Crystal structure of the co-crystalline adduct 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1<sup>3,8</sup>]dodecane (TATD)-4-iodo-phenol (1/2): supra-molecular assembly mediated by halogen and hydrogen bonding.
Rivera, Augusto; Rojas, Jicli José; Ríos-Motta, Jaime; Bolte, Michael; Acta crystallographica. Section E, Crystallographic communications 73 (2017) 1692–1695; doi:10.1107/S2056989017014943

data_2311489
_publ_section_title
;
 Crystal structure of the co-crystalline adduct
 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1<sup>3,8</sup>]dodecane
 (TATD)-4-iodo-phenol (1/2): supra-molecular assembly mediated by halogen
 and hydrogen bonding.
;
_journal_coeditor_code           SJ5537
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1692
_journal_page_last               1695
_journal_paper_doi               10.1107/S2056989017014943
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H16 N4, 2C6 H5 I O'
_chemical_formula_moiety         'C8 H16 N4, 2(C6 H5 I O)'
_chemical_formula_sum            'C20 H26 I2 N4 O2'
_chemical_formula_weight         608.25
_chemical_name_systematic
;
1,3,6,8-Tetraazatricyclo[4.4.1.1^3,8^]dodecane--4-iodophenol (1/2)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.8869(16)
_cell_length_b                   22.4197(13)
_cell_length_c                   9.6352(6)
_cell_measurement_reflns_used    15571
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      3.58
_cell_volume                     4512.0(5)
_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
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2016 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0287
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7213
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.528
_diffrn_reflns_theta_min         3.585
_exptl_absorpt_coefficient_mu    2.810
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.670
_refine_ls_abs_structure_details
;
Classical Flack (1983) method preferred over Parsons because s.u. lower
;
_refine_ls_abs_structure_Flack   -0.03(4)
_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     132
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+5.1297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                2079
_reflns_number_total             2102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5537sup1.cif
_cod_data_source_block           I
_cod_database_code               2311489
_shelx_estimated_absorpt_t_min   0.552
_shelx_estimated_absorpt_t_max   0.564
_shelx_hkl_checksum              19289
_shelx_res_checksum              50353