# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cp2
_database_code_depnum_ccdc_archive 'CCDC 2160655'
loop_
_audit_author_name
_audit_author_address
'Pi Cheng'
;Hunan Agricultural University
China
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            cp2
_chemical_formula_moiety         'C13 H11 N O'
_chemical_formula_sum            'C13 H11 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         197.23

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3315(6)
_cell_length_b                   7.7796(8)
_cell_length_c                   12.4238(14)
_cell_angle_alpha                72.694(6)
_cell_angle_beta                 78.711(5)
_cell_angle_gamma                89.961(5)
_cell_volume                     481.54(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4225
_cell_measurement_theta_min      3.8074
_cell_measurement_theta_max      72.3541
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             208

_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            5689
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         74.94
_diffrn_reflns_theta_full        74.94
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.935
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             1857
_reflns_number_gt                1596
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.1139
_refine_ls_wR_factor_gt          0.3700
_refine_ls_wR_factor_ref         0.3950
_refine_ls_goodness_of_fit_ref   1.833
_refine_ls_restrained_S_all      1.587
_refine_ls_number_reflns         1857
_refine_ls_number_parameters     272
_refine_ls_number_restraints     716
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.1235(8) 0.2367(5) 0.5031(4) 0.0459(9) Uani d U P D 0.732(3) A 1
N N1 0.3128(7) 0.2509(4) 0.4636(3) 0.0448(7) Uani d U P D 0.732(3) A 1
H H1 0.448896 0.249773 0.494024 0.054 Uiso calc U P R 0.732(3) A 1
C C1 0.0923(8) 0.2414(4) 0.6548(3) 0.0453(7) Uani d U P D 0.732(3) A 1
C C2 -0.1141(8) 0.1520(5) 0.7423(3) 0.0458(8) Uani d U P D 0.732(3) A 1
H H2 -0.25233 0.095974 0.724607 0.055 Uiso calc U P R 0.732(3) A 1
C C3 -0.1150(11) 0.1457(7) 0.8562(4) 0.0463(8) Uani d U P D 0.732(3) A 1
H H3 -0.254411 0.084864 0.915942 0.056 Uiso calc U P R 0.732(3) A 1
C C4 0.0873(10) 0.2281(8) 0.8827(5) 0.0464(8) Uani d U P D 0.732(3) A 1
H H4 0.085893 0.223603 0.96003 0.056 Uiso calc U P R 0.732(3) A 1
C C5 0.2915(10) 0.3173(7) 0.7946(3) 0.0466(8) Uani d U P D 0.732(3) A 1
H H5 0.429033 0.375037 0.811683 0.056 Uiso calc U P R 0.732(3) A 1
C C6 0.2930(9) 0.3212(5) 0.6822(3) 0.0462(8) Uani d U P D 0.732(3) A 1
H H6 0.434426 0.379778 0.622824 0.055 Uiso calc U P R 0.732(3) A 1
C C7 0.3547(9) 0.2595(4) 0.3458(3) 0.0449(7) Uani d U P D 0.732(3) A 1
C C8 0.1935(8) 0.3443(5) 0.2740(3) 0.0455(8) Uani d U P D 0.732(3) A 1
H H8 0.046077 0.397469 0.303825 0.055 Uiso calc U P R 0.732(3) A 1
C C9 0.2463(11) 0.3522(7) 0.1582(4) 0.0461(8) Uani d U P D 0.732(3) A 1
H H9 0.134376 0.410158 0.109623 0.055 Uiso calc U P R 0.732(3) A 1
C C10 0.4610(10) 0.2759(8) 0.1136(5) 0.0460(8) Uani d U P D 0.732(3) A 1
H H10 0.497236 0.281613 0.034584 0.055 Uiso calc U P R 0.732(3) A 1
C C11 0.6242(9) 0.1902(6) 0.1861(3) 0.0459(8) Uani d U P D 0.732(3) A 1
H H11 0.772297 0.137655 0.156274 0.055 Uiso calc U P R 0.732(3) A 1
C C12 0.5695(9) 0.1818(5) 0.3023(3) 0.0455(8) Uani d U P D 0.732(3) A 1
H H12 0.679688 0.122822 0.35145 0.055 Uiso calc U P R 0.732(3) A 1
C C13 0.0809(8) 0.2444(5) 0.5333(3) 0.0448(7) Uani d U P D 0.732(3) A 1
O O1A -0.119(2) 0.2753(15) 0.4904(12) 0.0453(10) Uani d U P D 0.268(3) A 2
N N1A 0.2739(18) 0.2493(12) 0.5406(6) 0.0449(8) Uani d U P D 0.268(3) A 2
H H1A 0.439579 0.253815 0.512818 0.054 Uiso calc U P R 0.268(3) A 2
C C1A 0.250(2) 0.2589(14) 0.3448(8) 0.0451(8) Uani d U P D 0.268(3) A 2
C C2A 0.139(2) 0.3486(16) 0.2527(8) 0.0455(8) Uani d U P D 0.268(3) A 2
H H2A -0.017995 0.404267 0.264313 0.055 Uiso calc U P R 0.268(3) A 2
C C3A 0.269(3) 0.354(2) 0.1419(11) 0.0459(8) Uani d U P D 0.268(3) A 2
H H3A 0.196649 0.415183 0.078001 0.055 Uiso calc U P R 0.268(3) A 2
C C4A 0.501(3) 0.273(2) 0.1211(13) 0.0460(8) Uani d U P D 0.268(3) A 2
H H4A 0.585563 0.279748 0.044966 0.055 Uiso calc U P R 0.268(3) A 2
C C5A 0.602(3) 0.1814(17) 0.2153(8) 0.0458(8) Uani d U P D 0.268(3) A 2
H H5A 0.754375 0.119829 0.205164 0.055 Uiso calc U P R 0.268(3) A 2
C C6A 0.478(2) 0.1808(15) 0.3250(8) 0.0454(8) Uani d U P D 0.268(3) A 2
H H6A 0.554356 0.12417 0.388598 0.054 Uiso calc U P R 0.268(3) A 2
C C7A 0.198(2) 0.2389(15) 0.6569(8) 0.0455(7) Uani d U P D 0.268(3) A 2
C C8A -0.035(2) 0.1552(17) 0.7227(8) 0.0459(8) Uani d U P D 0.268(3) A 2
H H8A -0.143738 0.10068 0.688284 0.055 Uiso calc U P R 0.268(3) A 2
C C9A -0.114(3) 0.149(2) 0.8366(9) 0.0462(8) Uani d U P D 0.268(3) A 2
H H9A -0.275741 0.092104 0.879676 0.055 Uiso calc U P R 0.268(3) A 2
C C10A 0.046(3) 0.226(2) 0.8873(14) 0.0464(8) Uani d U P D 0.268(3) A 2
H H10A -0.004134 0.221824 0.965863 0.056 Uiso calc U P R 0.268(3) A 2
C C11A 0.280(3) 0.3110(19) 0.8216(8) 0.0465(8) Uani d U P D 0.268(3) A 2
H H11A 0.387775 0.365211 0.856446 0.056 Uiso calc U P R 0.268(3) A 2
C C12A 0.361(2) 0.3187(15) 0.7064(8) 0.0460(8) Uani d U P D 0.268(3) A 2
H H12A 0.522303 0.37622 0.662981 0.055 Uiso calc U P R 0.268(3) A 2
C C13A 0.1131(19) 0.2530(13) 0.4650(7) 0.0449(8) Uani d U P D 0.268(3) 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.227(6) ?
N1 C13 . 1.355(5) ?
N1 C7 . 1.417(4) ?
N1 H1 . 0.88 ?
C1 C6 . 1.383(6) ?
C1 C2 . 1.400(5) ?
C1 C13 . 1.517(5) ?
C2 C3 . 1.400(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.395(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.395(6) ?
C4 H4 . 0.95 ?
C5 C6 . 1.387(5) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C12 . 1.386(7) ?
C7 C8 . 1.386(6) ?
C8 C9 . 1.393(5) ?
C8 H8 . 0.95 ?
C9 C10 . 1.384(7) ?
C9 H9 . 0.95 ?
C10 C11 . 1.401(6) ?
C10 H10 . 0.95 ?
C11 C12 . 1.397(4) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
O1A C13A . 1.244(13) ?
N1A C13A . 1.384(11) ?
N1A C7A . 1.400(10) ?
N1A H1A . 0.88 ?
C1A C6A . 1.371(11) ?
C1A C2A . 1.389(11) ?
C1A C13A . 1.516(11) ?
C2A C3A . 1.404(11) ?
C2A H2A . 0.95 ?
C3A C4A . 1.400(13) ?
C3A H3A . 0.95 ?
C4A C5A . 1.384(12) ?
C4A H4A . 0.95 ?
C5A C6A . 1.392(10) ?
C5A H5A . 0.95 ?
C6A H6A . 0.95 ?
C7A C8A . 1.389(11) ?
C7A C12A . 1.398(11) ?
C8A C9A . 1.382(11) ?
C8A H8A . 0.95 ?
C9A C10A . 1.386(13) ?
C9A H9A . 0.95 ?
C10A C11A . 1.394(12) ?
C10A H10A . 0.95 ?
C11A C12A . 1.395(10) ?
C11A H11A . 0.95 ?
C12A H12A . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 N1 C7 . . 125.5(3) ?
C13 N1 H1 . . 117.3 ?
C7 N1 H1 . . 117.3 ?
C6 C1 C2 . . 119.6(4) ?
C6 C1 C13 . . 123.6(3) ?
C2 C1 C13 . . 116.8(4) ?
C3 C2 C1 . . 119.4(4) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 120.5(5) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.5(6) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C5 C4 . . 119.8(5) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C1 C6 C5 . . 121.2(4) ?
C1 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C12 C7 C8 . . 119.8(4) ?
C12 C7 N1 . . 117.5(4) ?
C8 C7 N1 . . 122.7(4) ?
C7 C8 C9 . . 120.4(5) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C10 C9 C8 . . 120.4(6) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 119.3(5) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
C12 C11 C10 . . 120.1(5) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C7 C12 C11 . . 120.1(4) ?
C7 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
O1 C13 N1 . . 123.7(4) ?
O1 C13 C1 . . 121.8(4) ?
N1 C13 C1 . . 114.4(3) ?
C13A N1A C7A . . 126.4(9) ?
C13A N1A H1A . . 116.8 ?
C7A N1A H1A . . 116.8 ?
C6A C1A C2A . . 119.8(9) ?
C6A C1A C13A . . 122.0(8) ?
C2A C1A C13A . . 118.2(9) ?
C1A C2A C3A . . 117.5(11) ?
C1A C2A H2A . . 121.3 ?
C3A C2A H2A . . 121.2 ?
C4A C3A C2A . . 123.1(14) ?
C4A C3A H3A . . 118.5 ?
C2A C3A H3A . . 118.5 ?
C5A C4A C3A . . 117.6(14) ?
C5A C4A H4A . . 121.2 ?
C3A C4A H4A . . 121.2 ?
C4A C5A C6A . . 119.5(12) ?
C4A C5A H5A . . 120.3 ?
C6A C5A H5A . . 120.3 ?
C1A C6A C5A . . 122.4(10) ?
C1A C6A H6A . . 118.8 ?
C5A C6A H6A . . 118.8 ?
C8A C7A C12A . . 119.8(9) ?
C8A C7A N1A . . 121.5(9) ?
C12A C7A N1A . . 118.6(9) ?
C9A C8A C7A . . 121.9(11) ?
C9A C8A H8A . . 119.0 ?
C7A C8A H8A . . 119.1 ?
C10A C9A C8A . . 119.1(14) ?
C10A C9A H9A . . 120.4 ?
C8A C9A H9A . . 120.5 ?
C9A C10A C11A . . 119.2(15) ?
C9A C10A H10A . . 120.4 ?
C11A C10A H10A . . 120.4 ?
C12A C11A C10A . . 122.2(12) ?
C12A C11A H11A . . 118.9 ?
C10A C11A H11A . . 118.9 ?
C11A C12A C7A . . 117.8(10) ?
C11A C12A H12A . . 121.1 ?
C7A C12A H12A . . 121.1 ?
O1A C13A N1A . . 121.6(11) ?
O1A C13A C1A . . 123.2(10) ?
N1A C13A C1A . . 114.5(8) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.4(2) ?
C13 C1 C2 C3 . . . . -179.6(2) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 0.0(5) ?
C3 C4 C5 C6 . . . . -0.8(7) ?
C2 C1 C6 C5 . . . . -1.2(4) ?
C13 C1 C6 C5 . . . . 178.8(3) ?
C4 C5 C6 C1 . . . . 1.4(6) ?
C13 N1 C7 C12 . . . . -149.8(4) ?
C13 N1 C7 C8 . . . . 31.4(4) ?
C12 C7 C8 C9 . . . . -0.1(2) ?
N1 C7 C8 C9 . . . . 178.7(2) ?
C7 C8 C9 C10 . . . . -0.2(2) ?
C8 C9 C10 C11 . . . . 0.2(5) ?
C9 C10 C11 C12 . . . . 0.2(6) ?
C8 C7 C12 C11 . . . . 0.5(4) ?
N1 C7 C12 C11 . . . . -178.4(3) ?
C10 C11 C12 C7 . . . . -0.5(5) ?
C7 N1 C13 O1 . . . . 3.5(6) ?
C7 N1 C13 C1 . . . . -178.3(2) ?
C6 C1 C13 O1 . . . . -152.1(4) ?
C2 C1 C13 O1 . . . . 27.9(4) ?
C6 C1 C13 N1 . . . . 29.6(4) ?
C2 C1 C13 N1 . . . . -150.3(3) ?
C6A C1A C2A C3A . . . . 0.4(15) ?
C13A C1A C2A C3A . . . . 179.6(10) ?
C1A C2A C3A C4A . . . . 0.4(17) ?
C2A C3A C4A C5A . . . . 0.9(19) ?
C3A C4A C5A C6A . . . . -2.9(18) ?
C2A C1A C6A C5A . . . . -2.5(16) ?
C13A C1A C6A C5A . . . . 178.3(9) ?
C4A C5A C6A C1A . . . . 3.8(17) ?
C13A N1A C7A C8A . . . . 28.6(17) ?
C13A N1A C7A C12A . . . . -150.0(12) ?
C12A C7A C8A C9A . . . . 0.4(18) ?
N1A C7A C8A C9A . . . . -178.1(11) ?
C7A C8A C9A C10A . . . . -0.8(19) ?
C8A C9A C10A C11A . . . . 1.(2) ?
C9A C10A C11A C12A . . . . -1.(2) ?
C10A C11A C12A C7A . . . . 0.(2) ?
C8A C7A C12A C11A . . . . -0.2(18) ?
N1A C7A C12A C11A . . . . 178.4(11) ?
C7A N1A C13A O1A . . . . 11.3(17) ?
C7A N1A C13A C1A . . . . -178.3(8) ?
C6A C1A C13A O1A . . . . -159.2(11) ?
C2A C1A C13A O1A . . . . 21.6(15) ?
C6A C1A C13A N1A . . . . 30.6(14) ?
C2A C1A C13A N1A . . . . -148.7(10) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8^a H8^a O1^a . 0.95 2.41 2.892(6) 111.3 ?
N1A^b H1A^b O1A^b 1_655 0.88 2.31 3.167(15) 163.6 ?

