Direct N-H/α,α,β,β-C(sp(3))-H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles.
Du, Yanlong; Yu, Aimin; Jia, Jiru; Zhang, Youquan; Meng, Xiangtai; Chemical communications (Cambridge, England) 53 (2017) 1684–1687; doi:10.1039/c6cc08996h

data_7119392
_publ_section_title
;
 Direct N-H/\a,\a,\b,\b-C(sp(3))-H functionalization of piperidine via an
 azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted
 oxindoles.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1684
_journal_page_last               1687
_journal_paper_doi               10.1039/c6cc08996h
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C30 H28 N4 O4 S'
_chemical_formula_sum            'C30 H28 N4 O4 S'
_chemical_formula_weight         540.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-10-12 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.211(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.539(2)
_cell_length_b                   10.3664(9)
_cell_length_c                   17.820(2)
_cell_measurement_reflns_used    1905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3300
_cell_measurement_theta_min      2.3900
_cell_volume                     2551.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -75.00 120.00   1.00    6.00    --   30.00  54.00 240.00  195
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0304603000
_diffrn_orient_matrix_UB_12      -0.0126205000
_diffrn_orient_matrix_UB_13      -0.0233974000
_diffrn_orient_matrix_UB_21      0.0408644000
_diffrn_orient_matrix_UB_22      -0.0010452000
_diffrn_orient_matrix_UB_23      0.0345578000
_diffrn_orient_matrix_UB_31      -0.0064219000
_diffrn_orient_matrix_UB_32      -0.0672281000
_diffrn_orient_matrix_UB_33      0.0038685000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.304
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0552P)^2^+0.2084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3211
_reflns_number_total             4501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08996h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7119390--7119392.cif.'
_cod_original_cell_volume        2551.2(6)
_cod_database_code               7119392
_reflns_odcompleteness_completeness 84.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.89
_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:
 C00E(H00E), C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C00N(H00C,H00D), C00P(H00G,H00H), C00S(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C010(H010), C011(H011), C012(H012), C013(H013)
2.d Idealised Me refined as rotating group:
 C00Y(H00L,H00M,H00N), C00Z(H00O,H00P,H00S)
;
_shelx_res_checksum              66478
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.442
_oxdiff_exptl_absorpt_empirical_full_min 0.561