#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/88/1508831.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1508831
loop_
_publ_author_name
'Fourati, M. Amine'
'Skene, W. G.'
'Bazuin, C Géraldine'
'Prud'homme, Robert E.'
_publ_section_title
;
 Photophysical and Electrochemical Investigations of the Fluorescent
 Probe, 4,4'-Bis(2-benzoxazolyl)stilbene.
;
_journal_issue                   5
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              836
_journal_page_last               844
_journal_paper_doi               10.1021/jp312598c
_journal_volume                  117
_journal_year                    2013
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C14 H9 N O3'
_chemical_formula_sum            'C14 H9 N O3'
_chemical_formula_weight         239.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.436(6)
_cell_angle_beta                 95.574(7)
_cell_angle_gamma                97.222(7)
_cell_formula_units_Z            2
_cell_length_a                   4.7147(5)
_cell_length_b                   9.9033(10)
_cell_length_c                   17.3871(19)
_cell_measurement_reflns_used    3126
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.56
_cell_measurement_theta_min      2.61
_cell_volume                     783.15(15)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.087
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15190
_diffrn_reflns_theta_full        70.85
_diffrn_reflns_theta_max         70.85
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
Attempts to  model disordered solvent molecules
were unsuccessful. PLATON/SQUEEZE  was used to correct
the data for the presence of the disordered solvent.
A potential solvent volume of 270.4 Å³, 
34.5 % of the total unit-cell volume, was found.
130 electrons per unit cell worth of scattering were located
in the void. The reported structure is based on the 
PLATON/SQUEEZE corrected data. The actual solvent content is
unknown, so several quantities calculated like empirical formula, density, 
absorption coefficient, F(000) etc. may be incorrect.

Ref:  Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201.
;
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0835
_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)+(0.1615P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.2384
_reflns_number_gt                2033
_reflns_number_total             2917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jp312598c_si_002.cif
_cod_data_source_block           amin06
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        783.15(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508831
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.1789(5) -0.3632(2) 0.05026(15) 0.0273(6) Uani 1 1 d .
C2 C 0.0717(5) -0.2563(3) 0.08824(15) 0.0280(6) Uani 1 1 d .
C3 C 0.1401(5) -0.1405(3) 0.05510(15) 0.0280(6) Uani 1 1 d .
H3 H 0.0265 -0.1302 0.0090 0.034 Uiso 1 1 calc R
C4 C 0.3754(5) -0.0406(3) 0.09011(16) 0.0283(6) Uani 1 1 d .
H4 H 0.4219 0.0387 0.0681 0.034 Uiso 1 1 calc R
C5 C 0.5425(5) -0.0565(2) 0.15708(15) 0.0284(6) Uani 1 1 d .
C6 C 0.4728(6) -0.1712(3) 0.19070(16) 0.0310(6) Uani 1 1 d .
H6 H 0.5850 -0.1810 0.2371 0.037 Uiso 1 1 calc R
C7 C 0.2367(6) -0.2714(3) 0.15546(16) 0.0312(6) Uani 1 1 d .
H7 H 0.1891 -0.3502 0.1777 0.037 Uiso 1 1 calc R
C8 C 0.7928(5) 0.0461(2) 0.19273(15) 0.0267(6) Uani 1 1 d .
C9 C 1.0955(5) 0.2359(3) 0.20187(15) 0.0282(6) Uani 1 1 d .
C10 C 1.2431(6) 0.3582(3) 0.19039(18) 0.0374(7) Uani 1 1 d .
H10 H 1.1845 0.4013 0.1485 0.045 Uiso 1 1 calc R
C11 C 1.4852(6) 0.4132(3) 0.24540(19) 0.0400(7) Uani 1 1 d .
H11 H 1.5984 0.4968 0.2406 0.048 Uiso 1 1 calc R
C12 C 1.5674(6) 0.3505(3) 0.30711(19) 0.0398(7) Uani 1 1 d .
H12 H 1.7317 0.3934 0.3439 0.048 Uiso 1 1 calc R
C13 C 1.4150(6) 0.2267(3) 0.31626(17) 0.0360(6) Uani 1 1 d .
H13 H 1.4736 0.1828 0.3578 0.043 Uiso 1 1 calc R
C14 C 1.1741(5) 0.1699(3) 0.26226(15) 0.0289(6) Uani 1 1 d .
N1 N 0.9736(4) 0.0483(2) 0.25415(13) 0.0287(5) Uani 1 1 d .
O1 O 0.8516(4) 0.15659(18) 0.15631(11) 0.0305(5) Uani 1 1 d .
O2 O -0.2125(4) -0.47601(19) 0.07606(12) 0.0371(5) Uani 1 1 d .
H2 H -0.3594 -0.5287 0.0506 0.056 Uiso 1 1 calc R
O3 O -0.3423(4) -0.3395(2) -0.00576(11) 0.0365(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0234(13) 0.0202(12) 0.0386(14) 0.0029(10) 0.0062(9) 0.0079(9)
C2 0.0240(13) 0.0211(13) 0.0370(13) -0.0016(10) 0.0039(10) 0.0078(9)
C3 0.0226(13) 0.0262(13) 0.0363(13) 0.0075(10) 0.0014(9) 0.0089(9)
C4 0.0224(13) 0.0223(12) 0.0407(14) 0.0050(10) 0.0044(9) 0.0073(9)
C5 0.0262(14) 0.0196(13) 0.0390(14) 0.0019(10) 0.0057(10) 0.0072(9)
C6 0.0298(14) 0.0275(14) 0.0355(13) 0.0056(10) 0.0007(10) 0.0079(10)
C7 0.0267(14) 0.0248(13) 0.0415(14) 0.0045(10) 0.0037(10) 0.0059(9)
C8 0.0278(14) 0.0199(12) 0.0344(13) 0.0065(10) 0.0055(9) 0.0085(9)
C9 0.0234(13) 0.0258(13) 0.0329(13) 0.0012(10) -0.0003(9) 0.0056(9)
C10 0.0364(16) 0.0281(14) 0.0477(16) 0.0096(12) 0.0032(11) 0.0042(10)
C11 0.0336(16) 0.0295(15) 0.0522(17) 0.0027(12) 0.0037(12) -0.0023(10)
C12 0.0274(14) 0.0371(16) 0.0485(16) -0.0003(12) 0.0009(11) -0.0017(10)
C13 0.0311(15) 0.0386(16) 0.0387(15) 0.0076(12) 0.0010(10) 0.0100(10)
C14 0.0260(13) 0.0231(13) 0.0368(13) 0.0042(10) 0.0035(9) 0.0051(9)
N1 0.0245(11) 0.0238(11) 0.0370(12) 0.0050(8) 0.0018(8) 0.0047(7)
O1 0.0290(10) 0.0223(9) 0.0389(10) 0.0065(7) -0.0005(7) 0.0030(7)
O2 0.0310(11) 0.0240(10) 0.0539(12) 0.0052(8) 0.0019(8) 0.0025(7)
O3 0.0317(11) 0.0364(11) 0.0392(11) 0.0037(8) -0.0020(7) 0.0084(8)
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
_geom_angle_publ_flag
O3 C1 O2 123.8(2) y
O3 C1 C2 118.8(2) y
O2 C1 C2 117.3(2) y
C7 C2 C3 120.3(2) y
C7 C2 C1 120.5(2) y
C3 C2 C1 119.3(2) y
C4 C3 C2 119.5(2) y
C4 C3 H3 120.2 ?
C2 C3 H3 120.2 ?
C5 C4 C3 120.2(2) y
C5 C4 H4 119.9 ?
C3 C4 H4 119.9 ?
C4 C5 C6 120.4(2) y
C4 C5 C8 120.3(2) y
C6 C5 C8 119.3(2) y
C5 C6 C7 119.4(3) y
C5 C6 H6 120.3 ?
C7 C6 H6 120.3 ?
C2 C7 C6 120.3(3) y
C2 C7 H7 119.9 ?
C6 C7 H7 119.9 ?
N1 C8 O1 114.4(2) y
N1 C8 C5 129.0(2) y
O1 C8 C5 116.5(2) y
C10 C9 O1 127.4(2) y
C10 C9 C14 124.5(2) y
O1 C9 C14 108.1(2) y
C9 C10 C11 114.3(3) y
C9 C10 H10 122.8 ?
C11 C10 H10 122.8 ?
C12 C11 C10 122.5(3) y
C12 C11 H11 118.8 ?
C10 C11 H11 118.8 ?
C13 C12 C11 121.5(3) y
C13 C12 H12 119.2 ?
C11 C12 H12 119.2 ?
C14 C13 C12 117.0(3) y
C14 C13 H13 121.5 ?
C12 C13 H13 121.5 ?
C13 C14 C9 120.1(2) y
C13 C14 N1 132.0(2) y
C9 C14 N1 107.9(2) y
C8 N1 C14 105.4(2) y
C8 O1 C9 104.13(19) y
C1 O2 H2 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O3 1.260(3) y
C1 O2 1.282(3) y
C1 C2 1.486(3) y
C2 C7 1.384(4) y
C2 C3 1.399(4) y
C3 C4 1.391(3) y
C3 H3 0.9500 ?
C4 C5 1.388(4) y
C4 H4 0.9500 ?
C5 C6 1.395(4) y
C5 C8 1.455(4) y
C6 C7 1.395(4) y
C6 H6 0.9500 ?
C7 H7 0.9500 ?
C8 N1 1.295(3) y
C8 O1 1.381(3) y
C9 C10 1.379(4) y
C9 O1 1.384(3) y
C9 C14 1.387(4) y
C10 C11 1.393(4) y
C10 H10 0.9500 ?
C11 C12 1.390(5) y
C11 H11 0.9500 ?
C12 C13 1.387(4) y
C12 H12 0.9500 ?
C13 C14 1.382(4) y
C13 H13 0.9500 ?
C14 N1 1.409(3) y
O2 H2 0.8400 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.84 1.79 2.625(3) 170.9 2_445 y
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.032 -0.001 0.500 268.6 129.9
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 8075179 ChemSpider
