A multi-component synthetic route for 2-pyrazolines <i>via</i> acceptorless dehydrogenation of alcohols using homogeneous Ni(II) catalysts.
Kukreti, Prashant; Chauhan, Rahul; Panwar, Abhishek; Ghosh, Kaushik; Organic & biomolecular chemistry 22 (2024) 8273–8278; doi:10.1039/d4ob01352b

data_7160279
_publ_section_title
;
 A multi-component synthetic route for 2-pyrazolines <i>via</i>
 acceptorless dehydrogenation of alcohols using homogeneous Ni(II)
 catalysts.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8273
_journal_page_last               8278
_journal_paper_doi               10.1039/d4ob01352b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C12.5 H14.5 Cl N2.5 Ni0.5'
_chemical_formula_sum            'C12.5 H14.5 Cl N2.5 Ni0.5'
_chemical_formula_weight         264.57
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-06
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-07-11 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.8650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.0346(10)
_cell_length_b                   9.1005(4)
_cell_length_c                   14.6912(6)
_cell_measurement_reflns_used    9080
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      28.332
_cell_measurement_theta_min      2.474
_cell_volume                     2580.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      101.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            54316
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         2.111
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.9429. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic yellowish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0217P)^2^+8.0638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3025
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01352b2.cif
_cod_data_source_block           kg_pk_584_0297_0m_a
_cod_original_formula_sum        'C12.50 H14.50 Cl N2.50 Ni0.50'
_cod_database_code               7160279
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              6783
_olex2_submission_special_instructions 'No special instructions were received'