# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0055_Lan
_database_code_depnum_ccdc_archive 'CCDC 1416792'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(1S,2R,3R)-1-phenyl-3-(phenylamino)hexane-1,2-diol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N O2'
_chemical_formula_sum            'C18 H23 N O2'
_chemical_formula_weight         285.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.2823(3)
_cell_length_b                   10.7630(7)
_cell_length_c                   27.6349(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1571.14(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6387
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      66.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.615
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS (version 2012/4) as implemented in APEX2, version 2014.9-0, Bruker AXS
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'INCOATEC ImuS micro-focus source'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            10178
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         66.519
_diffrn_reflns_theta_full        66.519
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2739
_reflns_number_gt                2211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.978

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v.2014.9-0 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V.8.27 (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V.8.27 (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565

Mercury: visualization and analysis of crystal structures
C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, 
R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006 
;
_computing_publication_material  'APEX2 v.2014.9-0 (Bruker AXS Inc., 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.3640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     
;
dual-space method as implemented in SHELXT
;
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 729 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2739
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1745(6) 0.4164(4) 0.78209(13) 0.0293(9) Uani 1 1 d . . . . .
H1 H 0.2186 0.3331 0.7745 0.035 Uiso 1 1 calc R U . . .
C2 C 0.0009(7) 0.4396(4) 0.81872(13) 0.0322(9) Uani 1 1 d . . . . .
H2 H -0.0738 0.3726 0.8360 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0625(7) 0.5611(4) 0.82994(13) 0.0326(9) Uani 1 1 d . . . . .
H3 H -0.1835 0.5774 0.8546 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0497(7) 0.6592(4) 0.80543(13) 0.0300(9) Uani 1 1 d . . . . .
H4 H 0.0096 0.7425 0.8138 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2208(7) 0.6345(4) 0.76865(12) 0.0278(9) Uani 1 1 d . . . . .
H5 H 0.2959 0.7015 0.7515 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2844(6) 0.5131(3) 0.75640(12) 0.0258(8) Uani 1 1 d . . . . .
C7 C 0.4530(6) 0.4881(4) 0.71309(14) 0.0259(8) Uani 1 1 d . . . . .
H7 H 0.492(7) 0.396(3) 0.7117(13) 0.031 Uiso 1 1 d . U . . .
C8 C 0.3185(6) 0.5257(4) 0.66602(13) 0.0253(8) Uani 1 1 d . . . . .
H8 H 0.278(7) 0.621(4) 0.6702(13) 0.030 Uiso 1 1 d . U . . .
C9 C 0.4715(6) 0.5049(3) 0.61957(12) 0.0254(8) Uani 1 1 d . . . . .
H9 H 0.6397 0.5462 0.6238 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5191(7) 0.3688(3) 0.60745(13) 0.0268(8) Uani 1 1 d . . . . .
H10A H 0.3576 0.3296 0.5976 0.032 Uiso 1 1 calc R U . . .
H10B H 0.5806 0.3254 0.6368 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7128(7) 0.3528(4) 0.56692(13) 0.0309(9) Uani 1 1 d . . . . .
H11A H 0.6517 0.3972 0.5378 0.037 Uiso 1 1 calc R U . . .
H11B H 0.8742 0.3917 0.5770 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7622(8) 0.2186(4) 0.55380(14) 0.0373(10) Uani 1 1 d . . . . .
H12A H 0.8145 0.1728 0.5828 0.056 Uiso 1 1 calc R U . . .
H12B H 0.8968 0.2145 0.5295 0.056 Uiso 1 1 calc R U . . .
H12C H 0.6073 0.1816 0.5407 0.056 Uiso 1 1 calc R U . . .
C13 C 0.3239(6) 0.6932(4) 0.57457(12) 0.0253(8) Uani 1 1 d . . . . .
C14 C 0.4989(7) 0.7742(3) 0.59471(13) 0.0272(8) Uani 1 1 d . . . . .
H14 H 0.6312 0.7430 0.6146 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4808(7) 0.9008(3) 0.58589(13) 0.0304(9) Uani 1 1 d . . . . .
H15 H 0.6035 0.9553 0.5994 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2885(7) 0.9490(4) 0.55803(13) 0.0313(9) Uani 1 1 d . . . . .
H16 H 0.2784 1.0358 0.5521 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1094(7) 0.8685(4) 0.53879(13) 0.0297(9) Uani 1 1 d . . . . .
H17 H -0.0260 0.9009 0.5200 0.036 Uiso 1 1 calc R U . . .
C18 C 0.1256(6) 0.7430(4) 0.54660(12) 0.0279(9) Uani 1 1 d . . . . .
H18 H 0.0020 0.6891 0.5330 0.033 Uiso 1 1 calc R U . . .
N1 N 0.3439(5) 0.5643(3) 0.57876(10) 0.0259(7) Uani 1 1 d . . . . .
H1A H 0.201(7) 0.527(3) 0.5705(13) 0.031 Uiso 1 1 d . U . . .
O1 O 0.6827(4) 0.5605(3) 0.71492(9) 0.0322(6) Uani 1 1 d . . . . .
H1B H 0.745(8) 0.553(4) 0.7445(15) 0.048 Uiso 1 1 d . U . . .
O2 O 0.0886(4) 0.4567(3) 0.66146(9) 0.0291(6) Uani 1 1 d . . . . .
H2A H -0.022(8) 0.491(4) 0.6809(14) 0.044 Uiso 1 1 d . U . . .


_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
C1 C6 1.387(5) . ?
C1 C2 1.388(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.516(5) . ?
C7 O1 1.443(4) . ?
C7 C8 1.537(5) . ?
C7 H7 1.02(4) . ?
C8 O2 1.429(4) . ?
C8 C9 1.533(5) . ?
C8 H8 1.05(4) . ?
C9 N1 1.461(4) . ?
C9 C10 1.524(5) . ?
C9 H9 1.0000 . ?
C10 C11 1.526(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.512(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.387(5) . ?
C13 N1 1.397(5) . ?
C13 C18 1.407(5) . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1A 0.89(4) . ?
O1 H1B 0.88(4) . ?
O2 H2A 0.87(4) . ?

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
C6 C1 C2 121.0(4) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 121.1(3) . . ?
C5 C6 C7 120.1(3) . . ?
O1 C7 C6 111.7(3) . . ?
O1 C7 C8 106.0(3) . . ?
C6 C7 C8 110.5(3) . . ?
O1 C7 H7 111(2) . . ?
C6 C7 H7 109(2) . . ?
C8 C7 H7 109(2) . . ?
O2 C8 C9 107.3(3) . . ?
O2 C8 C7 109.3(3) . . ?
C9 C8 C7 115.3(3) . . ?
O2 C8 H8 110(2) . . ?
C9 C8 H8 110(2) . . ?
C7 C8 H8 105(2) . . ?
N1 C9 C10 109.1(3) . . ?
N1 C9 C8 109.8(3) . . ?
C10 C9 C8 114.3(3) . . ?
N1 C9 H9 107.8 . . ?
C10 C9 H9 107.8 . . ?
C8 C9 H9 107.8 . . ?
C9 C10 C11 112.3(3) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 113.6(3) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 122.7(3) . . ?
C14 C13 C18 118.5(3) . . ?
N1 C13 C18 118.7(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.8(4) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C13 N1 C9 122.3(3) . . ?
C13 N1 H1A 112(2) . . ?
C9 N1 H1A 113(2) . . ?
C7 O1 H1B 107(3) . . ?
C8 O2 H2A 107(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(5) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C2 C1 C6 C5 1.2(5) . . . . ?
C2 C1 C6 C7 -173.7(3) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 174.3(3) . . . . ?
C1 C6 C7 O1 -133.5(3) . . . . ?
C5 C6 C7 O1 51.7(4) . . . . ?
C1 C6 C7 C8 108.7(4) . . . . ?
C5 C6 C7 C8 -66.1(4) . . . . ?
O1 C7 C8 O2 179.6(3) . . . . ?
C6 C7 C8 O2 -59.2(4) . . . . ?
O1 C7 C8 C9 58.6(4) . . . . ?
C6 C7 C8 C9 179.9(3) . . . . ?
O2 C8 C9 N1 68.2(4) . . . . ?
C7 C8 C9 N1 -169.8(3) . . . . ?
O2 C8 C9 C10 -54.8(4) . . . . ?
C7 C8 C9 C10 67.2(4) . . . . ?
N1 C9 C10 C11 67.7(4) . . . . ?
C8 C9 C10 C11 -169.0(3) . . . . ?
C9 C10 C11 C12 -179.5(3) . . . . ?
N1 C13 C14 C15 174.6(3) . . . . ?
C18 C13 C14 C15 -2.0(5) . . . . ?
C13 C14 C15 C16 1.2(6) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
C16 C17 C18 C13 0.3(5) . . . . ?
C14 C13 C18 C17 1.2(5) . . . . ?
N1 C13 C18 C17 -175.5(3) . . . . ?
C14 C13 N1 C9 27.5(5) . . . . ?
C18 C13 N1 C9 -155.9(3) . . . . ?
C10 C9 N1 C13 -165.9(3) . . . . ?
C8 C9 N1 C13 68.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O1 0.87(4) 1.97(4) 2.833(3) 169(4) 1_455

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.047

