.402(2) . ?
C1 C19 1.449(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.4051(19) . ?
C7 C8 1.367(2) . ?
C7 N1 1.4022(18) . ?
C7 C19 1.427(2) . ?
C8 C9 1.411(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(2) . ?
C9 C17 1.434(2) . ?
C10 C11 1.356(2) . ?
C10 H10 0.9300 . ?
C11 O1 1.3859(18) . ?
C11 C15 1.412(2) . ?
C12 O2 1.208(2) . ?
C12 O1 1.3687(19) . ?
C12 C13 1.441(3) . ?
C13 C14 1.339(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.452(2) . ?
C14 C26 1.497(2) . ?
C15 C16 1.377(2) . ?
C16 C17 1.412(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.409(2) . ?
C18 C19 1.370(2) . ?
C18 H18 0.9300 . ?
C20 C21 1.385(2) . ?
C20 C25 1.390(2) . ?
C20 N1 1.4214(18) . ?
C21 C22 1.376(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.83(14) . . ?
C2 C1 C19 132.99(14) . . ?
C6 C1 C19 107.17(13) . . ?
C1 C2 C3 118.91(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.38(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 121.88(16) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.47(16) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C5 C6 C1 121.53(15) . . ?
C5 C6 N1 129.17(14) . . ?
C1 C6 N1 109.29(13) . . ?
C8 C7 N1 129.23(13) . . ?
C8 C7 C19 122.30(13) . . ?
N1 C7 C19 108.41(12) . . ?
C7 C8 C9 118.27(14) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 121.26(14) . . ?
C10 C9 C17 118.52(13) . . ?
C8 C9 C17 120.21(13) . . ?
C11 C10 C9 120.41(14) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 O1 116.31(14) . . ?
C10 C11 C15 122.74(14) . . ?
O1 C11 C15 120.95(13) . . ?
O2 C12 O1 116.69(17) . . ?
O2 C12 C13 126.00(16) . . ?
O1 C12 C13 117.31(15) . . ?
C14 C13 C12 123.43(15) . . ?
C14 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C13 C14 C15 118.54(15) . . ?
C13 C14 C26 121.91(15) . . ?
C15 C14 C26 119.53(15) . . ?
C16 C15 C11 117.46(13) . . ?
C16 C15 C14 124.45(14) . . ?
C11 C15 C14 118.09(14) . . ?
C15 C16 C17 122.23(14) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 122.04(14) . . ?
C18 C17 C9 119.42(13) . . ?
C16 C17 C9 118.54(14) . . ?
C19 C18 C17 119.95(14) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C7 119.67(14) . . ?
C18 C19 C1 133.54(14) . . ?
C7 C19 C1 106.79(12) . . ?
C21 C20 C25 119.33(14) . . ?
C21 C20 N1 120.17(14) . . ?
C25 C20 N1 120.47(13) . . ?
C22 C21 C20 120.27(15) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.43(16) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.61(16) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.62(16) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C20 119.71(15) . . ?
C24 C25 H25 120.1 . . ?
C20 C25 H25 120.1 . . ?
C14 C26 H26A 109.5 . . ?
C14 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C14 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 N1 C6 108.32(12) . . ?
C7 N1 C20 125.78(12) . . ?
C6 N1 C20 124.58(12) . . ?
C12 O1 C11 121.49(13) . . ?

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
C6 C1 C2 C3 -0.8(2) . . . . ?
C19 C1 C2 C3 177.52(16) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 N1 -179.05(15) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C19 C1 C6 C5 -177.68(14) . . . . ?
C2 C1 C6 N1 179.92(13) . . . . ?
C19 C1 C6 N1 1.23(16) . . . . ?
N1 C7 C8 C9 178.71(14) . . . . ?
C19 C7 C8 C9 -4.2(2) . . . . ?
C7 C8 C9 C10 -177.25(14) . . . . ?
C7 C8 C9 C17 2.1(2) . . . . ?
C8 C9 C10 C11 176.14(14) . . . . ?
C17 C9 C10 C11 -3.2(2) . . . . ?
C9 C10 C11 O1 -176.42(13) . . . . ?
C9 C10 C11 C15 2.8(2) . . . . ?
O2 C12 C13 C14 175.51(18) . . . . ?
O1 C12 C13 C14 -4.2(3) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C12 C13 C14 C26 -177.85(16) . . . . ?
C10 C11 C15 C16 0.1(2) . . . . ?
O1 C11 C15 C16 179.28(13) . . . . ?
C10 C11 C15 C14 -179.58(14) . . . . ?
O1 C11 C15 C14 -0.4(2) . . . . ?
C13 C14 C15 C16 -178.24(15) . . . . ?
C26 C14 C15 C16 0.5(2) . . . . ?
C13 C14 C15 C11 1.4(2) . . . . ?
C26 C14 C15 C11 -179.80(14) . . . . ?
C11 C15 C16 C17 -2.5(2) . . . . ?
C14 C15 C16 C17 177.17(13) . . . . ?
C15 C16 C17 C18 -178.09(14) . . . . ?
C15 C16 C17 C9 2.0(2) . . . . ?
C10 C9 C17 C18 -179.01(13) . . . . ?
C8 C9 C17 C18 1.6(2) . . . . ?
C10 C9 C17 C16 0.9(2) . . . . ?
C8 C9 C17 C16 -178.46(13) . . . . ?
C16 C17 C18 C19 176.72(13) . . . . ?
C9 C17 C18 C19 -3.4(2) . . . . ?
C17 C18 C19 C7 1.4(2) . . . . ?
C17 C18 C19 C1 -178.94(15) . . . . ?
C8 C7 C19 C18 2.5(2) . . . . ?
N1 C7 C19 C18 -179.86(13) . . . . ?
C8 C7 C19 C1 -177.23(14) . . . . ?
N1 C7 C19 C1 0.38(16) . . . . ?
C2 C1 C19 C18 0.9(3) . . . . ?
C6 C1 C19 C18 179.31(15) . . . . ?
C2 C1 C19 C7 -179.43(16) . . . . ?
C6 C1 C19 C7 -0.99(16) . . . . ?
C25 C20 C21 C22 -1.9(2) . . . . ?
N1 C20 C21 C22 176.43(14) . . . . ?
C20 C21 C22 C23 0.9(2) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 -0.9(3) . . . . ?
C23 C24 C25 C20 -0.1(2) . . . . ?
C21 C20 C25 C24 1.5(2) . . . . ?
N1 C20 C25 C24 -176.86(14) . . . . ?
C8 C7 N1 C6 177.76(15) . . . . ?
C19 C7 N1 C6 0.36(16) . . . . ?
C8 C7 N1 C20 -14.9(2) . . . . ?
C19 C7 N1 C20 167.70(13) . . . . ?
C5 C6 N1 C7 177.79(15) . . . . ?
C1 C6 N1 C7 -1.01(16) . . . . ?
C5 C6 N1 C20 10.3(2) . . . . ?
C1 C6 N1 C20 -168.53(13) . . . . ?
C21 C20 N1 C7 138.56(15) . . . . ?
C25 C20 N1 C7 -43.1(2) . . . . ?
C21 C20 N1 C6 -56.1(2) . . . . ?
C25 C20 N1 C6 122.22(16) . . . . ?
O2 C12 O1 C11 -174.54(15) . . . . ?
C13 C12 O1 C11 5.2(2) . . . . ?
C10 C11 O1 C12 176.15(14) . . . . ?
C15 C11 O1 C12 -3.1(2) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2292833'
loop_
_audit_author_name
_audit_author_address
'Sudhadevi Antharjanam'
;SAIF, Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2024-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N O2 '

_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35

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'
N N 0.0061 0.0033 '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                   7.7256(4)
_cell_length_b                   9.6168(6)
_cell_length_c                   11.7022(7)
_cell_angle_alpha                66.390(2)
_cell_angle_beta                 77.927(2)
_cell_angle_gamma                83.497(2)
_cell_volume                     778.60(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9469
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.23

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6531
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS(BRUKER 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26625
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.022
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3849
_reflns_number_gt                2771
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_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)+(0.0966P)²+0.6835P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3849
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2102
_refine_ls_wR_factor_gt          0.1763
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.1630(2) 0.4135(2) 0.62905(18) 0.0287(4) Uani 1 1 d . . . . .
C2 C 0.0437(3) 0.2232(3) 0.82970(19) 0.0351(5) Uani 1 1 d . . . . .
C3 C 0.1286(3) 0.1103(3) 0.7836(2) 0.0356(5) Uani 1 1 d . . . . .
H3 H 0.120383 0.008521 0.837972 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2201(3) 0.1460(2) 0.66409(18) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.2399(2) 0.3046(2) 0.58160(17) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.2981(4) 0.0243(3) 0.6176(2) 0.0507(7) Uani 1 1 d . . . . .
H6A H 0.357887 0.070118 0.531279 0.076 Uiso 1 1 calc R U . . .
H6B H 0.380959 -0.037891 0.669423 0.076 Uiso 1 1 calc R U . . .
H6C H 0.205305 -0.037227 0.622111 0.076 Uiso 1 1 calc R U . . .
C7 C 0.3331(3) 0.3576(2) 0.45605(17) 0.0290(4) Uani 1 1 d . . . . .
H7 H 0.386348 0.287519 0.422120 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3481(3) 0.5110(2) 0.38143(17) 0.0283(4) Uani 1 1 d . . . . .
C9 C 0.1783(3) 0.5670(2) 0.5573(2) 0.0336(4) Uani 1 1 d . . . . .
H9 H 0.126705 0.636707 0.592129 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2701(3) 0.6180(2) 0.43331(19) 0.0310(4) Uani 1 1 d . . . . .
C11 C 0.2856(4) 0.7853(3) 0.3574(2) 0.0460(6) Uani 1 1 d . . . . .
H11A H 0.352335 0.802300 0.274213 0.069 Uiso 1 1 calc R U . . .
H11B H 0.169432 0.831778 0.350458 0.069 Uiso 1 1 calc R U . . .
H11C H 0.344811 0.829072 0.398814 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4438(3) 0.5674(2) 0.24493(19) 0.0344(5) Uani 1 1 d . . . . .
H12A H 0.363541 0.636371 0.192506 0.041 Uiso 1 1 calc R U . . .
H12B H 0.542750 0.626063 0.237672 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5131(3) 0.4510(2) 0.19089(18) 0.0321(4) Uani 1 1 d . . . . .
C14 C 0.6856(3) 0.4297(3) 0.1399(2) 0.0379(5) Uani 1 1 d . . . . .
C15 C 0.5311(3) 0.2719(2) 0.10565(18) 0.0332(4) Uani 1 1 d . . . . .
C16 C 0.4114(3) 0.3511(2) 0.16894(18) 0.0314(4) Uani 1 1 d . . . . .
C17 C 0.2309(3) 0.3240(3) 0.1940(2) 0.0420(5) Uani 1 1 d . . . . .
H17 H 0.149682 0.374644 0.235934 0.050 Uiso 1 1 calc R U . . .
C18 C 0.1747(4) 0.2212(3) 0.1556(3) 0.0516(6) Uani 1 1 d . . . . .
H18 H 0.054371 0.203940 0.170805 0.062 Uiso 1 1 calc R U . . .
C19 C 0.2953(4) 0.1424(3) 0.0942(3) 0.0495(6) Uani 1 1 d . . . . .
H19 H 0.254105 0.072654 0.070397 0.059 Uiso 1 1 calc R U . . .
C20 C 0.4741(3) 0.1664(3) 0.0685(2) 0.0421(5) Uani 1 1 d . . . . .
H20 H 0.554277 0.113913 0.027742 0.050 Uiso 1 1 calc R U . . .
O1 O 0.0670(2) 0.37249(18) 0.75062(14) 0.0368(4) Uani 1 1 d . . . . .
O2 O -0.0493(2) 0.1981(2) 0.93266(16) 0.0523(5) Uani 1 1 d . . . . .
N1 N 0.6978(3) 0.3201(2) 0.09025(18) 0.0400(5) Uani 1 1 d . . . . .
H1A H 0.795(4) 0.298(4) 0.033(3) 0.070(10) Uiso 1 1 d . . . . .
H14A H 0.793(4) 0.479(3) 0.129(3) 0.054(8) 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
C1 C9 1.379(3) . ?
C1 O1 1.380(2) . ?
C1 C5 1.395(3) . ?
C2 O2 1.213(2) . ?
C2 O1 1.369(3) . ?
C2 C3 1.436(3) . ?
C3 C4 1.352(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.447(3) . ?
C4 C6 1.497(3) . ?
C5 C7 1.406(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C10 1.413(3) . ?
C8 C12 1.515(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.499(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.494(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.370(3) . ?
C13 C16 1.435(3) . ?
C14 N1 1.380(3) . ?
C14 H14A 0.97(3) . ?
C15 N1 1.370(3) . ?
C15 C20 1.395(3) . ?
C15 C16 1.411(3) . ?
C16 C17 1.396(3) . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.398(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 H1A 0.96(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
C9 C1 O1 116.69(17) . . ?
C9 C1 C5 121.95(17) . . ?
O1 C1 C5 121.36(18) . . ?
O2 C2 O1 116.68(19) . . ?
O2 C2 C3 125.7(2) . . ?
O1 C2 C3 117.65(17) . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 118.54(18) . . ?
C3 C4 C6 120.86(19) . . ?
C5 C4 C6 120.60(17) . . ?
C1 C5 C7 117.16(18) . . ?
C1 C5 C4 118.36(16) . . ?
C7 C5 C4 124.48(17) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 122.01(17) . . ?
C8 C7 H7 119.0 . . ?
C5 C7 H7 119.0 . . ?
C7 C8 C10 119.18(17) . . ?
C7 C8 C12 121.76(17) . . ?
C10 C8 C12 119.05(17) . . ?
C1 C9 C10 120.37(18) . . ?
C1 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C8 119.33(18) . . ?
C9 C10 C11 119.39(19) . . ?
C8 C10 C11 121.29(19) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C8 117.36(17) . . ?
C13 C12 H12A 108.0 . . ?
C8 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C8 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C14 C13 C16 106.18(19) . . ?
C14 C13 C12 126.4(2) . . ?
C16 C13 C12 127.10(18) . . ?
C13 C14 N1 110.2(2) . . ?
C13 C14 H14A 132.7(17) . . ?
N1 C14 H14A 117.0(17) . . ?
N1 C15 C20 130.4(2) . . ?
N1 C15 C16 107.83(19) . . ?
C20 C15 C16 121.8(2) . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 C13 133.79(19) . . ?
C15 C16 C13 107.17(18) . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.2(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C15 117.9(2) . . ?
C19 C20 H20 121.1 . . ?
C15 C20 H20 121.1 . . ?
C2 O1 C1 121.37(16) . . ?
C15 N1 C14 108.62(18) . . ?
C15 N1 H1A 121(2) . . ?
C14 N1 H1A 128(2) . . ?

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 C2 C3 C4 175.0(2) . . . . ?
O1 C2 C3 C4 -4.0(3) . . . . ?
C2 C3 C4 C5 2.9(3) . . . . ?
C2 C3 C4 C6 -176.6(2) . . . . ?
C9 C1 C5 C7 -0.6(3) . . . . ?
O1 C1 C5 C7 179.16(17) . . . . ?
C9 C1 C5 C4 178.91(18) . . . . ?
O1 C1 C5 C4 -1.3(3) . . . . ?
C3 C4 C5 C1 -0.2(3) . . . . ?
C6 C4 C5 C1 179.3(2) . . . . ?
C3 C4 C5 C7 179.24(19) . . . . ?
C6 C4 C5 C7 -1.3(3) . . . . ?
C1 C5 C7 C8 -0.4(3) . . . . ?
C4 C5 C7 C8 -179.86(18) . . . . ?
C5 C7 C8 C10 1.1(3) . . . . ?
C5 C7 C8 C12 -178.05(18) . . . . ?
O1 C1 C9 C10 -178.93(18) . . . . ?
C5 C1 C9 C10 0.8(3) . . . . ?
C1 C9 C10 C8 -0.1(3) . . . . ?
C1 C9 C10 C11 -179.73(19) . . . . ?
C7 C8 C10 C9 -0.8(3) . . . . ?
C12 C8 C10 C9 178.33(18) . . . . ?
C7 C8 C10 C11 178.78(19) . . . . ?
C12 C8 C10 C11 -2.1(3) . . . . ?
C7 C8 C12 C13 3.4(3) . . . . ?
C10 C8 C12 C13 -175.69(18) . . . . ?
C8 C12 C13 C14 -122.2(2) . . . . ?
C8 C12 C13 C16 65.4(3) . . . . ?
C16 C13 C14 N1 -1.4(2) . . . . ?
C12 C13 C14 N1 -175.15(19) . . . . ?
N1 C15 C16 C17 178.79(19) . . . . ?
C20 C15 C16 C17 -0.6(3) . . . . ?
N1 C15 C16 C13 0.3(2) . . . . ?
C20 C15 C16 C13 -179.07(18) . . . . ?
C14 C13 C16 C17 -177.5(2) . . . . ?
C12 C13 C16 C17 -3.8(4) . . . . ?
C14 C13 C16 C15 0.6(2) . . . . ?
C12 C13 C16 C15 174.34(18) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C13 C16 C17 C18 177.7(2) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
N1 C15 C20 C19 -178.5(2) . . . . ?
C16 C15 C20 C19 0.8(3) . . . . ?
O2 C2 O1 C1 -176.72(19) . . . . ?
C3 C2 O1 C1 2.4(3) . . . . ?
C9 C1 O1 C2 179.95(18) . . . . ?
C5 C1 O1 C2 0.2(3) . . . . ?
C20 C15 N1 C14 178.2(2) . . . . ?
C16 C15 N1 C14 -1.2(2) . . . . ?
C13 C14 N1 C15 1.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O2 0.93 2.61 3.445(3) 149.7 2_557 yes
N1 H1A O2 0.96(3) 1.95(3) 2.882(2) 162(3) 1_654 yes

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.057

