#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/25/2232591.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_2232591
loop_
_publ_author_name
'Thies, Steffen'
'Näther, Christian'
'Herges, Rainer'
_publ_section_title
;
 5-Chloro-2-(phenyldiazenyl)pyridine
;
_journal_coeditor_code           BT5703
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3298
_journal_paper_doi               10.1107/S1600536811047556
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H8 Cl N3'
_chemical_formula_moiety         'C11 H8 Cl N3'
_chemical_formula_sum            'C11 H8 Cl N3'
_chemical_formula_weight         217.65
_chemical_name_systematic
;
5-Chloro-2-(phenyldiazenyl)pyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.459(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1136(2)
_cell_length_b                   9.0940(4)
_cell_length_c                   18.6839(8)
_cell_measurement_reflns_used    23258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.22
_cell_measurement_theta_min      2.18
_cell_volume                     1038.43(7)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2008)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2008)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2008)'
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0126
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19329
_diffrn_reflns_theta_full        29.22
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.174
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0436
_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)+(0.0494P)²+0.1607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                2456
_reflns_number_total             2818
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bt5703.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232591
_cod_database_fobs_code          2232591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
Cl Cl1 0.82419(7) -0.02057(5) 0.37109(2) 0.07091(17) Uani d . 1 1
C C1 0.4709(2) 0.27818(16) 0.51393(7) 0.0521(3) Uani d . 1 1
C C2 0.4706(3) 0.12003(19) 0.42028(8) 0.0610(4) Uani d . 1 1
H H2 0.3950 0.0699 0.3840 0.073 Uiso calc R 1 1
N N1 0.3601(2) 0.20937(16) 0.46186(7) 0.0620(3) Uani d . 1 1
C C3 0.6925(2) 0.09777(16) 0.42821(7) 0.0529(3) Uani d . 1 1
C C4 0.8081(2) 0.17112(19) 0.48142(9) 0.0605(4) Uani d . 1 1
H H4 0.9585 0.1591 0.4872 0.073 Uiso calc R 1 1
C C5 0.6949(2) 0.26232(18) 0.52564(8) 0.0586(4) Uani d . 1 1
H H5 0.7666 0.3125 0.5627 0.070 Uiso calc R 1 1
N N2 0.3334(2) 0.37225(14) 0.55510(7) 0.0588(3) Uani d . 1 1
N N3 0.4247(2) 0.41302(15) 0.61134(7) 0.0593(3) Uani d . 1 1
C C6 0.2969(3) 0.51050(16) 0.65384(8) 0.0559(3) Uani d . 1 1
C C7 0.3993(3) 0.5565(2) 0.71665(9) 0.0685(4) Uani d . 1 1
H H7 0.5377 0.5211 0.7292 0.082 Uiso calc R 1 1
C C8 0.2973(4) 0.6544(2) 0.76071(9) 0.0773(5) Uani d . 1 1
H H8 0.3672 0.6861 0.8027 0.093 Uiso calc R 1 1
C C9 0.0916(4) 0.7056(2) 0.74256(10) 0.0778(5) Uani d . 1 1
H H9 0.0224 0.7721 0.7723 0.093 Uiso calc R 1 1
C C10 -0.0123(3) 0.6581(2) 0.68026(11) 0.0750(5) Uani d . 1 1
H H10 -0.1523 0.6919 0.6686 0.090 Uiso calc R 1 1
C C11 0.0890(3) 0.56153(19) 0.63543(9) 0.0626(4) Uani d . 1 1
H H11 0.0192 0.5307 0.5932 0.075 Uiso calc R 1 1
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
Cl1 0.0752(3) 0.0732(3) 0.0646(3) 0.0099(2) 0.00810(19) -0.00282(19)
C1 0.0511(7) 0.0541(7) 0.0511(7) -0.0032(6) -0.0005(6) 0.0062(6)
C2 0.0545(8) 0.0704(9) 0.0577(8) -0.0019(7) -0.0079(6) -0.0056(7)
N1 0.0487(6) 0.0749(8) 0.0619(7) 0.0003(6) -0.0077(5) -0.0061(6)
C3 0.0534(7) 0.0551(7) 0.0502(7) -0.0004(6) 0.0027(6) 0.0077(6)
C4 0.0429(7) 0.0727(9) 0.0658(9) -0.0039(6) -0.0015(6) 0.0023(7)
C5 0.0510(7) 0.0670(9) 0.0575(8) -0.0113(6) -0.0050(6) -0.0028(7)
N2 0.0553(7) 0.0622(7) 0.0587(7) -0.0034(6) -0.0047(5) 0.0004(6)
N3 0.0580(7) 0.0654(7) 0.0540(7) -0.0035(6) -0.0044(5) 0.0024(6)
C6 0.0605(8) 0.0544(8) 0.0529(7) -0.0063(6) 0.0053(6) 0.0058(6)
C7 0.0691(10) 0.0797(11) 0.0565(8) 0.0001(8) -0.0019(7) -0.0023(8)
C8 0.0968(14) 0.0797(12) 0.0554(9) -0.0021(10) 0.0015(9) -0.0046(8)
C9 0.1020(14) 0.0649(10) 0.0675(10) 0.0085(10) 0.0238(10) 0.0046(8)
C10 0.0705(10) 0.0715(11) 0.0835(12) 0.0104(8) 0.0104(9) 0.0137(9)
C11 0.0639(9) 0.0614(9) 0.0623(9) -0.0049(7) -0.0011(7) 0.0069(7)
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C5 123.29(15)
N1 C1 N2 112.26(13)
C5 C1 N2 124.44(13)
N1 C2 C3 123.00(14)
N1 C2 H2 118.5
C3 C2 H2 118.5
C2 N1 C1 117.49(13)
C2 C3 C4 119.51(14)
C2 C3 Cl1 119.90(12)
C4 C3 Cl1 120.59(12)
C5 C4 C3 118.09(14)
C5 C4 H4 121.0
C3 C4 H4 121.0
C4 C5 C1 118.60(14)
C4 C5 H5 120.7
C1 C5 H5 120.7
N3 N2 C1 112.15(13)
N2 N3 C6 114.60(13)
C7 C6 C11 120.09(15)
C7 C6 N3 114.62(14)
C11 C6 N3 125.27(14)
C8 C7 C6 120.23(17)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C9 119.86(18)
C7 C8 H8 120.1
C9 C8 H8 120.1
C8 C9 C10 120.02(18)
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 120.62(18)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C6 119.17(16)
C10 C11 H11 120.4
C6 C11 H11 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7288(15)
C1 N1 1.3278(19)
C1 C5 1.389(2)
C1 N2 1.436(2)
C2 N1 1.322(2)
C2 C3 1.376(2)
C2 H2 0.9300
C3 C4 1.377(2)
C4 C5 1.370(2)
C4 H4 0.9300
C5 H5 0.9300
N2 N3 1.2341(17)
N3 C6 1.435(2)
C6 C7 1.381(2)
C6 C11 1.388(2)
C7 C8 1.373(3)
C7 H7 0.9300
C8 C9 1.375(3)
C8 H8 0.9300
C9 C10 1.381(3)
C9 H9 0.9300
C10 C11 1.372(3)
C10 H10 0.9300
C11 H11 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26944406
