#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:28:49 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179665 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/18/4511898.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_4511898
loop_
_publ_author_name
'Bučar, Dejan-Krešimir'
'Henry, Rodger F.'
'Zhang, Geoff G. Z.'
'MacGillivray, Leonard R.'
_publ_section_title
;
 Synthon Hierarchies in Crystal Forms Composed of Theophylline and
 Hydroxybenzoic Acids: Cocrystal Screening via Solution-Mediated Phase
 Transformation
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5318
_journal_paper_doi               10.1021/cg501204k
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C7 H9 N4 O2 +1, C7 H5 O4 -1, O1 H2'
_chemical_formula_sum            'C14 H16 N4 O7'
_chemical_formula_weight         352.31
_chemical_name_common
'theopylline 2,6-dihydroxybenzoic acid salt monohydrate'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.0430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6593(19)
_cell_length_b                   6.5583(8)
_cell_length_c                   15.727(2)
_cell_measurement_reflns_used    4466
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4335
_cell_measurement_theta_min      2.5465
_cell_volume                     1508.2(3)
_computing_cell_refinement       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_data_collection       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Apex2 v2.1-4 (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows v2.01'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16040
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.074
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.6927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1635
_reflns_number_gt                2225
_reflns_number_total             3436
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg501204k_si_002.cif
_cod_data_source_block           T26
_cod_depositor_comments
'Adding full bibliography for 4511895--4511900.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4511898
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'
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
O1 O 0.69269(10) 0.0614(2) 0.00927(10) 0.0223(4) Uani 1 1 d .
O2 O 0.97523(10) 0.0394(2) 0.15255(10) 0.0231(4) Uani 1 1 d .
N1 N 0.61590(12) 0.0437(3) 0.18490(12) 0.0192(4) Uani 1 1 d .
H1N H 0.562(2) 0.054(4) 0.1496(19) 0.040(8) Uiso 1 1 d .
N2 N 0.83380(12) 0.0550(3) 0.08213(11) 0.0184(4) Uani 1 1 d .
N3 N 0.85318(12) 0.0329(3) 0.23273(11) 0.0176(4) Uani 1 1 d .
N4 N 0.70770(12) 0.0262(3) 0.30053(12) 0.0186(4) Uani 1 1 d .
H4N H 0.733(2) 0.001(5) 0.369(2) 0.064(11) Uiso 1 1 d .
C1 C 0.62010(15) 0.0321(3) 0.26890(14) 0.0193(5) Uani 1 1 d .
H1 H 0.5696 0.0286 0.3015 0.023 Uiso 1 1 calc R
C2 C 0.70400(14) 0.0454(3) 0.16018(14) 0.0170(4) Uani 1 1 d .
C3 C 0.73808(14) 0.0544(3) 0.07732(14) 0.0179(4) Uani 1 1 d .
C4 C 0.87824(15) 0.0696(4) 0.00138(15) 0.0244(5) Uani 1 1 d .
H4A H 0.8938 -0.0646 -0.0172 0.037 Uiso 1 1 calc R
H4B H 0.9328 0.1504 0.0097 0.037 Uiso 1 1 calc R
H4C H 0.8371 0.1325 -0.0410 0.037 Uiso 1 1 calc R
C5 C 0.89267(14) 0.0425(3) 0.15550(14) 0.0183(4) Uani 1 1 d .
C6 C 0.91313(15) 0.0253(4) 0.31098(14) 0.0224(5) Uani 1 1 d .
H6A H 0.8767 0.0164 0.3593 0.034 Uiso 1 1 calc R
H6B H 0.9498 0.1466 0.3154 0.034 Uiso 1 1 calc R
H6C H 0.9522 -0.0919 0.3097 0.034 Uiso 1 1 calc R
C7 C 0.76058(14) 0.0345(3) 0.23239(14) 0.0170(4) Uani 1 1 d .
O3 O 0.61338(10) -0.0466(2) 0.47797(10) 0.0232(4) Uani 1 1 d .
O4 O 0.76175(11) -0.0421(2) 0.45888(10) 0.0239(4) Uani 1 1 d .
O5 O 0.88013(10) -0.0481(2) 0.58563(11) 0.0237(4) Uani 1 1 d .
H5O H 0.853(2) -0.043(5) 0.528(2) 0.053(10) Uiso 1 1 d .
O6 O 0.55818(11) -0.0383(3) 0.62776(11) 0.0250(4) Uani 1 1 d .
H6O H 0.556(2) -0.043(5) 0.569(2) 0.051(10) Uiso 1 1 d .
C8 C 0.69510(15) -0.0443(3) 0.50721(14) 0.0198(5) Uani 1 1 d .
C9 C 0.71753(14) -0.0429(3) 0.60059(13) 0.0174(4) Uani 1 1 d .
C10 C 0.80917(15) -0.0432(3) 0.63580(14) 0.0193(4) Uani 1 1 d .
C11 C 0.82825(15) -0.0395(3) 0.72384(15) 0.0223(5) Uani 1 1 d .
H11 H 0.8885 -0.0392 0.7469 0.027 Uiso 1 1 calc R
C12 C 0.75689(16) -0.0363(3) 0.77646(15) 0.0236(5) Uani 1 1 d .
H12 H 0.7698 -0.0340 0.8352 0.028 Uiso 1 1 calc R
C13 C 0.66655(16) -0.0362(3) 0.74417(15) 0.0221(5) Uani 1 1 d .
H13 H 0.6194 -0.0344 0.7808 0.027 Uiso 1 1 calc R
C14 C 0.64718(14) -0.0391(3) 0.65681(14) 0.0195(5) Uani 1 1 d .
O7 O 0.46272(11) 0.0906(3) 0.08647(11) 0.0267(4) Uani 1 1 d D
H1W H 0.446(2) 0.2175(19) 0.074(2) 0.085(13) Uiso 1 1 d D
H2W H 0.4250(18) 0.011(3) 0.0542(17) 0.055(10) Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
C1 N1 C2 107.75(18)
C1 N1 O7 124.62(15)
C2 N1 O7 127.39(14)
C1 N1 H1N 125.0(18)
C2 N1 H1N 127.2(18)
O7 N1 H1N 2.7(17)
C5 N2 C3 127.18(19)
C5 N2 C4 115.63(17)
C3 N2 C4 117.19(18)
C7 N3 C5 118.46(18)
C7 N3 C6 123.06(18)
C5 N3 C6 118.47(17)
C1 N4 C7 106.75(18)
C1 N4 H4N 126.7(17)
C7 N4 H4N 126.2(17)
N1 C1 N4 110.35(19)
N1 C1 H1 124.8
N4 C1 H1 124.8
C7 C2 N1 107.05(19)
C7 C2 C3 122.11(19)
N1 C2 C3 130.83(19)
O1 C3 N2 122.0(2)
O1 C3 C2 126.7(2)
N2 C3 C2 111.37(18)
N2 C4 H4A 109.5
N2 C4 H4B 109.5
H4A C4 H4B 109.5
N2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O2 C5 N3 120.8(2)
O2 C5 N2 122.0(2)
N3 C5 N2 117.16(18)
N3 C6 H6A 109.5
N3 C6 H6B 109.5
H6A C6 H6B 109.5
N3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N3 C7 C2 123.7(2)
N3 C7 N4 128.2(2)
C2 C7 N4 108.08(19)
C8 O4 H4N 113.0(13)
C10 O5 H5O 105(2)
C14 O6 H6O 107(2)
O3 C8 O4 122.2(2)
O3 C8 C9 120.2(2)
O4 C8 C9 117.60(19)
C14 C9 C10 118.2(2)
C14 C9 C8 120.14(19)
C10 C9 C8 121.7(2)
O5 C10 C11 118.2(2)
O5 C10 C9 121.4(2)
C11 C10 C9 120.5(2)
C12 C11 C10 119.3(2)
C12 C11 H11 120.4
C10 C11 H11 120.4
C11 C12 C13 121.8(2)
C11 C12 H12 119.1
C13 C12 H12 119.1
C14 C13 C12 119.2(2)
C14 C13 H13 120.4
C12 C13 H13 120.4
O6 C14 C13 117.5(2)
O6 C14 C9 121.4(2)
C13 C14 C9 121.1(2)
N1 O7 H1W 116.7(19)
N1 O7 H2W 136.9(18)
H1W O7 H2W 105.6(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.221(3)
O2 C5 1.215(3)
N1 C1 1.320(3)
N1 C2 1.375(3)
N1 O7 2.654(2)
N1 H1N 0.94(3)
N2 C5 1.394(3)
N2 C3 1.400(3)
N2 C4 1.471(3)
N3 C7 1.357(3)
N3 C5 1.383(3)
N3 C6 1.462(3)
N4 C1 1.345(3)
N4 C7 1.367(3)
N4 H4N 1.12(3)
C1 H1 0.9300
C2 C7 1.360(3)
C2 C3 1.429(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
O3 C8 1.253(3)
O4 C8 1.280(3)
O4 H4N 1.48(3)
O5 C10 1.349(3)
O5 H5O 0.97(3)
O6 C14 1.352(3)
O6 H6O 0.93(3)
C8 C9 1.482(3)
C9 C14 1.405(3)
C9 C10 1.417(3)
C10 C11 1.393(3)
C11 C12 1.379(3)
C11 H11 0.9300
C12 C13 1.385(3)
C12 H12 0.9300
C13 C14 1.383(3)
C13 H13 0.9300
O7 H1W 0.887(10)
O7 H2W 0.891(10)
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
O7 H1W O3 0.887(10) 1.927(14) 2.788(2) 163(3) 2_655
O7 H2W O1 0.891(10) 1.990(16) 2.823(2) 155(3) 3_655
O6 H6O O3 0.93(3) 1.70(3) 2.545(2) 149(3) .
O5 H5O O4 0.97(3) 1.66(3) 2.549(2) 151(3) .
C1 H1 O3 0.93 2.85 3.337(3) 114.2 .
C1 H1 O6 0.93 2.25 3.174(3) 175.1 3_656
N1 H1N O7 0.94(3) 1.72(3) 2.654(2) 176(3) .
N4 H4N O3 1.12(3) 2.56(3) 3.236(2) 118(2) .
N4 H4N O4 1.12(3) 1.48(3) 2.598(2) 177(3) .
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
C2 N1 C1 N4 0.0(2)
O7 N1 C1 N4 -174.74(13)
C7 N4 C1 N1 0.0(2)
C1 N1 C2 C7 0.0(2)
O7 N1 C2 C7 174.55(14)
C1 N1 C2 C3 179.4(2)
O7 N1 C2 C3 -6.0(3)
C5 N2 C3 O1 -178.26(19)
C4 N2 C3 O1 1.4(3)
C5 N2 C3 C2 1.9(3)
C4 N2 C3 C2 -178.37(17)
C7 C2 C3 O1 178.9(2)
N1 C2 C3 O1 -0.5(4)
C7 C2 C3 N2 -1.3(3)
N1 C2 C3 N2 179.3(2)
C7 N3 C5 O2 -179.25(19)
C6 N3 C5 O2 1.9(3)
C7 N3 C5 N2 0.5(3)
C6 N3 C5 N2 -178.32(18)
C3 N2 C5 O2 178.2(2)
C4 N2 C5 O2 -1.5(3)
C3 N2 C5 N3 -1.6(3)
C4 N2 C5 N3 178.69(17)
C5 N3 C7 C2 -0.1(3)
C6 N3 C7 C2 178.7(2)
C5 N3 C7 N4 179.94(19)
C6 N3 C7 N4 -1.2(3)
N1 C2 C7 N3 -179.94(18)
C3 C2 C7 N3 0.6(3)
N1 C2 C7 N4 0.0(2)
C3 C2 C7 N4 -179.48(18)
C1 N4 C7 N3 180.0(2)
C1 N4 C7 C2 0.0(2)
H4N O4 C8 O3 12.2(14)
H4N O4 C8 C9 -167.5(14)
O3 C8 C9 C14 -1.6(3)
O4 C8 C9 C14 178.12(19)
O3 C8 C9 C10 179.08(19)
O4 C8 C9 C10 -1.2(3)
C14 C9 C10 O5 179.55(19)
C8 C9 C10 O5 -1.1(3)
C14 C9 C10 C11 -0.1(3)
C8 C9 C10 C11 179.26(19)
O5 C10 C11 C12 -179.41(19)
C9 C10 C11 C12 0.2(3)
C10 C11 C12 C13 -0.1(3)
C11 C12 C13 C14 -0.2(3)
C12 C13 C14 O6 -179.79(19)
C12 C13 C14 C9 0.3(3)
C10 C9 C14 O6 179.92(19)
C8 C9 C14 O6 0.5(3)
C10 C9 C14 C13 -0.2(3)
C8 C9 C14 C13 -179.54(19)
