#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224149.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_2224149
loop_
_publ_author_name
'Subashini, R.'
'Khan, F. Nawaz'
'Mittal, Suganya'
'Hathwar, Venkatesha R.'
'Ng, Seik Weng'
_publ_section_title
;
 Ethyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate
;
_journal_coeditor_code           CI2957
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2986
_journal_paper_doi               10.1107/S160053680904536X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H16 Cl N O2'
_chemical_formula_moiety         'C19 H16 Cl N O2'
_chemical_formula_sum            'C19 H16 Cl N O2'
_chemical_formula_weight         325.78
_chemical_name_systematic
;
Ethyl 6-chloro-2-methyl-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                110.440(2)
_cell_angle_beta                 101.588(2)
_cell_angle_gamma                94.860(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3622(3)
_cell_length_b                   10.1971(3)
_cell_length_c                   10.7052(3)
_cell_measurement_reflns_used    1153
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      1.7
_cell_volume                     825.91(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15008
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.9446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0475
_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)+(0.0795P)²+0.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                2854
_reflns_number_total             3775
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2957.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        825.91(4)
_cod_database_code               2224149
_cod_database_fobs_code          2224149
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 0.59565(8) 0.80991(7) 0.87661(5) 0.0711(2) Uani d . 1 . .
N N1 0.79494(19) 0.38099(15) 0.42954(15) 0.0465(4) Uani d . 1 . .
O O1 0.93549(17) 0.66715(14) 0.21071(12) 0.0523(3) Uani d . 1 . .
O O2 0.7449(2) 0.48238(16) 0.06011(14) 0.0690(4) Uani d . 1 . .
C C1 0.8150(2) 0.40465(18) 0.31986(18) 0.0433(4) Uani d . 1 . .
C C2 0.7883(2) 0.53430(18) 0.30236(17) 0.0407(4) Uani d . 1 . .
C C3 0.7375(2) 0.63972(17) 0.40021(16) 0.0387(4) Uani d . 1 . .
C C4 0.71546(19) 0.61552(17) 0.52007(16) 0.0387(4) Uani d . 1 . .
C C5 0.6644(2) 0.7151(2) 0.62823(17) 0.0451(4) Uani d . 1 . .
H H5 0.6412 0.8009 0.6230 0.054 Uiso calc R 1 . .
C C6 0.6496(2) 0.6845(2) 0.74006(17) 0.0481(4) Uani d . 1 . .
C C7 0.6778(2) 0.5543(2) 0.74986(18) 0.0523(5) Uani d . 1 . .
H H7 0.6647 0.5352 0.8264 0.063 Uiso calc R 1 . .
C C8 0.7245(2) 0.4561(2) 0.64596(19) 0.0508(4) Uani d . 1 . .
H H8 0.7428 0.3696 0.6520 0.061 Uiso calc R 1 . .
C C9 0.7459(2) 0.48359(18) 0.52871(17) 0.0422(4) Uani d . 1 . .
C C10 0.8700(3) 0.2882(2) 0.2144(2) 0.0569(5) Uani d . 1 . .
H H10A 0.8926 0.2145 0.2484 0.085 Uiso calc R 1 . .
H H10B 0.9685 0.3259 0.1968 0.085 Uiso calc R 1 . .
H H10C 0.7839 0.2500 0.1307 0.085 Uiso calc R 1 . .
C C11 0.8176(2) 0.55604(19) 0.17664(18) 0.0465(4) Uani d . 1 . .
C C12 0.9625(4) 0.7067(2) 0.0980(2) 0.0733(7) Uani d D 1 . .
H H12A 0.8579 0.6918 0.0321 0.088 Uiso calc R 1 . .
H H12B 1.0348 0.6487 0.0514 0.088 Uiso calc R 1 . .
C C13 1.0409(5) 0.8617(3) 0.1562(3) 0.1064(11) Uani d D 1 . .
H H13A 1.0569 0.8904 0.0826 0.160 Uiso calc R 1 . .
H H13B 1.1459 0.8749 0.2191 0.160 Uiso calc R 1 . .
H H13C 0.9696 0.9181 0.2038 0.160 Uiso calc R 1 . .
C C14 0.7035(2) 0.77328(18) 0.38081(17) 0.0408(4) Uani d . 1 . .
C C15 0.5843(2) 0.7689(2) 0.26713(19) 0.0492(4) Uani d . 1 . .
H H15 0.5239 0.6823 0.2036 0.059 Uiso calc R 1 . .
C C16 0.5557(3) 0.8940(2) 0.2488(2) 0.0609(5) Uani d . 1 . .
H H16 0.4755 0.8908 0.1733 0.073 Uiso calc R 1 . .
C C17 0.6458(3) 1.0230(2) 0.3421(3) 0.0625(6) Uani d . 1 . .
H H17 0.6263 1.1064 0.3293 0.075 Uiso calc R 1 . .
C C18 0.7641(3) 1.0279(2) 0.4538(2) 0.0629(5) Uani d . 1 . .
H H18 0.8251 1.1147 0.5165 0.075 Uiso calc R 1 . .
C C19 0.7927(2) 0.9034(2) 0.4729(2) 0.0521(4) Uani d . 1 . .
H H19 0.8731 0.9075 0.5487 0.063 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 . . 118.67(14) ?
C11 O1 C12 . . 115.60(15) ?
N1 C1 C2 . . 122.09(16) ?
N1 C1 C10 . . 116.33(15) ?
C2 C1 C10 . . 121.57(15) ?
C3 C2 C1 . . 120.68(15) ?
C3 C2 C11 . . 119.90(15) ?
C1 C2 C11 . . 119.42(15) ?
C2 C3 C4 . . 117.83(14) ?
C2 C3 C14 . . 121.20(14) ?
C4 C3 C14 . . 120.96(14) ?
C5 C4 C9 . . 119.10(15) ?
C5 C4 C3 . . 123.49(15) ?
C9 C4 C3 . . 117.41(15) ?
C6 C5 C4 . . 119.64(16) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C7 . . 122.02(17) ?
C5 C6 Cl1 . . 119.74(15) ?
C7 C6 Cl1 . . 118.23(13) ?
C8 C7 C6 . . 119.22(16) ?
C8 C7 H7 . . 120.4 ?
C6 C7 H7 . . 120.4 ?
C7 C8 C9 . . 121.19(17) ?
C7 C8 H8 . . 119.4 ?
C9 C8 H8 . . 119.4 ?
N1 C9 C8 . . 117.90(15) ?
N1 C9 C4 . . 123.31(15) ?
C8 C9 C4 . . 118.79(16) ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O2 C11 O1 . . 124.32(17) ?
O2 C11 C2 . . 124.75(18) ?
O1 C11 C2 . . 110.93(14) ?
O1 C12 C13 . . 108.36(17) ?
O1 C12 H12A . . 110.0 ?
C13 C12 H12A . . 110.0 ?
O1 C12 H12B . . 110.0 ?
C13 C12 H12B . . 110.0 ?
H12A C12 H12B . . 108.4 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C19 C14 C15 . . 118.78(16) ?
C19 C14 C3 . . 120.68(15) ?
C15 C14 C3 . . 120.52(16) ?
C16 C15 C14 . . 120.00(18) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C17 C16 C15 . . 120.37(19) ?
C17 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C18 C17 C16 . . 119.94(18) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C17 C18 C19 . . 119.9(2) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C14 C19 C18 . . 120.97(19) ?
C14 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
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 C6 . 1.7414(19) ?
N1 C1 . 1.317(2) ?
N1 C9 . 1.364(2) ?
O1 C11 . 1.329(2) ?
O1 C12 . 1.450(2) ?
O2 C11 . 1.206(2) ?
C1 C2 . 1.428(2) ?
C1 C10 . 1.503(3) ?
C2 C3 . 1.380(2) ?
C2 C11 . 1.501(2) ?
C3 C4 . 1.432(2) ?
C3 C14 . 1.489(2) ?
C4 C5 . 1.416(2) ?
C4 C9 . 1.421(2) ?
C5 C6 . 1.364(2) ?
C5 H5 . 0.93 ?
C6 C7 . 1.404(3) ?
C7 C8 . 1.362(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.419(2) ?
C8 H8 . 0.93 ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C12 C13 . 1.513(2) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
C14 C19 . 1.383(3) ?
C14 C15 . 1.394(2) ?
C15 C16 . 1.389(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.381(3) ?
C16 H16 . 0.93 ?
C17 C18 . 1.373(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.387(3) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?
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 C10 . . . . 179.69(16) ?
N1 C1 C2 C3 . . . . -1.0(3) ?
C10 C1 C2 C3 . . . . 179.86(16) ?
N1 C1 C2 C11 . . . . 178.43(16) ?
C10 C1 C2 C11 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 1.1(2) ?
C11 C2 C3 C4 . . . . -178.39(15) ?
C1 C2 C3 C14 . . . . -177.78(15) ?
C11 C2 C3 C14 . . . . 2.8(2) ?
C2 C3 C4 C5 . . . . 179.76(15) ?
C14 C3 C4 C5 . . . . -1.4(2) ?
C2 C3 C4 C9 . . . . -0.7(2) ?
C14 C3 C4 C9 . . . . 178.17(15) ?
C9 C4 C5 C6 . . . . 1.7(3) ?
C3 C4 C5 C6 . . . . -178.74(16) ?
C4 C5 C6 C7 . . . . -2.3(3) ?
C4 C5 C6 Cl1 . . . . 177.19(13) ?
C5 C6 C7 C8 . . . . 1.3(3) ?
Cl1 C6 C7 C8 . . . . -178.20(14) ?
C6 C7 C8 C9 . . . . 0.3(3) ?
C1 N1 C9 C8 . . . . 179.84(16) ?
C1 N1 C9 C4 . . . . -0.1(3) ?
C7 C8 C9 N1 . . . . 179.20(17) ?
C7 C8 C9 C4 . . . . -0.8(3) ?
C5 C4 C9 N1 . . . . 179.81(15) ?
C3 C4 C9 N1 . . . . 0.2(2) ?
C5 C4 C9 C8 . . . . -0.2(2) ?
C3 C4 C9 C8 . . . . -179.76(15) ?
C12 O1 C11 O2 . . . . 6.4(3) ?
C12 O1 C11 C2 . . . . -174.03(17) ?
C3 C2 C11 O2 . . . . -119.9(2) ?
C1 C2 C11 O2 . . . . 60.7(3) ?
C3 C2 C11 O1 . . . . 60.5(2) ?
C1 C2 C11 O1 . . . . -118.93(17) ?
C11 O1 C12 C13 . . . . 156.4(2) ?
C2 C3 C14 C19 . . . . -119.39(19) ?
C4 C3 C14 C19 . . . . 61.8(2) ?
C2 C3 C14 C15 . . . . 58.7(2) ?
C4 C3 C14 C15 . . . . -120.12(18) ?
C19 C14 C15 C16 . . . . -0.7(3) ?
C3 C14 C15 C16 . . . . -178.83(17) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C15 C16 C17 C18 . . . . -0.1(3) ?
C16 C17 C18 C19 . . . . -0.2(3) ?
C15 C14 C19 C18 . . . . 0.5(3) ?
C3 C14 C19 C18 . . . . 178.57(18) ?
C17 C18 C19 C14 . . . . 0.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 546888
