#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006593.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_2006593
loop_
_publ_author_name
'Abu-Surrah, A. S.'
'Laine, T. V.'
'Repo, T.'
'Fawzi, R.'
'Steimann, M.'
'Rieger, B.'
_publ_contact_author
;
 Bernhard Rieger
 Abteilung Makromolekulare Chemie
 Universit\"at Ulm
 D-89069 Ulm
 Germany
;
_publ_section_title
;
 An Enantiomerically Pure Schiff Base Ligand
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1458
_journal_page_last               1459
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C26 H24 N4'
_chemical_formula_weight         392.49
_chemical_name_systematic
;
 (1R,2R)-(-)-N,N'-bis(quinoline-2-methylene)-1,2-cyclohexyldiimine
;
_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'
_audit_creation_method           SHELXL-93
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9320(10)
_cell_length_b                   15.120(5)
_cell_length_c                   23.564(6)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      15
_cell_volume                     2113.5(10)
_computing_cell_refinement       'Siemens P4 Software'
_computing_data_collection       'Siemens P4 Software (Siemens, 1991a)'
_computing_data_reduction        'XDISK (Siemens, 1991b)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '\w scans (Sheldrick, 1993)'
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14322
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        6
_diffrn_standards_interval_count 58
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   '\y scan'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.116
_refine_ls_extinction_coef       0.0115(12)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.373
_refine_ls_goodness_of_fit_obs   1.486
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.373
_refine_ls_restrained_S_obs      1.486
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_obs          0.0318
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc
 w = exp[5.00(sin\q/\l)^2^]/[\s^2^(Fo^2^)+(0.0349P)^2^]
 where P = (0.333Fo^2^ + 0.667Fc^2^)
;
_refine_ls_wR_factor_all         0.0715
_refine_ls_wR_factor_obs         0.0677
_reflns_number_observed          2890
_reflns_number_total             3711
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ka1231.cif
_[local]_cod_data_source_block   rieger23
_cod_original_cell_volume        2114.0(10)
_cod_database_code               2006593
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
N1 0.0388(9) 0.0283(7) 0.0410(9) 0.0004(7) -0.0050(7) -0.0046(7)
N2 0.0354(8) 0.0263(7) 0.0356(8) 0.0011(6) -0.0029(7) -0.0030(6)
N3 0.0389(9) 0.0324(7) 0.0413(9) 0.0020(7) 0.0000(8) -0.0005(7)
N4 0.0321(8) 0.0273(7) 0.0394(9) -0.0005(6) -0.0002(7) -0.0010(6)
C1 0.0359(10) 0.0260(8) 0.0382(10) 0.0028(8) -0.0022(8) -0.0020(8)
C2 0.0491(13) 0.0283(9) 0.0506(12) -0.0044(9) -0.0083(10) 0.0017(8)
C3 0.0548(14) 0.0326(9) 0.0473(11) -0.0031(9) -0.0114(11) -0.0101(9)
C4 0.0583(13) 0.0369(10) 0.0339(10) 0.0017(10) -0.0073(10) -0.0046(8)
C5 0.0456(12) 0.0337(9) 0.0421(11) -0.0038(8) 0.0013(9) -0.0019(9)
C6 0.0373(10) 0.0246(8) 0.0384(10) 0.0004(8) -0.0051(8) -0.0028(8)
C7 0.0355(11) 0.0272(9) 0.0350(10) 0.0027(8) -0.0007(8) -0.0025(7)
C8 0.0363(10) 0.0266(8) 0.0327(10) 0.0020(7) 0.0015(8) -0.0017(7)
C9 0.0304(10) 0.0334(9) 0.0306(9) 0.0031(8) 0.0015(8) 0.0024(8)
C10 0.0320(10) 0.0362(9) 0.0308(9) -0.0051(8) -0.0020(8) 0.0033(8)
C11 0.0480(11) 0.0347(9) 0.0324(9) -0.0112(8) -0.0053(9) -0.0021(8)
C12 0.0488(12) 0.0249(8) 0.0425(11) -0.0024(8) 0.0020(10) -0.0027(8)
C13 0.0347(10) 0.0270(8) 0.0413(10) 0.0015(8) -0.0022(8) -0.0017(8)
C14 0.0331(10) 0.0241(7) 0.0291(9) -0.0021(7) -0.0001(8) 0.0011(7)
C15 0.0314(9) 0.0289(8) 0.0251(9) -0.0019(7) 0.0018(7) 0.0020(7)
C16 0.0331(10) 0.0262(8) 0.0308(8) -0.0008(7) 0.0001(8) -0.0015(7)
C17 0.0339(10) 0.0260(8) 0.0429(10) 0.0004(8) -0.0018(9) -0.0025(8)
C18 0.0355(10) 0.0295(9) 0.0510(12) 0.0014(8) -0.0006(9) 0.0059(8)
C19 0.0334(10) 0.0293(9) 0.0582(13) 0.0034(8) 0.0071(10) 0.0047(9)
C20 0.0426(11) 0.0328(9) 0.0583(14) -0.0021(8) 0.0155(10) -0.0048(9)
C21 0.0589(14) 0.0420(11) 0.0443(12) -0.0073(11) 0.0141(11) -0.0058(9)
C22 0.0524(14) 0.0401(10) 0.0433(11) -0.0070(10) 0.0007(10) -0.0015(9)
C23 0.0386(12) 0.0339(9) 0.0438(11) 0.0002(8) 0.0021(10) -0.0024(8)
C24 0.0351(10) 0.0227(8) 0.0439(10) -0.0052(7) 0.0029(8) -0.0021(7)
C25 0.0367(10) 0.0226(8) 0.0476(11) -0.0034(7) 0.0083(9) -0.0008(8)
C26 0.0356(10) 0.0205(7) 0.0431(10) -0.0042(7) 0.0003(8) -0.0006(7)
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
N1 0.3334(3) 1.00319(10) -0.18111(7) 0.0360(4) Uani d . 1 N
N2 0.4055(3) 1.21797(9) -0.12507(6) 0.0324(3) Uani d . 1 N
N3 -0.0119(3) 0.88630(9) -0.13283(7) 0.0375(4) Uani d . 1 N
N4 0.0583(3) 0.83813(9) 0.01273(7) 0.0329(4) Uani d . 1 N
C1 0.1041(3) 0.87008(11) -0.18645(8) 0.0334(4) Uani d . 1 C
H1B 0.2404(3) 0.83742(11) -0.17986(8) 0.060 Uiso d R 1 H
C2 -0.0525(4) 0.81516(12) -0.22391(9) 0.0426(5) Uani d . 1 C
H2B -0.1946(4) 0.84529(12) -0.22639(9) 0.060 Uiso d R 1 H
H2C -0.0787(4) 0.75844(12) -0.20683(9) 0.060 Uiso d R 1 H
C3 0.0378(4) 0.80333(12) -0.28380(9) 0.0449(5) Uani d . 1 C
H3B -0.0670(4) 0.76995(12) -0.30628(9) 0.060 Uiso d R 1 H
H3C 0.1765(4) 0.77079(12) -0.28181(9) 0.060 Uiso d R 1 H
C4 0.0818(4) 0.89320(12) -0.31080(8) 0.0430(5) Uani d . 1 C
H4B -0.0572(4) 0.92539(12) -0.31371(8) 0.060 Uiso d R 1 H
H4C 0.1417(4) 0.88532(12) -0.34831(8) 0.060 Uiso d R 1 H
C5 0.2480(4) 0.94542(13) -0.27502(8) 0.0405(5) Uani d . 1 C
H5A 0.2765(4) 1.00200(13) -0.29204(8) 0.060 Uiso d R 1 H
H5B 0.3880(4) 0.91368(13) -0.27348(8) 0.060 Uiso d R 1 H
C6 0.1601(3) 0.95854(11) -0.21457(8) 0.0334(4) Uani d . 1 C
H6A 0.0264(3) 0.99425(11) -0.21581(8) 0.060 Uiso d R 1 H
C7 0.3045(3) 1.08423(11) -0.17029(8) 0.0326(4) Uani d . 1 C
H7A 0.1700(3) 1.11301(11) -0.18343(8) 0.060 Uiso d R 1 H
C8 0.6793(3) 1.09965(11) -0.12188(7) 0.0319(4) Uani d . 1 C
H8A 0.7181(3) 1.04027(11) -0.13247(7) 0.060 Uiso d R 1 H
C9 0.8238(3) 1.14949(11) -0.09076(7) 0.0315(4) Uani d . 1 C
H9A 0.9677(3) 1.12621(11) -0.07961(7) 0.060 Uiso d R 1 H
C10 0.9005(3) 1.29207(12) -0.04189(8) 0.0330(4) Uani d . 1 C
H10A 1.0463(3) 1.27131(12) -0.03022(8) 0.060 Uiso d R 1 H
C11 0.8289(4) 1.37468(12) -0.02631(8) 0.0384(4) Uani d . 1 C
H11A 0.9205(4) 1.41108(12) -0.00217(8) 0.060 Uiso d R 1 H
C12 0.6183(3) 1.40588(11) -0.04453(8) 0.0387(5) Uani d . 1 C
H12A 0.5707(3) 1.46460(11) -0.03470(8) 0.060 Uiso d R 1 H
C13 0.4818(3) 1.35502(10) -0.07786(8) 0.0343(4) Uani d . 1 C
H13A 0.3383(3) 1.37733(10) -0.09012(8) 0.060 Uiso d R 1 H
C14 0.5502(3) 1.26839(10) -0.09344(7) 0.0288(4) Uani d . 1 C
C15 0.7619(3) 1.23716(11) -0.07537(7) 0.0285(4) Uani d . 1 C
C16 0.4704(3) 1.13633(10) -0.13796(7) 0.0300(4) Uani d . 1 C
C17 0.0659(3) 0.85286(11) -0.08774(8) 0.0343(4) Uani d . 1 C
H17A 0.2042(3) 0.81994(11) -0.08895(8) 0.060 Uiso d R 1 H
C18 -0.2774(3) 0.89597(12) -0.03174(9) 0.0387(5) Uani d . 1 C
H18A -0.3553(3) 0.90954(12) -0.06637(9) 0.060 Uiso d R 1 H
C19 -0.3787(3) 0.90722(12) 0.01924(9) 0.0403(5) Uani d . 1 C
H19A -0.5293(3) 0.93034(12) 0.02101(9) 0.060 Uiso d R 1 H
C20 -0.3517(4) 0.89981(12) 0.12493(9) 0.0446(5) Uani d . 1 C
H20A -0.4988(4) 0.92536(12) 0.12925(9) 0.060 Uiso d R 1 H
C21 -0.2320(4) 0.87623(13) 0.17175(9) 0.0484(5) Uani d . 1 C
H21A -0.2923(4) 0.88808(13) 0.20879(9) 0.060 Uiso d R 1 H
C22 -0.0206(4) 0.83656(12) 0.16632(9) 0.0453(5) Uani d . 1 C
H22A 0.0599(4) 0.81776(12) 0.19954(9) 0.060 Uiso d R 1 H
C23 0.0717(4) 0.82289(12) 0.11381(8) 0.0388(5) Uani d . 1 C
H23A 0.2177(4) 0.79604(12) 0.11020(8) 0.060 Uiso d R 1 H
C24 -0.0452(3) 0.84902(11) 0.06432(8) 0.0339(4) Uani d . 1 C
C25 -0.2624(3) 0.88603(11) 0.06980(9) 0.0356(4) Uani d . 1 C
C26 -0.0542(3) 0.86300(10) -0.03298(8) 0.0331(4) 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'
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 C6 117.5(2) yes
C16 N2 C14 117.41(15) ?
C17 N3 C1 119.2(2) yes
C26 N4 C24 117.5(2) ?
N3 C1 C2 107.8(2) ?
N3 C1 C6 109.30(14) yes
C2 C1 C6 110.94(15) ?
C3 C2 C1 112.7(2) ?
C2 C3 C4 110.08(15) ?
C5 C4 C3 110.1(2) ?
C4 C5 C6 111.3(2) ?
N1 C6 C1 108.86(15) yes
N1 C6 C5 108.8(2) ?
C1 C6 C5 111.35(14) ?
N1 C7 C16 122.2(2) yes
C9 C8 C16 118.9(2) ?
C8 C9 C15 119.5(2) ?
C11 C10 C15 120.4(2) ?
C10 C11 C12 120.1(2) ?
C13 C12 C11 121.0(2) ?
C12 C13 C14 119.9(2) ?
N2 C14 C15 122.51(15) ?
N2 C14 C13 118.4(2) ?
C15 C14 C13 119.1(2) ?
C14 C15 C10 119.5(2) ?
C14 C15 C9 117.8(2) ?
C10 C15 C9 122.7(2) ?
N2 C16 C8 124.0(2) ?
N2 C16 C7 114.9(2) ?
C8 C16 C7 121.07(15) ?
N3 C17 C26 121.0(2) yes
C19 C18 C26 118.5(2) ?
C18 C19 C25 120.2(2) ?
C21 C20 C25 120.7(2) ?
C20 C21 C22 120.5(2) ?
C23 C22 C21 120.5(2) ?
C22 C23 C24 120.5(2) ?
N4 C24 C25 122.5(2) ?
N4 C24 C23 118.6(2) ?
C25 C24 C23 118.9(2) ?
C24 C25 C19 117.3(2) ?
C24 C25 C20 118.9(2) ?
C19 C25 C20 123.8(2) ?
N4 C26 C18 123.8(2) ?
N4 C26 C17 116.0(2) ?
C18 C26 C17 120.3(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C7 1.263(2) yes
N1 C6 1.461(2) yes
N2 C16 1.328(2) ?
N2 C14 1.369(2) ?
N3 C17 1.264(2) yes
N3 C1 1.460(2) yes
N4 C26 1.322(2) ?
N4 C24 1.372(3) ?
C1 C2 1.527(3) ?
C1 C6 1.529(2) yes
C2 C3 1.520(3) ?
C3 C4 1.523(3) ?
C4 C5 1.518(3) ?
C5 C6 1.530(3) ?
C7 C16 1.473(2) yes
C8 C9 1.357(3) ?
C8 C16 1.409(3) ?
C9 C15 1.423(2) ?
C10 C11 1.370(3) ?
C10 C15 1.410(2) ?
C11 C12 1.403(3) ?
C12 C13 1.365(3) ?
C13 C14 1.419(2) ?
C14 C15 1.408(2) ?
C17 C26 1.482(3) yes
C18 C19 1.354(3) ?
C18 C26 1.415(3) ?
C19 C25 1.413(3) ?
C20 C21 1.359(3) ?
C20 C25 1.418(3) ?
C21 C22 1.396(3) ?
C22 C23 1.369(3) ?
C23 C24 1.413(3) ?
C24 C25 1.411(3) ?