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###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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  #
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data_global
_audit_creation_method     SHELXL
_journal_date_recd_electronic     2009-01-03
_journal_date_accepted     2009-01-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2009
_journal_volume     65
_journal_issue      3
_journal_page_first     o81
_journal_page_last     o84
_journal_paper_category     FO
_journal_coeditor_code     GD3269
_publ_contact_author
;
 Baggio, Ricardo F.
 Departamento de Física,
 Comisión Nacional de Energía Atómica.
 Av. gral Paz 1499,
 1650 San Martín, Buenos Aires, Argentina.
;
_publ_contact_author_email     baggio@cnea.gov.ar
_publ_contact_author_fax     54-11-6772_7121
_publ_contact_author_phone     54-11-6772_7109
_publ_section_title
;
4'-[2-(2-Ethoxyethoxy)ethoxy]biphenyl-4-carboxylic acid: correlation between its
crystalline and smectic phases
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rosana S. Montani' .
;
INQUISUR
Departamento de Química
Universidad Nacional del Sur
Bahía Blanca
Argentina
;
    'Raúl O. Garay' .
;
INQUISUR
Departamento de Química
Universidad Nacional del Sur
Bahía Blanca
Argentina
;
    'Fabio D. Cukiernik' .
;
Departamento de Química Inorgánica
Analítica y Química Física
Facultad de Ciencias Exactas y Naturales
UBA
Buenos Aires
Argentina
and
Instituto de Ciencias
Universidad Nacional de General Sarmiento
Buenos Aires
Argentina
;
    'Maria T. Garland' .
;
Departamento de Física
Facultad de Ciencias Físicas y Matemáticas and CIMAT
Universidad de Chile
Santiago de Chile
Chile
;
    'Ricardo Baggio' .
;
Departamento de Física
Centro Atómico Constituyentes
Comisión Nacional de Energía Atómica
Buenos Aires
Argentina
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4'-[2-(2-Ethoxyethoxy)ethoxy]biphenyl-4-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H22 O5'
_chemical_formula_sum     'C19 H22 O5'
_chemical_formula_iupac     'C19 H22 O5'
_chemical_formula_weight     330.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/c 1'
_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     25.430(7)
_cell_length_b     7.769(2)
_cell_length_c     8.656(2)
_cell_angle_alpha     90.00
_cell_angle_beta     96.187(5)
_cell_angle_gamma     90.00
_cell_volume     1700.3(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1583
_cell_measurement_theta_min     2.43
_cell_measurement_theta_max     22.94
_cell_measurement_temperature     294(2)
_exptl_crystal_description     plates
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.291
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS in SAINT-NT; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.95
_exptl_absorpt_correction_T_max     0.99
_exptl_special_details
;
 1HNMR and 13C NMR spectra were recorded on a Bruker ARX300 spectrometer at 25
 °C.
;
_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 SMART CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9420
_diffrn_reflns_av_R_equivalents     0.0260
_diffrn_reflns_av_sigmaI/netI     0.0370
_diffrn_reflns_theta_min     2.42
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -31
_diffrn_reflns_limit_h_max     31
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3634
_reflns_number_gt     2230
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1058
_refine_ls_R_factor_gt     0.0627
_refine_ls_wR_factor_gt     0.1649
_refine_ls_wR_factor_ref     0.1910
_refine_ls_goodness_of_fit_ref     0.986
_refine_ls_restrained_S_all     0.986
_refine_ls_number_reflns     3634
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1098P)²] 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     0.225
_refine_diff_density_min     -0.138
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
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 0.15576(9) 0.6058(3) 0.6032(3) 0.0555(6) Uani d . 1 . .
    H H1 0.1860 0.6742 0.6146 0.067 Uiso calc R 1 . .
    C C2 0.12236(9) 0.6057(3) 0.7180(3) 0.0568(6) Uani d . 1 . .
    H H2 0.1307 0.6724 0.8065 0.068 Uiso calc R 1 . .
    C C3 0.07696(8) 0.5086(3) 0.7045(2) 0.0465(5) Uani d . 1 . .
    C C4 0.06513(9) 0.4117(3) 0.5711(2) 0.0537(6) Uani d . 1 . .
    H H4 0.0341 0.3473 0.5584 0.064 Uiso calc R 1 . .
    C C5 0.09869(9) 0.4100(3) 0.4580(3) 0.0532(6) Uani d . 1 . .
    H H5 0.0902 0.3427 0.3700 0.064 Uiso calc R 1 . .
    C C6 0.14520(8) 0.5058(2) 0.4704(2) 0.0435(5) Uani d . 1 . .
    C C7 0.18191(8) 0.5016(2) 0.3475(2) 0.0435(5) Uani d . 1 . .
    C C8 0.16623(9) 0.4356(3) 0.2012(3) 0.0530(6) Uani d . 1 . .
    H H8 0.1318 0.3950 0.1799 0.064 Uiso calc R 1 . .
    C C9 0.19938(9) 0.4275(3) 0.0863(3) 0.0542(6) Uani d . 1 . .
    H H9 0.1873 0.3814 -0.0102 0.065 Uiso calc R 1 . .
    C C10 0.25055(8) 0.4876(3) 0.1139(2) 0.0461(5) Uani d . 1 . .
    C C11 0.26716(9) 0.5581(3) 0.2584(2) 0.0521(6) Uani d . 1 . .
    H H11 0.3013 0.6012 0.2781 0.063 Uiso calc R 1 . .
    C C12 0.23362(8) 0.5648(3) 0.3721(2) 0.0486(5) Uani d . 1 . .
    H H12 0.2456 0.6125 0.4680 0.058 Uiso calc R 1 . .
    O O13 0.28714(6) 0.4826(2) 0.00990(16) 0.0570(4) Uani d . 1 . .
    C C14 0.27139(10) 0.4136(3) -0.1402(3) 0.0620(6) Uani d . 1 . .
    H H14A 0.2450 0.4875 -0.1957 0.074 Uiso calc R 1 . .
    H H14B 0.2559 0.3004 -0.1307 0.074 Uiso calc R 1 . .
    C C15 0.31857(10) 0.4010(3) -0.2273(3) 0.0647(7) Uani d . 1 . .
    H H15A 0.3472 0.3456 -0.1627 0.078 Uiso calc R 1 . .
    H H15B 0.3101 0.3308 -0.3193 0.078 Uiso calc R 1 . .
    O O16 0.33485(6) 0.56469(19) -0.27114(18) 0.0604(5) Uani d . 1 . .
    C C17 0.37864(10) 0.5582(4) -0.3559(3) 0.0697(7) Uani d . 1 . .
    H H17A 0.3712 0.4799 -0.4428 0.084 Uiso calc R 1 . .
    H H17B 0.4089 0.5138 -0.2901 0.084 Uiso calc R 1 . .
    C C18 0.39175(11) 0.7302(4) -0.4150(3) 0.0718(7) Uani d . 1 . .
    H H18A 0.4166 0.7181 -0.4918 0.086 Uiso calc R 1 . .
    H H18B 0.3600 0.7844 -0.4647 0.086 Uiso calc R 1 . .
    O O19 0.41392(7) 0.8332(2) -0.2923(2) 0.0780(6) Uani d . 1 . .
    C C20 0.43138(15) 0.9941(5) -0.3457(4) 0.1064(11) Uani d . 1 . .
    H H20A 0.4014 1.0582 -0.3946 0.128 Uiso calc R 1 . .
    H H20B 0.4558 0.9751 -0.4226 0.128 Uiso calc R 1 . .
    C C21 0.45739(17) 1.0931(5) -0.2167(6) 0.1313(15) Uani d . 1 . .
    H H21A 0.4316 1.1301 -0.1505 0.197 Uiso calc R 1 . .
    H H21B 0.4743 1.1918 -0.2561 0.197 Uiso calc R 1 . .
    H H21C 0.4834 1.0226 -0.1583 0.197 Uiso calc R 1 . .
    C C22 0.04230(8) 0.5066(3) 0.8313(2) 0.0487(5) Uani d . 1 . .
    O O23 0.05595(7) 0.5912(2) 0.95267(18) 0.0711(5) Uani d . 1 . .
    O O24 0.00103(6) 0.4157(2) 0.81277(19) 0.0704(5) Uani d . 1 . .
    H H24 -0.0180 0.4142 0.8834 0.084 Uiso d R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 . 1.376(3) ?
    C1 C6 . 1.390(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.373(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.384(3) ?
    C3 C22 . 1.480(3) ?
    C4 C5 . 1.367(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.392(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.490(3) ?
    C7 C8 . 1.384(3) ?
    C7 C12 . 1.398(3) ?
    C8 C9 . 1.373(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.379(3) ?
    C9 H9 . 0.9300 ?
    C10 O13 . 1.363(2) ?
    C10 C11 . 1.389(3) ?
    C11 C12 . 1.371(3) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    O13 C14 . 1.423(3) ?
    C14 C15 . 1.487(3) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 O16 . 1.402(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    O16 C17 . 1.399(3) ?
    C17 C18 . 1.481(4) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 O19 . 1.399(3) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    O19 C20 . 1.420(3) ?
    C20 C21 . 1.455(5) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C22 O24 . 1.261(3) ?
    C22 O23 . 1.256(2) ?
    O24 H24 . 0.8201 ?
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 C6 . . 121.2(2) ?
    C2 C1 H1 . . 119.4 ?
    C6 C1 H1 . . 119.4 ?
    C3 C2 C1 . . 121.2(2) ?
    C3 C2 H2 . . 119.4 ?
    C1 C2 H2 . . 119.4 ?
    C2 C3 C4 . . 118.4(2) ?
    C2 C3 C22 . . 120.3(2) ?
    C4 C3 C22 . . 121.32(19) ?
    C5 C4 C3 . . 120.4(2) ?
    C5 C4 H4 . . 119.8 ?
    C3 C4 H4 . . 119.8 ?
    C4 C5 C6 . . 122.0(2) ?
    C4 C5 H5 . . 119.0 ?
    C6 C5 H5 . . 119.0 ?
    C5 C6 C1 . . 116.7(2) ?
    C5 C6 C7 . . 121.75(19) ?
    C1 C6 C7 . . 121.51(19) ?
    C8 C7 C12 . . 116.3(2) ?
    C8 C7 C6 . . 121.35(19) ?
    C12 C7 C6 . . 122.35(19) ?
    C9 C8 C7 . . 122.7(2) ?
    C9 C8 H8 . . 118.6 ?
    C7 C8 H8 . . 118.6 ?
    C8 C9 C10 . . 120.1(2) ?
    C8 C9 H9 . . 120.0 ?
    C10 C9 H9 . . 120.0 ?
    O13 C10 C9 . . 125.11(19) ?
    O13 C10 C11 . . 116.28(19) ?
    C9 C10 C11 . . 118.6(2) ?
    C12 C11 C10 . . 120.6(2) ?
    C12 C11 H11 . . 119.7 ?
    C10 C11 H11 . . 119.7 ?
    C11 C12 C7 . . 121.6(2) ?
    C11 C12 H12 . . 119.2 ?
    C7 C12 H12 . . 119.2 ?
    C10 O13 C14 . . 117.94(16) ?
    O13 C14 C15 . . 108.9(2) ?
    O13 C14 H14A . . 109.9 ?
    C15 C14 H14A . . 109.9 ?
    O13 C14 H14B . . 109.9 ?
    C15 C14 H14B . . 109.9 ?
    H14A C14 H14B . . 108.3 ?
    O16 C15 C14 . . 110.8(2) ?
    O16 C15 H15A . . 109.5 ?
    C14 C15 H15A . . 109.5 ?
    O16 C15 H15B . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 108.1 ?
    C15 O16 C17 . . 112.60(18) ?
    O16 C17 C18 . . 111.7(2) ?
    O16 C17 H17A . . 109.3 ?
    C18 C17 H17A . . 109.3 ?
    O16 C17 H17B . . 109.3 ?
    C18 C17 H17B . . 109.3 ?
    H17A C17 H17B . . 107.9 ?
    O19 C18 C17 . . 109.9(2) ?
    O19 C18 H18A . . 109.7 ?
    C17 C18 H18A . . 109.7 ?
    O19 C18 H18B . . 109.7 ?
    C17 C18 H18B . . 109.7 ?
    H18A C18 H18B . . 108.2 ?
    C18 O19 C20 . . 111.8(2) ?
    O19 C20 C21 . . 110.3(3) ?
    O19 C20 H20A . . 109.6 ?
    C21 C20 H20A . . 109.6 ?
    O19 C20 H20B . . 109.6 ?
    C21 C20 H20B . . 109.6 ?
    H20A C20 H20B . . 108.1 ?
    C20 C21 H21A . . 109.5 ?
    C20 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C20 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    O24 C22 O23 . . 123.4(2) ?
    O24 C22 C3 . . 117.73(19) ?
    O23 C22 C3 . . 118.8(2) ?
    C22 O24 H24 . . 117.6 ?
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
    C6 C1 C2 C3 . . . . -1.0(4) ?
    C1 C2 C3 C4 . . . . -0.7(3) ?
    C1 C2 C3 C22 . . . . 178.3(2) ?
    C2 C3 C4 C5 . . . . 1.6(3) ?
    C22 C3 C4 C5 . . . . -177.4(2) ?
    C3 C4 C5 C6 . . . . -0.9(3) ?
    C4 C5 C6 C1 . . . . -0.8(3) ?
    C4 C5 C6 C7 . . . . 179.3(2) ?
    C2 C1 C6 C5 . . . . 1.7(3) ?
    C2 C1 C6 C7 . . . . -178.3(2) ?
    C5 C6 C7 C8 . . . . 15.1(3) ?
    C1 C6 C7 C8 . . . . -164.9(2) ?
    C5 C6 C7 C12 . . . . -165.4(2) ?
    C1 C6 C7 C12 . . . . 14.6(3) ?
    C12 C7 C8 C9 . . . . 1.6(3) ?
    C6 C7 C8 C9 . . . . -178.9(2) ?
    C7 C8 C9 C10 . . . . -0.4(3) ?
    C8 C9 C10 O13 . . . . 178.5(2) ?
    C8 C9 C10 C11 . . . . -1.0(3) ?
    O13 C10 C11 C12 . . . . -178.34(19) ?
    C9 C10 C11 C12 . . . . 1.2(3) ?
    C10 C11 C12 C7 . . . . 0.0(3) ?
    C8 C7 C12 C11 . . . . -1.3(3) ?
    C6 C7 C12 C11 . . . . 179.17(19) ?
    C9 C10 O13 C14 . . . . 1.4(3) ?
    C11 C10 O13 C14 . . . . -179.1(2) ?
    C10 O13 C14 C15 . . . . -173.27(19) ?
    O13 C14 C15 O16 . . . . -72.1(3) ?
    C14 C15 O16 C17 . . . . -178.9(2) ?
    C15 O16 C17 C18 . . . . 174.1(2) ?
    O16 C17 C18 O19 . . . . 72.2(3) ?
    C17 C18 O19 C20 . . . . 174.8(2) ?
    C18 O19 C20 C21 . . . . -176.2(3) ?
    C2 C3 C22 O24 . . . . 179.8(2) ?
    C4 C3 C22 O24 . . . . -1.2(3) ?
    C2 C3 C22 O23 . . . . -1.9(3) ?
    C4 C3 C22 O23 . . . . 177.0(2) ?
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
    O24 H24 O23 3_567 0.82 1.80 2.619(2) 176
    C18 H18B O13 4_575 0.97 2.58 3.478(3) 154
    C1 H1 Cg2 4_576 0.93 2.83 2.83 138.
    C14 H14B Cg2 4_565 0.97 2.74 2.74 149
