#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/86/2218689.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_2218689
loop_
_publ_author_name
'Meneghetti, Fiorella'
'Bombieri, Gabriella'
'Tonelli, Michele'
_publ_section_title
;
 3-(4-Chlorophenyldiazenyl)-1-methyl-1,4,5,6-tetrahydropyridine
;
_journal_coeditor_code           FJ2123
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1297
_journal_paper_doi               10.1107/S1600536808018217
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H14 Cl N3'
_chemical_formula_moiety         'C12 H14 Cl N3'
_chemical_formula_sum            'C12 H14 Cl N3'
_chemical_formula_weight         235.71
_chemical_name_systematic
;
3-(4-Chlorophenyldiazenyl)-1-methyl-1,4,5,6-tetrahydropyridine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.590(10)
_cell_angle_beta                 78.450(10)
_cell_angle_gamma                87.01(2)
_cell_formula_units_Z            2
_cell_length_a                   6.251(2)
_cell_length_b                   8.483(3)
_cell_length_c                   11.824(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      9
_cell_volume                     599.9(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω/2θ'
_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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3028
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         3.91
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.495
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0613
_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)+(0.117P)²+0.0064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                1803
_reflns_number_total             2893
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2123.cif
_cod_data_source_block           I
_cod_database_code               2218689
_cod_database_fobs_code          2218689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 -0.62912(9) 0.77463(8) 0.36467(7) 0.0818(3) Uani d . 1
N N1 0.1713(3) 0.4296(2) 0.18348(17) 0.0586(5) Uani d . 1
N N2 0.2811(3) 0.3554(2) 0.26078(17) 0.0577(5) Uani d . 1
N N3 0.7609(3) 0.1111(2) 0.27394(19) 0.0677(6) Uani d . 1
C C1 -0.3925(3) 0.6722(2) 0.3139(2) 0.0592(6) Uani d . 1
C C2 -0.0779(3) 0.5151(3) 0.3523(2) 0.0630(6) Uani d . 1
H H2 0.0076 0.4626 0.4052 0.076 Uiso calc R 1
C C3 -0.3383(4) 0.6673(3) 0.1976(2) 0.0670(6) Uani d . 1
H H3 -0.4274 0.7175 0.1459 0.080 Uiso calc R 1
C C4 -0.1496(4) 0.5873(3) 0.1563(2) 0.0631(6) Uani d . 1
H H4 -0.1117 0.5847 0.0766 0.076 Uiso calc R 1
C C5 -0.0155(3) 0.5106(2) 0.2336(2) 0.0562(5) Uani d . 1
C C6 -0.2651(3) 0.5964(3) 0.3933(2) 0.0645(6) Uani d . 1
H H6 -0.3047 0.6002 0.4728 0.077 Uiso calc R 1
C C7 0.4609(3) 0.2732(2) 0.2171(2) 0.0585(6) Uani d . 1
C C8 0.5789(3) 0.1961(3) 0.2987(2) 0.0600(6) Uani d . 1
H H8 0.5286 0.2036 0.3769 0.072 Uiso calc R 1
C C9 0.5288(4) 0.2646(3) 0.0908(2) 0.0698(6) Uani d . 1
H H9A 0.6038 0.3629 0.0471 0.084 Uiso calc R 1
H H9B 0.4007 0.2552 0.0581 0.084 Uiso calc R 1
C C10 0.6793(5) 0.1200(4) 0.0783(3) 0.0841(8) Uani d . 1
H H10A 0.5929 0.0225 0.1014 0.101 Uiso calc R 1
H H10B 0.7492 0.1302 -0.0039 0.101 Uiso calc R 1
C C11 0.8530(4) 0.1044(3) 0.1526(3) 0.0780(8) Uani d . 1
H H11A 0.9306 0.0027 0.1504 0.094 Uiso calc R 1
H H11B 0.9574 0.1908 0.1194 0.094 Uiso calc R 1
C C12 0.8856(4) 0.0404(3) 0.3635(3) 0.0819(8) Uani d . 1
H H12A 0.8063 0.0531 0.4394 0.123 Uiso calc R 1
H H12B 1.0237 0.0936 0.3467 0.123 Uiso calc R 1
H H12C 0.9096 -0.0724 0.3637 0.123 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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C5 112.81(19)
N1 N2 C7 115.1(2)
C8 N3 C11 119.8(2)
C8 N3 C12 121.7(2)
C11 N3 C12 118.06(19)
C3 C1 C6 121.5(2)
C3 C1 Cl1 119.29(18)
C6 C1 Cl1 119.2(2)
C6 C2 C5 121.1(2)
C6 C2 H2 119.5
C5 C2 H2 119.5
C1 C3 C4 119.7(2)
C1 C3 H3 120.2
C4 C3 H3 120.2
C3 C4 C5 120.5(2)
C3 C4 H4 119.7
C5 C4 H4 119.7
C2 C5 C4 118.33(19)
C2 C5 N1 125.3(2)
C4 C5 N1 116.3(2)
C2 C6 C1 118.9(2)
C2 C6 H6 120.6
C1 C6 H6 120.6
N2 C7 C8 115.1(2)
N2 C7 C9 124.0(2)
C8 C7 C9 120.91(19)
N3 C8 C7 124.5(2)
N3 C8 H8 117.8
C7 C8 H8 117.8
C7 C9 C10 110.2(2)
C7 C9 H9A 109.6
C10 C9 H9A 109.6
C7 C9 H9B 109.6
C10 C9 H9B 109.6
H9A C9 H9B 108.1
C11 C10 C9 112.6(2)
C11 C10 H10A 109.1
C9 C10 H10A 109.1
C11 C10 H10B 109.1
C9 C10 H10B 109.1
H10A C10 H10B 107.8
N3 C11 C10 111.89(19)
N3 C11 H11A 109.2
C10 C11 H11A 109.2
N3 C11 H11B 109.2
C10 C11 H11B 109.2
H11A C11 H11B 107.9
N3 C12 H12A 109.5
N3 C12 H12B 109.5
H12A C12 H12B 109.5
N3 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.743(2)
N1 N2 1.289(3)
N1 C5 1.414(3)
N2 C7 1.363(3)
N3 C8 1.331(3)
N3 C11 1.447(3)
N3 C12 1.448(3)
C1 C3 1.358(4)
C1 C6 1.383(3)
C2 C6 1.383(3)
C2 C5 1.388(4)
C2 H2 0.9300
C3 C4 1.385(3)
C3 H3 0.9300
C4 C5 1.398(3)
C4 H4 0.9300
C6 H6 0.9300
C7 C8 1.366(3)
C7 C9 1.484(4)
C8 H8 0.9300
C9 C10 1.521(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.512(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24696766
