##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     'SHELXL-97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-04-26
_journal_date_accepted     2010-05-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1377
_journal_page_last     o1377
_journal_paper_category     QO
_journal_coeditor_code     JH2151
_publ_contact_author_name     'N.L.Mary'
_publ_contact_author_address
;
Department of Chemistry
Stella Maris college, Chennai
TamilNadu, India.
;
_publ_contact_author_email     maryterry13@yahoo.co.in
_publ_contact_author_fax     '  '
_publ_contact_author_phone     '+91-44-24914192'
_publ_section_title
;\
(N¹E,N²E)-N¹,N²-Bis(4-\
hexyloxy-3-methoxybenzylidene)ethane-1,2-diamine
;
loop_
    _publ_author_name
    _publ_author_address
    'Anju Paul'
;     Department of Chemistry
      Stella Maris college, Chennai
      TamilNadu, India
;
    'Sherin Susan Punnoose'
;     Department of Chemistry
      Stella Maris college, Chennai
      TamilNadu, India
;
    'N. L. Mary'
;     Department of Chemistry
      Stella Maris college, Chennai
      TamilNadu, India
;
    'T. Narasimhaswamy'
;     Polymer division
      C.L.R.I. Adyar, Chennai
      TamilNadu
      India
;
    'V. Ramkumar'
;     Department of Chemistry
      IIT Madras, Chennai
      TamilNadu
      India
;
_publ_section_synopsis
;
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(N¹E,N²E)-N¹,N²-Bis(4-
hexyloxy-3-methoxybenzylidene)ethane-1,2-diamine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C30 H44 N2 O4'
_chemical_formula_sum     'C30 H44 N2 O4'
_chemical_formula_iupac     'C30 H44 N2 O4'
_chemical_formula_weight     496.67
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.3025(6)
_cell_length_b     10.3777(14)
_cell_length_c     13.0463(17)
_cell_angle_alpha     84.667(6)
_cell_angle_beta     84.659(6)
_cell_angle_gamma     89.045(6)
_cell_volume     711.67(16)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     2606
_cell_measurement_theta_min     2.47
_cell_measurement_theta_max     24.75
_cell_measurement_temperature     298(2)
_exptl_crystal_description     rectangular
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.159
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     270
_exptl_absorpt_coefficient_mu     0.076
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.9666
_exptl_absorpt_correction_T_max     0.9924
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298(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 APEXII CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9758
_diffrn_reflns_av_R_equivalents     0.0233
_diffrn_reflns_av_sigmaI/netI     0.0321
_diffrn_reflns_theta_min     1.97
_diffrn_reflns_theta_max     28.32
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.917
_diffrn_measured_fraction_theta_full     0.957
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     3249
_reflns_number_gt     1873
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0970
_refine_ls_R_factor_gt     0.0530
_refine_ls_wR_factor_gt     0.1413
_refine_ls_wR_factor_ref     0.1669
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     3249
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0813P)²+0.0648P] 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     0.217
_refine_diff_density_min     -0.231
_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 (Bruker, 2004)'
_computing_data_reduction     'SAINT and XPREP (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997) '
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 1.3152(4) 0.4143(2) 0.8601(2) 0.0941(7) Uani d . 1 . .
    H H1A 1.4109 0.4622 0.9025 0.141 Uiso calc R 1 . .
    H H1B 1.4280 0.3615 0.8196 0.141 Uiso calc R 1 . .
    H H1C 1.1958 0.3602 0.9034 0.141 Uiso calc R 1 . .
    C C2 1.1755(4) 0.50694(19) 0.78939(16) 0.0719(6) Uani d . 1 . .
    H H2A 1.2985 0.5568 0.7428 0.086 Uiso calc R 1 . .
    H H2B 1.0780 0.4574 0.7477 0.086 Uiso calc R 1 . .
    C C3 0.9998(3) 0.59913(17) 0.84379(14) 0.0583(5) Uani d . 1 . .
    H H3A 1.0965 0.6484 0.8860 0.070 Uiso calc R 1 . .
    H H3B 0.8748 0.5497 0.8896 0.070 Uiso calc R 1 . .
    C C4 0.8650(3) 0.69171(18) 0.77122(14) 0.0581(5) Uani d . 1 . .
    H H4A 0.7761 0.6418 0.7268 0.070 Uiso calc R 1 . .
    H H4B 0.9911 0.7430 0.7274 0.070 Uiso calc R 1 . .
    C C5 0.6765(3) 0.78325(16) 0.82227(13) 0.0521(4) Uani d . 1 . .
    H H5A 0.5492 0.7336 0.8667 0.063 Uiso calc R 1 . .
    H H5B 0.7635 0.8366 0.8648 0.063 Uiso calc R 1 . .
    C C6 0.5513(3) 0.86768(16) 0.74259(13) 0.0515(4) Uani d . 1 . .
    H H6A 0.6769 0.9218 0.7011 0.062 Uiso calc R 1 . .
    H H6B 0.4736 0.8144 0.6971 0.062 Uiso calc R 1 . .
    C C7 0.2265(3) 1.02721(15) 0.72825(12) 0.0446(4) Uani d . 1 . .
    C C8 0.2641(3) 1.03991(17) 0.62159(12) 0.0555(5) Uani d . 1 . .
    H H8 0.3923 0.9928 0.5882 0.067 Uiso calc R 1 . .
    C C9 0.1123(3) 1.12212(18) 0.56439(13) 0.0591(5) Uani d . 1 . .
    H H9 0.1388 1.1290 0.4926 0.071 Uiso calc R 1 . .
    C C10 -0.0761(3) 1.19360(15) 0.61098(12) 0.0487(4) Uani d . 1 . .
    C C11 -0.1152(3) 1.18130(15) 0.71918(12) 0.0494(4) Uani d . 1 . .
    H H11 -0.2432 1.2293 0.7520 0.059 Uiso calc R 1 . .
    C C12 0.0324(3) 1.09964(14) 0.77722(11) 0.0447(4) Uani d . 1 . .
    C C13 -0.2366(4) 1.27834(18) 0.54763(14) 0.0602(5) Uani d . 1 . .
    H H13 -0.2200 1.2727 0.4766 0.072 Uiso calc R 1 . .
    C C14 -0.5432(4) 1.43145(18) 0.50776(15) 0.0694(6) Uani d . 1 . .
    H H14A -0.7211 1.4286 0.5331 0.083 Uiso calc R 1 . .
    H H14B -0.5236 1.3933 0.4424 0.083 Uiso calc R 1 . .
    C C15 -0.2111(4) 1.13500(19) 0.93525(13) 0.0670(5) Uani d . 1 . .
    H H15A -0.1983 1.2276 0.9260 0.101 Uiso calc R 1 . .
    H H15B -0.2181 1.1066 1.0076 0.101 Uiso calc R 1 . .
    H H15C -0.3621 1.1088 0.9078 0.101 Uiso calc R 1 . .
    N N1 -0.3933(3) 1.35719(15) 0.58257(12) 0.0671(5) Uani d . 1 . .
    O O1 0.3626(2) 0.94721(10) 0.79130(8) 0.0519(3) Uani d . 1 . .
    O O2 0.0049(2) 1.07846(12) 0.88225(8) 0.0605(4) Uani d . 1 . .
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
    C1 0.0811(16) 0.0828(16) 0.1147(19) 0.0396(13) -0.0043(14) -0.0015(14)
    C2 0.0653(12) 0.0674(12) 0.0814(13) 0.0241(10) 0.0002(10) -0.0095(10)
    C3 0.0479(10) 0.0593(11) 0.0672(11) 0.0142(8) -0.0050(8) -0.0067(9)
    C4 0.0467(10) 0.0634(11) 0.0629(11) 0.0134(9) -0.0027(8) -0.0038(9)
    C5 0.0451(9) 0.0534(10) 0.0577(10) 0.0132(8) -0.0068(7) -0.0043(8)
    C6 0.0430(9) 0.0546(10) 0.0564(10) 0.0115(8) -0.0023(7) -0.0076(8)
    C7 0.0454(9) 0.0438(9) 0.0441(9) 0.0079(7) -0.0086(7) 0.0017(7)
    C8 0.0561(10) 0.0636(11) 0.0444(9) 0.0144(9) 0.0013(8) -0.0004(8)
    C9 0.0700(12) 0.0654(11) 0.0395(9) 0.0083(10) -0.0055(8) 0.0058(8)
    C10 0.0595(11) 0.0427(9) 0.0442(9) 0.0042(8) -0.0163(7) 0.0047(7)
    C11 0.0590(10) 0.0427(9) 0.0472(9) 0.0153(8) -0.0132(8) -0.0016(7)
    C12 0.0539(10) 0.0414(8) 0.0388(8) 0.0091(8) -0.0094(7) -0.0007(6)
    C13 0.0760(13) 0.0563(11) 0.0489(10) 0.0035(10) -0.0167(9) 0.0026(8)
    C14 0.0782(14) 0.0599(11) 0.0704(12) 0.0094(10) -0.0297(10) 0.0136(9)
    C15 0.0789(13) 0.0752(13) 0.0447(9) 0.0331(10) -0.0010(9) -0.0037(8)
    N1 0.0792(11) 0.0629(10) 0.0585(9) 0.0163(9) -0.0208(8) 0.0088(8)
    O1 0.0519(7) 0.0569(7) 0.0461(6) 0.0233(6) -0.0072(5) -0.0009(5)
    O2 0.0727(8) 0.0701(8) 0.0373(6) 0.0373(6) -0.0073(5) -0.0017(5)
_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 C2 . 1.504(3) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C3 . 1.503(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.505(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.519(2) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C6 . 1.493(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 O1 . 1.4274(18) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 O1 . 1.3602(18) ?
    C7 C8 . 1.382(2) ?
    C7 C12 . 1.405(2) ?
    C8 C9 . 1.380(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.365(2) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.402(2) ?
    C10 C13 . 1.467(2) ?
    C11 C12 . 1.369(2) ?
    C11 H11 . 0.9300 ?
    C12 O2 . 1.3620(18) ?
    C13 N1 . 1.243(2) ?
    C13 H13 . 0.9300 ?
    C14 N1 . 1.470(2) ?
    C14 C14 2_486 1.492(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 O2 . 1.428(2) ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
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
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C3 C2 C1 . . 114.57(19) ?
    C3 C2 H2A . . 108.6 ?
    C1 C2 H2A . . 108.6 ?
    C3 C2 H2B . . 108.6 ?
    C1 C2 H2B . . 108.6 ?
    H2A C2 H2B . . 107.6 ?
    C2 C3 C4 . . 113.47(16) ?
    C2 C3 H3A . . 108.9 ?
    C4 C3 H3A . . 108.9 ?
    C2 C3 H3B . . 108.9 ?
    C4 C3 H3B . . 108.9 ?
    H3A C3 H3B . . 107.7 ?
    C3 C4 C5 . . 115.64(15) ?
    C3 C4 H4A . . 108.4 ?
    C5 C4 H4A . . 108.4 ?
    C3 C4 H4B . . 108.4 ?
    C5 C4 H4B . . 108.4 ?
    H4A C4 H4B . . 107.4 ?
    C6 C5 C4 . . 110.57(14) ?
    C6 C5 H5A . . 109.5 ?
    C4 C5 H5A . . 109.5 ?
    C6 C5 H5B . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 108.1 ?
    O1 C6 C5 . . 110.11(13) ?
    O1 C6 H6A . . 109.6 ?
    C5 C6 H6A . . 109.6 ?
    O1 C6 H6B . . 109.6 ?
    C5 C6 H6B . . 109.6 ?
    H6A C6 H6B . . 108.2 ?
    O1 C7 C8 . . 124.79(15) ?
    O1 C7 C12 . . 116.27(13) ?
    C8 C7 C12 . . 118.93(14) ?
    C9 C8 C7 . . 120.33(16) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C10 C9 C8 . . 121.35(15) ?
    C10 C9 H9 . . 119.3 ?
    C8 C9 H9 . . 119.3 ?
    C9 C10 C11 . . 118.64(15) ?
    C9 C10 C13 . . 119.84(15) ?
    C11 C10 C13 . . 121.51(16) ?
    C12 C11 C10 . . 120.86(15) ?
    C12 C11 H11 . . 119.6 ?
    C10 C11 H11 . . 119.6 ?
    O2 C12 C11 . . 125.23(14) ?
    O2 C12 C7 . . 114.87(13) ?
    C11 C12 C7 . . 119.88(14) ?
    N1 C13 C10 . . 124.35(17) ?
    N1 C13 H13 . . 117.8 ?
    C10 C13 H13 . . 117.8 ?
    N1 C14 C14 . 2_486 109.91(19) ?
    N1 C14 H14A . . 109.7 ?
    C14 C14 H14A 2_486 . 109.7 ?
    N1 C14 H14B . . 109.7 ?
    C14 C14 H14B 2_486 . 109.7 ?
    H14A C14 H14B . . 108.2 ?
    O2 C15 H15A . . 109.5 ?
    O2 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O2 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C13 N1 C14 . . 116.83(17) ?
    C7 O1 C6 . . 116.96(12) ?
    C12 O2 C15 . . 117.33(12) ?
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
    C1 C2 C3 C4 . . . . 179.30(18) ?
    C2 C3 C4 C5 . . . . 177.47(15) ?
    C3 C4 C5 C6 . . . . -178.66(15) ?
    C4 C5 C6 O1 . . . . 176.14(13) ?
    O1 C7 C8 C9 . . . . 178.75(15) ?
    C12 C7 C8 C9 . . . . -0.2(3) ?
    C7 C8 C9 C10 . . . . 0.6(3) ?
    C8 C9 C10 C11 . . . . -0.6(3) ?
    C8 C9 C10 C13 . . . . -178.96(16) ?
    C9 C10 C11 C12 . . . . 0.1(2) ?
    C13 C10 C11 C12 . . . . 178.52(15) ?
    C10 C11 C12 O2 . . . . -178.15(15) ?
    C10 C11 C12 C7 . . . . 0.2(2) ?
    O1 C7 C12 O2 . . . . -0.7(2) ?
    C8 C7 C12 O2 . . . . 178.37(15) ?
    O1 C7 C12 C11 . . . . -179.24(14) ?
    C8 C7 C12 C11 . . . . -0.2(2) ?
    C9 C10 C13 N1 . . . . -171.75(17) ?
    C11 C10 C13 N1 . . . . 9.9(3) ?
    C10 C13 N1 C14 . . . . -178.23(15) ?
    C14 C14 N1 C13 2_486 . . . -107.7(3) ?
    C8 C7 O1 C6 . . . . -2.4(2) ?
    C12 C7 O1 C6 . . . . 176.64(13) ?
    C5 C6 O1 C7 . . . . -178.19(13) ?
    C11 C12 O2 C15 . . . . 7.1(2) ?
    C7 C12 O2 C15 . . . . -171.33(15) ?
