#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:03:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180370 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/39/7203905.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7203905
loop_
_publ_author_name
'von Hirschheydt, Thomas'
'Wolfart, Volker'
'Gleiter, Rolf'
'Irngartinger, Hermann'
'Oeser, Thomas'
'Rominger, Frank'
'Eisenträger, Frank'
_publ_section_title
;
 A short survey of bicyclic diamines -- syntheses and
 properties of N,N'-bridged-1,10-diazabicyclooctadeca-5,14-diynes
;
_journal_issue                   2
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              175
_journal_paper_doi               10.1039/a907609c
_journal_year                    2000
_chemical_formula_sum            'C24 H36 N2'
_chemical_formula_weight         352.55
_chemical_name_systematic
; 
 1,10-Diazabicyclo[8.8.8]hexacosa-5,14,22-triyne (47) 
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   12.177(2)
_cell_length_b                   9.875(2)
_cell_length_c                   8.532(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.5
_cell_measurement_theta_min      10.5
_cell_volume                     1026.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  NONIUS_CAD4
_diffrn_measurement_method       ω2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1441
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        -3
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0348
_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)+(0.0706P)²+0.0387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1199
_reflns_number_total             1441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a907609c.txt
_cod_data_source_block           768tri8
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_database_code               7203905
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.32832(10) 0.19606(13) -0.18924(16) 0.0336(3) Uani 1 1 d . . .
C2 C 0.39624(14) 0.31614(16) -0.2133(2) 0.0403(4) Uani 1 1 d . . .
C3 C 0.51783(14) 0.28043(19) -0.2339(2) 0.0421(4) Uani 1 1 d . . .
C4 C 0.53576(14) 0.18768(18) -0.3746(2) 0.0391(4) Uani 1 1 d . . .
C5 C 0.64368(13) 0.12148(16) -0.3783(2) 0.0374(3) Uani 1 1 d . . .
C6 C 0.72678(13) 0.05937(17) -0.3775(2) 0.0387(4) Uani 1 1 d . . .
C7 C 0.82945(14) -0.0185(2) -0.3833(2) 0.0472(4) Uani 1 1 d . . .
C8 C 0.85824(13) -0.09845(19) -0.2353(2) 0.0427(4) Uani 1 1 d . . .
C9 C 0.78886(14) -0.22414(19) -0.2086(2) 0.0414(4) Uani 1 1 d . . .
C10 C 0.35421(13) 0.12133(16) -0.04599(19) 0.0338(3) Uani 1 1 d . . .
C11 C 0.34605(16) 0.19935(17) 0.1077(2) 0.0400(4) Uani 1 1 d . . .
C12 C 0.35499(14) 0.10765(18) 0.2516(2) 0.0415(4) Uani 1 1 d . . .
C13 C 0.45830(14) 0.03078(17) 0.25582(19) 0.0378(4) Uani 1 1 d . . .
H2A H 0.3696(16) 0.359(2) -0.316(3) 0.051(5) Uiso 1 1 d . . .
H2B H 0.3848(16) 0.385(2) -0.124(2) 0.049(5) Uiso 1 1 d . . .
H3A H 0.5590(18) 0.368(3) -0.246(3) 0.063(7) Uiso 1 1 d . . .
H3B H 0.5446(15) 0.2362(19) -0.137(2) 0.041(5) Uiso 1 1 d . . .
H4A H 0.520(2) 0.243(3) -0.469(3) 0.070(7) Uiso 1 1 d . . .
H4B H 0.4777(17) 0.122(2) -0.368(2) 0.046(5) Uiso 1 1 d . . .
H7A H 0.8222(18) -0.083(2) -0.474(3) 0.056(6) Uiso 1 1 d . . .
H7B H 0.8947(19) 0.044(2) -0.409(3) 0.067(7) Uiso 1 1 d . . .
H8A H 0.9362(16) -0.131(2) -0.245(2) 0.047(5) Uiso 1 1 d . . .
H8B H 0.8545(17) -0.0380(19) -0.142(2) 0.047(5) Uiso 1 1 d . . .
H9A H 0.7946(17) -0.285(2) -0.302(3) 0.054(6) Uiso 1 1 d . . .
H9B H 0.8147(17) -0.275(2) -0.117(3) 0.045(5) Uiso 1 1 d . . .
H10A H 0.3029(15) 0.0429(19) -0.040(2) 0.039(5) Uiso 1 1 d . . .
H10B H 0.4300(15) 0.080(2) -0.057(2) 0.041(5) Uiso 1 1 d . . .
H11A H 0.4047(19) 0.266(2) 0.110(3) 0.051(6) Uiso 1 1 d . . .
H11B H 0.281(2) 0.248(3) 0.111(3) 0.074(8) Uiso 1 1 d . . .
H12A H 0.3463(18) 0.164(2) 0.345(3) 0.059(6) Uiso 1 1 d . . .
H12B H 0.2921(17) 0.043(2) 0.254(2) 0.047(6) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10 113.92(13) . . ?
C2 N1 C9 112.50(13) . 2_655 ?
C10 N1 C9 113.60(13) . 2_655 ?
N1 C2 C3 112.13(13) . . ?
N1 C2 H2A 106.1(11) . . ?
C3 C2 H2A 107.7(11) . . ?
N1 C2 H2B 111.0(11) . . ?
C3 C2 H2B 111.5(11) . . ?
H2A C2 H2B 108.1(15) . . ?
C4 C3 C2 111.50(14) . . ?
C4 C3 H3A 111.5(13) . . ?
C2 C3 H3A 107.2(13) . . ?
C4 C3 H3B 110.2(11) . . ?
C2 C3 H3B 108.9(11) . . ?
H3A C3 H3B 107.4(17) . . ?
C5 C4 C3 114.33(14) . . ?
C5 C4 H4A 113.4(16) . . ?
C3 C4 H4A 106.4(15) . . ?
C5 C4 H4B 111.0(11) . . ?
C3 C4 H4B 104.7(12) . . ?
H4A C4 H4B 106.2(19) . . ?
C6 C5 C4 174.99(17) . . ?
C5 C6 C7 177.70(19) . . ?
C6 C7 C8 115.95(15) . . ?
C6 C7 H7A 106.4(13) . . ?
C8 C7 H7A 109.2(14) . . ?
C6 C7 H7B 110.3(12) . . ?
C8 C7 H7B 108.2(14) . . ?
H7A C7 H7B 106.4(18) . . ?
C9 C8 C7 114.72(16) . . ?
C9 C8 H8A 106.1(12) . . ?
C7 C8 H8A 108.1(11) . . ?
C9 C8 H8B 110.2(11) . . ?
C7 C8 H8B 109.8(11) . . ?
H8A C8 H8B 107.6(16) . . ?
N1 C9 C8 113.87(15) 2_655 . ?
N1 C9 H9A 105.8(12) 2_655 . ?
C8 C9 H9A 109.2(12) . . ?
N1 C9 H9B 108.6(12) 2_655 . ?
C8 C9 H9B 111.1(12) . . ?
H9A C9 H9B 108.0(17) . . ?
N1 C10 C11 116.75(13) . . ?
N1 C10 H10A 107.6(11) . . ?
C11 C10 H10A 107.8(11) . . ?
N1 C10 H10B 108.7(12) . . ?
C11 C10 H10B 110.2(11) . . ?
H10A C10 H10B 105.2(15) . . ?
C10 C11 C12 112.74(13) . . ?
C10 C11 H11A 108.1(13) . . ?
C12 C11 H11A 109.6(13) . . ?
C10 C11 H11B 110.0(16) . . ?
C12 C11 H11B 110.2(16) . . ?
H11A C11 H11B 105.9(18) . . ?
C13 C12 C11 112.75(14) . . ?
C13 C12 H12A 111.5(13) . . ?
C11 C12 H12A 108.0(13) . . ?
C13 C12 H12B 108.9(11) . . ?
C11 C12 H12B 110.1(11) . . ?
H12A C12 H12B 105.3(17) . . ?
C13 C13 C12 178.57(10) 2_655 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.460(2) . ?
N1 C10 1.462(2) . ?
N1 C9 1.463(2) 2_655 ?
C2 C3 1.532(2) . ?
C2 H2A 1.02(2) . ?
C2 H2B 1.03(2) . ?
C3 C4 1.526(2) . ?
C3 H3A 1.00(2) . ?
C3 H3B 0.99(2) . ?
C4 C5 1.468(2) . ?
C4 H4A 0.99(3) . ?
C4 H4B 0.96(2) . ?
C5 C6 1.183(2) . ?
C6 C7 1.469(2) . ?
C7 C8 1.529(2) . ?
C7 H7A 1.00(2) . ?
C7 H7B 1.03(2) . ?
C8 C9 1.519(3) . ?
C8 H8A 1.01(2) . ?
C8 H8B 1.00(2) . ?
C9 N1 1.463(2) 2_655 ?
C9 H9A 1.00(2) . ?
C9 H9B 0.98(2) . ?
C10 C11 1.524(2) . ?
C10 H10A 0.997(19) . ?
C10 H10B 1.014(19) . ?
C11 C12 1.529(2) . ?
C11 H11A 0.97(2) . ?
C11 H11B 0.93(3) . ?
C12 C13 1.470(2) . ?
C12 H12A 0.98(2) . ?
C12 H12B 1.00(2) . ?
C13 C13 1.184(3) 2_655 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C3 63.22(18) . . . . ?
C9 N1 C2 C3 -165.65(15) 2_655 . . . ?
N1 C2 C3 C4 59.8(2) . . . . ?
C2 C3 C4 C5 -165.02(15) . . . . ?
C3 C4 C5 C6 103(2) . . . . ?
C4 C5 C6 C7 99(5) . . . . ?
C5 C6 C7 C8 -150(4) . . . . ?
C6 C7 C8 C9 73.4(2) . . . . ?
C7 C8 C9 N1 -61.4(2) . . . 2_655 ?
C2 N1 C10 C11 57.82(18) . . . . ?
C9 N1 C10 C11 -72.77(19) 2_655 . . . ?
N1 C10 C11 C12 170.06(14) . . . . ?
C10 C11 C12 C13 58.5(2) . . . . ?
C11 C12 C13 C13 -23(10) . . . 2_655 ?
