#------------------------------------------------------------------------------
#$Date: 2020-05-06 05:55:05 +0300 (Wed, 06 May 2020) $
#$Revision: 251809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243385.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_2243385
loop_
_publ_author_name
'Tiouabi, Mustapha'
'Tabacchi, Raphaël'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 The crystal structure and Hirshfeld surface analysis of
 1-(2,5-dimethoxyphenyl)-2,2,6,6-tetramethylpiperidine
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              794
_journal_page_last               797
_journal_paper_doi               10.1107/S2056989020005952
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C17 H27 N O2'
_chemical_formula_moiety         'C17 H27 N O2'
_chemical_formula_sum            'C17 H27 N O2'
_chemical_formula_weight         277.39
_chemical_name_systematic
;
1-(2,5-Dimethoxyphenyl)-2,2,6,6-tetramethylpiperidine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.649(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8817(10)
_cell_length_b                   28.249(4)
_cell_length_c                   8.1369(13)
_cell_measurement_reflns_used    4940
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      1.44
_cell_volume                     1559.4(4)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2005)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2005)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2005)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'φ + ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10596
_diffrn_reflns_theta_full        25.179
_diffrn_reflns_theta_max         25.179
_diffrn_reflns_theta_min         1.442
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       rod
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.126
_refine_ls_extinction_coef       0.0127(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
(SHELXL2018/3; Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0237P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                1695
_reflns_number_total             2770
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2006sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243385
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.15231(15) 0.11464(4) 0.48898(14) 0.0359(3) Uani d 1 . .
O O2 0.47503(17) 0.23289(4) 0.44354(15) 0.0389(3) Uani d 1 . .
N N1 0.17336(17) 0.10517(4) 0.72612(15) 0.0239(3) Uani d 1 . .
C C1 0.1701(2) 0.14010(5) 0.59863(18) 0.0240(4) Uani d 1 . .
C C2 0.0023(2) 0.14458(5) 0.4777(2) 0.0274(4) Uani d 1 . .
C C3 -0.0050(2) 0.17837(6) 0.3529(2) 0.0320(4) Uani d 1 . .
H H3 -0.120713 0.181465 0.271592 0.038 Uiso calc 1 . .
C C4 0.1545(2) 0.20752(6) 0.3461(2) 0.0326(4) Uani d 1 . .
H H4 0.148437 0.230424 0.259885 0.039 Uiso calc 1 . .
C C5 0.3219(2) 0.20347(5) 0.4637(2) 0.0286(4) Uani d 1 . .
C C6 0.3285(2) 0.17020(5) 0.58934(19) 0.0264(4) Uani d 1 . .
H H6 0.443892 0.167808 0.671343 0.032 Uiso calc 1 . .
C C7 -0.3053(2) 0.11190(7) 0.3485(2) 0.0420(5) Uani d 1 . .
H H7C -0.398183 0.086893 0.366432 0.063 Uiso calc 1 . .
H H7B -0.248449 0.104630 0.248721 0.063 Uiso calc 1 . .
H H7A -0.374711 0.142279 0.333365 0.063 Uiso calc 1 . .
C C8 0.6384(3) 0.23518(6) 0.5748(2) 0.0407(5) Uani d 1 . .
H H8A 0.703032 0.204187 0.588607 0.061 Uiso calc 1 . .
H H8B 0.592985 0.244041 0.678454 0.061 Uiso calc 1 . .
H H8C 0.732223 0.258909 0.548061 0.061 Uiso calc 1 . .
C C9 0.1554(2) 0.12313(5) 0.89467(19) 0.0269(4) Uani d 1 . .
C C10 0.0977(2) 0.08181(6) 0.9977(2) 0.0342(4) Uani d 1 . .
H H10A 0.103522 0.092378 1.114443 0.041 Uiso calc 1 . .
H H10B -0.040201 0.072692 0.954118 0.041 Uiso calc 1 . .
C C11 0.2287(2) 0.03873(6) 0.9958(2) 0.0381(5) Uani d 1 . .
H H11A 0.365874 0.046683 1.046272 0.046 Uiso calc 1 . .
H H11B 0.182345 0.012857 1.061593 0.046 Uiso calc 1 . .
C C12 0.2215(3) 0.02299(6) 0.8172(2) 0.0364(4) Uani d 1 . .
H H12B 0.084985 0.013326 0.770843 0.044 Uiso calc 1 . .
H H12A 0.307259 -0.005084 0.815714 0.044 Uiso calc 1 . .
C C13 0.2870(2) 0.06129(5) 0.7049(2) 0.0294(4) Uani d 1 . .
C C14 -0.0136(2) 0.15863(6) 0.8748(2) 0.0352(4) Uani d 1 . .
H H14C -0.039727 0.167933 0.985055 0.053 Uiso calc 1 . .
H H14B -0.132032 0.144135 0.810935 0.053 Uiso calc 1 . .
H H14A 0.022371 0.186676 0.815626 0.053 Uiso calc 1 . .
C C15 0.3403(2) 0.14765(6) 0.9888(2) 0.0361(4) Uani d 1 . .
H H15C 0.316036 0.157724 1.098873 0.054 Uiso calc 1 . .
H H15B 0.371277 0.175361 0.925566 0.054 Uiso calc 1 . .
H H15A 0.451420 0.125506 1.002183 0.054 Uiso calc 1 . .
C C16 0.5112(2) 0.06636(6) 0.7429(2) 0.0350(4) Uani d 1 . .
H H16C 0.572685 0.036915 0.713805 0.053 Uiso calc 1 . .
H H16B 0.552574 0.072901 0.861923 0.053 Uiso calc 1 . .
H H16A 0.552219 0.092519 0.677366 0.053 Uiso calc 1 . .
C C17 0.2301(2) 0.04478(6) 0.5248(2) 0.0387(5) Uani d 1 . .
H H17A 0.280543 0.067303 0.450547 0.058 Uiso calc 1 . .
H H17B 0.086213 0.042978 0.495777 0.058 Uiso calc 1 . .
H H17C 0.287008 0.013449 0.512256 0.058 Uiso calc 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C7 . . 117.22(13) ?
C5 O2 C8 . . 117.75(13) ?
C1 N1 C9 . . 116.13(11) ?
C1 N1 C13 . . 115.76(12) ?
C9 N1 C13 . . 121.11(11) ?
C2 C1 C6 . . 118.02(14) ?
C2 C1 N1 . . 119.07(14) ?
C6 C1 N1 . . 122.90(13) ?
O1 C2 C3 . . 122.57(14) ?
O1 C2 C1 . . 117.18(14) ?
C3 C2 C1 . . 120.24(15) ?
C4 C3 C2 . . 120.51(15) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C5 C4 C3 . . 120.13(15) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
O2 C5 C4 . . 115.91(14) ?
O2 C5 C6 . . 124.65(14) ?
C4 C5 C6 . . 119.42(15) ?
C5 C6 C1 . . 121.67(14) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
O1 C7 H7C . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7C C7 H7B . . 109.5 ?
O1 C7 H7A . . 109.5 ?
H7C C7 H7A . . 109.5 ?
H7B C7 H7A . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C14 . . 107.86(12) ?
N1 C9 C10 . . 108.36(12) ?
C14 C9 C10 . . 107.30(14) ?
N1 C9 C15 . . 115.10(13) ?
C14 C9 C15 . . 108.04(13) ?
C10 C9 C15 . . 109.90(13) ?
C11 C10 C9 . . 113.44(14) ?
C11 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
C11 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C12 C11 C10 . . 108.78(14) ?
C12 C11 H11A . . 109.9 ?
C10 C11 H11A . . 109.9 ?
C12 C11 H11B . . 109.9 ?
C10 C11 H11B . . 109.9 ?
H11A C11 H11B . . 108.3 ?
C11 C12 C13 . . 113.56(14) ?
C11 C12 H12B . . 108.9 ?
C13 C12 H12B . . 108.9 ?
C11 C12 H12A . . 108.9 ?
C13 C12 H12A . . 108.9 ?
H12B C12 H12A . . 107.7 ?
N1 C13 C17 . . 108.08(12) ?
N1 C13 C16 . . 115.46(12) ?
C17 C13 C16 . . 108.10(14) ?
N1 C13 C12 . . 107.81(13) ?
C17 C13 C12 . . 107.65(13) ?
C16 C13 C12 . . 109.49(13) ?
C9 C14 H14C . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14C C14 H14B . . 109.5 ?
C9 C14 H14A . . 109.5 ?
H14C C14 H14A . . 109.5 ?
H14B C14 H14A . . 109.5 ?
C9 C15 H15C . . 109.5 ?
C9 C15 H15B . . 109.5 ?
H15C C15 H15B . . 109.5 ?
C9 C15 H15A . . 109.5 ?
H15C C15 H15A . . 109.5 ?
H15B C15 H15A . . 109.5 ?
C13 C16 H16C . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16C C16 H16B . . 109.5 ?
C13 C16 H16A . . 109.5 ?
H16C C16 H16A . . 109.5 ?
H16B C16 H16A . . 109.5 ?
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 ?
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
O1 C2 . 1.3743(19) ?
O1 C7 . 1.4204(18) ?
O2 C5 . 1.3732(19) ?
O2 C8 . 1.416(2) ?
N1 C1 . 1.4293(19) ?
N1 C9 . 1.4867(19) ?
N1 C13 . 1.4908(19) ?
C1 C2 . 1.392(2) ?
C1 C6 . 1.394(2) ?
C2 C3 . 1.388(2) ?
C3 C4 . 1.381(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.374(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.384(2) ?
C6 H6 . 0.9500 ?
C7 H7C . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7A . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C14 . 1.524(2) ?
C9 C10 . 1.528(2) ?
C9 C15 . 1.536(2) ?
C10 C11 . 1.516(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.513(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.532(2) ?
C12 H12B . 0.9900 ?
C12 H12A . 0.9900 ?
C13 C17 . 1.526(2) ?
C13 C16 . 1.529(2) ?
C14 H14C . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14A . 0.9800 ?
C15 H15C . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15A . 0.9800 ?
C16 H16C . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16A . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
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
C8 H8B O2 4_566 0.98 2.51 3.495(2) 180 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . -106.25(16) ?
C13 N1 C1 C2 . . . . 102.61(16) ?
C9 N1 C1 C6 . . . . 73.77(19) ?
C13 N1 C1 C6 . . . . -77.38(18) ?
C7 O1 C2 C3 . . . . 13.5(2) ?
C7 O1 C2 C1 . . . . -166.84(14) ?
C6 C1 C2 O1 . . . . -179.96(14) ?
N1 C1 C2 O1 . . . . 0.1(2) ?
C6 C1 C2 C3 . . . . -0.3(2) ?
N1 C1 C2 C3 . . . . 179.71(14) ?
O1 C2 C3 C4 . . . . -179.64(15) ?
C1 C2 C3 C4 . . . . 0.7(2) ?
C2 C3 C4 C5 . . . . -0.4(2) ?
C8 O2 C5 C4 . . . . 170.51(15) ?
C8 O2 C5 C6 . . . . -11.2(2) ?
C3 C4 C5 O2 . . . . 177.94(15) ?
C3 C4 C5 C6 . . . . -0.4(2) ?
O2 C5 C6 C1 . . . . -177.36(15) ?
C4 C5 C6 C1 . . . . 0.9(2) ?
C2 C1 C6 C5 . . . . -0.5(2) ?
N1 C1 C6 C5 . . . . 179.49(14) ?
C1 N1 C9 C14 . . . . 46.76(17) ?
C13 N1 C9 C14 . . . . -163.75(13) ?
C1 N1 C9 C10 . . . . 162.62(12) ?
C13 N1 C9 C10 . . . . -47.89(17) ?
C1 N1 C9 C15 . . . . -73.91(16) ?
C13 N1 C9 C15 . . . . 75.58(17) ?
N1 C9 C10 C11 . . . . 50.81(17) ?
C14 C9 C10 C11 . . . . 167.03(14) ?
C15 C9 C10 C11 . . . . -75.74(17) ?
C9 C10 C11 C12 . . . . -57.94(18) ?
C10 C11 C12 C13 . . . . 58.42(18) ?
C1 N1 C13 C17 . . . . -46.30(16) ?
C9 N1 C13 C17 . . . . 164.11(13) ?
C1 N1 C13 C16 . . . . 74.85(17) ?
C9 N1 C13 C16 . . . . -74.74(18) ?
C1 N1 C13 C12 . . . . -162.40(12) ?
C9 N1 C13 C12 . . . . 48.01(17) ?
C11 C12 C13 N1 . . . . -51.42(17) ?
C11 C12 C13 C17 . . . . -167.79(14) ?
C11 C12 C13 C16 . . . . 74.93(18) ?

_cod_database_fobs_code 2243385
