#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/23/2202374.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_2202374
loop_
_publ_author_name
'Khan, Arif Ali'
'Wismach, Cathleen'
'Jones, Peter G.'
'Streubel, Rainer'
_publ_section_title
;
 2,4,6-Tripiperidino-1,3,5-triazine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1757
_journal_page_last               o1758
_journal_paper_doi               10.1107/S1600536803020440
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C18 H30 N6'
_chemical_formula_moiety         'C18 H30 N6'
_chemical_formula_sum            'C18 H30 N6'
_chemical_formula_weight         330.48
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.377(3)
_cell_angle_beta                 101.455(3)
_cell_angle_gamma                108.361(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3527(8)
_cell_length_b                   9.8192(10)
_cell_length_c                   12.0219(12)
_cell_measurement_reflns_used    5270
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     893.88(16)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω- and φ'
_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    0.0290
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12279
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'cut tablet'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0399
_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)+(0.065P)²+0.0581P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                3407
_reflns_number_total             4407
_reflns_threshold_expression     I>2s(I)
_cod_data_source_file            bt6344.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        893.88(15)
_cod_database_code               2202374
_cod_database_fobs_code          2202374
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.18725(13) 0.04736(10) 0.21320(8) 0.0246(2) Uani d . 1 . . C
C2 0.33816(14) 0.28662(10) 0.30150(8) 0.0243(2) Uani d . 1 . . C
C3 0.06960(14) 0.17362(11) 0.32453(9) 0.0259(2) Uani d . 1 . . C
C4 0.31516(14) -0.09231(12) 0.09208(10) 0.0300(2) Uani d . 1 . . C
H4A 0.3674 -0.1570 0.1299 0.036 Uiso calc R 1 . . H
H4B 0.4073 0.0058 0.1071 0.036 Uiso calc R 1 . . H
C5 0.24791(16) -0.15620(14) -0.03807(10) 0.0386(3) Uani d . 1 . . C
H5A 0.3431 -0.1734 -0.0688 0.046 Uiso calc R 1 . . H
H5B 0.2112 -0.0848 -0.0771 0.046 Uiso calc R 1 . . H
C6 0.09321(16) -0.30125(14) -0.06577(10) 0.0394(3) Uani d . 1 . . C
H6A 0.0453 -0.3361 -0.1512 0.047 Uiso calc R 1 . . H
H6B 0.1331 -0.3769 -0.0356 0.047 Uiso calc R 1 . . H
C7 -0.04821(14) -0.28013(12) -0.01067(10) 0.0317(3) Uani d . 1 . . C
H7A -0.0980 -0.2138 -0.0479 0.038 Uiso calc R 1 . . H
H7B -0.1433 -0.3762 -0.0241 0.038 Uiso calc R 1 . . H
C8 0.02412(15) -0.21524(11) 0.11900(10) 0.0308(2) Uani d . 1 . . C
H8A -0.0680 -0.1950 0.1518 0.037 Uiso calc R 1 . . H
H8B 0.0604 -0.2870 0.1578 0.037 Uiso calc R 1 . . H
C9 -0.22720(15) 0.05333(12) 0.34689(10) 0.0326(3) Uani d . 1 . . C
H9A -0.2224 -0.0309 0.2930 0.039 Uiso calc R 1 . . H
H9B -0.3251 0.0808 0.3086 0.039 Uiso calc R 1 . . H
C10 -0.25786(14) 0.00891(12) 0.45900(10) 0.0322(3) Uani d . 1 . . C
H10A -0.1664 -0.0284 0.4929 0.039 Uiso calc R 1 . . H
H10B -0.3726 -0.0713 0.4418 0.039 Uiso calc R 1 . . H
C11 -0.25376(15) 0.14000(13) 0.54648(10) 0.0326(3) Uani d . 1 . . C
H11A -0.3525 0.1711 0.5159 0.039 Uiso calc R 1 . . H
H11B -0.2668 0.1110 0.6206 0.039 Uiso calc R 1 . . H
C12 -0.08223(14) 0.26768(12) 0.56851(9) 0.0293(2) Uani d . 1 . . C
H12A -0.0846 0.3542 0.6209 0.035 Uiso calc R 1 . . H
H12B 0.0153 0.2402 0.6075 0.035 Uiso calc R 1 . . H
C13 -0.05192(16) 0.30755(11) 0.45529(9) 0.0317(3) Uani d . 1 . . C
H13A -0.1406 0.3477 0.4215 0.038 Uiso calc R 1 . . H
H13B 0.0648 0.3846 0.4708 0.038 Uiso calc R 1 . . H
C14 0.47647(14) 0.55506(11) 0.36704(9) 0.0282(2) Uani d . 1 . . C
H14A 0.5912 0.6213 0.4187 0.034 Uiso calc R 1 . . H
H14B 0.3883 0.5450 0.4125 0.034 Uiso calc R 1 . . H
C15 0.42725(14) 0.62080(11) 0.26373(9) 0.0277(2) Uani d . 1 . . C
H15A 0.4275 0.7207 0.2924 0.033 Uiso calc R 1 . . H
H15B 0.3079 0.5591 0.2162 0.033 Uiso calc R 1 . . H
C16 0.55606(16) 0.62956(12) 0.18868(10) 0.0323(3) Uani d . 1 . . C
H16A 0.6720 0.7022 0.2330 0.039 Uiso calc R 1 . . H
H16B 0.5160 0.6638 0.1184 0.039 Uiso calc R 1 . . H
C17 0.57258(14) 0.47957(12) 0.15190(9) 0.0291(2) Uani d . 1 . . C
H17A 0.4618 0.4109 0.0971 0.035 Uiso calc R 1 . . H
H17B 0.6667 0.4906 0.1114 0.035 Uiso calc R 1 . . H
C18 0.61390(13) 0.41662(11) 0.25816(9) 0.0279(2) Uani d . 1 . . C
H18A 0.6149 0.3164 0.2327 0.034 Uiso calc R 1 . . H
H18B 0.7315 0.4790 0.3081 0.034 Uiso calc R 1 . . H
N1 0.33687(11) 0.16378(9) 0.23397(7) 0.0258(2) Uani d . 1 . . N
N2 0.21014(12) 0.29855(9) 0.34978(7) 0.0273(2) Uani d . 1 . . N
N3 0.04970(12) 0.04516(9) 0.25566(7) 0.0269(2) Uani d . 1 . . N
N4 0.17390(12) -0.07876(10) 0.14146(8) 0.0317(2) Uani d . 1 . . N
N5 -0.06290(13) 0.17814(10) 0.37227(8) 0.0333(2) Uani d . 1 . . N
N6 0.48509(12) 0.41008(9) 0.32508(7) 0.0270(2) Uani d . 1 . . N
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
N3 C1 N1 125.97(9) y
N3 C1 N4 117.03(9) ?
N1 C1 N4 116.99(10) ?
N2 C2 N1 125.97(9) y
N2 C2 N6 116.86(9) ?
N1 C2 N6 117.15(10) ?
N3 C3 N2 125.58(10) y
N3 C3 N5 117.33(9) ?
N2 C3 N5 117.09(9) ?
N4 C4 C5 110.56(9) ?
C4 C5 C6 111.20(10) ?
C7 C6 C5 110.27(10) ?
C8 C7 C6 111.07(9) ?
N4 C8 C7 110.49(9) ?
N5 C9 C10 109.98(9) ?
C9 C10 C11 110.55(9) ?
C12 C11 C10 110.27(9) ?
C13 C12 C11 110.92(9) ?
N5 C13 C12 110.61(9) ?
N6 C14 C15 109.69(8) ?
C14 C15 C16 110.58(9) ?
C15 C16 C17 111.25(9) ?
C18 C17 C16 110.30(9) ?
N6 C18 C17 111.00(8) ?
C2 N1 C1 113.82(9) y
C2 N2 C3 114.33(9) y
C1 N3 C3 114.27(9) y
C1 N4 C4 122.56(9) ?
C1 N4 C8 122.15(9) ?
C4 N4 C8 114.95(8) ?
C3 N5 C13 122.56(9) ?
C3 N5 C9 122.85(9) ?
C13 N5 C9 114.57(9) ?
C2 N6 C18 120.33(8) ?
C2 N6 C14 119.48(9) ?
C18 N6 C14 112.82(8) ?
N4 C4 H4A 109.5 ?
C5 C4 H4A 109.5 ?
N4 C4 H4B 109.5 ?
C5 C4 H4B 109.5 ?
H4A C4 H4B 108.1 ?
C4 C5 H5A 109.4 ?
C6 C5 H5A 109.4 ?
C4 C5 H5B 109.4 ?
C6 C5 H5B 109.4 ?
H5A C5 H5B 108.0 ?
C7 C6 H6A 109.6 ?
C5 C6 H6A 109.6 ?
C7 C6 H6B 109.6 ?
C5 C6 H6B 109.6 ?
H6A C6 H6B 108.1 ?
C8 C7 H7A 109.4 ?
C6 C7 H7A 109.4 ?
C8 C7 H7B 109.4 ?
C6 C7 H7B 109.4 ?
H7A C7 H7B 108.0 ?
N4 C8 H8A 109.6 ?
C7 C8 H8A 109.6 ?
N4 C8 H8B 109.6 ?
C7 C8 H8B 109.6 ?
H8A C8 H8B 108.1 ?
N5 C9 H9A 109.7 ?
C10 C9 H9A 109.7 ?
N5 C9 H9B 109.7 ?
C10 C9 H9B 109.7 ?
H9A C9 H9B 108.2 ?
C9 C10 H10A 109.5 ?
C11 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
C11 C10 H10B 109.5 ?
H10A C10 H10B 108.1 ?
C12 C11 H11A 109.6 ?
C10 C11 H11A 109.6 ?
C12 C11 H11B 109.6 ?
C10 C11 H11B 109.6 ?
H11A C11 H11B 108.1 ?
C13 C12 H12A 109.5 ?
C11 C12 H12A 109.5 ?
C13 C12 H12B 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 108.0 ?
N5 C13 H13A 109.5 ?
C12 C13 H13A 109.5 ?
N5 C13 H13B 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 108.1 ?
N6 C14 H14A 109.7 ?
C15 C14 H14A 109.7 ?
N6 C14 H14B 109.7 ?
C15 C14 H14B 109.7 ?
H14A C14 H14B 108.2 ?
C14 C15 H15A 109.5 ?
C16 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
C16 C15 H15B 109.5 ?
H15A C15 H15B 108.1 ?
C15 C16 H16A 109.4 ?
C17 C16 H16A 109.4 ?
C15 C16 H16B 109.4 ?
C17 C16 H16B 109.4 ?
H16A C16 H16B 108.0 ?
C18 C17 H17A 109.6 ?
C16 C17 H17A 109.6 ?
C18 C17 H17B 109.6 ?
C16 C17 H17B 109.6 ?
H17A C17 H17B 108.1 ?
N6 C18 H18A 109.4 ?
C17 C18 H18A 109.4 ?
N6 C18 H18B 109.4 ?
C17 C18 H18B 109.4 ?
H18A C18 H18B 108.0 ?
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
C1 N3 . 1.3422(14) y
C1 N1 . 1.3504(13) y
C1 N4 . 1.3614(13) y
C2 N2 . 1.3415(14) y
C2 N1 . 1.3480(13) y
C2 N6 . 1.3713(13) y
C3 N3 . 1.3465(13) y
C3 N2 . 1.3482(13) y
C3 N5 . 1.3535(15) y
C4 N4 . 1.4548(14) ?
C4 C5 . 1.5166(16) ?
C5 C6 . 1.5299(16) ?
C6 C7 . 1.5172(17) ?
C7 C8 . 1.5150(15) ?
C8 N4 . 1.4622(13) ?
C9 N5 . 1.4641(13) ?
C9 C10 . 1.5200(16) ?
C10 C11 . 1.5256(15) ?
C11 C12 . 1.5217(15) ?
C12 C13 . 1.5164(15) ?
C13 N5 . 1.4629(13) ?
C14 N6 . 1.4683(13) ?
C14 C15 . 1.5253(14) ?
C15 C16 . 1.5261(16) ?
C16 C17 . 1.5317(15) ?
C17 C18 . 1.5239(15) ?
C18 N6 . 1.4575(14) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
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
N4 C4 C5 C6 -53.74(13) ?
C4 C5 C6 C7 54.34(14) ?
C5 C6 C7 C8 -54.75(13) ?
C6 C7 C8 N4 54.65(12) ?
N5 C9 C10 C11 55.62(12) ?
C9 C10 C11 C12 -55.89(12) ?
C10 C11 C12 C13 55.10(12) ?
C11 C12 C13 N5 -54.20(13) ?
N6 C14 C15 C16 -56.30(11) ?
C14 C15 C16 C17 53.87(12) ?
C15 C16 C17 C18 -52.59(12) ?
C16 C17 C18 N6 54.63(11) ?
N2 C2 N1 C1 2.27(14) ?
N6 C2 N1 C1 -179.14(8) ?
N3 C1 N1 C2 -1.86(14) ?
N4 C1 N1 C2 177.27(9) ?
N1 C2 N2 C3 -0.85(15) ?
N6 C2 N2 C3 -179.45(8) ?
N3 C3 N2 C2 -1.25(15) ?
N5 C3 N2 C2 179.00(9) ?
N1 C1 N3 C3 0.10(15) ?
N4 C1 N3 C3 -179.03(9) ?
N2 C3 N3 C1 1.60(15) ?
N5 C3 N3 C1 -178.65(9) ?
N3 C1 N4 C4 -178.34(9) y
N1 C1 N4 C4 2.46(15) ?
N3 C1 N4 C8 -5.34(15) ?
N1 C1 N4 C8 175.46(9) ?
C5 C4 N4 C1 -130.84(11) ?
C5 C4 N4 C8 55.69(13) ?
C7 C8 N4 C1 130.37(11) ?
C7 C8 N4 C4 -56.14(13) ?
N3 C3 N5 C13 175.36(9) ?
N2 C3 N5 C13 -4.87(15) ?
N3 C3 N5 C9 -3.42(16) ?
N2 C3 N5 C9 176.35(9) y
C12 C13 N5 C3 -122.67(11) ?
C12 C13 N5 C9 56.21(13) ?
C10 C9 N5 C3 122.00(11) ?
C10 C9 N5 C13 -56.87(13) ?
N2 C2 N6 C18 -167.25(8) ?
N1 C2 N6 C18 14.03(13) y
N2 C2 N6 C14 -19.37(13) ?
N1 C2 N6 C14 161.91(8) ?
C17 C18 N6 C2 90.31(11) ?
C17 C18 N6 C14 -59.55(11) ?
C15 C14 N6 C2 -90.17(11) ?
C15 C14 N6 C18 59.98(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2105115
