# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_20230412_GTH_319_A_1
_database_code_depnum_ccdc_archive 'CCDC 2272052'
loop_
_audit_author_name
_audit_author_address
GTH
;Henan University of Technology
China
;
_audit_update_record             
;
2023-06-24 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         319.38

_chemical_melting_point          ?

_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                   8.2109(2)
_cell_length_b                   13.5877(3)
_cell_length_c                   15.4845(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.6590(10)
_cell_angle_gamma                90
_cell_volume                     1727.45(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7474
_cell_measurement_theta_min      3.2525
_cell_measurement_theta_max      65.1367
_cell_measurement_temperature    303.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      303.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'cu k\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            15879
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         65.13
_diffrn_reflns_theta_full        65.13
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             2942
_reflns_number_gt                1997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1161
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.1230P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1230)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.3500(2) 0.80067(12) 0.57826(14) 0.0747(5) Uani d . . . 1 . .
C C1 0.7674(3) 0.91085(19) 0.46351(16) 0.0884(7) Uani d . . . 1 . .
H H1 0.765624 0.973496 0.439314 0.106000 Uiso calc U . R 1 . .
C C2 0.6296(3) 0.87424(16) 0.50042(15) 0.0760(6) Uani d . . . 1 . .
H H7 0.535570 0.912382 0.501377 0.091000 Uiso calc U . R 1 . .
C C3 0.6286(2) 0.77902(13) 0.53714(12) 0.0576(4) Uani d . . . 1 . .
C C4 0.7726(2) 0.72205(13) 0.53344(11) 0.0543(4) Uani d . . . 1 . .
C C5 0.7734(2) 0.62675(13) 0.57065(11) 0.0521(4) Uani d . . . 1 . .
H H14 0.867999 0.589236 0.568731 0.062000 Uiso calc U . R 1 . .
C C6 0.63855(19) 0.58861(12) 0.60927(9) 0.0467(4) Uani d . . . 1 . .
C C7 0.65343(17) 0.49129(13) 0.65371(10) 0.0480(4) Uani d . . . 1 . .
C C8 0.6270(2) 0.48385(15) 0.74243(11) 0.0565(4) Uani d . . . 1 . .
H H10 0.592583 0.538781 0.773068 0.068000 Uiso calc U . R 1 . .
C C9 0.6514(2) 0.39576(18) 0.78507(13) 0.0668(5) Uani d . . . 1 . .
H H13 0.635960 0.392228 0.844396 0.080000 Uiso calc U . R 1 . .
C C10 0.6985(2) 0.31301(16) 0.74034(15) 0.0717(6) Uani d . . . 1 . .
H H2 0.713707 0.253658 0.769229 0.086000 Uiso calc U . R 1 . .
C C11 0.0678(2) 0.50921(18) 0.71941(14) 0.0719(6) Uani d . . . 1 . .
H H3 -0.021071 0.478376 0.744423 0.086000 Uiso calc U . R 1 . .
C C12 0.1119(2) 0.60294(18) 0.74469(15) 0.0719(5) Uani d . . . 1 . .
H H4 0.050769 0.635841 0.785824 0.086000 Uiso calc U . R 1 . .
C C13 0.2468(2) 0.64852(15) 0.70918(13) 0.0592(4) Uani d . . . 1 . .
C C14 0.34190(19) 0.59912(12) 0.64895(10) 0.0494(4) Uani d . . . 1 . .
C C15 0.2928(2) 0.50464(13) 0.62316(11) 0.0543(4) Uani d . . . 1 . .
H H6 0.353510 0.470606 0.582563 0.065000 Uiso calc U . R 1 . .
C C16 0.1560(2) 0.46160(15) 0.65709(13) 0.0643(5) Uani d . . . 1 . .
H H5 0.122895 0.399889 0.637722 0.077000 Uiso calc U . R 1 . .
C C17 0.4906(2) 0.64434(12) 0.61293(10) 0.0485(4) Uani d . . . 1 . .
C C18 0.4887(2) 0.73946(13) 0.57926(12) 0.0561(4) Uani d . . . 1 . .
C C19 0.9098(4) 0.85590(19) 0.46159(15) 0.0832(7) Uani d . . . 1 . .
H H8 1.003050 0.882340 0.437130 0.100000 Uiso calc U . R 1 . .
C C20 0.9135(3) 0.76330(17) 0.49548(13) 0.0690(5) Uani d . . . 1 . .
H H9 1.009257 0.726826 0.493698 0.083000 Uiso calc U . R 1 . .
C C21 0.7229(3) 0.31870(15) 0.65226(15) 0.0712(5) Uani d . . . 1 . .
H H12 0.753033 0.262903 0.621547 0.085000 Uiso calc U . R 1 . .
C C22 0.7023(2) 0.40764(14) 0.60993(12) 0.0598(4) Uani d . . . 1 . .
H H11 0.721761 0.411315 0.550961 0.072000 Uiso calc U . R 1 . .
C C23 0.2636(3) 0.80829(16) 0.64560(19) 0.0826(7) Uani d . . . 1 . .
H H15 0.175791 0.851494 0.642982 0.099000 Uiso calc U . R 1 . .
C C24 0.2902(3) 0.75431(17) 0.72820(16) 0.0768(6) Uani d . . . 1 . .
H H17 0.221113 0.780625 0.773042 0.092000 Uiso calc U . R 1 . .
H H16 0.402942 0.759617 0.747030 0.092000 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C23 . 1.272(3) ?
N1 C18 . 1.411(2) ?
C1 C2 . 1.367(3) ?
C1 C19 . 1.388(4) ?
C1 H1 . 0.930000 ?
C2 C3 . 1.413(3) ?
C2 H7 . 0.930000 ?
C3 C4 . 1.415(3) ?
C3 C18 . 1.431(3) ?
C4 C5 . 1.417(3) ?
C4 C20 . 1.419(3) ?
C5 C6 . 1.366(2) ?
C5 H14 . 0.930000 ?
C6 C17 . 1.433(2) ?
C6 C7 . 1.495(2) ?
C7 C22 . 1.385(2) ?
C7 C8 . 1.397(2) ?
C8 C9 . 1.380(3) ?
C8 H10 . 0.930000 ?
C9 C10 . 1.378(3) ?
C9 H13 . 0.930000 ?
C10 C21 . 1.383(3) ?
C10 H2 . 0.930000 ?
C11 C16 . 1.375(3) ?
C11 C12 . 1.379(3) ?
C11 H3 . 0.930000 ?
C12 C13 . 1.388(3) ?
C12 H4 . 0.930000 ?
C13 C14 . 1.395(2) ?
C13 C24 . 1.509(3) ?
C14 C15 . 1.402(2) ?
C14 C17 . 1.482(2) ?
C15 C16 . 1.376(3) ?
C15 H6 . 0.930000 ?
C16 H5 . 0.930000 ?
C17 C18 . 1.394(2) ?
C19 C20 . 1.364(3) ?
C19 H8 . 0.930000 ?
C20 H9 . 0.930000 ?
C21 C22 . 1.384(3) ?
C21 H12 . 0.930000 ?
C22 H11 . 0.930000 ?
C23 C24 . 1.488(4) ?
C23 H15 . 0.930000 ?
C24 H17 . 0.970000 ?
C24 H16 . 0.970000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 N1 C18 . . 119.8(2) ?
C2 C1 C19 . . 121.0(2) ?
C2 C1 H1 . . 119.500000 ?
C19 C1 H1 . . 119.500000 ?
C1 C2 C3 . . 120.7(2) ?
C1 C2 H7 . . 119.700000 ?
C3 C2 H7 . . 119.700000 ?
C2 C3 C4 . . 118.39(18) ?
C2 C3 C18 . . 122.38(19) ?
C4 C3 C18 . . 119.21(16) ?
C3 C4 C5 . . 118.88(16) ?
C3 C4 C20 . . 119.11(18) ?
C5 C4 C20 . . 121.97(18) ?
C6 C5 C4 . . 121.65(16) ?
C6 C5 H14 . . 119.200000 ?
C4 C5 H14 . . 119.200000 ?
C5 C6 C17 . . 120.54(15) ?
C5 C6 C7 . . 118.33(14) ?
C17 C6 C7 . . 120.94(14) ?
C22 C7 C8 . . 118.11(16) ?
C22 C7 C6 . . 121.54(13) ?
C8 C7 C6 . . 120.25(15) ?
C9 C8 C7 . . 120.64(18) ?
C9 C8 H10 . . 119.700000 ?
C7 C8 H10 . . 119.700000 ?
C10 C9 C8 . . 120.46(17) ?
C10 C9 H13 . . 119.800000 ?
C8 C9 H13 . . 119.800000 ?
C9 C10 C21 . . 119.65(18) ?
C9 C10 H2 . . 120.200000 ?
C21 C10 H2 . . 120.200000 ?
C16 C11 C12 . . 119.68(19) ?
C16 C11 H3 . . 120.200000 ?
C12 C11 H3 . . 120.200000 ?
C11 C12 C13 . . 120.5(2) ?
C11 C12 H4 . . 119.800000 ?
C13 C12 H4 . . 119.800000 ?
C12 C13 C14 . . 120.36(18) ?
C12 C13 C24 . . 122.38(19) ?
C14 C13 C24 . . 117.12(17) ?
C13 C14 C15 . . 117.99(16) ?
C13 C14 C17 . . 121.48(15) ?
C15 C14 C17 . . 120.53(15) ?
C16 C15 C14 . . 120.91(18) ?
C16 C15 H6 . . 119.500000 ?
C14 C15 H6 . . 119.500000 ?
C11 C16 C15 . . 120.44(18) ?
C11 C16 H5 . . 119.800000 ?
C15 C16 H5 . . 119.800000 ?
C18 C17 C6 . . 118.76(16) ?
C18 C17 C14 . . 121.31(15) ?
C6 C17 C14 . . 119.88(14) ?
C17 C18 N1 . . 123.80(17) ?
C17 C18 C3 . . 120.87(17) ?
N1 C18 C3 . . 115.19(17) ?
C20 C19 C1 . . 120.2(2) ?
C20 C19 H8 . . 119.900000 ?
C1 C19 H8 . . 119.900000 ?
C19 C20 C4 . . 120.6(2) ?
C19 C20 H9 . . 119.700000 ?
C4 C20 H9 . . 119.700000 ?
C10 C21 C22 . . 119.8(2) ?
C10 C21 H12 . . 120.100000 ?
C22 C21 H12 . . 120.100000 ?
C21 C22 C7 . . 121.26(17) ?
C21 C22 H11 . . 119.400000 ?
C7 C22 H11 . . 119.400000 ?
N1 C23 C24 . . 125.9(2) ?
N1 C23 H15 . . 117.100000 ?
C24 C23 H15 . . 117.100000 ?
C23 C24 C13 . . 105.64(19) ?
C23 C24 H17 . . 110.600000 ?
C13 C24 H17 . . 110.600000 ?
C23 C24 H16 . . 110.600000 ?
C13 C24 H16 . . 110.600000 ?
H17 C24 H16 . . 108.700000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C19 C1 C2 C3 . . . . -0.4(4) ?
C1 C2 C3 C4 . . . . -1.0(3) ?
C1 C2 C3 C18 . . . . 177.6(2) ?
C2 C3 C4 C5 . . . . 179.52(17) ?
C18 C3 C4 C5 . . . . 0.8(3) ?
C2 C3 C4 C20 . . . . 1.8(3) ?
C18 C3 C4 C20 . . . . -176.89(17) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C20 C4 C5 C6 . . . . 178.11(16) ?
C4 C5 C6 C17 . . . . 0.3(2) ?
C4 C5 C6 C7 . . . . -174.75(15) ?
C5 C6 C7 C22 . . . . -58.5(2) ?
C17 C6 C7 C22 . . . . 126.49(17) ?
C5 C6 C7 C8 . . . . 117.81(17) ?
C17 C6 C7 C8 . . . . -57.2(2) ?
C22 C7 C8 C9 . . . . 0.9(2) ?
C6 C7 C8 C9 . . . . -175.50(15) ?
C7 C8 C9 C10 . . . . -1.6(3) ?
C8 C9 C10 C21 . . . . 0.6(3) ?
C16 C11 C12 C13 . . . . -1.6(3) ?
C11 C12 C13 C14 . . . . -1.6(3) ?
C11 C12 C13 C24 . . . . 173.9(2) ?
C12 C13 C14 C15 . . . . 2.7(3) ?
C24 C13 C14 C15 . . . . -173.00(17) ?
C12 C13 C14 C17 . . . . -177.26(17) ?
C24 C13 C14 C17 . . . . 7.0(2) ?
C13 C14 C15 C16 . . . . -0.8(2) ?
C17 C14 C15 C16 . . . . 179.18(16) ?
C12 C11 C16 C15 . . . . 3.5(3) ?
C14 C15 C16 C11 . . . . -2.3(3) ?
C5 C6 C17 C18 . . . . -2.4(2) ?
C7 C6 C17 C18 . . . . 172.56(15) ?
C5 C6 C17 C14 . . . . 175.29(15) ?
C7 C6 C17 C14 . . . . -9.8(2) ?
C13 C14 C17 C18 . . . . -49.7(2) ?
C15 C14 C17 C18 . . . . 130.35(17) ?
C13 C14 C17 C6 . . . . 132.72(17) ?
C15 C14 C17 C6 . . . . -47.2(2) ?
C6 C17 C18 N1 . . . . 179.16(17) ?
C14 C17 C18 N1 . . . . 1.5(3) ?
C6 C17 C18 C3 . . . . 3.7(2) ?
C14 C17 C18 C3 . . . . -173.94(15) ?
C23 N1 C18 C17 . . . . 45.7(3) ?
C23 N1 C18 C3 . . . . -138.6(2) ?
C2 C3 C18 C17 . . . . 178.43(18) ?
C4 C3 C18 C17 . . . . -3.0(3) ?
C2 C3 C18 N1 . . . . 2.6(3) ?
C4 C3 C18 N1 . . . . -178.81(17) ?
C2 C1 C19 C20 . . . . 1.1(4) ?
C1 C19 C20 C4 . . . . -0.3(4) ?
C3 C4 C20 C19 . . . . -1.1(3) ?
C5 C4 C20 C19 . . . . -178.8(2) ?
C9 C10 C21 C22 . . . . 1.0(3) ?
C10 C21 C22 C7 . . . . -1.7(3) ?
C8 C7 C22 C21 . . . . 0.7(3) ?
C6 C7 C22 C21 . . . . 177.09(17) ?
C18 N1 C23 C24 . . . . -2.6(3) ?
N1 C23 C24 C13 . . . . -70.3(3) ?
C12 C13 C24 C23 . . . . -112.1(2) ?
C14 C13 C24 C23 . . . . 63.5(2) ?



