#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:03:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179522 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/19/4341915.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_4341915
loop_
_publ_author_name
'Chang, Mu-Chieh'
'Roewen, Peter'
'Travieso-Puente, Raquel'
'Lutz, Martin'
'Otten, Edwin'
_publ_section_title
;
 Formazanate Ligands as Structurally Versatile, Redox-Active Analogues of
 β-Diketiminates in Zinc Chemistry.
;
_journal_issue                   1
_journal_name_full               'Inorganic chemistry'
_journal_page_first              379
_journal_page_last               388
_journal_paper_doi               10.1021/ic5025873
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C46 H46 N8 Zn'
_chemical_formula_sum            'C46 H46 N8 Zn'
_chemical_formula_weight         776.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.906(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9988(6)
_cell_length_b                   11.4774(5)
_cell_length_c                   19.3454(5)
_cell_measurement_reflns_used    26123
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.11
_cell_volume                     3967.4(2)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex2
_computing_data_reduction        'Eval15, SADABS-2008/1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0091
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28246
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0254
_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)+(0.0391P)²+3.9002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0733
_reflns_number_gt                4357
_reflns_number_total             4542
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic5025873_si_002.cif
_cod_data_source_block           l0396a
_cod_depositor_comments
'Adding full bibliography for 4341915--4341919.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4341915
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Zn1 Zn 0.5000 0.381496(16) 0.2500 0.01652(7) Uani 1 2 d S
N1 N 0.47351(5) 0.49084(9) 0.16911(5) 0.0179(2) Uani 1 1 d .
N2 N 0.52020(6) 0.51704(9) 0.12501(5) 0.0184(2) Uani 1 1 d .
N3 N 0.59793(5) 0.34281(9) 0.14155(5) 0.0185(2) Uani 1 1 d .
N4 N 0.56416(6) 0.29470(9) 0.19085(5) 0.0178(2) Uani 1 1 d .
C1 C 0.40545(7) 0.55513(10) 0.15874(7) 0.0205(2) Uani 1 1 d .
C2 C 0.35255(7) 0.53106(12) 0.20384(8) 0.0262(3) Uani 1 1 d .
H2 H 0.3632 0.4749 0.2398 0.031 Uiso 1 1 calc R
C3 C 0.28429(8) 0.58916(13) 0.19625(9) 0.0351(3) Uani 1 1 d .
H3 H 0.2485 0.5729 0.2272 0.042 Uiso 1 1 calc R
C4 C 0.26830(8) 0.67036(14) 0.14394(10) 0.0397(4) Uani 1 1 d .
H4 H 0.2215 0.7095 0.1386 0.048 Uiso 1 1 calc R
C5 C 0.32130(8) 0.69450(14) 0.09914(9) 0.0371(3) Uani 1 1 d .
H5 H 0.3104 0.7505 0.0632 0.044 Uiso 1 1 calc R
C6 C 0.38982(8) 0.63789(12) 0.10623(8) 0.0279(3) Uani 1 1 d .
H6 H 0.4258 0.6553 0.0756 0.033 Uiso 1 1 calc R
C7 C 0.58248(7) 0.45330(10) 0.12038(6) 0.0183(2) Uani 1 1 d .
C8 C 0.63481(7) 0.50181(11) 0.07401(6) 0.0196(2) Uani 1 1 d .
C9 C 0.70975(7) 0.46767(12) 0.08234(7) 0.0251(3) Uani 1 1 d .
H9 H 0.7275 0.4162 0.1191 0.030 Uiso 1 1 calc R
C10 C 0.75870(7) 0.50821(13) 0.03737(8) 0.0281(3) Uani 1 1 d .
H10 H 0.8094 0.4831 0.0436 0.034 Uiso 1 1 calc R
C11 C 0.73503(8) 0.58459(12) -0.01641(7) 0.0271(3) Uani 1 1 d .
C12 C 0.66073(8) 0.62038(12) -0.02333(7) 0.0290(3) Uani 1 1 d .
H12 H 0.6435 0.6737 -0.0593 0.035 Uiso 1 1 calc R
C13 C 0.61102(7) 0.58023(12) 0.02093(7) 0.0246(3) Uani 1 1 d .
H13 H 0.5606 0.6064 0.0150 0.030 Uiso 1 1 calc R
C14 C 0.78800(10) 0.62617(15) -0.06616(9) 0.0385(4) Uani 1 1 d .
H14A H 0.7876 0.5708 -0.1048 0.058 Uiso 1 1 calc R
H14B H 0.8388 0.6316 -0.0416 0.058 Uiso 1 1 calc R
H14C H 0.7720 0.7030 -0.0844 0.058 Uiso 1 1 calc R
C15 C 0.57105(6) 0.16989(10) 0.19094(6) 0.0177(2) Uani 1 1 d .
C16 C 0.54569(7) 0.10498(11) 0.13131(7) 0.0223(2) Uani 1 1 d .
C17 C 0.54939(8) -0.01610(12) 0.13594(7) 0.0265(3) Uani 1 1 d .
H17 H 0.5315 -0.0611 0.0962 0.032 Uiso 1 1 calc R
C18 C 0.57833(8) -0.07333(11) 0.19652(7) 0.0263(3) Uani 1 1 d .
C19 C 0.60351(7) -0.00655(11) 0.25436(7) 0.0238(3) Uani 1 1 d .
H19 H 0.6235 -0.0446 0.2961 0.029 Uiso 1 1 calc R
C20 C 0.60037(7) 0.11480(11) 0.25303(7) 0.0200(2) Uani 1 1 d .
C21 C 0.51338(9) 0.16066(14) 0.06351(7) 0.0332(3) Uani 1 1 d .
H21A H 0.5540 0.1805 0.0361 0.050 Uiso 1 1 calc R
H21B H 0.4862 0.2316 0.0733 0.050 Uiso 1 1 calc R
H21C H 0.4790 0.1060 0.0372 0.050 Uiso 1 1 calc R
C22 C 0.58278(10) -0.20483(13) 0.19865(10) 0.0408(4) Uani 1 1 d .
H22A H 0.5341 -0.2378 0.1805 0.061 Uiso 1 1 calc R
H22B H 0.5963 -0.2306 0.2468 0.061 Uiso 1 1 calc R
H22C H 0.6209 -0.2314 0.1700 0.061 Uiso 1 1 calc R
C23 C 0.63153(8) 0.18483(13) 0.31544(7) 0.0279(3) Uani 1 1 d .
H23A H 0.6525 0.1321 0.3526 0.042 Uiso 1 1 calc R
H23B H 0.5915 0.2314 0.3318 0.042 Uiso 1 1 calc R
H23C H 0.6709 0.2367 0.3026 0.042 Uiso 1 1 calc R
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
N4 Zn1 N4 119.86(6) . 2_655
N4 Zn1 N1 87.98(4) . .
N4 Zn1 N1 131.19(4) 2_655 .
N4 Zn1 N1 131.19(4) . 2_655
N4 Zn1 N1 87.98(4) 2_655 2_655
N1 Zn1 N1 103.08(6) . 2_655
N2 N1 C1 113.59(10) . .
N2 N1 Zn1 122.72(8) . .
C1 N1 Zn1 123.42(8) . .
N1 N2 C7 121.63(10) . .
N4 N3 C7 121.23(10) . .
N3 N4 C15 111.87(9) . .
N3 N4 Zn1 123.99(8) . .
C15 N4 Zn1 123.68(8) . .
C2 C1 C6 119.85(12) . .
C2 C1 N1 116.75(11) . .
C6 C1 N1 123.40(11) . .
C3 C2 C1 120.02(13) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C4 C3 C2 120.33(14) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 119.54(13) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C6 C5 C4 120.89(14) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C1 119.37(13) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
N2 C7 N3 129.10(11) . .
N2 C7 C8 115.39(10) . .
N3 C7 C8 114.36(10) . .
C13 C8 C9 118.26(11) . .
C13 C8 C7 121.75(11) . .
C9 C8 C7 119.98(11) . .
C10 C9 C8 120.68(12) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C11 C10 C9 121.33(12) . .
C11 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
C10 C11 C12 117.65(12) . .
C10 C11 C14 121.11(13) . .
C12 C11 C14 121.24(14) . .
C13 C12 C11 121.74(13) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C12 C13 C8 120.31(12) . .
C12 C13 H13 119.8 . .
C8 C13 H13 119.8 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C20 121.09(11) . .
C16 C15 N4 120.58(11) . .
C20 C15 N4 118.26(11) . .
C17 C16 C15 117.94(12) . .
C17 C16 C21 119.20(12) . .
C15 C16 C21 122.84(12) . .
C18 C17 C16 122.40(13) . .
C18 C17 H17 118.8 . .
C16 C17 H17 118.8 . .
C19 C18 C17 118.19(12) . .
C19 C18 C22 121.26(13) . .
C17 C18 C22 120.55(14) . .
C18 C19 C20 121.93(12) . .
C18 C19 H19 119.0 . .
C20 C19 H19 119.0 . .
C19 C20 C15 118.44(12) . .
C19 C20 C23 120.63(12) . .
C15 C20 C23 120.85(11) . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C18 C22 H22A 109.5 . .
C18 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C18 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N4 1.9882(10) .
Zn1 N4 1.9883(10) 2_655
Zn1 N1 2.0179(10) .
Zn1 N1 2.0179(10) 2_655
N1 N2 1.3026(14) .
N1 C1 1.4235(15) .
N2 C7 1.3504(15) .
N3 N4 1.3129(14) .
N3 C7 1.3512(16) .
N4 C15 1.4378(15) .
C1 C2 1.3942(18) .
C1 C6 1.3945(19) .
C2 C3 1.3901(19) .
C2 H2 0.9500 .
C3 C4 1.380(2) .
C3 H3 0.9500 .
C4 C5 1.392(2) .
C4 H4 0.9500 .
C5 C6 1.3862(19) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.4849(16) .
C8 C13 1.3937(17) .
C8 C9 1.3953(17) .
C9 C10 1.3905(18) .
C9 H9 0.9500 .
C10 C11 1.388(2) .
C10 H10 0.9500 .
C11 C12 1.390(2) .
C11 C14 1.5113(18) .
C12 C13 1.3894(18) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.4026(17) .
C15 C20 1.4031(17) .
C16 C17 1.3936(18) .
C16 C21 1.5112(18) .
C17 C18 1.389(2) .
C17 H17 0.9500 .
C18 C19 1.387(2) .
C18 C22 1.5116(19) .
C19 C20 1.3940(17) .
C19 H19 0.9500 .
C20 C23 1.5019(18) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
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
N4 Zn1 N1 N2 -32.73(9) .
N4 Zn1 N1 N2 -161.86(8) 2_655
N1 Zn1 N1 N2 99.21(10) 2_655
N4 Zn1 N1 C1 153.67(10) .
N4 Zn1 N1 C1 24.54(12) 2_655
N1 Zn1 N1 C1 -74.39(9) 2_655
C1 N1 N2 C7 -170.10(11) .
Zn1 N1 N2 C7 15.72(15) .
C7 N3 N4 C15 162.50(11) .
C7 N3 N4 Zn1 -9.93(15) .
N4 Zn1 N4 N3 167.58(10) 2_655
N1 Zn1 N4 N3 29.88(9) .
N1 Zn1 N4 N3 -75.79(11) 2_655
N4 Zn1 N4 C15 -3.98(8) 2_655
N1 Zn1 N4 C15 -141.67(10) .
N1 Zn1 N4 C15 112.66(10) 2_655
N2 N1 C1 C2 179.59(11) .
Zn1 N1 C1 C2 -6.28(16) .
N2 N1 C1 C6 0.33(18) .
Zn1 N1 C1 C6 174.46(10) .
C6 C1 C2 C3 0.2(2) .
N1 C1 C2 C3 -179.05(13) .
C1 C2 C3 C4 0.4(2) .
C2 C3 C4 C5 -0.6(3) .
C3 C4 C5 C6 0.2(3) .
C4 C5 C6 C1 0.4(2) .
C2 C1 C6 C5 -0.6(2) .
N1 C1 C6 C5 178.61(13) .
N1 N2 C7 N3 20.20(19) .
N1 N2 C7 C8 -172.91(10) .
N4 N3 C7 N2 -23.69(19) .
N4 N3 C7 C8 169.31(10) .
N2 C7 C8 C13 -22.33(17) .
N3 C7 C8 C13 146.53(12) .
N2 C7 C8 C9 158.65(12) .
N3 C7 C8 C9 -32.49(17) .
C13 C8 C9 C10 -2.0(2) .
C7 C8 C9 C10 177.08(12) .
C8 C9 C10 C11 0.8(2) .
C9 C10 C11 C12 0.7(2) .
C9 C10 C11 C14 -178.55(14) .
C10 C11 C12 C13 -1.1(2) .
C14 C11 C12 C13 178.21(14) .
C11 C12 C13 C8 -0.1(2) .
C9 C8 C13 C12 1.6(2) .
C7 C8 C13 C12 -177.40(12) .
N3 N4 C15 C16 -57.43(14) .
Zn1 N4 C15 C16 115.03(11) .
N3 N4 C15 C20 125.60(11) .
Zn1 N4 C15 C20 -61.93(13) .
C20 C15 C16 C17 0.99(18) .
N4 C15 C16 C17 -175.89(11) .
C20 C15 C16 C21 179.69(12) .
N4 C15 C16 C21 2.81(19) .
C15 C16 C17 C18 -1.2(2) .
C21 C16 C17 C18 -179.98(12) .
C16 C17 C18 C19 0.7(2) .
C16 C17 C18 C22 -178.66(13) .
C17 C18 C19 C20 0.07(19) .
C22 C18 C19 C20 179.44(13) .
C18 C19 C20 C15 -0.29(19) .
C18 C19 C20 C23 -176.99(12) .
C16 C15 C20 C19 -0.26(18) .
N4 C15 C20 C19 176.69(11) .
C16 C15 C20 C23 176.43(11) .
N4 C15 C20 C23 -6.62(17) .
