#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229321.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229321
loop_
_publ_author_name
'Issa-Madongo, Mathurin'
'Mu, Ying'
_publ_section_title
;
 [N-((E)-2-{[2-(Dimethylamino)ethyl]iminomethyl}phenyl)-N-(2,6-dimethylphenyl)anilinido-κ³N,N',N'']ethylzinc
;
_journal_coeditor_code           BH2336
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m364
_journal_paper_doi               10.1107/S1600536811005514
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Zn (C2 H5) (C19 H24 N3)]'
_chemical_formula_moiety         'C21 H29 N3 Zn'
_chemical_formula_sum            'C21 H29 N3 Zn'
_chemical_formula_weight         388.84
_chemical_name_systematic
;
[N-((E)-2-{[2-(Dimethylamino)ethyl]iminomethyl}phenyl)-
N-(2,6-dimethylphenyl)anilinido-
κ³N,N',N'']ethylzinc
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 99.26(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3664(15)
_cell_length_b                   13.849(3)
_cell_length_c                   20.296(4)
_cell_measurement_reflns_used    10491
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.92
_cell_measurement_theta_min      6.23
_cell_volume                     2043.6(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.1155
_diffrn_reflns_av_sigmaI/netI    0.1049
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18874
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_max  0.8028
_exptl_absorpt_correction_T_min  0.7684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.626
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                2619
_reflns_number_total             4571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2336.cif
_cod_data_source_block           I
_cod_original_cell_volume        2043.5(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229321
_cod_database_fobs_code          2229321
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7787(7) 0.8763(3) 0.8847(2) 0.0497(10) Uani d . 1 . .
C C2 0.7141(7) 0.8858(3) 0.8154(2) 0.0558(11) Uani d . 1 . .
H H2 0.7400 0.8373 0.7866 0.067 Uiso calc R 1 . .
C C3 0.6141(8) 0.9649(4) 0.7893(3) 0.0672(14) Uani d . 1 . .
H H3 0.5740 0.9683 0.7435 0.081 Uiso calc R 1 . .
C C4 0.5719(8) 1.0393(4) 0.8297(3) 0.0671(14) Uani d . 1 . .
H H4 0.5068 1.0931 0.8115 0.080 Uiso calc R 1 . .
C C5 0.6275(7) 1.0321(3) 0.8964(3) 0.0580(12) Uani d . 1 . .
H H5 0.5944 1.0808 0.9237 0.070 Uiso calc R 1 . .
C C6 0.7337(6) 0.9537(3) 0.9266(2) 0.0483(10) Uani d . 1 . .
C C7 0.7748(7) 0.9542(3) 0.9974(2) 0.0512(11) Uani d . 1 . .
H H7 0.7175 1.0017 1.0190 0.061 Uiso calc R 1 . .
C C8 0.8819(8) 0.8962(3) 1.1069(2) 0.0581(12) Uani d . 1 . .
H H8A 0.8122 0.9508 1.1194 0.070 Uiso calc R 1 . .
H H8B 1.0066 0.9005 1.1310 0.070 Uiso calc R 1 . .
C C9 0.7926(8) 0.8012(3) 1.1237(2) 0.0594(12) Uani d . 1 . .
H H9A 0.7967 0.7965 1.1716 0.071 Uiso calc R 1 . .
H H9B 0.6646 0.8003 1.1027 0.071 Uiso calc R 1 . .
C C10 0.7658(10) 0.6345(4) 1.0890(3) 0.090(2) Uani d . 1 . .
H H10A 0.8310 0.5805 1.0745 0.135 Uiso calc R 1 . .
H H10B 0.6627 0.6499 1.0554 0.135 Uiso calc R 1 . .
H H10C 0.7229 0.6183 1.1299 0.135 Uiso calc R 1 . .
C C11 1.0496(9) 0.6923(4) 1.1502(3) 0.0737(16) Uani d . 1 . .
H H11A 1.0089 0.6737 1.1910 0.111 Uiso calc R 1 . .
H H11B 1.1306 0.7468 1.1584 0.111 Uiso calc R 1 . .
H H11C 1.1138 0.6393 1.1339 0.111 Uiso calc R 1 . .
C C12 0.9206(7) 0.7257(3) 0.8645(2) 0.0505(10) Uani d . 1 . .
C C13 0.8071(8) 0.6443(3) 0.8554(2) 0.0580(12) Uani d . 1 . .
C C14 0.8532(8) 0.5707(3) 0.8151(2) 0.0662(14) Uani d . 1 . .
H H14 0.7762 0.5174 0.8068 0.079 Uiso calc R 1 . .
C C15 1.0110(9) 0.5750(3) 0.7871(3) 0.0701(16) Uani d . 1 . .
H H15 1.0435 0.5233 0.7621 0.084 Uiso calc R 1 . .
C C16 1.1190(9) 0.6548(4) 0.7958(2) 0.0667(14) Uani d . 1 . .
H H16 1.2234 0.6577 0.7755 0.080 Uiso calc R 1 . .
C C17 1.0774(8) 0.7330(3) 0.8347(2) 0.0579(12) Uani d . 1 . .
C C18 1.1964(9) 0.8214(4) 0.8426(3) 0.0718(15) Uani d . 1 . .
H H18A 1.1236 0.8770 0.8275 0.108 Uiso calc R 1 . .
H H18B 1.2934 0.8144 0.8165 0.108 Uiso calc R 1 . .
H H18C 1.2486 0.8294 0.8887 0.108 Uiso calc R 1 . .
C C19 0.6367(9) 0.6368(4) 0.8876(3) 0.0818(17) Uani d . 1 . .
H H19A 0.5704 0.5792 0.8724 0.123 Uiso calc R 1 . .
H H19B 0.5598 0.6921 0.8758 0.123 Uiso calc R 1 . .
H H19C 0.6714 0.6342 0.9353 0.123 Uiso calc R 1 . .
C C20 1.2613(7) 0.7185(3) 1.0170(3) 0.0611(12) Uani d . 1 . .
H H20A 1.3406 0.7502 0.9898 0.073 Uiso calc R 1 . .
H H20B 1.3175 0.7252 1.0634 0.073 Uiso calc R 1 . .
C C21 1.2474(9) 0.6109(3) 0.9989(3) 0.0777(16) Uani d . 1 . .
H H21A 1.1714 0.5788 1.0263 0.117 Uiso calc R 1 . .
H H21B 1.3680 0.5827 1.0062 0.117 Uiso calc R 1 . .
H H21C 1.1941 0.6038 0.9528 0.117 Uiso calc R 1 . .
N N1 0.8827(6) 0.8962(2) 1.03518(17) 0.0499(9) Uani d . 1 . .
N N2 0.8894(6) 0.7183(2) 1.10019(19) 0.0564(10) Uani d . 1 . .
N N3 0.8810(6) 0.8002(2) 0.91016(18) 0.0520(9) Uani d . 1 . .
Zn Zn1 1.01743(8) 0.78379(3) 1.00320(2) 0.0531(2) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 C1 C2 . . 122.1(4) ?
N3 C1 C6 . . 121.5(4) ?
C2 C1 C6 . . 116.4(4) ?
C3 C2 C1 . . 122.0(4) ?
C3 C2 H2 . . 119.0 ?
C1 C2 H2 . . 119.0 ?
C2 C3 C4 . . 121.5(5) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 118.5(4) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
C4 C5 C6 . . 123.1(4) ?
C4 C5 H5 . . 118.5 ?
C6 C5 H5 . . 118.5 ?
C5 C6 C7 . . 116.6(4) ?
C5 C6 C1 . . 118.6(4) ?
C7 C6 C1 . . 124.7(4) ?
N1 C7 C6 . . 127.6(4) ?
N1 C7 H7 . . 116.2 ?
C6 C7 H7 . . 116.2 ?
N1 C8 C9 . . 107.1(4) ?
N1 C8 H8A . . 110.3 ?
C9 C8 H8A . . 110.3 ?
N1 C8 H8B . . 110.3 ?
C9 C8 H8B . . 110.3 ?
H8A C8 H8B . . 108.6 ?
N2 C9 C8 . . 110.5(4) ?
N2 C9 H9A . . 109.6 ?
C8 C9 H9A . . 109.6 ?
N2 C9 H9B . . 109.6 ?
C8 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
N2 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 121.4(4) ?
C17 C12 N3 . . 119.6(4) ?
C13 C12 N3 . . 118.8(4) ?
C14 C13 C12 . . 118.3(5) ?
C14 C13 C19 . . 120.3(5) ?
C12 C13 C19 . . 121.3(4) ?
C15 C14 C13 . . 121.1(5) ?
C15 C14 H14 . . 119.4 ?
C13 C14 H14 . . 119.4 ?
C16 C15 C14 . . 119.9(4) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 121.7(5) ?
C15 C16 H16 . . 119.1 ?
C17 C16 H16 . . 119.1 ?
C12 C17 C16 . . 117.4(5) ?
C12 C17 C18 . . 121.7(4) ?
C16 C17 C18 . . 120.9(5) ?
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 ?
C13 C19 H19A . . 109.5 ?
C13 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C13 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C21 C20 Zn1 . . 112.5(4) ?
C21 C20 H20A . . 109.1 ?
Zn1 C20 H20A . . 109.1 ?
C21 C20 H20B . . 109.1 ?
Zn1 C20 H20B . . 109.1 ?
H20A C20 H20B . . 107.8 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C7 N1 C8 . . 119.6(4) ?
C7 N1 Zn1 . . 125.3(3) ?
C8 N1 Zn1 . . 113.8(3) ?
C10 N2 C9 . . 110.2(4) ?
C10 N2 C11 . . 108.7(4) ?
C9 N2 C11 . . 110.1(4) ?
C10 N2 Zn1 . . 118.1(3) ?
C9 N2 Zn1 . . 103.7(2) ?
C11 N2 Zn1 . . 105.7(3) ?
C1 N3 C12 . . 118.0(4) ?
C1 N3 Zn1 . . 127.9(3) ?
C12 N3 Zn1 . . 113.6(3) ?
C20 Zn1 N3 . . 119.23(18) ?
C20 Zn1 N1 . . 142.01(18) ?
N3 Zn1 N1 . . 91.01(14) ?
C20 Zn1 N2 . . 99.88(18) ?
N3 Zn1 N2 . . 126.21(16) ?
N1 Zn1 N2 . . 75.94(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N3 . 1.349(5) ?
C1 C2 . 1.417(6) ?
C1 C6 . 1.441(6) ?
C2 C3 . 1.376(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.353(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.418(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.419(6) ?
C7 N1 . 1.292(6) ?
C7 H7 . 0.9300 ?
C8 N1 . 1.457(5) ?
C8 C9 . 1.533(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N2 . 1.471(6) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N2 . 1.470(7) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 N2 . 1.472(7) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C17 . 1.391(7) ?
C12 C13 . 1.398(7) ?
C12 N3 . 1.447(5) ?
C13 C14 . 1.383(6) ?
C13 C19 . 1.510(8) ?
C14 C15 . 1.375(8) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.356(8) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.404(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.499(7) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 C21 . 1.534(6) ?
Zn1 C20 . 1.991(5) yes
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
Zn1 N1 . 2.009(3) yes
Zn1 N2 . 2.487(4) yes
Zn1 N3 . 2.004(4) yes
