#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008093.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_2008093
loop_
_publ_author_name
'Bengaard, H. S.'
'Larsen, S.'
'S\/orensen, H. O.'
'Robinson, K. J.'
'Wallis, J. D.'
_publ_section_title
;
 Interaction between an oxygen and an alkynyl-carbon atom in
 1-(2-nitrophenyl)-4-phenylbutadiyne
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              106
_journal_page_last               108
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C16 H9 N O2'
_chemical_formula_structural     (C6H5)CCCC(C6H4NO2)
_chemical_formula_sum            'C16 H9 N O2'
_chemical_formula_weight         247.24
_chemical_melting_point          433
_chemical_name_systematic
;
 1-(2-nitrophenyl)-4-phenylbutadiyne
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.532(5)
_cell_length_b                   13.278(2)
_cell_length_c                   23.7103(10)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      43.190
_cell_measurement_theta_min      35.469
_cell_volume                     2371.3(16)
_computing_cell_refinement       'CAD-4 Express'
_computing_data_collection       'CAD-4 Express (Enraf-Nonius, 1994)'
_computing_data_reduction        'DREADD (Blessing, 1987)'
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6580
_diffrn_reflns_theta_max         74.89
_diffrn_reflns_theta_min         3.73
_diffrn_standards_decay_%        4.0
_diffrn_standards_interval_time  166.7
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    '1.385 (measured at 122 K)'
_exptl_crystal_density_meas      '1.305 (measured at 295 K)'
_exptl_crystal_density_method    'flotation in aqueous KI'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.236
_refine_ls_extinction_coef       0.0041(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   3.456
_refine_ls_goodness_of_fit_obs   3.572
_refine_ls_hydrogen_treatment
; H atoms were refined freely with individual
isotropic displacement parameters
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.456
_refine_ls_restrained_S_obs      3.572
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_obs          0.0364
_refine_ls_shift/esd_max         0.017
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      'calc w = 1/[\s^2^(Fo^2^)]'
_refine_ls_wR_factor_all         0.0888
_refine_ls_wR_factor_obs         0.0885
_reflns_number_observed          2249
_reflns_number_total             2404
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ln1068.cif
_[local]_cod_data_source_block   fh374
_cod_database_code               2008093
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0515(7) 0.0209(5) 0.0315(5) 0.0066(5) 0.0115(5) 0.0073(4)
O2 0.0493(7) 0.0322(5) 0.0291(5) 0.0054(5) 0.0179(5) 0.0001(4)
N 0.0244(5) 0.0215(5) 0.0228(6) -0.0005(4) 0.0023(4) 0.0003(4)
C1 0.0215(6) 0.0231(6) 0.0190(6) -0.0009(5) -0.0004(5) -0.0005(5)
C2 0.0221(6) 0.0231(6) 0.0204(6) -0.0005(5) 0.0001(5) -0.0005(5)
C3 0.0228(6) 0.0235(6) 0.0200(6) -0.0010(5) 0.0004(5) -0.0008(5)
C4 0.0219(6) 0.0230(6) 0.0217(6) -0.0011(5) -0.0005(5) -0.0009(5)
C11 0.0194(6) 0.0169(6) 0.0203(6) -0.0011(5) -0.0030(5) -0.0010(5)
C12 0.0196(6) 0.0196(6) 0.0182(6) -0.0029(5) -0.0032(5) 0.0009(5)
C13 0.0247(6) 0.0237(7) 0.0216(6) -0.0009(5) -0.0013(5) -0.0029(5)
C14 0.0294(7) 0.0197(6) 0.0295(7) 0.0000(5) -0.0065(6) -0.0032(5)
C15 0.0291(7) 0.0197(6) 0.0260(7) -0.0062(5) -0.0062(5) 0.0055(5)
C16 0.0219(6) 0.0249(7) 0.0209(6) -0.0046(5) -0.0014(5) 0.0026(5)
C21 0.0200(6) 0.0213(6) 0.0207(6) -0.0025(5) -0.0021(5) 0.0021(5)
C22 0.0260(6) 0.0231(6) 0.0258(6) 0.0007(5) -0.0015(6) -0.0014(5)
C23 0.0295(7) 0.0196(6) 0.0327(7) -0.0006(6) -0.0052(6) 0.0027(5)
C24 0.0263(7) 0.0265(7) 0.0283(7) -0.0058(6) -0.0039(5) 0.0096(6)
C25 0.0249(7) 0.0305(7) 0.0230(7) -0.0014(6) 0.0028(5) 0.0041(5)
C26 0.0228(6) 0.0206(6) 0.0251(7) 0.0005(5) 0.0001(5) 0.0014(5)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O1 0.1311(2) 0.01525(7) 0.32021(4) 0.0347(3) Uani d 1 O
O2 0.2143(2) 0.07953(8) 0.24093(4) 0.0369(3) Uani d 1 O
N 0.14290(15) 0.08618(8) 0.28768(5) 0.0229(2) Uani d 1 N
C1 -0.0859(2) 0.11124(10) 0.38890(5) 0.0212(3) Uani d 1 C
C2 -0.1383(2) 0.05055(10) 0.42271(5) 0.0219(3) Uani d 1 C
C3 -0.1971(2) -0.01961(10) 0.46083(5) 0.0221(3) Uani d 1 C
C4 -0.2476(2) -0.08086(9) 0.49459(5) 0.0222(3) Uani d 1 C
C11 0.0692(2) 0.18398(9) 0.30442(5) 0.0188(3) Uani d 1 C
C12 -0.0365(2) 0.19249(9) 0.35274(5) 0.0191(3) Uani d 1 C
C13 -0.1018(2) 0.28933(10) 0.36545(5) 0.0233(3) Uani d 1 C
C14 -0.0632(2) 0.37115(10) 0.33167(6) 0.0262(3) Uani d 1 C
C15 0.0436(2) 0.35999(10) 0.28436(6) 0.0249(3) Uani d 1 C
C16 0.1098(2) 0.26606(10) 0.27052(6) 0.0226(3) Uani d 1 C
C21 -0.3068(2) -0.15196(9) 0.53581(5) 0.0207(3) Uani d 1 C
C22 -0.2646(2) -0.25486(10) 0.53059(6) 0.0250(3) Uani d 1 C
C23 -0.3230(2) -0.32206(10) 0.57131(6) 0.0273(3) Uani d 1 C
C24 -0.4208(2) -0.28904(10) 0.61699(6) 0.0270(3) Uani d 1 C
C25 -0.4628(2) -0.18703(11) 0.62241(6) 0.0261(3) Uani d 1 C
C26 -0.4063(2) -0.11905(10) 0.58189(6) 0.0229(3) Uani d 1 C
H13 -0.179(2) 0.2986(11) 0.3976(6) 0.025(4) Uiso d 1 H
H14 -0.109(2) 0.4407(12) 0.3420(6) 0.035(4) Uiso d 1 H
H15 0.068(2) 0.4183(12) 0.2603(6) 0.038(5) Uiso d 1 H
H16 0.184(2) 0.2568(11) 0.2380(6) 0.021(4) Uiso d 1 H
H22 -0.187(2) -0.2762(11) 0.4987(6) 0.028(4) Uiso d 1 H
H23 -0.295(2) -0.3935(12) 0.5666(6) 0.036(4) Uiso d 1 H
H24 -0.460(2) -0.3356(13) 0.6462(6) 0.038(5) Uiso d 1 H
H25 -0.538(2) -0.1639(11) 0.6548(6) 0.030(4) Uiso d 1 H
H26 -0.433(2) -0.0481(11) 0.5838(6) 0.026(4) Uiso d 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 0.0181 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
O1 N O2 122.93(11) yes
O1 N C11 118.98(10) yes
O2 N C11 118.09(11) yes
C2 C1 C12 172.72(13) yes
C1 C2 C3 179.27(14) yes
C4 C3 C2 179.43(13) yes
C3 C4 C21 178.60(13) yes
C16 C11 C12 122.39(12) yes
C16 C11 N 117.06(11) yes
C12 C11 N 120.54(11) yes
C11 C12 C13 116.57(11) yes
C11 C12 C1 125.38(12) yes
C13 C12 C1 118.03(11) yes
C14 C13 C12 121.35(12) yes
C14 C13 H13 119.0(9) ?
C12 C13 H13 119.6(9) ?
C13 C14 C15 120.45(12) yes
C13 C14 H14 120.2(9) ?
C15 C14 H14 119.3(9) ?
C16 C15 C14 119.79(12) yes
C16 C15 H15 120.5(10) ?
C14 C15 H15 119.7(10) ?
C15 C16 C11 119.43(12) yes
C15 C16 H16 121.1(9) ?
C11 C16 H16 119.5(9) ?
C26 C21 C22 119.60(12) ?
C26 C21 C4 119.74(11) ?
C22 C21 C4 120.67(12) ?
C23 C22 C21 119.44(13) ?
C23 C22 H22 122.1(9) ?
C21 C22 H22 118.4(9) ?
C24 C23 C22 120.74(13) ?
C24 C23 H23 120.7(9) ?
C22 C23 H23 118.5(9) ?
C23 C24 C25 120.05(13) ?
C23 C24 H24 121.0(10) ?
C25 C24 H24 118.9(10) ?
C26 C25 C24 119.90(13) ?
C26 C25 H25 120.4(9) ?
C24 C25 H25 119.7(9) ?
C25 C26 C21 120.28(12) ?
C25 C26 H26 122.6(9) ?
C21 C26 H26 117.1(9) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N 1.2207(14) yes
O2 N 1.2352(14) yes
N C11 1.467(2) yes
C1 C2 1.203(2) yes
C1 C12 1.428(2) yes
C2 C3 1.371(2) yes
C3 C4 1.203(2) yes
C4 C21 1.430(2) yes
C11 C16 1.388(2) yes
C11 C12 1.399(2) yes
C12 C13 1.409(2) yes
C13 C14 1.381(2) yes
C13 H13 0.964(14) ?
C14 C15 1.388(2) yes
C14 H14 1.02(2) ?
C15 C16 1.383(2) yes
C15 H15 0.98(2) ?
C16 H16 0.960(14) ?
C21 C26 1.395(2) ?
C21 C22 1.408(2) ?
C22 C23 1.387(2) ?
C22 H22 1.00(2) ?
C23 C24 1.381(2) ?
C23 H23 0.98(2) ?
C24 C25 1.397(2) ?
C24 H24 0.97(2) ?
C25 C26 1.385(2) ?
C25 H25 1.00(2) ?
C26 H26 0.964(15) ?