#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012077.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_2012077
loop_
_publ_author_name
'Gao,  En-Qing '
'Liao, Dai-Zheng'
'Jiang, Zong-Hui'
'Yan, Shi-Ping'
_publ_section_title
;
 A novel hydrogen-bonded microporous framework constructed from two
 different metal complexes
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              807
_journal_page_last               809
_journal_paper_doi               10.1107/S0108270101006849
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac
'[Ni(C16 H36 N4 )][Ni(C10 H4 N2 O6 )] , 2H2 O'
_chemical_formula_moiety
'C16 H36 N4 Ni 2+ , C10 H4 N2 Ni O6 2- , 2H2 O'
_chemical_formula_sum            'C26 H44 N6 Ni2 O8'
_chemical_formula_weight         686.09
_chemical_name_systematic
;
 meso-5,7,7,12,14,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane nickel(II)
 1,2-phenylenebis(oxamato)cuprate(II) dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                92.488(2)
_cell_angle_beta                 110.247(2)
_cell_angle_gamma                99.408(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0460(8)
_cell_length_b                   12.4964(10)
_cell_length_c                   12.7901(10)
_cell_measurement_reflns_used    4890
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.25
_cell_volume                     1477.5(2)
_computing_cell_refinement       'SMART1000 software'
_computing_data_collection       'SMART1000 software (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1996)'
_computing_molecular_graphics    'XP (Sheldrick, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full .993
_diffrn_measured_fraction_theta_max .993
_diffrn_measurement_device       'BRUKER SMART 1000'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .015
_diffrn_reflns_av_sigmaI/netI    .0259
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6157
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.66
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    1.333
_exptl_absorpt_correction_T_max  .8783
_exptl_absorpt_correction_T_min  .6906
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             724
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .1
_refine_diff_density_max         .430
_refine_diff_density_min         -.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         5173
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          .0398
_refine_ls_R_factor_gt           .0322
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0545P)²+0.3612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0913
_reflns_number_gt                4408
_reflns_number_total             5173
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1170.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

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               2012077
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Ni1 .5 .5 .5 .02707(12) Uani d S 1 . . Ni
Ni2 0 0 0 .03056(13) Uani d S 1 . . Ni
Ni3 .88728(3) .75816(2) .50559(3) .03268(11) Uani d . 1 . . Ni
O1 .8391(2) .67964(16) .61494(17) .0489(5) Uani d . 1 . . O
O2 .7268(2) .69986(16) .37633(16) .0472(5) Uani d . 1 . . O
O3 .8906(2) .88163(18) .23166(16) .0528(5) Uani d . 1 . . O
O5 .9337(3) .66372(19) .79683(19) .0634(6) Uani d . 1 . . O
O4 .6458(2) .7157(2) .19357(19) .0690(7) Uani d . 1 . . O
O6 1.1557(2) .83919(18) .81282(15) .0541(5) Uani d . 1 . . O
N1 1.0517(2) .82356(16) .61960(16) .0312(5) Uani d . 1 . . N
N2 .9551(2) .84050(16) .41470(16) .0306(4) Uani d . 1 . . N
C1 1.0631(3) .8000(2) .7220(2) .0361(6) Uani d . 1 . . C
C2 .9373(3) .7072(2) .7135(2) .0421(6) Uani d . 1 . . C
C3 .7348(3) .7424(2) .2879(2) .0450(7) Uani d . 1 . . C
C4 .8705(3) .8314(2) .3078(2) .0357(6) Uani d . 1 . . C
C5 1.0914(3) .90860(19) .4701(2) .0296(5) Uani d . 1 . . C
C6 1.1713(3) .9776(2) .4230(2) .0392(6) Uani d . 1 . . C
H6A 1.1356 .985 .3467 .047 Uiso calc R 1 . . H
C7 1.3055(3) 1.0359(2) .4913(3) .0485(7) Uani d . 1 . . C
H7A 1.3605 1.082 .4602 .058 Uiso calc R 1 . . H
C8 1.3585(3) 1.0267(2) .6041(3) .0481(7) Uani d . 1 . . C
H8A 1.4489 1.0667 .6482 .058 Uiso calc R 1 . . H
C9 1.2796(3) .9587(2) .6533(2) .0387(6) Uani d . 1 . . C
H9A 1.3157 .9531 .73 .046 Uiso calc R 1 . . H
C10 1.1458(3) .89929(19) .5861(2) .0292(5) Uani d . 1 . . C
N3 .3316(2) .53726(17) .38712(18) .0326(5) Uani d D 1 . . N
N4 .4273(2) .51884(17) .62182(18) .0330(5) Uani d D 1 . . N
C11 .3567(3) .5460(3) .2797(2) .0455(7) Uani d . 1 . . C
H11A .4073 .6187 .2784 .055 Uiso calc R 1 . . H
H11B .2654 .5314 .217 .055 Uiso calc R 1 . . H
C12 .5542(3) .5366(2) .7277(2) .0456(7) Uani d . 1 . . C
H12A .5231 .5276 .7912 .055 Uiso calc R 1 . . H
H12B .6099 .6097 .7371 .055 Uiso calc R 1 . . H
C13 .2654(3) .6285(2) .4171(2) .0412(6) Uani d . 1 . . C
C14 .2148(3) .5965(2) .5123(2) .0444(7) Uani d . 1 . . C
H14A .1527 .6457 .5203 .053 Uiso calc R 1 . . H
H14B .1559 .5238 .4906 .053 Uiso calc R 1 . . H
C15 .3304(3) .5969(2) .6259(2) .0427(6) Uani d . 1 . . C
H15A .3897 .6704 .6477 .051 Uiso calc R 1 . . H
C16 .1319(4) .6403(3) .3172(3) .0695(10) Uani d . 1 . . C
H16A .0627 .5731 .2978 .104 Uiso calc R 1 . . H
H16B .1598 .6572 .2543 .104 Uiso calc R 1 . . H
H16C .0896 .6979 .3368 .104 Uiso calc R 1 . . H
C17 .3782(4) .7341(2) .4507(3) .0598(9) Uani d . 1 . . C
H17A .4604 .7247 .5135 .09 Uiso calc R 1 . . H
H17B .3371 .7922 .4711 .09 Uiso calc R 1 . . H
H17C .4079 .7516 .3888 .09 Uiso calc R 1 . . H
C18 .2612(4) .5718(3) .7131(3) .0729(11) Uani d . 1 . . C
H18A .3354 .5732 .7851 .109 Uiso calc R 1 . . H
H18B .2003 .5008 .6924 .109 Uiso calc R 1 . . H
H18C .2043 .6255 .7169 .109 Uiso calc R 1 . . H
N5 .1022(2) -.12291(18) .02236(17) .0341(5) Uani d D 1 . . N
N6 .1694(2) .10498(19) .00537(17) .0353(5) Uani d D 1 . . N
C22 .3470(3) -.0135(2) .0670(2) .0418(6) Uani d . 1 . . C
H22A .3329 -.0249 -.0119 .05 Uiso calc R 1 . . H
H22B .4481 -.013 .1091 .05 Uiso calc R 1 . . H
C23 .3162(3) .0989(2) .0900(2) .0387(6) Uani d . 1 . . C
C24 .3174(3) -.2121(3) .0835(3) .0574(8) Uani d . 1 . . C
H24A .2607 -.2728 .1019 .086 Uiso calc R 1 . . H
H24B .416 -.2022 .1337 .086 Uiso calc R 1 . . H
H24C .3128 -.2263 .0078 .086 Uiso calc R 1 . . H
C25 .4322(3) .1853(3) .0740(3) .0552(8) Uani d . 1 . . C
H25A .4331 .1726 -.0003 .083 Uiso calc R 1 . . H
H25B .525 .1812 .1279 .083 Uiso calc R 1 . . H
H25C .4112 .2564 .0843 .083 Uiso calc R 1 . . H
C26 .3130(3) .1174(3) .2077(2) .0526(8) Uani d . 1 . . C
H26A .2401 .0625 .2166 .079 Uiso calc R 1 . . H
H26B .2913 .1882 .2184 .079 Uiso calc R 1 . . H
H26C .4055 .1133 .262 .079 Uiso calc R 1 . . H
OW1 1.1023(4) .5286(3) .9507(3) .1003(10) Uani d D 1 . . O
OW2 .6433(5) .5527(4) .0291(4) .0638(12) Uani d P .5 . . O
OW2' .5845(7) .4370(6) -.0278(6) .106(2) Uani d P .5 . . O
C20 .1395(3) .2168(2) .0078(3) .0487(7) Uani d . 1 . . C
H20A .1992 .2637 -.0239 .058 Uiso calc R 1 . . H
H20B .1612 .2466 .0844 .058 Uiso calc R 1 . . H
C21 .2583(3) -.1095(2) .0946(2) .0400(6) Uani d . 1 . . C
H21A .2667 -.0955 .1729 .048 Uiso calc R 1 . . H
C19 .0168(3) -.2112(2) .0594(3) .0455(7) Uani d . 1 . . C
H19A .0344 -.196 .1386 .055 Uiso calc R 1 . . H
H19B .0445 -.2803 .0479 .055 Uiso calc R 1 . . H
H6N .173(3) .086(2) -.0625(12) .034(7) Uiso d D 1 . . H
H3N .260(2) .4784(16) .376(2) .047(8) Uiso d D 1 . . H
H5N .090(3) -.150(2) -.0477(12) .040(8) Uiso d D 1 . . H
H4N .374(3) .4526(13) .621(3) .053(9) Uiso d D 1 . . H
H1W 1.087(4) .579(3) .903(3) .091(14) Uiso d D 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 0 0 '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'
O O .0106 .006 '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'
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 Ni1 N3 . 2_666 180.0000(10) yes
N3 Ni1 N4 . . 93.79(9) yes
N3 Ni1 N4 2_666 . 86.21(9) no
N3 Ni1 N4 . 2_666 86.21(9) yes
N3 Ni1 N4 2_666 2_666 93.79(9) no
N4 Ni1 N4 . 2_666 180.0000(10) ?
N6 Ni2 N6 . 2 180.00(16) yes
N6 Ni2 N5 . 2 86.32(9) yes
N6 Ni2 N5 2 2 93.68(9) no
N6 Ni2 N5 . . 93.68(9) yes
N6 Ni2 N5 2 . 86.32(9) no
N5 Ni2 N5 2 . 180.00(11) yes
N2 Ni3 N1 . . 86.54(9) yes
N2 Ni3 O2 . . 86.58(9) yes
N1 Ni3 O2 . . 173.10(9) yes
N2 Ni3 O1 . . 172.77(9) yes
N1 Ni3 O1 . . 86.25(9) yes
O2 Ni3 O1 . . 100.62(9) yes
C2 O1 Ni3 . . 111.56(16) yes
C3 O2 Ni3 . . 112.25(17) yes
C1 N1 C10 . . 128.9(2) no
C1 N1 Ni3 . . 116.85(18) yes
C10 N1 Ni3 . . 114.14(15) yes
C4 N2 C5 . . 128.9(2) no
C4 N2 Ni3 . . 116.79(17) yes
C5 N2 Ni3 . . 114.28(15) yes
O6 C1 N1 . . 129.7(3) no
O6 C1 C2 . . 121.5(2) no
N1 C1 C2 . . 108.8(2) yes
O5 C2 O1 . . 123.5(3) no
O5 C2 C1 . . 120.5(3) no
O1 C2 C1 . . 116.0(2) yes
O4 C3 O2 . . 124.4(3) no
O4 C3 C4 . . 120.3(3) no
O2 C3 C4 . . 115.3(2) yes
O3 C4 N2 . . 128.5(3) no
O3 C4 C3 . . 122.5(2) no
N2 C4 C3 . . 109.0(2) yes
C6 C5 C10 . . 120.0(2) no
C6 C5 N2 . . 127.4(2) no
C10 C5 N2 . . 112.5(2) no
C5 C6 C7 . . 118.8(3) no
C8 C7 C6 . . 121.1(3) no
C7 C8 C9 . . 121.0(3) no
C10 C9 C8 . . 118.6(3) no
C9 C10 C5 . . 120.4(2) no
C9 C10 N1 . . 127.0(2) no
C5 C10 N1 . . 112.5(2) no
C11 N3 C13 . . 113.4(2) no
C11 N3 Ni1 . . 109.68(15) no
C13 N3 Ni1 . . 119.02(17) no
C12 N4 C15 . . 109.7(2) no
C12 N4 Ni1 . . 106.72(16) no
C15 N4 Ni1 . . 124.20(16) no
N3 C11 C12 . 2_666 106.9(2) no
N4 C12 C11 . 2_666 107.1(2) no
N3 C13 C14 . . 107.6(2) no
N3 C13 C17 . . 109.1(2) no
C14 C13 C17 . . 111.8(3) no
N3 C13 C16 . . 109.7(2) no
C14 C13 C16 . . 107.4(2) no
C17 C13 C16 . . 111.1(3) no
C15 C14 C13 . . 117.0(2) no
N4 C15 C14 . . 111.4(2) no
N4 C15 C18 . . 111.4(2) no
C14 C15 C18 . . 110.1(3) no
C19 N5 C21 . . 109.2(2) no
C19 N5 Ni2 . . 107.64(15) no
C21 N5 Ni2 . . 122.10(18) no
C20 N6 C23 . . 111.7(2) no
C20 N6 Ni2 . . 109.92(16) no
C23 N6 Ni2 . . 119.54(16) no
C21 C22 C23 . . 117.0(2) no
N6 C23 C22 . . 107.3(2) no
N6 C23 C26 . . 108.8(2) no
C22 C23 C26 . . 111.9(2) no
N6 C23 C25 . . 109.8(2) no
C22 C23 C25 . . 108.6(2) no
C26 C23 C25 . . 110.4(2) no
N6 C20 C19 . 2 108.0(2) no
N5 C21 C22 . . 110.8(2) no
N5 C21 C24 . . 111.6(2) no
C22 C21 C24 . . 110.1(2) no
N5 C19 C20 . 2 108.1(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 N3 . 1.947(2) yes
Ni1 N3 2_666 1.947(2) no
Ni1 N4 . 1.957(2) yes
Ni1 N4 2_666 1.957(2) no
Ni2 N6 . 1.951(2) yes
Ni2 N6 2 1.951(2) no
Ni2 N5 2 1.961(2) no
Ni2 N5 . 1.961(2) yes
Ni3 N2 . 1.8159(19) yes
Ni3 N1 . 1.819(2) yes
Ni3 O2 . 1.8790(18) yes
Ni3 O1 . 1.8935(18) yes
O1 C2 . 1.293(4) yes
O2 C3 . 1.293(4) yes
O3 C4 . 1.237(3) yes
O5 C2 . 1.226(3) yes
O4 C3 . 1.219(3) yes
O6 C1 . 1.228(3) yes
N1 C1 . 1.325(3) yes
N1 C10 . 1.413(3) no
N2 C4 . 1.325(3) yes
N2 C5 . 1.413(3) no
C1 C2 . 1.539(4) yes
C3 C4 . 1.549(4) yes
C5 C6 . 1.380(3) no
C5 C10 . 1.410(3) no
C6 C7 . 1.385(4) no
C7 C8 . 1.371(4) no
C8 C9 . 1.386(4) no
C9 C10 . 1.384(3) no
N3 C11 . 1.486(3) no
N3 C13 . 1.508(3) no
N4 C12 . 1.481(3) no
N4 C15 . 1.497(3) no
C11 C12 2_666 1.492(4) no
C12 C11 2_666 1.492(4) no
C13 C14 . 1.519(4) no
C13 C17 . 1.528(4) no
C13 C16 . 1.532(4) no
C14 C15 . 1.514(4) no
C15 C18 . 1.524(4) no
N5 C19 . 1.482(3) no
N5 C21 . 1.497(3) no
N6 C20 . 1.478(4) no
N6 C23 . 1.514(3) no
C22 C21 . 1.505(4) no
C22 C23 . 1.524(4) no
C23 C26 . 1.525(4) no
C23 C25 . 1.529(4) no
C24 C21 . 1.519(4) no
OW2 OW2' . 1.517(8) no
C20 C19 2 1.494(4) no
C19 C20 2 1.494(4) 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
OW1 H1W O5 . .89(4) 2.13(4) 2.917(5) 147(4) yes
N3 H3N O1 2_666 .91(2) 2.09(2) 2.955(3) 159.0(19) yes
N4 H4N O2 2_666 .91(2) 2.01(2) 2.918(3) 175(3) yes
N5 H5N O6 1_444 .904(17) 2.11(2) 2.944(3) 153(2) yes
N6 H6N O3 2_665 .904(19) 2.111(16) 2.897(3) 145(2) yes
OW2 ? O4 . ? ? 2.855(5) ? yes
OW2' ? O4 2_665 ? ? 2.881(8) ? yes
OW1 ? OW1 2_767 ? ? 2.778(6) ? yes
OW1 ? OW2 2_766 ? ? 2.836(7) ? yes
OW1 ? OW2' 2_766 ? ? 2.904(9) ? yes
OW2 ? OW2 2_665 ? ? 2.788 ? yes
OW2' ? OW2' 2_665 ? ? 2.735 ? yes
