#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017345.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_2017345
loop_
_publ_author_name
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 Hydrogen-bonded structures of the isomeric compounds of quinoline with
 2-chloro-5-nitrobenzoic acid, 3-chloro-2-nitrobenzoic acid,
 4-chloro-2-nitrobenzoic acid and 5-chloro-2-nitrobenzoic acid
;
_journal_coeditor_code           GD3308
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o534
_journal_page_last               o538
_journal_paper_doi               10.1107/S0108270109037688
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H3.53 Cl N O4, C9 H7.47 N'
_chemical_formula_moiety         'C7 H3.53 Cl N O4, C9 H7.47 N'
_chemical_formula_sum            'C16 H11 Cl N2 O4'
_chemical_formula_weight         330.73
_chemical_name_systematic
;
4-chloro-2-nitrobenzoic acid--quinoline (1/1)
;
_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
_cell_angle_alpha                88.959(2)
_cell_angle_beta                 80.348(3)
_cell_angle_gamma                78.671(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9684(8)
_cell_length_b                   8.6178(7)
_cell_length_c                   11.1202(9)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    185.0(10)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.0
_cell_volume                     738.06(11)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and WinGX (Farrugia, 1999)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      185.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11936
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0372
_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)+(0.0635P)²+0.1264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                3681
_reflns_number_total             4237
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3308.cif
_cod_data_source_block           III
_cod_original_formula_sum        'C16 H11 Cl N2 O4 '
_cod_database_code               2017345
_cod_database_fobs_code          2017345
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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
Cl Cl1 0.44149(4) 0.01184(3) 0.78073(2) 0.03670(10) Uani d . 1 . .
O O1 0.75936(10) 0.41131(10) 0.30316(8) 0.03226(18) Uani d . 1 . .
H H1 0.766(4) 0.465(4) 0.249(4) 0.039 Uiso d P 0.53(3) . .
O O2 0.48528(12) 0.44258(13) 0.27182(9) 0.0448(2) Uani d . 1 . .
O O3 0.93926(13) 0.09385(14) 0.35728(11) 0.0573(3) Uani d . 1 . .
O O4 0.96626(15) 0.2538(2) 0.49643(12) 0.0776(5) Uani d . 1 . .
N N1 0.88154(12) 0.18311(14) 0.44458(10) 0.0396(3) Uani d . 1 . .
N N2 0.80002(11) 0.59677(10) 0.12311(8) 0.02490(17) Uani d . 1 . .
H H2 0.792(4) 0.529(4) 0.194(3) 0.030 Uiso d P 0.47(3) . .
C C1 0.56693(12) 0.28796(11) 0.43825(9) 0.02345(19) Uani d . 1 . .
C C2 0.69549(12) 0.19857(12) 0.49544(9) 0.02463(19) Uani d . 1 . .
C C3 0.66070(13) 0.11225(12) 0.59936(9) 0.0262(2) Uani d . 1 . .
H H3 0.7519 0.0526 0.6359 0.031 Uiso calc R 1 . .
C C4 0.48841(13) 0.11573(12) 0.64835(9) 0.02481(19) Uani d . 1 . .
C C5 0.35483(13) 0.19985(13) 0.59393(10) 0.0282(2) Uani d . 1 . .
H H5 0.2372 0.1992 0.6275 0.034 Uiso calc R 1 . .
C C6 0.39571(13) 0.28507(12) 0.48970(10) 0.0269(2) Uani d . 1 . .
H H6 0.3044 0.3431 0.4524 0.032 Uiso calc R 1 . .
C C7 0.60165(14) 0.38830(12) 0.32806(10) 0.0265(2) Uani d . 1 . .
C C8 0.69009(14) 0.61092(12) 0.04541(10) 0.0280(2) Uani d . 1 . .
H H8 0.5922 0.5618 0.0641 0.034 Uiso calc R 1 . .
C C9 0.71070(15) 0.69512(13) -0.06374(10) 0.0303(2) Uani d . 1 . .
H H9 0.6286 0.7024 -0.1175 0.036 Uiso calc R 1 . .
C C10 0.85079(15) 0.76620(13) -0.09110(10) 0.0297(2) Uani d . 1 . .
H H10 0.8675 0.8234 -0.1646 0.036 Uiso calc R 1 . .
C C11 0.97095(13) 0.75437(11) -0.00960(9) 0.02514(19) Uani d . 1 . .
C C12 1.12012(15) 0.82365(13) -0.03319(12) 0.0338(2) Uani d . 1 . .
H H12 1.1420 0.8816 -0.1057 0.041 Uiso calc R 1 . .
C C13 1.23235(15) 0.80694(15) 0.04862(14) 0.0392(3) Uani d . 1 . .
H H13 1.3316 0.8545 0.0330 0.047 Uiso calc R 1 . .
C C14 1.20253(15) 0.71999(15) 0.15591(13) 0.0378(3) Uani d . 1 . .
H H14 1.2828 0.7088 0.2113 0.045 Uiso calc R 1 . .
C C15 1.05948(15) 0.65113(13) 0.18181(10) 0.0309(2) Uani d . 1 . .
H H15 1.0402 0.5932 0.2546 0.037 Uiso calc R 1 . .
C C16 0.94107(12) 0.66765(11) 0.09858(9) 0.02343(19) 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'
O O 0.0106 0.0060 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 H1 . . 108(2) ?
O4 N1 O3 . . 125.17(12) ?
O4 N1 C2 . . 117.50(12) ?
O3 N1 C2 . . 117.22(11) ?
C8 N2 C16 . . 119.42(9) ?
C8 N2 H2 . . 122.4(19) ?
C16 N2 H2 . . 117.9(19) ?
C2 C1 C6 . . 116.61(9) ?
C2 C1 C7 . . 124.38(9) ?
C6 C1 C7 . . 119.00(9) ?
C3 C2 C1 . . 123.46(9) ?
C3 C2 N1 . . 114.83(9) ?
C1 C2 N1 . . 121.63(9) ?
C2 C3 C4 . . 117.70(9) ?
C2 C3 H3 . . 121.2 ?
C4 C3 H3 . . 121.2 ?
C3 C4 C5 . . 121.43(9) ?
C3 C4 Cl1 . . 118.53(8) ?
C5 C4 Cl1 . . 120.04(8) ?
C4 C5 C6 . . 118.92(10) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 121.84(9) ?
C5 C6 H6 . . 119.1 ?
C1 C6 H6 . . 119.1 ?
O2 C7 O1 . . 125.42(10) ?
O2 C7 C1 . . 120.23(10) ?
O1 C7 C1 . . 114.34(9) ?
N2 C8 C9 . . 123.16(10) ?
N2 C8 H8 . . 118.4 ?
C9 C8 H8 . . 118.4 ?
C10 C9 C8 . . 118.77(10) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
C9 C10 C11 . . 119.67(10) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C10 C11 C16 . . 118.19(9) ?
C10 C11 C12 . . 122.53(10) ?
C16 C11 C12 . . 119.27(10) ?
C13 C12 C11 . . 119.82(11) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.73(11) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C15 C14 C13 . . 121.09(11) ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C14 C15 C16 . . 119.10(11) ?
C14 C15 H15 . . 120.4 ?
C16 C15 H15 . . 120.4 ?
N2 C16 C15 . . 119.22(9) ?
N2 C16 C11 . . 120.79(9) ?
C15 C16 C11 . . 119.98(10) ?
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
Cl1 C4 . 1.7342(10) ?
O1 C7 . 1.2940(13) ?
O1 H1 . 0.75(4) ?
O2 C7 . 1.2179(13) ?
O3 N1 . 1.2183(17) ?
O4 N1 . 1.2102(18) ?
N1 C2 . 1.4762(13) ?
N2 C8 . 1.3178(14) ?
N2 C16 . 1.3681(13) ?
N2 H2 . 0.97(4) ?
C1 C2 . 1.3921(13) ?
C1 C6 . 1.3930(14) ?
C1 C7 . 1.5058(14) ?
C2 C3 . 1.3813(14) ?
C3 C4 . 1.3843(14) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3862(15) ?
C5 C6 . 1.3877(15) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C8 C9 . 1.4052(15) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3645(16) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.4135(15) ?
C10 H10 . 0.9500 ?
C11 C16 . 1.4154(14) ?
C11 C12 . 1.4166(15) ?
C12 C13 . 1.3658(19) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.408(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3725(17) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.4151(14) ?
C15 H15 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N2 . 0.75(4) 1.81(4) 2.5569(12) 175(3) y
N2 H2 O1 . 0.97(3) 1.59(3) 2.5569(12) 173(3) y
C8 H8 O2 . 0.95 2.59 3.2445(15) 126 y
C9 H9 O2 2_665 0.95 2.52 3.3527(16) 146 y
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
C6 C1 C2 C3 . . . . -1.24(16) ?
C7 C1 C2 C3 . . . . 177.33(10) ?
C6 C1 C2 N1 . . . . 175.61(10) ?
C7 C1 C2 N1 . . . . -5.82(17) ?
O4 N1 C2 C3 . . . . -75.93(15) ?
O3 N1 C2 C3 . . . . 100.52(12) ?
O4 N1 C2 C1 . . . . 106.96(14) ?
O3 N1 C2 C1 . . . . -76.59(14) ?
C1 C2 C3 C4 . . . . 0.01(16) ?
N1 C2 C3 C4 . . . . -177.04(10) ?
C2 C3 C4 C5 . . . . 1.40(16) ?
C2 C3 C4 Cl1 . . . . -178.58(8) ?
C3 C4 C5 C6 . . . . -1.50(16) ?
Cl1 C4 C5 C6 . . . . 178.48(8) ?
C4 C5 C6 C1 . . . . 0.18(16) ?
C2 C1 C6 C5 . . . . 1.13(16) ?
C7 C1 C6 C5 . . . . -177.52(10) ?
C2 C1 C7 O2 . . . . 168.26(11) ?
C6 C1 C7 O2 . . . . -13.20(16) ?
C2 C1 C7 O1 . . . . -13.00(15) ?
C6 C1 C7 O1 . . . . 165.55(10) ?
C16 N2 C8 C9 . . . . 0.57(15) ?
N2 C8 C9 C10 . . . . -0.12(16) ?
C8 C9 C10 C11 . . . . -0.26(16) ?
C9 C10 C11 C16 . . . . 0.17(15) ?
C9 C10 C11 C12 . . . . 179.21(10) ?
C10 C11 C12 C13 . . . . -179.42(10) ?
C16 C11 C12 C13 . . . . -0.40(16) ?
C11 C12 C13 C14 . . . . 0.67(18) ?
C12 C13 C14 C15 . . . . -0.65(18) ?
C13 C14 C15 C16 . . . . 0.32(17) ?
C8 N2 C16 C15 . . . . -179.52(9) ?
C8 N2 C16 C11 . . . . -0.64(14) ?
C14 C15 C16 N2 . . . . 178.85(10) ?
C14 C15 C16 C11 . . . . -0.04(15) ?
C10 C11 C16 N2 . . . . 0.27(14) ?
C12 C11 C16 N2 . . . . -178.79(9) ?
C10 C11 C16 C15 . . . . 179.15(9) ?
C12 C11 C16 C15 . . . . 0.08(15) ?
