#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/32/2103234.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_2103234
loop_
_publ_author_name
'Zakaria, Choudhury M.'
'Ferguson, George'
'Lough, Alan J.'
'Glidewell, Christopher'
_publ_section_title
;
 [Ni(cyclam)(OCOR)₂], a finite molecular complex:
 hydrogen-bonded supramolecular aggregation in one, two and three
 dimensions, and coordination polymers in one and two dimensions
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              78
_journal_page_last               93
_journal_paper_doi               10.1107/S010876810101850X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C24 H30 N8 Ni O12'
_chemical_formula_sum            'C24 H30 N8 Ni O12'
_chemical_formula_weight         681.27
_chemical_name_systematic
;
Bis-(3,5-dinitrobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(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
_cell_angle_alpha                99.826(2)
_cell_angle_beta                 97.966(2)
_cell_angle_gamma                108.388(2)
_cell_formula_units_Z            1
_cell_length_a                   7.7663(3)
_cell_length_b                   9.7845(6)
_cell_length_c                   10.4026(7)
_cell_measurement_reflns_used    5718
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.82
_cell_volume                     723.30(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    ' PLATON (Spek, 2001)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .986
_diffrn_measured_fraction_theta_max .972
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .075
_diffrn_reflns_av_sigmaI/netI    .0638
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17662
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    .748
_exptl_absorpt_correction_T_max  .9852
_exptl_absorpt_correction_T_min  .8067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .02
_refine_diff_density_max         .285
_refine_diff_density_min         -.431
_refine_ls_extinction_coef       .013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          .0578
_refine_ls_R_factor_gt           .0421
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)P)²+0.3293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .0887
_refine_ls_wR_factor_ref         .0968
_reflns_number_gt                2560
_reflns_number_total             3135
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0129.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2103234
_cod_database_fobs_code          2103234
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Ni1 .5000 .5000 .5000 .03420(15) Uani d S 1 Ni
N1 .2732(3) .5215(2) .57420(19) .0407(5) Uani d . 1 N
C2 .2156(4) .4009(3) .6446(3) .0529(7) Uani d . 1 C
C3 .2281(4) .2618(3) .5626(3) .0538(7) Uani d . 1 C
N4 .4181(3) .2920(2) .5391(2) .0415(5) Uani d . 1 N
C5 .4378(4) .1739(3) .4400(3) .0469(6) Uani d . 1 C
C6 .6350(4) .2085(3) .4189(3) .0494(6) Uani d . 1 C
C7 .7033(4) .3306(3) .3461(3) .0484(6) Uani d . 1 C
O11 .3435(2) .40263(19) .30221(16) .0456(4) Uani d . 1 O
O12 .1530(2) .5311(2) .28440(18) .0547(5) Uani d . 1 O
O32 .0894(3) -.0360(3) -.2587(2) .0800(7) Uani d . 1 O
O31 .2989(3) .0153(2) -.0804(2) .0681(6) Uani d . 1 O
O51 -.3909(3) .3286(3) -.0794(2) .0696(6) Uani d . 1 O
O52 -.4066(3) .1585(2) -.2464(2) .0704(6) Uani d . 1 O
N3 .1675(4) .0330(2) -.1442(2) .0537(6) Uani d . 1 N
N5 -.3274(3) .2430(3) -.1391(2) .0520(6) Uani d . 1 N
C11 .1133(3) .3314(2) .1059(2) .0362(5) Uani d . 1 C
C12 .1873(3) .2326(3) .0429(2) .0402(5) Uani d . 1 C
C13 .0918(3) .1419(3) -.0800(2) .0422(6) Uani d . 1 C
C14 -.0744(4) .1447(3) -.1438(2) .0454(6) Uani d . 1 C
C15 -.1450(3) .2432(3) -.0773(2) .0406(5) Uani d . 1 C
C16 -.0543(3) .3368(3) .0452(2) .0387(5) Uani d . 1 C
C17 .2114(3) .4321(3) .2431(2) .0373(5) Uani d . 1 C
H1 .1802 .5011 .5024 .049 Uiso calc R 1 H
H2A .0894 .3839 .6563 .063 Uiso calc R 1 H
H2B .2958 .4277 .7319 .063 Uiso calc R 1 H
H3A .1973 .1828 .6097 .065 Uiso calc R 1 H
H3B .1406 .2307 .4781 .065 Uiso calc R 1 H
H4 .4912 .2983 .6178 .050 Uiso calc R 1 H
H5A .3560 .1601 .3558 .056 Uiso calc R 1 H
H5B .3999 .0820 .4694 .056 Uiso calc R 1 H
H6A .6451 .1189 .3693 .059 Uiso calc R 1 H
H6B .7172 .2355 .5054 .059 Uiso calc R 1 H
H7A .8211 .3316 .3244 .058 Uiso calc R 1 H
H7B .6156 .3098 .2631 .058 Uiso calc R 1 H
H12 .2993 .2276 .0829 .048 Uiso calc R 1 H
H14 -.1359 .0836 -.2272 .055 Uiso calc R 1 H
H16 -.1049 .4026 .0865 .046 Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni .3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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
N4 Ni1 N4 . 2_666 180.0 no
N4 Ni1 N1 . . 85.46(8) no
N4 Ni1 N1 2_666 . 94.54(8) no
N4 Ni1 N1 . 2_666 94.54(8) no
N4 Ni1 N1 2_666 2_666 85.46(8) no
N1 Ni1 N1 . 2_666 180.0 no
N4 Ni1 O11 . 2_666 91.86(7) no
N4 Ni1 O11 2_666 2_666 88.14(7) no
N1 Ni1 O11 . 2_666 86.49(7) no
N1 Ni1 O11 2_666 2_666 93.51(7) no
N4 Ni1 O11 . . 88.14(7) no
N4 Ni1 O11 2_666 . 91.86(7) no
N1 Ni1 O11 . . 93.51(7) no
N1 Ni1 O11 2_666 . 86.49(7) no
O11 Ni1 O11 2_666 . 180 no
C2 N1 C7 . 2_666 114.0(2) no
C2 N1 Ni1 . . 105.8(2) no
C7 N1 Ni1 2_666 . 116.7(2) no
C2 N1 H1 . . 106.6 no
C7 N1 H1 2_666 . 106.6 no
Ni1 N1 H1 . . 106.6 no
N1 C2 C3 . . 108.7(2) no
N1 C2 H2A . . 109.9 no
C3 C2 H2A . . 109.9 no
N1 C2 H2B . . 109.9 no
C3 C2 H2B . . 109.9 no
H2A C2 H2B . . 108.3 no
N4 C3 C2 . . 109.3(2) no
N4 C3 H3A . . 109.8 no
C2 C3 H3A . . 109.8 no
N4 C3 H3B . . 109.8 no
C2 C3 H3B . . 109.8 no
H3A C3 H3B . . 108.3 no
C5 N4 C3 . . 113.9(2) no
C5 N4 Ni1 . . 115.8(2) no
C3 N4 Ni1 . . 106.1(2) no
C5 N4 H4 . . 106.8 no
C3 N4 H4 . . 106.8 no
Ni1 N4 H4 . . 106.8 no
N4 C5 C6 . . 112.4(2) no
N4 C5 H5A . . 109.1 no
C6 C5 H5A . . 109.1 no
N4 C5 H5B . . 109.1 no
C6 C5 H5B . . 109.1 no
H5A C5 H5B . . 107.9 no
C5 C6 C7 . . 116.2(2) no
C5 C6 H6A . . 108.2 no
C7 C6 H6A . . 108.2 no
C5 C6 H6B . . 108.2 no
C7 C6 H6B . . 108.2 no
H6A C6 H6B . . 107.4 no
N1 C7 C6 2_666 . 112.6(2) no
N1 C7 H7A 2_666 . 109.1 no
C6 C7 H7A . . 109.1 no
N1 C7 H7B 2_666 . 109.1 no
C6 C7 H7B . . 109.1 no
H7A C7 H7B . . 107.8 no
C17 O11 Ni1 . . 127.9(2) no
O31 N3 O32 . . 124.4(3) no
O31 N3 C13 . . 118.5(2) no
O32 N3 C13 . . 117.0(3) no
O52 N5 O51 . . 123.7(2) no
O52 N5 C15 . . 118.5(2) no
O51 N5 C15 . . 117.9(2) no
C16 C11 C12 . . 119.8(2) no
C16 C11 C17 . . 119.2(2) no
C12 C11 C17 . . 121.0(2) no
C13 C12 C11 . . 118.9(2) no
C13 C12 H12 . . 120.6 no
C11 C12 H12 . . 120.6 no
C14 C13 C12 . . 123.0(2) no
C14 C13 N3 . . 118.3(2) no
C12 C13 N3 . . 118.6(2) no
C13 C14 C15 . . 116.5(2) no
C13 C14 H14 . . 121.8 no
C15 C14 H14 . . 121.8 no
C16 C15 C14 . . 122.8(2) no
C16 C15 N5 . . 119.3(2) no
C14 C15 N5 . . 117.9(2) no
C15 C16 C11 . . 119.1(2) no
C15 C16 H16 . . 120.5 no
C11 C16 H16 . . 120.5 no
O12 C17 O11 . . 127.2(2) no
O12 C17 C11 . . 117.4(2) no
O11 C17 C11 . . 115.4(2) no
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 . 2.073(2) no
Ni1 N1 2_666 2.073(2) no
Ni1 N4 . 2.062(2) no
Ni1 N4 2_666 2.062(2) no
Ni1 O11 2_666 2.127(2) no
Ni1 O11 . 2.127(2) no
N1 C2 . 1.477(3) no
N1 C7 2_666 1.482(3) no
N1 H1 . .91 no
C2 C3 . 1.516(4) no
C2 H2A . .97 no
C2 H2B . .97 no
C3 N4 . 1.474(3) no
C3 H3A . .97 no
C3 H3B . .97 no
N4 C5 . 1.473(3) no
N4 H4 . .91 no
C5 C6 . 1.516(4) no
C5 H5A . .97 no
C5 H5B . .97 no
C6 C7 . 1.517(4) no
C6 H6A . .97 no
C6 H6B . .97 no
C7 N1 2_666 1.482(3) no
C7 H7A . .97 no
C7 H7B . .97 no
O11 C17 . 1.259(3) no
O12 C17 . 1.233(3) no
O31 N3 . 1.214(3) no
O32 N3 . 1.229(3) no
O51 N5 . 1.224(3) no
O52 N5 . 1.218(3) no
N3 C13 . 1.479(3) no
N5 C15 . 1.472(3) no
C11 C12 . 1.391(3) no
C11 C16 . 1.386(3) no
C11 C17 . 1.527(3) no
C12 C13 . 1.381(3) no
C12 H12 . .93 no
C13 C14 . 1.377(4) no
C14 C15 . 1.386(4) no
C14 H14 . .93 no
C15 C16 . 1.380(3) no
C16 H16 . .93 no
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
_geom_hbond_publ_flag
N1 H1 O12 . .91 2.33 3.056(3) 137 y
N4 H4 O52 1_656 .91 2.35 3.132(3) 144 y
C2 H2A O12 2_566 .97 2.40 3.287(4) 152 y
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N4 Ni1 N1 C2 . . 15.0(2) no
N4 Ni1 N1 C2 2_666 . -165.0(2) no
O11 Ni1 N1 C2 2_666 . -77.1(2) no
O11 Ni1 N1 C2 . . 102.9(2) no
N4 Ni1 N1 C7 . 2_666 143.0(2) no
N4 Ni1 N1 C7 2_666 2_666 -37.0(2) no
O11 Ni1 N1 C7 2_666 2_666 50.9(2) no
O11 Ni1 N1 C7 . 2_666 -129.2(2) no
C7 N1 C2 C3 2_666 . -170.5(2) no
Ni1 N1 C2 C3 . . -41.0(2) no
N1 C2 C3 N4 . . 56.4(3) no
C2 C3 N4 C5 . . -169.1(2) no
C2 C3 N4 Ni1 . . -40.5(2) no
N1 Ni1 N4 C5 . . 141.5(12) no
N1 Ni1 N4 C5 2_666 . -38.5(2) no
O11 Ni1 N4 C5 2_666 . -132.1(2) no
O11 Ni1 N4 C5 . . 47.9(2) no
N1 Ni1 N4 C3 . . 14.1(2) no
N1 Ni1 N4 C3 2_666 . -165.9(2) no
O11 Ni1 N4 C3 2_666 . 100.4(2) no
O11 Ni1 N4 C3 . . -79.6(2) no
C3 N4 C5 C6 . . -179.8(2) no
Ni1 N4 C5 C6 . . 56.8(3) no
N4 C5 C6 C7 . . -71.0(3) no
C5 C6 C7 N1 . 2_666 68.7(3) no
N4 Ni1 O11 C17 . . 121.4(2) no
N4 Ni1 O11 C17 2_666 . -58.6(2) no
N1 Ni1 O11 C17 . . 36.0(2) no
N1 Ni1 O11 C17 2_666 . -144.0(2) no
C16 C11 C12 C13 . . .4(3) no
C17 C11 C12 C13 . . 178.8(2) no
C11 C12 C13 C14 . . .0(4) no
C11 C12 C13 N3 . . -177.7(2) no
O31 N3 C13 C14 . . -169.6(2) no
O32 N3 C13 C14 . . 9.0(3) no
O31 N3 C13 C12 . . 8.2(3) no
O32 N3 C13 C12 . . -173.2(2) no
C12 C13 C14 C15 . . -.9(4) no
N3 C13 C14 C15 . . 176.9(2) no
C13 C14 C15 C16 . . 1.3(4) no
C13 C14 C15 N5 . . -176.6(2) no
O52 N5 C15 C16 . . -179.1(2) no
O51 N5 C15 C16 . . 1.0(3) no
O52 N5 C15 C14 . . -1.1(3) no
O51 N5 C15 C14 . . 179.0(2) no
C14 C15 C16 C11 . . -.9(4) no
N5 C15 C16 C11 . . 177.0(2) no
C12 C11 C16 C15 . . .0(3) no
C17 C11 C16 C15 . . -178.4(2) no
Ni1 O11 C17 O12 . . 5.5(4) no
Ni1 O11 C17 C11 . . -173.8(2) no
C16 C11 C17 O12 . . -11.8(3) no
C12 C11 C17 O12 . . 169.8(2) no
C16 C11 C17 O11 . . 167.5(2) no
C12 C11 C17 O11 . . -10.9(3) no
