#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/78/2017843.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017843
loop_
_publ_author_name
'Trilleras, Jorge'
'López, Luis G.'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 10-Benzyl-4-oxo-2,3,4,10-tetrahydropyrimido[4,5-b]quinolin-2-iminium
 chloride sesquihydrate: a polarized electronic structure within a complex
 hydrogen-bonded sheet structure
;
_journal_coeditor_code           GZ3179
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o469
_journal_page_last               o472
_journal_paper_doi               10.1107/S010827011003115X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H15 N4 O +, Cl -, 1.5H2 O'
_chemical_formula_moiety         'C18 H15 N4 O +, Cl -, 1.5(H2 O)'
_chemical_formula_sum            'C18 H18 Cl N4 O2.5'
_chemical_formula_weight         365.82
_chemical_name_systematic
;
10-Benzyl-4-oxo-2,3,4,10-tetrahydropyrimido[4,5-b]quinolin-2-iminium
chloride sesquihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 134.307(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.8725(10)
_cell_length_b                   18.4777(8)
_cell_length_c                   13.417(2)
_cell_measurement_reflns_used    3842
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.02
_cell_volume                     3348.2(7)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33176
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0424P)²+5.0661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                2297
_reflns_number_total             3122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3179.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C18 H18 Cl1 N4 O2.5'
_cod_database_code               2017843
_cod_database_fobs_code          2017843
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
N N1 0.28366(14) 0.40754(11) 0.6729(2) 0.0212(5) Uani d . 1 . .
C C2 0.28792(17) 0.33596(14) 0.6676(2) 0.0219(5) Uani d . 1 . .
N N3 0.20691(14) 0.29246(11) 0.5844(2) 0.0227(5) Uani d . 1 . .
H H3 0.2130 0.2384 0.5851 0.027 Uiso d R 1 . .
C C4 0.11264(17) 0.31881(13) 0.4844(2) 0.0230(5) Uani d . 1 . .
C C4A 0.10571(17) 0.39758(13) 0.4807(2) 0.0208(5) Uani d . 1 . .
C C5 0.01754(17) 0.43065(13) 0.3871(2) 0.0221(5) Uani d . 1 . .
H H5 -0.0408 0.4028 0.3199 0.027 Uiso calc R 1 . .
C C5A 0.01147(17) 0.50636(13) 0.3883(2) 0.0221(5) Uani d . 1 . .
C C6 -0.07907(18) 0.54281(14) 0.2909(3) 0.0256(6) Uani d . 1 . .
H H6 -0.1380 0.5161 0.2213 0.031 Uiso calc R 1 . .
C C7 -0.08343(19) 0.61584(14) 0.2949(3) 0.0285(6) Uani d . 1 . .
H H7 -0.1447 0.6404 0.2267 0.034 Uiso calc R 1 . .
C C8 0.00229(19) 0.65428(14) 0.3994(3) 0.0291(6) Uani d . 1 . .
H H8 -0.0015 0.7053 0.4035 0.035 Uiso calc R 1 . .
C C9 0.09212(19) 0.62104(13) 0.4967(3) 0.0254(6) Uani d . 1 . .
H H9 0.1498 0.6487 0.5672 0.031 Uiso calc R 1 . .
C C9A 0.09856(17) 0.54620(13) 0.4916(2) 0.0219(5) Uani d . 1 . .
N N10 0.18806(14) 0.51003(10) 0.58560(19) 0.0206(4) Uani d . 1 . .
C C10A 0.19477(17) 0.43727(13) 0.5820(2) 0.0196(5) Uani d . 1 . .
N N2 0.37444(14) 0.30473(11) 0.7505(2) 0.0261(5) Uani d . 1 . .
H H21 0.4296 0.3276 0.7958 0.031 Uiso d R 1 . .
H H22 0.3772 0.2569 0.7381 0.031 Uiso d R 1 . .
O O4 0.04242(13) 0.27879(9) 0.40847(19) 0.0350(5) Uani d . 1 . .
C C101 0.28004(17) 0.55194(13) 0.6920(2) 0.0230(5) Uani d . 1 . .
H H10A 0.3337 0.5185 0.7650 0.028 Uiso calc R 1 . .
H H10B 0.2694 0.5869 0.7365 0.028 Uiso calc R 1 . .
C C111 0.31152(17) 0.59210(13) 0.6315(2) 0.0207(5) Uani d . 1 . .
C C112 0.3348(2) 0.66459(14) 0.6589(3) 0.0311(6) Uani d . 1 . .
H H112 0.3304 0.6894 0.7164 0.037 Uiso calc R 1 . .
C C113 0.3642(2) 0.70135(15) 0.6040(3) 0.0348(7) Uani d . 1 . .
H H113 0.3810 0.7512 0.6247 0.042 Uiso calc R 1 . .
C C114 0.3695(2) 0.66629(17) 0.5195(3) 0.0400(7) Uani d . 1 . .
H H114 0.3888 0.6918 0.4802 0.048 Uiso calc R 1 . .
C C115 0.3469(2) 0.59412(17) 0.4921(3) 0.0438(8) Uani d . 1 . .
H H115 0.3508 0.5696 0.4339 0.053 Uiso calc R 1 . .
C C116 0.31856(19) 0.55699(14) 0.5480(3) 0.0301(6) Uani d . 1 . .
H H116 0.3037 0.5068 0.5291 0.036 Uiso calc R 1 . .
Cl Cl1 0.26888(4) 0.13346(3) 0.62419(6) 0.02335(17) Uani d . 1 . .
O O1 0.53555(13) 0.40476(11) 0.8831(2) 0.0353(5) Uani d D 1 . .
H H11 0.527(2) 0.4339(15) 0.921(3) 0.053 Uiso d D 1 . .
H H12 0.5928(15) 0.3928(17) 0.937(3) 0.053 Uiso d D 1 . .
O O2 0.5044(3) 0.4776(2) 1.0251(5) 0.0466(11) Uani d P 0.50 . .
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'
Cl Cl 0.1484 0.1585 '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
C10A N1 C2 . . 116.7(2) ?
N2 C2 N1 . . 118.8(2) ?
N2 C2 N3 . . 117.3(2) ?
N1 C2 N3 . . 123.8(2) ?
C2 N3 C4 . . 122.8(2) ?
C2 N3 H3 . . 121.7 ?
C4 N3 H3 . . 115.2 ?
O4 C4 N3 . . 121.3(2) ?
O4 C4 C4A . . 124.3(2) ?
N3 C4 C4A . . 114.4(2) ?
C5 C4A C10A . . 121.7(2) ?
C5 C4A C4 . . 120.6(2) ?
C10A C4A C4 . . 117.7(2) ?
C4A C5 C5A . . 120.0(2) ?
C4A C5 H5 . . 120.0 ?
C5A C5 H5 . . 120.0 ?
C6 C5A C5 . . 121.6(2) ?
C6 C5A C9A . . 119.5(2) ?
C5 C5A C9A . . 118.9(2) ?
C7 C6 C5A . . 120.7(2) ?
C7 C6 H6 . . 119.7 ?
C5A C6 H6 . . 119.7 ?
C6 C7 C8 . . 119.4(2) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C9 C8 C7 . . 122.0(2) ?
C9 C8 H8 . . 119.0 ?
C7 C8 H8 . . 119.0 ?
C8 C9 C9A . . 119.5(2) ?
C8 C9 H9 . . 120.3 ?
C9A C9 H9 . . 120.3 ?
N10 C9A C9 . . 121.8(2) ?
N10 C9A C5A . . 119.2(2) ?
C9 C9A C5A . . 119.0(2) ?
C10A N10 C9A . . 122.1(2) ?
C10A N10 C101 . . 118.6(2) ?
C9A N10 C101 . . 119.3(2) ?
N1 C10A N10 . . 118.0(2) ?
N1 C10A C4A . . 124.0(2) ?
N10 C10A C4A . . 118.0(2) ?
C2 N2 H21 . . 124.0 ?
C2 N2 H22 . . 118.2 ?
H21 N2 H22 . . 114.3 ?
N10 C101 C111 . . 112.30(19) ?
N10 C101 H10A . . 109.1 ?
C111 C101 H10A . . 109.1 ?
N10 C101 H10B . . 109.1 ?
C111 C101 H10B . . 109.1 ?
H10A C101 H10B . . 107.9 ?
C112 C111 C116 . . 118.7(2) ?
C112 C111 C101 . . 120.8(2) ?
C116 C111 C101 . . 120.5(2) ?
C113 C112 C111 . . 120.7(2) ?
C113 C112 H112 . . 119.6 ?
C111 C112 H112 . . 119.6 ?
C114 C113 C112 . . 120.1(3) ?
C114 C113 H113 . . 120.0 ?
C112 C113 H113 . . 120.0 ?
C113 C114 C115 . . 119.6(3) ?
C113 C114 H114 . . 120.2 ?
C115 C114 H114 . . 120.2 ?
C116 C115 C114 . . 120.6(3) ?
C116 C115 H115 . . 119.7 ?
C114 C115 H115 . . 119.7 ?
C115 C116 C111 . . 120.3(2) ?
C115 C116 H116 . . 119.8 ?
C111 C116 H116 . . 119.8 ?
H11 O1 H12 . . 110(2) ?
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
N1 C2 . 1.330(3) y
C2 N3 . 1.358(3) y
N3 C4 . 1.367(3) y
C4 C4A . 1.459(3) y
C4A C5 . 1.342(3) y
C5 C5A . 1.405(3) y
C5A C6 . 1.401(3) y
C6 C7 . 1.355(3) y
C7 C8 . 1.385(4) y
C8 C9 . 1.365(4) y
C9 C9A . 1.394(3) y
C9A N10 . 1.384(3) y
N10 C10A . 1.354(3) y
C10A N1 . 1.321(3) y
C4A C10A . 1.421(3) y
C5A C9A . 1.408(3) y
C2 N2 . 1.304(3) y
C4 O4 . 1.206(3) y
N3 H3 . 1.0052 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
N10 C101 . 1.480(3) ?
N2 H21 . 0.8643 ?
N2 H22 . 0.9072 ?
C101 C111 . 1.495(3) ?
C101 H10A . 0.9900 ?
C101 H10B . 0.9900 ?
C111 C112 . 1.377(3) ?
C111 C116 . 1.380(3) ?
C112 C113 . 1.373(4) ?
C112 H112 . 0.9500 ?
C113 C114 . 1.368(4) ?
C113 H113 . 0.9500 ?
C114 C115 . 1.370(4) ?
C114 H114 . 0.9500 ?
C115 C116 . 1.370(4) ?
C115 H115 . 0.9500 ?
C116 H116 . 0.9500 ?
O1 H11 . 0.83(4) ?
O1 H12 . 0.81(4) ?
O2 O2 5_667 1.005(8) ?
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
N2 H21 O1 . 0.86 2.03 2.876(4) 165 y
N2 H22 Cl1 . 0.91 2.71 3.484(2) 144 y
N2 H22 O4 8_556 0.91 2.33 2.745(3) 108 y
N3 H3 Cl1 . 1.00 2.09 3.068(2) 163 y
O1 H11 O2 . 0.83(4) 1.90(4) 2.711(7) 165(3) y
O1 H11 O2 5_667 0.83(4) 2.04(4) 2.847(6) 165(3) y
O1 H12 Cl1 8_556 0.81(3) 2.43(3) 3.233(3) 172(3) y
C5 H5 Cl1 8_455 0.95 2.66 3.570(3) 161 y
C101 H10A O2 5_667 0.99 2.29 3.112(6) 139 y
C101 H10B Cl1 4_556 0.99 2.58 3.519(3) 159 y
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
C10A N1 C2 N2 . . . . 176.5(2) ?
C10A N1 C2 N3 . . . . -6.3(3) ?
N2 C2 N3 C4 . . . . -173.9(2) ?
N1 C2 N3 C4 . . . . 8.8(4) ?
C2 N3 C4 O4 . . . . 177.1(2) ?
C2 N3 C4 C4A . . . . -3.9(3) ?
O4 C4 C4A C5 . . . . -1.4(4) ?
N3 C4 C4A C5 . . . . 179.7(2) ?
O4 C4 C4A C10A . . . . 176.6(2) ?
N3 C4 C4A C10A . . . . -2.3(3) ?
C10A C4A C5 C5A . . . . -0.5(3) ?
C4 C4A C5 C5A . . . . 177.4(2) ?
C4A C5 C5A C6 . . . . 179.0(2) ?
C4A C5 C5A C9A . . . . -2.1(3) ?
C5 C5A C6 C7 . . . . 179.2(2) ?
C9A C5A C6 C7 . . . . 0.3(3) ?
C5A C6 C7 C8 . . . . -2.1(4) ?
C6 C7 C8 C9 . . . . 2.0(4) ?
C7 C8 C9 C9A . . . . 0.0(4) ?
C8 C9 C9A N10 . . . . 178.5(2) ?
C8 C9 C9A C5A . . . . -1.8(3) ?
C6 C5A C9A N10 . . . . -178.6(2) ?
C5 C5A C9A N10 . . . . 2.5(3) ?
C6 C5A C9A C9 . . . . 1.7(3) ?
C5 C5A C9A C9 . . . . -177.3(2) ?
C9 C9A N10 C10A . . . . 179.5(2) ?
C5A C9A N10 C10A . . . . -0.3(3) ?
C9 C9A N10 C101 . . . . -1.9(3) ?
C5A C9A N10 C101 . . . . 178.40(19) ?
C2 N1 C10A N10 . . . . 179.5(2) ?
C2 N1 C10A C4A . . . . -0.5(3) ?
C9A N10 C10A N1 . . . . 177.8(2) ?
C101 N10 C10A N1 . . . . -0.9(3) ?
C9A N10 C10A C4A . . . . -2.2(3) ?
C101 N10 C10A C4A . . . . 179.07(19) ?
C5 C4A C10A N1 . . . . -177.3(2) ?
C4 C4A C10A N1 . . . . 4.7(3) ?
C5 C4A C10A N10 . . . . 2.7(3) ?
C4 C4A C10A N10 . . . . -175.3(2) ?
C10A N10 C101 C111 . . . . 104.9(2) ?
C9A N10 C101 C111 . . . . -73.8(3) ?
N10 C101 C111 C112 . . . . 130.2(2) ?
N10 C101 C111 C116 . . . . -50.3(3) ?
C116 C111 C112 C113 . . . . 0.1(4) ?
C101 C111 C112 C113 . . . . 179.6(2) ?
C111 C112 C113 C114 . . . . 0.9(4) ?
C112 C113 C114 C115 . . . . -1.1(5) ?
C113 C114 C115 C116 . . . . 0.3(5) ?
C114 C115 C116 C111 . . . . 0.7(5) ?
C112 C111 C116 C115 . . . . -0.9(4) ?
C101 C111 C116 C115 . . . . 179.6(3) ?
