# Supplementary Information (SI) for ChemComm.
# 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_JW_imine_2
_database_code_depnum_ccdc_archive 'CCDC 2370061'
loop_
_audit_author_name
_audit_author_address
'Olga Anhalt'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2024-07-11 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
(E)-N,1-bis(1-methyl-1H-pyrazol-4-yl)methanimine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N5'
_chemical_formula_sum            'C9 H11 N5'
_chemical_formula_weight         189.23

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'

_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                   12.5417(18)
_cell_length_b                   8.2315(10)
_cell_length_c                   9.3787(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.952(7)
_cell_angle_gamma                90
_cell_volume                     947.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      72.33

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.710
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18611
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.602
_diffrn_reflns_theta_max         72.323
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1870
_reflns_number_gt                1723
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0407P)²+0.3303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1870
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.29195(7) 0.66563(11) 0.69622(9) 0.0216(2) Uani 1 1 d . . . . .
N2 N 0.28870(8) 0.81506(11) 0.63337(10) 0.0235(2) Uani 1 1 d . . . . .
N3 N 0.61571(7) 0.75900(11) 0.55726(10) 0.0230(2) Uani 1 1 d . . . . .
N4 N 0.88372(7) 0.72597(11) 0.49047(10) 0.0228(2) Uani 1 1 d . . . . .
N5 N 0.88630(8) 0.58895(11) 0.57129(10) 0.0252(2) Uani 1 1 d . . . . .
C1 C 0.55958(9) 0.65651(13) 0.61368(11) 0.0228(2) Uani 1 1 d . . . . .
H1 H 0.590751 0.553627 0.643362 0.027 Uiso 1 1 calc R U . . .
C2 C 0.45066(9) 0.69121(13) 0.63397(11) 0.0218(2) Uani 1 1 d . . . . .
C3 C 0.38656(9) 0.58921(13) 0.69830(11) 0.0234(2) Uani 1 1 d . . . . .
H3 H 0.406115 0.484135 0.736895 0.028 Uiso 1 1 calc R U . . .
C4 C 0.38496(9) 0.83018(13) 0.59567(11) 0.0228(2) Uani 1 1 d . . . . .
H4 H 0.406729 0.923074 0.548756 0.027 Uiso 1 1 calc R U . . .
C5 C 0.19886(9) 0.60687(14) 0.75085(12) 0.0258(3) Uani 1 1 d . . . . .
H5A H 0.189073 0.673919 0.833533 0.039 Uiso 1 1 calc R U . . .
H5B H 0.211395 0.493782 0.782558 0.039 Uiso 1 1 calc R U . . .
H5C H 0.133258 0.613257 0.673337 0.039 Uiso 1 1 calc R U . . .
C6 C 0.72214(9) 0.71405(13) 0.54626(11) 0.0216(2) Uani 1 1 d . . . . .
C7 C 0.78725(9) 0.80409(13) 0.47379(12) 0.0234(2) Uani 1 1 d . . . . .
H7 H 0.767814 0.902477 0.421966 0.028 Uiso 1 1 calc R U . . .
C8 C 0.97983(9) 0.77465(15) 0.43780(13) 0.0290(3) Uani 1 1 d . . . . .
H8A H 1.029727 0.833288 0.514941 0.044 Uiso 1 1 calc R U . . .
H8B H 0.958310 0.845591 0.352791 0.044 Uiso 1 1 calc R U . . .
H8C H 1.016391 0.677974 0.410106 0.044 Uiso 1 1 calc R U . . .
C9 C 0.78823(9) 0.58117(13) 0.60444(12) 0.0240(2) Uani 1 1 d . . . . .
H9 H 0.765506 0.496633 0.660358 0.029 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 C3 1.3396(14) . ?
N1 N2 1.3609(12) . ?
N1 C5 1.4516(14) . ?
N2 C4 1.3323(14) . ?
N3 C1 1.2813(15) . ?
N3 C6 1.4093(13) . ?
N4 C7 1.3503(14) . ?
N4 N5 1.3556(13) . ?
N4 C8 1.4506(14) . ?
N5 C9 1.3312(15) . ?
C1 C2 1.4463(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.3842(16) . ?
C2 C4 1.4121(15) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.3813(15) . ?
C6 C9 1.4120(15) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 0.9500 . ?

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
C3 N1 N2 112.19(9) . . ?
C3 N1 C5 127.82(9) . . ?
N2 N1 C5 119.99(9) . . ?
C4 N2 N1 104.59(9) . . ?
C1 N3 C6 117.84(9) . . ?
C7 N4 N5 112.22(9) . . ?
C7 N4 C8 128.08(9) . . ?
N5 N4 C8 119.66(9) . . ?
C9 N5 N4 104.73(9) . . ?
N3 C1 C2 122.62(10) . . ?
N3 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C4 103.97(10) . . ?
C3 C2 C1 125.96(10) . . ?
C4 C2 C1 130.08(10) . . ?
N1 C3 C2 107.55(9) . . ?
N1 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
N2 C4 C2 111.71(9) . . ?
N2 C4 H4 124.1 . . ?
C2 C4 H4 124.1 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N3 124.09(10) . . ?
C7 C6 C9 104.25(9) . . ?
N3 C6 C9 131.62(10) . . ?
N4 C7 C6 107.11(9) . . ?
N4 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 C6 111.68(10) . . ?
N5 C9 H9 124.2 . . ?
C6 C9 H9 124.2 . . ?

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
C3 N1 N2 C4 0.04(11) . . . . ?
C5 N1 N2 C4 -179.75(9) . . . . ?
C7 N4 N5 C9 0.59(12) . . . . ?
C8 N4 N5 C9 178.58(9) . . . . ?
C6 N3 C1 C2 178.31(9) . . . . ?
N3 C1 C2 C3 -177.70(10) . . . . ?
N3 C1 C2 C4 2.31(18) . . . . ?
N2 N1 C3 C2 0.01(12) . . . . ?
C5 N1 C3 C2 179.77(9) . . . . ?
C4 C2 C3 N1 -0.05(12) . . . . ?
C1 C2 C3 N1 179.97(10) . . . . ?
N1 N2 C4 C2 -0.07(12) . . . . ?
C3 C2 C4 N2 0.07(12) . . . . ?
C1 C2 C4 N2 -179.94(10) . . . . ?
C1 N3 C6 C7 172.56(10) . . . . ?
C1 N3 C6 C9 -9.96(17) . . . . ?
N5 N4 C7 C6 -0.42(12) . . . . ?
C8 N4 C7 C6 -178.19(10) . . . . ?
N3 C6 C7 N4 178.13(9) . . . . ?
C9 C6 C7 N4 0.07(12) . . . . ?
N4 N5 C9 C6 -0.54(12) . . . . ?
C7 C6 C9 N5 0.31(12) . . . . ?
N3 C6 C9 N5 -177.54(10) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035



_exptl_crystal_recrystallization_method Evaporation
_chemical_properties_physical    Light-sensitive
