#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224589.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_2224589
loop_
_publ_author_name
'Sundar, J. Kalyana'
'Natarajan, S.'
'Sarveswari, S.'
'Vijayakumar, V.'
'Suresh, J.'
'Lakshman, P. L. Nilantha'
_publ_section_title
;
 Methyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate
;
_journal_coeditor_code           CI2981
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o169
_journal_paper_doi               10.1107/S1600536809052891
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H14 Cl N O2'
_chemical_formula_moiety         'C18 H14 Cl N O2'
_chemical_formula_sum            'C18 H14 Cl N O2'
_chemical_formula_weight         311.75
_chemical_name_systematic
;
Methyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.369(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.828(5)
_cell_length_b                   7.535(4)
_cell_length_c                   18.829(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1531.8(12)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius MACH-3'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0106
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3320
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.290
_refine_ls_extinction_coef       0.0132(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.5537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                2309
_reflns_number_total             2682
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2981.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224589
_cod_database_fobs_code          2224589
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.46859(14) 0.2554(2) -0.02447(8) 0.0362(3) Uani d . 1 . .
C C3 0.53086(13) 0.25646(19) 0.04444(8) 0.0346(3) Uani d . 1 . .
C C4 0.46120(13) 0.30371(19) 0.10339(8) 0.0339(3) Uani d . 1 . .
C C5 0.33707(13) 0.33626(19) 0.08882(8) 0.0340(3) Uani d . 1 . .
C C6 0.28365(13) 0.3408(2) 0.01735(8) 0.0358(3) Uani d . 1 . .
C C7 0.15150(15) 0.3971(3) 0.00113(10) 0.0487(4) Uani d . 1 . .
H H7A 0.1384 0.4275 -0.0484 0.073 Uiso calc R 1 . .
H H7B 0.1343 0.4985 0.0297 0.073 Uiso calc R 1 . .
H H7C 0.0973 0.3015 0.0117 0.073 Uiso calc R 1 . .
C C8 0.25152(14) 0.3699(2) 0.14669(8) 0.0410(4) Uani d . 1 . .
C C9 0.0887(2) 0.2382(3) 0.20546(13) 0.0727(6) Uani d . 1 . .
H H9A 0.1254 0.2793 0.2505 0.109 Uiso calc R 1 . .
H H9B 0.0525 0.1233 0.2114 0.109 Uiso calc R 1 . .
H H9C 0.0257 0.3200 0.1878 0.109 Uiso calc R 1 . .
C C10 0.53354(17) 0.2038(2) -0.08359(9) 0.0485(4) Uani d . 1 . .
H H10 0.4928 0.2031 -0.1289 0.058 Uiso calc R 1 . .
C C11 0.65448(17) 0.1555(2) -0.07501(10) 0.0529(5) Uani d . 1 . .
H H11 0.6968 0.1224 -0.1141 0.063 Uiso calc R 1 . .
C C12 0.71432(14) 0.1561(2) -0.00690(11) 0.0472(4) Uani d . 1 . .
C C13 0.65654(14) 0.2040(2) 0.05190(9) 0.0427(4) Uani d . 1 . .
H H13 0.6994 0.2022 0.0966 0.051 Uiso calc R 1 . .
C C14 0.52259(14) 0.3155(2) 0.17690(8) 0.0386(4) Uani d . 1 . .
C C15 0.62527(15) 0.4262(2) 0.19060(9) 0.0451(4) Uani d . 1 . .
H H15 0.6545 0.4927 0.1538 0.054 Uiso calc R 1 . .
C C16 0.68357(17) 0.4376(3) 0.25823(10) 0.0548(5) Uani d . 1 . .
H H16 0.7522 0.5109 0.2667 0.066 Uiso calc R 1 . .
C C17 0.6404(2) 0.3406(3) 0.31331(10) 0.0608(5) Uani d . 1 . .
H H17 0.6805 0.3469 0.3587 0.073 Uiso calc R 1 . .
C C18 0.5376(2) 0.2341(3) 0.30062(10) 0.0608(5) Uani d . 1 . .
H H18 0.5072 0.1710 0.3380 0.073 Uiso calc R 1 . .
C C19 0.47923(17) 0.2203(2) 0.23292(9) 0.0489(4) Uani d . 1 . .
H H19 0.4106 0.1467 0.2249 0.059 Uiso calc R 1 . .
N N1 0.34737(12) 0.30270(18) -0.03732(7) 0.0394(3) Uani d . 1 . .
O O1 0.24231(13) 0.50480(19) 0.17883(8) 0.0677(4) Uani d . 1 . .
O O2 0.18315(11) 0.22595(16) 0.15517(7) 0.0536(3) Uani d . 1 . .
Cl Cl1 0.86967(4) 0.09440(7) 0.00332(4) 0.0739(2) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C2 C10 . . 117.46(14) ?
N1 C2 C3 . . 123.08(13) ?
C10 C2 C3 . . 119.45(14) ?
C13 C3 C2 . . 118.49(14) ?
C13 C3 C4 . . 123.48(14) ?
C2 C3 C4 . . 117.97(13) ?
C5 C4 C3 . . 117.02(13) ?
C5 C4 C14 . . 122.34(13) ?
C3 C4 C14 . . 120.64(13) ?
C4 C5 C6 . . 120.93(13) ?
C4 C5 C8 . . 122.19(13) ?
C6 C5 C8 . . 116.88(13) ?
N1 C6 C5 . . 122.37(13) ?
N1 C6 C7 . . 116.85(14) ?
C5 C6 C7 . . 120.75(14) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O1 C8 O2 . . 124.49(15) ?
O1 C8 C5 . . 126.29(15) ?
O2 C8 C5 . . 109.17(13) ?
O2 C9 H9A . . 109.5 ?
O2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C2 . . 120.85(17) ?
C11 C10 H10 . . 119.6 ?
C2 C10 H10 . . 119.6 ?
C10 C11 C12 . . 119.08(15) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C13 C12 C11 . . 122.66(15) ?
C13 C12 Cl1 . . 118.74(15) ?
C11 C12 Cl1 . . 118.60(13) ?
C12 C13 C3 . . 119.47(16) ?
C12 C13 H13 . . 120.3 ?
C3 C13 H13 . . 120.3 ?
C19 C14 C15 . . 118.62(15) ?
C19 C14 C4 . . 121.47(14) ?
C15 C14 C4 . . 119.91(14) ?
C16 C15 C14 . . 120.58(16) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C17 C16 C15 . . 120.24(17) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C18 C17 C16 . . 119.57(16) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C17 C18 C19 . . 120.69(18) ?
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C18 C19 C14 . . 120.28(17) ?
C18 C19 H19 . . 119.9 ?
C14 C19 H19 . . 119.9 ?
C6 N1 C2 . . 118.28(13) ?
C8 O2 C9 . . 116.98(15) ?
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
C2 N1 . 1.364(2) ?
C2 C10 . 1.416(2) ?
C2 C3 . 1.416(2) ?
C3 C13 . 1.414(2) ?
C3 C4 . 1.434(2) ?
C4 C5 . 1.373(2) ?
C4 C14 . 1.492(2) ?
C5 C6 . 1.424(2) ?
C5 C8 . 1.505(2) ?
C6 N1 . 1.3139(19) ?
C6 C7 . 1.501(2) ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 O1 . 1.191(2) ?
C8 O2 . 1.330(2) ?
C9 O2 . 1.448(2) ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C10 C11 . 1.357(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.392(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.361(2) ?
C12 Cl1 . 1.7418(16) ?
C13 H13 . 0.93 ?
C14 C19 . 1.387(2) ?
C14 C15 . 1.398(2) ?
C15 C16 . 1.380(2) ?
C15 H15 . 0.93 ?
C16 C17 . 1.379(3) ?
C16 H16 . 0.93 ?
C17 C18 . 1.378(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.383(3) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?
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
C9 H9B Cg1 2_545 0.96 2.80 3.744(3) 166
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
N1 C2 C3 C13 . . . . 179.65(14) ?
C10 C2 C3 C13 . . . . -0.5(2) ?
N1 C2 C3 C4 . . . . 2.2(2) ?
C10 C2 C3 C4 . . . . -177.96(14) ?
C13 C3 C4 C5 . . . . -174.20(14) ?
C2 C3 C4 C5 . . . . 3.1(2) ?
C13 C3 C4 C14 . . . . 5.6(2) ?
C2 C3 C4 C14 . . . . -177.17(14) ?
C3 C4 C5 C6 . . . . -6.4(2) ?
C14 C4 C5 C6 . . . . 173.85(14) ?
C3 C4 C5 C8 . . . . 174.07(13) ?
C14 C4 C5 C8 . . . . -5.7(2) ?
C4 C5 C6 N1 . . . . 4.7(2) ?
C8 C5 C6 N1 . . . . -175.70(14) ?
C4 C5 C6 C7 . . . . -172.83(15) ?
C8 C5 C6 C7 . . . . 6.7(2) ?
C4 C5 C8 O1 . . . . 77.7(2) ?
C6 C5 C8 O1 . . . . -101.9(2) ?
C4 C5 C8 O2 . . . . -104.54(17) ?
C6 C5 C8 O2 . . . . 75.90(17) ?
N1 C2 C10 C11 . . . . 179.81(16) ?
C3 C2 C10 C11 . . . . 0.0(3) ?
C2 C10 C11 C12 . . . . 0.4(3) ?
C10 C11 C12 C13 . . . . -0.2(3) ?
C10 C11 C12 Cl1 . . . . -179.82(14) ?
C11 C12 C13 C3 . . . . -0.3(3) ?
Cl1 C12 C13 C3 . . . . 179.26(12) ?
C2 C3 C13 C12 . . . . 0.7(2) ?
C4 C3 C13 C12 . . . . 177.98(14) ?
C5 C4 C14 C19 . . . . 54.6(2) ?
C3 C4 C14 C19 . . . . -125.18(17) ?
C5 C4 C14 C15 . . . . -124.62(17) ?
C3 C4 C14 C15 . . . . 55.6(2) ?
C19 C14 C15 C16 . . . . 1.2(3) ?
C4 C14 C15 C16 . . . . -179.56(16) ?
C14 C15 C16 C17 . . . . -0.5(3) ?
C15 C16 C17 C18 . . . . -0.9(3) ?
C16 C17 C18 C19 . . . . 1.6(3) ?
C17 C18 C19 C14 . . . . -0.9(3) ?
C15 C14 C19 C18 . . . . -0.6(3) ?
C4 C14 C19 C18 . . . . -179.76(17) ?
C5 C6 N1 C2 . . . . 0.7(2) ?
C7 C6 N1 C2 . . . . 178.37(14) ?
C10 C2 N1 C6 . . . . 176.04(14) ?
C3 C2 N1 C6 . . . . -4.1(2) ?
O1 C8 O2 C9 . . . . 2.1(3) ?
C5 C8 O2 C9 . . . . -175.75(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744105
