#------------------------------------------------------------------------------
#$Date: 2017-03-26 20:07:39 +0300 (Sun, 26 Mar 2017) $
#$Revision: 194528 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/16/2201685.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_2201685
loop_
_publ_author_name
'Zhuang, Jun-Peng'
'Zheng, Yan'
_publ_section_title
r-1,c-2,t-3,t-4-1,2-Bis(4-methoxyphenyl)-3,4-bis(5-phenyl-1,3,4-oxadiazol-2-yl)cyclobutane
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1195
_journal_page_last               o1197
_journal_paper_doi               10.1107/S1600536802017713
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C34 H28 N4 O4'
_chemical_formula_moiety         'C34 H28 N4 O4'
_chemical_formula_sum            'C34 H28 N4 O4'
_chemical_formula_weight         556.60
_chemical_name_systematic
;
r-1,c-2,t-3,t-4-1,2-Bis(4-methoxyphenyl)-3,4-bis(5-phenyl-1,3,4-
oxadiazol-2-yl)cyclobutane
;
_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
_cell_angle_alpha                91.648(2)
_cell_angle_beta                 107.925(2)
_cell_angle_gamma                91.642(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1746(8)
_cell_length_b                   11.3853(10)
_cell_length_c                   14.5431(12)
_cell_measurement_reflns_used    5978
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.47
_cell_volume                     1443.6(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0116
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6052
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0437
_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)+(0.0766P)²+0.0284P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                3382
_reflns_number_total             5079
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6038.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Marking atoms 'C10', 'H10A', 'H10B', 'H10C' and 'C10'', 'H10D', 'H10E', 'H10F'
 as belonging to disorder groups A/1 and A/2 respectively.

 Antanas Vaitkus,
 2017-03-06

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2201685
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
O1 0.50164(12) 0.37503(9) 0.19416(9) 0.0552(3) Uani d . 1 . . O
N1 0.71024(18) 0.44520(14) 0.30374(13) 0.0706(5) Uani d . 1 . . N
C1 0.6322(2) 0.23538(14) 0.31280(13) 0.0552(5) Uani d . 1 . . C
H1A 0.7371 0.2239 0.3540 0.066 Uiso calc R 1 . . H
O2 0.37046(14) 0.37125(10) 0.35694(9) 0.0609(3) Uani d . 1 . . O
C2 0.57560(19) 0.12783(14) 0.24310(12) 0.0521(4) Uani d . 1 . . C
H2A 0.4865 0.1502 0.1902 0.062 Uiso calc R 1 . . H
N2 0.64559(19) 0.53618(13) 0.24209(13) 0.0718(5) Uani d . 1 . . N
O3 0.93683(19) -0.24599(12) 0.54582(11) 0.0950(5) Uani d . 1 . . O
N3 0.24367(18) 0.22046(14) 0.26664(13) 0.0713(5) Uani d . 1 . . N
C3 0.5156(2) 0.07018(15) 0.32276(13) 0.0567(5) Uani d . 1 . . C
H3A 0.4116 0.0354 0.2956 0.068 Uiso calc R 1 . . H
N4 0.15029(18) 0.31896(15) 0.24854(14) 0.0734(5) Uani d . 1 . . N
C4 0.5160(2) 0.19590(16) 0.36706(14) 0.0595(5) Uani d . 1 . . C
H4A 0.5590 0.2014 0.4377 0.071 Uiso calc R 1 . . H
O4 0.9684(2) -0.11107(17) 0.07510(14) 0.1064(6) Uani d . 1 . . O
C5 0.62279(19) 0.35372(15) 0.27309(13) 0.0544(5) Uani d . 1 . . C
C6 0.5242(2) 0.49087(14) 0.17950(14) 0.0540(4) Uani d . 1 . . C
C7 0.3697(2) 0.25519(16) 0.32924(14) 0.0593(5) Uani d . 1 . . C
C8 0.2294(2) 0.40444(16) 0.30246(14) 0.0581(5) Uani d . 1 . . C
C9 0.9382(3) -0.36345(18) 0.51319(17) 0.0856(7) Uani d . 1 . . C
H9A 1.0178 -0.4033 0.5591 0.128 Uiso calc R 1 . . H
H9B 0.9568 -0.3650 0.4517 0.128 Uiso calc R 1 . . H
H9C 0.8409 -0.4021 0.5064 0.128 Uiso calc R 1 . . H
C10 1.1249(6) -0.0921(5) 0.0994(4) 0.1022(17) Uani d P 0.50 A 1 C
H10A 1.1649 -0.1440 0.0607 0.153 Uiso calc PR 0.50 A 1 H
H10B 1.1712 -0.1072 0.1666 0.153 Uiso calc PR 0.50 A 1 H
H10C 1.1476 -0.0120 0.0880 0.153 Uiso calc PR 0.50 A 1 H
C10' 0.9176(9) -0.1814(7) 0.0021(7) 0.174(3) Uani d P 0.50 A 2 C
H10D 0.8085 -0.1923 -0.0129 0.261 Uiso calc PR 0.50 A 2 H
H10E 0.9646 -0.2557 0.0163 0.261 Uiso calc PR 0.50 A 2 H
H10F 0.9411 -0.1494 -0.0522 0.261 Uiso calc PR 0.50 A 2 H
C11 0.6236(2) -0.01364(15) 0.38470(13) 0.0558(5) Uani d . 1 . . C
C12 0.6231(2) -0.12840(15) 0.35276(14) 0.0617(5) Uani d . 1 . . C
H12A 0.5515 -0.1531 0.2943 0.074 Uiso calc R 1 . . H
C13 0.7242(2) -0.20894(16) 0.40350(15) 0.0657(5) Uani d . 1 . . C
H13A 0.7201 -0.2858 0.3791 0.079 Uiso calc R 1 . . H
C14 0.8301(2) -0.17500(16) 0.48956(14) 0.0675(5) Uani d . 1 . . C
C15 0.8348(3) -0.06057(18) 0.52350(16) 0.0916(8) Uani d . 1 . . C
H15A 0.9069 -0.0362 0.5818 0.110 Uiso calc R 1 . . H
C16 0.7332(3) 0.01805(17) 0.47159(16) 0.0835(7) Uani d . 1 . . C
H16A 0.7385 0.0951 0.4958 0.100 Uiso calc R 1 . . H
C21 0.6822(2) 0.06601(14) 0.19986(12) 0.0519(4) Uani d . 1 . . C
C22 0.6251(2) -0.01983(17) 0.12780(15) 0.0680(5) Uani d . 1 . . C
H22A 0.5204 -0.0383 0.1068 0.082 Uiso calc R 1 . . H
C23 0.7195(3) -0.07921(19) 0.08594(16) 0.0783(6) Uani d . 1 . . C
H23A 0.6783 -0.1370 0.0376 0.094 Uiso calc R 1 . . H
C24 0.8749(3) -0.05263(18) 0.11598(16) 0.0702(6) Uani d . 1 . . C
C25 0.9338(2) 0.03328(18) 0.18649(15) 0.0688(5) Uani d . 1 . . C
H25A 1.0383 0.0525 0.2064 0.083 Uiso calc R 1 . . H
C26 0.8387(2) 0.09148(16) 0.22821(14) 0.0621(5) Uani d . 1 . . C
H26A 0.8806 0.1492 0.2765 0.074 Uiso calc R 1 . . H
C31 0.4161(2) 0.54561(15) 0.09864(13) 0.0546(5) Uani d . 1 . . C
C32 0.4515(3) 0.65460(17) 0.07104(16) 0.0729(6) Uani d . 1 . . C
H32A 0.5436 0.6937 0.1049 0.087 Uiso calc R 1 . . H
C33 0.3509(3) 0.70593(19) -0.00667(17) 0.0821(7) Uani d . 1 . . C
H33A 0.3758 0.7795 -0.0250 0.098 Uiso calc R 1 . . H
C34 0.2163(3) 0.6502(2) -0.05652(17) 0.0828(7) Uani d . 1 . . C
H34A 0.1493 0.6850 -0.1093 0.099 Uiso calc R 1 . . H
C35 0.1795(3) 0.5426(2) -0.02887(18) 0.0956(8) Uani d . 1 . . C
H35A 0.0864 0.5046 -0.0624 0.115 Uiso calc R 1 . . H
C36 0.2796(2) 0.4898(2) 0.04862(17) 0.0830(7) Uani d . 1 . . C
H36A 0.2542 0.4163 0.0668 0.100 Uiso calc R 1 . . H
C41 0.1906(2) 0.52707(16) 0.30812(14) 0.0577(5) Uani d . 1 . . C
C42 0.3027(2) 0.61386(18) 0.34783(16) 0.0714(6) Uani d . 1 . . C
H42A 0.4045 0.5940 0.3737 0.086 Uiso calc R 1 . . H
C43 0.2637(3) 0.72967(19) 0.34902(18) 0.0816(6) Uani d . 1 . . C
H43A 0.3391 0.7882 0.3755 0.098 Uiso calc R 1 . . H
C44 0.1131(3) 0.7587(2) 0.31096(18) 0.0834(7) Uani d . 1 . . C
H44A 0.0868 0.8369 0.3120 0.100 Uiso calc R 1 . . H
C45 0.0021(3) 0.6733(2) 0.27161(18) 0.0835(7) Uani d . 1 . . C
H45A -0.0995 0.6935 0.2456 0.100 Uiso calc R 1 . . H
C46 0.0400(2) 0.55800(18) 0.27043(15) 0.0712(6) Uani d . 1 . . C
H46A -0.0362 0.5001 0.2441 0.085 Uiso calc R 1 . . H
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C5 103.09(13) ?
C5 N1 N2 106.55(15) ?
C5 C1 C2 119.08(15) ?
C5 C1 C4 119.34(14) ?
C2 C1 C4 88.40(13) y
C5 C1 H1A 109.4 ?
C2 C1 H1A 109.4 ?
C4 C1 H1A 109.4 ?
C8 O2 C7 102.63(14) ?
C21 C2 C1 120.77(15) ?
C21 C2 C3 121.71(14) ?
C1 C2 C3 88.14(13) y
C21 C2 H2A 108.1 ?
C1 C2 H2A 108.1 ?
C3 C2 H2A 108.1 ?
C6 N2 N1 106.24(14) ?
C14 O3 C9 117.95(16) y
C7 N3 N4 106.34(16) ?
C11 C3 C4 116.45(15) ?
C11 C3 C2 114.27(14) ?
C4 C3 C2 87.64(13) y
C11 C3 H3A 112.1 ?
C4 C3 H3A 112.1 ?
C2 C3 H3A 112.1 ?
C8 N4 N3 106.36(16) ?
C7 C4 C3 114.17(16) ?
C7 C4 C1 110.68(15) ?
C3 C4 C1 87.89(13) y
C7 C4 H4A 113.8 ?
C3 C4 H4A 113.8 ?
C1 C4 H4A 113.8 ?
C10' O4 C24 122.8(4) ?
C10' O4 C10 111.7(4) ?
C24 O4 C10 125.1(3) y
N1 C5 O1 112.13(15) ?
N1 C5 C1 129.65(17) ?
O1 C5 C1 118.17(15) ?
N2 C6 O1 111.99(16) ?
N2 C6 C31 129.02(16) ?
O1 C6 C31 118.99(15) ?
N3 C7 O2 112.50(16) ?
N3 C7 C4 130.89(18) ?
O2 C7 C4 116.21(17) ?
N4 C8 O2 112.16(16) ?
N4 C8 C41 129.04(17) ?
O2 C8 C41 118.73(17) ?
O3 C9 H9A 109.5 ?
O3 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O3 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
O4 C10 H10A 109.5 ?
O4 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
O4 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
O4 C10' H10D 109.5 ?
O4 C10' H10E 109.5 ?
H10D C10' H10E 109.5 ?
O4 C10' H10F 109.5 ?
H10D C10' H10F 109.5 ?
H10E C10' H10F 109.5 ?
C12 C11 C16 115.86(17) ?
C12 C11 C3 119.77(17) ?
C16 C11 C3 124.27(16) ?
C11 C12 C13 123.01(18) ?
C11 C12 H12A 118.5 ?
C13 C12 H12A 118.5 ?
C14 C13 C12 119.62(17) ?
C14 C13 H13A 120.2 ?
C12 C13 H13A 120.2 ?
C13 C14 O3 125.08(17) y
C13 C14 C15 119.01(18) ?
O3 C14 C15 115.90(18) y
C14 C15 C16 120.3(2) ?
C14 C15 H15A 119.8 ?
C16 C15 H15A 119.8 ?
C15 C16 C11 122.19(19) ?
C15 C16 H16A 118.9 ?
C11 C16 H16A 118.9 ?
C22 C21 C26 117.19(18) ?
C22 C21 C2 119.83(16) ?
C26 C21 C2 122.98(16) ?
C21 C22 C23 121.72(19) ?
C21 C22 H22A 119.1 ?
C23 C22 H22A 119.1 ?
C24 C23 C22 119.9(2) ?
C24 C23 H23A 120.1 ?
C22 C23 H23A 120.1 ?
O4 C24 C25 120.5(2) y
O4 C24 C23 120.1(2) y
C25 C24 C23 119.44(19) ?
C24 C25 C26 120.2(2) ?
C24 C25 H25A 119.9 ?
C26 C25 H25A 119.9 ?
C25 C26 C21 121.56(19) ?
C25 C26 H26A 119.2 ?
C21 C26 H26A 119.2 ?
C36 C31 C32 119.16(19) ?
C36 C31 C6 120.95(17) ?
C32 C31 C6 119.89(17) ?
C31 C32 C33 120.2(2) ?
C31 C32 H32A 119.9 ?
C33 C32 H32A 119.9 ?
C34 C33 C32 120.6(2) ?
C34 C33 H33A 119.7 ?
C32 C33 H33A 119.7 ?
C33 C34 C35 119.6(2) ?
C33 C34 H34A 120.2 ?
C35 C34 H34A 120.2 ?
C34 C35 C36 120.4(2) ?
C34 C35 H35A 119.8 ?
C36 C35 H35A 119.8 ?
C31 C36 C35 120.1(2) ?
C31 C36 H36A 120.0 ?
C35 C36 H36A 120.0 ?
C46 C41 C42 119.23(18) ?
C46 C41 C8 119.57(18) ?
C42 C41 C8 121.17(17) ?
C43 C42 C41 120.0(2) ?
C43 C42 H42A 120.0 ?
C41 C42 H42A 120.0 ?
C44 C43 C42 119.9(2) ?
C44 C43 H43A 120.1 ?
C42 C43 H43A 120.1 ?
C45 C44 C43 120.3(2) ?
C45 C44 H44A 119.8 ?
C43 C44 H44A 119.8 ?
C44 C45 C46 120.1(2) ?
C44 C45 H45A 120.0 ?
C46 C45 H45A 120.0 ?
C45 C46 C41 120.5(2) ?
C45 C46 H46A 119.8 ?
C41 C46 H46A 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.3621(19) ?
O1 C5 . 1.3631(19) ?
N1 C5 . 1.278(2) ?
N1 N2 . 1.411(2) ?
C1 C5 . 1.475(2) y
C1 C2 . 1.538(2) y
C1 C4 . 1.572(3) y
C1 H1A . 0.9800 ?
O2 C8 . 1.364(2) ?
O2 C7 . 1.369(2) ?
C2 C21 . 1.497(2) y
C2 C3 . 1.579(2) y
C2 H2A . 0.9800 ?
N2 C6 . 1.285(2) ?
O3 C14 . 1.368(2) y
O3 C9 . 1.408(2) y
N3 C7 . 1.276(2) ?
N3 N4 . 1.412(2) ?
C3 C11 . 1.503(2) y
C3 C4 . 1.552(2) y
C3 H3A . 0.9800 ?
N4 C8 . 1.286(2) ?
C4 C7 . 1.476(2) y
C4 H4A . 0.9800 ?
O4 C10' . 1.269(8) ?
O4 C24 . 1.362(3) y
O4 C10 . 1.378(5) y
C6 C31 . 1.454(2) ?
C8 C41 . 1.457(2) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C10' H10D . 0.9600 ?
C10' H10E . 0.9600 ?
C10' H10F . 0.9600 ?
C11 C12 . 1.373(2) ?
C11 C16 . 1.382(3) ?
C12 C13 . 1.383(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.364(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.375(3) ?
C15 C16 . 1.376(3) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
C21 C22 . 1.379(2) ?
C21 C26 . 1.385(2) ?
C22 C23 . 1.383(3) ?
C22 H22A . 0.9300 ?
C23 C24 . 1.378(3) ?
C23 H23A . 0.9300 ?
C24 C25 . 1.368(3) ?
C25 C26 . 1.380(3) ?
C25 H25A . 0.9300 ?
C26 H26A . 0.9300 ?
C31 C36 . 1.366(3) ?
C31 C32 . 1.376(3) ?
C32 C33 . 1.378(3) ?
C32 H32A . 0.9300 ?
C33 C34 . 1.353(3) ?
C33 H33A . 0.9300 ?
C34 C35 . 1.366(3) ?
C34 H34A . 0.9300 ?
C35 C36 . 1.382(3) ?
C35 H35A . 0.9300 ?
C36 H36A . 0.9300 ?
C41 C46 . 1.381(3) ?
C41 C42 . 1.382(3) ?
C42 C43 . 1.377(3) ?
C42 H42A . 0.9300 ?
C43 C44 . 1.375(3) ?
C43 H43A . 0.9300 ?
C44 C45 . 1.365(3) ?
C44 H44A . 0.9300 ?
C45 C46 . 1.369(3) ?
C45 H45A . 0.9300 ?
C46 H46A . 0.9300 ?
