Sustainable solid form screening: mechanochemical control over nucleobase hydrogen-bonded organic framework polymorphism
Stolar, Tomislav; Alić, Jasna; Lončarić, Ivor; Etter, Martin; Jung, Dahee; Farha, Omar K.; Đilović, Ivica; Meštrović, Ernest; Užarević, Krunoslav; CrystEngComm  (2022) –; doi:10.1039/D2CE00668E

data_7245423
_publ_section_title
;
 Sustainable solid form screening: mechanochemical control over nucleobase
 hydrogen-bonded organic framework polymorphism
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00668E
_journal_year                    2022
_chemical_formula_moiety         'C5 H6 N6'
_chemical_formula_sum            'C5 H6 N6'
_chemical_formula_weight         150.16
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-23 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                109.619(3)
_cell_angle_beta                 108.625(3)
_cell_angle_gamma                107.919(3)
_cell_formula_units_Z            6
_cell_length_a                   10.7265(5)
_cell_length_b                   11.3448(2)
_cell_length_c                   11.6327(4)
_cell_measurement_reflns_used    16920
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.9580
_cell_measurement_theta_min      4.5660
_cell_volume                     1118.77(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -109.00 -40.00   0.50    0.20    --  -46.91 -64.00-162.00  138
  2  \w    -57.00  11.00   0.50    0.20    --  -46.91  64.00 -26.00  136
  3  \w     64.00 101.00   0.50    0.20    --   46.91  64.00 -26.00   74
  4  \w     -2.00  62.00   0.50    0.20    --   46.91 -64.00-162.00  128
  5  \w   -154.00-108.00   0.50    0.80    --  -86.25 -64.00-162.00   92
  6  \w    -69.00 -44.00   0.50    0.80    --  -86.25  64.00 -26.00   50
  7  \w     35.00  75.00   0.50    0.80    --  107.75 -64.00-162.00   80
  8  \w     98.00 167.00   0.50    0.80    --  107.75  64.00 -26.00  138
  9  \w   -110.00 -75.00   0.50    0.20    --  -46.91-125.00  30.00   70
 10  \w   -116.00 -74.00   0.50    0.20    --  -46.91-125.00-150.00   84
 11  \w    -27.00  29.00   0.50    0.20    --  -46.91  19.00 -90.00  112
 12  \w    -25.00  27.00   0.50    0.20    --   46.91 -19.00  90.00  104
 13  \w     35.00  94.00   0.50    0.20    --   46.91-125.00  60.00  118
 14  \w    -47.00 -16.00   0.50    0.80    --  -86.25  45.00-180.00   62
 15  \w    -51.00 -14.00   0.50    0.80    --  -86.25  45.00 150.00   74
 16  \w     79.00 108.00   0.50    0.80    --  107.75-111.00 -58.68   58
 17  \w     36.00  62.00   0.50    0.80    --  107.75-111.00 -58.68   52
 18  \w     35.00 100.00   0.50    0.80    --  107.75 -95.00  90.00  130
 19  \w     35.00  71.00   0.50    0.80    --  107.75 -61.00 150.00   72
 20  \w     40.00  69.00   0.50    0.80    --  107.75-125.00   0.00   58
 21  \w     74.00 111.00   0.50    0.80    --  107.75-125.00   0.00   74
 22  \w     78.00 103.00   0.50    0.80    --  107.75 -95.00-150.00   50
 23  \w    117.00 176.00   0.50    0.80    --  107.75  38.00 -84.84  118
 24  \w     95.00 140.00   0.50    0.80    --  107.75 125.00 -90.00   90
 25  \w     42.00  97.00   0.50    0.80    --  107.75 -95.00   0.00  110
 26  \w     39.00  64.00   0.50    0.80    --  107.75-125.00-180.00   50
 27  \w     87.00 112.00   0.50    0.80    --  107.75-125.00-180.00   50
 28  \w    145.00 174.00   0.50    0.80    --  107.75 125.00 -90.00   58
 29  \w    105.00 177.00   0.50    0.80    --  107.75  26.00-119.12  144
 30  \w     37.00  63.00   0.50    0.80    --  107.75 -61.00 -90.00   52
 31  \w     95.00 178.00   0.50    0.80    --  107.75  45.00  90.00  166
 32  \w     39.00  80.00   0.50    0.80    --  107.75 -77.00-120.00   82
 33  \w     40.00 102.00   0.50    0.80    --  107.75 -95.00  60.00  124
 34  \w    117.00 174.00   0.50    0.80    --  107.75  30.00-180.00  114
 35  \w     41.00  66.00   0.50    0.80    --  107.75 -95.00 120.00   50
 36  \w     37.00  68.00   0.50    0.80    --  107.75 -95.00 -30.00   62
 37  \w     77.00 103.00   0.50    0.80    --  107.75 -95.00  30.00   52
 38  \w     98.00 127.00   0.50    0.80    --  107.75 125.00  60.00   58
 39  \w     36.00 103.00   0.50    0.80    --  107.75 -95.00 150.00  134
 40  \w    123.00 176.00   0.50    0.80    --  107.75  77.00-180.00  106
 41  \w     76.00 108.00   0.50    0.80    --  107.75-109.00  50.89   64
 42  \w     35.00  60.00   0.50    0.80    --  107.75 -95.00  30.00   50
 43  \w     63.00 112.00   0.50    0.80    --  107.75-125.00-150.00   98
 44  \w     39.00  90.00   0.50    0.80    --  107.75-125.00  30.00  102
 45  \w     61.00 107.00   0.50    0.80    --  107.75-106.00-110.40   92
 46  \w    150.00 175.00   0.50    0.80    --  107.75 125.00  60.00   50
 47  \w     35.00  62.00   0.50    0.80    --  107.75 -61.00  90.00   54
 48  \w     52.00  78.00   0.50    0.80    --  107.75-125.00 150.00   52
 49  \w     86.00 112.00   0.50    0.80    --  107.75-125.00 150.00   52
 50  \w     43.00  69.00   0.50    0.80    --  107.75 -77.00 120.00   52
 51  \w     38.00  64.00   0.50    0.80    --  107.75 -77.00 150.00   52
 52  \w     43.00  70.00   0.50    0.80    --  107.75 -95.00 -90.00   54
 53  \w     64.00 112.00   0.50    0.80    --  107.75-125.00  60.00   96
 54  \w    104.00 129.00   0.50    0.80    --  107.75  91.00  39.20   50
 55  \w    137.00 178.00   0.50    0.80    --  107.75  91.00  39.20   82
 56  \w    105.00 172.00   0.50    0.80    --  107.75  30.00  30.00  134
 57  \w    126.00 158.00   0.50    0.80    --  107.75  -3.00  94.12   64
 58  \w     75.00 111.00   0.50    0.80    --  107.75-124.00 -45.82   72
 59  \w     42.00 112.00   0.50    0.80    --  107.75-125.00-120.00  140
 60  \w     36.00  67.00   0.50    0.80    --  107.75 -61.00   0.00   62
 61  \w     44.00  83.00   0.50    0.80    --  107.75-141.00 109.00   78
 62  \w    -79.00 -35.00   0.50    0.20    --  -46.91 130.00  -5.00   88
 63  \w    -13.00  15.00   0.50    0.20    --   46.91 -19.00 -30.00   56
 64  \w    145.00 171.00   0.50    0.80    --  107.75  15.00 -30.00   52
 65  \w     61.00  87.00   0.50    0.80    --  107.75-135.00  17.98   52
 66  \w     38.00  65.00   0.50    0.80    --  107.75 -77.00   0.00   54
 67  \w     67.00  93.00   0.50    0.80    --  107.75 -77.00   0.00   52
 68  \w     80.00 105.00   0.50    0.80    --  107.75 -95.00  60.00   50
 69  \w     43.00  69.00   0.50    0.80    --  107.75 -61.00-180.00   52
 70  \w     37.00  75.00   0.50    0.80    --  107.75 -77.00-180.00   76
 71  \w     94.00 119.00   0.50    0.80    --  107.75-135.00  17.98   50
 72  \w    116.00 173.00   0.50    0.80    --  107.75  45.00 150.00  114
 73  \w     94.00 147.00   0.50    0.80    --  107.75  77.00  60.00  106
 74  \w     47.00  73.00   0.50    0.80    --  107.75 -77.00 -60.00   52
 75  \w     80.00 105.00   0.50    0.80    --  107.75 -77.00 -60.00   50
 76  \w     50.00  88.00   0.50    0.80    --  107.75-125.00 150.00   76
 77  \w    146.00 172.00   0.50    0.80    --  107.75 125.00  90.00   52
 78  \w    107.00 139.00   0.50    0.80    --  107.75  15.00 -30.00   64
 79  \w     96.00 122.00   0.50    0.80    --  107.75-141.00 109.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0299184000
_diffrn_orient_matrix_UB_12      -0.1219036000
_diffrn_orient_matrix_UB_13      0.0088048000
_diffrn_orient_matrix_UB_21      0.1587386000
_diffrn_orient_matrix_UB_22      0.1076000000
_diffrn_orient_matrix_UB_23      0.1176734000
_diffrn_orient_matrix_UB_31      -0.0566252000
_diffrn_orient_matrix_UB_32      0.0084621000
_diffrn_orient_matrix_UB_33      0.1072286000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7318
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        65.995
_diffrn_reflns_theta_max         65.995
_diffrn_reflns_theta_min         4.674
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_recrystallization_method isopropanol
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         7318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0804
_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^)+(0.1757P)^2^+0.4101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2401
_refine_ls_wR_factor_ref         0.2466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6644
_reflns_number_total             7318
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 118.3424\% 
around [0.90 -0.30 -0.31] (reciprocal) or [1.00 -0.01 0.00] (direct)
;
_cod_data_source_file            d2ce00668e2.cif
_cod_data_source_block           manu_2_comp_twin1_hklf4
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C15 H18 N18'
_cod_original_formula_weight         450.47
_cod_original_formula_moiety         '3(C5 H6 N6)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1118.77(8)
_cod_database_code               7245423
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         '(C5 H6 N6)3 OH2'
_chemical_oxdiff_usercomment     'C5 H6 N6'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7487(18)
 0.2513(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3.a Rotating group:
 N36(H36A), N26(H26A)
3.b Aromatic/amide H refined with riding coordinates:
 N33(H33), N13(H13), N23(H23), C35(H35), C25(H25), C15(H15)
3.c X=CH2 refined with riding coordinates:
 N35(H35A,H35B), N15(H15A,H15B), N25(H25A,H25B), N16(H16A,H16B)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              45500
_shelx_hkl_checksum              86844
_shelx_fab_checksum              89670
_olex2_exptl_crystal_mounting_method 'Mounted in cryo mesh'
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.603
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2