First hydrogen-bonded adduct of sterically hindered 2-<i>tert</i>-butyl-4-methylphenol (TBMP) with 1,3,6,8-tetraazatricyclo[4.4.1.1^3,8^]dodecane (TATD) <i>via</i> coupling of classical hydrogen bonds and C—H···π non-covalent interactions
Rivera, Augusto; Ríos-Motta, Jaime; Bolte, Michael; Acta Crystallographica Section E 78 (2022) –; doi:10.1107/S2056989022004972

data_2244094
_publ_section_title
;
 First hydrogen-bonded adduct of sterically hindered
 2-<i>tert</i>-butyl-4-methylphenol (TBMP) with
 1,3,6,8-tetraazatricyclo[4.4.1.1^3,8^]dodecane (TATD) <i>via</i> coupling
 of classical hydrogen bonds and C---H&#x00B7;&#x00B7;&#x00B7;\p
 non-covalent interactions
;
_journal_coeditor_code           YZ2019
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022004972
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C8 H16 N4, 2C11 H16 O'
_chemical_formula_moiety         'C8 H16 N4, 2(C11 H16 O)'
_chemical_formula_sum            'C30 H48 N4 O2'
_chemical_formula_weight         496.72
_chemical_name_systematic
;
2-<i>tert</i>-Butyl-4-methylphenol--\
1,3,6,8-tetraazatricyclo[4.4.1.1^3,8^]dodecane (2/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 108.166(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4741(10)
_cell_length_b                   7.6770(5)
_cell_length_c                   17.2226(14)
_cell_measurement_reflns_used    17127
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      3.55
_cell_volume                     1441.5(2)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-Area (Stoe & Cie, 2001)
;
_computing_molecular_graphics
;
XP in SHELXTL-Plus (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17127
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.640
_diffrn_reflns_theta_min         3.639
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-Area; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2016/6 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0663P)^2^+0.4499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                2862
_reflns_number_total             3307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yz2019sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2244094
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.992
_shelx_hkl_checksum              71688
_shelx_res_checksum              66729
_cod_database_fobs_code 2244094