#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:43:10 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301803 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/66/2206624.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_2206624
loop_
_publ_author_name
'Nengfang, She'
'Huizhen Guo'
'Guodong Yin'
'Anxin Wu'
_publ_section_title
;
 2,2,6,6-Tetramethylpiperidin-4-ol
;
_journal_coeditor_code           BH6018
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2902
_journal_page_last               o2903
_journal_paper_doi               10.1107/S1600536805024372
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H19 N O'
_chemical_formula_moiety         'C9 H19 N O'
_chemical_formula_sum            'C9 H19 N O'
_chemical_formula_weight         157.25
_chemical_name_systematic
;
2,2,6,6-Tetramethyl-piperidin-4-ol
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.149(2)
_cell_length_b                   10.1346(15)
_cell_length_c                   13.3806(18)
_cell_measurement_reflns_used    635
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      21.64
_cell_measurement_theta_min      2.88
_cell_volume                     1918.7(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0932
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4310
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.0144(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0525
_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)+(0.0544P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                627
_reflns_number_total             1091
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh6018.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               2206624
_cod_database_fobs_code          2206624
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'
loop_
_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_type_symbol
C1 0.0000 0.1505(2) 0.72631(15) 0.0407(6) Uani d S 1 C
H1 0.0000 0.0689 0.7656 0.049 Uiso calc SR 1 H
C2 0.08643(10) 0.23024(15) 0.75302(12) 0.0454(5) Uani d . 1 C
H2A 0.0871 0.3101 0.7131 0.054 Uiso calc R 1 H
H2B 0.1424 0.1797 0.7362 0.054 Uiso calc R 1 H
C3 0.09076(11) 0.26771(15) 0.86296(12) 0.0446(5) Uani d . 1 C
C4 0.11645(17) 0.1471(2) 0.92716(15) 0.0774(7) Uani d . 1 C
H4A 0.1132 0.1704 0.9966 0.116 Uiso calc R 1 H
H4B 0.1794 0.1187 0.9112 0.116 Uiso calc R 1 H
H4C 0.0728 0.0768 0.9138 0.116 Uiso calc R 1 H
C5 0.16759(13) 0.37157(19) 0.87969(14) 0.0691(7) Uani d . 1 C
H5A 0.1546 0.4476 0.8392 0.104 Uiso calc R 1 H
H5B 0.2279 0.3355 0.8615 0.104 Uiso calc R 1 H
H5C 0.1685 0.3968 0.9489 0.104 Uiso calc R 1 H
N1 0.0000 0.33160(17) 0.89140(14) 0.0407(5) Uani d S 1 N
O1 0.0000 0.11754(18) 0.62227(11) 0.0533(6) Uani d S 1 O
H1A 0.0000 0.028(3) 0.620(2) 0.079(9) Uiso d S 1 H
H1B 0.0000 0.342(2) 0.9548(16) 0.046(7) Uiso d S 1 H
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
C1 0.0551(15) 0.0380(12) 0.0290(12) 0.000 0.000 0.0000(9)
C2 0.0455(10) 0.0442(9) 0.0464(11) 0.0038(7) 0.0037(7) -0.0041(8)
C3 0.0465(10) 0.0430(9) 0.0444(10) 0.0084(7) -0.0083(8) -0.0050(8)
C4 0.1036(18) 0.0664(13) 0.0622(14) 0.0284(11) -0.0316(11) 0.0002(10)
C5 0.0466(12) 0.0739(14) 0.0867(15) 0.0040(10) -0.0122(10) -0.0284(11)
N1 0.0500(13) 0.0417(11) 0.0305(12) 0.000 0.000 -0.0032(9)
O1 0.0813(14) 0.0480(10) 0.0307(10) 0.000 0.000 -0.0055(7)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 C1 C2 . . 110.82(11)
O1 C1 C2 . 12 110.82(11)
C2 C1 C2 . 12 108.31(18)
O1 C1 H1 . . 108.9
C2 C1 H1 . . 108.9
C2 C1 H1 12 . 108.9
C1 C2 C3 . . 113.30(14)
C1 C2 H2A . . 108.9
C3 C2 H2A . . 108.9
C1 C2 H2B . . 108.9
C3 C2 H2B . . 108.9
H2A C2 H2B . . 107.7
N1 C3 C2 . . 108.75(13)
N1 C3 C5 . . 106.05(13)
C2 C3 C5 . . 110.00(14)
N1 C3 C4 . . 114.03(15)
C2 C3 C4 . . 110.57(13)
C5 C3 C4 . . 107.30(14)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C3 C5 H5A . . 109.5
C3 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C3 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
C3 N1 C3 . 12 119.35(17)
C3 N1 H1B . . 108.0(6)
C3 N1 H1B 12 . 108.0(6)
C1 O1 H1A . . 105.7(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O1 . 1.432(2)
C1 C2 . 1.5087(19)
C1 C2 12 1.5087(19)
C1 H1 . 0.9800
C2 C3 . 1.520(2)
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 N1 . 1.4877(18)
C3 C5 . 1.530(2)
C3 C4 . 1.538(2)
C4 H4A . 0.9600
C4 H4B . 0.9600
C4 H4C . 0.9600
C5 H5A . 0.9600
C5 H5B . 0.9600
C5 H5C . 0.9600
N1 C3 12 1.4877(18)
N1 H1B . 0.85(2)
O1 H1A . 0.91(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
_geom_hbond_publ_flag
N1 H1B O1 2 0.85(2) 2.28(2) 3.132(3) 177(2) yes
O1 H1A N1 10_557 0.91(3) 1.99(3) 2.904(2) 178(3) yes
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_4
_geom_torsion
O1 C1 C2 C3 . . -179.67(13)
C2 C1 C2 C3 12 . 58.6(2)
C1 C2 C3 N1 . . -52.19(18)
C1 C2 C3 C5 . . -167.93(14)
C1 C2 C3 C4 . . 73.74(19)
C2 C3 N1 C3 . 12 48.4(2)
C5 C3 N1 C3 . 12 166.62(13)
C4 C3 N1 C3 . 12 -75.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 75471
