#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:18:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180177 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/73/7107346.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_7107346
loop_
_publ_author_name
'Sharon E. Baillie'
'Victoria L. Blair'
'David C. Blakemore'
'Duncan Hay'
'Alan R. Kennedy'
'David C. Pryde'
'Eva Hevia'
_publ_section_title
;
 New lithium-zincate approaches for the selective functionalisation of
 pyrazine: direct dideprotozincation vs. nucleophilic alkylation
;
_journal_name_full               Chem.Commun.
_journal_page_first              1985
_journal_paper_doi               10.1039/c2cc16959b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C40 H70 N8 Zn3'
_chemical_formula_sum            'C40 H70 N8 Zn3'
_chemical_formula_weight         859.15
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.028(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.469(2)
_cell_length_b                   12.6321(5)
_cell_length_c                   16.5424(11)
_cell_measurement_reflns_used    4386
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.0669
_cell_measurement_theta_min      2.9382
_cell_volume                     4700.4(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, E'
_diffrn_measurement_method       'omega 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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15271
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    1.552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         6041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0403
_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)+(0.0313P)²+0.4997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                4389
_reflns_number_total             6041
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc16959b.txt
_cod_data_source_block           vb24
_cod_original_cell_volume        4700.4(5)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7107346
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 0.186457(11) 0.89879(2) 0.278635(18) 0.02130(8) Uani 1 1 d .
Zn2 Zn 0.0000 0.46526(3) 0.2500 0.02214(10) Uani 1 2 d S
N1 N 0.05817(8) 0.59680(15) 0.24946(13) 0.0238(4) Uani 1 1 d .
N2 N 0.12783(8) 0.75414(15) 0.24336(13) 0.0230(4) Uani 1 1 d .
N3 N 0.11798(8) 0.97062(16) 0.12929(13) 0.0242(4) Uani 1 1 d .
N4 N 0.03990(8) 1.07071(18) -0.05234(14) 0.0318(5) Uani 1 1 d .
C1 C 0.03500(10) 0.6860(2) 0.19849(16) 0.0278(6) Uani 1 1 d .
H1 H -0.0068 0.6958 0.1616 0.033 Uiso 1 1 calc R
C2 C 0.06911(10) 0.7648(2) 0.19693(16) 0.0274(5) Uani 1 1 d .
H2 H 0.0504 0.8284 0.1620 0.033 Uiso 1 1 calc R
C3 C 0.15140(10) 0.66351(18) 0.29173(16) 0.0235(5) Uani 1 1 d .
H3 H 0.1928 0.6517 0.3244 0.028 Uiso 1 1 calc R
C4 C 0.11693(10) 0.58582(18) 0.29558(16) 0.0243(5) Uani 1 1 d .
H4 H 0.1357 0.5230 0.3321 0.029 Uiso 1 1 calc R
C5 C 0.08442(10) 0.9164(2) 0.04490(16) 0.0268(5) Uani 1 1 d .
H5 H 0.0871 0.8413 0.0465 0.032 Uiso 1 1 calc R
C6 C 0.04613(10) 0.9664(2) -0.04420(17) 0.0294(6) Uani 1 1 d .
H6 H 0.0233 0.9244 -0.1021 0.035 Uiso 1 1 calc R
C7 C 0.07436(10) 1.1246(2) 0.03139(17) 0.0323(6) Uani 1 1 d .
H7 H 0.0722 1.1997 0.0292 0.039 Uiso 1 1 calc R
C8 C 0.11300(10) 1.07587(19) 0.12115(17) 0.0271(5) Uani 1 1 d .
H8 H 0.1367 1.1182 0.1786 0.032 Uiso 1 1 calc R
C9 C 0.25188(10) 0.86232(18) 0.26259(16) 0.0238(5) Uani 1 1 d .
C10 C 0.23255(12) 0.7907(2) 0.17445(19) 0.0402(7) Uani 1 1 d .
H10A H 0.2018 0.8264 0.1133 0.060 Uiso 1 1 calc R
H10B H 0.2167 0.7243 0.1810 0.060 Uiso 1 1 calc R
H10C H 0.2669 0.7754 0.1725 0.060 Uiso 1 1 calc R
C11 C 0.30341(11) 0.8080(2) 0.35559(19) 0.0398(7) Uani 1 1 d .
H11A H 0.2909 0.7376 0.3617 0.060 Uiso 1 1 calc R
H11B H 0.3151 0.8505 0.4137 0.060 Uiso 1 1 calc R
H11C H 0.3373 0.8012 0.3510 0.060 Uiso 1 1 calc R
C12 C 0.27535(11) 0.9655(2) 0.24896(19) 0.0350(6) Uani 1 1 d .
H12A H 0.3079 0.9499 0.2424 0.052 Uiso 1 1 calc R
H12B H 0.2900 1.0113 0.3064 0.052 Uiso 1 1 calc R
H12C H 0.2432 1.0016 0.1893 0.052 Uiso 1 1 calc R
C13 C 0.18079(12) 0.9683(2) 0.38332(18) 0.0325(6) Uani 1 1 d .
C14 C 0.23724(17) 1.0355(3) 0.4480(2) 0.0720(12) Uani 1 1 d .
H14A H 0.2375 1.0929 0.4083 0.108 Uiso 1 1 calc R
H14B H 0.2724 0.9908 0.4737 0.108 Uiso 1 1 calc R
H14C H 0.2378 1.0657 0.5031 0.108 Uiso 1 1 calc R
C15 C 0.12718(17) 1.0390(3) 0.3456(2) 0.0744(12) Uani 1 1 d .
H15A H 0.0907 0.9973 0.3047 0.112 Uiso 1 1 calc R
H15B H 0.1274 1.0964 0.3059 0.112 Uiso 1 1 calc R
H15C H 0.1288 1.0691 0.4016 0.112 Uiso 1 1 calc R
C16 C 0.18024(14) 0.8851(2) 0.44894(19) 0.0468(8) Uani 1 1 d .
H16A H 0.1816 0.9199 0.5031 0.070 Uiso 1 1 calc R
H16B H 0.2149 0.8389 0.4760 0.070 Uiso 1 1 calc R
H16C H 0.1438 0.8429 0.4101 0.070 Uiso 1 1 calc R
C17 C 0.04159(11) 0.4077(2) 0.38798(19) 0.0379(7) Uani 1 1 d .
C18 C -0.00421(13) 0.3457(3) 0.3943(2) 0.0544(9) Uani 1 1 d .
H18A H 0.0153 0.3149 0.4603 0.082 Uiso 1 1 calc R
H18B H -0.0212 0.2890 0.3449 0.082 Uiso 1 1 calc R
H18C H -0.0359 0.3936 0.3817 0.082 Uiso 1 1 calc R
C19 C 0.09003(13) 0.3297(3) 0.4080(3) 0.0698(11) Uani 1 1 d .
H19A H 0.1199 0.3670 0.4041 0.105 Uiso 1 1 calc R
H19B H 0.0722 0.2730 0.3587 0.105 Uiso 1 1 calc R
H19C H 0.1090 0.2993 0.4741 0.105 Uiso 1 1 calc R
C20 C 0.06907(15) 0.4912(3) 0.46821(19) 0.0713(12) Uani 1 1 d .
H20A H 0.0894 0.4569 0.5329 0.107 Uiso 1 1 calc R
H20B H 0.0378 0.5379 0.4592 0.107 Uiso 1 1 calc R
H20C H 0.0978 0.5330 0.4644 0.107 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
Zn Zn 0.2839 1.4301 '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'
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'
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
C9 Zn1 C13 136.36(10) . .
C9 Zn1 N3 101.13(8) . .
C13 Zn1 N3 109.60(9) . .
C9 Zn1 N2 109.61(8) . .
C13 Zn1 N2 100.18(9) . .
N3 Zn1 N2 91.12(7) . .
C17 Zn2 C17 137.65(17) . 2
C17 Zn2 N1 108.71(9) . .
C17 Zn2 N1 101.49(9) 2 .
C17 Zn2 N1 101.49(9) . 2
C17 Zn2 N1 108.71(9) 2 2
N1 Zn2 N1 87.94(10) . 2
C1 N1 C4 115.50(19) . .
C1 N1 Zn2 122.13(15) . .
C4 N1 Zn2 122.27(15) . .
C3 N2 C2 116.2(2) . .
C3 N2 Zn1 120.45(15) . .
C2 N2 Zn1 120.54(15) . .
C8 N3 C5 115.81(19) . .
C8 N3 Zn1 118.80(15) . .
C5 N3 Zn1 125.18(16) . .
C6 N4 C7 115.4(2) . .
N1 C1 C2 122.8(2) . .
N1 C1 H1 118.6 . .
C2 C1 H1 118.6 . .
N2 C2 C1 121.7(2) . .
N2 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
N2 C3 C4 121.7(2) . .
N2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
N1 C4 C3 122.1(2) . .
N1 C4 H4 119.0 . .
C3 C4 H4 119.0 . .
N3 C5 C6 121.8(2) . .
N3 C5 H5 119.1 . .
C6 C5 H5 119.1 . .
N4 C6 C5 122.6(2) . .
N4 C6 H6 118.7 . .
C5 C6 H6 118.7 . .
N4 C7 C8 122.7(2) . .
N4 C7 H7 118.7 . .
C8 C7 H7 118.7 . .
N3 C8 C7 121.6(2) . .
N3 C8 H8 119.2 . .
C7 C8 H8 119.2 . .
C12 C9 C10 108.02(19) . .
C12 C9 C11 107.8(2) . .
C10 C9 C11 107.9(2) . .
C12 C9 Zn1 107.95(16) . .
C10 C9 Zn1 114.40(16) . .
C11 C9 Zn1 110.51(16) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C15 C13 C16 107.2(2) . .
C15 C13 C14 108.3(3) . .
C16 C13 C14 107.7(2) . .
C15 C13 Zn1 115.85(18) . .
C16 C13 Zn1 110.40(18) . .
C14 C13 Zn1 107.00(18) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C20 C17 C19 108.9(3) . .
C20 C17 C18 108.1(2) . .
C19 C17 C18 107.5(2) . .
C20 C17 Zn2 114.5(2) . .
C19 C17 Zn2 109.6(2) . .
C18 C17 Zn2 107.91(17) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C17 C20 H20A 109.5 . .
C17 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C17 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 C9 2.015(2) .
Zn1 C13 2.026(2) .
Zn1 N3 2.2650(18) .
Zn1 N2 2.2791(19) .
Zn2 C17 2.013(2) .
Zn2 C17 2.013(2) 2
Zn2 N1 2.3087(19) .
Zn2 N1 2.3087(19) 2
N1 C1 1.330(3) .
N1 C4 1.339(3) .
N2 C3 1.332(3) .
N2 C2 1.337(3) .
N3 C8 1.335(3) .
N3 C5 1.338(3) .
N4 C6 1.326(3) .
N4 C7 1.332(3) .
C1 C2 1.378(3) .
C1 H1 0.9500 .
C2 H2 0.9500 .
C3 C4 1.390(3) .
C3 H3 0.9500 .
C4 H4 0.9500 .
C5 C6 1.378(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.379(3) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C12 1.528(3) .
C9 C10 1.529(3) .
C9 C11 1.530(3) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C15 1.517(4) .
C13 C16 1.517(3) .
C13 C14 1.538(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C20 1.515(4) .
C17 C19 1.531(4) .
C17 C18 1.535(4) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 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
C17 Zn2 N1 C1 -139.27(19) .
C17 Zn2 N1 C1 70.84(19) 2
N1 Zn2 N1 C1 -37.84(15) 2
C17 Zn2 N1 C4 44.75(19) .
C17 Zn2 N1 C4 -105.13(18) 2
N1 Zn2 N1 C4 146.19(19) 2
C9 Zn1 N2 C3 56.34(18) .
C13 Zn1 N2 C3 -91.28(18) .
N3 Zn1 N2 C3 158.58(17) .
C9 Zn1 N2 C2 -143.24(16) .
C13 Zn1 N2 C2 69.15(18) .
N3 Zn1 N2 C2 -41.00(16) .
C9 Zn1 N3 C8 -101.33(18) .
C13 Zn1 N3 C8 47.22(19) .
N2 Zn1 N3 C8 148.44(18) .
C9 Zn1 N3 C5 73.09(19) .
C13 Zn1 N3 C5 -138.37(19) .
N2 Zn1 N3 C5 -37.15(18) .
C4 N1 C1 C2 -3.3(3) .
Zn2 N1 C1 C2 -179.53(17) .
C3 N2 C2 C1 -0.5(3) .
Zn1 N2 C2 C1 -161.75(18) .
N1 C1 C2 N2 3.2(4) .
C2 N2 C3 C4 -1.6(3) .
Zn1 N2 C3 C4 159.65(17) .
C1 N1 C4 C3 1.1(3) .
Zn2 N1 C4 C3 177.35(16) .
N2 C3 C4 N1 1.3(4) .
C8 N3 C5 C6 -1.5(3) .
Zn1 N3 C5 C6 -176.11(17) .
C7 N4 C6 C5 1.6(4) .
N3 C5 C6 N4 -0.1(4) .
C6 N4 C7 C8 -1.5(4) .
C5 N3 C8 C7 1.7(3) .
Zn1 N3 C8 C7 176.60(18) .
N4 C7 C8 N3 -0.2(4) .
C13 Zn1 C9 C12 -70.3(2) .
N3 Zn1 C9 C12 64.24(16) .
N2 Zn1 C9 C12 159.47(14) .
C13 Zn1 C9 C10 169.39(17) .
N3 Zn1 C9 C10 -56.04(18) .
N2 Zn1 C9 C10 39.20(19) .
C13 Zn1 C9 C11 47.3(2) .
N3 Zn1 C9 C11 -178.09(16) .
N2 Zn1 C9 C11 -82.85(17) .
C9 Zn1 C13 C15 142.6(2) .
N3 Zn1 C13 C15 10.5(3) .
N2 Zn1 C13 C15 -84.4(2) .
C9 Zn1 C13 C16 -95.3(2) .
N3 Zn1 C13 C16 132.61(18) .
N2 Zn1 C13 C16 37.7(2) .
C9 Zn1 C13 C14 21.7(3) .
N3 Zn1 C13 C14 -110.4(2) .
N2 Zn1 C13 C14 154.7(2) .
C17 Zn2 C17 C20 176.2(2) 2
N1 Zn2 C17 C20 43.1(2) .
N1 Zn2 C17 C20 -48.6(2) 2
C17 Zn2 C17 C19 53.53(19) 2
N1 Zn2 C17 C19 -79.6(2) .
N1 Zn2 C17 C19 -171.3(2) 2
C17 Zn2 C17 C18 -63.28(19) 2
N1 Zn2 C17 C18 163.59(19) .
N1 Zn2 C17 C18 71.9(2) 2
