# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

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

data_11
_database_code_depnum_ccdc_archive 'CCDC 2118497'
loop_
_audit_author_name
_audit_author_address
'we sd'
;SHZ University
China
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_audit_creation_date             2021-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 N'
_chemical_formula_sum            'C19 H14 N'
_chemical_formula_weight         256.31
_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           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   14.1719(5)
_cell_length_b                   8.9226(3)
_cell_length_c                   5.6638(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     716.19(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5296
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.04
_cell_measurement_theta_min      5.86
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1108 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.8730. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8521
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.166
_diffrn_reflns_theta_min         4.956
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1360
_reflns_number_total             1417
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.008(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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1417
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.091
_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)+(0.0518P)²+0.0881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C10A \\sim C10 \\sim C9 \\sim C9A \\sim C9 \\sim C9A: within 3.8A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C10) \\sim Ueq, Uanis(C10A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C7, C9, C10, C9, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C9A, C10A, C9A, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C10A)=Sof(H10C)=Sof(H10D)=0.5*(1-FVAR(2))
 Sof(C10)=Sof(H10A)=Sof(H10B)=0.5*FVAR(2)
 Sof(C9)=Sof(H9)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C9A(H9A)
;
_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
N1 N 0.500000 0.5086(3) 0.4554(6) 0.0432(7) Uani 1 2 d S T P A .
C1 C 0.32068(13) 0.2191(2) 0.4977(4) 0.0325(5) Uani 1 1 d . . . . .
C2 C 0.30559(14) 0.2998(2) 0.2902(4) 0.0355(5) Uani 1 1 d . . . . .
H2 H 0.354625 0.307638 0.176523 0.043 Uiso 1 1 calc R . . . .
C3 C 0.21935(15) 0.3687(2) 0.2489(5) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.209303 0.422054 0.105948 0.048 Uiso 1 1 calc R . . . .
C4 C 0.14823(14) 0.3600(3) 0.4143(5) 0.0440(6) Uani 1 1 d . . . . .
H4 H 0.089883 0.409492 0.387123 0.053 Uiso 1 1 calc R . . . .
C5 C 0.16179(16) 0.2796(3) 0.6189(5) 0.0466(6) Uani 1 1 d . . . . .
H5 H 0.112516 0.272583 0.732051 0.056 Uiso 1 1 calc R . . . .
C6 C 0.24743(16) 0.2088(2) 0.6599(4) 0.0425(5) Uani 1 1 d . . . . .
H6 H 0.256068 0.152512 0.800679 0.051 Uiso 1 1 calc R . . . .
C7 C 0.41244(14) 0.1455(2) 0.5475(4) 0.0397(5) Uani 1 1 d . U . . .
C8 C 0.500000 0.2211(3) 0.5197(5) 0.0315(6) Uani 1 2 d S T P A .
C11 C 0.500000 0.3807(3) 0.4813(6) 0.0315(6) Uani 1 2 d S T P . .
C9 C 0.4098(6) 0.0078(12) 0.669(3) 0.055(2) Uani 0.57(2) 1 d . U . A 1
H9 H 0.352740 -0.047498 0.680275 0.066 Uiso 0.57(2) 1 calc R . . A 1
C9A C 0.4219(9) -0.0183(12) 0.575(3) 0.046(2) Uani 0.43(2) 1 d . U . A 2
H9A H 0.376237 -0.084433 0.509593 0.056 Uiso 0.43(2) 1 calc R . . A 2
C10 C 0.500000 -0.0506(14) 0.781(3) 0.051(2) Uani 0.57(2) 2 d S TU P A 1
H10A H 0.499999 -0.161376 0.770898 0.061 Uiso 0.57(2) 2 calc RS T P A 1
H10B H 0.500001 -0.023065 0.950013 0.061 Uiso 0.57(2) 2 calc RS T P A 1
C10A C 0.500000 -0.0739(15) 0.699(3) 0.040(3) Uani 0.43(2) 2 d S TU P A 2
H10C H 0.499999 -0.184809 0.700675 0.048 Uiso 0.43(2) 2 calc RS T P A 2
H10D H 0.500000 -0.037030 0.864209 0.048 Uiso 0.43(2) 2 calc RS T P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.150(4) . ?
C1 C2 1.395(3) . ?
C1 C6 1.389(3) . ?
C1 C7 1.484(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.421(2) . ?
C7 C9 1.408(9) . ?
C7 C9A 1.476(11) . ?
C8 C11 1.440(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.519(10) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.403(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?

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 C7 121.55(19) . . ?
C6 C1 C2 118.48(18) . . ?
C6 C1 C7 120.0(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.96(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C1 122.27(17) . . ?
C8 C7 C9A 113.8(5) . . ?
C9 C7 C1 117.1(4) . . ?
C9 C7 C8 119.4(4) . . ?
C9A C7 C1 122.5(5) . . ?
C7 C8 C7 121.6(2) . 3_655 ?
C7 C8 C11 119.09(11) 3_655 . ?
C7 C8 C11 119.09(11) . . ?
N1 C11 C8 178.6(3) . . ?
C7 C9 H9 120.6 . . ?
C7 C9 C10 118.7(7) . . ?
C10 C9 H9 120.6 . . ?
C7 C9A H9A 120.9 . . ?
C10A C9A C7 118.3(8) . . ?
C10A C9A H9A 120.9 . . ?
C9 C10 C9 114.6(8) . 3_655 ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 3_655 . ?
C9 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 3_655 . ?
H10A C10 H10B 107.6 . . ?
C9A C10A C9A 104.2(12) . 3_655 ?
C9A C10A H10C 110.9 . . ?
C9A C10A H10C 110.9 3_655 . ?
C9A C10A H10D 110.9 . . ?
C9A C10A H10D 110.9 3_655 . ?
H10C C10A H10D 108.9 . . ?

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 C7 C8 C7 -174.26(17) . . . 3_655 ?
C1 C7 C8 C11 10.9(4) . . . . ?
C1 C7 C9 C10 -163.8(6) . . . . ?
C1 C7 C9A C10A -158.0(7) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C2 C1 C7 C8 47.8(3) . . . . ?
C2 C1 C7 C9 -144.7(8) . . . . ?
C2 C1 C7 C9A -117.5(8) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C1 C7 C8 -132.0(2) . . . . ?
C6 C1 C7 C9 35.5(8) . . . . ?
C6 C1 C7 C9A 62.7(8) . . . . ?
C7 C1 C2 C3 -179.42(19) . . . . ?
C7 C1 C6 C5 178.55(19) . . . . ?
C7 C9 C10 C9 -24.6(16) . . . 3_655 ?
C7 C9A C10A C9A -58.4(15) . . . 3_655 ?
C8 C7 C9 C10 4.1(12) . . . . ?
C8 C7 C9A C10A 35.5(12) . . . . ?
C9 C7 C8 C7 18.5(9) . . . 3_655 ?
C9 C7 C8 C11 -156.4(8) . . . . ?
C9A C7 C8 C7 -7.8(8) . . . 3_655 ?
C9A C7 C8 C11 177.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
