#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:42:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178578 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/88/4068837.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_4068837
loop_
_publ_author_name
'Theilmann, Oliver'
'Saak, Wolfgang'
'Haase, Detlev'
'Beckhaus, Rüdiger'
_publ_section_title
;
 Reactions of Low-Valent Titanocene(II) Fragments
 withtrans-4,4′-Azobispyridine (RNNR, R = C5H4N): Formation
 of Tetranuclear Molecular Squares bytrans−cisIsomerization
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2799
_journal_paper_doi               10.1021/om801123k
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C16 H16 N4'
_chemical_formula_weight         264.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8618(11)
_cell_length_b                   12.8618(11)
_cell_length_c                   17.9097(17)
_cell_measurement_temperature    153(2)
_cell_volume                     2962.7(5)
_computing_cell_refinement       'IPDS (Stoe, 1999)'
_computing_data_collection       'IPDS (Stoe, 1999)'
_computing_data_reduction        'XRED (Stoe, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia,1997)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS'
_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  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14083
_diffrn_reflns_theta_full        26.20
_diffrn_reflns_theta_max         26.20
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9854
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.021
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.731
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.731
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0204P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0423
_refine_ls_wR_factor_ref         0.0465
_reflns_number_gt                834
_reflns_number_total             1480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om801123k_si_005.cif
_cod_data_source_block           OTH019
_cod_original_sg_symbol_H-M      I41/a
_cod_database_code               4068837
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
N1 N 0.46097(7) 0.21244(8) 0.05445(5) 0.0395(3) Uani 1 1 d
H1N H 0.4699(9) 0.1534(10) 0.0910(7) 0.063(4) Uiso 1 1 d
N2 N 0.21129(7) 0.22542(8) -0.09476(5) 0.0419(3) Uani 1 1 d
C1 C 0.37970(8) 0.21981(8) 0.00624(6) 0.0310(3) Uani 1 1 d
C2 C 0.30270(8) 0.14203(9) 0.00603(6) 0.0348(3) Uani 1 1 d
H2 H 0.3059(8) 0.0741(8) 0.0415(6) 0.036(3) Uiso 1 1 d
C3 C 0.22277(9) 0.14868(10) -0.04433(7) 0.0391(3) Uani 1 1 d
H3 H 0.1672(9) 0.0952(9) -0.0431(6) 0.049(4) Uiso 1 1 d
C4 C 0.28472(9) 0.29968(10) -0.09282(7) 0.0400(3) Uani 1 1 d
H4 H 0.2778(9) 0.3552(8) -0.1296(6) 0.043(3) Uiso 1 1 d
C5 C 0.36783(9) 0.30098(9) -0.04484(6) 0.0351(3) Uani 1 1 d
H5 H 0.4187(9) 0.3569(8) -0.0460(6) 0.044(3) Uiso 1 1 d
C6 C 0.28538(11) 0.30192(10) 0.18788(7) 0.0483(3) Uani 1 1 d
H6 H 0.3097(9) 0.3386(9) 0.1431(7) 0.060(4) Uiso 1 1 d
C7 C 0.19456(11) 0.24565(10) 0.18414(7) 0.0490(3) Uani 1 1 d
H7 H 0.1544(10) 0.2418(9) 0.1364(7) 0.064(4) Uiso 1 1 d
C8 C 0.15876(10) 0.19371(10) 0.24660(8) 0.0502(3) Uani 1 1 d
H8 H 0.0951(10) 0.1555(10) 0.2417(7) 0.062(4) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0324(5) 0.0453(6) 0.0409(5) 0.0080(5) -0.0035(5) -0.0120(4)
N2 0.0346(6) 0.0520(7) 0.0390(6) -0.0022(5) 0.0003(5) 0.0001(5)
C1 0.0290(6) 0.0356(6) 0.0284(6) -0.0017(5) 0.0055(5) -0.0020(5)
C2 0.0318(6) 0.0361(6) 0.0365(7) 0.0015(6) 0.0047(6) -0.0056(5)
C3 0.0316(6) 0.0442(7) 0.0414(7) -0.0042(6) 0.0062(6) -0.0072(6)
C4 0.0392(7) 0.0448(7) 0.0360(7) 0.0064(6) 0.0058(6) 0.0049(6)
C5 0.0319(7) 0.0359(7) 0.0375(7) 0.0018(6) 0.0071(6) -0.0045(6)
C6 0.0592(9) 0.0396(7) 0.0462(8) 0.0047(6) 0.0171(7) 0.0028(6)
C7 0.0540(9) 0.0466(8) 0.0465(8) -0.0003(6) 0.0026(7) 0.0059(7)
C8 0.0459(8) 0.0464(8) 0.0583(9) -0.0029(7) 0.0098(7) -0.0022(6)
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
C1 N1 N1 120.39(9) . 6_554
C1 N1 H1N 123.5(7) . .
N1 N1 H1N 116.1(7) 6_554 .
C4 N2 C3 115.26(11) . .
N1 C1 C5 123.53(10) . .
N1 C1 C2 119.55(10) . .
C5 C1 C2 116.91(11) . .
C3 C2 C1 119.02(11) . .
C3 C2 H2 117.8(5) . .
C1 C2 H2 123.1(6) . .
N2 C3 C2 124.74(12) . .
N2 C3 H3 116.4(7) . .
C2 C3 H3 118.8(7) . .
N2 C4 C5 124.94(12) . .
N2 C4 H4 116.0(7) . .
C5 C4 H4 119.0(7) . .
C4 C5 C1 119.11(11) . .
C4 C5 H5 121.3(6) . .
C1 C5 H5 119.6(6) . .
C7 C6 C8 120.40(13) . 13
C7 C6 H6 118.9(7) . .
C8 C6 H6 120.7(7) 13 .
C6 C7 C8 119.85(13) . .
C6 C7 H7 120.4(7) . .
C8 C7 H7 119.8(7) . .
C6 C8 C7 119.75(13) 13 .
C6 C8 H8 123.0(8) 13 .
C7 C8 H8 117.2(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3591(14) .
N1 N1 1.3934(18) 6_554
N1 H1N 1.010(13) .
N2 C4 1.3437(15) .
N2 C3 1.3461(16) .
C1 C5 1.3965(15) .
C1 C2 1.4078(14) .
C2 C3 1.3702(16) .
C2 H2 1.081(11) .
C3 H3 0.992(12) .
C4 C5 1.3716(16) .
C4 H4 0.975(11) .
C5 H5 0.972(11) .
C6 C7 1.3758(18) .
C6 C8 1.3770(19) 13
C6 H6 0.982(13) .
C7 C8 1.3818(18) .
C7 H7 1.001(13) .
C8 C6 1.3770(19) 13
C8 H8 0.959(13) .
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_4
N1 N1 C1 C5 -0.65(17) 6_554 .
N1 N1 C1 C2 178.70(10) 6_554 .
N1 C1 C2 C3 -178.09(10) . .
C5 C1 C2 C3 1.30(16) . .
C4 N2 C3 C2 -0.83(17) . .
C1 C2 C3 N2 -0.17(17) . .
C3 N2 C4 C5 0.69(18) . .
N2 C4 C5 C1 0.44(18) . .
N1 C1 C5 C4 177.94(11) . .
C2 C1 C5 C4 -1.42(16) . .
C8 C6 C7 C8 0.4(2) 13 .
C6 C7 C8 C6 -0.4(2) . 13
