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_7059002
_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           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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            4
_cell_length_a                   7.0748(4)
_cell_length_b                   8.1131(4)
_cell_length_c                   16.9559(9)
_cell_measurement_reflns_used    1450
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      3.12
_cell_volume                     973.24(9)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0190
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3251
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.306
_diffrn_reflns_theta_min         3.751
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_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            Colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       Needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.7013
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0491P)^2^+0.1516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                1595
_reflns_number_total             1736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj02807b2.cif
_cod_data_source_block           5b
_cod_database_code               7059002
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              52397