#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/32/2203246.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_2203246
loop_
_publ_author_name
'Beghidja, Adel'
'Benboudiaf, Ali'
'Beghidja, Chahrazed'
'Welter, Richard'
_publ_section_title
;
 2-Chloro-3-chloromethylbenzo[h]quinoline
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o228
_journal_page_last               o229
_journal_paper_doi               10.1107/S1600536804000650
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C14 H9 Cl2 N'
_chemical_formula_moiety         'C14 H9 Cl2 N'
_chemical_formula_sum            'C14 H9 Cl2 N'
_chemical_formula_weight         262.12
_chemical_name_systematic
;
2-Chloro-3-chloromethylbenzo[h]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                79.21(10)
_cell_angle_beta                 76.19(10)
_cell_angle_gamma                85.84(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9211(10)
_cell_length_b                   8.3176(10)
_cell_length_c                   10.6480(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.49
_cell_volume                     584.5(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON98 (Spek, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/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  0.0849
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3498
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.351
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0601
_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)+(0.0861P)²+0.6126P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.2095
_reflns_number_gt                2022
_reflns_number_total             3288
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6143.cif
_cod_data_source_block           I
_cod_database_code               2203246
_cod_database_fobs_code          2203246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_occupancy
_atom_site_type_symbol
Cl1 0.28019(15) 0.70060(15) 0.16077(9) 0.0591(3) Uani d 1 Cl
Cl2 0.82046(18) 0.68971(13) -0.00730(9) 0.0620(3) Uani d 1 Cl
N1 0.3487(4) 0.7533(3) 0.3781(2) 0.0354(6) Uani d 1 N
C12 0.3725(5) 0.8215(4) 0.5841(3) 0.0343(6) Uani d 1 C
C13 0.4594(4) 0.7496(4) 0.4678(3) 0.0323(6) Uani d 1 C
C1 0.4295(5) 0.6894(4) 0.2745(3) 0.0370(7) Uani d 1 C
C4 0.6520(5) 0.6802(4) 0.4515(3) 0.0371(7) Uani d 1 C
C2 0.6185(5) 0.6131(4) 0.2473(3) 0.0376(7) Uani d 1 C
C7 0.4866(5) 0.8197(4) 0.6778(3) 0.0412(7) Uani d 1 C
C3 0.7278(5) 0.6109(4) 0.3398(3) 0.0399(7) Uani d 1 C
H3 0.8547 0.5623 0.3275 0.048 Uiso calc 1 H
C11 0.1802(5) 0.8921(4) 0.6047(3) 0.0438(7) Uani d 1 C
H11 0.1041 0.8931 0.5434 0.053 Uiso calc 1 H
C6 0.6826(6) 0.7478(5) 0.6567(3) 0.0495(9) Uani d 1 C
H6 0.7574 0.7471 0.7187 0.059 Uiso calc 1 H
C8 0.4022(7) 0.8905(5) 0.7894(3) 0.0530(10) Uani d 1 C
H8 0.4751 0.8906 0.8523 0.064 Uiso calc 1 H
C14 0.7003(6) 0.5386(5) 0.1273(4) 0.0495(8) Uani d 1 C
H14A 0.5931 0.4917 0.1030 0.059 Uiso calc 1 H
H14B 0.7954 0.4512 0.1462 0.059 Uiso calc 1 H
C9 0.2150(7) 0.9588(5) 0.8064(4) 0.0578(11) Uani d 1 C
H9 0.1619 1.0053 0.8806 0.069 Uiso calc 1 H
C5 0.7623(5) 0.6809(5) 0.5490(4) 0.0488(8) Uani d 1 C
H5 0.8903 0.6347 0.5381 0.059 Uiso calc 1 H
C10 0.1032(6) 0.9600(5) 0.7149(4) 0.0558(10) Uani d 1 C
H10 -0.0246 1.0069 0.7279 0.067 Uiso calc 1 H
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
_geom_angle_publ_flag
C1 N1 C13 117.1(3) yes
C11 C12 C7 119.5(3) no
C11 C12 C13 121.9(3) no
C7 C12 C13 118.7(3) no
N1 C13 C4 122.2(3) yes
N1 C13 C12 118.0(3) yes
C4 C13 C12 119.8(3) no
N1 C1 C2 126.6(3) yes
N1 C1 Cl1 115.0(2) yes
C2 C1 Cl1 118.4(2) yes
C3 C4 C13 117.8(3) no
C3 C4 C5 122.5(3) no
C13 C4 C5 119.7(3) no
C3 C2 C1 115.1(3) no
C3 C2 C14 121.0(3) no
C1 C2 C14 123.8(3) no
C8 C7 C12 118.3(4) no
C8 C7 C6 122.2(3) no
C12 C7 C6 119.5(3) no
C2 C3 C4 121.1(3) no
C10 C11 C12 120.4(3) no
C5 C6 C7 121.6(3) no
C9 C8 C7 120.8(3) no
C2 C14 Cl2 110.8(3) no
C8 C9 C10 120.9(3) no
C6 C5 C4 120.7(3) no
C11 C10 C9 120.1(4) no
C2 C3 H3 119.3 no
C4 C3 H3 119.3 no
C10 C11 H11 119.7 no
C12 C11 H11 119.7 no
C5 C6 H6 119.2 no
C7 C6 H6 119.2 no
C9 C8 H8 119.6 no
C7 C8 H8 119.6 no
C2 C14 H14A 109.6 no
Cl2 C14 H14A 109.6 no
C2 C14 H14B 109.6 no
Cl2 C14 H14B 109.6 no
H14A C14 H14B 108.1 no
C8 C9 H9 119.4 no
C10 C9 H9 119.4 no
C6 C5 H5 119.6 no
C4 C5 H5 119.6 no
C11 C10 H10 120.1 no
C9 C10 H10 120.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.756(3) yes
Cl2 C14 1.799(4) yes
N1 C1 1.302(4) yes
N1 C13 1.354(4) yes
C12 C11 1.400(5) no
C12 C7 1.410(4) no
C12 C13 1.457(4) no
C13 C4 1.398(4) no
C1 C2 1.402(5) no
C4 C3 1.392(4) no
C4 C5 1.428(5) no
C2 C3 1.375(5) no
C2 C14 1.496(4) no
C7 C8 1.407(5) no
C7 C6 1.427(6) no
C11 C10 1.373(5) no
C6 C5 1.350(5) no
C8 C9 1.361(7) no
C9 C10 1.379(6) no
C3 H3 0.9300 no
C11 H11 0.9300 no
C6 H6 0.9300 no
C8 H8 0.9300 no
C14 H14A 0.9700 no
C14 H14B 0.9700 no
C9 H9 0.9300 no
C5 H5 0.9300 no
C10 H10 0.9300 no
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
C1 N1 C13 C4 -0.3(4)
C1 N1 C13 C12 179.5(3)
C11 C12 C13 N1 0.3(4)
C7 C12 C13 N1 -179.5(3)
C11 C12 C13 C4 -179.9(3)
C7 C12 C13 C4 0.3(4)
C13 N1 C1 C2 1.8(5)
C13 N1 C1 Cl1 -179.1(2)
N1 C13 C4 C3 -1.1(5)
C12 C13 C4 C3 179.1(3)
N1 C13 C4 C5 179.6(3)
C12 C13 C4 C5 -0.2(5)
N1 C1 C2 C3 -1.7(5)
Cl1 C1 C2 C3 179.2(2)
N1 C1 C2 C14 178.5(3)
Cl1 C1 C2 C14 -0.7(5)
C11 C12 C7 C8 -0.3(5)
C13 C12 C7 C8 179.5(3)
C11 C12 C7 C6 -180.0(3)
C13 C12 C7 C6 -0.1(4)
C1 C2 C3 C4 0.2(5)
C14 C2 C3 C4 180.0(3)
C13 C4 C3 C2 1.1(5)
C5 C4 C3 C2 -179.6(3)
C7 C12 C11 C10 0.4(5)
C13 C12 C11 C10 -179.5(3)
C8 C7 C6 C5 -179.7(4)
C12 C7 C6 C5 -0.1(5)
C12 C7 C8 C9 0.1(5)
C6 C7 C8 C9 179.7(3)
C3 C2 C14 Cl2 -93.2(4)
C1 C2 C14 Cl2 86.6(4)
C7 C8 C9 C10 0.2(6)
C7 C6 C5 C4 0.2(6)
C3 C4 C5 C6 -179.3(3)
C13 C4 C5 C6 0.0(5)
C12 C11 C10 C9 -0.1(6)
C8 C9 C10 C11 -0.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131085
