A visible-light photocatalytic N-radical cascade of hydrazones for the synthesis of dihydropyrazole-fused benzosultams.
Zhao, Quan-Qing; Hu, Xiao-Qiang; Yang, Meng-Nan; Chen, Jia-Rong; Xiao, Wen-Jing; Chemical communications (Cambridge, England) 52 (2016) 12749–12752; doi:10.1039/c6cc05897c

data_7124960
_publ_section_title
;
 A visible-light photocatalytic N-radical cascade of hydrazones for the
 synthesis of dihydropyrazole-fused benzosultams.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12749
_journal_page_last               12752
_journal_paper_doi               10.1039/c6cc05897c
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C19 H20 N2 O2 S'
_chemical_formula_sum            'C19 H20 N2 O2 S'
_chemical_formula_weight         340.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-18 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                69.5060(10)
_cell_angle_beta                 77.9270(10)
_cell_angle_gamma                89.1630(10)
_cell_formula_units_Z            4
_cell_length_a                   9.3100(9)
_cell_length_b                   13.2449(13)
_cell_length_c                   14.8906(15)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      31.815
_cell_measurement_theta_min      2.241
_cell_volume                     1678.5(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20351
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         32.042
_diffrn_reflns_theta_min         1.496
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         10676
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0611P)^2^+0.7303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9233
_reflns_number_total             10676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05897c2.cif
_cod_data_source_block           qqz-108
_cod_database_code               7124960
_shelx_estimated_absorpt_t_max   0.980
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C8 \\sim C8-C9'
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C11') \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C9) = Uanis(C9')
4. Others
 Sof(H31C)=Sof(H31D)=Sof(N3')=Sof(N4')=Sof(C30')=Sof(H30')=Sof(O5)=Sof(O4')=1-
 FVAR(1)
 Sof(O3)=Sof(O4)=Sof(N3)=Sof(N4)=Sof(C30)=Sof(H30)=Sof(H31A)=Sof(H31B)=FVAR(1)
 Sof(H12C)=Sof(H12D)=Sof(N1')=Sof(N2')=Sof(C11')=Sof(H11')=Sof(O1')=Sof(O2')=
 Sof(C9')=Sof(H9'A)=Sof(H9'B)=Sof(H9'C)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(N1)=Sof(N2)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C11)=
 Sof(H11)=Sof(H12A)=Sof(H12B)=FVAR(2)
5.a Riding coordinates:
 C30(H30)
5.b Ternary CH refined with riding coordinates:
 C30'(H30'), C11(H11), C11'(H11')
5.c Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C31(H31C,H31D), C12(H12A,H12B), C12(H12C,H12D)
5.d Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C34(H34), C35(H35),
 C37(H37), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18)
5.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C38(H38A,H38B,H38C), C9(H9A,H9B,
 H9C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C9'(H9'A,H9'B,H9'C)
;
_shelx_res_checksum              71843
_shelx_hkl_checksum              79124
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'