# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bo2923
_database_code_depnum_ccdc_archive 'CCDC 1063152'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Mela-DM?HCl
_chemical_name_common            'dimethyl melamine hydrochloride'
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N6, Cl'
_chemical_formula_sum            'C5 H11 Cl N6'
_chemical_formula_weight         190.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pmna
_symmetry_space_group_name_Hall  '-P 2ac 2'

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

_cell_length_a                   6.4782(13)
_cell_length_b                   9.5193(19)
_cell_length_c                   14.311(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     882.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2947
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      29.2

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9059
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7576
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         29.12
_reflns_number_total             1283
_reflns_number_gt                1053
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1283
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instructions_details 
;
TITL bo2923 in Pmna
CELL 0.71073   6.4782   9.5193  14.3112  90.000  90.000  90.000
ZERR    4.00   0.0013   0.0019   0.0029   0.000   0.000   0.000
LATT 1
SYMM 0.5+X, Y, 0.5-Z
SYMM 0.5+X, -Y, 0.5+Z
SYMM X, -Y, -Z
SFAC C  H  N  Cl
UNIT 20 44 24 4
 
EQIV $1 X, 1+Y, Z
EQIV $2 1-X, 1-Y, 1-z
 
HTAB N3 CL1_$1
HTAB N4 CL1
HTAB N5 CL1_$1
HTAB N6 N1_$2
HTAB N6 CL1_$2
 
L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 10
 
WGHT    0.060000    0.700000
FVAR       0.76824
CL1   4    0.500000    0.084728    0.640662    10.50000    0.08305    0.01382 =
         0.02491    0.00127    0.00000    0.00000
N1    3    0.500000    0.525887    0.635971    10.50000    0.02690    0.01410 =
         0.01644   -0.00044    0.00000    0.00000
N2    3    0.500000    0.615123    0.794591    10.50000    0.02330    0.01533 =
         0.01760   -0.00066    0.00000    0.00000
N3    3    0.500000    0.768410    0.665763    10.50000    0.03281    0.01274 =
         0.01613    0.00012    0.00000    0.00000
H3    2    0.500000    0.868390    0.643920    10.50000   -1.20000
N4    3    0.500000    0.378992    0.761877    10.50000    0.03102    0.01455 =
         0.01846    0.00101    0.00000    0.00000
H4D   2    0.500000    0.309368    0.721080    10.50000   -1.20000
N5    3    0.500000    0.857180    0.814065    10.50000    0.03873    0.01518 =
         0.01786   -0.00288    0.00000    0.00000
H5D   2    0.500000    0.941088    0.786875    10.50000   -1.20000
N6    3    0.500000    0.686553    0.515144    10.50000    0.05002    0.01601 =
         0.01564   -0.00114    0.00000    0.00000
H6A   2    0.500000    0.624560    0.475288    10.50000   -1.20000
H6B   2    0.500000    0.783500    0.494676    10.50000   -1.20000
C1    1    0.500000    0.657495    0.605664    10.50000    0.02444    0.01548 =
         0.01788   -0.00198    0.00000    0.00000
C2    1    0.500000    0.509898    0.730652    10.50000    0.01733    0.01686 =
         0.01721   -0.00020    0.00000    0.00000
C3    1    0.500000    0.744223    0.759971    10.50000    0.02097    0.01677 =
         0.01678   -0.00203    0.00000    0.00000
C4    1    0.500000    0.339972    0.860111    10.50000    0.03794    0.02176 =
         0.02151    0.00627    0.00000    0.00000
AFIX 137
H4A   2    0.566886    0.250678    0.867546    10.50000   -1.50000
H4B   2    0.360327    0.333627    0.882124    10.50000   -1.50000
H4C   2    0.572787    0.409851    0.895519    10.50000   -1.50000
AFIX   0
C5    1    0.500000    0.852342    0.915593    10.50000    0.04512    0.02709 =
         0.01821   -0.00714    0.00000    0.00000
AFIX 137
H5A   2    0.367446    0.881309    0.938575    10.50000   -1.50000
H5B   2    0.604514    0.914344    0.939271    10.50000   -1.50000
H5C   2    0.528040    0.758179    0.935979    10.50000   -1.50000
 
HKLF 4
 
REM  bo2923 in Pmna
REM R1 =  0.0355 for   1053 Fo > 4sig(Fo)  and  0.0476 for all   1283 data
REM     85 parameters refined using      0 restraints
 
END  
;

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5000 0.08473(6) 0.64066(5) 0.0406(3) Uani 1 2 d S . .
N1 N 0.5000 0.5259(2) 0.63597(13) 0.0191(4) Uani 1 2 d S . .
N2 N 0.5000 0.6151(2) 0.79459(13) 0.0187(4) Uani 1 2 d S . .
N3 N 0.5000 0.7684(2) 0.66576(13) 0.0206(4) Uani 1 2 d S . .
H3 H 0.5000 0.868(3) 0.644(2) 0.025 Uiso 1 2 d S . .
N4 N 0.5000 0.3790(2) 0.76188(14) 0.0213(4) Uani 1 2 d S . .
H4D H 0.5000 0.309(3) 0.721(2) 0.026 Uiso 1 2 d S . .
N5 N 0.5000 0.8572(2) 0.81406(14) 0.0239(5) Uani 1 2 d S . .
H5D H 0.5000 0.941(3) 0.787(2) 0.029 Uiso 1 2 d S . .
N6 N 0.5000 0.6866(2) 0.51514(15) 0.0272(5) Uani 1 2 d S . .
H6A H 0.5000 0.625(4) 0.475(2) 0.033 Uiso 1 2 d S . .
H6B H 0.5000 0.783(3) 0.495(2) 0.033 Uiso 1 2 d S . .
C1 C 0.5000 0.6575(2) 0.60566(16) 0.0193(5) Uani 1 2 d S . .
C2 C 0.5000 0.5099(2) 0.73065(15) 0.0171(4) Uani 1 2 d S . .
C3 C 0.5000 0.7442(2) 0.75997(15) 0.0182(4) Uani 1 2 d S . .
C4 C 0.5000 0.3400(3) 0.86011(17) 0.0271(5) Uani 1 2 d S . .
H4A H 0.5669 0.2507 0.8675 0.041 Uiso 0.50 1 calc PR . .
H4B H 0.3603 0.3336 0.8821 0.041 Uiso 0.50 1 calc PR . .
H4C H 0.5728 0.4099 0.8955 0.041 Uiso 0.50 1 calc PR . .
C5 C 0.5000 0.8523(3) 0.91559(17) 0.0301(6) Uani 1 2 d S . .
H5A H 0.3674 0.8813 0.9386 0.045 Uiso 0.50 1 calc PR . .
H5B H 0.6045 0.9143 0.9393 0.045 Uiso 0.50 1 calc PR . .
H5C H 0.5280 0.7582 0.9360 0.045 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0831(6) 0.0138(3) 0.0249(3) 0.0013(2) 0.000 0.000
N1 0.0269(10) 0.0141(8) 0.0164(8) -0.0004(7) 0.000 0.000
N2 0.0233(10) 0.0153(9) 0.0176(8) -0.0007(7) 0.000 0.000
N3 0.0328(11) 0.0127(9) 0.0161(8) 0.0001(7) 0.000 0.000
N4 0.0310(11) 0.0146(8) 0.0185(9) 0.0010(7) 0.000 0.000
N5 0.0387(13) 0.0152(9) 0.0179(9) -0.0029(7) 0.000 0.000
N6 0.0500(14) 0.0160(9) 0.0156(9) -0.0011(7) 0.000 0.000
C1 0.0244(12) 0.0155(10) 0.0179(10) -0.0020(8) 0.000 0.000
C2 0.0173(10) 0.0169(10) 0.0172(10) -0.0002(7) 0.000 0.000
C3 0.0210(11) 0.0168(10) 0.0168(10) -0.0020(8) 0.000 0.000
C4 0.0379(15) 0.0218(11) 0.0215(11) 0.0063(9) 0.000 0.000
C5 0.0451(17) 0.0271(12) 0.0182(11) -0.0071(9) 0.000 0.000

_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 1.326(3) . ?
N1 C2 1.364(3) . ?
N2 C3 1.325(3) . ?
N2 C2 1.357(3) . ?
N3 C1 1.362(3) . ?
N3 C3 1.368(3) . ?
N3 H3 1.00(3) . ?
N4 C2 1.324(3) . ?
N4 C4 1.454(3) . ?
N4 H4D 0.88(3) . ?
N5 C3 1.325(3) . ?
N5 C5 1.454(3) . ?
N5 H5D 0.89(3) . ?
N6 C1 1.325(3) . ?
N6 H6A 0.82(3) . ?
N6 H6B 0.97(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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 C2 115.51(19) . . ?
C3 N2 C2 115.63(19) . . ?
C1 N3 C3 119.48(19) . . ?
C1 N3 H3 122.7(17) . . ?
C3 N3 H3 117.9(17) . . ?
C2 N4 C4 124.5(2) . . ?
C2 N4 H4D 118.9(19) . . ?
C4 N4 H4D 116.6(19) . . ?
C3 N5 C5 123.9(2) . . ?
C3 N5 H5D 118(2) . . ?
C5 N5 H5D 118(2) . . ?
C1 N6 H6A 122(2) . . ?
C1 N6 H6B 119.7(19) . . ?
H6A N6 H6B 118(3) . . ?
N6 C1 N1 121.1(2) . . ?
N6 C1 N3 117.1(2) . . ?
N1 C1 N3 121.7(2) . . ?
N4 C2 N2 117.9(2) . . ?
N4 C2 N1 116.1(2) . . ?
N2 C2 N1 126.0(2) . . ?
N5 C3 N2 122.3(2) . . ?
N5 C3 N3 116.1(2) . . ?
N2 C3 N3 121.6(2) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
N3 H3 Cl1 1.00(3) 2.06(3) 3.032(2) 163(2) 1_565
N4 H4D Cl1 0.88(3) 2.43(3) 3.295(2) 167(3) .
N5 H5D Cl1 0.89(3) 2.50(3) 3.294(2) 149(3) 1_565
N6 H6A N1 0.82(3) 2.14(4) 2.961(3) 176(3) 5_666
N6 H6B Cl1 0.97(3) 2.31(3) 3.116(2) 141(3) 5_666

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.093
