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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3_741062_MelEDTA
_audit_creation_date             2014-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
'bis-1,2,3-Triamino-2,4,6-triazinium ethylenetriaminetetraacetate diaqua'
_chemical_formula_moiety         'C10 H14 N2 O8, 2(C3 H7 N6), 2(H2 O)'
_chemical_formula_sum            'C16 H32 N14 O10'
_chemical_formula_weight         580.55
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0884(3)
_cell_length_b                   7.7150(2)
_cell_length_c                   11.6340(5)
_cell_angle_alpha                80.755(3)
_cell_angle_beta                 78.037(4)
_cell_angle_gamma                83.455(3)
_cell_volume                     612.18(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.326
_diffrn_reflns_theta_min         2.684
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_device_type  
'XCalibur S 95mm CCD camera (sapphire) on κ-goniostat'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1834
_reflns_number_total             2953
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      0.897
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0541P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0892
_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 > 2sigma(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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B), C31(H31A,H31B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O11 O 1.07521(13) 0.17711(11) 0.00989(8) 0.0323(2) Uani 1 1 d . . . . .
O12 O 1.11531(14) 0.38869(12) -0.14660(9) 0.0390(3) Uani 1 1 d . . . . .
O21 O 0.59629(16) 0.22371(14) 0.30584(8) 0.0468(3) Uani 1 1 d . . . . .
O22 O 0.72759(16) -0.01238(13) 0.22287(9) 0.0461(3) Uani 1 1 d . . . . .
N11 N 0.70620(15) 0.14057(14) -0.00239(9) 0.0264(3) Uani 1 1 d . . . . .
C11 C 1.02287(19) 0.27371(16) -0.07646(11) 0.0273(3) Uani 1 1 d . . . . .
C12 C 0.83026(19) 0.24355(17) -0.10504(11) 0.0308(3) Uani 1 1 d . . . . .
H12A H 0.7617 0.3566 -0.1261 0.037 Uiso 1 1 calc R . . . .
H12B H 0.8540 0.1804 -0.1730 0.037 Uiso 1 1 calc R . . . .
C21 C 0.6546(2) 0.14092(19) 0.21953(12) 0.0333(3) Uani 1 1 d . . . . .
C22 C 0.6338(2) 0.24519(17) 0.09867(11) 0.0320(3) Uani 1 1 d . . . . .
H22A H 0.4985 0.2844 0.1001 0.038 Uiso 1 1 calc R . . . .
H22B H 0.7050 0.3491 0.0851 0.038 Uiso 1 1 calc R . . . .
C31 C 0.54926(19) 0.06985(17) -0.04598(11) 0.0306(3) Uani 1 1 d . . . . .
H31A H 0.6045 0.0199 -0.1182 0.037 Uiso 1 1 calc R . . . .
H31B H 0.4543 0.1656 -0.0645 0.037 Uiso 1 1 calc R . . . .
H11 H 0.779(2) 0.051(2) 0.0229(13) 0.041(4) Uiso 1 1 d . . . . .
N1 N 0.78814(16) -0.04351(15) 0.67091(10) 0.0345(3) Uani 1 1 d . . . . .
N2 N 0.76774(18) -0.06732(19) 0.47581(11) 0.0423(3) Uani 1 1 d . . . . .
N3 N 0.90086(17) -0.31177(16) 0.58734(9) 0.0373(3) Uani 1 1 d . . . . .
N4 N 0.9125(2) -0.28756(19) 0.77711(11) 0.0404(3) Uani 1 1 d . . . . .
N5 N 0.6547(2) 0.18797(19) 0.55382(15) 0.0497(4) Uani 1 1 d . . . . .
N6 N 0.8746(2) -0.3213(3) 0.39521(13) 0.0573(4) Uani 1 1 d . . . . .
C1 C 0.86687(19) -0.21171(18) 0.67585(11) 0.0317(3) Uani 1 1 d . . . . .
C2 C 0.7363(2) 0.02596(19) 0.56946(12) 0.0367(3) Uani 1 1 d . . . . .
C3 C 0.8481(2) -0.2346(2) 0.48749(12) 0.0391(4) Uani 1 1 d . . . . .
H4A H 0.972(2) -0.388(2) 0.7809(14) 0.049(5) Uiso 1 1 d . . . . .
H4B H 0.906(2) -0.2238(19) 0.8365(14) 0.041(4) Uiso 1 1 d . . . . .
H5A H 0.615(3) 0.255(3) 0.6130(18) 0.079(7) Uiso 1 1 d . . . . .
H5B H 0.630(2) 0.230(2) 0.4875(17) 0.053(5) Uiso 1 1 d . . . . .
H6A H 0.926(3) -0.425(3) 0.3979(17) 0.066(7) Uiso 1 1 d . . . . .
H6B H 0.838(3) -0.268(3) 0.330(2) 0.081(7) Uiso 1 1 d . . . . .
H2 H 0.738(2) -0.021(2) 0.4099(17) 0.058(5) Uiso 1 1 d . . . . .
O91 O 0.49382(19) 0.58720(18) 0.26406(12) 0.0559(3) Uani 1 1 d . . . . .
H91A H 0.620(4) 0.615(4) 0.224(2) 0.129(10) Uiso 1 1 d . . . . .
H91B H 0.501(3) 0.478(3) 0.296(2) 0.091(8) Uiso 1 1 d . . . . .


_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
O11 C11 1.2462(15) . ?
O12 C11 1.2492(15) . ?
O21 C21 1.2495(17) . ?
O22 C21 1.2337(17) . ?
N11 C12 1.4999(15) . ?
N11 C22 1.5025(16) . ?
N11 C31 1.5012(17) . ?
N11 H11 0.866(16) . ?
C11 C12 1.5213(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C21 C22 1.5302(18) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C31 C31 1.512(2) 2_655 ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
N1 C1 1.3502(17) . ?
N1 C2 1.3216(18) . ?
N2 C2 1.3673(19) . ?
N2 C3 1.348(2) . ?
N2 H2 0.849(19) . ?
N3 C1 1.3508(17) . ?
N3 C3 1.3234(18) . ?
N4 C1 1.3146(18) . ?
N4 H4A 0.835(17) . ?
N4 H4B 0.902(16) . ?
N5 C2 1.318(2) . ?
N5 H5A 0.91(2) . ?
N5 H5B 0.833(19) . ?
N6 C3 1.324(2) . ?
N6 H6A 0.84(2) . ?
N6 H6B 0.87(2) . ?
O91 H91A 0.95(3) . ?
O91 H91B 0.87(3) . ?

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
C12 N11 C22 111.97(10) . . ?
C12 N11 C31 109.16(10) . . ?
C12 N11 H11 106.8(9) . . ?
C22 N11 H11 107.4(10) . . ?
C31 N11 C22 114.13(10) . . ?
C31 N11 H11 107.0(10) . . ?
O11 C11 O12 127.21(13) . . ?
O11 C11 C12 117.27(11) . . ?
O12 C11 C12 115.44(11) . . ?
N11 C12 C11 112.03(10) . . ?
N11 C12 H12A 109.2 . . ?
N11 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O21 C21 C22 115.08(12) . . ?
O22 C21 O21 126.61(13) . . ?
O22 C21 C22 118.30(12) . . ?
N11 C22 C21 113.20(11) . . ?
N11 C22 H22A 108.9 . . ?
N11 C22 H22B 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
N11 C31 C31 111.27(13) . 2_655 ?
N11 C31 H31A 109.4 . . ?
N11 C31 H31B 109.4 . . ?
C31 C31 H31A 109.4 2_655 . ?
C31 C31 H31B 109.4 2_655 . ?
H31A C31 H31B 108.0 . . ?
C2 N1 C1 115.55(12) . . ?
C2 N2 H2 121.0(12) . . ?
C3 N2 C2 119.80(13) . . ?
C3 N2 H2 119.2(12) . . ?
C3 N3 C1 115.27(12) . . ?
C1 N4 H4A 119.3(12) . . ?
C1 N4 H4B 120.2(10) . . ?
H4A N4 H4B 118.9(16) . . ?
C2 N5 H5A 123.7(13) . . ?
C2 N5 H5B 119.1(12) . . ?
H5A N5 H5B 117.0(18) . . ?
C3 N6 H6A 121.5(14) . . ?
C3 N6 H6B 118.7(14) . . ?
H6A N6 H6B 120(2) . . ?
N1 C1 N3 126.45(12) . . ?
N4 C1 N1 117.21(13) . . ?
N4 C1 N3 116.33(13) . . ?
N1 C2 N2 121.10(14) . . ?
N5 C2 N1 121.59(15) . . ?
N5 C2 N2 117.30(15) . . ?
N3 C3 N2 121.79(13) . . ?
N3 C3 N6 120.13(16) . . ?
N6 C3 N2 118.07(16) . . ?
H91A O91 H91B 108(2) . . ?

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
N11 H11 O11 0.866(16) 1.985(15) 2.7500(14) 146.7(14) 2_755
N4 H4A O12 0.835(17) 2.053(18) 2.8445(17) 158.1(16) 1_546
N4 H4B O11 0.902(16) 1.912(17) 2.7675(16) 157.7(14) 2_756

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
O11 C11 C12 N11 17.94(15) . . . . ?
O12 C11 C12 N11 -165.23(10) . . . . ?
O21 C21 C22 N11 179.86(12) . . . . ?
O22 C21 C22 N11 0.69(18) . . . . ?
C12 N11 C22 C21 -134.20(12) . . . . ?
C12 N11 C31 C31 166.18(13) . . . 2_655 ?
C22 N11 C12 C11 69.27(13) . . . . ?
C22 N11 C31 C31 -67.69(16) . . . 2_655 ?
C31 N11 C12 C11 -163.37(10) . . . . ?
C31 N11 C22 C21 101.16(13) . . . . ?
C1 N1 C2 N2 -2.00(19) . . . . ?
C1 N1 C2 N5 178.79(13) . . . . ?
C1 N3 C3 N2 0.5(2) . . . . ?
C1 N3 C3 N6 -179.85(13) . . . . ?
C2 N1 C1 N3 1.64(19) . . . . ?
C2 N1 C1 N4 -177.18(13) . . . . ?
C2 N2 C3 N3 -1.0(2) . . . . ?
C2 N2 C3 N6 179.38(13) . . . . ?
C3 N2 C2 N1 1.8(2) . . . . ?
C3 N2 C2 N5 -178.96(13) . . . . ?
C3 N3 C1 N1 -0.9(2) . . . . ?
C3 N3 C1 N4 177.92(13) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 741062'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_741063_MelDMSO
_audit_creation_date             2014-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        'Melamine DMSO solvate'
_chemical_formula_moiety         'C3 H6 N6, C2 H6 O S'
_chemical_formula_sum            'C5 H12 N6 O S'
_chemical_formula_weight         204.27
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4296(6)
_cell_length_b                   12.3333(11)
_cell_length_c                   11.9384(11)
_cell_angle_alpha                90
_cell_angle_beta                 114.070(6)
_cell_angle_gamma                90
_cell_volume                     998.81(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector 
scaling and absorption correction
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11113
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1483
_reflns_number_total             2035
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0236P)²+0.6979P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N1 N 0.6369(3) 0.27390(14) 0.51408(16) 0.0153(4) Uani 1 1 d . . . . .
N2 N 0.5356(2) 0.10913(14) 0.39774(15) 0.0162(4) Uani 1 1 d . . . . .
N3 N 0.6610(3) 0.25727(14) 0.32102(16) 0.0161(4) Uani 1 1 d . . . . .
N4 N 0.5232(3) 0.12859(17) 0.58565(18) 0.0201(4) Uani 1 1 d . . . . .
H4A H 0.566(3) 0.160(2) 0.659(2) 0.024(7) Uiso 1 1 d . . . . .
H4B H 0.502(4) 0.060(2) 0.582(3) 0.037(8) Uiso 1 1 d . . . . .
N5 N 0.5446(3) 0.10434(17) 0.20703(18) 0.0205(4) Uani 1 1 d . . . . .
H5A H 0.480(3) 0.047(2) 0.193(2) 0.017(6) Uiso 1 1 d . . . . .
H5B H 0.571(4) 0.135(2) 0.149(3) 0.039(8) Uiso 1 1 d . . . . .
N6 N 0.7663(3) 0.41107(15) 0.43713(19) 0.0182(4) Uani 1 1 d . . . . .
H6A H 0.838(3) 0.4205(18) 0.395(2) 0.018(6) Uiso 1 1 d . . . . .
H6B H 0.806(3) 0.4432(19) 0.506(2) 0.021(7) Uiso 1 1 d . . . . .
C1 C 0.6873(3) 0.31037(17) 0.42465(19) 0.0146(5) Uani 1 1 d . . . . .
C2 C 0.5800(3) 0.15819(17) 0.31141(19) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.5669(3) 0.17169(17) 0.49689(19) 0.0151(5) Uani 1 1 d . . . . .
S1 S 1.18475(8) 0.38288(5) 0.29063(5) 0.02399(17) Uani 1 1 d . . . . .
O1S O 1.0755(3) 0.44980(15) 0.34741(16) 0.0342(5) Uani 1 1 d . . . . .
C1S C 1.0746(5) 0.4142(3) 0.1315(3) 0.0376(7) Uani 1 1 d . . . . .
H1SA H 0.920(5) 0.404(2) 0.101(3) 0.049(8) Uiso 1 1 d . . . . .
H1SB H 1.123(5) 0.364(3) 0.090(4) 0.081(13) Uiso 1 1 d . . . . .
H1SC H 1.107(4) 0.485(3) 0.124(3) 0.049(9) Uiso 1 1 d . . . . .
C2S C 1.0936(4) 0.2474(2) 0.2803(3) 0.0356(7) Uani 1 1 d . . . . .
H2SA H 0.953(4) 0.249(2) 0.246(2) 0.033(7) Uiso 1 1 d . . . . .
H2SB H 1.145(4) 0.224(2) 0.365(3) 0.053(9) Uiso 1 1 d . . . . .
H2SC H 1.143(4) 0.202(3) 0.225(3) 0.058(9) Uiso 1 1 d . . . . .


_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
N1 C1 1.345(3) . ?
N1 C3 1.347(3) . ?
N2 C2 1.347(3) . ?
N2 C3 1.351(3) . ?
N3 C1 1.342(3) . ?
N3 C2 1.346(3) . ?
N4 H4A 0.89(3) . ?
N4 H4B 0.86(3) . ?
N4 C3 1.338(3) . ?
N5 H5A 0.83(2) . ?
N5 H5B 0.88(3) . ?
N5 C2 1.340(3) . ?
N6 H6A 0.88(3) . ?
N6 H6B 0.85(3) . ?
N6 C1 1.356(3) . ?
S1 O1S 1.4995(17) . ?
S1 C1S 1.778(3) . ?
S1 C2S 1.788(3) . ?
C1S H1SA 1.06(3) . ?
C1S H1SB 0.95(4) . ?
C1S H1SC 0.92(3) . ?
C2S H2SA 0.96(3) . ?
C2S H2SB 0.97(3) . ?
C2S H2SC 1.03(3) . ?

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
C1 N1 C3 114.03(18) . . ?
C2 N2 C3 113.91(18) . . ?
C1 N3 C2 114.44(18) . . ?
H4A N4 H4B 118(2) . . ?
C3 N4 H4A 120.0(16) . . ?
C3 N4 H4B 116.4(18) . . ?
H5A N5 H5B 120(2) . . ?
C2 N5 H5A 119.6(16) . . ?
C2 N5 H5B 119.9(18) . . ?
H6A N6 H6B 116(2) . . ?
C1 N6 H6A 113.2(15) . . ?
C1 N6 H6B 119.9(16) . . ?
N1 C1 N6 117.87(19) . . ?
N3 C1 N1 125.85(19) . . ?
N3 C1 N6 116.25(19) . . ?
N3 C2 N2 125.66(19) . . ?
N5 C2 N2 118.19(19) . . ?
N5 C2 N3 116.14(19) . . ?
N1 C3 N2 125.84(19) . . ?
N4 C3 N1 117.02(19) . . ?
N4 C3 N2 117.13(19) . . ?
O1S S1 C1S 105.37(14) . . ?
O1S S1 C2S 106.61(13) . . ?
C1S S1 C2S 97.65(15) . . ?
S1 C1S H1SA 107.7(16) . . ?
S1 C1S H1SB 108(2) . . ?
S1 C1S H1SC 106.8(19) . . ?
H1SA C1S H1SB 109(3) . . ?
H1SA C1S H1SC 112(2) . . ?
H1SB C1S H1SC 113(3) . . ?
S1 C2S H2SA 108.9(16) . . ?
S1 C2S H2SB 103.1(18) . . ?
S1 C2S H2SC 108.9(17) . . ?
H2SA C2S H2SB 111(2) . . ?
H2SA C2S H2SC 110(2) . . ?
H2SB C2S H2SC 115(2) . . ?

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
C1 N1 C3 N2 -3.7(3) . . . . ?
C1 N1 C3 N4 176.77(18) . . . . ?
C1 N3 C2 N2 -3.6(3) . . . . ?
C1 N3 C2 N5 177.57(19) . . . . ?
C2 N2 C3 N1 -0.4(3) . . . . ?
C2 N2 C3 N4 179.08(18) . . . . ?
C2 N3 C1 N1 -1.4(3) . . . . ?
C2 N3 C1 N6 -179.22(18) . . . . ?
C3 N1 C1 N3 4.7(3) . . . . ?
C3 N1 C1 N6 -177.50(18) . . . . ?
C3 N2 C2 N3 4.4(3) . . . . ?
C3 N2 C2 N5 -176.76(19) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 741063'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4_741064_MelSO4

_audit_creation_date             2014-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        'dimelaminium sulfate'
_chemical_formula_moiety         '2(C3 H7 N6), O4 S'
_chemical_formula_sum            'C6 H14 N12 O4 S'
_chemical_formula_weight         350.35
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.041(2)
_cell_length_b                   10.6373(14)
_cell_length_c                   14.289(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.652(14)
_cell_angle_gamma                90
_cell_volume                     2664.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1014
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.9649
_cell_measurement_theta_min      2.3191
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.041
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.2339
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6922
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.980
_diffrn_reflns_theta_min         2.323
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.1340
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_device_type  
'XCalibur S 95mm CCD camera (sapphire) on κ-goniostat'
_diffrn_measurement_method       ?
_diffrn_orient_matrix_UB_11      0.0013519186
_diffrn_orient_matrix_UB_12      0.0318785378
_diffrn_orient_matrix_UB_13      -0.0431425230
_diffrn_orient_matrix_UB_21      0.0261689637
_diffrn_orient_matrix_UB_22      -0.0453253410
_diffrn_orient_matrix_UB_23      -0.0093733689
_diffrn_orient_matrix_UB_31      -0.0308344756
_diffrn_orient_matrix_UB_32      -0.0370972495
_diffrn_orient_matrix_UB_33      -0.0257152421
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                918
_reflns_number_total             2897
_reflns_odcompleteness_completeness 93.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.2244
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      0.772
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0322P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0972
_refine_special_details          
;
olex2_refinement_description
1. Restrained distances
 N13-H13 = N17-H17A = N17-H17B = N18-H18A = N18-H18B = N19-H19A = N19-H19B
 0.87 with sigma of 0.05
 N23-H23 = N27-H27A = N27-H27B = N28-H28A = N28-H28B = N29-H29A = N29-H29B
 0.87 with sigma of 0.05
2. Others
 Fixed Uiso: H13(0.05) H19A(0.05) H19B(0.05) H27A(0.05) H28B(0.05) H29B(0.05)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N11 N 0.0772(2) 0.6518(3) 0.1117(3) 0.0339(13) Uani 1 1 d . . . . .
C12 C 0.1337(3) 0.5996(4) 0.0814(4) 0.0343(15) Uani 1 1 d . . . . .
N13 N 0.1373(2) 0.4732(3) 0.0674(4) 0.0325(13) Uani 1 1 d D . . . .
C14 C 0.0831(3) 0.3971(4) 0.0909(4) 0.0338(15) Uani 1 1 d . . . . .
N15 N 0.0246(2) 0.4443(3) 0.1201(3) 0.0328(13) Uani 1 1 d . . . . .
C16 C 0.0230(3) 0.5704(4) 0.1260(4) 0.0357(16) Uani 1 1 d . . . . .
N17 N -0.0390(2) 0.6209(4) 0.1438(3) 0.0420(13) Uani 1 1 d D . . . .
N18 N 0.1904(2) 0.6680(4) 0.0646(3) 0.0435(13) Uani 1 1 d D . . . .
N19 N 0.0894(2) 0.2748(3) 0.0807(3) 0.0417(13) Uani 1 1 d D . . . .
H13 H 0.173(2) 0.439(3) 0.035(3) 0.050 Uiso 1 1 d D . . . .
H17A H -0.045(2) 0.705(3) 0.149(3) 0.045(14) Uiso 1 1 d D . . . .
H17B H -0.076(2) 0.575(3) 0.149(3) 0.040(14) Uiso 1 1 d D . . . .
H18A H 0.225(2) 0.630(4) 0.037(3) 0.058(15) Uiso 1 1 d D . . . .
H18B H 0.193(2) 0.754(3) 0.073(3) 0.054(14) Uiso 1 1 d D . . . .
H19A H 0.050(2) 0.223(3) 0.094(3) 0.050 Uiso 1 1 d D . . . .
H19B H 0.130(2) 0.240(3) 0.078(3) 0.050 Uiso 1 1 d D . . . .
N21 N 0.02378(19) 0.1017(3) 0.3685(3) 0.0248(11) Uani 1 1 d . . . . .
C22 C 0.0835(2) 0.1430(4) 0.3377(4) 0.0247(13) Uani 1 1 d . . . . .
N23 N 0.1367(2) 0.0626(3) 0.3174(4) 0.0297(13) Uani 1 1 d D . . . .
C24 C 0.1306(3) -0.0631(4) 0.3358(4) 0.0318(15) Uani 1 1 d . . . . .
N25 N 0.0730(2) -0.1088(3) 0.3675(3) 0.0305(12) Uani 1 1 d . . . . .
C26 C 0.0188(3) -0.0240(4) 0.3763(4) 0.0253(13) Uani 1 1 d . . . . .
N27 N 0.0922(2) 0.2642(3) 0.3257(3) 0.0346(12) Uani 1 1 d D . . . .
N28 N 0.1850(2) -0.1387(4) 0.3227(4) 0.0469(14) Uani 1 1 d D . . . .
N29 N -0.0431(2) -0.0692(4) 0.3977(3) 0.0351(12) Uani 1 1 d D . . . .
H23 H 0.163(2) 0.088(4) 0.270(3) 0.049(14) Uiso 1 1 d D . . . .
H27A H 0.1324(19) 0.301(3) 0.313(3) 0.050 Uiso 1 1 d D . . . .
H27B H 0.0542(19) 0.321(3) 0.339(3) 0.036(12) Uiso 1 1 d D . . . .
H28A H 0.186(2) -0.222(3) 0.331(4) 0.068(17) Uiso 1 1 d D . . . .
H28B H 0.217(2) -0.119(4) 0.287(3) 0.050 Uiso 1 1 d D . . . .
H29A H -0.074(3) -0.022(4) 0.405(4) 0.07(2) Uiso 1 1 d D . . . .
H29B H -0.050(2) -0.151(3) 0.398(4) 0.050 Uiso 1 1 d D . . . .
S1 S 0.24991(10) 0.01542(10) 0.12641(18) 0.0342(3) Uani 1 1 d . . . . .
O1 O 0.19886(17) 0.0955(3) 0.1633(3) 0.0613(13) Uani 1 1 d . . . . .
O2 O 0.30188(17) 0.0928(3) 0.0873(3) 0.0607(12) Uani 1 1 d . . . . .
O3 O 0.20614(19) -0.0641(3) 0.0487(3) 0.0570(12) Uani 1 1 d . . . . .
O4 O 0.29228(19) -0.0646(3) 0.2036(3) 0.0652(13) Uani 1 1 d . . . . .


_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
N11 C12 1.320(5) . ?
N11 C16 1.357(5) . ?
C12 N13 1.363(5) . ?
C12 N18 1.322(5) . ?
N13 C14 1.371(5) . ?
N13 H13 0.96(3) . ?
C14 N15 1.322(5) . ?
C14 N19 1.317(5) . ?
N15 C16 1.344(5) . ?
C16 N17 1.319(5) . ?
N17 H17A 0.90(3) . ?
N17 H17B 0.85(3) . ?
N18 H18A 0.91(3) . ?
N18 H18B 0.93(3) . ?
N19 H19A 0.96(3) . ?
N19 H19B 0.83(3) . ?
N21 C22 1.331(5) . ?
N21 C26 1.347(4) . ?
C22 N23 1.366(5) . ?
C22 N27 1.315(5) . ?
N23 C24 1.372(5) . ?
N23 H23 0.95(3) . ?
C24 N25 1.320(5) . ?
C24 N28 1.317(5) . ?
N25 C26 1.357(5) . ?
C26 N29 1.317(5) . ?
N27 H27A 0.88(3) . ?
N27 H27B 0.97(3) . ?
N28 H28A 0.90(3) . ?
N28 H28B 0.88(3) . ?
N29 H29A 0.77(3) . ?
N29 H29B 0.88(3) . ?
S1 O1 1.443(3) . ?
S1 O2 1.455(3) . ?
S1 O3 1.470(4) . ?
S1 O4 1.459(4) . ?

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
C12 N11 C16 114.8(4) . . ?
N11 C12 N13 122.0(4) . . ?
N11 C12 N18 121.2(4) . . ?
N18 C12 N13 116.8(4) . . ?
C12 N13 C14 119.1(4) . . ?
C12 N13 H13 120(2) . . ?
C14 N13 H13 120(2) . . ?
N15 C14 N13 121.4(4) . . ?
N19 C14 N13 118.1(4) . . ?
N19 C14 N15 120.4(4) . . ?
C14 N15 C16 115.4(4) . . ?
N15 C16 N11 126.9(4) . . ?
N17 C16 N11 116.3(4) . . ?
N17 C16 N15 116.7(4) . . ?
C16 N17 H17A 123(2) . . ?
C16 N17 H17B 120(3) . . ?
H17A N17 H17B 117(3) . . ?
C12 N18 H18A 118(3) . . ?
C12 N18 H18B 123(2) . . ?
H18A N18 H18B 118(4) . . ?
C14 N19 H19A 118(2) . . ?
C14 N19 H19B 123(3) . . ?
H19A N19 H19B 118(4) . . ?
C22 N21 C26 115.4(3) . . ?
N21 C22 N23 121.8(4) . . ?
N27 C22 N21 119.8(4) . . ?
N27 C22 N23 118.4(4) . . ?
C22 N23 C24 118.5(4) . . ?
C22 N23 H23 118(3) . . ?
C24 N23 H23 119(3) . . ?
N25 C24 N23 122.0(4) . . ?
N28 C24 N23 118.2(4) . . ?
N28 C24 N25 119.9(4) . . ?
C24 N25 C26 115.4(4) . . ?
N21 C26 N25 126.1(4) . . ?
N29 C26 N21 117.3(4) . . ?
N29 C26 N25 116.6(4) . . ?
C22 N27 H27A 127(3) . . ?
C22 N27 H27B 119(2) . . ?
H27A N27 H27B 115(3) . . ?
C24 N28 H28A 126(3) . . ?
C24 N28 H28B 123(3) . . ?
H28A N28 H28B 108(4) . . ?
C26 N29 H29A 118(4) . . ?
C26 N29 H29B 119(3) . . ?
H29A N29 H29B 123(4) . . ?
O1 S1 O2 109.35(17) . . ?
O1 S1 O3 109.9(2) . . ?
O1 S1 O4 109.5(3) . . ?
O2 S1 O3 108.4(3) . . ?
O2 S1 O4 110.5(3) . . ?
O4 S1 O3 109.14(18) . . ?

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
N13 H13 O2 0.96(3) 1.93(4) 2.780(6) 147(4) 7
N17 H17B O2 0.85(3) 2.17(4) 2.809(5) 131(4) 3_455
N18 H18B O3 0.93(3) 1.98(3) 2.877(5) 162(4) 1_565
N19 H19B O1 0.83(3) 2.16(4) 2.797(5) 133(4) .
N23 H23 O1 0.95(3) 1.79(4) 2.720(5) 163(4) .
N27 H27A O4 0.88(3) 2.02(3) 2.872(4) 161(4) 4

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
N11 C12 N13 C14 -4.0(8) . . . . ?
C12 N11 C16 N15 5.9(8) . . . . ?
C12 N11 C16 N17 -171.3(5) . . . . ?
C12 N13 C14 N15 5.0(8) . . . . ?
C12 N13 C14 N19 -177.1(5) . . . . ?
N13 C14 N15 C16 -0.8(7) . . . . ?
C14 N15 C16 N11 -5.0(7) . . . . ?
C14 N15 C16 N17 172.2(6) . . . . ?
C16 N11 C12 N13 -1.0(8) . . . . ?
C16 N11 C12 N18 -180.0(5) . . . . ?
N18 C12 N13 C14 175.0(5) . . . . ?
N19 C14 N15 C16 -178.6(5) . . . . ?
N21 C22 N23 C24 -4.6(8) . . . . ?
C22 N21 C26 N25 8.8(8) . . . . ?
C22 N21 C26 N29 -173.8(5) . . . . ?
C22 N23 C24 N25 3.7(7) . . . . ?
C22 N23 C24 N28 -175.1(5) . . . . ?
N23 C24 N25 C26 2.8(8) . . . . ?
C24 N25 C26 N21 -9.6(8) . . . . ?
C24 N25 C26 N29 172.9(5) . . . . ?
C26 N21 C22 N23 -1.2(7) . . . . ?
C26 N21 C22 N27 178.4(4) . . . . ?
N27 C22 N23 C24 175.8(4) . . . . ?
N28 C24 N25 C26 -178.4(5) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 741064'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5_741065_MelNO3
_audit_creation_date             2014-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        'melaminium dinitrate'
_chemical_formula_moiety         'C3 H8 N6, 2(N O3)'
_chemical_formula_sum            'C3 H8 N8 O6'
_chemical_formula_weight         252.17
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7710(14)
_cell_length_b                   9.8924(18)
_cell_length_c                   12.186(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.198(9)
_cell_angle_gamma                90
_cell_volume                     918.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    100
_cell_measurement_theta_max      64.94
_cell_measurement_theta_min      5.80
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.516
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector 
scaling and absorption correction'
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2218
_diffrn_reflns_av_unetI/netI     0.6454
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5198
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.118
_diffrn_reflns_theta_min         5.804
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker X8 Proteum Microstar CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                901
_reflns_number_total             1518
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3022
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0638P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.017) H2(0.019) H4A(0.022) H4B(0.022) H5A(0.019) H5B(0.019)
 H6A(0.022) H6B(0.022)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N 0.68880(15) 0.35541(12) 0.57915(16) 0.0138(4) Uani 1 1 d . . . . .
H1 H 0.635(2) 0.3716(19) 0.6372(19) 0.017 Uiso 1 1 d R . . . .
N2 N 0.78154(15) 0.18509(13) 0.47504(17) 0.0156(5) Uani 1 1 d . . . . .
H2 H 0.789(2) 0.1024(18) 0.4647(18) 0.019 Uiso 1 1 d R . . . .
N3 N 0.83415(15) 0.41329(12) 0.43111(16) 0.0137(5) Uani 1 1 d . . . . .
N4 N 0.64401(17) 0.13223(13) 0.62046(17) 0.0182(5) Uani 1 1 d . . . . .
H4A H 0.6570(18) 0.038(2) 0.6070(16) 0.022 Uiso 1 1 d R . . . .
H4B H 0.603(3) 0.153(2) 0.663(2) 0.022 Uiso 1 1 d R . . . .
N5 N 0.93033(17) 0.23817(13) 0.33541(16) 0.0159(5) Uani 1 1 d . . . . .
H5A H 0.972(2) 0.2939(19) 0.3035(19) 0.019 Uiso 1 1 d R . . . .
H5B H 0.948(2) 0.1430(19) 0.3181(18) 0.019 Uiso 1 1 d R . . . .
N6 N 0.72518(18) 0.57782(12) 0.53072(17) 0.0181(5) Uani 1 1 d . . . . .
H6A H 0.768(2) 0.6184(18) 0.497(2) 0.022 Uiso 1 1 d R . . . .
H6B H 0.671(2) 0.6000(18) 0.578(2) 0.022 Uiso 1 1 d R . . . .
C1 C 0.70318(17) 0.22075(15) 0.56033(19) 0.0146(6) Uani 1 1 d . . . . .
C2 C 0.84922(17) 0.28081(16) 0.4143(2) 0.0135(5) Uani 1 1 d . . . . .
C3 C 0.75169(18) 0.44913(16) 0.51175(18) 0.0139(5) Uani 1 1 d . . . . .
N10 N 0.56158(16) 0.81554(13) 0.69336(18) 0.0145(5) Uani 1 1 d . . . . .
O11 O 0.53376(13) 0.69148(10) 0.70594(13) 0.0189(4) Uani 1 1 d . . . . .
O13 O 0.50203(14) 0.90299(10) 0.75019(14) 0.0203(4) Uani 1 1 d . . . . .
O12 O 0.64602(13) 0.84936(11) 0.62066(13) 0.0229(5) Uani 1 1 d . . . . .
N20 N 0.13069(16) 0.36589(13) 0.13084(15) 0.0156(5) Uani 1 1 d . . . . .
O21 O 0.11766(13) 0.24040(11) 0.13672(15) 0.0197(4) Uani 1 1 d . . . . .
O22 O 0.07772(13) 0.44104(10) 0.20069(13) 0.0218(4) Uani 1 1 d . . . . .
O23 O 0.19571(15) 0.41634(10) 0.05347(14) 0.0259(4) Uani 1 1 d . . . . .


_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
N1 H1 0.90(2) . ?
N1 C1 1.360(2) . ?
N1 C3 1.389(2) . ?
N2 H2 0.832(17) . ?
N2 C1 1.350(2) . ?
N2 C2 1.369(2) . ?
N3 C2 1.335(2) . ?
N3 C3 1.322(2) . ?
N4 H4A 0.96(2) . ?
N4 H4B 0.69(2) . ?
N4 C1 1.283(2) . ?
N5 H5A 0.78(2) . ?
N5 H5B 0.980(18) . ?
N5 C2 1.317(2) . ?
N6 H6A 0.71(2) . ?
N6 H6B 0.80(2) . ?
N6 C3 1.317(2) . ?
N10 O11 1.2607(18) . ?
N10 O13 1.2516(19) . ?
N10 O12 1.246(2) . ?
N20 O21 1.2487(18) . ?
N20 O22 1.2580(19) . ?
N20 O23 1.256(2) . ?

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
C1 N1 H1 111.8(12) . . ?
C1 N1 C3 120.28(16) . . ?
C3 N1 H1 127.9(12) . . ?
C1 N2 H2 115.3(14) . . ?
C1 N2 C2 120.94(15) . . ?
C2 N2 H2 123.7(14) . . ?
C3 N3 C2 116.57(16) . . ?
H4A N4 H4B 120(2) . . ?
C1 N4 H4A 120.5(11) . . ?
C1 N4 H4B 119.3(19) . . ?
H5A N5 H5B 119.1(18) . . ?
C2 N5 H5A 116.1(14) . . ?
C2 N5 H5B 124.8(12) . . ?
H6A N6 H6B 129(2) . . ?
C3 N6 H6A 109.7(15) . . ?
C3 N6 H6B 120.7(14) . . ?
N2 C1 N1 116.75(16) . . ?
N4 C1 N1 121.46(17) . . ?
N4 C1 N2 121.79(15) . . ?
N3 C2 N2 122.79(17) . . ?
N5 C2 N2 117.52(15) . . ?
N5 C2 N3 119.69(17) . . ?
N3 C3 N1 122.53(14) . . ?
N6 C3 N1 117.16(16) . . ?
N6 C3 N3 120.31(16) . . ?
O13 N10 O11 121.00(15) . . ?
O12 N10 O11 118.31(15) . . ?
O12 N10 O13 120.66(12) . . ?
O21 N20 O22 120.52(15) . . ?
O21 N20 O23 119.13(15) . . ?
O23 N20 O22 120.34(12) . . ?

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
N4 H4A O12 0.96(2) 1.88(2) 2.7983(17) 161.3(16) 1_545

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
C1 N1 C3 N3 -3.2(3) . . . . ?
C1 N1 C3 N6 176.45(19) . . . . ?
C1 N2 C2 N3 -3.6(3) . . . . ?
C1 N2 C2 N5 177.17(17) . . . . ?
C2 N2 C1 N1 2.7(2) . . . . ?
C2 N2 C1 N4 -177.73(19) . . . . ?
C2 N3 C3 N1 2.3(3) . . . . ?
C2 N3 C3 N6 -177.28(18) . . . . ?
C3 N1 C1 N2 0.5(3) . . . . ?
C3 N1 C1 N4 -179.05(16) . . . . ?
C3 N3 C2 N2 1.0(3) . . . . ?
C3 N3 C2 N5 -179.82(16) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 741065'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2_995318_MelTheobr

_audit_creation_date             2014-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        'tri-theobromine melamine'
_chemical_formula_moiety         'C3 H6 N6, 3(C7 H8 N4 O2)'
_chemical_formula_sum            'C24 H30 N18 O6'
_chemical_formula_weight         666.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H30 N18 O6'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.3308(8)
_cell_length_b                   16.2228(10)
_cell_length_c                   13.1104(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.388(7)
_cell_angle_gamma                90
_cell_volume                     2875.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2894
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      66.5936
_cell_measurement_theta_min      4.2536
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.3657
_exptl_crystal_size_mid          0.1922
_exptl_crystal_size_min          0.0903
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10236
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.704
_diffrn_reflns_theta_min         4.257
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       39.8381  -38.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       39.8381   38.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega  131.00  165.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  103.00  163.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   20.00   47.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   16.00   48.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   24.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00   69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   65.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   22.00   50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00   83.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   90.00  117.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 15 omega   20.00   67.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega   58.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -52.0000  -19.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   14.00   49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 18 omega   21.00  122.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -57.0000 101

#__ type_ start__ end____ width___ exp.time_
 19 omega -114.00  -10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8381  -57.0000 -180.0000 104

#__ type_ start__ end____ width___ exp.time_
 20 omega  -69.00   34.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8381   57.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 21 omega -119.00   -6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8381  -77.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
 22 omega   63.00   88.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   41.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   17.0000  -95.0000 135
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0903049000
_diffrn_orient_matrix_UB_12      -0.0215783000
_diffrn_orient_matrix_UB_13      0.0337700000
_diffrn_orient_matrix_UB_21      -0.0662758000
_diffrn_orient_matrix_UB_22      0.0003127000
_diffrn_orient_matrix_UB_23      -0.1196428000
_diffrn_orient_matrix_UB_31      0.0208595000
_diffrn_orient_matrix_UB_32      -0.0924782000
_diffrn_orient_matrix_UB_33      -0.0081661000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1916
_reflns_number_total             2523
_reflns_odcompleteness_completeness 94.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1351P)²+3.2614P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2244
_refine_special_details          
;
 ?
;
_refinement_special_details      'both theobromine molecules disordered'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N13, C13}
{C15, N15}
{C33, N33}
3. Uiso/Uaniso restraints and constraints
Uanis(N13) = Uanis(C13)
Uanis(C15) = Uanis(N15)
Uanis(C18) = Uanis(C18A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C33) = Uanis(N33)
4. Others
 Fixed Sof: N13(0.75) C13(0.25) C15(0.75) N15(0.25) N17(0.75) N17A(0.25)
 C18(0.75) H18(0.75) C18A(0.25) H18A(0.25) C22(0.75) H22A(0.75) H22B(0.75)
 H22C(0.75) C22A(0.25) H22D(0.25) H22E(0.25) H22F(0.25) C23(0.75) H23A(0.75)
 H23B(0.75) H23C(0.75) C23A(0.25) H23D(0.25) H23E(0.25) H23F(0.25) C33(0.5)
 N33(0.5) N35(0.5) C36(0.5) H36(0.5) C39(0.5) H39A(0.5) H39B(0.5) H39C(0.5)
 C40(0.5) H40A(0.5) H40B(0.5) H40C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N11(H11), C18(H18), C18A(H18A), N31(H31), C36(H36)
5.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
5.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F), C23(H23A,H23B,H23C), C23A(H23D,
 H23E,H23F), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N 0.5000 0.4790(2) 0.7500 0.0475(8) Uani 1 2 d S T P . .
C2 C 0.41793(17) 0.5247(2) 0.7026(2) 0.0448(7) Uani 1 1 d . . . . .
N3 N 0.41314(15) 0.60659(16) 0.70093(18) 0.0456(6) Uani 1 1 d . . . . .
C4 C 0.5000 0.6458(3) 0.7500 0.0438(9) Uani 1 2 d S T P . .
N5 N 0.33457(16) 0.48261(17) 0.6526(2) 0.0557(7) Uani 1 1 d . . . . .
H5A H 0.2792 0.5093 0.6201 0.067 Uiso 1 1 calc R . . . .
H5B H 0.3354 0.4284 0.6523 0.067 Uiso 1 1 calc R . . . .
N6 N 0.5000 0.7266(3) 0.7500 0.0471(9) Uani 1 2 d S T P . .
H6 H 0.450(3) 0.753(2) 0.724(3) 0.057 Uiso 1 1 d R . . . .
N11 N 0.27171(16) 0.80368(16) 0.39265(19) 0.0489(7) Uani 1 1 d . . . . .
H11 H 0.2154 0.8297 0.3622 0.059 Uiso 1 1 calc R . . . .
C12 C 0.26795(19) 0.7202(2) 0.3804(2) 0.0489(7) Uani 1 1 d . . . . .
N13 N 0.35745(18) 0.67889(19) 0.4225(2) 0.0526(7) Uani 0.75 1 d . . . A 1
C13 C 0.35745(18) 0.67889(19) 0.4225(2) 0.0526(7) Uani 0.25 1 d . . . A 2
C14 C 0.4423(2) 0.7236(2) 0.4759(2) 0.0525(8) Uani 1 1 d . . . . .
C15 C 0.44050(19) 0.8068(2) 0.4879(2) 0.0550(8) Uani 0.75 1 d . . . B 1
N15 N 0.44050(19) 0.8068(2) 0.4879(2) 0.0550(8) Uani 0.25 1 d . . . B 2
C16 C 0.35230(19) 0.8538(2) 0.4468(2) 0.0510(8) Uani 1 1 d . . . . .
N17 N 0.5367(2) 0.8237(3) 0.5447(3) 0.0510(9) Uani 0.75 1 d . . . B 1
N17A N 0.3960(15) 0.6132(12) 0.4385(15) 0.071(5) Uani 0.25 1 d . . . A 2
C18 C 0.5873(3) 0.7535(3) 0.5601(3) 0.0551(10) Uani 0.75 1 d . . . B 1
H18 H 0.6563 0.7505 0.5979 0.066 Uiso 0.75 1 calc R . . B 1
C18A C 0.4951(8) 0.6147(9) 0.4858(10) 0.0551(10) Uani 0.25 1 d . . . A 2
H18A H 0.5348 0.5665 0.4953 0.066 Uiso 0.25 1 calc R . . A 2
N19 N 0.53231(17) 0.68776(18) 0.5176(2) 0.0558(7) Uani 1 1 d . . . . .
O20 O 0.34392(14) 0.92773(15) 0.4536(2) 0.0646(7) Uani 1 1 d . . . . .
O21 O 0.18997(15) 0.68423(13) 0.33336(17) 0.0549(6) Uani 1 1 d . . . . .
C22 C 0.3604(5) 0.5877(4) 0.4136(5) 0.0562(14) Uani 0.75 1 d . . . A 1
H22A H 0.4283 0.5701 0.4239 0.084 Uiso 0.75 1 calc GR . . A 1
H22B H 0.3170 0.5705 0.3419 0.084 Uiso 0.75 1 calc GR . . A 1
H22C H 0.3379 0.5624 0.4692 0.084 Uiso 0.75 1 calc GR . . A 1
C22A C 0.5346(13) 0.8689(13) 0.5506(13) 0.0562(14) Uani 0.25 1 d . . . B 2
H22D H 0.5919 0.8358 0.5919 0.084 Uiso 0.25 1 calc GR . . B 2
H22E H 0.5155 0.9055 0.5999 0.084 Uiso 0.25 1 calc GR . . B 2
H22F H 0.5518 0.9021 0.4970 0.084 Uiso 0.25 1 calc GR . . B 2
C23 C 0.5754(3) 0.9054(3) 0.5838(5) 0.0679(13) Uani 0.75 1 d . . . B 1
H23A H 0.6435 0.9003 0.6334 0.102 Uiso 0.75 1 calc GR . . B 1
H23B H 0.5342 0.9305 0.6219 0.102 Uiso 0.75 1 calc GR . . B 1
H23C H 0.5745 0.9402 0.5224 0.102 Uiso 0.75 1 calc GR . . B 1
C23A C 0.3344(10) 0.5418(11) 0.4019(15) 0.0679(13) Uani 0.25 1 d . . . A 2
H23D H 0.2787 0.5439 0.4295 0.102 Uiso 0.25 1 calc GR . . A 2
H23E H 0.3733 0.4918 0.4286 0.102 Uiso 0.25 1 calc GR . . A 2
H23F H 0.3092 0.5409 0.3227 0.102 Uiso 0.25 1 calc GR . . A 2
N31 N 1.0000 0.7968(2) 0.7500 0.0467(8) Uani 1 2 d S T P C .
H31 H 1.0000 0.8511 0.7500 0.056 Uiso 1 2 calc RS T P . .
C32 C 0.90913(19) 0.7585(2) 0.6994(2) 0.0473(7) Uani 1 1 d . . . . .
C33 C 0.9120(2) 0.6740(2) 0.6989(2) 0.0565(8) Uani 0.5 1 d . . . C 1
N33 N 0.9120(2) 0.6740(2) 0.6989(2) 0.0565(8) Uani 0.5 1 d . . . C 2
C34 C 1.0000 0.6314(3) 0.7500 0.0565(11) Uani 1 2 d S T P . .
N35 N 0.8553(6) 0.6086(4) 0.6696(6) 0.0571(17) Uani 0.5 1 d . . . C 1
C36 C 0.9048(5) 0.5378(5) 0.6969(6) 0.070(2) Uani 0.5 1 d . . . C 1
H36 H 0.8751 0.4849 0.6803 0.083 Uiso 0.5 1 calc R . . C 1
N37 N 1.0000 0.5497(3) 0.7500 0.0647(11) Uani 1 2 d S T P C 1
O38 O 0.83356(13) 0.80030(14) 0.65957(17) 0.0531(6) Uani 1 1 d . . . D 1
C39 C 0.7498(7) 0.6182(5) 0.6076(7) 0.075(2) Uani 0.5 1 d . . . C 1
H39A H 0.7414 0.6618 0.5535 0.113 Uiso 0.5 1 calc GR . . C 1
H39B H 0.7137 0.6331 0.6567 0.113 Uiso 0.5 1 calc GR . . C 1
H39C H 0.7237 0.5662 0.5713 0.113 Uiso 0.5 1 calc GR . . C 1
C40 C 0.8129(7) 0.6295(6) 0.6363(8) 0.059(2) Uani 0.5 1 d . . . C 2
H40A H 0.7843 0.6542 0.5644 0.089 Uiso 0.5 1 calc GR . . C 2
H40B H 0.7664 0.6355 0.6763 0.089 Uiso 0.5 1 calc GR . . C 2
H40C H 0.8257 0.5708 0.6288 0.089 Uiso 0.5 1 calc GR . . C 2


_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
N1 C2 1.354(3) 2_656 ?
N1 C2 1.354(3) . ?
C2 N3 1.330(4) . ?
C2 N5 1.343(4) . ?
N3 C4 1.355(3) . ?
C4 N3 1.355(3) 2_656 ?
C4 N6 1.310(6) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 H6 0.81(4) . ?
N11 H11 0.8800 . ?
N11 C12 1.363(4) . ?
N11 C16 1.398(4) . ?
C12 N13 1.389(4) . ?
C12 O21 1.229(4) . ?
N13 C14 1.389(4) . ?
N13 C22 1.485(7) . ?
C14 C15 1.360(5) . ?
C14 N19 1.354(4) . ?
C15 C16 1.420(4) . ?
C15 N17 1.360(4) . ?
C16 O20 1.212(4) . ?
N17 C18 1.328(6) . ?
N17 C23 1.463(6) . ?
N17A C18A 1.35(2) . ?
N17A C23A 1.44(2) . ?
C18 H18 0.9500 . ?
C18 N19 1.333(5) . ?
C18A H18A 0.9500 . ?
C18A N19 1.310(15) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
N31 H31 0.8800 . ?
N31 C32 1.396(3) 2_756 ?
N31 C32 1.396(3) . ?
C32 C33 1.371(5) . ?
C32 O38 1.237(3) . ?
C33 C34 1.398(4) . ?
C33 N35 1.314(8) . ?
C34 C33 1.398(4) 2_756 ?
C34 N33 1.398(4) 2_756 ?
C34 C36 2.006(8) . ?
C34 C36 2.006(8) 2_756 ?
C34 N37 1.325(6) . ?
N35 C36 1.335(11) . ?
N35 C39 1.468(9) . ?
C36 H36 0.9500 . ?
C36 N37 1.324(6) . ?
N37 C36 1.324(6) 2_756 ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
C2 N1 C2 113.6(4) 2_656 . ?
N3 C2 N1 125.9(3) . . ?
N3 C2 N5 117.9(2) . . ?
N5 C2 N1 116.2(3) . . ?
C2 N3 C4 115.3(3) . . ?
N3 C4 N3 124.0(4) . 2_656 ?
N6 C4 N3 118.0(2) . 2_656 ?
N6 C4 N3 118.0(2) . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C4 N6 H6 122(3) . . ?
C12 N11 H11 115.4 . . ?
C12 N11 C16 129.2(2) . . ?
C16 N11 H11 115.4 . . ?
N11 C12 N13 115.9(3) . . ?
O21 C12 N11 121.6(3) . . ?
O21 C12 N13 122.4(3) . . ?
C12 N13 C14 119.1(3) . . ?
C12 N13 C22 119.7(3) . . ?
C14 N13 C22 121.1(3) . . ?
N19 C14 C15 115.6(3) . . ?
C14 C15 C16 122.5(3) . . ?
C14 C15 N17 102.0(3) . . ?
N17 C15 C16 135.4(4) . . ?
N11 C16 C15 111.2(3) . . ?
O20 C16 N11 121.8(3) . . ?
O20 C16 C15 126.9(3) . . ?
C15 N17 C14 39.0(2) . . ?
C15 N17 C23 124.9(4) . . ?
C18 N17 C14 69.3(3) . . ?
C18 N17 C15 108.3(4) . . ?
C18 N17 C23 126.8(3) . . ?
C23 N17 C14 163.7(3) . . ?
C18A N17A C14 69.1(10) . . ?
C18A N17A C23A 127.1(18) . . ?
C23A N17A C14 163.7(17) . . ?
C14 C18 H18 163.3 . . ?
N17 C18 C14 73.6(2) . . ?
N17 C18 H18 123.0 . . ?
N17 C18 N19 113.9(3) . . ?
N19 C18 C14 40.29(18) . . ?
N19 C18 H18 123.0 . . ?
C14 C18A H18A 167.5 . . ?
N17A C18A C14 69.6(10) . . ?
N17A C18A H18A 122.7 . . ?
N19 C18A C14 45.1(5) . . ?
N19 C18A N17A 114.7(13) . . ?
N19 C18A H18A 122.7 . . ?
C18 N19 C14 100.2(3) . . ?
C18A N19 C14 91.6(5) . . ?
N13 C22 H22A 109.5 . . ?
N13 C22 H22B 109.5 . . ?
N13 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
N17 C23 H23A 109.5 . . ?
N17 C23 H23B 109.5 . . ?
N17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N17A C23A H23D 109.5 . . ?
N17A C23A H23E 109.5 . . ?
N17A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C32 N31 H31 116.5 . . ?
C32 N31 H31 116.5 2_756 . ?
C32 N31 C32 127.1(4) 2_756 . ?
C33 C32 N31 115.0(3) . . ?
O38 C32 N31 120.2(3) . . ?
O38 C32 C33 124.7(3) . . ?
C32 C33 C34 121.0(3) . . ?
N35 C33 C32 142.3(4) . . ?
N35 C33 C34 96.5(4) . . ?
C33 C34 C33 120.8(4) 2_756 . ?
C33 C34 C36 160.4(4) 2_756 . ?
C33 C34 C36 160.4(4) . 2_756 ?
C33 C34 C36 78.8(3) . . ?
C33 C34 C36 78.8(3) 2_756 2_756 ?
C36 C34 C36 81.6(5) . 2_756 ?
N37 C34 C33 119.6(2) . . ?
N37 C34 C33 119.6(2) . 2_756 ?
N37 C34 C36 40.8(2) . . ?
N37 C34 C36 40.8(2) . 2_756 ?
C33 N35 C36 113.2(6) . . ?
C33 N35 C39 120.0(6) . . ?
C36 N35 C39 126.7(7) . . ?
C34 C36 H36 164.7 . . ?
N35 C36 C34 71.4(5) . . ?
N35 C36 H36 123.9 . . ?
N37 C36 C34 40.8(3) . . ?
N37 C36 N35 112.2(7) . . ?
N37 C36 H36 123.9 . . ?
C36 N37 C34 98.4(4) 2_756 . ?
C36 N37 C34 98.4(4) . . ?
C36 N37 C36 163.2(8) . 2_756 ?
N35 C39 H39A 109.5 . . ?
N35 C39 H39B 109.5 . . ?
N35 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
N5 H5A O20 0.8800 1.9900 2.869(3) 178.00 7_566
N5 H5B O38 0.8800 2.0800 2.959(4) 176.00 3_445
N6 H6 O21 0.81(4) 2.15(4) 2.954(3) 174(4) 7_566
N11 H11 N3 0.8800 2.0300 2.913(3) 177.00 7_566
C18 H18 O38 0.9500 2.5300 3.417(5) 156.00 .
C22 H22A N19 0.9800 2.4800 2.887(7) 104.00 .
C23 H23C O20 0.9800 2.4100 3.047(5) 122.00 5_676
N31 H31 N1 0.8800 2.0700 2.956(5) 180.00 3_555


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
N1 C2 N3 C4 1.4(4) . . . . ?
C2 N1 C2 N3 -0.74(19) 2_656 . . . ?
C2 N1 C2 N5 178.9(3) 2_656 . . . ?
C2 N3 C4 N3 -0.64(16) . . . 2_656 ?
C2 N3 C4 N6 179.37(16) . . . . ?
N5 C2 N3 C4 -178.2(2) . . . . ?
N11 C12 N13 C14 1.9(4) . . . . ?
N11 C12 N13 C22 179.6(4) . . . . ?
C12 N11 C16 C15 3.3(4) . . . . ?
C12 N11 C16 O20 -178.0(3) . . . . ?
C14 C15 C16 N11 -1.1(4) . . . . ?
C14 C15 C16 O20 -179.8(3) . . . . ?
C14 C15 N17 C18 1.2(4) . . . . ?
C14 C15 N17 C23 -177.2(4) . . . . ?
C14 N17 C18 N19 0.7(3) . . . . ?
C14 N17A C18A N19 2.5(10) . . . . ?
C14 C18 N19 C18A -173(3) . . . . ?
C14 C18A N19 C18 173(3) . . . . ?
C15 C14 N19 C18 1.8(4) . . . . ?
C15 C14 N19 C18A -179.5(6) . . . . ?
C15 N17 C18 C14 -0.8(3) . . . . ?
C15 N17 C18 N19 -0.1(5) . . . . ?
C16 N11 C12 N13 -3.7(4) . . . . ?
C16 N11 C12 O21 177.3(3) . . . . ?
C16 C15 N17 C14 179.2(5) . . . . ?
C16 C15 N17 C18 -179.7(3) . . . . ?
C16 C15 N17 C23 2.0(6) . . . . ?
N17 C15 C16 N11 179.8(3) . . . . ?
N17 C15 C16 O20 1.1(6) . . . . ?
N17 C18 N19 C14 -1.0(4) . . . . ?
N17 C18 N19 C18A -174(3) . . . . ?
N17A C18A N19 C14 -3.3(13) . . . . ?
N17A C18A N19 C18 170(2) . . . . ?
N19 C14 C15 C16 178.8(3) . . . . ?
N19 C14 C15 N17 -1.9(4) . . . . ?
O21 C12 N13 C14 -179.1(3) . . . . ?
O21 C12 N13 C22 -1.4(5) . . . . ?
C23 N17 C18 C14 177.5(4) . . . . ?
C23 N17 C18 N19 178.2(4) . . . . ?
C23A N17A C18A C14 -178(2) . . . . ?
C23A N17A C18A N19 -175.8(18) . . . . ?
N31 C32 C33 C34 2.5(4) . . . . ?
N31 C32 C33 N35 177.0(6) . . . . ?
C32 N31 C32 C33 -1.26(18) 2_756 . . . ?
C32 N31 C32 O38 178.5(3) 2_756 . . . ?
C32 C33 C34 C33 -1.37(19) . . . 2_756 ?
C32 C33 C34 N33 -1.37(19) . . . 2_756 ?
C32 C33 C34 C36 177.8(3) . . . . ?
C32 C33 C34 C36 -179.0(7) . . . 2_756 ?
C32 C33 C34 N37 178.63(19) . . . . ?
C32 C33 N35 C36 -177.2(5) . . . . ?
C32 C33 N35 C39 6.1(11) . . . . ?
C33 C34 N37 C36 -1.2(4) 2_756 . . 2_756 ?
C33 C34 N37 C36 -1.2(4) . . . . ?
C33 C34 N37 C36 178.8(4) . . . 2_756 ?
C33 C34 N37 C36 178.8(4) 2_756 . . . ?
C33 N35 C36 C34 1.4(5) . . . . ?
C33 N35 C36 N37 1.5(9) . . . . ?
N33 C34 N37 C36 -1.2(4) 2_756 . . 2_756 ?
N33 C34 N37 C36 178.8(4) 2_756 . . . ?
C34 C33 N35 C36 -1.9(6) . . . . ?
C34 C33 N35 C39 -178.7(6) . . . . ?
C34 C36 N37 C36 179.995(5) . . . 2_756 ?
N35 C33 C34 C33 -178.0(4) . . . 2_756 ?
N35 C33 C34 N33 -178.0(4) . . . 2_756 ?
N35 C33 C34 C36 1.2(4) . . . . ?
N35 C33 C34 C36 4.4(9) . . . 2_756 ?
N35 C33 C34 N37 2.0(4) . . . . ?
N35 C36 N37 C34 -0.1(6) . . . . ?
N35 C36 N37 C36 179.9(6) . . . 2_756 ?
C36 C34 N37 C36 180.001(2) . . . 2_756 ?
C36 C34 N37 C36 179.999(1) 2_756 . . . ?
O38 C32 C33 C34 -177.2(2) . . . . ?
O38 C32 C33 N35 -2.7(8) . . . . ?
C39 N35 C36 C34 177.9(8) . . . . ?
C39 N35 C36 N37 178.0(7) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 995318'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 10 2 0.0987 -2.0000 9.9998 2.0000 0.0324 -0.1036 -0.9828
-4 1 8 0.1706 -4.0000 0.9997 8.0000 0.6098 -0.6917 -0.2412
4 -5 -7 0.0816 4.0000 -4.9997 -7.0000 -0.4897 0.5708 0.6030
-4 -5 -5 0.0483 -4.0000 -4.9997 -5.0000 0.3003 0.8618 0.4198
4 5 5 0.0420 4.0000 4.9997 5.0000 -0.3003 -0.8618 -0.4198
6 -5 3 0.0628 6.0000 -5.0001 3.0000 -0.3326 -0.7581 0.5631
-6 5 -4 0.0568 -6.0000 5.0001 -4.0000 0.2989 0.8778 -0.5549
-2 -10 3 0.0789 -2.0000 -10.0000 3.0000 0.4977 -0.2295 0.8586
5 0 -8 0.1192 5.0000 0.0003 -8.0000 -0.7217 0.6258 0.1696
