data_global
 

 
# 1. SUBMISSION DETAILS
#----------------------
 
_publ_contact_author_name
     'Skelton, B. W.'
_publ_contact_author_address
;
 Chemistry, 
School of Biomedical, Biomolecular and Chemical Science, 
M313, University of Western Australia, 
Perth, WA 6009,
 Australia
;
_publ_contact_author_email            brian.skelton@uwa.edu.au
_publ_contact_author_fax               (+61)_08_6488_1118
_publ_contact_author_phone             (+61)_08_6488_7107
 

 
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
 
 
'Skelton, Brian W.' .
; 
Chemistry, 
School of Biomedical, Biomolecular and Chemical Science, 
M313, University of Western Australia, 
Perth, WA 6009,
 Australia
;


_publ_section_references
;
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. 
 
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138.
 Oak Ridge National Laboratory, Tennessee, USA. 

Oxford Diffraction (2006). CrysAlis CCD. Oxford Diffraction Ltd, 
Abingdon, England.

Oxford Diffraction (2006). CrysAlis RED. Oxford Diffraction Ltd, 
Abingdon, England.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;


 
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#
 
data_jpg096
 
_audit_creation_date                    2010-05-30T15:14:37-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_sum                   'C13 H10 N2 O'
_chemical_formula_moiety                'C13 H10 N2 O'
_chemical_formula_weight                210.23
_chemical_absolute_configuration        unk
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
 
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P c a 21'
_symmetry_space_group_name_Hall        'p 2c -2ac '
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
 
_cell_length_a                          13.664(3)
_cell_length_b                          3.9005(8)
_cell_length_c                          36.748(6)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1958.5(7)
_cell_formula_units_Z                   8
_cell_measurement_temperature           100(2)
_cell_measurement_reflns_used           899
_cell_measurement_theta_min             2.9627
_cell_measurement_theta_max             28.0832
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              needle
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.46
_exptl_crystal_size_mid                 0.07
_exptl_crystal_size_min                 0.03
_exptl_crystal_density_diffrn           1.426
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    880
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           0.093
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
        Empirical absorption correction using spherical harmonic
;
_exptl_absorpt_correction_T_min         0.919
_exptl_absorpt_correction_T_max         1
 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_ambient_temperature             100(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_detector_area_resol_mean        16.0009
_diffrn_orient_matrix_ub_11             -0.0492244855
_diffrn_orient_matrix_ub_12             -0.0284801645
_diffrn_orient_matrix_ub_13             -0.0050108077
_diffrn_orient_matrix_ub_21             -0.0156781819
_diffrn_orient_matrix_ub_22             0.103255009
_diffrn_orient_matrix_ub_23             0.0146399842
_diffrn_orient_matrix_ub_31             0.0015989169
_diffrn_orient_matrix_ub_32             0.1449193472
_diffrn_orient_matrix_ub_33             -0.0114313769
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Sapphire3'
_diffrn_measurement_method              'ω scans'
_diffrn_reflns_av_R_equivalents         0.103
_diffrn_reflns_av_unetI/netI            0.1103
_diffrn_reflns_number                   12227
_diffrn_reflns_limit_h_min              -17
_diffrn_reflns_limit_h_max              17
_diffrn_reflns_limit_k_min              -5
_diffrn_reflns_limit_k_max              5
_diffrn_reflns_limit_l_min              -32
_diffrn_reflns_limit_l_max              47
_diffrn_reflns_theta_min                2.98
_diffrn_reflns_theta_max                28.09
_diffrn_reflns_theta_full               27
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_measured_fraction_theta_max
                                        0.945
_reflns_number_total                    2283
_reflns_number_gt                       1252
_reflns_threshold_expression            I>2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics          'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material        'WinGX Farrugia, L. J. (1999)'

 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2283
_refine_ls_number_parameters            291
_refine_ls_number_restraints            1
_refine_ls_R_factor_all                 0.1049
_refine_ls_R_factor_gt                  0.0504
_refine_ls_wR_factor_ref                0.1009
_refine_ls_wR_factor_gt                 0.0894
_refine_ls_goodness_of_fit_ref          0.844
_refine_ls_restrained_S_all             0.844
_refine_ls_shift/su_max                 0.003
_refine_ls_shift/su_mean                0.001
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack          ?
_refine_diff_density_max                0.221
_refine_diff_density_min                -0.189
_refine_diff_density_rms                0.051
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
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
C11 C 0.6287(3) 0.2388(12) 0.50001(13) 0.0254(12) Uani 1 1 d . . .
H11 H 0.6867 0.2677 0.5139 0.03 Uiso 1 1 calc R . .
C12 C 0.6323(4) 0.0847(13) 0.46731(14) 0.0228(12) Uani 1 1 d . . .
H12 H 0.6942 0.0139 0.4582 0.027 Uiso 1 1 calc R . .
C13 C 0.5596(4) -0.1424(14) 0.41124(13) 0.0325(13) Uani 1 1 d . . .
H13A H 0.5053 -0.3033 0.4078 0.049 Uiso 1 1 calc R . .
H13B H 0.6217 -0.2673 0.4103 0.049 Uiso 1 1 calc R . .
H13C H 0.5581 0.0305 0.3919 0.049 Uiso 1 1 calc R . .
N13 N 0.5500(3) 0.0248(10) 0.44631(13) 0.0219(12) Uani 1 1 d . . .
C14 C 0.4579(4) 0.1271(13) 0.45799(14) 0.0252(12) Uani 1 1 d . . .
O14 O 0.3838(3) 0.0669(10) 0.43828(10) 0.0324(10) Uani 1 1 d . . .
C14A C 0.4530(3) 0.2977(12) 0.49326(11) 0.0217(11) Uani 1 1 d . . .
C15 C 0.3610(3) 0.4098(12) 0.50671(14) 0.0232(11) Uani 1 1 d . . .
H15 H 0.3051 0.37 0.4919 0.028 Uiso 1 1 calc R . .
N16 N 0.3475(3) 0.5609(11) 0.53735(13) 0.0232(11) Uani 1 1 d . . .
C16A C 0.4289(3) 0.6378(13) 0.55838(12) 0.0219(11) Uani 1 1 d . . .
C17 C 0.4157(4) 0.8119(12) 0.59091(13) 0.0274(12) Uani 1 1 d . . .
H17 H 0.3514 0.8735 0.5982 0.033 Uiso 1 1 calc R . .
C18 C 0.4937(4) 0.8979(14) 0.61295(14) 0.0290(12) Uani 1 1 d . . .
H18 H 0.4837 1.0221 0.6349 0.035 Uiso 1 1 calc R . .
C19 C 0.5890(4) 0.7971(13) 0.60219(13) 0.0290(13) Uani 1 1 d . . .
H19 H 0.6431 0.8511 0.6173 0.035 Uiso 1 1 calc R . .
C110 C 0.6041(4) 0.6254(13) 0.57073(12) 0.0225(11) Uani 1 1 d . . .
H110 H 0.6689 0.5653 0.5639 0.027 Uiso 1 1 calc R . .
C111 C 0.5270(4) 0.5362(13) 0.54846(15) 0.0188(13) Uani 1 1 d . . .
C112 C 0.5368(3) 0.3589(13) 0.51376(12) 0.0205(11) Uani 1 1 d . . .
C21 C 0.3694(3) 0.2656(12) 0.28609(13) 0.0215(12) Uani 1 1 d . . .
H21 H 0.4284 0.2243 0.2732 0.026 Uiso 1 1 calc R . .
C22 C 0.3709(4) 0.4247(13) 0.31843(15) 0.0250(13) Uani 1 1 d . . .
H22 H 0.4326 0.4847 0.3285 0.03 Uiso 1 1 calc R . .
C23 C 0.2975(4) 0.6771(15) 0.37314(14) 0.0328(13) Uani 1 1 d . . .
H23A H 0.2981 0.5048 0.3925 0.049 Uiso 1 1 calc R . .
H23B H 0.2419 0.8322 0.3767 0.049 Uiso 1 1 calc R . .
H23C H 0.3586 0.8087 0.3738 0.049 Uiso 1 1 calc R . .
N23 N 0.2885(3) 0.5052(9) 0.33764(14) 0.0219(13) Uani 1 1 d . . .
C24 C 0.1950(4) 0.4298(13) 0.32535(13) 0.0231(12) Uani 1 1 d . . .
O24 O 0.1218(3) 0.5052(8) 0.34277(10) 0.0306(11) Uani 1 1 d . . .
C24A C 0.1924(3) 0.2415(12) 0.29067(12) 0.0200(11) Uani 1 1 d . . .
C25 C 0.1007(3) 0.1374(13) 0.27682(13) 0.0238(12) Uani 1 1 d . . .
H25 H 0.0444 0.1931 0.2908 0.029 Uiso 1 1 calc R . .
N26 N 0.0865(4) -0.0280(10) 0.24660(15) 0.0275(13) Uani 1 1 d . . .
C26A C 0.1702(4) -0.1102(14) 0.22697(13) 0.0250(12) Uani 1 1 d . . .
C27 C 0.1560(3) -0.2936(12) 0.19387(13) 0.0249(12) Uani 1 1 d . . .
H27 H 0.0918 -0.353 0.1862 0.03 Uiso 1 1 calc R . .
C28 C 0.2345(4) -0.3837(12) 0.17321(14) 0.0255(12) Uani 1 1 d . . .
H28 H 0.2242 -0.5054 0.1511 0.031 Uiso 1 1 calc R . .
C29 C 0.3301(3) -0.3011(12) 0.18372(13) 0.0236(12) Uani 1 1 d . . .
H29 H 0.384 -0.3674 0.169 0.028 Uiso 1 1 calc R . .
C210 C 0.3454(3) -0.1236(13) 0.21548(13) 0.0234(12) Uani 1 1 d . . .
H210 H 0.4103 -0.0681 0.2226 0.028 Uiso 1 1 calc R . .
C211 C 0.2646(4) -0.0197(11) 0.23826(16) 0.0185(13) Uani 1 1 d . . .
C212 C 0.2771(3) 0.1588(13) 0.27138(13) 0.0196(11) Uani 1 1 d . . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
C11 C12 1.344(7) . ?
C11 C112 1.432(6) . ?
C11 H11 0.95 . ?
C12 N13 1.383(7) . ?
C12 H12 0.95 . ?
C13 N13 1.450(7) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
N13 C14 1.388(7) . ?
C14 O14 1.267(6) . ?
C14 C14A 1.459(6) . ?
C14A C112 1.392(6) . ?
C14A C15 1.420(6) . ?
C15 N16 1.284(7) . ?
C15 H15 0.95 . ?
N16 C16A 1.386(6) . ?
C16A C17 1.386(6) . ?
C16A C111 1.445(7) . ?
C17 C18 1.380(7) . ?
C17 H17 0.95 . ?
C18 C19 1.416(7) . ?
C18 H18 0.95 . ?
C19 C110 1.352(7) . ?
C19 H19 0.95 . ?
C110 C111 1.379(7) . ?
C110 H110 0.95 . ?
C111 C112 1.457(7) . ?
C21 C22 1.341(7) . ?
C21 C212 1.434(6) . ?
C21 H21 0.95 . ?
C22 N23 1.366(7) . ?
C22 H22 0.95 . ?
C23 N23 1.472(7) . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
N23 C24 1.387(7) . ?
C24 O24 1.223(6) . ?
C24 C24A 1.471(6) . ?
C24A C212 1.395(6) . ?
C24A C25 1.413(6) . ?
C25 N26 1.299(6) . ?
C25 H25 0.95 . ?
N26 C26A 1.390(7) . ?
C26A C211 1.400(8) . ?
C26A C27 1.425(7) . ?
C27 C28 1.361(6) . ?
C27 H27 0.95 . ?
C28 C29 1.399(7) . ?
C28 H28 0.95 . ?
C29 C210 1.373(7) . ?
C29 H29 0.95 . ?
C210 C211 1.443(7) . ?
C210 H210 0.95 . ?
C211 C212 1.412(7) . ?
 
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
C12 C11 C112 119.6(5) . . ?
C12 C11 H11 120.2 . . ?
C112 C11 H11 120.2 . . ?
C11 C12 N13 123.0(5) . . ?
C11 C12 H12 118.5 . . ?
N13 C12 H12 118.5 . . ?
N13 C13 H13A 109.5 . . ?
N13 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N13 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 N13 C14 121.1(5) . . ?
C12 N13 C13 119.9(5) . . ?
C14 N13 C13 119.0(5) . . ?
O14 C14 N13 119.7(5) . . ?
O14 C14 C14A 123.7(5) . . ?
N13 C14 C14A 116.6(5) . . ?
C112 C14A C15 119.2(4) . . ?
C112 C14A C14 121.4(4) . . ?
C15 C14A C14 119.4(4) . . ?
N16 C15 C14A 125.0(5) . . ?
N16 C15 H15 117.5 . . ?
C14A C15 H15 117.5 . . ?
C15 N16 C16A 118.3(5) . . ?
C17 C16A N16 118.9(5) . . ?
C17 C16A C111 118.2(5) . . ?
N16 C16A C111 122.9(5) . . ?
C18 C17 C16A 121.7(5) . . ?
C18 C17 H17 119.2 . . ?
C16A C17 H17 119.2 . . ?
C17 C18 C19 118.6(5) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C110 C19 C18 121.2(5) . . ?
C110 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C110 C111 121.0(5) . . ?
C19 C110 H110 119.5 . . ?
C111 C110 H110 119.5 . . ?
C110 C111 C16A 119.4(5) . . ?
C110 C111 C112 124.6(5) . . ?
C16A C111 C112 115.9(4) . . ?
C14A C112 C11 118.3(4) . . ?
C14A C112 C111 118.6(4) . . ?
C11 C112 C111 123.0(4) . . ?
C22 C21 C212 118.8(5) . . ?
C22 C21 H21 120.6 . . ?
C212 C21 H21 120.6 . . ?
C21 C22 N23 123.5(5) . . ?
C21 C22 H22 118.3 . . ?
N23 C22 H22 118.3 . . ?
N23 C23 H23A 109.5 . . ?
N23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N23 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 N23 C24 122.9(5) . . ?
C22 N23 C23 119.6(4) . . ?
C24 N23 C23 117.6(4) . . ?
O24 C24 N23 122.1(5) . . ?
O24 C24 C24A 123.7(5) . . ?
N23 C24 C24A 114.2(5) . . ?
C212 C24A C25 119.1(4) . . ?
C212 C24A C24 122.4(4) . . ?
C25 C24A C24 118.5(4) . . ?
N26 C25 C24A 125.7(5) . . ?
N26 C25 H25 117.2 . . ?
C24A C25 H25 117.2 . . ?
C25 N26 C26A 115.8(5) . . ?
N26 C26A C211 123.1(5) . . ?
N26 C26A C27 116.5(4) . . ?
C211 C26A C27 120.4(5) . . ?
C28 C27 C26A 119.9(4) . . ?
C28 C27 H27 120.1 . . ?
C26A C27 H27 120.1 . . ?
C27 C28 C29 121.5(5) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C210 C29 C28 119.5(4) . . ?
C210 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C210 C211 121.2(5) . . ?
C29 C210 H210 119.4 . . ?
C211 C210 H210 119.4 . . ?
C26A C211 C212 119.4(5) . . ?
C26A C211 C210 117.5(5) . . ?
C212 C211 C210 123.1(5) . . ?
C24A C212 C211 116.9(4) . . ?
C24A C212 C21 118.1(4) . . ?
C211 C212 C21 125.0(4) . . ?
#===END
