Alkylidene Dihydropyridines As Synthetic Intermediates: Model Studies toward the Synthesis of the Bis(piperidine) Alkaloid Xestoproxamine C.
Lansakara, Ashabha I.; Mariappan, S. V. Santhana; Pigge, F. Christopher; The Journal of organic chemistry 81 (2016) 10266–10278; doi:10.1021/acs.joc.6b01269

data_4037020
_publ_section_title
;
 Alkylidene Dihydropyridines As Synthetic Intermediates: Model Studies
 toward the Synthesis of the Bis(piperidine) Alkaloid Xestoproxamine C.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10266
_journal_page_last               10278
_journal_paper_doi               10.1021/acs.joc.6b01269
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'Cl, C20 H31 N2 O'
_chemical_formula_sum            'C20 H31 Cl N2 O'
_chemical_formula_weight         350.92
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 95.083(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0891(19)
_cell_length_b                   10.1206(10)
_cell_length_c                   9.7640(10)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      55.73
_cell_measurement_theta_min      5.809
_cell_volume                     1878.9(3)
_computing_cell_refinement       'apexII (Bruker AXS, 2010)'
_computing_data_collection       'apexII (Bruker AXS, 2010)'
_computing_data_reduction        'apexII (Bruker AXS, 2010)'
_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      190.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.280
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0537 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.9519.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0790P)^2^+2.2570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2847
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01269_si_002.cif
_cod_data_source_block           fcp166
_cod_database_code               4037020
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.918
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C20, C19, C18, C17, C16, C15, C14, C13, C12, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B), C20(H20A,H20B), C19(H19A,H19B),
 C18(H18A,H18B), C17(H17A,H17B), C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B),
  C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C1(H1A)
;
_shelx_res_checksum              77967
_shelx_hkl_checksum              62915
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'