On the mechanochemical synthesis of C-scorpionates with an oxime moiety and their application in the copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction
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; New Journal of Chemistry 48 (2024) 874–886; doi:10.1039/D3NJ05017C

data_7062923
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0422P)^2^+0.3590P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              6999