#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:37:32 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179799 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/95/7009576.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_7009576
loop_
_publ_author_name
'Pennemann, Helmut'
'Wassmann, Suzanne'
'Wilken, Jörg'
'Gröger, Harald'
'Wallbaum, Sabine'
'Kossenjans, Michael'
'Haase, Detlev'
'Saak, Wolfgang'
'Pohl, Siegfried'
'Martens, Jürgen'
_publ_section_title
;
 Preparation of an enantiomerically pure helical nickel(II) complex
 using a new chiral tetradentate ligand derived from an industrial
 waste material †
;
_journal_issue                   14
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              2467
_journal_paper_doi               10.1039/b002130j
_journal_year                    2000
_chemical_formula_sum            'C18 H30 N2 Ni O6'
_chemical_formula_weight         429.13
_chemical_name_common            '[Ni(edda)(H2O)]xH2O'
_chemical_temperature_decomposition_gt 447.15
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 104.860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3020(10)
_cell_length_b                   15.2160(10)
_cell_length_c                   8.9250(10)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    295(2)
_cell_volume                     958.47(19)
_computing_cell_refinement       'STADI 4 (Stoe, 1993)'
_computing_data_collection       'STADI4 (Stoe, 1993)'
_computing_data_reduction        'XRED (Stoe, 1993)'
_computing_molecular_graphics    'Schakal97 (E. Keller, 1997)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL Plus'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe AED2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2336
_diffrn_reflns_theta_full        27.01
_diffrn_reflns_theta_max         27.01
_diffrn_reflns_theta_min         3.23
_diffrn_standards_interval_time  45
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.2902
_exptl_absorpt_correction_T_min  0.2015
_exptl_absorpt_correction_type   'empirical psi-scan'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       'square crystals'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .6
_exptl_crystal_size_min          .4
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0349
_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)+(0.0700P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                2104
_reflns_number_total             2172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002130j.txt
_cod_data_source_block           '[Ni(edda)(H2O)]xH2O'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified 'more than' ('>') a certain temperature. The value '>174 C
(decomposition)' was changed to '447.15' - it was converted from
degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        958.47(18)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7009576
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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
Ni1 Ni 0.22164(5) 0.2524 0.08144(4) 0.03078(13) Uani 1 1 d . . .
O1 O 0.3892(4) 0.3252(2) -0.0140(4) 0.0470(7) Uani 1 1 d . . .
O2 O 0.6832(4) 0.3664(2) 0.0055(4) 0.0546(8) Uani 1 1 d . . .
O3 O 0.0581(4) 0.20607(17) 0.2100(3) 0.0366(5) Uani 1 1 d . . .
O4 O -0.0783(4) 0.0841(2) 0.2665(3) 0.0465(6) Uani 1 1 d . . .
O5W O -0.0023(4) 0.3108(3) -0.0590(4) 0.0608(10) Uani 1 1 d . . .
O6W O 0.1291(5) 0.4067(2) 0.7386(4) 0.0568(8) Uani 1 1 d . . .
C1 C 0.4453(5) 0.0972(2) 0.1350(4) 0.0353(7) Uani 1 1 d . . .
H1A H 0.5429 0.1123 0.0834 0.080 Uiso 1 1 calc R . .
H1B H 0.4523 0.0343 0.1540 0.080 Uiso 1 1 calc R . .
C2 C 0.4847(5) 0.1452(2) 0.2897(4) 0.0351(7) Uani 1 1 d . . .
H2A H 0.3973 0.1253 0.3480 0.080 Uiso 1 1 calc R . .
H2B H 0.6126 0.1326 0.3500 0.080 Uiso 1 1 calc R . .
N3 N 0.4619(4) 0.2418(2) 0.2611(3) 0.0306(6) Uani 1 1 d . . .
C4 C 0.6269(5) 0.2798(2) 0.2106(4) 0.0358(7) Uani 1 1 d . . .
H4 H 0.7122 0.2318 0.2001 0.080 Uiso 1 1 calc R . .
C5 C 0.5637(5) 0.3276(2) 0.0553(5) 0.0381(7) Uani 1 1 d . . .
C6 C 0.7325(6) 0.3414(4) 0.3414(5) 0.0556(11) Uani 1 1 d . . .
H6A H 0.8676 0.3298 0.3670 0.080 Uiso 1 1 calc R . .
H6B H 0.7114 0.4023 0.3095 0.080 Uiso 1 1 calc R . .
C7 C 0.6540(5) 0.3233(3) 0.4809(4) 0.0448(8) Uani 1 1 d . . .
H7 H 0.7292 0.2789 0.5494 0.080 Uiso 1 1 calc R . .
C8 C 0.6235(8) 0.4044(4) 0.5707(6) 0.0630(12) Uani 1 1 d . . .
H8A H 0.6161 0.3884 0.6742 0.080 Uiso 1 1 calc R . .
H8B H 0.7269 0.4457 0.5793 0.080 Uiso 1 1 calc R . .
C9 C 0.4410(8) 0.4441(4) 0.4814(7) 0.0667(13) Uani 1 1 d . . .
H9A H 0.4656 0.4941 0.4220 0.080 Uiso 1 1 calc R . .
H9B H 0.3681 0.4641 0.5517 0.080 Uiso 1 1 calc R . .
C10 C 0.3312(7) 0.3738(3) 0.3729(6) 0.0581(12) Uani 1 1 d . . .
H10A H 0.3108 0.3919 0.2657 0.080 Uiso 1 1 calc R . .
H10B H 0.2090 0.3636 0.3939 0.080 Uiso 1 1 calc R . .
C11 C 0.4533(5) 0.2898(3) 0.4043(4) 0.0377(7) Uani 1 1 d . . .
H11 H 0.4092 0.2508 0.4751 0.080 Uiso 1 1 calc R . .
N12 N 0.2574(4) 0.1187(2) 0.0311(3) 0.0312(6) Uani 1 1 d . . .
C13 C 0.0966(5) 0.0735(2) 0.0763(4) 0.0325(6) Uani 1 1 d . . .
H13 H 0.1341 0.0140 0.1138 0.080 Uiso 1 1 calc R . .
C14 C 0.0225(5) 0.1241(2) 0.1965(4) 0.0323(6) Uani 1 1 d . . .
C15 C -0.0582(5) 0.0696(3) -0.0751(4) 0.0432(8) Uani 1 1 d . . .
H15A H -0.1246 0.1252 -0.0960 0.080 Uiso 1 1 calc R . .
H15B H -0.1490 0.0236 -0.0714 0.080 Uiso 1 1 calc R . .
C16 C 0.0475(6) 0.0496(3) -0.1981(4) 0.0464(9) Uani 1 1 d . . .
H16 H 0.0491 -0.0141 -0.2149 0.080 Uiso 1 1 calc R . .
C17 C -0.0225(9) 0.0965(6) -0.3547(6) 0.0786(19) Uani 1 1 d . . .
H17A H -0.0205 0.0570 -0.4396 0.080 Uiso 1 1 calc R . .
H17B H -0.1506 0.1182 -0.3679 0.080 Uiso 1 1 calc R . .
C18 C 0.1096(13) 0.1694(7) -0.3494(10) 0.126(4) Uani 1 1 d . . .
H18A H 0.1260 0.1800 -0.4524 0.080 Uiso 1 1 calc R . .
H18B H 0.0584 0.2223 -0.3152 0.080 Uiso 1 1 calc R . .
C19 C 0.2921(8) 0.1489(4) -0.2435(6) 0.0625(13) Uani 1 1 d . . .
H19B H 0.3495 0.2014 -0.1897 0.080 Uiso 1 1 calc R . .
H19A H 0.3776 0.1241 -0.2994 0.080 Uiso 1 1 calc R . .
C20 C 0.2505(6) 0.0824(3) -0.1294(4) 0.0413(8) Uani 1 1 d . . .
H20 H 0.3388 0.0330 -0.1195 0.080 Uiso 1 1 calc 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 for Crystallography
 (1976, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;International Tables for Crystallography
 (1976, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;International Tables for Crystallography
 (1976, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;International Tables for Crystallography
 (1976, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni 0.3393 1.1124
;International Tables for Crystallography
 (1976, 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
O3 Ni1 O5W 90.21(12) . . ?
O3 Ni1 O1 165.70(13) . . ?
O5W Ni1 O1 88.75(12) . . ?
O3 Ni1 N3 92.35(11) . . ?
O5W Ni1 N3 157.23(15) . . ?
O1 Ni1 N3 83.25(11) . . ?
O3 Ni1 N12 84.64(10) . . ?
O5W Ni1 N12 114.87(16) . . ?
O1 Ni1 N12 108.69(13) . . ?
N3 Ni1 N12 87.89(12) . . ?
C5 O1 Ni1 117.3(2) . . ?
C14 O3 Ni1 115.6(2) . . ?
N12 C1 C2 113.0(3) . . ?
N3 C2 C1 109.3(3) . . ?
C11 N3 C2 111.3(3) . . ?
C11 N3 C4 106.4(3) . . ?
C2 N3 C4 111.5(3) . . ?
C11 N3 Ni1 114.6(2) . . ?
C2 N3 Ni1 104.2(2) . . ?
C4 N3 Ni1 109.0(2) . . ?
N3 C4 C5 112.0(3) . . ?
N3 C4 C6 106.9(3) . . ?
C5 C4 C6 111.9(3) . . ?
O2 C5 O1 123.8(4) . . ?
O2 C5 C4 118.7(3) . . ?
O1 C5 C4 117.4(3) . . ?
C7 C6 C4 106.8(3) . . ?
C8 C7 C6 115.0(4) . . ?
C8 C7 C11 104.6(3) . . ?
C6 C7 C11 102.3(3) . . ?
C9 C8 C7 106.1(4) . . ?
C8 C9 C10 107.9(4) . . ?
C9 C10 C11 106.3(4) . . ?
N3 C11 C7 107.4(3) . . ?
N3 C11 C10 113.6(3) . . ?
C7 C11 C10 104.3(3) . . ?
C1 N12 C13 113.1(3) . . ?
C1 N12 C20 108.1(3) . . ?
C13 N12 C20 104.3(3) . . ?
C1 N12 Ni1 103.0(2) . . ?
C13 N12 Ni1 103.62(19) . . ?
C20 N12 Ni1 124.9(2) . . ?
N12 C13 C15 103.5(3) . . ?
N12 C13 C14 113.6(3) . . ?
C15 C13 C14 109.1(3) . . ?
O4 C14 O3 124.5(3) . . ?
O4 C14 C13 118.0(3) . . ?
O3 C14 C13 117.4(3) . . ?
C13 C15 C16 104.4(3) . . ?
C15 C16 C20 105.2(3) . . ?
C15 C16 C17 116.8(4) . . ?
C20 C16 C17 105.9(4) . . ?
C18 C17 C16 105.1(5) . . ?
C19 C18 C17 110.2(6) . . ?
C18 C19 C20 105.7(4) . . ?
C19 C20 N12 115.1(4) . . ?
C19 C20 C16 106.7(4) . . ?
N12 C20 C16 106.8(3) . . ?
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 O3 1.985(2) . ?
Ni1 O5W 1.995(3) . ?
Ni1 O1 1.996(3) . ?
Ni1 N3 2.057(3) . ?
Ni1 N12 2.114(3) . ?
O1 C5 1.266(5) . ?
O2 C5 1.227(5) . ?
O3 C14 1.273(5) . ?
O4 C14 1.240(4) . ?
C1 N12 1.483(4) . ?
C1 C2 1.523(5) . ?
C2 N3 1.494(4) . ?
N3 C11 1.488(4) . ?
N3 C4 1.506(4) . ?
C4 C5 1.528(5) . ?
C4 C6 1.541(6) . ?
C6 C7 1.523(6) . ?
C7 C8 1.518(7) . ?
C7 C11 1.537(5) . ?
C8 C9 1.494(8) . ?
C9 C10 1.525(7) . ?
C10 C11 1.542(6) . ?
N12 C13 1.502(4) . ?
N12 C20 1.523(4) . ?
C13 C15 1.524(5) . ?
C13 C14 1.527(5) . ?
C15 C16 1.526(5) . ?
C16 C20 1.535(6) . ?
C16 C17 1.536(7) . ?
C17 C18 1.462(11) . ?
C18 C19 1.457(9) . ?
C19 C20 1.520(6) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Ni1 O1 C5 80.4(6) . . . . ?
O5W Ni1 O1 C5 166.3(3) . . . . ?
N3 Ni1 O1 C5 7.7(3) . . . . ?
N12 Ni1 O1 C5 -77.8(3) . . . . ?
O5W Ni1 O3 C14 106.8(3) . . . . ?
O1 Ni1 O3 C14 -167.5(4) . . . . ?
N3 Ni1 O3 C14 -95.9(3) . . . . ?
N12 Ni1 O3 C14 -8.2(3) . . . . ?
N12 C1 C2 N3 -55.0(4) . . . . ?
C1 C2 N3 C11 166.5(3) . . . . ?
C1 C2 N3 C4 -74.9(4) . . . . ?
C1 C2 N3 Ni1 42.4(3) . . . . ?
O3 Ni1 N3 C11 -56.4(2) . . . . ?
O5W Ni1 N3 C11 39.8(4) . . . . ?
O1 Ni1 N3 C11 110.0(3) . . . . ?
N12 Ni1 N3 C11 -140.9(2) . . . . ?
O3 Ni1 N3 C2 65.6(2) . . . . ?
O5W Ni1 N3 C2 161.7(3) . . . . ?
O1 Ni1 N3 C2 -128.1(2) . . . . ?
N12 Ni1 N3 C2 -19.0(2) . . . . ?
O3 Ni1 N3 C4 -175.4(2) . . . . ?
O5W Ni1 N3 C4 -79.2(4) . . . . ?
O1 Ni1 N3 C4 -9.0(2) . . . . ?
N12 Ni1 N3 C4 100.1(2) . . . . ?
C11 N3 C4 C5 -114.6(3) . . . . ?
C2 N3 C4 C5 123.9(3) . . . . ?
Ni1 N3 C4 C5 9.4(3) . . . . ?
C11 N3 C4 C6 8.3(4) . . . . ?
C2 N3 C4 C6 -113.2(4) . . . . ?
Ni1 N3 C4 C6 132.3(3) . . . . ?
Ni1 O1 C5 O2 176.5(3) . . . . ?
Ni1 O1 C5 C4 -4.1(5) . . . . ?
N3 C4 C5 O2 175.4(3) . . . . ?
C6 C4 C5 O2 55.4(5) . . . . ?
N3 C4 C5 O1 -4.0(5) . . . . ?
C6 C4 C5 O1 -124.0(4) . . . . ?
N3 C4 C6 C7 12.2(5) . . . . ?
C5 C4 C6 C7 135.2(4) . . . . ?
C4 C6 C7 C8 -139.5(4) . . . . ?
C4 C6 C7 C11 -26.8(5) . . . . ?
C6 C7 C8 C9 79.7(5) . . . . ?
C11 C7 C8 C9 -31.6(5) . . . . ?
C7 C8 C9 C10 18.7(6) . . . . ?
C8 C9 C10 C11 1.4(6) . . . . ?
C2 N3 C11 C7 95.8(3) . . . . ?
C4 N3 C11 C7 -25.8(4) . . . . ?
Ni1 N3 C11 C7 -146.3(3) . . . . ?
C2 N3 C11 C10 -149.4(3) . . . . ?
C4 N3 C11 C10 89.0(4) . . . . ?
Ni1 N3 C11 C10 -31.4(4) . . . . ?
C8 C7 C11 N3 152.8(4) . . . . ?
C6 C7 C11 N3 32.6(4) . . . . ?
C8 C7 C11 C10 32.0(5) . . . . ?
C6 C7 C11 C10 -88.2(4) . . . . ?
C9 C10 C11 N3 -137.3(4) . . . . ?
C9 C10 C11 C7 -20.6(5) . . . . ?
C2 C1 N12 C13 -76.4(4) . . . . ?
C2 C1 N12 C20 168.6(3) . . . . ?
C2 C1 N12 Ni1 34.7(3) . . . . ?
O3 Ni1 N12 C1 -100.6(2) . . . . ?
O5W Ni1 N12 C1 171.66(19) . . . . ?
O1 Ni1 N12 C1 74.1(2) . . . . ?
N3 Ni1 N12 C1 -8.0(2) . . . . ?
O3 Ni1 N12 C13 17.5(2) . . . . ?
O5W Ni1 N12 C13 -70.3(2) . . . . ?
O1 Ni1 N12 C13 -167.8(2) . . . . ?
N3 Ni1 N12 C13 110.0(2) . . . . ?
O3 Ni1 N12 C20 136.1(3) . . . . ?
O5W Ni1 N12 C20 48.4(3) . . . . ?
O1 Ni1 N12 C20 -49.2(3) . . . . ?
N3 Ni1 N12 C20 -131.3(3) . . . . ?
C1 N12 C13 C15 -155.1(3) . . . . ?
C20 N12 C13 C15 -37.9(3) . . . . ?
Ni1 N12 C13 C15 94.1(3) . . . . ?
C1 N12 C13 C14 86.8(3) . . . . ?
C20 N12 C13 C14 -156.0(3) . . . . ?
Ni1 N12 C13 C14 -24.0(3) . . . . ?
Ni1 O3 C14 O4 -179.3(3) . . . . ?
Ni1 O3 C14 C13 -4.3(4) . . . . ?
N12 C13 C14 O4 -163.9(3) . . . . ?
C15 C13 C14 O4 81.3(4) . . . . ?
N12 C13 C14 O3 20.7(4) . . . . ?
C15 C13 C14 O3 -94.1(4) . . . . ?
N12 C13 C15 C16 38.8(4) . . . . ?
C14 C13 C15 C16 160.0(3) . . . . ?
C13 C15 C16 C20 -24.2(4) . . . . ?
C13 C15 C16 C17 -141.2(5) . . . . ?
C15 C16 C17 C18 100.6(7) . . . . ?
C20 C16 C17 C18 -16.0(8) . . . . ?
C16 C17 C18 C19 25.8(10) . . . . ?
C17 C18 C19 C20 -24.9(10) . . . . ?
C18 C19 C20 N12 -104.8(7) . . . . ?
C18 C19 C20 C16 13.6(7) . . . . ?
C1 N12 C20 C19 -98.2(4) . . . . ?
C13 N12 C20 C19 141.2(4) . . . . ?
Ni1 N12 C20 C19 22.9(4) . . . . ?
C1 N12 C20 C16 143.6(3) . . . . ?
C13 N12 C20 C16 22.9(4) . . . . ?
Ni1 N12 C20 C16 -95.4(3) . . . . ?
C15 C16 C20 C19 -122.7(4) . . . . ?
C17 C16 C20 C19 1.6(5) . . . . ?
C15 C16 C20 N12 1.0(4) . . . . ?
C17 C16 C20 N12 125.2(4) . . . . ?
