##############################################################################
#                                                                            #
# 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 Acta Crystallographica Section E, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2014-12-10
_journal_date_accepted     2014-12-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      2
_journal_page_first     o121
_journal_page_last     o121
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989014028266
_journal_coeditor_code     SU5042
_publ_contact_author_name     'Dr N. K. Lokanath'
_publ_contact_author_address
;
Department of Studies in Physics
University of Mysore
Manasagangotri
Mysuru 570 006
India
;
_publ_contact_author_email     'lokanath@physics.uni-mysore.ac.in'
_publ_contact_author_fax     '+91 821 2419610'
_publ_contact_author_phone     '+91 821 2419333'
_publ_section_title
;
Crystal structure of ethyl
6-bromo-2-[(E)-2-phenylethenyl]quinoline-4-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Shrungesh Kumar, T. O.'
;
Department of Chemistry,
Kuvempu University,
Jnanasahyadri,
Shankaraghatta 577 451, India
;
    'Naveen, S.'
;
Institution of Excellence,
University of Mysore,
Manasagangotri,
Mysuru 570 006, India
;
    'Kumara, M. N.'
;
Department of Chemistry,
Yuvaraja's College,
University of Mysore,
Mysuru 570 005, India
;
    'Mahadevan, K. M.'
;
Department of Chemistry,
Kuvempu University,
Jnanasahyadri,
Shankaraghatta 577451, India
;
    'Lokanath, N. K.'
;
Department of Studies in Physics,
University of Mysore,
Manasagangotri,
Mysuru 570 006, India
;
data_I
_database_code_depnum_ccdc_archive     'CCDC 1041593'
_chemical_name_systematic
;
Ethyl 6-bromo-2-[(E)-2-phenylethenyl]quinoline-4-carboxylate
;
_chemical_formula_moiety     'C20 H16 Br N O2'
_chemical_formula_sum     'C20 H16 Br N O2'
_chemical_formula_iupac     'C20 H16 Br N O2'
_chemical_formula_weight     382.24
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,-y,1/2+z
    3 1/2+x,1/2-y,-z
    4 -x,1/2+y,1/2-z
    5 -x,-y,-z
    6 1/2+x,y,1/2-z
    7 1/2-x,1/2+y,z
    8 x,1/2-y,1/2+z
_cell_length_a     14.0819(7)
_cell_length_b     9.7470(5)
_cell_length_c     24.0399(12)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3299.6(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2722
_cell_measurement_theta_min     5.82
_cell_measurement_theta_max     64.46
_cell_measurement_temperature     293
_cell_special_details
;
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'green'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.25
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.539
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     1552
_exptl_absorpt_coefficient_mu     3.489
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_absorpt_correction_T_min     0.421
_exptl_absorpt_correction_T_max     0.476
_exptl_special_details
;
;
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'CuK\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_monochromator     'Helios multilayer optics'
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     18.4
_diffrn_reflns_number     12970
_diffrn_reflns_av_R_equivalents     0.0705
_diffrn_reflns_av_sigmaI/netI     0.0629
_diffrn_reflns_theta_min     5.82
_diffrn_reflns_theta_max     64.46
_diffrn_reflns_theta_full     64.46
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     27
_diffrn_reflns_reduction_process
;
;
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs 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     2722
_reflns_number_gt     2213
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0566
_refine_ls_R_factor_gt     0.0459
_refine_ls_wR_factor_gt     0.1228
_refine_ls_wR_factor_ref     0.1341
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_restrained_S_all     1.043
_refine_ls_number_reflns     2722
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0857P)²] 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     0.000
_refine_diff_density_max     0.782
_refine_diff_density_min     -0.923
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 ' 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'
    Br Br -0.6763 1.2805
                        ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br11 0.40232(3) 0.12926(3) 0.45926(2) 0.0260(2) Uani d . 1.000 . .
    O O13 0.3502(2) 0.6096(2) 0.39081(10) 0.0299(8) Uani d . 1.000 . .
    O O14 0.32650(17) 0.8275(2) 0.41637(9) 0.0225(7) Uani d . 1.000 . .
    N N1 0.3740(2) 0.6330(3) 0.60400(12) 0.0194(9) Uani d . 1.000 . .
    C C2 0.3819(2) 0.5243(3) 0.56849(15) 0.0186(9) Uani d . 1.000 . .
    C C3 0.4009(2) 0.3948(4) 0.59271(17) 0.0235(11) Uani d . 1.000 . .
    C C4 0.4086(2) 0.2801(4) 0.56073(17) 0.0252(11) Uani d . 1.000 . .
    C C5 0.3971(2) 0.2916(3) 0.50306(16) 0.0212(10) Uani d . 1.000 . .
    C C6 0.3799(2) 0.4140(3) 0.47707(15) 0.0186(10) Uani d . 1.000 . .
    C C7 0.3720(2) 0.5345(3) 0.50974(14) 0.0169(9) Uani d . 1.000 . .
    C C8 0.3536(2) 0.6688(3) 0.48784(14) 0.0170(9) Uani d . 1.000 . .
    C C9 0.3445(2) 0.7753(3) 0.52462(14) 0.0194(10) Uani d . 1.000 . .
    C C10 0.3557(2) 0.7552(3) 0.58248(14) 0.0183(9) Uani d . 1.000 . .
    C C12 0.3436(2) 0.6941(3) 0.42679(14) 0.0191(10) Uani d . 1.000 . .
    C C15 0.3129(3) 0.8638(3) 0.35775(15) 0.0256(11) Uani d . 1.000 . .
    C C16 0.4064(3) 0.8926(4) 0.33011(17) 0.0305(11) Uani d . 1.000 . .
    C C17 0.3493(2) 0.8754(3) 0.61965(15) 0.0208(10) Uani d . 1.000 . .
    C C18 0.3704(3) 0.8739(3) 0.67333(15) 0.0208(11) Uani d . 1.000 . .
    C C19 0.3718(2) 0.9924(3) 0.71107(14) 0.0189(9) Uani d . 1.000 . .
    C C20 0.3281(3) 1.1179(3) 0.69823(15) 0.0237(11) Uani d . 1.000 . .
    C C21 0.3389(3) 1.2296(3) 0.73304(16) 0.0251(10) Uani d . 1.000 . .
    C C22 0.3913(2) 1.2187(4) 0.78153(15) 0.0237(11) Uani d . 1.000 . .
    C C23 0.4324(3) 1.0941(4) 0.79619(15) 0.0246(10) Uani d . 1.000 . .
    C C24 0.4218(3) 0.9823(3) 0.76129(14) 0.0216(10) Uani d . 1.000 . .
    H H3 0.40820 0.38790 0.63110 0.0280 Uiso c R 1.000 . .
    H H4 0.42130 0.19540 0.57690 0.0300 Uiso c R 1.000 . .
    H H6 0.37340 0.41800 0.43860 0.0220 Uiso c R 1.000 . .
    H H9 0.33080 0.86260 0.51130 0.0230 Uiso c R 1.000 . .
    H H15A 0.27260 0.94430 0.35520 0.0310 Uiso c R 1.000 . .
    H H15B 0.28130 0.78890 0.33870 0.0310 Uiso c R 1.000 . .
    H H16A 0.43890 0.96390 0.35000 0.0460 Uiso c R 1.000 . .
    H H16B 0.39560 0.92140 0.29240 0.0460 Uiso c R 1.000 . .
    H H16C 0.44440 0.81090 0.33020 0.0460 Uiso c R 1.000 . .
    H H17 0.32900 0.95800 0.60430 0.0250 Uiso c R 1.000 . .
    H H18 0.38580 0.78920 0.68870 0.0250 Uiso c R 1.000 . .
    H H20 0.29170 1.12590 0.66610 0.0280 Uiso c R 1.000 . .
    H H21 0.31060 1.31280 0.72380 0.0300 Uiso c R 1.000 . .
    H H22 0.39920 1.29490 0.80430 0.0290 Uiso c R 1.000 . .
    H H23 0.46650 1.08590 0.82910 0.0300 Uiso c R 1.000 . .
    H H24 0.44850 0.89860 0.77140 0.0260 Uiso c R 1.000 . .
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br11 C5 . . 1.902(3) no
    O13 C12 . . 1.198(4) no
    O14 C12 . . 1.346(4) no
    O14 C15 . . 1.466(4) no
    N1 C2 . . 1.365(4) no
    N1 C10 . . 1.324(4) no
    C2 C3 . . 1.416(5) no
    C2 C7 . . 1.423(5) no
    C3 C4 . . 1.361(6) no
    C4 C5 . . 1.400(6) no
    C5 C6 . . 1.368(4) no
    C6 C7 . . 1.417(4) no
    C7 C8 . . 1.435(4) no
    C8 C9 . . 1.370(4) no
    C8 C12 . . 1.495(5) no
    C9 C10 . . 1.414(5) no
    C10 C17 . . 1.476(4) no
    C15 C16 . . 1.501(6) no
    C17 C18 . . 1.324(5) no
    C18 C19 . . 1.469(4) no
    C19 C20 . . 1.404(4) no
    C19 C24 . . 1.401(5) no
    C20 C21 . . 1.382(5) no
    C21 C22 . . 1.384(5) no
    C22 C23 . . 1.391(5) no
    C23 C24 . . 1.383(5) no
    C3 H3 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C9 H9 . . 0.9300 no
    C15 H15A . . 0.9700 no
    C15 H15B . . 0.9700 no
    C16 H16A . . 0.9600 no
    C16 H16B . . 0.9600 no
    C16 H16C . . 0.9600 no
    C17 H17 . . 0.9300 no
    C18 H18 . . 0.9300 no
    C20 H20 . . 0.9300 no
    C21 H21 . . 0.9300 no
    C22 H22 . . 0.9300 no
    C23 H23 . . 0.9300 no
    C24 H24 . . 0.9300 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C12 O14 C15 . . . 115.8(2) no
    C2 N1 C10 . . . 118.0(3) no
    N1 C2 C3 . . . 116.8(3) no
    N1 C2 C7 . . . 124.0(3) no
    C3 C2 C7 . . . 119.3(3) no
    C2 C3 C4 . . . 121.0(4) no
    C3 C4 C5 . . . 119.0(3) no
    Br11 C5 C4 . . . 118.5(2) no
    Br11 C5 C6 . . . 118.6(3) no
    C4 C5 C6 . . . 122.8(3) no
    C5 C6 C7 . . . 118.9(3) no
    C2 C7 C6 . . . 119.0(3) no
    C2 C7 C8 . . . 116.5(3) no
    C6 C7 C8 . . . 124.5(3) no
    C7 C8 C9 . . . 118.1(3) no
    C7 C8 C12 . . . 121.9(3) no
    C9 C8 C12 . . . 120.0(3) no
    C8 C9 C10 . . . 121.3(3) no
    N1 C10 C9 . . . 122.1(3) no
    N1 C10 C17 . . . 119.3(3) no
    C9 C10 C17 . . . 118.6(3) no
    O13 C12 O14 . . . 122.9(3) no
    O13 C12 C8 . . . 126.0(3) no
    O14 C12 C8 . . . 111.0(3) no
    O14 C15 C16 . . . 110.9(3) no
    C10 C17 C18 . . . 124.6(3) no
    C17 C18 C19 . . . 126.6(3) no
    C18 C19 C20 . . . 122.9(3) no
    C18 C19 C24 . . . 118.9(3) no
    C20 C19 C24 . . . 118.1(3) no
    C19 C20 C21 . . . 120.4(3) no
    C20 C21 C22 . . . 120.6(3) no
    C21 C22 C23 . . . 120.2(3) no
    C22 C23 C24 . . . 119.3(3) no
    C19 C24 C23 . . . 121.4(3) no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 119.00 no
    C3 C4 H4 . . . 121.00 no
    C5 C4 H4 . . . 120.00 no
    C5 C6 H6 . . . 121.00 no
    C7 C6 H6 . . . 121.00 no
    C8 C9 H9 . . . 119.00 no
    C10 C9 H9 . . . 119.00 no
    O14 C15 H15A . . . 109.00 no
    O14 C15 H15B . . . 109.00 no
    C16 C15 H15A . . . 109.00 no
    C16 C15 H15B . . . 110.00 no
    H15A C15 H15B . . . 108.00 no
    C15 C16 H16A . . . 109.00 no
    C15 C16 H16B . . . 109.00 no
    C15 C16 H16C . . . 109.00 no
    H16A C16 H16B . . . 110.00 no
    H16A C16 H16C . . . 110.00 no
    H16B C16 H16C . . . 109.00 no
    C10 C17 H17 . . . 118.00 no
    C18 C17 H17 . . . 118.00 no
    C17 C18 H18 . . . 117.00 no
    C19 C18 H18 . . . 117.00 no
    C19 C20 H20 . . . 120.00 no
    C21 C20 H20 . . . 120.00 no
    C20 C21 H21 . . . 120.00 no
    C22 C21 H21 . . . 120.00 no
    C21 C22 H22 . . . 120.00 no
    C23 C22 H22 . . . 120.00 no
    C22 C23 H23 . . . 120.00 no
    C24 C23 H23 . . . 120.00 no
    C19 C24 H24 . . . 119.00 no
    C23 C24 H24 . . . 119.00 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C15 O14 C12 O13 . . . . 2.1(4) no
    C15 O14 C12 C8 . . . . -178.5(3) no
    C12 O14 C15 C16 . . . . -86.7(3) no
    C2 N1 C10 C17 . . . . -178.4(3) no
    C2 N1 C10 C9 . . . . -0.1(4) no
    C10 N1 C2 C3 . . . . -179.6(3) no
    C10 N1 C2 C7 . . . . 0.2(4) no
    C7 C2 C3 C4 . . . . -0.8(4) no
    C3 C2 C7 C6 . . . . 1.0(4) no
    N1 C2 C7 C6 . . . . -178.8(3) no
    N1 C2 C7 C8 . . . . 0.7(4) no
    N1 C2 C3 C4 . . . . 179.0(3) no
    C3 C2 C7 C8 . . . . -179.5(3) no
    C2 C3 C4 C5 . . . . -0.2(4) no
    C3 C4 C5 C6 . . . . 1.1(4) no
    C3 C4 C5 Br11 . . . . -177.2(2) no
    Br11 C5 C6 C7 . . . . 177.4(2) no
    C4 C5 C6 C7 . . . . -0.9(4) no
    C5 C6 C7 C2 . . . . -0.2(4) no
    C5 C6 C7 C8 . . . . -179.6(3) no
    C6 C7 C8 C9 . . . . 177.8(3) no
    C6 C7 C8 C12 . . . . -1.8(4) no
    C2 C7 C8 C9 . . . . -1.7(4) no
    C2 C7 C8 C12 . . . . 178.8(3) no
    C7 C8 C9 C10 . . . . 1.9(4) no
    C12 C8 C9 C10 . . . . -178.6(3) no
    C7 C8 C12 O13 . . . . -0.6(5) no
    C9 C8 C12 O14 . . . . 0.4(4) no
    C7 C8 C12 O14 . . . . 179.9(3) no
    C9 C8 C12 O13 . . . . 179.9(3) no
    C8 C9 C10 N1 . . . . -1.0(4) no
    C8 C9 C10 C17 . . . . 177.3(3) no
    N1 C10 C17 C18 . . . . 7.5(5) no
    C9 C10 C17 C18 . . . . -170.9(3) no
    C10 C17 C18 C19 . . . . 175.3(3) no
    C17 C18 C19 C20 . . . . 16.4(6) no
    C17 C18 C19 C24 . . . . -161.1(4) no
    C18 C19 C20 C21 . . . . -174.2(4) no
    C24 C19 C20 C21 . . . . 3.4(5) no
    C18 C19 C24 C23 . . . . 174.4(4) no
    C20 C19 C24 C23 . . . . -3.3(5) no
    C19 C20 C21 C22 . . . . -1.3(6) no
    C20 C21 C22 C23 . . . . -1.1(6) no
    C21 C22 C23 C24 . . . . 1.2(6) no
    C22 C23 C24 C19 . . . . 1.0(6) no
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
    C6 H6 O13 . 0.93 2.22 2.848(4) 124 yes
    C15 H15A O13 7_555 0.97 2.51 3.413(4) 154 yes
