# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       abourahm@tcnj.edu
_publ_contact_author_name        'Abourahma, Heba'
loop_
_publ_author_name
'Abourahma, Heba'
'Urban, Jennifer'
'Morozowich, Nicole'
'Chan, Benny'

data_mm54new
_database_code_depnum_ccdc_archive 'CCDC 879008'
#TrackingRef '- NM54NEW.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Theophylline-melamine
_chemical_melting_point          179
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 N10 O3 S'
_chemical_formula_weight         384.44

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   15.4964(11)
_cell_length_b                   8.8674(6)
_cell_length_c                   13.2985(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.4230(10)
_cell_angle_gamma                90.00
_cell_volume                     1723.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19732
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         28.58
_reflns_number_total             4187
_reflns_number_gt                3477
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0423P)^2^+0.8437P] where P=(Fo^2^+2Fc^2^)/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         4187
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.03579(3) -0.58836(4) 0.15039(3) 0.01765(10) Uani 0.94 1 d P A 1
O3 O 0.03318(7) -0.42205(11) 0.12642(8) 0.0207(2) Uani 1 1 d . A 1
C11 C 0.14587(11) -0.6229(2) 0.24453(13) 0.0309(4) Uani 1 1 d . A 1
H10A H 0.1917 -0.6021 0.2125 0.046 Uiso 1 1 calc R A 1
H10B H 0.1502 -0.7265 0.2666 0.046 Uiso 1 1 calc R A 1
H10C H 0.1553 -0.5588 0.3054 0.046 Uiso 1 1 calc R A 1
C12 C -0.02923(11) -0.6088(2) 0.23798(15) 0.0354(4) Uani 1 1 d . A 1
H20A H -0.0059 -0.5415 0.2974 0.053 Uiso 1 1 calc R A 1
H20B H -0.0246 -0.7108 0.2634 0.053 Uiso 1 1 calc R A 1
H20C H -0.0922 -0.5851 0.2003 0.053 Uiso 1 1 calc R A 1
S1B S 0.0470(8) -0.5157(13) 0.2363(9) 0.055(3) Uiso 0.06 1 d P B 2
O2 O 0.25685(7) -0.54034(12) 0.84104(8) 0.0195(2) Uani 1 1 d . . .
O1 O 0.46127(7) -0.15240(11) 0.88475(8) 0.0205(2) Uani 1 1 d . . .
N6 N 0.11823(8) -0.58643(13) 0.51605(9) 0.0150(2) Uani 1 1 d . . .
N7 N 0.27495(8) -0.65264(13) 0.55140(9) 0.0144(2) Uani 1 1 d . . .
N5 N 0.23563(8) -0.39715(13) 0.57779(9) 0.0147(2) Uani 1 1 d . . .
N2 N 0.35872(8) -0.34840(13) 0.85525(9) 0.0157(2) Uani 1 1 d . . .
N3 N 0.40269(8) -0.60439(13) 0.85502(9) 0.0153(2) Uani 1 1 d . . .
N10 N 0.16010(8) -0.82779(13) 0.48671(10) 0.0175(2) Uani 1 1 d . . .
N4 N 0.56347(8) -0.64175(13) 0.87513(9) 0.0168(2) Uani 1 1 d . . .
N1 N 0.60444(8) -0.39762(13) 0.89395(9) 0.0153(2) Uani 1 1 d . . .
N8 N 0.38448(8) -0.46761(14) 0.60950(10) 0.0174(2) Uani 1 1 d . . .
N9 N 0.08389(9) -0.34223(14) 0.54296(11) 0.0203(3) Uani 1 1 d . . .
C8 C 0.29641(9) -0.50579(15) 0.57894(10) 0.0137(3) Uani 1 1 d . . .
C10 C 0.18493(9) -0.68373(15) 0.51860(10) 0.0138(3) Uani 1 1 d . . .
C9 C 0.14822(9) -0.44422(15) 0.54695(10) 0.0145(3) Uani 1 1 d . . .
C2 C 0.51175(9) -0.40393(15) 0.87829(10) 0.0146(3) Uani 1 1 d . . .
C3 C 0.44664(9) -0.28866(16) 0.87397(10) 0.0156(3) Uani 1 1 d . . .
C1 C 0.63115(9) -0.54140(16) 0.89108(11) 0.0166(3) Uani 1 1 d . . .
H8 H 0.6911 -0.5685 0.8994 0.020 Uiso 1 1 calc R . .
C4 C 0.33501(9) -0.50103(16) 0.84957(10) 0.0157(3) Uani 1 1 d . . .
C7 C 0.38217(10) -0.76598(16) 0.85287(12) 0.0202(3) Uani 1 1 d . . .
H11A H 0.3533 -0.7979 0.7804 0.030 Uiso 1 1 calc R . .
H11B H 0.3419 -0.7845 0.8929 0.030 Uiso 1 1 calc R . .
H11C H 0.4380 -0.8214 0.8839 0.030 Uiso 1 1 calc R . .
C6 C 0.28340(10) -0.24232(17) 0.84529(12) 0.0208(3) Uani 1 1 d . . .
H12A H 0.3060 -0.1408 0.8502 0.031 Uiso 1 1 calc R . .
H12B H 0.2588 -0.2603 0.9016 0.031 Uiso 1 1 calc R . .
H12C H 0.2363 -0.2566 0.7776 0.031 Uiso 1 1 calc R . .
C5 C 0.48967(9) -0.55404(15) 0.86777(10) 0.0145(3) Uani 1 1 d . . .
H2 H 0.4260(12) -0.534(2) 0.6061(14) 0.021(4) Uiso 1 1 d . . .
H3 H 0.1963(13) -0.877(2) 0.4594(15) 0.029(5) Uiso 1 1 d . . .
H1 H 0.3991(12) -0.373(2) 0.6207(14) 0.024(5) Uiso 1 1 d . . .
H4 H 0.1000(14) -0.844(2) 0.4578(15) 0.027(5) Uiso 1 1 d . . .
H10 H 0.6427(14) -0.313(2) 0.9103(16) 0.040(6) Uiso 1 1 d . . .
H12 H 0.0989(13) -0.252(2) 0.5666(15) 0.030(5) Uiso 1 1 d . . .
H11 H 0.0239(14) -0.368(2) 0.5247(15) 0.032(5) Uiso 1 1 d . . .

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
S1A 0.01919(18) 0.01201(18) 0.01864(18) 0.00233(13) 0.00213(14) -0.00129(13)
O3 0.0207(5) 0.0144(5) 0.0267(5) 0.0058(4) 0.0075(4) 0.0004(4)
C11 0.0244(8) 0.0363(9) 0.0314(9) 0.0135(7) 0.0085(7) 0.0101(7)
C12 0.0247(8) 0.0374(10) 0.0473(11) 0.0210(8) 0.0160(8) 0.0016(7)
O2 0.0143(5) 0.0213(5) 0.0230(5) 0.0004(4) 0.0064(4) -0.0042(4)
O1 0.0174(5) 0.0148(5) 0.0299(6) -0.0023(4) 0.0087(4) -0.0023(4)
N6 0.0127(5) 0.0142(6) 0.0182(6) -0.0015(4) 0.0052(4) 0.0010(4)
N7 0.0128(5) 0.0120(5) 0.0187(6) -0.0007(4) 0.0056(4) 0.0012(4)
N5 0.0138(5) 0.0129(5) 0.0179(5) -0.0001(4) 0.0060(4) 0.0016(4)
N2 0.0132(5) 0.0154(6) 0.0186(6) -0.0008(4) 0.0056(4) -0.0003(4)
N3 0.0136(5) 0.0140(6) 0.0184(6) -0.0005(4) 0.0053(4) -0.0034(4)
N10 0.0132(6) 0.0145(6) 0.0252(6) -0.0050(5) 0.0068(5) -0.0001(5)
N4 0.0157(6) 0.0160(6) 0.0188(6) 0.0008(4) 0.0057(4) -0.0011(5)
N1 0.0123(5) 0.0151(6) 0.0182(6) 0.0002(4) 0.0050(4) -0.0019(4)
N8 0.0128(6) 0.0118(6) 0.0270(6) -0.0023(5) 0.0058(5) 0.0012(5)
N9 0.0143(6) 0.0140(6) 0.0324(7) -0.0043(5) 0.0074(5) 0.0022(5)
C8 0.0149(6) 0.0142(6) 0.0124(6) 0.0006(5) 0.0050(5) -0.0002(5)
C10 0.0145(6) 0.0139(6) 0.0134(6) 0.0008(5) 0.0054(5) 0.0010(5)
C9 0.0153(6) 0.0146(6) 0.0145(6) 0.0002(5) 0.0062(5) 0.0016(5)
C2 0.0130(6) 0.0167(6) 0.0140(6) -0.0001(5) 0.0046(5) -0.0033(5)
C3 0.0152(6) 0.0170(7) 0.0146(6) -0.0007(5) 0.0047(5) -0.0027(5)
C1 0.0140(6) 0.0172(7) 0.0189(7) 0.0011(5) 0.0060(5) 0.0000(5)
C4 0.0154(6) 0.0178(7) 0.0135(6) -0.0001(5) 0.0043(5) -0.0032(5)
C7 0.0202(7) 0.0142(7) 0.0277(7) -0.0012(6) 0.0099(6) -0.0052(5)
C6 0.0153(7) 0.0185(7) 0.0288(8) -0.0007(6) 0.0076(6) 0.0015(5)
C5 0.0147(6) 0.0160(6) 0.0126(6) 0.0005(5) 0.0044(5) -0.0015(5)

_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
S1A O3 1.5065(10) . ?
S1A C11 1.7750(16) . ?
S1A C12 1.7849(17) . ?
C11 H10A 0.9600 . ?
C11 H10B 0.9600 . ?
C11 H10C 0.9600 . ?
C12 H20A 0.9600 . ?
C12 H20B 0.9600 . ?
C12 H20C 0.9600 . ?
O2 C4 1.2289(17) . ?
O1 C3 1.2290(17) . ?
N6 C10 1.3382(17) . ?
N6 C9 1.3594(17) . ?
N7 C10 1.3444(17) . ?
N7 C8 1.3636(17) . ?
N5 C8 1.3438(17) . ?
N5 C9 1.3446(17) . ?
N2 C4 1.3978(18) . ?
N2 C3 1.4047(17) . ?
N2 C6 1.4704(18) . ?
N3 C5 1.3758(17) . ?
N3 C4 1.3765(18) . ?
N3 C7 1.4660(17) . ?
N10 C10 1.3606(17) . ?
N10 H3 0.878(19) . ?
N10 H4 0.89(2) . ?
N4 C1 1.3374(18) . ?
N4 C5 1.3595(18) . ?
N1 C1 1.3450(18) . ?
N1 C2 1.3823(17) . ?
N1 H10 0.94(2) . ?
N8 C8 1.3317(18) . ?
N8 H2 0.881(18) . ?
N8 H1 0.87(2) . ?
N9 C9 1.3338(18) . ?
N9 H12 0.86(2) . ?
N9 H11 0.91(2) . ?
C2 C5 1.3699(19) . ?
C2 C3 1.4239(19) . ?
C1 H8 0.9300 . ?
C7 H11A 0.9600 . ?
C7 H11B 0.9600 . ?
C7 H11C 0.9600 . ?
C6 H12A 0.9600 . ?
C6 H12B 0.9600 . ?
C6 H12C 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
O3 S1A C11 105.67(7) . . ?
O3 S1A C12 104.85(7) . . ?
C11 S1A C12 98.10(8) . . ?
C10 N6 C9 114.01(11) . . ?
C10 N7 C8 114.65(11) . . ?
C8 N5 C9 114.34(11) . . ?
C4 N2 C3 126.64(12) . . ?
C4 N2 C6 115.34(11) . . ?
C3 N2 C6 117.95(11) . . ?
C5 N3 C4 119.24(12) . . ?
C5 N3 C7 121.13(11) . . ?
C4 N3 C7 119.55(11) . . ?
C10 N10 H3 116.1(12) . . ?
C10 N10 H4 115.6(12) . . ?
H3 N10 H4 117.4(17) . . ?
C1 N4 C5 103.14(12) . . ?
C1 N1 C2 105.76(11) . . ?
C1 N1 H10 126.3(13) . . ?
C2 N1 H10 127.7(13) . . ?
C8 N8 H2 120.4(11) . . ?
C8 N8 H1 118.6(12) . . ?
H2 N8 H1 119.8(16) . . ?
C9 N9 H12 120.4(13) . . ?
C9 N9 H11 121.7(12) . . ?
H12 N9 H11 117.3(17) . . ?
N8 C8 N5 117.68(12) . . ?
N8 C8 N7 117.29(12) . . ?
N5 C8 N7 125.04(12) . . ?
N6 C10 N7 125.83(12) . . ?
N6 C10 N10 117.48(12) . . ?
N7 C10 N10 116.68(12) . . ?
N9 C9 N5 117.74(12) . . ?
N9 C9 N6 116.17(12) . . ?
N5 C9 N6 126.05(12) . . ?
C5 C2 N1 105.45(12) . . ?
C5 C2 C3 122.94(12) . . ?
N1 C2 C3 131.60(12) . . ?
O1 C3 N2 121.46(13) . . ?
O1 C3 C2 126.89(13) . . ?
N2 C3 C2 111.65(12) . . ?
N4 C1 N1 113.75(12) . . ?
N4 C1 H8 123.1 . . ?
N1 C1 H8 123.1 . . ?
O2 C4 N3 121.76(13) . . ?
O2 C4 N2 120.86(13) . . ?
N3 C4 N2 117.37(12) . . ?
N3 C7 H11A 109.5 . . ?
N3 C7 H11B 109.5 . . ?
H11A C7 H11B 109.5 . . ?
N3 C7 H11C 109.5 . . ?
H11A C7 H11C 109.5 . . ?
H11B C7 H11C 109.5 . . ?
N2 C6 H12A 109.5 . . ?
N2 C6 H12B 109.5 . . ?
H12A C6 H12B 109.5 . . ?
N2 C6 H12C 109.5 . . ?
H12A C6 H12C 109.5 . . ?
H12B C6 H12C 109.5 . . ?
N4 C5 C2 111.90(12) . . ?
N4 C5 N3 126.12(12) . . ?
C2 C5 N3 121.95(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
N8 H2 O1 0.881(18) 2.010(19) 2.8781(16) 168.4(16) 2_646
N10 H3 O2 0.878(19) 2.209(19) 3.0495(16) 160.1(17) 4_545
N8 H1 N4 0.87(2) 2.13(2) 2.9887(17) 171.4(16) 2_656
N10 H4 O3 0.89(2) 2.11(2) 2.9893(16) 167.7(17) 2_545
N1 H10 N7 0.94(2) 1.86(2) 2.7995(16) 176.0(19) 2_656
N9 H12 O3 0.86(2) 2.145(19) 2.8145(16) 134.4(17) 4_556
N9 H11 N6 0.91(2) 2.12(2) 3.0317(17) 176.4(18) 3_546

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054