#------------------------------------------------------------------------------
#$Date: 2017-07-25 13:42:55 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/67/1546720.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_1546720
loop_
_publ_author_name
'Filali Baba, Yassir'
'Kandri Rodi, Youssef'
'Hayani, Sonia'
'Jasinski, Jerry P.'
'Kaur, Manpreet'
'Essassi, El Mokhtar'
_publ_section_title
;
 Ethyl 1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate
;
_journal_coeditor_code           SJ4124
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x170917
_journal_paper_doi               10.1107/S2414314617009178
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C13 H13 N O3'
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_chemical_name_systematic
;
Ethyl 1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2269(4)
_cell_length_b                   6.7034(3)
_cell_length_c                   14.0817(5)
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5340
_cell_measurement_theta_min      4.7530
_cell_volume                     1154.16(8)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.449
_diffrn_reflns_theta_min         4.790
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0710P)²+0.1102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                1036
_reflns_number_total             1219
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj4124sup1.cif
_cod_data_source_block           I
_cod_database_code               1546720
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.36454(11) 0.2500 0.25521(9) 0.0580(4) Uani d 1 . .
O O2 0.36344(10) 0.2500 0.67503(9) 0.0544(4) Uani d 1 . .
O O3 0.22613(9) 0.2500 0.57140(8) 0.0446(4) Uani d 1 . .
N N1 0.52409(11) 0.2500 0.33834(9) 0.0352(4) Uani d 1 . .
C C1 0.41212(13) 0.2500 0.33222(12) 0.0386(4) Uani d 1 . .
C C2 0.35321(13) 0.2500 0.42157(12) 0.0367(4) Uani d 1 . .
H H2 0.2772 0.2500 0.4198 0.044 Uiso calc 1 . .
C C3 0.40269(13) 0.2500 0.50701(11) 0.0313(4) Uani d 1 . .
C C4 0.52145(12) 0.2500 0.51177(11) 0.0303(4) Uani d 1 . .
C C5 0.58205(13) 0.2500 0.59667(12) 0.0370(4) Uani d 1 . .
H H5 0.5454 0.2500 0.6546 0.044 Uiso calc 1 . .
C C6 0.69501(14) 0.2500 0.59553(13) 0.0439(4) Uani d 1 . .
H H6 0.7339 0.2500 0.6523 0.053 Uiso calc 1 . .
C C7 0.75009(14) 0.2500 0.50994(13) 0.0447(4) Uani d 1 . .
H H7 0.8262 0.2500 0.5096 0.054 Uiso calc 1 . .
C C8 0.69445(13) 0.2500 0.42541(12) 0.0390(4) Uani d 1 . .
H H8 0.7328 0.2500 0.3684 0.047 Uiso calc 1 . .
C C9 0.57974(13) 0.2500 0.42483(11) 0.0312(4) Uani d 1 . .
C C10 0.33175(13) 0.2500 0.59438(12) 0.0346(4) Uani d 1 . .
C C11 0.14893(14) 0.2500 0.64993(14) 0.0491(5) Uani d 1 . .
H H11A 0.1592 0.3675 0.6891 0.059 Uiso calc 0.5 . .
H H11B 0.1592 0.1325 0.6891 0.059 Uiso calc 0.5 . .
C C12 0.03753(17) 0.2500 0.60706(19) 0.0834(9) Uani d 1 . .
H H12A 0.0232 0.3779 0.5790 0.125 Uiso calc 0.5 A -1
H H12B -0.0158 0.2236 0.6555 0.125 Uiso calc 0.5 A -1
H H12C 0.0334 0.1485 0.5591 0.125 Uiso calc 0.5 A -1
C C13 0.58549(16) 0.2500 0.24866(12) 0.0499(5) Uani d 1 . .
H H13A 0.6393 0.1458 0.2500 0.075 Uiso calc 0.5 B -1
H H13B 0.6212 0.3764 0.2406 0.075 Uiso calc 0.5 B -1
H H13C 0.5361 0.2278 0.1967 0.075 Uiso calc 0.5 B -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O3 C11 116.42(13)
C1 N1 C9 122.79(13)
C1 N1 C13 117.13(13)
C9 N1 C13 120.08(14)
O1 C1 N1 121.81(15)
O1 C1 C2 122.00(15)
N1 C1 C2 116.19(14)
C1 C2 H2 118.2
C3 C2 C1 123.52(15)
C3 C2 H2 118.2
C2 C3 C4 119.33(14)
C2 C3 C10 118.12(14)
C4 C3 C10 122.55(13)
C5 C4 C3 124.43(14)
C5 C4 C9 118.00(14)
C9 C4 C3 117.57(13)
C4 C5 H5 119.4
C6 C5 C4 121.12(15)
C6 C5 H5 119.4
C5 C6 H6 120.1
C7 C6 C5 119.86(15)
C7 C6 H6 120.1
C6 C7 H7 119.5
C8 C7 C6 121.05(16)
C8 C7 H7 119.5
C7 C8 H8 120.0
C7 C8 C9 120.08(15)
C9 C8 H8 120.0
N1 C9 C4 120.60(14)
N1 C9 C8 119.52(13)
C8 C9 C4 119.88(13)
O2 C10 O3 122.91(15)
O2 C10 C3 125.97(14)
O3 C10 C3 111.12(13)
O3 C11 H11A 110.4
O3 C11 H11B 110.4
O3 C11 C12 106.58(17)
H11A C11 H11B 108.6
C12 C11 H11A 110.4
C12 C11 H11B 110.4
C11 C12 H12A 109.5
C11 C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N1 C13 H13A 109.5
N1 C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.231(2)
O2 C10 1.200(2)
O3 C10 1.3312(19)
O3 C11 1.454(2)
N1 C1 1.372(2)
N1 C9 1.3952(19)
N1 C13 1.469(2)
C1 C2 1.450(2)
C2 H2 0.9300
C2 C3 1.347(2)
C3 C4 1.454(2)
C3 C10 1.505(2)
C4 C5 1.407(2)
C4 C9 1.417(2)
C5 H5 0.9300
C5 C6 1.381(2)
C6 H6 0.9300
C6 C7 1.381(3)
C7 H7 0.9300
C7 C8 1.371(2)
C8 H8 0.9300
C8 C9 1.403(2)
C11 H11A 0.9700
C11 H11B 0.9700
C11 C12 1.490(3)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
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
C5 H5 O2 . 0.93 2.24 2.892(2) 126.2
C8 H8 O1 4 0.93 2.37 3.285(2) 167.5

_cod_database_fobs_code 1546720
