#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/76/2227656.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227656
loop_
_publ_author_name
'Zhou, Xingqin'
'Qin, Xiaofen'
'Zhang, Jiankang'
_publ_section_title
;
 2-(4-Methylphenyl)-2H-indazole
;
_journal_coeditor_code           IM2233
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2732
_journal_paper_doi               10.1107/S1600536810038948
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H12 N2'
_chemical_formula_moiety         'C14 H12 N2'
_chemical_formula_sum            'C14 H12 N2'
_chemical_formula_weight         208.26
_chemical_name_systematic
;
2-(4-Methylphenyl)-2H-indazole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.636(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.539(4)
_cell_length_b                   6.029(2)
_cell_length_c                   14.401(5)
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      2.835
_cell_volume                     1086.5(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5372
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0491
_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)+(0.0692P)²+0.1862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                1236
_reflns_number_total             1915
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2233.cif
_cod_data_source_block           I
_cod_original_cell_volume        1086.4(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227656
_cod_database_fobs_code          2227656
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_type_symbol
_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
N N1 0.57580(13) 0.0040(3) 0.35143(12) 0.0442(5) Uani d . 1 . .
N N2 0.55544(13) 0.2100(3) 0.38504(11) 0.0420(5) Uani d . 1 . .
C C1 0.64349(16) 0.3229(4) 0.41472(14) 0.0457(6) Uani d . 1 . .
H H1 0.6458 0.4648 0.4401 0.055 Uiso calc R 1 . .
C C2 0.72979(16) 0.1879(4) 0.40029(13) 0.0433(5) Uani d . 1 . .
C C3 0.84218(17) 0.2057(4) 0.41335(16) 0.0566(7) Uani d . 1 . .
H H3 0.8738 0.3327 0.4393 0.068 Uiso calc R 1 . .
C C4 0.90270(19) 0.0330(5) 0.38714(17) 0.0631(7) Uani d . 1 . .
H H4 0.9767 0.0421 0.3958 0.076 Uiso calc R 1 . .
C C5 0.85600(18) -0.1603(4) 0.34703(16) 0.0573(7) Uani d . 1 . .
H H5 0.9002 -0.2748 0.3295 0.069 Uiso calc R 1 . .
C C6 0.74854(17) -0.1839(4) 0.33324(15) 0.0490(6) Uani d . 1 . .
H H6 0.7188 -0.3122 0.3067 0.059 Uiso calc R 1 . .
C C7 0.68372(16) -0.0084(3) 0.36036(13) 0.0409(5) Uani d . 1 . .
C C8 0.44707(16) 0.2872(3) 0.38157(13) 0.0417(5) Uani d . 1 . .
C C9 0.36778(16) 0.1513(4) 0.41005(14) 0.0473(6) Uani d . 1 . .
H H9 0.3846 0.0112 0.4338 0.057 Uiso calc R 1 . .
C C10 0.26299(17) 0.2226(4) 0.40340(15) 0.0516(6) Uani d . 1 . .
H H10 0.2097 0.1297 0.4231 0.062 Uiso calc R 1 . .
C C11 0.23572(17) 0.4304(4) 0.36780(15) 0.0486(6) Uani d . 1 . .
C C12 0.31752(18) 0.5648(4) 0.34099(16) 0.0538(6) Uani d . 1 . .
H H12 0.3012 0.7054 0.3177 0.065 Uiso calc R 1 . .
C C13 0.42283(18) 0.4963(4) 0.34777(15) 0.0508(6) Uani d . 1 . .
H H13 0.4767 0.5901 0.3298 0.061 Uiso calc R 1 . .
C C14 0.12148(18) 0.5069(5) 0.35741(19) 0.0705(8) Uani d . 1 . .
H H14A 0.0757 0.3925 0.3788 0.106 Uiso calc R 1 . .
H H14B 0.1025 0.5382 0.2931 0.106 Uiso calc R 1 . .
H H14C 0.1133 0.6386 0.3937 0.106 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 103.03(16) ?
C1 N2 N1 . . 113.95(17) ?
C1 N2 C8 . . 127.16(19) ?
N1 N2 C8 . . 118.82(16) ?
N2 C1 C2 . . 106.85(19) ?
N2 C1 H1 . . 126.6 ?
C2 C1 H1 . . 126.6 ?
C1 C2 C3 . . 136.0(2) ?
C1 C2 C7 . . 104.43(17) ?
C3 C2 C7 . . 119.5(2) ?
C4 C3 C2 . . 118.4(2) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 121.5(2) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C6 C5 C4 . . 121.9(2) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C7 . . 117.8(2) ?
C5 C6 H6 . . 121.1 ?
C7 C6 H6 . . 121.1 ?
N1 C7 C6 . . 127.45(19) ?
N1 C7 C2 . . 111.74(18) ?
C6 C7 C2 . . 120.80(19) ?
C9 C8 C13 . . 120.3(2) ?
C9 C8 N2 . . 119.91(19) ?
C13 C8 N2 . . 119.78(19) ?
C8 C9 C10 . . 119.9(2) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C9 C10 C11 . . 121.2(2) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C11 C10 . . 117.6(2) ?
C12 C11 C14 . . 120.8(2) ?
C10 C11 C14 . . 121.6(2) ?
C11 C12 C13 . . 121.9(2) ?
C11 C12 H12 . . 119.0 ?
C13 C12 H12 . . 119.0 ?
C8 C13 C12 . . 119.1(2) ?
C8 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
N1 C7 . 1.353(2) ?
N1 N2 . 1.362(2) ?
N2 C1 . 1.344(2) ?
N2 C8 . 1.434(3) ?
C1 C2 . 1.380(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.414(3) ?
C2 C7 . 1.422(3) ?
C3 C4 . 1.356(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.411(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.357(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.405(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.371(3) ?
C8 C13 . 1.378(3) ?
C9 C10 . 1.380(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.388(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.381(3) ?
C11 C14 . 1.503(3) ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9249760
