#------------------------------------------------------------------------------
#$Date: 2019-11-24 10:13:53 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/84/4088469.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_4088469
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            'C46 H44 N10 Zn2'
_chemical_formula_weight         867.65
_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                101.272(3)
_cell_angle_beta                 105.138(2)
_cell_angle_gamma                95.015(2)
_cell_formula_units_Z            1
_cell_length_a                   8.9002(4)
_cell_length_b                   10.8554(6)
_cell_length_c                   11.3702(6)
_cell_measurement_reflns_used    9087
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      32.93
_cell_measurement_theta_min      2.38
_cell_volume                     1028.78(9)
_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 1.000
_diffrn_measured_fraction_theta_max 0.909
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            56655
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.310
_diffrn_reflns_theta_min         1.934
_exptl_absorpt_coefficient_mu    1.212
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 TWINABS - Bruker AXS scaling for twinned crystals - Version 2008/4
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       prism
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         7229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0280
_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)+(0.0455P)²+0.2508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6398
_reflns_number_total             7229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00116_si_002.cif
_cod_data_source_block           chs_088_tw4
_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               4088469
_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   0.822
_shelx_estimated_absorpt_t_max   0.900
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
Zn1 Zn 0.13695(2) 0.82609(2) -0.04002(2) 0.01224(5) Uani 1 1 d . .
N1 N 0.31625(11) 0.79633(9) -0.10364(9) 0.01334(17) Uani 1 1 d . .
N2 N 0.16922(11) 0.72233(9) 0.08469(9) 0.01371(17) Uani 1 1 d . .
N3 N -0.07194(11) 0.82688(9) -0.16078(9) 0.01266(17) Uani 1 1 d . .
N4 N -0.14670(11) 0.92152(9) -0.13158(9) 0.01348(17) Uani 1 1 d . .
N5 N -0.07567(11) 1.00826(9) -0.03139(9) 0.01328(17) Uani 1 1 d . .
C1 C 0.42094(13) 0.72677(11) -0.05372(11) 0.0143(2) Uani 1 1 d . .
C2 C 0.41122(14) 0.66774(11) 0.04386(11) 0.0157(2) Uani 1 1 d . .
H2 H 0.4944 0.6210 0.0695 0.019 Uiso 1 1 calc R U
C3 C 0.29746(13) 0.66693(11) 0.10974(11) 0.0142(2) Uani 1 1 d . .
C4 C 0.56276(15) 0.71169(13) -0.10140(13) 0.0223(2) Uani 1 1 d . .
H4A H 0.5288 0.6644 -0.1889 0.034 Uiso 1 1 calc R U
H4B H 0.6333 0.6652 -0.0508 0.034 Uiso 1 1 calc R U
H4C H 0.6184 0.7957 -0.0955 0.034 Uiso 1 1 calc R U
C5 C 0.32790(16) 0.60009(13) 0.21607(12) 0.0217(2) Uani 1 1 d . .
H5A H 0.2544 0.5208 0.1924 0.033 Uiso 1 1 calc R U
H5B H 0.3130 0.6549 0.2903 0.033 Uiso 1 1 calc R U
H5C H 0.4361 0.5811 0.2347 0.033 Uiso 1 1 calc R U
C6 C 0.33521(13) 0.84928(11) -0.20568(11) 0.0142(2) Uani 1 1 d . .
C7 C 0.27692(16) 0.77738(13) -0.32780(12) 0.0203(2) Uani 1 1 d . .
H7 H 0.2301 0.6916 -0.3430 0.024 Uiso 1 1 calc R U
C8 C 0.28703(17) 0.83062(14) -0.42766(12) 0.0243(3) Uani 1 1 d . .
H8 H 0.2467 0.7809 -0.5108 0.029 Uiso 1 1 calc R U
C9 C 0.35504(17) 0.95491(14) -0.40713(13) 0.0245(3) Uani 1 1 d . .
H9 H 0.3616 0.9909 -0.4757 0.029 Uiso 1 1 calc R U
C10 C 0.41365(19) 1.02664(14) -0.28592(14) 0.0281(3) Uani 1 1 d . .
H10 H 0.4621 1.1119 -0.2712 0.034 Uiso 1 1 calc R U
C11 C 0.40218(17) 0.97489(13) -0.18509(12) 0.0231(3) Uani 1 1 d . .
H11 H 0.4402 1.0255 -0.1023 0.028 Uiso 1 1 calc R U
C12 C 0.06272(14) 0.72136(12) 0.15956(11) 0.0153(2) Uani 1 1 d . .
C13 C 0.06465(17) 0.83100(13) 0.24730(12) 0.0220(2) Uani 1 1 d . .
H13 H 0.1400 0.9035 0.2600 0.026 Uiso 1 1 calc R U
C14 C -0.0436(2) 0.83472(15) 0.31647(14) 0.0297(3) Uani 1 1 d . .
H14 H -0.0421 0.9100 0.3759 0.036 Uiso 1 1 calc R U
C15 C -0.15322(18) 0.72939(16) 0.29914(15) 0.0291(3) Uani 1 1 d . .
H15 H -0.2263 0.7321 0.3470 0.035 Uiso 1 1 calc R U
C16 C -0.15595(16) 0.62035(14) 0.21195(14) 0.0253(3) Uani 1 1 d . .
H16 H -0.2308 0.5478 0.2002 0.030 Uiso 1 1 calc R U
C17 C -0.04923(15) 0.61618(13) 0.14102(12) 0.0200(2) Uani 1 1 d . .
H17 H -0.0530 0.5415 0.0800 0.024 Uiso 1 1 calc R U
C18 C -0.15313(13) 0.73999(11) -0.27420(10) 0.01312(19) Uani 1 1 d . .
C19 C -0.29474(14) 0.75707(12) -0.35373(11) 0.0175(2) Uani 1 1 d . .
H19 H -0.3415 0.8308 -0.3334 0.021 Uiso 1 1 calc R U
C20 C -0.36638(16) 0.66563(14) -0.46248(12) 0.0219(2) Uani 1 1 d . .
H20 H -0.4635 0.6766 -0.5159 0.026 Uiso 1 1 calc R U
C21 C -0.29868(16) 0.55811(13) -0.49471(12) 0.0220(2) Uani 1 1 d . .
H21 H -0.3488 0.4963 -0.5697 0.026 Uiso 1 1 calc R U
C22 C -0.15768(16) 0.54195(12) -0.41667(12) 0.0199(2) Uani 1 1 d . .
H22 H -0.1102 0.4691 -0.4385 0.024 Uiso 1 1 calc R U
C23 C -0.08511(14) 0.63216(11) -0.30626(11) 0.0167(2) Uani 1 1 d . .
H23 H 0.0112 0.6202 -0.2525 0.020 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'
Zn Zn 0.2839 1.4301 '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
N1 Zn1 N2 99.76(4) . .
N1 Zn1 N3 119.11(4) . .
N2 Zn1 N3 123.90(4) . .
N1 Zn1 N5 128.78(4) . 2_575
N2 Zn1 N5 109.47(4) . 2_575
N3 Zn1 N5 77.25(4) . 2_575
C1 N1 C6 119.82(10) . .
C1 N1 Zn1 120.67(8) . .
C6 N1 Zn1 119.51(7) . .
C3 N2 C12 120.52(10) . .
C3 N2 Zn1 120.58(8) . .
C12 N2 Zn1 118.39(7) . .
N4 N3 C18 113.88(9) . .
N4 N3 Zn1 116.16(7) . .
C18 N3 Zn1 129.95(8) . .
N5 N4 N3 117.21(9) . .
N4 N5 N5 115.69(11) . 2_575
N4 N5 Zn1 130.69(7) . 2_575
N5 N5 Zn1 113.25(10) 2_575 2_575
N1 C1 C2 124.46(10) . .
N1 C1 C4 118.93(11) . .
C2 C1 C4 116.59(10) . .
C1 C2 C3 130.14(11) . .
N2 C3 C2 124.12(10) . .
N2 C3 C5 119.30(10) . .
C2 C3 C5 116.57(10) . .
C11 C6 C7 119.19(11) . .
C11 C6 N1 120.71(11) . .
C7 C6 N1 119.97(11) . .
C8 C7 C6 120.23(12) . .
C9 C8 C7 120.57(13) . .
C8 C9 C10 119.43(12) . .
C9 C10 C11 120.53(13) . .
C6 C11 C10 120.03(12) . .
C13 C12 C17 119.33(11) . .
C13 C12 N2 119.04(11) . .
C17 C12 N2 121.49(11) . .
C12 C13 C14 120.15(13) . .
C15 C14 C13 120.38(14) . .
C16 C15 C14 119.73(13) . .
C15 C16 C17 120.34(13) . .
C12 C17 C16 120.05(12) . .
C23 C18 C19 119.54(11) . .
C23 C18 N3 116.75(10) . .
C19 C18 N3 123.71(10) . .
C20 C19 C18 119.42(12) . .
C19 C20 C21 121.14(12) . .
C22 C21 C20 119.41(12) . .
C21 C22 C23 120.18(12) . .
C22 C23 C18 120.30(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 1.9432(10) .
Zn1 N2 1.9571(10) .
Zn1 N3 2.0040(10) .
Zn1 N5 2.0055(10) 2_575
N1 C1 1.3322(15) .
N1 C6 1.4322(14) .
N2 C3 1.3276(14) .
N2 C12 1.4306(15) .
N3 N4 1.3076(13) .
N3 C18 1.4120(14) .
N4 N5 1.2979(13) .
N5 N5 1.3950(19) 2_575
N5 Zn1 2.0055(10) 2_575
C1 C2 1.4027(16) .
C1 C4 1.5076(16) .
C2 C3 1.4083(16) .
C3 C5 1.5059(16) .
C6 C11 1.3890(17) .
C6 C7 1.3913(17) .
C7 C8 1.3901(18) .
C8 C9 1.379(2) .
C9 C10 1.383(2) .
C10 C11 1.3941(19) .
C12 C13 1.3912(17) .
C12 C17 1.3922(17) .
C13 C14 1.3921(19) .
C14 C15 1.384(2) .
C15 C16 1.381(2) .
C16 C17 1.3957(18) .
C18 C23 1.3935(16) .
C18 C19 1.3971(16) .
C19 C20 1.3851(17) .
C20 C21 1.389(2) .
C21 C22 1.382(2) .
C22 C23 1.3919(17) .
