#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/35/2213579.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_2213579
loop_
_publ_author_name
'Poethig, Alexander'
'Ahrens, Sebastian'
'Strassner, Thomas'
_publ_section_title
;
 1,3,5-Tricyclopropyl-1,3,5-triazinane
;
_journal_coeditor_code           SK3113
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2398
_journal_page_last               o2399
_journal_paper_doi               10.1107/S1600536807015498
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H21 N3'
_chemical_formula_moiety         'C12 H21 N3'
_chemical_formula_sum            'C12 H21 N3'
_chemical_formula_weight         207.32
_chemical_name_common            1,3,5-Tricyclopropyl-1,3,5-triazinane
_chemical_name_systematic
;
1,3,5-tricyclopropyl-1,3,5-triazinane
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7050(10)
_cell_length_b                   16.2310(10)
_cell_length_c                   8.514(2)
_cell_measurement_reflns_used    61
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      19.351
_cell_measurement_theta_min      4.197
_cell_volume                     1203.0(3)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'EvalCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'enCIFer (Allen et al.,  2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7497
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.8393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.143
_refine_ls_abs_structure_details 'not possible'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1191
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0320
_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)+(0.0481P)²+0.0772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                1042
_reflns_number_total             1191
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3113.cif
_cod_data_source_block           I
_cod_database_code               2213579
_cod_database_fobs_code          2213579
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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_refinement_flags
_atom_site_occupancy
N N1 0.82155(17) 0.02211(10) 0.50653(19) 0.0287(4) Uani d . 1
N N2 0.75402(17) -0.05661(9) 0.73890(19) 0.0281(4) Uani d . 1
N N3 0.71919(17) 0.08968(8) 0.73811(18) 0.0274(4) Uani d . 1
C C1 0.8227(2) 0.09588(12) 0.6022(2) 0.0322(5) Uani d . 1
C C2 0.7634(2) 0.01857(12) 0.8333(3) 0.0316(5) Uani d . 1
C C3 0.8573(2) -0.04895(12) 0.6031(2) 0.0316(5) Uani d . 1
C C4 0.6821(2) 0.01260(11) 0.4169(2) 0.0286(4) Uani d . 1
C C5 0.6958(2) -0.03324(12) 0.2646(3) 0.0361(5) Uani d . 1
C C6 0.6747(2) 0.05862(12) 0.2644(2) 0.0358(5) Uani d . 1
C C7 0.7263(2) 0.16415(12) 0.8308(2) 0.0340(5) Uani d . 1
C C8 0.6263(3) 0.23424(12) 0.7814(3) 0.0437(5) Uani d . 1
C C9 0.5894(3) 0.18672(12) 0.9278(2) 0.0401(5) Uani d . 1
C C10 0.7969(2) -0.12719(13) 0.8325(2) 0.0369(5) Uani d . 1
C C11 0.6753(3) -0.16634(12) 0.9316(3) 0.0426(6) Uani d . 1
C C12 0.7319(3) -0.20850(12) 0.7855(3) 0.0484(6) Uani d . 1
H H1A 0.6943 0.0140 0.9252 0.038 Uiso calc R 1
H H1B 0.8697 0.0259 0.8723 0.038 Uiso calc R 1
H H5A 0.8290 0.1789 0.8752 0.041 Uiso calc R 1
H H6A 0.9037 -0.1275 0.8759 0.044 Uiso calc R 1
H H7A 0.7915 0.1435 0.5369 0.039 Uiso calc R 1
H H7B 0.9286 0.1061 0.6399 0.039 Uiso calc R 1
H H8A 0.7641 0.0931 0.2351 0.043 Uiso calc R 1
H H8B 0.5738 0.0806 0.2310 0.043 Uiso calc R 1
H H9A 0.9645 -0.0444 0.6408 0.038 Uiso calc R 1
H H9B 0.8496 -0.0994 0.5382 0.038 Uiso calc R 1
H H10A 0.5841 0.0062 0.4769 0.034 Uiso calc R 1
H H11A 0.6078 0.2140 1.0301 0.048 Uiso calc R 1
H H11B 0.4996 0.1493 0.9253 0.048 Uiso calc R 1
H H12A 0.5711 -0.1418 0.9293 0.051 Uiso calc R 1
H H12B 0.7064 -0.1897 1.0342 0.051 Uiso calc R 1
H H13A 0.6077 -0.0677 0.2314 0.043 Uiso calc R 1
H H13B 0.7980 -0.0552 0.2355 0.043 Uiso calc R 1
H H14A 0.5592 0.2260 0.6888 0.052 Uiso calc R 1
H H14B 0.6673 0.2908 0.7936 0.052 Uiso calc R 1
H H15A 0.7976 -0.2578 0.7984 0.058 Uiso calc R 1
H H15B 0.6624 -0.2100 0.6935 0.058 Uiso calc R 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 0.0000 '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 0.0000 '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
N1 C1 N3 112.45(14) yes
N1 C3 N2 112.47(15) yes
N1 C4 C5 116.36(16) yes
N1 C4 C6 116.18(16) yes
N1 C1 H7A 109.1 ?
N1 C1 H7B 109.1 ?
N2 C2 H1A 109.7 ?
N2 C2 H1B 109.7 ?
N2 C10 C12 117.10(18) ?
N2 C10 C11 117.71(17) ?
N2 C10 H6A 116.6 ?
N3 C2 N2 109.81(16) yes
N3 C7 C8 117.28(17) yes
N3 C7 C9 118.19(16) yes
N3 C2 H1A 109.7 ?
N3 C2 H1B 109.7 ?
N3 C7 H5A 116.4 ?
N3 C1 H7A 109.1 ?
N3 C1 H7B 109.1 ?
C1 N1 C3 109.71(15) ?
C2 N2 C3 109.10(15) yes
C2 N3 C1 109.20(15) yes
C4 N1 C1 113.08(14) yes
C4 N1 C3 113.30(14) ?
C4 C6 H8B 117.8 ?
C4 C6 C5 59.95(12) yes
C4 C6 H8A 117.8 ?
C5 C6 H8B 117.8 ?
C5 C6 H8A 117.8 ?
C6 C4 C5 60.12(13) yes
C7 N3 C2 110.26(15) ?
C7 N3 C1 110.27(14) ?
C8 C7 C9 60.30(14) yes
C8 C7 H5A 116.4 ?
C9 C7 H5A 116.4 ?
C10 N2 C2 110.09(16) ?
C10 N2 C3 110.07(14) ?
C11 C10 H6A 116.6 ?
C12 C10 C11 60.42(14) ?
C12 C10 H6A 116.6 ?
H7A C1 H7B 107.8 ?
H8A C6 H8B 114.9 ?
N1 C3 H9A 109.1 ?
N2 C3 H9A 109.1 ?
N1 C3 H9B 109.1 ?
N2 C3 H9B 109.1 ?
H9A C3 H9B 107.8 ?
N1 C4 H10A 117.3 ?
C6 C4 H10A 117.3 ?
C5 C4 H10A 117.3 ?
C7 C9 C8 59.76(14) ?
C7 C9 H11A 117.8 ?
C8 C9 H11A 117.8 ?
C7 C9 H11B 117.8 ?
C8 C9 H11B 117.8 ?
H11A C9 H11B 114.9 ?
C10 C11 C12 59.63(14) yes
C10 C11 H12A 117.8 ?
C12 C11 H12A 117.8 ?
C10 C11 H12B 117.8 ?
C12 C11 H12B 117.8 ?
H12A C11 H12B 114.9 ?
C4 C5 C6 59.93(13) ?
C4 C5 H13A 117.8 ?
C6 C5 H13A 117.8 ?
C4 C5 H13B 117.8 ?
C6 C5 H13B 117.8 ?
H13A C5 H13B 114.9 ?
C7 C8 C9 59.94(14) ?
C7 C8 H14A 117.8 ?
C9 C8 H14A 117.8 ?
C7 C8 H14B 117.8 ?
C9 C8 H14B 117.8 ?
H14A C8 H14B 114.9 ?
C10 C12 C11 59.95(14) ?
C10 C12 H15A 117.8 ?
C11 C12 H15A 117.8 ?
C10 C12 H15B 117.8 ?
C11 C12 H15B 117.8 ?
H1A C2 H1B 108.2 ?
H15A C12 H15B 114.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.448(2) yes
N1 C3 1.450(2) yes
N1 C4 1.442(2) yes
N2 C2 1.464(2) yes
N2 C3 1.470(2) yes
N2 C10 1.445(2) yes
N3 C1 1.470(2) yes
N3 C2 1.462(2) yes
N3 C7 1.445(2) yes
C1 H7A 0.9900 ?
C1 H7B 0.9900 ?
C2 H1A 0.9900 ?
C2 H1B 0.9900 ?
C3 H9A 0.9900 ?
C3 H9B 0.9900 ?
C4 C5 1.500(3) yes
C4 H10A 1.0000 ?
C5 H13A 0.9900 ?
C5 H13B 0.9900 ?
C6 C4 1.499(3) yes
C6 C5 1.502(3) yes
C6 H8A 0.9900 ?
C6 H8B 0.9900 ?
C7 C8 1.493(3) ?
C7 C9 1.496(3) ?
C7 H5A 1.0000 ?
C8 H14A 0.9900 ?
C8 H14B 0.9900 ?
C9 C8 1.501(3) ?
C9 H11A 0.9900 ?
C9 H11B 0.9900 ?
C10 C12 1.491(3) ?
C10 C11 1.496(3) ?
C10 H6A 1.0000 ?
C11 C12 1.503(3) ?
C11 H12A 0.9900 ?
C11 H12B 0.9900 ?
C12 H15A 0.9900 ?
C12 H15B 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
C7 N3 C2 N2 179.30(15) ?
C1 N3 C2 N2 -59.40(18) ?
C10 N2 C2 N3 -179.73(15) ?
C3 N2 C2 N3 59.38(18) ?
C2 N3 C7 C8 -154.53(17) ?
C1 N3 C7 C8 84.8(2) ?
C2 N3 C7 C9 -85.4(2) ?
C1 N3 C7 C9 153.95(17) ?
C2 N2 C10 C12 153.83(18) ?
C3 N2 C10 C12 -85.9(2) ?
C1 N1 C4 C6 83.23(19) yes
C2 N2 C10 C11 84.8(2) yes
C2 N3 C1 N1 57.84(19) yes
C3 N2 C10 C11 -154.92(18) ?
C4 N1 C1 N3 72.45(19) yes
C3 N1 C1 N3 -55.09(19) ?
C7 N3 C1 N1 179.13(15) ?
C4 N1 C3 N2 -72.3(2) ?
C1 N1 C3 N2 55.15(19) ?
C10 N2 C3 N1 -178.74(16) ?
C2 N2 C3 N1 -57.84(19) ?
C3 N1 C4 C6 -151.14(16) ?
C1 N1 C4 C5 151.15(16) ?
C3 N1 C4 C5 -83.2(2) ?
C5 C6 C4 N1 106.75(18) ?
N3 C7 C9 C8 -107.0(2) ?
N2 C10 C11 C12 107.1(2) ?
N1 C4 C5 C6 -106.44(18) ?
N3 C7 C8 C9 108.53(19) ?
N2 C10 C12 C11 -108.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16410343
