##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.1
_journal_date_recd_electronic     2008-06-13
_journal_date_accepted     2008-07-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      9
_journal_page_first     o502
_journal_page_last     o504
_journal_paper_category     FO
_journal_coeditor_code     SK3246
_publ_contact_author_name     'Novaković, Slađana B.'
_publ_contact_author_address
;
'Vinča' Institute of Nuclear Sciences
Laboratory of Theoretical Physics and Condensed Matter Physics
PO Box 522
11001 Belgrade
Republic of Serbia
;
_publ_contact_author_email     snovak@vin.bg.ac.yu
_publ_contact_author_fax     '381 11 8065829'
_publ_contact_author_phone     '381 11 8065828'
_publ_section_title
;
Weak intermolecular interactions in
11-chloro-2,3,4,5-tetrahydro-1H-cyclohepta[b]quinoline
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Novaković, Slađana B.' .
;
'Vinča' Institute of Nuclear Sciences
Laboratory of Theoretical Physics and Condensed Matter Physics
PO Box 522
11001 Belgrade
Republic of Serbia
;
    'Vitorović-Todorović, Maja D.'
;
Current adress: Faculty of Chemistry, University of Belgrade,
Studentski Trg 12-16, 11000 Belgrade, Republic of Serbia.
;
;Military-Technical Institute,
Ratka  Resanovića  1,
11000 Belgrade,
Republic of Serbia
;
    'Bogdanović, Goran A.' .
;
'Vinča' Institute of Nuclear Sciences
Laboratory of Theoretical Physics and Condensed Matter Physics
PO Box 522
11001 Belgrade
Republic of Serbia
;
    'Drakulić, Branko J.' .
;
Department  of  Chemistry--IChTM, University of Belgrade,
Njegoševa 12, 11000 Belgrade, Republic of Serbia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
11-chloro-2,3,4,5-tetrahydro-1H-cyclohepta[b]quinoline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 Cl N'
_chemical_formula_sum     'C14 H14 Cl N'
_chemical_formula_iupac     'C14 H14 Cl N'
_chemical_formula_weight     231.71
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.213(2)
_cell_length_b     8.727(2)
_cell_length_c     9.042(3)
_cell_angle_alpha     90.50(2)
_cell_angle_beta     95.32(3)
_cell_angle_gamma     113.86(3)
_cell_volume     589.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     11.46
_cell_measurement_theta_max     15.20
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.56
_exptl_crystal_size_mid     0.44
_exptl_crystal_size_min     0.42
_exptl_crystal_density_diffrn     1.306
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     244
_exptl_absorpt_coefficient_mu     0.294
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
Melting point was obtained on Buchi apparatus in open capillary tube and is
 uncorrected. NMR spectra were recorded on Varian Gemini 200 (200/50 MHz)
 spectrometer in CDCl3, using tetramethylsilane (TMS) as internal standard.
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2548
_diffrn_reflns_av_R_equivalents     0.0112
_diffrn_reflns_av_sigmaI/netI     0.0121
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     25.97
_diffrn_reflns_theta_full     25.97
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     3
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2309
_reflns_number_gt     2003
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0422
_refine_ls_R_factor_gt     0.0368
_refine_ls_wR_factor_gt     0.1043
_refine_ls_wR_factor_ref     0.1067
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     2309
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0537P)²+0.133P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.185
_refine_diff_density_min     -0.198
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                                'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
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 0.6756(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_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
    C1 0.0615(10) 0.0509(9) 0.0416(8) 0.0232(8) 0.0118(7) 0.0098(7)
    C2 0.0713(11) 0.0645(11) 0.0413(9) 0.0292(9) -0.0028(8) 0.0058(8)
    C3 0.0520(10) 0.0675(11) 0.0575(10) 0.0235(9) -0.0065(8) 0.0015(8)
    C4 0.0433(8) 0.0588(10) 0.0548(9) 0.0177(7) 0.0070(7) 0.0075(7)
    C4A 0.0432(8) 0.0376(7) 0.0428(8) 0.0173(6) 0.0077(6) 0.0068(6)
    C5A 0.0493(8) 0.0341(7) 0.0418(8) 0.0176(6) 0.0047(6) 0.0057(6)
    C6 0.0658(10) 0.0544(9) 0.0411(8) 0.0262(8) 0.0042(7) 0.0042(7)
    C7 0.0870(13) 0.0565(10) 0.0489(10) 0.0297(10) -0.0022(9) 0.0138(8)
    C8 0.0837(13) 0.0572(10) 0.0618(11) 0.0381(10) -0.0205(10) -0.0007(8)
    C9 0.0568(10) 0.0638(11) 0.0726(12) 0.0328(9) -0.0101(9) -0.0014(9)
    C10 0.0458(9) 0.0519(9) 0.0687(11) 0.0132(7) -0.0033(8) 0.0087(8)
    C10A 0.0430(8) 0.0339(7) 0.0499(8) 0.0152(6) 0.0034(6) 0.0064(6)
    C11 0.0424(8) 0.0363(7) 0.0507(8) 0.0159(6) 0.0139(6) 0.0106(6)
    C11A 0.0475(8) 0.0338(7) 0.0407(7) 0.0184(6) 0.0087(6) 0.0071(5)
    Cl1 0.0522(3) 0.0795(3) 0.0717(3) 0.0225(2) 0.0281(2) 0.0234(2)
    N5 0.0456(7) 0.0440(7) 0.0417(7) 0.0175(6) 0.0092(5) 0.0090(5)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 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_
    _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
    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) ?
