#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224146.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_2224146
loop_
_publ_author_name
'Roopan, S. Mohana'
'Khan, F. Nawaz'
'Vijetha, M.'
'Hathwar, Venkatesha R.'
'Ng, Seik Weng'
_publ_section_title
;
 Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate
;
_journal_coeditor_code           CI2954
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2982
_journal_paper_doi               10.1107/S1600536809045334
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H13 Cl2 N O2'
_chemical_formula_moiety         'C18 H13 Cl2 N O2'
_chemical_formula_sum            'C18 H13 Cl2 N O2'
_chemical_formula_weight         346.19
_chemical_name_systematic
;
Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate
;
_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                110.537(5)
_cell_angle_beta                 101.421(4)
_cell_angle_gamma                95.980(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3553(3)
_cell_length_b                   10.1861(5)
_cell_length_c                   10.6731(6)
_cell_measurement_reflns_used    1235
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      21.3
_cell_measurement_theta_min      1.7
_cell_volume                     818.74(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18102
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.9056
_exptl_absorpt_correction_T_min  0.8747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3700
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.07P)²+0.2927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1440
_reflns_number_gt                2537
_reflns_number_total             3700
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2954.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        818.73(7)
_cod_database_code               2224146
_cod_database_fobs_code          2224146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 0.38082(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_
_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_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_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_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) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1363070
