Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions.
Chen, Yunwei; Sun, Xiang; Wu, Ningjie; Li, Jingbai; Jin, Shengnan; Zhong, Yongliang; Liu, Zirui; Rogachev, Andrey; Chong, Hyun-Soon; Organic & biomolecular chemistry 14 (2016) 920–939; doi:10.1039/c5ob01692d

data_7154811
_publ_section_title
;
 Synthetic and theoretical investigation on the one-pot halogenation of
 \b-amino alcohols and nucleophilic ring opening of aziridinium ions.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              920
_journal_page_last               939
_journal_paper_doi               10.1039/c5ob01692d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H20 Cl N'
_chemical_formula_sum            'C17 H20 Cl N'
_chemical_formula_weight         273.79
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-04-26 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.479(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.547(3)
_cell_length_b                   7.1510(19)
_cell_length_c                   12.171(3)
_cell_measurement_reflns_used    2969
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      3.37
_cell_volume                     773.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0094
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4374
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008/1)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0354P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                2884
_reflns_number_total             3064
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01692d2.cif
_cod_data_source_block           11209c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154811.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7154811
_chemical_name_iupac             Dibenzyl[(2R)-2-chloropropyl]amine