#------------------------------------------------------------------------------
#$Date: 2016-02-18 10:40:55 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176722 $
#$URL: svn://www.crystallography.net/cod/cif/3/00/00/3000008.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_3000008
loop_
_publ_author_name
'Alfonso Fernández-Botello'
'Miguel Quirós'
'Juan M. Salas'
_journal_name_full               'Personal Communication to COD'
_chemical_formula_sum            'C54 H74 N14 Ni O24'
_chemical_formula_weight         1361.98
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 125.301(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.063(3)
_cell_length_b                   16.3490(13)
_cell_length_c                   17.5384(15)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.31
_cell_measurement_theta_min      4.99
_cell_volume                     6333.1(11)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2θ/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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6415
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  0.9543
_exptl_absorpt_correction_T_min  0.8194
_exptl_absorpt_correction_type   integration
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2864
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         5565
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                4558
_reflns_number_total             5565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nitefen.cif
_cod_data_source_block           nitefen
_cod_depositor_comments
'Releasing structure 3000008 into public domain as published material.'
_cod_original_cell_volume        6333.0(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               3000008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Ni Ni 0.5000 0.41231(2) 0.2500 0.03070(13) Uani 1 2 d S
N1P N 0.43586(8) 0.32697(11) 0.22887(12) 0.0336(4) Uani 1 1 d .
C2P C 0.43255(10) 0.31964(13) 0.30304(16) 0.0346(5) Uani 1 1 d .
C3P C 0.47811(10) 0.36063(14) 0.38778(16) 0.0355(5) Uani 1 1 d .
N4P N 0.52006(9) 0.40555(12) 0.38661(13) 0.0376(4) Uani 1 1 d .
C5P C 0.56411(12) 0.44035(18) 0.46610(18) 0.0498(6) Uani 1 1 d .
H5P H 0.5928 0.4714 0.4659 0.060 Uiso 1 1 d R
C6P C 0.56914(14) 0.4323(2) 0.54942(19) 0.0614(8) Uani 1 1 d .
H6P H 0.6011 0.4569 0.6038 0.074 Uiso 1 1 d R
C7P C 0.52705(15) 0.3888(2) 0.5505(2) 0.0613(8) Uani 1 1 d .
H7P H 0.5298 0.3839 0.6057 0.074 Uiso 1 1 d R
C8P C 0.47908(13) 0.35098(16) 0.46844(18) 0.0477(6) Uani 1 1 d .
C9P C 0.43191(15) 0.30363(18) 0.4621(2) 0.0576(8) Uani 1 1 d .
H9P H 0.4313 0.2985 0.5144 0.069 Uiso 1 1 d R
C10P C 0.38889(13) 0.26688(17) 0.3823(2) 0.0539(7) Uani 1 1 d .
H10P H 0.3587 0.2373 0.3801 0.065 Uiso 1 1 d R
C11P C 0.38830(11) 0.27219(15) 0.30042(18) 0.0431(6) Uani 1 1 d .
C12P C 0.34656(12) 0.23087(17) 0.2166(2) 0.0522(7) Uani 1 1 d .
H12P H 0.3159 0.1997 0.2111 0.063 Uiso 1 1 d R
C13P C 0.35122(12) 0.23663(17) 0.14341(19) 0.0538(7) Uani 1 1 d .
H13P H 0.3246 0.2080 0.0884 0.065 Uiso 1 1 d R
C14P C 0.39614(11) 0.28586(15) 0.15170(17) 0.0435(6) Uani 1 1 d .
H14P H 0.3985 0.2901 0.1010 0.052 Uiso 1 1 d R
C3Q C 0.46778(10) 0.58445(13) 0.22707(15) 0.0341(5) Uani 1 1 d .
N4Q N 0.44017(8) 0.51045(12) 0.21032(13) 0.0363(4) Uani 1 1 d .
C5Q C 0.38052(11) 0.51031(17) 0.16684(19) 0.0484(6) Uani 1 1 d .
H5Q H 0.3610 0.4604 0.1556 0.058 Uiso 1 1 d R
C6Q C 0.34572(13) 0.58165(19) 0.1369(2) 0.0587(7) Uani 1 1 d .
H6Q H 0.3039 0.5787 0.1058 0.070 Uiso 1 1 d R
C7Q C 0.37314(13) 0.65512(18) 0.15418(19) 0.0549(7) Uani 1 1 d .
H7Q H 0.3503 0.7029 0.1343 0.066 Uiso 1 1 d R
C8Q C 0.43634(12) 0.65883(15) 0.20157(17) 0.0441(6) Uani 1 1 d .
C9Q C 0.46977(14) 0.73386(16) 0.22616(19) 0.0572(7) Uani 1 1 d .
H9Q H 0.4491 0.7834 0.2083 0.069 Uiso 1 1 d R
N1 N 0.55054(10) 0.13941(13) 0.58380(14) 0.0457(5) Uani 1 1 d .
C1 C 0.60856(14) 0.1691(2) 0.6664(2) 0.0631(8) Uani 1 1 d .
H11 H 0.6414 0.1458 0.6672 0.076 Uiso 1 1 d R
H12 H 0.6120 0.1533 0.7221 0.076 Uiso 1 1 d R
H13 H 0.6100 0.2276 0.6638 0.076 Uiso 1 1 d R
C2 C 0.54356(12) 0.14441(16) 0.49860(18) 0.0457(6) Uani 1 1 d .
O2 O 0.58239(9) 0.17569(14) 0.49277(14) 0.0632(5) Uani 1 1 d .
N3 N 0.49195(9) 0.11243(13) 0.42154(14) 0.0418(5) Uani 1 1 d .
C3 C 0.48548(13) 0.11007(18) 0.33262(18) 0.0512(7) Uani 1 1 d .
H31 H 0.4805 0.1647 0.3091 0.061 Uiso 1 1 d R
H32 H 0.4507 0.0779 0.2883 0.061 Uiso 1 1 d R
H33 H 0.5211 0.0861 0.3423 0.061 Uiso 1 1 d R
C4 C 0.44734(11) 0.08269(15) 0.42906(18) 0.0413(5) Uani 1 1 d .
C5 C 0.45431(11) 0.08158(14) 0.51235(17) 0.0402(5) Uani 1 1 d .
C6 C 0.50884(12) 0.10582(15) 0.59848(18) 0.0432(6) Uani 1 1 d .
O6 O 0.52029(10) 0.09897(12) 0.67641(13) 0.0584(5) Uani 1 1 d .
N7 N 0.40089(10) 0.04912(13) 0.49352(16) 0.0474(5) Uani 1 1 d .
C71 C 0.38088(13) 0.04642(16) 0.5551(2) 0.0518(7) Uani 1 1 d .
H71 H 0.4161 0.0411 0.6192 0.062 Uiso 1 1 d R
H72 H 0.3557 -0.0015 0.5402 0.062 Uiso 1 1 d R
C72 C 0.34522(12) 0.12257(16) 0.54668(19) 0.0459(6) Uani 1 1 d .
O71 O 0.32362(10) 0.12108(13) 0.59287(15) 0.0627(6) Uani 1 1 d .
O72 O 0.34276(13) 0.18014(14) 0.5002(2) 0.0889(9) Uani 1 1 d .
C8 C 0.36625(13) 0.03476(18) 0.4019(2) 0.0550(7) Uani 1 1 d .
H8 H 0.3274 0.0133 0.3709 0.066 Uiso 1 1 d R
N9 N 0.39282(10) 0.05338(15) 0.35823(16) 0.0522(5) Uani 1 1 d .
O1W O 0.69208(10) 0.25840(17) 0.58713(16) 0.0712(6) Uani 1 1 d D
H11W H 0.7019(17) 0.280(2) 0.6383(17) 0.085 Uiso 1 1 d D
H12W H 0.6571(10) 0.238(2) 0.563(2) 0.085 Uiso 1 1 d D
O2W O 0.25386(11) 0.28685(17) 0.38996(17) 0.0773(7) Uani 1 1 d D
H21W H 0.2308(15) 0.308(2) 0.402(3) 0.093 Uiso 1 1 d D
H22W H 0.2795(15) 0.255(2) 0.436(2) 0.093 Uiso 1 1 d D
O3W O 0.27970(13) 0.39764(19) -0.02116(18) 0.0869(8) Uani 1 1 d D
H31W H 0.2519(16) 0.422(2) -0.071(2) 0.104 Uiso 1 1 d D
H32W H 0.2933(19) 0.358(2) -0.036(3) 0.104 Uiso 1 1 d D
O4W O 0.31246(16) 0.4399(2) 0.4076(3) 0.1052(10) Uani 1 1 d D
H41W H 0.293(2) 0.3906(19) 0.393(3) 0.126 Uiso 1 1 d D
H42W H 0.2830(17) 0.473(3) 0.401(3) 0.126 Uiso 1 1 d D
O5W O 0.24381(16) 0.39946(18) 0.0974(2) 0.0930(8) Uani 1 1 d D
H51W H 0.258(2) 0.392(3) 0.064(3) 0.112 Uiso 1 1 d D
H52W H 0.228(2) 0.3536(18) 0.098(3) 0.112 Uiso 1 1 d D
O6W O 0.31551(17) -0.02192(19) 0.66150(19) 0.1176(13) Uani 1 1 d D
H61W H 0.3414(19) -0.023(3) 0.7202(15) 0.141 Uiso 1 1 d D
H62W H 0.328(2) 0.022(2) 0.652(4) 0.141 Uiso 1 1 d D
O7W O 0.29286(18) 0.5025(2) 0.2478(2) 0.1089(10) Uani 1 1 d D
H71W H 0.292(2) 0.475(3) 0.291(3) 0.131 Uiso 1 1 d D
H72W H 0.280(2) 0.465(2) 0.206(3) 0.131 Uiso 1 1 d D
O8W O 0.72596(18) 0.3290(2) 0.7480(2) 0.1035(10) Uani 1 1 d D
H81W H 0.723(2) 0.3797(14) 0.754(3) 0.124 Uiso 1 1 d D
H82W H 0.731(2) 0.299(3) 0.791(3) 0.124 Uiso 1 1 d 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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0600
-1.00 0.00 0.00 0.0600
1.00 1.00 0.00 0.2000
-1.00 1.00 0.00 0.2000
-1.00 -1.00 0.00 0.2000
1.00 -1.00 0.00 0.2000
1.00 1.00 -1.00 0.2000
1.00 -1.00 -1.00 0.2000
-1.00 -1.00 1.00 0.2000
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
N1P Ni N1P 96.07(10) . 2_655
N1P Ni N4Q 167.50(7) . 2_655
N1P Ni N4Q 92.82(7) 2_655 2_655
N1P Ni N4Q 92.82(7) . .
N1P Ni N4Q 167.50(7) 2_655 .
N4Q Ni N4Q 79.87(10) 2_655 .
N1P Ni N4P 79.07(7) . .
N1P Ni N4P 96.91(7) 2_655 .
N4Q Ni N4P 91.17(7) 2_655 .
N4Q Ni N4P 93.39(7) . .
N1P Ni N4P 96.91(7) . 2_655
N1P Ni N4P 79.07(7) 2_655 2_655
N4Q Ni N4P 93.39(7) 2_655 2_655
N4Q Ni N4P 91.17(7) . 2_655
N4P Ni N4P 174.05(11) . 2_655
C14P N1P C2P 118.0(2) . .
C14P N1P Ni 128.38(16) . .
C2P N1P Ni 113.39(14) . .
N1P C2P C11P 122.9(2) . .
N1P C2P C3P 117.21(19) . .
C11P C2P C3P 119.8(2) . .
N4P C3P C8P 122.9(2) . .
N4P C3P C2P 117.44(19) . .
C8P C3P C2P 119.6(2) . .
C5P N4P C3P 117.7(2) . .
C5P N4P Ni 130.39(17) . .
C3P N4P Ni 111.82(15) . .
N4P C5P C6P 123.0(3) . .
C7P C6P C5P 119.4(3) . .
C6P C7P C8P 120.3(2) . .
C7P C8P C3P 116.7(2) . .
C7P C8P C9P 124.6(2) . .
C3P C8P C9P 118.7(3) . .
C10P C9P C8P 121.2(2) . .
C9P C10P C11P 121.4(2) . .
C2P C11P C12P 117.0(2) . .
C2P C11P C10P 119.1(2) . .
C12P C11P C10P 123.9(2) . .
C13P C12P C11P 119.7(2) . .
C12P C13P C14P 119.4(2) . .
N1P C14P C13P 122.9(2) . .
N4Q C3Q C8Q 123.1(2) . .
N4Q C3Q C3Q 117.24(12) . 2_655
C8Q C3Q C3Q 119.68(15) . 2_655
C5Q N4Q C3Q 117.3(2) . .
C5Q N4Q Ni 129.77(18) . .
C3Q N4Q Ni 112.75(14) . .
N4Q C5Q C6Q 123.1(3) . .
C7Q C6Q C5Q 119.6(3) . .
C6Q C7Q C8Q 119.6(2) . .
C3Q C8Q C7Q 117.3(2) . .
C3Q C8Q C9Q 119.0(2) . .
C7Q C8Q C9Q 123.7(2) . .
C9Q C9Q C8Q 121.20(15) 2_655 .
C2 N1 C6 126.3(2) . .
C2 N1 C1 116.2(2) . .
C6 N1 C1 117.4(2) . .
O2 C2 N3 120.8(2) . .
O2 C2 N1 121.5(2) . .
N3 C2 N1 117.7(2) . .
C2 N3 C4 119.5(2) . .
C2 N3 C3 119.2(2) . .
C4 N3 C3 121.4(2) . .
N9 C4 C5 112.5(2) . .
N9 C4 N3 126.0(2) . .
C5 C4 N3 121.5(2) . .
C4 C5 N7 105.7(2) . .
C4 C5 C6 123.3(2) . .
N7 C5 C6 130.9(2) . .
O6 C6 N1 122.0(2) . .
O6 C6 C5 126.7(2) . .
N1 C6 C5 111.3(2) . .
C8 N7 C5 105.4(2) . .
C8 N7 C71 125.6(2) . .
C5 N7 C71 127.9(2) . .
N7 C71 C72 112.7(2) . .
O72 C72 O71 125.8(3) . .
O72 C72 C71 118.7(2) . .
O71 C72 C71 115.4(2) . .
N7 C8 N9 114.1(2) . .
C4 N9 C8 102.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni N1P 2.0865(18) .
Ni N1P 2.0865(18) 2_655
Ni N4Q 2.0924(19) 2_655
Ni N4Q 2.0924(19) .
Ni N4P 2.1318(18) .
Ni N4P 2.1318(18) 2_655
N1P C14P 1.326(3) .
N1P C2P 1.360(3) .
C2P C11P 1.405(3) .
C2P C3P 1.435(3) .
C3P N4P 1.362(3) .
C3P C8P 1.408(3) .
N4P C5P 1.329(3) .
C5P C6P 1.393(4) .
C6P C7P 1.353(5) .
C7P C8P 1.407(4) .
C8P C9P 1.441(4) .
C9P C10P 1.338(4) .
C10P C11P 1.430(4) .
C11P C12P 1.405(4) .
C12P C13P 1.363(4) .
C13P C14P 1.394(4) .
C3Q N4Q 1.362(3) .
C3Q C8Q 1.401(3) .
C3Q C3Q 1.438(5) 2_655
N4Q C5Q 1.328(3) .
C5Q C6Q 1.397(4) .
C6Q C7Q 1.351(4) .
C7Q C8Q 1.406(4) .
C8Q C9Q 1.435(4) .
C9Q C9Q 1.340(6) 2_655
N1 C2 1.396(3) .
N1 C6 1.406(3) .
N1 C1 1.473(4) .
C2 O2 1.225(3) .
C2 N3 1.367(3) .
N3 C4 1.377(3) .
N3 C3 1.466(3) .
C4 N9 1.353(3) .
C4 C5 1.361(3) .
C5 N7 1.389(3) .
C5 C6 1.428(4) .
C6 O6 1.219(3) .
N7 C8 1.332(4) .
N7 C71 1.462(3) .
C71 C72 1.529(4) .
C72 O72 1.221(3) .
C72 O71 1.243(3) .
C8 N9 1.354(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H11W O8W 0.849(18) 1.824(19) 2.673(4) 177(4) .
O1W H12W O2 0.850(18) 1.94(2) 2.775(3) 166(4) .
O2W H21W O71 0.846(19) 1.91(2) 2.735(3) 164(4) 7_556
O2W H22W O72 0.871(18) 1.86(2) 2.682(3) 157(4) .
O3W H31W O6W 0.852(19) 1.83(2) 2.664(4) 166(4) 4
O3W H32W O1W 0.852(19) 2.01(2) 2.851(4) 168(4) 2_655
O4W H41W O2W 0.917(19) 1.98(2) 2.882(4) 166(4) .
O5W H51W O3W 0.867(19) 1.90(2) 2.756(4) 167(5) .
O5W H52W O1W 0.862(19) 2.03(2) 2.892(4) 173(4) 8_455
O6W H61W N9 0.85(2) 2.04(2) 2.864(4) 166(5) 6_556
O6W H62W O71 0.85(2) 1.89(3) 2.696(3) 158(5) .
O7W H71W O4W 0.891(19) 1.87(3) 2.731(5) 161(5) .
O7W H72W O5W 0.861(19) 1.89(2) 2.742(4) 168(5) .
O8W H81W O7W 0.848(19) 1.97(2) 2.810(5) 173(5) 5_666
O8W H82W O2W 0.849(19) 2.03(2) 2.860(4) 167(5) 8_556
