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_1547100
_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_absolute_configuration ad
_chemical_formula_moiety         'C25 H30 N2 O4 S'
_chemical_formula_sum            'C25 H30 N2 O4 S'
_chemical_formula_weight         454.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.0693(16)
_cell_length_b                   54.037(5)
_cell_length_c                   10.9426(11)
_cell_measurement_reflns_used    8108
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.28
_cell_volume                     9501.9(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       68
_diffrn_reflns_limit_k_min       -68
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19328
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.283
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             3872
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5064
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0515P)^2^+2.2541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                4689
_reflns_number_total             5064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01609_si_003.cif
_cod_data_source_block           t
_cod_original_cell_volume        9501.8(16)
_cod_database_code               1547100
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.980
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C25(H25A,H25B,
 H25C)
;
_shelx_res_checksum              13724
_shelx_hkl_checksum              6185
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'