#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/16/1501634.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_1501634
loop_
_publ_author_name
'M. Amine Fourati'
'Thierry Maris'
'William G. Skene'
'C. Géraldine Bazuin'
'Robert E. Prud'homme'
_publ_section_title
;
 Photophysical, Electrochemical and Crystallographic Investigations of the
 Fluorophore 2,5-Bis(5-tert-butyl-benzoxazol-2-yl)thiophene
;
_journal_name_full               'The Journal of Physical Chemistry B'
_journal_page_first              12362
_journal_page_last               12369
_journal_paper_doi               10.1021/jp207136k
_journal_volume                  115
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C26 H26 N2 O2 S'
_chemical_formula_sum            'C26 H26 N2 O2 S'
_chemical_formula_weight         430.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 107.512(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9167(7)
_cell_length_b                   6.2563(2)
_cell_length_c                   21.1871(8)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      3.86
_cell_volume                     2264.84(14)
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.052
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27199
_diffrn_reflns_theta_full        67.13
_diffrn_reflns_theta_max         67.13
_diffrn_reflns_theta_min         3.86
_exptl_absorpt_coefficient_mu    1.462
_exptl_absorpt_correction_T_max  0.9295
_exptl_absorpt_correction_T_min  0.7317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0636P)²+1.5822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                3173
_reflns_number_total             4009
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           amin02
_cod_original_cell_volume        2264.87(15)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1501634
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S1 S 0.86939(4) 0.05844(9) 0.39097(3) 0.03673(19) Uani 1 1 d .
C1 C 0.86115(15) -0.3224(4) 0.34455(12) 0.0386(6) Uani 1 1 d .
H1 H 0.8411 -0.4541 0.3241 0.046 Uiso 1 1 calc R
C2 C 0.81527(15) -0.1557(4) 0.35095(11) 0.0356(6) Uani 1 1 d .
C3 C 0.73113(15) -0.1368(4) 0.32891(11) 0.0367(6) Uani 1 1 d .
C4 C 0.61168(15) -0.0420(4) 0.30619(12) 0.0362(5) Uani 1 1 d .
C5 C 0.61350(14) -0.2409(4) 0.27793(11) 0.0358(5) Uani 1 1 d .
C6 C 0.54669(16) -0.3489(4) 0.24330(12) 0.0421(6) Uani 1 1 d .
H6 H 0.5487 -0.4859 0.2245 0.051 Uiso 1 1 calc R
C7 C 0.47689(15) -0.2467(4) 0.23752(12) 0.0413(6) Uani 1 1 d .
H7 H 0.4297 -0.3150 0.2130 0.050 Uiso 1 1 calc R
C8 C 0.47191(15) -0.0453(4) 0.26626(11) 0.0377(6) Uani 1 1 d .
C9 C 0.54055(15) 0.0570(4) 0.30060(12) 0.0384(6) Uani 1 1 d .
H9 H 0.5391 0.1931 0.3201 0.046 Uiso 1 1 calc R
C10 C 0.39076(15) 0.0475(4) 0.25956(13) 0.0420(6) Uani 1 1 d .
C11 C 0.3461(2) -0.1041(6) 0.2907(2) 0.0840(12) Uani 1 1 d .
H11A H 0.3373 -0.2395 0.2662 0.126 Uiso 1 1 calc R
H11B H 0.2956 -0.0404 0.2890 0.126 Uiso 1 1 calc R
H11C H 0.3764 -0.1307 0.3368 0.126 Uiso 1 1 calc R
C12 C 0.3467(2) 0.0882(8) 0.18778(16) 0.0930(14) Uani 1 1 d .
H12A H 0.3766 0.1871 0.1689 0.140 Uiso 1 1 calc R
H12B H 0.2955 0.1510 0.1845 0.140 Uiso 1 1 calc R
H12C H 0.3392 -0.0471 0.1633 0.140 Uiso 1 1 calc R
C13 C 0.39607(19) 0.2595(5) 0.2971(2) 0.0737(10) Uani 1 1 d .
H13A H 0.4268 0.2387 0.3435 0.111 Uiso 1 1 calc R
H13B H 0.3433 0.3080 0.2948 0.111 Uiso 1 1 calc R
H13C H 0.4215 0.3672 0.2770 0.111 Uiso 1 1 calc R
C14 C 0.94107(15) -0.2789(4) 0.37142(11) 0.0372(6) Uani 1 1 d .
H14 H 0.9812 -0.3777 0.3710 0.045 Uiso 1 1 calc R
C15 C 0.95526(15) -0.0775(4) 0.39845(11) 0.0362(6) Uani 1 1 d .
C16 C 1.02933(14) 0.0284(4) 0.42435(11) 0.0340(5) Uani 1 1 d .
C17 C 1.14761(15) 0.1330(4) 0.45239(11) 0.0352(5) Uani 1 1 d .
C18 C 1.10410(14) 0.2954(4) 0.46804(11) 0.0352(5) Uani 1 1 d .
C19 C 1.13628(16) 0.4858(4) 0.49593(13) 0.0415(6) Uani 1 1 d .
H19 H 1.1054 0.5962 0.5062 0.050 Uiso 1 1 calc R
C20 C 1.21597(16) 0.5068(4) 0.50808(13) 0.0421(6) Uani 1 1 d .
H20 H 1.2403 0.6356 0.5277 0.050 Uiso 1 1 calc R
C21 C 1.26323(15) 0.3462(4) 0.49283(12) 0.0376(6) Uani 1 1 d .
C22 C 1.22801(15) 0.1566(4) 0.46483(12) 0.0384(6) Uani 1 1 d .
H22 H 1.2583 0.0451 0.4544 0.046 Uiso 1 1 calc R
C23 C 1.35030(16) 0.3903(4) 0.50367(13) 0.0428(6) Uani 1 1 d .
C24 C 1.35748(18) 0.5372(5) 0.44776(14) 0.0552(7) Uani 1 1 d .
H24A H 1.3340 0.4671 0.4050 0.083 Uiso 1 1 calc R
H24B H 1.4129 0.5663 0.4534 0.083 Uiso 1 1 calc R
H24C H 1.3301 0.6719 0.4491 0.083 Uiso 1 1 calc R
C25 C 1.39630(18) 0.1844(5) 0.50269(19) 0.0661(9) Uani 1 1 d .
H25A H 1.3912 0.0882 0.5377 0.099 Uiso 1 1 calc R
H25B H 1.4516 0.2192 0.5102 0.099 Uiso 1 1 calc R
H25C H 1.3755 0.1143 0.4596 0.099 Uiso 1 1 calc R
C26 C 1.38762(19) 0.5033(6) 0.56945(15) 0.0641(9) Uani 1 1 d .
H26A H 1.3610 0.6397 0.5700 0.096 Uiso 1 1 calc R
H26B H 1.4431 0.5296 0.5748 0.096 Uiso 1 1 calc R
H26C H 1.3828 0.4131 0.6058 0.096 Uiso 1 1 calc R
O1 O 1.02688(10) 0.2307(2) 0.45009(8) 0.0371(4) Uani 1 1 d .
N2 N 0.68894(12) 0.0208(3) 0.33876(10) 0.0389(5) Uani 1 1 d .
N1 N 1.09758(12) -0.0370(3) 0.42436(10) 0.0387(5) Uani 1 1 d .
O2 O 0.69047(10) -0.3040(3) 0.29218(8) 0.0392(4) Uani 1 1 d .
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'
S S 0.3331 0.5567 '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
C2 S1 C15 90.94(12) y
C2 C1 C14 112.7(2) y
C2 C1 H1 123.7 ?
C14 C1 H1 123.7 ?
C1 C2 C3 129.4(2) y
C1 C2 S1 112.24(19) y
C3 C2 S1 118.36(18) y
N2 C3 O2 115.7(2) y
N2 C3 C2 127.8(2) y
O2 C3 C2 116.4(2) y
C5 C4 C9 120.2(2) y
C5 C4 N2 108.4(2) y
C9 C4 N2 131.3(2) y
O2 C5 C6 128.9(2) y
O2 C5 C4 108.3(2) y
C6 C5 C4 122.7(2) y
C7 C6 C5 116.1(2) y
C7 C6 H6 121.9 ?
C5 C6 H6 121.9 ?
C6 C7 C8 123.3(2) y
C6 C7 H7 118.4 ?
C8 C7 H7 118.4 ?
C9 C8 C7 118.5(2) y
C9 C8 C10 122.8(2) y
C7 C8 C10 118.6(2) y
C8 C9 C4 119.1(2) y
C8 C9 H9 120.5 ?
C4 C9 H9 120.5 ?
C12 C10 C11 111.1(3) y
C12 C10 C8 110.6(2) y
C11 C10 C8 109.5(2) y
C12 C10 C13 108.0(3) y
C11 C10 C13 105.9(3) y
C8 C10 C13 111.7(2) y
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C10 C12 H12A 109.5 ?
C10 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C10 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C10 C13 H13A 109.5 ?
C10 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C10 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C15 C14 C1 112.7(2) y
C15 C14 H14 123.6 ?
C1 C14 H14 123.6 ?
C14 C15 C16 128.0(2) y
C14 C15 S1 111.46(19) y
C16 C15 S1 120.29(18) y
N1 C16 O1 115.6(2) y
N1 C16 C15 128.4(2) y
O1 C16 C15 115.9(2) y
C18 C17 C22 120.2(2) y
C18 C17 N1 109.0(2) y
C22 C17 N1 130.8(2) y
C19 C18 C17 123.1(2) y
C19 C18 O1 128.8(2) y
C17 C18 O1 108.0(2) y
C18 C19 C20 116.0(2) y
C18 C19 H19 122 ?
C20 C19 H19 122 ?
C19 C20 C21 123.2(2) y
C19 C20 H20 118.4 ?
C21 C20 H20 118.4 ?
C22 C21 C20 118.6(2) y
C22 C21 C23 121.9(2) y
C20 C21 C23 119.4(2) y
C21 C22 C17 118.8(2) y
C21 C22 H22 120.6 ?
C17 C22 H22 120.6 ?
C26 C23 C21 111.5(2) y
C26 C23 C25 108.2(3) y
C21 C23 C25 112.0(2) y
C26 C23 C24 108.2(2) y
C21 C23 C24 108.1(2) y
C25 C23 C24 108.8(3) y
C23 C24 H24A 109.5 ?
C23 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
C23 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C23 C25 H25A 109.5 ?
C23 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C23 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
C23 C26 H26A 109.5 ?
C23 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
C23 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
C18 O1 C16 103.21(18) y
C3 N2 C4 104.2(2) y
C16 N1 C17 104.2(2) y
C3 O2 C5 103.37(18) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.720(2) y
S1 C15 1.723(3) y
C1 C2 1.360(3) y
C1 C14 1.399(4) y
C1 H1 0.95 ?
C2 C3 1.443(4) y
C3 N2 1.297(3) y
C3 O2 1.375(3) y
C4 C5 1.386(3) y
C4 C9 1.390(4) y
C4 N2 1.404(3) y
C5 O2 1.378(3) y
C5 C6 1.378(3) y
C6 C7 1.377(4) y
C6 H6 0.95 ?
C7 C8 1.414(4) y
C7 H7 0.95 ?
C8 C9 1.383(3) y
C8 C10 1.532(4) y
C9 H9 0.95 ?
C10 C12 1.510(4) y
C10 C11 1.514(4) y
C10 C13 1.535(4) y
C11 H11a 0.98 ?
C11 H11b 0.98 ?
C11 H11c 0.98 ?
C12 H12a 0.98 ?
C12 H12b 0.98 ?
C12 H12c 0.98 ?
C13 H13a 0.98 ?
C13 H13b 0.98 ?
C13 H13c 0.98 ?
C14 C15 1.376(3) y
C14 H14 0.95 ?
C15 C16 1.436(3) y
C16 N1 1.289(3) y
C16 O1 1.385(3) y
C17 C18 1.380(3) y
C17 C22 1.392(3) y
C17 N1 1.402(3) y
C18 C19 1.377(3) y
C18 O1 1.381(3) y
C19 C20 1.379(4) y
C19 H19 0.95 ?
C20 C21 1.413(4) y
C20 H20 0.95 ?
C21 C22 1.390(3) y
C21 C23 1.532(4) y
C22 H22 0.95 ?
C23 C26 1.526(4) y
C23 C25 1.533(4) y
C23 C24 1.535(4) y
C24 H24a 0.98 ?
C24 H24b 0.98 ?
C24 H24c 0.98 ?
C25 H25a 0.98 ?
C25 H25b 0.98 ?
C25 H25c 0.98 ?
C26 H26a 0.98 ?
C26 H26b 0.98 ?
C26 H26c 0.98 ?
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
_geom_torsion_publ_flag
C14 C1 C2 C3 178.9(2) y
C14 C1 C2 S1 -0.6(3) y
C15 S1 C2 C1 0.61(19) y
C15 S1 C2 C3 -178.90(19) y
C1 C2 C3 N2 176.2(3) y
S1 C2 C3 N2 -4.4(3) y
C1 C2 C3 O2 -4.9(4) y
S1 C2 C3 O2 174.53(16) y
C9 C4 C5 O2 -178.5(2) y
N2 C4 C5 O2 0.0(3) y
C9 C4 C5 C6 0.3(4) y
N2 C4 C5 C6 178.8(2) y
O2 C5 C6 C7 179.1(2) y
C4 C5 C6 C7 0.6(4) y
C5 C6 C7 C8 -1.6(4) y
C6 C7 C8 C9 1.6(4) y
C6 C7 C8 C10 -176.8(2) y
C7 C8 C9 C4 -0.6(4) y
C10 C8 C9 C4 177.8(2) y
C5 C4 C9 C8 -0.3(4) y
N2 C4 C9 C8 -178.4(2) y
C9 C8 C10 C12 118.4(3) y
C7 C8 C10 C12 -63.2(3) y
C9 C8 C10 C11 -118.9(3) y
C7 C8 C10 C11 59.5(3) y
C9 C8 C10 C13 -1.9(4) y
C7 C8 C10 C13 176.5(2) y
C2 C1 C14 C15 0.2(3) y
C1 C14 C15 C16 -173.5(2) y
C1 C14 C15 S1 0.3(3) y
C2 S1 C15 C14 -0.50(19) y
C2 S1 C15 C16 173.78(19) y
C14 C15 C16 N1 4.4(4) y
S1 C15 C16 N1 -168.8(2) y
C14 C15 C16 O1 -178.6(2) y
S1 C15 C16 O1 8.1(3) y
C22 C17 C18 C19 0.2(4) y
N1 C17 C18 C19 -179.4(2) y
C22 C17 C18 O1 179.5(2) y
N1 C17 C18 O1 -0.2(3) y
C17 C18 C19 C20 -0.3(4) y
O1 C18 C19 C20 -179.4(2) y
C18 C19 C20 C21 0.6(4) y
C19 C20 C21 C22 -0.7(4) y
C19 C20 C21 C23 175.7(2) y
C20 C21 C22 C17 0.6(3) y
C23 C21 C22 C17 -175.8(2) y
C18 C17 C22 C21 -0.3(3) y
N1 C17 C22 C21 179.2(2) y
C22 C21 C23 C26 -140.5(3) y
C20 C21 C23 C26 43.2(3) y
C22 C21 C23 C25 -19.1(3) y
C20 C21 C23 C25 164.6(3) y
C22 C21 C23 C24 100.7(3) y
C20 C21 C23 C24 -75.6(3) y
C19 C18 O1 C16 179.3(2) y
C17 C18 O1 C16 0.1(2) y
N1 C16 O1 C18 -0.1(3) y
C15 C16 O1 C18 -177.41(19) y
O2 C3 N2 C4 0.2(3) y
C2 C3 N2 C4 179.2(2) y
C5 C4 N2 C3 -0.1(3) y
C9 C4 N2 C3 178.1(3) y
O1 C16 N1 C17 0.0(3) y
C15 C16 N1 C17 176.9(2) y
C18 C17 N1 C16 0.1(3) y
C22 C17 N1 C16 -179.5(2) y
N2 C3 O2 C5 -0.2(3) y
C2 C3 O2 C5 -179.3(2) y
C6 C5 O2 C3 -178.5(2) y
C4 C5 O2 C3 0.1(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 258050
