#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/31/2213171.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_2213171
loop_
_publ_author_name
'Hartung, Jens'
'Stapf, Georg'
'Bergsträsser, Uwe'
_publ_section_title
;
 cis-(Piperidine-2,6-diyl)dimethanol
;
_journal_coeditor_code           BT2325
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2586
_journal_page_last               o2587
_journal_paper_doi               10.1107/S1600536807017771
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H15 N O2'
_chemical_formula_moiety         'C7 H15 N O2'
_chemical_formula_sum            'C7 H15 N O2'
_chemical_formula_weight         145.20
_chemical_melting_point          401
_chemical_name_systematic
;
cis-(Piperidine-2,6-diyl)dimethanol
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.95(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.555(3)
_cell_length_b                   8.5120(19)
_cell_length_c                   9.906(2)
_cell_measurement_reflns_used    2655
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.5387
_cell_measurement_theta_min      2.8247
_cell_volume                     802.7(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1399
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'Oxford Diffraction KM-4 Xcalibur2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5200
_diffrn_reflns_theta_full        28.63
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.171
_refine_ls_extinction_coef       0.015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0439P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                1307
_reflns_number_total             1809
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2325.cif
_cod_data_source_block           I
_cod_database_code               2213171
_cod_database_fobs_code          2213171
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_occupancy
C C6 0.17413(10) 0.14147(12) 0.71734(10) 0.0235(2) Uani d 1
O O1 0.20757(9) -0.02910(10) 1.11084(8) 0.0391(2) Uani d 1
N N1 0.16566(8) 0.02789(9) 0.82905(8) 0.0211(2) Uani d 1
O O2 -0.05154(7) 0.24582(10) 0.76241(7) 0.0335(2) Uani d 1
C C5 0.25992(11) 0.06787(13) 0.61174(11) 0.0299(3) Uani d 1
C C61 0.02793(11) 0.18151(14) 0.66017(10) 0.0289(3) Uani d 1
C C2 0.30407(9) -0.00716(11) 0.89769(10) 0.0224(2) Uani d 1
C C3 0.39334(10) -0.08515(13) 0.79726(10) 0.0260(2) Uani d 1
C C11 0.28643(11) -0.11074(12) 1.01870(10) 0.0265(3) Uani d 1
C C4 0.40377(11) 0.01705(14) 0.67247(12) 0.0325(3) Uani d 1
H H11B 0.3781(12) -0.1386(13) 1.0607(11) 0.030(3) Uiso d 1
H H11A 0.2394(11) -0.2090(13) 0.9892(11) 0.028(3) Uiso d 1
H H4B 0.4547(12) -0.0384(15) 0.6046(13) 0.046(3) Uiso d 1
H H3B 0.3501(10) -0.1851(13) 0.7714(11) 0.026(3) Uiso d 1
H H6 0.2209(10) 0.2386(14) 0.7494(11) 0.027(3) Uiso d 1
H H61B -0.0202(11) 0.0853(14) 0.6219(11) 0.028(3) Uiso d 1
H H8 -0.0846(14) 0.3380(19) 0.7359(15) 0.053(4) Uiso d 1
H H1 0.3522(10) 0.0922(14) 0.9309(11) 0.026(3) Uiso d 1
H H3 0.1123(11) 0.0669(13) 0.8881(12) 0.027(3) Uiso d 1
H H5B 0.2059(11) -0.0218(13) 0.5713(11) 0.032(3) Uiso d 1
H H5A 0.2681(12) 0.1416(14) 0.5415(12) 0.038(3) Uiso d 1
H H4A 0.4591(12) 0.1103(15) 0.7001(13) 0.037(3) Uiso d 1
H H3A 0.4864(11) -0.1048(13) 0.8415(11) 0.028(3) Uiso d 1
H H9 0.1620(16) -0.096(2) 1.1508(16) 0.066(5) Uiso d 1
H H61A 0.0323(11) 0.2581(14) 0.5845(12) 0.031(3) Uiso d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C6 0.0277(5) 0.0180(5) 0.0249(5) -0.0011(4) 0.0034(4) 0.0025(4)
O1 0.0536(5) 0.0329(5) 0.0329(4) 0.0049(4) 0.0157(4) 0.0041(4)
N1 0.0217(4) 0.0198(4) 0.0219(4) 0.0012(3) 0.0032(3) 0.0015(3)
O2 0.0358(4) 0.0307(4) 0.0350(4) 0.0132(3) 0.0095(3) 0.0089(3)
C5 0.0363(6) 0.0281(6) 0.0262(5) 0.0021(5) 0.0080(4) 0.0048(5)
C61 0.0341(6) 0.0262(6) 0.0263(5) 0.0066(5) 0.0023(4) 0.0039(4)
C2 0.0222(5) 0.0192(5) 0.0251(5) -0.0020(4) -0.0013(4) -0.0007(4)
C3 0.0210(5) 0.0242(5) 0.0326(6) 0.0010(4) 0.0013(4) -0.0013(4)
C11 0.0270(5) 0.0248(5) 0.0271(5) 0.0022(4) -0.0014(4) 0.0011(4)
C4 0.0300(6) 0.0323(6) 0.0368(6) -0.0011(5) 0.0126(5) 0.0009(5)
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
N1 C6 C61 108.78(8)
N1 C6 C5 108.29(8)
C61 C6 C5 111.96(9)
N1 C6 H6 111.2(6)
C61 C6 H6 108.3(6)
C5 C6 H6 108.2(6)
C11 O1 H9 107.3(11)
C2 N1 C6 112.05(8)
C2 N1 H3 108.8(7)
C6 N1 H3 109.0(7)
C61 O2 H8 109.3(9)
C4 C5 C6 111.67(9)
C4 C5 H5B 111.4(6)
C6 C5 H5B 107.7(6)
C4 C5 H5A 110.6(7)
C6 C5 H5A 108.5(7)
H5B C5 H5A 106.8(9)
O2 C61 C6 110.76(8)
O2 C61 H61B 109.2(6)
C6 C61 H61B 109.9(6)
O2 C61 H61A 110.0(6)
C6 C61 H61A 109.5(6)
H61B C61 H61A 107.4(9)
N1 C2 C11 109.24(8)
N1 C2 C3 108.71(8)
C11 C2 C3 111.88(8)
N1 C2 H1 110.5(6)
C11 C2 H1 108.1(6)
C3 C2 H1 108.4(6)
C2 C3 C4 111.23(9)
C2 C3 H3B 107.8(6)
C4 C3 H3B 110.0(6)
C2 C3 H3A 108.9(6)
C4 C3 H3A 110.1(6)
H3B C3 H3A 108.7(9)
O1 C11 C2 109.12(8)
O1 C11 H11B 110.9(6)
C2 C11 H11B 109.0(6)
O1 C11 H11A 110.8(6)
C2 C11 H11A 109.9(6)
H11B C11 H11A 107.0(9)
C5 C4 C3 111.41(9)
C5 C4 H4B 110.5(7)
C3 C4 H4B 110.6(7)
C5 C4 H4A 109.2(7)
C3 C4 H4A 107.9(7)
H4B C4 H4A 107.0(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 N1 1.4770(12)
C6 C61 1.5006(15)
C6 C5 1.5188(14)
C6 H6 0.980(11)
O1 C11 1.4151(13)
O1 H9 0.837(17)
N1 C2 1.4647(13)
N1 H3 0.874(11)
O2 C61 1.4264(12)
O2 H8 0.878(16)
C5 C4 1.5151(16)
C5 H5B 0.987(11)
C5 H5A 0.945(12)
C61 H61B 0.997(12)
C61 H61A 0.997(12)
C2 C11 1.5092(14)
C2 C3 1.5180(14)
C2 H1 1.004(12)
C3 C4 1.5219(15)
C3 H3B 0.971(11)
C3 H3A 0.971(11)
C11 H11B 0.966(11)
C11 H11A 0.982(12)
C4 H4B 0.984(13)
C4 H4A 0.980(13)
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 H9 O2 3_557 0.837(17) 1.906(18) 2.7432(13) 177.7(16)
O2 H8 N1 2_556 0.878(16) 1.881(17) 2.7575(13) 175.8(14)
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_publ_flag
C61 C6 N1 C2 -175.25(8) ?
C5 C6 N1 C2 62.86(10) .
N1 C6 C5 C4 -55.97(11) .
C61 C6 C5 C4 -175.89(9) ?
N1 C6 C61 O2 58.55(11) y
C5 C6 C61 O2 178.19(8) ?
C6 N1 C2 C11 174.44(8) ?
C6 N1 C2 C3 -63.23(10) .
N1 C2 C3 C4 56.29(11) .
C11 C2 C3 C4 177.01(8) ?
N1 C2 C11 O1 -62.04(10) y
C3 C2 C11 O1 177.55(8) ?
C6 C5 C4 C3 51.76(12) .
C2 C3 C4 C5 -51.63(12) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4415422
