A 2-(1-methylhydrazinyl)pyridine-directed C-H functionalization/spirocyclization cascade: facile access to spirosuccinimide derivatives.
Zhao, Hua; Shao, Xiaoru; Wang, Taimin; Zhai, Shengxian; Qiu, Shuxian; Tao, Cheng; Wang, Huifei; Zhai, Hongbin; Chemical communications (Cambridge, England) 54 (2018) 4927–4930; doi:10.1039/c8cc01774c

data_7121486
_publ_section_title
;
 A 2-(1-methylhydrazinyl)pyridine-directed C-H
 functionalization/spirocyclization cascade: facile access to
 spirosuccinimide derivatives.
;
_journal_issue                   39
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4927
_journal_page_last               4930
_journal_paper_doi               10.1039/c8cc01774c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C19 H17 Br N4 O4'
_chemical_formula_sum            'C19 H17 Br N4 O4'
_chemical_formula_weight         445.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-07 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4667(5)
_cell_length_b                   8.4993(2)
_cell_length_c                   12.0129(4)
_cell_measurement_reflns_used    6350
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9330
_cell_measurement_theta_min      2.6240
_cell_volume                     1885.47(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  30.00   1.00    4.00    --   11.74 -19.00   0.00   96
  2  \w     -5.00  28.00   1.00    4.00    --  -11.59 -99.00-120.00   33
  3  \w     11.00  53.00   1.00    4.00    --   11.74 -99.00-120.00   42
  4  \w     40.00  68.00   1.00    4.00    --   11.74-178.00  30.00   28
  5  \w     12.00  50.00   1.00    4.00    --   11.74 -99.00  30.00   38
  6  \w     -8.00  86.00   1.00    4.00    --   11.74  37.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0066100000
_diffrn_orient_matrix_UB_12      0.0396438000
_diffrn_orient_matrix_UB_13      0.0283084000
_diffrn_orient_matrix_UB_21      0.0523798000
_diffrn_orient_matrix_UB_22      0.0358825000
_diffrn_orient_matrix_UB_23      -0.0186852000
_diffrn_orient_matrix_UB_31      -0.0646343000
_diffrn_orient_matrix_UB_32      0.0250322000
_diffrn_orient_matrix_UB_33      -0.0180253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16347
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.541
_diffrn_reflns_theta_min         2.206
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.409
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.017(15)
_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     257
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0516P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                3795
_reflns_number_total             4391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01774c2.cif
_cod_data_source_block           46-4
_cod_depositor_comments          'Adding full bibliography for 7121486.cif.'
_cod_database_code               7121486
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.777
_shelx_estimated_absorpt_t_min   0.718
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.017(15)
 -0.017(15)
2. 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
3.a Riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C0AA(H0AA), C1AA(H1AA), C18(H18), C24(H24), C58(H58)
3.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C49(H49A,H49B,H49C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.774