Additive-driven microwave crystallization of tyramine polymorphs and salts: a quantum crystallography perspective.
Grabowski, Szymon; Nowakowska, Klaudia; Butkiewicz, Helena; Hoser, Anna; Wesełucha-Birczyńska, Aleksandra; Seidler, Tomasz; Moskal, Paulina; Gryl, Marlena; IUCrJ 12 (2025) –; doi:10.1107/S2052252525002210

data_1574547
_publ_section_title
;
 Additive-driven microwave crystallization of tyramine polymorphs and
 salts: a quantum crystallography perspective.
;
_journal_issue                   3
_journal_name_full               IUCrJ
_journal_paper_doi               10.1107/S2052252525002210
_journal_volume                  12
_journal_year                    2025
_chemical_formula_sum            'C32 H47 N5 O7'
_chemical_formula_weight         613.74
_chemical_name_common
'tyramine barbitalate water \\langle 1:1:1^+^/1^-^/1 \\rangle'
_chemical_name_systematic
;
2-(4-Hydroxyphenyl)ethanaminium
5,5-diethyl-2,4,6-trioxotetrahydro-2<i>H</i>-pyrimidin-1-ide
monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.6480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.11920(10)
_cell_length_b                   19.0384(2)
_cell_length_c                   10.01720(10)
_cell_measurement_reflns_used    24881
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      80.2140
_cell_measurement_theta_min      4.4110
_cell_volume                     1730.69(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'WinGX, (Farrugia, 2012)'
_computing_publication_material  'Mercury, (Macrae, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            36090
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.508
_diffrn_reflns_theta_min         4.435
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 3265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         7442
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+0.1557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                7120
_reflns_number_total             7442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            pen5003.cif
_cod_data_source_block           C1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1574547
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.954
_oxdiff_exptl_absorpt_empirical_full_min 0.800
_oxdiff_exptl_absorpt_empirical_full_max 1.273
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
_shelx_res_checksum              33757
_shelx_hkl_checksum              62854