#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/22/2202224.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_2202224
loop_
_publ_author_name
'Mei-su Zhou'
'Dian-sheng Liu'
'Shu-ping Huang'
'Hong-bo Tong'
_publ_section_title
;
 2-tert-Butyl-4-piperidino-β-diketimine
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o310
_journal_page_last               o311
_journal_paper_doi               10.1107/S1600536803002605
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C12 H23 N3'
_chemical_formula_moiety         'C12 H23 N3'
_chemical_formula_sum            'C12 H23 N3'
_chemical_formula_weight         209.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.386(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.409(2)
_cell_length_b                   6.133(2)
_cell_length_c                   19.665(4)
_cell_measurement_reflns_used    1558
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.308
_cell_volume                     1249.8(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Siemens CCD area-detector'
_diffrn_measurement_method       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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5024
_diffrn_reflns_theta_full        25.51
_diffrn_reflns_theta_max         25.51
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        3.43
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0538P)²+0.7086P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1444
_reflns_number_gt                1807
_reflns_number_total             2317
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6060.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_cell_volume        1249.7(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2202224
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 -0.07866(16) 0.7472(3) 0.14258(9) 0.0263(5) Uani d . 1 . . N
N2 0.2245(2) 0.3046(4) 0.21482(10) 0.0311(5) Uani d . 1 . . N
N3 -0.0106(2) 0.4759(4) 0.22529(10) 0.0357(5) Uani d . 1 . . N
C2 0.1179(2) 0.5456(4) 0.13388(11) 0.0254(5) Uani d . 1 . . C
H2 0.1206 0.6155 0.0921 0.030 Uiso calc R 1 . . H
C3 0.0072(2) 0.5878(4) 0.17113(11) 0.0261(5) Uani d . 1 . . C
C4 -0.2012(2) 0.7748(4) 0.17193(11) 0.0310(6) Uani d . 1 . . C
H4A -0.1872 0.8555 0.2144 0.037 Uiso calc R 1 . . H
H4B -0.2361 0.6330 0.1820 0.037 Uiso calc R 1 . . H
C5 -0.2969(2) 0.8965(4) 0.12273(12) 0.0325(6) Uani d . 1 . . C
H5A -0.3179 0.8077 0.0824 0.039 Uiso calc R 1 . . H
H5B -0.3759 0.9206 0.1442 0.039 Uiso calc R 1 . . H
C1 0.2188(2) 0.4120(4) 0.15476(11) 0.0235(5) Uani d . 1 . . C
C9 0.3336(2) 0.3795(4) 0.11313(11) 0.0260(5) Uani d . 1 . . C
C8 -0.0237(2) 0.9584(4) 0.12413(12) 0.0301(6) Uani d . 1 . . C
H8A 0.0572 0.9336 0.1046 0.036 Uiso calc R 1 . . H
H8B -0.0058 1.0460 0.1650 0.036 Uiso calc R 1 . . H
C10 0.3492(2) 0.1359(4) 0.09740(13) 0.0344(6) Uani d . 1 . . C
H10A 0.3645 0.0563 0.1394 0.052 Uiso calc R 1 . . H
H10B 0.4210 0.1165 0.0707 0.052 Uiso calc R 1 . . H
H10C 0.2720 0.0828 0.0723 0.052 Uiso calc R 1 . . H
C6 -0.2441(2) 1.1139(5) 0.10165(13) 0.0381(7) Uani d . 1 . . C
H6A -0.2339 1.2107 0.1408 0.046 Uiso calc R 1 . . H
H6B -0.3043 1.1808 0.0672 0.046 Uiso calc R 1 . . H
C7 -0.1147(2) 1.0812(4) 0.07337(12) 0.0372(6) Uani d . 1 . . C
H7A -0.1268 1.0001 0.0309 0.045 Uiso calc R 1 . . H
H7B -0.0777 1.2219 0.0638 0.045 Uiso calc R 1 . . H
C11 0.4562(2) 0.4619(4) 0.15537(13) 0.0399(7) Uani d . 1 . . C
H11A 0.4463 0.6135 0.1659 0.060 Uiso calc R 1 . . H
H11B 0.5293 0.4436 0.1295 0.060 Uiso calc R 1 . . H
H11C 0.4695 0.3799 0.1970 0.060 Uiso calc R 1 . . H
C12 0.3195(2) 0.5043(4) 0.04579(12) 0.0359(6) Uani d . 1 . . C
H12A 0.2433 0.4558 0.0187 0.054 Uiso calc R 1 . . H
H12B 0.3937 0.4782 0.0214 0.054 Uiso calc R 1 . . H
H12C 0.3126 0.6575 0.0548 0.054 Uiso calc R 1 . . H
H4 0.153(2) 0.304(4) 0.2371(11) 0.028(7) Uiso d . 1 . . H
H1 -0.078(2) 0.523(4) 0.2436(12) 0.039(7) Uiso d . 1 . . H
H3 0.286(3) 0.209(5) 0.2245(12) 0.040(8) Uiso d . 1 . . H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C4 118.01(18) ?
C3 N1 C8 117.53(17) ?
C4 N1 C8 111.65(18) ?
C1 N2 H4 117.2(15) ?
C1 N2 H3 119.1(17) ?
H4 N2 H3 121(2) ?
C3 N3 H1 110.3(17) ?
C1 C2 C3 125.7(2) yes
C1 C2 H2 117.2 ?
C3 C2 H2 117.2 ?
N3 C3 N1 124.2(2) ?
N3 C3 C2 120.3(2) yes
N1 C3 C2 115.43(19) yes
N1 C4 C5 110.56(18) ?
N1 C4 H4A 109.5 ?
C5 C4 H4A 109.5 ?
N1 C4 H4B 109.5 ?
C5 C4 H4B 109.5 ?
H4A C4 H4B 108.1 ?
C6 C5 C4 111.94(19) ?
C6 C5 H5A 109.2 ?
C4 C5 H5A 109.2 ?
C6 C5 H5B 109.2 ?
C4 C5 H5B 109.2 ?
H5A C5 H5B 107.9 ?
N2 C1 C2 121.8(2) yes
N2 C1 C9 115.7(2) ?
C2 C1 C9 122.49(19) yes
C1 C9 C12 112.63(18) ?
C1 C9 C10 109.79(19) ?
C12 C9 C10 108.44(19) ?
C1 C9 C11 108.62(18) ?
C12 C9 C11 108.1(2) ?
C10 C9 C11 109.19(19) ?
N1 C8 C7 111.51(19) ?
N1 C8 H8A 109.3 ?
C7 C8 H8A 109.3 ?
N1 C8 H8B 109.3 ?
C7 C8 H8B 109.3 ?
H8A C8 H8B 108.0 ?
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C5 C6 C7 110.0(2) ?
C5 C6 H6A 109.7 ?
C7 C6 H6A 109.7 ?
C5 C6 H6B 109.7 ?
C7 C6 H6B 109.7 ?
H6A C6 H6B 108.2 ?
C8 C7 C6 110.3(2) ?
C8 C7 H7A 109.6 ?
C6 C7 H7A 109.6 ?
C8 C7 H7B 109.6 ?
C6 C7 H7B 109.6 ?
H7A C7 H7B 108.1 ?
C9 C11 H11A 109.5 ?
C9 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C9 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C9 C12 H12A 109.5 ?
C9 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C9 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 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
N1 C3 . 1.405(3) yes
N1 C4 . 1.458(3) ?
N1 C8 . 1.475(3) ?
N2 C1 . 1.349(3) yes
N2 H4 . 0.90(2) ?
N2 H3 . 0.88(3) ?
N3 C3 . 1.295(3) yes
N3 H1 . 0.87(3) ?
C2 C1 . 1.364(3) yes
C2 C3 . 1.446(3) yes
C2 H2 . 0.9300 ?
C4 C5 . 1.518(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.515(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C1 C9 . 1.524(3) yes
C9 C12 . 1.524(3) ?
C9 C10 . 1.538(3) ?
C9 C11 . 1.542(3) ?
C8 C7 . 1.511(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C6 C7 . 1.518(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654698
2 PubChem 139065910
