Ligand Redox-Controlled Tandem Synthesis of Azines from Aromatic Alcohols and Hydrazine in Air: One-Pot Synthesis of Phthalazine.
Chakraborty, Mou; Sengupta, Debabrata; Saha, Tanushri; Goswami, Sreebrata; The Journal of organic chemistry 83 (2018) 7771–7778; doi:10.1021/acs.joc.8b00661

data_4035597
_publ_section_title
;
 Ligand Redox-Controlled Tandem Synthesis of Azines from Aromatic Alcohols
 and Hydrazine in Air: One-Pot Synthesis of Phthalazine.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7771
_journal_page_last               7778
_journal_paper_doi               10.1021/acs.joc.8b00661
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H17 Cl2 N5 Ni O, O1.5'
_chemical_formula_sum            'C18 H17 Cl2 N5 Ni O2.5'
_chemical_formula_weight         472.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.78(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.39(2)
_cell_length_b                   8.148(7)
_cell_length_c                   20.029(16)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.5
_cell_volume                     4551(6)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi SCANS'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2113
_diffrn_reflns_av_unetI/netI     0.2898
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10889
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.050
_diffrn_reflns_theta_min         1.460
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.111
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.2660
_refine_ls_R_factor_gt           0.0857
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0844P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1392
_reflns_number_total             4177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00661_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'EMPIRICAL' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2021-10-24
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H34 Cl4 N10 Ni2 O5'
_cod_original_formula_weight         945.91
_cod_original_formula_moiety         '2(C18 H17 Cl2 N5 Ni O), O2, O'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        4552(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4035597
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              42955
_shelx_hkl_checksum              9721