#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/40/2234046.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_2234046
loop_
_publ_author_name
'Gültekin, Zeynep'
'Bolte, Michael'
'Hökelek, Tuncer'
_publ_section_title
;
 Dimethyl 6-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate
;
_journal_coeditor_code           XU5460
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o606
_journal_paper_doi               10.1107/S1600536812003650
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H17 N O5'
_chemical_formula_moiety         'C16 H17 N O5'
_chemical_formula_sum            'C16 H17 N O5'
_chemical_formula_weight         303.31
_chemical_name_systematic
;
Dimethyl 6-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate
;
_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           SHELXL97
_cell_angle_alpha                89.308(7)
_cell_angle_beta                 74.436(7)
_cell_angle_gamma                71.568(7)
_cell_formula_units_Z            2
_cell_length_a                   7.9853(7)
_cell_length_b                   8.3950(7)
_cell_length_c                   12.4416(11)
_cell_measurement_reflns_used    11792
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      3.5
_cell_volume                     759.82(12)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12439
_diffrn_reflns_theta_full        25.63
_diffrn_reflns_theta_max         25.63
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0649P)²+0.2357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                2507
_reflns_number_total             2833
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5460.cif
_cod_data_source_block           I
_cod_database_code               2234046
_cod_database_fobs_code          2234046
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_symmetry_multiplicity
O O1 0.6972(2) -0.1203(2) 0.18082(12) 0.0633(4) Uani d . 1 1
O O2 0.69874(15) -0.00298(16) 0.34026(9) 0.0414(3) Uani d . 1 1
O O3 0.12719(16) 0.61353(14) 0.44347(9) 0.0371(3) Uani d . 1 1
O O4 0.29430(17) 0.43432(16) 0.53946(10) 0.0443(3) Uani d . 1 1
O O5 0.26090(17) 0.80610(14) 0.09807(10) 0.0407(3) Uani d . 1 1
N N1 0.31769(19) 0.06145(17) 0.22877(11) 0.0332(3) Uani d . 1 1
H H1 0.322(3) -0.019(3) 0.1868(16) 0.037(5) Uiso d . 1 1
C C2 0.4058(2) 0.01893(18) 0.31827(12) 0.0297(3) Uani d . 1 1
C C3 0.34378(19) 0.17245(19) 0.39857(12) 0.0286(3) Uani d . 1 1
H H3 0.3402 0.1582 0.4733 0.034 Uiso calc R 1 1
C C4 0.29367(18) 0.32849(18) 0.36578(12) 0.0271(3) Uani d . 1 1
C C5 0.27307(19) 0.50723(18) 0.20096(12) 0.0278(3) Uani d . 1 1
H H5 0.2688 0.5999 0.2431 0.033 Uiso calc R 1 1
C C6 0.26233(19) 0.52543(19) 0.09059(12) 0.0285(3) Uani d . 1 1
C C7 0.2661(2) 0.38508(19) 0.02853(12) 0.0312(3) Uani d . 1 1
H H7 0.2549 0.3960 -0.0439 0.037 Uiso calc R 1 1
C C8 0.2861(2) 0.23170(19) 0.07329(13) 0.0317(3) Uani d . 1 1
H H8 0.2896 0.1398 0.0307 0.038 Uiso calc R 1 1
C C9 0.30114(19) 0.21314(18) 0.18284(12) 0.0278(3) Uani d . 1 1
C C10 0.28990(18) 0.35501(18) 0.24904(12) 0.0266(3) Uani d . 1 1
C C11 0.3554(3) -0.1283(2) 0.37615(15) 0.0416(4) Uani d . 1 1
H H11A 0.3912 -0.2219 0.3219 0.062 Uiso calc R 1 1
H H11B 0.2252 -0.0943 0.4101 0.062 Uiso calc R 1 1
H H11C 0.4185 -0.1609 0.4327 0.062 Uiso calc R 1 1
C C12 0.6168(2) -0.04291(18) 0.26972(12) 0.0317(3) Uani d . 1 1
C C13 0.8977(2) -0.0641(3) 0.30643(17) 0.0581(6) Uani d . 1 1
H H13A 0.9424 -0.0192 0.3594 0.087 Uiso calc R 1 1
H H13B 0.9422 -0.0287 0.2337 0.087 Uiso calc R 1 1
H H13C 0.9403 -0.1849 0.3038 0.087 Uiso calc R 1 1
C C14 0.2280(2) 0.47500(19) 0.45107(12) 0.0291(3) Uani d . 1 1
C C15 0.2295(3) 0.5639(3) 0.63061(15) 0.0539(5) Uani d . 1 1
H H15A 0.2683 0.5165 0.6940 0.081 Uiso calc R 1 1
H H15B 0.0977 0.6081 0.6507 0.081 Uiso calc R 1 1
H H15C 0.2795 0.6528 0.6075 0.081 Uiso calc R 1 1
C C16 0.2474(2) 0.69166(19) 0.04489(12) 0.0307(3) Uani d . 1 1
C C17 0.2142(3) 0.7197(2) -0.06869(14) 0.0419(4) Uani d . 1 1
H H17A 0.1961 0.8356 -0.0833 0.063 Uiso calc R 1 1
H H17B 0.1068 0.6923 -0.0700 0.063 Uiso calc R 1 1
H H17C 0.3186 0.6491 -0.1250 0.063 Uiso calc R 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O2 C13 116.35(13)
C14 O4 C15 116.25(14)
C2 N1 H1 117.4(13)
C9 N1 C2 120.53(12)
C9 N1 H1 116.4(13)
N1 C2 C3 108.66(12)
N1 C2 C11 109.05(12)
N1 C2 C12 110.27(12)
C3 C2 C11 111.68(13)
C3 C2 C12 110.74(11)
C11 C2 C12 106.42(13)
C2 C3 H3 119.0
C4 C3 C2 122.03(13)
C4 C3 H3 119.0
C3 C4 C10 120.21(13)
C3 C4 C14 119.01(13)
C10 C4 C14 120.62(13)
C6 C5 H5 119.0
C10 C5 C6 121.90(13)
C10 C5 H5 119.0
C5 C6 C7 118.37(13)
C5 C6 C16 118.55(13)
C7 C6 C16 123.08(13)
C6 C7 H7 119.5
C8 C7 C6 121.02(13)
C8 C7 H7 119.5
C7 C8 C9 120.37(13)
C7 C8 H8 119.8
C9 C8 H8 119.8
N1 C9 C8 120.72(13)
N1 C9 C10 119.52(13)
C8 C9 C10 119.69(13)
C5 C10 C4 124.87(13)
C5 C10 C9 118.57(13)
C9 C10 C4 116.55(13)
C2 C11 H11A 109.5
C2 C11 H11B 109.5
C2 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O1 C12 O2 124.00(15)
O1 C12 C2 124.45(14)
O2 C12 C2 111.53(12)
O2 C13 H13A 109.5
O2 C13 H13B 109.5
O2 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O3 C14 O4 123.01(14)
O3 C14 C4 125.35(14)
O4 C14 C4 111.64(13)
O4 C15 H15A 109.5
O4 C15 H15B 109.5
O4 C15 H15C 109.5
H15A C15 H15B 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O5 C16 C6 120.92(14)
O5 C16 C17 119.68(14)
C6 C16 C17 119.41(13)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.196(2)
O2 C12 1.3287(19)
O2 C13 1.447(2)
O3 C14 1.2063(19)
O4 C14 1.3401(19)
O4 C15 1.4476(19)
O5 C16 1.2211(19)
N1 C2 1.4540(19)
N1 C9 1.372(2)
N1 H1 0.85(2)
C2 C11 1.531(2)
C2 C12 1.543(2)
C3 C2 1.505(2)
C3 C4 1.336(2)
C3 H3 0.9300
C4 C14 1.496(2)
C5 C6 1.402(2)
C5 H5 0.9300
C6 C7 1.404(2)
C6 C16 1.482(2)
C7 H7 0.9300
C8 C7 1.376(2)
C8 H8 0.9300
C9 C8 1.403(2)
C10 C4 1.474(2)
C10 C5 1.387(2)
C10 C9 1.422(2)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C17 1.509(2)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 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
_geom_hbond_publ_flag
N1 H1 O5 1_545 0.85(2) 2.10(2) 2.9223(19) 166(2) yes
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
C13 O2 C12 O1 -2.3(3)
C13 O2 C12 C2 176.23(15)
C15 O4 C14 O3 3.7(2)
C15 O4 C14 C4 -176.03(14)
C9 N1 C2 C3 41.36(19)
C9 N1 C2 C11 163.31(14)
C9 N1 C2 C12 -80.19(17)
C2 N1 C9 C8 154.73(14)
C2 N1 C9 C10 -28.4(2)
N1 C2 C12 O1 -33.1(2)
N1 C2 C12 O2 148.35(13)
C3 C2 C12 O1 -153.45(17)
C3 C2 C12 O2 28.05(17)
C11 C2 C12 O1 85.0(2)
C11 C2 C12 O2 -93.51(15)
C4 C3 C2 N1 -28.33(19)
C4 C3 C2 C11 -148.66(14)
C4 C3 C2 C12 92.93(16)
C2 C3 C4 C10 2.8(2)
C2 C3 C4 C14 178.09(12)
C3 C4 C14 O3 -155.01(15)
C3 C4 C14 O4 24.69(19)
C10 C4 C14 O3 20.3(2)
C10 C4 C14 O4 -159.98(12)
C10 C5 C6 C7 1.0(2)
C10 C5 C6 C16 -179.06(13)
C5 C6 C7 C8 -2.2(2)
C16 C6 C7 C8 177.88(14)
C5 C6 C16 O5 6.5(2)
C5 C6 C16 C17 -173.14(13)
C7 C6 C16 O5 -173.48(14)
C7 C6 C16 C17 6.8(2)
C9 C8 C7 C6 0.7(2)
N1 C9 C8 C7 178.80(14)
C10 C9 C8 C7 2.0(2)
C5 C10 C4 C3 -167.68(14)
C5 C10 C4 C14 17.1(2)
C9 C10 C4 C3 13.5(2)
C9 C10 C4 C14 -161.74(13)
C4 C10 C5 C6 -177.15(13)
C9 C10 C5 C6 1.6(2)
C4 C10 C9 N1 -1.1(2)
C4 C10 C9 C8 175.78(12)
C5 C10 C9 N1 -179.95(13)
C5 C10 C9 C8 -3.1(2)
