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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2286672'
loop_
_audit_author_name
_audit_author_address
'Julio Zukerman Schpector'
;Universidade Federal de Sao Carlos
Brazil
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

_vrf_PLAT029_shelx               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.770 Why?
RESPONSE: Due to the very low diffraction quality of the crystal. Even though
the main objective was attained which was confirming the structure and
the number of reflections per parameteris over 10.
;
_vrf_PLAT911_shelx               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 544 Report
RESPONSE: Due to the very low diffraction quality of the crystal. Even though
the main objective was attained which was confirming the structure and
the number of reflections per parameteris over 10.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28

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                   11.280(3)
_cell_length_b                   9.997(3)
_cell_length_c                   11.637(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.08(2)
_cell_angle_gamma                90
_cell_volume                     1312.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1149
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      22.94

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3755
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(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            4406
_diffrn_reflns_av_unetI/netI     0.1538
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         26.655
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.757
_diffrn_measured_fraction_theta_full 0.770
_diffrn_reflns_Laue_measured_fraction_max 0.757
_diffrn_reflns_Laue_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_point_group_measured_fraction_full 0.770
_reflns_number_total             2093
_reflns_number_gt                875
_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    SIR2014
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2093
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   0.703
_refine_ls_restrained_S_all      0.703
_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 0.1359(2) 0.8182(3) 0.3795(2) 0.0461(7) Uani 1 1 d . . . . .
C2 C 0.1134(2) 0.6765(3) 0.3643(2) 0.0450(7) Uani 1 1 d . . . . .
H2 H 0.0760 0.6395 0.2999 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1527(2) 0.6063(2) 0.4538(2) 0.0356(6) Uani 1 1 d . . . . .
C4 C 0.20156(19) 0.7038(2) 0.5392(2) 0.0377(6) Uani 1 1 d . . . . .
H4 H 0.1888 0.6878 0.6211 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3065(2) 0.7867(2) 0.5045(2) 0.0429(7) Uani 1 1 d . . . . .
H5 H 0.3437 0.7605 0.4325 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3841(2) 0.8567(3) 0.5879(2) 0.0443(7) Uani 1 1 d . . . . .
C7 C 0.5069(2) 0.8445(3) 0.5802(3) 0.0602(8) Uani 1 1 d . . . . .
H7 H 0.5399 0.7911 0.5237 0.072 Uiso 1 1 calc R U . . .
C8 C 0.5781(3) 0.9121(3) 0.6568(3) 0.0779(11) Uani 1 1 d . . . . .
H8 H 0.6600 0.9049 0.6518 0.093 Uiso 1 1 calc R U . . .
C9 C 0.5301(3) 0.9907(4) 0.7414(3) 0.0770(11) Uani 1 1 d . . . . .
H9 H 0.5798 1.0361 0.7927 0.092 Uiso 1 1 calc R U . . .
C10 C 0.4099(2) 1.0025(3) 0.7505(3) 0.0678(10) Uani 1 1 d . . . . .
H10 H 0.3775 1.0552 0.8078 0.081 Uiso 1 1 calc R U . . .
C11 C 0.3380(2) 0.9356(3) 0.6739(2) 0.0542(8) Uani 1 1 d . . . . .
H11 H 0.2562 0.9434 0.6798 0.065 Uiso 1 1 calc R U . . .
C12 C 0.15282(19) 0.4623(3) 0.4722(2) 0.0366(6) Uani 1 1 d . . . . .
C13 C 0.1059(2) 0.3751(3) 0.3904(2) 0.0455(7) Uani 1 1 d . . . . .
H13 H 0.0731 0.4091 0.3225 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1074(2) 0.2389(3) 0.4085(3) 0.0541(8) Uani 1 1 d . . . . .
H14 H 0.0760 0.1821 0.3524 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1542(2) 0.1860(3) 0.5072(3) 0.0559(8) Uani 1 1 d . . . . .
H15 H 0.1549 0.0939 0.5186 0.067 Uiso 1 1 calc R U . . .
C16 C 0.2003(2) 0.2701(3) 0.5897(3) 0.0599(8) Uani 1 1 d . . . . .
H16 H 0.2323 0.2352 0.6576 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1991(2) 0.4071(3) 0.5719(2) 0.0491(7) Uani 1 1 d . . . . .
H17 H 0.2304 0.4632 0.6285 0.059 Uiso 1 1 calc R U . . .
N N 0.18247(18) 0.8385(2) 0.49341(19) 0.0405(5) Uani 1 1 d . . . . .
O O 0.12087(17) 0.91028(19) 0.31248(17) 0.0662(6) 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 O 1.216(3) . ?
C1 N 1.430(3) . ?
C1 C2 1.450(3) . ?
C2 C3 1.326(3) . ?
C2 H2 0.9300 . ?
C3 C12 1.455(3) . ?
C3 C4 1.491(3) . ?
C4 N 1.462(3) . ?
C4 C5 1.507(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.471(4) . ?
C5 N 1.495(3) . ?
C5 H5 0.9800 . ?
C6 C11 1.384(3) . ?
C6 C7 1.395(3) . ?
C7 C8 1.367(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.378(4) . ?
C12 C13 1.388(3) . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 H17 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
O C1 N 122.1(3) . . ?
O C1 C2 129.7(3) . . ?
N C1 C2 108.2(2) . . ?
C3 C2 C1 111.5(2) . . ?
C3 C2 H2 124.3 . . ?
C1 C2 H2 124.3 . . ?
C2 C3 C12 129.7(2) . . ?
C2 C3 C4 107.0(2) . . ?
C12 C3 C4 123.3(2) . . ?
N C4 C3 108.0(2) . . ?
N C4 C5 60.46(15) . . ?
C3 C4 C5 117.6(2) . . ?
N C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 N 115.9(2) . . ?
C6 C5 C4 123.0(2) . . ?
N C5 C4 58.30(14) . . ?
C6 C5 H5 115.7 . . ?
N C5 H5 115.7 . . ?
C4 C5 H5 115.7 . . ?
C11 C6 C7 118.9(3) . . ?
C11 C6 C5 121.4(2) . . ?
C7 C6 C5 119.6(2) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C6 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
C17 C12 C13 117.3(2) . . ?
C17 C12 C3 121.3(2) . . ?
C13 C12 C3 121.4(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.7(3) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C1 N C4 104.9(2) . . ?
C1 N C5 111.0(2) . . ?
C4 N C5 61.23(15) . . ?

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
O C1 C2 C3 173.6(3) . . . . ?
N C1 C2 C3 -6.3(3) . . . . ?
C1 C2 C3 C12 -177.2(2) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
C2 C3 C4 N 2.4(3) . . . . ?
C12 C3 C4 N -178.0(2) . . . . ?
C2 C3 C4 C5 -63.1(3) . . . . ?
C12 C3 C4 C5 116.5(2) . . . . ?
N C4 C5 C6 102.1(3) . . . . ?
C3 C4 C5 C6 -161.9(2) . . . . ?
C3 C4 C5 N 96.0(2) . . . . ?
N C5 C6 C11 18.9(4) . . . . ?
C4 C5 C6 C11 -48.7(4) . . . . ?
N C5 C6 C7 -160.6(2) . . . . ?
C4 C5 C6 C7 131.8(3) . . . . ?
C11 C6 C7 C8 -0.8(4) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C6 0.0(5) . . . . ?
C7 C6 C11 C10 0.6(4) . . . . ?
C5 C6 C11 C10 -178.9(3) . . . . ?
C2 C3 C12 C17 179.5(3) . . . . ?
C4 C3 C12 C17 0.0(3) . . . . ?
C2 C3 C12 C13 -0.8(4) . . . . ?
C4 C3 C12 C13 179.7(2) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C3 C12 C13 C14 179.5(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C13 C12 C17 C16 0.7(4) . . . . ?
C3 C12 C17 C16 -179.5(2) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
O C1 N C4 -172.6(2) . . . . ?
C2 C1 N C4 7.3(3) . . . . ?
O C1 N C5 -108.1(3) . . . . ?
C2 C1 N C5 71.8(2) . . . . ?
C3 C4 N C1 -6.0(3) . . . . ?
C5 C4 N C1 106.1(2) . . . . ?
C3 C4 N C5 -112.1(2) . . . . ?
C6 C5 N C1 149.7(2) . . . . ?
C4 C5 N C1 -95.9(2) . . . . ?
C6 C5 N C4 -114.4(3) . . . . ?

_refine_diff_density_max         0.098
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.026

_shelxl_version_number           2014/6



