New nitroindazolylacetonitriles: efficient synthetic access via vicarious nucleophilic substitution and tautomeric switching mediated by anions
Eddahmi, Mohammed; Moura, Nuno M. M.; Bouissane, Latifa; Gamouh, Ahmed; Faustino, Maria A. F.; Cavaleiro, José A. S.; Paz, Filipe A. A.; Mendes, Ricardo F.; Lodeiro, Carlos; Santos, Sérgio M.; Neves, Maria G. P. M. S.; Rakib, El Mostapha; New Journal of Chemistry 43 (2019) 14355–; doi:10.1039/C9NJ02807B

data_7059003
_publ_section_title
;
 New nitroindazolylacetonitriles: efficient synthetic access via vicarious
 nucleophilic substitution and tautomeric switching mediated by anions
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14355
_journal_paper_doi               10.1039/C9NJ02807B
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C10 H8 N4 O2'
_chemical_formula_sum            'C10 H8 N4 O2'
_chemical_formula_weight         216.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             '08 May 2019'
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_update_record
;
2019-05-08 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.5388(7)
_cell_length_b                   18.888(2)
_cell_length_c                   15.6064(18)
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.52
_cell_volume                     1927.5(4)
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_collection       'APEX2 2012.4 (Bruker, 2012b)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       '\w / \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9213
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         3.546
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       Block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.6727
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0465P)^2^+1.6229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                891
_reflns_number_total             962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj02807b2.cif
_cod_data_source_block           5a
_cod_original_cell_volume        1927.4(4)
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               7059003
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              17572