Copper-catalysed dehydrogenative self-coupling/cyclization of 5-aminopyrazoles: synthesis and photophysical study of pyridazines.
Rastogi, Gaurav K.; Deb, Mohit L.; Baruah, Pranjal K.; Chemical communications (Cambridge, England) 59 (2023) 9642–9645; doi:10.1039/d3cc02424e

data_7131900
_publ_section_title
;
 Copper-catalysed dehydrogenative self-coupling/cyclization of
 5-aminopyrazoles: synthesis and photophysical study of pyridazines.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9642
_journal_page_last               9645
_journal_paper_doi               10.1039/d3cc02424e
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C5 H7 N3'
_chemical_formula_sum            'C5 H7 N3'
_chemical_formula_weight         109.14
_chemical_name_systematic        orthorhombic
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-09-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2023-05-13 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.861(6)
_cell_length_b                   6.7837(16)
_cell_length_c                   7.501(2)
_cell_measurement_reflns_used    467
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.3510
_cell_measurement_theta_min      3.1260
_cell_volume                     1112.4(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         3.144
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_correction_T_min  0.8654
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Bruker APEX-II CCD'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.008(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0835
_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^)+(0.0834P)^2^+0.5343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2080
_refine_ls_wR_factor_ref         0.2484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                548
_reflns_number_total             975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02424e2.cif
_cod_data_source_block           exp_513
_cod_depositor_comments          'Adding full bibliography for 7131900.cif.'
_cod_database_code               7131900
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              27245
_shelx_hkl_checksum              28442
_olex2_submission_special_instructions 'No special instructions were received'