Preparation of trans-2-Substituted-4-halopiperidines and cis-2-Substituted-4-halotetrahydropyrans via AlCl3-Catalyzed Prins Reaction.
Liu, Gong-Qing; Cui, Bin; Xu, Rong; Li, Yue-Ming; The Journal of organic chemistry 81 (2016) 5144–5161; doi:10.1021/acs.joc.6b00725

data_4036855
_publ_section_title
;
 Preparation of trans-2-Substituted-4-halopiperidines and
 cis-2-Substituted-4-halotetrahydropyrans via AlCl3-Catalyzed Prins
 Reaction.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5144
_journal_page_last               5161
_journal_paper_doi               10.1021/acs.joc.6b00725
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C18 H19 Br N2 O4 S'
_chemical_formula_sum            'C18 H19 Br N2 O4 S'
_chemical_formula_weight         439.32
_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
_audit_creation_date             2015-08-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.16 svn.r3037 for OlexSys, GUI svn.r4914)
;
_cell_angle_alpha                92.49(3)
_cell_angle_beta                 92.80(3)
_cell_angle_gamma                91.60(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4043(13)
_cell_length_b                   7.3316(15)
_cell_length_c                   19.670(4)
_cell_measurement_temperature    113(2)
_cell_volume                     921.2(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.1382
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7019
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.831
_diffrn_reflns_theta_min         2.075
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.595
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0785
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1664P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2850
_reflns_number_total             4161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00725_si_002.cif
_cod_data_source_block           shelxl_2
_cod_database_code               4036855
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.764
_shelx_estimated_absorpt_t_min   0.648
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.825(2) 0.175(2)
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. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'