##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-[(3-Methylpiperidin-1-yl)(3-nitrophenyl)methyl]naphthalen-2-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H24 N2 O3'
_chemical_formula_sum     'C23 H24 N2 O3'
_chemical_formula_iupac     'C23 H24 N2 O3'
_chemical_formula_weight     376.44
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_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'
    '-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     11.980(2)
_cell_length_b     10.965(2)
_cell_length_c     30.30(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3980(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4541
_cell_measurement_theta_min     2.29
_cell_measurement_theta_max     27.46
_cell_measurement_temperature     295(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Colourless'
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.256
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1600
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.982
_exptl_absorpt_correction_T_max     0.992
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku SCXmini'
_diffrn_measurement_method     'CCD_Profile_fitting'
_diffrn_detector_area_resol_mean     13.6612
_diffrn_reflns_number     34080
_diffrn_reflns_av_R_equivalents     0.1096
_diffrn_reflns_av_sigmaI/netI     0.0434
_diffrn_reflns_theta_min     2.61
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -37
_diffrn_reflns_limit_l_max     37
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     3877
_reflns_number_gt     2409
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1386
_refine_ls_R_factor_gt     0.0832
_refine_ls_wR_factor_gt     0.1530
_refine_ls_wR_factor_ref     0.1737
_refine_ls_goodness_of_fit_ref     1.122
_refine_ls_restrained_S_all     1.122
_refine_ls_number_reflns     3877
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0563P)²+1.4193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.137
_refine_diff_density_min     -0.148
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL/PC (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.7000(2) 0.9558(2) 0.65000(10) 0.0433(7) Uani d . 1 . .
    C C2 0.6194(2) 1.0425(3) 0.64171(11) 0.0523(8) Uani d . 1 . .
    C C3 0.5315(3) 1.0634(3) 0.67144(13) 0.0659(9) Uani d . 1 . .
    H H3 0.4769 1.1206 0.6646 0.079 Uiso calc R 1 . .
    C C4 0.5255(3) 1.0015(4) 0.70975(13) 0.0707(10) Uani d . 1 . .
    H H4 0.4661 1.0161 0.7288 0.085 Uiso calc R 1 . .
    C C5 0.6075(3) 0.9147(3) 0.72156(11) 0.0584(9) Uani d . 1 . .
    C C6 0.6961(2) 0.8920(3) 0.69134(10) 0.0478(7) Uani d . 1 . .
    C C7 0.7785(3) 0.8061(3) 0.70421(10) 0.0552(8) Uani d . 1 . .
    H H7 0.8381 0.7905 0.6854 0.066 Uiso calc R 1 . .
    C C8 0.7725(3) 0.7459(3) 0.74356(11) 0.0708(10) Uani d . 1 . .
    H H8 0.8279 0.6904 0.7513 0.085 Uiso calc R 1 . .
    C C9 0.6840(3) 0.7671(4) 0.77209(12) 0.0820(12) Uani d . 1 . .
    H H9 0.6796 0.7246 0.7986 0.098 Uiso calc R 1 . .
    C C10 0.6041(3) 0.8493(4) 0.76161(12) 0.0774(11) Uani d . 1 . .
    H H10 0.5457 0.8630 0.7812 0.093 Uiso calc R 1 . .
    C C11 0.7905(2) 0.9244(2) 0.61686(9) 0.0422(7) Uani d . 1 . .
    H H11 0.8033 0.8363 0.6189 0.051 Uiso calc R 1 . .
    C C12 0.6680(3) 0.8576(3) 0.55808(11) 0.0599(9) Uani d . 1 . .
    H H12A 0.6106 0.8529 0.5806 0.072 Uiso calc R 1 . .
    H H12B 0.7044 0.7787 0.5564 0.072 Uiso calc R 1 . .
    C C13 0.6143(3) 0.8861(3) 0.51400(13) 0.0728(11) Uani d . 1 . .
    H H13 0.5776 0.9657 0.5166 0.087 Uiso calc R 1 . .
    C C14 0.7021(4) 0.8968(4) 0.47882(13) 0.0945(14) Uani d . 1 . .
    H H14A 0.6680 0.9242 0.4515 0.113 Uiso calc R 1 . .
    H H14B 0.7353 0.8175 0.4736 0.113 Uiso calc R 1 . .
    C C15 0.7918(3) 0.9860(4) 0.49260(11) 0.0828(12) Uani d . 1 . .
    H H15A 0.8513 0.9851 0.4709 0.099 Uiso calc R 1 . .
    H H15B 0.7605 1.0676 0.4933 0.099 Uiso calc R 1 . .
    C C16 0.8395(3) 0.9559(3) 0.53738(10) 0.0633(9) Uani d . 1 . .
    H H16A 0.8776 0.8780 0.5361 0.076 Uiso calc R 1 . .
    H H16B 0.8936 1.0176 0.5457 0.076 Uiso calc R 1 . .
    C C17 0.5250(4) 0.7925(3) 0.50331(16) 0.1061(16) Uani d . 1 . .
    H H17A 0.4876 0.8153 0.4765 0.159 Uiso calc R 1 . .
    H H17B 0.4719 0.7892 0.5270 0.159 Uiso calc R 1 . .
    H H17C 0.5590 0.7139 0.4996 0.159 Uiso calc R 1 . .
    C C18 0.9014(2) 0.9868(3) 0.62676(9) 0.0428(7) Uani d . 1 . .
    C C19 1.0000(2) 0.9224(3) 0.62142(9) 0.0472(7) Uani d . 1 . .
    H H19 0.9988 0.8410 0.6128 0.057 Uiso calc R 1 . .
    C C20 1.0999(3) 0.9808(3) 0.62900(10) 0.0553(8) Uani d . 1 . .
    C C21 1.1060(3) 1.1004(4) 0.64166(12) 0.0710(10) Uani d . 1 . .
    H H21 1.1746 1.1379 0.6463 0.085 Uiso calc R 1 . .
    C C22 1.0079(3) 1.1635(3) 0.64731(13) 0.0748(10) Uani d . 1 . .
    H H22 1.0099 1.2448 0.6560 0.090 Uiso calc R 1 . .
    C C23 0.9067(3) 1.1075(3) 0.64020(11) 0.0584(8) Uani d . 1 . .
    H H23 0.8410 1.1512 0.6445 0.070 Uiso calc R 1 . .
    N N1 0.7505(2) 0.9505(2) 0.57076(7) 0.0469(6) Uani d . 1 . .
    N N2 1.2039(3) 0.9098(4) 0.62304(11) 0.0788(9) Uani d . 1 . .
    O O1 0.61885(19) 1.11174(19) 0.60442(8) 0.0645(6) Uani d . 1 . .
    H H1 0.6631 1.0833 0.5865 0.097 Uiso calc R 1 . .
    O O2 1.1967(2) 0.8052(3) 0.61087(11) 0.1051(10) Uani d . 1 . .
    O O3 1.2920(2) 0.9589(3) 0.63113(13) 0.1305(14) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.379(4) ?
    C1 C6 . 1.435(4) ?
    C1 C11 . 1.517(4) ?
    C2 O1 . 1.361(4) ?
    C2 C3 . 1.404(4) ?
    C3 C4 . 1.347(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.413(5) ?
    C4 H4 . 0.9300 ?
    C5 C10 . 1.410(5) ?
    C5 C6 . 1.424(4) ?
    C6 C7 . 1.419(4) ?
    C7 C8 . 1.365(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.387(5) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.353(5) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 N1 . 1.505(4) ?
    C11 C18 . 1.524(4) ?
    C11 H11 . 0.9800 ?
    C12 N1 . 1.471(4) ?
    C12 C13 . 1.515(5) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C14 . 1.502(5) ?
    C13 C17 . 1.518(5) ?
    C13 H13 . 0.9800 ?
    C14 C15 . 1.511(5) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.509(5) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 N1 . 1.471(4) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 C19 . 1.386(4) ?
    C18 C23 . 1.387(4) ?
    C19 C20 . 1.376(4) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.368(5) ?
    C20 N2 . 1.481(4) ?
    C21 C22 . 1.375(5) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.376(4) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 0.9300 ?
    N2 O2 . 1.207(4) ?
    N2 O3 . 1.210(4) ?
    O1 H1 . 0.8200 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C6 . . 118.2(3) ?
    C2 C1 C11 . . 122.5(3) ?
    C6 C1 C11 . . 119.3(2) ?
    O1 C2 C1 . . 122.6(3) ?
    O1 C2 C3 . . 116.0(3) ?
    C1 C2 C3 . . 121.4(3) ?
    C4 C3 C2 . . 120.7(3) ?
    C4 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    C3 C4 C5 . . 121.3(3) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    C10 C5 C4 . . 122.7(3) ?
    C10 C5 C6 . . 119.0(3) ?
    C4 C5 C6 . . 118.3(3) ?
    C7 C6 C5 . . 117.3(3) ?
    C7 C6 C1 . . 122.8(3) ?
    C5 C6 C1 . . 120.0(3) ?
    C8 C7 C6 . . 121.7(3) ?
    C8 C7 H7 . . 119.2 ?
    C6 C7 H7 . . 119.2 ?
    C7 C8 C9 . . 120.2(4) ?
    C7 C8 H8 . . 119.9 ?
    C9 C8 H8 . . 119.9 ?
    C10 C9 C8 . . 120.4(3) ?
    C10 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C9 C10 C5 . . 121.4(3) ?
    C9 C10 H10 . . 119.3 ?
    C5 C10 H10 . . 119.3 ?
    N1 C11 C1 . . 110.1(2) ?
    N1 C11 C18 . . 112.0(2) ?
    C1 C11 C18 . . 113.0(2) ?
    N1 C11 H11 . . 107.1 ?
    C1 C11 H11 . . 107.1 ?
    C18 C11 H11 . . 107.1 ?
    N1 C12 C13 . . 111.9(3) ?
    N1 C12 H12A . . 109.2 ?
    C13 C12 H12A . . 109.2 ?
    N1 C12 H12B . . 109.2 ?
    C13 C12 H12B . . 109.2 ?
    H12A C12 H12B . . 107.9 ?
    C14 C13 C12 . . 110.1(3) ?
    C14 C13 C17 . . 113.3(4) ?
    C12 C13 C17 . . 110.3(3) ?
    C14 C13 H13 . . 107.6 ?
    C12 C13 H13 . . 107.6 ?
    C17 C13 H13 . . 107.6 ?
    C13 C14 C15 . . 110.6(3) ?
    C13 C14 H14A . . 109.5 ?
    C15 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    C15 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 108.1 ?
    C16 C15 C14 . . 112.1(3) ?
    C16 C15 H15A . . 109.2 ?
    C14 C15 H15A . . 109.2 ?
    C16 C15 H15B . . 109.2 ?
    C14 C15 H15B . . 109.2 ?
    H15A C15 H15B . . 107.9 ?
    N1 C16 C15 . . 110.6(3) ?
    N1 C16 H16A . . 109.5 ?
    C15 C16 H16A . . 109.5 ?
    N1 C16 H16B . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 108.1 ?
    C13 C17 H17A . . 109.5 ?
    C13 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C13 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C19 C18 C23 . . 118.8(3) ?
    C19 C18 C11 . . 119.5(3) ?
    C23 C18 C11 . . 121.7(3) ?
    C20 C19 C18 . . 119.0(3) ?
    C20 C19 H19 . . 120.5 ?
    C18 C19 H19 . . 120.5 ?
    C21 C20 C19 . . 122.6(3) ?
    C21 C20 N2 . . 119.6(3) ?
    C19 C20 N2 . . 117.8(3) ?
    C20 C21 C22 . . 118.1(3) ?
    C20 C21 H21 . . 120.9 ?
    C22 C21 H21 . . 120.9 ?
    C21 C22 C23 . . 120.6(3) ?
    C21 C22 H22 . . 119.7 ?
    C23 C22 H22 . . 119.7 ?
    C22 C23 C18 . . 120.8(3) ?
    C22 C23 H23 . . 119.6 ?
    C18 C23 H23 . . 119.6 ?
    C12 N1 C16 . . 109.6(2) ?
    C12 N1 C11 . . 109.0(2) ?
    C16 N1 C11 . . 114.5(2) ?
    O2 N2 O3 . . 123.2(4) ?
    O2 N2 C20 . . 118.5(3) ?
    O3 N2 C20 . . 118.3(4) ?
    C2 O1 H1 . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 O1 . . . . 176.9(3) ?
    C11 C1 C2 O1 . . . . -4.2(4) ?
    C6 C1 C2 C3 . . . . -3.8(4) ?
    C11 C1 C2 C3 . . . . 175.1(3) ?
    O1 C2 C3 C4 . . . . -178.7(3) ?
    C1 C2 C3 C4 . . . . 2.0(5) ?
    C2 C3 C4 C5 . . . . 0.7(5) ?
    C3 C4 C5 C10 . . . . 179.3(3) ?
    C3 C4 C5 C6 . . . . -1.4(5) ?
    C10 C5 C6 C7 . . . . -1.8(4) ?
    C4 C5 C6 C7 . . . . 178.9(3) ?
    C10 C5 C6 C1 . . . . 178.8(3) ?
    C4 C5 C6 C1 . . . . -0.5(4) ?
    C2 C1 C6 C7 . . . . -176.4(3) ?
    C11 C1 C6 C7 . . . . 4.7(4) ?
    C2 C1 C6 C5 . . . . 3.0(4) ?
    C11 C1 C6 C5 . . . . -175.9(2) ?
    C5 C6 C7 C8 . . . . 1.1(4) ?
    C1 C6 C7 C8 . . . . -179.5(3) ?
    C6 C7 C8 C9 . . . . 0.4(5) ?
    C7 C8 C9 C10 . . . . -1.3(6) ?
    C8 C9 C10 C5 . . . . 0.6(6) ?
    C4 C5 C10 C9 . . . . -179.8(4) ?
    C6 C5 C10 C9 . . . . 1.0(5) ?
    C2 C1 C11 N1 . . . . -26.7(3) ?
    C6 C1 C11 N1 . . . . 152.2(2) ?
    C2 C1 C11 C18 . . . . 99.5(3) ?
    C6 C1 C11 C18 . . . . -81.7(3) ?
    N1 C12 C13 C14 . . . . 57.6(4) ?
    N1 C12 C13 C17 . . . . -176.7(3) ?
    C12 C13 C14 C15 . . . . -52.7(4) ?
    C17 C13 C14 C15 . . . . -176.8(3) ?
    C13 C14 C15 C16 . . . . 53.0(4) ?
    C14 C15 C16 N1 . . . . -56.1(4) ?
    N1 C11 C18 C19 . . . . -95.4(3) ?
    C1 C11 C18 C19 . . . . 139.5(3) ?
    N1 C11 C18 C23 . . . . 83.3(3) ?
    C1 C11 C18 C23 . . . . -41.7(4) ?
    C23 C18 C19 C20 . . . . -0.9(4) ?
    C11 C18 C19 C20 . . . . 177.8(3) ?
    C18 C19 C20 C21 . . . . 0.0(5) ?
    C18 C19 C20 N2 . . . . 180.0(3) ?
    C19 C20 C21 C22 . . . . 0.6(5) ?
    N2 C20 C21 C22 . . . . -179.4(3) ?
    C20 C21 C22 C23 . . . . -0.2(6) ?
    C21 C22 C23 C18 . . . . -0.7(6) ?
    C19 C18 C23 C22 . . . . 1.3(5) ?
    C11 C18 C23 C22 . . . . -177.5(3) ?
    C13 C12 N1 C16 . . . . -60.4(3) ?
    C13 C12 N1 C11 . . . . 173.6(3) ?
    C15 C16 N1 C12 . . . . 58.8(3) ?
    C15 C16 N1 C11 . . . . -178.4(3) ?
    C1 C11 N1 C12 . . . . -72.9(3) ?
    C18 C11 N1 C12 . . . . 160.5(2) ?
    C1 C11 N1 C16 . . . . 164.0(2) ?
    C18 C11 N1 C16 . . . . 37.3(3) ?
    C21 C20 N2 O2 . . . . -178.3(4) ?
    C19 C20 N2 O2 . . . . 1.7(5) ?
    C21 C20 N2 O3 . . . . 2.6(5) ?
    C19 C20 N2 O3 . . . . -177.4(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O1 H1 N1 . 0.82 1.86 2.579(3) 146.5
data_global
_journal_date_recd_electronic     2010-11-03
_journal_date_accepted     2010-11-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3118
_journal_page_last     o3118
_journal_paper_category     QO
_journal_coeditor_code     BX2327
_publ_contact_author_name     'Hong Zhao'
_publ_contact_author_address
;
School of Chemistry and Chemical
Engineering, Southeast University,
Nanjing 210096, People's Republic of China
;
_publ_contact_author_email     'zhaohong@seu.edu.cn'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
1-[(3-Methylpiperidin-1-yl)(3-nitrophenyl)methyl]naphthalen-2-ol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chen, Jin Mei' .
;
School of Chemistry and Chemical Engineering, Southeast University,
Nanjing 210096, People's Republic of China
;
    'Zhao, Hong' .
;
School of Chemistry and Chemical Engineering, Southeast University,
Nanjing 210096, People's Republic of China
;
