# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_I

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'melamine barbital addition compound'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 N2 O3, C3 H6 N6'
_chemical_formula_sum            'C11 H18 N8 O3'
_chemical_formula_weight         310.33

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   9.5289(3)
_cell_length_b                   9.1191(3)
_cell_length_c                   8.6670(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     753.12(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    8667
_cell_measurement_theta_min      3.0857
_cell_measurement_theta_max      45.3807

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            32340
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.092
_diffrn_reflns_theta_max         45.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6553
_reflns_number_gt                3971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SIR-97 (ALTOMARE et al., 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 0 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.000
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6553
_refine_ls_number_parameters     144
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.898
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2A O 0.5000 0.14287(14) 0.64262(13) 0.0160(2) Uani 1 2 d S T P . .
N3B N 0.12557(9) 0.12688(10) 0.71045(10) 0.01222(15) Uani 1 1 d . . . . .
N4B N 0.0000 0.22349(17) 0.91277(15) 0.0158(2) Uani 1 2 d DS T P . .
N1B N 0.0000 0.02349(15) 0.49635(16) 0.0131(2) Uani 1 2 d S T P . .
C4B C 0.0000 0.15799(16) 0.77447(16) 0.0110(2) Uani 1 2 d S T P . .
H4B H -0.0840(12) 0.2679(16) 0.9497(18) 0.013 Uiso 1 1 d D U . . .
C5A C 0.5000 0.43922(17) 1.00219(19) 0.0140(3) Uani 1 2 d S T P . .
C2A C 0.5000 0.22795(17) 0.75191(17) 0.0122(2) Uani 1 2 d S T P . .
N1A N 0.37722(10) 0.27840(11) 0.81509(11) 0.01347(16) Uani 1 1 d D . . . .
H1A H 0.2885(13) 0.2321(16) 0.7811(18) 0.016 Uiso 1 1 d D U . . .
C4A C 0.36693(12) 0.37011(12) 0.94041(12) 0.01475(19) Uani 1 1 d . . . . .
N2B N 0.24074(10) 0.02946(12) 0.50216(12) 0.01872(19) Uani 1 1 d D . . . .
H2B2 H 0.3285(13) 0.0581(17) 0.5493(17) 0.022 Uiso 1 1 d D U . . .
H2B1 H 0.2365(18) -0.0207(18) 0.4065(13) 0.022 Uiso 1 1 d D U . . .
O4A O 0.25227(9) 0.39843(11) 0.99502(12) 0.02398(19) Uani 1 1 d . . . . .
C2B C 0.11863(11) 0.06051(12) 0.57057(11) 0.01202(17) Uani 1 1 d . . . . .
C8A C 0.5000 0.4354(2) 1.18084(19) 0.0186(3) Uani 1 2 d DS T P . .
H81 H 0.5849(14) 0.4863(18) 1.2198(19) 0.022 Uiso 1 1 d D U . . .
C7A C 0.5000 0.60307(18) 0.9496(2) 0.0178(3) Uani 1 2 d DS T P . .
H71 H 0.5884(13) 0.6418(16) 0.9955(18) 0.021 Uiso 1 1 d D U . . .
C10A C 0.5000 0.6287(2) 0.7759(2) 0.0266(4) Uani 1 2 d DS T P . .
H11 H 0.5845(15) 0.5877(19) 0.728(2) 0.032 Uiso 1 1 d D U . . .
H12 H 0.5000 0.7366(15) 0.758(3) 0.032 Uiso 1 2 d DS U P . .
C9A C 0.5000 0.2816(3) 1.2499(3) 0.0360(5) Uani 1 2 d DS T P . .
H91 H 0.5840(17) 0.225(2) 1.219(2) 0.043 Uiso 1 1 d D U . . .
H92 H 0.5000 0.288(3) 1.3634(15) 0.043 Uiso 1 2 d DS U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2A C2A 1.2244(19) . ?
N3B C4B 1.3491(11) . ?
N3B C2B 1.3566(13) . ?
N4B C4B 1.339(2) . ?
N4B H4B 0.952(10) . ?
N1B C2B 1.3437(13) 3 ?
N1B C2B 1.3438(13) . ?
C4B N3B 1.3491(11) 3 ?
C5A C4A 1.5138(14) . ?
C5A C4A 1.5138(14) 3_655 ?
C5A C8A 1.549(2) . ?
C5A C7A 1.562(2) . ?
C2A N1A 1.3713(12) . ?
C2A N1A 1.3713(12) 3_655 ?
N1A C4A 1.3743(14) . ?
N1A H1A 0.990(11) . ?
C4A O4A 1.2184(14) . ?
N2B C2B 1.3363(14) . ?
N2B H2B2 0.967(11) . ?
N2B H2B1 0.948(11) . ?
C8A C9A 1.525(3) . ?
C8A H81 0.992(11) . ?
C7A C10A 1.524(3) . ?
C7A H71 0.996(11) . ?
C10A H11 0.979(11) . ?
C10A H12 0.997(12) . ?
C9A H91 0.988(12) . ?
C9A H92 0.985(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4B N3B C2B 114.72(9) . . ?
C4B N4B H4B 119.4(10) . . ?
C2B N1B C2B 114.54(13) 3 . ?
N4B C4B N3B 117.51(6) . 3 ?
N4B C4B N3B 117.51(6) . . ?
N3B C4B N3B 124.97(13) 3 . ?
C4A C5A C4A 113.78(13) . 3_655 ?
C4A C5A C8A 110.14(9) . . ?
C4A C5A C8A 110.14(9) 3_655 . ?
C4A C5A C7A 107.15(9) . . ?
C4A C5A C7A 107.15(9) 3_655 . ?
C8A C5A C7A 108.25(13) . . ?
O2A C2A N1A 121.43(7) . . ?
O2A C2A N1A 121.43(7) . 3_655 ?
N1A C2A N1A 117.13(13) . 3_655 ?
C2A N1A C4A 125.49(10) . . ?
C2A N1A H1A 117.8(9) . . ?
C4A N1A H1A 115.7(9) . . ?
O4A C4A N1A 120.00(10) . . ?
O4A C4A C5A 121.70(11) . . ?
N1A C4A C5A 118.24(10) . . ?
C2B N2B H2B2 120.5(9) . . ?
C2B N2B H2B1 116.9(10) . . ?
H2B2 N2B H2B1 122.5(15) . . ?
N2B C2B N1B 117.83(10) . . ?
N2B C2B N3B 116.66(10) . . ?
N1B C2B N3B 125.51(10) . . ?
C9A C8A C5A 114.41(15) . . ?
C9A C8A H81 107.3(10) . . ?
C5A C8A H81 109.3(10) . . ?
C10A C7A C5A 115.78(14) . . ?
C10A C7A H71 109.9(9) . . ?
C5A C7A H71 102.8(9) . . ?
C7A C10A H11 111.0(11) . . ?
C7A C10A H12 107.8(17) . . ?
H11 C10A H12 108.1(14) . . ?
C8A C9A H91 111.7(13) . . ?
C8A C9A H92 109.6(16) . . ?
H91 C9A H92 107.7(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2B N3B C4B N4B 179.93(13) . . . . ?
C2B N3B C4B N3B 0.6(2) . . . 3 ?
O2A C2A N1A C4A 177.85(13) . . . . ?
N1A C2A N1A C4A -3.0(2) 3_655 . . . ?
C2A N1A C4A O4A -173.86(13) . . . . ?
C2A N1A C4A C5A 8.99(18) . . . . ?
C4A C5A C4A O4A 169.24(9) 3_655 . . . ?
C8A C5A C4A O4A 45.03(17) . . . . ?
C7A C5A C4A O4A -72.51(16) . . . . ?
C4A C5A C4A N1A -13.67(19) 3_655 . . . ?
C8A C5A C4A N1A -137.88(12) . . . . ?
C7A C5A C4A N1A 104.58(12) . . . . ?
C2B N1B C2B N2B -178.80(8) 3 . . . ?
C2B N1B C2B N3B 1.4(2) 3 . . . ?
C4B N3B C2B N2B 179.17(11) . . . . ?
C4B N3B C2B N1B -1.05(16) . . . . ?
C4A C5A C8A C9A 63.15(9) . . . . ?
C4A C5A C8A C9A -63.15(9) 3_655 . . . ?
C7A C5A C8A C9A 180.000(1) . . . . ?
C4A C5A C7A C10A -61.24(9) . . . . ?
C4A C5A C7A C10A 61.24(9) 3_655 . . . ?
C8A C5A C7A C10A 180.000(1) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4B H4B O4A 0.952(10) 2.036(11) 2.9718(12) 167.3(14) 3
N2B H2B2 O2A 0.967(11) 1.981(11) 2.9419(12) 172.7(14) .
N1A H1A N3B 0.990(11) 1.925(11) 2.9124(12) 174.9(13) .
N2B H2B1 N3B 0.948(11) 2.357(13) 3.1698(14) 143.6(14) 2_554

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 967146'
