#------------------------------------------------------------------------------
#$Date: 2018-06-26 18:43:34 +0300 (Tue, 26 Jun 2018) $
#$Revision: 208651 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/25/2242544.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_2242544
loop_
_publ_author_name
'Peters, Morten K.'
'Näther, Christian'
'Herges, Rainer'
_publ_section_title
;
 Crystal structure of 2-[2-(pyridin-3-yl)diazen-1-yl]aniline
;
_journal_coeditor_code           WM5450
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1013
_journal_page_last               1016
_journal_paper_doi               10.1107/S2056989018008605
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C11 H10 N4'
_chemical_formula_moiety         'C11 H10 N4'
_chemical_formula_sum            'C11 H10 N4'
_chemical_formula_weight         198.23
_chemical_name_systematic
;
2-[2-(Pyridin-3-yl)diazen-1-yl]aniline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 113.046(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2798(8)
_cell_length_b                   5.9792(3)
_cell_length_c                   13.4130(9)
_cell_measurement_reflns_used    8233
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      3.301
_cell_volume                     980.03(11)
_computing_cell_refinement
;
X-AREA (Stoe, 2008)
;
_computing_data_collection
;
X-AREA (Stoe, 2008)
;
_computing_data_reduction
;
X-AREA (Stoe, 2008)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008) and DIAMOND (Brandenburg, 2014)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Stoe IPDS-1'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8233
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.301
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.182
_refine_ls_extinction_coef       0.054(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0675P)²+0.0778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                1731
_reflns_number_total             2137
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5450sup1.cif
_cod_data_source_block           I
_cod_database_code               2242544
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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_occupancy
C C1 0.42109(8) 0.49909(17) 0.67373(8) 0.0197(3) Uani d 1
C C2 0.40530(8) 0.65338(19) 0.74372(9) 0.0240(3) Uani d 1
H H2 0.3449 0.6313 0.7638 0.029 Uiso calc 1
N N1 0.46934(7) 0.83068(16) 0.78456(8) 0.0264(3) Uani d 1
C C3 0.55368(9) 0.85966(19) 0.75476(9) 0.0252(3) Uani d 1
H H3 0.5997 0.9861 0.7817 0.030 Uiso calc 1
C C4 0.57689(9) 0.71309(19) 0.68624(9) 0.0261(3) Uani d 1
H H4 0.6382 0.7387 0.6680 0.031 Uiso calc 1
C C5 0.51034(9) 0.53033(18) 0.64487(9) 0.0236(3) Uani d 1
H H5 0.5248 0.4281 0.5979 0.028 Uiso calc 1
N N2 0.34292(7) 0.32432(14) 0.63669(7) 0.0218(2) Uani d 1
N N3 0.35904(7) 0.19490(15) 0.56895(7) 0.0216(2) Uani d 1
C C6 0.28594(8) 0.01793(17) 0.52757(8) 0.0205(3) Uani d 1
C C7 0.19205(8) -0.03083(18) 0.55077(8) 0.0221(3) Uani d 1
C C8 0.13128(9) -0.22461(19) 0.50278(9) 0.0272(3) Uani d 1
H H8 0.0687 -0.2617 0.5171 0.033 Uiso calc 1
C C9 0.16052(9) -0.3602(2) 0.43605(9) 0.0294(3) Uani d 1
H H9 0.1186 -0.4903 0.4059 0.035 Uiso calc 1
C C10 0.25156(10) -0.30942(19) 0.41168(9) 0.0291(3) Uani d 1
H H10 0.2705 -0.4022 0.3642 0.035 Uiso calc 1
C C11 0.31265(9) -0.12381(19) 0.45757(9) 0.0247(3) Uani d 1
H H11 0.3747 -0.0897 0.4418 0.030 Uiso calc 1
N N4 0.15968(9) 0.09982(18) 0.61468(9) 0.0308(3) Uani d 1
H H1N4 0.2024(12) 0.210(2) 0.6510(12) 0.034(4) Uiso d 1
H H2N4 0.1081(13) 0.045(3) 0.6365(13) 0.045(4) Uiso d 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
C2 C1 C5 117.88(10)
C2 C1 N2 116.26(9)
C5 C1 N2 125.86(10)
N1 C2 C1 124.34(10)
N1 C2 H2 117.8
C1 C2 H2 117.8
C2 N1 C3 116.94(9)
N1 C3 C4 122.94(10)
N1 C3 H3 118.5
C4 C3 H3 118.5
C5 C4 C3 119.55(10)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C1 118.35(10)
C4 C5 H5 120.8
C1 C5 H5 120.8
N3 N2 C1 113.14(9)
N2 N3 C6 117.34(9)
N3 C6 C11 113.80(9)
N3 C6 C7 126.78(10)
C11 C6 C7 119.42(10)
N4 C7 C8 119.78(10)
N4 C7 C6 122.88(10)
C8 C7 C6 117.34(10)
C9 C8 C7 121.61(10)
C9 C8 H8 119.2
C7 C8 H8 119.2
C8 C9 C10 120.92(10)
C8 C9 H9 119.5
C10 C9 H9 119.5
C11 C10 C9 118.89(10)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C6 121.81(10)
C10 C11 H11 119.1
C6 C11 H11 119.1
C7 N4 H1N4 119.2(9)
C7 N4 H2N4 117.8(10)
H1N4 N4 H2N4 119.8(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3895(15)
C1 C5 1.3959(14)
C1 N2 1.4186(13)
C2 N1 1.3350(14)
C2 H2 0.9500
N1 C3 1.3397(13)
C3 C4 1.3892(15)
C3 H3 0.9500
C4 C5 1.3781(15)
C4 H4 0.9500
C5 H5 0.9500
N2 N3 1.2738(12)
N3 C6 1.3958(13)
C6 C11 1.4094(15)
C6 C7 1.4283(14)
C7 N4 1.3484(15)
C7 C8 1.4148(15)
C8 C9 1.3716(17)
C8 H8 0.9500
C9 C10 1.4035(17)
C9 H9 0.9500
C10 C11 1.3703(16)
C10 H10 0.9500
C11 H11 0.9500
N4 H1N4 0.881(16)
N4 H2N4 0.904(16)
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
N4 H1N4 N2 . 0.881(16) 2.066(15) 2.6922(14) 127.3(12)
N4 H2N4 N1 2_546 0.904(16) 2.163(16) 3.0274(14) 159.7(14)
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
C5 C1 C2 N1 0.57(16)
N2 C1 C2 N1 -178.53(10)
C1 C2 N1 C3 0.34(16)
C2 N1 C3 C4 -1.12(16)
N1 C3 C4 C5 0.96(17)
C3 C4 C5 C1 0.01(16)
C2 C1 C5 C4 -0.72(15)
N2 C1 C5 C4 178.28(10)
C2 C1 N2 N3 176.88(9)
C5 C1 N2 N3 -2.14(15)
C1 N2 N3 C6 -179.80(8)
N2 N3 C6 C11 -176.92(9)
N2 N3 C6 C7 1.96(15)
N3 C6 C7 N4 2.90(17)
C11 C6 C7 N4 -178.27(10)
N3 C6 C7 C8 -177.68(9)
C11 C6 C7 C8 1.15(15)
N4 C7 C8 C9 179.05(10)
C6 C7 C8 C9 -0.39(15)
C7 C8 C9 C10 -0.88(17)
C8 C9 C10 C11 1.36(17)
C9 C10 C11 C6 -0.56(17)
N3 C6 C11 C10 178.29(9)
C7 C6 C11 C10 -0.69(16)
C1 N2 N3 C6 -179.80(8)

_cod_database_fobs_code 2242544
