#------------------------------------------------------------------------------
#$Date: 2016-03-25 08:23:00 +0100 (vie 25 de mar de 2016) $
#$Revision: 179720 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/22/7002285.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7002285
loop_
_publ_author_name
'Choudhury, Somnath Ray'
'Dey, Biswajit'
'Das, Suranjana'
'Robertazzi, Arturo'
'Jana, Atish Dipankar'
'Chen, Chih-Yuan'
'Lee, Hon Man'
'Gamez, Patrick'
'Mukhopadhyay, Subrata'
_publ_section_title
;
 Robust recognition of malonate and 2-amino-4-picolinium in conjunction
 with M(ii) as a triad (M = Ni/Co/Mn): role of this highly stable
 hydrogen-bonded motif in driving supramolecular self-assembly
;
_journal_issue                   37
_journal_name_full               'Dalton Transactions'
_journal_page_first              7617
_journal_page_last               7624
_journal_paper_doi               10.1039/b905127a
_journal_year                    2009
_chemical_formula_moiety         'C6 H8 Ni O10, 2(C6 H9 N2), 4(H2 O)'
_chemical_formula_sum            'C18 H34 N4 Ni O14'
_chemical_formula_weight         589.20
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                94.6690(10)
_cell_angle_beta                 92.1650(10)
_cell_angle_gamma                111.4180(10)
_cell_formula_units_Z            1
_cell_length_a                   7.4284(2)
_cell_length_b                   8.9640(2)
_cell_length_c                   10.5124(2)
_cell_measurement_temperature    150(2)
_cell_volume                     647.78(3)
_computing_cell_refinement       'SAINT v6.280a (Bruker, 2004)'
_computing_data_collection       'APEX2 v1.0-22 (Bruker, 2004)'
_computing_data_reduction        'SAINT v6.280a (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL 5.1'
_computing_publication_material  'SHELXTL 5.1'
_computing_structure_refinement  'SHELXTL 5.1'
_computing_structure_solution    'SHELXTL 5.1 (Sheldrick, 1998)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9820
_diffrn_reflns_theta_full        28.63
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         1.95
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  0.7903
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            parallelepipe
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       green
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.053(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   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0282P)²+0.2662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                3133
_reflns_number_total             3285
_reflns_threshold_expression     I>2σ
_cod_data_source_file            b905127a.txt
_cod_data_source_block           h2
_cod_database_code               7002285
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65775(15) 0.34408(13) -0.03591(11) 0.0148(2) Uani 1 1 d . . .
C2 C 0.59254(16) 0.37020(13) 0.09681(11) 0.0163(2) Uani 1 1 d . . .
H2A H 0.4497 0.3370 0.0904 0.020 Uiso 1 1 calc R . .
H2B H 0.6484 0.4868 0.1259 0.020 Uiso 1 1 calc R . .
C3 C 0.64902(16) 0.27950(13) 0.19781(11) 0.0161(2) Uani 1 1 d . . .
C4 C 0.2044(2) 0.30005(18) 0.33215(14) 0.0308(3) Uani 1 1 d . . .
H4A H 0.0957 0.3321 0.3541 0.046 Uiso 1 1 calc R . .
H4B H 0.1703 0.2308 0.2510 0.046 Uiso 1 1 calc R . .
H4C H 0.3191 0.3963 0.3236 0.046 Uiso 1 1 calc R . .
C7 C 0.24731(18) 0.20956(15) 0.43592(12) 0.0219(2) Uani 1 1 d . . .
C8 C 0.3113(2) 0.28799(16) 0.56105(13) 0.0258(3) Uani 1 1 d . . .
H8 H 0.3278 0.3979 0.5796 0.031 Uiso 1 1 calc R . .
C9 C 0.3489(2) 0.20475(16) 0.65418(13) 0.0255(3) Uani 1 1 d . . .
H9 H 0.3942 0.2576 0.7377 0.031 Uiso 1 1 calc R . .
C5 C 0.26110(17) -0.03441(14) 0.51152(11) 0.0187(2) Uani 1 1 d . . .
C6 C 0.22446(18) 0.05109(15) 0.41239(12) 0.0209(2) Uani 1 1 d . . .
H2 H 0.347(3) -0.003(2) 0.6874(17) 0.032(4) Uiso 1 1 d . . .
H6 H 0.189(2) -0.002(2) 0.3316(17) 0.028(4) Uiso 1 1 d . . .
H6A H -0.049(3) 0.558(2) 0.2810(18) 0.039(5) Uiso 1 1 d . . .
H7A H 0.949(3) 0.731(2) 0.122(2) 0.047(6) Uiso 1 1 d . . .
H5B H 0.141(3) -0.062(3) 0.0223(19) 0.045(5) Uiso 1 1 d . . .
H6B H 0.111(3) 0.604(2) 0.2171(19) 0.039(5) Uiso 1 1 d . . .
H7B H 0.872(3) 0.674(3) 0.007(2) 0.043(5) Uiso 1 1 d . . .
N1 N 0.23903(16) -0.18845(13) 0.49314(10) 0.0241(2) Uani 1 1 d . . .
H1A H 0.2641 -0.2371 0.5571 0.029 Uiso 1 1 calc R . .
H1B H 0.1993 -0.2420 0.4170 0.029 Uiso 1 1 calc R . .
N2 N 0.32224(15) 0.04609(13) 0.62912(10) 0.0200(2) Uani 1 1 d . . .
Ni1 Ni 0.5000 0.0000 0.0000 0.01289(7) Uani 1 2 d S . .
O1 O 0.60680(12) 0.20202(9) -0.08954(8) 0.01755(17) Uani 1 1 d . . .
O2 O 0.75585(13) 0.46626(10) -0.08850(8) 0.02058(18) Uani 1 1 d . . .
O3 O 0.60954(13) 0.12927(10) 0.17431(8) 0.02035(18) Uani 1 1 d . . .
O4 O 0.73055(13) 0.35866(10) 0.30153(8) 0.02269(19) Uani 1 1 d . . .
O5 O 0.23710(13) 0.02515(11) 0.02449(10) 0.0246(2) Uani 1 1 d . . .
H5A H 0.2179 0.0820 -0.0302 0.037 Uiso 1 1 calc R . .
O6 O 0.03944(14) 0.63631(11) 0.26085(9) 0.02184(18) Uani 1 1 d . . .
O7 O 0.91408(13) 0.75762(11) 0.05607(10) 0.02256(19) Uani 1 1 d . . .
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'
Ni Ni 0.3393 1.1124 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 123.09(10) . . ?
O2 C1 C2 118.00(10) . . ?
O1 C1 C2 118.88(9) . . ?
C1 C2 C3 114.94(9) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O4 C3 O3 123.47(10) . . ?
O4 C3 C2 117.30(10) . . ?
O3 C3 C2 119.23(10) . . ?
C7 C4 H4A 109.5 . . ?
C7 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C7 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C7 C8 118.85(11) . . ?
C6 C7 C4 121.16(12) . . ?
C8 C7 C4 119.99(12) . . ?
C9 C8 C7 119.45(12) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 N2 120.74(12) . . ?
C8 C9 H9 119.6 . . ?
N2 C9 H9 119.6 . . ?
N1 C5 N2 119.24(11) . . ?
N1 C5 C6 122.75(11) . . ?
N2 C5 C6 118.00(11) . . ?
C7 C6 C5 120.80(11) . . ?
C7 C6 H6 121.2(10) . . ?
C5 C6 H6 117.9(10) . . ?
C5 N1 H1A 120.0 . . ?
C5 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5 N2 C9 122.15(11) . . ?
C5 N2 H2 118.6(12) . . ?
C9 N2 H2 119.2(12) . . ?
O1 Ni1 O1 180.0 2_655 . ?
O1 Ni1 O3 89.15(3) 2_655 . ?
O1 Ni1 O3 90.86(3) . . ?
O1 Ni1 O3 90.86(3) 2_655 2_655 ?
O1 Ni1 O3 89.14(3) . 2_655 ?
O3 Ni1 O3 180.0 . 2_655 ?
O1 Ni1 O5 86.50(3) 2_655 . ?
O1 Ni1 O5 93.50(3) . . ?
O3 Ni1 O5 90.37(4) . . ?
O3 Ni1 O5 89.63(4) 2_655 . ?
O1 Ni1 O5 93.50(3) 2_655 2_655 ?
O1 Ni1 O5 86.50(3) . 2_655 ?
O3 Ni1 O5 89.63(4) . 2_655 ?
O3 Ni1 O5 90.37(4) 2_655 2_655 ?
O5 Ni1 O5 180.0 . 2_655 ?
C1 O1 Ni1 125.09(7) . . ?
C3 O3 Ni1 124.47(7) . . ?
Ni1 O5 H5B 114.9(14) . . ?
Ni1 O5 H5A 109.5 . . ?
H5B O5 H5A 110.1 . . ?
H6A O6 H6B 108.2(18) . . ?
H7A O7 H7B 104.5(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.2579(14) . ?
C1 O1 1.2639(13) . ?
C1 C2 1.5222(16) . ?
C2 C3 1.5232(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O4 1.2528(14) . ?
C3 O3 1.2699(13) . ?
C4 C7 1.5021(17) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C7 C6 1.3680(18) . ?
C7 C8 1.4173(19) . ?
C8 C9 1.3578(18) . ?
C8 H8 0.9500 . ?
C9 N2 1.3641(16) . ?
C9 H9 0.9500 . ?
C5 N1 1.3265(16) . ?
C5 N2 1.3522(16) . ?
C5 C6 1.4172(16) . ?
C6 H6 0.919(17) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2 0.834(18) . ?
Ni1 O1 2.0198(8) 2_655 ?
Ni1 O1 2.0198(8) . ?
Ni1 O3 2.0532(8) . ?
Ni1 O3 2.0532(8) 2_655 ?
Ni1 O5 2.0691(9) . ?
Ni1 O5 2.0691(9) 2_655 ?
O5 H5B 0.84(2) . ?
O5 H5A 0.8400 . ?
O6 H6A 0.81(2) . ?
O6 H6B 0.83(2) . ?
O7 H7A 0.82(2) . ?
O7 H7B 0.83(2) . ?
