An experimental and theoretical charge density study of theophylline and malonic acid cocrystallization
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.; RSC Advances 12 (2022) 15670–15684; doi:10.1039/D1RA08389A

data_7244973
_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         'C3 H4 O4'
_chemical_formula_sum            'C3 H4 O4'
_chemical_formula_weight         103.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-03 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                108.1080(10)
_cell_angle_beta                 101.2440(10)
_cell_angle_gamma                95.2650(10)
_cell_formula_units_Z            2
_cell_length_a                   5.15560(10)
_cell_length_b                   5.32510(10)
_cell_length_c                   8.19420(10)
_cell_measurement_reflns_used    53972
_cell_measurement_temperature    149.9(5)
_cell_measurement_theta_max      65.4590
_cell_measurement_theta_min      4.0460
_cell_volume                     206.898(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00 150.00  109
  2  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00  60.00  109
  3  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-120.00  109
  4  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00 -30.00  109
  5  \w    -31.00  70.00   1.00    5.93    --   41.57 -57.00-180.00  101
  6  \w     13.00 114.00   1.00    5.93    --   41.57  57.00-150.00  101
  7  \w     13.00 114.00   1.00    5.93    --   41.57  57.00 -30.00  101
  8  \w     13.00 114.00   1.00    5.93    --   41.57  57.00 120.00  101
  9  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00  30.00  109
 10  \w     62.00 158.00   1.00   35.00    --   90.50  59.00  29.18   96
 11  \w     64.00 158.00   1.00   35.00    --   90.50  50.00-169.21   94
 12  \w     62.00 158.00   1.00   35.00    --   90.50  57.00 -91.18   96
 13  \w     62.00 158.00   1.00   35.00    --   90.50  60.00 -20.94   96
 14  \w     62.00 158.00   1.00   35.00    --   90.50  60.00 136.33   96
 15  \w     63.00 158.00   1.00   35.00    --   90.50  56.00  58.10   95
 16  \w     13.00 124.00   1.00   35.00    --   90.50 -80.00 -78.01  111
 17  \w     62.00 158.00   1.00   35.00    --   90.50  57.00 115.81   96
 18  \w     13.00 124.00   1.00   35.00    --   90.50 -80.00 165.81  111
 19  \w     13.00 123.00   1.00   35.00    --   90.50 -79.00  11.62  110
 20  \w     63.00 158.00   1.00   35.00    --   90.50  56.00 -37.04   95
 21  \w     13.00 123.00   1.00   35.00    --   90.50 -79.00  93.92  110
 22  \w     62.00 158.00   1.00   35.00    --   90.50  57.00 151.35   96
 23  \w     62.00 158.00   1.00   35.00    --   90.50  60.00  91.21   96
 24  \w     62.00 158.00   1.00   35.00    --   90.50  57.00 -50.85   96
 25  \w     63.00 158.00   1.00   35.00    --   90.50  56.00 -75.71   95
 26  \w     64.00 158.00   1.00   35.00    --   90.50  47.00  18.20   94
 27  \w     65.00 158.00   1.00   35.00    --   90.50  45.00-150.00   93
 28  \w     17.00  77.00   1.00   35.00    --   90.50 -45.00 -90.00   60
 29  \w     17.00  77.00   1.00   35.00    --   90.50 -45.00-180.00   60
 30  \w     65.00 158.00   1.00   35.00    --   90.50  45.00-120.00   93
 31  \w     62.00 158.00   1.00   35.00    --   90.50  57.00-119.31   96
 32  \w     17.00  77.00   1.00   35.00    --   90.50 -45.00   0.00   60
 33  \w     62.00 158.00   1.00   35.00    --   90.50  58.00  81.17   96
 34  \w   -114.00 -13.00   1.00    5.93    --  -41.57 -57.00   0.00  101
 35  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00   0.00  109
 36  \w   -114.00 -13.00   1.00    5.93    --  -41.57 -57.00-180.00  101
 37  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00 120.00  109
 38  \w   -114.00 -13.00   1.00    5.93    --  -41.57 -57.00-120.00  101
 39  \w   -115.00 -16.00   1.00    5.93    --  -41.57 -41.00  65.86   99
 40  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00 -60.00  109
 41  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00-120.00  109
 42  \w    -31.00  70.00   1.00    5.93    --   41.57 -57.00-150.00  101
 43  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00 -90.00  109
 44  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00-150.00  109
 45  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00-180.00  109
 46  \w     17.00  77.00   1.00   35.00    --   90.50 -45.00  60.00   60
 47  \w     13.00 123.00   1.00   35.00    --   90.50 -79.00  93.92  110
 48  \w     63.00 158.00   1.00   35.00    --   90.50  56.00-104.06   95
 49  \w     65.00 158.00   1.00   35.00    --   90.50  45.00-180.00   93
 50  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00 -60.00  109
 51  \w     63.00 158.00   1.00   35.00    --   90.50  52.00 -26.01   95
 52  \w     13.00 124.00   1.00   35.00    --   90.50 -80.00  39.67  111
 53  \w     62.00 158.00   1.00   35.00    --   90.50  59.00 101.61   96
 54  \w     65.00 158.00   1.00   35.00    --   90.50  45.00  90.00   93
 55  \w     65.00 158.00   1.00   35.00    --   90.50  45.00 150.00   93
 56  \w     13.00 123.00   1.00   35.00    --   90.50 -79.00 122.30  110
 57  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00  30.00  109
 58  \w     13.00 124.00   1.00   35.00    --   90.50 -80.00 -78.01  111
 59  \w     13.00 124.00   1.00   35.00    --   90.50 -80.00 165.81  111
 60  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00-120.00  109
 61  \w     13.00 123.00   1.00   35.00    --   90.50 -79.00 134.50  110
 62  \w     13.00 123.00   1.00   35.00    --   90.50 -79.00  11.62  110
 63  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00-180.00  109
 64  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00   0.00  109
 65  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00 -30.00  109
 66  \w     65.00 158.00   1.00   35.00    --   90.50  45.00  30.00   93
 67  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00 -90.00  109
 68  \w     14.00 123.00   1.00   35.00    --   90.50 -77.00-150.00  109
 69  \w     63.00 158.00   1.00   35.00    --   90.50  53.00  54.77   95
 70  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-180.00  109
 71  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-150.00  109
 72  \w   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-120.00  109
 73  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00  30.00  109
 74  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00 120.00  109
 75  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00 150.00  109
 76  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00  90.00  109
 77  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00  60.00  109
 78  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00   0.00  109
 79  \w    -35.00  74.00   1.00    5.93    --   41.57 -77.00 -30.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0815093000
_diffrn_orient_matrix_UB_12      0.0650888000
_diffrn_orient_matrix_UB_13      0.0864512000
_diffrn_orient_matrix_UB_21      -0.1162741000
_diffrn_orient_matrix_UB_22      0.0093654000
_diffrn_orient_matrix_UB_23      0.0342670000
_diffrn_orient_matrix_UB_31      0.0072683000
_diffrn_orient_matrix_UB_32      -0.1259137000
_diffrn_orient_matrix_UB_33      0.0116535000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_number            3476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.294
_diffrn_reflns_theta_min         4.063
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             108
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.36
_refine_diff_density_max         1.043
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.35(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0388
_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/[\s^2^(Fo^2^)+(0.0553P)^2^+0.0378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3302
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra08389a2.cif
_cod_data_source_block           16jd001
_cod_database_code               7244973
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C3H4O4
_chemical_oxdiff_usercomment     'Malonic Acid'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.890
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     45.18
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O01-H01
 1.015 with sigma of 0.02
 O04-H04
 1.015 with sigma of 0.02
 H02A-C02
 1.098 with sigma of 0.002
 H02B-C02
 1.098 with sigma of 0.002
;
_shelx_res_checksum              67173
_ins_header
;
TITL 16JD001 in P-1 
REM P-1 (#2 in standard setting)
CELL 0.71073   5.155569   5.325063   8.194224 108.1076 101.2440  95.2653
ZERR    2.00   0.000064   0.000070   0.000098   0.0011   0.0010   0.0010
LATT  1
SFAC C H O
UNIT 6.00 8.00 8.00
REM  CrysAlisPro recorded range (K): Min=149.6; max=150.3; aver:149.9
TEMP -123
SIZE 0.36 0.62 0.74
TREF
HKLF 4
END
;
_olex2_exptl_crystal_mounting_method Paratone-N
_olex2_submission_original_sample_id 'THEO AN II'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.772