##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2015-08-10
_journal_date_accepted     2015-08-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2015
_journal_volume     71
_journal_issue      9
_journal_page_first     804
_journal_page_last     813
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229615015119
_journal_coeditor_code     SK3598
_publ_contact_author_name     'Michael Bolte'
_publ_contact_author_address
;
Institut für Anorganische und Analytische Chemie
Goethe-Universität Frankfurt
Max-von-Laue-Strasse 7
60438 Frankfurt am Main
Germany
;
_publ_contact_author_email     'bolte@chemie.uni-frankfurt.de'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Cocrystals of 2,6-dichloroaniline and 2,6-dichlorophenol plus three new
pseudopolymorphs of their coformers
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Gerhardt, Valeska' .
;
Institut für Organische Chemie und Chemische Biologie
Goethe-Universität Frankfurt
Max-von-Laue-Strasse 7
60438 Frankfurt am Main
Germany
;
    'Bolte, Michael' .
;
Institut für Anorganische und Analytische Chemie
Goethe-Universität Frankfurt
Max-von-Laue-Strasse 7
60438 Frankfurt am Main
Germany
;
_publ_section_synopsis
;
Noncoplanar arrangements of 2,6-dichlorophenol and 2,6-dichloroaniline with
respect to their coformers are favoured, which is in agreement with the
frequent occurance of structural analogues in pharmacology and biology.
Additionally, the integration of these compounds into synthon-based networks
enhances their ability to form two-dimensional networks, either strongly
involved or just as stabilizing compounds.
;
_database_code_depnum_ccdc_archive     'CCDC 1418575'
_chemical_name_systematic
;
2,4-Diamino-6-methyl-1,3,5-triazine--N,N-dimethylacetamide (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H7 N5, C4 H9 N O'
_chemical_formula_sum     'C8 H16 N6 O'
_chemical_formula_iupac     'C4 H7 N5, C4 H9 N O'
_chemical_formula_weight     212.27
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'F d d 2'
_symmetry_space_group_name_Hall     'F 2 -2d'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'x+1/4, -y+1/4, z+1/4'
    '-x+1/4, y+1/4, z+1/4'
    'x, y+1/2, z+1/2'
    '-x, -y+1/2, z+1/2'
    'x+1/4, -y+3/4, z+3/4'
    '-x+1/4, y+3/4, z+3/4'
    'x+1/2, y, z+1/2'
    '-x+1/2, -y, z+1/2'
    'x+3/4, -y+1/4, z+3/4'
    '-x+3/4, y+1/4, z+3/4'
    'x+1/2, y+1/2, z'
    '-x+1/2, -y+1/2, z'
    'x+3/4, -y+3/4, z+1/4'
    '-x+3/4, y+3/4, z+1/4'
_cell_length_a     23.198(3)
_cell_length_b     26.327(3)
_cell_length_c     7.2880(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     4451.0(10)
_cell_formula_units_Z     16
_cell_measurement_reflns_used     8606
_cell_measurement_theta_min     3.505
_cell_measurement_theta_max     25.77
_cell_measurement_temperature     173(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.14
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.267
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1824
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_absorpt_correction_T_min     0.884
_exptl_absorpt_correction_T_max     0.922
_exptl_special_details
;
 ;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator     'Genix 3D multilayer optics'
_diffrn_measurement_device_type     'Stoe IPDS II two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17579
_diffrn_reflns_av_R_equivalents     0.1086
_diffrn_reflns_av_sigmaI/netI     0.0436
_diffrn_reflns_theta_min     3.51
_diffrn_reflns_theta_max     25.64
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -31
_diffrn_reflns_limit_k_max     31
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1139
_reflns_number_gt     996
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0787
_refine_ls_R_factor_gt     0.0660
_refine_ls_wR_factor_gt     0.1531
_refine_ls_wR_factor_ref     0.1589
_refine_ls_goodness_of_fit_ref     1.136
_refine_ls_restrained_S_all     1.133
_refine_ls_number_reflns     1139
_refine_ls_number_parameters     148
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0846P)²+6.4135P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.235
_refine_diff_density_min     -0.279
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     -
_refine_ls_abs_structure_Flack     ?
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'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL  (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.50038(16) 0.36665(13) 0.5231(5) 0.0230(9) Uani d . 1 1 . .
    C C2 0.50245(19) 0.41755(16) 0.5102(6) 0.0204(9) Uani d . 1 1 . .
    N N2 0.45481(15) 0.44296(14) 0.5518(6) 0.0247(9) Uani d D 1 1 . .
    H H21 0.4229(15) 0.4268(17) 0.584(7) 0.030 Uiso d D 1 1 . .
    H H22 0.451(2) 0.4764(10) 0.539(7) 0.030 Uiso d D 1 1 . .
    N N3 0.54958(16) 0.44451(13) 0.4587(6) 0.0229(8) Uani d . 1 1 . .
    C C4 0.59571(18) 0.41644(16) 0.4191(6) 0.0204(10) Uani d . 1 1 . .
    N N4 0.64339(16) 0.44023(15) 0.3637(6) 0.0285(10) Uani d D 1 1 . .
    H H41 0.6757(15) 0.4232(18) 0.346(8) 0.034 Uiso d D 1 1 . .
    H H42 0.642(2) 0.4728(11) 0.332(8) 0.034 Uiso d D 1 1 . .
    N N5 0.59932(17) 0.36526(14) 0.4306(6) 0.0258(9) Uani d . 1 1 . .
    C C6 0.5497(2) 0.34317(15) 0.4814(7) 0.0230(9) Uani d . 1 1 . .
    C C61 0.5499(2) 0.28668(17) 0.4904(10) 0.0388(13) Uani d . 1 1 . .
    H H61A 0.5882 0.2740 0.4571 0.058 Uiso calc R 1 1 . .
    H H61B 0.5212 0.2731 0.4047 0.058 Uiso calc R 1 1 . .
    H H61C 0.5404 0.2758 0.6154 0.058 Uiso calc R 1 1 . .
    C C1X 0.5649(3) 0.5457(3) 0.0886(10) 0.0545(17) Uani d . 1 1 . .
    H H1X1 0.5400 0.5731 0.0440 0.082 Uiso calc R 1 1 . .
    H H1X2 0.5452 0.5272 0.1870 0.082 Uiso calc R 1 1 . .
    H H1X3 0.5735 0.5223 -0.0124 0.082 Uiso calc R 1 1 . .
    C C2X 0.6213(3) 0.5683(2) 0.1627(8) 0.0471(15) Uani d . 1 1 . .
    O O2X 0.65926(18) 0.54120(14) 0.2260(7) 0.0509(11) Uani d . 1 1 . .
    N N3X 0.6268(3) 0.6178(2) 0.1502(8) 0.0600(16) Uani d . 1 1 . .
    C C4X 0.6817(4) 0.6403(3) 0.2137(11) 0.075(2) Uani d . 1 1 . .
    H H4X1 0.6805 0.6772 0.1973 0.112 Uiso calc R 1 1 . .
    H H4X2 0.7137 0.6262 0.1421 0.112 Uiso calc R 1 1 . .
    H H4X3 0.6874 0.6323 0.3439 0.112 Uiso calc R 1 1 . .
    C C5X 0.5813(4) 0.6515(3) 0.0847(14) 0.092(3) Uani d . 1 1 . .
    H H5X1 0.5951 0.6867 0.0872 0.138 Uiso calc R 1 1 . .
    H H5X2 0.5474 0.6482 0.1640 0.138 Uiso calc R 1 1 . .
    H H5X3 0.5709 0.6422 -0.0413 0.138 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C6 . 1.335(6) ?
    N1 C2 . 1.344(6) ?
    C2 N2 . 1.327(6) ?
    C2 N3 . 1.356(6) ?
    N2 H21 . 0.89(2) ?
    N2 H22 . 0.89(2) ?
    N3 C4 . 1.332(5) ?
    C4 N4 . 1.334(6) ?
    C4 N5 . 1.352(6) ?
    N4 H41 . 0.88(2) ?
    N4 H42 . 0.89(2) ?
    N5 C6 . 1.342(6) ?
    C6 C61 . 1.489(6) ?
    C61 H61A . 0.9800 ?
    C61 H61B . 0.9800 ?
    C61 H61C . 0.9800 ?
    C1X C2X . 1.536(9) ?
    C1X H1X1 . 0.9800 ?
    C1X H1X2 . 0.9800 ?
    C1X H1X3 . 0.9800 ?
    C2X O2X . 1.224(7) ?
    C2X N3X . 1.311(8) ?
    N3X C5X . 1.459(9) ?
    N3X C4X . 1.479(9) ?
    C4X H4X1 . 0.9800 ?
    C4X H4X2 . 0.9800 ?
    C4X H4X3 . 0.9800 ?
    C5X H5X1 . 0.9800 ?
    C5X H5X2 . 0.9800 ?
    C5X H5X3 . 0.9800 ?
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
    C6 N1 C2 . . 114.5(4) ?
    N2 C2 N1 . . 117.2(4) ?
    N2 C2 N3 . . 118.1(4) ?
    N1 C2 N3 . . 124.7(4) ?
    C2 N2 H21 . . 121(3) ?
    C2 N2 H22 . . 124(3) ?
    H21 N2 H22 . . 115(5) ?
    C4 N3 C2 . . 114.6(3) ?
    N3 C4 N4 . . 118.1(4) ?
    N3 C4 N5 . . 126.1(4) ?
    N4 C4 N5 . . 115.8(4) ?
    C4 N4 H41 . . 121(4) ?
    C4 N4 H42 . . 120(3) ?
    H41 N4 H42 . . 119(5) ?
    C6 N5 C4 . . 113.3(4) ?
    N1 C6 N5 . . 126.7(4) ?
    N1 C6 C61 . . 117.1(4) ?
    N5 C6 C61 . . 116.3(4) ?
    C6 C61 H61A . . 109.5 ?
    C6 C61 H61B . . 109.5 ?
    H61A C61 H61B . . 109.5 ?
    C6 C61 H61C . . 109.5 ?
    H61A C61 H61C . . 109.5 ?
    H61B C61 H61C . . 109.5 ?
    C2X C1X H1X1 . . 109.5 ?
    C2X C1X H1X2 . . 109.5 ?
    H1X1 C1X H1X2 . . 109.5 ?
    C2X C1X H1X3 . . 109.5 ?
    H1X1 C1X H1X3 . . 109.5 ?
    H1X2 C1X H1X3 . . 109.5 ?
    O2X C2X N3X . . 122.4(6) ?
    O2X C2X C1X . . 121.3(5) ?
    N3X C2X C1X . . 116.3(6) ?
    C2X N3X C5X . . 123.8(7) ?
    C2X N3X C4X . . 117.4(6) ?
    C5X N3X C4X . . 118.8(7) ?
    N3X C4X H4X1 . . 109.5 ?
    N3X C4X H4X2 . . 109.5 ?
    H4X1 C4X H4X2 . . 109.5 ?
    N3X C4X H4X3 . . 109.5 ?
    H4X1 C4X H4X3 . . 109.5 ?
    H4X2 C4X H4X3 . . 109.5 ?
    N3X C5X H5X1 . . 109.5 ?
    N3X C5X H5X2 . . 109.5 ?
    H5X1 C5X H5X2 . . 109.5 ?
    N3X C5X H5X3 . . 109.5 ?
    H5X1 C5X H5X3 . . 109.5 ?
    H5X2 C5X H5X3 . . 109.5 ?
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
    C6 N1 C2 N2 . . . . -179.4(4) ?
    C6 N1 C2 N3 . . . . 0.4(7) ?
    N2 C2 N3 C4 . . . . -180.0(4) ?
    N1 C2 N3 C4 . . . . 0.3(7) ?
    C2 N3 C4 N4 . . . . 178.6(4) ?
    C2 N3 C4 N5 . . . . -1.8(7) ?
    N3 C4 N5 C6 . . . . 2.4(7) ?
    N4 C4 N5 C6 . . . . -178.0(4) ?
    C2 N1 C6 N5 . . . . 0.4(7) ?
    C2 N1 C6 C61 . . . . -179.1(5) ?
    C4 N5 C6 N1 . . . . -1.7(7) ?
    C4 N5 C6 C61 . . . . 177.9(5) ?
    O2X C2X N3X C5X . . . . -176.6(7) ?
    C1X C2X N3X C5X . . . . 4.9(9) ?
    O2X C2X N3X C4X . . . . 0.9(9) ?
    C1X C2X N3X C4X . . . . -177.6(6) ?
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
    N2 H21 N5 15_455 0.89(2) 2.15(3) 3.037(5) 175(5)
    N2 H22 N3 2_665 0.89(2) 2.16(3) 3.041(5) 169(5)
    N4 H41 N1 7_554 0.88(2) 2.10(3) 2.973(5) 174(6)
    N4 H42 O2X . 0.89(2) 2.00(3) 2.865(5) 163(5)
data_II
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2015-08-10
_journal_date_accepted     2015-08-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2015
_journal_volume     71
_journal_issue      9
_journal_page_first     804
_journal_page_last     813
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229615015119
_journal_coeditor_code     SK3598
_database_code_depnum_ccdc_archive     'CCDC 1418576'
_chemical_name_systematic
;
2,4-Diamino-6-methyl-1,3,5-triazine--N-methylpyrrolidin-2-one (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H7 N5, C5 H9 N O'
_chemical_formula_sum     'C9 H16 N6 O'
_chemical_formula_iupac     'C4 H7 N5, C5 H9 N O'
_chemical_formula_weight     224.28
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'F d d 2'
_symmetry_space_group_name_Hall     'F 2 -2d'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'x+1/4, -y+1/4, z+1/4'
    '-x+1/4, y+1/4, z+1/4'
    'x, y+1/2, z+1/2'
    '-x, -y+1/2, z+1/2'
    'x+1/4, -y+3/4, z+3/4'
    '-x+1/4, y+3/4, z+3/4'
    'x+1/2, y, z+1/2'
    '-x+1/2, -y, z+1/2'
    'x+3/4, -y+1/4, z+3/4'
    '-x+3/4, y+1/4, z+3/4'
    'x+1/2, y+1/2, z'
    '-x+1/2, -y+1/2, z'
    'x+3/4, -y+3/4, z+1/4'
    '-x+3/4, y+3/4, z+1/4'
_cell_length_a     23.178(2)
_cell_length_b     26.3327(17)
_cell_length_c     7.3428(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     4481.7(6)
_cell_formula_units_Z     16
_cell_measurement_reflns_used     15487
_cell_measurement_theta_min     3.515
_cell_measurement_theta_max     25.97
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.330
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1920
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_absorpt_correction_T_min     0.623
_exptl_absorpt_correction_T_max     0.776
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator     'Genix 3D multilayer optics'
_diffrn_measurement_device_type     'Stoe IPDS II two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     27934
_diffrn_reflns_av_R_equivalents     0.1040
_diffrn_reflns_av_sigmaI/netI     0.0343
_diffrn_reflns_theta_min     3.52
_diffrn_reflns_theta_max     25.64
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -32
_diffrn_reflns_limit_k_max     31
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1147
_reflns_number_gt     1050
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0613
_refine_ls_R_factor_gt     0.0519
_refine_ls_wR_factor_gt     0.1007
_refine_ls_wR_factor_ref     0.1034
_refine_ls_goodness_of_fit_ref     1.216
_refine_ls_restrained_S_all     1.215
_refine_ls_number_reflns     1147
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0505P)²+1.9967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.156
_refine_diff_density_min     -0.203
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     -
_refine_ls_abs_structure_Flack     ?
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'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.49594(12) 0.36682(10) 0.5730(4) 0.0228(7) Uani d . 1 1 . .
    C C2 0.49845(14) 0.41812(12) 0.5642(5) 0.0200(7) Uani d . 1 1 . .
    N N2 0.45130(13) 0.44390(12) 0.6090(5) 0.0249(7) Uani d . 1 1 . .
    H H21 0.4501(17) 0.4796(17) 0.595(5) 0.030 Uiso d . 1 1 . .
    H H22 0.4216(18) 0.4258(16) 0.627(6) 0.030 Uiso d . 1 1 . .
    N N3 0.54562(12) 0.44473(10) 0.5151(5) 0.0209(6) Uani d . 1 1 . .
    C C4 0.59207(14) 0.41692(12) 0.4753(5) 0.0199(8) Uani d . 1 1 . .
    N N4 0.63988(13) 0.44089(12) 0.4230(5) 0.0233(7) Uani d . 1 1 . .
    H H41 0.6692(19) 0.4242(16) 0.388(6) 0.028 Uiso d . 1 1 . .
    H H42 0.6392(16) 0.4738(16) 0.406(6) 0.028 Uiso d . 1 1 . .
    N N5 0.59445(12) 0.36540(10) 0.4812(4) 0.0224(7) Uani d . 1 1 . .
    C C6 0.54485(15) 0.34311(12) 0.5305(6) 0.0227(8) Uani d . 1 1 . .
    C C61 0.54503(18) 0.28666(13) 0.5392(7) 0.0377(11) Uani d . 1 1 . .
    H H61A 0.5523 0.2758 0.6647 0.056 Uiso calc R 1 1 . .
    H H61B 0.5754 0.2734 0.4595 0.056 Uiso calc R 1 1 . .
    H H61C 0.5075 0.2737 0.4991 0.056 Uiso calc R 1 1 . .
    N N1X 0.58914(12) 0.58571(12) 0.1681(5) 0.0305(8) Uani d . 1 1 . .
    C C1X 0.55352(18) 0.54228(16) 0.1290(7) 0.0385(10) Uani d . 1 1 . .
    H H1X1 0.5742 0.5112 0.1623 0.058 Uiso calc R 1 1 . .
    H H1X2 0.5444 0.5416 -0.0013 0.058 Uiso calc R 1 1 . .
    H H1X3 0.5177 0.5445 0.1994 0.058 Uiso calc R 1 1 . .
    C C2X 0.64175(16) 0.58309(15) 0.2446(6) 0.0308(9) Uani d . 1 1 . .
    O O2X 0.66470(12) 0.54405(11) 0.2990(5) 0.0427(8) Uani d . 1 1 . .
    C C3X 0.66724(16) 0.63528(14) 0.2470(6) 0.0316(9) Uani d . 1 1 . .
    H H3X1 0.7003 0.6374 0.1621 0.038 Uiso calc R 1 1 . .
    H H3X2 0.6808 0.6441 0.3710 0.038 Uiso calc R 1 1 . .
    C C4X 0.61915(17) 0.67100(14) 0.1875(6) 0.0333(9) Uani d . 1 1 . .
    H H4X1 0.6330 0.6946 0.0921 0.040 Uiso calc R 1 1 . .
    H H4X2 0.6049 0.6911 0.2921 0.040 Uiso calc R 1 1 . .
    C C5X 0.57135(16) 0.63644(14) 0.1128(6) 0.0314(9) Uani d . 1 1 . .
    H H5X1 0.5335 0.6453 0.1663 0.038 Uiso calc R 1 1 . .
    H H5X2 0.5688 0.6390 -0.0215 0.038 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C6 . 1.331(4) ?
    N1 C2 . 1.354(4) ?
    C2 N2 . 1.328(5) ?
    C2 N3 . 1.348(4) ?
    N2 H21 . 0.95(4) ?
    N2 H22 . 0.85(4) ?
    N3 C4 . 1.334(4) ?
    C4 N4 . 1.332(4) ?
    C4 N5 . 1.358(4) ?
    N4 H41 . 0.85(5) ?
    N4 H42 . 0.88(4) ?
    N5 C6 . 1.341(4) ?
    C6 C61 . 1.488(5) ?
    C61 H61A . 0.9800 ?
    C61 H61B . 0.9800 ?
    C61 H61C . 0.9800 ?
    N1X C2X . 1.344(5) ?
    N1X C1X . 1.439(5) ?
    N1X C5X . 1.456(5) ?
    C1X H1X1 . 0.9800 ?
    C1X H1X2 . 0.9800 ?
    C1X H1X3 . 0.9800 ?
    C2X O2X . 1.224(5) ?
    C2X C3X . 1.496(5) ?
    C3X C4X . 1.522(5) ?
    C3X H3X1 . 0.9900 ?
    C3X H3X2 . 0.9900 ?
    C4X C5X . 1.535(6) ?
    C4X H4X1 . 0.9900 ?
    C4X H4X2 . 0.9900 ?
    C5X H5X1 . 0.9900 ?
    C5X H5X2 . 0.9900 ?
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
    C6 N1 C2 . . 114.8(3) ?
    N2 C2 N3 . . 117.9(3) ?
    N2 C2 N1 . . 117.6(3) ?
    N3 C2 N1 . . 124.5(3) ?
    C2 N2 H21 . . 120(2) ?
    C2 N2 H22 . . 115(3) ?
    H21 N2 H22 . . 124(4) ?
    C4 N3 C2 . . 115.3(3) ?
    N4 C4 N3 . . 118.3(3) ?
    N4 C4 N5 . . 116.7(3) ?
    N3 C4 N5 . . 125.0(3) ?
    C4 N4 H41 . . 121(3) ?
    C4 N4 H42 . . 120(3) ?
    H41 N4 H42 . . 119(4) ?
    C6 N5 C4 . . 114.2(3) ?
    N1 C6 N5 . . 126.0(3) ?
    N1 C6 C61 . . 117.4(3) ?
    N5 C6 C61 . . 116.5(3) ?
    C6 C61 H61A . . 109.5 ?
    C6 C61 H61B . . 109.5 ?
    H61A C61 H61B . . 109.5 ?
    C6 C61 H61C . . 109.5 ?
    H61A C61 H61C . . 109.5 ?
    H61B C61 H61C . . 109.5 ?
    C2X N1X C1X . . 124.3(3) ?
    C2X N1X C5X . . 114.9(3) ?
    C1X N1X C5X . . 120.7(3) ?
    N1X C1X H1X1 . . 109.5 ?
    N1X C1X H1X2 . . 109.5 ?
    H1X1 C1X H1X2 . . 109.5 ?
    N1X C1X H1X3 . . 109.5 ?
    H1X1 C1X H1X3 . . 109.5 ?
    H1X2 C1X H1X3 . . 109.5 ?
    O2X C2X N1X . . 125.0(4) ?
    O2X C2X C3X . . 126.6(4) ?
    N1X C2X C3X . . 108.4(3) ?
    C2X C3X C4X . . 106.0(3) ?
    C2X C3X H3X1 . . 110.5 ?
    C4X C3X H3X1 . . 110.5 ?
    C2X C3X H3X2 . . 110.5 ?
    C4X C3X H3X2 . . 110.5 ?
    H3X1 C3X H3X2 . . 108.7 ?
    C3X C4X C5X . . 105.4(3) ?
    C3X C4X H4X1 . . 110.7 ?
    C5X C4X H4X1 . . 110.7 ?
    C3X C4X H4X2 . . 110.7 ?
    C5X C4X H4X2 . . 110.7 ?
    H4X1 C4X H4X2 . . 108.8 ?
    N1X C5X C4X . . 103.9(3) ?
    N1X C5X H5X1 . . 111.0 ?
    C4X C5X H5X1 . . 111.0 ?
    N1X C5X H5X2 . . 111.0 ?
    C4X C5X H5X2 . . 111.0 ?
    H5X1 C5X H5X2 . . 109.0 ?
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
    C6 N1 C2 N2 . . . . -178.6(4) ?
    C6 N1 C2 N3 . . . . 0.7(6) ?
    N2 C2 N3 C4 . . . . 178.6(3) ?
    N1 C2 N3 C4 . . . . -0.6(6) ?
    C2 N3 C4 N4 . . . . 179.0(3) ?
    C2 N3 C4 N5 . . . . 0.0(6) ?
    N4 C4 N5 C6 . . . . -178.5(3) ?
    N3 C4 N5 C6 . . . . 0.4(5) ?
    C2 N1 C6 N5 . . . . -0.1(6) ?
    C2 N1 C6 C61 . . . . 179.5(4) ?
    C4 N5 C6 N1 . . . . -0.4(6) ?
    C4 N5 C6 C61 . . . . 180.0(4) ?
    C1X N1X C2X O2X . . . . -4.0(6) ?
    C5X N1X C2X O2X . . . . -179.5(4) ?
    C1X N1X C2X C3X . . . . 174.7(4) ?
    C5X N1X C2X C3X . . . . -0.8(5) ?
    O2X C2X C3X C4X . . . . -173.0(4) ?
    N1X C2X C3X C4X . . . . 8.3(4) ?
    C2X C3X C4X C5X . . . . -12.1(4) ?
    C2X N1X C5X C4X . . . . -6.9(5) ?
    C1X N1X C5X C4X . . . . 177.4(4) ?
    C3X C4X C5X N1X . . . . 11.4(4) ?
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
    N2 H21 N3 2_665 0.95(4) 2.08(4) 3.013(4) 169(4)
    N2 H22 N5 15_455 0.85(4) 2.23(5) 3.062(4) 168(4)
    N4 H41 N1 7_554 0.85(5) 2.14(5) 2.982(4) 175(4)
    N4 H42 O2X . 0.88(4) 2.09(4) 2.922(4) 157(4)
data_III
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2015-08-10
_journal_date_accepted     2015-08-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2015
_journal_volume     71
_journal_issue      9
_journal_page_first     804
_journal_page_last     813
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229615015119
_journal_coeditor_code     SK3598
_database_code_depnum_ccdc_archive     'CCDC 1418577'
_chemical_name_systematic
;
2,4-Diamino-6-methyl-1,3,5-triazine--2,6-dichlorophenol (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H4 Cl2 O, C4 H7 N5 '
_chemical_formula_sum     'C10 H11 Cl2 N5 O'
_chemical_formula_iupac     'C6 H4 Cl2 O, C4 H7 N5 '
_chemical_formula_weight     288.14
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.0318(7)
_cell_length_b     8.5779(11)
_cell_length_c     15.008(2)
_cell_angle_alpha     93.929(11)
_cell_angle_beta     96.214(11)
_cell_angle_gamma     100.121(11)
_cell_volume     631.41(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2942
_cell_measurement_theta_min     3.49
_cell_measurement_theta_max     26.04
_cell_measurement_temperature     173(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.516
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     296
_exptl_absorpt_coefficient_mu     0.509
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_absorpt_correction_T_min     0.719
_exptl_absorpt_correction_T_max     0.872
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator     'Genix 3D multilayer optics'
_diffrn_measurement_device_type     'Stoe IPDS II two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5126
_diffrn_reflns_av_R_equivalents     0.0326
_diffrn_reflns_av_sigmaI/netI     0.0370
_diffrn_reflns_theta_min     3.49
_diffrn_reflns_theta_max     25.61
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2354
_reflns_number_gt     1864
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0484
_refine_ls_R_factor_gt     0.0332
_refine_ls_wR_factor_gt     0.0766
_refine_ls_wR_factor_ref     0.0809
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     2354
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0448P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.189
_refine_diff_density_min     -0.213
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1B 0.9771(3) 0.16148(16) 0.42259(10) 0.0264(3) Uani d . 1 1 . .
    C C2B 0.8271(4) 0.21542(19) 0.48369(12) 0.0246(4) Uani d . 1 1 . .
    N N2B 0.7876(4) 0.1316(2) 0.55389(12) 0.0329(4) Uani d . 1 1 . .
    H H2B1 0.706(5) 0.168(3) 0.5937(16) 0.040 Uiso d . 1 1 . .
    H H2B2 0.853(5) 0.048(3) 0.5601(16) 0.040 Uiso d . 1 1 . .
    N N3B 0.7150(3) 0.34583(16) 0.47818(10) 0.0248(3) Uani d . 1 1 . .
    C C4B 0.7728(4) 0.42905(19) 0.40828(11) 0.0227(4) Uani d . 1 1 . .
    N N4B 0.6633(4) 0.55767(19) 0.39815(12) 0.0294(4) Uani d . 1 1 . .
    H H4B1 0.679(5) 0.603(3) 0.3510(16) 0.035 Uiso d . 1 1 . .
    H H4B2 0.545(5) 0.579(3) 0.4332(16) 0.035 Uiso d . 1 1 . .
    N N5B 0.9340(3) 0.39039(16) 0.34689(10) 0.0256(3) Uani d . 1 1 . .
    C C6B 1.0255(4) 0.2552(2) 0.35688(12) 0.0246(4) Uani d . 1 1 . .
    C C61B 1.1942(4) 0.2055(2) 0.28837(14) 0.0332(5) Uani d . 1 1 . .
    H H6B1 1.3221 0.1434 0.3158 0.050 Uiso calc PR 0.71(2) 1 A 1
    H H6B2 1.2956 0.3000 0.2659 0.050 Uiso calc PR 0.71(2) 1 A 1
    H H6B3 1.0758 0.1404 0.2383 0.050 Uiso calc PR 0.71(2) 1 A 1
    H H6BA 1.3856 0.2532 0.3069 0.050 Uiso calc PR 0.29(2) 1 A 2
    H H6BB 1.1342 0.2412 0.2302 0.050 Uiso calc PR 0.29(2) 1 A 2
    H H6BC 1.1738 0.0894 0.2829 0.050 Uiso calc PR 0.29(2) 1 A 2
    C C1A 0.1526(4) 0.6818(2) 0.19030(12) 0.0261(4) Uani d . 1 1 . .
    O O1A 0.1896(3) 0.62854(16) 0.27128(9) 0.0325(3) Uani d . 1 1 . .
    H H1A 0.083(6) 0.545(3) 0.2841(17) 0.049 Uiso d . 1 1 . .
    C C2A -0.0606(4) 0.6224(2) 0.12390(13) 0.0326(4) Uani d . 1 1 . .
    Cl Cl2A -0.30587(12) 0.46466(7) 0.14567(4) 0.04572(17) Uani d . 1 1 . .
    C C3A -0.0874(5) 0.6851(3) 0.04147(15) 0.0466(6) Uani d . 1 1 . .
    H H3A -0.2353 0.6409 -0.0030 0.056 Uiso calc R 1 1 . .
    C C4A 0.1029(6) 0.8121(3) 0.02492(16) 0.0551(7) Uani d . 1 1 . .
    H H4A 0.0858 0.8563 -0.0313 0.066 Uiso calc R 1 1 . .
    C C5A 0.3175(6) 0.8757(3) 0.08890(16) 0.0473(6) Uani d . 1 1 . .
    H H5A 0.4482 0.9638 0.0773 0.057 Uiso calc R 1 1 . .
    C C6A 0.3417(4) 0.8105(2) 0.17021(13) 0.0315(4) Uani d . 1 1 . .
    Cl Cl6A 0.61299(11) 0.88885(6) 0.25170(4) 0.04033(16) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    N1B C6B . 1.330(2) ?
    N1B C2B . 1.356(2) ?
    C2B N2B . 1.329(2) ?
    C2B N3B . 1.342(2) ?
    N2B H2B1 . 0.84(2) ?
    N2B H2B2 . 0.85(3) ?
    N3B C4B . 1.338(2) ?
    C4B N4B . 1.328(2) ?
    C4B N5B . 1.354(2) ?
    N4B H4B1 . 0.83(2) ?
    N4B H4B2 . 0.87(3) ?
    N5B C6B . 1.332(2) ?
    C6B C61B . 1.488(3) ?
    C61B H6B1 . 0.9800 ?
    C61B H6B2 . 0.9800 ?
    C61B H6B3 . 0.9800 ?
    C61B H6BA . 0.9800 ?
    C61B H6BB . 0.9800 ?
    C61B H6BC . 0.9800 ?
    C1A O1A . 1.333(2) ?
    C1A C2A . 1.382(3) ?
    C1A C6A . 1.397(3) ?
    O1A H1A . 0.86(3) ?
    C2A C3A . 1.385(3) ?
    C2A Cl2A . 1.738(2) ?
    C3A C4A . 1.374(4) ?
    C3A H3A . 0.9500 ?
    C4A C5A . 1.372(4) ?
    C4A H4A . 0.9500 ?
    C5A C6A . 1.379(3) ?
    C5A H5A . 0.9500 ?
    C6A Cl6A . 1.736(2) ?
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
    C6B N1B C2B . . 114.68(15) ?
    N2B C2B N3B . . 117.89(17) ?
    N2B C2B N1B . . 117.13(16) ?
    N3B C2B N1B . . 124.98(15) ?
    C2B N2B H2B1 . . 117.3(15) ?
    C2B N2B H2B2 . . 121.3(16) ?
    H2B1 N2B H2B2 . . 121(2) ?
    C4B N3B C2B . . 114.98(15) ?
    N4B C4B N3B . . 117.81(17) ?
    N4B C4B N5B . . 117.79(16) ?
    N3B C4B N5B . . 124.40(16) ?
    C4B N4B H4B1 . . 118.5(15) ?
    C4B N4B H4B2 . . 119.1(14) ?
    H4B1 N4B H4B2 . . 121(2) ?
    C6B N5B C4B . . 115.45(14) ?
    N1B C6B N5B . . 125.32(17) ?
    N1B C6B C61B . . 117.75(16) ?
    N5B C6B C61B . . 116.93(15) ?
    C6B C61B H6B1 . . 109.5 ?
    C6B C61B H6B2 . . 109.5 ?
    C6B C61B H6B3 . . 109.5 ?
    C6B C61B H6BA . . 109.5 ?
    C6B C61B H6BB . . 109.5 ?
    H6BA C61B H6BB . . 109.5 ?
    C6B C61B H6BC . . 109.5 ?
    H6BA C61B H6BC . . 109.5 ?
    H6BB C61B H6BC . . 109.5 ?
    O1A C1A C2A . . 125.68(17) ?
    O1A C1A C6A . . 117.98(18) ?
    C2A C1A C6A . . 116.34(17) ?
    C1A O1A H1A . . 120.0(17) ?
    C1A C2A C3A . . 122.5(2) ?
    C1A C2A Cl2A . . 118.49(14) ?
    C3A C2A Cl2A . . 119.03(18) ?
    C4A C3A C2A . . 119.1(2) ?
    C4A C3A H3A . . 120.4 ?
    C2A C3A H3A . . 120.4 ?
    C5A C4A C3A . . 120.5(2) ?
    C5A C4A H4A . . 119.7 ?
    C3A C4A H4A . . 119.7 ?
    C4A C5A C6A . . 119.4(2) ?
    C4A C5A H5A . . 120.3 ?
    C6A C5A H5A . . 120.3 ?
    C5A C6A C1A . . 122.1(2) ?
    C5A C6A Cl6A . . 119.97(17) ?
    C1A C6A Cl6A . . 117.89(14) ?
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
    C6B N1B C2B N2B . . . . -175.78(18) ?
    C6B N1B C2B N3B . . . . 4.6(3) ?
    N2B C2B N3B C4B . . . . 177.00(17) ?
    N1B C2B N3B C4B . . . . -3.4(3) ?
    C2B N3B C4B N4B . . . . 178.67(16) ?
    C2B N3B C4B N5B . . . . -0.9(3) ?
    N4B C4B N5B C6B . . . . -176.09(17) ?
    N3B C4B N5B C6B . . . . 3.5(3) ?
    C2B N1B C6B N5B . . . . -1.7(3) ?
    C2B N1B C6B C61B . . . . 178.69(17) ?
    C4B N5B C6B N1B . . . . -2.1(3) ?
    C4B N5B C6B C61B . . . . 177.56(16) ?
    O1A C1A C2A C3A . . . . 179.3(2) ?
    C6A C1A C2A C3A . . . . 0.3(3) ?
    O1A C1A C2A Cl2A . . . . 0.1(3) ?
    C6A C1A C2A Cl2A . . . . -178.86(14) ?
    C1A C2A C3A C4A . . . . -0.6(3) ?
    Cl2A C2A C3A C4A . . . . 178.52(19) ?
    C2A C3A C4A C5A . . . . 0.3(4) ?
    C3A C4A C5A C6A . . . . 0.3(4) ?
    C4A C5A C6A C1A . . . . -0.6(3) ?
    C4A C5A C6A Cl6A . . . . 179.68(19) ?
    O1A C1A C6A C5A . . . . -178.74(19) ?
    C2A C1A C6A C5A . . . . 0.3(3) ?
    O1A C1A C6A Cl6A . . . . 1.0(2) ?
    C2A C1A C6A Cl6A . . . . -179.97(14) ?
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
    N4B H4B1 O1A . 0.83(2) 2.68(2) 3.060(2) 110(2)
    N4B H4B1 Cl6A . 0.83(2) 3.01(2) 3.7354(17) 147(2)
    N2B H2B1 O1A 2_666 0.84(2) 2.53(2) 3.200(2) 139(2)
    N2B H2B2 N1B 2_756 0.85(3) 2.14(3) 2.987(2) 179(2)
    N4B H4B2 N3B 2_666 0.87(3) 2.11(3) 2.977(2) 174(2)
    O1A H1A N5B 1_455 0.86(3) 1.78(3) 2.6123(19) 160(3)
data_IV
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2015-08-10
_journal_date_accepted     2015-08-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2015
_journal_volume     71
_journal_issue      9
_journal_page_first     804
_journal_page_last     813
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229615015119
_journal_coeditor_code     SK3598
_database_code_depnum_ccdc_archive     'CCDC 1418578'
_chemical_name_systematic
;
2,6-Diaminopyrimidin-4(3H)-one--N-methylpyrrolidin-2-one (1/1)
;
_chemical_name_common
;
6-Aminoisocytosine--N-methylpyrrolidin-2-one (1/1)
;
_chemical_formula_moiety     'C4 H6 N4 O, C5 H9 N O'
_chemical_formula_sum     'C9 H15 N5 O2'
_chemical_formula_weight     225.26
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.1456(5)
_cell_length_b     9.2289(6)
_cell_length_c     14.9731(9)
_cell_angle_alpha     90.00
_cell_angle_beta     96.463(5)
_cell_angle_gamma     90.00
_cell_volume     1118.45(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25481
_cell_measurement_theta_min     3.34
_cell_measurement_theta_max     26.01
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.45
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.338
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_absorpt_correction_T_min     0.869
_exptl_absorpt_correction_T_max     0.914
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator     'Genix 3D multilayer optics'
_diffrn_measurement_device_type     'Stoe IPDS II two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     28235
_diffrn_reflns_av_R_equivalents     0.0730
_diffrn_reflns_av_sigmaI/netI     0.0219
_diffrn_reflns_theta_min     3.35
_diffrn_reflns_theta_max     25.72
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2098
_reflns_number_gt     1912
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0694
_refine_ls_R_factor_gt     0.0650
_refine_ls_wR_factor_gt     0.1752
_refine_ls_wR_factor_ref     0.1790
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.112
_refine_ls_number_reflns     2098
_refine_ls_number_parameters     212
_refine_ls_number_restraints     32
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0893P)²+0.8169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.606
_refine_diff_density_min     -0.408
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.022(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.3959(2) 0.33450(19) 0.70055(13) 0.0351(5) Uani d . 1 1 . .
    C C2 0.4815(3) 0.4517(2) 0.72640(15) 0.0352(5) Uani d . 1 1 . .
    N N2 0.6421(2) 0.4574(2) 0.71351(16) 0.0426(6) Uani d . 1 1 . .
    H H21 0.689(4) 0.371(3) 0.7025(19) 0.048(7) Uiso d . 1 1 . .
    H H22 0.704(4) 0.530(3) 0.745(2) 0.051(8) Uiso d . 1 1 . .
    N N3 0.4148(2) 0.5680(2) 0.76271(14) 0.0360(5) Uani d . 1 1 . .
    H H3 0.479(4) 0.646(4) 0.7774(19) 0.052(8) Uiso d . 1 1 . .
    C C4 0.2487(3) 0.5746(2) 0.77620(15) 0.0347(5) Uani d . 1 1 . .
    O O4 0.19854(19) 0.68802(17) 0.81076(12) 0.0420(5) Uani d . 1 1 . .
    C C5 0.1561(3) 0.4521(2) 0.74841(16) 0.0365(6) Uani d . 1 1 . .
    H H5 0.0416 0.4482 0.7553 0.044 Uiso calc R 1 1 . .
    C C6 0.2316(3) 0.3366(2) 0.71089(15) 0.0337(5) Uani d . 1 1 . .
    N N6 0.1494(3) 0.2150(2) 0.68309(16) 0.0409(5) Uani d . 1 1 . .
    H H61 0.191(4) 0.162(3) 0.644(2) 0.049(8) Uiso d . 1 1 . .
    H H62 0.038(5) 0.214(3) 0.686(2) 0.060(9) Uiso d . 1 1 . .
    O O2X 0.2800(4) -0.0024(3) 0.5758(2) 0.1088(12) Uani d D 1 1 . .
    C C5X 0.2443(8) -0.3733(4) 0.5204(3) 0.1028(17) Uani d D 1 1 . .
    H H5X1 0.2862 -0.4544 0.5598 0.123 Uiso calc PR 0.591(9) 1 A 1
    H H5X2 0.2510 -0.3983 0.4566 0.123 Uiso calc PR 0.591(9) 1 A 1
    H H5XA 0.1878 -0.3978 0.4602 0.123 Uiso d PR 0.409(9) 1 A 2
    H H5XB 0.2311 -0.4547 0.5620 0.123 Uiso d PR 0.409(9) 1 A 2
    N N1X 0.3228(8) -0.2372(5) 0.5459(3) 0.0684(18) Uani d PD 0.591(9) 1 A 1
    C C1X 0.4979(10) -0.2377(10) 0.5403(8) 0.085(3) Uani d PD 0.591(9) 1 A 1
    H H1X1 0.5350 -0.3373 0.5317 0.127 Uiso calc PR 0.591(9) 1 A 1
    H H1X2 0.5556 -0.1984 0.5960 0.127 Uiso calc PR 0.591(9) 1 A 1
    H H1X3 0.5224 -0.1779 0.4894 0.127 Uiso calc PR 0.591(9) 1 A 1
    C C2X 0.2360(11) -0.1221(7) 0.5557(9) 0.063(3) Uani d PD 0.591(9) 1 A 1
    C C3X 0.0540(8) -0.1597(11) 0.5493(6) 0.095(3) Uani d PD 0.591(9) 1 A 1
    H H3X1 0.0050 -0.1331 0.6046 0.114 Uiso calc PR 0.591(9) 1 A 1
    H H3X2 -0.0097 -0.1138 0.4966 0.114 Uiso calc PR 0.591(9) 1 A 1
    C C4X 0.0661(13) -0.3216(12) 0.5385(10) 0.142(6) Uani d PD 0.591(9) 1 A 1
    H H4X1 -0.0148 -0.3529 0.4878 0.171 Uiso calc PR 0.591(9) 1 A 1
    H H4X2 0.0363 -0.3692 0.5937 0.171 Uiso calc PR 0.591(9) 1 A 1
    N N1X' 0.1840(11) -0.2455(8) 0.5520(5) 0.080(3) Uani d PD 0.409(9) 1 A 2
    C C1X' 0.0141(14) -0.2659(16) 0.5624(11) 0.082(4) Uani d PD 0.409(9) 1 A 2
    H H1XA -0.0177 -0.3661 0.5472 0.123 Uiso calc PR 0.409(9) 1 A 2
    H H1XB -0.0531 -0.1995 0.5224 0.123 Uiso calc PR 0.409(9) 1 A 2
    H H1XC -0.0041 -0.2461 0.6249 0.123 Uiso calc PR 0.409(9) 1 A 2
    C C2X' 0.2852(17) -0.1335(11) 0.5626(19) 0.093(6) Uani d PD 0.409(9) 1 A 2
    C C3X' 0.4550(19) -0.1781(14) 0.5369(13) 0.122(7) Uani d PD 0.409(9) 1 A 2
    H H3XA 0.4828 -0.1242 0.4834 0.147 Uiso calc PR 0.409(9) 1 A 2
    H H3XB 0.5428 -0.1619 0.5872 0.147 Uiso calc PR 0.409(9) 1 A 2
    C C4X' 0.4317(13) -0.3364(12) 0.5169(8) 0.104(5) Uani d PD 0.409(9) 1 A 2
    H H4XA 0.5014 -0.3948 0.5619 0.125 Uiso calc PR 0.409(9) 1 A 2
    H H4XB 0.4640 -0.3587 0.4566 0.125 Uiso calc PR 0.409(9) 1 A 2
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 . 1.321(3) ?
    N1 C6 . 1.365(3) ?
    C2 N2 . 1.345(3) ?
    C2 N3 . 1.345(3) ?
    N2 H21 . 0.91(3) ?
    N2 H22 . 0.94(3) ?
    N3 C4 . 1.391(3) ?
    N3 H3 . 0.91(3) ?
    C4 O4 . 1.256(3) ?
    C4 C5 . 1.397(3) ?
    C5 C6 . 1.381(3) ?
    C5 H5 . 0.9500 ?
    C6 N6 . 1.348(3) ?
    N6 H61 . 0.87(3) ?
    N6 H62 . 0.92(4) ?
    O2X C2X . 1.189(7) ?
    O2X C2X' . 1.228(9) ?
    C5X N1X' . 1.381(7) ?
    C5X N1X . 1.441(6) ?
    C5X C4X' . 1.571(9) ?
    C5X C4X . 1.580(9) ?
    C5X H5X1 . 0.9900 ?
    C5X H5X2 . 0.9900 ?
    C5X H5XA . 0.9900 ?
    C5X H5XB . 0.9901 ?
    N1X C2X . 1.293(8) ?
    N1X C1X . 1.438(8) ?
    C1X H1X1 . 0.9800 ?
    C1X H1X2 . 0.9800 ?
    C1X H1X3 . 0.9800 ?
    C2X C3X . 1.515(8) ?
    C3X C4X . 1.507(9) ?
    C3X H3X1 . 0.9900 ?
    C3X H3X2 . 0.9900 ?
    C4X H4X1 . 0.9900 ?
    C4X H4X2 . 0.9900 ?
    N1X' C2X' . 1.321(9) ?
    N1X' C1X' . 1.423(9) ?
    C1X' H1XA . 0.9800 ?
    C1X' H1XB . 0.9800 ?
    C1X' H1XC . 0.9800 ?
    C2X' C3X' . 1.534(10) ?
    C3X' C4X' . 1.499(10) ?
    C3X' H3XA . 0.9900 ?
    C3X' H3XB . 0.9900 ?
    C4X' H4XA . 0.9900 ?
    C4X' H4XB . 0.9900 ?
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
    C2 N1 C6 . . 116.57(18) ?
    N1 C2 N2 . . 118.7(2) ?
    N1 C2 N3 . . 123.2(2) ?
    N2 C2 N3 . . 118.1(2) ?
    C2 N2 H21 . . 115.3(18) ?
    C2 N2 H22 . . 115.4(18) ?
    H21 N2 H22 . . 121(3) ?
    C2 N3 C4 . . 122.52(19) ?
    C2 N3 H3 . . 119.2(19) ?
    C4 N3 H3 . . 118.3(19) ?
    O4 C4 N3 . . 117.61(19) ?
    O4 C4 C5 . . 127.4(2) ?
    N3 C4 C5 . . 114.99(19) ?
    C6 C5 C4 . . 119.7(2) ?
    C6 C5 H5 . . 120.1 ?
    C4 C5 H5 . . 120.1 ?
    N6 C6 N1 . . 114.36(19) ?
    N6 C6 C5 . . 122.6(2) ?
    N1 C6 C5 . . 122.99(19) ?
    C6 N6 H61 . . 117(2) ?
    C6 N6 H62 . . 117(2) ?
    H61 N6 H62 . . 120(3) ?
    N1X' C5X N1X . . 47.9(4) ?
    N1X' C5X C4X' . . 102.2(6) ?
    N1X C5X C4X' . . 54.3(5) ?
    N1X' C5X C4X . . 46.7(6) ?
    N1X C5X C4X . . 94.6(6) ?
    C4X' C5X C4X . . 148.8(6) ?
    N1X' C5X H5X1 . . 123.6 ?
    N1X C5X H5X1 . . 112.8 ?
    C4X' C5X H5X1 . . 85.0 ?
    C4X C5X H5X1 . . 112.8 ?
    N1X' C5X H5X2 . . 126.2 ?
    N1X C5X H5X2 . . 112.8 ?
    C4X' C5X H5X2 . . 81.9 ?
    C4X C5X H5X2 . . 112.8 ?
    H5X1 C5X H5X2 . . 110.3 ?
    N1X' C5X H5XA . . 111.1 ?
    N1X C5X H5XA . . 125.9 ?
    C4X' C5X H5XA . . 111.9 ?
    C4X C5X H5XA . . 83.3 ?
    H5X1 C5X H5XA . . 117.6 ?
    N1X' C5X H5XB . . 111.4 ?
    N1X C5X H5XB . . 124.8 ?
    C4X' C5X H5XB . . 111.1 ?
    C4X C5X H5XB . . 87.4 ?
    H5X2 C5X H5XB . . 116.9 ?
    H5XA C5X H5XB . . 109.1 ?
    C2X N1X C1X . . 124.6(7) ?
    C2X N1X C5X . . 121.0(6) ?
    C1X N1X C5X . . 113.3(6) ?
    N1X C1X H1X1 . . 109.5 ?
    N1X C1X H1X2 . . 109.5 ?
    H1X1 C1X H1X2 . . 109.5 ?
    N1X C1X H1X3 . . 109.5 ?
    H1X1 C1X H1X3 . . 109.5 ?
    H1X2 C1X H1X3 . . 109.5 ?
    O2X C2X N1X . . 129.7(8) ?
    O2X C2X C3X . . 119.6(7) ?
    N1X C2X C3X . . 110.3(6) ?
    C4X C3X C2X . . 99.1(7) ?
    C4X C3X H3X1 . . 111.9 ?
    C2X C3X H3X1 . . 111.9 ?
    C4X C3X H3X2 . . 111.9 ?
    C2X C3X H3X2 . . 111.9 ?
    H3X1 C3X H3X2 . . 109.6 ?
    C3X C4X C5X . . 113.0(7) ?
    C3X C4X H4X1 . . 109.0 ?
    C5X C4X H4X1 . . 109.0 ?
    C3X C4X H4X2 . . 109.0 ?
    C5X C4X H4X2 . . 109.0 ?
    H4X1 C4X H4X2 . . 107.8 ?
    C2X' N1X' C5X . . 117.9(8) ?
    C2X' N1X' C1X' . . 133.8(10) ?
    C5X N1X' C1X' . . 108.2(8) ?
    N1X' C1X' H1XA . . 109.5 ?
    N1X' C1X' H1XB . . 109.5 ?
    H1XA C1X' H1XB . . 109.5 ?
    N1X' C1X' H1XC . . 109.5 ?
    H1XA C1X' H1XC . . 109.5 ?
    H1XB C1X' H1XC . . 109.5 ?
    O2X C2X' N1X' . . 139.4(12) ?
    O2X C2X' C3X' . . 110.7(9) ?
    N1X' C2X' C3X' . . 109.2(9) ?
    C4X' C3X' C2X' . . 102.4(9) ?
    C4X' C3X' H3XA . . 111.3 ?
    C2X' C3X' H3XA . . 111.3 ?
    C4X' C3X' H3XB . . 111.3 ?
    C2X' C3X' H3XB . . 111.3 ?
    H3XA C3X' H3XB . . 109.2 ?
    C3X' C4X' C5X . . 107.8(8) ?
    C3X' C4X' H4XA . . 110.1 ?
    C5X C4X' H4XA . . 110.1 ?
    C3X' C4X' H4XB . . 110.1 ?
    C5X C4X' H4XB . . 110.1 ?
    H4XA C4X' H4XB . . 108.5 ?
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
    C6 N1 C2 N2 . . . . -176.8(2) ?
    C6 N1 C2 N3 . . . . 1.1(3) ?
    N1 C2 N3 C4 . . . . 0.0(4) ?
    N2 C2 N3 C4 . . . . 178.0(2) ?
    C2 N3 C4 O4 . . . . 179.9(2) ?
    C2 N3 C4 C5 . . . . -0.6(3) ?
    O4 C4 C5 C6 . . . . 179.5(2) ?
    N3 C4 C5 C6 . . . . 0.0(3) ?
    C2 N1 C6 N6 . . . . 179.6(2) ?
    C2 N1 C6 C5 . . . . -1.7(3) ?
    C4 C5 C6 N6 . . . . 179.7(2) ?
    C4 C5 C6 N1 . . . . 1.1(3) ?
    N1X' C5X N1X C2X . . . . -14.8(9) ?
    C4X' C5X N1X C2X . . . . 164.6(10) ?
    C4X C5X N1X C2X . . . . -13.1(10) ?
    N1X' C5X N1X C1X . . . . 177.3(8) ?
    C4X' C5X N1X C1X . . . . -3.3(7) ?
    C4X C5X N1X C1X . . . . 179.0(7) ?
    C2X' O2X C2X N1X . . . . -10(4) ?
    C2X' O2X C2X C3X . . . . 162(6) ?
    C1X N1X C2X O2X . . . . -13(2) ?
    C5X N1X C2X O2X . . . . -179.6(10) ?
    C1X N1X C2X C3X . . . . 174.2(8) ?
    C5X N1X C2X C3X . . . . 7.7(13) ?
    O2X C2X C3X C4X . . . . -170.9(12) ?
    N1X C2X C3X C4X . . . . 2.6(13) ?
    C2X C3X C4X C5X . . . . -10.8(12) ?
    N1X' C5X C4X C3X . . . . 15.6(7) ?
    N1X C5X C4X C3X . . . . 13.8(10) ?
    C4X' C5X C4X C3X . . . . 10(2) ?
    N1X C5X N1X' C2X' . . . . 5.6(15) ?
    C4X' C5X N1X' C2X' . . . . 5.2(16) ?
    C4X C5X N1X' C2X' . . . . -172.0(18) ?
    N1X C5X N1X' C1X' . . . . -177.0(10) ?
    C4X' C5X N1X' C1X' . . . . -177.4(9) ?
    C4X C5X N1X' C1X' . . . . 5.4(13) ?
    C2X O2X C2X' N1X' . . . . -18(2) ?
    C2X O2X C2X' C3X' . . . . 150(7) ?
    C5X N1X' C2X' O2X . . . . 167(3) ?
    C1X' N1X' C2X' O2X . . . . -9(5) ?
    C5X N1X' C2X' C3X' . . . . -1(2) ?
    C1X' N1X' C2X' C3X' . . . . -177.6(14) ?
    O2X C2X' C3X' C4X' . . . . -175.7(18) ?
    N1X' C2X' C3X' C4X' . . . . -4(2) ?
    C2X' C3X' C4X' C5X . . . . 6.7(18) ?
    N1X' C5X C4X' C3X' . . . . -7.3(12) ?
    N1X C5X C4X' C3X' . . . . -7.7(10) ?
    C4X C5X C4X' C3X' . . . . -3.2(19) ?
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
    N2 H21 O4 2_646 0.91(3) 1.94(3) 2.846(3) 175(3)
    N2 H22 N6 2_656 0.94(3) 2.28(3) 3.216(3) 177(3)
    N3 H3 N1 2_656 0.91(3) 2.02(3) 2.922(3) 173(3)
    N6 H61 O2X . 0.87(3) 2.01(3) 2.850(3) 165(3)
    N6 H62 O4 2_546 0.92(4) 1.94(4) 2.857(3) 173(3)
data_V
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 1418579'
_chemical_name_systematic
;
2,6-Diaminopyrimidin-4(3H)-one--2,6-dichloroaniline--\
N,N-dimethylacetamide (1/1/1)
;
_chemical_name_common
;
6-Aminoisocytosine--2,6-dichloroaniline--N,N-dimethylacetamide
;
_chemical_formula_moiety     'C6 H5 Cl2 N, C4 H6 N4 O, C4 H9 N O'
_chemical_formula_sum     'C14 H20 Cl2 N6 O2'
_chemical_formula_iupac     'C6 H5 Cl2 N, C4 H6 N4 O, C4 H9 N O'
_chemical_formula_weight     375.26
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.1060(5)
_cell_length_b     9.0448(5)
_cell_length_c     12.5656(8)
_cell_angle_alpha     90.00
_cell_angle_beta     102.859(5)
_cell_angle_gamma     90.00
_cell_volume     898.17(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     23474
_cell_measurement_theta_min     3.32
_cell_measurement_theta_max     26.415
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.388
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     392
_exptl_absorpt_coefficient_mu     0.381
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_absorpt_correction_T_min     0.794
_exptl_absorpt_correction_T_max     0.916
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator     'Genix 3D multilayer optics'
_diffrn_measurement_device_type     'Stoe IPDS II two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21925
_diffrn_reflns_av_R_equivalents     0.0457
_diffrn_reflns_av_sigmaI/netI     0.0252
_diffrn_reflns_theta_min     3.33
_diffrn_reflns_theta_max     26.11
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3534
_reflns_number_gt     3330
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0332
_refine_ls_R_factor_gt     0.0305
_refine_ls_wR_factor_gt     0.0790
_refine_ls_wR_factor_ref     0.0800
_refine_ls_goodness_of_fit_ref     1.096
_refine_ls_restrained_S_all     1.098
_refine_ls_number_reflns     3534
_refine_ls_number_parameters     257
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0462P)²+0.1437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.264
_refine_diff_density_min     -0.181
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
;
Flack   (1983),   Number of Bijvoet pairs: 1646
;
_refine_ls_abs_structure_Flack     0.04(5)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1A 0.7878(3) 0.9517(2) 0.87440(16) 0.0252(4) Uani d . 1 1 . .
    N N1A 0.7379(3) 0.8483(2) 0.79611(17) 0.0352(5) Uani d . 1 1 . .
    H H1A1 0.789(4) 0.853(3) 0.750(2) 0.042 Uiso d . 1 1 . .
    H H1A2 0.642(4) 0.814(3) 0.791(2) 0.042 Uiso d . 1 1 . .
    C C2A 0.9313(3) 1.0404(3) 0.87964(17) 0.0306(4) Uani d . 1 1 . .
    Cl Cl2A 1.04435(8) 1.01771(7) 0.77792(5) 0.04277(16) Uani d . 1 1 . .
    C C3A 0.9862(3) 1.1433(3) 0.9603(2) 0.0407(6) Uani d . 1 1 . .
    H H3A 1.0855 1.1994 0.9610 0.049 Uiso calc R 1 1 . .
    C C4A 0.8958(4) 1.1648(3) 1.0406(2) 0.0441(6) Uani d . 1 1 . .
    H H4A 0.9326 1.2354 1.0968 0.053 Uiso calc R 1 1 . .
    C C5A 0.7518(3) 1.0823(3) 1.03762(19) 0.0369(5) Uani d . 1 1 . .
    H H5A 0.6876 1.0974 1.0914 0.044 Uiso calc R 1 1 . .
    C C6A 0.7011(3) 0.9790(3) 0.95776(17) 0.0298(5) Uani d . 1 1 . .
    Cl Cl6A 0.51908(8) 0.87668(7) 0.95601(5) 0.04686(18) Uani d . 1 1 . .
    N N1B 0.56730(19) 0.42237(18) 0.43752(13) 0.0186(3) Uani d . 1 1 . .
    C C2B 0.5014(2) 0.5401(2) 0.47486(14) 0.0184(4) Uani d . 1 1 . .
    N N2B 0.3341(2) 0.5485(2) 0.46373(15) 0.0250(4) Uani d . 1 1 . .
    H H21B 0.269(3) 0.468(3) 0.439(2) 0.030 Uiso d . 1 1 . .
    H H22B 0.292(3) 0.620(3) 0.496(2) 0.030 Uiso d . 1 1 . .
    N N3B 0.5969(2) 0.6551(2) 0.52280(13) 0.0205(3) Uani d . 1 1 . .
    H H3B 0.548(3) 0.729(3) 0.5441(19) 0.025 Uiso d . 1 1 . .
    C C4B 0.7719(2) 0.6587(2) 0.53695(15) 0.0192(4) Uani d . 1 1 . .
    O O4B 0.84738(16) 0.76997(15) 0.58309(12) 0.0232(3) Uani d . 1 1 . .
    C C5B 0.8424(2) 0.5367(2) 0.49467(15) 0.0204(4) Uani d . 1 1 . .
    H H5B 0.9609 0.5322 0.4993 0.024 Uiso calc R 1 1 . .
    C C6B 0.7383(2) 0.4227(2) 0.44609(15) 0.0183(4) Uani d . 1 1 . .
    N N6B 0.7971(2) 0.30113(19) 0.40550(15) 0.0226(3) Uani d . 1 1 . .
    H H61B 0.902(3) 0.299(3) 0.4059(19) 0.027 Uiso d . 1 1 . .
    H H62B 0.728(3) 0.252(3) 0.361(2) 0.027 Uiso d . 1 1 . .
    C C1X 0.3033(3) -0.0586(4) 0.2158(3) 0.0550(8) Uani d D 1 1 . .
    H H11X 0.2927 -0.1661 0.2077 0.082 Uiso calc PR 0.635(9) 1 A 1
    H H12X 0.2497 -0.0108 0.1468 0.082 Uiso calc PR 0.635(9) 1 A 1
    H H13X 0.2475 -0.0258 0.2733 0.082 Uiso calc PR 0.635(9) 1 A 1
    H H4AX 0.2186 -0.1377 0.2029 0.082 Uiso d PR 0.365(9) 1 A 2
    H H4BX 0.2839 0.0056 0.2747 0.082 Uiso d PR 0.365(9) 1 A 2
    H H4CX 0.2939 -0.0003 0.1490 0.082 Uiso d PR 0.365(9) 1 A 2
    O O2X 0.5497(2) 0.11334(17) 0.26385(14) 0.0350(4) Uani d D 1 1 . .
    C C4X 0.5361(5) -0.2831(3) 0.2364(2) 0.0531(8) Uani d D 1 1 . .
    H H41X 0.6320 -0.3517 0.2514 0.080 Uiso calc PR 0.635(9) 1 A 1
    H H42X 0.4776 -0.2908 0.1594 0.080 Uiso calc PR 0.635(9) 1 A 1
    H H43X 0.4574 -0.3079 0.2827 0.080 Uiso calc PR 0.635(9) 1 A 1
    H H1AX 0.4378 -0.3491 0.2226 0.080 Uiso d PR 0.365(9) 1 A 2
    H H1BX 0.5925 -0.2886 0.1751 0.080 Uiso d PR 0.365(9) 1 A 2
    H H1CX 0.6153 -0.3133 0.3037 0.080 Uiso d PR 0.365(9) 1 A 2
    C C5X 0.7811(3) -0.0953(3) 0.2912(2) 0.0437(6) Uani d D 1 1 . .
    H H51X 0.8461 -0.1875 0.2990 0.066 Uiso calc PR 0.635(9) 1 A 1
    H H52X 0.8058 -0.0416 0.3607 0.066 Uiso calc PR 0.635(9) 1 A 1
    H H53X 0.8125 -0.0340 0.2345 0.066 Uiso calc PR 0.635(9) 1 A 1
    H H5AX 0.7706 -0.2032 0.2869 0.066 Uiso d PR 0.365(9) 1 A 2
    H H5BX 0.8425 -0.0604 0.2371 0.066 Uiso d PR 0.365(9) 1 A 2
    H H5CX 0.8431 -0.0668 0.3645 0.066 Uiso d PR 0.365(9) 1 A 2
    C C2X 0.4921(6) -0.0160(5) 0.2469(3) 0.0257(11) Uani d PD 0.635(9) 1 A 1
    N N3X 0.5987(5) -0.1294(4) 0.2602(2) 0.0316(12) Uani d PD 0.635(9) 1 A 1
    N N3X' 0.4761(9) -0.1240(8) 0.2466(4) 0.038(2) Uani d PD 0.365(9) 1 A 2
    C C2X' 0.5992(10) -0.0249(8) 0.2677(5) 0.027(2) Uani d PD 0.365(9) 1 A 2
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    C1A N1A . 1.353(3) ?
    C1A C2A . 1.402(3) ?
    C1A C6A . 1.407(3) ?
    N1A H1A1 . 0.79(3) ?
    N1A H1A2 . 0.83(3) ?
    C2A C3A . 1.375(3) ?
    C2A Cl2A . 1.743(2) ?
    C3A C4A . 1.386(4) ?
    C3A H3A . 0.9500 ?
    C4A C5A . 1.378(4) ?
    C4A H4A . 0.9500 ?
    C5A C6A . 1.366(3) ?
    C5A H5A . 0.9500 ?
    C6A Cl6A . 1.738(2) ?
    N1B C2B . 1.323(2) ?
    N1B C6B . 1.366(2) ?
    C2B N2B . 1.334(2) ?
    C2B N3B . 1.355(3) ?
    N2B H21B . 0.91(3) ?
    N2B H22B . 0.87(3) ?
    N3B C4B . 1.390(2) ?
    N3B H3B . 0.85(3) ?
    C4B O4B . 1.252(2) ?
    C4B C5B . 1.400(3) ?
    C5B C6B . 1.385(3) ?
    C5B H5B . 0.9500 ?
    C6B N6B . 1.344(3) ?
    N6B H61B . 0.85(3) ?
    N6B H62B . 0.83(3) ?
    C1X N3X' . 1.490(8) ?
    C1X C2X . 1.542(5) ?
    C1X H11X . 0.9800 ?
    C1X H12X . 0.9800 ?
    C1X H13X . 0.9800 ?
    C1X H4AX . 0.9800 ?
    C1X H4BX . 0.9799 ?
    C1X H4CX . 0.9802 ?
    O2X C2X . 1.260(5) ?
    O2X C2X' . 1.311(8) ?
    C4X N3X . 1.487(5) ?
    C4X N3X' . 1.533(8) ?
    C4X H41X . 0.9800 ?
    C4X H42X . 0.9800 ?
    C4X H43X . 0.9800 ?
    C4X H1AX . 0.9800 ?
    C4X H1BX . 0.9801 ?
    C4X H1CX . 0.9799 ?
    C5X N3X . 1.475(5) ?
    C5X C2X' . 1.573(8) ?
    C5X H51X . 0.9800 ?
    C5X H52X . 0.9800 ?
    C5X H53X . 0.9800 ?
    C5X H5AX . 0.9800 ?
    C5X H5BX . 0.9800 ?
    C5X H5CX . 0.9800 ?
    C2X N3X . 1.327(6) ?
    N3X' C2X' . 1.324(11) ?
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
    N1A C1A C2A . . 122.7(2) ?
    N1A C1A C6A . . 123.0(2) ?
    C2A C1A C6A . . 114.28(19) ?
    C1A N1A H1A1 . . 112(2) ?
    C1A N1A H1A2 . . 117(2) ?
    H1A1 N1A H1A2 . . 127(3) ?
    C3A C2A C1A . . 123.4(2) ?
    C3A C2A Cl2A . . 118.92(18) ?
    C1A C2A Cl2A . . 117.64(16) ?
    C2A C3A C4A . . 119.6(2) ?
    C2A C3A H3A . . 120.2 ?
    C4A C3A H3A . . 120.2 ?
    C5A C4A C3A . . 119.1(2) ?
    C5A C4A H4A . . 120.5 ?
    C3A C4A H4A . . 120.5 ?
    C6A C5A C4A . . 120.3(2) ?
    C6A C5A H5A . . 119.9 ?
    C4A C5A H5A . . 119.9 ?
    C5A C6A C1A . . 123.2(2) ?
    C5A C6A Cl6A . . 119.31(18) ?
    C1A C6A Cl6A . . 117.44(17) ?
    C2B N1B C6B . . 116.92(16) ?
    N1B C2B N2B . . 119.33(17) ?
    N1B C2B N3B . . 122.67(16) ?
    N2B C2B N3B . . 117.99(18) ?
    C2B N2B H21B . . 119.3(15) ?
    C2B N2B H22B . . 119.1(17) ?
    H21B N2B H22B . . 119(2) ?
    C2B N3B C4B . . 122.70(17) ?
    C2B N3B H3B . . 119.0(16) ?
    C4B N3B H3B . . 118.3(16) ?
    O4B C4B N3B . . 117.26(17) ?
    O4B C4B C5B . . 127.63(17) ?
    N3B C4B C5B . . 115.10(17) ?
    C6B C5B C4B . . 119.56(16) ?
    C6B C5B H5B . . 120.2 ?
    C4B C5B H5B . . 120.2 ?
    N6B C6B N1B . . 114.07(17) ?
    N6B C6B C5B . . 122.93(16) ?
    N1B C6B C5B . . 122.98(17) ?
    C6B N6B H61B . . 117.0(17) ?
    C6B N6B H62B . . 116.5(17) ?
    H61B N6B H62B . . 122(2) ?
    N3X' C1X H11X . . 71.9 ?
    C2X C1X H11X . . 109.5 ?
    N3X' C1X H12X . . 127.6 ?
    C2X C1X H12X . . 109.5 ?
    H11X C1X H12X . . 109.5 ?
    N3X' C1X H13X . . 119.4 ?
    C2X C1X H13X . . 109.5 ?
    H11X C1X H13X . . 109.5 ?
    H12X C1X H13X . . 109.5 ?
    N3X' C1X H4AX . . 109.6 ?
    C2X C1X H4AX . . 147.5 ?
    H12X C1X H4AX . . 91.1 ?
    H13X C1X H4AX . . 85.5 ?
    N3X' C1X H4BX . . 109.8 ?
    C2X C1X H4BX . . 88.7 ?
    H11X C1X H4BX . . 129.9 ?
    H12X C1X H4BX . . 107.1 ?
    H4AX C1X H4BX . . 109.5 ?
    N3X' C1X H4CX . . 109.0 ?
    C2X C1X H4CX . . 88.1 ?
    H11X C1X H4CX . . 117.1 ?
    H13X C1X H4CX . . 120.6 ?
    H4AX C1X H4CX . . 109.5 ?
    H4BX C1X H4CX . . 109.5 ?
    N3X C4X H41X . . 109.5 ?
    N3X' C4X H41X . . 146.3 ?
    N3X C4X H42X . . 109.5 ?
    N3X' C4X H42X . . 93.2 ?
    H41X C4X H42X . . 109.5 ?
    N3X C4X H43X . . 109.5 ?
    N3X' C4X H43X . . 84.6 ?
    H41X C4X H43X . . 109.5 ?
    H42X C4X H43X . . 109.5 ?
    N3X C4X H1AX . . 146.4 ?
    N3X' C4X H1AX . . 109.0 ?
    H41X C4X H1AX . . 103.1 ?
    H42X C4X H1AX . . 65.6 ?
    H43X C4X H1AX . . 49.8 ?
    N3X C4X H1BX . . 90.4 ?
    N3X' C4X H1BX . . 109.0 ?
    H41X C4X H1BX . . 68.3 ?
    H42X C4X H1BX . . 55.2 ?
    H43X C4X H1BX . . 158.9 ?
    H1AX C4X H1BX . . 109.5 ?
    N3X C4X H1CX . . 87.6 ?
    N3X' C4X H1CX . . 110.4 ?
    H41X C4X H1CX . . 47.0 ?
    H42X C4X H1CX . . 155.7 ?
    H43X C4X H1CX . . 79.2 ?
    H1AX C4X H1CX . . 109.5 ?
    H1BX C4X H1CX . . 109.5 ?
    N3X C5X H51X . . 109.5 ?
    C2X' C5X H51X . . 145.5 ?
    N3X C5X H52X . . 109.5 ?
    C2X' C5X H52X . . 88.0 ?
    H51X C5X H52X . . 109.5 ?
    N3X C5X H53X . . 109.5 ?
    C2X' C5X H53X . . 91.1 ?
    H51X C5X H53X . . 109.5 ?
    H52X C5X H53X . . 109.5 ?
    N3X C5X H5AX . . 73.0 ?
    C2X' C5X H5AX . . 109.1 ?
    H52X C5X H5AX . . 122.7 ?
    H53X C5X H5AX . . 123.8 ?
    N3X C5X H5BX . . 121.2 ?
    C2X' C5X H5BX . . 109.9 ?
    H51X C5X H5BX . . 89.9 ?
    H52X C5X H5BX . . 115.1 ?
    H5AX C5X H5BX . . 109.5 ?
    N3X C5X H5CX . . 125.3 ?
    C2X' C5X H5CX . . 109.5 ?
    H51X C5X H5CX . . 88.7 ?
    H53X C5X H5CX . . 111.9 ?
    H5AX C5X H5CX . . 109.5 ?
    H5BX C5X H5CX . . 109.5 ?
    O2X C2X N3X . . 119.3(5) ?
    O2X C2X C1X . . 125.7(4) ?
    N3X C2X C1X . . 114.9(4) ?
    C2X N3X C5X . . 117.3(4) ?
    C2X N3X C4X . . 120.9(4) ?
    C5X N3X C4X . . 121.7(3) ?
    C2X N3X H5AX . . 155.5 ?
    C4X N3X H5AX . . 83.6 ?
    C2X' N3X' C1X . . 114.0(7) ?
    C2X' N3X' C4X . . 114.4(7) ?
    C1X N3X' C4X . . 130.4(5) ?
    O2X C2X' N3X' . . 115.3(8) ?
    O2X C2X' C5X . . 131.3(6) ?
    N3X' C2X' C5X . . 113.4(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
    N1A C1A C2A C3A . . . . -178.2(2) ?
    C6A C1A C2A C3A . . . . 1.4(3) ?
    N1A C1A C2A Cl2A . . . . 1.8(3) ?
    C6A C1A C2A Cl2A . . . . -178.56(15) ?
    C1A C2A C3A C4A . . . . -1.2(4) ?
    Cl2A C2A C3A C4A . . . . 178.7(2) ?
    C2A C3A C4A C5A . . . . -0.1(4) ?
    C3A C4A C5A C6A . . . . 1.2(4) ?
    C4A C5A C6A C1A . . . . -1.0(4) ?
    C4A C5A C6A Cl6A . . . . -180.0(2) ?
    N1A C1A C6A C5A . . . . 179.4(2) ?
    C2A C1A C6A C5A . . . . -0.3(3) ?
    N1A C1A C6A Cl6A . . . . -1.7(3) ?
    C2A C1A C6A Cl6A . . . . 178.68(16) ?
    C6B N1B C2B N2B . . . . 176.80(17) ?
    C6B N1B C2B N3B . . . . -2.0(3) ?
    N1B C2B N3B C4B . . . . -0.2(3) ?
    N2B C2B N3B C4B . . . . -179.01(17) ?
    C2B N3B C4B O4B . . . . -179.43(17) ?
    C2B N3B C4B C5B . . . . 2.1(3) ?
    O4B C4B C5B C6B . . . . 179.93(18) ?
    N3B C4B C5B C6B . . . . -1.8(3) ?
    C2B N1B C6B N6B . . . . -179.18(16) ?
    C2B N1B C6B C5B . . . . 2.3(3) ?
    C4B C5B C6B N6B . . . . -178.78(18) ?
    C4B C5B C6B N1B . . . . -0.4(3) ?
    C2X' O2X C2X N3X . . . . -1.8(4) ?
    C2X' O2X C2X C1X . . . . 175.3(6) ?
    N3X' C1X C2X O2X . . . . -172.9(6) ?
    N3X' C1X C2X N3X . . . . 4.4(4) ?
    O2X C2X N3X C5X . . . . -1.9(4) ?
    C1X C2X N3X C5X . . . . -179.3(3) ?
    O2X C2X N3X C4X . . . . -177.4(3) ?
    C1X C2X N3X C4X . . . . 5.2(4) ?
    C2X' C5X N3X C2X . . . . 2.8(4) ?
    C2X' C5X N3X C4X . . . . 178.3(5) ?
    N3X' C4X N3X C2X . . . . -8.3(4) ?
    N3X' C4X N3X C5X . . . . 176.4(5) ?
    C2X C1X N3X' C2X' . . . . 1.5(4) ?
    C2X C1X N3X' C4X . . . . -165.0(8) ?
    N3X C4X N3X' C2X' . . . . 2.2(4) ?
    N3X C4X N3X' C1X . . . . 168.7(8) ?
    C2X O2X C2X' N3X' . . . . -4.5(4) ?
    C2X O2X C2X' C5X . . . . 174.2(9) ?
    C1X N3X' C2X' O2X . . . . 3.4(7) ?
    C4X N3X' C2X' O2X . . . . 172.2(4) ?
    C1X N3X' C2X' C5X . . . . -175.5(4) ?
    C4X N3X' C2X' C5X . . . . -6.8(6) ?
    N3X C5X C2X' O2X . . . . -175.7(8) ?
    N3X C5X C2X' N3X' . . . . 3.1(3) ?
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
    N1A H1A1 O4B . 0.79(3) 2.37(3) 3.084(3) 151(3)
    N1A H1A1 Cl2A . 0.79(3) 2.51(3) 2.971(2) 119(3)
    N1A H1A2 O2X 2_656 0.83(3) 2.39(3) 3.120(3) 149(3)
    N1A H1A2 Cl6A . 0.83(3) 2.56(3) 2.972(2) 112(2)
    N2B H21B O4B 2_646 0.91(3) 2.02(3) 2.911(2) 167(2)
    N2B H22B N6B 2_656 0.87(3) 2.27(3) 3.135(3) 174(2)
    N3B H3B N1B 2_656 0.85(3) 2.02(3) 2.857(2) 168(2)
    N6B H61B O4B 2_746 0.85(3) 2.02(3) 2.867(2) 173(2)
    N6B H62B O2X . 0.83(3) 2.09(3) 2.913(2) 173(2)
