Beyond hydrogen bonds: unveiling the structure-directing role of side-on X···π interactions in adamantane-thiourea crystals
Al-Wahaibi, Lamya H.; Blacque, Olivier; Al-Mutairi, Aamal A; El-Emam, Ali A.; Gomila, Rosa Maria; Frontera, Antonio; Tiekink, Edward R. T.; CrystEngComm  (2025) –; doi:10.1039/D5CE00817D

data_7251061
_publ_section_title
;
 Beyond hydrogen bonds: unveiling the structure-directing role of side-on
 X&#x00B7;&#x00B7;&#x00B7;\p interactions in adamantane-thiourea crystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00817D
_journal_year                    2025
_chemical_formula_moiety         'C18 H22 N4 O2 S'
_chemical_formula_sum            'C18 H22 N4 O2 S'
_chemical_formula_weight         358.45
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-08-21 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                96.592(2)
_cell_angle_beta                 97.243(2)
_cell_angle_gamma                104.197(2)
_cell_formula_units_Z            2
_cell_length_a                   6.34180(10)
_cell_length_b                   11.5247(3)
_cell_length_c                   12.2090(2)
_cell_measurement_reflns_used    11716
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      78.4540
_cell_measurement_theta_min      3.6950
_cell_volume                     848.26(3)
_computing_cell_refinement       'CrysAlisPRO (OD, 2024)'
_computing_data_collection       'CrysAlisPRO (OD, 2024)'
_computing_data_reduction        'CrysAlisPRO (OD, 2024)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18883
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.336
_diffrn_reflns_theta_min         3.692
_exptl_absorpt_coefficient_mu    1.863
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0556P)^2^+0.2982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3243
_reflns_number_total             3566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00817d2.cif
_cod_data_source_block           shelx_CCDC3
_cod_database_code               7251061
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.685
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              97142