#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/55/2005584.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_2005584
loop_
_publ_author_name
'Hager, O.'
'Foces-Foces, C.'
'Jagerovic, N.'
'Elguero, J.'
'Trofimenko, S.'
_publ_contact_author
;
     C. Foces-Foces
     Instituto de Quimica-Fisica Rocasolano, CSIC
     Dpto. de Cristalografia
     Serrano, 119
     E-28006 Madrid
     Spain
;
_publ_section_title
;
 5-Phenylindazole
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2894
_journal_page_last               2896
_journal_paper_doi               10.1107/S0108270196007068
_journal_volume                  52
_journal_year                    1996
_chemical_formula_analytical     'C13 H10 N2'
_chemical_formula_moiety         'C13 H10 N2'
_chemical_formula_sum            'C13 H10 N2'
_chemical_formula_weight         194.23
_chemical_name_systematic        5-Phenylindazole
_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'
_audit_creation_method           from_xtal_archive_file_using_CIFIO
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_formula_units_Z            8
_cell_length_a                   5.9740(4)
_cell_length_b                   8.2261(7)
_cell_length_c                   40.685(4)
_cell_measurement_reflns_used    58
_cell_measurement_temperature    293
_cell_measurement_theta_max      45
_cell_measurement_theta_min      2
_cell_volume                     1999.4(3)
_computing_cell_refinement       'LSUCRE (Appleman, 1983)'
_computing_data_collection       'Seifert XRD3000-S diffractometer'
_computing_data_reduction
'Xtal3.2 DIFDAT SORTREF ADDREF (Hall, Flack & Stewart, 1994)'
_computing_molecular_graphics    Xtal3.2
_computing_publication_material  Xtal3.2_BONDLA_CIFIO
_computing_structure_refinement  Xtal3.2_CRYLSQ
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Seifert XRD3000-S diffractometer'
_diffrn_measurement_method       'ω/2θ scans in bisecting geometry'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  .001
_diffrn_reflns_av_sigmaI/netI    .015
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1931
_diffrn_reflns_reduction_process equatorial_monochr_Lp
_diffrn_reflns_theta_max         64.89
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  '100 min'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         .32
_refine_diff_density_min         -.23
_refine_ls_abs_structure_details none
_refine_ls_extinction_coef       96(10)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   .456
_refine_ls_goodness_of_fit_obs   .424
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .065
_refine_ls_R_factor_obs          .038
_refine_ls_shift/esd_max         .013
_refine_ls_shift/esd_mean        .001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .057
_refine_ls_wR_factor_obs         .044
_reflns_number_observed          1122
_reflns_number_total             1550
_reflns_observed_criterion       refl_observed_if_I____>_2_sigma(I___)
_cod_data_source_file            bm1080.cif
_cod_data_source_block           PHINDA
_cod_database_code               2005584
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,+y,1/2-z
1/2-x,1/2+y,+z
+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
N1 .0480(10) .0530(10) .0370(10) .0020(10) .0040(10) -.0010(10)
N2 .0500(10) .0560(10) .0430(10) -.0010(10) -.0054(9) -.0060(10)
C3 .0430(10) .0490(10) .0450(10) -.0030(10) -.0030(10) -.0020(10)
C31 .0360(10) .0410(10) .0400(10) .0010(10) -.0012(9) .0020(10)
C4 .0350(10) .0450(10) .0390(10) -.0010(10) .0031(9) .0010(10)
C5 .0360(10) .0430(10) .0370(10) .0020(10) .0006(9) .0010(10)
C6 .0360(10) .0460(10) .0450(10) -.0020(10) .0010(10) .0020(10)
C7 .0370(10) .0450(10) .0450(10) .0000(10) .0070(10) .0030(10)
C71 .0380(10) .0390(10) .0400(10) .0050(10) .0022(9) .0040(10)
C8 .0370(10) .0460(10) .0420(10) .0030(10) -.0005(9) -.0020(10)
C9 .056(2) .061(2) .0480(10) -.011(2) .0100(10) -.0080(10)
C10 .066(2) .071(2) .0470(10) -.005(2) .0130(10) .0000(10)
C11 .060(2) .067(2) .0410(10) .007(2) -.0010(10) -.0070(10)
C12 .063(2) .065(2) .054(2) -.008(2) -.0080(10) -.011(2)
C13 .0520(10) .060(2) .0490(10) -.010(2) .0010(10) -.0020(10)
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_calc_attached_atom
N1 .5520(4) .3310(3) .52819(5) .046(1) Uani yes yes
N2 .3534(4) .2507(3) .52585(5) .049(1) Uani yes yes
C3 .2488(5) .2743(3) .55408(6) .046(1) Uani yes yes
C31 .3804(4) .3697(3) .57590(6) .039(1) Uani yes yes
C4 .3551(4) .4281(3) .60811(6) .040(1) Uani yes yes
C5 .5252(4) .5195(3) .62202(5) .039(1) Uani yes yes
C6 .7219(4) .5500(3) .60295(6) .042(1) Uani yes yes
C7 .7504(5) .4951(3) .57158(6) .042(1) Uani yes yes
C71 .5770(4) .4026(3) .55812(6) .039(1) Uani yes yes
C8 .5099(4) .5805(3) .65648(6) .041(1) Uani yes yes
C9 .3743(5) .5046(4) .67962(7) .055(2) Uani yes yes
C10 .3626(6) .5599(4) .71174(7) .061(2) Uani yes yes
C11 .4855(5) .6919(4) .72154(6) .056(2) Uani yes yes
C12 .6211(6) .7685(4) .69918(7) .060(2) Uani yes yes
C13 .6326(5) .7142(4) .66699(7) .054(2) Uani yes yes
H1 .648(5) .326(3) .5115(7) .019(7) Uiso ? ?
H3 .101(6) .224(4) .5593(8) .039(9) Uiso ? ?
H4 .221(5) .406(3) .6209(6) .017(7) Uiso ? ?
H6 .846(5) .616(3) .6135(7) .021(7) Uiso ? ?
H7 .892(5) .518(4) .5581(7) .024(7) Uiso ? ?
H9 .292(5) .409(4) .6728(7) .030(8) Uiso ? ?
H10 .277(6) .506(4) .7275(8) .041(9) Uiso ? ?
H11 .475(5) .728(4) .7449(8) .032(8) Uiso ? ?
H12 .701(6) .865(4) .7055(8) .05(1) Uiso ? ?
H13 .723(6) .774(4) .6511(7) .033(8) Uiso ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .017 .009 IntTabIV
N .029 .018 IntTabIV
H 0 0 IntTabIV
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -1 8
0 2 10
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
H1 N1 C71 129(2) ?
H1 N1 N2 119(2) ?
C71 N1 N2 111.6(2) yes
C3 N2 N1 106.2(2) yes
H3 C3 N2 123(2) ?
H3 C3 C31 126(2) ?
N2 C3 C31 111.3(2) yes
C4 C31 C71 120.3(2) yes
C4 C31 C3 135.4(2) yes
C71 C31 C3 104.3(2) yes
H4 C4 C5 119(2) ?
H4 C4 C31 122(2) ?
C5 C4 C31 119.2(2) yes
C4 C5 C6 118.4(2) yes
C4 C5 C8 121.5(2) ?
C6 C5 C8 120.1(2) ?
H6 C6 C7 119(2) ?
H6 C6 C5 118(2) ?
C7 C6 C5 123.5(2) yes
H7 C7 C6 123(2) ?
H7 C7 C71 120(2) ?
C6 C7 C71 117.0(2) yes
N1 C71 C7 131.9(2) yes
N1 C71 C31 106.6(2) yes
C7 C71 C31 121.5(2) yes
C13 C8 C9 117.0(2) yes
C13 C8 C5 121.6(2) ?
C9 C8 C5 121.4(2) ?
H9 C9 C10 121(2) ?
H9 C9 C8 118(2) ?
C10 C9 C8 121.4(3) ?
H10 C10 C11 118(2) ?
H10 C10 C9 121(2) ?
C11 C10 C9 120.5(3) ?
H11 C11 C10 119(2) ?
H11 C11 C12 122(2) ?
C10 C11 C12 119.2(3) ?
H12 C12 C11 120(2) ?
H12 C12 C13 120(2) ?
C11 C12 C13 120.5(3) ?
H13 C13 C12 119(2) ?
H13 C13 C8 119(2) ?
C12 C13 C8 121.4(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C71 1.361(3) yes
N1 N2 1.362(3) yes
N2 C3 1.322(3) yes
C3 H3 1.00(4) ?
C3 C31 1.422(4) yes
C31 C4 1.404(3) yes
C31 C71 1.405(3) yes
C4 H4 .97(3) ?
C4 C5 1.385(3) yes
C5 C6 1.431(3) yes
C5 C8 1.492(3) yes
C6 H6 1.02(3) ?
C6 C7 1.365(3) yes
C7 H7 1.03(3) ?
C7 C71 1.397(4) yes
C8 C13 1.389(4) ?
C8 C9 1.390(4) ?
C9 H9 .97(3) ?
C9 C10 1.386(4) ?
C10 H10 .93(3) ?
C10 C11 1.370(5) ?
C11 H11 1.00(3) ?
C11 C12 1.372(4) ?
C12 H12 .96(4) ?
C12 C13 1.385(4) ?
C13 H13 .98(3) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 C5 C8 C9 1_555 1_555 1_555 1_555 23.8(4) yes
C4 C5 C8 C13 1_555 1_555 1_555 1_555 -157.1(3) ?
