##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-02-21
_journal_date_accepted     2007-03-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      4
_journal_page_first     o1924
_journal_page_last     o1925
_journal_paper_category     EO
_journal_coeditor_code     SI2004
_publ_contact_author_name     ' Nagaraja, K.S.'
_publ_contact_author_address
;
       Department of Chemistry
       Loyola Institute of Frontier Energy
       Loyola College
       Chennai-600034
       Tamil Nadu
       India
;
_publ_contact_author_email     ksnraja@loyolacollege.edu
_publ_contact_author_fax     '+91-044-22574204'
_publ_contact_author_phone     '+91-044-28178200'
_publ_section_title
;
2,2'-[1,1'-(Propane-1,3-diyl)bis(nitriloethylidyne)diphenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Selvakumar, J.'
;
      Department of Chemistry
      Loyola Institute of Frontier Energy
      Loyola College
      Chennai 600 034
      Tamil Nadu
      India
;
    'Babu Varghese'
;
      Sophisticated Analytical Instruments Facility
      Indian Institute of Technology Madras
      Chennai 600 036
      India
;
    'Raghunathan, V. S.'
;
      Visiting Scientist
      Non-Ferrous Materials Technology Development Centre
      Hyderabad 500 058
      India
;
    'Nagaraja, K. S.'
;
      Department of Chemistry
      Loyola Institute of Frontier Energy
      Loyola College
      Chennai 600 034
      Tamil Nadu
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,2'-[1,1'-(Propane-1,3-diyl)bis(nitriloethylidyne)diphenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H22 N2 O2'
_chemical_formula_sum     'C19 H22 N2 O2'
_chemical_formula_iupac     'C19 H22 N2 O2'
_chemical_formula_weight     310.39
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     12.4524(4)
_cell_length_b     15.3347(5)
_cell_length_c     8.8832(2)
_cell_angle_alpha     90.00
_cell_angle_beta     96.991(2)
_cell_angle_gamma     90.00
_cell_volume     1683.67(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7073
_cell_measurement_theta_min     2.1
_cell_measurement_theta_max     28.
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.224
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.080
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.857
_exptl_absorpt_correction_T_max     0.984
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa-APEX2'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20405
_diffrn_reflns_av_R_equivalents     0.0372
_diffrn_reflns_av_sigmaI/netI     0.0253
_diffrn_reflns_theta_min     1.65
_diffrn_reflns_theta_max     28.69
_diffrn_reflns_theta_full     28.69
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4335
_reflns_number_gt     2848
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0820
_refine_ls_R_factor_gt     0.0523
_refine_ls_wR_factor_gt     0.1565
_refine_ls_wR_factor_ref     0.1932
_refine_ls_goodness_of_fit_ref     1.017
_refine_ls_restrained_S_all     1.017
_refine_ls_number_reflns     4335
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1092P)²+0.2308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.261
_refine_diff_density_min     -0.259
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'APEX2 and SAINT-Plus (Bruker, 2004)'
_computing_data_reduction     'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution
               'SIR92 (Altomare et al., 1993\\bbr00q) in WinGX (Farrugia, 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP32 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97'
loop_
    _atom_site_type_symbol
    _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
    C C1 0.08793(16) 0.85107(12) 1.1554(2) 0.0605(4) Uani d . 1 . .
    C C2 0.0515(2) 0.83451(15) 1.2956(2) 0.0795(6) Uani d . 1 . .
    H H2 0.1000 0.8150 1.3765 0.095 Uiso calc R 1 . .
    C C3 -0.0559(2) 0.84689(15) 1.3148(2) 0.0818(7) Uani d . 1 . .
    H H3 -0.0790 0.8359 1.4087 0.098 Uiso calc R 1 . .
    C C4 -0.12882(18) 0.87509(14) 1.1971(2) 0.0726(6) Uani d . 1 . .
    H H4 -0.2008 0.8840 1.2113 0.087 Uiso calc R 1 . .
    C C5 -0.09523(15) 0.89015(12) 1.0578(2) 0.0612(5) Uani d . 1 . .
    H H5 -0.1455 0.9089 0.9783 0.073 Uiso calc R 1 . .
    C C6 0.01260(13) 0.87813(10) 1.03197(18) 0.0497(4) Uani d . 1 . .
    C C7 0.04743(13) 0.89107(10) 0.88117(18) 0.0485(4) Uani d . 1 . .
    C C8 -0.03427(15) 0.91290(15) 0.7489(2) 0.0659(5) Uani d . 1 . .
    H H8A 0.0014 0.9193 0.6596 0.099 Uiso calc R 1 . .
    H H8B -0.0698 0.9665 0.7685 0.099 Uiso calc R 1 . .
    H H8C -0.0868 0.8669 0.7336 0.099 Uiso calc R 1 . .
    C C9 0.19118(14) 0.88534(13) 0.7236(2) 0.0592(4) Uani d . 1 . .
    H H9A 0.1767 0.9425 0.6790 0.071 Uiso calc R 1 . .
    H H9B 0.1558 0.8422 0.6548 0.071 Uiso calc R 1 . .
    C C10 0.31163(14) 0.86895(13) 0.7459(2) 0.0619(5) Uani d . 1 . .
    H H10A 0.3471 0.9175 0.8016 0.074 Uiso calc R 1 . .
    H H10B 0.3260 0.8169 0.8071 0.074 Uiso calc R 1 . .
    C C11 0.35990(15) 0.85764(12) 0.5993(2) 0.0627(5) Uani d . 1 . .
    H H11A 0.4358 0.8424 0.6214 0.075 Uiso calc R 1 . .
    H H11B 0.3233 0.8104 0.5412 0.075 Uiso calc R 1 . .
    C C12 0.38548(12) 0.94528(10) 0.38155(18) 0.0489(4) Uani d . 1 . .
    C C13 0.44276(15) 0.87288(13) 0.3096(2) 0.0670(5) Uani d . 1 . .
    H H13A 0.4458 0.8222 0.3735 0.101 Uiso calc R 1 . .
    H H13B 0.5149 0.8911 0.2971 0.101 Uiso calc R 1 . .
    H H13C 0.4041 0.8591 0.2124 0.101 Uiso calc R 1 . .
    C C14 0.37098(11) 1.03009(10) 0.30374(17) 0.0473(4) Uani d . 1 . .
    C C15 0.40440(14) 1.04511(13) 0.1617(2) 0.0634(5) Uani d . 1 . .
    H H15 0.4353 0.9996 0.1127 0.076 Uiso calc R 1 . .
    C C16 0.39290(16) 1.12563(16) 0.0914(2) 0.0726(6) Uani d . 1 . .
    H H16 0.4167 1.1341 -0.0027 0.087 Uiso calc R 1 . .
    C C17 0.34599(15) 1.19306(14) 0.1621(2) 0.0667(5) Uani d . 1 . .
    H H17 0.3382 1.2474 0.1154 0.080 Uiso calc R 1 . .
    C C18 0.31083(14) 1.18080(11) 0.3001(2) 0.0578(4) Uani d . 1 . .
    H H18 0.2789 1.2269 0.3461 0.069 Uiso calc R 1 . .
    C C19 0.32189(12) 1.10045(10) 0.37325(17) 0.0474(4) Uani d . 1 . .
    N N1 0.14839(11) 0.88058(9) 0.86902(16) 0.0534(3) Uani d . 1 . .
    N N2 0.34936(11) 0.93775(9) 0.51000(16) 0.0525(3) Uani d . 1 . .
    O O1 0.19250(11) 0.83961(11) 1.14088(16) 0.0791(4) Uani d . 1 . .
    H H1 0.2032 0.8515 1.0539 0.119 Uiso calc R 1 . .
    O O2 0.28584(11) 1.09222(8) 0.50796(13) 0.0617(3) Uani d . 1 . .
    H H2A 0.2646 1.0422 0.5179 0.093 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 O1 . 1.336(2) ?
    C1 C2 . 1.400(3) ?
    C1 C6 . 1.415(2) ?
    C2 C3 . 1.382(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.369(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.373(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.402(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.471(2) ?
    C7 N1 . 1.285(2) ?
    C7 C8 . 1.496(2) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 N1 . 1.458(2) ?
    C9 C10 . 1.510(2) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.509(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 N2 . 1.460(2) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 N2 . 1.2817(19) ?
    C12 C14 . 1.473(2) ?
    C12 C13 . 1.504(2) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 C15 . 1.395(2) ?
    C14 C19 . 1.418(2) ?
    C15 C16 . 1.383(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.376(3) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.364(3) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.392(2) ?
    C18 H18 . 0.9300 ?
    C19 O2 . 1.3343(18) ?
    O1 H1 . 0.8200 ?
    O2 H2A . 0.8200 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 C2 . . 119.14(18) ?
    O1 C1 C6 . . 121.74(16) ?
    C2 C1 C6 . . 119.12(19) ?
    C3 C2 C1 . . 120.5(2) ?
    C3 C2 H2 . . 119.7 ?
    C1 C2 H2 . . 119.7 ?
    C4 C3 C2 . . 120.74(19) ?
    C4 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    C3 C4 C5 . . 119.7(2) ?
    C3 C4 H4 . . 120.2 ?
    C5 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 121.90(19) ?
    C4 C5 H5 . . 119.1 ?
    C6 C5 H5 . . 119.1 ?
    C5 C6 C1 . . 118.01(16) ?
    C5 C6 C7 . . 121.73(15) ?
    C1 C6 C7 . . 120.25(15) ?
    N1 C7 C6 . . 117.36(14) ?
    N1 C7 C8 . . 122.74(15) ?
    C6 C7 C8 . . 119.87(15) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N1 C9 C10 . . 109.86(15) ?
    N1 C9 H9A . . 109.7 ?
    C10 C9 H9A . . 109.7 ?
    N1 C9 H9B . . 109.7 ?
    C10 C9 H9B . . 109.7 ?
    H9A C9 H9B . . 108.2 ?
    C11 C10 C9 . . 113.56(16) ?
    C11 C10 H10A . . 108.9 ?
    C9 C10 H10A . . 108.9 ?
    C11 C10 H10B . . 108.9 ?
    C9 C10 H10B . . 108.9 ?
    H10A C10 H10B . . 107.7 ?
    N2 C11 C10 . . 110.69(14) ?
    N2 C11 H11A . . 109.5 ?
    C10 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    N2 C12 C14 . . 117.45(13) ?
    N2 C12 C13 . . 123.21(16) ?
    C14 C12 C13 . . 119.33(14) ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C15 C14 C19 . . 117.39(15) ?
    C15 C14 C12 . . 122.48(14) ?
    C19 C14 C12 . . 120.14(13) ?
    C16 C15 C14 . . 121.97(17) ?
    C16 C15 H15 . . 119.0 ?
    C14 C15 H15 . . 119.0 ?
    C17 C16 C15 . . 119.45(17) ?
    C17 C16 H16 . . 120.3 ?
    C15 C16 H16 . . 120.3 ?
    C18 C17 C16 . . 120.45(18) ?
    C18 C17 H17 . . 119.8 ?
    C16 C17 H17 . . 119.8 ?
    C17 C18 C19 . . 121.15(17) ?
    C17 C18 H18 . . 119.4 ?
    C19 C18 H18 . . 119.4 ?
    O2 C19 C18 . . 118.52(14) ?
    O2 C19 C14 . . 121.90(14) ?
    C18 C19 C14 . . 119.58(15) ?
    C7 N1 C9 . . 122.34(14) ?
    C12 N2 C11 . . 122.80(14) ?
    C1 O1 H1 . . 109.5 ?
    C19 O2 H2A . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . 179.1(2) ?
    C6 C1 C2 C3 . . . . -1.9(3) ?
    C1 C2 C3 C4 . . . . 0.3(3) ?
    C2 C3 C4 C5 . . . . 0.9(3) ?
    C3 C4 C5 C6 . . . . -0.5(3) ?
    C4 C5 C6 C1 . . . . -1.1(3) ?
    C4 C5 C6 C7 . . . . 177.60(16) ?
    O1 C1 C6 C5 . . . . -178.82(17) ?
    C2 C1 C6 C5 . . . . 2.2(3) ?
    O1 C1 C6 C7 . . . . 2.5(3) ?
    C2 C1 C6 C7 . . . . -176.45(16) ?
    C5 C6 C7 N1 . . . . 178.38(15) ?
    C1 C6 C7 N1 . . . . -3.0(2) ?
    C5 C6 C7 C8 . . . . -3.4(2) ?
    C1 C6 C7 C8 . . . . 175.25(16) ?
    N1 C9 C10 C11 . . . . 170.33(15) ?
    C9 C10 C11 N2 . . . . 64.1(2) ?
    N2 C12 C14 C15 . . . . -178.23(15) ?
    C13 C12 C14 C15 . . . . 2.8(2) ?
    N2 C12 C14 C19 . . . . 2.0(2) ?
    C13 C12 C14 C19 . . . . -176.92(15) ?
    C19 C14 C15 C16 . . . . 1.4(3) ?
    C12 C14 C15 C16 . . . . -178.30(17) ?
    C14 C15 C16 C17 . . . . -0.8(3) ?
    C15 C16 C17 C18 . . . . -0.1(3) ?
    C16 C17 C18 C19 . . . . 0.4(3) ?
    C17 C18 C19 O2 . . . . -179.88(15) ?
    C17 C18 C19 C14 . . . . 0.3(2) ?
    C15 C14 C19 O2 . . . . 179.02(15) ?
    C12 C14 C19 O2 . . . . -1.2(2) ?
    C15 C14 C19 C18 . . . . -1.2(2) ?
    C12 C14 C19 C18 . . . . 178.58(14) ?
    C6 C7 N1 C9 . . . . 175.41(14) ?
    C8 C7 N1 C9 . . . . -2.8(3) ?
    C10 C9 N1 C7 . . . . -179.11(16) ?
    C14 C12 N2 C11 . . . . -179.17(15) ?
    C13 C12 N2 C11 . . . . -0.3(3) ?
    C10 C11 N2 C12 . . . . 178.99(15) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O1 H1 N1 . 0.82 1.76 2.4912(19) 147.9
    O2 H2A N2 . 0.82 1.92 2.4967(17) 126.1
    C8 H8B \P1 3_577 0.96 2.875 3.558 129.0
    C11 H11A \P2 3_576 0.97 2.822 3.678 147.6
