# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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#######################################################################

data_mo_201127c_0m
_database_code_depnum_ccdc_archive 'CCDC 2055069'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Central China Normal University
China
;
_audit_update_record             
;
2021-01-11 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2020-12-04
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_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 0.0033 0.0016 '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 0.0061 0.0033 '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                   9.856(4)
_cell_length_b                   4.9044(18)
_cell_length_c                   12.905(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.965(7)
_cell_angle_gamma                90
_cell_volume                     623.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1131
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.18
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3871
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                703
_reflns_number_total             1058
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.604
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1058
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.1493
_refine_ls_R_factor_gt           0.1243
_refine_ls_restrained_S_all      1.729
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3495
_refine_ls_wR_factor_ref         0.3918
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2. Restrained distances 
 C8-C4 
 1.42 with sigma of 0.01 
 N2-C5 = N2-C9 = N1-C9 = N1-C8 
 1.38 with sigma of 0.01 
 C9-C10 
 1.45 with sigma of 0.02 
 C8-C4 = N1-C8 = N1-C9 = N2-C9 = N2-C5 
 1.39 with sigma of 0.01 
 C3-C1 \\sim C1-C7 
 with sigma of 0.01 
 C12-C16 \\sim C16-C14 
 with sigma of 0.01 
 C10-N1 \\sim N1-N2 
 with sigma of 0.01 
 C11-C9 \\sim C9-C15 
 with sigma of 0.01 
3. Uiso/Uaniso restraints and constraints 
Uanis(C5) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(N1) \\sim 
Ueq, Uanis(C10) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C11) \\sim Ueq, 
Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 
4. Others 
 Fixed Sof: C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5) C1(0.5) H1A(0.5) H1B(0.5) 
 H1C(0.5) C13(0.5) C12(0.5) H12(0.5) C11(0.5) H11(0.5) C10(0.5) C15(0.5) 
 H15(0.5) C14(0.5) H14(0.5) C2(0.5) C7(0.5) H7(0.5) C6(0.5) H6(0.5) C5(0.5) 
 C4(0.5) C3(0.5) H3(0.5) C8(0.5) H8(0.5) C9(0.5) N1(0.5) N2(0.5) 
5.a Aromatic/amide H refined with riding coordinates: 
 C12(H12), C11(H11), C15(H15), C14(H14), C7(H7), C6(H6), C3(H3), C8(H8) 
5.b Fitted hexagon refined as free rotating group: 
 C13(C12,C11,C10,C15,C14), C2(C7,C6,C5,C4,C3) 
5.c Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C) 
;
_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
C16 C 0.1001(14) 1.346(4) -0.1659(11) 0.060(3) Uani 0.5 1 d D . P A -1
H16A H 0.0620 1.4455 -0.1104 0.089 Uiso 0.5 1 calc GR . P A -1
H16B H 0.0286 1.2573 -0.2065 0.089 Uiso 0.5 1 calc GR . P A -1
H16C H 0.1473 1.4695 -0.2092 0.089 Uiso 0.5 1 calc GR . P A -1
C1 C 0.9283(17) -0.362(4) 0.1387(11) 0.064(4) Uani 0.5 1 d D . P A -1
H1A H 0.9969 -0.3988 0.0904 0.095 Uiso 0.5 1 calc GR . P A -1
H1B H 0.8825 -0.5283 0.1546 0.095 Uiso 0.5 1 calc GR . P A -1
H1C H 0.9698 -0.2862 0.2011 0.095 Uiso 0.5 1 calc GR . P A -1
C13 C 0.1949(9) 1.1418(18) -0.1231(6) 0.041(2) Uani 0.5 1 d . . P A -1
C12 C 0.1918(8) 1.0689(18) -0.0192(5) 0.055(2) Uani 0.5 1 d DG . P A -1
H12 H 0.1302 1.1518 0.0230 0.065 Uiso 0.5 1 calc R . P A -1
C11 C 0.2808(9) 0.8719(18) 0.0217(5) 0.064(2) Uani 0.5 1 d DG U P A -1
H11 H 0.2787 0.8231 0.0912 0.077 Uiso 0.5 1 calc R . P A -1
C10 C 0.3728(9) 0.7479(17) -0.0414(5) 0.065(3) Uani 0.5 1 d DG U P A -1
C15 C 0.3759(9) 0.8208(19) -0.1453(5) 0.072(3) Uani 0.5 1 d DG U P A -1
H15 H 0.4375 0.7378 -0.1875 0.087 Uiso 0.5 1 calc R . P A -1
C14 C 0.2870(10) 1.018(2) -0.1862(4) 0.053(2) Uani 0.5 1 d DG . P A -1
H14 H 0.2890 1.0665 -0.2557 0.064 Uiso 0.5 1 calc R . P A -1
C2 C 0.8218(10) -0.151(2) 0.0887(6) 0.053(3) Uani 0.5 1 d . . P A -1
C7 C 0.8258(11) -0.080(2) -0.0153(6) 0.068(3) Uani 0.5 1 d DG . P A -1
H7 H 0.8900 -0.1587 -0.0564 0.082 Uiso 0.5 1 calc R . P A -1
C6 C 0.7338(12) 0.109(2) -0.0581(5) 0.083(3) Uani 0.5 1 d G U P A -1
H6 H 0.7365 0.1565 -0.1277 0.099 Uiso 0.5 1 calc R . P A -1
C5 C 0.6379(10) 0.2269(19) 0.0032(6) 0.067(3) Uani 0.5 1 d DG U P A -1
C4 C 0.6339(9) 0.1559(19) 0.1073(6) 0.059(2) Uani 0.5 1 d DG . P A -1
C3 C 0.7258(10) -0.033(2) 0.1500(5) 0.058(3) Uani 0.5 1 d DG . P A -1
H3 H 0.7232 -0.0804 0.2197 0.070 Uiso 0.5 1 calc R . P A -1
C8 C 0.5355(8) 0.2986(15) 0.1594(6) 0.080(2) Uani 0.5 1 d D . P A -1
H8 H 0.5269 0.2596 0.2293 0.096 Uiso 0.5 1 calc R . P A -1
C9 C 0.4684(9) 0.5417(18) 0.0096(5) 0.063(3) Uani 0.5 1 d D U P A -1
N1 N 0.4501(6) 0.4938(12) 0.1146(4) 0.073(2) Uani 0.5 1 d D U P A -1
N2 N 0.5585(9) 0.4190(19) -0.0505(6) 0.076(3) Uani 0.5 1 d D U P A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C13 1.46(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.59(2) . ?
C13 C12 1.3900 . ?
C13 C14 1.3900 . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 C15 1.3900 . ?
C10 C9 1.510(9) . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 H14 0.9300 . ?
C2 C7 1.3900 . ?
C2 C3 1.3900 . ?
C7 H7 0.9300 . ?
C7 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C5 N2 1.387(6) . ?
C4 C3 1.3900 . ?
C4 C8 1.397(6) . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C8 N1 1.382(6) . ?
C9 N1 1.396(6) . ?
C9 N2 1.351(6) . ?

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
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C12 C13 C16 119.8(4) . . ?
C12 C13 C14 120.0 . . ?
C14 C13 C16 120.2(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 C15 120.0 . . ?
C11 C10 C9 116.7(3) . . ?
C15 C10 C9 123.3(3) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C7 C2 C1 120.3(4) . . ?
C7 C2 C3 120.0 . . ?
C3 C2 C1 119.7(4) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 C4 120.0 . . ?
N2 C5 C6 112.4(6) . . ?
N2 C5 C4 127.6(6) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C8 113.3(6) . . ?
C3 C4 C8 126.7(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C8 H8 117.7 . . ?
N1 C8 C4 124.6(7) . . ?
N1 C8 H8 117.7 . . ?
N1 C9 C10 115.3(5) . . ?
N2 C9 C10 117.5(5) . . ?
N2 C9 N1 127.2(6) . . ?
C8 N1 C9 114.6(6) . . ?
C9 N2 C5 112.7(7) . . ?

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
C16 C13 C12 C11 179.2(10) . . . . ?
C16 C13 C14 C15 -179.2(10) . . . . ?
C1 C2 C7 C6 -178.8(12) . . . . ?
C1 C2 C3 C4 178.8(11) . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C12 C11 C10 C15 0.0 . . . . ?
C12 C11 C10 C9 178.4(9) . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C11 C10 C9 N1 1.8(10) . . . . ?
C11 C10 C9 N2 180.0(6) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
C10 C9 N1 C8 178.1(7) . . . . ?
C10 C9 N2 C5 -177.9(11) . . . . ?
C15 C10 C9 N1 -179.9(6) . . . . ?
C15 C10 C9 N2 -1.7(11) . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C2 C7 C6 C5 0.0 . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C7 C6 C5 N2 177.3(9) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C5 C4 C8 177.8(8) . . . . ?
C6 C5 N2 C9 -177.7(7) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C4 C8 N1 -0.6(10) . . . . ?
C4 C5 N2 C9 -0.6(13) . . . . ?
C4 C8 N1 C9 0.1(11) . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C3 C4 C8 N1 177.0(7) . . . . ?
C8 C4 C3 C2 -177.4(10) . . . . ?
C9 C10 C15 C14 -178.3(9) . . . . ?
N1 C9 N2 C5 0.0(12) . . . . ?
N2 C5 C4 C3 -176.9(11) . . . . ?
N2 C5 C4 C8 0.9(12) . . . . ?
N2 C9 N1 C8 0.2(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
