#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/74/2017472.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_2017472
loop_
_publ_author_name
'Fourati, M. Amine'
'Maris, Thierry'
'Bazuin, C. Géraldine'
'Prud'homme, Robert E.'
_publ_section_title
;
 (E)-4,4'-Bis(1,3-benzoxazol-2-yl)stilbene at 150 and 375K
;
_journal_coeditor_code           GD3316
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o11
_journal_page_last               o14
_journal_paper_doi               10.1107/S0108270109050379
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C28 H18 N2 O2'
_chemical_formula_moiety         'C28 H18 N2 O2'
_chemical_formula_sum            'C28 H18 N2 O2'
_chemical_formula_weight         414.44
_chemical_name_systematic
;
(E)-4,4'-Bis(1,3-benzoxazol-2-yl)stilbene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 96.4280(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2449(4)
_cell_length_b                   6.0053(2)
_cell_length_c                   29.0699(11)
_cell_measurement_reflns_used    7849
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.66
_cell_measurement_theta_min      3.06
_cell_volume                     1950.72(12)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Material Studio (Accelrys, 2005)
;
_computing_publication_material
;
UdMX (Maris, 2004) and publCIF (Westrip, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            17375
_diffrn_reflns_theta_full        68.07
_diffrn_reflns_theta_max         68.07
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.8744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1778
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0457P)²+1.0947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1606
_reflns_number_total             1778
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3316.cif
_cod_data_source_block           I_150K
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2017472
_cod_database_fobs_code          2017472
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'
'-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_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 0.70388(11) -0.2125(2) 0.01025(4) 0.0310(3) Uani d . 1 . .
H H1 0.6318 -0.2958 0.0053 0.037 Uiso calc R 1 . .
C C2 0.70240(11) -0.01447(19) 0.03964(4) 0.0283(3) Uani d . 1 . .
C C3 0.59417(11) 0.0526(2) 0.05470(4) 0.0309(3) Uani d . 1 . .
H H3 0.5239 -0.0317 0.0458 0.037 Uiso calc R 1 . .
C C4 0.58684(11) 0.2389(2) 0.08234(4) 0.0298(3) Uani d . 1 . .
H H4 0.5122 0.2819 0.0920 0.036 Uiso calc R 1 . .
C C5 0.68940(11) 0.36286(19) 0.09584(4) 0.0272(3) Uani d . 1 A .
C C6 0.79834(11) 0.2958(2) 0.08159(4) 0.0305(3) Uani d . 1 . .
H H6 0.8689 0.3784 0.0911 0.037 Uiso calc R 1 . .
C C7 0.80464(11) 0.1112(2) 0.05392(4) 0.0310(3) Uani d . 1 . .
H H7 0.8795 0.0686 0.0444 0.037 Uiso calc R 1 . .
C C8 0.68404(11) 0.55915(19) 0.12471(4) 0.0309(3) Uani d D 1 . .
C C9 0.62569(10) 0.82678(19) 0.16546(4) 0.0267(3) Uani d D 1 . .
C C10 0.74851(11) 0.84592(19) 0.16490(4) 0.0269(3) Uani d D 1 A .
C C11 0.81518(11) 1.0152(2) 0.18713(4) 0.0311(3) Uani d . 1 . .
H H11 0.8992 1.0266 0.1863 0.037 Uiso calc R 1 A .
C C12 0.75200(11) 1.1676(2) 0.21069(4) 0.0330(3) Uani d . 1 A .
H H12 0.7939 1.2865 0.2268 0.040 Uiso calc R 1 . .
C C13 0.62859(12) 1.1507(2) 0.21132(4) 0.0331(3) Uani d . 1 . .
H H13 0.5885 1.2591 0.2277 0.040 Uiso calc R 1 A .
C C14 0.56258(11) 0.9804(2) 0.18867(4) 0.0319(3) Uani d . 1 A .
H H14 0.4784 0.9696 0.1891 0.038 Uiso calc R 1 . .
N N1A 0.5897(4) 0.6394(13) 0.1385(4) 0.0298(7) Uani d PD 0.669(10) A 1
O O1A 0.7880(3) 0.6741(12) 0.1391(3) 0.0277(7) Uani d PD 0.669(10) A 1
O O1B 0.5818(6) 0.644(2) 0.1405(6) 0.0277(7) Uani d PD 0.331(10) A 2
N N1B 0.7791(7) 0.668(3) 0.1371(9) 0.0298(7) Uani d PD 0.331(10) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 C1 C2 7_645 . . 126.56(15) ?
C1 C1 H1 7_645 . . 116.7 ?
C2 C1 H1 . . . 116.7 ?
C3 C2 C7 . . . 117.83(11) ?
C3 C2 C1 . . . 118.91(11) ?
C7 C2 C1 . . . 123.25(11) ?
C4 C3 C2 . . . 121.65(11) ?
C4 C3 H3 . . . 119.2 ?
C2 C3 H3 . . . 119.2 ?
C3 C4 C5 . . . 119.63(11) ?
C3 C4 H4 . . . 120.2 ?
C5 C4 H4 . . . 120.2 ?
C4 C5 C6 . . . 119.29(11) ?
C4 C5 C8 . . . 120.69(11) ?
C6 C5 C8 . . . 120.02(11) ?
C7 C6 C5 . . . 120.68(11) ?
C7 C6 H6 . . . 119.7 ?
C5 C6 H6 . . . 119.7 ?
C6 C7 C2 . . . 120.91(11) ?
C6 C7 H7 . . . 119.5 ?
C2 C7 H7 . . . 119.5 ?
N1A C8 O1A . . . 115.02(12) ?
N1B C8 O1B . . . 114.91(13) ?
N1A C8 C5 . . . 125.47(19) ?
N1B C8 C5 . . . 119.6(2) ?
O1A C8 C5 . . . 119.51(16) ?
O1B C8 C5 . . . 125.51(17) ?
O1B C9 C14 . . . 128.0(2) ?
O1B C9 C10 . . . 111.0(2) ?
C14 C9 C10 . . . 121.04(11) ?
C14 C9 N1A . . . 132.4(2) ?
C10 C9 N1A . . . 106.5(2) ?
O1A C10 C11 . . . 127.97(17) ?
O1A C10 C9 . . . 109.03(15) ?
C11 C10 C9 . . . 122.99(11) ?
C11 C10 N1B . . . 132.4(3) ?
C9 C10 N1B . . . 104.6(3) ?
C10 C11 C12 . . . 115.86(11) ?
C10 C11 H11 . . . 122.1 ?
C12 C11 H11 . . . 122.1 ?
C11 C12 C13 . . . 121.67(11) ?
C11 C12 H12 . . . 119.2 ?
C13 C12 H12 . . . 119.2 ?
C14 C13 C12 . . . 121.90(11) ?
C14 C13 H13 . . . 119.1 ?
C12 C13 H13 . . . 119.1 ?
C9 C14 C13 . . . 116.53(12) ?
C9 C14 H14 . . . 121.7 ?
C13 C14 H14 . . . 121.7 ?
C8 N1A C9 . . . 106.3(3) ?
C10 O1A C8 . . . 103.1(2) ?
C9 O1B C8 . . . 101.9(3) ?
C8 N1B C10 . . . 107.6(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C1 . 7_645 1.331(2) ?
C1 C2 . . 1.4656(17) ?
C1 H1 . . 0.95 ?
C2 C3 . . 1.3981(17) ?
C2 C7 . . 1.3990(17) ?
C3 C4 . . 1.3853(17) ?
C3 H3 . . 0.95 ?
C4 C5 . . 1.3917(17) ?
C4 H4 . . 0.95 ?
C5 C6 . . 1.3957(17) ?
C5 C8 . . 1.4520(17) ?
C6 C7 . . 1.3760(17) ?
C6 H6 . . 0.95 ?
C7 H7 . . 0.95 ?
C8 N1a . . 1.270(5) ?
C8 N1b . . 1.270(5) ?
C8 O1a . . 1.382(4) ?
C8 O1b . . 1.382(4) ?
C9 O1b . . 1.377(3) ?
C9 C14 . . 1.3845(17) ?
C9 C10 . . 1.3878(17) ?
C9 N1a . . 1.405(4) ?
C10 O1a . . 1.377(3) ?
C10 C11 . . 1.3802(17) ?
C10 N1b . . 1.405(4) ?
C11 C12 . . 1.3855(17) ?
C11 H11 . . 0.95 ?
C12 C13 . . 1.3935(18) ?
C12 H12 . . 0.95 ?
C13 C14 . . 1.3862(18) ?
C13 H13 . . 0.95 ?
C14 H14 . . 0.95 ?
