#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:23:12 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289595 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/29/7062923.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7062923
loop_
_publ_author_name
'Gomes, Carla'
'Costa, Mariana'
'Lopes, Susana M. M.'
'Nogueira, Bernardo Albuquerque'
'Fausto, Rui'
'Paixão, José A.'
'Pinho e Melo, Teresa M. V. D.'
'Martins, Luísa M. D. R. S.'
'Pineiro, Marta'
_publ_section_title
;
 On the mechanochemical synthesis of C-scorpionates with an oxime moiety
 and their application in the copper-catalyzed azide--alkyne cycloaddition
 (CuAAC) reaction
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              874
_journal_page_last               886
_journal_paper_doi               10.1039/D3NJ05017C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C11 H11 N7 O'
_chemical_formula_sum            'C11 H11 N7 O'
_chemical_formula_weight         257.27
_chemical_melting_point          417.3
_chemical_name_common
;     
 [(1-Hydroxyimino)methyl]tris(1H-pyrazol-1-yl)methane
;
_chemical_name_systematic
;
(E)-2,2,2-tri(1H-pyrazol-1-yl)acetaldehyde oxime
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-14 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.395(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2989(3)
_cell_length_b                   9.5354(3)
_cell_length_c                   12.3745(4)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.164
_cell_measurement_theta_min      5.085
_cell_volume                     1214.87(7)
_computing_cell_refinement       'APEXIII (Bruker AXS, 2016)'
_computing_data_collection       'APEXIII (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker APEXII CCD area-detector diffractometer  
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            114886
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.369
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, dichloromethane'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   0.746
_exptl_transmission_factor_min   0.682
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0353
_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)+(0.0422P)²+0.3590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2285
_reflns_number_total             2792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj05017c2.cif
_cod_data_source_block           csg503b_a
_cod_depositor_comments          'Adding full bibliography for 7062923.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062923
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.984
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'
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 . . .
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'
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_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_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
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) . . . . ?
