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#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/43/2204367.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_2204367
loop_
_publ_author_name
'Sänger, Inge'
'Lerner, Hans-Wolfram'
'Bolte, Michael'
_publ_section_title
;
 Redetermination of trans-2,5,7,10-tetraazabicyclo[4.4.0]decane
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1847
_journal_page_last               o1848
_journal_paper_doi               10.1107/S1600536804022688
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C6 H14 N4'
_chemical_formula_moiety         'C6 H14 N4'
_chemical_formula_sum            'C6 H14 N4'
_chemical_formula_weight         142.21
_chemical_name_systematic
;
trans-2,5,7,10-tetraazabicyclo[4.4.0]decane
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.283(2)
_cell_length_b                   15.937(4)
_cell_length_c                   4.6205(18)
_cell_measurement_reflns_used    2510
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      4.2
_cell_volume                     368.3(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS-II two-circle'
_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  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0802
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2406
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.81
_diffrn_reflns_theta_min         4.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0499
_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)+(0.0894P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1444
_reflns_number_gt                362
_reflns_number_total             449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6274.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2204367
_cod_database_fobs_code          2204367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.1960(3) 0.42558(6) 0.8009(2) 0.0312(5) Uani d . 1 . . N
H1' 0.356(8) 0.4282(14) 0.877(7) 0.030(10) Uiso d P 0.54(4) A 1 H
H1'' 0.062(6) 0.4260(13) 0.890(6) 0.013(9) Uiso d P 0.46(4) A 2 H
C1 0.1446(3) 0.5000 0.6067(3) 0.0277(5) Uani d S 1 . . C
H1 0.268(4) 0.5000 0.479(4) 0.023(4) Uiso d S 1 . . H
C2 0.1424(2) 0.34970(8) 0.6111(3) 0.0341(5) Uani d . 1 . . C
H2A 0.168(4) 0.2997(10) 0.740(4) 0.039(4) Uiso d . 1 . . H
H2B 0.283(3) 0.3459(9) 0.500(4) 0.035(4) Uiso d . 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
N1 0.0308(8) 0.0329(7) 0.0247(7) 0.0010(3) 0.0018(5) 0.0016(3)
C1 0.0259(9) 0.0318(9) 0.0222(9) 0.000 0.0035(7) 0.000
C2 0.0353(8) 0.0311(7) 0.0310(8) 0.0030(4) 0.0041(5) 0.0011(4)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 109.91(10) y
C1 N1 H1' . . 100.8(18) ?
C2 N1 H1' . . 106.0(18) ?
C1 N1 H1'' . . 104.5(14) ?
C2 N1 H1'' . . 104.1(14) ?
H1' N1 H1'' . . 131(3) ?
N1 C1 N1 6_565 . 108.77(13) y
N1 C1 C1 6_565 5_566 110.26(10) ?
N1 C1 C1 . 5_566 110.25(10) y
N1 C1 H1 6_565 . 109.3(5) ?
N1 C1 H1 . . 109.3(5) ?
C1 C1 H1 5_566 . 108.9(10) ?
N1 C2 C2 . 2_556 111.18(9) y
N1 C2 H2A . . 110.3(9) ?
C2 C2 H2A 2_556 . 108.8(11) ?
N1 C2 H2B . . 108.3(9) ?
C2 C2 H2B 2_556 . 112.2(8) ?
H2A C2 H2B . . 105.9(13) ?
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 C1 . 1.4591(13) y
N1 C2 . 1.4669(14) y
N1 H1' . 0.80(4) ?
N1 H1'' . 0.93(3) ?
C1 N1 6_565 1.4590(13) ?
C1 C1 5_566 1.528(3) ?
C1 H1 . 1.011(19) ?
C2 C2 2_556 1.524(2) ?
C2 H2A . 0.977(17) ?
C2 H2B . 1.031(16) ?
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
N1 H1' N1 2_657 0.80(4) 2.36(4) 3.146(3) 167(3)
N1 H1'' N1 2_557 0.93(3) 2.27(3) 3.182(3) 168(2)
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_4
_geom_torsion
C2 N1 C1 N1 6_565 179.27(7)
C2 N1 C1 C1 5_566 58.26(19)
C1 N1 C2 C2 2_556 -56.40(18)
