# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_htr-4-ip_auto
_database_code_depnum_ccdc_archive 'CCDC 2312583'
loop_
_audit_author_name
_audit_author_address
'Kota Hattori'
;Shizuoka University
Japan
;
_audit_update_record             
;
2023-12-07 deposited with the CCDC.	2024-02-16 downloaded from the CCDC.
;
_audit_creation_date             2023-06-02
_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 H9 N'
_chemical_formula_sum            'C17 H9 N'
_chemical_formula_weight         227.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         CN
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/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                   3.8023(2)
_cell_length_b                   17.9097(9)
_cell_length_c                   15.9061(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.960(4)
_cell_angle_gamma                90
_cell_volume                     1080.59(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6100
_cell_measurement_theta_min      3.7230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.41
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5540
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.081
_diffrn_reflns_theta_min         3.722
_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
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  67.00   0.50    0.51    --  107.20 -57.00 120.00   54
  2  ω     35.00  60.00   0.50    0.51    --  107.20 -57.00  90.00   50
  3  ω     35.00  64.00   0.50    0.51    --  107.20 -57.00  30.00   58
  4  ω     44.00  69.00   0.50    0.51    --  107.20 -57.00  60.00   50
  5  ω     35.00  67.00   0.50    0.51    --  107.20 -57.00 -90.00   64
  6  ω    117.00 152.00   0.50    0.51    --  107.20 107.00   4.00   70
  7  ω    -18.00  12.00   0.50    0.13    --   46.86 -19.00   0.00   60
  8  ω     10.00  81.00   0.50    0.13    --   46.86-107.00 -93.00  142
  9  ω     64.00  90.00   0.50    0.51    --  107.20-107.00 -93.00   52
 10  ω     67.00 106.00   0.50    0.51    --  107.20 -99.00  90.00   78
 11  ω     37.00  63.00   0.50    0.51    --  107.20 -99.00  90.00   52
 12  ω    -33.00  25.00   0.50    0.13    --  -46.86  38.00 120.00  116
 13  ω    -62.00 -37.00   0.50    0.51    -- -104.50  57.00   0.00   50
 14  ω    -61.00 -36.00   0.50    0.51    -- -104.50  57.00 -60.00   50
 15  ω    -22.00  26.00   0.50    0.13    --  -46.86  19.00-150.00   96
 16  ω    -18.00   7.00   0.50    0.13    --  -46.86  19.00-180.00   50
 17  ω    -62.00 -32.00   0.50    0.51    -- -104.50  57.00-150.00   60
 18  ω   -154.00-129.00   0.50    0.51    -- -104.50 -19.00 -60.00   50
 19  ω   -150.00 -85.00   0.50    0.51    -- -104.50-107.00 -93.00  130
 20  ω   -173.00 -94.00   0.50    0.51    -- -104.50 -19.00  90.00  158
 21  ω    -77.00 -50.00   0.50    0.13    --  -46.86 107.00   4.00   54
 22  ω   -106.00 -59.00   0.50    0.51    -- -104.50 107.00   4.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118270000
_diffrn_orient_matrix_UB_12      -0.0592092000
_diffrn_orient_matrix_UB_13      -0.0704180000
_diffrn_orient_matrix_UB_21      -0.1459195000
_diffrn_orient_matrix_UB_22      0.0588269000
_diffrn_orient_matrix_UB_23      -0.0639849000
_diffrn_orient_matrix_UB_31      0.3784869000
_diffrn_orient_matrix_UB_32      0.0207757000
_diffrn_orient_matrix_UB_33      -0.0197074000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1798
_reflns_number_total             2163
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (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         0.915
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0870
_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)+(0.1374P)²+1.1394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2486
_refine_ls_wR_factor_ref         0.2583
_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:
 C007(H007), C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
;
_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
N001 N 0.3688(7) 0.52154(14) 0.61076(15) 0.0322(6) Uani 1 1 d . . . . .
C002 C 0.4210(7) 0.45585(15) 0.74494(16) 0.0221(6) Uani 1 1 d . . . . .
C003 C 0.3572(7) 0.39010(14) 0.79150(16) 0.0216(6) Uani 1 1 d . . . . .
C004 C 0.1819(7) 0.32775(15) 0.75197(17) 0.0233(6) Uani 1 1 d . . . . .
C005 C 0.4640(7) 0.38721(15) 0.87900(16) 0.0239(6) Uani 1 1 d . . . . .
C006 C 0.1178(7) 0.26272(15) 0.79940(19) 0.0273(7) Uani 1 1 d . . . . .
C007 C 0.1401(7) 0.39727(16) 0.61811(17) 0.0256(6) Uani 1 1 d . . . . .
H007 H 0.067462 0.400151 0.559844 0.031 Uiso 1 1 calc R U . . .
C008 C 0.6382(7) 0.44891(16) 0.91640(17) 0.0276(7) Uani 1 1 d . . . . .
H008 H 0.716712 0.447047 0.974375 0.033 Uiso 1 1 calc R U . . .
C009 C 0.0740(7) 0.33053(15) 0.66409(17) 0.0249(6) Uani 1 1 d . . . . .
C00A C 0.3047(7) 0.45622(15) 0.65662(17) 0.0234(6) Uani 1 1 d . . . . .
C00B C 0.5921(7) 0.51651(15) 0.78526(18) 0.0262(6) Uani 1 1 d . . . . .
H00B H 0.636075 0.560505 0.754312 0.031 Uiso 1 1 calc R U . . .
C00C C 0.6976(7) 0.51248(16) 0.87023(18) 0.0281(7) Uani 1 1 d . . . . .
H00C H 0.812419 0.554033 0.897181 0.034 Uiso 1 1 calc R U . . .
C00D C 0.2252(8) 0.26145(16) 0.88763(19) 0.0310(7) Uani 1 1 d . . . . .
H00D H 0.179093 0.218443 0.920056 0.037 Uiso 1 1 calc R U . . .
C00E C 0.3914(8) 0.32076(17) 0.92532(18) 0.0302(7) Uani 1 1 d . . . . .
H00E H 0.461634 0.318346 0.983746 0.036 Uiso 1 1 calc R U . . .
C00F C -0.0929(8) 0.26854(16) 0.62605(19) 0.0295(7) Uani 1 1 d . . . . .
H00F H -0.166040 0.269975 0.567743 0.035 Uiso 1 1 calc R U . . .
C00G C -0.1525(8) 0.20554(17) 0.6721(2) 0.0330(7) Uani 1 1 d . . . . .
H00G H -0.262724 0.163535 0.645011 0.040 Uiso 1 1 calc R U . . .
C00H C -0.0533(8) 0.20228(16) 0.7582(2) 0.0332(7) Uani 1 1 d . . . . .
H00H H -0.102381 0.158612 0.789199 0.040 Uiso 1 1 calc R U . . .
C00I C 0.4192(10) 0.57636(19) 0.5740(2) 0.0400(8) 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
N001 C00A 1.409(4) . ?
N001 C00I 1.165(4) . ?
C002 C003 1.421(4) . ?
C002 C00A 1.443(4) . ?
C002 C00B 1.399(4) . ?
C003 C004 1.424(4) . ?
C003 C005 1.424(4) . ?
C004 C006 1.418(4) . ?
C004 C009 1.430(4) . ?
C005 C008 1.400(4) . ?
C005 C00E 1.437(4) . ?
C006 C00D 1.434(4) . ?
C006 C00H 1.402(4) . ?
C007 H007 0.9500 . ?
C007 C009 1.433(4) . ?
C007 C00A 1.352(4) . ?
C008 H008 0.9500 . ?
C008 C00C 1.382(4) . ?
C009 C00F 1.396(4) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.385(4) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00E 1.355(5) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00F C00G 1.373(4) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.396(5) . ?
C00H H00H 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
C00I N001 C00A 178.7(3) . . ?
C003 C002 C00A 117.3(2) . . ?
C00B C002 C003 119.7(2) . . ?
C00B C002 C00A 123.0(3) . . ?
C002 C003 C004 120.7(2) . . ?
C002 C003 C005 119.5(2) . . ?
C005 C003 C004 119.8(2) . . ?
C003 C004 C009 119.9(2) . . ?
C006 C004 C003 120.1(3) . . ?
C006 C004 C009 120.0(3) . . ?
C003 C005 C00E 118.7(3) . . ?
C008 C005 C003 118.8(2) . . ?
C008 C005 C00E 122.6(3) . . ?
C004 C006 C00D 119.1(3) . . ?
C00H C006 C004 118.5(3) . . ?
C00H C006 C00D 122.5(3) . . ?
C009 C007 H007 119.6 . . ?
C00A C007 H007 119.6 . . ?
C00A C007 C009 120.8(2) . . ?
C005 C008 H008 119.5 . . ?
C00C C008 C005 121.0(3) . . ?
C00C C008 H008 119.5 . . ?
C004 C009 C007 118.7(2) . . ?
C00F C009 C004 119.1(3) . . ?
C00F C009 C007 122.2(3) . . ?
N001 C00A C002 117.1(2) . . ?
C007 C00A N001 120.3(2) . . ?
C007 C00A C002 122.6(2) . . ?
C002 C00B H00B 120.0 . . ?
C00C C00B C002 120.1(3) . . ?
C00C C00B H00B 120.0 . . ?
C008 C00C C00B 121.0(3) . . ?
C008 C00C H00C 119.5 . . ?
C00B C00C H00C 119.5 . . ?
C006 C00D H00D 119.6 . . ?
C00E C00D C006 120.9(3) . . ?
C00E C00D H00D 119.6 . . ?
C005 C00E H00E 119.2 . . ?
C00D C00E C005 121.5(3) . . ?
C00D C00E H00E 119.2 . . ?
C009 C00F H00F 119.7 . . ?
C00G C00F C009 120.6(3) . . ?
C00G C00F H00F 119.7 . . ?
C00F C00G H00G 119.5 . . ?
C00F C00G C00H 121.0(3) . . ?
C00H C00G H00G 119.5 . . ?
C006 C00H H00H 119.6 . . ?
C00G C00H C006 120.8(3) . . ?
C00G C00H H00H 119.6 . . ?

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
C002 C003 C004 C006 -179.5(2) . . . . ?
C002 C003 C004 C009 1.2(4) . . . . ?
C002 C003 C005 C008 -1.7(4) . . . . ?
C002 C003 C005 C00E 178.9(2) . . . . ?
C002 C00B C00C C008 0.4(4) . . . . ?
C003 C002 C00A N001 -180.0(2) . . . . ?
C003 C002 C00A C007 0.2(4) . . . . ?
C003 C002 C00B C00C -0.2(4) . . . . ?
C003 C004 C006 C00D 1.3(4) . . . . ?
C003 C004 C006 C00H -179.6(2) . . . . ?
C003 C004 C009 C007 -1.2(4) . . . . ?
C003 C004 C009 C00F 179.1(2) . . . . ?
C003 C005 C008 C00C 1.8(4) . . . . ?
C003 C005 C00E C00D 0.0(4) . . . . ?
C004 C003 C005 C008 179.5(2) . . . . ?
C004 C003 C005 C00E 0.1(4) . . . . ?
C004 C006 C00D C00E -1.2(4) . . . . ?
C004 C006 C00H C00G 1.2(4) . . . . ?
C004 C009 C00F C00G -0.2(4) . . . . ?
C005 C003 C004 C006 -0.8(4) . . . . ?
C005 C003 C004 C009 179.9(2) . . . . ?
C005 C008 C00C C00B -1.2(4) . . . . ?
C006 C004 C009 C007 179.5(2) . . . . ?
C006 C004 C009 C00F -0.2(4) . . . . ?
C006 C00D C00E C005 0.5(4) . . . . ?
C007 C009 C00F C00G -179.9(2) . . . . ?
C008 C005 C00E C00D -179.4(3) . . . . ?
C009 C004 C006 C00D -179.4(2) . . . . ?
C009 C004 C006 C00H -0.3(4) . . . . ?
C009 C007 C00A N001 179.9(2) . . . . ?
C009 C007 C00A C002 -0.3(4) . . . . ?
C009 C00F C00G C00H 1.1(4) . . . . ?
C00A C002 C003 C004 -0.7(4) . . . . ?
C00A C002 C003 C005 -179.4(2) . . . . ?
C00A C002 C00B C00C -179.9(2) . . . . ?
C00A C007 C009 C004 0.7(4) . . . . ?
C00A C007 C009 C00F -179.5(3) . . . . ?
C00B C002 C003 C004 179.7(2) . . . . ?
C00B C002 C003 C005 0.9(4) . . . . ?
C00B C002 C00A N001 -0.3(4) . . . . ?
C00B C002 C00A C007 179.8(2) . . . . ?
C00D C006 C00H C00G -179.7(2) . . . . ?
C00E C005 C008 C00C -178.8(2) . . . . ?
C00F C00G C00H C006 -1.6(4) . . . . ?
C00H C006 C00D C00E 179.7(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 2.914
_oxdiff_exptl_absorpt_empirical_full_min 0.389
_exptl_crystal_preparation       Luminescent
