#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2004771.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_2004771
loop_
_publ_author_name
'Cannadine, J. C.'
'Corden, J. P.'
'Errington, W.'
'Moore, P.'
'Wallbridge, M. G. H.'
_publ_section_title
;
 Two Schiff Base Ligands Derived from 1,2-Diaminocyclohexane
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1014
_journal_page_last               1017
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C20 H22 N2 O2'
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.40
_chemical_name_systematic
;
2,2'-[(1,2-cyclohexanediyl)bis(nitrilomethylidyne)]bisphenol
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.50(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.013(6)
_cell_length_b                   11.860(6)
_cell_length_c                   9.643(2)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.15
_cell_volume                     1811.2(12)
_computing_cell_refinement       MADNES
_computing_data_collection       'MADNES (Pflugrath & Messerschmidt, 1992)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1994)'
_computing_structure_solution    SHELXTL-Plus
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device
;
Delft Instruments FAST TV area-detector diffractometer
;
_diffrn_measurement_method       'flat plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3417
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.141
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   1.4(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.022
_refine_ls_goodness_of_fit_obs   1.064
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1932
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.136
_refine_ls_restrained_S_obs      1.064
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_obs          0.0436
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+( 0.0729P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1219
_refine_ls_wR_factor_obs         0.1071
_reflns_number_observed          1728
_reflns_number_total             1936
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ka1152.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C c'
_cod_database_code               2004771
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'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.073(2) 0.112(2) 0.0726(15) -0.0064(14) 0.0008(12) 0.0364(13)
O2 0.120(2) 0.0602(13) 0.0679(13) -0.0082(13) -0.0036(12) 0.0097(10)
N1 0.0491(14) 0.0641(14) 0.0519(13) 0.0014(12) 0.0016(11) -0.0019(11)
N2 0.0494(14) 0.0574(15) 0.0543(14) 0.0013(11) 0.0048(10) 0.0026(10)
C1 0.054(2) 0.072(2) 0.048(2) 0.0047(15) 0.0052(13) -0.0003(13)
C2 0.060(2) 0.095(2) 0.069(2) -0.008(2) 0.019(2) -0.002(2)
C3 0.050(2) 0.092(2) 0.094(2) 0.010(2) 0.009(2) -0.003(2)
C4 0.059(2) 0.081(2) 0.100(2) 0.021(2) -0.002(2) 0.009(2)
C5 0.061(2) 0.063(2) 0.088(2) 0.008(2) 0.008(2) 0.0145(15)
C6 0.052(2) 0.057(2) 0.054(2) 0.0044(13) 0.0043(12) -0.0026(13)
C7 0.050(2) 0.0563(15) 0.0543(15) 0.0036(13) 0.0045(12) 0.0015(13)
C8 0.047(2) 0.059(2) 0.054(2) -0.0033(13) -0.0016(12) 0.0017(12)
C9 0.066(2) 0.075(2) 0.058(2) 0.003(2) -0.0052(14) -0.0088(14)
C10 0.068(2) 0.092(2) 0.071(2) -0.014(2) -0.013(2) -0.004(2)
C11 0.045(2) 0.100(2) 0.076(2) -0.009(2) -0.0041(14) 0.010(2)
C12 0.049(2) 0.089(2) 0.071(2) 0.001(2) 0.0063(15) 0.006(2)
C13 0.046(2) 0.059(2) 0.052(2) -0.0017(13) 0.0011(12) 0.0037(12)
C14 0.0407(14) 0.056(2) 0.0536(15) 0.0057(13) 0.0090(11) 0.0028(12)
C15 0.0432(15) 0.054(2) 0.055(2) 0.0062(13) 0.0100(11) 0.0015(12)
C16 0.058(2) 0.057(2) 0.060(2) 0.0027(14) 0.0082(14) 0.0008(13)
C17 0.065(2) 0.069(2) 0.067(2) -0.007(2) 0.0086(15) -0.0150(15)
C18 0.061(2) 0.089(2) 0.054(2) 0.008(2) 0.0058(14) -0.011(2)
C19 0.078(2) 0.074(2) 0.051(2) 0.014(2) 0.006(2) 0.0048(15)
C20 0.063(2) 0.057(2) 0.052(2) 0.0064(15) 0.0070(14) 0.0000(13)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 1.0259(2) 0.2372(2) -0.1151(2) 0.0865(7) Uani d . 1 O
H1 0.9602(2) 0.2147(2) -0.1231(2) 0.104 Uiso d R 1 H
O2 0.8539(2) 0.1559(2) 0.3976(2) 0.0845(7) Uani d . 1 O
H2A 0.8404(2) 0.1576(2) 0.2814(2) 0.101 Uiso d R 1 H
N1 0.89210(15) 0.1387(2) -0.0487(2) 0.0556(6) Uani d . 1 N
N2 0.7976(2) 0.2349(2) 0.1494(2) 0.0540(6) Uani d . 1 N
C1 1.0726(2) 0.1683(2) -0.0234(3) 0.0580(7) Uani d . 1 C
C2 1.1599(2) 0.1739(3) -0.0062(3) 0.0736(9) Uani d . 1 C
H2 1.1864(2) 0.2242(3) -0.0593(3) 0.088 Uiso d R 1 H
C3 1.2079(2) 0.1053(3) 0.0885(4) 0.0784(9) Uani d . 1 C
H3 1.2665(2) 0.1089(3) 0.0985(4) 0.094 Uiso d R 1 H
C4 1.1704(2) 0.0303(3) 0.1688(4) 0.0811(10) Uani d . 1 C
H4 1.2034(2) -0.0146(3) 0.2344(4) 0.097 Uiso d R 1 H
C5 1.0836(2) 0.0227(3) 0.1522(3) 0.0709(8) Uani d . 1 C
H5 1.0584(2) -0.0278(3) 0.2070(3) 0.085 Uiso d R 1 H
C6 1.0326(2) 0.0899(2) 0.0559(3) 0.0546(7) Uani d . 1 C
C7 0.9416(2) 0.0787(2) 0.0372(3) 0.0539(6) Uani d . 1 C
H7 0.9199(2) 0.0148(2) 0.1007(3) 0.065 Uiso d R 1 H
C8 0.8011(2) 0.1204(2) -0.0594(3) 0.0542(7) Uani d . 1 C
H8 0.7913(2) 0.0528(2) -0.0056(3) 0.065 Uiso calc R 1 H
C9 0.7620(2) 0.1021(3) -0.2118(3) 0.0676(8) Uani d . 1 C
H9A 0.7877(2) 0.0368(3) -0.2490(3) 0.081 Uiso d R 1 H
H9B 0.7735(2) 0.1674(3) -0.2667(3) 0.081 Uiso d R 1 H
C10 0.6676(2) 0.0849(3) -0.2245(4) 0.0795(9) Uani d . 1 C
H10A 0.6439(2) 0.0773(3) -0.3226(4) 0.095 Uiso d R 1 H
H10B 0.6566(2) 0.0155(3) -0.1772(4) 0.095 Uiso d R 1 H
C11 0.6249(2) 0.1821(3) -0.1601(3) 0.0750(9) Uani d . 1 C
H11A 0.5656(2) 0.1647(3) -0.1620(3) 0.090 Uiso d R 1 H
H11B 0.6289(2) 0.2495(3) -0.2156(3) 0.090 Uiso d R 1 H
C12 0.6650(2) 0.2028(3) -0.0086(3) 0.0700(8) Uani d . 1 C
H12A 0.6396(2) 0.2692(3) 0.0266(3) 0.084 Uiso d R 1 H
H12B 0.6540(2) 0.1393(3) 0.0494(3) 0.084 Uiso d R 1 H
C13 0.7596(2) 0.2206(2) 0.0021(3) 0.0529(7) Uani d . 1 C
H13 0.7701(2) 0.2887(2) -0.0503(3) 0.064 Uiso calc R 1 H
C14 0.8311(2) 0.3288(2) 0.1894(3) 0.0498(6) Uani d . 1 C
H14 0.8401(2) 0.3985(2) 0.1201(3) 0.060 Uiso d R 1 H
C15 0.8746(2) 0.3473(2) 0.3306(3) 0.0506(7) Uani d . 1 C
C16 0.9080(2) 0.4527(2) 0.3702(3) 0.0587(7) Uani d . 1 C
H16 0.8978(2) 0.5130(2) 0.3083(3) 0.070 Uiso d R 1 H
C17 0.9563(2) 0.4695(3) 0.5003(3) 0.0673(8) Uani d . 1 C
H17 0.9789(2) 0.5401(3) 0.5253(3) 0.081 Uiso d R 1 H
C18 0.9702(2) 0.3800(3) 0.5923(3) 0.0685(9) Uani d . 1 C
H18 1.0038(2) 0.3897(3) 0.6787(3) 0.082 Uiso d R 1 H
C19 0.9359(2) 0.2760(3) 0.5576(3) 0.0681(9) Uani d . 1 C
H19 0.9447(2) 0.2167(3) 0.6212(3) 0.082 Uiso d R 1 H
C20 0.8874(2) 0.2588(2) 0.4284(3) 0.0574(7) Uani d . 1 C
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'
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
C7 N1 C8 118.7(2) y
C14 N2 C13 119.4(2) y
O1 C1 C2 120.1(3) ?
O1 C1 C6 120.1(2) y
C2 C1 C6 119.8(3) ?
C3 C2 C1 120.5(3) ?
C2 C3 C4 120.7(3) ?
C3 C4 C5 119.6(3) ?
C4 C5 C6 121.5(3) ?
C5 C6 C1 117.9(3) ?
C5 C6 C7 120.7(2) ?
C1 C6 C7 121.4(2) ?
N1 C7 C6 123.2(2) y
N1 C8 C13 110.2(2) y
N1 C8 C9 110.6(2) ?
C13 C8 C9 110.2(2) ?
C10 C9 C8 111.1(3) ?
C9 C10 C11 111.7(3) ?
C10 C11 C12 111.3(3) ?
C13 C12 C11 111.2(2) ?
N2 C13 C12 110.4(2) ?
N2 C13 C8 108.9(2) y
C12 C13 C8 110.7(2) ?
N2 C14 C15 122.6(2) y
C16 C15 C20 118.4(3) ?
C16 C15 C14 120.3(2) ?
C20 C15 C14 121.3(2) ?
C17 C16 C15 121.2(3) ?
C18 C17 C16 119.1(3) ?
C19 C18 C17 120.9(3) ?
C18 C19 C20 120.3(3) ?
O2 C20 C19 119.0(3) ?
O2 C20 C15 120.9(3) y
C19 C20 C15 120.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.347(4) y
O2 C20 1.348(3) y
N1 C7 1.276(3) y
N1 C8 1.462(4) y
N2 C14 1.270(3) y
N2 C13 1.470(4) y
C1 C2 1.385(4) ?
C1 C6 1.415(4) ?
C2 C3 1.371(5) ?
C3 C4 1.375(5) ?
C4 C5 1.378(5) ?
C5 C6 1.393(4) ?
C6 C7 1.447(4) y
C8 C13 1.524(4) y
C8 C9 1.526(4) ?
C9 C10 1.513(5) ?
C10 C11 1.518(5) ?
C11 C12 1.526(5) ?
C12 C13 1.518(4) ?
C14 C15 1.452(4) y
C15 C16 1.391(4) ?
C15 C20 1.406(4) ?
C16 C17 1.388(4) ?
C17 C18 1.380(4) ?
C18 C19 1.372(5) ?
C19 C20 1.382(4) ?
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
O1 C1 C2 C3 179.0(3) ?
C6 C1 C2 C3 -1.0(4) ?
C1 C2 C3 C4 -0.5(5) ?
C2 C3 C4 C5 1.1(5) ?
C3 C4 C5 C6 -0.3(5) ?
C4 C5 C6 C1 -1.1(4) ?
C4 C5 C6 C7 178.3(3) ?
O1 C1 C6 C5 -178.2(3) ?
C2 C1 C6 C5 1.7(4) ?
O1 C1 C6 C7 2.4(4) y
C2 C1 C6 C7 -177.7(2) ?
C8 N1 C7 C6 -180.0(2) y
C5 C6 C7 N1 179.5(3) ?
C1 C6 C7 N1 -1.1(4) y
C7 N1 C8 C13 110.0(3) y
C7 N1 C8 C9 -128.0(3) ?
N1 C8 C9 C10 -179.1(3) ?
C13 C8 C9 C10 -57.1(3) ?
C8 C9 C10 C11 55.6(4) ?
C9 C10 C11 C12 -54.2(4) ?
C10 C11 C12 C13 54.6(4) ?
C14 N2 C13 C12 -114.9(3) ?
C14 N2 C13 C8 123.4(2) y
C11 C12 C13 N2 -177.3(3) ?
C11 C12 C13 C8 -56.6(3) ?
N1 C8 C13 N2 -58.6(3) y
C9 C8 C13 N2 179.1(2) ?
N1 C8 C13 C12 179.9(2) ?
C9 C8 C13 C12 57.6(3) ?
C13 N2 C14 C15 -175.9(2) y
N2 C14 C15 C16 -178.1(2) ?
N2 C14 C15 C20 4.8(4) y
C20 C15 C16 C17 3.1(4) ?
C14 C15 C16 C17 -174.1(2) ?
C15 C16 C17 C18 -1.0(4) ?
C16 C17 C18 C19 -1.1(4) ?
C17 C18 C19 C20 0.8(4) ?
C18 C19 C20 O2 -179.4(3) ?
C18 C19 C20 C15 1.4(4) ?
C16 C15 C20 O2 177.5(3) ?
C14 C15 C20 O2 -5.2(4) y
C16 C15 C20 C19 -3.3(4) ?
C14 C15 C20 C19 173.9(3) ?