# Supplementary Information (SI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_SPA989
_database_code_depnum_ccdc_archive 'CCDC 2406006'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   12.003(2)
_cell_length_b                   11.347(2)
_cell_length_c                   10.802(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.75(3)
_cell_angle_gamma                90
_cell_volume                     1440.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    221(2)
_cell_measurement_reflns_used    41997
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.054
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      221(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13250
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.536
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        22.210
_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             3639
_reflns_number_gt                2423
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0667P)²+0.1120P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.074(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3639
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.98526(12) 0.27122(11) 0.60224(15) 0.0659(4) Uani 1 1 d . . . . .
N1 N 0.68972(11) 0.74108(11) 0.45051(13) 0.0458(4) Uani 1 1 d . . . . .
C1 C 0.71583(13) 0.85810(13) 0.49503(14) 0.0402(3) Uani 1 1 d . . . . .
C2 C 0.63877(14) 0.92241(15) 0.54611(15) 0.0462(4) Uani 1 1 d . . . . .
H2 H 0.568222 0.889165 0.551649 0.055 Uiso 1 1 calc R U . . .
C3 C 0.66517(15) 1.03573(15) 0.58920(16) 0.0506(4) Uani 1 1 d . . . . .
H3 H 0.612248 1.079612 0.623421 0.061 Uiso 1 1 calc R U . . .
C4 C 0.76843(15) 1.08445(14) 0.58220(15) 0.0495(4) Uani 1 1 d . . . . .
H4 H 0.786649 1.161202 0.612382 0.059 Uiso 1 1 calc R U . . .
C5 C 0.84493(15) 1.02046(14) 0.53088(16) 0.0491(4) Uani 1 1 d . . . . .
H5 H 0.915414 1.053996 0.525581 0.059 Uiso 1 1 calc R U . . .
C6 C 0.81942(14) 0.90736(14) 0.48696(16) 0.0454(4) Uani 1 1 d . . . . .
H6 H 0.872174 0.864146 0.451795 0.055 Uiso 1 1 calc R U . . .
C7 C 0.58203(13) 0.72055(13) 0.37093(14) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.54502(15) 0.78973(16) 0.26604(16) 0.0509(4) Uani 1 1 d . . . . .
H8 H 0.592285 0.849148 0.244601 0.061 Uiso 1 1 calc R U . . .
C9 C 0.43781(16) 0.77141(19) 0.19217(16) 0.0612(5) Uani 1 1 d . . . . .
H9 H 0.412513 0.819078 0.120812 0.073 Uiso 1 1 calc R U . . .
C10 C 0.36818(16) 0.68482(19) 0.22168(18) 0.0597(5) Uani 1 1 d . . . . .
H10 H 0.295565 0.672884 0.170983 0.072 Uiso 1 1 calc R U . . .
C11 C 0.40539(15) 0.61594(17) 0.3256(2) 0.0605(5) Uani 1 1 d . . . . .
H11 H 0.358171 0.556206 0.346538 0.073 Uiso 1 1 calc R U . . .
C12 C 0.51149(14) 0.63358(15) 0.39978(17) 0.0509(4) Uani 1 1 d . . . . .
H12 H 0.536223 0.585674 0.471075 0.061 Uiso 1 1 calc R U . . .
C13 C 0.75987(13) 0.64770(13) 0.50078(14) 0.0403(4) Uani 1 1 d . . . . .
C14 C 0.76245(14) 0.54439(14) 0.43075(15) 0.0453(4) Uani 1 1 d . . . . .
H14 H 0.715944 0.537793 0.349763 0.054 Uiso 1 1 calc R U . . .
C15 C 0.83204(14) 0.45289(14) 0.47911(16) 0.0457(4) Uani 1 1 d . . . . .
H15 H 0.832373 0.383746 0.431253 0.055 Uiso 1 1 calc R U . . .
C16 C 0.90222(14) 0.46096(13) 0.59807(16) 0.0442(4) Uani 1 1 d . . . . .
C17 C 0.90008(14) 0.56374(14) 0.66643(16) 0.0472(4) Uani 1 1 d . . . . .
H17 H 0.947932 0.570686 0.746604 0.057 Uiso 1 1 calc R U . . .
C18 C 0.82982(14) 0.65569(14) 0.62002(15) 0.0451(4) Uani 1 1 d . . . . .
H18 H 0.828953 0.724140 0.668830 0.054 Uiso 1 1 calc R U . . .
C19 C 0.97836(16) 0.36602(15) 0.65094(19) 0.0553(5) Uani 1 1 d . . . . .
H19 H 1.026443 0.379541 0.729899 0.066 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.208(2) . ?
N1 C13 1.3930(19) . ?
N1 C7 1.418(2) . ?
N1 C1 1.4252(19) . ?
C1 C2 1.378(2) . ?
C1 C6 1.382(2) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.373(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.376(2) . ?
C7 C12 1.377(2) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.369(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.374(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.390(2) . ?
C13 C14 1.399(2) . ?
C14 C15 1.368(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.383(2) . ?
C16 C19 1.452(2) . ?
C17 C18 1.371(2) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C13 N1 C7 121.02(12) . . ?
C13 N1 C1 120.22(12) . . ?
C7 N1 C1 117.92(12) . . ?
C2 C1 C6 119.79(14) . . ?
C2 C1 N1 120.59(15) . . ?
C6 C1 N1 119.62(15) . . ?
C1 C2 C3 120.05(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.23(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.65(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.70(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.57(16) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 119.02(15) . . ?
C8 C7 N1 120.47(15) . . ?
C12 C7 N1 120.47(14) . . ?
C7 C8 C9 119.69(18) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.88(17) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.28(16) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.31(18) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.82(17) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 N1 120.98(14) . . ?
C18 C13 C14 118.69(14) . . ?
N1 C13 C14 120.32(14) . . ?
C15 C14 C13 120.57(15) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.77(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.41(14) . . ?
C17 C16 C19 119.61(15) . . ?
C15 C16 C19 121.98(15) . . ?
C18 C17 C16 121.56(15) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.99(15) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C16 125.65(18) . . ?
O1 C19 H19 117.2 . . ?
C16 C19 H19 117.2 . . ?

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
C13 N1 C1 C2 -121.81(17) . . . . ?
C7 N1 C1 C2 47.7(2) . . . . ?
C13 N1 C1 C6 58.1(2) . . . . ?
C7 N1 C1 C6 -132.34(16) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
N1 C1 C2 C3 179.87(14) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
N1 C1 C6 C5 -179.58(14) . . . . ?
C13 N1 C7 C8 -139.54(17) . . . . ?
C1 N1 C7 C8 51.0(2) . . . . ?
C13 N1 C7 C12 42.6(2) . . . . ?
C1 N1 C7 C12 -126.88(17) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
N1 C7 C8 C9 -177.48(15) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
N1 C7 C12 C11 177.65(16) . . . . ?
C7 N1 C13 C18 -146.29(16) . . . . ?
C1 N1 C13 C18 22.9(2) . . . . ?
C7 N1 C13 C14 34.8(2) . . . . ?
C1 N1 C13 C14 -156.03(16) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
N1 C13 C14 C15 179.32(15) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C14 C15 C16 C19 -178.95(16) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C19 C16 C17 C18 179.80(16) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
N1 C13 C18 C17 -178.51(15) . . . . ?
C14 C13 C18 C17 0.5(2) . . . . ?
C17 C16 C19 O1 177.55(18) . . . . ?
C15 C16 C19 O1 -3.5(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
C6 H6 O1 0.94 2.46 3.384(2) 168.9 3_766 yes

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040























####################################################################### 
# 
# 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_SPA991
_database_code_depnum_ccdc_archive 'CCDC 2406012'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   12.004(2)
_cell_length_b                   11.352(2)
_cell_length_c                   10.797(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.70(3)
_cell_angle_gamma                90
_cell_volume                     1440.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    42497
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13225
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.536
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3618
_reflns_number_gt                2798
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0672P)²+0.1123P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.155(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3618
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.01459(9) 0.27111(9) 0.39748(12) 0.0633(3) Uani 1 1 d . . . . .
N1 N 0.31028(9) 0.74125(9) 0.54935(10) 0.0435(3) Uani 1 1 d . . . . .
C1 C 0.28403(10) 0.85787(10) 0.50469(11) 0.0381(3) Uani 1 1 d . . . . .
C2 C 0.36136(11) 0.92253(11) 0.45360(12) 0.0442(3) Uani 1 1 d . . . . .
H2 H 0.431984 0.889518 0.447996 0.053 Uiso 1 1 calc R U . . .
C3 C 0.33461(12) 1.03556(12) 0.41089(12) 0.0483(3) Uani 1 1 d . . . . .
H3 H 0.387494 1.079527 0.376682 0.058 Uiso 1 1 calc R U . . .
C4 C 0.23142(12) 1.08449(11) 0.41787(12) 0.0473(3) Uani 1 1 d . . . . .
H4 H 0.213294 1.161245 0.387750 0.057 Uiso 1 1 calc R U . . .
C5 C 0.15491(11) 1.02040(11) 0.46921(13) 0.0465(3) Uani 1 1 d . . . . .
H5 H 0.084381 1.053779 0.474563 0.056 Uiso 1 1 calc R U . . .
C6 C 0.18064(10) 0.90767(10) 0.51292(12) 0.0432(3) Uani 1 1 d . . . . .
H6 H 0.127942 0.864590 0.548335 0.052 Uiso 1 1 calc R U . . .
C7 C 0.41790(10) 0.72054(10) 0.62906(11) 0.0389(3) Uani 1 1 d . . . . .
C8 C 0.45488(12) 0.78980(12) 0.73400(12) 0.0489(3) Uani 1 1 d . . . . .
H8 H 0.407680 0.849299 0.755389 0.059 Uiso 1 1 calc R U . . .
C9 C 0.56218(13) 0.77129(15) 0.80801(12) 0.0593(4) Uani 1 1 d . . . . .
H9 H 0.587395 0.818740 0.879548 0.071 Uiso 1 1 calc R U . . .
C10 C 0.63179(12) 0.68493(15) 0.77831(14) 0.0586(4) Uani 1 1 d . . . . .
H10 H 0.704395 0.673141 0.829005 0.070 Uiso 1 1 calc R U . . .
C11 C 0.59483(12) 0.61573(14) 0.67405(15) 0.0579(4) Uani 1 1 d . . . . .
H11 H 0.642091 0.556006 0.653253 0.069 Uiso 1 1 calc R U . . .
C12 C 0.48849(11) 0.63355(12) 0.59966(13) 0.0495(3) Uani 1 1 d . . . . .
H12 H 0.463800 0.585927 0.528140 0.059 Uiso 1 1 calc R U . . .
C13 C 0.24014(10) 0.64749(10) 0.49913(11) 0.0384(3) Uani 1 1 d . . . . .
C14 C 0.23770(11) 0.54451(11) 0.56943(12) 0.0431(3) Uani 1 1 d . . . . .
H14 H 0.284208 0.538028 0.650414 0.052 Uiso 1 1 calc R U . . .
C15 C 0.16789(11) 0.45288(11) 0.52104(13) 0.0438(3) Uani 1 1 d . . . . .
H15 H 0.167428 0.383828 0.568976 0.053 Uiso 1 1 calc R U . . .
C16 C 0.09775(10) 0.46095(11) 0.40183(12) 0.0424(3) Uani 1 1 d . . . . .
C17 C 0.09988(11) 0.56374(11) 0.33341(12) 0.0453(3) Uani 1 1 d . . . . .
H17 H 0.051987 0.570719 0.253267 0.054 Uiso 1 1 calc R U . . .
C18 C 0.17026(11) 0.65568(11) 0.37983(12) 0.0428(3) Uani 1 1 d . . . . .
H18 H 0.171233 0.724110 0.331042 0.051 Uiso 1 1 calc R U . . .
C19 C 0.02166(12) 0.36593(12) 0.34908(15) 0.0533(3) Uani 1 1 d . . . . .
H19 H -0.026396 0.379525 0.270137 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2071(17) . ?
N1 C13 1.3966(15) . ?
N1 C7 1.4192(16) . ?
N1 C1 1.4222(15) . ?
C1 C2 1.3829(17) . ?
C1 C6 1.3830(17) . ?
C2 C3 1.3792(18) . ?
C2 H2 0.9400 . ?
C3 C4 1.3735(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.3735(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3772(17) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.3766(18) . ?
C7 C12 1.3795(18) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.368(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.371(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.3782(19) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3904(17) . ?
C13 C14 1.3973(17) . ?
C14 C15 1.3709(18) . ?
C14 H14 0.9400 . ?
C15 C16 1.3908(19) . ?
C15 H15 0.9400 . ?
C16 C17 1.3841(17) . ?
C16 C19 1.4529(18) . ?
C17 C18 1.3721(17) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C13 N1 C7 120.80(10) . . ?
C13 N1 C1 120.21(10) . . ?
C7 N1 C1 118.14(10) . . ?
C2 C1 C6 119.50(11) . . ?
C2 C1 N1 120.59(11) . . ?
C6 C1 N1 119.91(11) . . ?
C3 C2 C1 119.84(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.61(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.49(12) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.58(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.97(11) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 C12 119.19(12) . . ?
C8 C7 N1 120.42(12) . . ?
C12 C7 N1 120.34(11) . . ?
C7 C8 C9 119.62(14) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.90(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.47(13) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.11(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.70(13) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C18 C13 N1 120.77(11) . . ?
C18 C13 C14 118.94(11) . . ?
N1 C13 C14 120.27(11) . . ?
C15 C14 C13 120.42(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.75(11) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.44(11) . . ?
C17 C16 C19 119.66(12) . . ?
C15 C16 C19 121.89(12) . . ?
C18 C17 C16 121.53(12) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.91(12) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C16 125.88(15) . . ?
O1 C19 H19 117.1 . . ?
C16 C19 H19 117.1 . . ?

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
C13 N1 C1 C2 -121.99(13) . . . . ?
C7 N1 C1 C2 47.56(16) . . . . ?
C13 N1 C1 C6 58.39(16) . . . . ?
C7 N1 C1 C6 -132.06(12) . . . . ?
C6 C1 C2 C3 -0.30(18) . . . . ?
N1 C1 C2 C3 -179.91(11) . . . . ?
C1 C2 C3 C4 -0.40(19) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C2 C1 C6 C5 0.66(19) . . . . ?
N1 C1 C6 C5 -179.72(11) . . . . ?
C13 N1 C7 C8 -139.58(12) . . . . ?
C1 N1 C7 C8 50.94(16) . . . . ?
C13 N1 C7 C12 42.83(17) . . . . ?
C1 N1 C7 C12 -126.65(13) . . . . ?
C12 C7 C8 C9 0.16(19) . . . . ?
N1 C7 C8 C9 -177.45(12) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C8 C7 C12 C11 0.0(2) . . . . ?
N1 C7 C12 C11 177.62(12) . . . . ?
C7 N1 C13 C18 -146.42(12) . . . . ?
C1 N1 C13 C18 22.84(17) . . . . ?
C7 N1 C13 C14 34.78(17) . . . . ?
C1 N1 C13 C14 -155.96(11) . . . . ?
C18 C13 C14 C15 0.36(18) . . . . ?
N1 C13 C14 C15 179.18(11) . . . . ?
C13 C14 C15 C16 -0.49(19) . . . . ?
C14 C15 C16 C17 -0.17(18) . . . . ?
C14 C15 C16 C19 -179.02(12) . . . . ?
C15 C16 C17 C18 0.98(19) . . . . ?
C19 C16 C17 C18 179.86(12) . . . . ?
C16 C17 C18 C13 -1.1(2) . . . . ?
N1 C13 C18 C17 -178.38(11) . . . . ?
C14 C13 C18 C17 0.43(19) . . . . ?
C17 C16 C19 O1 177.52(14) . . . . ?
C15 C16 C19 O1 -3.6(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
C6 H6 O1 0.94 2.46 3.3862(17) 168.7 3_566 yes

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.044























####################################################################### 
# 
# 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_SPA990
_database_code_depnum_ccdc_archive 'CCDC 2406007'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   12.008(2)
_cell_length_b                   11.352(2)
_cell_length_c                   10.791(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.70(3)
_cell_angle_gamma                90
_cell_volume                     1440.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    221(2)
_cell_measurement_reflns_used    42994
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      221(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13307
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.535
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3441
_reflns_number_gt                2803
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0608P)²+0.2304P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.083(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3441
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.01474(9) 0.72880(8) 0.39785(13) 0.0561(3) Uani 1 1 d . . . . .
N1 N 0.31035(8) 0.25895(8) 0.54948(11) 0.0356(3) Uani 1 1 d . . . . .
C1 C 0.28408(9) 0.14217(9) 0.50462(11) 0.0300(3) Uani 1 1 d . . . . .
C2 C 0.36153(11) 0.07765(11) 0.45376(13) 0.0359(3) Uani 1 1 d . . . . .
H2 H 0.432153 0.110682 0.448298 0.043 Uiso 1 1 calc R U . . .
C3 C 0.33478(12) -0.03555(12) 0.41100(13) 0.0409(3) Uani 1 1 d . . . . .
H3 H 0.387759 -0.079584 0.377032 0.049 Uiso 1 1 calc R U . . .
C4 C 0.23140(12) -0.08444(11) 0.41763(13) 0.0393(3) Uani 1 1 d . . . . .
H4 H 0.213268 -0.161127 0.387277 0.047 Uiso 1 1 calc R U . . .
C5 C 0.15482(11) -0.02046(11) 0.46891(13) 0.0385(3) Uani 1 1 d . . . . .
H5 H 0.084307 -0.053900 0.474130 0.046 Uiso 1 1 calc R U . . .
C6 C 0.18050(10) 0.09265(10) 0.51293(13) 0.0355(3) Uani 1 1 d . . . . .
H6 H 0.127850 0.135773 0.548354 0.043 Uiso 1 1 calc R U . . .
C7 C 0.41787(10) 0.27955(10) 0.62909(12) 0.0309(3) Uani 1 1 d . . . . .
C8 C 0.48857(11) 0.36658(12) 0.60000(14) 0.0410(3) Uani 1 1 d . . . . .
H8 H 0.463928 0.414345 0.528540 0.049 Uiso 1 1 calc R U . . .
C9 C 0.59486(12) 0.38436(13) 0.67437(16) 0.0500(4) Uani 1 1 d . . . . .
H9 H 0.642043 0.444221 0.653737 0.060 Uiso 1 1 calc R U . . .
C10 C 0.63180(12) 0.31494(15) 0.77827(15) 0.0509(4) Uani 1 1 d . . . . .
H10 H 0.704459 0.326604 0.828868 0.061 Uiso 1 1 calc R U . . .
C11 C 0.56215(13) 0.22827(15) 0.80809(14) 0.0509(4) Uani 1 1 d . . . . .
H11 H 0.587383 0.180713 0.879578 0.061 Uiso 1 1 calc R U . . .
C12 C 0.45464(11) 0.20992(12) 0.73379(13) 0.0410(3) Uani 1 1 d . . . . .
H12 H 0.407391 0.150360 0.754937 0.049 Uiso 1 1 calc R U . . .
C13 C 0.24006(9) 0.35238(10) 0.49906(11) 0.0301(3) Uani 1 1 d . . . . .
C14 C 0.23771(10) 0.45556(10) 0.56973(12) 0.0349(3) Uani 1 1 d . . . . .
H14 H 0.284072 0.461959 0.650834 0.042 Uiso 1 1 calc R U . . .
C15 C 0.16800(10) 0.54730(10) 0.52104(13) 0.0355(3) Uani 1 1 d . . . . .
H15 H 0.167574 0.616443 0.568866 0.043 Uiso 1 1 calc R U . . .
C16 C 0.09822(10) 0.53915(10) 0.40216(13) 0.0347(3) Uani 1 1 d . . . . .
C17 C 0.09992(11) 0.43659(11) 0.33320(13) 0.0372(3) Uani 1 1 d . . . . .
H17 H 0.052023 0.429761 0.253016 0.045 Uiso 1 1 calc R U . . .
C18 C 0.17055(10) 0.34438(10) 0.38000(12) 0.0348(3) Uani 1 1 d . . . . .
H18 H 0.171623 0.275970 0.331170 0.042 Uiso 1 1 calc R U . . .
C19 C 0.02162(12) 0.63430(12) 0.34901(16) 0.0456(3) Uani 1 1 d . . . . .
H19 H -0.026431 0.620782 0.270022 0.055 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2054(17) . ?
N1 C13 1.3954(14) . ?
N1 C7 1.4177(15) . ?
N1 C1 1.4246(14) . ?
C1 C2 1.3818(17) . ?
C1 C6 1.3843(16) . ?
C2 C3 1.3810(18) . ?
C2 H2 0.9400 . ?
C3 C4 1.3749(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.3732(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3820(17) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.3763(18) . ?
C7 C8 1.3797(17) . ?
C8 C9 1.3778(19) . ?
C8 H8 0.9400 . ?
C9 C10 1.369(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.371(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3858(17) . ?
C13 C14 1.4010(16) . ?
C14 C15 1.3722(17) . ?
C14 H14 0.9400 . ?
C15 C16 1.3858(19) . ?
C15 H15 0.9400 . ?
C16 C17 1.3842(17) . ?
C16 C19 1.4587(17) . ?
C17 C18 1.3772(17) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C13 N1 C7 121.02(9) . . ?
C13 N1 C1 120.01(10) . . ?
C7 N1 C1 118.11(9) . . ?
C2 C1 C6 119.76(11) . . ?
C2 C1 N1 120.51(11) . . ?
C6 C1 N1 119.73(11) . . ?
C3 C2 C1 119.75(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.63(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.53(12) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.59(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.72(11) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 119.23(12) . . ?
C12 C7 N1 120.26(11) . . ?
C8 C7 N1 120.47(11) . . ?
C9 C8 C7 120.82(13) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.07(14) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.57(13) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.76(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.55(14) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C18 C13 N1 120.97(11) . . ?
C18 C13 C14 118.99(11) . . ?
N1 C13 C14 120.04(11) . . ?
C15 C14 C13 120.27(12) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.74(11) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.80(11) . . ?
C17 C16 C19 119.23(13) . . ?
C15 C16 C19 121.96(12) . . ?
C18 C17 C16 121.15(12) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 120.03(11) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C16 125.50(15) . . ?
O1 C19 H19 117.2 . . ?
C16 C19 H19 117.2 . . ?

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
C13 N1 C1 C2 122.12(13) . . . . ?
C7 N1 C1 C2 -47.37(17) . . . . ?
C13 N1 C1 C6 -58.37(17) . . . . ?
C7 N1 C1 C6 132.14(12) . . . . ?
C6 C1 C2 C3 0.33(19) . . . . ?
N1 C1 C2 C3 179.85(12) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C2 C1 C6 C5 -0.76(19) . . . . ?
N1 C1 C6 C5 179.73(11) . . . . ?
C13 N1 C7 C12 139.75(13) . . . . ?
C1 N1 C7 C12 -50.87(17) . . . . ?
C13 N1 C7 C8 -42.69(18) . . . . ?
C1 N1 C7 C8 126.69(13) . . . . ?
C12 C7 C8 C9 -0.1(2) . . . . ?
N1 C7 C8 C9 -177.65(13) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
N1 C7 C12 C11 177.47(12) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?
C7 N1 C13 C18 146.21(12) . . . . ?
C1 N1 C13 C18 -22.97(18) . . . . ?
C7 N1 C13 C14 -34.78(18) . . . . ?
C1 N1 C13 C14 156.04(12) . . . . ?
C18 C13 C14 C15 -0.40(19) . . . . ?
N1 C13 C14 C15 -179.42(11) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C17 0.07(19) . . . . ?
C14 C15 C16 C19 178.77(13) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C19 C16 C17 C18 -179.72(13) . . . . ?
C16 C17 C18 C13 1.2(2) . . . . ?
N1 C13 C18 C17 178.52(12) . . . . ?
C14 C13 C18 C17 -0.50(19) . . . . ?
C17 C16 C19 O1 -177.64(14) . . . . ?
C15 C16 C19 O1 3.7(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
C6 H6 O1 0.94 2.46 3.3834(17) 168.7 3_566 yes

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044



# start Validation Reply Form
_vrf_PLAT029_SPA990              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.957 Why?
RESPONSE: Since the Pohang Accelerator Laboratory 2D Beamline goniostat has
only one omega-axis, diffrn_measured_fraction_theta_full is not fully covered as 
0.957, especially for the low symmetry such as the monoclinic system. 
As this is an inherent problem, other command and option were not helpful to 
improve the completeness.
;
# end Validation Reply Form


















####################################################################### 
# 
# 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_SPA988
_database_code_depnum_ccdc_archive 'CCDC 2406008'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   12.012(2)
_cell_length_b                   11.349(2)
_cell_length_c                   10.792(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.68(3)
_cell_angle_gamma                90
_cell_volume                     1440.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    221(2)
_cell_measurement_reflns_used    42966
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      221(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14738
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.534
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        22.210
_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             4060
_reflns_number_gt                3226
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0585P)²+0.2422P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.083(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4060
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.98524(9) 0.27117(8) 0.60220(13) 0.0578(3) Uani 1 1 d . . . . .
N1 N 0.68970(9) 0.74118(8) 0.45078(10) 0.0375(3) Uani 1 1 d . . . . .
C1 C 0.71598(10) 0.85799(10) 0.49532(11) 0.0320(2) Uani 1 1 d . . . . .
C2 C 0.63874(11) 0.92261(11) 0.54637(12) 0.0376(3) Uani 1 1 d . . . . .
H2 H 0.568198 0.889530 0.552042 0.045 Uiso 1 1 calc R U . . .
C3 C 0.66532(12) 1.03578(12) 0.58903(12) 0.0425(3) Uani 1 1 d . . . . .
H3 H 0.612396 1.079781 0.623122 0.051 Uiso 1 1 calc R U . . .
C4 C 0.76867(12) 1.08476(11) 0.58206(12) 0.0408(3) Uani 1 1 d . . . . .
H4 H 0.786749 1.161587 0.612030 0.049 Uiso 1 1 calc R U . . .
C5 C 0.84517(11) 1.02049(11) 0.53098(13) 0.0402(3) Uani 1 1 d . . . . .
H5 H 0.915783 1.053740 0.525915 0.048 Uiso 1 1 calc R U . . .
C6 C 0.81937(10) 0.90744(10) 0.48698(13) 0.0369(3) Uani 1 1 d . . . . .
H6 H 0.871956 0.864283 0.451480 0.044 Uiso 1 1 calc R U . . .
C7 C 0.58222(10) 0.72057(10) 0.37116(11) 0.0328(2) Uani 1 1 d . . . . .
C8 C 0.51163(11) 0.63347(12) 0.40040(14) 0.0431(3) Uani 1 1 d . . . . .
H8 H 0.536226 0.585802 0.471929 0.052 Uiso 1 1 calc R U . . .
C9 C 0.40545(12) 0.61560(14) 0.32587(16) 0.0521(4) Uani 1 1 d . . . . .
H9 H 0.358272 0.555725 0.346521 0.063 Uiso 1 1 calc R U . . .
C10 C 0.36851(12) 0.68498(15) 0.22169(14) 0.0523(4) Uani 1 1 d . . . . .
H10 H 0.295965 0.673208 0.170980 0.063 Uiso 1 1 calc R U . . .
C11 C 0.43805(13) 0.77149(16) 0.19208(13) 0.0529(4) Uani 1 1 d . . . . .
H11 H 0.412852 0.819087 0.120622 0.063 Uiso 1 1 calc R U . . .
C12 C 0.54524(12) 0.78986(13) 0.26613(12) 0.0433(3) Uani 1 1 d . . . . .
H12 H 0.592442 0.849351 0.244728 0.052 Uiso 1 1 calc R U . . .
C13 C 0.75988(9) 0.64774(10) 0.50089(11) 0.0322(2) Uani 1 1 d . . . . .
C14 C 0.76231(11) 0.54439(11) 0.43061(12) 0.0370(3) Uani 1 1 d . . . . .
H14 H 0.715791 0.537830 0.349649 0.044 Uiso 1 1 calc R U . . .
C15 C 0.83199(10) 0.45273(10) 0.47897(13) 0.0376(3) Uani 1 1 d . . . . .
H15 H 0.832339 0.383602 0.431073 0.045 Uiso 1 1 calc R U . . .
C16 C 0.90207(10) 0.46086(10) 0.59791(12) 0.0362(3) Uani 1 1 d . . . . .
C17 C 0.90011(11) 0.56366(11) 0.66676(12) 0.0390(3) Uani 1 1 d . . . . .
H17 H 0.947976 0.570554 0.746919 0.047 Uiso 1 1 calc R U . . .
C18 C 0.82961(10) 0.65571(10) 0.62021(12) 0.0368(3) Uani 1 1 d . . . . .
H18 H 0.828543 0.724090 0.669109 0.044 Uiso 1 1 calc R U . . .
C19 C 0.97831(12) 0.36585(12) 0.65084(15) 0.0471(3) Uani 1 1 d . . . . .
H19 H 1.026334 0.379411 0.729802 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2061(17) . ?
N1 C13 1.3939(15) . ?
N1 C7 1.4180(16) . ?
N1 C1 1.4236(15) . ?
C1 C2 1.3818(17) . ?
C1 C6 1.3823(17) . ?
C2 C3 1.3798(18) . ?
C2 H2 0.9400 . ?
C3 C4 1.376(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.3731(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3813(17) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.3772(17) . ?
C7 C8 1.3799(17) . ?
C8 C9 1.3782(19) . ?
C8 H8 0.9400 . ?
C9 C10 1.371(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.368(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3898(17) . ?
C13 C14 1.4002(16) . ?
C14 C15 1.3705(18) . ?
C14 H14 0.9400 . ?
C15 C16 1.3883(19) . ?
C15 H15 0.9400 . ?
C16 C17 1.3859(17) . ?
C16 C19 1.4546(18) . ?
C17 C18 1.3744(17) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C13 N1 C7 120.96(10) . . ?
C13 N1 C1 120.14(10) . . ?
C7 N1 C1 118.08(9) . . ?
C2 C1 C6 119.68(11) . . ?
C2 C1 N1 120.53(11) . . ?
C6 C1 N1 119.79(11) . . ?
C3 C2 C1 119.89(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.54(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.46(12) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.64(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.78(11) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 119.11(12) . . ?
C12 C7 N1 120.46(11) . . ?
C8 C7 N1 120.39(11) . . ?
C9 C8 C7 120.73(13) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.12(15) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.49(13) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.85(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.71(14) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C18 C13 N1 120.91(11) . . ?
C18 C13 C14 118.79(11) . . ?
N1 C13 C14 120.29(11) . . ?
C15 C14 C13 120.51(11) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.72(11) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.60(11) . . ?
C17 C16 C19 119.41(12) . . ?
C15 C16 C19 121.97(12) . . ?
C18 C17 C16 121.33(12) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 120.03(11) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C16 125.66(15) . . ?
O1 C19 H19 117.2 . . ?
C16 C19 H19 117.2 . . ?

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
C13 N1 C1 C2 -122.13(13) . . . . ?
C7 N1 C1 C2 47.61(16) . . . . ?
C13 N1 C1 C6 58.14(16) . . . . ?
C7 N1 C1 C6 -132.12(12) . . . . ?
C6 C1 C2 C3 -0.20(18) . . . . ?
N1 C1 C2 C3 -179.93(11) . . . . ?
C1 C2 C3 C4 -0.49(19) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C2 C1 C6 C5 0.71(19) . . . . ?
N1 C1 C6 C5 -179.56(11) . . . . ?
C13 N1 C7 C12 -139.47(13) . . . . ?
C1 N1 C7 C12 50.87(16) . . . . ?
C13 N1 C7 C8 42.82(17) . . . . ?
C1 N1 C7 C8 -126.84(13) . . . . ?
C12 C7 C8 C9 0.0(2) . . . . ?
N1 C7 C8 C9 177.75(12) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C8 C7 C12 C11 0.27(19) . . . . ?
N1 C7 C12 C11 -177.47(12) . . . . ?
C10 C11 C12 C7 -0.3(2) . . . . ?
C7 N1 C13 C18 -146.29(12) . . . . ?
C1 N1 C13 C18 23.16(18) . . . . ?
C7 N1 C13 C14 34.57(17) . . . . ?
C1 N1 C13 C14 -155.98(12) . . . . ?
C18 C13 C14 C15 0.20(19) . . . . ?
N1 C13 C14 C15 179.36(11) . . . . ?
C13 C14 C15 C16 -0.52(19) . . . . ?
C14 C15 C16 C17 -0.01(19) . . . . ?
C14 C15 C16 C19 -178.95(12) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C19 C16 C17 C18 179.84(12) . . . . ?
C16 C17 C18 C13 -1.2(2) . . . . ?
N1 C13 C18 C17 -178.51(12) . . . . ?
C14 C13 C18 C17 0.65(19) . . . . ?
C17 C16 C19 O1 177.53(14) . . . . ?
C15 C16 C19 O1 -3.5(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
C6 H6 O1 0.94 2.46 3.3850(17) 168.6 3_766 yes

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050











































####################################################################### 
# 
# 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_SPA986
_database_code_depnum_ccdc_archive 'CCDC 2406011'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   12.075(2)
_cell_length_b                   11.371(2)
_cell_length_c                   10.787(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.73(3)
_cell_angle_gamma                90
_cell_volume                     1450.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    221(2)
_cell_measurement_reflns_used    42814
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      221(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14865
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.527
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4081
_reflns_number_gt                3029
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0782P)²+0.3721P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.131(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4081
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1841
_refine_ls_wR_factor_gt          0.1714
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.01533(14) 0.27162(13) 0.39937(18) 0.0691(5) Uani 1 1 d . . . . .
N1 N 0.31090(12) 0.74079(12) 0.54798(14) 0.0449(4) Uani 1 1 d . . . . .
C1 C 0.28478(14) 0.85723(14) 0.50356(15) 0.0392(3) Uani 1 1 d . . . . .
C5 C 0.15512(16) 1.01930(16) 0.46777(18) 0.0490(4) Uani 1 1 d . . . . .
H5 H 0.084704 1.052140 0.472671 0.059 Uiso 1 1 calc R U . . .
C6 C 0.18091(14) 0.90603(15) 0.51135(17) 0.0448(4) Uani 1 1 d . . . . .
H6 H 0.128445 0.862393 0.546020 0.054 Uiso 1 1 calc R U . . .
C7 C 0.41804(14) 0.72055(15) 0.62815(15) 0.0413(4) Uani 1 1 d . . . . .
C8 C 0.48822(16) 0.63362(18) 0.59995(19) 0.0536(5) Uani 1 1 d . . . . .
H8 H 0.463768 0.585592 0.528714 0.064 Uiso 1 1 calc R U . . .
C9 C 0.59397(17) 0.6160(2) 0.6747(2) 0.0632(6) Uani 1 1 d . . . . .
H9 H 0.640867 0.556070 0.654347 0.076 Uiso 1 1 calc R U . . .
C10 C 0.63076(17) 0.6853(2) 0.7785(2) 0.0631(6) Uani 1 1 d . . . . .
H10 H 0.702996 0.673808 0.829255 0.076 Uiso 1 1 calc R U . . .
C11 C 0.56137(19) 0.7718(2) 0.80775(17) 0.0641(6) Uani 1 1 d . . . . .
H11 H 0.586160 0.819093 0.879472 0.077 Uiso 1 1 calc R U . . .
C12 C 0.45448(17) 0.79049(19) 0.73262(17) 0.0522(5) Uani 1 1 d . . . . .
H12 H 0.407661 0.850407 0.753137 0.063 Uiso 1 1 calc R U . . .
C13 C 0.24096(13) 0.64734(14) 0.49912(15) 0.0396(3) Uani 1 1 d . . . . .
C14 C 0.17137(15) 0.65429(15) 0.37958(16) 0.0452(4) Uani 1 1 d . . . . .
H14 H 0.172402 0.722143 0.330048 0.054 Uiso 1 1 calc R U . . .
C15 C 0.10101(16) 0.56220(16) 0.33359(17) 0.0490(4) Uani 1 1 d . . . . .
H15 H 0.053355 0.568647 0.253317 0.059 Uiso 1 1 calc R U . . .
C16 C 0.09904(15) 0.46045(15) 0.40308(18) 0.0461(4) Uani 1 1 d . . . . .
C17 C 0.16877(15) 0.45307(15) 0.52232(18) 0.0473(4) Uani 1 1 d . . . . .
H17 H 0.168184 0.384519 0.570888 0.057 Uiso 1 1 calc R U . . .
C18 C 0.23841(15) 0.54456(15) 0.56993(16) 0.0456(4) Uani 1 1 d . . . . .
H18 H 0.284891 0.538264 0.650899 0.055 Uiso 1 1 calc R U . . .
C19 C 0.02225(18) 0.36499(18) 0.3500(2) 0.0582(5) Uani 1 1 d . . . . .
H19 H -0.025426 0.378101 0.270775 0.070 Uiso 1 1 calc R U . . .
C2 C 0.36138(15) 0.92220(17) 0.45325(16) 0.0466(4) Uani 1 1 d . . . . .
H2 H 0.431716 0.889595 0.447591 0.056 Uiso 1 1 calc R U . . .
C3 C 0.33440(17) 1.03558(17) 0.41111(17) 0.0521(5) Uani 1 1 d . . . . .
H3 H 0.387029 1.080128 0.377690 0.063 Uiso 1 1 calc R U . . .
C4 C 0.23077(17) 1.08388(16) 0.41774(17) 0.0506(4) Uani 1 1 d . . . . .
H4 H 0.212471 1.160592 0.388052 0.061 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.198(3) . ?
N1 C13 1.392(2) . ?
N1 C7 1.421(2) . ?
N1 C1 1.421(2) . ?
C1 C2 1.378(2) . ?
C1 C6 1.390(2) . ?
C5 C4 1.366(3) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.376(3) . ?
C7 C12 1.376(2) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.394(3) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.391(2) . ?
C13 C18 1.400(2) . ?
C14 C15 1.376(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.389(3) . ?
C16 C19 1.466(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9400 . ?
C4 H4 0.9400 . ?

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
C13 N1 C7 120.91(13) . . ?
C13 N1 C1 120.48(13) . . ?
C7 N1 C1 117.91(13) . . ?
C2 C1 C6 119.73(16) . . ?
C2 C1 N1 120.75(16) . . ?
C6 C1 N1 119.51(15) . . ?
C4 C5 C6 120.80(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.62(17) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 119.18(16) . . ?
C8 C7 N1 120.48(15) . . ?
C12 C7 N1 120.30(17) . . ?
C7 C8 C9 120.92(19) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.37(18) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.89(19) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.5(2) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 N1 120.87(15) . . ?
C14 C13 C18 118.50(15) . . ?
N1 C13 C18 120.63(14) . . ?
C15 C14 C13 120.23(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.28(16) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 118.62(16) . . ?
C15 C16 C19 119.16(17) . . ?
C17 C16 C19 122.21(17) . . ?
C18 C17 C16 120.75(16) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 120.61(16) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O1 C19 C16 125.3(2) . . ?
O1 C19 H19 117.3 . . ?
C16 C19 H19 117.3 . . ?
C1 C2 C3 119.78(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.57(18) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.49(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?

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
C13 N1 C1 C2 -123.10(18) . . . . ?
C7 N1 C1 C2 47.4(2) . . . . ?
C13 N1 C1 C6 57.1(2) . . . . ?
C7 N1 C1 C6 -132.39(17) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 -179.79(15) . . . . ?
C13 N1 C7 C8 43.2(2) . . . . ?
C1 N1 C7 C8 -127.31(19) . . . . ?
C13 N1 C7 C12 -139.11(18) . . . . ?
C1 N1 C7 C12 50.4(2) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
N1 C7 C8 C9 177.74(19) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
N1 C7 C12 C11 -177.89(17) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C7 N1 C13 C14 -146.41(17) . . . . ?
C1 N1 C13 C14 23.8(3) . . . . ?
C7 N1 C13 C18 34.2(2) . . . . ?
C1 N1 C13 C18 -155.55(17) . . . . ?
N1 C13 C14 C15 -178.67(17) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C14 C15 C16 C19 179.80(18) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C19 C16 C17 C18 -179.05(18) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
N1 C13 C18 C17 179.37(16) . . . . ?
C15 C16 C19 O1 177.7(2) . . . . ?
C17 C16 C19 O1 -3.5(3) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
N1 C1 C2 C3 -179.70(15) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C2 C3 C4 C5 0.8(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
C6 H6 O1 0.94 2.47 3.399(2) 169.7 3_566 yes

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.049























####################################################################### 
# 
# 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_SPA992
_database_code_depnum_ccdc_archive 'CCDC 2406009'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   12.005(2)
_cell_length_b                   11.349(2)
_cell_length_c                   10.792(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.71(3)
_cell_angle_gamma                90
_cell_volume                     1439.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    42895
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14776
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.536
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3948
_reflns_number_gt                3346
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0611P)²+0.2816P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.119(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3948
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.01459(8) 0.27112(8) 0.39773(12) 0.0541(3) Uani 1 1 d . . . . .
N1 N 0.31032(7) 0.74110(7) 0.54952(10) 0.0343(2) Uani 1 1 d . . . . .
C1 C 0.28406(8) 0.85782(8) 0.50486(10) 0.0289(2) Uani 1 1 d . . . . .
C2 C 0.18036(9) 0.90748(9) 0.51318(11) 0.0339(2) Uani 1 1 d . . . . .
H2 H 0.127742 0.864404 0.548732 0.041 Uiso 1 1 calc R U . . .
C3 C 0.15459(9) 1.02057(10) 0.46899(12) 0.0371(3) Uani 1 1 d . . . . .
H3 H 0.083990 1.053945 0.474031 0.045 Uiso 1 1 calc R U . . .
C4 C 0.23132(10) 1.08470(9) 0.41772(11) 0.0380(3) Uani 1 1 d . . . . .
H4 H 0.213178 1.161439 0.387456 0.046 Uiso 1 1 calc R U . . .
C5 C 0.33496(10) 1.03574(10) 0.41099(12) 0.0394(3) Uani 1 1 d . . . . .
H5 H 0.387970 1.079820 0.377102 0.047 Uiso 1 1 calc R U . . .
C6 C 0.36161(9) 0.92238(10) 0.45364(11) 0.0346(2) Uani 1 1 d . . . . .
H6 H 0.432135 0.889208 0.447911 0.042 Uiso 1 1 calc R U . . .
C7 C 0.41795(8) 0.72048(9) 0.62910(10) 0.0298(2) Uani 1 1 d . . . . .
C8 C 0.48851(10) 0.63328(10) 0.59962(13) 0.0399(3) Uani 1 1 d . . . . .
H8 H 0.463804 0.585564 0.528124 0.048 Uiso 1 1 calc R U . . .
C9 C 0.59497(10) 0.61562(12) 0.67425(15) 0.0486(3) Uani 1 1 d . . . . .
H9 H 0.642252 0.555863 0.653550 0.058 Uiso 1 1 calc R U . . .
C10 C 0.63199(10) 0.68500(13) 0.77853(13) 0.0495(3) Uani 1 1 d . . . . .
H10 H 0.704585 0.673188 0.829272 0.059 Uiso 1 1 calc R U . . .
C11 C 0.56224(11) 0.77177(14) 0.80821(12) 0.0492(3) Uani 1 1 d . . . . .
H11 H 0.587475 0.819419 0.879644 0.059 Uiso 1 1 calc R U . . .
C12 C 0.45488(10) 0.79004(11) 0.73403(12) 0.0398(3) Uani 1 1 d . . . . .
H12 H 0.407603 0.849552 0.755265 0.048 Uiso 1 1 calc R U . . .
C13 C 0.24009(8) 0.64773(8) 0.49919(10) 0.0291(2) Uani 1 1 d . . . . .
C14 C 0.23796(9) 0.54439(9) 0.56968(11) 0.0336(2) Uani 1 1 d . . . . .
H14 H 0.284641 0.537839 0.650606 0.040 Uiso 1 1 calc R U . . .
C15 C 0.16802(9) 0.45265(9) 0.52114(12) 0.0343(2) Uani 1 1 d . . . . .
H15 H 0.167575 0.383514 0.569003 0.041 Uiso 1 1 calc R U . . .
C16 C 0.09797(9) 0.46090(9) 0.40213(11) 0.0331(2) Uani 1 1 d . . . . .
C17 C 0.09971(9) 0.56362(9) 0.33314(11) 0.0355(2) Uani 1 1 d . . . . .
H17 H 0.051819 0.570430 0.252941 0.043 Uiso 1 1 calc R U . . .
C18 C 0.17032(9) 0.65591(9) 0.37991(11) 0.0338(2) Uani 1 1 d . . . . .
H18 H 0.171303 0.724383 0.331148 0.041 Uiso 1 1 calc R U . . .
C19 C 0.02154(10) 0.36581(10) 0.34892(14) 0.0437(3) Uani 1 1 d . . . . .
H19 H -0.026443 0.379342 0.269868 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2072(15) . ?
N1 C13 1.3938(13) . ?
N1 C7 1.4182(13) . ?
N1 C1 1.4230(13) . ?
C1 C6 1.3850(15) . ?
C1 C2 1.3859(14) . ?
C2 C3 1.3822(15) . ?
C2 H2 0.9400 . ?
C3 C4 1.3753(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.3779(17) . ?
C4 H4 0.9400 . ?
C5 C6 1.3818(16) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.3778(16) . ?
C7 C8 1.3811(15) . ?
C8 C9 1.3800(17) . ?
C8 H8 0.9400 . ?
C9 C10 1.371(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.372(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.3878(18) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3890(16) . ?
C13 C14 1.4010(14) . ?
C14 C15 1.3728(15) . ?
C14 H14 0.9400 . ?
C15 C16 1.3882(17) . ?
C15 H15 0.9400 . ?
C16 C17 1.3856(15) . ?
C16 C19 1.4568(15) . ?
C17 C18 1.3772(14) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C13 N1 C7 121.01(8) . . ?
C13 N1 C1 120.06(8) . . ?
C7 N1 C1 118.08(8) . . ?
C6 C1 C2 119.75(10) . . ?
C6 C1 N1 120.47(9) . . ?
C2 C1 N1 119.78(9) . . ?
C3 C2 C1 119.75(10) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.60(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.56(10) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.56(10) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.77(10) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 119.33(10) . . ?
C12 C7 N1 120.31(10) . . ?
C8 C7 N1 120.31(10) . . ?
C9 C8 C7 120.55(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.20(13) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.49(11) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.79(12) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.65(12) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C18 C13 N1 120.91(9) . . ?
C18 C13 C14 119.01(9) . . ?
N1 C13 C14 120.08(10) . . ?
C15 C14 C13 120.33(10) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.70(10) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.78(9) . . ?
C17 C16 C19 119.24(11) . . ?
C15 C16 C19 121.97(10) . . ?
C18 C17 C16 121.21(11) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 119.96(10) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C16 125.54(13) . . ?
O1 C19 H19 117.2 . . ?
C16 C19 H19 117.2 . . ?

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
C13 N1 C1 C6 -121.98(12) . . . . ?
C7 N1 C1 C6 47.55(15) . . . . ?
C13 N1 C1 C2 58.31(15) . . . . ?
C7 N1 C1 C2 -132.16(11) . . . . ?
C6 C1 C2 C3 0.73(17) . . . . ?
N1 C1 C2 C3 -179.56(10) . . . . ?
C1 C2 C3 C4 -0.52(18) . . . . ?
C2 C3 C4 C5 -0.30(18) . . . . ?
C3 C4 C5 C6 0.91(18) . . . . ?
C4 C5 C6 C1 -0.70(18) . . . . ?
C2 C1 C6 C5 -0.12(17) . . . . ?
N1 C1 C6 C5 -179.83(10) . . . . ?
C13 N1 C7 C12 -139.68(11) . . . . ?
C1 N1 C7 C12 50.90(15) . . . . ?
C13 N1 C7 C8 42.70(16) . . . . ?
C1 N1 C7 C8 -126.73(12) . . . . ?
C12 C7 C8 C9 0.03(18) . . . . ?
N1 C7 C8 C9 177.68(11) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C8 C7 C12 C11 0.17(18) . . . . ?
N1 C7 C12 C11 -177.48(11) . . . . ?
C10 C11 C12 C7 -0.19(19) . . . . ?
C7 N1 C13 C18 -146.25(11) . . . . ?
C1 N1 C13 C18 22.97(16) . . . . ?
C7 N1 C13 C14 34.63(16) . . . . ?
C1 N1 C13 C14 -156.15(10) . . . . ?
C18 C13 C14 C15 0.15(17) . . . . ?
N1 C13 C14 C15 179.28(10) . . . . ?
C13 C14 C15 C16 -0.38(17) . . . . ?
C14 C15 C16 C17 -0.11(17) . . . . ?
C14 C15 C16 C19 -179.01(11) . . . . ?
C15 C16 C17 C18 0.85(17) . . . . ?
C19 C16 C17 C18 179.78(11) . . . . ?
C16 C17 C18 C13 -1.09(18) . . . . ?
N1 C13 C18 C17 -178.55(10) . . . . ?
C14 C13 C18 C17 0.58(17) . . . . ?
C17 C16 C19 O1 177.64(13) . . . . ?
C15 C16 C19 O1 -3.5(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
C2 H2 O1 0.94 2.45 3.3799(15) 168.5 3_566 yes

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046























####################################################################### 
# 
# 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_SPA987
_database_code_depnum_ccdc_archive 'CCDC 2406010'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-11-28 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   12.006(2)
_cell_length_b                   11.351(2)
_cell_length_c                   10.793(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.67(3)
_cell_angle_gamma                90
_cell_volume                     1440.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    42468
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14738
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.535
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4059
_reflns_number_gt                2724
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0647P)²+0.0414P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4059
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.01490(10) 0.27111(9) 0.39784(13) 0.0688(4) Uani 1 1 d . . . . .
N1 N 0.31048(9) 0.74109(9) 0.54909(11) 0.0473(3) Uani 1 1 d . . . . .
C1 C 0.28401(11) 0.85795(11) 0.50449(12) 0.0421(3) Uani 1 1 d . . . . .
C4 C 0.23124(13) 1.08438(12) 0.41796(14) 0.0513(4) Uani 1 1 d . . . . .
H4 H 0.213090 1.161196 0.388044 0.062 Uiso 1 1 calc R U . . .
C5 C 0.15515(12) 1.02014(12) 0.46879(14) 0.0510(4) Uani 1 1 d . . . . .
H5 H 0.084452 1.053361 0.473696 0.061 Uiso 1 1 calc R U . . .
C6 C 0.18061(11) 0.90749(12) 0.51287(14) 0.0474(3) Uani 1 1 d . . . . .
H6 H 0.127955 0.864509 0.548479 0.057 Uiso 1 1 calc R U . . .
C7 C 0.41802(11) 0.72050(11) 0.62905(13) 0.0428(3) Uani 1 1 d . . . . .
C8 C 0.45461(13) 0.78977(14) 0.73370(14) 0.0537(4) Uani 1 1 d . . . . .
H8 H 0.407263 0.849208 0.754928 0.064 Uiso 1 1 calc R U . . .
C9 C 0.56183(14) 0.77153(16) 0.80789(14) 0.0626(4) Uani 1 1 d . . . . .
H9 H 0.586954 0.819083 0.879385 0.075 Uiso 1 1 calc R U . . .
C10 C 0.63151(14) 0.68499(16) 0.77814(16) 0.0634(5) Uani 1 1 d . . . . .
H10 H 0.704153 0.673229 0.828690 0.076 Uiso 1 1 calc R U . . .
C11 C 0.59452(13) 0.61607(15) 0.67454(17) 0.0626(4) Uani 1 1 d . . . . .
H11 H 0.641770 0.556213 0.653983 0.075 Uiso 1 1 calc R U . . .
C12 C 0.48863(12) 0.63346(13) 0.59990(15) 0.0538(4) Uani 1 1 d . . . . .
H12 H 0.464170 0.585663 0.528461 0.065 Uiso 1 1 calc R U . . .
C13 C 0.24034(11) 0.64763(11) 0.49930(12) 0.0423(3) Uani 1 1 d . . . . .
C14 C 0.23737(12) 0.54439(12) 0.56929(13) 0.0476(3) Uani 1 1 d . . . . .
H14 H 0.283561 0.537876 0.650431 0.057 Uiso 1 1 calc R U . . .
C15 C 0.16806(12) 0.45291(12) 0.52103(14) 0.0477(3) Uani 1 1 d . . . . .
H15 H 0.167786 0.383807 0.568967 0.057 Uiso 1 1 calc R U . . .
C16 C 0.09792(12) 0.46080(11) 0.40187(14) 0.0461(3) Uani 1 1 d . . . . .
C17 C 0.10010(12) 0.56351(12) 0.33348(14) 0.0495(3) Uani 1 1 d . . . . .
H17 H 0.052419 0.570427 0.253224 0.059 Uiso 1 1 calc R U . . .
C18 C 0.17030(11) 0.65561(12) 0.38011(13) 0.0472(3) Uani 1 1 d . . . . .
H18 H 0.171012 0.724148 0.331381 0.057 Uiso 1 1 calc R U . . .
C19 C 0.02204(13) 0.36590(13) 0.34947(17) 0.0583(4) Uani 1 1 d . . . . .
H19 H -0.026029 0.379469 0.270543 0.070 Uiso 1 1 calc R U . . .
C2 C 0.36109(12) 0.92264(12) 0.45383(13) 0.0482(3) Uani 1 1 d . . . . .
H2 H 0.431792 0.889696 0.448483 0.058 Uiso 1 1 calc R U . . .
C3 C 0.33463(13) 1.03543(13) 0.41107(14) 0.0527(4) Uani 1 1 d . . . . .
H3 H 0.387594 1.079346 0.376896 0.063 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2065(18) . ?
N1 C13 1.3929(16) . ?
N1 C7 1.4198(17) . ?
N1 C1 1.4249(16) . ?
C1 C2 1.3781(19) . ?
C1 C6 1.3824(19) . ?
C4 C5 1.367(2) . ?
C4 C3 1.376(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.3770(19) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.3734(19) . ?
C7 C12 1.379(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.363(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.375(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3903(19) . ?
C13 C14 1.3986(18) . ?
C14 C15 1.3663(19) . ?
C14 H14 0.9400 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.3830(19) . ?
C16 C19 1.450(2) . ?
C17 C18 1.3730(19) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C2 C3 1.376(2) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?

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
C13 N1 C7 120.91(10) . . ?
C13 N1 C1 120.16(10) . . ?
C7 N1 C1 118.16(10) . . ?
C2 C1 C6 119.55(13) . . ?
C2 C1 N1 120.55(12) . . ?
C6 C1 N1 119.90(12) . . ?
C5 C4 C3 119.32(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.94(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.65(13) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 119.25(13) . . ?
C8 C7 N1 120.40(13) . . ?
C12 C7 N1 120.31(12) . . ?
C7 C8 C9 119.63(15) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.74(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.38(14) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.50(16) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.50(15) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C18 C13 N1 120.84(12) . . ?
C18 C13 C14 118.53(12) . . ?
N1 C13 C14 120.61(12) . . ?
C15 C14 C13 120.73(13) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.79(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.34(12) . . ?
C17 C16 C19 119.76(13) . . ?
C15 C16 C19 121.89(13) . . ?
C18 C17 C16 121.52(13) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 120.08(13) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C16 126.00(16) . . ?
O1 C19 H19 117.0 . . ?
C16 C19 H19 117.0 . . ?
C3 C2 C1 120.06(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.48(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C2 -122.44(14) . . . . ?
C7 N1 C1 C2 47.59(18) . . . . ?
C13 N1 C1 C6 58.08(18) . . . . ?
C7 N1 C1 C6 -131.88(14) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
N1 C1 C6 C5 -179.53(12) . . . . ?
C13 N1 C7 C8 -139.32(14) . . . . ?
C1 N1 C7 C8 50.72(18) . . . . ?
C13 N1 C7 C12 43.04(19) . . . . ?
C1 N1 C7 C12 -126.91(15) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
N1 C7 C8 C9 -177.38(13) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C7 -0.3(2) . . . . ?
C8 C7 C12 C11 0.0(2) . . . . ?
N1 C7 C12 C11 177.62(14) . . . . ?
C7 N1 C13 C18 -146.65(13) . . . . ?
C1 N1 C13 C18 23.1(2) . . . . ?
C7 N1 C13 C14 34.53(19) . . . . ?
C1 N1 C13 C14 -155.72(13) . . . . ?
C18 C13 C14 C15 0.7(2) . . . . ?
N1 C13 C14 C15 179.54(12) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C14 C15 C16 C19 -178.82(14) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C19 C16 C17 C18 179.64(14) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
N1 C13 C18 C17 -178.75(13) . . . . ?
C14 C13 C18 C17 0.1(2) . . . . ?
C17 C16 C19 O1 177.52(15) . . . . ?
C15 C16 C19 O1 -3.7(3) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
N1 C1 C2 C3 -179.99(12) . . . . ?
C5 C4 C3 C2 0.5(2) . . . . ?
C1 C2 C3 C4 -0.3(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
C6 H6 O1 0.94 2.46 3.3857(19) 168.5 3_566 yes

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038























