# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_230522lt2_auto
_database_code_depnum_ccdc_archive 'CCDC 2283773'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-07-23 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-05-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 N2'
_chemical_formula_sum            'C17 H10 N2'
_chemical_formula_weight         242.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.50440(10)
_cell_length_b                   12.6636(5)
_cell_length_c                   19.6473(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1120.72(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      71.0840
_cell_measurement_theta_min      3.4820
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12127
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         4.153
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     52.00 104.00   0.50    0.76    --   80.07  15.00 150.00  104
  2  ω     55.00 124.00   0.50    0.76    --   80.07  15.00  30.00  138
  3  ω     42.00  89.00   0.50    0.76    --   70.49   0.00 -30.00   94
  4  ω     62.00 119.00   0.50    0.76    --   74.85  15.00-120.00  114
  5  ω     50.00  79.00   0.50    0.76    --   74.85   0.00 -30.00   58
  6  ω     26.00  80.00   0.50    0.76    --   61.96   0.00  30.00  108
  7  ω     31.00  97.00   0.50    0.76    --   61.96   0.00  90.00  132
  8  ω     37.00  95.00   0.50    0.76    --   61.96   0.00 150.00  116
  9  ω     29.00  55.00   0.50    0.76    --   61.96 -95.00 150.00   52
 10  ω     37.00  62.00   0.50    0.76    --   74.85-125.00 150.00   50
 11  ω     65.00  99.00   0.50    0.76    --   70.49-125.00 -30.00   68
 12  ω     39.00  67.00   0.50    0.76    --   80.07-125.00-150.00   56
 13  ω     30.00  56.00   0.50    0.76    --   70.49-125.00 -30.00   52
 14  ω     37.00 108.00   0.50    0.76    --   80.07-125.00-180.00  142
 15  ω     84.00 109.00   0.50    0.76    --   80.07-125.00 -60.00   50
 16  ω     83.00 108.00   0.50    0.76    --   80.07-125.00-150.00   50
 17  ω     38.00  67.00   0.50    0.76    --   80.07-125.00 -60.00   58
 18  ω     34.00  59.00   0.50    0.76    --   70.49-106.00  66.00   50
 19  ω     43.00  68.00   0.50    0.76    --   80.07-106.00  66.00   50
 20  ω     24.00  52.00   0.50    0.76    --   61.96 -95.00  90.00   56
 21  ω     24.00  67.00   0.50    0.76    --   61.96-106.00  66.00   86
 22  ω     73.00 109.00   0.50    0.76    --   80.07-125.00 120.00   72
 23  ω     40.00  65.00   0.50    0.76    --   80.07-125.00 120.00   50
 24  ω     32.00  66.00   0.50    0.76    --   61.96 -95.00 120.00   68
 25  ω     53.00  78.00   0.50    0.76    --   74.85 -95.00   0.00   50
 26  ω     46.00  73.00   0.50    0.76    --   74.85 -95.00 -60.00   54
 27  ω     32.00  63.00   0.50    0.76    --   61.96 -95.00-120.00   62
 28  ω     64.00  89.00   0.50    0.76    --   80.07 -95.00-150.00   50
 29  ω     79.00 104.00   0.50    0.76    --   80.07 125.00  90.00   50
 30  ω    -90.00 -65.00   0.50    0.76    --  -77.57 106.00 165.00   50
 31  ω    -65.00 -28.00   0.50    0.76    --  -64.74 106.00 165.00   74
 32  ω    -68.00 -42.00   0.50    0.76    --  -74.46 106.00 165.00   52
 33  ω    -99.00 -34.00   0.50    0.76    --  -77.57 125.00   0.00  130
 34  ω    -63.00 -37.00   0.50    0.76    --  -74.46 125.00 -60.00   52
 35  ω   -103.00 -78.00   0.50    0.76    --  -74.46 125.00 -60.00   50
 36  ω   -121.00 -93.00   0.50    0.76    --  -77.57-125.00  30.00   56
 37  ω   -119.00 -78.00   0.50    0.76    --  -77.57-125.00  90.00   82
 38  ω   -118.00 -80.00   0.50    0.76    --  -77.57-125.00   0.00   76
 39  ω   -106.00 -74.00   0.50    0.76    --  -77.57-125.00-150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1069165000
_diffrn_orient_matrix_UB_12      -0.0515838000
_diffrn_orient_matrix_UB_13      -0.0667135000
_diffrn_orient_matrix_UB_21      0.0383469000
_diffrn_orient_matrix_UB_22      0.1060613000
_diffrn_orient_matrix_UB_23      -0.0372313000
_diffrn_orient_matrix_UB_31      0.3225682000
_diffrn_orient_matrix_UB_32      -0.0297613000
_diffrn_orient_matrix_UB_33      -0.0177265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1836
_reflns_number_total             2008
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.3(13)
_refine_ls_extinction_coef       0.0032(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0919P)²+0.3346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1530
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.3(13)
 -0.3(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5149(8) 0.5503(3) 0.69194(18) 0.0297(8) Uani 1 1 d . . . . .
C2 C 0.7189(8) 0.5199(3) 0.74484(19) 0.0304(9) Uani 1 1 d . . . . .
C3 C 0.8483(8) 0.4167(3) 0.74059(17) 0.0302(9) Uani 1 1 d . . . . .
C4 C 0.7738(8) 0.3439(3) 0.68715(18) 0.0327(8) Uani 1 1 d . . . . .
H4 H 0.861562 0.275747 0.686018 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5752(8) 0.3735(3) 0.63779(17) 0.0279(8) Uani 1 1 d . . . . .
C7 C 0.2923(9) 0.3486(3) 0.53994(18) 0.0347(9) Uani 1 1 d . . . . .
H7 H 0.234235 0.304171 0.503339 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1638(8) 0.4527(3) 0.54294(17) 0.0308(9) Uani 1 1 d . . . . .
C9 C -0.0411(8) 0.5020(3) 0.50006(19) 0.0347(9) Uani 1 1 d . . . . .
H9 H -0.118975 0.465925 0.461614 0.042 Uiso 1 1 calc R U . . .
C10 C -0.1301(9) 0.6060(3) 0.5148(2) 0.0381(10) Uani 1 1 d . . . . .
H10 H -0.268565 0.639192 0.485209 0.046 Uiso 1 1 calc R U . . .
C11 C -0.0248(8) 0.6632(3) 0.57087(18) 0.0354(9) Uani 1 1 d . . . . .
H11 H -0.092953 0.732948 0.579297 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1842(7) 0.6154(3) 0.61466(18) 0.0300(8) Uani 1 1 d . . . . .
C13 C 0.2599(8) 0.5129(3) 0.59691(18) 0.0305(8) Uani 1 1 d . . . . .
C15 C 0.7937(8) 0.5860(3) 0.79931(18) 0.0344(9) Uani 1 1 d . . . . .
H15 H 0.705008 0.653878 0.802648 0.041 Uiso 1 1 calc R U . . .
C16 C 0.9934(9) 0.5542(3) 0.84800(19) 0.0385(9) Uani 1 1 d . . . . .
H16 H 1.043380 0.600205 0.884412 0.046 Uiso 1 1 calc R U . . .
C17 C 1.1223(9) 0.4548(3) 0.84407(19) 0.0395(10) Uani 1 1 d . . . . .
H17 H 1.259930 0.433146 0.877951 0.047 Uiso 1 1 calc R U . . .
C18 C 1.0533(8) 0.3881(3) 0.79220(18) 0.0342(9) Uani 1 1 d . . . . .
H18 H 1.144749 0.320509 0.790470 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3484(8) 0.6396(3) 0.67565(18) 0.0310(8) Uani 1 1 d . . . . .
H19 H 0.344043 0.704208 0.700146 0.037 Uiso 1 1 calc R U . . .
N6 N 0.4848(7) 0.3104(3) 0.58426(15) 0.0346(8) Uani 1 1 d . . . . .
N14 N 0.4611(7) 0.4741(2) 0.64329(15) 0.0289(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.440(5) . ?
C1 C19 1.393(5) . ?
C1 N14 1.380(5) . ?
C2 C3 1.433(5) . ?
C2 C15 1.400(5) . ?
C3 C4 1.437(5) . ?
C3 C18 1.419(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(5) . ?
C5 N6 1.382(4) . ?
C5 N14 1.379(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.440(6) . ?
C7 N6 1.321(5) . ?
C8 C9 1.397(5) . ?
C8 C13 1.376(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.407(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.401(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.412(5) . ?
C12 C13 1.387(5) . ?
C12 C19 1.441(5) . ?
C13 N14 1.376(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.360(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 C1 C2 136.6(3) . . ?
N14 C1 C2 115.1(3) . . ?
N14 C1 C19 108.3(3) . . ?
C3 C2 C1 117.5(3) . . ?
C15 C2 C1 123.1(4) . . ?
C15 C2 C3 119.5(3) . . ?
C2 C3 C4 122.2(3) . . ?
C18 C3 C2 117.2(3) . . ?
C18 C3 C4 120.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 N6 125.0(3) . . ?
C4 C5 N14 116.1(3) . . ?
N14 C5 N6 119.0(3) . . ?
C8 C7 H7 117.6 . . ?
N6 C7 H7 117.6 . . ?
N6 C7 C8 124.9(3) . . ?
C9 C8 C7 130.5(4) . . ?
C13 C8 C7 114.3(3) . . ?
C13 C8 C9 115.2(4) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.9(4) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 118.4 . . ?
C11 C10 C9 123.3(4) . . ?
C11 C10 H10 118.4 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.9(4) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C19 139.3(4) . . ?
C13 C12 C11 114.3(3) . . ?
C13 C12 C19 106.4(3) . . ?
C8 C13 C12 129.4(3) . . ?
C8 C13 N14 121.4(3) . . ?
N14 C13 C12 109.2(3) . . ?
C2 C15 H15 119.5 . . ?
C16 C15 C2 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C3 C18 H18 119.2 . . ?
C17 C18 C3 121.7(4) . . ?
C17 C18 H18 119.2 . . ?
C1 C19 C12 107.2(3) . . ?
C1 C19 H19 126.4 . . ?
C12 C19 H19 126.4 . . ?
C7 N6 C5 118.9(3) . . ?
C5 N14 C1 129.5(3) . . ?
C13 N14 C1 109.0(3) . . ?
C13 N14 C5 121.6(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
C1 C2 C3 C4 -1.8(5) . . . . ?
C1 C2 C3 C18 178.9(3) . . . . ?
C1 C2 C15 C16 -178.9(3) . . . . ?
C2 C1 C19 C12 -179.2(4) . . . . ?
C2 C1 N14 C5 -0.3(5) . . . . ?
C2 C1 N14 C13 179.0(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C2 C3 C18 C17 0.8(5) . . . . ?
C2 C15 C16 C17 -0.6(6) . . . . ?
C3 C2 C15 C16 1.2(5) . . . . ?
C3 C4 C5 N6 -179.6(3) . . . . ?
C3 C4 C5 N14 0.5(5) . . . . ?
C4 C3 C18 C17 -178.5(3) . . . . ?
C4 C5 N6 C7 -179.8(4) . . . . ?
C4 C5 N14 C1 -0.7(5) . . . . ?
C4 C5 N14 C13 -180.0(3) . . . . ?
C7 C8 C9 C10 -179.8(4) . . . . ?
C7 C8 C13 C12 179.5(3) . . . . ?
C7 C8 C13 N14 -0.3(5) . . . . ?
C8 C7 N6 C5 -0.4(5) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C8 C13 N14 C1 -179.4(3) . . . . ?
C8 C13 N14 C5 0.0(5) . . . . ?
C9 C8 C13 C12 -0.4(6) . . . . ?
C9 C8 C13 N14 179.8(3) . . . . ?
C9 C10 C11 C12 0.9(6) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C10 C11 C12 C19 -179.5(4) . . . . ?
C11 C12 C13 C8 0.9(5) . . . . ?
C11 C12 C13 N14 -179.3(3) . . . . ?
C11 C12 C19 C1 178.4(4) . . . . ?
C12 C13 N14 C1 0.8(4) . . . . ?
C12 C13 N14 C5 -179.8(3) . . . . ?
C13 C8 C9 C10 0.1(5) . . . . ?
C13 C12 C19 C1 -0.2(4) . . . . ?
C15 C2 C3 C4 178.0(3) . . . . ?
C15 C2 C3 C18 -1.3(5) . . . . ?
C15 C16 C17 C18 0.1(6) . . . . ?
C16 C17 C18 C3 -0.2(6) . . . . ?
C18 C3 C4 C5 -180.0(3) . . . . ?
C19 C1 C2 C3 -178.6(4) . . . . ?
C19 C1 C2 C15 1.5(7) . . . . ?
C19 C1 N14 C5 179.8(3) . . . . ?
C19 C1 N14 C13 -0.9(4) . . . . ?
C19 C12 C13 C8 179.8(4) . . . . ?
C19 C12 C13 N14 -0.4(4) . . . . ?
N6 C5 N14 C1 179.4(3) . . . . ?
N6 C5 N14 C13 0.1(5) . . . . ?
N6 C7 C8 C9 -179.6(4) . . . . ?
N6 C7 C8 C13 0.5(5) . . . . ?
N14 C1 C2 C3 1.6(5) . . . . ?
N14 C1 C2 C15 -178.3(3) . . . . ?
N14 C1 C19 C12 0.6(4) . . . . ?
N14 C5 N6 C7 0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.668
_oxdiff_exptl_absorpt_empirical_full_min 0.493
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.3(13)
2 -0.3(13)

####################################################################### 
# 
# 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_230766lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2288008'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 N2 O'
_chemical_formula_sum            'C24 H14 N2 O'
_chemical_formula_weight         346.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.67160(10)
_cell_length_b                   9.16801(15)
_cell_length_c                   12.73071(19)
_cell_angle_alpha                106.1712(14)
_cell_angle_beta                 91.1629(11)
_cell_angle_gamma                109.9674(13)
_cell_volume                     801.64(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5872
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5450
_cell_measurement_theta_min      5.3630
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8120
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.754
_diffrn_reflns_theta_min         5.388
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00 -30.00   0.50    0.05    --  -75.32 111.00  90.00   84
  2  ω    -52.00 -26.00   0.50    0.05    --  -72.13 125.00  60.00   52
  3  ω    -97.00 -34.00   0.50    0.05    --  -79.90 114.00  22.16  126
  4  ω    -62.00 -29.00   0.50    0.05    --  -72.13 125.00   0.00   66
  5  ω    -93.00 -35.00   0.50    0.05    --  -79.90 104.00-178.33  116
  6  ω   -126.00 -42.00   0.50    0.05    --  -75.32 -15.00-150.00  168
  7  ω    -87.00 -36.00   0.50    0.05    --  -59.44 -15.00-120.00  102
  8  ω   -124.00 -40.00   0.50    0.05    --  -75.32 -15.00 120.00  168
  9  ω    -86.00 -37.00   0.50    0.05    --  -59.44 -15.00 120.00   98
 10  ω     23.00  58.00   0.50    0.05    --   56.25-125.00  60.00   70
 11  ω     39.00  64.00   0.50    0.05    --   83.87-111.00  30.00   50
 12  ω     27.00  52.00   0.50    0.05    --   69.31 -95.00 -30.00   50
 13  ω     37.00  82.00   0.50    0.05    --   75.94 -95.00 -30.00   90
 14  ω     34.00  72.00   0.50    0.05    --   75.94 -95.00 -60.00   76
 15  ω     41.00  81.00   0.50    0.05    --   75.94 -95.00-120.00   80
 16  ω     66.00  91.00   0.50    0.05    --   83.87 -95.00-120.00   50
 17  ω     30.00  63.00   0.50    0.05    --   69.31 -95.00-180.00   66
 18  ω     31.00  57.00   0.50    0.05    --   75.94-111.00-150.00   52
 19  ω     14.00  42.00   0.50    0.05    --   56.25 -95.00 -90.00   56
 20  ω     41.00  92.00   0.50    0.05    --   83.87 -95.00 -90.00  102
 21  ω     62.00  92.00   0.50    0.05    --   83.87 -95.00 -30.00   60
 22  ω     41.00  67.00   0.50    0.05    --   83.87 -95.00  30.00   52
 23  ω     48.00  90.00   0.50    0.05    --   83.87 -95.00  90.00   84
 24  ω     54.00  91.00   0.50    0.05    --   83.87 -95.00 120.00   74
 25  ω     54.00  90.00   0.50    0.05    --   83.87 -95.00 150.00   72
 26  ω     49.00 133.00   0.50    0.05    --   83.87  15.00 150.00  168
 27  ω     48.00 132.00   0.50    0.05    --   83.87  15.00  60.00  168
 28  ω     75.00 116.00   0.50    0.05    --   83.87  15.00 -60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0361295000
_diffrn_orient_matrix_UB_12      -0.1838452000
_diffrn_orient_matrix_UB_13      -0.0387809000
_diffrn_orient_matrix_UB_21      0.0767700000
_diffrn_orient_matrix_UB_22      0.0155732000
_diffrn_orient_matrix_UB_23      -0.1088476000
_diffrn_orient_matrix_UB_31      0.1980123000
_diffrn_orient_matrix_UB_32      0.0342211000
_diffrn_orient_matrix_UB_33      0.0527934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2922
_reflns_number_total             3101
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.2909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39270(15) 1.14813(14) 0.48066(9) 0.0184(2) Uani 1 1 d . . . . .
C2 C 0.35442(15) 1.00838(14) 0.38624(9) 0.0193(2) Uani 1 1 d . . . . .
C3 C 0.22772(16) 0.85083(14) 0.38431(10) 0.0206(3) Uani 1 1 d . . . . .
H3 H 0.207622 0.759453 0.321227 0.025 Uiso 1 1 calc R U . . .
C4 C 0.13613(15) 0.83211(14) 0.47292(10) 0.0193(2) Uani 1 1 d . . . . .
C6 C -0.06353(16) 0.67993(14) 0.57060(10) 0.0223(3) Uani 1 1 d . . . . .
H6 H -0.146584 0.577365 0.573484 0.027 Uiso 1 1 calc R U . . .
C7 C -0.02844(16) 0.81986(14) 0.66714(10) 0.0206(3) Uani 1 1 d . . . . .
C8 C -0.09907(16) 0.83002(14) 0.76768(10) 0.0224(3) Uani 1 1 d . . . . .
H8 H -0.187151 0.736625 0.780401 0.027 Uiso 1 1 calc R U . . .
C9 C -0.03695(17) 0.98176(15) 0.84993(10) 0.0239(3) Uani 1 1 d . . . . .
H9 H -0.086459 0.988279 0.918170 0.029 Uiso 1 1 calc R U . . .
C10 C 0.09345(16) 1.12374(14) 0.83725(10) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.132799 1.222843 0.896121 0.026 Uiso 1 1 calc R U . . .
C11 C 0.16595(15) 1.11762(14) 0.73539(10) 0.0195(2) Uani 1 1 d . . . . .
C12 C 0.09689(15) 0.96443(14) 0.65713(9) 0.0190(2) Uani 1 1 d . . . . .
C14 C 0.30416(15) 1.12647(13) 0.57695(9) 0.0182(2) Uani 1 1 d . . . . .
C15 C 0.44532(16) 1.02763(15) 0.29282(10) 0.0217(3) Uani 1 1 d . . . . .
H15 H 0.423032 0.935119 0.230230 0.026 Uiso 1 1 calc R U . . .
C16 C 0.56489(17) 1.17677(15) 0.29052(10) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.625045 1.186916 0.227036 0.028 Uiso 1 1 calc R U . . .
C17 C 0.59817(16) 1.31456(15) 0.38236(10) 0.0227(3) Uani 1 1 d . . . . .
H17 H 0.679352 1.418246 0.380281 0.027 Uiso 1 1 calc R U . . .
C18 C 0.51394(16) 1.30043(14) 0.47542(10) 0.0208(3) Uani 1 1 d . . . . .
H18 H 0.537891 1.394674 0.536943 0.025 Uiso 1 1 calc R U . . .
C19 C 0.30212(15) 1.22234(14) 0.68512(9) 0.0191(2) Uani 1 1 d . . . . .
C20 C 0.43400(16) 1.38767(13) 0.74395(9) 0.0188(2) Uani 1 1 d . . . . .
C22 C 0.36742(16) 1.49674(14) 0.83041(9) 0.0208(3) Uani 1 1 d . . . . .
C23 C 0.18327(17) 1.49010(14) 0.82060(10) 0.0243(3) Uani 1 1 d . . . . .
H23 H 0.095779 1.410686 0.760403 0.029 Uiso 1 1 calc R U . . .
C24 C 0.12750(18) 1.59934(16) 0.89867(11) 0.0293(3) Uani 1 1 d . . . . .
H24 H 0.002071 1.594795 0.891742 0.035 Uiso 1 1 calc R U . . .
C25 C 0.2550(2) 1.71502(17) 0.98672(11) 0.0335(3) Uani 1 1 d . . . . .
H25 H 0.216179 1.788671 1.040614 0.040 Uiso 1 1 calc R U . . .
C26 C 0.43898(19) 1.72360(17) 0.99640(11) 0.0315(3) Uani 1 1 d . . . . .
H26 H 0.526162 1.803531 1.056548 0.038 Uiso 1 1 calc R U . . .
C27 C 0.49555(17) 1.61551(15) 0.91829(10) 0.0243(3) Uani 1 1 d . . . . .
H27 H 0.621875 1.622269 0.924573 0.029 Uiso 1 1 calc R U . . .
N5 N 0.01136(14) 0.68545(12) 0.48000(8) 0.0224(2) Uani 1 1 d . . . . .
N13 N 0.17695(13) 0.97068(11) 0.56318(8) 0.0181(2) Uani 1 1 d . . . . .
O21 O 0.59825(11) 1.43798(10) 0.72586(7) 0.0254(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.4295(16) . ?
C1 C14 1.4426(15) . ?
C1 C18 1.4095(16) . ?
C2 C3 1.4325(16) . ?
C2 C15 1.4136(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3614(17) . ?
C4 N5 1.3871(15) . ?
C4 N13 1.3903(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.4496(17) . ?
C6 N5 1.3049(16) . ?
C7 C8 1.3916(16) . ?
C7 C12 1.3879(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.4051(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3984(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.4156(16) . ?
C11 C12 1.3917(16) . ?
C11 C19 1.4516(16) . ?
C12 N13 1.3620(14) . ?
C14 C19 1.4161(15) . ?
C14 N13 1.3873(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.3707(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.4046(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3774(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.4736(15) . ?
C20 C22 1.4936(15) . ?
C20 O21 1.2359(14) . ?
C22 C23 1.3946(17) . ?
C22 C27 1.3962(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.3890(17) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.3862(17) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C14 118.22(10) . . ?
C18 C1 C2 118.75(10) . . ?
C18 C1 C14 123.03(10) . . ?
C1 C2 C3 121.81(11) . . ?
C15 C2 C1 118.56(11) . . ?
C15 C2 C3 119.63(10) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.97(11) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 N5 124.74(11) . . ?
C3 C4 N13 116.56(10) . . ?
N5 C4 N13 118.67(10) . . ?
C7 C6 H6 117.8 . . ?
N5 C6 H6 117.8 . . ?
N5 C6 C7 124.37(11) . . ?
C8 C7 C6 129.86(11) . . ?
C12 C7 C6 114.30(11) . . ?
C12 C7 C8 115.83(11) . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.40(11) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 118.1 . . ?
C10 C9 C8 123.86(11) . . ?
C10 C9 H9 118.1 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.02(11) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C19 139.65(11) . . ?
C12 C11 C10 114.19(10) . . ?
C12 C11 C19 106.07(10) . . ?
C7 C12 C11 128.67(11) . . ?
N13 C12 C7 121.61(11) . . ?
N13 C12 C11 109.68(10) . . ?
C19 C14 C1 138.19(11) . . ?
N13 C14 C1 114.62(10) . . ?
N13 C14 C19 107.12(10) . . ?
C2 C15 H15 119.3 . . ?
C16 C15 C2 121.48(11) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.77(11) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.47(11) . . ?
C18 C17 H17 119.8 . . ?
C1 C18 H18 119.5 . . ?
C17 C18 C1 120.93(11) . . ?
C17 C18 H18 119.5 . . ?
C11 C19 C20 125.02(10) . . ?
C14 C19 C11 107.06(10) . . ?
C14 C19 C20 127.13(10) . . ?
C19 C20 C22 118.61(10) . . ?
O21 C20 C19 122.42(10) . . ?
O21 C20 C22 118.95(10) . . ?
C23 C22 C20 121.19(11) . . ?
C23 C22 C27 119.46(11) . . ?
C27 C22 C20 119.18(11) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.14(12) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.98(12) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.23(12) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.98(12) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.19(12) . . ?
C26 C27 H27 119.9 . . ?
C6 N5 C4 119.75(10) . . ?
C12 N13 C4 121.29(10) . . ?
C12 N13 C14 110.04(9) . . ?
C14 N13 C4 128.57(10) . . ?

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
C1 C2 C3 C4 1.80(17) . . . . ?
C1 C2 C15 C16 -1.38(17) . . . . ?
C1 C14 C19 C11 175.99(13) . . . . ?
C1 C14 C19 C20 -13.8(2) . . . . ?
C1 C14 N13 C4 5.71(17) . . . . ?
C1 C14 N13 C12 -177.96(9) . . . . ?
C2 C1 C14 C19 178.33(13) . . . . ?
C2 C1 C14 N13 -5.11(15) . . . . ?
C2 C1 C18 C17 -1.63(17) . . . . ?
C2 C3 C4 N5 -179.73(10) . . . . ?
C2 C3 C4 N13 -1.74(16) . . . . ?
C2 C15 C16 C17 -0.33(18) . . . . ?
C3 C2 C15 C16 178.78(10) . . . . ?
C3 C4 N5 C6 177.40(11) . . . . ?
C3 C4 N13 C12 -178.21(10) . . . . ?
C3 C4 N13 C14 -2.25(17) . . . . ?
C6 C7 C8 C9 177.96(11) . . . . ?
C6 C7 C12 C11 -177.03(11) . . . . ?
C6 C7 C12 N13 0.42(16) . . . . ?
C7 C6 N5 C4 1.20(17) . . . . ?
C7 C8 C9 C10 -0.58(18) . . . . ?
C7 C12 N13 C4 0.12(17) . . . . ?
C7 C12 N13 C14 -176.52(10) . . . . ?
C8 C7 C12 C11 2.13(18) . . . . ?
C8 C7 C12 N13 179.58(10) . . . . ?
C8 C9 C10 C11 1.37(18) . . . . ?
C9 C10 C11 C12 -0.45(16) . . . . ?
C9 C10 C11 C19 -176.40(13) . . . . ?
C10 C11 C12 C7 -1.35(18) . . . . ?
C10 C11 C12 N13 -179.04(9) . . . . ?
C10 C11 C19 C14 177.68(14) . . . . ?
C10 C11 C19 C20 7.3(2) . . . . ?
C11 C12 N13 C4 178.01(10) . . . . ?
C11 C12 N13 C14 1.37(13) . . . . ?
C11 C19 C20 C22 -39.14(16) . . . . ?
C11 C19 C20 O21 139.41(12) . . . . ?
C12 C7 C8 C9 -1.05(16) . . . . ?
C12 C11 C19 C14 1.52(12) . . . . ?
C12 C11 C19 C20 -168.90(11) . . . . ?
C14 C1 C2 C3 1.84(16) . . . . ?
C14 C1 C2 C15 -177.99(10) . . . . ?
C14 C1 C18 C17 178.70(10) . . . . ?
C14 C19 C20 C22 152.37(11) . . . . ?
C14 C19 C20 O21 -29.08(18) . . . . ?
C15 C2 C3 C4 -178.37(10) . . . . ?
C15 C16 C17 C18 1.09(18) . . . . ?
C16 C17 C18 C1 -0.08(18) . . . . ?
C18 C1 C2 C3 -177.84(10) . . . . ?
C18 C1 C2 C15 2.33(16) . . . . ?
C18 C1 C14 C19 -2.0(2) . . . . ?
C18 C1 C14 N13 174.56(10) . . . . ?
C19 C11 C12 C7 175.92(11) . . . . ?
C19 C11 C12 N13 -1.77(13) . . . . ?
C19 C14 N13 C4 -176.69(10) . . . . ?
C19 C14 N13 C12 -0.36(12) . . . . ?
C19 C20 C22 C23 -33.75(16) . . . . ?
C19 C20 C22 C27 151.07(11) . . . . ?
C20 C22 C23 C24 -176.13(11) . . . . ?
C20 C22 C27 C26 176.65(11) . . . . ?
C22 C23 C24 C25 -0.16(19) . . . . ?
C23 C22 C27 C26 1.39(18) . . . . ?
C23 C24 C25 C26 0.9(2) . . . . ?
C24 C25 C26 C27 -0.5(2) . . . . ?
C25 C26 C27 C22 -0.7(2) . . . . ?
C27 C22 C23 C24 -0.96(18) . . . . ?
N5 C4 N13 C12 -0.10(16) . . . . ?
N5 C4 N13 C14 175.87(10) . . . . ?
N5 C6 C7 C8 179.87(11) . . . . ?
N5 C6 C7 C12 -1.12(17) . . . . ?
N13 C4 N5 C6 -0.55(16) . . . . ?
N13 C14 C19 C11 -0.73(12) . . . . ?
N13 C14 C19 C20 169.43(10) . . . . ?
O21 C20 C22 C23 147.65(11) . . . . ?
O21 C20 C22 C27 -27.53(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_231020lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2301524'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-10-16 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-10-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H14 N2'
_chemical_formula_sum            'C25 H14 N2'
_chemical_formula_weight         342.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.78180(10)
_cell_length_b                   12.8402(3)
_cell_length_c                   21.6872(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1610.05(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4593
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.0390
_cell_measurement_theta_min      6.8820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9467
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.793
_diffrn_reflns_theta_min         4.001
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 121.00   0.50    0.38    --   83.87  15.00   0.00   52
  2  ω     48.00  92.00   0.50    0.38    --   83.87  15.00   0.00   88
  3  ω     41.00  86.00   0.50    0.38    --   56.25  15.00 -60.00   90
  4  ω     74.00 120.00   0.50    0.38    --   83.87  15.00-120.00   92
  5  ω     48.00  85.00   0.50    0.38    --   83.87 -95.00 -60.00   74
  6  ω     64.00  99.00   0.50    0.38    --   75.94-123.00 -47.00   70
  7  ω     32.00  57.00   0.50    0.38    --   56.25-128.00  45.00   50
  8  ω     36.00  61.00   0.50    0.38    --   69.31-128.00  45.00   50
  9  ω     45.00  70.00   0.50    0.38    --   83.87-128.00  45.00   50
 10  ω     52.00 101.00   0.50    0.38    --   75.94-128.00  45.00   98
 11  ω     31.00  56.00   0.50    0.38    --   56.25-123.00 -47.00   50
 12  ω     25.00  61.00   0.50    0.38    --   69.31-123.00 -47.00   72
 13  ω     44.00  69.00   0.50    0.38    --   83.87-123.00 -47.00   50
 14  ω     33.00  81.00   0.50    0.38    --   75.94 -95.00-150.00   96
 15  ω     18.00  44.00   0.50    0.38    --   56.25 -95.00 -60.00   52
 16  ω   -126.00 -86.00   0.50    0.38    --  -75.32 -15.00   0.00   80
 17  ω    -82.00 -40.00   0.50    0.38    --  -75.32 -15.00   0.00   84
 18  ω    -71.00 -46.00   0.50    0.38    --  -72.13 128.00 120.00   50
 19  ω    -89.00 -64.00   0.50    0.38    --  -75.32 128.00 120.00   50
 20  ω    -54.00 -16.00   0.50    0.38    --  -59.44 128.00 120.00   76
 21  ω    -73.00 -48.00   0.50    0.38    --  -59.44 123.00  33.00   50
 22  ω    -88.00 -63.00   0.50    0.38    --  -75.32 123.00  33.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0274257000
_diffrn_orient_matrix_UB_12      0.0151242000
_diffrn_orient_matrix_UB_13      0.0701064000
_diffrn_orient_matrix_UB_21      -0.0105358000
_diffrn_orient_matrix_UB_22      0.1188605000
_diffrn_orient_matrix_UB_23      -0.0092943000
_diffrn_orient_matrix_UB_31      -0.2647243000
_diffrn_orient_matrix_UB_32      -0.0063614000
_diffrn_orient_matrix_UB_33      -0.0069157000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.630
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                2665
_reflns_number_total             2997
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.8(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.1240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.2(8)
 0.8(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6845(4) 0.7104(2) 0.37516(11) 0.0269(5) Uani 1 1 d . . . . .
C2 C 0.5118(4) 0.7611(2) 0.40976(11) 0.0312(6) Uani 1 1 d . . . . .
H2 H 0.510168 0.834894 0.412829 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3442(5) 0.7021(2) 0.43933(11) 0.0311(6) Uani 1 1 d . . . . .
H3 H 0.228591 0.737915 0.462104 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3343(4) 0.5912(2) 0.43777(11) 0.0280(5) Uani 1 1 d . . . . .
C5 C 0.5083(4) 0.53901(19) 0.40461(11) 0.0274(5) Uani 1 1 d . . . . .
C6 C 0.5515(4) 0.4285(2) 0.39630(12) 0.0298(6) Uani 1 1 d . . . . .
H6 H 0.448908 0.381073 0.415888 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8754(4) 0.4547(2) 0.33410(12) 0.0283(5) Uani 1 1 d . . . . .
C9 C 1.0580(4) 0.4243(2) 0.29893(12) 0.0316(6) Uani 1 1 d . . . . .
H9 H 1.087933 0.352318 0.292785 0.038 Uiso 1 1 calc R U . . .
C10 C 1.2061(4) 0.5010(2) 0.27100(11) 0.0301(6) Uani 1 1 d . . . . .
C11 C 1.1687(4) 0.6097(2) 0.27951(11) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.9759(4) 0.6422(2) 0.31728(11) 0.0280(5) Uani 1 1 d . . . . .
C14 C 0.6688(4) 0.60167(19) 0.37533(10) 0.0262(5) Uani 1 1 d . . . . .
C15 C 0.8824(4) 0.7353(2) 0.33806(11) 0.0295(5) Uani 1 1 d . . . . .
H15 H 0.939085 0.803149 0.329319 0.035 Uiso 1 1 calc R U . . .
C16 C 1.3977(4) 0.4702(2) 0.23476(13) 0.0352(6) Uani 1 1 d . . . . .
H16 H 1.427218 0.398190 0.228492 0.042 Uiso 1 1 calc R U . . .
C17 C 1.5420(5) 0.5431(2) 0.20842(12) 0.0371(6) Uani 1 1 d . . . . .
H17 H 1.669739 0.520819 0.184201 0.045 Uiso 1 1 calc R U . . .
C18 C 1.5020(5) 0.6497(2) 0.21706(12) 0.0359(6) Uani 1 1 d . . . . .
H18 H 1.602288 0.699404 0.198702 0.043 Uiso 1 1 calc R U . . .
C19 C 1.3178(4) 0.6822(2) 0.25207(11) 0.0327(6) Uani 1 1 d . . . . .
H19 H 1.291209 0.754617 0.257756 0.039 Uiso 1 1 calc R U . . .
C20 C 0.1545(4) 0.5373(2) 0.46984(11) 0.0293(5) Uani 1 1 d . . . . .
C21 C 0.0027(4) 0.4951(2) 0.49844(11) 0.0296(5) Uani 1 1 d . . . . .
C22 C -0.1792(4) 0.4482(2) 0.53419(11) 0.0285(5) Uani 1 1 d . . . . .
C23 C -0.1853(4) 0.3406(2) 0.54418(12) 0.0330(6) Uani 1 1 d . . . . .
H23 H -0.065875 0.297534 0.528202 0.040 Uiso 1 1 calc R U . . .
C24 C -0.3652(4) 0.2968(2) 0.57732(13) 0.0359(6) Uani 1 1 d . . . . .
H24 H -0.369399 0.223604 0.583535 0.043 Uiso 1 1 calc R U . . .
C25 C -0.5388(4) 0.3584(2) 0.60146(12) 0.0348(6) Uani 1 1 d . . . . .
H25 H -0.661888 0.327640 0.624035 0.042 Uiso 1 1 calc R U . . .
C26 C -0.5327(4) 0.4651(2) 0.59267(12) 0.0334(6) Uani 1 1 d . . . . .
H26 H -0.650501 0.507676 0.609877 0.040 Uiso 1 1 calc R U . . .
C27 C -0.3555(4) 0.5100(2) 0.55886(11) 0.0306(5) Uani 1 1 d . . . . .
H27 H -0.353750 0.583144 0.552404 0.037 Uiso 1 1 calc R U . . .
N7 N 0.7209(4) 0.38941(17) 0.36387(10) 0.0311(5) Uani 1 1 d . . . . .
N13 N 0.8424(3) 0.56149(16) 0.34118(9) 0.0263(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.408(3) . ?
C1 C14 1.400(3) . ?
C1 C15 1.435(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.425(3) . ?
C4 C5 1.407(3) . ?
C4 C20 1.430(4) . ?
C5 C6 1.452(4) . ?
C5 C14 1.383(3) . ?
C6 H6 0.9500 . ?
C6 N7 1.306(3) . ?
C8 C9 1.360(4) . ?
C8 N7 1.385(3) . ?
C8 N13 1.393(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.438(4) . ?
C10 C11 1.425(4) . ?
C10 C16 1.415(4) . ?
C11 C12 1.445(3) . ?
C11 C19 1.402(4) . ?
C12 C15 1.387(4) . ?
C12 N13 1.392(3) . ?
C14 N13 1.350(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.378(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.401(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.373(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.203(4) . ?
C21 C22 1.439(3) . ?
C22 C23 1.399(4) . ?
C22 C27 1.398(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(4) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C15 139.6(2) . . ?
C14 C1 C2 114.4(2) . . ?
C14 C1 C15 106.0(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 117.9 . . ?
C2 C3 C4 124.2(2) . . ?
C4 C3 H3 117.9 . . ?
C3 C4 C20 120.1(2) . . ?
C5 C4 C3 117.3(2) . . ?
C5 C4 C20 122.5(2) . . ?
C4 C5 C6 130.7(2) . . ?
C14 C5 C4 116.0(2) . . ?
C14 C5 C6 113.3(2) . . ?
C5 C6 H6 117.6 . . ?
N7 C6 C5 124.8(2) . . ?
N7 C6 H6 117.6 . . ?
C9 C8 N7 126.1(2) . . ?
C9 C8 N13 116.8(2) . . ?
N7 C8 N13 117.1(2) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 121.7(2) . . ?
C16 C10 C9 120.6(2) . . ?
C16 C10 C11 117.7(2) . . ?
C10 C11 C12 118.3(2) . . ?
C19 C11 C10 120.2(2) . . ?
C19 C11 C12 121.5(2) . . ?
C15 C12 C11 137.2(2) . . ?
C15 C12 N13 107.7(2) . . ?
N13 C12 C11 115.1(2) . . ?
C5 C14 C1 128.7(2) . . ?
N13 C14 C1 109.4(2) . . ?
N13 C14 C5 121.9(2) . . ?
C1 C15 H15 126.2 . . ?
C12 C15 C1 107.5(2) . . ?
C12 C15 H15 126.2 . . ?
C10 C16 H16 119.5 . . ?
C17 C16 C10 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C11 C19 H19 119.7 . . ?
C18 C19 C11 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C4 177.4(3) . . ?
C20 C21 C22 177.8(3) . . ?
C23 C22 C21 121.0(2) . . ?
C27 C22 C21 120.1(2) . . ?
C27 C22 C23 118.9(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C22 C27 H27 119.8 . . ?
C26 C27 C22 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C6 N7 C8 120.2(2) . . ?
C12 N13 C8 128.0(2) . . ?
C14 N13 C8 122.6(2) . . ?
C14 N13 C12 109.4(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
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C14 N13 C8 178.3(2) . . . . ?
C1 C14 N13 C12 -0.4(3) . . . . ?
C2 C1 C14 C5 0.0(4) . . . . ?
C2 C1 C14 N13 -179.7(2) . . . . ?
C2 C1 C15 C12 180.0(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 C20 180.0(2) . . . . ?
C3 C4 C5 C6 177.3(2) . . . . ?
C3 C4 C5 C14 -1.7(3) . . . . ?
C4 C5 C6 N7 179.8(2) . . . . ?
C4 C5 C14 C1 1.4(4) . . . . ?
C4 C5 C14 N13 -178.9(2) . . . . ?
C5 C6 N7 C8 -0.2(4) . . . . ?
C5 C14 N13 C8 -1.4(3) . . . . ?
C5 C14 N13 C12 179.8(2) . . . . ?
C6 C5 C14 C1 -177.8(2) . . . . ?
C6 C5 C14 N13 1.9(3) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C8 C9 C10 C16 179.5(2) . . . . ?
C9 C8 N7 C6 -179.8(2) . . . . ?
C9 C8 N13 C12 -1.0(4) . . . . ?
C9 C8 N13 C14 -179.4(2) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 C19 179.4(2) . . . . ?
C9 C10 C16 C17 -179.2(2) . . . . ?
C10 C11 C12 C15 178.3(3) . . . . ?
C10 C11 C12 N13 -0.8(3) . . . . ?
C10 C11 C19 C18 -0.4(3) . . . . ?
C10 C16 C17 C18 0.1(4) . . . . ?
C11 C10 C16 C17 -0.3(4) . . . . ?
C11 C12 C15 C1 -179.9(3) . . . . ?
C11 C12 N13 C8 1.5(3) . . . . ?
C11 C12 N13 C14 -179.92(19) . . . . ?
C12 C11 C19 C18 179.1(2) . . . . ?
C14 C1 C2 C3 -1.0(3) . . . . ?
C14 C1 C15 C12 0.4(3) . . . . ?
C14 C5 C6 N7 -1.1(3) . . . . ?
C15 C1 C2 C3 179.4(3) . . . . ?
C15 C1 C14 C5 179.7(2) . . . . ?
C15 C1 C14 N13 0.0(3) . . . . ?
C15 C12 N13 C8 -177.9(2) . . . . ?
C15 C12 N13 C14 0.7(3) . . . . ?
C16 C10 C11 C12 -179.0(2) . . . . ?
C16 C10 C11 C19 0.5(3) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C11 0.1(4) . . . . ?
C19 C11 C12 C15 -1.1(4) . . . . ?
C19 C11 C12 N13 179.7(2) . . . . ?
C20 C4 C5 C6 -1.8(4) . . . . ?
C20 C4 C5 C14 179.2(2) . . . . ?
C21 C22 C23 C24 -178.3(2) . . . . ?
C21 C22 C27 C26 179.2(2) . . . . ?
C22 C23 C24 C25 -0.8(4) . . . . ?
C23 C22 C27 C26 0.1(4) . . . . ?
C23 C24 C25 C26 -0.2(4) . . . . ?
C24 C25 C26 C27 1.1(4) . . . . ?
C25 C26 C27 C22 -1.1(4) . . . . ?
C27 C22 C23 C24 0.8(4) . . . . ?
N7 C8 C9 C10 -179.5(2) . . . . ?
N7 C8 N13 C12 178.5(2) . . . . ?
N7 C8 N13 C14 0.0(3) . . . . ?
N13 C8 C9 C10 -0.1(3) . . . . ?
N13 C8 N7 C6 0.8(3) . . . . ?
N13 C12 C15 C1 -0.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.794
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.2(8)
2 0.8(8)

####################################################################### 
# 
# 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_230521lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2283774'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-07-23 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-05-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.3278(3)
_cell_length_b                   7.4345(2)
_cell_length_c                   21.1425(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.071(2)
_cell_angle_gamma                90
_cell_volume                     2534.37(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5360
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6350
_cell_measurement_theta_min      4.2140
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8719
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.235
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00  85.00   0.50    0.17    --   61.65  25.00 106.00   50
  2  ω    -93.00 -67.00   0.50    0.17    --  -64.43 -25.00 -57.00   52
  3  ω     66.00  91.00   0.50    0.17    --   70.49  25.00 106.00   50
  4  ω   -122.00 -75.00   0.50    0.17    --  -74.46 -25.00 -57.00   94
  5  ω     79.00 104.00   0.50    0.17    --   74.66  25.00 106.00   50
  6  ω   -121.00 -96.00   0.50    0.17    --  -77.38 -25.00 -57.00   50
  7  ω     73.00 127.00   0.50    0.17    --   80.07  25.00 106.00  108
  8  ω     35.00  61.00   0.50    0.17    --   61.65 -95.00-180.00   52
  9  ω     28.00  57.00   0.50    0.17    --   61.65 -95.00-120.00   58
 10  ω     30.00 105.00   0.50    0.17    --   61.65  15.00-150.00  150
 11  ω   -108.00 -33.00   0.50    0.17    --  -64.43 -15.00-180.00  150
 12  ω     34.00 105.00   0.50    0.17    --   70.49   0.00 -90.00  142
 13  ω     38.00  82.00   0.50    0.17    --   74.66 -95.00 -90.00   88
 14  ω     43.00  69.00   0.50    0.17    --   74.66 -95.00-180.00   52
 15  ω     43.00  78.00   0.50    0.17    --   74.66 -95.00   0.00   70
 16  ω     39.00  83.00   0.50    0.17    --   74.66 -95.00  90.00   88
 17  ω     42.00  83.00   0.50    0.17    --   74.66 -95.00-150.00   82
 18  ω   -118.00 -74.00   0.50    0.17    --  -77.38-125.00-180.00   88
 19  ω     87.00 112.00   0.50    0.17    --   80.07 125.00-180.00   50
 20  ω     55.00  88.00   0.50    0.17    --   80.07 -95.00 120.00   66
 21  ω     79.00 124.00   0.50    0.17    --   80.07 125.00 150.00   90
 22  ω     44.00  86.00   0.50    0.17    --   80.07 -95.00 -60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0305537000
_diffrn_orient_matrix_UB_12      0.0601635000
_diffrn_orient_matrix_UB_13      -0.0694421000
_diffrn_orient_matrix_UB_21      0.0904901500
_diffrn_orient_matrix_UB_22      0.0277552500
_diffrn_orient_matrix_UB_23      -0.0102907000
_diffrn_orient_matrix_UB_31      0.0034631000
_diffrn_orient_matrix_UB_32      -0.1962887000
_diffrn_orient_matrix_UB_33      -0.0227216000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1954
_reflns_number_total             2263
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00065(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+1.3174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C19(H19), N9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28804(8) 0.19933(18) 0.26796(7) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.25502(9) 0.15295(19) 0.32128(7) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.201122 0.105439 0.321827 0.031 Uiso 1 1 calc R U . . .
C3 C 0.31632(9) 0.1889(2) 0.37615(7) 0.0271(3) Uani 1 1 d . . . . .
C4 C 0.31938(10) 0.1657(2) 0.44205(7) 0.0331(4) Uani 1 1 d . . . . .
H4 H 0.273033 0.117198 0.458283 0.040 Uiso 1 1 calc R U . . .
C5 C 0.39036(11) 0.2139(2) 0.48373(7) 0.0362(4) Uani 1 1 d . . . . .
H5 H 0.392736 0.197416 0.528538 0.043 Uiso 1 1 calc R U . . .
C6 C 0.45825(10) 0.2865(2) 0.46001(7) 0.0338(4) Uani 1 1 d . . . . .
H6 H 0.506147 0.319362 0.489305 0.041 Uiso 1 1 calc R U . . .
C7 C 0.45801(9) 0.3121(2) 0.39484(7) 0.0287(3) Uani 1 1 d . . . . .
C8 C 0.38617(9) 0.26018(19) 0.35272(7) 0.0252(3) Uani 1 1 d . . . . .
C10 C 0.25624(8) 0.18241(18) 0.19902(7) 0.0217(3) Uani 1 1 d . . . . .
C11 C 0.31189(8) 0.13364(19) 0.15792(7) 0.0238(3) Uani 1 1 d . . . . .
H11 H 0.368088 0.110023 0.175423 0.029 Uiso 1 1 calc R U . . .
C12 C 0.28711(9) 0.11899(19) 0.09254(7) 0.0261(3) Uani 1 1 d . . . . .
H12 H 0.325843 0.084526 0.065633 0.031 Uiso 1 1 calc R U . . .
C13 C 0.20545(9) 0.1549(2) 0.06642(7) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.187983 0.147118 0.021467 0.033 Uiso 1 1 calc R U . . .
C14 C 0.14954(9) 0.20212(19) 0.10656(7) 0.0258(3) Uani 1 1 d . . . . .
H14 H 0.093563 0.226069 0.088530 0.031 Uiso 1 1 calc R U . . .
C15 C 0.17312(8) 0.21538(18) 0.17233(7) 0.0226(3) Uani 1 1 d . . . . .
C16 C 0.11030(8) 0.2660(2) 0.21517(7) 0.0252(3) Uani 1 1 d . . . . .
H16A H 0.096852 0.158042 0.238981 0.030 Uiso 1 1 calc R U . . .
H16B H 0.135234 0.356337 0.246864 0.030 Uiso 1 1 calc R U . . .
C17 C 0.03371(9) 0.3392(2) 0.17900(7) 0.0292(4) Uani 1 1 d . . . . .
C19 C 0.52961(9) 0.3906(2) 0.37257(7) 0.0317(4) Uani 1 1 d . . . . .
H19 H 0.575429 0.423065 0.403989 0.038 Uiso 1 1 calc R U . . .
N9 N 0.36835(7) 0.26443(16) 0.28758(5) 0.0240(3) Uani 1 1 d . . . . .
H9 H 0.402146 0.302286 0.261849 0.029 Uiso 1 1 calc R U . . .
N18 N -0.02664(8) 0.3911(2) 0.14956(7) 0.0403(4) Uani 1 1 d . . . . .
O20 O 0.53555(6) 0.41818(15) 0.31645(5) 0.0339(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3683(19) . ?
C1 C10 1.4735(19) . ?
C1 N9 1.3979(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.433(2) . ?
C3 C4 1.397(2) . ?
C3 C8 1.416(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(2) . ?
C7 C8 1.410(2) . ?
C7 C19 1.450(2) . ?
C8 N9 1.3624(18) . ?
C10 C11 1.4004(18) . ?
C10 C15 1.4068(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 C16 1.5189(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.464(2) . ?
C17 N18 1.1462(19) . ?
C19 H19 0.9500 . ?
C19 O20 1.2230(18) . ?
N9 H9 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 132.09(13) . . ?
C2 C1 N9 108.41(12) . . ?
N9 C1 C10 119.40(12) . . ?
C1 C2 H2 126.1 . . ?
C1 C2 C3 107.72(13) . . ?
C3 C2 H2 126.1 . . ?
C4 C3 C2 134.04(14) . . ?
C4 C3 C8 119.39(14) . . ?
C8 C3 C2 106.56(12) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.77(15) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.19(15) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.08(15) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 117.40(14) . . ?
C6 C7 C19 120.04(14) . . ?
C8 C7 C19 122.56(13) . . ?
C7 C8 C3 121.15(13) . . ?
N9 C8 C3 107.87(12) . . ?
N9 C8 C7 130.98(13) . . ?
C11 C10 C1 118.29(12) . . ?
C11 C10 C15 118.40(13) . . ?
C15 C10 C1 123.30(12) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.65(13) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.65(13) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.33(13) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.77(13) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C16 120.23(12) . . ?
C14 C15 C10 119.19(12) . . ?
C14 C15 C16 120.59(12) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.46(12) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
N18 C17 C16 177.67(17) . . ?
C7 C19 H19 117.5 . . ?
O20 C19 C7 125.02(14) . . ?
O20 C19 H19 117.5 . . ?
C1 N9 H9 125.3 . . ?
C8 N9 C1 109.44(11) . . ?
C8 N9 H9 125.3 . . ?

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
C1 C2 C3 C4 -178.29(16) . . . . ?
C1 C2 C3 C8 0.67(16) . . . . ?
C1 C10 C11 C12 -178.54(12) . . . . ?
C1 C10 C15 C14 177.75(12) . . . . ?
C1 C10 C15 C16 -1.9(2) . . . . ?
C2 C1 C10 C11 -140.85(16) . . . . ?
C2 C1 C10 C15 40.1(2) . . . . ?
C2 C1 N9 C8 -0.22(15) . . . . ?
C2 C3 C4 C5 179.32(16) . . . . ?
C2 C3 C8 C7 179.34(13) . . . . ?
C2 C3 C8 N9 -0.81(16) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C8 N9 C1 0.65(15) . . . . ?
C4 C3 C8 C7 -1.5(2) . . . . ?
C4 C3 C8 N9 178.34(13) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C5 C6 C7 C19 179.06(14) . . . . ?
C6 C7 C8 C3 1.6(2) . . . . ?
C6 C7 C8 N9 -178.26(14) . . . . ?
C6 C7 C19 O20 179.80(14) . . . . ?
C7 C8 N9 C1 -179.52(14) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
C8 C7 C19 O20 -0.6(2) . . . . ?
C10 C1 C2 C3 175.85(14) . . . . ?
C10 C1 N9 C8 -176.93(12) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C10 C15 C16 C17 165.35(13) . . . . ?
C11 C10 C15 C14 -1.3(2) . . . . ?
C11 C10 C15 C16 179.10(12) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C10 0.9(2) . . . . ?
C13 C14 C15 C16 -179.49(13) . . . . ?
C14 C15 C16 C17 -14.27(19) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?
C19 C7 C8 C3 -178.09(13) . . . . ?
C19 C7 C8 N9 2.1(2) . . . . ?
N9 C1 C2 C3 -0.29(16) . . . . ?
N9 C1 C10 C11 34.94(18) . . . . ?
N9 C1 C10 C15 -144.08(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.701
####################################################################### 
# 
# 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_230884lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2292226'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-09-01 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.43235(13)
_cell_length_b                   12.20419(15)
_cell_length_c                   11.52302(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.4803(11)
_cell_angle_gamma                90
_cell_volume                     1707.04(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7341
_cell_measurement_temperature    109(6)
_cell_measurement_theta_max      74.2820
_cell_measurement_theta_min      3.5720
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.736
_diffrn_reflns_theta_min         3.641
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  92.00   0.50    0.05    --   75.94-111.00 150.00   88
  2  ω     58.00  84.00   0.50    0.05    --   83.87-102.00  52.00   52
  3  ω     36.00  61.00   0.50    0.05    --   75.94-102.00  52.00   50
  4  ω     14.00  39.00   0.50    0.05    --   56.25 -95.00 150.00   50
  5  ω     48.00  80.00   0.50    0.05    --   69.31-102.00  52.00   64
  6  ω     55.00  83.00   0.50    0.05    --   83.87 -95.00 150.00   56
  7  ω     12.00  68.00   0.50    0.05    --   56.25-102.00  52.00  112
  8  ω     54.00  83.00   0.50    0.05    --   83.87 -95.00  90.00   58
  9  ω     47.00  91.00   0.50    0.05    --   83.87 -95.00   0.00   88
 10  ω     14.00  52.00   0.50    0.05    --   56.25 -95.00-120.00   76
 11  ω     32.00  76.00   0.50    0.05    --   69.31 -95.00-150.00   88
 12  ω     50.00  92.00   0.50    0.05    --   83.87 -95.00-120.00   84
 13  ω     53.00 117.00   0.50    0.05    --   83.87  15.00  90.00  128
 14  ω     60.00 110.00   0.50    0.05    --   69.31  15.00  30.00  100
 15  ω     70.00  95.00   0.50    0.05    --   83.87  15.00 -60.00   50
 16  ω     98.00 134.00   0.50    0.05    --   83.87  15.00 -60.00   72
 17  ω     81.00 126.00   0.50    0.05    --   75.94  15.00-150.00   90
 18  ω     51.00 111.00   0.50    0.05    --   75.94  15.00-180.00  120
 19  ω    -87.00 -30.00   0.50    0.05    --  -75.32 111.00 -60.00  114
 20  ω    -91.00 -39.00   0.50    0.05    --  -75.32 -15.00-150.00  104
 21  ω    -80.00 -55.00   0.50    0.05    --  -72.13 102.00 155.00   50
 22  ω    -78.00 -52.00   0.50    0.05    --  -75.32 102.00 155.00   52
 23  ω    -50.00 -25.00   0.50    0.05    --  -59.44 102.00 155.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0421176000
_diffrn_orient_matrix_UB_12      0.0301352000
_diffrn_orient_matrix_UB_13      -0.1318977000
_diffrn_orient_matrix_UB_21      -0.0459372000
_diffrn_orient_matrix_UB_22      -0.1168236000
_diffrn_orient_matrix_UB_23      -0.0254156000
_diffrn_orient_matrix_UB_31      -0.1105478000
_diffrn_orient_matrix_UB_32      0.0371625000
_diffrn_orient_matrix_UB_33      0.0267127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3024
_reflns_number_total             3318
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.4946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), N9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26772(9) 0.02587(9) 0.30585(9) 0.0190(2) Uani 1 1 d . . . . .
C2 C 0.18054(8) 0.07353(9) 0.34298(9) 0.0193(2) Uani 1 1 d . . . . .
C3 C 0.18780(9) 0.03716(9) 0.46371(9) 0.0198(2) Uani 1 1 d . . . . .
C4 C 0.12230(9) 0.05329(9) 0.54743(10) 0.0232(2) Uani 1 1 d . . . . .
H4 H 0.059829 0.100072 0.529618 0.028 Uiso 1 1 calc R U . . .
C5 C 0.14952(10) 0.00046(10) 0.65610(10) 0.0267(3) Uani 1 1 d . . . . .
H5 H 0.105089 0.010741 0.712727 0.032 Uiso 1 1 calc R U . . .
C6 C 0.24157(10) -0.06775(10) 0.68328(10) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.258232 -0.103433 0.758300 0.031 Uiso 1 1 calc R U . . .
C7 C 0.30971(9) -0.08510(9) 0.60387(10) 0.0223(2) Uani 1 1 d . . . . .
C8 C 0.28066(9) -0.03230(9) 0.49269(9) 0.0194(2) Uani 1 1 d . . . . .
C10 C 0.09118(9) 0.13943(9) 0.27087(10) 0.0209(2) Uani 1 1 d . . . . .
C11 C 0.04999(10) 0.23198(10) 0.31813(11) 0.0269(3) Uani 1 1 d . . . . .
H11 H 0.082206 0.255046 0.396698 0.032 Uiso 1 1 calc R U . . .
C12 C -0.03779(10) 0.29057(11) 0.25100(12) 0.0336(3) Uani 1 1 d . . . . .
H12 H -0.065153 0.353167 0.284257 0.040 Uiso 1 1 calc R U . . .
C13 C -0.08556(10) 0.25859(11) 0.13643(12) 0.0338(3) Uani 1 1 d . . . . .
H13 H -0.145890 0.298546 0.091251 0.041 Uiso 1 1 calc R U . . .
C14 C -0.04484(10) 0.16794(11) 0.08805(11) 0.0298(3) Uani 1 1 d . . . . .
H14 H -0.077088 0.145859 0.009150 0.036 Uiso 1 1 calc R U . . .
C15 C 0.04281(9) 0.10909(10) 0.15406(10) 0.0239(2) Uani 1 1 d . . . . .
H15 H 0.070403 0.047348 0.119546 0.029 Uiso 1 1 calc R U . . .
C16 C 0.30074(8) 0.03219(9) 0.19027(9) 0.0198(2) Uani 1 1 d . . . . .
C17 C 0.32435(9) 0.13241(9) 0.14173(9) 0.0211(2) Uani 1 1 d . . . . .
C18 C 0.35614(10) 0.13304(10) 0.03277(10) 0.0265(3) Uani 1 1 d . . . . .
H18 H 0.372091 0.200756 -0.000534 0.032 Uiso 1 1 calc R U . . .
C19 C 0.36477(10) 0.03640(11) -0.02754(10) 0.0302(3) Uani 1 1 d . . . . .
H19 H 0.386213 0.038141 -0.101809 0.036 Uiso 1 1 calc R U . . .
C20 C 0.34209(10) -0.06293(10) 0.02055(10) 0.0286(3) Uani 1 1 d . . . . .
H20 H 0.348118 -0.129374 -0.020517 0.034 Uiso 1 1 calc R U . . .
C21 C 0.31065(9) -0.06479(10) 0.12859(10) 0.0239(2) Uani 1 1 d . . . . .
H21 H 0.295535 -0.133007 0.161453 0.029 Uiso 1 1 calc R U . . .
C22 C 0.31728(9) 0.23900(9) 0.20775(10) 0.0235(2) Uani 1 1 d . . . . .
H22A H 0.243148 0.271328 0.179954 0.028 Uiso 1 1 calc R U . . .
H22B H 0.327413 0.223559 0.293779 0.028 Uiso 1 1 calc R U . . .
C23 C 0.40069(9) 0.31792(9) 0.18928(10) 0.0226(2) Uani 1 1 d . . . . .
C25 C 0.40821(10) -0.15195(10) 0.63864(10) 0.0278(3) Uani 1 1 d . . . . .
H25 H 0.423362 -0.182017 0.716529 0.033 Uiso 1 1 calc R U . . .
N9 N 0.32774(7) -0.03812(7) 0.39628(8) 0.0194(2) Uani 1 1 d . . . . .
H9 H 0.386795 -0.076424 0.392254 0.023 Uiso 1 1 calc R U . . .
N24 N 0.46759(8) 0.37714(8) 0.17414(9) 0.0285(2) Uani 1 1 d . . . . .
O26 O 0.47286(7) -0.17248(8) 0.57583(8) 0.0342(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3772(15) . ?
C1 C16 1.4780(14) . ?
C1 N9 1.3844(13) . ?
C2 C3 1.4444(15) . ?
C2 C10 1.4739(15) . ?
C3 C4 1.4043(15) . ?
C3 C8 1.4128(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3838(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3949(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3910(16) . ?
C7 C8 1.4095(15) . ?
C7 C25 1.4539(16) . ?
C8 N9 1.3649(13) . ?
C10 C11 1.3983(16) . ?
C10 C15 1.4003(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3914(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3816(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3832(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3869(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.4021(15) . ?
C16 C21 1.3997(16) . ?
C17 C18 1.3954(15) . ?
C17 C22 1.5190(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.3847(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3870(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3833(16) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.4641(15) . ?
C23 N24 1.1434(15) . ?
C25 H25 0.9500 . ?
C25 O26 1.2182(15) . ?
N9 H9 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C16 130.42(10) . . ?
C2 C1 N9 109.68(9) . . ?
N9 C1 C16 119.88(9) . . ?
C1 C2 C3 106.25(9) . . ?
C1 C2 C10 127.10(10) . . ?
C3 C2 C10 126.39(9) . . ?
C4 C3 C2 133.93(10) . . ?
C4 C3 C8 119.16(10) . . ?
C8 C3 C2 106.85(9) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.45(11) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.63(10) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.00(10) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 117.09(10) . . ?
C6 C7 C25 120.04(10) . . ?
C8 C7 C25 122.84(10) . . ?
C7 C8 C3 121.66(10) . . ?
N9 C8 C3 108.12(9) . . ?
N9 C8 C7 130.18(10) . . ?
C11 C10 C2 121.07(10) . . ?
C11 C10 C15 118.08(10) . . ?
C15 C10 C2 120.82(10) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.52(12) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.64(12) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.46(11) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.39(12) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.90(11) . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C1 121.86(10) . . ?
C21 C16 C1 119.04(10) . . ?
C21 C16 C17 119.09(10) . . ?
C16 C17 C22 120.49(10) . . ?
C18 C17 C16 119.22(10) . . ?
C18 C17 C22 120.28(10) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.97(11) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.96(11) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.69(11) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.07(11) . . ?
C20 C21 H21 119.5 . . ?
C17 C22 H22A 109.3 . . ?
C17 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 C17 111.78(9) . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
N24 C23 C22 178.07(12) . . ?
C7 C25 H25 117.4 . . ?
O26 C25 C7 125.18(11) . . ?
O26 C25 H25 117.4 . . ?
C1 N9 H9 125.5 . . ?
C8 N9 C1 109.09(9) . . ?
C8 N9 H9 125.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -177.23(12) . . . . ?
C1 C2 C3 C8 -0.31(12) . . . . ?
C1 C2 C10 C11 -140.87(12) . . . . ?
C1 C2 C10 C15 41.10(16) . . . . ?
C1 C16 C17 C18 179.39(10) . . . . ?
C1 C16 C17 C22 0.37(16) . . . . ?
C1 C16 C21 C20 -179.53(10) . . . . ?
C2 C1 C16 C17 58.27(16) . . . . ?
C2 C1 C16 C21 -122.91(13) . . . . ?
C2 C1 N9 C8 -0.26(12) . . . . ?
C2 C3 C4 C5 176.23(11) . . . . ?
C2 C3 C8 C7 -177.98(10) . . . . ?
C2 C3 C8 N9 0.16(12) . . . . ?
C2 C10 C11 C12 -177.00(10) . . . . ?
C2 C10 C15 C14 176.84(10) . . . . ?
C3 C2 C10 C11 45.75(16) . . . . ?
C3 C2 C10 C15 -132.28(12) . . . . ?
C3 C4 C5 C6 0.47(17) . . . . ?
C3 C8 N9 C1 0.05(12) . . . . ?
C4 C3 C8 C7 -0.52(16) . . . . ?
C4 C3 C8 N9 177.62(9) . . . . ?
C4 C5 C6 C7 0.39(18) . . . . ?
C5 C6 C7 C8 -1.25(16) . . . . ?
C5 C6 C7 C25 176.53(11) . . . . ?
C6 C7 C8 C3 1.32(16) . . . . ?
C6 C7 C8 N9 -176.37(11) . . . . ?
C6 C7 C25 O26 179.68(12) . . . . ?
C7 C8 N9 C1 177.98(11) . . . . ?
C8 C3 C4 C5 -0.39(16) . . . . ?
C8 C7 C25 O26 -2.68(18) . . . . ?
C10 C2 C3 C4 -2.72(19) . . . . ?
C10 C2 C3 C8 174.19(10) . . . . ?
C10 C11 C12 C13 -0.21(18) . . . . ?
C11 C10 C15 C14 -1.25(16) . . . . ?
C11 C12 C13 C14 -0.54(19) . . . . ?
C12 C13 C14 C15 0.38(18) . . . . ?
C13 C14 C15 C10 0.53(18) . . . . ?
C15 C10 C11 C12 1.09(16) . . . . ?
C16 C1 C2 C3 178.92(11) . . . . ?
C16 C1 C2 C10 4.47(19) . . . . ?
C16 C1 N9 C8 -179.01(9) . . . . ?
C16 C17 C18 C19 -0.11(17) . . . . ?
C16 C17 C22 C23 145.50(10) . . . . ?
C17 C16 C21 C20 -0.68(17) . . . . ?
C17 C18 C19 C20 -0.26(19) . . . . ?
C18 C17 C22 C23 -33.50(14) . . . . ?
C18 C19 C20 C21 0.16(19) . . . . ?
C19 C20 C21 C16 0.31(18) . . . . ?
C21 C16 C17 C18 0.57(16) . . . . ?
C21 C16 C17 C22 -178.44(10) . . . . ?
C22 C17 C18 C19 178.91(11) . . . . ?
C25 C7 C8 C3 -176.39(10) . . . . ?
C25 C7 C8 N9 5.92(18) . . . . ?
N9 C1 C2 C3 0.35(12) . . . . ?
N9 C1 C2 C10 -174.10(10) . . . . ?
N9 C1 C16 C17 -123.28(11) . . . . ?
N9 C1 C16 C21 55.54(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.790
####################################################################### 
# 
# 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_231041lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2301731'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-10-17 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 N3 O'
_chemical_formula_sum            'C17 H9 N3 O'
_chemical_formula_weight         271.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   3.77916(13)
_cell_length_b                   16.2226(5)
_cell_length_c                   19.1757(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.565(3)
_cell_angle_gamma                90
_cell_volume                     1173.34(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3179
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2430
_cell_measurement_theta_min      3.5780
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6065
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.802
_diffrn_reflns_theta_min         3.572
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  77.00   0.50    0.17    --   75.94 -95.00-150.00   84
  2  ω     39.00  65.00   0.50    0.17    --   83.87-111.00-150.00   52
  3  ω     16.00  41.00   0.50    0.17    --   56.05 -95.00 -90.00   50
  4  ω     53.00  88.00   0.50    0.17    --   83.87 -95.00-120.00   70
  5  ω     15.00  58.00   0.50    0.17    --   56.05 -95.00   0.00   86
  6  ω     30.00  67.00   0.50    0.17    --   69.01 -95.00  60.00   74
  7  ω     33.00  60.00   0.50    0.17    --   75.94 -95.00  60.00   54
  8  ω     49.00  83.00   0.50    0.17    --   83.87 -95.00  90.00   68
  9  ω     53.00  79.00   0.50    0.17    --   75.94  15.00   0.00   52
 10  ω     49.00 120.00   0.50    0.17    --   83.87  15.00-150.00  142
 11  ω     77.00 120.00   0.50    0.17    --   83.87  15.00 -60.00   86
 12  ω     55.00 126.00   0.50    0.17    --   75.94  15.00 150.00  142
 13  ω    -90.00 -61.00   0.50    0.17    --  -75.32 -15.00 -60.00   58
 14  ω   -126.00 -95.00   0.50    0.17    --  -75.32 -15.00 -60.00   62
 15  ω    -92.00 -31.00   0.50    0.17    --  -75.32 111.00 -90.00  122
 16  ω    -91.00 -31.00   0.50    0.17    --  -75.32 111.00 120.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3373883000
_diffrn_orient_matrix_UB_12      -0.0130433000
_diffrn_orient_matrix_UB_13      -0.0398027000
_diffrn_orient_matrix_UB_21      0.1218676000
_diffrn_orient_matrix_UB_22      -0.0680278000
_diffrn_orient_matrix_UB_23      0.0521344000
_diffrn_orient_matrix_UB_31      -0.1953598000
_diffrn_orient_matrix_UB_32      -0.0649102000
_diffrn_orient_matrix_UB_33      -0.0467036000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1756
_reflns_number_total             2257
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.1630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O21 O -0.6212(3) -0.25594(7) 0.19751(6) 0.0392(3) Uani 1 1 d . . . . .
N5 N 0.2442(4) 0.03188(8) 0.39405(7) 0.0317(3) Uani 1 1 d . . . . .
N13 N -0.0479(3) -0.08919(8) 0.34934(6) 0.0270(3) Uani 1 1 d . . . . .
N20 N -0.4870(4) -0.25415(8) 0.25966(7) 0.0327(3) Uani 1 1 d . . . . .
C1 C -0.1206(4) -0.21430(9) 0.41121(8) 0.0278(4) Uani 1 1 d . . . . .
C2 C 0.0588(4) -0.17407(10) 0.46988(8) 0.0291(4) Uani 1 1 d . . . . .
C3 C 0.1878(4) -0.09172(10) 0.46511(8) 0.0299(4) Uani 1 1 d . . . . .
H3 H 0.311453 -0.066988 0.504374 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1345(4) -0.04851(10) 0.40466(8) 0.0285(4) Uani 1 1 d . . . . .
C6 C 0.1680(4) 0.06837(10) 0.33419(8) 0.0323(4) Uani 1 1 d . . . . .
H6 H 0.243177 0.123821 0.329178 0.039 Uiso 1 1 calc R U . . .
C7 C -0.0239(4) 0.02974(10) 0.27482(8) 0.0305(4) Uani 1 1 d . . . . .
C8 C -0.1175(4) 0.06055(10) 0.20851(8) 0.0332(4) Uani 1 1 d . . . . .
H8 H -0.062743 0.115785 0.196742 0.040 Uiso 1 1 calc R U . . .
C9 C -0.2942(5) 0.00851(11) 0.15930(8) 0.0348(4) Uani 1 1 d . . . . .
H9 H -0.354095 0.029832 0.113954 0.042 Uiso 1 1 calc R U . . .
C10 C -0.3868(4) -0.07295(10) 0.17337(8) 0.0321(4) Uani 1 1 d . . . . .
H10 H -0.506401 -0.105935 0.138399 0.038 Uiso 1 1 calc R U . . .
C11 C -0.2997(4) -0.10496(10) 0.24008(8) 0.0288(4) Uani 1 1 d . . . . .
C12 C -0.1206(4) -0.05118(10) 0.28631(8) 0.0281(3) Uani 1 1 d . . . . .
C14 C -0.1745(4) -0.16853(9) 0.34771(8) 0.0277(3) Uani 1 1 d . . . . .
C15 C -0.2420(4) -0.29593(10) 0.41803(8) 0.0308(4) Uani 1 1 d . . . . .
H15 H -0.358793 -0.323175 0.379244 0.037 Uiso 1 1 calc R U . . .
C16 C -0.1907(4) -0.33595(10) 0.48114(8) 0.0348(4) Uani 1 1 d . . . . .
H16 H -0.270753 -0.391107 0.485568 0.042 Uiso 1 1 calc R U . . .
C17 C -0.0214(4) -0.29618(11) 0.53898(9) 0.0342(4) Uani 1 1 d . . . . .
H17 H 0.007508 -0.324261 0.582431 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1024(4) -0.21745(10) 0.53346(8) 0.0320(4) Uani 1 1 d . . . . .
H18 H 0.219224 -0.191672 0.572978 0.038 Uiso 1 1 calc R U . . .
C19 C -0.3367(4) -0.18120(10) 0.27944(7) 0.0279(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O21 N20 1.2662(17) . ?
N5 C4 1.387(2) . ?
N5 C6 1.308(2) . ?
N13 C4 1.3946(19) . ?
N13 C12 1.3695(19) . ?
N13 C14 1.373(2) . ?
N20 C19 1.357(2) . ?
C1 C2 1.434(2) . ?
C1 C14 1.430(2) . ?
C1 C15 1.410(2) . ?
C2 C3 1.427(2) . ?
C2 C18 1.408(2) . ?
C3 C4 1.359(2) . ?
C6 C7 1.454(2) . ?
C7 C8 1.391(2) . ?
C7 C12 1.384(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.398(2) . ?
C10 C11 1.401(2) . ?
C11 C12 1.389(2) . ?
C11 C19 1.460(2) . ?
C14 C19 1.425(2) . ?
C15 C16 1.376(2) . ?
C16 C17 1.403(2) . ?
C17 C18 1.367(2) . ?

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
C6 N5 C4 120.18(13) . . ?
C12 N13 C4 121.38(14) . . ?
C12 N13 C14 110.59(12) . . ?
C14 N13 C4 128.03(13) . . ?
O21 N20 C19 114.80(13) . . ?
C14 C1 C2 117.86(14) . . ?
C15 C1 C2 119.69(14) . . ?
C15 C1 C14 122.45(14) . . ?
C3 C2 C1 121.50(14) . . ?
C18 C2 C1 118.41(15) . . ?
C18 C2 C3 120.08(14) . . ?
C4 C3 C2 120.30(14) . . ?
N5 C4 N13 118.13(14) . . ?
C3 C4 N5 125.46(14) . . ?
C3 C4 N13 116.41(14) . . ?
N5 C6 C7 124.36(15) . . ?
C8 C7 C6 130.33(16) . . ?
C12 C7 C6 114.08(14) . . ?
C12 C7 C8 115.57(15) . . ?
C7 C8 C9 118.79(15) . . ?
C10 C9 C8 123.59(15) . . ?
C9 C10 C11 118.64(15) . . ?
C10 C11 C19 139.60(15) . . ?
C12 C11 C10 115.30(15) . . ?
C12 C11 C19 105.11(13) . . ?
N13 C12 C7 121.82(14) . . ?
N13 C12 C11 110.07(14) . . ?
C7 C12 C11 128.10(15) . . ?
N13 C14 C1 115.87(13) . . ?
N13 C14 C19 106.58(13) . . ?
C19 C14 C1 137.53(15) . . ?
C16 C15 C1 119.71(15) . . ?
C15 C16 C17 120.70(16) . . ?
C18 C17 C16 120.68(15) . . ?
C17 C18 C2 120.79(15) . . ?
N20 C19 C11 130.26(14) . . ?
N20 C19 C14 122.09(14) . . ?
C14 C19 C11 107.65(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.850
####################################################################### 
# 
# 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_230861lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2290023'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-08-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.22512(19)
_cell_length_b                   10.0169(4)
_cell_length_c                   12.1195(4)
_cell_angle_alpha                104.088(3)
_cell_angle_beta                 101.613(2)
_cell_angle_gamma                109.165(3)
_cell_volume                     870.66(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7364
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6990
_cell_measurement_theta_min      3.9400
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9944
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.836
_diffrn_reflns_theta_min         3.951
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  56.00   0.50    0.05    --   56.25-125.00 -90.00   74
  2  ω     28.00  54.00   0.50    0.05    --   69.31-125.00-120.00   52
  3  ω     15.00  41.00   0.50    0.05    --   56.25-103.00-161.00   52
  4  ω     29.00  54.00   0.50    0.05    --   69.31-103.00-161.00   50
  5  ω     36.00  61.00   0.50    0.05    --   75.94-103.00-161.00   50
  6  ω     64.00  92.00   0.50    0.05    --   83.87-103.00-161.00   56
  7  ω     33.00  58.00   0.50    0.05    --   75.94 -95.00 -90.00   50
  8  ω     17.00  56.00   0.50    0.05    --   56.25 -95.00 -60.00   78
  9  ω     27.00  52.00   0.50    0.05    --   69.31 -95.00  30.00   50
 10  ω     35.00  60.00   0.50    0.05    --   75.94 -95.00  60.00   50
 11  ω     29.00  56.00   0.50    0.05    --   69.31 -95.00  90.00   54
 12  ω     35.00  67.00   0.50    0.05    --   75.94 -95.00 120.00   64
 13  ω     40.00  84.00   0.50    0.05    --   75.94 -95.00 150.00   88
 14  ω     47.00  87.00   0.50    0.05    --   83.87 -95.00 120.00   80
 15  ω     49.00  88.00   0.50    0.05    --   83.87 -95.00  90.00   78
 16  ω     41.00  66.00   0.50    0.05    --   83.87 -95.00  30.00   50
 17  ω     66.00  91.00   0.50    0.05    --   83.87 -95.00   0.00   50
 18  ω     43.00  90.00   0.50    0.05    --   83.87 -95.00 -60.00   94
 19  ω     41.00  92.00   0.50    0.05    --   83.87 -95.00-120.00  102
 20  ω     56.00 127.00   0.50    0.05    --   83.87  15.00   0.00  142
 21  ω     94.00 119.00   0.50    0.05    --   69.31  15.00 -30.00   50
 22  ω     48.00 107.00   0.50    0.05    --   75.94  15.00 -60.00  118
 23  ω     58.00  84.00   0.50    0.05    --   69.31  15.00 -30.00   52
 24  ω     80.00 105.00   0.50    0.05    --   83.87  15.00 120.00   50
 25  ω     37.00  81.00   0.50    0.05    --   56.25  15.00  90.00   88
 26  ω    -64.00 -38.00   0.50    0.05    --  -59.44 -15.00  30.00   52
 27  ω   -126.00 -39.00   0.50    0.05    --  -75.32 -15.00 -30.00  174
 28  ω   -109.00 -73.00   0.50    0.05    --  -59.44 -15.00  30.00   72
 29  ω   -125.00 -48.00   0.50    0.05    --  -75.32 -15.00  60.00  154
 30  ω   -121.00 -88.00   0.50    0.05    --  -72.13 -15.00 120.00   66
 31  ω    -62.00 -36.00   0.50    0.05    --  -72.13 -15.00 120.00   52
 32  ω    -83.00 -56.00   0.50    0.05    --  -75.32 103.00 -59.00   54
 33  ω    -58.00 -33.00   0.50    0.05    --  -75.32 111.00-150.00   50
 34  ω    -97.00 -34.00   0.50    0.05    --  -79.90 115.00 -46.85  126
 35  ω    -97.00 -64.00   0.50    0.05    --  -79.90 114.00  25.30   66
 36  ω    -59.00 -34.00   0.50    0.05    --  -79.90 114.00  25.30   50
 37  ω    -63.00 -36.00   0.50    0.05    --  -75.32 111.00 150.00   54
 38  ω    -52.00 -26.00   0.50    0.05    --  -59.44 103.00 -59.00   52
 39  ω    -56.00 -31.00   0.50    0.05    --  -72.13 103.00 -59.00   50
 40  ω    -92.00 -66.00   0.50    0.05    --  -75.32 111.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0010757000
_diffrn_orient_matrix_UB_12      0.1295215000
_diffrn_orient_matrix_UB_13      -0.0470116000
_diffrn_orient_matrix_UB_21      -0.0055386000
_diffrn_orient_matrix_UB_22      -0.0927760000
_diffrn_orient_matrix_UB_23      -0.1234909000
_diffrn_orient_matrix_UB_31      -0.2082708000
_diffrn_orient_matrix_UB_32      -0.0668390000
_diffrn_orient_matrix_UB_33      -0.0387559000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3127
_reflns_number_total             3312
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0093(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.2543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0858
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), N9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41510(14) 0.24729(11) -0.17199(9) 0.0209(2) Uani 1 1 d . . . . .
C2 C 0.30780(14) 0.32789(11) -0.17162(9) 0.0208(2) Uani 1 1 d . . . . .
C3 C 0.21443(14) 0.30002(11) -0.08544(9) 0.0211(2) Uani 1 1 d . . . . .
C4 C 0.08453(14) 0.34449(12) -0.04735(9) 0.0235(2) Uani 1 1 d . . . . .
H4 H 0.039781 0.406422 -0.081264 0.028 Uiso 1 1 calc R U . . .
C5 C 0.02180(15) 0.29716(12) 0.04047(10) 0.0259(2) Uani 1 1 d . . . . .
H5 H -0.065979 0.327476 0.066551 0.031 Uiso 1 1 calc R U . . .
C6 C 0.08567(15) 0.20582(12) 0.09099(10) 0.0250(2) Uani 1 1 d . . . . .
H6 H 0.043351 0.177523 0.152629 0.030 Uiso 1 1 calc R U . . .
C7 C 0.21072(14) 0.15522(12) 0.05258(9) 0.0228(2) Uani 1 1 d . . . . .
C8 C 0.27240(14) 0.20216(11) -0.03735(9) 0.0210(2) Uani 1 1 d . . . . .
C10 C 0.28791(13) 0.42631(12) -0.24209(9) 0.0211(2) Uani 1 1 d . . . . .
C11 C 0.30416(14) 0.57065(12) -0.18148(10) 0.0240(2) Uani 1 1 d . . . . .
H11 H 0.331486 0.602706 -0.096965 0.029 Uiso 1 1 calc R U . . .
C12 C 0.28147(15) 0.66786(12) -0.24138(11) 0.0281(3) Uani 1 1 d . . . . .
H12 H 0.291669 0.764673 -0.198304 0.034 Uiso 1 1 calc R U . . .
C13 C 0.24379(16) 0.62305(13) -0.36461(11) 0.0312(3) Uani 1 1 d . . . . .
H13 H 0.229409 0.689368 -0.406362 0.037 Uiso 1 1 calc R U . . .
C14 C 0.22725(16) 0.48077(13) -0.42643(10) 0.0290(3) Uani 1 1 d . . . . .
H14 H 0.202065 0.450574 -0.510776 0.035 Uiso 1 1 calc R U . . .
C15 C 0.24685(14) 0.38123(12) -0.36728(9) 0.0230(2) Uani 1 1 d . . . . .
C16 C 0.22352(15) 0.22488(13) -0.43821(9) 0.0262(2) Uani 1 1 d . . . . .
H16A H 0.340708 0.228695 -0.449420 0.031 Uiso 1 1 calc R U . . .
H16B H 0.189684 0.157424 -0.391530 0.031 Uiso 1 1 calc R U . . .
C17 C 0.08560(15) 0.16176(13) -0.55588(10) 0.0265(2) Uani 1 1 d . . . . .
C19 C 0.54225(14) 0.23554(12) -0.23999(9) 0.0226(2) Uani 1 1 d . . . . .
C20 C 0.54283(16) 0.09558(13) -0.29408(10) 0.0274(2) Uani 1 1 d . . . . .
H20 H 0.461987 0.008097 -0.286240 0.033 Uiso 1 1 calc R U . . .
C21 C 0.66135(18) 0.08430(16) -0.35919(11) 0.0363(3) Uani 1 1 d . . . . .
H21 H 0.661309 -0.011034 -0.395852 0.044 Uiso 1 1 calc R U . . .
C22 C 0.77937(18) 0.21088(18) -0.37100(11) 0.0400(3) Uani 1 1 d . . . . .
H22 H 0.860335 0.202467 -0.415611 0.048 Uiso 1 1 calc R U . . .
C23 C 0.77980(16) 0.35002(16) -0.31788(11) 0.0363(3) Uani 1 1 d . . . . .
H23 H 0.861299 0.436927 -0.326053 0.044 Uiso 1 1 calc R U . . .
C24 C 0.66134(15) 0.36317(14) -0.25255(10) 0.0283(3) Uani 1 1 d . . . . .
H24 H 0.661519 0.458767 -0.216596 0.034 Uiso 1 1 calc R U . . .
C25 C 0.27032(15) 0.05445(12) 0.10181(10) 0.0258(2) Uani 1 1 d . . . . .
H25 H 0.223543 0.025254 0.161715 0.031 Uiso 1 1 calc R U . . .
N9 N 0.39124(12) 0.16993(10) -0.09218(7) 0.0210(2) Uani 1 1 d . . . . .
H9 H 0.444253 0.109542 -0.078866 0.025 Uiso 1 1 calc R U . . .
N18 N -0.02310(15) 0.11028(12) -0.64709(9) 0.0364(3) Uani 1 1 d . . . . .
O26 O 0.37729(10) 0.00542(9) 0.07019(7) 0.0293(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3779(14) . ?
C1 C19 1.4722(14) . ?
C1 N9 1.3843(13) . ?
C2 C3 1.4431(14) . ?
C2 C10 1.4791(14) . ?
C3 C4 1.4014(14) . ?
C3 C8 1.4147(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3892(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3953(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3970(15) . ?
C7 C8 1.4078(15) . ?
C7 C25 1.4545(15) . ?
C8 N9 1.3658(13) . ?
C10 C11 1.4016(14) . ?
C10 C15 1.4071(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3853(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3870(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3867(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3931(15) . ?
C15 C16 1.5197(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.4693(15) . ?
C17 N18 1.1442(15) . ?
C19 C20 1.3976(15) . ?
C19 C24 1.3964(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.3872(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3920(16) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 O26 1.2207(13) . ?
N9 H9 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C19 130.53(9) . . ?
C2 C1 N9 109.54(9) . . ?
N9 C1 C19 119.93(9) . . ?
C1 C2 C3 106.39(9) . . ?
C1 C2 C10 128.93(9) . . ?
C3 C2 C10 124.67(9) . . ?
C4 C3 C2 134.08(10) . . ?
C4 C3 C8 119.04(9) . . ?
C8 C3 C2 106.84(9) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.39(10) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.06(10) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.20(10) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 117.52(10) . . ?
C6 C7 C25 120.86(10) . . ?
C8 C7 C25 121.61(10) . . ?
C7 C8 C3 121.69(9) . . ?
N9 C8 C3 107.99(9) . . ?
N9 C8 C7 130.32(9) . . ?
C11 C10 C2 118.27(9) . . ?
C11 C10 C15 118.04(9) . . ?
C15 C10 C2 123.65(9) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.83(10) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.63(10) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.53(10) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.30(10) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C16 120.46(9) . . ?
C14 C15 C10 119.66(10) . . ?
C14 C15 C16 119.88(9) . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.30(9) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
N18 C17 C16 178.77(13) . . ?
C20 C19 C1 120.06(10) . . ?
C24 C19 C1 120.55(10) . . ?
C24 C19 C20 119.39(10) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.07(11) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.36(12) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.05(11) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.29(12) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 120.1 . . ?
C23 C24 C19 119.85(11) . . ?
C23 C24 H24 120.1 . . ?
C7 C25 H25 118.3 . . ?
O26 C25 C7 123.44(10) . . ?
O26 C25 H25 118.3 . . ?
C1 N9 H9 125.4 . . ?
C8 N9 C1 109.22(8) . . ?
C8 N9 H9 125.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -177.57(11) . . . . ?
C1 C2 C3 C8 0.15(11) . . . . ?
C1 C2 C10 C11 -129.74(11) . . . . ?
C1 C2 C10 C15 52.73(16) . . . . ?
C1 C19 C20 C21 179.34(10) . . . . ?
C1 C19 C24 C23 -179.52(10) . . . . ?
C2 C1 C19 C20 -135.65(12) . . . . ?
C2 C1 C19 C24 43.46(16) . . . . ?
C2 C1 N9 C8 -1.47(12) . . . . ?
C2 C3 C4 C5 -179.60(11) . . . . ?
C2 C3 C8 C7 178.20(9) . . . . ?
C2 C3 C8 N9 -1.03(11) . . . . ?
C2 C10 C11 C12 -177.85(10) . . . . ?
C2 C10 C15 C14 178.77(10) . . . . ?
C2 C10 C15 C16 -1.14(16) . . . . ?
C3 C2 C10 C11 49.54(14) . . . . ?
C3 C2 C10 C15 -127.99(11) . . . . ?
C3 C4 C5 C6 -0.19(16) . . . . ?
C3 C8 N9 C1 1.53(11) . . . . ?
C4 C3 C8 C7 -3.67(15) . . . . ?
C4 C3 C8 N9 177.10(9) . . . . ?
C4 C5 C6 C7 -1.92(17) . . . . ?
C5 C6 C7 C8 1.18(16) . . . . ?
C5 C6 C7 C25 -177.14(10) . . . . ?
C6 C7 C8 C3 1.62(15) . . . . ?
C6 C7 C8 N9 -179.34(10) . . . . ?
C6 C7 C25 O26 178.97(10) . . . . ?
C7 C8 N9 C1 -177.61(11) . . . . ?
C8 C3 C4 C5 2.90(15) . . . . ?
C8 C7 C25 O26 0.72(17) . . . . ?
C10 C2 C3 C4 3.01(18) . . . . ?
C10 C2 C3 C8 -179.27(9) . . . . ?
C10 C11 C12 C13 -0.81(17) . . . . ?
C10 C15 C16 C17 145.30(10) . . . . ?
C11 C10 C15 C14 1.23(15) . . . . ?
C11 C10 C15 C16 -178.67(9) . . . . ?
C11 C12 C13 C14 0.74(17) . . . . ?
C12 C13 C14 C15 0.33(18) . . . . ?
C13 C14 C15 C10 -1.32(17) . . . . ?
C13 C14 C15 C16 178.58(10) . . . . ?
C14 C15 C16 C17 -34.60(14) . . . . ?
C15 C10 C11 C12 -0.18(15) . . . . ?
C19 C1 C2 C3 -178.57(10) . . . . ?
C19 C1 C2 C10 0.81(19) . . . . ?
C19 C1 N9 C8 177.97(9) . . . . ?
C19 C20 C21 C22 0.03(17) . . . . ?
C20 C19 C24 C23 -0.41(15) . . . . ?
C20 C21 C22 C23 -0.08(18) . . . . ?
C21 C22 C23 C24 -0.11(18) . . . . ?
C22 C23 C24 C19 0.36(17) . . . . ?
C24 C19 C20 C21 0.22(16) . . . . ?
C25 C7 C8 C3 179.92(10) . . . . ?
C25 C7 C8 N9 -1.04(18) . . . . ?
N9 C1 C2 C3 0.79(11) . . . . ?
N9 C1 C2 C10 -179.83(10) . . . . ?
N9 C1 C19 C20 45.05(14) . . . . ?
N9 C1 C19 C24 -135.84(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.119
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_231019lt
_database_code_depnum_ccdc_archive 'CCDC 2301525'
loop_
_audit_author_name
_audit_author_address
'Vikas Sadaphal'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-10-16 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2023-10-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 N2'
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.6032(6)
_cell_length_b                   3.85280(10)
_cell_length_c                   18.9019(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.580(3)
_cell_angle_gamma                90
_cell_volume                     1264.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8241
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      73.7850
_cell_measurement_theta_min      3.1220
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17727
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.864
_diffrn_reflns_theta_min         3.177
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  62.00   0.50    2.30    --   56.25-115.00-147.00   52
  2  ω    -49.00 -19.00   0.50    2.30    --  -59.44 115.00 -57.00   60
  3  ω     33.00  58.00   0.50    2.30    --   69.31-115.00-147.00   50
  4  ω    -83.00 -58.00   0.50    2.30    --  -72.13 115.00 -57.00   50
  5  ω    -92.00 -48.00   0.50    2.30    --  -75.32 115.00 -57.00   88
  6  ω     63.00  88.00   0.50    2.30    --   75.94-115.00-147.00   50
  7  ω     71.00  97.00   0.50    2.30    --   83.87-115.00-147.00   52
  8  ω     14.00  63.00   0.50    2.30    --   56.25 -95.00  30.00   98
  9  ω     31.00  56.00   0.50    2.30    --   56.25-125.00 -60.00   50
 10  ω     15.00  63.00   0.50    2.30    --   56.25 -95.00 -30.00   96
 11  ω     53.00  78.00   0.50    2.30    --   56.25  15.00 -90.00   50
 12  ω     26.00  83.00   0.50    2.30    --   56.25-125.00-180.00  114
 13  ω     18.00  43.00   0.50    2.30    --   56.25 -95.00 -90.00   50
 14  ω     16.00  48.00   0.50    2.30    --   56.25 -95.00  90.00   64
 15  ω   -108.00 -41.00   0.50    2.30    --  -59.44 -15.00  90.00  134
 16  ω    -67.00 -26.00   0.50    2.30    --  -72.13 125.00  60.00   82
 17  ω    -59.00 -26.00   0.50    2.30    --  -72.13 125.00   0.00   66
 18  ω    -98.00 -72.00   0.50    2.30    --  -72.13 125.00  60.00   52
 19  ω   -103.00 -40.00   0.50    2.30    --  -75.32 -15.00 150.00  126
 20  ω   -126.00 -58.00   0.50    2.30    --  -75.32 -15.00-120.00  136
 21  ω   -126.00 -53.00   0.50    2.30    --  -75.32 -15.00  30.00  146
 22  ω   -126.00 -40.00   0.50    2.30    --  -75.32 -15.00 -60.00  172
 23  ω     53.00  83.00   0.50    2.30    --   75.94 -95.00 120.00   60
 24  ω     37.00  82.00   0.50    2.30    --   75.94 -95.00  60.00   90
 25  ω     34.00  82.00   0.50    2.30    --   75.94 -95.00-150.00   96
 26  ω     33.00  58.00   0.50    2.30    --   75.94 -95.00 -60.00   50
 27  ω    -97.00 -42.00   0.50    2.30    --  -79.90 114.00-104.12  110
 28  ω     66.00  91.00   0.50    2.30    --   83.87 -95.00  60.00   50
 29  ω     41.00  92.00   0.50    2.30    --   83.87 -95.00-150.00  102
 30  ω     58.00  92.00   0.50    2.30    --   83.87 -95.00 120.00   68
 31  ω     43.00  92.00   0.50    2.30    --   83.87 -95.00-120.00   98
 32  ω     39.00  64.00   0.50    2.30    --   83.87-111.00 -90.00   50
 33  ω     67.00  92.00   0.50    2.30    --   83.87 -95.00  90.00   50
 34  ω     41.00  92.00   0.50    2.30    --   83.87 -95.00 150.00  102
 35  ω     41.00  92.00   0.50    2.30    --   83.87 -95.00   0.00  102
 36  ω     43.00  91.00   0.50    2.30    --   83.87 -95.00 -90.00   96
 37  ω     51.00 106.00   0.50    2.30    --   83.87  15.00  90.00  110
 38  ω     56.00 134.00   0.50    2.30    --   83.87  15.00 -60.00  156
 39  ω     42.00  92.00   0.50    2.30    --   83.87 -95.00 -30.00  100
 40  ω     39.00  66.00   0.50    2.30    --   83.87-111.00 120.00   54
 41  ω     42.00  92.00   0.50    2.30    --   83.87 -95.00  30.00  100
 42  ω     42.00  68.00   0.50    2.30    --   83.87 -95.00-180.00   52
 43  ω     50.00 130.00   0.50    2.30    --   83.87  15.00-150.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0765264000
_diffrn_orient_matrix_UB_12      -0.1407716000
_diffrn_orient_matrix_UB_13      0.0177174000
_diffrn_orient_matrix_UB_21      0.0368329000
_diffrn_orient_matrix_UB_22      -0.0328082000
_diffrn_orient_matrix_UB_23      0.0795933000
_diffrn_orient_matrix_UB_31      -0.0256056000
_diffrn_orient_matrix_UB_32      0.3729789000
_diffrn_orient_matrix_UB_33      0.0136741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2234
_reflns_number_total             2556
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1064P)²+0.4753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1814
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.b X=CH2 refined with riding coordinates:
 C21(H21A,H21B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37123(11) 0.6775(4) 0.70880(9) 0.0383(4) Uani 1 1 d . . . . .
C2 C 0.42310(11) 0.6605(5) 0.77627(10) 0.0406(4) Uani 1 1 d . . . . .
C3 C 0.49716(11) 0.5066(5) 0.77856(11) 0.0437(5) Uani 1 1 d . . . . .
C4 C 0.52014(11) 0.3634(5) 0.71449(11) 0.0451(5) Uani 1 1 d . . . . .
H4 H 0.569734 0.262387 0.716906 0.054 Uiso 1 1 calc R U . . .
C5 C 0.47123(11) 0.3730(5) 0.65121(11) 0.0418(5) Uani 1 1 d . . . . .
C7 C 0.43274(12) 0.2638(5) 0.52862(11) 0.0447(5) Uani 1 1 d . . . . .
H7 H 0.444700 0.166724 0.485601 0.054 Uiso 1 1 calc R U . . .
C8 C 0.35806(11) 0.4294(4) 0.52465(10) 0.0422(5) Uani 1 1 d . . . . .
C9 C 0.29798(12) 0.4776(5) 0.46785(10) 0.0454(5) Uani 1 1 d . . . . .
C10 C 0.23052(12) 0.6458(5) 0.48208(10) 0.0456(5) Uani 1 1 d . . . . .
H10 H 0.189258 0.677277 0.443291 0.055 Uiso 1 1 calc R U . . .
C11 C 0.22096(12) 0.7681(5) 0.54954(10) 0.0440(5) Uani 1 1 d . . . . .
H11 H 0.174345 0.878777 0.555912 0.053 Uiso 1 1 calc R U . . .
C12 C 0.28103(11) 0.7258(4) 0.60796(10) 0.0391(4) Uani 1 1 d . . . . .
C13 C 0.34617(11) 0.5568(4) 0.59133(9) 0.0383(4) Uani 1 1 d . . . . .
C15 C 0.54729(12) 0.4909(5) 0.84506(11) 0.0506(5) Uani 1 1 d . . . . .
H15 H 0.596938 0.390211 0.847640 0.061 Uiso 1 1 calc R U . . .
C16 C 0.52463(13) 0.6208(6) 0.90641(12) 0.0535(5) Uani 1 1 d . . . . .
H16 H 0.558650 0.607434 0.950961 0.064 Uiso 1 1 calc R U . . .
C17 C 0.45218(12) 0.7715(5) 0.90334(11) 0.0495(5) Uani 1 1 d . . . . .
H17 H 0.437315 0.861046 0.945832 0.059 Uiso 1 1 calc R U . . .
C18 C 0.40212(12) 0.7918(5) 0.83961(10) 0.0441(5) Uani 1 1 d . . . . .
H18 H 0.352927 0.895371 0.838289 0.053 Uiso 1 1 calc R U . . .
C19 C 0.29828(10) 0.8004(4) 0.68310(9) 0.0388(4) Uani 1 1 d . . . . .
H19 H 0.265200 0.914844 0.710525 0.047 Uiso 1 1 calc R U . . .
C20 C 0.30473(15) 0.3527(5) 0.39492(11) 0.0558(6) Uani 1 1 d . . . . .
H20 H 0.347450 0.208192 0.390650 0.067 Uiso 1 1 calc R U . . .
C21 C 0.25713(17) 0.4240(6) 0.33609(12) 0.0698(7) Uani 1 1 d . . . . .
H21A H 0.213607 0.567577 0.337831 0.084 Uiso 1 1 calc R U . . .
H21B H 0.266016 0.332282 0.291533 0.084 Uiso 1 1 calc R U . . .
N6 N 0.48503(10) 0.2368(4) 0.58634(9) 0.0465(4) Uani 1 1 d . . . . .
N14 N 0.39994(8) 0.5287(4) 0.65053(8) 0.0375(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.441(3) . ?
C1 C19 1.379(3) . ?
C1 N14 1.408(2) . ?
C2 C3 1.426(3) . ?
C2 C18 1.405(3) . ?
C3 C4 1.448(3) . ?
C3 C15 1.412(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.353(3) . ?
C5 N6 1.392(2) . ?
C5 N14 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.452(3) . ?
C7 N6 1.309(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.401(2) . ?
C9 C10 1.417(3) . ?
C9 C20 1.483(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.405(3) . ?
C12 C13 1.399(2) . ?
C12 C19 1.431(3) . ?
C13 N14 1.344(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.305(3) . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 C1 C2 137.98(16) . . ?
C19 C1 N14 107.39(16) . . ?
N14 C1 C2 114.63(16) . . ?
C3 C2 C1 119.14(17) . . ?
C18 C2 C1 121.35(17) . . ?
C18 C2 C3 119.51(19) . . ?
C2 C3 C4 120.94(18) . . ?
C15 C3 C2 118.52(18) . . ?
C15 C3 C4 120.53(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.24(17) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 N6 126.15(17) . . ?
C4 C5 N14 117.44(17) . . ?
N14 C5 N6 116.40(17) . . ?
C8 C7 H7 117.2 . . ?
N6 C7 H7 117.2 . . ?
N6 C7 C8 125.66(17) . . ?
C9 C8 C7 131.71(17) . . ?
C9 C8 C13 116.12(17) . . ?
C13 C8 C7 112.16(18) . . ?
C8 C9 C10 117.96(17) . . ?
C8 C9 C20 120.45(19) . . ?
C10 C9 C20 121.59(19) . . ?
C9 C10 H10 118.0 . . ?
C11 C10 C9 124.05(19) . . ?
C11 C10 H10 118.0 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.29(18) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C19 139.81(17) . . ?
C13 C12 C11 114.53(16) . . ?
C13 C12 C19 105.66(17) . . ?
C12 C13 C8 128.03(19) . . ?
N14 C13 C8 122.07(17) . . ?
N14 C13 C12 109.90(15) . . ?
C3 C15 H15 119.8 . . ?
C16 C15 C3 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.67(19) . . ?
C18 C17 H17 119.7 . . ?
C2 C18 H18 119.8 . . ?
C17 C18 C2 120.43(19) . . ?
C17 C18 H18 119.8 . . ?
C1 C19 C12 108.17(16) . . ?
C1 C19 H19 125.9 . . ?
C12 C19 H19 125.9 . . ?
C9 C20 H20 117.1 . . ?
C21 C20 C9 125.7(2) . . ?
C21 C20 H20 117.1 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C7 N6 C5 120.17(16) . . ?
C5 N14 C1 127.59(17) . . ?
C13 N14 C1 108.88(14) . . ?
C13 N14 C5 123.53(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C15 -179.82(15) . . . . ?
C1 C2 C18 C17 179.66(16) . . . . ?
C2 C1 C19 C12 -179.32(19) . . . . ?
C2 C1 N14 C5 -0.3(2) . . . . ?
C2 C1 N14 C13 179.22(13) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C15 C16 0.3(3) . . . . ?
C3 C2 C18 C17 -0.2(3) . . . . ?
C3 C4 C5 N6 -178.05(17) . . . . ?
C3 C4 C5 N14 1.0(3) . . . . ?
C3 C15 C16 C17 -0.5(3) . . . . ?
C4 C3 C15 C16 -178.59(18) . . . . ?
C4 C5 N6 C7 -179.87(17) . . . . ?
C4 C5 N14 C1 -0.8(3) . . . . ?
C4 C5 N14 C13 179.73(15) . . . . ?
C7 C8 C9 C10 178.54(18) . . . . ?
C7 C8 C9 C20 -0.9(3) . . . . ?
C7 C8 C13 C12 -179.03(16) . . . . ?
C7 C8 C13 N14 1.1(2) . . . . ?
C8 C7 N6 C5 0.1(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C8 C9 C20 C21 -170.1(2) . . . . ?
C8 C13 N14 C1 -179.59(15) . . . . ?
C8 C13 N14 C5 0.0(3) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C9 C8 C13 N14 -179.59(15) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C9 C20 C21 10.5(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C10 C11 C12 C19 -179.8(2) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C11 C12 C13 N14 -179.86(14) . . . . ?
C11 C12 C19 C1 179.3(2) . . . . ?
C12 C13 N14 C1 0.51(19) . . . . ?
C12 C13 N14 C5 -179.92(15) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
C13 C8 C9 C20 179.91(16) . . . . ?
C13 C12 C19 C1 -0.02(19) . . . . ?
C15 C3 C4 C5 178.65(16) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C2 0.1(3) . . . . ?
C18 C2 C3 C4 178.94(16) . . . . ?
C18 C2 C3 C15 0.1(3) . . . . ?
C19 C1 C2 C3 -179.2(2) . . . . ?
C19 C1 C2 C18 0.9(3) . . . . ?
C19 C1 N14 C5 179.94(16) . . . . ?
C19 C1 N14 C13 -0.51(19) . . . . ?
C19 C12 C13 C8 179.80(17) . . . . ?
C19 C12 C13 N14 -0.30(19) . . . . ?
C20 C9 C10 C11 179.93(18) . . . . ?
N6 C5 N14 C1 178.37(15) . . . . ?
N6 C5 N14 C13 -1.1(2) . . . . ?
N6 C7 C8 C9 179.67(18) . . . . ?
N6 C7 C8 C13 -1.2(3) . . . . ?
N14 C1 C2 C3 1.2(2) . . . . ?
N14 C1 C2 C18 -178.74(15) . . . . ?
N14 C1 C19 C12 0.32(19) . . . . ?
N14 C5 N6 C7 1.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.673
_oxdiff_exptl_absorpt_empirical_full_min 0.493
