#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/91/2219175.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_2219175
loop_
_publ_author_name
'Zhu, Xue-Wen'
'Yang, Xu-Zhao'
_publ_section_title
;Bis{(E)-2-ethoxy-6-[2-(ethylammonio)ethyliminomethyl]phenolato}nickel(II)
 bis(perchlorate)
;
_journal_coeditor_code           SJ2526
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1096
_journal_page_last               m1097
_journal_paper_doi               10.1107/S1600536808023684
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Ni (C13 H20 N2 O2)2] (Cl O4)2'
_chemical_formula_moiety         'C26 H40 N4 Ni O4 2+, 2(Cl O4 -)'
_chemical_formula_sum            'C26 H40 Cl2 N4 Ni O12'
_chemical_formula_weight         730.23
_chemical_name_systematic
;Bis{(E)-2-Ethoxy-6-[2-(ethylammonio)ethyliminomethyl]phenolato}nickel(II)
bis(perchlorate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.068(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.386(3)
_cell_length_b                   8.566(3)
_cell_length_c                   21.862(6)
_cell_measurement_reflns_used    3252
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.5
_cell_volume                     1550.8(9)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12509
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.8458
_exptl_absorpt_correction_T_min  0.8256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.343
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.4599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2770
_reflns_number_total             3363
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2526.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2219175
_cod_database_fobs_code          2219175
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Ni Ni1 1.0000 0.5000 0.0000 0.02592(13) Uani d S 1
Cl Cl1 0.39043(7) 0.71469(7) 0.09059(3) 0.03882(17) Uani d . 1
O O1 1.06353(18) 0.41002(18) 0.07614(7) 0.0333(4) Uani d . 1
O O2 1.1550(2) 0.2125(2) 0.16406(8) 0.0451(4) Uani d . 1
O O3 0.4539(3) 0.6169(2) 0.04665(9) 0.0624(6) Uani d . 1
O O4 0.5075(2) 0.8315(2) 0.11174(9) 0.0547(5) Uani d . 1
O O5 0.3594(3) 0.6194(2) 0.14062(9) 0.0652(6) Uani d . 1
O O6 0.2480(3) 0.7874(3) 0.06108(13) 0.0790(7) Uani d . 1
N N1 0.8973(2) 0.6697(2) 0.03503(8) 0.0272(4) Uani d . 1
N N2 0.6314(2) 0.7051(2) -0.07021(9) 0.0342(4) Uani d . 1
H H2A 0.6031 0.6259 -0.0471 0.041 Uiso calc R 1
H H2B 0.7139 0.6718 -0.0886 0.041 Uiso calc R 1
C C1 0.8960(3) 0.5512(3) 0.13583(10) 0.0307(5) Uani d . 1
C C2 1.0022(3) 0.4303(3) 0.12705(9) 0.0281(5) Uani d . 1
C C3 1.0473(3) 0.3232(3) 0.17637(10) 0.0322(5) Uani d . 1
C C4 0.9828(3) 0.3361(3) 0.22998(10) 0.0385(6) Uani d . 1
H H4 1.0109 0.2640 0.2616 0.046 Uiso calc R 1
C C5 0.8759(3) 0.4560(3) 0.23756(11) 0.0436(6) Uani d . 1
H H5 0.8327 0.4634 0.2741 0.052 Uiso calc R 1
C C6 0.8344(3) 0.5623(3) 0.19183(11) 0.0399(6) Uani d . 1
H H6 0.7644 0.6433 0.1976 0.048 Uiso calc R 1
C C7 0.8602(3) 0.6692(3) 0.09004(10) 0.0308(5) Uani d . 1
H H7 0.8036 0.7555 0.1010 0.037 Uiso calc R 1
C C8 0.8632(3) 0.8182(2) 0.00079(11) 0.0317(5) Uani d . 1
H H8A 0.9308 0.8242 -0.0313 0.038 Uiso calc R 1
H H8B 0.8923 0.9044 0.0291 0.038 Uiso calc R 1
C C9 0.6887(3) 0.8363(3) -0.02871(11) 0.0333(5) Uani d . 1
H H9A 0.6219 0.8436 0.0036 0.040 Uiso calc R 1
H H9B 0.6765 0.9328 -0.0522 0.040 Uiso calc R 1
C C10 0.4917(3) 0.7422(3) -0.11922(13) 0.0487(7) Uani d . 1
H H10A 0.5245 0.8215 -0.1464 0.058 Uiso calc R 1
H H10B 0.4629 0.6493 -0.1439 0.058 Uiso calc R 1
C C11 0.3475(3) 0.7982(4) -0.09446(14) 0.0568(8) Uani d . 1
H H11A 0.3152 0.7211 -0.0670 0.085 Uiso calc R 1
H H11B 0.2610 0.8158 -0.1281 0.085 Uiso calc R 1
H H11C 0.3728 0.8940 -0.0723 0.085 Uiso calc R 1
C C12 1.1937(3) 0.0850(3) 0.20663(12) 0.0465(6) Uani d . 1
H H12A 1.2110 0.1255 0.2486 0.056 Uiso calc R 1
H H12B 1.2937 0.0372 0.1992 0.056 Uiso calc R 1
C C13 1.0661(5) -0.0355(4) 0.2011(2) 0.0790(11) Uani d . 1
H H13A 0.9690 0.0091 0.2116 0.119 Uiso calc R 1
H H13B 1.1007 -0.1201 0.2288 0.119 Uiso calc R 1
H H13C 1.0458 -0.0737 0.1593 0.119 Uiso calc R 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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
O1 Ni1 O1 3_765 . 180.0 y
O1 Ni1 N1 3_765 3_765 92.33(7) ?
O1 Ni1 N1 . 3_765 87.67(7) ?
O1 Ni1 N1 3_765 . 87.67(7) y
O1 Ni1 N1 . . 92.33(7) y
N1 Ni1 N1 3_765 . 180.0 y
O6 Cl1 O5 . . 111.19(15) ?
O6 Cl1 O4 . . 109.16(13) ?
O5 Cl1 O4 . . 110.69(13) ?
O6 Cl1 O3 . . 109.13(15) ?
O5 Cl1 O3 . . 108.15(12) ?
O4 Cl1 O3 . . 108.46(13) ?
C2 O1 Ni1 . . 128.20(14) ?
C3 O2 C12 . . 119.27(19) ?
C7 N1 C8 . . 114.76(18) ?
C7 N1 Ni1 . . 124.19(15) ?
C8 N1 Ni1 . . 120.95(14) ?
C9 N2 C10 . . 114.96(19) ?
C9 N2 H2A . . 108.5 ?
C10 N2 H2A . . 108.5 ?
C9 N2 H2B . . 108.5 ?
C10 N2 H2B . . 108.5 ?
H2A N2 H2B . . 107.5 ?
C2 C1 C6 . . 119.9(2) ?
C2 C1 C7 . . 119.90(19) ?
C6 C1 C7 . . 120.0(2) ?
O1 C2 C1 . . 123.96(19) ?
O1 C2 C3 . . 117.8(2) ?
C1 C2 C3 . . 118.25(19) ?
O2 C3 C4 . . 126.0(2) ?
O2 C3 C2 . . 113.84(19) ?
C4 C3 C2 . . 120.2(2) ?
C3 C4 C5 . . 120.7(2) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 120.7(2) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
N1 C7 C1 . . 127.2(2) ?
N1 C7 H7 . . 116.4 ?
C1 C7 H7 . . 116.4 ?
N1 C8 C9 . . 113.63(18) ?
N1 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
N1 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
N2 C9 C8 . . 112.54(18) ?
N2 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
N2 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
C11 C10 N2 . . 113.6(2) ?
C11 C10 H10A . . 108.8 ?
N2 C10 H10A . . 108.8 ?
C11 C10 H10B . . 108.8 ?
N2 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O2 C12 C13 . . 113.0(2) ?
O2 C12 H12A . . 109.0 ?
C13 C12 H12A . . 109.0 ?
O2 C12 H12B . . 109.0 ?
C13 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
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
Ni1 O1 3_765 1.836(2) ?
Ni1 O1 . 1.836(2) y
Ni1 N1 3_765 1.910(2) ?
Ni1 N1 . 1.910(2) y
Cl1 O6 . 1.410(2) ?
Cl1 O5 . 1.421(2) ?
Cl1 O4 . 1.4268(18) ?
Cl1 O3 . 1.4384(19) ?
O1 C2 . 1.309(2) ?
O2 C3 . 1.365(3) ?
O2 C12 . 1.439(3) ?
N1 C7 . 1.289(3) ?
N1 C8 . 1.481(3) ?
N2 C9 . 1.476(3) ?
N2 C10 . 1.492(3) ?
N2 H2A . 0.9000 ?
N2 H2B . 0.9000 ?
C1 C2 . 1.399(3) ?
C1 C6 . 1.405(3) ?
C1 C7 . 1.421(3) ?
C2 C3 . 1.421(3) ?
C3 C4 . 1.370(3) ?
C4 C5 . 1.390(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.357(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.512(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.481(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.478(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2B O2 3_765 0.90 2.34 3.013(3) 131
N2 H2B O1 3_765 0.90 1.97 2.764(2) 146
N2 H2A O3 . 0.90 2.56 3.242(3) 132
N2 H2A O3 3_665 0.90 2.13 2.916(3) 145
