#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/67/2016777.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_2016777
loop_
_publ_author_name
'Novaković, Sladjana B.'
'Vitorović-Todorović, Maja D.'
'Bogdanović, Goran A.'
'Drakulić, Branko J.'
_publ_section_title
;
 Weak intermolecular interactions in
 11-chloro-2,3,4,5-tetrahydro-1H-cyclohepta[b]quinoline
;
_journal_coeditor_code           SK3246
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o502
_journal_page_last               o504
_journal_paper_doi               10.1107/S0108270108022221
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H14 Cl N'
_chemical_formula_moiety         'C14 H14 Cl N'
_chemical_formula_sum            'C14 H14 Cl N'
_chemical_formula_weight         231.71
_chemical_name_systematic
;
11-chloro-2,3,4,5-tetrahydro-1H-cyclohepta[b]quinoline
;
_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                90.50(2)
_cell_angle_beta                 95.32(3)
_cell_angle_gamma                113.86(3)
_cell_formula_units_Z            2
_cell_length_a                   8.213(2)
_cell_length_b                   8.727(2)
_cell_length_c                   9.042(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.20
_cell_measurement_theta_min      11.46
_cell_volume                     589.4(3)
_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 (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
_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  'Enraf--Nonius CAD-4'
_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  0.0112
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2548
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0368
_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)+(0.0537P)²+0.133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                2003
_reflns_number_total             2309
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3246.cif
_cod_data_source_block           I
_cod_database_code               2016777
_cod_database_fobs_code          2016777
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
C C1 0.6756(2) 0.2078(2) 0.37705(18) 0.0508(4) Uani d . 1
H H1 0.5854 0.1643 0.4395 0.061 Uiso calc R 1
C C2 0.8504(3) 0.2616(2) 0.43426(19) 0.0591(4) Uani d . 1
H H2 0.8782 0.2527 0.5350 0.071 Uiso calc R 1
C C3 0.9886(2) 0.3302(2) 0.3424(2) 0.0601(4) Uani d . 1
H H3 1.1074 0.3681 0.3828 0.072 Uiso calc R 1
C C4 0.9495(2) 0.3415(2) 0.19432(19) 0.0531(4) Uani d . 1
H H4 1.0420 0.3877 0.1344 0.064 Uiso calc R 1
C C4A 0.76991(19) 0.28386(18) 0.13073(16) 0.0407(3) Uani d . 1
C C5A 0.5718(2) 0.24434(17) -0.07907(16) 0.0415(3) Uani d . 1
C C6 0.5489(2) 0.2602(2) -0.24480(17) 0.0533(4) Uani d . 1
H H6A 0.4697 0.1514 -0.2908 0.064 Uiso calc R 1
H H6B 0.6642 0.2917 -0.2826 0.064 Uiso calc R 1
C C7 0.4727(3) 0.3889(2) -0.2919(2) 0.0645(5) Uani d . 1
H H7A 0.5307 0.4882 -0.2256 0.077 Uiso calc R 1
H H7B 0.5033 0.4217 -0.3913 0.077 Uiso calc R 1
C C8 0.2719(3) 0.3287(2) -0.2915(2) 0.0664(5) Uani d . 1
H H8B 0.2139 0.2314 -0.3602 0.080 Uiso calc R 1
H H8A 0.2370 0.4161 -0.3287 0.080 Uiso calc R 1
C C9 0.2027(3) 0.2822(2) -0.1411(2) 0.0629(5) Uani d . 1
H H9B 0.0753 0.2552 -0.1510 0.075 Uiso calc R 1
H H9A 0.2609 0.3790 -0.0721 0.075 Uiso calc R 1
C C10 0.2338(2) 0.1327(2) -0.0748(2) 0.0582(4) Uani d . 1
H H10B 0.1470 0.0817 -0.0047 0.070 Uiso calc R 1
H H10A 0.2128 0.0493 -0.1542 0.070 Uiso calc R 1
C C10A 0.41920(19) 0.17982(17) 0.00316(17) 0.0425(3) Uani d . 1
C C11 0.4537(2) 0.16740(18) 0.15295(17) 0.0425(3) Uani d . 1
C C11A 0.6304(2) 0.21762(17) 0.22388(16) 0.0398(3) Uani d . 1
Cl Cl1 0.27868(6) 0.09149(6) 0.26571(5) 0.06761(19) Uani d . 1
N N5 0.73866(16) 0.29468(15) -0.01926(14) 0.0437(3) 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
C2 C1 C11A 120.61(15)
C2 C1 H1 119.7
C11A C1 H1 119.7
C1 C2 C3 120.58(15)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 120.24(16)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C4A 120.70(15)
C3 C4 H4 119.7
C4A C4 H4 119.7
N5 C4A C4 118.09(13)
N5 C4A C11A 122.82(13)
C4 C4A C11A 119.09(14)
N5 C5A C10A 124.20(13)
N5 C5A C6 115.23(14)
C10A C5A C6 120.57(14)
C5A C6 C7 114.31(14)
C5A C6 H6A 108.7
C7 C6 H6A 108.7
C5A C6 H6B 108.7
C7 C6 H6B 108.7
H6A C6 H6B 107.6
C8 C7 C6 115.12(15)
C8 C7 H7A 108.5
C6 C7 H7A 108.5
C8 C7 H7B 108.5
C6 C7 H7B 108.5
H7A C7 H7B 107.5
C7 C8 C9 115.18(15)
C7 C8 H8B 108.5
C9 C8 H8B 108.5
C7 C8 H8A 108.5
C9 C8 H8A 108.5
H8B C8 H8A 107.5
C8 C9 C10 114.14(16)
C8 C9 H9B 108.7
C10 C9 H9B 108.7
C8 C9 H9A 108.7
C10 C9 H9A 108.7
H9B C9 H9A 107.6
C10A C10 C9 113.83(14)
C10A C10 H10B 108.8
C9 C10 H10B 108.8
C10A C10 H10A 108.8
C9 C10 H10A 108.8
H10B C10 H10A 107.7
C11 C10A C5A 116.21(13)
C11 C10A C10 123.68(14)
C5A C10A C10 120.10(14)
C10A C11 C11A 122.32(13)
C10A C11 Cl1 120.60(12)
C11A C11 Cl1 117.07(11)
C1 C11A C4A 118.76(14)
C1 C11A C11 125.36(14)
C4A C11A C11 115.88(13)
C5A N5 C4A 118.53(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.364(2) yes
C1 C11A 1.413(2) yes
C1 H1 0.9300 .
C2 C3 1.405(3) yes
C2 H2 0.9300 ?
C3 C4 1.361(2) yes
C3 H3 0.9300 ?
C4 C4A 1.413(2) yes
C4 H4 0.9300 ?
C4A N5 1.3680(19) yes
C4A C11A 1.417(2) yes
C5A N5 1.3169(19) yes
C5A C10A 1.432(2) yes
C5A C6 1.508(2) yes
C6 C7 1.537(2) yes
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.515(3) yes
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.518(3) yes
C8 H8B 0.9700 ?
C8 H8A 0.9700 ?
C9 C10 1.543(2) yes
C9 H9B 0.9700 ?
C9 H9A 0.9700 ?
C10 C10A 1.508(2) yes
C10 H10B 0.9700 ?
C10 H10A 0.9700 ?
C10A C11 1.372(2) yes
C11 C11A 1.420(2) yes
C11 Cl1 1.7485(15) yes
C8 H8A 0.9700 ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726272
