#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/71/2237112.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237112
loop_
_publ_author_name
'Pienaar, Daniel P.'
'Khorasani, Sanaz'
'de Koning, Charles B.'
'Michael, Joseph P.'
_publ_section_title
;
 3-Hydroxy-1-(4-methoxybenzyl)piperidin-2-one
;
_journal_coeditor_code           BH2468
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o51
_journal_paper_doi               10.1107/S1600536812049501
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H17 N O3'
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.28
_chemical_melting_point          347
_chemical_name_systematic
;
3-Hydroxy-1-(4-methoxybenzyl)piperidin-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.497(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.980(3)
_cell_length_b                   7.6143(17)
_cell_length_c                   12.189(3)
_cell_measurement_reflns_used    958
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      3.52
_cell_volume                     1204.6(5)
_computing_cell_refinement       'SAINT-NT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-NT (Bruker, 2005)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and SCHAKAL99
(Keller, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8378
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0421
_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/[σ²(Fo²)+(0.0660P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2271
_reflns_number_total             2895
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2468.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237112
_cod_database_fobs_code          2237112
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
C C2 0.11028(9) 0.10275(17) 0.35921(10) 0.0283(3) Uani d . 1 1
C C3 0.06871(9) -0.07971(17) 0.32619(11) 0.0304(3) Uani d . 1 1
H H3 -0.0060 -0.0662 0.3072 0.037 Uiso calc R 1 1
C C4 0.12221(11) -0.15543(17) 0.22690(12) 0.0353(3) Uani d . 1 1
H H4A 0.0856 -0.2621 0.2013 0.042 Uiso calc R 1 1
H H4B 0.1939 -0.1883 0.2463 0.042 Uiso calc R 1 1
C C5 0.12221(11) -0.01793(18) 0.13695(11) 0.0374(3) Uani d . 1 1
H H5A 0.1507 -0.0688 0.0689 0.045 Uiso calc R 1 1
H H5B 0.0508 0.0209 0.1214 0.045 Uiso calc R 1 1
C C6 0.18684(10) 0.13727(17) 0.17295(10) 0.0323(3) Uani d . 1 1
H H6A 0.2605 0.1038 0.1716 0.039 Uiso calc R 1 1
H H6B 0.1766 0.2349 0.1204 0.039 Uiso calc R 1 1
C C7 0.20555(10) 0.36915(17) 0.31491(12) 0.0334(3) Uani d . 1 1
H H7A 0.1693 0.4153 0.3800 0.040 Uiso calc R 1 1
H H7B 0.1951 0.4535 0.2540 0.040 Uiso calc R 1 1
C C8 0.31965(10) 0.35530(15) 0.34078(11) 0.0296(3) Uani d . 1 1
C C9 0.35322(10) 0.27078(17) 0.43529(11) 0.0343(3) Uani d . 1 1
H H9 0.3037 0.2227 0.4838 0.041 Uiso calc R 1 1
C C10 0.45748(11) 0.25429(18) 0.46121(11) 0.0349(3) Uani d . 1 1
H H10 0.4786 0.1967 0.5268 0.042 Uiso calc R 1 1
C C11 0.53038(10) 0.32307(16) 0.39013(11) 0.0321(3) Uani d . 1 1
C C12 0.49838(10) 0.4107(2) 0.29565(12) 0.0389(3) Uani d . 1 1
H H12 0.5479 0.4600 0.2477 0.047 Uiso calc R 1 1
C C13 0.39415(10) 0.42600(19) 0.27143(11) 0.0365(3) Uani d . 1 1
H H13 0.3730 0.4856 0.2066 0.044 Uiso calc R 1 1
C C14 0.66904(13) 0.2242(2) 0.50439(15) 0.0495(4) Uani d . 1 1
H H14A 0.6450 0.2894 0.5686 0.074 Uiso calc R 1 1
H H14B 0.7445 0.2192 0.5055 0.074 Uiso calc R 1 1
H H14C 0.6411 0.1047 0.5061 0.074 Uiso calc R 1 1
N N1 0.16062(8) 0.19805(13) 0.28388(8) 0.0270(2) Uani d . 1 1
O O1 0.09468(8) 0.15790(15) 0.45317(8) 0.0444(3) Uani d . 1 1
O O2 0.07623(8) -0.19755(14) 0.41449(10) 0.0457(3) Uani d . 1 1
H H2 0.0256(18) -0.165(3) 0.4675(17) 0.069 Uiso d . 1 1
O O3 0.63479(7) 0.31060(14) 0.40678(9) 0.0431(3) Uani d . 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C2 N1 122.21(12)
O1 C2 C3 119.16(11)
N1 C2 C3 118.62(11)
O2 C3 C4 109.87(11)
O2 C3 C2 110.71(11)
C4 C3 C2 112.93(10)
O2 C3 H3 107.7
C4 C3 H3 107.7
C2 C3 H3 107.7
C3 C4 C5 108.54(11)
C3 C4 H4A 110.0
C5 C4 H4A 110.0
C3 C4 H4B 110.0
C5 C4 H4B 110.0
H4A C4 H4B 108.4
C6 C5 C4 109.47(10)
C6 C5 H5A 109.8
C4 C5 H5A 109.8
C6 C5 H5B 109.8
C4 C5 H5B 109.8
H5A C5 H5B 108.2
N1 C6 C5 112.35(11)
N1 C6 H6A 109.1
C5 C6 H6A 109.1
N1 C6 H6B 109.1
C5 C6 H6B 109.1
H6A C6 H6B 107.9
N1 C7 C8 112.04(10)
N1 C7 H7A 109.2
C8 C7 H7A 109.2
N1 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
C9 C8 C13 117.85(12)
C9 C8 C7 120.32(11)
C13 C8 C7 121.84(12)
C8 C9 C10 121.88(12)
C8 C9 H9 119.1
C10 C9 H9 119.1
C11 C10 C9 119.33(13)
C11 C10 H10 120.3
C9 C10 H10 120.3
O3 C11 C10 123.94(12)
O3 C11 C12 116.31(12)
C10 C11 C12 119.75(13)
C13 C12 C11 120.02(12)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C8 121.16(13)
C12 C13 H13 119.4
C8 C13 H13 119.4
O3 C14 H14A 109.5
O3 C14 H14B 109.5
H14A C14 H14B 109.5
O3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C2 N1 C6 125.13(11)
C2 N1 C7 119.67(11)
C6 N1 C7 114.78(10)
C3 O2 H2 107.9(12)
C11 O3 C14 117.08(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O1 1.2381(15)
C2 N1 1.3443(16)
C2 C3 1.5426(18)
C3 O2 1.4039(16)
C3 C4 1.5145(19)
C3 H3 1.0000
C4 C5 1.5160(19)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5121(19)
C5 H5A 0.9900
C5 H5B 0.9900
C6 N1 1.4717(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 N1 1.4753(16)
C7 C8 1.5154(18)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.3865(19)
C8 C13 1.3977(18)
C9 C10 1.393(2)
C9 H9 0.9500
C10 C11 1.3909(19)
C10 H10 0.9500
C11 O3 1.3719(16)
C11 C12 1.391(2)
C12 C13 1.3871(19)
C12 H12 0.9500
C13 H13 0.9500
C14 O3 1.4272(19)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
O2 H2 0.96(2)
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
_geom_hbond_publ_flag
O2 H2 O1 3_556 0.96(2) 1.84(2) 2.7708(16) 161.6(19) y
C6 H6B O1 4_565 0.99 2.43 3.3142(17) 148 y
C14 H14B O2 3_656 0.98 2.52 3.449(2) 158 y
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
O1 C2 C3 O2 -36.84(16)
N1 C2 C3 O2 144.47(12)
O1 C2 C3 C4 -160.52(12)
N1 C2 C3 C4 20.79(15)
O2 C3 C4 C5 -174.31(10)
C2 C3 C4 C5 -50.17(14)
C3 C4 C5 C6 64.96(14)
C4 C5 C6 N1 -48.71(15)
N1 C7 C8 C9 -70.61(15)
N1 C7 C8 C13 109.37(14)
C13 C8 C9 C10 -0.5(2)
C7 C8 C9 C10 179.46(12)
C8 C9 C10 C11 -0.5(2)
C9 C10 C11 O3 -178.55(12)
C9 C10 C11 C12 1.5(2)
O3 C11 C12 C13 178.67(13)
C10 C11 C12 C13 -1.3(2)
C11 C12 C13 C8 0.3(2)
C9 C8 C13 C12 0.7(2)
C7 C8 C13 C12 -179.32(12)
O1 C2 N1 C6 176.47(12)
C3 C2 N1 C6 -4.89(17)
O1 C2 N1 C7 4.33(18)
C3 C2 N1 C7 -177.02(10)
C5 C6 N1 C2 19.25(17)
C5 C6 N1 C7 -168.28(10)
C8 C7 N1 C2 98.18(13)
C8 C7 N1 C6 -74.74(14)
C10 C11 O3 C14 -1.19(19)
C12 C11 O3 C14 178.80(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26528220
