Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles.
Duan, Xiao-Yong; Yang, Xiu-Long; Jia, Pan-Pan; Zhang, Man; Han, Bing; Organic letters 17 (2015) 6022–6025; doi:10.1021/acs.orglett.5b03003

data_1555440
_publ_section_title
;
 Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the
 Synthesis of Pyrazoline-Functionalized Oxindoles.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6022
_journal_page_last               6025
_journal_paper_doi               10.1021/acs.orglett.5b03003
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C29 H30 Br N3 O'
_chemical_formula_sum            'C29 H30 Br N3 O'
_chemical_formula_weight         516.47
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                91.311(7)
_cell_angle_beta                 97.750(7)
_cell_angle_gamma                93.388(9)
_cell_formula_units_Z            2
_cell_length_a                   8.9762(10)
_cell_length_b                   9.2143(10)
_cell_length_c                   15.8055(10)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2200
_cell_measurement_theta_min      4.8080
_cell_volume                     1292.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1583809000
_diffrn_orient_matrix_UB_12      0.0503825000
_diffrn_orient_matrix_UB_13      0.0076810000
_diffrn_orient_matrix_UB_21      -0.0649705000
_diffrn_orient_matrix_UB_22      -0.1588033000
_diffrn_orient_matrix_UB_23      -0.0118073000
_diffrn_orient_matrix_UB_31      0.0285462000
_diffrn_orient_matrix_UB_32      -0.0179415000
_diffrn_orient_matrix_UB_33      0.0974034000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8604
_diffrn_reflns_theta_full        25.84
_diffrn_reflns_theta_max         25.84
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1097P)^2^+0.4890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2043
_reflns_number_gt                3870
_reflns_number_total             4844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03003_si_002.cif
_cod_data_source_block           duanxy0630_2
_cod_database_code               1555440
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C30) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27)
\\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29') \\sim Ueq, Uanis(C30') \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H28(0.5) H28A(0.5) C29(0.5) H29(0.5) C30(0.5) H30(0.5) C29'(0.5)
 H29'(0.5) C30'(0.5) H30'(0.5)
4.a Ternary CH refined with riding coordinates:
 C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
 C26(H26), C27(H27), C28(H28), C28(H28A), C29(H29), C30(H30), C29'(H29'),
 C30'(H30')
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;