#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:14:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179745 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/41/7004150.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_7004150
loop_
_publ_author_name
'Havlíčková, Jana'
'Medová, Hana'
'Vitha, Tomáš'
'Kotek, Jan'
'Císařová, Ivana'
'Hermann, Petr'
_publ_section_title
;
 Coordination properties of cyclam (1,4,8,11-tetraazacyclotetradecane)
 endowed with two methylphosphonic acid pendant arms in the
 1,4-positions
;
_journal_issue                   39
_journal_name_full               'Dalton Transactions'
_journal_page_first              5378
_journal_page_last               5386
_journal_paper_doi               10.1039/b803235a
_journal_year                    2008
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C12 H29 N4 Ni O6 P2, H2 O, Cl'
_chemical_formula_sum            'C12 H31 Cl N4 Ni O7 P2'
_chemical_formula_weight         499.51
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9420(2)
_cell_length_b                   9.4016(3)
_cell_length_c                   27.8565(8)
_cell_measurement_reflns_used    2720
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2079.98(10)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            4739
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.256
_exptl_absorpt_correction_T_max  0.8847
_exptl_absorpt_correction_T_min  0.6676
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0248P)²+2.9831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                4236
_reflns_number_total             4739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803235a.txt
_cod_data_source_block           ni14dip
_cod_database_code               7004150
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.74989(5) 0.28049(4) 0.155184(13) 0.01461(10) Uani 1 1 d . . .
N1 N 0.6195(4) 0.3966(3) 0.10106(10) 0.0171(6) Uani 1 1 d . . .
C2 C 0.6447(5) 0.3076(4) 0.05767(12) 0.0206(7) Uani 1 1 d . . .
H21 H 0.6196 0.3644 0.0286 0.025 Uiso 1 1 calc R . .
H22 H 0.5663 0.2258 0.0585 0.025 Uiso 1 1 calc R . .
C3 C 0.8239(5) 0.2542(4) 0.05543(12) 0.0227(8) Uani 1 1 d . . .
H31 H 0.8402 0.1984 0.0257 0.027 Uiso 1 1 calc R . .
H32 H 0.9022 0.3361 0.0546 0.027 Uiso 1 1 calc R . .
N4 N 0.8626(4) 0.1634(3) 0.09788(10) 0.0187(6) Uani 1 1 d . . .
C5 C 1.0475(4) 0.1514(4) 0.10469(13) 0.0237(8) Uani 1 1 d . . .
H51 H 1.0969 0.2480 0.1035 0.028 Uiso 1 1 calc R . .
H52 H 1.0949 0.0965 0.0775 0.028 Uiso 1 1 calc R . .
C6 C 1.1018(4) 0.0803(4) 0.15170(14) 0.0279(8) Uani 1 1 d . . .
H61 H 1.0415 -0.0115 0.1547 0.033 Uiso 1 1 calc R . .
H62 H 1.2236 0.0588 0.1497 0.033 Uiso 1 1 calc R . .
C7 C 1.0708(4) 0.1661(4) 0.19703(14) 0.0249(8) Uani 1 1 d . . .
H71 H 1.1283 0.1192 0.2243 0.030 Uiso 1 1 calc R . .
H72 H 1.1208 0.2619 0.1931 0.030 Uiso 1 1 calc R . .
N8 N 0.8901(4) 0.1813(3) 0.20844(10) 0.0181(6) Uani 1 1 d . . .
H81 H 0.8460 0.0906 0.2129 0.022 Uiso 1 1 calc R . .
C9 C 0.8591(5) 0.2638(4) 0.25269(12) 0.0256(8) Uani 1 1 d . . .
H91 H 0.9268 0.3522 0.2523 0.031 Uiso 1 1 calc R . .
H92 H 0.8922 0.2073 0.2812 0.031 Uiso 1 1 calc R . .
C10 C 0.6724(5) 0.2998(4) 0.25512(12) 0.0242(8) Uani 1 1 d . . .
H101 H 0.6050 0.2114 0.2568 0.029 Uiso 1 1 calc R . .
H102 H 0.6488 0.3572 0.2841 0.029 Uiso 1 1 calc R . .
N11 N 0.6269(4) 0.3814(3) 0.21143(9) 0.0185(6) Uani 1 1 d . . .
H111 H 0.6716 0.4724 0.2144 0.022 Uiso 1 1 calc R . .
C12 C 0.4430(4) 0.3950(4) 0.20484(13) 0.0234(8) Uani 1 1 d . . .
H121 H 0.3940 0.4422 0.2334 0.028 Uiso 1 1 calc R . .
H122 H 0.3928 0.2990 0.2023 0.028 Uiso 1 1 calc R . .
C13 C 0.3982(4) 0.4805(4) 0.16014(13) 0.0232(7) Uani 1 1 d . . .
H131 H 0.2764 0.5026 0.1612 0.028 Uiso 1 1 calc R . .
H132 H 0.4598 0.5719 0.1613 0.028 Uiso 1 1 calc R . .
C14 C 0.4366(4) 0.4088(4) 0.11238(13) 0.0219(7) Uani 1 1 d . . .
H141 H 0.3869 0.3122 0.1126 0.026 Uiso 1 1 calc R . .
H142 H 0.3811 0.4633 0.0864 0.026 Uiso 1 1 calc R . .
C15 C 0.6960(4) 0.5408(3) 0.09370(12) 0.0195(7) Uani 1 1 d . . .
H151 H 0.6086 0.6128 0.0954 0.023 Uiso 1 1 d R . .
H152 H 0.7459 0.5448 0.0619 0.023 Uiso 1 1 d R . .
P1 P 0.85687(11) 0.57984(9) 0.13798(3) 0.01842(18) Uani 1 1 d . . .
O11 O 0.9364(3) 0.4390(2) 0.15013(9) 0.0211(5) Uani 1 1 d . . .
O12 O 0.7786(3) 0.6521(2) 0.18191(8) 0.0210(5) Uani 1 1 d . . .
H12O H 0.7464 0.7625 0.1832 0.025 Uiso 1 1 d R . .
O13 O 0.9781(3) 0.6920(2) 0.11596(9) 0.0260(6) Uani 1 1 d . . .
H13O H 1.0665 0.6532 0.0904 0.031 Uiso 1 1 d R . .
C16 C 0.7837(4) 0.0191(3) 0.09208(12) 0.0221(8) Uani 1 1 d . . .
H161 H 0.8732 -0.0541 0.0907 0.026 Uiso 1 1 calc R . .
H162 H 0.7203 0.0158 0.0615 0.026 Uiso 1 1 calc R . .
P2 P 0.64223(11) -0.01994(9) 0.14162(3) 0.01720(18) Uani 1 1 d . . .
O21 O 0.5643(3) 0.1186(2) 0.15549(9) 0.0189(5) Uani 1 1 d . . .
O22 O 0.5136(3) -0.1339(3) 0.12245(9) 0.0243(6) Uani 1 1 d . . .
H22O H 0.4095 -0.1203 0.1125 0.029 Uiso 1 1 d R . .
O23 O 0.7353(3) -0.0934(2) 0.18253(7) 0.0206(5) Uani 1 1 d . . .
Cl1 Cl 0.36147(13) 0.93599(11) 0.02891(3) 0.0342(2) Uani 1 1 d . . .
O1W O 0.1548(4) 0.6448(3) 0.04010(10) 0.0424(7) Uani 1 1 d . . .
H1W1 H 0.2399 0.6957 0.0348 0.051 Uiso 1 1 d R . .
H1W2 H 0.0688 0.6392 0.0209 0.051 Uiso 1 1 d R . .
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'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 '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
N11 Ni1 N8 85.31(11) . . ?
N11 Ni1 O11 93.33(10) . . ?
N8 Ni1 O11 89.34(10) . . ?
N11 Ni1 O21 89.89(10) . . ?
N8 Ni1 O21 92.72(10) . . ?
O11 Ni1 O21 176.32(10) . . ?
N11 Ni1 N1 94.09(10) . . ?
N8 Ni1 N1 175.36(11) . . ?
O11 Ni1 N1 86.10(10) . . ?
O21 Ni1 N1 91.88(10) . . ?
N11 Ni1 N4 175.52(12) . . ?
N8 Ni1 N4 94.47(11) . . ?
O11 Ni1 N4 91.14(10) . . ?
O21 Ni1 N4 85.66(10) . . ?
N1 Ni1 N4 86.48(11) . . ?
C2 N1 C14 110.3(3) . . ?
C2 N1 C15 110.1(3) . . ?
C14 N1 C15 110.7(3) . . ?
C2 N1 Ni1 102.8(2) . . ?
C14 N1 Ni1 111.3(2) . . ?
C15 N1 Ni1 111.3(2) . . ?
N1 C2 C3 110.4(3) . . ?
N1 C2 H21 109.6 . . ?
C3 C2 H21 109.6 . . ?
N1 C2 H22 109.6 . . ?
C3 C2 H22 109.6 . . ?
H21 C2 H22 108.1 . . ?
N4 C3 C2 110.6(3) . . ?
N4 C3 H31 109.5 . . ?
C2 C3 H31 109.5 . . ?
N4 C3 H32 109.5 . . ?
C2 C3 H32 109.5 . . ?
H31 C3 H32 108.1 . . ?
C5 N4 C3 110.4(3) . . ?
C5 N4 C16 110.9(3) . . ?
C3 N4 C16 110.2(3) . . ?
C5 N4 Ni1 111.0(2) . . ?
C3 N4 Ni1 102.22(19) . . ?
C16 N4 Ni1 111.8(2) . . ?
N4 C5 C6 114.9(3) . . ?
N4 C5 H51 108.5 . . ?
C6 C5 H51 108.5 . . ?
N4 C5 H52 108.5 . . ?
C6 C5 H52 108.5 . . ?
H51 C5 H52 107.5 . . ?
C7 C6 C5 115.6(3) . . ?
C7 C6 H61 108.4 . . ?
C5 C6 H61 108.4 . . ?
C7 C6 H62 108.4 . . ?
C5 C6 H62 108.4 . . ?
H61 C6 H62 107.4 . . ?
N8 C7 C6 112.8(3) . . ?
N8 C7 H71 109.0 . . ?
C6 C7 H71 109.0 . . ?
N8 C7 H72 109.0 . . ?
C6 C7 H72 109.0 . . ?
H71 C7 H72 107.8 . . ?
C9 N8 C7 113.1(3) . . ?
C9 N8 Ni1 105.7(2) . . ?
C7 N8 Ni1 114.2(2) . . ?
C9 N8 H81 107.8 . . ?
C7 N8 H81 107.8 . . ?
Ni1 N8 H81 107.8 . . ?
N8 C9 C10 108.4(3) . . ?
N8 C9 H91 110.0 . . ?
C10 C9 H91 110.0 . . ?
N8 C9 H92 110.0 . . ?
C10 C9 H92 110.0 . . ?
H91 C9 H92 108.4 . . ?
N11 C10 C9 108.4(3) . . ?
N11 C10 H101 110.0 . . ?
C9 C10 H101 110.0 . . ?
N11 C10 H102 110.0 . . ?
C9 C10 H102 110.0 . . ?
H101 C10 H102 108.4 . . ?
C12 N11 C10 112.8(3) . . ?
C12 N11 Ni1 114.3(2) . . ?
C10 N11 Ni1 105.6(2) . . ?
C12 N11 H111 108.0 . . ?
C10 N11 H111 108.0 . . ?
Ni1 N11 H111 108.0 . . ?
N11 C12 C13 112.2(3) . . ?
N11 C12 H121 109.2 . . ?
C13 C12 H121 109.2 . . ?
N11 C12 H122 109.2 . . ?
C13 C12 H122 109.2 . . ?
H121 C12 H122 107.9 . . ?
C14 C13 C12 115.7(3) . . ?
C14 C13 H131 108.4 . . ?
C12 C13 H131 108.4 . . ?
C14 C13 H132 108.4 . . ?
C12 C13 H132 108.4 . . ?
H131 C13 H132 107.4 . . ?
N1 C14 C13 114.5(3) . . ?
N1 C14 H141 108.6 . . ?
C13 C14 H141 108.6 . . ?
N1 C14 H142 108.6 . . ?
C13 C14 H142 108.6 . . ?
H141 C14 H142 107.6 . . ?
N1 C15 P1 112.0(2) . . ?
N1 C15 H151 109.5 . . ?
P1 C15 H151 109.3 . . ?
N1 C15 H152 109.0 . . ?
P1 C15 H152 109.0 . . ?
H151 C15 H152 108.0 . . ?
O11 P1 O12 112.38(14) . . ?
O11 P1 O13 115.18(14) . . ?
O12 P1 O13 105.42(14) . . ?
O11 P1 C15 105.70(14) . . ?
O12 P1 C15 110.32(14) . . ?
O13 P1 C15 107.77(15) . . ?
P1 O11 Ni1 110.01(12) . . ?
P1 O12 H12O 123.7 . . ?
P1 O13 H13O 116.1 . . ?
N4 C16 P2 111.0(2) . . ?
N4 C16 H161 109.4 . . ?
P2 C16 H161 109.4 . . ?
N4 C16 H162 109.4 . . ?
P2 C16 H162 109.4 . . ?
H161 C16 H162 108.0 . . ?
O21 P2 O23 113.76(13) . . ?
O21 P2 O22 114.37(14) . . ?
O23 P2 O22 105.09(13) . . ?
O21 P2 C16 106.06(14) . . ?
O23 P2 C16 111.08(15) . . ?
O22 P2 C16 106.34(14) . . ?
P2 O21 Ni1 109.72(12) . . ?
P2 O22 H22O 128.1 . . ?
H1W1 O1W H1W2 123.8 . . ?
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
Ni1 N11 2.076(3) . ?
Ni1 N8 2.076(3) . ?
Ni1 O11 2.106(2) . ?
Ni1 O21 2.119(2) . ?
Ni1 N1 2.130(3) . ?
Ni1 N4 2.136(3) . ?
N1 C2 1.483(4) . ?
N1 C14 1.490(4) . ?
N1 C15 1.500(4) . ?
C2 C3 1.511(5) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.490(4) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.485(4) . ?
N4 C16 1.503(4) . ?
C5 C6 1.533(5) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.519(5) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N8 1.477(4) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
N8 C9 1.477(4) . ?
N8 H81 0.9300 . ?
C9 C10 1.523(5) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 N11 1.483(4) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
N11 C12 1.477(4) . ?
N11 H111 0.9300 . ?
C12 C13 1.524(5) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
C13 C14 1.522(5) . ?
C13 H131 0.9900 . ?
C13 H132 0.9900 . ?
C14 H141 0.9900 . ?
C14 H142 0.9900 . ?
C15 P1 1.813(3) . ?
C15 H151 0.9703 . ?
C15 H152 0.9698 . ?
P1 O11 1.505(2) . ?
P1 O12 1.531(2) . ?
P1 O13 1.554(2) . ?
O12 H12O 1.0703 . ?
O13 H13O 1.0650 . ?
C16 P2 1.817(3) . ?
C16 H161 0.9900 . ?
C16 H162 0.9900 . ?
P2 O21 1.493(2) . ?
P2 O23 1.523(2) . ?
P2 O22 1.573(2) . ?
O22 H22O 0.8811 . ?
O1W H1W1 0.8410 . ?
O1W H1W2 0.8686 . ?
