# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Maria Diaz de Villegas'
'Jose A. Galvez Lafuente'
'Ramon Badorrey'
'Pilar Lopez-Ram-de-Viu'
_publ_contact_author_email       loladiaz@unizar.es
_publ_contact_author_name        'Maria  Diaz de Villegas'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 837207'
#TrackingRef '9e.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(R)-2-[(R)-1-hydroxy-3-phenylpropyl]piperidine
;
_chemical_name_common            ?
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H21 N O'
_chemical_formula_sum            'C14 H21 N O'
_chemical_formula_weight         219.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.3355(6)
_cell_length_b                   7.4390(8)
_cell_length_c                   26.291(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1239.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4795
_cell_measurement_theta_min      3.1557
_cell_measurement_theta_max      24.8706

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21730
_diffrn_reflns_av_R_equivalents  0.1681
_diffrn_reflns_av_sigmaI/netI    0.0915
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         29.02
_reflns_number_total             2988
_reflns_number_gt                1856
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.57414(16) 0.38082(19) 0.20345(5) 0.0452(3) Uani 1 1 d . . .
HO H 0.5731 0.4909 0.2021 0.068 Uiso 1 1 calc R . .
N N 0.4421(2) 0.2841(2) 0.30126(5) 0.0386(4) Uani 1 1 d . . .
C1 C 0.4055(2) 0.3460(3) 0.35350(6) 0.0486(5) Uani 1 1 d . . .
H1A H 0.4167 0.4760 0.3550 0.058 Uiso 1 1 calc R . .
H1B H 0.5112 0.2952 0.3760 0.058 Uiso 1 1 calc R . .
C2 C 0.1885(3) 0.2883(3) 0.37039(6) 0.0476(5) Uani 1 1 d . . .
H2A H 0.1605 0.3346 0.4042 0.057 Uiso 1 1 calc R . .
H2B H 0.1819 0.1581 0.3718 0.057 Uiso 1 1 calc R . .
C3 C 0.0234(2) 0.3574(3) 0.33386(5) 0.0413(5) Uani 1 1 d . . .
H3A H 0.0161 0.4874 0.3362 0.050 Uiso 1 1 calc R . .
H3B H -0.1135 0.3093 0.3433 0.050 Uiso 1 1 calc R . .
C4 C 0.0738(2) 0.3039(3) 0.27934(5) 0.0355(4) Uani 1 1 d . . .
H4A H 0.0648 0.1743 0.2759 0.043 Uiso 1 1 calc R . .
H4B H -0.0288 0.3573 0.2565 0.043 Uiso 1 1 calc R . .
C5 C 0.2931(2) 0.3661(3) 0.26492(5) 0.0299(4) Uani 1 1 d . . .
H5 H 0.2999 0.4971 0.2686 0.036 Uiso 1 1 calc R . .
C6 C 0.3645(2) 0.3166(3) 0.21142(5) 0.0339(4) Uani 1 1 d . . .
H6 H 0.3687 0.1851 0.2094 0.041 Uiso 1 1 calc R . .
C7 C 0.2164(2) 0.3828(3) 0.17005(5) 0.0351(4) Uani 1 1 d . . .
H7A H 0.2103 0.5130 0.1713 0.042 Uiso 1 1 calc R . .
H7B H 0.0756 0.3374 0.1767 0.042 Uiso 1 1 calc R . .
C8 C 0.2838(3) 0.3246(3) 0.11699(5) 0.0475(5) Uani 1 1 d . . .
H8A H 0.4237 0.3717 0.1101 0.057 Uiso 1 1 calc R . .
H8B H 0.2921 0.1945 0.1159 0.057 Uiso 1 1 calc R . .
C9 C 0.1348(3) 0.3880(3) 0.07593(5) 0.0376(5) Uani 1 1 d . . .
C10 C -0.0617(3) 0.3098(3) 0.07017(6) 0.0447(5) Uani 1 1 d . . .
H10 H -0.1032 0.2188 0.0923 0.054 Uiso 1 1 calc R . .
C11 C -0.1968(3) 0.3645(3) 0.03233(6) 0.0500(5) Uani 1 1 d . . .
H11 H -0.3285 0.3106 0.0291 0.060 Uiso 1 1 calc R . .
C12 C -0.1381(3) 0.4980(3) -0.00061(7) 0.0536(6) Uani 1 1 d . . .
H12 H -0.2289 0.5337 -0.0265 0.064 Uiso 1 1 calc R . .
C13 C 0.0551(3) 0.5789(3) 0.00470(6) 0.0533(5) Uani 1 1 d . . .
H13 H 0.0953 0.6707 -0.0173 0.064 Uiso 1 1 calc R . .
C14 C 0.1894(3) 0.5233(3) 0.04289(6) 0.0461(5) Uani 1 1 d . . .
H14 H 0.3202 0.5788 0.0464 0.055 Uiso 1 1 calc R . .
HN H 0.567(2) 0.325(2) 0.2917(5) 0.031(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0297(6) 0.0603(9) 0.0455(6) 0.0054(7) 0.0037(5) 0.0010(7)
N 0.0261(8) 0.0549(10) 0.0347(7) 0.0065(7) -0.0022(7) 0.0015(8)
C1 0.0424(11) 0.0702(16) 0.0331(8) 0.0035(10) -0.0051(7) -0.0056(11)
C2 0.0493(12) 0.0603(14) 0.0331(9) 0.0017(9) 0.0043(8) -0.0064(11)
C3 0.0334(9) 0.0477(13) 0.0428(9) -0.0041(9) 0.0068(7) -0.0042(9)
C4 0.0296(9) 0.0392(11) 0.0376(8) 0.0009(8) -0.0025(7) -0.0005(9)
C5 0.0279(8) 0.0307(10) 0.0312(7) 0.0002(8) -0.0033(6) 0.0007(8)
C6 0.0318(9) 0.0339(11) 0.0359(8) 0.0004(8) 0.0008(7) 0.0015(8)
C7 0.0351(9) 0.0398(11) 0.0306(7) -0.0006(8) -0.0012(7) 0.0032(9)
C8 0.0485(11) 0.0617(14) 0.0322(8) -0.0004(9) -0.0008(8) 0.0150(11)
C9 0.0448(10) 0.0421(12) 0.0261(8) -0.0044(8) 0.0037(7) 0.0075(9)
C10 0.0503(11) 0.0475(13) 0.0364(9) 0.0028(8) 0.0028(9) -0.0024(11)
C11 0.0445(11) 0.0599(14) 0.0457(10) -0.0120(11) -0.0026(9) -0.0058(11)
C12 0.0635(14) 0.0596(15) 0.0375(9) -0.0046(10) -0.0127(9) 0.0131(12)
C13 0.0703(14) 0.0488(14) 0.0407(10) 0.0076(9) 0.0008(10) 0.0025(13)
C14 0.0477(12) 0.0501(13) 0.0406(9) -0.0017(9) 0.0005(9) -0.0029(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C6 1.4270(19) . ?
N C1 1.467(2) . ?
N C5 1.4752(19) . ?
C1 C2 1.507(2) . ?
C2 C3 1.510(2) . ?
C3 C4 1.522(2) . ?
C4 C5 1.513(2) . ?
C5 C6 1.5226(19) . ?
C6 C7 1.519(2) . ?
C7 C8 1.522(2) . ?
C8 C9 1.509(2) . ?
C9 C14 1.374(3) . ?
C9 C10 1.382(2) . ?
C10 C11 1.374(2) . ?
C11 C12 1.369(3) . ?
C12 C13 1.371(3) . ?
C13 C14 1.380(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C5 112.03(14) . . ?
N C1 C2 109.29(15) . . ?
C1 C2 C3 110.33(14) . . ?
C2 C3 C4 111.37(14) . . ?
C5 C4 C3 110.42(13) . . ?
N C5 C4 107.39(13) . . ?
N C5 C6 107.95(13) . . ?
C4 C5 C6 115.47(13) . . ?
O C6 C7 111.18(13) . . ?
O C6 C5 109.33(13) . . ?
C7 C6 C5 113.56(13) . . ?
C6 C7 C8 113.02(14) . . ?
C9 C8 C7 113.04(14) . . ?
C14 C9 C10 117.76(15) . . ?
C14 C9 C8 121.55(17) . . ?
C10 C9 C8 120.68(17) . . ?
C11 C10 C9 121.05(18) . . ?
C12 C11 C10 120.24(19) . . ?
C11 C12 C13 119.78(17) . . ?
C12 C13 C14 119.53(18) . . ?
C9 C14 C13 121.63(18) . . ?

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043