# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_SHUO
_audit_block_doi                 10.5517/cc1442kx
_database_code_depnum_ccdc_archive 'CCDC 1046608'
_audit_update_record             
;
2015-01-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'theophylline-salicylic acid cocrystal'
_chemical_name_common            ?
_chemical_melting_point          118.5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 O5'
_chemical_formula_weight         318.29

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   6.9599(5)
_cell_length_b                   25.9822(13)
_cell_length_c                   8.0100(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.224(7)
_cell_angle_gamma                90.00
_cell_volume                     1397.64(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8181
_exptl_absorpt_correction_T_max  0.8898

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4694
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.97
_diffrn_reflns_theta_max         66.59
_reflns_number_total             2472
_reflns_number_gt                2053
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0855P)²+3.4677P] 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         2472
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.2085
_refine_ls_wR_factor_gt          0.1994
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4711(5) 0.12155(10) 0.7346(3) 0.0381(7) Uani 1 1 d . . .
H1 H 0.538(8) 0.102(2) 0.816(7) 0.057 Uiso 1 1 d . . .
O2 O 0.4752(4) 0.04727(10) 0.5960(3) 0.0386(7) Uani 1 1 d . . .
O3 O 0.3176(4) 0.04439(10) 0.2571(3) 0.0369(7) Uani 1 1 d . . .
H3 H 0.375(8) 0.030(2) 0.351(7) 0.055 Uiso 1 1 d . . .
O4 O -0.0121(4) 0.06410(10) 0.6200(3) 0.0319(6) Uani 1 1 d . . .
O5 O -0.2443(4) 0.22296(9) 0.4200(3) 0.0348(7) Uani 1 1 d . . .
C1 C 0.3362(5) 0.12089(13) 0.4345(4) 0.0254(8) Uani 1 1 d . . .
C2 C 0.2845(5) 0.09481(13) 0.2749(5) 0.0270(8) Uani 1 1 d . . .
C3 C 0.1957(6) 0.12195(14) 0.1241(5) 0.0303(8) Uani 1 1 d . . .
H3A H 0.164(7) 0.1016(17) 0.023(6) 0.036 Uiso 1 1 d . . .
C4 C 0.1567(6) 0.17376(15) 0.1311(5) 0.0320(8) Uani 1 1 d . . .
H4 H 0.091(7) 0.1933(17) 0.028(6) 0.038 Uiso 1 1 d . . .
C5 C 0.2053(6) 0.19997(15) 0.2891(5) 0.0338(9) Uani 1 1 d . . .
H5 H 0.174(7) 0.2351(18) 0.291(6) 0.041 Uiso 1 1 d . . .
C6 C 0.2943(6) 0.17367(14) 0.4367(5) 0.0305(8) Uani 1 1 d . . .
H6 H 0.336(7) 0.1907(16) 0.545(6) 0.037 Uiso 1 1 d . . .
C7 C 0.4328(5) 0.09287(14) 0.5947(5) 0.0284(8) Uani 1 1 d . . .
C8 C -0.2700(5) 0.10714(13) 0.1928(4) 0.0239(7) Uani 1 1 d . . .
C9 C -0.2594(6) 0.03444(15) 0.0734(5) 0.0321(9) Uani 1 1 d . . .
H9 H -0.277(6) 0.0070(18) -0.004(6) 0.039 Uiso 1 1 d . . .
C10 C -0.1797(5) 0.07415(13) 0.3216(4) 0.0244(7) Uani 1 1 d . . .
C11 C -0.1033(5) 0.09014(13) 0.4973(4) 0.0237(7) Uani 1 1 d . . .
C12 C -0.2295(5) 0.17763(13) 0.3884(5) 0.0258(8) Uani 1 1 d . . .
C13 C -0.0695(6) 0.16310(15) 0.6940(5) 0.0344(9) Uani 1 1 d . . .
H13A H 0.0734 0.1620 0.7271 0.052 Uiso 1 1 calc R . .
H13B H -0.1199 0.1428 0.7733 0.052 Uiso 1 1 calc R . .
H13C H -0.1133 0.1981 0.6964 0.052 Uiso 1 1 calc R . .
C14 C -0.3713(6) 0.19447(14) 0.0805(5) 0.0317(8) Uani 1 1 d . . .
H14A H -0.2634 0.2051 0.0345 0.048 Uiso 1 1 calc R . .
H14B H -0.4268 0.2240 0.1227 0.048 Uiso 1 1 calc R . .
H14C H -0.4722 0.1781 -0.0088 0.048 Uiso 1 1 calc R . .
N1 N -0.3216(5) 0.08268(11) 0.0374(4) 0.0284(7) Uani 1 1 d . . .
N2 N -0.1728(5) 0.02744(11) 0.2429(4) 0.0283(7) Uani 1 1 d . . .
H2A H -0.111(6) -0.0002(18) 0.292(6) 0.034 Uiso 1 1 d . . .
N3 N -0.1439(4) 0.14231(11) 0.5185(4) 0.0251(7) Uani 1 1 d . . .
N4 N -0.2978(4) 0.15824(11) 0.2224(4) 0.0244(7) 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
O1 C7 1.313(4) . ?
O1 H1 0.85(6) . ?
O2 C7 1.220(5) . ?
O3 C2 1.344(4) . ?
O3 H3 0.85(6) . ?
O4 C11 1.224(4) . ?
O5 C12 1.215(4) . ?
C1 C2 1.408(5) . ?
C1 C6 1.403(5) . ?
C1 C7 1.475(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.377(5) . ?
C3 H3A 0.94(5) . ?
C4 C5 1.399(5) . ?
C4 H4 0.98(5) . ?
C5 C6 1.365(6) . ?
C5 H5 0.94(5) . ?
C6 H6 0.95(5) . ?
C8 N1 1.359(4) . ?
C8 C10 1.362(5) . ?
C8 N4 1.371(4) . ?
C9 N1 1.333(5) . ?
C9 N2 1.345(5) . ?
C9 H9 0.93(5) . ?
C10 N2 1.374(4) . ?
C10 C11 1.429(5) . ?
C11 N3 1.404(4) . ?
C12 N4 1.384(4) . ?
C12 N3 1.399(5) . ?
C13 N3 1.468(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N4 1.461(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 H2A 0.88(5) . ?

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
C7 O1 H1 106(4) . . ?
C2 O3 H3 113(4) . . ?
C2 C1 C6 118.5(3) . . ?
C2 C1 C7 120.1(3) . . ?
C6 C1 C7 121.3(3) . . ?
O3 C2 C3 116.8(3) . . ?
O3 C2 C1 123.7(3) . . ?
C3 C2 C1 119.5(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 125(3) . . ?
C2 C3 H3A 114(3) . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 122(3) . . ?
C5 C4 H4 117(3) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 122(3) . . ?
C4 C5 H5 119(3) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 H6 121(3) . . ?
C1 C6 H6 117(3) . . ?
O2 C7 O1 123.3(3) . . ?
O2 C7 C1 122.7(3) . . ?
O1 C7 C1 114.0(3) . . ?
N1 C8 C10 111.0(3) . . ?
N1 C8 N4 126.6(3) . . ?
C10 C8 N4 122.4(3) . . ?
N1 C9 N2 112.3(3) . . ?
N1 C9 H9 127(3) . . ?
N2 C9 H9 121(3) . . ?
C8 C10 N2 105.8(3) . . ?
C8 C10 C11 122.8(3) . . ?
N2 C10 C11 131.3(3) . . ?
O4 C11 N3 121.0(3) . . ?
O4 C11 C10 127.6(3) . . ?
N3 C11 C10 111.4(3) . . ?
O5 C12 N4 121.8(3) . . ?
O5 C12 N3 121.6(3) . . ?
N4 C12 N3 116.6(3) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 N1 C8 104.4(3) . . ?
C9 N2 C10 106.5(3) . . ?
C9 N2 H2A 127(3) . . ?
C10 N2 H2A 126(3) . . ?
C12 N3 C11 127.1(3) . . ?
C12 N3 C13 116.5(3) . . ?
C11 N3 C13 116.1(3) . . ?
C8 N4 C12 119.4(3) . . ?
C8 N4 C14 121.7(3) . . ?
C12 N4 C14 118.3(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.080
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: choloroform'
