#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006482.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_2006482
loop_
_publ_author_name
'Kubicki, M.'
'Szkaradzinska, M. B.'
'Codding, P. W.'
_publ_section_title
;
 3,4-Dihydro-2,6,7-trimethyl-4-oxo-3-(2-pyridyl)quinazoline-8-carboxylic
 Acid
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1291
_journal_page_last               1293
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C17 H15 N3 O3'
_chemical_formula_weight         309.32
_chemical_name_systematic
;
2,6,7-Trimethyl-3-(2'-pyridine)-3,4-dihydro-4-oxoquinazoline-8-carboxylic
Acid
;
_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                 90.703(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9397(12)
_cell_length_b                   4.9019(4)
_cell_length_c                   23.1800(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41
_cell_measurement_theta_min      8
_cell_volume                     1470.18(18)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'ENPROC (Rettig, 1978)'
_computing_molecular_graphics    'Stereochemical Workstation (Siemens, 1989)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4F diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  Ni-filter
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3095
_diffrn_reflns_theta_max         74.86
_diffrn_reflns_theta_min         3.81
_diffrn_standards_decay_%        1.7
_diffrn_standards_interval_time  33
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.226
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.307
_refine_ls_goodness_of_fit_obs   0.993
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.310
_refine_ls_restrained_S_obs      0.993
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_obs          0.0534
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0216P)^2^+1.2940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1949
_refine_ls_wR_factor_obs         0.1214
_reflns_number_gt                2079
_reflns_number_total             2978
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fg1307.cif
_[local]_cod_data_source_block   1
_[local]_cod_cif_authors_sg_H-M  'P 1 21 /n 1'
_cod_original_cell_volume        1470.2(3)
_cod_database_code               2006482
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 0.0515(14) 0.064(2) 0.0409(13) 0.0016(13) 0.0089(11) 0.0046(12)
C2 0.049(2) 0.059(2) 0.0412(15) -0.0012(15) 0.0072(12) -0.0001(14)
C21 0.060(2) 0.082(3) 0.050(2) 0.021(2) 0.010(2) 0.006(2)
N3 0.0420(12) 0.061(2) 0.0385(12) 0.0033(12) 0.0102(10) 0.0001(12)
N1' 0.0534(15) 0.081(2) 0.057(2) -0.010(2) 0.0204(12) -0.014(2)
C2' 0.047(2) 0.058(2) 0.042(2) 0.0039(15) 0.0109(12) 0.0000(14)
C3' 0.063(2) 0.066(2) 0.049(2) -0.005(2) 0.011(2) -0.003(2)
C4' 0.085(3) 0.075(3) 0.047(2) 0.003(2) 0.011(2) -0.008(2)
C5' 0.063(2) 0.089(3) 0.048(2) 0.008(2) 0.021(2) 0.002(2)
C6' 0.055(2) 0.094(3) 0.063(2) -0.007(2) 0.023(2) -0.010(2)
C4 0.0418(15) 0.061(2) 0.042(2) -0.0039(14) 0.0058(12) 0.0001(14)
O4 0.0589(13) 0.074(2) 0.0440(12) 0.0090(12) 0.0080(10) 0.0098(11)
C4A 0.0405(14) 0.058(2) 0.047(2) -0.0026(14) 0.0086(12) -0.0012(15)
C5 0.046(2) 0.062(2) 0.052(2) 0.000(2) 0.0054(14) -0.003(2)
C6 0.043(2) 0.069(2) 0.062(2) -0.001(2) 0.0101(14) -0.010(2)
C61 0.056(2) 0.081(3) 0.087(3) 0.008(2) 0.008(2) -0.017(3)
C7 0.049(2) 0.080(3) 0.051(2) -0.010(2) 0.0149(14) -0.015(2)
C71 0.084(3) 0.127(5) 0.062(3) 0.022(3) 0.031(2) -0.013(3)
C8 0.048(2) 0.066(2) 0.043(2) -0.009(2) 0.0123(13) -0.0054(15)
C81 0.071(2) 0.083(3) 0.043(2) -0.006(2) 0.018(2) -0.001(2)
O81 0.135(3) 0.131(3) 0.055(2) 0.027(2) 0.046(2) 0.015(2)
O82 0.091(2) 0.110(2) 0.0451(13) 0.025(2) 0.0144(13) 0.0135(15)
C8A 0.0418(14) 0.057(2) 0.0413(15) -0.0036(14) 0.0079(11) -0.0014(14)
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_occupancy
_atom_site_type_symbol
N1 0.5643(2) 0.1811(6) 0.59454(11) 0.0519(7) Uani d 1 N
C2 0.5135(2) 0.2243(7) 0.64116(13) 0.0499(8) Uani d 1 C
C21 0.4237(3) 0.4146(10) 0.6400(2) 0.0641(10) Uani d 1 C
H21A 0.419(3) 0.534(10) 0.6751(19) 0.099(9) Uiso d 1 H
H21B 0.360(3) 0.291(10) 0.6398(19) 0.099(9) Uiso d 1 H
H21C 0.424(3) 0.500(10) 0.602(2) 0.099(9) Uiso d 1 H
N3 0.5388(2) 0.0988(6) 0.69259(10) 0.0472(6) Uani d 1 N
N1' 0.3929(2) -0.0288(7) 0.74374(12) 0.0635(8) Uani d 1 N
C2' 0.4744(2) 0.1325(7) 0.74275(12) 0.0488(8) Uani d 1 C
C3' 0.4981(3) 0.3227(8) 0.78375(14) 0.0592(9) Uani d 1 C
H3' 0.559(3) 0.432(9) 0.780(2) 0.084(13) Uiso d 1 H
C4' 0.4298(3) 0.3516(9) 0.8288(2) 0.0688(11) Uani d 1 C
H4' 0.446(3) 0.487(10) 0.8583(18) 0.092(14) Uiso d 1 H
C5' 0.3444(3) 0.1877(9) 0.8314(2) 0.0667(11) Uani d 1 C
H5' 0.295(3) 0.204(8) 0.8640(16) 0.072(11) Uiso d 1 H
C6' 0.3299(3) 0.0014(10) 0.7886(2) 0.0705(11) Uani d 1 C
H6' 0.269(4) -0.133(10) 0.7886(19) 0.110(16) Uiso d 1 H
C4 0.6219(2) -0.0851(7) 0.69784(13) 0.0482(8) Uani d 1 C
O4 0.6430(2) -0.1878(5) 0.74455(9) 0.0589(7) Uani d 1 O
C4a 0.6753(2) -0.1379(7) 0.64426(13) 0.0484(8) Uani d 1 C
C5 0.7557(2) -0.3290(8) 0.64340(15) 0.0534(8) Uani d 1 C
H5 0.774(3) -0.421(8) 0.6810(15) 0.062(10) Uiso d 1 H
C6 0.8073(2) -0.3822(8) 0.59297(15) 0.0579(9) Uani d 1 C
C61 0.8937(3) -0.5908(10) 0.5954(2) 0.0745(12) Uani d 1 C
H61A 0.963(3) -0.506(10) 0.5838(18) 0.096(9) Uiso d 1 H
H61B 0.883(3) -0.739(10) 0.5690(19) 0.096(9) Uiso d 1 H
H61C 0.903(3) -0.659(10) 0.636(2) 0.096(9) Uiso d 1 H
C7 0.7792(2) -0.2469(8) 0.54164(14) 0.0598(10) Uani d 1 C
C71 0.8397(4) -0.3135(14) 0.4880(2) 0.091(2) Uani d 1 C
H71A 0.866(5) -0.166(14) 0.474(3) 0.149(14) Uiso d 1 H
H71B 0.797(4) -0.383(14) 0.455(3) 0.149(14) Uiso d 1 H
H71C 0.897(5) -0.420(14) 0.497(3) 0.149(14) Uiso d 1 H
C8 0.6975(2) -0.0557(8) 0.54148(13) 0.0523(8) Uani d 1 C
C81 0.6654(3) 0.0922(9) 0.48693(14) 0.0654(10) Uani d 1 C
O81 0.7089(3) 0.0642(8) 0.44173(12) 0.1064(12) Uani d 1 O
O82 0.5869(2) 0.2630(7) 0.48927(11) 0.0818(9) Uani d 1 O
H82 0.563(3) 0.270(10) 0.535(2) 0.109(16) Uiso d 1 H
C8a 0.6456(2) -0.0047(7) 0.59385(12) 0.0465(7) Uani d 1 C
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
_geom_angle_publ_flag
C2 N1 C8a 120.7(3) yes
N1 C2 N3 122.3(3) yes
N1 C2 C21 119.5(3) yes
N3 C2 C21 118.2(3) n
C2 C21 H21A 114(3) ?
C2 C21 H21B 105(3) ?
H21A C21 H21B 107(3) ?
C2 C21 H21C 106(3) ?
H21A C21 H21C 119(4) ?
H21B C21 H21C 105(4) ?
C2 N3 C4 122.2(2) n
C2 N3 C2' 120.8(3) yes
C4 N3 C2' 116.8(2) yes
C2' N1' C6' 116.3(3) yes
N1' C2' C3' 124.8(3) n
N1' C2' N3 114.4(3) n
C3' C2' N3 120.7(3) n
C2' C3' C4' 117.1(4) n
C2' C3' H3' 119(2) ?
C4' C3' H3' 124(3) ?
C5' C4' C3' 119.8(4) n
C5' C4' H4' 122(3) ?
C3' C4' H4' 118(3) ?
C6' C5' C4' 117.8(3) n
C6' C5' H5' 121(2) ?
C4' C5' H5' 121(2) ?
N1' C6' C5' 124.2(4) n
N1' C6' H6' 114(3) ?
C5' C6' H6' 122(3) ?
O4 C4 N3 120.2(3) n
O4 C4 C4A 125.5(3) n
N3 C4 C4A 114.3(3) n
C8A C4A C5 120.0(3) n
C8A C4A C4 120.4(3) n
C5 C4A C4 119.5(3) n
C6 C5 C4A 120.4(3) n
C6 C5 H5 123(2) ?
C4A C5 H5 117(2) ?
C5 C6 C7 120.3(3) n
C5 C6 C61 117.5(4) n
C7 C6 C61 122.2(3) n
C6 C61 H61A 112(3) ?
C6 C61 H61B 112(3) ?
H61A C61 H61B 105(3) ?
C6 C61 H61C 110(3) ?
H61A C61 H61C 106(3) ?
H61B C61 H61C 112(4) ?
C6 C7 C8 120.1(3) n
C6 C7 C71 117.5(4) n
C8 C7 C71 122.4(4) n
C7 C71 H71A 110(4) ?
C7 C71 H71B 115(3) ?
H71A C71 H71B 102(5) ?
C7 C71 H71C 111(4) ?
H71A C71 H71C 104(5) ?
H71B C71 H71C 114(5) ?
C7 C8 C8A 118.5(3) n
C7 C8 C81 121.2(3) n
C8a C8 C81 120.3(3) yes
O81 C81 O82 118.5(4) yes
O81 C81 C8 123.2(4) yes
O82 C81 C8 118.3(3) yes
C81 O82 H82 106(2) ?
C4A C8A N1 120.0(3) n
C4A C8A C8 120.6(3) n
N1 C8A C8 119.5(3) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.289(4) yes
N1 C8a 1.391(4) yes
C2 N3 1.377(4) n
C2 C21 1.490(5) n
C21 H21A 1.01(5) ?
C21 H21B 1.02(5) ?
C21 H21C 0.98(5) ?
N3 C4 1.408(4) n
N3 C2' 1.448(3) n
N1' C2' 1.318(4) n
N1' C6' 1.338(4) n
C2' C3' 1.364(5) n
C3' C4' 1.385(5) n
C3' H3' 0.96(4) ?
C4' C5' 1.368(6) n
C4' H4' 0.97(5) ?
C5' C6' 1.360(6) n
C5' H5' 1.00(4) ?
C6' H6' 1.03(5) ?
C4 O4 1.222(4) n
C4 C4A 1.452(4) n
C4A C8A 1.389(4) n
C4A C5 1.401(5) n
C5 C6 1.378(4) n
C5 H5 1.01(3) ?
C6 C7 1.407(5) n
C6 C61 1.515(5) n
C61 H61A 1.03(4) ?
C61 H61B 0.96(5) ?
C61 H61C 1.01(5) ?
C7 C8 1.413(5) n
C7 C71 1.513(5) n
C71 H71A 0.87(7) ?
C71 H71B 1.00(6) ?
C71 H71C 0.93(6) ?
C8 C8A 1.417(4) n
C8 C81 1.511(5) yes
C81 O81 1.203(4) yes
C81 O82 1.319(5) yes
O82 H82 1.12(5) ?
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
O82 H82 N1 1_555 1.12(5) 1.44(5) 2.494(3) 155(4) yes
C3' H3' O4 1_565 0.96(4) 2.31(4) 3.184(5) 151(3) yes
C5' H5' O81 2_455 1.00(4) 2.41(4) 3.347(4) 155(3) yes
C21 H21C O82 3_666 0.98(5) 2.41(5) 3.388(5) 175(4) yes
C5 H5 O4 4_757 1.01(3) 2.41(4) 3.387(4) 164(3) 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
C8A N1 C2 N3 2.4(5)
C8A N1 C2 C21 -177.1(3)
N1 C2 N3 C4 0.1(5)
C21 C2 N3 C4 179.6(3)
N1 C2 N3 C2' -174.3(3)
C21 C2 N3 C2' 5.3(5)
C6' N1' C2' C3' 0.3(6)
C6' N1' C2' N3 -178.2(3)
C2 N3 C2' N1' 82.0(4)
C4 N3 C2' N1' -92.7(4)
C2 N3 C2' C3' -96.6(4)
C4 N3 C2' C3' 88.7(4)
N1' C2' C3' C4' -1.7(6)
N3 C2' C3' C4' 176.8(3)
C2' C3' C4' C5' 1.6(6)
C3' C4' C5' C6' -0.4(6)
C2' N1' C6' C5' 1.1(6)
C4' C5' C6' N1' -1.1(7)
C2 N3 C4 O4 178.5(3)
C2' N3 C4 O4 -6.9(5)
C2 N3 C4 C4A -2.3(4)
C2' N3 C4 C4A 172.3(3)
O4 C4 C4A C8A -178.8(3)
N3 C4 C4A C8A 2.1(4)
O4 C4 C4A C5 2.7(5)
N3 C4 C4A C5 -176.5(3)
C8A C4A C5 C6 1.4(5)
C4 C4A C5 C6 179.9(3)
C4A C5 C6 C7 -0.6(5)
C4A C5 C6 C61 179.8(3)
C5 C6 C7 C8 -0.2(5)
C61 C6 C7 C8 179.4(3)
C5 C6 C7 C71 179.5(4)
C61 C6 C7 C71 -0.9(6)
C6 C7 C8 C8A 0.1(5)
C71 C7 C8 C8A -179.5(4)
C6 C7 C8 C81 -179.9(3)
C71 C7 C8 C81 0.5(6)
C7 C8 C81 O81 -2.7(6)
C8A C8 C81 O81 177.4(4)
C7 C8 C81 O82 178.3(3)
C8A C8 C81 O82 -1.7(5)
C5 C4A C8A N1 178.7(3)
C4 C4A C8A N1 0.2(5)
C5 C4A C8A C8 -1.4(5)
C4 C4A C8A C8 -180.0(3)
C2 N1 C8A C4A -2.5(5)
C2 N1 C8A C8 177.6(3)
C7 C8 C8A C4A 0.7(5)
C81 C8 C8A C4A -179.3(3)
C7 C8 C8A N1 -179.5(3)
C81 C8 C8A N1 0.5(5)