#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150349.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_7150349
loop_
_publ_author_name
'Kreher, David'
'Batsanov, Andrei S.'
'Wang, Changsheng'
'Bryce, Martin R.'
_publ_section_title
;
 Functionalisation reactions of 2,5-diphenyl-1,3,4-oxadiazoles bearing
 a terminal ethynyl or butadiynyl substituent: X-ray crystal structures
 of the products.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              858
_journal_page_last               862
_journal_paper_doi               10.1039/b315694j
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C28 H24 N2 O5 S2'
_chemical_formula_sum            'C28 H24 N2 O5 S2'
_chemical_formula_weight         532.61
_chemical_melting_point          475.1(10)
_chemical_name_systematic
;
2-(3-{4-[5-(4-tert-Butylphenyl)-1,3,4-oxadiazol-2-yl]-phenyl}-
prop-2-ynylidene)-1,3-dithiole-4,5-dicarboxylic acid dimethyl
ester
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.866(10)
_cell_angle_beta                 105.881(10)
_cell_angle_gamma                97.048(10)
_cell_formula_units_Z            2
_cell_length_a                   10.878(1)
_cell_length_b                   11.000(1)
_cell_length_c                   12.705(1)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      12.05
_cell_volume                     1276.5(3)
_computing_cell_refinement       'SMART version 5.060 (Bruker, 1999)'
_computing_data_collection       'SMART version 5.060 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material  'SHELXTL version 5.10 (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15831
_diffrn_reflns_theta_full        29.06
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP (SHELXTL)'
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         6727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0351
_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)+(0.0450P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                5969
_reflns_number_total             6727
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b315694j.txt
_cod_data_source_block           (11)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '201--203\% C' was changed to
'475.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        1276.48(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150349
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.69356(3) 1.14390(3) 0.69850(3) 0.02408(8) Uani 1 1 d . . .
S2 S 0.49023(3) 0.88848(3) 0.61947(3) 0.02293(8) Uani 1 1 d . . .
O1 O 0.21597(9) -0.03108(9) 0.04501(8) 0.02429(18) Uani 1 1 d . . .
O2 O 0.69395(9) 1.39392(9) 0.90262(8) 0.0292(2) Uani 1 1 d . . .
O4 O 0.28678(9) 1.07015(10) 0.75848(8) 0.02858(19) Uani 1 1 d . . .
O3 O 0.53026(10) 1.30539(10) 0.94903(9) 0.0331(2) Uani 1 1 d . . .
O5 O 0.40000(10) 0.97584(11) 0.86659(10) 0.0349(2) Uani 1 1 d . . .
N1 N 0.04179(12) -0.10524(12) 0.08179(11) 0.0320(2) Uani 1 1 d . . .
N2 N 0.09825(12) 0.03748(12) 0.16576(11) 0.0316(2) Uani 1 1 d . . .
C1 C 0.11385(12) -0.14038(13) 0.01335(12) 0.0252(2) Uani 1 1 d . . .
C2 C 0.19932(13) 0.07620(13) 0.14043(11) 0.0250(2) Uani 1 1 d . . .
C3 C 0.00733(13) -0.67561(13) -0.41691(12) 0.0279(3) Uani 1 1 d . . .
C4 C 0.08207(14) -0.67124(14) -0.50221(13) 0.0310(3) Uani 1 1 d . . .
H41 H 0.1767(18) -0.6461(17) -0.4595(16) 0.034(4) Uiso 1 1 d . . .
H42 H 0.0608(19) -0.603(2) -0.5283(17) 0.046(5) Uiso 1 1 d . . .
H43 H 0.0550(18) -0.7646(19) -0.5787(17) 0.042(5) Uiso 1 1 d . . .
C5 C -0.14266(14) -0.72248(17) -0.49275(14) 0.0368(3) Uani 1 1 d . . .
H51 H -0.1679(17) -0.6556(18) -0.5220(16) 0.035(4) Uiso 1 1 d . . .
H52 H -0.160(2) -0.812(2) -0.564(2) 0.057(6) Uiso 1 1 d . . .
H53 H -0.1981(19) -0.735(2) -0.4476(17) 0.046(5) Uiso 1 1 d . . .
C6 C 0.04328(18) -0.78239(16) -0.37408(17) 0.0410(3) Uani 1 1 d . . .
H61 H 0.138(2) -0.7562(19) -0.3301(17) 0.043(5) Uiso 1 1 d . . .
H62 H 0.0194(19) -0.874(2) -0.4467(19) 0.050(5) Uiso 1 1 d . . .
H63 H -0.003(2) -0.791(2) -0.3219(19) 0.052(5) Uiso 1 1 d . . .
C7 C 0.53612(13) 0.62494(13) 0.36925(11) 0.0266(2) Uani 1 1 d . . .
C8 C 0.59836(13) 0.74567(13) 0.42498(11) 0.0262(2) Uani 1 1 d . . .
C9 C 0.66323(12) 0.88990(13) 0.50118(11) 0.0256(2) Uani 1 1 d . . .
H9 H 0.7360(17) 0.9339(17) 0.4898(15) 0.033(4) Uiso 1 1 d . . .
C10 C 0.62281(12) 0.96627(12) 0.59443(11) 0.0223(2) Uani 1 1 d . . .
C11 C 0.09525(12) -0.27541(13) -0.09060(12) 0.0255(2) Uani 1 1 d . . .
C12 C 0.17423(12) -0.29432(13) -0.16281(12) 0.0249(2) Uani 1 1 d . . .
H12 H 0.2470(17) -0.2206(18) -0.1408(15) 0.035(4) Uiso 1 1 d . . .
C13 C 0.14691(12) -0.42263(13) -0.26700(12) 0.0253(2) Uani 1 1 d . . .
H13 H 0.2010(16) -0.4338(17) -0.3164(15) 0.030(4) Uiso 1 1 d . . .
C14 C 0.04154(12) -0.53457(12) -0.30161(11) 0.0250(2) Uani 1 1 d . . .
C15 C -0.03296(14) -0.51491(15) -0.22430(14) 0.0355(3) Uani 1 1 d . . .
H15 H -0.1032(18) -0.5899(19) -0.2420(17) 0.042(5) Uiso 1 1 d . . .
C16 C -0.00720(15) -0.38805(15) -0.12106(14) 0.0370(3) Uani 1 1 d . . .
H16 H -0.059(2) -0.372(2) -0.0714(19) 0.053(5) Uiso 1 1 d . . .
C17 C 0.58383(12) 1.15759(12) 0.77865(10) 0.0221(2) Uani 1 1 d . . .
C18 C 0.49117(12) 1.04075(12) 0.74136(10) 0.0216(2) Uani 1 1 d . . .
C19 C 0.59727(12) 1.29202(12) 0.88540(11) 0.0239(2) Uani 1 1 d . . .
C20 C 0.38946(12) 1.02690(12) 0.79884(11) 0.0234(2) Uani 1 1 d . . .
C21 C 0.28930(12) 0.21484(13) 0.19819(11) 0.0241(2) Uani 1 1 d . . .
C22 C 0.39173(13) 0.24135(13) 0.15722(11) 0.0254(2) Uani 1 1 d . . .
H22 H 0.4072(17) 0.1704(18) 0.0939(16) 0.035(4) Uiso 1 1 d . . .
C23 C 0.47328(13) 0.37525(13) 0.21236(11) 0.0262(2) Uani 1 1 d . . .
H23 H 0.5423(17) 0.3917(18) 0.1844(16) 0.035(4) Uiso 1 1 d . . .
C24 C 0.45557(12) 0.48449(13) 0.31067(11) 0.0246(2) Uani 1 1 d . . .
C25 C 0.35515(14) 0.45589(14) 0.35323(13) 0.0327(3) Uani 1 1 d . . .
H25 H 0.3418(19) 0.525(2) 0.4164(17) 0.044(5) Uiso 1 1 d . . .
C26 C 0.27253(15) 0.32302(15) 0.29728(13) 0.0329(3) Uani 1 1 d . . .
H26 H 0.207(2) 0.304(2) 0.3246(18) 0.051(5) Uiso 1 1 d . . .
C27 C 0.71642(17) 1.52829(14) 1.00892(14) 0.0356(3) Uani 1 1 d . . .
H271 H 0.633(2) 1.5571(19) 1.0008(17) 0.045(5) Uiso 1 1 d . . .
H272 H 0.746(2) 1.520(2) 1.084(2) 0.062(6) Uiso 1 1 d . . .
H273 H 0.778(2) 1.590(3) 1.006(2) 0.072(7) Uiso 1 1 d . . .
C28 C 0.18346(15) 1.06002(18) 0.80955(15) 0.0344(3) Uani 1 1 d . . .
H281 H 0.1547(19) 0.970(2) 0.7972(17) 0.047(5) Uiso 1 1 d . . .
H282 H 0.215(2) 1.119(2) 0.897(2) 0.054(6) Uiso 1 1 d . . .
H283 H 0.117(2) 1.084(2) 0.770(2) 0.058(6) Uiso 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 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.1900
0.00 1.00 -1.00 0.1900
1.00 0.00 1.00 0.1900
-1.00 0.00 -1.00 0.1900
-1.00 0.00 1.00 0.0850
1.00 0.00 -1.00 0.0850
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C17 95.45(6) . . ?
C18 S2 C10 95.37(6) . . ?
C1 O1 C2 102.71(10) . . ?
C19 O2 C27 114.55(11) . . ?
C20 O4 C28 114.66(10) . . ?
C1 N1 N2 106.24(11) . . ?
C2 N2 N1 106.26(11) . . ?
N1 C1 O1 112.45(11) . . ?
N1 C1 C11 128.41(12) . . ?
O1 C1 C11 119.11(11) . . ?
N2 C2 O1 112.34(11) . . ?
N2 C2 C21 128.31(12) . . ?
O1 C2 C21 119.33(11) . . ?
C14 C3 C4 112.70(11) . . ?
C14 C3 C6 108.45(11) . . ?
C4 C3 C6 108.92(12) . . ?
C14 C3 C5 109.49(11) . . ?
C4 C3 C5 108.02(12) . . ?
C6 C3 C5 109.21(12) . . ?
C3 C4 H41 110.9(10) . . ?
C3 C4 H42 109.2(12) . . ?
H41 C4 H42 109.0(15) . . ?
C3 C4 H43 110.8(10) . . ?
H41 C4 H43 108.6(14) . . ?
H42 C4 H43 108.3(15) . . ?
C3 C5 H51 110.6(10) . . ?
C3 C5 H52 106.6(13) . . ?
H51 C5 H52 108.7(15) . . ?
C3 C5 H53 113.8(11) . . ?
H51 C5 H53 109.0(15) . . ?
H52 C5 H53 108.0(17) . . ?
C3 C6 H61 109.7(11) . . ?
C3 C6 H62 109.3(12) . . ?
H61 C6 H62 107.7(16) . . ?
C3 C6 H63 112.5(12) . . ?
H61 C6 H63 109.7(16) . . ?
H62 C6 H63 107.8(17) . . ?
C8 C7 C24 174.73(14) . . ?
C7 C8 C9 172.81(14) . . ?
C10 C9 C8 119.15(12) . . ?
C10 C9 H9 119.2(10) . . ?
C8 C9 H9 121.6(10) . . ?
C9 C10 S1 125.09(10) . . ?
C9 C10 S2 120.61(9) . . ?
S1 C10 S2 114.30(7) . . ?
C12 C11 C16 119.03(12) . . ?
C12 C11 C1 121.83(11) . . ?
C16 C11 C1 119.11(12) . . ?
C11 C12 C13 120.00(11) . . ?
C11 C12 H12 120.1(10) . . ?
C13 C12 H12 119.9(10) . . ?
C12 C13 C14 121.63(12) . . ?
C12 C13 H13 119.2(10) . . ?
C14 C13 H13 119.2(10) . . ?
C13 C14 C15 117.31(12) . . ?
C13 C14 C3 122.83(11) . . ?
C15 C14 C3 119.85(11) . . ?
C16 C15 C14 121.54(12) . . ?
C16 C15 H15 118.2(11) . . ?
C14 C15 H15 120.3(11) . . ?
C15 C16 C11 120.37(13) . . ?
C15 C16 H16 122.3(13) . . ?
C11 C16 H16 117.2(13) . . ?
C18 C17 C19 122.31(11) . . ?
C18 C17 S1 116.93(9) . . ?
C19 C17 S1 120.72(9) . . ?
C17 C18 C20 126.15(10) . . ?
C17 C18 S2 117.89(9) . . ?
C20 C18 S2 115.92(8) . . ?
O3 C19 O2 125.07(11) . . ?
O3 C19 C17 123.55(11) . . ?
O2 C19 C17 111.37(10) . . ?
O5 C20 O4 125.99(12) . . ?
O5 C20 C18 122.75(11) . . ?
O4 C20 C18 111.14(10) . . ?
C26 C21 C22 119.75(12) . . ?
C26 C21 C2 118.65(12) . . ?
C22 C21 C2 121.60(11) . . ?
C23 C22 C21 119.97(11) . . ?
C23 C22 H22 118.7(11) . . ?
C21 C22 H22 121.3(11) . . ?
C22 C23 C24 120.43(12) . . ?
C22 C23 H23 119.2(10) . . ?
C24 C23 H23 120.3(10) . . ?
C25 C24 C23 119.06(12) . . ?
C25 C24 C7 118.54(11) . . ?
C23 C24 C7 122.40(12) . . ?
C26 C25 C24 120.62(12) . . ?
C26 C25 H25 118.7(12) . . ?
C24 C25 H25 120.6(12) . . ?
C25 C26 C21 120.13(13) . . ?
C25 C26 H26 120.8(13) . . ?
C21 C26 H26 119.1(13) . . ?
O2 C27 H271 109.8(11) . . ?
O2 C27 H272 108.5(13) . . ?
H271 C27 H272 110.4(17) . . ?
O2 C27 H273 105.9(15) . . ?
H271 C27 H273 109.1(18) . . ?
H272 C27 H273 113(2) . . ?
O4 C28 H281 111.1(12) . . ?
O4 C28 H282 111.6(13) . . ?
H281 C28 H282 105.7(17) . . ?
O4 C28 H283 105.8(14) . . ?
H281 C28 H283 111.4(18) . . ?
H282 C28 H283 111.4(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.7492(12) . ?
S1 C17 1.7507(12) . ?
S2 C18 1.7348(12) . ?
S2 C10 1.7580(12) . ?
O1 C1 1.3646(15) . ?
O1 C2 1.3655(15) . ?
O2 C19 1.3375(15) . ?
O2 C27 1.4561(16) . ?
O4 C20 1.3262(15) . ?
O4 C28 1.4580(15) . ?
O3 C19 1.2064(15) . ?
O5 C20 1.1991(15) . ?
N1 C1 1.2980(17) . ?
N1 N2 1.4058(16) . ?
N2 C2 1.2991(17) . ?
C1 C11 1.4565(17) . ?
C2 C21 1.4566(17) . ?
C3 C14 1.5297(17) . ?
C3 C4 1.5343(19) . ?
C3 C6 1.537(2) . ?
C3 C5 1.5400(19) . ?
C4 H41 0.964(18) . ?
C4 H42 0.96(2) . ?
C4 H43 1.008(18) . ?
C5 H51 0.989(18) . ?
C5 H52 0.97(2) . ?
C5 H53 0.97(2) . ?
C6 H61 0.97(2) . ?
C6 H62 0.98(2) . ?
C6 H63 0.96(2) . ?
C7 C8 1.2040(18) . ?
C7 C24 1.4326(18) . ?
C8 C9 1.4185(17) . ?
C9 C10 1.3570(17) . ?
C9 H9 0.954(17) . ?
C11 C12 1.3921(17) . ?
C11 C16 1.3960(18) . ?
C12 C13 1.3940(17) . ?
C12 H12 0.945(17) . ?
C13 C14 1.3950(17) . ?
C13 H13 0.954(17) . ?
C14 C15 1.4029(19) . ?
C15 C16 1.382(2) . ?
C15 H15 0.954(19) . ?
C16 H16 0.94(2) . ?
C17 C18 1.3420(17) . ?
C17 C19 1.4830(16) . ?
C18 C20 1.5084(16) . ?
C21 C26 1.3977(18) . ?
C21 C22 1.4010(18) . ?
C22 C23 1.3851(18) . ?
C22 H22 0.929(17) . ?
C23 C24 1.4027(17) . ?
C23 H23 0.943(18) . ?
C24 C25 1.4023(19) . ?
C25 C26 1.380(2) . ?
C25 H25 0.904(19) . ?
C26 H26 0.91(2) . ?
C27 H271 0.99(2) . ?
C27 H272 0.97(2) . ?
C27 H273 0.92(3) . ?
C28 H281 0.94(2) . ?
C28 H282 0.95(2) . ?
C28 H283 0.90(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4052380
