# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cu_xx394_0m
_database_code_depnum_ccdc_archive 'CCDC 1436041'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(1R,2R)-2-(4-phenylpiperidin-1-yl)-1,2-dihydronaphthalen-1-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2 O'
_chemical_formula_sum            'C20 H22 N2 O'
_chemical_formula_weight         306.40
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   6.3758(2)
_cell_length_b                   10.5378(4)
_cell_length_c                   23.8709(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1603.81(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9183
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      69.03

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.30
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5024
_exptl_absorpt_correction_T_max  0.8870
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8344
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         69.17
_reflns_number_total             2848
_reflns_number_gt                2836
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1106P)²+0.5598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0088(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         2848
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1554
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
O1 O 1.1984(2) 0.65799(14) 0.75617(6) 0.0170(4) Uani 1 1 d . . .
H1 H 1.1014 0.6972 0.7725 0.026 Uiso 1 1 calc R . .
N1 N 1.0940(3) 0.22606(17) 0.58123(8) 0.0163(4) Uani 1 1 d . . .
N2 N 1.0308(3) 0.35990(16) 0.68546(7) 0.0139(4) Uani 1 1 d . . .
C1 C 1.1085(5) -0.0764(2) 0.46403(10) 0.0286(6) Uani 1 1 d . . .
H1A H 1.1107 -0.1447 0.4381 0.034 Uiso 1 1 calc R . .
C2 C 1.2803(5) -0.0516(2) 0.49779(10) 0.0273(6) Uani 1 1 d . . .
H2 H 1.4020 -0.1033 0.4948 0.033 Uiso 1 1 calc R . .
C3 C 1.2768(4) 0.0483(2) 0.53608(9) 0.0232(5) Uani 1 1 d . . .
H3 H 1.3971 0.0647 0.5584 0.028 Uiso 1 1 calc R . .
C4 C 1.0991(4) 0.1249(2) 0.54213(9) 0.0176(5) Uani 1 1 d . . .
C5 C 1.2399(3) 0.2122(2) 0.62854(9) 0.0177(5) Uani 1 1 d . . .
H5A H 1.3830 0.1970 0.6140 0.021 Uiso 1 1 calc R . .
H5B H 1.1986 0.1375 0.6511 0.021 Uiso 1 1 calc R . .
C6 C 1.2420(4) 0.3295(2) 0.66585(9) 0.0164(5) Uani 1 1 d . . .
H6A H 1.3345 0.3142 0.6985 0.020 Uiso 1 1 calc R . .
H6B H 1.2991 0.4024 0.6446 0.020 Uiso 1 1 calc R . .
C7 C 1.0287(3) 0.4643(2) 0.72735(8) 0.0143(5) Uani 1 1 d . . .
H7 H 1.1208 0.4359 0.7589 0.017 Uiso 1 1 calc R . .
C8 C 1.1154(3) 0.5940(2) 0.70801(9) 0.0136(5) Uani 1 1 d . . .
H8 H 1.2332 0.5782 0.6812 0.016 Uiso 1 1 calc R . .
C9 C 0.9547(4) 0.67665(19) 0.67911(9) 0.0155(5) Uani 1 1 d . . .
C10 C 1.0133(4) 0.7627(2) 0.63741(10) 0.0192(5) Uani 1 1 d . . .
H10 H 1.1528 0.7628 0.6234 0.023 Uiso 1 1 calc R . .
C11 C 0.8673(4) 0.8482(2) 0.61649(10) 0.0226(6) Uani 1 1 d . . .
H11 H 0.9065 0.9061 0.5878 0.027 Uiso 1 1 calc R . .
C12 C 0.6654(4) 0.8493(2) 0.63729(10) 0.0224(5) Uani 1 1 d . . .
H12 H 0.5672 0.9100 0.6239 0.027 Uiso 1 1 calc R . .
C13 C 0.9347(4) 0.0001(2) 0.46889(10) 0.0265(6) Uani 1 1 d . . .
H13 H 0.8164 -0.0158 0.4457 0.032 Uiso 1 1 calc R . .
C14 C 0.9275(4) 0.1007(2) 0.50708(9) 0.0203(5) Uani 1 1 d . . .
H14 H 0.8061 0.1528 0.5092 0.024 Uiso 1 1 calc R . .
C15 C 0.9002(4) 0.38480(19) 0.63596(9) 0.0155(5) Uani 1 1 d . . .
H15A H 0.9613 0.4556 0.6141 0.019 Uiso 1 1 calc R . .
H15B H 0.7577 0.4102 0.6480 0.019 Uiso 1 1 calc R . .
C16 C 0.8862(4) 0.2673(2) 0.59928(9) 0.0170(5) Uani 1 1 d . . .
H16A H 0.8176 0.1981 0.6205 0.020 Uiso 1 1 calc R . .
H16B H 0.7990 0.2862 0.5660 0.020 Uiso 1 1 calc R . .
C17 C 0.6052(4) 0.7619(2) 0.67778(9) 0.0181(5) Uani 1 1 d . . .
H17 H 0.4655 0.7623 0.6916 0.022 Uiso 1 1 calc R . .
C18 C 0.7484(3) 0.6735(2) 0.69832(9) 0.0148(5) Uani 1 1 d . . .
C19 C 0.6871(3) 0.5755(2) 0.73877(9) 0.0148(5) Uani 1 1 d . . .
H19 H 0.5538 0.5812 0.7564 0.018 Uiso 1 1 calc R . .
C20 C 0.8128(3) 0.47852(19) 0.75153(8) 0.0147(5) Uani 1 1 d . . .
H20 H 0.7637 0.4159 0.7770 0.018 Uiso 1 1 calc R . .


_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
O1 C8 1.434(2) . ?
O1 H1 0.8400 . ?
N1 C4 1.418(3) . ?
N1 C16 1.460(3) . ?
N1 C5 1.470(3) . ?
N2 C6 1.461(3) . ?
N2 C15 1.469(3) . ?
N2 C7 1.486(3) . ?
C1 C13 1.376(4) . ?
C1 C2 1.385(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(4) . ?
C3 H3 0.9500 . ?
C4 C14 1.401(3) . ?
C5 C6 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C20 1.500(3) . ?
C7 C8 1.545(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.511(3) . ?
C8 H8 1.0000 . ?
C9 C18 1.394(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C17 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.467(3) . ?
C19 C20 1.334(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C8 O1 H1 109.5 . . ?
C4 N1 C16 116.06(18) . . ?
C4 N1 C5 114.64(17) . . ?
C16 N1 C5 112.14(17) . . ?
C6 N2 C15 107.68(16) . . ?
C6 N2 C7 112.74(16) . . ?
C15 N2 C7 113.81(16) . . ?
C13 C1 C2 118.6(2) . . ?
C13 C1 H1A 120.7 . . ?
C2 C1 H1A 120.7 . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C14 117.8(2) . . ?
C3 C4 N1 121.4(2) . . ?
C14 C4 N1 120.8(2) . . ?
N1 C5 C6 112.00(17) . . ?
N1 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C6 C5 110.93(17) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C20 109.97(17) . . ?
N2 C7 C8 116.75(16) . . ?
C20 C7 C8 110.78(17) . . ?
N2 C7 H7 106.2 . . ?
C20 C7 H7 106.2 . . ?
C8 C7 H7 106.2 . . ?
O1 C8 C9 110.15(17) . . ?
O1 C8 C7 107.98(16) . . ?
C9 C8 C7 113.82(18) . . ?
O1 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C18 C9 C10 120.1(2) . . ?
C18 C9 C8 118.42(19) . . ?
C10 C9 C8 121.2(2) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C17 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C17 C12 H12 119.9 . . ?
C1 C13 C14 121.7(2) . . ?
C1 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C4 120.1(2) . . ?
C13 C14 H14 120.0 . . ?
C4 C14 H14 120.0 . . ?
N2 C15 C16 110.57(17) . . ?
N2 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N1 C16 C15 111.09(18) . . ?
N1 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C12 C17 C18 120.5(2) . . ?
C12 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C9 119.1(2) . . ?
C17 C18 C19 121.9(2) . . ?
C9 C18 C19 118.99(19) . . ?
C20 C19 C18 122.0(2) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C7 122.71(19) . . ?
C19 C20 H20 118.6 . . ?
C7 C20 H20 118.6 . . ?

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
C13 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C14 -2.2(3) . . . . ?
C2 C3 C4 N1 179.6(2) . . . . ?
C16 N1 C4 C3 -157.6(2) . . . . ?
C5 N1 C4 C3 -24.3(3) . . . . ?
C16 N1 C4 C14 24.2(3) . . . . ?
C5 N1 C4 C14 157.5(2) . . . . ?
C4 N1 C5 C6 174.50(18) . . . . ?
C16 N1 C5 C6 -50.4(2) . . . . ?
C15 N2 C6 C5 -60.4(2) . . . . ?
C7 N2 C6 C5 173.19(16) . . . . ?
N1 C5 C6 N2 55.4(2) . . . . ?
C6 N2 C7 C20 -172.20(17) . . . . ?
C15 N2 C7 C20 64.8(2) . . . . ?
C6 N2 C7 C8 60.5(2) . . . . ?
C15 N2 C7 C8 -62.5(2) . . . . ?
N2 C7 C8 O1 -151.30(17) . . . . ?
C20 C7 C8 O1 81.8(2) . . . . ?
N2 C7 C8 C9 86.1(2) . . . . ?
C20 C7 C8 C9 -40.8(2) . . . . ?
O1 C8 C9 C18 -85.2(2) . . . . ?
C7 C8 C9 C18 36.2(3) . . . . ?
O1 C8 C9 C10 89.2(2) . . . . ?
C7 C8 C9 C10 -149.40(19) . . . . ?
C18 C9 C10 C11 2.2(3) . . . . ?
C8 C9 C10 C11 -172.1(2) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C17 -2.3(3) . . . . ?
C2 C1 C13 C14 -0.4(4) . . . . ?
C1 C13 C14 C4 -0.8(3) . . . . ?
C3 C4 C14 C13 2.1(3) . . . . ?
N1 C4 C14 C13 -179.7(2) . . . . ?
C6 N2 C15 C16 62.2(2) . . . . ?
C7 N2 C15 C16 -172.08(17) . . . . ?
C4 N1 C16 C15 -173.81(16) . . . . ?
C5 N1 C16 C15 51.8(2) . . . . ?
N2 C15 C16 N1 -58.5(2) . . . . ?
C11 C12 C17 C18 0.9(3) . . . . ?
C12 C17 C18 C9 2.1(3) . . . . ?
C12 C17 C18 C19 -176.58(19) . . . . ?
C10 C9 C18 C17 -3.7(3) . . . . ?
C8 C9 C18 C17 170.82(18) . . . . ?
C10 C9 C18 C19 175.09(18) . . . . ?
C8 C9 C18 C19 -10.4(3) . . . . ?
C17 C18 C19 C20 168.7(2) . . . . ?
C9 C18 C19 C20 -10.0(3) . . . . ?
C18 C19 C20 C7 2.2(3) . . . . ?
N2 C7 C20 C19 -107.2(2) . . . . ?
C8 C7 C20 C19 23.3(3) . . . . ?

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
O1 H1 N2 0.84 2.16 2.933(2) 153.5 3_756

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        69.17
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.080
