# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_mo_d8v20106_0m
_database_code_depnum_ccdc_archive 'CCDC 1996923'
loop_
_audit_author_name
_audit_author_address
'Chenxu Yan'
;East China University Of Science and Technology
China
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        QM-NH2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N4'
_chemical_formula_weight         338.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   7.3713(4)
_cell_length_b                   11.8588(6)
_cell_length_c                   20.5481(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.123(2)
_cell_angle_gamma                90
_cell_volume                     1794.97(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2482
_cell_measurement_theta_min      5.530
_cell_measurement_theta_max      49.243

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8798
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3494
_reflns_number_gt                2219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.1439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3494
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.24291(19) 0.44735(11) 0.38195(8) 0.0534(4) Uani 1 1 d . . . . .
N2 N 0.5205(3) 1.15700(14) 0.29002(12) 0.0727(6) Uani 1 1 d . . . . .
N3 N 0.2957(3) 0.64674(15) 0.63873(9) 0.0798(6) Uani 1 1 d . . . . .
N4 N 0.1900(3) 0.30206(15) 0.67555(10) 0.0838(6) Uani 1 1 d . . . . .
C1 C 0.1876(2) 0.34947(14) 0.41326(11) 0.0557(5) Uani 1 1 d . . . . .
C2 C 0.1437(3) 0.25269(16) 0.37611(12) 0.0712(6) Uani 1 1 d . . . . .
H2 H 0.1591 0.2528 0.3314 0.085 Uiso 1 1 calc R U . . .
C3 C 0.0788(3) 0.15871(17) 0.40577(15) 0.0866(8) Uani 1 1 d . . . . .
H3 H 0.0522 0.0946 0.3811 0.104 Uiso 1 1 calc R U . . .
C4 C 0.0522(4) 0.15777(17) 0.47174(14) 0.0889(8) Uani 1 1 d . . . . .
H4 H 0.0032 0.0943 0.4910 0.107 Uiso 1 1 calc R U . . .
C5 C 0.0975(3) 0.24977(15) 0.50902(11) 0.0731(6) Uani 1 1 d . . . . .
H5 H 0.0803 0.2475 0.5536 0.088 Uiso 1 1 calc R U . . .
C6 C 0.1695(2) 0.34778(14) 0.48132(10) 0.0539(5) Uani 1 1 d . . . . .
C7 C 0.2169(2) 0.44659(13) 0.51923(10) 0.0508(5) Uani 1 1 d . . . . .
C8 C 0.2544(2) 0.54276(14) 0.48311(10) 0.0525(5) Uani 1 1 d . . . . .
H8 H 0.2719 0.6102 0.5056 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2673(2) 0.54466(14) 0.41691(10) 0.0513(5) Uani 1 1 d . . . . .
C10 C 0.2998(2) 0.64984(14) 0.38288(10) 0.0550(5) Uani 1 1 d . . . . .
H10 H 0.2611 0.6550 0.3394 0.066 Uiso 1 1 calc R U . . .
C11 C 0.3818(2) 0.73949(14) 0.41010(10) 0.0564(5) Uani 1 1 d . . . . .
H11 H 0.4271 0.7309 0.4527 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4077(2) 0.84935(14) 0.38017(10) 0.0535(5) Uani 1 1 d . . . . .
C13 C 0.5224(3) 0.92882(16) 0.41041(11) 0.0664(6) Uani 1 1 d . . . . .
H13 H 0.5764 0.9121 0.4509 0.080 Uiso 1 1 calc R U . . .
C14 C 0.5580(3) 1.03120(16) 0.38191(11) 0.0676(6) Uani 1 1 d . . . . .
H14 H 0.6356 1.0821 0.4032 0.081 Uiso 1 1 calc R U . . .
C15 C 0.4792(3) 1.05899(14) 0.32183(10) 0.0557(5) Uani 1 1 d . . . . .
C16 C 0.3583(3) 0.98190(15) 0.29306(10) 0.0580(5) Uani 1 1 d . . . . .
H16 H 0.2991 1.0001 0.2537 0.070 Uiso 1 1 calc R U . . .
C17 C 0.3249(3) 0.88014(15) 0.32130(10) 0.0564(5) Uani 1 1 d . . . . .
H17 H 0.2444 0.8303 0.3005 0.068 Uiso 1 1 calc R U . . .
C18 C 0.2827(3) 0.44466(16) 0.31190(10) 0.0620(6) Uani 1 1 d . . . . .
H18A H 0.3360 0.3722 0.3019 0.074 Uiso 1 1 calc R U . . .
H18B H 0.3720 0.5023 0.3033 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1187(3) 0.46316(18) 0.26711(11) 0.0770(7) Uani 1 1 d . . . . .
H19A H 0.1526 0.4548 0.2227 0.116 Uiso 1 1 calc R U . . .
H19B H 0.0720 0.5377 0.2735 0.116 Uiso 1 1 calc R U . . .
H19C H 0.0269 0.4087 0.2766 0.116 Uiso 1 1 calc R U . . .
C20 C 0.2215(2) 0.45426(14) 0.58793(10) 0.0535(5) Uani 1 1 d . . . . .
C21 C 0.2627(3) 0.56043(17) 0.61668(10) 0.0587(5) Uani 1 1 d . . . . .
C22 C 0.2021(3) 0.36684(16) 0.63443(11) 0.0615(5) Uani 1 1 d . . . . .
H2A H 0.577(3) 1.2078(18) 0.3128(10) 0.079(7) Uiso 1 1 d . . . . .
H2B H 0.440(4) 1.180(2) 0.2545(13) 0.113(10) Uiso 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
N1 C9 1.368(2) . ?
N1 C1 1.395(2) . ?
N1 C18 1.480(2) . ?
N2 C15 1.373(2) . ?
N2 H2A 0.86(2) . ?
N2 H2B 0.96(3) . ?
N3 C21 1.142(2) . ?
N4 C22 1.148(2) . ?
C1 C2 1.409(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(2) . ?
C7 C8 1.394(2) . ?
C7 C20 1.414(3) . ?
C8 C9 1.367(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.454(2) . ?
C10 C11 1.335(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.456(2) . ?
C11 H11 0.9300 . ?
C12 C17 1.384(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(2) . ?
C16 C17 1.365(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.508(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.419(3) . ?
C20 C22 1.421(3) . ?

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
C9 N1 C1 119.65(17) . . ?
C9 N1 C18 120.14(15) . . ?
C1 N1 C18 120.16(15) . . ?
C15 N2 H2A 116.4(15) . . ?
C15 N2 H2B 117.3(15) . . ?
H2A N2 H2B 119(2) . . ?
N1 C1 C2 119.52(19) . . ?
N1 C1 C6 120.62(16) . . ?
C2 C1 C6 119.83(17) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.65(18) . . ?
C5 C6 C7 122.69(19) . . ?
C1 C6 C7 119.60(16) . . ?
C8 C7 C20 118.76(16) . . ?
C8 C7 C6 115.20(18) . . ?
C20 C7 C6 126.00(16) . . ?
C9 C8 C7 124.45(17) . . ?
C9 C8 H8 117.8 . . ?
C7 C8 H8 117.8 . . ?
C8 C9 N1 119.73(16) . . ?
C8 C9 C10 120.75(16) . . ?
N1 C9 C10 119.48(18) . . ?
C11 C10 C9 124.17(19) . . ?
C11 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C10 C11 C12 126.84(19) . . ?
C10 C11 H11 116.6 . . ?
C12 C11 H11 116.6 . . ?
C17 C12 C13 116.82(17) . . ?
C17 C12 C11 123.02(17) . . ?
C13 C12 C11 120.16(19) . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.59(18) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
N2 C15 C14 122.19(19) . . ?
N2 C15 C16 120.2(2) . . ?
C14 C15 C16 117.58(17) . . ?
C17 C16 C15 121.49(19) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 121.60(18) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
N1 C18 C19 114.03(16) . . ?
N1 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
N1 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C20 C21 118.02(16) . . ?
C7 C20 C22 128.71(16) . . ?
C21 C20 C22 113.13(18) . . ?
N3 C21 C20 178.8(2) . . ?
N4 C22 C20 174.8(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
C9 N1 C1 C2 173.23(16) . . . . ?
C18 N1 C1 C2 -9.4(3) . . . . ?
C9 N1 C1 C6 -4.7(3) . . . . ?
C18 N1 C1 C6 172.67(16) . . . . ?
N1 C1 C2 C3 -175.97(19) . . . . ?
C6 C1 C2 C3 2.0(3) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C3 C4 C5 -2.6(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 2.2(3) . . . . ?
C4 C5 C6 C7 179.4(2) . . . . ?
N1 C1 C6 C5 174.35(16) . . . . ?
C2 C1 C6 C5 -3.6(3) . . . . ?
N1 C1 C6 C7 -2.9(3) . . . . ?
C2 C1 C6 C7 179.15(17) . . . . ?
C5 C6 C7 C8 -168.67(17) . . . . ?
C1 C6 C7 C8 8.5(2) . . . . ?
C5 C6 C7 C20 8.9(3) . . . . ?
C1 C6 C7 C20 -173.95(17) . . . . ?
C20 C7 C8 C9 175.04(16) . . . . ?
C6 C7 C8 C9 -7.2(3) . . . . ?
C7 C8 C9 N1 -0.1(3) . . . . ?
C7 C8 C9 C10 177.53(16) . . . . ?
C1 N1 C9 C8 6.3(2) . . . . ?
C18 N1 C9 C8 -171.06(16) . . . . ?
C1 N1 C9 C10 -171.37(15) . . . . ?
C18 N1 C9 C10 11.3(2) . . . . ?
C8 C9 C10 C11 25.1(3) . . . . ?
N1 C9 C10 C11 -157.22(17) . . . . ?
C9 C10 C11 C12 -175.61(16) . . . . ?
C10 C11 C12 C17 10.0(3) . . . . ?
C10 C11 C12 C13 -169.09(19) . . . . ?
C17 C12 C13 C14 -2.7(3) . . . . ?
C11 C12 C13 C14 176.44(18) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 N2 -175.66(19) . . . . ?
C13 C14 C15 C16 2.5(3) . . . . ?
N2 C15 C16 C17 175.12(18) . . . . ?
C14 C15 C16 C17 -3.1(3) . . . . ?
C15 C16 C17 C12 0.8(3) . . . . ?
C13 C12 C17 C16 2.1(3) . . . . ?
C11 C12 C17 C16 -176.98(17) . . . . ?
C9 N1 C18 C19 -95.8(2) . . . . ?
C1 N1 C18 C19 86.8(2) . . . . ?
C8 C7 C20 C21 0.6(3) . . . . ?
C6 C7 C20 C21 -176.90(17) . . . . ?
C8 C7 C20 C22 -174.69(18) . . . . ?
C6 C7 C20 C22 7.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B N4 0.96(3) 2.42(3) 3.358(3) 165(2) 4_575
N2 H2A N3 0.86(2) 2.19(2) 3.041(3) 172(2) 3_676

_refine_diff_density_max         0.113
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4



