#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221238.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_2221238
loop_
_publ_author_name
'Natarajan, S.'
'Rajesh, K.'
'Vijayakumar, V.'
'Suresh, J.'
'Lakshman, P. L. Nilantha'
_publ_section_title
;
 4-Azido-2-chloro-6-methylquinoline
;
_journal_coeditor_code           AT2729
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o671
_journal_paper_doi               10.1107/S1600536809007041
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H7 Cl N4'
_chemical_formula_moiety         'C10 H7 Cl N4'
_chemical_formula_sum            'C10 H7 Cl N4'
_chemical_formula_weight         218.65
_chemical_name_systematic
;
4-Azido-2-chloro-6-methylquinoline
;
_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                75.694(7)
_cell_angle_beta                 82.147(8)
_cell_angle_gamma                76.532(7)
_cell_formula_units_Z            2
_cell_length_a                   6.9517(4)
_cell_length_b                   7.6078(6)
_cell_length_c                   10.0191(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     497.57(7)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius MACH-3'
_diffrn_measurement_method       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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2209
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.350
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0573
_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)+(0.1143P)²+0.0878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1798
_reflns_number_gt                1206
_reflns_number_total             1743
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2729.cif
_cod_data_source_block           I
_cod_database_code               2221238
_cod_database_fobs_code          2221238
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1775(5) 0.7084(4) 0.2969(3) 0.0365(8) Uani d . 1 . .
C C2 0.2459(4) 0.5180(3) 0.3035(3) 0.0334(7) Uani d . 1 . .
H H2 0.2656 0.4702 0.2246 0.040 Uiso calc R 1 . .
C C3 0.2820(4) 0.4060(3) 0.4303(3) 0.0294(7) Uani d . 1 . .
C C4 0.2518(4) 0.4825(4) 0.5495(3) 0.0291(7) Uani d . 1 . .
C C5 0.1836(4) 0.6769(4) 0.5274(3) 0.0328(7) Uani d . 1 . .
C C6 0.1508(5) 0.7579(4) 0.6436(3) 0.0432(8) Uani d . 1 . .
H H6 0.1047 0.8853 0.6320 0.052 Uiso calc R 1 . .
C C7 0.1857(5) 0.6525(4) 0.7709(3) 0.0448(9) Uani d . 1 . .
H H7 0.1636 0.7094 0.8454 0.054 Uiso calc R 1 . .
C C8 0.2548(5) 0.4583(5) 0.7950(3) 0.0407(8) Uani d . 1 . .
C C9 0.2849(4) 0.3774(4) 0.6839(3) 0.0354(7) Uani d . 1 . .
H H9 0.3283 0.2495 0.6978 0.043 Uiso calc R 1 . .
C C10 0.2945(6) 0.3461(6) 0.9386(3) 0.0581(10) Uani d . 1 . .
H H10A 0.1764 0.3662 0.9996 0.087 Uiso calc R 1 . .
H H10B 0.3994 0.3836 0.9706 0.087 Uiso calc R 1 . .
H H10C 0.3331 0.2169 0.9371 0.087 Uiso calc R 1 . .
Cl Cl1 0.13068(16) 0.85050(11) 0.13412(9) 0.0604(4) Uani d . 1 . .
N N1 0.1475(4) 0.7888(3) 0.4003(3) 0.0395(7) Uani d . 1 . .
N N2 0.3501(4) 0.2108(3) 0.4540(3) 0.0396(7) Uani d . 1 . .
N N3 0.3912(4) 0.1499(3) 0.3461(3) 0.0418(7) Uani d . 1 . .
N N4 0.4337(5) 0.0798(4) 0.2571(3) 0.0614(10) Uani 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 126.1(3) ?
N1 C1 Cl1 . . 117.0(2) ?
C2 C1 Cl1 . . 116.9(2) ?
C3 C2 C1 . . 117.2(2) ?
C3 C2 H2 . . 121.4 ?
C1 C2 H2 . . 121.4 ?
C2 C3 N2 . . 124.0(2) ?
C2 C3 C4 . . 120.3(2) ?
N2 C3 C4 . . 115.7(2) ?
C9 C4 C5 . . 119.6(2) ?
C9 C4 C3 . . 124.1(2) ?
C5 C4 C3 . . 116.3(3) ?
N1 C5 C4 . . 123.2(2) ?
N1 C5 C6 . . 118.8(2) ?
C4 C5 C6 . . 117.9(3) ?
C7 C6 C5 . . 120.7(3) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 122.2(3) ?
C6 C7 H7 . . 118.9 ?
C8 C7 H7 . . 118.9 ?
C9 C8 C7 . . 117.8(3) ?
C9 C8 C10 . . 121.7(3) ?
C7 C8 C10 . . 120.5(3) ?
C8 C9 C4 . . 121.8(3) ?
C8 C9 H9 . . 119.1 ?
C4 C9 H9 . . 119.1 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C1 N1 C5 . . 116.7(2) ?
N3 N2 C3 . . 114.1(2) ?
N4 N3 N2 . . 173.6(3) ?
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
C1 N1 . 1.298(4) ?
C1 C2 . 1.403(4) ?
C1 Cl1 . 1.745(3) ?
C2 C3 . 1.362(4) ?
C2 H2 . 0.9300 ?
C3 N2 . 1.419(3) ?
C3 C4 . 1.424(3) ?
C4 C9 . 1.404(4) ?
C4 C5 . 1.415(4) ?
C5 N1 . 1.364(4) ?
C5 C6 . 1.416(4) ?
C6 C7 . 1.348(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.413(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.371(4) ?
C8 C10 . 1.505(5) ?
C9 H9 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
N2 N3 . 1.251(3) ?
N3 N4 . 1.121(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
N1 C1 C2 C3 . . . . 0.9(5) ?
Cl1 C1 C2 C3 . . . . -179.7(2) ?
C1 C2 C3 N2 . . . . 179.5(3) ?
C1 C2 C3 C4 . . . . -0.4(4) ?
C2 C3 C4 C9 . . . . 179.8(3) ?
N2 C3 C4 C9 . . . . -0.1(4) ?
C2 C3 C4 C5 . . . . 0.0(4) ?
N2 C3 C4 C5 . . . . -179.9(3) ?
C9 C4 C5 N1 . . . . -179.9(3) ?
C3 C4 C5 N1 . . . . 0.0(4) ?
C9 C4 C5 C6 . . . . -0.1(4) ?
C3 C4 C5 C6 . . . . 179.7(3) ?
N1 C5 C6 C7 . . . . -179.6(3) ?
C4 C5 C6 C7 . . . . 0.7(5) ?
C5 C6 C7 C8 . . . . -0.4(5) ?
C6 C7 C8 C9 . . . . -0.5(5) ?
C6 C7 C8 C10 . . . . 179.2(3) ?
C7 C8 C9 C4 . . . . 1.0(5) ?
C10 C8 C9 C4 . . . . -178.6(3) ?
C5 C4 C9 C8 . . . . -0.7(4) ?
C3 C4 C9 C8 . . . . 179.5(3) ?
C2 C1 N1 C5 . . . . -0.9(5) ?
Cl1 C1 N1 C5 . . . . 179.7(2) ?
C4 C5 N1 C1 . . . . 0.4(5) ?
C6 C5 N1 C1 . . . . -179.3(3) ?
C2 C3 N2 N3 . . . . 5.8(4) ?
C4 C3 N2 N3 . . . . -174.3(3) ?
C3 N2 N3 N4 . . . . 176(3) ?
