#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/93/2019390.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_2019390
loop_
_publ_author_name
'Buist, Amanda R.'
'Kennedy, Alan R.'
'Manzie, Craig'
_publ_section_title
;
 Four salt phases of theophylline
;
_journal_coeditor_code           GZ3251
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              220
_journal_page_last               224
_journal_paper_doi               10.1107/S2053229614000825
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C7 H9 N4 O2 +, Br1 -, H2 O1'
_chemical_formula_moiety         'C7 H9 N4 O2 +, Br1 -, H2 O1'
_chemical_formula_sum            'C7 H11 Br N4 O3'
_chemical_formula_weight         279.11
_chemical_name_systematic
;
1,3-Dimethyl-2,6-dioxo-7H-purin-9-ium chloride monohydrate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0120(5)
_cell_length_b                   6.6151(3)
_cell_length_c                   11.5297(4)
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.8524
_cell_measurement_theta_min      2.9016
_cell_volume                     1068.70(7)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7635
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.92
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.481
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1553
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0245P)²+0.5427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0577
_reflns_number_gt                1378
_reflns_number_total             1553
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3251sup1.cif
_cod_data_source_block           III
_cod_database_code               2019390
_cod_database_fobs_code          2019390
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.238793(17) 0.2500 0.030738(19) 0.01977(9) Uani d S 1 2 . .
O O1 0.42192(12) 0.2500 0.32740(15) 0.0270(4) Uani d S 1 2 . .0
O O2 0.36669(15) 0.2500 0.71829(16) 0.0376(5) Uani d S 1 2 . .
N N1 0.20447(15) 0.2500 0.30119(17) 0.0178(4) Uani d SD 1 2 . .
N N2 0.11254(14) 0.2500 0.45350(17) 0.0187(4) Uani d SD 1 2 . .
N N3 0.39277(14) 0.2500 0.52399(17) 0.0198(4) Uani d S 1 2 . .
N N4 0.23609(14) 0.2500 0.60213(17) 0.0187(4) Uani d S 1 2 . .
C C1 0.11501(17) 0.2500 0.3368(2) 0.0207(5) Uani d S 1 2 . .
H H1 0.0606 0.2500 0.2877 0.025 Uiso calc SR 1 2 . .
C C2 0.26338(16) 0.2500 0.3970(2) 0.0163(5) Uani d S 1 2 . .
C C3 0.20478(17) 0.2500 0.4915(2) 0.0159(4) Uani d S 1 2 . .
C C4 0.36473(17) 0.2500 0.4072(2) 0.0183(5) Uani d S 1 2 . .
C C5 0.33321(18) 0.2500 0.6207(2) 0.0214(5) Uani d S 1 2 . .
C C6 0.49547(18) 0.2500 0.5505(2) 0.0294(6) Uani d S 1 2 . .
H H6A 0.5320 0.2500 0.4780 0.044 Uiso calc SR 1 2 . .
H H6B 0.5114 0.1290 0.5956 0.044 Uiso calc PR 0.50 1 . .
H H6C 0.5114 0.3710 0.5956 0.044 Uiso calc PR 0.50 1 . .
C C7 0.16970(19) 0.2500 0.6999(2) 0.0277(6) Uani d S 1 2 . .
H H7A 0.2057 0.2500 0.7728 0.042 Uiso calc SR 1 2 . .
H H7B 0.1294 0.1290 0.6962 0.042 Uiso calc PR 0.50 1 . .
H H7C 0.1294 0.3710 0.6962 0.042 Uiso calc PR 0.50 1 . .
O O1W -0.04826(17) 0.221(2) 0.5711(2) 0.032(3) Uani d PD 0.50 1 A -1
H H1W -0.094(2) 0.286(7) 0.535(3) 0.048 Uiso d PD 0.50 1 B -1
H H2W -0.057(2) 0.280(7) 0.6387(19) 0.048 Uiso d PD 0.50 1 C -1
H H1N 0.225(2) 0.2500 0.2308(12) 0.036(9) Uiso d SD 1 2 . .
H H2N 0.0595(13) 0.2500 0.490(2) 0.033(9) Uiso d SD 1 2 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 108.6(2)
C1 N1 H1N 127(2)
C2 N1 H1N 124(2)
C1 N2 C3 107.2(2)
C1 N2 H2N 121(2)
C3 N2 H2N 132(2)
C5 N3 C4 126.9(2)
C5 N3 C6 114.8(2)
C4 N3 C6 118.3(2)
C3 N4 C5 117.9(2)
C3 N4 C7 121.5(2)
C5 N4 C7 120.6(2)
N1 C1 N2 109.6(2)
N1 C1 H1 125.2
N2 C1 H1 125.2
C3 C2 N1 106.2(2)
C3 C2 C4 122.3(2)
N1 C2 C4 131.5(2)
N4 C3 C2 124.0(2)
N4 C3 N2 127.7(2)
C2 C3 N2 108.3(2)
O1 C4 N3 122.7(2)
O1 C4 C2 126.4(2)
N3 C4 C2 111.0(2)
O2 C5 N4 121.5(2)
O2 C5 N3 120.6(2)
N4 C5 N3 117.9(2)
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
N4 C7 H7A 109.5
N4 C7 H7B 109.5
H7A C7 H7B 109.5
N4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
H1W O1W H2W 96(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.220(3)
O2 C5 1.219(3)
N1 C1 1.319(3)
N1 C2 1.379(3)
N1 H1N 0.860(10)
N2 C1 1.345(3)
N2 C3 1.365(3)
N2 H2N 0.855(10)
N3 C5 1.393(3)
N3 C4 1.403(3)
N3 C6 1.471(3)
N4 C3 1.349(3)
N4 C5 1.378(3)
N4 C7 1.461(3)
C1 H1 0.9500
C2 C3 1.364(3)
C2 C4 1.425(3)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
O1W H1W 0.882(10)
O1W H2W 0.880(10)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N Br1 . 0.860(10) 2.315(13) 3.1551(19) 166(3)
N2 H2N O1W . 0.855(10) 1.785(11) 2.637(3) 173.5(12)
O1W H2W O2 6_557 0.880(10) 1.97(3) 2.712(3) 140(4)
O1W H1W Br1 6_556 0.882(10) 2.47(3) 3.212(3) 143(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
C2 N1 C1 N2 0.0
C3 N2 C1 N1 0.0
C1 N1 C2 C3 0.0
C1 N1 C2 C4 180.0
C5 N4 C3 C2 0.0
C7 N4 C3 C2 180.0
C5 N4 C3 N2 180.0
C7 N4 C3 N2 0.0
N1 C2 C3 N4 180.0
C4 C2 C3 N4 0.0
N1 C2 C3 N2 0.0
C4 C2 C3 N2 180.0
C1 N2 C3 N4 180.0
C1 N2 C3 C2 0.0
C5 N3 C4 O1 180.0
C6 N3 C4 O1 0.0
C5 N3 C4 C2 0.0
C6 N3 C4 C2 180.0
C3 C2 C4 O1 180.0
N1 C2 C4 O1 0.0
C3 C2 C4 N3 0.0
N1 C2 C4 N3 180.0
C3 N4 C5 O2 180.0
C7 N4 C5 O2 0.0
C3 N4 C5 N3 0.0
C7 N4 C5 N3 180.0
C4 N3 C5 O2 180.0
C6 N3 C5 O2 0.0
C4 N3 C5 N4 0.0
C6 N3 C5 N4 180.0
