#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150347.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_7150347
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         'C27 H28 N2 O3'
_chemical_formula_sum            'C27 H28 N2 O3'
_chemical_formula_weight         428.51
_chemical_melting_point          415.1(10)
_chemical_name_systematic
;
2-(4-tert-Butylphenyl)-5-[4-(5,5-diethoxy-1,3-pentadiyn-1-yl)-
phenyl]-1,3,4-oxadiazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.14(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.835(5)
_cell_length_b                   6.161(1)
_cell_length_c                   25.549(3)
_cell_measurement_reflns_used    759
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.46
_cell_measurement_theta_min      12.07
_cell_volume                     2334.7(9)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19697
_diffrn_reflns_theta_full        29.06
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0561
_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)+(0.0740P)²+0.6572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                4459
_reflns_number_total             6234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b315694j.txt
_cod_data_source_block           (4)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 '141--143\% C' was changed to
'415.1(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_sg_symbol_H-M      P2(1)/c
_cod_database_code               7150347
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'
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
O1 O 0.39789(7) 0.52895(18) 0.21761(4) 0.0209(2) Uani 1 1 d . . .
O2 O 0.81485(8) 0.14954(19) -0.18377(4) 0.0269(3) Uani 1 1 d . . .
O3 O 0.83892(7) -0.15732(19) -0.13629(5) 0.0282(3) Uani 1 1 d . . .
N1 N 0.40465(9) 0.8612(2) 0.25052(5) 0.0248(3) Uani 1 1 d . . .
N2 N 0.45463(9) 0.8566(2) 0.20420(5) 0.0249(3) Uani 1 1 d . . .
C1 C 0.37374(10) 0.6662(3) 0.25674(6) 0.0204(3) Uani 1 1 d . . .
C2 C 0.44905(10) 0.6593(3) 0.18681(6) 0.0198(3) Uani 1 1 d . . .
C3 C 0.13510(10) 0.3885(3) 0.42101(6) 0.0242(3) Uani 1 1 d . . .
C4 C 0.13030(14) 0.1434(3) 0.42945(8) 0.0349(4) Uani 1 1 d . . .
H41 H 0.1105(14) 0.064(4) 0.3960(8) 0.041(6) Uiso 1 1 d . . .
H42 H 0.0845(14) 0.109(3) 0.4575(8) 0.039(6) Uiso 1 1 d . . .
H43 H 0.1883(16) 0.087(4) 0.4437(9) 0.056(7) Uiso 1 1 d . . .
C5 C 0.15812(18) 0.4921(4) 0.47421(8) 0.0475(6) Uani 1 1 d . . .
H51 H 0.1121(14) 0.434(4) 0.5001(8) 0.043(6) Uiso 1 1 d . . .
H52 H 0.1516(18) 0.657(5) 0.4733(10) 0.068(8) Uiso 1 1 d . . .
H53 H 0.2243(18) 0.441(4) 0.4868(10) 0.068(8) Uiso 1 1 d . . .
C6 C 0.04263(13) 0.4710(4) 0.40145(10) 0.0440(5) Uani 1 1 d . . .
H61 H -0.0054(16) 0.433(4) 0.4258(9) 0.053(7) Uiso 1 1 d . . .
H62 H 0.0281(15) 0.395(4) 0.3667(10) 0.055(7) Uiso 1 1 d . . .
H63 H 0.0463(17) 0.635(5) 0.3979(10) 0.064(8) Uiso 1 1 d . . .
C7 C 0.60826(10) 0.3161(3) 0.00451(6) 0.0240(3) Uani 1 1 d . . .
C8 C 0.64285(10) 0.2426(3) -0.03367(6) 0.0244(3) Uani 1 1 d . . .
C9 C 0.68323(10) 0.1560(3) -0.07693(6) 0.0241(3) Uani 1 1 d . . .
C10 C 0.72051(10) 0.0832(3) -0.11437(6) 0.0247(3) Uani 1 1 d . . .
C11 C 0.31797(10) 0.5859(3) 0.29883(6) 0.0203(3) Uani 1 1 d . . .
C12 C 0.30108(11) 0.7218(3) 0.34115(6) 0.0237(3) Uani 1 1 d . . .
H12 H 0.3298(13) 0.858(3) 0.3432(8) 0.034(5) Uiso 1 1 d . . .
C13 C 0.24570(11) 0.6533(3) 0.38070(7) 0.0249(3) Uani 1 1 d . . .
H13 H 0.2343(14) 0.753(4) 0.4087(8) 0.041(6) Uiso 1 1 d . . .
C14 C 0.20422(10) 0.4503(3) 0.37983(6) 0.0211(3) Uani 1 1 d . . .
C15 C 0.22422(12) 0.3137(3) 0.33800(7) 0.0289(4) Uani 1 1 d . . .
H15 H 0.2011(13) 0.168(4) 0.3361(8) 0.036(5) Uiso 1 1 d . . .
C16 C 0.28088(12) 0.3791(3) 0.29845(7) 0.0283(4) Uani 1 1 d . . .
H16 H 0.2966(13) 0.281(4) 0.2717(8) 0.038(6) Uiso 1 1 d . . .
C17 C 0.85393(13) 0.0778(3) -0.23177(7) 0.0330(4) Uani 1 1 d . . .
H171 H 0.8052(13) 0.052(3) -0.2573(8) 0.034(5) Uiso 1 1 d . . .
H172 H 0.8878(14) -0.052(4) -0.2251(8) 0.035(5) Uiso 1 1 d . . .
C18 C 0.91496(15) 0.2539(4) -0.25069(9) 0.0443(5) Uani 1 1 d . . .
H181 H 0.9651(17) 0.284(4) -0.2250(10) 0.060(7) Uiso 1 1 d . . .
H182 H 0.8811(15) 0.388(4) -0.2526(8) 0.045(6) Uiso 1 1 d . . .
H183 H 0.9398(16) 0.213(4) -0.2850(10) 0.060(7) Uiso 1 1 d . . .
C19 C 0.80420(12) -0.3571(3) -0.11638(8) 0.0340(4) Uani 1 1 d . . .
H191 H 0.7752(15) -0.439(4) -0.1477(9) 0.052(7) Uiso 1 1 d . . .
H192 H 0.7581(14) -0.318(4) -0.0883(8) 0.042(6) Uiso 1 1 d . . .
C20 C 0.88297(14) -0.4821(3) -0.09426(10) 0.0400(5) Uani 1 1 d . . .
H201 H 0.9290(18) -0.506(4) -0.1238(10) 0.065(8) Uiso 1 1 d . . .
H202 H 0.9144(16) -0.400(4) -0.0655(10) 0.058(7) Uiso 1 1 d . . .
H203 H 0.8633(16) -0.628(4) -0.0799(10) 0.059(7) Uiso 1 1 d . . .
C21 C 0.48917(10) 0.5687(3) 0.14011(6) 0.0203(3) Uani 1 1 d . . .
C22 C 0.54959(10) 0.6955(3) 0.11199(6) 0.0221(3) Uani 1 1 d . . .
H22 H 0.5656(13) 0.831(3) 0.1237(8) 0.033(5) Uiso 1 1 d . . .
C23 C 0.58834(11) 0.6137(3) 0.06744(6) 0.0235(3) Uani 1 1 d . . .
H23 H 0.6292(12) 0.700(3) 0.0479(7) 0.028(5) Uiso 1 1 d . . .
C24 C 0.56710(10) 0.4035(3) 0.05013(6) 0.0223(3) Uani 1 1 d . . .
C25 C 0.50588(11) 0.2777(3) 0.07820(6) 0.0236(3) Uani 1 1 d . . .
H25 H 0.4902(12) 0.132(3) 0.0665(7) 0.025(5) Uiso 1 1 d . . .
C26 C 0.46795(11) 0.3594(3) 0.12311(6) 0.0225(3) Uani 1 1 d . . .
H26 H 0.4270(12) 0.270(3) 0.1413(7) 0.029(5) Uiso 1 1 d . . .
C27 C 0.77150(11) -0.0166(3) -0.15717(6) 0.0245(3) Uani 1 1 d . . .
H27 H 0.7306(12) -0.102(3) -0.1808(7) 0.023(4) 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0250
-1.00 0.00 0.00 0.0250
0.00 1.00 0.00 0.2800
0.00 -1.00 0.00 0.2800
0.00 0.00 1.00 0.1200
-1.00 0.00 -3.00 0.1100
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
C1 O1 C2 102.41(12) . . ?
C27 O2 C17 112.87(13) . . ?
C27 O3 C19 113.75(12) . . ?
C1 N1 N2 106.12(12) . . ?
C2 N2 N1 105.99(13) . . ?
N1 C1 O1 112.73(13) . . ?
N1 C1 C11 127.77(14) . . ?
O1 C1 C11 119.50(14) . . ?
N2 C2 O1 112.74(13) . . ?
N2 C2 C21 128.06(14) . . ?
O1 C2 C21 119.20(13) . . ?
C4 C3 C14 112.10(14) . . ?
C4 C3 C5 107.23(17) . . ?
C14 C3 C5 111.42(14) . . ?
C4 C3 C6 109.21(16) . . ?
C14 C3 C6 107.45(14) . . ?
C5 C3 C6 109.40(18) . . ?
C3 C4 H41 111.7(12) . . ?
C3 C4 H42 109.7(12) . . ?
H41 C4 H42 107.7(17) . . ?
C3 C4 H43 110.8(15) . . ?
H41 C4 H43 111.9(18) . . ?
H42 C4 H43 104.8(17) . . ?
C3 C5 H51 106.6(12) . . ?
C3 C5 H52 112.0(15) . . ?
H51 C5 H52 107(2) . . ?
C3 C5 H53 109.4(14) . . ?
H51 C5 H53 108.7(18) . . ?
H52 C5 H53 112(2) . . ?
C3 C6 H61 111.6(14) . . ?
C3 C6 H62 107.6(13) . . ?
H61 C6 H62 107.2(19) . . ?
C3 C6 H63 108.0(15) . . ?
H61 C6 H63 110(2) . . ?
H62 C6 H63 113(2) . . ?
C8 C7 C24 179.89(19) . . ?
C7 C8 C9 179.06(18) . . ?
C10 C9 C8 178.30(18) . . ?
C9 C10 C27 175.03(17) . . ?
C16 C11 C12 118.65(15) . . ?
C16 C11 C1 122.51(14) . . ?
C12 C11 C1 118.84(14) . . ?
C13 C12 C11 120.19(15) . . ?
C13 C12 H12 120.4(12) . . ?
C11 C12 H12 119.3(12) . . ?
C12 C13 C14 122.09(15) . . ?
C12 C13 H13 117.7(13) . . ?
C14 C13 H13 120.1(13) . . ?
C13 C14 C15 116.90(14) . . ?
C13 C14 C3 120.87(14) . . ?
C15 C14 C3 122.09(14) . . ?
C16 C15 C14 121.55(16) . . ?
C16 C15 H15 117.1(12) . . ?
C14 C15 H15 121.4(12) . . ?
C15 C16 C11 120.49(15) . . ?
C15 C16 H16 120.2(13) . . ?
C11 C16 H16 119.2(13) . . ?
O2 C17 C18 108.01(17) . . ?
O2 C17 H171 108.3(11) . . ?
C18 C17 H171 110.3(12) . . ?
O2 C17 H172 108.9(12) . . ?
C18 C17 H172 110.1(12) . . ?
H171 C17 H172 111.2(17) . . ?
C17 C18 H181 111.6(15) . . ?
C17 C18 H182 108.5(13) . . ?
H181 C18 H182 105(2) . . ?
C17 C18 H183 110.0(15) . . ?
H181 C18 H183 110.0(19) . . ?
H182 C18 H183 111.9(19) . . ?
O3 C19 C20 106.98(15) . . ?
O3 C19 H191 107.0(13) . . ?
C20 C19 H191 110.4(13) . . ?
O3 C19 H192 107.1(12) . . ?
C20 C19 H192 112.4(12) . . ?
H191 C19 H192 112.5(17) . . ?
C19 C20 H201 108.5(14) . . ?
C19 C20 H202 111.5(14) . . ?
H201 C20 H202 108(2) . . ?
C19 C20 H203 111.3(14) . . ?
H201 C20 H203 110(2) . . ?
H202 C20 H203 108(2) . . ?
C26 C21 C22 119.97(14) . . ?
C26 C21 C2 121.11(14) . . ?
C22 C21 C2 118.92(14) . . ?
C23 C22 C21 120.11(15) . . ?
C23 C22 H22 119.4(12) . . ?
C21 C22 H22 120.5(12) . . ?
C22 C23 C24 120.15(15) . . ?
C22 C23 H23 120.4(11) . . ?
C24 C23 H23 119.4(11) . . ?
C25 C24 C23 119.54(14) . . ?
C25 C24 C7 119.96(15) . . ?
C23 C24 C7 120.50(15) . . ?
C26 C25 C24 120.10(15) . . ?
C26 C25 H25 119.5(11) . . ?
C24 C25 H25 120.4(11) . . ?
C25 C26 C21 120.13(15) . . ?
C25 C26 H26 118.2(12) . . ?
C21 C26 H26 121.7(12) . . ?
O2 C27 O3 107.66(12) . . ?
O2 C27 C10 107.70(13) . . ?
O3 C27 C10 110.10(13) . . ?
O2 C27 H27 112.0(10) . . ?
O3 C27 H27 108.5(10) . . ?
C10 C27 H27 110.8(10) . . ?
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
O1 C1 1.3628(18) . ?
O1 C2 1.3653(18) . ?
O2 C27 1.393(2) . ?
O2 C17 1.436(2) . ?
O3 C27 1.420(2) . ?
O3 C19 1.431(2) . ?
N1 C1 1.297(2) . ?
N1 N2 1.4093(19) . ?
N2 C2 1.296(2) . ?
C1 C11 1.457(2) . ?
C2 C21 1.455(2) . ?
C3 C4 1.527(3) . ?
C3 C14 1.532(2) . ?
C3 C5 1.534(3) . ?
C3 C6 1.537(3) . ?
C4 H41 1.02(2) . ?
C4 H42 1.02(2) . ?
C4 H43 0.99(2) . ?
C5 H51 1.03(2) . ?
C5 H52 1.02(3) . ?
C5 H53 1.07(3) . ?
C6 H61 0.98(2) . ?
C6 H62 1.02(3) . ?
C6 H63 1.02(3) . ?
C7 C8 1.200(2) . ?
C7 C24 1.432(2) . ?
C8 C9 1.375(2) . ?
C9 C10 1.201(2) . ?
C10 C27 1.476(2) . ?
C11 C16 1.388(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.94(2) . ?
C13 C14 1.394(2) . ?
C13 H13 0.96(2) . ?
C14 C15 1.397(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.96(2) . ?
C16 H16 0.95(2) . ?
C17 C18 1.499(3) . ?
C17 H171 0.98(2) . ?
C17 H172 0.96(2) . ?
C18 H181 1.00(3) . ?
C18 H182 0.97(2) . ?
C18 H183 0.99(3) . ?
C19 C20 1.500(3) . ?
C19 H191 1.03(2) . ?
C19 H192 1.03(2) . ?
C20 H201 1.04(3) . ?
C20 H202 1.00(3) . ?
C20 H203 1.01(3) . ?
C21 C26 1.395(2) . ?
C21 C22 1.398(2) . ?
C22 C23 1.380(2) . ?
C22 H22 0.92(2) . ?
C23 C24 1.402(2) . ?
C23 H23 0.956(19) . ?
C24 C25 1.402(2) . ?
C25 C26 1.383(2) . ?
C25 H25 0.971(19) . ?
C26 H26 0.95(2) . ?
C27 H27 0.999(18) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4052378
