#------------------------------------------------------------------------------
#$Date: 2016-01-01 02:29:23 +0200 (Fri, 01 Jan 2016) $
#$Revision: 171809 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/37/4513790.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4513790
loop_
_publ_author_name
'Eddleston, Mark D.'
'Arhangelskis, Mihails'
'Fábián, Laszlo'
'Tizzard, Graham J.'
'Coles, Simon J.'
'Jones, William'
_publ_section_title
;
 Investigation of an Amide-Pseudo Amide Hydrogen Bonding Motif within a
 Series of Theophylline:Amide Cocrystals
;
_journal_name_full               'Crystal Growth & Design'
_journal_paper_doi               10.1021/acs.cgd.5b00905
_journal_year                    2015
_chemical_formula_moiety         'C7 H8 N4 O2, C2 H5 N O'
_chemical_formula_sum            'C9 H13 N5 O3'
_chemical_formula_weight         239.24
_chemical_name_common
'1:1 theophylline N-methylformamide cocrystal'
_chemical_name_systematic
; 
 1,3-dimethyl-7H-purine-2,6-dione N-methylformamide complex
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.441(2)
_cell_angle_beta                 92.929(2)
_cell_angle_gamma                90.609(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6316(3)
_cell_length_b                   8.7905(4)
_cell_length_c                   9.5955(4)
_cell_measurement_reflns_used    6120
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.02
_cell_volume                     558.09(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8110
_diffrn_reflns_theta_full        30.11
_diffrn_reflns_theta_max         30.11
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.039
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.1504
_refine_ls_R_factor_gt           0.1168
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2978
_refine_ls_wR_factor_ref         0.3293
_reflns_number_gt                2192
_reflns_number_total             3252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00905_si_002.cif
_cod_data_source_block           wj1055
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.2616(5) 0.9199(3) -0.1784(3) 0.0324(6) Uani 1 1 d .
N1 N 0.2626(4) 0.7838(3) -0.1077(3) 0.0322(6) Uani 1 1 d .
O1 O 0.2660(4) 0.9226(3) -0.3057(2) 0.0493(7) Uani 1 1 d .
C2 C 0.2549(4) 0.7674(3) 0.0359(3) 0.0293(6) Uani 1 1 d .
O2 O 0.2557(4) 0.6410(2) 0.0852(2) 0.0400(6) Uani 1 1 d .
N2 N 0.2476(4) 0.8982(2) 0.1192(2) 0.0298(5) Uani 1 1 d .
O3 O 0.2498(4) 0.3327(2) 0.6459(2) 0.0457(6) Uani 1 1 d .
C3 C 0.2465(4) 1.0373(3) 0.0586(3) 0.0259(5) Uani 1 1 d .
N3 N 0.2491(4) 1.2030(2) -0.1053(2) 0.0294(5) Uani 1 1 d .
H3 H 0.2524 1.2465 -0.1861 0.035 Uiso 1 1 calc R
C4 C 0.2531(4) 1.0487(3) -0.0831(3) 0.0262(6) Uani 1 1 d .
N4 N 0.2368(4) 1.1769(2) 0.1255(3) 0.0311(6) Uani 1 1 d .
N5 N 0.2461(5) 0.3225(3) 0.4105(3) 0.0408(7) Uani 1 1 d .
H5N H 0.2446 0.2629 0.3344 0.049 Uiso 1 1 calc R
C5 C 0.2390(4) 1.2731(3) 0.0208(3) 0.0307(6) Uani 1 1 d .
H5 H 0.2340 1.3806 0.0348 0.037 Uiso 1 1 calc R
C6 C 0.2668(6) 0.6403(3) -0.1921(4) 0.0449(8) Uani 1 1 d .
H6A H 0.3836 0.5808 -0.1610 0.067 Uiso 1 1 calc R
H6B H 0.2771 0.6627 -0.2907 0.067 Uiso 1 1 calc R
H6C H 0.1425 0.5818 -0.1807 0.067 Uiso 1 1 calc R
C7 C 0.2430(6) 0.8897(4) 0.2709(3) 0.0415(7) Uani 1 1 d .
H7A H 0.2286 0.7831 0.2952 0.062 Uiso 1 1 calc R
H7B H 0.1285 0.9478 0.3044 0.062 Uiso 1 1 calc R
H7C H 0.3690 0.9324 0.3149 0.062 Uiso 1 1 calc R
C8 C 0.2482(5) 0.2590(3) 0.5327(3) 0.0403(7) Uani 1 1 d .
H8 H 0.2484 0.1510 0.5340 0.048 Uiso 1 1 calc R
C9 C 0.2463(5) 0.4855(3) 0.3959(3) 0.0405(7) Uani 1 1 d .
H9A H 0.3170 0.5104 0.3125 0.061 Uiso 1 1 calc R
H9B H 0.3151 0.5357 0.4785 0.061 Uiso 1 1 calc R
H9C H 0.1068 0.5209 0.3869 0.061 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 122.4(3)
O1 C1 C4 126.5(3)
N1 C1 C4 111.1(2)
C2 N1 C1 127.3(2)
C2 N1 C6 115.1(2)
C1 N1 C6 117.6(2)
O2 C2 N2 121.6(3)
O2 C2 N1 121.0(3)
N2 C2 N1 117.4(2)
C2 N2 C3 119.3(2)
C2 N2 C7 120.4(2)
C3 N2 C7 120.3(2)
N4 C3 C4 111.7(2)
N4 C3 N2 126.8(2)
C4 C3 N2 121.5(2)
C5 N3 C4 106.2(2)
C5 N3 H3 126.9
C4 N3 H3 126.9
C3 C4 N3 105.4(2)
C3 C4 C1 123.4(2)
N3 C4 C1 131.2(2)
C5 N4 C3 103.2(2)
C8 N5 C9 123.0(3)
C8 N5 H5N 118.5
C9 N5 H5N 118.5
N3 C5 N4 113.5(2)
N3 C5 H5 123.2
N4 C5 H5 123.2
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N2 C7 H7A 109.5
N2 C7 H7B 109.5
H7A C7 H7B 109.5
N2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O3 C8 N5 123.5(3)
O3 C8 H8 118.2
N5 C8 H8 118.2
N5 C9 H9A 109.5
N5 C9 H9B 109.5
H9A C9 H9B 109.5
N5 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.224(4)
C1 N1 1.400(3)
C1 C4 1.428(4)
N1 C2 1.395(4)
N1 C6 1.471(4)
C2 O2 1.226(3)
C2 N2 1.375(3)
N2 C3 1.377(3)
N2 C7 1.462(4)
O3 C8 1.241(4)
C3 N4 1.364(3)
C3 C4 1.370(4)
N3 C5 1.340(4)
N3 C4 1.383(3)
N3 H3 0.8800
N4 C5 1.341(3)
N5 C8 1.319(4)
N5 C9 1.446(4)
N5 H5N 0.8800
C5 H5 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8 0.9500
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
O1 C1 N1 C2 -179.0(3)
C4 C1 N1 C2 0.5(4)
O1 C1 N1 C6 -0.7(5)
C4 C1 N1 C6 178.8(3)
C1 N1 C2 O2 179.6(3)
C6 N1 C2 O2 1.3(4)
C1 N1 C2 N2 -0.8(4)
C6 N1 C2 N2 -179.1(3)
O2 C2 N2 C3 -179.8(3)
N1 C2 N2 C3 0.5(4)
O2 C2 N2 C7 0.7(4)
N1 C2 N2 C7 -178.9(3)
C2 N2 C3 N4 179.0(2)
C7 N2 C3 N4 -1.6(4)
C2 N2 C3 C4 -0.2(4)
C7 N2 C3 C4 179.2(3)
N4 C3 C4 N3 0.6(3)
N2 C3 C4 N3 179.8(2)
N4 C3 C4 C1 -179.3(3)
N2 C3 C4 C1 0.0(4)
C5 N3 C4 C3 -0.4(3)
C5 N3 C4 C1 179.4(3)
O1 C1 C4 C3 179.3(3)
N1 C1 C4 C3 -0.1(4)
O1 C1 C4 N3 -0.5(5)
N1 C1 C4 N3 -179.9(3)
C4 C3 N4 C5 -0.4(3)
N2 C3 N4 C5 -179.7(3)
C4 N3 C5 N4 0.2(3)
C3 N4 C5 N3 0.1(3)
C9 N5 C8 O3 0.2(5)
