Synthesis, crystal structure, and Hirshfeld surface analysis of 3-ferrocenyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine
Joekar, Delara; Hiscock, Lana K.; Dawe, Louise N.; Acta Crystallographica Section E Crystallographic Communications 79 (2023) –; doi:10.1107/S2056989023008101

data_2022865
_publ_section_title
;
 Synthesis, crystal structure, and Hirshfeld surface analysis of
 3-ferrocenyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine
;
_journal_coeditor_code           WM5693
_journal_issue                   10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023008101
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '[Fe (C5 H5) (C13 H11 N4)]'
_chemical_formula_moiety         'C18 H16 Fe N4'
_chemical_formula_sum            'C18 H16 Fe N4'
_chemical_formula_weight         344.20
_chemical_name_systematic
;
3-Ferrocenyl-1-(pyridin-2-yl)-1<i>H</i>-pyrazol-5-amine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.878(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.349(8)
_cell_length_b                   6.894(3)
_cell_length_c                   12.173(5)
_cell_measurement_reflns_used    7455
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      3.35
_cell_volume                     1454.1(11)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37974
_diffrn_reflns_theta_full        25.056
_diffrn_reflns_theta_max         25.056
_diffrn_reflns_theta_min         2.351
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_T_max  0.9561
_exptl_absorpt_correction_T_min  0.8290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0216P)^2^+2.1580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                1877
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5693sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1454.0(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022865
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.962
_shelx_hkl_checksum              66365
_shelx_res_checksum              58000
_cod_database_fobs_code 2022865