#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/77/2007707.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_2007707
loop_
_publ_author_name
'König, Burkhard'
'Pelka, Mario'
'Dix, Ina'
'Jones, Peter G.'
_publ_section_title
;
 3,3'-[Ethane-1,2-diylbis(aminomethylene)]bis(pentane-2,4-dione) and
 the Nickel(II) Complex of a Condensation Product
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1468
_journal_page_last               1471
_journal_paper_doi               10.1107/S0108270198009263
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          '[Ni (C16 H22 N4 O2)], 2C D Cl3'
_chemical_formula_moiety         '(C16 H22 N4 Ni O2) 2(C D Cl3)'
_chemical_formula_sum            'C18 H22 Cl6 D2 N4 Ni O2'
_chemical_formula_weight         601.83
_chemical_name_systematic
;
 [{6,13-diacetyl-5,12-dimethyl-1,4,8,11-tetraazacyclotetradeca-
 4,6,11,13-tetraenato(2-)}nickel(II)] deuterochloroform solvate (1:2)
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                   8.542(3)
_cell_length_b                   9.406(3)
_cell_length_c                   30.213(8)
_cell_measurement_reflns_used    60
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      5.9
_cell_volume                     2427.5(13)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            4120
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         3.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.484
_exptl_absorpt_correction_T_max  0.690
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   '\y scans (XEMP; Siemens, 1994a)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.33
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.422(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.031
_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)+(0.0271P)²+2.643P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.069
_reflns_number_gt                3587
_reflns_number_total             3996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1271.cif
_cod_data_source_block           2
_cod_original_cell_volume        2427.3(13)
_cod_original_formula_sum        'C18 H22 D2 Cl6 N4 Ni O2'
_cod_database_code               2007707
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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
Ni 0.47261(4) 0.75128(5) 0.455300(18) 0.01651(9) Uani d . 1 . . Ni
O1 0.9552(4) 0.7996(4) 0.33716(10) 0.0373(8) Uani d . 1 . . O
O2 -0.0139(3) 0.6732(3) 0.56859(9) 0.0280(7) Uani d . 1 . . O
N1 0.2685(3) 0.8176(3) 0.46619(8) 0.0179(7) Uani d . 1 . . N
N4 0.4438(3) 0.8036(3) 0.39734(9) 0.0187(7) Uani d . 1 . . N
N8 0.6764(3) 0.6834(3) 0.44451(9) 0.0189(7) Uani d . 1 . . N
N11 0.5005(4) 0.7006(3) 0.51355(10) 0.0188(7) Uani d . 1 . . N
C2 0.2136(4) 0.9063(4) 0.42871(12) 0.0238(8) Uani d . 1 . . C
H2A 0.2494 1.0058 0.4324 0.029 Uiso calc R 1 . . H
H2B 0.0978 0.9057 0.4271 0.029 Uiso calc R 1 . . H
C3 0.2824(4) 0.8426(4) 0.38756(12) 0.0250(9) Uani d . 1 . . C
H3A 0.2219 0.7575 0.3786 0.030 Uiso calc R 1 . . H
H3B 0.2791 0.9123 0.3630 0.030 Uiso calc R 1 . . H
C5 0.5503(4) 0.8098(4) 0.36667(11) 0.0209(8) Uani d . 1 . . C
H5 0.5185 0.8477 0.3389 0.025 Uiso calc R 1 . . H
C6 0.7073(4) 0.7665(4) 0.37008(11) 0.0210(8) Uani d . 1 . . C
C7 0.7607(4) 0.6903(4) 0.40835(11) 0.0187(7) Uani d . 1 . . C
C9 0.7316(4) 0.5990(4) 0.48303(11) 0.0219(8) Uani d . 1 . . C
H9A 0.8474 0.5992 0.4843 0.026 Uiso calc R 1 . . H
H9B 0.6952 0.4994 0.4806 0.026 Uiso calc R 1 . . H
C10 0.6648(4) 0.6675(4) 0.52355(12) 0.0227(8) Uani d . 1 . . C
H10A 0.6716 0.6020 0.5491 0.027 Uiso calc R 1 . . H
H10B 0.7230 0.7555 0.5308 0.027 Uiso calc R 1 . . H
C12 0.3949(4) 0.6882(4) 0.54378(12) 0.0199(8) Uani d . 1 . . C
H12 0.4272 0.6498 0.5714 0.024 Uiso calc R 1 . . H
C13 0.2359(4) 0.7264(4) 0.53968(11) 0.0196(8) Uani d . 1 . . C
C14 0.1830(4) 0.8068(4) 0.50193(11) 0.0179(7) Uani d . 1 . . C
C15 0.8120(5) 0.8031(4) 0.33364(12) 0.0258(9) Uani d . 1 . . C
C16 0.7424(6) 0.8497(5) 0.28983(12) 0.0370(10) Uani d . 1 . . C
H16A 0.8255 0.8560 0.2675 0.044 Uiso calc R 1 . . H
H16B 0.6929 0.9431 0.2933 0.044 Uiso calc R 1 . . H
H16C 0.6638 0.7803 0.2803 0.044 Uiso calc R 1 . . H
C17 0.1295(5) 0.6778(4) 0.57389(11) 0.0222(8) Uani d . 1 . . C
C18 0.1935(5) 0.6252(4) 0.61777(12) 0.0301(9) Uani d . 1 . . C
H18A 0.1064 0.6004 0.6374 0.036 Uiso calc R 1 . . H
H18B 0.2567 0.7002 0.6315 0.036 Uiso calc R 1 . . H
H18C 0.2588 0.5411 0.6128 0.036 Uiso calc R 1 . . H
C19 0.9108(5) 0.6047(4) 0.40623(12) 0.0264(8) Uani d . 1 . . C
H19A 0.9900 0.6491 0.4252 0.032 Uiso calc R 1 . . H
H19B 0.9488 0.6020 0.3756 0.032 Uiso calc R 1 . . H
H19C 0.8907 0.5075 0.4165 0.032 Uiso calc R 1 . . H
C20 0.0331(4) 0.8901(4) 0.50523(12) 0.0248(8) Uani d . 1 . . C
H20A 0.0525 0.9891 0.4968 0.030 Uiso calc R 1 . . H
H20B -0.0057 0.8867 0.5357 0.030 Uiso calc R 1 . . H
H20C -0.0452 0.8487 0.4853 0.030 Uiso calc R 1 . . H
C98 1.1642(6) 0.6357(5) 0.26528(15) 0.0452(12) Uani d . 1 . . C
D98 1.0654 0.6710 0.2792 0.054 Uiso calc R 1 . . H
Cl1 1.2603(2) 0.77874(16) 0.24173(6) 0.0888(6) Uani d . 1 . . Cl
Cl2 1.11536(19) 0.51169(17) 0.22455(4) 0.0714(4) Uani d . 1 . . Cl
Cl3 1.2788(2) 0.55532(16) 0.30627(5) 0.0841(6) Uani d . 1 . . Cl
C99 -0.2182(5) 0.8356(5) 0.63637(13) 0.0338(10) Uani d . 1 . . C
D99 -0.1635 0.7625 0.6180 0.041 Uiso calc R 1 . . H
Cl4 -0.25694(16) 0.98359(13) 0.60290(4) 0.0542(3) Uani d . 1 . . Cl
Cl5 -0.09560(17) 0.88261(18) 0.67983(4) 0.0688(4) Uani d . 1 . . Cl
Cl6 -0.39145(15) 0.76011(14) 0.65704(4) 0.0553(3) Uani d . 1 . . Cl
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'
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_publ_flag
N4 Ni N11 179.42(16) y
N4 Ni N1 87.35(12) y
N11 Ni N1 92.22(13) y
N4 Ni N8 92.84(12) y
N11 Ni N8 87.58(13) y
N1 Ni N8 179.54(14) y
C14 N1 C2 119.9(3) y
C14 N1 Ni 129.5(2) y
C2 N1 Ni 110.3(2) y
C5 N4 C3 120.4(3) y
C5 N4 Ni 126.8(3) y
C3 N4 Ni 112.8(2) y
C7 N8 C9 120.3(3) y
C7 N8 Ni 129.5(2) y
C9 N8 Ni 109.8(2) y
C12 N11 C10 120.2(3) y
C12 N11 Ni 127.6(3) y
C10 N11 Ni 112.1(2) y
N1 C2 C3 106.5(3) ?
N4 C3 C2 107.7(3) ?
N4 C5 C6 127.1(3) ?
C5 C6 C7 120.5(3) ?
C5 C6 C15 117.4(3) ?
C7 C6 C15 122.1(3) ?
N8 C7 C6 121.5(3) ?
N8 C7 C19 118.3(3) ?
C6 C7 C19 120.0(3) ?
N8 C9 C10 106.8(3) ?
N11 C10 C9 106.7(3) ?
N11 C12 C13 126.1(3) ?
C12 C13 C14 120.3(3) ?
C12 C13 C17 117.4(3) ?
C14 C13 C17 122.2(3) ?
N1 C14 C13 121.3(3) ?
N1 C14 C20 119.3(3) ?
C13 C14 C20 119.2(3) ?
O1 C15 C6 122.6(4) ?
O1 C15 C16 118.3(4) ?
C6 C15 C16 119.1(4) ?
O2 C17 C13 122.7(3) ?
O2 C17 C18 117.3(3) ?
C13 C17 C18 120.0(3) ?
Cl1 C98 Cl2 110.1(2) ?
Cl1 C98 Cl3 111.2(3) ?
Cl2 C98 Cl3 110.1(3) ?
Cl5 C99 Cl4 110.4(2) ?
Cl5 C99 Cl6 110.0(2) ?
Cl4 C99 Cl6 111.6(2) ?
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
Ni N4 . 1.835(3) y
Ni N11 . 1.839(3) y
Ni N1 . 1.881(3) y
Ni N8 . 1.882(3) y
O1 C15 . 1.228(5) ?
O2 C17 . 1.237(4) ?
N1 C14 . 1.307(4) ?
N1 C2 . 1.483(4) ?
N4 C5 . 1.300(5) ?
N4 C3 . 1.458(5) ?
N8 C7 . 1.310(4) ?
N8 C9 . 1.485(4) ?
N11 C12 . 1.289(5) ?
N11 C10 . 1.469(5) ?
C2 C3 . 1.500(5) ?
C5 C6 . 1.406(5) ?
C6 C7 . 1.434(5) ?
C6 C15 . 1.460(5) ?
C7 C19 . 1.516(5) ?
C9 C10 . 1.497(5) ?
C12 C13 . 1.411(5) ?
C13 C14 . 1.441(5) ?
C13 C17 . 1.450(5) ?
C14 C20 . 1.504(5) ?
C15 C16 . 1.516(5) ?
C17 C18 . 1.517(5) ?
C98 Cl1 . 1.729(5) ?
C98 Cl2 . 1.746(5) ?
C98 Cl3 . 1.751(5) ?
C99 Cl5 . 1.737(4) ?
C99 Cl4 . 1.752(4) ?
C99 Cl6 . 1.756(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_publ_flag
C98 D98 O1 1.00 2.33 3.206(6) 146.2 y
C99 D99 O2 1.00 2.14 3.094(5) 159.7 y
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_publ_flag
N4 Ni N1 C14 172.2(3) ?
N11 Ni N1 C14 -8.2(3) ?
N8 Ni N1 C14 57(16) ?
N4 Ni N1 C2 -14.9(2) y
N11 Ni N1 C2 164.8(2) ?
N8 Ni N1 C2 -130(16) ?
N11 Ni N4 C5 126(15) ?
N1 Ni N4 C5 169.2(3) ?
N8 Ni N4 C5 -11.2(3) ?
N11 Ni N4 C3 -53(16) ?
N1 Ni N4 C3 -9.8(3) y
N8 Ni N4 C3 169.8(3) ?
N4 Ni N8 C7 5.9(3) ?
N11 Ni N8 C7 -173.7(3) ?
N1 Ni N8 C7 121(16) ?
N4 Ni N8 C9 -167.2(2) ?
N11 Ni N8 C9 13.2(2) y
N1 Ni N8 C9 -52(16) ?
N4 Ni N11 C12 57(16) ?
N1 Ni N11 C12 14.4(3) ?
N8 Ni N11 C12 -165.2(3) ?
N4 Ni N11 C10 -125(16) ?
N1 Ni N11 C10 -167.9(3) ?
N8 Ni N11 C10 12.5(3) y
C14 N1 C2 C3 -151.5(3) y
Ni N1 C2 C3 34.8(3) y
C5 N4 C3 C2 -147.5(3) y
Ni N4 C3 C2 31.5(4) y
N1 C2 C3 N4 -41.7(4) y
C3 N4 C5 C6 -175.2(3) ?
Ni N4 C5 C6 5.9(6) ?
N4 C5 C6 C7 8.6(6) ?
N4 C5 C6 C15 -170.9(4) ?
C9 N8 C7 C6 177.6(3) ?
Ni N8 C7 C6 5.1(5) ?
C9 N8 C7 C19 2.9(5) ?
Ni N8 C7 C19 -169.6(2) ?
C5 C6 C7 N8 -13.8(5) ?
C15 C6 C7 N8 165.6(3) ?
C5 C6 C7 C19 160.8(3) ?
C15 C6 C7 C19 -19.7(5) ?
C7 N8 C9 C10 151.3(3) y
Ni N8 C9 C10 -34.9(3) y
C12 N11 C10 C9 143.3(3) y
Ni N11 C10 C9 -34.7(3) y
N8 C9 C10 N11 43.9(4) y
C10 N11 C12 C13 174.9(3) ?
Ni N11 C12 C13 -7.5(5) ?
N11 C12 C13 C14 -10.4(6) ?
N11 C12 C13 C17 167.6(3) ?
C2 N1 C14 C13 -177.3(3) ?
Ni N1 C14 C13 -4.9(5) ?
C2 N1 C14 C20 -2.7(5) ?
Ni N1 C14 C20 169.7(2) ?
C12 C13 C14 N1 16.3(5) ?
C17 C13 C14 N1 -161.6(3) ?
C12 C13 C14 C20 -158.3(3) ?
C17 C13 C14 C20 23.7(5) ?
C5 C6 C15 O1 163.3(4) ?
C7 C6 C15 O1 -16.2(6) ?
C5 C6 C15 C16 -15.7(5) ?
C7 C6 C15 C16 164.8(3) ?
C12 C13 C17 O2 -161.4(4) ?
C14 C13 C17 O2 16.6(6) ?
C12 C13 C17 C18 16.5(5) ?
C14 C13 C17 C18 -165.4(3) ?
