# 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 2023

####################################################################### 
# 
# 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_csg503b_a
_database_code_depnum_ccdc_archive 'CCDC 2096452'
loop_
_audit_author_name
_audit_author_address
'Jose Antonio Paixao'
;University of Coimbra
Portugal
;
_audit_update_record             
;
2021-07-14 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
(E)-2,2,2-tri(1H-pyrazol-1-yl)acetaldehyde oxime
;
_chemical_name_common            
;     
 [(1-Hydroxyimino)methyl]tris(1H-pyrazol-1-yl)methane
;
_chemical_melting_point          417.3
_chemical_formula_moiety         'C11 H11 N7 O'
_chemical_formula_sum            'C11 H11 N7 O'
_chemical_formula_weight         257.27

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'
O O 0.0106 0.0060 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.2989(3)
_cell_length_b                   9.5354(3)
_cell_length_c                   12.3745(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.395(2)
_cell_angle_gamma                90
_cell_volume                     1214.87(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      5.085
_cell_measurement_theta_max      49.164

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   0.682
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  
;
Bruker APEXII CCD area-detector diffractometer  
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            114886
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.369
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2792
_reflns_number_gt                2285
_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       'APEXIII (Bruker AXS, 2016)'
_computing_cell_refinement       'APEXIII (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0422P)²+0.3590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2792
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1 O 0.54282(10) 0.59101(10) 0.37986(8) 0.0442(2) Uani 1 1 d . . . . .
H1 H 0.5577(17) 0.6139(19) 0.4548(15) 0.066 Uiso 1 1 d . U . . .
N1 N 0.48687(11) 0.45835(12) 0.38222(8) 0.0399(3) Uani 1 1 d . . . . .
N2 N 0.36140(10) 0.24657(11) 0.16577(8) 0.0333(2) Uani 1 1 d . . . . .
N3 N 0.29901(12) 0.35381(13) 0.11518(9) 0.0472(3) Uani 1 1 d . . . . .
N4 N 0.50228(9) 0.15852(11) 0.30132(8) 0.0332(2) Uani 1 1 d . . . . .
N5 N 0.62023(10) 0.17497(13) 0.25636(8) 0.0416(3) Uani 1 1 d . . . . .
N6 N 0.29495(10) 0.24362(11) 0.34647(8) 0.0346(2) Uani 1 1 d . . . . .
N7 N 0.31050(12) 0.25073(15) 0.45530(9) 0.0518(3) Uani 1 1 d . . . . .
C1 C 0.40572(11) 0.26521(13) 0.27736(9) 0.0304(2) Uani 1 1 d . . . . .
C2 C 0.46467(12) 0.41014(13) 0.28988(9) 0.0344(3) Uani 1 1 d . . . . .
H2 H 0.484164 0.462785 0.229120 0.041 Uiso 1 1 calc R U . . .
C3 C 0.25410(15) 0.2973(2) 0.02448(11) 0.0554(4) Uani 1 1 d . . . . .
H3 H 0.206807 0.346548 -0.028065 0.066 Uiso 1 1 calc R U . . .
C4 C 0.28510(15) 0.1570(2) 0.01622(11) 0.0554(4) Uani 1 1 d . . . . .
H4 H 0.263770 0.096501 -0.040439 0.067 Uiso 1 1 calc R U . . .
C5 C 0.35341(14) 0.12596(16) 0.10844(11) 0.0446(3) Uani 1 1 d . . . . .
H5 H 0.387774 0.039221 0.128199 0.053 Uiso 1 1 calc R U . . .
C6 C 0.67504(15) 0.05020(18) 0.26689(12) 0.0522(4) Uani 1 1 d . . . . .
H6 H 0.758116 0.029173 0.243914 0.063 Uiso 1 1 calc R U . . .
C7 C 0.59441(17) -0.04567(18) 0.31614(14) 0.0587(4) Uani 1 1 d . . . . .
H7 H 0.612431 -0.139100 0.332013 0.070 Uiso 1 1 calc R U . . .
C8 C 0.48364(15) 0.02565(16) 0.33627(12) 0.0488(3) Uani 1 1 d . . . . .
H8 H 0.409476 -0.009754 0.367875 0.059 Uiso 1 1 calc R U . . .
C9 C 0.19168(15) 0.23615(17) 0.49122(12) 0.0528(4) Uani 1 1 d . . . . .
H9 H 0.171414 0.236161 0.564043 0.063 Uiso 1 1 calc R U . . .
C10 C 0.10096(14) 0.22088(17) 0.40808(13) 0.0517(4) Uani 1 1 d . . . . .
H10 H 0.011779 0.209129 0.414077 0.062 Uiso 1 1 calc R U . . .
C11 C 0.16907(12) 0.22661(15) 0.31600(11) 0.0411(3) Uani 1 1 d . . . . .
H11 H 0.135775 0.220129 0.245640 0.049 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
O1 N1 1.3906(14) . ?
O1 H1 0.961(19) . ?
N1 C2 1.2477(15) . ?
N2 C5 1.3527(17) . ?
N2 N3 1.3531(15) . ?
N2 C1 1.4548(14) . ?
N3 C3 1.3185(18) . ?
N4 C8 1.3540(18) . ?
N4 N5 1.3574(14) . ?
N4 C1 1.4483(15) . ?
N5 C6 1.3220(19) . ?
N6 C11 1.3511(16) . ?
N6 N7 1.3541(14) . ?
N6 C1 1.4569(15) . ?
N7 C9 1.3194(19) . ?
C1 C2 1.5158(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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
N1 O1 H1 104.0(11) . . ?
C2 N1 O1 112.50(11) . . ?
C5 N2 N3 112.20(10) . . ?
C5 N2 C1 127.98(11) . . ?
N3 N2 C1 118.77(10) . . ?
C3 N3 N2 103.76(12) . . ?
C8 N4 N5 111.98(11) . . ?
C8 N4 C1 128.37(11) . . ?
N5 N4 C1 116.86(10) . . ?
C6 N5 N4 103.88(12) . . ?
C11 N6 N7 111.90(10) . . ?
C11 N6 C1 127.80(10) . . ?
N7 N6 C1 120.09(10) . . ?
C9 N7 N6 103.97(11) . . ?
N4 C1 N2 107.85(9) . . ?
N4 C1 N6 108.91(9) . . ?
N2 C1 N6 107.92(9) . . ?
N4 C1 C2 110.38(9) . . ?
N2 C1 C2 108.91(9) . . ?
N6 C1 C2 112.72(10) . . ?
N1 C2 C1 119.57(11) . . ?
N1 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N3 C3 C4 112.47(13) . . ?
N3 C3 H3 123.8 . . ?
C4 C3 H3 123.8 . . ?
C5 C4 C3 105.36(13) . . ?
C5 C4 H4 127.3 . . ?
C3 C4 H4 127.3 . . ?
N2 C5 C4 106.20(14) . . ?
N2 C5 H5 126.9 . . ?
C4 C5 H5 126.9 . . ?
N5 C6 C7 112.20(13) . . ?
N5 C6 H6 123.9 . . ?
C7 C6 H6 123.9 . . ?
C8 C7 C6 105.40(14) . . ?
C8 C7 H7 127.3 . . ?
C6 C7 H7 127.3 . . ?
N4 C8 C7 106.51(14) . . ?
N4 C8 H8 126.7 . . ?
C7 C8 H8 126.7 . . ?
N7 C9 C10 112.12(13) . . ?
N7 C9 H9 123.9 . . ?
C10 C9 H9 123.9 . . ?
C11 C10 C9 105.54(12) . . ?
C11 C10 H10 127.2 . . ?
C9 C10 H10 127.2 . . ?
N6 C11 C10 106.46(12) . . ?
N6 C11 H11 126.8 . . ?
C10 C11 H11 126.8 . . ?

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
C5 N2 N3 C3 -0.99(15) . . . . ?
C1 N2 N3 C3 -170.19(11) . . . . ?
C8 N4 N5 C6 -1.53(14) . . . . ?
C1 N4 N5 C6 -164.23(10) . . . . ?
C11 N6 N7 C9 0.68(16) . . . . ?
C1 N6 N7 C9 175.85(12) . . . . ?
C8 N4 C1 N2 -86.54(14) . . . . ?
N5 N4 C1 N2 72.87(12) . . . . ?
C8 N4 C1 N6 30.34(16) . . . . ?
N5 N4 C1 N6 -170.25(9) . . . . ?
C8 N4 C1 C2 154.59(13) . . . . ?
N5 N4 C1 C2 -46.00(13) . . . . ?
C5 N2 C1 N4 30.60(16) . . . . ?
N3 N2 C1 N4 -162.11(10) . . . . ?
C5 N2 C1 N6 -86.92(14) . . . . ?
N3 N2 C1 N6 80.36(13) . . . . ?
C5 N2 C1 C2 150.40(12) . . . . ?
N3 N2 C1 C2 -42.32(14) . . . . ?
C11 N6 C1 N4 -124.52(13) . . . . ?
N7 N6 C1 N4 61.15(14) . . . . ?
C11 N6 C1 N2 -7.69(17) . . . . ?
N7 N6 C1 N2 177.99(11) . . . . ?
C11 N6 C1 C2 112.62(14) . . . . ?
N7 N6 C1 C2 -61.70(15) . . . . ?
O1 N1 C2 C1 178.99(10) . . . . ?
N4 C1 C2 N1 -75.07(14) . . . . ?
N2 C1 C2 N1 166.71(11) . . . . ?
N6 C1 C2 N1 46.97(15) . . . . ?
N2 N3 C3 C4 0.51(17) . . . . ?
N3 C3 C4 C5 0.12(19) . . . . ?
N3 N2 C5 C4 1.09(16) . . . . ?
C1 N2 C5 C4 169.07(12) . . . . ?
C3 C4 C5 N2 -0.71(17) . . . . ?
N4 N5 C6 C7 0.77(16) . . . . ?
N5 C6 C7 C8 0.23(18) . . . . ?
N5 N4 C8 C7 1.71(15) . . . . ?
C1 N4 C8 C7 161.93(12) . . . . ?
C6 C7 C8 N4 -1.13(16) . . . . ?
N6 N7 C9 C10 -0.39(18) . . . . ?
N7 C9 C10 C11 -0.02(19) . . . . ?
N7 N6 C11 C10 -0.72(16) . . . . ?
C1 N6 C11 C10 -175.42(12) . . . . ?
C9 C10 C11 N6 0.43(17) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 N1 0.961(19) 2.190(19) 3.0044(14) 141.7(15) 3_666 yes
O1 H1 N7 0.961(19) 2.162(18) 2.9274(15) 135.7(14) 3_666 yes
C6 H6 O1 0.93 2.66 3.4856(19) 149.0 2_645 yes
C8 H8 N3 0.93 2.52 3.4066(19) 158.6 2_545 yes
C9 H9 N5 0.93 2.59 3.4846(18) 160.9 4_566 yes

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, dichloromethane'
