#------------------------------------------------------------------------------
#$Date: 2019-11-24 10:13:53 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/84/4088468.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_4088468
loop_
_publ_author_name
'Stienen, Christian'
'Gondzik, Sebastian'
'Gehlhaar, Alexander'
'Haack, Rebekka'
'Wölper, Christoph'
'Jansen, Georg'
'Schulz, Stephan'
_publ_contact_author
;
         Prof. Dr. Schulz, Stephan
         Fachbereich Chemie der
         Universität Duisburg-Essen
         Campus Essen, Universitätsstr. 7
         D-45141 Essen, Germany
;
_publ_section_title
;
 (MeZn)2(μ-η2:η2-N6Ph2): A Powerful Starting Reagent for the Synthesis
 of Metal Hexazene Complexes
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1022
_journal_paper_doi               10.1021/acs.organomet.6b00116
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C24 H38 Al2 N6 O2'
_chemical_formula_weight         496.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                113.086(9)
_cell_angle_beta                 91.855(9)
_cell_angle_gamma                105.457(9)
_cell_formula_units_Z            1
_cell_length_a                   7.6535(13)
_cell_length_b                   9.2634(16)
_cell_length_c                   10.463(2)
_cell_measurement_reflns_used    7412
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.17
_cell_measurement_theta_min      2.51
_cell_volume                     649.8(2)
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_data_collection       'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.906
_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       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14620
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.369
_diffrn_reflns_theta_min         2.142
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0752P)²+0.4580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2833
_reflns_number_total             3552
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00116_si_002.cif
_cod_data_source_block           chs_102m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4088468
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Al1 Al 0.43592(7) 0.54153(6) 0.23181(5) 0.01684(15) Uani 1 1 d . .
O1 O 0.26299(15) 0.68397(14) 0.26236(12) 0.0179(3) Uani 1 1 d . .
N1 N 0.59404(19) 0.39182(17) 0.13339(15) 0.0178(3) Uani 1 1 d . .
N2 N 0.62395(19) 0.37283(17) 0.00676(15) 0.0179(3) Uani 1 1 d . .
N3 N 0.55128(19) 0.45466(17) -0.04544(14) 0.0175(3) Uani 1 1 d . .
C1 C 0.6654(2) 0.2922(2) 0.18250(18) 0.0177(3) Uani 1 1 d . .
C2 C 0.6962(2) 0.3399(2) 0.32765(19) 0.0230(4) Uani 1 1 d . .
H2 H 0.6708 0.4361 0.3899 0.028 Uiso 1 1 calc R U
C3 C 0.7640(3) 0.2464(2) 0.3809(2) 0.0255(4) Uani 1 1 d . .
H3 H 0.7851 0.2792 0.4796 0.031 Uiso 1 1 calc R U
C4 C 0.8014(2) 0.1048(2) 0.2905(2) 0.0259(4) Uani 1 1 d . .
H4 H 0.8498 0.0421 0.3273 0.031 Uiso 1 1 calc R U
C5 C 0.7673(3) 0.0561(2) 0.1464(2) 0.0257(4) Uani 1 1 d . .
H5 H 0.7906 -0.0415 0.0845 0.031 Uiso 1 1 calc R U
C6 C 0.6994(2) 0.1482(2) 0.09130(19) 0.0216(3) Uani 1 1 d . .
H6 H 0.6762 0.1136 -0.0076 0.026 Uiso 1 1 calc R U
C7 C 0.3191(2) 0.8623(2) 0.30567(19) 0.0213(3) Uani 1 1 d . .
H7A H 0.4000 0.8933 0.2427 0.026 Uiso 1 1 calc R U
H7B H 0.3855 0.9209 0.4032 0.026 Uiso 1 1 calc R U
C8 C 0.1420(2) 0.9045(2) 0.2954(2) 0.0241(4) Uani 1 1 d . .
H8A H 0.1617 1.0016 0.2731 0.029 Uiso 1 1 calc R U
H8B H 0.0895 0.9263 0.3838 0.029 Uiso 1 1 calc R U
C9 C 0.0183(2) 0.7480(2) 0.17420(18) 0.0216(3) Uani 1 1 d . .
H9A H -0.1131 0.7383 0.1788 0.026 Uiso 1 1 calc R U
H9B H 0.0459 0.7455 0.0817 0.026 Uiso 1 1 calc R U
C10 C 0.0688(2) 0.6135(2) 0.20076(19) 0.0211(3) Uani 1 1 d . .
H10A H -0.0064 0.5823 0.2664 0.025 Uiso 1 1 calc R U
H10B H 0.0496 0.5145 0.1117 0.025 Uiso 1 1 calc R U
C11 C 0.6291(2) 0.72396(18) 0.38736(16) 0.0133(3) Uani 1 1 d . .
H11A H 0.7393 0.6901 0.3916 0.020 Uiso 1 1 calc R U
H11B H 0.5825 0.7476 0.4772 0.020 Uiso 1 1 calc R U
H11C H 0.6598 0.8231 0.3691 0.020 Uiso 1 1 calc R U
C12 C 0.2466(2) 0.3628(2) 0.25425(19) 0.0196(3) Uani 1 1 d . .
H12A H 0.1656 0.2920 0.1644 0.029 Uiso 1 1 calc R U
H12B H 0.1744 0.4110 0.3257 0.029 Uiso 1 1 calc R U
H12C H 0.3065 0.2973 0.2837 0.029 Uiso 1 1 calc R U
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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N3 Al1 C12 120.12(7) 2_665 .
N3 Al1 C11 114.93(7) 2_665 .
C12 Al1 C11 124.93(7) . .
N3 Al1 O1 87.29(5) 2_665 .
C12 Al1 O1 92.18(6) . .
C11 Al1 O1 91.81(6) . .
N3 Al1 N1 73.85(6) 2_665 .
C12 Al1 N1 94.16(6) . .
C11 Al1 N1 99.32(6) . .
O1 Al1 N1 160.79(6) . .
C10 O1 C7 109.53(12) . .
C10 O1 Al1 122.02(10) . .
C7 O1 Al1 125.87(10) . .
N2 N1 C1 113.32(13) . .
N2 N1 Al1 118.62(10) . .
C1 N1 Al1 127.84(11) . .
N1 N2 N3 115.24(13) . .
N2 N3 N3 113.50(16) . 2_665
N2 N3 Al1 127.72(10) . 2_665
N3 N3 Al1 118.76(13) 2_665 2_665
C2 C1 C6 119.70(15) . .
C2 C1 N1 117.64(14) . .
C6 C1 N1 122.62(15) . .
C3 C2 C1 119.96(16) . .
C2 C3 C4 120.45(17) . .
C5 C4 C3 119.44(16) . .
C4 C5 C6 120.85(17) . .
C5 C6 C1 119.57(17) . .
O1 C7 C8 105.37(14) . .
C7 C8 C9 102.44(13) . .
C10 C9 C8 102.05(14) . .
O1 C10 C9 105.38(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Al1 N3 1.9693(15) 2_665
Al1 C12 1.9857(17) .
Al1 C11 2.0116(16) .
Al1 O1 2.0548(12) .
Al1 N1 2.0745(14) .
O1 C10 1.463(2) .
O1 C7 1.463(2) .
N1 N2 1.303(2) .
N1 C1 1.427(2) .
N2 N3 1.3084(19) .
N3 N3 1.414(2) 2_665
N3 Al1 1.9692(15) 2_665
C1 C2 1.397(2) .
C1 C6 1.400(2) .
C2 C3 1.389(2) .
C3 C4 1.393(3) .
C4 C5 1.387(3) .
C5 C6 1.390(2) .
C7 C8 1.519(2) .
C8 C9 1.535(2) .
C9 C10 1.517(2) .
