#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/38/2203806.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_2203806
loop_
_publ_author_name
'Riddle, Gordon B.'
'Grossie, David A.'
'Turnbull, Kenneth'
_publ_section_title
;
 3-(2-Biphenyl)sydnone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o977
_journal_page_last               o978
_journal_paper_doi               10.1107/S1600536804010773
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C14 H10 N2 O2'
_chemical_formula_moiety         'C14 H10 N2 O2'
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_chemical_melting_point          418
_chemical_name_systematic
;
3-(2-biphenyl)sydnone
;
_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           SHELXL97
_cell_angle_alpha                90.000
_cell_angle_beta                 108.406(15)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   11.012(15)
_cell_length_b                   8.310(15)
_cell_length_c                   12.941(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1124(3)
_computing_cell_refinement       'DENZO (Otwinowski and Minor, 1997)'
_computing_data_collection       'MarControl (MARResearch, 2000)'
_computing_data_reduction        'SCALEPACK (Fox and Holmes, 1966)'
_computing_molecular_graphics    'ORTEX (McArdle, 1994)'
_computing_publication_material  'OSCAIL (McArdle, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Mar CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.70998
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16475
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         26.67
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0495
_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)+(0.0767P)²+0.6398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2019
_reflns_number_total             2210
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6100.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2203806
_cod_database_fobs_code          2203806
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_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_type_symbol
O5 0.44588(12) 1.14144(13) 1.10069(10) 0.0285(3) Uani d . 1 O
O1 0.28415(12) 1.02296(13) 1.14705(10) 0.0277(3) Uani d . 1 O
N2 0.21119(15) 0.88504(16) 1.12291(13) 0.0269(4) Uani d . 1 N
C1' 0.19971(15) 0.65566(17) 1.01464(13) 0.0208(4) Uani d . 1 C
C5' 0.17153(16) 0.38668(19) 1.06716(15) 0.0258(4) Uani d . 1 C
H5' 0.1805 0.3085 1.1205 0.031 Uiso calc R 1 H
C2' 0.13860(15) 0.62399(17) 0.90473(14) 0.0208(4) Uani d . 1 C
N3 0.25200(13) 0.81280(15) 1.05005(11) 0.0201(3) Uani d . 1 N
C6' 0.21655(16) 0.54137(18) 1.09574(14) 0.0230(4) Uani d . 1 C
H6' 0.2574 0.5680 1.1682 0.028 Uiso calc R 1 H
C3' 0.09731(16) 0.46585(18) 0.87856(15) 0.0245(4) Uani d . 1 C
H3' 0.0584 0.4379 0.8060 0.029 Uiso calc R 1 H
C4' 0.11319(16) 0.34974(19) 0.95864(15) 0.0268(4) Uani d . 1 C
H4' 0.0842 0.2455 0.9391 0.032 Uiso calc R 1 H
C4 0.34393(15) 0.88986(18) 1.02302(14) 0.0219(4) Uani d . 1 C
H4 0.3824 0.8571 0.9721 0.026 Uiso calc R 1 H
C5 0.37117(16) 1.03043(18) 1.08679(14) 0.0222(4) Uani d . 1 C
C7 0.11251(15) 0.74965(18) 0.81879(13) 0.0216(4) Uani d . 1 C
C8 0.14163(16) 0.72250(19) 0.72304(14) 0.0243(4) Uani d . 1 C
H8 0.1795 0.6260 0.7135 0.029 Uiso calc R 1 H
C9 0.11455(16) 0.8382(2) 0.64202(14) 0.0258(4) Uani d . 1 C
H9 0.1345 0.8190 0.5784 0.031 Uiso calc R 1 H
C10 0.05779(16) 0.98262(19) 0.65513(14) 0.0258(4) Uani d . 1 C
H10 0.0405 1.0605 0.6008 0.031 Uiso calc R 1 H
C11 0.02689(16) 1.01049(19) 0.74951(14) 0.0248(4) Uani d . 1 C
H11 -0.0121 1.1066 0.7581 0.030 Uiso calc R 1 H
C12 0.05423(16) 0.89503(18) 0.83104(14) 0.0239(4) Uani d . 1 C
H12 0.0337 0.9143 0.8943 0.029 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
N2 O1 C5 111.06(12) yes
N3 N2 O1 103.66(14) yes
C6' C1' C2' 123.41(17) yes
C6' C1' N3 115.84(17) yes
C2' C1' N3 120.74(14) yes
C4' C5' C6' 119.33(15) yes
C4' C5' H5' 120.3 no
C6' C5' H5' 120.3 no
C1' C2' C3' 116.14(15) yes
C1' C2' C7 123.25(16) yes
C3' C2' C7 120.56(18) yes
N2 N3 C4 115.44(15) yes
N2 N3 C1' 116.74(13) yes
C4 N3 C1' 127.66(13) yes
C1' C6' C5' 118.91(18) yes
C1' C6' H6' 120.5 no
C5' C6' H6' 120.5 no
C4' C3' C2' 121.27(19) yes
C4' C3' H3' 119.4 no
C2' C3' H3' 119.4 no
C5' C4' C3' 120.91(17) yes
C5' C4' H4' 119.5 no
C3' C4' H4' 119.5 no
N3 C4 C5 106.47(15) yes
N3 C4 H4 126.8 no
C5 C4 H4 126.8 no
O5 C5 C4 136.77(16) yes
O5 C5 O1 119.87(15) yes
C4 C5 O1 103.35(14) yes
C8 C7 C12 118.88(15) yes
C8 C7 C2' 120.51(16) yes
C12 C7 C2' 120.58(16) yes
C9 C8 C7 120.43(17) yes
C9 C8 H8 119.8 no
C7 C8 H8 119.8 no
C8 C9 C10 120.38(17) yes
C8 C9 H9 119.8 no
C10 C9 H9 119.8 no
C11 C10 C9 119.81(16) yes
C11 C10 H10 120.1 no
C9 C10 H10 120.1 no
C10 C11 C12 119.98(17) yes
C10 C11 H11 120.0 no
C12 C11 H11 120.0 no
C11 C12 C7 120.52(17) yes
C11 C12 H12 119.7 no
C7 C12 H12 119.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O5 C5 1.211(2) yes
O1 N2 1.378(3) yes
O1 C5 1.415(2) yes
N2 N3 1.311(2) yes
C1' C6' 1.384(3) yes
C1' C2' 1.393(3) yes
C1' N3 1.442(3) yes
C5' C4' 1.382(3) yes
C5' C6' 1.385(3) yes
C5' H5' 0.9300 no
C2' C3' 1.397(3) yes
C2' C7 1.486(3) yes
N3 C4 1.335(2) yes
C6' H6' 0.9300 no
C3' C4' 1.386(3) yes
C3' H3' 0.9300 no
C4' H4' 0.9300 no
C4 C5 1.407(3) yes
C4 H4 0.9300 no
C7 C8 1.393(3) yes
C7 C12 1.400(3) yes
C8 C9 1.384(3) yes
C8 H8 0.9300 no
C9 C10 1.388(3) yes
C9 H9 0.9300 no
C10 C11 1.387(3) yes
C10 H10 0.9300 no
C11 C12 1.387(3) yes
C11 H11 0.9300 no
C12 H12 0.9300 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O5 3_677 0.93 2.36 3.214(6) 152 yes
C6' H6' O1 2_547 0.93 2.60 3.335(6) 136 yes
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
C5 O1 N2 N3 -0.52(18) no
C6' C1' C2' C3' -2.0(2) no
N3 C1' C2' C3' 176.79(13) no
C6' C1' C2' C7 175.53(14) no
N3 C1' C2' C7 -5.7(2) no
O1 N2 N3 C4 -0.51(19) no
O1 N2 N3 C1' 175.15(13) no
C6' C1' N3 N2 -57.4(2) no
C2' C1' N3 N2 123.71(18) no
C6' C1' N3 C4 117.66(19) no
C2' C1' N3 C4 -61.2(2) no
C2' C1' C6' C5' 0.5(2) no
N3 C1' C6' C5' -178.40(13) no
C4' C5' C6' C1' 1.1(2) no
C1' C2' C3' C4' 2.0(2) no
C7 C2' C3' C4' -175.59(14) no
C6' C5' C4' C3' -1.1(2) no
C2' C3' C4' C5' -0.5(2) no
N2 N3 C4 C5 1.3(2) no
C1' N3 C4 C5 -173.79(15) no
N3 C4 C5 O5 177.0(2) no
N3 C4 C5 O1 -1.47(17) no
N2 O1 C5 O5 -177.56(15) no
N2 O1 C5 C4 1.26(18) no
C1' C2' C7 C8 132.61(18) no
C3' C2' C7 C8 -49.9(2) no
C1' C2' C7 C12 -49.6(2) no
C3' C2' C7 C12 127.84(18) no
C12 C7 C8 C9 0.7(2) no
C2' C7 C8 C9 178.50(15) no
C7 C8 C9 C10 -0.1(2) no
C8 C9 C10 C11 -0.7(2) no
C9 C10 C11 C12 0.8(2) no
C10 C11 C12 C7 -0.3(2) no
C8 C7 C12 C11 -0.5(2) no
C2' C7 C12 C11 -178.31(15) no
