Synthesis and structure of a 1:1 co-crystal of hexamethylenetetramine carboxyborane and acetaminophen
Ayudhya, Theppawut; Raymond, Casey; Dingra, Nin; Acta Crystallographica Section E 76 (2020) 1854–1858; doi:10.1107/S2056989020015327

data_2243685
_publ_section_title
;
 Synthesis and structure of a 1:1 co-crystal of hexamethylenetetramine
 carboxyborane and acetaminophen
;
_journal_coeditor_code           HB7947
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1854
_journal_page_last               1858
_journal_paper_doi               10.1107/S2056989020015327
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C15 H22 B N5 O3, C8 H9 N O2'
_chemical_formula_moiety         'C15 H22 B N5 O3, C8 H9 N O2'
_chemical_formula_sum            'C23 H31 B N6 O5'
_chemical_formula_weight         482.35
_chemical_name_common
;
Hexamethylenetetramine carboacetaminophenborane--acetaminophen (1/1)
;
_chemical_name_systematic
;
Hexamethylenetetramine 4-acetamidophenyl
2-boranylacetate--4-acetamidophenol (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.929(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.760(4)
_cell_length_b                   9.5527(19)
_cell_length_c                   12.045(2)
_cell_measurement_reflns_used    7373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.104
_cell_measurement_theta_min      5.797
_cell_volume                     2387.3(8)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2014/7</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.963
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0180P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                3044
_reflns_number_total             4870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7947sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2387.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243685
_cod_database_fobs_code          2243685
_shelx_hkl_checksum              18515
_shelx_res_checksum              19720