#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006121.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_2006121
loop_
_publ_author_name
'Sudha, L.'
'Subramanian, K.'
'Steiner, Th.'
'Koellner, G.'
'Ramakrishnan, V. T. R.'
'Sriraghavan, K.'
_publ_contact_author
;
Prof. T. Steiner
Institut f\"ur Kristallographie
Freie Universit\"at Berlin
Takustrasse 6
D-14195 Berlin
Germany
;
_publ_section_title
;
 5-Dimethylamino-8-methyl-2-quinolone
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              606
_journal_page_last               607
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C12 H14 N2 O'
_chemical_formula_structural     'C12 H14 N2 O'
_chemical_formula_sum            'C12 H14 N2 O'
_chemical_formula_weight         202.25
_chemical_name_common            ' 5-(Dimethylamino)-8-methyl-2-quinolone'
_chemical_name_systematic
;
 5-(Dimethylamino)-8-methyl-2-quinolone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.89(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.133(2)
_cell_length_b                   8.642(2)
_cell_length_c                   8.7698(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.9
_cell_measurement_theta_min      10.3
_cell_volume                     1068.7(3)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonus, 1989)'
_computing_data_reduction        'CAD4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius Turbo-CAD4'
_diffrn_measurement_method       '\w--2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54176
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1988
_diffrn_reflns_theta_max         59.80
_diffrn_reflns_theta_min         5.77
_diffrn_standards_decay_%        1.4
_diffrn_standards_interval_time  30
_diffrn_standards_number         25
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   '\y scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.095
_refine_ls_goodness_of_fit_obs   1.197
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_restrained_S_obs      1.197
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_obs          0.0446
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.2396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1270
_refine_ls_wR_factor_obs         0.1222
_reflns_number_observed          1257
_reflns_number_total             1578
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    jz1147.cif
_[local]_cod_data_source_block   shelxl
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2006121
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'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0403(9) 0.0372(9) 0.0417(9) -0.0062(7) -0.0036(7) 0.0020(7)
C2 0.0455(11) 0.0367(12) 0.0455(11) -0.0024(9) -0.0041(9) 0.0052(9)
O2 0.0758(11) 0.0448(10) 0.0651(10) -0.0204(8) -0.0197(8) 0.0166(8)
C3 0.0434(11) 0.0384(11) 0.0451(11) -0.0011(9) -0.0077(9) 0.0045(9)
C4 0.0374(10) 0.0392(11) 0.0446(11) -0.0026(9) -0.0030(8) -0.0027(9)
C5 0.0451(11) 0.0359(11) 0.0397(11) -0.0034(9) 0.0054(8) -0.0019(9)
C6 0.0565(13) 0.0358(11) 0.0482(12) -0.0040(10) 0.0014(10) 0.0063(9)
C7 0.0503(12) 0.0486(13) 0.0431(11) 0.0054(10) -0.0023(9) 0.0093(10)
C8 0.0355(10) 0.0438(12) 0.0404(11) 0.0016(9) -0.0002(8) -0.0001(9)
C8' 0.0455(12) 0.0544(14) 0.0527(13) -0.0021(10) -0.0098(10) 0.0071(11)
C9 0.0344(10) 0.0335(10) 0.0379(10) 0.0022(8) 0.0045(8) 0.0001(8)
C10 0.0368(10) 0.0346(10) 0.0366(10) 0.0003(8) 0.0024(8) -0.0021(8)
N11 0.0556(11) 0.0389(10) 0.0492(10) -0.0141(8) 0.0000(8) 0.0011(8)
C12 0.0498(14) 0.075(2) 0.078(2) -0.0139(13) 0.0073(12) -0.0026(15)
C13 0.087(2) 0.0485(14) 0.068(2) -0.0212(13) 0.0015(14) 0.0040(12)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.55305(11) 0.2095(2) 0.4686(2) 0.0400(4) Uani d . 1 N
H1 0.50344(11) 0.1488(2) 0.4209(2) 0.067(7) Uiso calc R 1 H
C2 0.59998(14) 0.1508(2) 0.5968(2) 0.0429(5) Uani d . 1 C
O2 0.57727(11) 0.0242(2) 0.6505(2) 0.0630(5) Uani d . 1 O
C3 0.67573(13) 0.2451(2) 0.6644(2) 0.0428(5) Uani d . 1 C
H3 0.71155(13) 0.2093(2) 0.7602(2) 0.048(6) Uiso calc R 1 H
C4 0.69918(13) 0.3800(2) 0.6013(2) 0.0407(5) Uani d . 1 C
H4 0.75317(13) 0.4412(2) 0.6499(2) 0.043(5) Uiso calc R 1 H
C5 0.67126(14) 0.5826(2) 0.3989(2) 0.0401(5) Uani d . 1 C
C6 0.61288(14) 0.6375(2) 0.2785(2) 0.0470(5) Uani d . 1 C
H6 0.62581(14) 0.7406(2) 0.2325(2) 0.051(6) Uiso calc R 1 H
C7 0.53589(15) 0.5495(2) 0.2210(2) 0.0476(5) Uani d . 1 C
H7 0.49460(15) 0.5926(2) 0.1340(2) 0.056(6) Uiso calc R 1 H
C8 0.51379(13) 0.4069(2) 0.2774(2) 0.0400(5) Uani d . 1 C
C8' 0.43036(14) 0.3155(3) 0.2115(2) 0.0515(6) Uani d . 1 C
H8'1 0.3855(5) 0.2961(14) 0.2928(5) 0.076(8) Uiso calc R 1 H
H8'2 0.4528(2) 0.2145(7) 0.1719(15) 0.071(7) Uiso calc R 1 H
H8'3 0.3972(6) 0.3752(8) 0.1260(11) 0.073(7) Uiso calc R 1 H
C9 0.57229(12) 0.3515(2) 0.4024(2) 0.0352(5) Uani d . 1 C
C10 0.64890(12) 0.4389(2) 0.4659(2) 0.0360(5) Uani d . 1 C
N11 0.75160(12) 0.6656(2) 0.4625(2) 0.0481(5) Uani d . 1 N
C12 0.8436(2) 0.5948(3) 0.4322(3) 0.0677(7) Uani d . 1 C
H12A 0.8947(2) 0.6407(14) 0.5026(14) 0.091(9) Uiso calc R 1 H
H12B 0.8577(6) 0.6151(17) 0.3239(6) 0.111(11) Uiso calc R 1 H
H12C 0.8405(4) 0.4806(4) 0.4498(19) 0.092(9) Uiso calc R 1 H
C13 0.7521(2) 0.8310(3) 0.4308(3) 0.0682(7) Uani d . 1 C
H13A 0.8053(7) 0.8811(4) 0.4936(13) 0.067(7) Uiso calc R 1 H
H13B 0.6904(5) 0.8773(4) 0.4573(17) 0.092(9) Uiso calc R 1 H
H13C 0.7608(11) 0.8481(3) 0.3199(4) 0.104(10) Uiso calc R 1 H
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'
O O 0.0492 0.0322 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C9 125.0(2) ?
C2 N1 H1 117.50(11) ?
C9 N1 H1 117.50(10) ?
O2 C2 N1 121.1(2) ?
O2 C2 C3 123.1(2) yes
N1 C2 C3 115.8(2) yes
C4 C3 C2 121.3(2) ?
C4 C3 H3 119.36(12) ?
C2 C3 H3 119.36(11) ?
C3 C4 C10 121.8(2) ?
C3 C4 H4 119.10(12) ?
C10 C4 H4 119.10(11) ?
C6 C5 C10 118.7(2) ?
C6 C5 N11 123.1(2) ?
C10 C5 N11 118.2(2) ?
C5 C6 C7 120.1(2) ?
C5 C6 H6 119.97(12) ?
C7 C6 H6 119.97(12) ?
C8 C7 C6 123.4(2) ?
C8 C7 H7 118.29(12) ?
C6 C7 H7 118.29(12) ?
C7 C8 C9 116.7(2) ?
C7 C8 C8' 121.7(2) ?
C9 C8 C8' 121.6(2) ?
C8 C8' H8'1 109.47(11) ?
C8 C8' H8'2 109.47(11) ?
H8'1 C8' H8'2 109.5 ?
C8 C8' H8'3 109.47(11) ?
H8'1 C8' H8'3 109.5 ?
H8'2 C8' H8'3 109.5 ?
N1 C9 C10 118.4(2) ?
N1 C9 C8 120.2(2) ?
C10 C9 C8 121.4(2) ?
C9 C10 C5 119.6(2) ?
C9 C10 C4 117.6(2) ?
C5 C10 C4 122.8(2) yes
C5 N11 C13 115.7(2) ?
C5 N11 C12 114.2(2) ?
C13 N11 C12 110.9(2) ?
N11 C12 H12A 109.47(12) ?
N11 C12 H12B 109.47(13) ?
H12A C12 H12B 109.5 ?
N11 C12 H12C 109.47(12) ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
N11 C13 H13A 109.47(13) ?
N11 C13 H13B 109.47(14) ?
H13A C13 H13B 109.5 ?
N11 C13 H13C 109.47(13) ?
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
_geom_bond_publ_flag
N1 C2 1.364(2) yes
N1 C9 1.393(2) yes
N1 H1 0.95 ?
C2 O2 1.242(2) yes
C2 C3 1.440(3) yes
C3 C4 1.342(3) yes
C3 H3 1.00 ?
C4 C10 1.435(3) ?
C4 H4 1.00 ?
C5 C6 1.379(3) ?
C5 C10 1.419(3) ?
C5 N11 1.424(2) yes
C6 C7 1.394(3) ?
C6 H6 1.00 ?
C7 C8 1.372(3) ?
C7 H7 1.00 ?
C8 C9 1.411(3) ?
C8 C8' 1.502(3) ?
C8' H8'1 1.00 ?
C8' H8'2 1.00 ?
C8' H8'3 1.00 ?
C9 C10 1.404(3) ?
N11 C13 1.456(3) yes
N11 C12 1.476(3) yes
C12 H12A 1.00 ?
C12 H12B 1.00 ?
C12 H12C 1.00 ?
C13 H13A 1.00 ?
C13 H13B 1.00 ?
C13 H13C 1.00 ?
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
_geom_torsion_publ_flag
C6 C5 N11 C12 -110.7(2) yes
C6 C5 N11 C13 19.9(3) yes