#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/95/2229547.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_2229547
loop_
_publ_author_name
'Gültekin, Zeynep'
'Frey, Wolfgang'
'Hökelek, Tuncer'
_publ_section_title
;
 Dimethyl
 5,6,7-trimethoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate
;
_journal_coeditor_code           XU5153
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o576
_journal_paper_doi               10.1107/S1600536811004028
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H21 N O7'
_chemical_formula_moiety         'C17 H21 N O7'
_chemical_formula_sum            'C17 H21 N O7'
_chemical_formula_weight         351.35
_chemical_name_systematic
;
Dimethyl 5,6,7-trimethoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.476(2)
_cell_length_b                   16.552(4)
_cell_length_c                   20.238(4)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     3509.2(13)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nicolet P3'
_diffrn_measurement_method       'Wyckoff scan'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3447
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.174
_refine_ls_extinction_coef       0.0031(3)
_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   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0697
_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)+(0.0359P)²+3.1120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                1839
_reflns_number_total             3447
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5153.cif
_cod_data_source_block           I
_cod_database_code               2229547
_cod_database_fobs_code          2229547
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O O1 0.5908(3) 1.03546(16) 0.62717(15) 0.0881(10) Uani d . 1 . .
O O2 0.6233(3) 0.93649(16) 0.55547(13) 0.0713(8) Uani d . 1 . .
O O3 0.2547(3) 0.7747(2) 0.51994(16) 0.1002(11) Uani d . 1 . .
O O4 0.1503(3) 0.75844(14) 0.61564(14) 0.0745(8) Uani d . 1 . .
O O5 0.0584(2) 0.91803(14) 0.58046(11) 0.0540(6) Uani d . 1 . .
O O6 -0.0366(2) 1.05816(15) 0.63970(12) 0.0637(7) Uani d . 1 . .
O O7 0.1046(3) 1.13852(16) 0.72647(13) 0.0736(8) Uani d . 1 . .
N N1 0.4420(3) 0.9400(2) 0.70665(15) 0.0590(9) Uani d . 1 . .
H H21 0.485(4) 0.973(2) 0.733(2) 0.091(16) Uiso d . 1 . .
C C1 0.5191(3) 0.9018(2) 0.65584(19) 0.0525(9) Uani d . 1 . .
C C2 0.4333(3) 0.8467(2) 0.61660(18) 0.0536(9) Uani d . 1 . .
H H2 0.4696 0.8031 0.5946 0.064 Uiso calc R 1 . .
C C3 0.3086(3) 0.85768(19) 0.61218(16) 0.0479(8) Uani d . 1 . .
C C4 0.2492(3) 0.92839(19) 0.64312(15) 0.0445(8) Uani d . 1 . .
C C5 0.1281(3) 0.9578(2) 0.62794(16) 0.0457(8) Uani d . 1 . .
C C6 0.0824(3) 1.0285(2) 0.65599(17) 0.0489(9) Uani d . 1 . .
C C7 0.1567(3) 1.0694(2) 0.70186(17) 0.0541(9) Uani d . 1 . .
C C8 0.2776(3) 1.0412(2) 0.71861(17) 0.0566(10) Uani d . 1 . .
H H8 0.3272 1.0688 0.7493 0.068 Uiso calc R 1 . .
C C9 0.3233(3) 0.9712(2) 0.68871(16) 0.0489(9) Uani d . 1 . .
C C10 0.6265(4) 0.8538(2) 0.6884(2) 0.0730(12) Uani d . 1 . .
H H10A 0.6801 0.8899 0.7132 0.109 Uiso calc R 1 . .
H H10B 0.6763 0.8274 0.6550 0.109 Uiso calc R 1 . .
H H10C 0.5907 0.8141 0.7176 0.109 Uiso calc R 1 . .
C C11 0.5798(3) 0.9663(2) 0.61161(19) 0.0528(9) Uani d . 1 . .
C C12 0.6849(5) 0.9931(3) 0.5108(2) 0.1013(16) Uani d . 1 . .
H H12A 0.6974 0.9678 0.4686 0.152 Uiso calc R 1 . .
H H12B 0.7660 1.0088 0.5287 0.152 Uiso calc R 1 . .
H H12C 0.6319 1.0400 0.5055 0.152 Uiso calc R 1 . .
C C13 0.2345(4) 0.7940(2) 0.5758(2) 0.0613(10) Uani d . 1 . .
C C14 0.0782(5) 0.6925(3) 0.5864(3) 0.118(2) Uani d . 1 . .
H H14A 0.0260 0.6676 0.6197 0.177 Uiso calc R 1 . .
H H14B 0.1362 0.6532 0.5686 0.177 Uiso calc R 1 . .
H H14C 0.0249 0.7130 0.5517 0.177 Uiso calc R 1 . .
C C15 -0.0622(3) 0.8868(2) 0.6031(2) 0.0755(12) Uani d . 1 . .
H H15A -0.1022 0.8569 0.5682 0.113 Uiso calc R 1 . .
H H15B -0.1164 0.9308 0.6160 0.113 Uiso calc R 1 . .
H H15C -0.0483 0.8519 0.6403 0.113 Uiso calc R 1 . .
C C16 -0.0349(5) 1.1165(3) 0.5882(2) 0.0906(15) Uani d . 1 . .
H H16A -0.1179 1.1406 0.5842 0.136 Uiso calc R 1 . .
H H16B -0.0124 1.0907 0.5474 0.136 Uiso calc R 1 . .
H H16C 0.0268 1.1576 0.5984 0.136 Uiso calc R 1 . .
C C17 0.1819(4) 1.1883(2) 0.7671(2) 0.0896(15) Uani d . 1 . .
H H17A 0.1360 1.2367 0.7781 0.134 Uiso calc R 1 . .
H H17B 0.2587 1.2022 0.7438 0.134 Uiso calc R 1 . .
H H17C 0.2033 1.1597 0.8069 0.134 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'
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
C11 O2 C12 . . 116.6(3) ?
C13 O4 C14 . . 115.5(4) ?
C5 O5 C15 . . 114.5(3) ?
C6 O6 C16 . . 113.9(3) ?
C7 O7 C17 . . 118.1(3) ?
C1 N1 H21 . . 114(3) ?
C9 N1 C1 . . 118.2(3) ?
C9 N1 H21 . . 112(3) ?
N1 C1 C2 . . 107.7(3) ?
N1 C1 C10 . . 109.3(3) ?
N1 C1 C11 . . 109.9(3) ?
C2 C1 C10 . . 110.7(3) ?
C2 C1 C11 . . 111.2(3) ?
C10 C1 C11 . . 108.0(3) ?
C1 C2 H2 . . 118.6 ?
C3 C2 C1 . . 122.8(3) ?
C3 C2 H2 . . 118.6 ?
C2 C3 C4 . . 120.1(3) ?
C2 C3 C13 . . 116.6(3) ?
C4 C3 C13 . . 123.4(3) ?
C5 C4 C3 . . 124.9(3) ?
C5 C4 C9 . . 118.3(3) ?
C9 C4 C3 . . 116.7(3) ?
O5 C5 C4 . . 118.1(3) ?
O5 C5 C6 . . 120.5(3) ?
C6 C5 C4 . . 121.3(3) ?
O6 C6 C5 . . 120.9(3) ?
O6 C6 C7 . . 119.6(3) ?
C5 C6 C7 . . 119.5(3) ?
O7 C7 C6 . . 115.4(3) ?
O7 C7 C8 . . 123.9(3) ?
C6 C7 C8 . . 120.7(3) ?
C7 C8 C9 . . 119.1(3) ?
C7 C8 H8 . . 120.5 ?
C9 C8 H8 . . 120.5 ?
N1 C9 C4 . . 118.7(3) ?
C8 C9 N1 . . 120.1(3) ?
C8 C9 C4 . . 121.1(3) ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O1 C11 O2 . . 123.6(4) ?
O1 C11 C1 . . 123.7(4) ?
O2 C11 C1 . . 112.7(3) ?
O2 C12 H12A . . 109.5 ?
O2 C12 H12B . . 109.5 ?
O2 C12 H12C . . 109.5 ?
H12A C12 H12B . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O3 C13 O4 . . 124.9(4) ?
O3 C13 C3 . . 124.1(4) ?
O4 C13 C3 . . 110.9(3) ?
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 ?
O5 C15 H15A . . 109.5 ?
O5 C15 H15B . . 109.5 ?
O5 C15 H15C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O6 C16 H16A . . 109.5 ?
O6 C16 H16B . . 109.5 ?
O6 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O7 C17 H17A . . 109.5 ?
O7 C17 H17B . . 109.5 ?
O7 C17 H17C . . 109.5 ?
H17A C17 H17B . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.193(4) ?
O2 C11 . 1.320(4) ?
O2 C12 . 1.453(5) ?
O3 C13 . 1.194(4) ?
O4 C13 . 1.332(4) ?
O4 C14 . 1.453(5) ?
O5 C5 . 1.374(4) ?
O5 C15 . 1.440(4) ?
O6 C6 . 1.380(4) ?
O6 C16 . 1.421(5) ?
O7 C7 . 1.362(4) ?
O7 C17 . 1.418(4) ?
N1 C1 . 1.453(4) ?
N1 C9 . 1.394(4) ?
N1 H21 . 0.89(4) ?
C1 C2 . 1.507(5) ?
C1 C10 . 1.527(5) ?
C1 C11 . 1.532(5) ?
C2 C3 . 1.322(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.466(5) ?
C3 C13 . 1.502(5) ?
C4 C5 . 1.393(5) ?
C4 C9 . 1.399(4) ?
C5 C6 . 1.386(5) ?
C6 C7 . 1.387(5) ?
C7 C8 . 1.391(5) ?
C8 C9 . 1.393(5) ?
C8 H8 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
C14 H14A O1 8_655 0.96 2.51 3.251(6) 134 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 O2 C11 O1 . . . . -1.3(6) ?
C12 O2 C11 C1 . . . . -178.8(3) ?
C14 O4 C13 O3 . . . . -1.0(6) ?
C14 O4 C13 C3 . . . . -176.6(3) ?
C15 O5 C5 C4 . . . . 120.6(3) ?
C15 O5 C5 C6 . . . . -64.2(4) ?
C16 O6 C6 C5 . . . . -94.5(4) ?
C16 O6 C6 C7 . . . . 86.5(4) ?
C17 O7 C7 C6 . . . . -172.3(3) ?
C17 O7 C7 C8 . . . . 5.6(5) ?
C9 N1 C1 C2 . . . . -45.4(4) ?
C9 N1 C1 C10 . . . . -165.7(3) ?
C9 N1 C1 C11 . . . . 76.0(4) ?
C1 N1 C9 C8 . . . . -145.0(3) ?
C1 N1 C9 C4 . . . . 38.5(5) ?
N1 C1 C2 C3 . . . . 24.7(5) ?
C10 C1 C2 C3 . . . . 144.2(4) ?
C11 C1 C2 C3 . . . . -95.8(4) ?
N1 C1 C11 O1 . . . . 18.8(5) ?
N1 C1 C11 O2 . . . . -163.7(3) ?
C2 C1 C11 O1 . . . . 138.0(4) ?
C2 C1 C11 O2 . . . . -44.5(4) ?
C10 C1 C11 O1 . . . . -100.4(4) ?
C10 C1 C11 O2 . . . . 77.1(4) ?
C1 C2 C3 C4 . . . . 3.5(5) ?
C1 C2 C3 C13 . . . . -175.2(3) ?
C2 C3 C4 C5 . . . . 162.3(3) ?
C2 C3 C4 C9 . . . . -14.3(5) ?
C13 C3 C4 C5 . . . . -19.0(5) ?
C13 C3 C4 C9 . . . . 164.4(3) ?
C2 C3 C13 O3 . . . . -57.5(6) ?
C2 C3 C13 O4 . . . . 118.1(4) ?
C4 C3 C13 O3 . . . . 123.8(5) ?
C4 C3 C13 O4 . . . . -60.6(4) ?
C3 C4 C5 O5 . . . . -0.1(5) ?
C3 C4 C5 C6 . . . . -175.2(3) ?
C9 C4 C5 O5 . . . . 176.5(3) ?
C9 C4 C5 C6 . . . . 1.3(5) ?
C3 C4 C9 N1 . . . . -6.3(4) ?
C3 C4 C9 C8 . . . . 177.2(3) ?
C5 C4 C9 N1 . . . . 176.8(3) ?
C5 C4 C9 C8 . . . . 0.3(5) ?
O5 C5 C6 O6 . . . . 3.6(5) ?
O5 C5 C6 C7 . . . . -177.4(3) ?
C4 C5 C6 O6 . . . . 178.7(3) ?
C4 C5 C6 C7 . . . . -2.3(5) ?
C5 C6 C7 O7 . . . . 179.6(3) ?
C5 C6 C7 C8 . . . . 1.7(5) ?
O6 C6 C7 O7 . . . . -1.4(5) ?
O6 C6 C7 C8 . . . . -179.3(3) ?
O7 C7 C8 C9 . . . . -177.8(3) ?
C6 C7 C8 C9 . . . . 0.0(5) ?
C7 C8 C9 N1 . . . . -177.4(3) ?
C7 C8 C9 C4 . . . . -1.0(5) ?
