#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/51/1505175.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_1505175
loop_
_publ_author_name
'Childs, Scott L.'
'Stahly, G. Patrick'
'Park, Aeri'
_publ_section_title
;
 The Salt−Cocrystal Continuum:  The Influence of Crystal
 Structure on Ionization State
;
_journal_issue                   3
_journal_name_full               'Molecular Pharmaceutics'
_journal_page_first              323
_journal_paper_doi               10.1021/mp0601345
_journal_volume                  4
_journal_year                    2007
_chemical_formula_moiety         'C7 H9 N4 O2, C7 H6 O3'
_chemical_formula_sum            'C14 H15 N4 O5'
_chemical_formula_weight         319.30
_chemical_name_common            'theophylline:salicylic acid cocrystal (1:1)'
_chemical_name_systematic
; 
 theophylline salicylic acid 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.754(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9183(3)
_cell_length_b                   25.9086(10)
_cell_length_c                   7.9749(4)
_cell_measurement_reflns_used    2105
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.67
_cell_measurement_theta_min      3.41
_cell_volume                     1382.32(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.583
_diffrn_measured_fraction_theta_max 0.583
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3694
_diffrn_reflns_theta_full        65.68
_diffrn_reflns_theta_max         65.68
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0659P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                996
_reflns_number_total             1396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            mp0601345si20061227_041052.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1505175
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'
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 0.2601(5) 0.03470(12) 0.4248(7) 0.0157(12) Uani 1 1 d .
H2 H 0.2741 0.0081 0.5091 0.019 Uiso 1 1 calc R
C2 C 0.2743(6) 0.10716(12) 0.3058(6) 0.0114(11) Uani 1 1 d .
C3 C 0.2362(6) 0.17791(13) 0.1101(6) 0.0123(10) Uani 1 1 d .
C4 C 0.1080(6) 0.08975(13) 0.0035(7) 0.0126(12) Uani 1 1 d .
C5 C 0.1824(6) 0.07430(12) 0.1769(6) 0.0094(11) Uani 1 1 d .
C6 C 0.3765(6) 0.19505(12) 0.4170(5) 0.0183(11) Uani 1 1 d .
H6A H 0.2668 0.2047 0.4681 0.027 Uiso 1 1 d R
H6B H 0.4279 0.2260 0.3724 0.027 Uiso 1 1 d R
H6C H 0.4838 0.1789 0.5058 0.027 Uiso 1 1 d R
C7 C 0.0764(5) 0.16223(12) -0.1965(5) 0.0196(11) Uani 1 1 d .
H7A H -0.0700 0.1631 -0.2274 0.029 Uiso 1 1 d R
H7B H 0.1219 0.1398 -0.2778 0.029 Uiso 1 1 d R
H7C H 0.1283 0.1972 -0.2024 0.029 Uiso 1 1 d R
C8 C 0.6703(5) 0.12080(12) 0.0658(5) 0.0096(11) Uani 1 1 d .
C9 C 0.7182(6) 0.09489(13) 0.2246(6) 0.0136(11) Uani 1 1 d .
C10 C 0.8073(5) 0.12190(13) 0.3766(5) 0.0161(11) Uani 1 1 d .
H10 H 0.8398 0.1046 0.4852 0.019 Uiso 1 1 calc R
C11 C 0.8477(5) 0.17384(12) 0.3679(5) 0.0163(10) Uani 1 1 d .
H11 H 0.9079 0.1921 0.4714 0.020 Uiso 1 1 calc R
C12 C 0.8022(5) 0.19989(13) 0.2109(5) 0.0162(11) Uani 1 1 d .
H12 H 0.8320 0.2356 0.2063 0.019 Uiso 1 1 calc R
C13 C 0.7143(5) 0.17369(12) 0.0636(5) 0.0154(11) Uani 1 1 d .
H13 H 0.6817 0.1916 -0.0438 0.018 Uiso 1 1 calc R
C14 C 0.5722(6) 0.09322(13) -0.0950(6) 0.0160(11) Uani 1 1 d .
N1 N 0.1737(5) 0.02748(12) 0.2570(6) 0.0147(9) Uani 1 1 d .
N2 N 0.3253(5) 0.08305(10) 0.4631(4) 0.0137(9) Uani 1 1 d .
N3 N 0.3029(4) 0.15852(10) 0.2748(4) 0.0101(9) Uani 1 1 d .
N4 N 0.1498(4) 0.14209(10) -0.0200(4) 0.0112(9) Uani 1 1 d .
O1 O 0.2495(3) 0.22353(8) 0.0755(3) 0.0198(7) Uani 1 1 d .
O2 O 0.0140(4) 0.06407(9) -0.1221(4) 0.0172(8) Uani 1 1 d .
O3 O 0.6833(4) 0.04394(9) 0.2429(4) 0.0217(8) Uani 1 1 d .
O4 O 0.5264(4) 0.04717(8) -0.0971(3) 0.0234(8) Uani 1 1 d .
O5 O 0.5341(4) 0.12187(9) -0.2370(4) 0.0220(8) Uani 1 1 d .
H1 H 0.119(5) -0.0009(15) 0.196(5) 0.038(14) Uiso 1 1 d .
H5O H 0.458(6) 0.1025(14) -0.344(6) 0.057(17) Uiso 1 1 d .
H3O H 0.624(7) 0.0334(16) 0.140(6) 0.07(2) Uiso 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 N2 113.5(4)
C5 C2 N2 111.7(3)
C5 C2 N3 122.0(4)
N2 C2 N3 126.3(4)
O1 C3 N3 122.9(4)
O1 C3 N4 120.9(4)
N3 C3 N4 116.2(3)
O2 C4 C5 128.9(3)
O2 C4 N4 119.5(4)
C5 C4 N4 111.6(4)
C2 C5 N1 105.5(4)
C2 C5 C4 123.3(3)
N1 C5 C4 131.1(4)
C9 C8 C13 118.5(4)
C9 C8 C14 120.4(3)
C13 C8 C14 121.0(4)
O3 C9 C8 123.9(4)
O3 C9 C10 116.4(4)
C8 C9 C10 119.7(3)
C11 C10 C9 119.6(4)
C10 C11 C12 121.2(4)
C13 C12 C11 119.1(3)
C12 C13 C8 121.9(4)
O4 C14 O5 122.4(4)
O4 C14 C8 122.7(4)
O5 C14 C8 114.8(3)
C1 N1 C5 106.3(4)
C1 N2 C2 103.0(3)
C3 N3 C2 119.8(3)
C3 N3 C6 118.1(3)
C2 N3 C6 121.5(3)
C3 N4 C4 126.8(4)
C3 N4 C7 116.9(3)
C4 N4 C7 116.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.332(4)
C1 N2 1.340(4)
C2 C5 1.361(5)
C2 N2 1.364(4)
C2 N3 1.377(4)
C3 O1 1.223(4)
C3 N3 1.372(4)
C3 N4 1.407(4)
C4 O2 1.240(4)
C4 C5 1.406(5)
C4 N4 1.409(4)
C5 N1 1.379(4)
C6 N3 1.465(4)
C7 N4 1.465(4)
C8 C9 1.397(5)
C8 C13 1.405(4)
C8 C14 1.474(5)
C9 O3 1.356(4)
C9 C10 1.400(5)
C10 C11 1.380(4)
C11 C12 1.387(5)
C12 C13 1.358(5)
C14 O4 1.233(4)
C14 O5 1.323(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
N2 C2 C5 N1 0.5(4)
N3 C2 C5 N1 -177.6(3)
N2 C2 C5 C4 177.6(3)
N3 C2 C5 C4 -0.6(5)
O2 C4 C5 C2 -176.2(3)
N4 C4 C5 C2 3.0(4)
O2 C4 C5 N1 0.1(6)
N4 C4 C5 N1 179.2(3)
C13 C8 C9 O3 -179.9(3)
C14 C8 C9 O3 1.3(5)
C13 C8 C9 C10 0.2(5)
C14 C8 C9 C10 -178.6(3)
O3 C9 C10 C11 179.8(3)
C8 C9 C10 C11 -0.3(5)
C9 C10 C11 C12 -0.2(5)
C10 C11 C12 C13 0.7(5)
C11 C12 C13 C8 -0.7(5)
C9 C8 C13 C12 0.3(5)
C14 C8 C13 C12 179.1(3)
C9 C8 C14 O4 0.9(5)
C13 C8 C14 O4 -177.9(3)
C9 C8 C14 O5 179.9(3)
C13 C8 C14 O5 1.1(5)
N2 C1 N1 C5 0.3(4)
C2 C5 N1 C1 -0.5(3)
C4 C5 N1 C1 -177.2(3)
N1 C1 N2 C2 0.0(4)
C5 C2 N2 C1 -0.3(3)
N3 C2 N2 C1 177.7(3)
O1 C3 N3 C2 176.8(3)
N4 C3 N3 C2 -3.1(4)
O1 C3 N3 C6 5.6(5)
N4 C3 N3 C6 -174.3(3)
C5 C2 N3 C3 0.6(5)
N2 C2 N3 C3 -177.3(3)
C5 C2 N3 C6 171.4(3)
N2 C2 N3 C6 -6.4(5)
O1 C3 N4 C4 -173.6(3)
N3 C3 N4 C4 6.4(4)
O1 C3 N4 C7 -0.4(4)
N3 C3 N4 C7 179.5(3)
O2 C4 N4 C3 173.2(3)
C5 C4 N4 C3 -6.1(4)
O2 C4 N4 C7 -0.1(4)
C5 C4 N4 C7 -179.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651569 ChemSpider
