Domino Reaction of Pyrrolidinium Ylides: Michael Addition/[1,2]-Stevens Rearrangement.
Kowalkowska, Anna; Jończyk, Andrzej; Maurin, Jan K.; The Journal of organic chemistry 83 (2018) 4105–4110; doi:10.1021/acs.joc.7b03278

data_4035505
_publ_section_title
;
 Domino Reaction of Pyrrolidinium Ylides: Michael Addition/[1,2]-Stevens
 Rearrangement.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4105
_journal_page_last               4110
_journal_paper_doi               10.1021/acs.joc.7b03278
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H19 N3'
_chemical_formula_sum            'C16 H19 N3'
_chemical_formula_weight         253.34
_chemical_melting_point          395
_chemical_name_systematic
; 
2-cyano-2-(2-cyanoethyl)1-methyl-3-phenylpiperidine
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-02-02 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.1770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.12920(10)
_cell_length_b                   9.77300(10)
_cell_length_c                   21.1929(2)
_cell_measurement_reflns_used    11588
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1760
_cell_measurement_theta_min      4.1740
_cell_volume                     1470.56(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.25a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.25a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.25a (Rigaku OD, 2015)'
_computing_molecular_graphics    'XP (Bruker AXS, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4922
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23250
_diffrn_reflns_theta_full        71.27
_diffrn_reflns_theta_max         71.27
_diffrn_reflns_theta_min         4.19
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.25a (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0678P)^2^+0.2060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2500
_reflns_number_total             2845
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03278_si_002.cif
_cod_data_source_block           pw14abs
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035505