#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/08/2210886.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_2210886
loop_
_publ_author_name
'Duriska, Martin B.'
'Batten, Stuart R.'
_publ_section_title
;
 (1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7,16-diacetato)nickel(II)
;
_journal_coeditor_code           BI2080
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2930
_journal_page_last               m2931
_journal_paper_doi               10.1107/S1600536806042103
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Ni (C16 H28 N2 O8)]'
_chemical_formula_moiety         'C16 H28 N2 Ni O8'
_chemical_formula_sum            'C16 H28 N2 Ni O8'
_chemical_formula_weight         435.11
_chemical_name_systematic
;
(1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7,16-diacetato)nickel(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.522(2)
_cell_angle_beta                 70.068(2)
_cell_angle_gamma                87.206(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9320(2)
_cell_length_b                   7.4993(2)
_cell_length_c                   9.0751(2)
_cell_measurement_reflns_used    237
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.68
_cell_measurement_theta_min      3.13
_cell_volume                     437.44(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-SEED (Barbour, 1999)'
_computing_publication_material  X-SEED
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker X8 APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5085
_diffrn_reflns_theta_full        30.70
_diffrn_reflns_theta_max         30.70
_diffrn_reflns_theta_min         2.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.159
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             230
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.472
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.026P)²+0.241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                2458
_reflns_number_total             2619
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2080.cif
_cod_data_source_block           I
_cod_database_code               2210886
_cod_database_fobs_code          2210886
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5000 0.0000 0.0000 0.01098(7) Uani d S 1
O O1 0.45496(15) -0.23545(13) 0.42830(11) 0.01321(19) Uani d . 1
N N1 0.55857(17) 0.10629(15) 0.17969(13) 0.0109(2) Uani d . 1
C C1 0.3298(2) -0.37276(18) 0.41596(16) 0.0140(2) Uani d . 1
H H1B 0.2417 -0.4256 0.5241 0.017 Uiso calc R 1
H H1A 0.4195 -0.4699 0.3685 0.017 Uiso calc R 1
O O2 0.68716(15) 0.26407(13) -0.15170(11) 0.01366(19) Uani d . 1
C C2 0.6444(2) -0.20278(18) 0.29875(16) 0.0132(2) Uani d . 1
H H2B 0.6338 -0.2481 0.2053 0.016 Uiso calc R 1
H H2A 0.7564 -0.2688 0.3283 0.016 Uiso calc R 1
O O3 0.23856(15) 0.13588(13) 0.07362(11) 0.01399(19) Uani d . 1
C C3 0.6936(2) -0.00315(18) 0.25711(15) 0.0128(2) Uani d . 1
H H3A 0.6827 0.0439 0.3553 0.015 Uiso calc R 1
H H3B 0.8377 0.0136 0.1851 0.015 Uiso calc R 1
O O4 0.04772(16) 0.27894(14) 0.27123(13) 0.0182(2) Uani d . 1
C C4 0.6568(2) 0.28830(17) 0.11111(16) 0.0135(2) Uani d . 1
H H4B 0.7294 0.3214 0.1798 0.016 Uiso calc R 1
H H4A 0.5490 0.3794 0.1092 0.016 Uiso calc R 1
C C5 0.8062(2) 0.29173(19) -0.05406(16) 0.0144(2) Uani d . 1
H H5A 0.8793 0.4095 -0.0930 0.017 Uiso calc R 1
H H5B 0.9087 0.1946 -0.0561 0.017 Uiso calc R 1
C C6 0.8052(2) 0.30931(19) -0.31836(16) 0.0148(2) Uani d . 1
H H6B 0.8826 0.2018 -0.3563 0.018 Uiso calc R 1
H H6A 0.9058 0.4057 -0.3329 0.018 Uiso calc R 1
C C7 0.3525(2) 0.13618(18) 0.29396(15) 0.0124(2) Uani d . 1
H H7A 0.3613 0.2322 0.3543 0.015 Uiso calc R 1
H H7B 0.3040 0.0238 0.3704 0.015 Uiso calc R 1
C C8 0.1990(2) 0.19141(17) 0.20721(15) 0.0124(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'
O O 0.0106 0.0060 '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
N1 Ni1 O2 . . 80.35(4) y
N1 Ni1 O2 2_655 . 99.65(4) y
N1 Ni1 O3 . . 82.26(4) y
O2 Ni1 O3 . . 92.79(4) y
O3 Ni1 N1 2_655 . 97.74(4) y
O3 Ni1 O2 2_655 . 87.21(4) y
O3 Ni1 O3 . 2_655 180.0 ?
O3 Ni1 N1 . 2_655 97.74(4) ?
O3 Ni1 N1 2_655 2_655 82.26(4) ?
N1 Ni1 N1 2_655 . 180.0 ?
O3 Ni1 O2 . 2_655 87.21(4) ?
O3 Ni1 O2 2_655 2_655 92.79(4) ?
N1 Ni1 O2 2_655 2_655 80.35(4) ?
N1 Ni1 O2 . 2_655 99.65(4) ?
O2 Ni1 O2 . 2_655 180.00(3) ?
C1 O1 C2 . . 114.52(10) ?
C7 N1 C3 . . 112.60(10) ?
C7 N1 C4 . . 106.93(10) ?
C3 N1 C4 . . 107.70(10) ?
C7 N1 Ni1 . . 104.64(8) ?
C3 N1 Ni1 . . 116.28(8) ?
C4 N1 Ni1 . . 108.28(8) ?
O1 C1 C6 . 2_655 114.50(11) ?
O1 C1 H1B . . 108.6 ?
C6 C1 H1B 2_655 . 108.6 ?
O1 C1 H1A . . 108.6 ?
C6 C1 H1A 2_655 . 108.6 ?
H1B C1 H1A . . 107.6 ?
C5 O2 C6 . . 111.15(10) ?
C5 O2 Ni1 . . 100.10(7) ?
C6 O2 Ni1 . . 131.97(8) ?
O1 C2 C3 . . 110.25(11) ?
O1 C2 H2B . . 109.6 ?
C3 C2 H2B . . 109.6 ?
O1 C2 H2A . . 109.6 ?
C3 C2 H2A . . 109.6 ?
H2B C2 H2A . . 108.1 ?
C8 O3 Ni1 . . 115.88(9) ?
N1 C3 C2 . . 114.54(11) ?
N1 C3 H3A . . 108.6 ?
C2 C3 H3A . . 108.6 ?
N1 C3 H3B . . 108.6 ?
C2 C3 H3B . . 108.6 ?
H3A C3 H3B . . 107.6 ?
N1 C4 C5 . . 111.87(10) ?
N1 C4 H4B . . 109.2 ?
C5 C4 H4B . . 109.2 ?
N1 C4 H4A . . 109.2 ?
C5 C4 H4A . . 109.2 ?
H4B C4 H4A . . 107.9 ?
O2 C5 C4 . . 106.42(11) ?
O2 C5 H5A . . 110.4 ?
C4 C5 H5A . . 110.4 ?
O2 C5 H5B . . 110.4 ?
C4 C5 H5B . . 110.4 ?
H5A C5 H5B . . 108.6 ?
O2 C6 C1 . 2_655 111.73(11) ?
O2 C6 H6B . . 109.3 ?
C1 C6 H6B 2_655 . 109.3 ?
O2 C6 H6A . . 109.3 ?
C1 C6 H6A 2_655 . 109.3 ?
H6B C6 H6A . . 107.9 ?
N1 C7 C8 . . 110.75(10) ?
N1 C7 H7A . . 109.5 ?
C8 C7 H7A . . 109.5 ?
N1 C7 H7B . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.1 ?
O4 C8 O3 . . 125.59(13) ?
O4 C8 C7 . . 118.58(12) ?
O3 C8 C7 . . 115.80(11) ?
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 N1 . 2.0906(11) y
Ni1 O2 . 2.3738(9) y
Ni1 O3 . 1.9970(10) y
Ni1 N1 2_655 2.0906(11) ?
Ni1 O2 2_655 2.3738(9) ?
Ni1 O3 2_655 1.9970(10) ?
O1 C1 . 1.4203(16) ?
O1 C2 . 1.4321(16) ?
N1 C7 . 1.4840(17) ?
N1 C3 . 1.4924(17) ?
N1 C4 . 1.4953(16) ?
C1 C6 2_655 1.507(2) ?
C1 H1B . 0.990 ?
C1 H1A . 0.990 ?
O2 C5 . 1.4441(16) ?
O2 C6 . 1.4446(16) ?
C2 C3 . 1.5086(18) ?
C2 H2B . 0.990 ?
C2 H2A . 0.990 ?
O3 C8 . 1.2834(16) ?
C3 H3A . 0.990 ?
C3 H3B . 0.990 ?
O4 C8 . 1.2294(17) ?
C4 C5 . 1.5005(19) ?
C4 H4B . 0.990 ?
C4 H4A . 0.990 ?
C5 H5A . 0.990 ?
C5 H5B . 0.990 ?
C6 C1 2_655 1.507(2) ?
C6 H6B . 0.990 ?
C6 H6A . 0.990 ?
C7 C8 . 1.5308(19) ?
C7 H7A . 0.990 ?
C7 H7B . 0.990 ?
