#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/69/1516990.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_1516990
loop_
_publ_author_name
'Markus Graser'
'Holger Kopacka'
'Klaus Wurst'
'Thomas Muller'
'Benno Bildstein'
_publ_section_title
;
 Structurally diverse pyridyl or quinolyl enolato/enamido metal complexes
 of Li, Zr, Fe, Co, Ni, Cu and Zn
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              38
_journal_page_last               49
_journal_volume                  401
_journal_year                    2013
_chemical_formula_sum            'C20 H26 N2'
_chemical_formula_weight         294.43
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.795(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   24.1856(4)
_cell_length_b                   11.2518(4)
_cell_length_c                   26.7160(9)
_cell_measurement_reflns_used    54598
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      24.0
_cell_measurement_theta_min      1.0
_cell_volume                     7254.3(4)
_computing_data_collection       COLLECT
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and 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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14815
_diffrn_reflns_theta_full        23.00
_diffrn_reflns_theta_max         23.00
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5008
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0571
_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)+(0.0664P)²+3.6972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                3603
_reflns_number_total             5008
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-401-38-49-12.CIF
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1516990
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
N1 N 0.03126(7) 0.48936(18) 0.13568(7) 0.0593(5) Uani 1 1 d D
H1N H 0.0349(9) 0.4774(19) 0.1684(6) 0.060(7) Uiso 1 1 d D
N2 N 0.09436(8) 0.48431(15) 0.22350(7) 0.0565(5) Uani 1 1 d .
N3 N 0.19490(8) 0.89378(17) 0.12084(7) 0.0599(5) Uani 1 1 d D
H3N H 0.2227(8) 0.855(2) 0.1380(9) 0.080(8) Uiso 1 1 d D
N4 N 0.26858(8) 0.71400(17) 0.12620(8) 0.0671(6) Uani 1 1 d .
C1 C 0.07999(9) 0.50735(19) 0.11428(8) 0.0541(6) Uani 1 1 d .
C2 C 0.07804(11) 0.5148(3) 0.05826(9) 0.0763(7) Uani 1 1 d .
H2A H 0.0637 0.4410 0.0439 0.114 Uiso 1 1 calc R
H2B H 0.1151 0.5285 0.0476 0.114 Uiso 1 1 calc R
H2C H 0.0541 0.5800 0.0469 0.114 Uiso 1 1 calc R
C3 C 0.12894(9) 0.5158(2) 0.14213(9) 0.0562(6) Uani 1 1 d .
H3 H 0.1603 0.5337 0.1246 0.067 Uiso 1 1 calc .
C4 C 0.13800(9) 0.50035(18) 0.19531(8) 0.0532(6) Uani 1 1 d .
C5 C 0.19207(10) 0.4994(2) 0.21808(11) 0.0749(7) Uani 1 1 d .
H5 H 0.2226 0.5117 0.1987 0.090 Uiso 1 1 calc .
C6 C 0.20011(14) 0.4804(3) 0.26879(13) 0.0934(9) Uani 1 1 d .
H6 H 0.2362 0.4791 0.2842 0.112 Uiso 1 1 calc .
C7 C 0.15554(16) 0.4635(3) 0.29668(11) 0.0867(9) Uani 1 1 d .
H7 H 0.1602 0.4497 0.3314 0.104 Uiso 1 1 calc .
C8 C 0.10434(12) 0.4671(2) 0.27293(10) 0.0717(7) Uani 1 1 d .
H8 H 0.0737 0.4568 0.2924 0.086 Uiso 1 1 calc .
C9 C -0.02110(9) 0.4637(2) 0.10956(8) 0.0559(6) Uani 1 1 d .
C10 C -0.03864(10) 0.3455(2) 0.10555(9) 0.0635(6) Uani 1 1 d .
C11 C -0.09116(11) 0.3240(2) 0.08277(10) 0.0725(7) Uani 1 1 d .
H11 H -0.1040 0.2453 0.0796 0.087 Uiso 1 1 calc .
C12 C -0.12426(11) 0.4146(3) 0.06495(9) 0.0735(7) Uani 1 1 d .
H12 H -0.1597 0.3979 0.0500 0.088 Uiso 1 1 calc .
C13 C -0.10627(10) 0.5302(2) 0.06864(9) 0.0689(7) Uani 1 1 d .
H13 H -0.1293 0.5916 0.0556 0.083 Uiso 1 1 calc .
C14 C -0.05441(10) 0.5576(2) 0.09138(8) 0.0598(6) Uani 1 1 d .
C15 C 0.17558(9) 0.8432(2) 0.07734(9) 0.0604(6) Uani 1 1 d .
C16 C 0.12413(12) 0.8945(3) 0.05147(11) 0.0886(9) Uani 1 1 d .
H16A H 0.0934 0.8848 0.0726 0.133 Uiso 1 1 calc R
H16B H 0.1159 0.8534 0.0199 0.133 Uiso 1 1 calc R
H16C H 0.1298 0.9783 0.0451 0.133 Uiso 1 1 calc R
C17 C 0.20144(11) 0.7478(2) 0.05790(9) 0.0664(7) Uani 1 1 d .
H17 H 0.1879 0.7225 0.0259 0.080 Uiso 1 1 calc .
C18 C 0.24686(11) 0.6818(2) 0.08072(10) 0.0633(7) Uani 1 1 d .
C19 C 0.26795(14) 0.5813(2) 0.05647(12) 0.0892(9) Uani 1 1 d .
H19 H 0.2537 0.5600 0.0241 0.107 Uiso 1 1 calc .
C20 C 0.30928(16) 0.5155(3) 0.08045(17) 0.1013(11) Uani 1 1 d .
H20 H 0.3233 0.4482 0.0647 0.122 Uiso 1 1 calc .
C21 C 0.33018(13) 0.5472(3) 0.12716(16) 0.0958(10) Uani 1 1 d .
H21 H 0.3582 0.5022 0.1442 0.115 Uiso 1 1 calc .
C22 C 0.30917(11) 0.6467(3) 0.14848(11) 0.0845(8) Uani 1 1 d .
H22 H 0.3239 0.6694 0.1805 0.101 Uiso 1 1 calc .
C23 C 0.16973(8) 0.98859(19) 0.14712(8) 0.0526(6) Uani 1 1 d .
C24 C 0.14018(9) 0.96065(19) 0.18880(8) 0.0557(6) Uani 1 1 d .
C25 C 0.12012(11) 1.0542(2) 0.21637(9) 0.0669(7) Uani 1 1 d .
H25 H 0.1002 1.0375 0.2446 0.080 Uiso 1 1 calc .
C26 C 0.12874(11) 1.1706(2) 0.20322(10) 0.0738(7) Uani 1 1 d .
H26 H 0.1152 1.2325 0.2226 0.089 Uiso 1 1 calc .
C27 C 0.15704(11) 1.1962(2) 0.16178(10) 0.0691(7) Uani 1 1 d .
H27 H 0.1619 1.2760 0.1526 0.083 Uiso 1 1 calc .
C28 C 0.17868(9) 1.1069(2) 0.13296(9) 0.0590(6) Uani 1 1 d .
C101 C -0.00266(11) 0.2441(2) 0.12647(11) 0.0783(8) Uani 1 1 d .
H101 H 0.0355 0.2749 0.1326 0.094 Uiso 1 1 calc .
C102 C -0.02165(15) 0.2018(3) 0.17565(13) 0.1143(12) Uani 1 1 d .
H10A H 0.0023 0.1381 0.1885 0.171 Uiso 1 1 calc .
H10B H -0.0594 0.1729 0.1709 0.171 Uiso 1 1 calc .
H10C H -0.0201 0.2671 0.1994 0.171 Uiso 1 1 calc .
C103 C -0.0004(2) 0.1394(3) 0.09025(16) 0.1439(16) Uani 1 1 d .
H10D H 0.0118 0.1671 0.0584 0.216 Uiso 1 1 calc .
H10E H -0.0370 0.1043 0.0851 0.216 Uiso 1 1 calc .
H10F H 0.0254 0.0803 0.1042 0.216 Uiso 1 1 calc .
C141 C -0.03660(10) 0.6871(2) 0.09771(10) 0.0702(7) Uani 1 1 d .
H141 H 0.0034 0.6873 0.1081 0.084 Uiso 1 1 calc .
C142 C -0.06670(13) 0.7446(3) 0.13965(13) 0.1017(10) Uani 1 1 d .
H14A H -0.0611 0.6973 0.1699 0.153 Uiso 1 1 calc .
H14B H -0.1060 0.7493 0.1299 0.153 Uiso 1 1 calc .
H14C H -0.0522 0.8240 0.1459 0.153 Uiso 1 1 calc .
C143 C -0.04416(18) 0.7581(3) 0.04936(14) 0.1263(14) Uani 1 1 d .
H14D H -0.0309 0.8386 0.0553 0.190 Uiso 1 1 calc .
H14E H -0.0831 0.7601 0.0382 0.190 Uiso 1 1 calc .
H14F H -0.0233 0.7211 0.0238 0.190 Uiso 1 1 calc .
C241 C 0.12952(10) 0.8338(2) 0.20436(9) 0.0661(7) Uani 1 1 d .
H241 H 0.1430 0.7809 0.1782 0.079 Uiso 1 1 calc .
C242 C 0.16128(15) 0.8037(3) 0.25320(13) 0.1005(10) Uani 1 1 d .
H24A H 0.1540 0.7219 0.2620 0.151 Uiso 1 1 calc .
H24B H 0.1496 0.8559 0.2794 0.151 Uiso 1 1 calc .
H24C H 0.2006 0.8141 0.2496 0.151 Uiso 1 1 calc .
C243 C 0.06860(13) 0.8096(3) 0.20769(17) 0.1193(13) Uani 1 1 d .
H24D H 0.0634 0.7278 0.2179 0.179 Uiso 1 1 calc .
H24E H 0.0493 0.8227 0.1752 0.179 Uiso 1 1 calc .
H24F H 0.0538 0.8626 0.2321 0.179 Uiso 1 1 calc .
C281 C 0.21202(11) 1.1409(2) 0.08911(10) 0.0755(7) Uani 1 1 d .
H281 H 0.2208 1.0675 0.0708 0.091 Uiso 1 1 calc .
C282 C 0.26660(12) 1.1992(3) 0.10819(14) 0.1080(11) Uani 1 1 d .
H28A H 0.2882 1.2185 0.0799 0.162 Uiso 1 1 calc .
H28B H 0.2874 1.1448 0.1304 0.162 Uiso 1 1 calc .
H28C H 0.2588 1.2714 0.1263 0.162 Uiso 1 1 calc .
C283 C 0.18044(14) 1.2242(3) 0.05257(12) 0.1075(11) Uani 1 1 d .
H28D H 0.2035 1.2442 0.0254 0.161 Uiso 1 1 calc .
H28E H 0.1708 1.2962 0.0700 0.161 Uiso 1 1 calc .
H28F H 0.1469 1.1854 0.0390 0.161 Uiso 1 1 calc .
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
H1N N1 C1 114.0(14)
H1N N1 C9 118.5(14)
C1 N1 C9 126.01(19)
C8 N2 C4 118.2(2)
H3N N3 C15 116.2(16)
H3N N3 C23 115.7(16)
C15 N3 C23 126.9(2)
C18 N4 C22 118.6(2)
N1 C1 C3 121.9(2)
N1 C1 C2 117.3(2)
C3 C1 C2 120.8(2)
C1 C3 C4 127.20(19)
N2 C4 C5 119.8(2)
N2 C4 C3 119.7(2)
C5 C4 C3 120.5(2)
C6 C5 C4 119.7(3)
C7 C6 C5 119.7(3)
C8 C7 C6 118.1(3)
N2 C8 C7 124.4(3)
C14 C9 C10 121.9(2)
C14 C9 N1 119.2(2)
C10 C9 N1 118.8(2)
C11 C10 C9 117.5(2)
C11 C10 C101 120.9(2)
C9 C10 C101 121.5(2)
C12 C11 C10 121.4(2)
C11 C12 C13 120.5(2)
C12 C13 C14 120.9(2)
C13 C14 C9 117.8(2)
C13 C14 C141 120.0(2)
C9 C14 C141 122.1(2)
N3 C15 C17 121.3(2)
N3 C15 C16 117.7(2)
C17 C15 C16 121.0(2)
C15 C17 C18 127.3(2)
N4 C18 C19 120.0(3)
N4 C18 C17 119.3(2)
C19 C18 C17 120.7(3)
C20 C19 C18 119.5(3)
C21 C20 C19 120.1(3)
C20 C21 C22 118.0(3)
N4 C22 C21 123.7(3)
C24 C23 C28 121.57(19)
C24 C23 N3 118.58(19)
C28 C23 N3 119.67(19)
C25 C24 C23 117.8(2)
C25 C24 C241 119.8(2)
C23 C24 C241 122.41(19)
C26 C25 C24 121.4(2)
C27 C26 C25 119.9(2)
C26 C27 C28 121.5(2)
C27 C28 C23 117.8(2)
C27 C28 C281 119.0(2)
C23 C28 C281 123.2(2)
C102 C101 C10 111.1(2)
C102 C101 C103 109.7(3)
C10 C101 C103 112.9(3)
C143 C141 C142 111.4(3)
C143 C141 C14 113.0(2)
C142 C141 C14 110.1(2)
C243 C241 C242 110.6(3)
C243 C241 C24 111.8(2)
C242 C241 C24 111.3(2)
C28 C281 C283 112.4(2)
C28 C281 C282 110.0(2)
C283 C281 C282 109.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 H1N 0.883(16)
N1 C1 1.359(3)
N1 C9 1.434(3)
N2 C8 1.341(3)
N2 C4 1.349(3)
N3 H3N 0.899(16)
N3 C15 1.349(3)
N3 C23 1.435(3)
N4 C18 1.341(3)
N4 C22 1.347(3)
C1 C3 1.359(3)
C1 C2 1.497(3)
C3 C4 1.434(3)
C4 C5 1.405(3)
C5 C6 1.373(4)
C6 C7 1.364(4)
C7 C8 1.354(4)
C9 C14 1.397(3)
C9 C10 1.398(3)
C10 C11 1.393(3)
C10 C101 1.519(4)
C11 C12 1.363(4)
C12 C13 1.373(4)
C13 C14 1.392(3)
C14 C141 1.525(3)
C15 C17 1.363(3)
C15 C16 1.498(3)
C17 C18 1.429(4)
C18 C19 1.415(3)
C19 C20 1.369(5)
C20 C21 1.363(5)
C21 C22 1.369(4)
C23 C24 1.398(3)
C23 C28 1.404(3)
C24 C25 1.390(3)
C24 C241 1.514(3)
C25 C26 1.375(3)
C26 C27 1.370(3)
C27 C28 1.389(3)
C28 C281 1.515(3)
C101 C102 1.498(4)
C101 C103 1.528(5)
C141 C143 1.520(4)
C141 C142 1.521(4)
C241 C243 1.507(4)
C241 C242 1.508(4)
C281 C283 1.522(4)
C281 C282 1.531(4)
