#------------------------------------------------------------------------------
#$Date: 2022-05-24 04:11:22 +0300 (Tue, 24 May 2022) $
#$Revision: 275622 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244971.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_7244971
loop_
_publ_author_name
'Hawkins, Bryson A.'
'Du, Jonathan J.'
'Lai, Felcia'
'Stanton, Stephen A.'
'Williams, Peter A.'
'Groundwater, Paul W.'
'Platts, James A.'
'Overgaard, Jacob'
'Hibbs, David E.'
_publ_section_title
;
 An experimental and theoretical charge density study of theophylline and
 malonic acid cocrystallization
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              15670
_journal_page_last               15684
_journal_paper_doi               10.1039/D1RA08389A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C7 H8 N4 O2, C3 H4 O4'
_chemical_formula_sum            'C10 H12 N4 O6'
_chemical_formula_weight         284.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-05 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.949(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1509(5)
_cell_length_b                   8.3690(2)
_cell_length_c                   17.4870(5)
_cell_measurement_reflns_used    10197
_cell_measurement_temperature    20(0)
_cell_measurement_theta_max      18.052
_cell_measurement_theta_min      1.061
_cell_volume                     2400.99(15)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      20(0)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'BL02B1 beamline'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.30988
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9839
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        10.715
_diffrn_reflns_theta_max         18.052
_diffrn_reflns_theta_min         1.061
_exptl_absorpt_coefficient_mu    0.037
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         9839
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7942
_reflns_number_total             9839
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra08389a2.cif
_cod_data_source_block           shelx
_cod_database_code               7244971
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Restrained distances
 C1-H1A
 1.083 with sigma of 0.2
 N1-H1
 1.009 with sigma of 0.2
 C7-H7A
 1.059 with sigma of 0.2
 C7-H7B
 1.059 with sigma of 0.2
 C7-H7C
 1.059 with sigma of 0.2
 C6-H6A
 1.059 with sigma of 0.2
 C6-H6B
 1.059 with sigma of 0.2
 C6-H6C
 1.059 with sigma of 0.2
 C02-H02A
 1.092 with sigma of 0.2
 C02-H02B
 1.092 with sigma of 0.2
 O01-H01
 1.015 with sigma of 0.2
 O04-H04
 1.015 with sigma of 0.2
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51456(2) 0.09071(4) 0.64171(2) 0.00906(4) Uani 1 1 d . . . . .
O2 O 0.68360(2) -0.27065(4) 0.57372(2) 0.01151(5) Uani 1 1 d . . . . .
O01 O 0.70308(2) 0.89747(4) 0.26776(2) 0.00990(5) Uani 1 1 d D . . . .
O02 O 0.69226(2) 0.67342(4) 0.19460(2) 0.01165(5) Uani 1 1 d . . . . .
O03 O 0.69950(2) 0.45689(4) 0.32769(2) 0.01031(5) Uani 1 1 d . . . . .
O04 O 0.59548(2) 0.49855(4) 0.37740(2) 0.01211(5) Uani 1 1 d D . . . .
N1 N 0.70641(2) -0.01634(4) 0.45488(2) 0.00821(5) Uani 1 1 d D . . . .
N2 N 0.64169(2) 0.21736(4) 0.44432(2) 0.00783(5) Uani 1 1 d . . . . .
N3 N 0.57023(2) 0.16556(4) 0.54356(2) 0.00706(4) Uani 1 1 d . . . . .
N4 N 0.59837(2) -0.08851(4) 0.60623(2) 0.00696(4) Uani 1 1 d . . . . .
C1 C 0.69331(2) 0.12622(5) 0.41840(2) 0.00852(5) Uani 1 1 d D . . . .
C2 C 0.62193(2) 0.12546(4) 0.50014(2) 0.00656(5) Uani 1 1 d . . . . .
C3 C 0.55819(2) 0.05942(4) 0.59956(2) 0.00662(5) Uani 1 1 d . . . . .
C4 C 0.65111(2) -0.13754(4) 0.56300(2) 0.00724(5) Uani 1 1 d . . . . .
C5 C 0.66087(2) -0.01959(4) 0.50813(2) 0.00705(5) Uani 1 1 d . . . . .
C6 C 0.53554(3) 0.32612(5) 0.53727(2) 0.00982(5) Uani 1 1 d D . . . .
C7 C 0.58514(3) -0.19627(5) 0.66772(2) 0.00960(5) Uani 1 1 d D . . . .
C01 C 0.67478(2) 0.75193(5) 0.24556(2) 0.00813(5) Uani 1 1 d . . . . .
C02 C 0.61603(3) 0.69399(5) 0.28880(3) 0.01062(6) Uani 1 1 d D . . . .
C03 C 0.64219(2) 0.53859(4) 0.33273(2) 0.00720(5) Uani 1 1 d . . . . .
H1A H 0.7189(6) 0.1570(11) 0.3800(6) 0.014(2) Uiso 1 1 d D . . . .
H1 H 0.7421(7) -0.0967(14) 0.4466(6) 0.024(3) Uiso 1 1 d D . . . .
H6A H 0.5773(7) 0.4030(13) 0.5590(7) 0.025(3) Uiso 1 1 d D . . . .
H6B H 0.4976(7) 0.3294(13) 0.5675(6) 0.022(2) Uiso 1 1 d D . . . .
H6C H 0.5092(7) 0.3490(13) 0.4821(6) 0.021(2) Uiso 1 1 d D . . . .
H7A H 0.6124(7) -0.2946(14) 0.6621(7) 0.028(3) Uiso 1 1 d D . . . .
H7B H 0.5277(7) -0.2108(13) 0.6593(6) 0.021(2) Uiso 1 1 d D . . . .
H7C H 0.6082(6) -0.1519(13) 0.7204(6) 0.020(2) Uiso 1 1 d D . . . .
H01 H 0.7380(8) 0.9265(16) 0.2394(8) 0.042(4) Uiso 1 1 d D . . . .
H02A H 0.5665(7) 0.6698(13) 0.2475(6) 0.024(3) Uiso 1 1 d D . . . .
H02B H 0.6060(8) 0.7756(15) 0.3256(7) 0.031(3) Uiso 1 1 d D . . . .
H04 H 0.6106(9) 0.3994(17) 0.4029(9) 0.049(4) 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 -0.0019 0.0002 '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 -0.0030 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0036 0.0009 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C01 O01 H01 109.1(8) . . ?
C03 O04 H04 112.0(9) . . ?
C1 N1 C5 106.83(3) . . ?
C1 N1 H1 125.7(7) . . ?
C5 N1 H1 127.4(7) . . ?
C1 N2 C2 104.33(3) . . ?
C2 N3 C3 119.42(3) . . ?
C2 N3 C6 120.00(3) . . ?
C3 N3 C6 120.21(3) . . ?
C3 N4 C7 115.12(3) . . ?
C4 N4 C3 126.32(3) . . ?
C4 N4 C7 118.50(3) . . ?
N1 C1 N2 112.34(3) . . ?
N1 C1 H1A 122.4(6) . . ?
N2 C1 H1A 125.2(6) . . ?
N2 C2 N3 126.68(3) . . ?
N2 C2 C5 110.93(3) . . ?
N3 C2 C5 122.39(3) . . ?
O1 C3 N3 122.28(3) . . ?
O1 C3 N4 120.69(3) . . ?
N3 C3 N4 117.03(3) . . ?
O2 C4 N4 121.11(3) . . ?
O2 C4 C5 126.34(4) . . ?
N4 C4 C5 112.55(3) . . ?
N1 C5 C4 132.18(3) . . ?
C2 C5 N1 105.56(3) . . ?
C2 C5 C4 122.26(3) . . ?
N3 C6 H6A 110.3(7) . . ?
N3 C6 H6B 108.4(7) . . ?
N3 C6 H6C 108.8(7) . . ?
H6A C6 H6B 108.3(9) . . ?
H6A C6 H6C 110.2(9) . . ?
H6B C6 H6C 110.8(9) . . ?
N4 C7 H7A 105.4(7) . . ?
N4 C7 H7B 109.6(6) . . ?
N4 C7 H7C 110.7(7) . . ?
H7A C7 H7B 112.5(10) . . ?
H7A C7 H7C 110.4(9) . . ?
H7B C7 H7C 108.2(9) . . ?
O01 C01 C02 112.97(3) . . ?
O02 C01 O01 124.36(4) . . ?
O02 C01 C02 122.65(4) . . ?
C01 C02 C03 112.94(3) . . ?
C01 C02 H02A 105.4(7) . . ?
C01 C02 H02B 111.9(7) . . ?
C03 C02 H02A 105.5(7) . . ?
C03 C02 H02B 110.3(7) . . ?
H02A C02 H02B 110.5(10) . . ?
O03 C03 O04 122.87(4) . . ?
O03 C03 C02 124.83(4) . . ?
O04 C03 C02 112.30(3) . . ?
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 C3 1.2221(5) . ?
O2 C4 1.2352(5) . ?
O01 C01 1.3267(5) . ?
O01 H01 0.915(15) . ?
O02 C01 1.2131(5) . ?
O03 C03 1.2214(5) . ?
O04 C03 1.3150(5) . ?
O04 H04 0.942(14) . ?
N1 C1 1.3407(5) . ?
N1 C5 1.3791(5) . ?
N1 H1 0.949(11) . ?
N2 C1 1.3435(5) . ?
N2 C2 1.3609(5) . ?
N3 C2 1.3667(5) . ?
N3 C3 1.3815(5) . ?
N3 C6 1.4607(5) . ?
N4 C3 1.4050(5) . ?
N4 C4 1.3989(5) . ?
N4 C7 1.4708(5) . ?
C1 H1A 0.939(10) . ?
C2 C5 1.3729(5) . ?
C4 C5 1.4200(5) . ?
C6 H6A 0.955(11) . ?
C6 H6B 0.951(11) . ?
C6 H6C 0.958(11) . ?
C7 H7A 0.966(12) . ?
C7 H7B 0.960(11) . ?
C7 H7C 0.964(10) . ?
C01 C02 1.5053(6) . ?
C02 C03 1.5105(5) . ?
C02 H02A 0.962(11) . ?
C02 H02B 0.987(13) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C5 N1 -0.74(7) . . . . ?
O2 C4 C5 C2 179.79(4) . . . . ?
O01 C01 C02 C03 -122.89(4) . . . . ?
O02 C01 C02 C03 58.66(5) . . . . ?
N2 C2 C5 N1 -0.03(4) . . . . ?
N2 C2 C5 C4 179.56(3) . . . . ?
N3 C2 C5 N1 179.48(3) . . . . ?
N3 C2 C5 C4 -0.93(6) . . . . ?
N4 C4 C5 N1 179.56(4) . . . . ?
N4 C4 C5 C2 0.10(5) . . . . ?
C1 N1 C5 C2 0.07(4) . . . . ?
C1 N1 C5 C4 -179.46(4) . . . . ?
C1 N2 C2 N3 -179.51(4) . . . . ?
C1 N2 C2 C5 -0.02(4) . . . . ?
C2 N2 C1 N1 0.07(4) . . . . ?
C2 N3 C3 O1 177.83(3) . . . . ?
C2 N3 C3 N4 -2.38(5) . . . . ?
C3 N3 C2 N2 -178.45(3) . . . . ?
C3 N3 C2 C5 2.12(5) . . . . ?
C3 N4 C4 O2 179.76(4) . . . . ?
C3 N4 C4 C5 -0.53(5) . . . . ?
C4 N4 C3 O1 -178.52(3) . . . . ?
C4 N4 C3 N3 1.69(5) . . . . ?
C5 N1 C1 N2 -0.09(5) . . . . ?
C6 N3 C2 N2 -5.44(6) . . . . ?
C6 N3 C2 C5 175.13(4) . . . . ?
C6 N3 C3 O1 4.83(5) . . . . ?
C6 N3 C3 N4 -175.38(3) . . . . ?
C7 N4 C3 O1 -1.43(5) . . . . ?
C7 N4 C3 N3 178.78(3) . . . . ?
C7 N4 C4 O2 2.76(5) . . . . ?
C7 N4 C4 C5 -177.53(3) . . . . ?
C01 C02 C03 O03 -7.74(6) . . . . ?
C01 C02 C03 O04 172.86(4) . . . . ?
