#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223131.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_2223131
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Hakim Al-Arique, Q. N. M.'
'Yathirajan, H. S.'
'Narayana, B.'
_publ_section_title
;
 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium
 2,4,6-trinitrophenolate
;
_journal_coeditor_code           IS2446
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2201
_journal_page_last               o2202
_journal_paper_doi               10.1107/S1600536809032693
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H12 Cl N2 O +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C11 H12 Cl N2 O +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C17 H14 Cl N5 O8'
_chemical_formula_weight         451.78
_chemical_name_common
;
3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a] pyrimidinium-4-one
picrate
;
_chemical_name_systematic
;
3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium
2,4,6-trinitrophenolate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.642(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2718(5)
_cell_length_b                   12.8159(9)
_cell_length_c                   19.940(3)
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      74.1343
_cell_measurement_theta_min      4.1062
_cell_volume                     1841.8(3)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6948
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.04
_diffrn_reflns_theta_min         4.11
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.405
_exptl_absorpt_correction_T_max  0.575
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.063P)²+0.629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                3198
_reflns_number_total             3616
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2446.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223131
_cod_database_fobs_code          2223131
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_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
Cl Cl1A 0.86173(5) 0.88220(3) 0.687448(19) 0.02115(12) Uani d . 1 . .
O O1A 0.51748(16) 0.63234(9) 0.76768(5) 0.0210(2) Uani d . 1 . .
N N1A 0.37082(17) 0.50513(9) 0.69885(6) 0.0150(3) Uani d . 1 . .
C C1A 0.5193(2) 0.58121(11) 0.71692(8) 0.0162(3) Uani d . 1 . .
C C2A 0.6526(2) 0.58732(11) 0.66975(7) 0.0153(3) Uani d . 1 . .
C C3A 0.6432(2) 0.52080(11) 0.61613(7) 0.0154(3) Uani d . 1 . .
N N4A 0.50951(17) 0.44532(10) 0.60742(6) 0.0162(3) Uani d . 1 . .
H H4AA 0.5124 0.4000 0.5744 0.019 Uiso calc R 1 . .
C C5A 0.3734(2) 0.43685(11) 0.64690(7) 0.0157(3) Uani d . 1 . .
C C6A 0.2346(2) 0.35986(12) 0.63478(8) 0.0196(3) Uani d . 1 . .
H H6AA 0.2378 0.3105 0.5994 0.024 Uiso calc R 1 . .
C C7A 0.0949(2) 0.35698(13) 0.67466(9) 0.0226(3) Uani d . 1 . .
H H7AA 0.0018 0.3046 0.6677 0.027 Uiso calc R 1 . .
C C8A 0.0903(2) 0.43233(13) 0.72609(8) 0.0227(3) Uani d . 1 . .
H H8AA -0.0095 0.4328 0.7524 0.027 Uiso calc R 1 . .
C C9A 0.2275(2) 0.50377(12) 0.73803(8) 0.0190(3) Uani d . 1 . .
H H9AA 0.2254 0.5532 0.7734 0.023 Uiso calc R 1 . .
C C10A 0.7963(2) 0.67205(12) 0.68363(8) 0.0171(3) Uani d . 1 . .
H H10A 0.9037 0.6568 0.6595 0.021 Uiso calc R 1 . .
H H10B 0.8409 0.6754 0.7327 0.021 Uiso calc R 1 . .
C C11A 0.7098(2) 0.77552(12) 0.65971(8) 0.0187(3) Uani d . 1 . .
H H11A 0.5904 0.7844 0.6778 0.022 Uiso calc R 1 . .
H H11B 0.6843 0.7757 0.6097 0.022 Uiso calc R 1 . .
C C12A 0.7717(2) 0.52487(13) 0.56313(8) 0.0202(3) Uani d . 1 . .
H H12A 0.9003 0.5188 0.5848 0.030 Uiso calc R 1 . .
H H12B 0.7554 0.5914 0.5388 0.030 Uiso calc R 1 . .
H H12C 0.7433 0.4671 0.5312 0.030 Uiso calc R 1 . .
O O1B 0.57412(15) 0.30604(8) 0.51298(5) 0.0185(2) Uani d . 1 . .
O O21B 0.81068(17) 0.36265(9) 0.42333(6) 0.0246(3) Uani d . 1 . .
O O22B 0.75216(16) 0.25511(9) 0.33919(6) 0.0223(3) Uani d . 1 . .
O O41B 0.88575(16) -0.10609(9) 0.40701(6) 0.0233(3) Uani d . 1 . .
O O42B 0.78903(17) -0.16264(9) 0.49860(6) 0.0248(3) Uani d . 1 . .
O O61B 0.52961(16) 0.07476(10) 0.64703(6) 0.0250(3) Uani d . 1 . .
O O62B 0.61759(18) 0.23621(9) 0.64474(6) 0.0257(3) Uani d . 1 . .
N N2B 0.76693(17) 0.27587(10) 0.40009(7) 0.0174(3) Uani d . 1 . .
N N4B 0.81817(17) -0.09140(10) 0.45962(7) 0.0175(3) Uani d . 1 . .
N N6B 0.59534(18) 0.14919(11) 0.61918(6) 0.0180(3) Uani d . 1 . .
C C1B 0.6503(2) 0.21995(11) 0.50651(7) 0.0145(3) Uani d . 1 . .
C C2B 0.7355(2) 0.19261(12) 0.44702(7) 0.0153(3) Uani d . 1 . .
C C3B 0.7866(2) 0.09381(12) 0.43082(7) 0.0158(3) Uani d . 1 . .
H H3BA 0.8335 0.0804 0.3894 0.019 Uiso calc R 1 . .
C C4B 0.76828(19) 0.01382(12) 0.47634(7) 0.0156(3) Uani d . 1 . .
C C5B 0.70412(19) 0.03312(12) 0.53788(7) 0.0157(3) Uani d . 1 . .
H H5BA 0.6955 -0.0220 0.5691 0.019 Uiso calc R 1 . .
C C6B 0.6534(2) 0.13254(12) 0.55290(7) 0.0151(3) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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
C5A N1A C9A . . 120.69(13) ?
C5A N1A C1A . . 122.17(12) ?
C9A N1A C1A . . 117.12(13) ?
O1A C1A C2A . . 126.96(14) ?
O1A C1A N1A . . 118.57(14) ?
C2A C1A N1A . . 114.47(13) ?
C3A C2A C1A . . 120.70(14) ?
C3A C2A C10A . . 123.83(14) ?
C1A C2A C10A . . 115.46(13) ?
C2A C3A N4A . . 120.25(13) ?
C2A C3A C12A . . 124.01(14) ?
N4A C3A C12A . . 115.73(13) ?
C5A N4A C3A . . 123.23(13) ?
C5A N4A H4AA . . 118.4 ?
C3A N4A H4AA . . 118.4 ?
N4A C5A N1A . . 118.62(13) ?
N4A C5A C6A . . 121.39(14) ?
N1A C5A C6A . . 119.99(14) ?
C7A C6A C5A . . 119.23(15) ?
C7A C6A H6AA . . 120.4 ?
C5A C6A H6AA . . 120.4 ?
C6A C7A C8A . . 119.56(15) ?
C6A C7A H7AA . . 120.2 ?
C8A C7A H7AA . . 120.2 ?
C9A C8A C7A . . 120.20(15) ?
C9A C8A H8AA . . 119.9 ?
C7A C8A H8AA . . 119.9 ?
C8A C9A N1A . . 120.20(15) ?
C8A C9A H9AA . . 119.9 ?
N1A C9A H9AA . . 119.9 ?
C2A C10A C11A . . 108.90(12) ?
C2A C10A H10A . . 109.9 ?
C11A C10A H10A . . 109.9 ?
C2A C10A H10B . . 109.9 ?
C11A C10A H10B . . 109.9 ?
H10A C10A H10B . . 108.3 ?
C10A C11A Cl1A . . 110.85(11) ?
C10A C11A H11A . . 109.5 ?
Cl1A C11A H11A . . 109.5 ?
C10A C11A H11B . . 109.5 ?
Cl1A C11A H11B . . 109.5 ?
H11A C11A H11B . . 108.1 ?
C3A C12A H12A . . 109.5 ?
C3A C12A H12B . . 109.5 ?
H12A C12A H12B . . 109.5 ?
C3A C12A H12C . . 109.5 ?
H12A C12A H12C . . 109.5 ?
H12B C12A H12C . . 109.5 ?
O21B N2B O22B . . 123.36(13) ?
O21B N2B C2B . . 118.35(13) ?
O22B N2B C2B . . 118.27(13) ?
O41B N4B O42B . . 122.99(13) ?
O41B N4B C4B . . 118.67(13) ?
O42B N4B C4B . . 118.33(13) ?
O62B N6B O61B . . 123.63(13) ?
O62B N6B C6B . . 118.15(13) ?
O61B N6B C6B . . 118.20(13) ?
O1B C1B C6B . . 125.86(14) ?
O1B C1B C2B . . 122.74(13) ?
C6B C1B C2B . . 111.23(13) ?
C3B C2B C1B . . 125.03(13) ?
C3B C2B N2B . . 117.04(13) ?
C1B C2B N2B . . 117.92(13) ?
C2B C3B C4B . . 118.42(14) ?
C2B C3B H3BA . . 120.8 ?
C4B C3B H3BA . . 120.8 ?
C3B C4B C5B . . 121.21(14) ?
C3B C4B N4B . . 119.28(13) ?
C5B C4B N4B . . 119.51(13) ?
C6B C5B C4B . . 119.29(14) ?
C6B C5B H5BA . . 120.4 ?
C4B C5B H5BA . . 120.4 ?
C5B C6B C1B . . 124.09(14) ?
C5B C6B N6B . . 116.97(13) ?
C1B C6B N6B . . 118.92(13) ?
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
Cl1A C11A . 1.7979(15) ?
O1A C1A . 1.2073(19) ?
N1A C5A . 1.3582(19) ?
N1A C9A . 1.3835(19) ?
N1A C1A . 1.4636(19) ?
C1A C2A . 1.440(2) ?
C2A C3A . 1.362(2) ?
C2A C10A . 1.507(2) ?
C3A N4A . 1.3659(19) ?
C3A C12A . 1.502(2) ?
N4A C5A . 1.3485(19) ?
N4A H4AA . 0.8800 ?
C5A C6A . 1.409(2) ?
C6A C7A . 1.372(2) ?
C6A H6AA . 0.9500 ?
C7A C8A . 1.412(2) ?
C7A H7AA . 0.9500 ?
C8A C9A . 1.352(2) ?
C8A H8AA . 0.9500 ?
C9A H9AA . 0.9500 ?
C10A C11A . 1.517(2) ?
C10A H10A . 0.9900 ?
C10A H10B . 0.9900 ?
C11A H11A . 0.9900 ?
C11A H11B . 0.9900 ?
C12A H12A . 0.9800 ?
C12A H12B . 0.9800 ?
C12A H12C . 0.9800 ?
O1B C1B . 1.2489(18) ?
O21B N2B . 1.2303(18) ?
O22B N2B . 1.2337(17) ?
O41B N4B . 1.2307(17) ?
O42B N4B . 1.2355(18) ?
O61B N6B . 1.2317(18) ?
O62B N6B . 1.2279(18) ?
N2B C2B . 1.4572(19) ?
N4B C4B . 1.4469(19) ?
N6B C6B . 1.4559(19) ?
C1B C6B . 1.451(2) ?
C1B C2B . 1.452(2) ?
C2B C3B . 1.370(2) ?
C3B C4B . 1.387(2) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.392(2) ?
C5B C6B . 1.371(2) ?
C5B H5BA . 0.9500 ?
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
N4A H4AA O1B . 0.88 1.82 2.6811(16) 167.0
N4A H4AA O62B . 0.88 2.58 2.8632(17) 99.5
C5B H5BA Cl1A 1_545 0.95 2.79 3.6112(16) 145.5
C7A H7AA O1A 2_546 0.95 2.57 3.2446(19) 128.2
C12A H12C O1B . 0.98 2.41 3.2477(19) 143.7
C9A H9AA O61B 2_556 0.95 2.61 3.2734(19) 127.2
C12A H12A O21B 3_766 0.98 2.62 3.340(2) 130.8
C10A H10B O62B 2_656 0.99 2.54 3.494(2) 160.7
C11A H11A O22B 3_666 0.99 2.52 3.385(2) 145.8
C11A H11B O42B 1_565 0.99 2.56 3.431(2) 146.6
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
C5A N1A C1A O1A . . . . -172.72(13) ?
C9A N1A C1A O1A . . . . 6.0(2) ?
C5A N1A C1A C2A . . . . 8.26(19) ?
C9A N1A C1A C2A . . . . -173.04(12) ?
O1A C1A C2A C3A . . . . 176.59(15) ?
N1A C1A C2A C3A . . . . -4.5(2) ?
O1A C1A C2A C10A . . . . -4.5(2) ?
N1A C1A C2A C10A . . . . 174.42(12) ?
C1A C2A C3A N4A . . . . -1.8(2) ?
C10A C2A C3A N4A . . . . 179.40(13) ?
C1A C2A C3A C12A . . . . 177.36(14) ?
C10A C2A C3A C12A . . . . -1.5(2) ?
C2A C3A N4A C5A . . . . 5.2(2) ?
C12A C3A N4A C5A . . . . -174.00(13) ?
C3A N4A C5A N1A . . . . -1.5(2) ?
C3A N4A C5A C6A . . . . 177.89(14) ?
C9A N1A C5A N4A . . . . 175.85(13) ?
C1A N1A C5A N4A . . . . -5.5(2) ?
C9A N1A C5A C6A . . . . -3.5(2) ?
C1A N1A C5A C6A . . . . 175.12(13) ?
N4A C5A C6A C7A . . . . -177.42(14) ?
N1A C5A C6A C7A . . . . 2.0(2) ?
C5A C6A C7A C8A . . . . 1.3(2) ?
C6A C7A C8A C9A . . . . -3.1(2) ?
C7A C8A C9A N1A . . . . 1.6(2) ?
C5A N1A C9A C8A . . . . 1.8(2) ?
C1A N1A C9A C8A . . . . -176.96(13) ?
C3A C2A C10A C11A . . . . 100.58(17) ?
C1A C2A C10A C11A . . . . -78.29(16) ?
C2A C10A C11A Cl1A . . . . 170.43(10) ?
O1B C1B C2B C3B . . . . -165.97(15) ?
C6B C1B C2B C3B . . . . 9.5(2) ?
O1B C1B C2B N2B . . . . 13.0(2) ?
C6B C1B C2B N2B . . . . -171.52(12) ?
O21B N2B C2B C3B . . . . -145.18(14) ?
O22B N2B C2B C3B . . . . 33.30(19) ?
O21B N2B C2B C1B . . . . 35.76(19) ?
O22B N2B C2B C1B . . . . -145.77(14) ?
C1B C2B C3B C4B . . . . -4.6(2) ?
N2B C2B C3B C4B . . . . 176.39(13) ?
C2B C3B C4B C5B . . . . -1.6(2) ?
C2B C3B C4B N4B . . . . 178.83(13) ?
O41B N4B C4B C3B . . . . 4.1(2) ?
O42B N4B C4B C3B . . . . -175.13(13) ?
O41B N4B C4B C5B . . . . -175.43(13) ?
O42B N4B C4B C5B . . . . 5.3(2) ?
C3B C4B C5B C6B . . . . 1.8(2) ?
N4B C4B C5B C6B . . . . -178.67(13) ?
C4B C5B C6B C1B . . . . 4.3(2) ?
C4B C5B C6B N6B . . . . -177.30(13) ?
O1B C1B C6B C5B . . . . 166.06(15) ?
C2B C1B C6B C5B . . . . -9.2(2) ?
O1B C1B C6B N6B . . . . -12.4(2) ?
C2B C1B C6B N6B . . . . 172.34(12) ?
O62B N6B C6B C5B . . . . 152.45(14) ?
O61B N6B C6B C5B . . . . -26.3(2) ?
O62B N6B C6B C1B . . . . -29.02(19) ?
O61B N6B C6B C1B . . . . 152.23(13) ?
