Photocatalytic Hydrazonyl Radical-Mediated Radical Cyclization/Allylation Cascade: Synthesis of Dihydropyrazoles and Tetrahydropyridazines.
Zhao, Quan-Qing; Chen, Jun; Yan, Dong-Mei; Chen, Jia-Rong; Xiao, Wen-Jing; Organic letters 19 (2017) 3620–3623; doi:10.1021/acs.orglett.7b01609

data_1546381
_publ_section_title
;
 Photocatalytic Hydrazonyl Radical-Mediated Radical Cyclization/Allylation
 Cascade: Synthesis of Dihydropyrazoles and Tetrahydropyridazines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3620
_journal_page_last               3623
_journal_paper_doi               10.1021/acs.orglett.7b01609
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H28 N2 O4 S'
_chemical_formula_sum            'C24 H28 N2 O4 S'
_chemical_formula_weight         440.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                93.5160(10)
_cell_angle_beta                 114.8320(10)
_cell_angle_gamma                111.0780(10)
_cell_formula_units_Z            2
_cell_length_a                   10.4274(9)
_cell_length_b                   11.0126(10)
_cell_length_c                   11.6840(10)
_cell_measurement_reflns_used    7949
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      32.0243
_cell_measurement_theta_min      2.3782
_cell_volume                     1099.88(17)
_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      100.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10498
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         1.984
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0545P)^2^+0.3607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5196
_reflns_number_total             5747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01609_si_002.cif
_cod_data_source_block           mo_121619a_0m
_cod_depositor_comments          'Adding full bibliography for 1546381.cif.'
_cod_database_code               1546381
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C19(H19), C20(H20), C22(H22), C23(H23)
2.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              43345
_shelx_hkl_checksum              85042
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'