#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/92/4509245.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509245
loop_
_publ_author_name
'Siegler, Maxime A.'
'Lutz, Martin'
_publ_section_title
;
 Ni(salen): a System That Forms Many Solvates with Interacting Ni Atoms
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1194
_journal_paper_doi               10.1021/cg801109n
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C16 H14 N2 Ni O2, C H4 O, 0.5(C H4 O)'
_chemical_formula_sum            'C17.5 H20 N2 Ni O3.5'
_chemical_formula_weight         373.07
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-05-06 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.3435(5)
_cell_length_b                   6.7923(2)
_cell_length_c                   26.7611(6)
_cell_measurement_reflns_used    18932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.52
_cell_volume                     3334.29(15)
_computing_cell_refinement       'PEAKREF (Schreurs, 2005)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF08 (Beurskens et al., 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50128
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.184
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2006)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0278
_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)+(0.0206P)²+2.8651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0636
_reflns_number_gt                2619
_reflns_number_total             3278
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg801109nsup1.cif
_cod_data_source_block           5
_cod_original_formula_sum        'C17.50 H20 N2 Ni O3.50'
_cod_database_code               4509245
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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
Ni1 Ni 0.235345(13) 0.22733(3) 0.092504(8) 0.01878(8) Uani 1 1 d .
C1 C 0.15597(11) 0.2465(3) 0.00175(7) 0.0219(4) Uani 1 1 d .
C2 C 0.22000(10) 0.2483(3) -0.02772(7) 0.0222(4) Uani 1 1 d .
C3 C 0.21453(12) 0.2697(3) -0.07994(7) 0.0295(5) Uani 1 1 d .
H3 H 0.2577 0.2674 -0.0996 0.035 Uiso 1 1 calc R
C4 C 0.14852(13) 0.2939(3) -0.10306(8) 0.0354(5) Uani 1 1 d .
H4 H 0.1457 0.3085 -0.1383 0.042 Uiso 1 1 calc R
C5 C 0.08578(13) 0.2965(3) -0.07404(8) 0.0363(5) Uani 1 1 d .
H5 H 0.0398 0.3157 -0.0897 0.044 Uiso 1 1 calc R
C6 C 0.08883(11) 0.2720(3) -0.02309(8) 0.0316(5) Uani 1 1 d .
H6 H 0.0449 0.2721 -0.0043 0.038 Uiso 1 1 calc R
C7 C 0.29071(11) 0.2331(3) -0.00562(7) 0.0235(4) Uani 1 1 d .
H7 H 0.3314 0.2277 -0.0275 0.028 Uiso 1 1 calc R
C8 C 0.17862(12) 0.1747(3) 0.19049(7) 0.0261(5) Uani 1 1 d .
C9 C 0.24898(12) 0.1523(3) 0.21130(7) 0.0264(5) Uani 1 1 d .
C10 C 0.25624(15) 0.0994(3) 0.26185(8) 0.0358(5) Uani 1 1 d .
H10 H 0.3037 0.0852 0.2757 0.043 Uiso 1 1 calc R
C11 C 0.19692(16) 0.0679(3) 0.29158(9) 0.0434(6) Uani 1 1 d .
H11 H 0.2029 0.0320 0.3256 0.052 Uiso 1 1 calc R
C12 C 0.12777(16) 0.0890(4) 0.27134(9) 0.0449(6) Uani 1 1 d .
H12 H 0.0862 0.0672 0.2918 0.054 Uiso 1 1 calc R
C13 C 0.11846(14) 0.1414(3) 0.22179(8) 0.0353(5) Uani 1 1 d .
H13 H 0.0706 0.1550 0.2087 0.042 Uiso 1 1 calc R
C14 C 0.31277(12) 0.1905(3) 0.18260(8) 0.0277(5) Uani 1 1 d .
H14 H 0.3583 0.1870 0.1996 0.033 Uiso 1 1 calc R
C15 C 0.38270(11) 0.2844(3) 0.11121(8) 0.0283(5) Uani 1 1 d .
H15A H 0.4245 0.2271 0.1295 0.034 Uiso 1 1 calc R
H15B H 0.3883 0.4293 0.1106 0.034 Uiso 1 1 calc R
C16 C 0.37965(11) 0.2042(3) 0.05865(8) 0.0269(5) Uani 1 1 d .
H16A H 0.4130 0.2788 0.0366 0.032 Uiso 1 1 calc R
H16B H 0.3942 0.0638 0.0582 0.032 Uiso 1 1 calc R
N1 N 0.30363(8) 0.2262(2) 0.04166(6) 0.0210(3) Uani 1 1 d .
N2 N 0.31377(8) 0.2294(2) 0.13550(6) 0.0229(4) Uani 1 1 d .
O1 O 0.15579(7) 0.2257(2) 0.05052(5) 0.0228(3) Uani 1 1 d .
O2 O 0.16677(7) 0.2244(2) 0.14329(5) 0.0238(3) Uani 1 1 d .
C1S C -0.02110(14) 0.2115(4) 0.10700(10) 0.0506(7) Uani 1 1 d .
H1A H -0.0173 0.0902 0.1266 0.076 Uiso 1 1 calc R
H1B H -0.0065 0.1852 0.0724 0.076 Uiso 1 1 calc R
H1C H -0.0716 0.2585 0.1076 0.076 Uiso 1 1 calc R
O1S O 0.02482(9) 0.3558(3) 0.12758(7) 0.0438(4) Uani 1 1 d D
H1S H 0.0678(7) 0.317(4) 0.1292(11) 0.066 Uiso 1 1 d D
C2S C 0.0000 0.5988(6) 0.2500 0.0550(11) Uani 1 2 d SD
H2A H -0.009(3) 0.719(4) 0.2699(17) 0.082 Uiso 0.50 1 d PD
H2B H 0.0488(13) 0.548(7) 0.259(2) 0.082 Uiso 0.50 1 d PD
H2C H -0.036(2) 0.500(5) 0.2605(19) 0.082 Uiso 0.50 1 d PD
O2S O -0.0122(3) 0.6433(6) 0.20011(16) 0.0653(12) Uani 0.50 1 d PD
H2S H -0.008(4) 0.536(6) 0.185(2) 0.098 Uiso 0.50 1 d PD
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
O1 Ni1 N2 178.94(7) .
O1 Ni1 N1 95.04(6) .
N2 Ni1 N1 86.02(7) .
O1 Ni1 O2 84.80(6) .
N2 Ni1 O2 94.14(6) .
N1 Ni1 O2 179.12(7) .
O1 C1 C6 118.67(18) .
O1 C1 C2 123.86(18) .
C6 C1 C2 117.47(18) .
C3 C2 C1 119.65(18) .
C3 C2 C7 118.85(18) .
C1 C2 C7 121.48(17) .
C4 C3 C2 121.6(2) .
C4 C3 H3 119.2 .
C2 C3 H3 119.2 .
C3 C4 C5 118.8(2) .
C3 C4 H4 120.6 .
C5 C4 H4 120.6 .
C6 C5 C4 121.3(2) .
C6 C5 H5 119.4 .
C4 C5 H5 119.4 .
C5 C6 C1 121.2(2) .
C5 C6 H6 119.4 .
C1 C6 H6 119.4 .
N1 C7 C2 125.17(18) .
N1 C7 H7 117.4 .
C2 C7 H7 117.4 .
O2 C8 C13 118.7(2) .
O2 C8 C9 123.54(19) .
C13 C8 C9 117.71(19) .
C10 C9 C8 119.5(2) .
C10 C9 C14 119.2(2) .
C8 C9 C14 121.21(18) .
C11 C10 C9 121.7(2) .
C11 C10 H10 119.2 .
C9 C10 H10 119.2 .
C10 C11 C12 119.0(2) .
C10 C11 H11 120.5 .
C12 C11 H11 120.5 .
C13 C12 C11 120.9(2) .
C13 C12 H12 119.5 .
C11 C12 H12 119.5 .
C12 C13 C8 121.1(2) .
C12 C13 H13 119.5 .
C8 C13 H13 119.5 .
N2 C14 C9 125.25(19) .
N2 C14 H14 117.4 .
C9 C14 H14 117.4 .
N2 C15 C16 106.77(16) .
N2 C15 H15A 110.4 .
C16 C15 H15A 110.4 .
N2 C15 H15B 110.4 .
C16 C15 H15B 110.4 .
H15A C15 H15B 108.6 .
N1 C16 C15 106.62(15) .
N1 C16 H16A 110.4 .
C15 C16 H16A 110.4 .
N1 C16 H16B 110.4 .
C15 C16 H16B 110.4 .
H16A C16 H16B 108.6 .
C7 N1 C16 118.73(17) .
C7 N1 Ni1 126.72(14) .
C16 N1 Ni1 114.46(12) .
C14 N2 C15 119.81(17) .
C14 N2 Ni1 126.76(15) .
C15 N2 Ni1 113.43(13) .
C1 O1 Ni1 127.14(12) .
C8 O2 Ni1 126.22(13) .
O1S C1S H1A 109.5 .
O1S C1S H1B 109.5 .
H1A C1S H1B 109.5 .
O1S C1S H1C 109.5 .
H1A C1S H1C 109.5 .
H1B C1S H1C 109.5 .
C1S O1S H1S 112(2) .
O2S C2S H2A 48(3) 4
O2S C2S H2B 73(3) 4
H2A C2S H2B 107.9(14) .
O2S C2S H2C 89(3) 4
H2A C2S H2C 107.8(15) .
H2B C2S H2C 107.9(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 1.8417(13) .
Ni1 N2 1.8422(15) .
Ni1 N1 1.8495(16) .
Ni1 O2 1.8519(13) .
C1 O1 1.313(2) .
C1 C6 1.410(3) .
C1 C2 1.415(3) .
C2 C3 1.409(3) .
C2 C7 1.429(3) .
C3 C4 1.370(3) .
C3 H3 0.9500 .
C4 C5 1.389(3) .
C4 H4 0.9500 .
C5 C6 1.375(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 N1 1.288(2) .
C7 H7 0.9500 .
C8 O2 1.325(2) .
C8 C13 1.404(3) .
C8 C9 1.414(3) .
C9 C10 1.406(3) .
C9 C14 1.424(3) .
C10 C11 1.365(3) .
C10 H10 0.9500 .
C11 C12 1.387(4) .
C11 H11 0.9500 .
C12 C13 1.384(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 N2 1.288(3) .
C14 H14 0.9500 .
C15 N2 1.470(3) .
C15 C16 1.509(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 N1 1.474(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C1S O1S 1.405(3) .
C1S H1A 0.9800 .
C1S H1B 0.9800 .
C1S H1C 0.9800 .
O1S H1S 0.833(10) .
C2S O2S 1.387(4) 4
C2S H2A 0.987(10) .
C2S H2B 0.987(10) .
C2S H2C 0.988(10) .
O2S H2S 0.839(10) .
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
O1S H1S O2 0.833(10) 1.958(11) 2.785(2) 172(3)
O2S H2S O1S 0.839(10) 2.05(3) 2.836(4) 155(7)
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
O1 C1 C2 C3 179.41(18)
C6 C1 C2 C3 -1.6(3)
O1 C1 C2 C7 -2.0(3)
C6 C1 C2 C7 176.95(18)
C1 C2 C3 C4 1.6(3)
C7 C2 C3 C4 -177.02(19)
C2 C3 C4 C5 -0.2(3)
C3 C4 C5 C6 -1.2(4)
C4 C5 C6 C1 1.1(4)
O1 C1 C6 C5 179.3(2)
C2 C1 C6 C5 0.3(3)
C3 C2 C7 N1 175.15(19)
C1 C2 C7 N1 -3.4(3)
O2 C8 C9 C10 179.94(17)
C13 C8 C9 C10 -0.3(3)
O2 C8 C9 C14 2.6(3)
C13 C8 C9 C14 -177.66(18)
C8 C9 C10 C11 0.3(3)
C14 C9 C10 C11 177.68(19)
C9 C10 C11 C12 -0.1(3)
C10 C11 C12 C13 -0.1(4)
C11 C12 C13 C8 0.0(4)
O2 C8 C13 C12 179.9(2)
C9 C8 C13 C12 0.2(3)
C10 C9 C14 N2 175.95(19)
C8 C9 C14 N2 -6.7(3)
N2 C15 C16 N1 36.9(2)
C2 C7 N1 C16 178.10(18)
C2 C7 N1 Ni1 1.7(3)
C15 C16 N1 C7 156.66(18)
C15 C16 N1 Ni1 -26.52(19)
O1 Ni1 N1 C7 3.18(17)
N2 Ni1 N1 C7 -176.75(17)
O1 Ni1 N1 C16 -173.34(13)
N2 Ni1 N1 C16 6.73(13)
C9 C14 N2 C15 174.26(18)
C9 C14 N2 Ni1 -5.0(3)
C16 C15 N2 C14 146.65(18)
C16 C15 N2 Ni1 -33.99(19)
N1 Ni1 N2 C14 -164.55(17)
O2 Ni1 N2 C14 14.59(17)
N1 Ni1 N2 C15 16.15(13)
O2 Ni1 N2 C15 -164.72(13)
C6 C1 O1 Ni1 -170.18(14)
C2 C1 O1 Ni1 8.8(3)
N1 Ni1 O1 C1 -8.33(16)
O2 Ni1 O1 C1 172.54(16)
C13 C8 O2 Ni1 -167.07(14)
C9 C8 O2 Ni1 12.6(3)
O1 Ni1 O2 C8 161.80(16)
N2 Ni1 O2 C8 -18.30(16)
