Mechanochemical synthesis and crystal structure of a 1:2 co-crystal of 1,3,6,8-tetraazatricyclo[4.3.1.1^3,8^]undecane (TATU) and 4-chloro-3,5-dimethylphenol
Rivera, Augusto; Rojas, Jicli José; Sadat-Bernal, John; Ríos-Motta, Jaime; Bolte, Michael; Acta Crystallographica Section E 72 (2016) 1651–1653; doi:10.1107/S2056989016016650

data_2241905
_publ_section_title
;
 Mechanochemical synthesis and crystal structure of a 1:2 co-crystal of
 1,3,6,8-tetraazatricyclo[4.3.1.1^3,8^]undecane (TATU) and
 4-chloro-3,5-dimethylphenol
;
_journal_coeditor_code           SJ5512
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1651
_journal_page_last               1653
_journal_paper_doi               10.1107/S2056989016016650
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C7 H14 N4, 2C8 H9 Cl O'
_chemical_formula_moiety         'C7 H14 N4, 2(C8 H9 Cl O)'
_chemical_formula_sum            'C23 H32 Cl2 N4 O2'
_chemical_formula_weight         467.42
_chemical_name_systematic
;
1,3,6,8-Tetraazatricyclo[4.3.1.1^3,8^]undecane--4-chloro-3,5-dimethylphenol
(1/2)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.824(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5170(8)
_cell_length_b                   7.6178(4)
_cell_length_c                   22.1756(11)
_cell_measurement_reflns_used    23030
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      3.27
_cell_volume                     2400.3(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
;
<i>SHELXL2014/7</i> (Sheldrick, 2015)
;
_computing_structure_refinement
;
<i>SHELXL2014/7</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'STOE IPDS II two-circle'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23030
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.718
_diffrn_reflns_theta_min         3.267
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-Area; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0488P)^2^+0.6672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                3584
_reflns_number_total             4501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5512sup1.cif
_cod_data_source_block           I
_cod_database_code               2241905
_cod_database_fobs_code          2241905
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.932
_shelx_hkl_checksum              59009
_shelx_res_checksum              50818