#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:18:57 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179747 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/43/7004392.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_7004392
loop_
_publ_author_name
'Khalaf, Majid S.'
'Coles, Martyn P.'
'Hitchcock, Peter B.'
_publ_section_title
;
 A structural, theoretical and coordinative evaluation of the bicyclic
 guanidinate derived from 1,4,6-triazabicyclo[3.3.0]oct-4-ene
;
_journal_issue                   32
_journal_name_full               'Dalton Transactions'
_journal_page_first              4288
_journal_page_last               4295
_journal_paper_doi               10.1039/b806510a
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H28 Al2 N6'
_chemical_formula_sum            'C14 H28 Al2 N6'
_chemical_formula_weight         334.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2007-08-10T14:02:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                99.825(2)
_cell_angle_beta                 103.853(2)
_cell_angle_gamma                114.523(1)
_cell_formula_units_Z            2
_cell_length_a                   8.5214(2)
_cell_length_b                   10.1796(3)
_cell_length_c                   12.2236(2)
_cell_measurement_reflns_used    9271
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.395
_cell_measurement_wavelength     0.71073
_cell_volume                     891.79(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.29314E-2
_diffrn_orient_matrix_UB_12      0.669751E-1
_diffrn_orient_matrix_UB_13      -0.514131E-1
_diffrn_orient_matrix_UB_21      -0.135901
_diffrn_orient_matrix_UB_22      -0.408178E-1
_diffrn_orient_matrix_UB_23      -0.216849E-1
_diffrn_orient_matrix_UB_31      0.205933E-1
_diffrn_orient_matrix_UB_32      0.819066E-1
_diffrn_orient_matrix_UB_33      0.68687E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13658
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.4610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                3242
_reflns_number_total             3495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806510a.txt
_cod_data_source_block           (2)-aug807
_cod_database_code               7004392
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Al1 Al 0.27049(6) 0.41408(5) 0.73962(4) 0.02574(13) Uani 1 1 d . . .
Al2 Al 0.20906(6) 0.05078(5) 0.84411(4) 0.02260(13) Uani 1 1 d . . .
N1 N 0.47094(17) 0.37263(14) 0.75091(11) 0.0265(3) Uani 1 1 d . . .
N2 N 0.42871(16) 0.14717(14) 0.80948(11) 0.0236(3) Uani 1 1 d . . .
N3 N 0.68548(17) 0.29254(15) 0.77431(11) 0.0276(3) Uani 1 1 d . . .
N4 N 0.04917(19) 0.23350(16) 0.64118(11) 0.0291(3) Uani 1 1 d . C .
N5 N 0.00199(17) 0.01993(14) 0.71753(11) 0.0269(3) Uani 1 1 d . C .
C1 C 0.51469(19) 0.26816(16) 0.77777(12) 0.0224(3) Uani 1 1 d . . .
C2 C 0.6344(2) 0.48463(19) 0.73127(16) 0.0355(4) Uani 1 1 d . . .
H2A H 0.663 0.5898 0.7693 0.043 Uiso 1 1 calc R . .
H2B H 0.6126 0.4691 0.6457 0.043 Uiso 1 1 calc R . .
C3 C 0.7901(2) 0.45357(19) 0.78841(16) 0.0357(4) Uani 1 1 d . . .
H3A H 0.8788 0.4726 0.7459 0.043 Uiso 1 1 calc R . .
H3B H 0.8559 0.5147 0.8728 0.043 Uiso 1 1 calc R . .
C4 C 0.7450(2) 0.2128(2) 0.84915(15) 0.0324(4) Uani 1 1 d . . .
H4A H 0.8126 0.2774 0.9326 0.039 Uiso 1 1 calc R . .
H4B H 0.8221 0.1749 0.8203 0.039 Uiso 1 1 calc R . .
C5 C 0.5585(2) 0.08320(19) 0.83374(15) 0.0308(3) Uani 1 1 d . . .
H5A H 0.5218 -0.0059 0.7667 0.037 Uiso 1 1 calc R . .
H5B H 0.5619 0.0525 0.9065 0.037 Uiso 1 1 calc R . .
C6 C -0.0440(2) 0.09694(18) 0.65058(13) 0.0278(3) Uani 1 1 d . . .
C7 C -0.0815(3) 0.2472(2) 0.54319(16) 0.0459(5) Uani 1 1 d . . .
H7A H -0.0223 0.2846 0.4864 0.055 Uiso 1 1 calc R A 1
H7B H -0.1233 0.318 0.575 0.055 Uiso 1 1 calc R A 1
C10 C -0.1680(2) -0.1299(2) 0.68156(17) 0.0416(4) Uani 1 1 d . . .
H10A H -0.2279 -0.1344 0.742 0.05 Uiso 1 1 calc R B 1
H10B H -0.1381 -0.2143 0.671 0.05 Uiso 1 1 calc R B 1
C11 C 0.2553(2) 0.4851(2) 0.89433(15) 0.0332(4) Uani 1 1 d . . .
H11A H 0.1604 0.4012 0.9086 0.05 Uiso 1 1 calc R . .
H11B H 0.2239 0.5675 0.8954 0.05 Uiso 1 1 calc R . .
H11C H 0.3742 0.5222 0.9563 0.05 Uiso 1 1 calc R . .
C12 C 0.3026(3) 0.5581(2) 0.64624(19) 0.0485(5) Uani 1 1 d . . .
H12A H 0.4129 0.655 0.6924 0.073 Uiso 1 1 calc R . .
H12B H 0.1949 0.5743 0.6274 0.073 Uiso 1 1 calc R . .
H12C H 0.316 0.5165 0.5727 0.073 Uiso 1 1 calc R . .
C13 C 0.2333(3) 0.1644(2) 0.99966(15) 0.0377(4) Uani 1 1 d . . .
H13A H 0.2963 0.1355 1.0616 0.057 Uiso 1 1 calc R . .
H13B H 0.1109 0.1409 1.0026 0.057 Uiso 1 1 calc R . .
H13C H 0.3047 0.2733 1.0124 0.057 Uiso 1 1 calc R . .
C14 C 0.1693(3) -0.15708(19) 0.83357(16) 0.0366(4) Uani 1 1 d . . .
H14A H 0.147 -0.2106 0.7522 0.055 Uiso 1 1 calc R . .
H14B H 0.0626 -0.2113 0.856 0.055 Uiso 1 1 calc R . .
H14C H 0.2785 -0.1525 0.8873 0.055 Uiso 1 1 calc R . .
C8 C -0.2413(3) 0.0885(3) 0.48411(16) 0.0457(5) Uani 0.866(10) 1 d P C 1
H8A H -0.3596 0.0903 0.4596 0.055 Uiso 0.866(10) 1 calc PR C 1
H8B H -0.2275 0.0357 0.414 0.055 Uiso 0.866(10) 1 calc PR C 1
C9 C -0.2919(2) -0.1388(2) 0.56558(17) 0.0439(5) Uani 0.866(10) 1 d P C 1
H9A H -0.2742 -0.1907 0.497 0.053 Uiso 0.866(10) 1 calc PR C 1
H9B H -0.4231 -0.1913 0.5579 0.053 Uiso 0.866(10) 1 calc PR C 1
N6 N -0.2294(3) 0.0165(2) 0.5771(2) 0.0327(7) Uani 0.866(10) 1 d P C 1
C8A C -0.2413(3) 0.0885(3) 0.48411(16) 0.0457(5) Uani 0.134(10) 1 d P C 2
H8A1 H -0.3559 0.0806 0.4952 0.055 Uiso 0.134(10) 1 calc PR C 2
H8A2 H -0.2629 0.0522 0.3987 0.055 Uiso 0.134(10) 1 calc PR C 2
C9A C -0.2919(2) -0.1388(2) 0.56558(17) 0.0439(5) Uani 0.134(10) 1 d P C 2
H9A1 H -0.4101 -0.1493 0.5717 0.053 Uiso 0.134(10) 1 calc PR C 2
H9A2 H -0.3172 -0.2259 0.5008 0.053 Uiso 0.134(10) 1 calc PR C 2
N6B N -0.1768(18) 0.0202(11) 0.5428(12) 0.020(3) Uiso 0.134(10) 1 d P C 2
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 '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
N1 Al1 N4 108.04(6) . . ?
N1 Al1 C11 112.88(7) . . ?
N4 Al1 C11 110.85(7) . . ?
N1 Al1 C12 104.76(8) . . ?
N4 Al1 C12 104.92(8) . . ?
C11 Al1 C12 114.82(9) . . ?
N2 Al2 N5 109.86(6) . . ?
N2 Al2 C13 110.83(7) . . ?
N5 Al2 C13 113.62(7) . . ?
N2 Al2 C14 105.10(7) . . ?
N5 Al2 C14 103.40(7) . . ?
C13 Al2 C14 113.48(8) . . ?
C1 N1 C2 105.45(13) . . ?
C1 N1 Al1 137.08(10) . . ?
C2 N1 Al1 117.40(10) . . ?
C1 N2 C5 105.47(12) . . ?
C1 N2 Al2 138.42(10) . . ?
C5 N2 Al2 115.80(10) . . ?
C1 N3 C4 106.64(12) . . ?
C1 N3 C3 106.34(13) . . ?
C4 N3 C3 124.81(13) . . ?
C6 N4 C7 105.44(14) . . ?
C6 N4 Al1 134.98(11) . . ?
C7 N4 Al1 117.77(12) . . ?
C6 N5 C10 105.27(13) . . ?
C6 N5 Al2 138.61(11) . . ?
C10 N5 Al2 116.03(11) . . ?
N2 C1 N1 132.68(13) . . ?
N2 C1 N3 113.70(13) . . ?
N1 C1 N3 113.61(13) . . ?
N1 C2 C3 104.45(13) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N3 C3 C2 100.12(13) . . ?
N3 C3 H3A 111.7 . . ?
C2 C3 H3A 111.7 . . ?
N3 C3 H3B 111.7 . . ?
C2 C3 H3B 111.7 . . ?
H3A C3 H3B 109.5 . . ?
N3 C4 C5 99.98(12) . . ?
N3 C4 H4A 111.8 . . ?
C5 C4 H4A 111.8 . . ?
N3 C4 H4B 111.8 . . ?
C5 C4 H4B 111.8 . . ?
H4A C4 H4B 109.5 . . ?
N2 C5 C4 104.43(13) . . ?
N2 C5 H5A 110.9 . . ?
C4 C5 H5A 110.9 . . ?
N2 C5 H5B 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
N5 C6 N4 132.83(14) . . ?
N5 C6 N6B 119.1(4) . . ?
N4 C6 N6B 103.1(5) . . ?
N5 C6 N6 112.26(15) . . ?
N4 C6 N6 114.91(15) . . ?
N4 C7 C8 105.14(15) . . ?
N4 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
N4 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
N5 C10 C9 105.07(15) . . ?
N5 C10 H10A 110.7 . . ?
C9 C10 H10A 110.7 . . ?
N5 C10 H10B 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
Al1 C11 H11A 109.5 . . ?
Al1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Al1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Al1 C12 H12A 109.5 . . ?
Al1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Al1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Al2 C13 H13A 109.5 . . ?
Al2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Al2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Al2 C14 H14A 109.5 . . ?
Al2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Al2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N6 C8 C7 102.83(14) . . ?
N6 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
N6 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
N6 C9 C10 101.00(15) . . ?
N6 C9 H9A 111.6 . . ?
C10 C9 H9A 111.6 . . ?
N6 C9 H9B 111.6 . . ?
C10 C9 H9B 111.6 . . ?
H9A C9 H9B 109.4 . . ?
C6 N6 C9 108.09(15) . . ?
C6 N6 C8 104.9(2) . . ?
C9 N6 C8 128.65(19) . . ?
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
Al1 N1 1.9026(14) . ?
Al1 N4 1.9143(15) . ?
Al1 C11 1.9605(17) . ?
Al1 C12 1.9790(18) . ?
Al2 N2 1.9084(13) . ?
Al2 N5 1.9166(13) . ?
Al2 C13 1.9644(17) . ?
Al2 C14 1.9747(17) . ?
N1 C1 1.329(2) . ?
N1 C2 1.4942(19) . ?
N2 C1 1.3244(19) . ?
N2 C5 1.4973(19) . ?
N3 C1 1.3837(19) . ?
N3 C4 1.458(2) . ?
N3 C3 1.459(2) . ?
N4 C6 1.326(2) . ?
N4 C7 1.497(2) . ?
N5 C6 1.326(2) . ?
N5 C10 1.500(2) . ?
C2 C3 1.526(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.527(2) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 N6B 1.352(10) . ?
C6 N6 1.403(2) . ?
C7 C8 1.513(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C10 C9 1.514(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C8 N6 1.460(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 N6 1.411(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
