# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ZXM_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2078447'
loop_
_audit_author_name
_audit_author_address
'xiaomin Zhang'
;xian jiao tong university
China
;

_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;
_publcif_datablock.id            {59e1dc38-2cea-46e3-87f9-2957d0b094c0}

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21

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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   14.159(3)
_cell_length_b                   17.002(4)
_cell_length_c                   7.4730(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1799.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4987
_cell_measurement_theta_min      4.792
_cell_measurement_theta_max      50.713
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   0.989
_exptl_transmission_factor_max   0.991
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS;Bruker,2000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15648
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_full        25.021
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1593
_reflns_number_gt                1305
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0423P)²+0.5264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1593
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.41470(7) 0.55705(6) 0.65911(13) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.39680(9) 0.47622(7) 0.67144(16) 0.0275(3) Uani 1 1 d . . . . .
N2 N 0.45293(8) 0.60114(7) 0.79214(15) 0.0354(3) Uani 1 1 d . . . . .
C2 C 0.41796(9) 0.43354(8) 0.82519(17) 0.0325(3) Uani 1 1 d . . . . .
H1 H 0.443585 0.458419 0.924819 0.039 Uiso 1 1 calc R U . . .
C3 C 0.40034(10) 0.35375(9) 0.8275(2) 0.0382(4) Uani 1 1 d . . . . .
H2 H 0.415251 0.324365 0.928609 0.046 Uiso 1 1 calc R U . . .
N3 N 0.45839(9) 0.67379(7) 0.72973(16) 0.0399(3) Uani 1 1 d . . . . .
C4 C 0.36028(10) 0.31694(8) 0.6790(2) 0.0399(4) Uani 1 1 d . . . . .
H3 H 0.348297 0.263174 0.681881 0.048 Uiso 1 1 calc R U . . .
C5 C 0.33838(9) 0.35965(8) 0.5284(2) 0.0364(4) Uani 1 1 d . . . . .
H4 H 0.310882 0.334421 0.431060 0.044 Uiso 1 1 calc R U . . .
C6 C 0.35686(9) 0.44089(8) 0.51900(17) 0.0292(3) Uani 1 1 d . . . . .
C7 C 0.33644(9) 0.48768(8) 0.36278(17) 0.0320(3) Uani 1 1 d . . . . .
H5 H 0.310115 0.463245 0.263240 0.038 Uiso 1 1 calc R U . . .
C8 C 0.35412(9) 0.56565(8) 0.35569(17) 0.0307(3) Uani 1 1 d . . . . .
C9 C 0.39594(9) 0.60180(8) 0.51115(17) 0.0282(3) Uani 1 1 d . . . . .
C10 C 0.42480(10) 0.67595(8) 0.56019(19) 0.0350(3) Uani 1 1 d . . . . .
H6 H 0.421725 0.720522 0.488283 0.042 Uiso 1 1 calc R U . . .
C11 C 0.33177(10) 0.61737(9) 0.19849(19) 0.0424(4) Uani 1 1 d . . . . .
H7 H 0.387361 0.645920 0.164026 0.064 Uiso 1 1 calc R U . . .
H8 H 0.282820 0.653768 0.230760 0.064 Uiso 1 1 calc R U . . .
H9 H 0.310836 0.585483 0.100168 0.064 Uiso 1 1 calc R U . . .


_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 N2 1.3577(15) . ?
N1 C9 1.3683(16) . ?
N1 C1 1.4004(17) . ?
C1 C2 1.3916(18) . ?
C1 C6 1.4065(17) . ?
N2 N3 1.3226(16) . ?
C2 C3 1.379(2) . ?
C2 H1 0.9300 . ?
C3 C4 1.395(2) . ?
C3 H2 0.9300 . ?
N3 C10 1.3538(19) . ?
C4 C5 1.375(2) . ?
C4 H3 0.9300 . ?
C5 C6 1.4076(19) . ?
C5 H4 0.9300 . ?
C6 C7 1.4420(18) . ?
C7 C8 1.350(2) . ?
C7 H5 0.9300 . ?
C8 C9 1.4415(18) . ?
C8 C11 1.5011(19) . ?
C9 C10 1.3750(19) . ?
C10 H6 0.9300 . ?
C11 H7 0.9600 . ?
C11 H8 0.9600 . ?
C11 H9 0.9600 . ?

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
N2 N1 C9 111.23(11) . . ?
N2 N1 C1 124.46(11) . . ?
C9 N1 C1 124.31(11) . . ?
C2 C1 N1 121.80(11) . . ?
C2 C1 C6 122.18(12) . . ?
N1 C1 C6 116.01(11) . . ?
N3 N2 N1 106.31(11) . . ?
C3 C2 C1 118.97(13) . . ?
C3 C2 H1 120.5 . . ?
C1 C2 H1 120.5 . . ?
C2 C3 C4 120.32(13) . . ?
C2 C3 H2 119.8 . . ?
C4 C3 H2 119.8 . . ?
N2 N3 C10 109.56(11) . . ?
C5 C4 C3 120.41(13) . . ?
C5 C4 H3 119.8 . . ?
C3 C4 H3 119.8 . . ?
C4 C5 C6 121.15(13) . . ?
C4 C5 H4 119.4 . . ?
C6 C5 H4 119.4 . . ?
C1 C6 C5 116.95(13) . . ?
C1 C6 C7 120.05(12) . . ?
C5 C6 C7 122.99(12) . . ?
C8 C7 C6 122.43(12) . . ?
C8 C7 H5 118.8 . . ?
C6 C7 H5 118.8 . . ?
C7 C8 C9 117.59(12) . . ?
C7 C8 C11 124.53(13) . . ?
C9 C8 C11 117.87(12) . . ?
N1 C9 C10 103.69(11) . . ?
N1 C9 C8 119.60(12) . . ?
C10 C9 C8 136.70(13) . . ?
N3 C10 C9 109.21(12) . . ?
N3 C10 H6 125.4 . . ?
C9 C10 H6 125.4 . . ?
C8 C11 H7 109.5 . . ?
C8 C11 H8 109.5 . . ?
H7 C11 H8 109.5 . . ?
C8 C11 H9 109.5 . . ?
H7 C11 H9 109.5 . . ?
H8 C11 H9 109.5 . . ?

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
N2 N1 C1 C2 -0.39(19) . . . . ?
C9 N1 C1 C2 179.56(12) . . . . ?
N2 N1 C1 C6 -179.98(11) . . . . ?
C9 N1 C1 C6 -0.03(17) . . . . ?
C9 N1 N2 N3 0.15(14) . . . . ?
C1 N1 N2 N3 -179.89(11) . . . . ?
N1 C1 C2 C3 -178.71(12) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
N1 N2 N3 C10 -0.30(14) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C2 C1 C6 C5 0.34(19) . . . . ?
N1 C1 C6 C5 179.93(11) . . . . ?
C2 C1 C6 C7 -179.86(11) . . . . ?
N1 C1 C6 C7 -0.27(17) . . . . ?
C4 C5 C6 C1 -1.22(19) . . . . ?
C4 C5 C6 C7 178.99(12) . . . . ?
C1 C6 C7 C8 -0.08(19) . . . . ?
C5 C6 C7 C8 179.71(12) . . . . ?
C6 C7 C8 C9 0.70(19) . . . . ?
C6 C7 C8 C11 -178.23(12) . . . . ?
N2 N1 C9 C10 0.05(14) . . . . ?
C1 N1 C9 C10 -179.91(11) . . . . ?
N2 N1 C9 C8 -179.39(11) . . . . ?
C1 N1 C9 C8 0.65(18) . . . . ?
C7 C8 C9 N1 -0.97(18) . . . . ?
C11 C8 C9 N1 178.03(11) . . . . ?
C7 C8 C9 C10 179.82(15) . . . . ?
C11 C8 C9 C10 -1.2(2) . . . . ?
N2 N3 C10 C9 0.34(16) . . . . ?
N1 C9 C10 N3 -0.24(15) . . . . ?
C8 C9 C10 N3 179.05(14) . . . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.031


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
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