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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-10-27
_journal_date_accepted     2009-10-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o2982
_journal_page_last     o2982
_journal_paper_category     QO
_journal_coeditor_code     CI2954
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Roopan, S. Mohana'
;
Chemistry Division
School of Science and Humanities
VIT University
Vellore 632 014, Tamil Nadu
India
;
    'Khan, F. Nawaz'
;
Chemistry Division
School of Science and Humanities
VIT University
Vellore 632 014, Tamil Nadu
India
;
    'Vijetha, M.'
;
Chemistry Division
School of Science and Humanities
VIT University
Vellore 632 014, Tamil Nadu
India
;
    'Hathwar, Venkatesha R.'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012, Karnataka
India
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H13 Cl2 N O2'
_chemical_formula_sum     'C18 H13 Cl2 N O2'
_chemical_formula_iupac     'C18 H13 Cl2 N O2'
_chemical_formula_weight     346.19
_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     8.3553(3)
_cell_length_b     10.1861(5)
_cell_length_c     10.6731(6)
_cell_angle_alpha     110.537(5)
_cell_angle_beta     101.421(4)
_cell_angle_gamma     95.980(4)
_cell_volume     818.73(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1235
_cell_measurement_theta_min     1.7
_cell_measurement_theta_max     21.3
_cell_measurement_temperature     295(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.404
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     356
_exptl_absorpt_coefficient_mu     0.404
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8747
_exptl_absorpt_correction_T_max     0.9056
_diffrn_ambient_temperature     290(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     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18102
_diffrn_reflns_av_R_equivalents     0.0308
_diffrn_reflns_av_sigmaI/netI     0.0273
_diffrn_reflns_theta_min     3.39
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_reflns_number_total     3700
_reflns_number_gt     2537
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0717
_refine_ls_R_factor_gt     0.0459
_refine_ls_wR_factor_gt     0.1316
_refine_ls_wR_factor_ref     0.1440
_refine_ls_goodness_of_fit_ref     1.023
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     3700
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.07P)²+0.2927P] 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     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.409
_refine_diff_density_min     -0.355
_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'
    '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'
_computing_data_collection     'SMART (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2009)'
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 0.38082(9) 0.27696(7) 0.20007(7) 0.0656(2) Uani d . 1 . .
    Cl Cl2 0.09541(10) 0.80809(9) 0.87358(6) 0.0737(3) Uani d . 1 . .
    N N1 0.2968(2) 0.38235(19) 0.42803(19) 0.0464(4) Uani d . 1 . .
    O O1 0.4425(2) 0.66274(18) 0.20689(15) 0.0522(4) Uani d . 1 . .
    O O2 0.2357(2) 0.48698(19) 0.05569(16) 0.0651(5) Uani d . 1 . .
    C C1 0.3141(3) 0.4086(2) 0.3210(2) 0.0432(5) Uani d . 1 . .
    C C2 0.2874(3) 0.5342(2) 0.2978(2) 0.0394(5) Uani d . 1 . .
    C C3 0.2357(3) 0.6384(2) 0.3963(2) 0.0372(5) Uani d . 1 . .
    C C4 0.2145(3) 0.6144(2) 0.5166(2) 0.0381(5) Uani d . 1 . .
    C C5 0.1637(3) 0.7137(2) 0.6250(2) 0.0436(5) Uani d . 1 . .
    H H5 0.1397 0.7989 0.6195 0.052 Uiso calc R 1 . .
    C C6 0.1503(3) 0.6832(3) 0.7373(2) 0.0479(5) Uani d . 1 . .
    C C7 0.1808(3) 0.5550(3) 0.7485(2) 0.0534(6) Uani d . 1 . .
    H H7 0.1695 0.5368 0.8261 0.064 Uiso calc R 1 . .
    C C8 0.2271(3) 0.4575(3) 0.6448(2) 0.0509(6) Uani d . 1 . .
    H H8 0.2459 0.3714 0.6512 0.061 Uiso calc R 1 . .
    C C9 0.2472(3) 0.4845(2) 0.5278(2) 0.0421(5) Uani d . 1 . .
    C C10 0.2017(3) 0.7710(2) 0.3758(2) 0.0399(5) Uani d . 1 . .
    C C11 0.0839(3) 0.7647(3) 0.2608(2) 0.0479(5) Uani d . 1 . .
    H H11 0.0235 0.6769 0.1963 0.057 Uiso calc R 1 . .
    C C12 0.0565(3) 0.8896(3) 0.2421(3) 0.0607(7) Uani d . 1 . .
    H H12 -0.0235 0.8855 0.1659 0.073 Uiso calc R 1 . .
    C C13 0.1478(4) 1.0192(3) 0.3363(3) 0.0650(7) Uani d . 1 . .
    H H13 0.1301 1.1024 0.3227 0.078 Uiso calc R 1 . .
    C C14 0.2633(4) 1.0268(3) 0.4490(3) 0.0641(7) Uani d . 1 . .
    H H14 0.3240 1.1151 0.5123 0.077 Uiso calc R 1 . .
    C C15 0.2910(3) 0.9030(2) 0.4697(2) 0.0506(6) Uani d . 1 . .
    H H15 0.3701 0.9088 0.5472 0.061 Uiso calc R 1 . .
    C C16 0.3163(3) 0.5558(2) 0.1716(2) 0.0443(5) Uani d . 1 . .
    C C17 0.4740(4) 0.7060(3) 0.0971(3) 0.0749(9) Uani d D 1 . .
    H H17A 0.3713 0.6852 0.0267 0.090 Uiso calc R 1 . .
    H H17B 0.5522 0.6533 0.0547 0.090 Uiso calc R 1 . .
    C C18 0.5432(6) 0.8615(3) 0.1550(4) 0.1137(15) Uani d D 1 . .
    H H18A 0.5572 0.8916 0.0815 0.170 Uiso calc R 1 . .
    H H18B 0.6490 0.8806 0.2195 0.170 Uiso calc R 1 . .
    H H18C 0.4683 0.9129 0.2016 0.170 Uiso calc R 1 . .
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 C1 . 1.732(2) ?
    Cl2 C6 . 1.742(2) ?
    N1 C1 . 1.292(3) ?
    N1 C9 . 1.369(3) ?
    O1 C16 . 1.325(3) ?
    O1 C17 . 1.448(3) ?
    O2 C16 . 1.199(3) ?
    C1 C2 . 1.417(3) ?
    C2 C3 . 1.382(3) ?
    C2 C16 . 1.499(3) ?
    C3 C4 . 1.429(3) ?
    C3 C10 . 1.488(3) ?
    C4 C5 . 1.416(3) ?
    C4 C9 . 1.419(3) ?
    C5 C6 . 1.361(3) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.397(4) ?
    C7 C8 . 1.356(4) ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.407(3) ?
    C8 H8 . 0.93 ?
    C10 C15 . 1.385(3) ?
    C10 C11 . 1.390(3) ?
    C11 C12 . 1.389(3) ?
    C11 H11 . 0.93 ?
    C12 C13 . 1.375(4) ?
    C12 H12 . 0.93 ?
    C13 C14 . 1.358(4) ?
    C13 H13 . 0.93 ?
    C14 C15 . 1.389(4) ?
    C14 H14 . 0.93 ?
    C15 H15 . 0.93 ?
    C17 C18 . 1.485(2) ?
    C17 H17A . 0.97 ?
    C17 H17B . 0.97 ?
    C18 H18A . 0.96 ?
    C18 H18B . 0.96 ?
    C18 H18C . 0.96 ?
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
    C1 N1 C9 . . 117.23(18) ?
    C16 O1 C17 . . 116.36(18) ?
    N1 C1 C2 . . 125.8(2) ?
    N1 C1 Cl1 . . 115.05(16) ?
    C2 C1 Cl1 . . 119.09(17) ?
    C3 C2 C1 . . 118.10(19) ?
    C3 C2 C16 . . 120.40(18) ?
    C1 C2 C16 . . 121.50(19) ?
    C2 C3 C4 . . 118.21(18) ?
    C2 C3 C10 . . 120.49(18) ?
    C4 C3 C10 . . 121.30(18) ?
    C5 C4 C9 . . 118.57(19) ?
    C5 C4 C3 . . 123.39(19) ?
    C9 C4 C3 . . 118.04(19) ?
    C6 C5 C4 . . 119.4(2) ?
    C6 C5 H5 . . 120.3 ?
    C4 C5 H5 . . 120.3 ?
    C5 C6 C7 . . 122.4(2) ?
    C5 C6 Cl2 . . 119.40(19) ?
    C7 C6 Cl2 . . 118.20(17) ?
    C8 C7 C6 . . 119.2(2) ?
    C8 C7 H7 . . 120.4 ?
    C6 C7 H7 . . 120.4 ?
    C7 C8 C9 . . 121.1(2) ?
    C7 C8 H8 . . 119.5 ?
    C9 C8 H8 . . 119.5 ?
    N1 C9 C8 . . 118.0(2) ?
    N1 C9 C4 . . 122.57(19) ?
    C8 C9 C4 . . 119.4(2) ?
    C15 C10 C11 . . 118.9(2) ?
    C15 C10 C3 . . 120.20(19) ?
    C11 C10 C3 . . 120.90(19) ?
    C12 C11 C10 . . 120.0(2) ?
    C12 C11 H11 . . 120.0 ?
    C10 C11 H11 . . 120.0 ?
    C13 C12 C11 . . 120.0(2) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C14 C13 C12 . . 120.6(2) ?
    C14 C13 H13 . . 119.7 ?
    C12 C13 H13 . . 119.7 ?
    C13 C14 C15 . . 120.1(3) ?
    C13 C14 H14 . . 120.0 ?
    C15 C14 H14 . . 120.0 ?
    C10 C15 C14 . . 120.5(2) ?
    C10 C15 H15 . . 119.8 ?
    C14 C15 H15 . . 119.8 ?
    O2 C16 O1 . . 125.1(2) ?
    O2 C16 C2 . . 124.8(2) ?
    O1 C16 C2 . . 110.14(18) ?
    O1 C17 C18 . . 109.4(2) ?
    O1 C17 H17A . . 109.8 ?
    C18 C17 H17A . . 109.8 ?
    O1 C17 H17B . . 109.8 ?
    C18 C17 H17B . . 109.8 ?
    H17A C17 H17B . . 108.2 ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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
    C9 N1 C1 C2 . . . . 0.5(3) ?
    C9 N1 C1 Cl1 . . . . 178.84(15) ?
    N1 C1 C2 C3 . . . . -1.1(3) ?
    Cl1 C1 C2 C3 . . . . -179.37(16) ?
    N1 C1 C2 C16 . . . . 178.0(2) ?
    Cl1 C1 C2 C16 . . . . -0.3(3) ?
    C1 C2 C3 C4 . . . . 0.8(3) ?
    C16 C2 C3 C4 . . . . -178.25(19) ?
    C1 C2 C3 C10 . . . . -178.5(2) ?
    C16 C2 C3 C10 . . . . 2.4(3) ?
    C2 C3 C4 C5 . . . . 179.40(19) ?
    C10 C3 C4 C5 . . . . -1.3(3) ?
    C2 C3 C4 C9 . . . . -0.2(3) ?
    C10 C3 C4 C9 . . . . 179.14(19) ?
    C9 C4 C5 C6 . . . . 1.1(3) ?
    C3 C4 C5 C6 . . . . -178.5(2) ?
    C4 C5 C6 C7 . . . . -1.7(3) ?
    C4 C5 C6 Cl2 . . . . 177.61(16) ?
    C5 C6 C7 C8 . . . . 0.7(4) ?
    Cl2 C6 C7 C8 . . . . -178.63(18) ?
    C6 C7 C8 C9 . . . . 1.0(4) ?
    C1 N1 C9 C8 . . . . 179.8(2) ?
    C1 N1 C9 C4 . . . . 0.3(3) ?
    C7 C8 C9 N1 . . . . 179.0(2) ?
    C7 C8 C9 C4 . . . . -1.6(3) ?
    C5 C4 C9 N1 . . . . 179.98(19) ?
    C3 C4 C9 N1 . . . . -0.4(3) ?
    C5 C4 C9 C8 . . . . 0.5(3) ?
    C3 C4 C9 C8 . . . . -179.88(19) ?
    C2 C3 C10 C15 . . . . -119.8(2) ?
    C4 C3 C10 C15 . . . . 60.9(3) ?
    C2 C3 C10 C11 . . . . 58.2(3) ?
    C4 C3 C10 C11 . . . . -121.1(2) ?
    C15 C10 C11 C12 . . . . -0.5(3) ?
    C3 C10 C11 C12 . . . . -178.6(2) ?
    C10 C11 C12 C13 . . . . 1.0(4) ?
    C11 C12 C13 C14 . . . . -0.9(4) ?
    C12 C13 C14 C15 . . . . 0.3(4) ?
    C11 C10 C15 C14 . . . . -0.1(4) ?
    C3 C10 C15 C14 . . . . 178.0(2) ?
    C13 C14 C15 C10 . . . . 0.2(4) ?
    C17 O1 C16 O2 . . . . 5.6(3) ?
    C17 O1 C16 C2 . . . . -173.7(2) ?
    C3 C2 C16 O2 . . . . -114.0(3) ?
    C1 C2 C16 O2 . . . . 66.9(3) ?
    C3 C2 C16 O1 . . . . 65.3(3) ?
    C1 C2 C16 O1 . . . . -113.8(2) ?
    C16 O1 C17 C18 . . . . 148.7(3) ?
