##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Dimethyl 2,6,8-trimethyl-1,2-dihydroquinoline-2,4-dicarboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H19 N O4'
_chemical_formula_sum     'C16 H19 N O4'
_chemical_formula_iupac     'C16 H19 N O4'
_chemical_formula_weight     289.33
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     7.7944(5)
_cell_length_b     23.4621(8)
_cell_length_c     8.2551(5)
_cell_angle_alpha     90.00
_cell_angle_beta     93.729(5)
_cell_angle_gamma     90.00
_cell_volume     1506.44(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     26
_cell_measurement_theta_min     12
_cell_measurement_theta_max     14
_cell_measurement_temperature     294(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.276
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nicolet P3'
_diffrn_measurement_method     Wyckoff-Scan
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3188
_diffrn_reflns_av_R_equivalents     0.0296
_diffrn_reflns_av_sigmaI/netI     0.0450
_diffrn_reflns_theta_min     1.74
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     3
_diffrn_standards_interval_count     50
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     2
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2971
_reflns_number_gt     1999
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0948
_refine_ls_R_factor_gt     0.0562
_refine_ls_wR_factor_gt     0.1226
_refine_ls_wR_factor_ref     0.1438
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.068
_refine_ls_number_reflns     2971
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0504P)²+0.6624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.186
_refine_diff_density_min     -0.207
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0030 0.0020
                         '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' 0.0060 0.0030
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0110 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'XSCANS (Siemens, 1996)'
_computing_cell_refinement     'XSCANS (Siemens, 1996)'
_computing_data_reduction     'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury
(Macrae et al., 2006)
;
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
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
    O O1 0.7764(3) 0.59692(11) -0.3063(2) 0.0640(6) Uani d . 1 . .
    O O2 0.5173(2) 0.61471(9) -0.2180(2) 0.0502(5) Uani d . 1 . .
    O O3 1.1234(3) 0.60687(11) 0.3726(3) 0.0738(7) Uani d . 1 . .
    O O4 1.1641(2) 0.56175(9) 0.1411(2) 0.0539(6) Uani d . 1 . .
    N N1 0.7690(3) 0.60501(9) 0.3076(3) 0.0393(5) Uani d . 1 . .
    H H1 0.792(4) 0.6030(12) 0.417(4) 0.054(9) Uiso d . 1 . .
    C C1 0.7476(3) 0.61554(11) -0.0238(3) 0.0334(5) Uani d . 1 . .
    C C2 0.8247(3) 0.56972(11) 0.0436(3) 0.0352(6) Uani d . 1 . .
    H H2 0.849(3) 0.5376(11) -0.018(3) 0.035(7) Uiso d . 1 . .
    C C3 0.8769(3) 0.56643(10) 0.2214(3) 0.0353(6) Uani d . 1 . .
    C C4 0.7347(3) 0.65906(11) 0.2432(3) 0.0341(5) Uani d . 1 . .
    C C5 0.7101(3) 0.70451(12) 0.3481(3) 0.0415(6) Uani d . 1 . .
    H H5 0.733(3) 0.6993(10) 0.464(3) 0.033(6) Uiso d . 1 . .
    C C6 0.6669(3) 0.75784(12) 0.2865(3) 0.0447(7) Uani d . 1 . .
    C C7 0.6494(4) 0.76513(12) 0.1202(4) 0.0466(7) Uani d . 1 . .
    H H7 0.620(3) 0.8011(12) 0.074(3) 0.046(8) Uiso d . 1 . .
    C C8 0.6763(3) 0.72106(11) 0.0118(3) 0.0403(6) Uani d . 1 . .
    C C9 0.7161(3) 0.66663(11) 0.0741(3) 0.0342(5) Uani d . 1 . .
    C C10 0.6878(3) 0.60882(11) -0.1978(3) 0.0389(6) Uani d . 1 . .
    C C11 0.4423(5) 0.60908(19) -0.3831(4) 0.0605(9) Uani d . 1 . .
    H H111 0.475(5) 0.6429(16) -0.448(4) 0.084(12) Uiso d . 1 . .
    H H112 0.485(5) 0.5743(16) -0.428(4) 0.077(12) Uiso d . 1 . .
    H H113 0.322(6) 0.6056(16) -0.371(5) 0.095(13) Uiso d . 1 . .
    C C12 0.8522(4) 0.50594(13) 0.2861(4) 0.0500(7) Uani d . 1 . .
    H H121 0.873(4) 0.5072(12) 0.407(4) 0.057(9) Uiso d . 1 . .
    H H123 0.734(4) 0.4934(13) 0.252(4) 0.064(9) Uiso d . 1 . .
    H H122 0.926(4) 0.4786(14) 0.238(4) 0.070(10) Uiso d . 1 . .
    C C13 1.0681(3) 0.58165(11) 0.2556(3) 0.0376(6) Uani d . 1 . .
    C C14 1.3481(4) 0.57041(17) 0.1667(5) 0.0720(10) Uani d . 1 . .
    H H14A 1.4029 0.5604 0.0698 0.108 Uiso calc R 1 . .
    H H14B 1.3924 0.5468 0.2549 0.108 Uiso calc R 1 . .
    H H14C 1.3709 0.6097 0.1924 0.108 Uiso calc R 1 . .
    C C15 0.6472(6) 0.80746(16) 0.4010(5) 0.0637(9) Uani d . 1 . .
    H H151 0.582(6) 0.7969(18) 0.496(5) 0.108(15) Uiso d . 1 . .
    H H152 0.588(6) 0.840(2) 0.347(5) 0.115(16) Uiso d . 1 . .
    H H153 0.754(6) 0.8168(18) 0.450(5) 0.109(16) Uiso d . 1 . .
    C C16 0.6685(4) 0.73525(12) -0.1667(3) 0.0536(8) Uani d . 1 . .
    H H16A 0.7586 0.7154 -0.2172 0.080 Uiso calc R 1 . .
    H H16B 0.6828 0.7756 -0.1802 0.080 Uiso calc R 1 . .
    H H16C 0.5591 0.7238 -0.2163 0.080 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O1 C10 . 1.199(3) ?
    O2 C10 . 1.336(3) ?
    O2 C11 . 1.454(3) ?
    O3 C13 . 1.189(3) ?
    O4 C13 . 1.328(3) ?
    O4 C14 . 1.450(3) ?
    N1 C3 . 1.453(3) ?
    N1 C4 . 1.394(3) ?
    N1 H1 . 0.91(3) ?
    C1 C2 . 1.335(3) ?
    C1 C9 . 1.475(3) ?
    C1 C10 . 1.490(3) ?
    C2 H2 . 0.94(3) ?
    C3 C2 . 1.499(3) ?
    C3 C12 . 1.533(4) ?
    C3 C13 . 1.541(3) ?
    C4 C5 . 1.395(4) ?
    C4 C9 . 1.405(3) ?
    C5 H5 . 0.97(2) ?
    C6 C5 . 1.384(4) ?
    C6 C7 . 1.381(4) ?
    C6 C15 . 1.513(4) ?
    C7 H7 . 0.95(3) ?
    C8 C7 . 1.392(4) ?
    C8 C16 . 1.508(4) ?
    C9 C8 . 1.404(3) ?
    C11 H111 . 1.00(4) ?
    C11 H112 . 0.96(4) ?
    C11 H113 . 0.95(4) ?
    C12 H121 . 1.01(3) ?
    C12 H122 . 0.97(3) ?
    C12 H123 . 0.99(3) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 H151 . 0.99(4) ?
    C15 H153 . 0.93(5) ?
    C15 H152 . 0.98(5) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
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
    C10 O2 C11 . . 116.3(2) ?
    C13 O4 C14 . . 116.4(2) ?
    C3 N1 H1 . . 111.9(19) ?
    C4 N1 C3 . . 118.9(2) ?
    C4 N1 H1 . . 116.5(18) ?
    C2 C1 C9 . . 120.9(2) ?
    C2 C1 C10 . . 114.9(2) ?
    C9 C1 C10 . . 124.1(2) ?
    C1 C2 C3 . . 122.4(2) ?
    C1 C2 H2 . . 121.5(15) ?
    C3 C2 H2 . . 116.2(15) ?
    N1 C3 C2 . . 108.6(2) ?
    N1 C3 C12 . . 108.4(2) ?
    N1 C3 C13 . . 110.5(2) ?
    C2 C3 C12 . . 110.9(2) ?
    C2 C3 C13 . . 111.4(2) ?
    C12 C3 C13 . . 107.0(2) ?
    N1 C4 C5 . . 119.3(2) ?
    N1 C4 C9 . . 119.9(2) ?
    C5 C4 C9 . . 120.7(2) ?
    C4 C5 H5 . . 119.5(15) ?
    C6 C5 C4 . . 120.2(2) ?
    C6 C5 H5 . . 120.1(15) ?
    C5 C6 C15 . . 119.9(3) ?
    C7 C6 C5 . . 118.9(3) ?
    C7 C6 C15 . . 121.2(3) ?
    C6 C7 C8 . . 122.5(3) ?
    C6 C7 H7 . . 121.0(16) ?
    C8 C7 H7 . . 116.5(16) ?
    C7 C8 C9 . . 118.6(2) ?
    C7 C8 C16 . . 117.8(2) ?
    C9 C8 C16 . . 123.5(2) ?
    C4 C9 C1 . . 115.5(2) ?
    C8 C9 C1 . . 125.4(2) ?
    C8 C9 C4 . . 119.0(2) ?
    O1 C10 O2 . . 123.2(2) ?
    O1 C10 C1 . . 125.8(2) ?
    O2 C10 C1 . . 110.9(2) ?
    O2 C11 H111 . . 109(2) ?
    O2 C11 H112 . . 108(2) ?
    O2 C11 H113 . . 104(2) ?
    H111 C11 H112 . . 111(3) ?
    H113 C11 H111 . . 114(3) ?
    H113 C11 H112 . . 110(3) ?
    C3 C12 H121 . . 107.6(17) ?
    C3 C12 H122 . . 112.1(19) ?
    C3 C12 H123 . . 108.2(18) ?
    H121 C12 H122 . . 112(3) ?
    H121 C12 H123 . . 112(2) ?
    H123 C12 H122 . . 105(3) ?
    O3 C13 O4 . . 124.2(2) ?
    O3 C13 C3 . . 124.0(2) ?
    O4 C13 C3 . . 111.8(2) ?
    O4 C14 H14A . . 109.5 ?
    O4 C14 H14B . . 109.5 ?
    O4 C14 H14C . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C6 C15 H151 . . 112(3) ?
    C6 C15 H152 . . 112(3) ?
    C6 C15 H153 . . 109(3) ?
    H151 C15 H152 . . 108(4) ?
    H151 C15 H153 . . 102(4) ?
    H153 C15 H152 . . 113(4) ?
    C8 C16 H16A . . 109.5 ?
    C8 C16 H16B . . 109.5 ?
    C8 C16 H16C . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
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
    C11 O2 C10 O1 . . . . -3.4(4) ?
    C11 O2 C10 C1 . . . . 180.0(3) ?
    C14 O4 C13 O3 . . . . 2.1(4) ?
    C14 O4 C13 C3 . . . . -176.1(2) ?
    C4 N1 C3 C2 . . . . -43.0(3) ?
    C4 N1 C3 C12 . . . . -163.6(2) ?
    C4 N1 C3 C13 . . . . 79.5(3) ?
    C3 N1 C4 C5 . . . . -148.5(2) ?
    C3 N1 C4 C9 . . . . 34.8(3) ?
    C9 C1 C2 C3 . . . . 2.5(4) ?
    C10 C1 C2 C3 . . . . -173.5(2) ?
    C2 C1 C9 C4 . . . . -14.1(3) ?
    C2 C1 C9 C8 . . . . 163.4(2) ?
    C10 C1 C9 C4 . . . . 161.5(2) ?
    C10 C1 C9 C8 . . . . -21.0(4) ?
    C2 C1 C10 O1 . . . . -58.1(4) ?
    C2 C1 C10 O2 . . . . 118.4(2) ?
    C9 C1 C10 O1 . . . . 126.0(3) ?
    C9 C1 C10 O2 . . . . -57.5(3) ?
    N1 C3 C2 C1 . . . . 24.7(3) ?
    C12 C3 C2 C1 . . . . 143.8(3) ?
    C13 C3 C2 C1 . . . . -97.2(3) ?
    N1 C3 C13 O3 . . . . 23.5(4) ?
    N1 C3 C13 O4 . . . . -158.4(2) ?
    C2 C3 C13 O3 . . . . 144.2(3) ?
    C2 C3 C13 O4 . . . . -37.6(3) ?
    C12 C3 C13 O3 . . . . -94.4(3) ?
    C12 C3 C13 O4 . . . . 83.7(3) ?
    N1 C4 C5 C6 . . . . -176.6(2) ?
    C9 C4 C5 C6 . . . . 0.0(4) ?
    N1 C4 C9 C1 . . . . -4.2(3) ?
    N1 C4 C9 C8 . . . . 178.1(2) ?
    C5 C4 C9 C1 . . . . 179.2(2) ?
    C5 C4 C9 C8 . . . . 1.5(4) ?
    C7 C6 C5 C4 . . . . -0.3(4) ?
    C15 C6 C5 C4 . . . . -177.6(3) ?
    C5 C6 C7 C8 . . . . -1.0(4) ?
    C15 C6 C7 C8 . . . . 176.3(3) ?
    C9 C8 C7 C6 . . . . 2.6(4) ?
    C16 C8 C7 C6 . . . . -174.9(3) ?
    C1 C9 C8 C7 . . . . 179.8(2) ?
    C1 C9 C8 C16 . . . . -2.9(4) ?
    C4 C9 C8 C7 . . . . -2.7(4) ?
    C4 C9 C8 C16 . . . . 174.5(2) ?
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 O1 1_556 0.91(3) 2.30(3) 3.190(3) 166(3) yes
    C2 H2 O4 3_765 0.94(3) 2.54(3) 3.444(3) 162(2) yes
data_global
_journal_date_recd_electronic     2010-10-06
_journal_date_accepted     2010-10-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     11
_journal_page_first     o2891
_journal_page_last     o2892
_journal_paper_category     QO
_journal_coeditor_code     SU2218
_publ_contact_author
;
Dr Tuncer Hökelek
Hacettepe University
Department of Physics
06532 Beytepe
Ankara
Turkey
;
_publ_contact_author_email     merzifon@hacettepe.edu.tr
_publ_contact_author_fax     '90(312)2352550'
_publ_contact_author_phone     '90(312)2977242'
_publ_section_title
;
Dimethyl 2,6,8-trimethyl-1,2-dihydroquinoline-2,4-dicarboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Gültekin, Zeynep'
;
Department of Chemistry
Çankırı Karatekin University
TR-18100
Çankırı
Turkey
;
    'Frey, Wolfgang'
;
Universität Stuttgart
Pfaffenwaldring 55
D-70569
Stuttgart
Germany
;
    'Tercan, Barış'
;
Department of Physics
Karabük University
78050 Karabük
Turkey
;
    'Hökelek*, Tuncer'
;
Department of Physics
Hacettepe University
06800 Beytepe
Ankara
Turkey
;
