#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/67/2016706.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_2016706
loop_
_publ_author_name
'Sopková-de Oliveira Santos, Jana'
'Verhaeghe, Pierre'
'Lohier, Jean-François'
'Rathelot, Pascal'
'Vanelle, Patrice'
'Rault, Sylvain'
_publ_section_title
;
 Nitrated isomers of 2-(trichloromethyl)quinoline
;
_journal_coeditor_code           FA3148
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o441
_journal_page_last               o444
_journal_paper_doi               10.1107/S0108270108020374
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H5 Cl3 N2 O2'
_chemical_formula_moiety         'C10 H5 Cl3 N2 O2'
_chemical_formula_sum            'C10 H5 Cl3 N2 O2'
_chemical_formula_weight         291.51
_chemical_name_systematic
;
8-nitro-2-(trichloromethyl)quinoline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.693(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1941(14)
_cell_length_b                   5.5843(5)
_cell_length_c                   12.9620(12)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      40.52
_cell_measurement_theta_min      2.68
_cell_volume                     1099.33(17)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            42809
_diffrn_reflns_theta_full        39.44
_diffrn_reflns_theta_max         39.44
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'translucent pale brown'
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         6463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0322P)²+0.4692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                5214
_reflns_number_total             6463
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3148.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2016706
_cod_database_fobs_code          2016706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
N N1 0.25586(5) 0.13830(12) 0.38627(5) 0.01198(11) Uani d 1
C C2 0.19037(5) 0.04973(14) 0.43786(6) 0.01207(12) Uani d 1
C C3 0.17025(6) 0.11502(16) 0.53996(7) 0.01553(13) Uani d 1
H H3 0.1234(11) 0.042(3) 0.5734(13) 0.030(4) Uiso d 1
C C4 0.21938(6) 0.29098(16) 0.58703(7) 0.01604(14) Uani d 1
H H4 0.2074(11) 0.341(3) 0.6565(12) 0.028(4) Uiso d 1
C C4A 0.28789(5) 0.40223(15) 0.53319(6) 0.01318(12) Uani d 1
C C5 0.33666(6) 0.59993(16) 0.57266(7) 0.01620(14) Uani d 1
H H5 0.3260(11) 0.652(3) 0.6398(12) 0.026(4) Uiso d 1
C C6 0.39971(6) 0.70626(16) 0.51478(7) 0.01674(14) Uani d 1
H H6 0.4306(11) 0.842(3) 0.5415(14) 0.035(5) Uiso d 1
C C7 0.41971(6) 0.61457(15) 0.41662(7) 0.01485(13) Uani d 1
H H7 0.4650(11) 0.679(3) 0.3806(13) 0.027(4) Uiso d 1
C C8 0.37476(5) 0.41900(14) 0.38058(6) 0.01223(12) Uani d 1
C C8A 0.30532(5) 0.31090(14) 0.43403(6) 0.01135(11) Uani d 1
C C21 0.12911(5) -0.11660(14) 0.37547(6) 0.01346(12) Uani d 1
Cl Cl1 0.050976(14) 0.06787(4) 0.307478(18) 0.01832(5) Uani d 1
Cl Cl2 0.186136(15) -0.28881(4) 0.284842(18) 0.01848(5) Uani d 1
Cl Cl3 0.071609(17) -0.31494(4) 0.45575(2) 0.02278(5) Uani d 1
N N2 0.39872(5) 0.31463(13) 0.28171(6) 0.01413(12) Uani d 1
O O1 0.38648(6) 0.43392(14) 0.20358(5) 0.02407(15) Uani d 1
O O2 0.43089(6) 0.11444(14) 0.28351(6) 0.02433(15) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C8A 116.89(7)
N1 C2 C3 124.59(8)
N1 C2 C21 114.73(7)
C3 C2 C21 120.42(7)
C4 C3 C2 118.20(7)
C4 C3 H3 121.2(10)
C2 C3 H3 120.5(10)
C3 C4 C4A 119.73(8)
C3 C4 H4 120.6(10)
C4A C4 H4 119.7(10)
C4 C4A C8A 116.76(8)
C4 C4A C5 123.30(8)
C8A C4A C5 119.93(7)
C6 C5 C4A 120.46(8)
C6 C5 H5 121.3(10)
C4A C5 H5 118.2(10)
C5 C6 C7 120.58(8)
C5 C6 H6 119.4(11)
C7 C6 H6 120.0(11)
C8 C7 C6 118.68(8)
C8 C7 H7 121.0(10)
C6 C7 H7 120.1(10)
C7 C8 C8A 123.19(7)
C7 C8 N2 118.95(7)
C8A C8 N2 117.86(7)
N1 C8A C8 119.31(7)
N1 C8A C4A 123.59(7)
C8 C8A C4A 116.96(7)
C2 C21 Cl2 112.32(6)
C2 C21 Cl3 111.89(6)
Cl2 C21 Cl3 108.13(4)
C2 C21 Cl1 107.22(5)
Cl2 C21 Cl1 108.56(5)
Cl3 C21 Cl1 108.61(4)
O2 N2 O1 124.50(8)
O2 N2 C8 117.27(7)
O1 N2 C8 118.23(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3121(10)
N1 C8A 1.3600(11)
C2 C3 1.4148(12)
C2 C21 1.5293(12)
C3 C4 1.3667(13)
C3 H3 0.939(17)
C4 C4A 1.4139(12)
C4 H4 0.965(16)
C4A C8A 1.4151(11)
C4A C5 1.4169(12)
C5 C6 1.3695(13)
C5 H5 0.935(16)
C6 C7 1.4129(12)
C6 H6 0.950(18)
C7 C8 1.3633(12)
C7 H7 0.916(17)
C8 C8A 1.4145(11)
C8 N2 1.4636(11)
C21 Cl2 1.7651(9)
C21 Cl3 1.7682(8)
C21 Cl1 1.7848(8)
N2 O2 1.2201(11)
N2 O1 1.2219(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10025455
